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Abstract

E ver  since  the  creation  of  Man,  humanity  has  been  on  a  never-­‐ending  quest  of  discovery  and  

invention.  From  the  most  important  discovery  of  all  time-­‐fire,  to  the  most  important  invention  
of  all  time-­‐  the  wheel,  mankind  never  stopped  asking  questions  about  everything  and  anything.  
The   following   pages   are   an   attempt   to   follow   in   the   footsteps   of   those   great   inventors,  
explorers,   and   scientists;   the   following   is   a   literature   survey,   a   feeble   attempt   at   finding   out  
everything  there  is  to  find  out  about  a  popular  chemical  substance:  Acetone.  

[We   realize   that   this   is   an   unusual   passage,   but   since   we   did   not   come   up   with   any   original  
material,  the  abstract  was  our  only  shot  at  creativity.  
Contents  

Summary…………………………………………………………………………………..3  

Introduction………………………………………………………………………………4  

Properties  of  Acetone:    

       i-­‐Chemical  Identity………………………………………………………………..5  

       ii-­‐Physical  Properties   ………………………………………………………….6  

       iii-­‐Thermodynamic  Properties……………………………………………….7  

       iv-­‐Chemical  Properties………………………………………………………….8  

History  of  Acetone:  Discovery  and  Early  Mass-­‐Production………10                                                                                                              

Modern  Production  Methods  (Main  Production  Methods)……..11  

Applications  of  Acetone………………………………………………………….15  

Storage  and  Handling………………………………………………………………17  

Emissions  and  Environmental  Effects………………………………………23  

Specifications,  Standards,  and  Quality  Control…………………………26  

References……………………………………………………………………………….28  

Appendices………………………………………………………………………………..30  

   

  2  
Summary  
Man  has  officially  isolated  acetone  in  the  late  14th  century,  but  acetone  has  been  with  mankind  
since   the   species’   very   beginning;   it   is   a   natural   product   of   a   mammal’s   metabolic   reactions.  
Acetone  is  a  colorless  substance  with  a  fruity  odor  and  a  pleasant  taste.  The  world  produces  3  
million  metric  tons  of  acetone  each  year  since  the  year  2000,  and  over  50%  of  that  amount  is  
used   to   make   various   polymers.   The   remaining   50%   is   used   in   solvents,   food   packaging,  
exfoliation,  domestic  cleaners,  and  cryogenic  experiments.  

Historically,  acetone  was  made  by  the  distillation  of  lead-­‐acetate.  But  as  demand  grew,  some  
plants  resorted  to  the  biofermentation  of  carbohydrates,  and  as  the  demand  for  pure  acetone  
grew   even   higher   during   the   20th   century,   the   newly   discovered   Cumene   Hydroperoxide  
method  was  adopted  by  most  countries.  

The  cumene  hydroperoxide  method  remains  the  most  popular  method  for  acetone  production,  
the   other   method   being   of   smaller   importance,   namely   the   dehydrogenation   of   isopropyl  
alcohol.  

Acetone  is  a  flammable  as  a  liquid,  and  as  a  vapor  it  has  a  narrow  flammability  range.  Special  
precautions  are  taken  during  its  transportation,  handling,  and  storage.  Workers  who  may  come  
in  direct  contact  with  acetone  are  advised  to  use  personal  respirators,  eye  and  skin  protection  
(equipment  must  be  OSHA-­‐Approved)  to  avoid  adverse  health  effects.  

Acetone   is   naturally   biodegradable,   with   no   known   negative   effects   on   air,   soil,   or   water   it  
might  be  released  into.  

  3  
Introduction    
Acetone  is   an  organic   compound  with   the  formula  (CH3)2CO.   This   colorless,   mobile,   flammable  
liquid  is  the  simplest  example  of  ketones.  Acetone  is  miscible  in  water.  More  than  3  million  tons  
are  produced  annually,  mainly  as  a  precursor  to  polymers.  Familiar  household  uses  of  acetone  
are   as   the   active   ingredient   in  nail   polish   remover  and   as   paint   thinner   and   sanitary-­‐cleaner  
base.   It   is   a   common   building   block   in   organic   chemistry.   Acetone   is   naturally   produced   and  
disposed   of   in   the   human   body   as   a   result   of   normal   metabolic   processes   (you   can   smell  
acetone   in   a   person’s   breath   if   they   haven’t   eaten   for   a   long   time).   It   also   serves   as   an  
important  solvent  on   its   own,   typically   as   the   solvent   of   choice   for   cleaning   purposes   in   the  
laboratory.  

   

  4  
Properties  of  Acetone    
 

1-­‐Chemical  Identity  

Chemical  name                                                    Acetone  

Synonym        Dimethyl  Ketal,  Dimethyl  Ketone,  Ketopropane,  Methylacetal,  2-­‐Propanone,  and  Pyroacetic  Ether.  

Chemical  formula                                        C3H6O  

         

Proposed  Chemical  Structure          

  5  
2-­‐Physical  properties  

Acetone   is   a   clear   and   colorless   liquid   with   a   strong   "fruity"   odor.   It   is   miscible   in   water   and  
organic   solvents   such   as   ether,   methanol,   ethanol   and   esters.   Physical   properties   of   acetone  
such  as  high  evaporation  rate,  low  viscosity  and  miscibility,  make  it  suitable  for  use  as  a  solvent.  

  6  
3-­‐Thermodynamic  Properties  

Property   Value  

Specific  Heat  of  Liquid  at  20oC   2.6J/g  

Specific  Heat  of  Vapor  at  102oC                                                              92.1J/(mol.K)  


   

Heat  of  Vaporization  at  56.1oC                                                                29.1kJ/mol  


   

Enthalpy  of  Vaporization                                                                                    30.836kJ/mol  


 

Enthalpy  of  Fusion  at  melting  point                                              5691.22J/mol  


     

Heat  of  Combustion  of  Liquid                                                                    1787J/mol  


   

Enthalpy  of  Combustion                                                                                        -­‐1659.17kJ/mol  


 

Entropy  of  Liquid                                                                                                                200.1J/(mol.K)  

Entropy  of  Ideal  Gas                                                                                                      296.349J/(mol.K)  

Gibbs  Energy  of  Formation                                                                              -­‐152.716kJ/mol  


 

Enthalpy  of  Formation:    

Ideal  Gas                                                                                                                                             -­‐217.15kJ/mol  

Non-­‐Ideal  Gas                                                                                                                            -­‐216.5kJ/mol  

Liquid   -­‐248  kJ/mol  

  7  
4-­‐Chemical  Properties  

The   closed   cup   flash   point   of   acetone   is   -­‐1.8°C   and   open   cup   -­‐9°   C.   The   auto   ignition  
temperature  is  465°C,  and  the  flammability  limits  are  2.6  to  13  vol  %  in  air  at  20°C.  

Acetone   shows   the   typical   reactions   of   saturated   aliphatic   ketones.   It   forms   crystalline  
compounds   such   as   acetone   sodium   bisulfite   (CH3)2C(OH)SO3Na   with   alkali   bisulfite.   The   highly  
reactive   compound   ketene   CH2=C=O,   results   from   the   pyrolysis   of   acetone.   Reducing   agents  
convert   acetone   to   pinacol   ,   isopropyl   alcohol,   or   propane.   Reductive   ammonolysis   produces  
isopropyl   amines.   Acetone   is   stable   to   many   of   the   usual   oxidants   such   as   Fehling's   solution,  
silver  nitrate,  cold  nitric  acid,  and  neutral  potassium  permanganate,  but  it  can  be  oxidized  by  
some  of  the  stronger  oxidants  such  as  alkaline  permanganate,  chromic  acid,  and  hot  nitric  acid.  
Metal  hypohalite,  or  a  halogen  in  the  presence  of  a  base,  oxidizes  acetone  to  a  metal  acetate  
and   a   haloform,   e.g.   iodoform.   Halogens   alone   substitute   for   the   H   atoms,   yielding   halo-­‐
acetones.   Acetone   is   a   metabolic   product   in   humans   and   some   other   mammals   and   is   a   normal  
constituent  of  their  blood  and  urine.  In  people  suffering  from  diabetes,  it  is  present  in  relatively  
larger  amounts.  

Compounds  with  active  hydrogen  add  to  the  carbonyl  group  of  acetone,  often  followed  by  the  
condensation   of   another   molecule   of   the   addition   or   loss   of   water.   Hydrogen   sulfide   forms  
hexamethyl   1,3,5-­‐trithiane,   probably   through   the   transitory   intermediate   thioacetone   which  
readily   trimerizes.   Hydrogen   cyanide   forms   acetone   cyanohydrin     (CH3)2C(OH)CN,   which   is  
further   processed   into   methaciylates.   Ammonia   and   hydrogen   cyanide   give   (CH3)2C(NH2)CN    
from  which  the  widely  used  polymerization  initiator,  AIBN(Azo-­‐bis-­‐isobutyronitrile)  is  made  .  

Primary   amines   form   Schiff   bases,   (CH3)2C=NR.   Ammonia   induces   an   aldol   condensation  
followed  by  1,4-­‐addition  of  ammonia  to  produce:  ketone  amine  (from  mesityl  oxide),  4-­‐amino-­‐
4-­‐methyl   -­‐2-­‐pentanone,   (CH3)2C(NH)Ch2yCOCH3,   and   triacetone   amine   (from   phorone),  
2,2)6,6-­‐tetramethyl-­‐4-­‐piperidinone  .  Hydroxylamine  forms  the  oxime  and  hydrazine  compounds  
(RNHNH2)   formhydrazones   (RNHN=C(CH3)2).   Acetone   and   nitrous   acid   give   the   isonitroso  
compound  which  is  the  monoxime  of  pyruvaldehyde  CH3COCH=NOH.  

With   aldehydes,   primary   alcohols   readily   form   acetals,   RCH(OR')2.   Acetone   also   forms   acetals  
(often  called  totals),  (CH3)2C(OR)2  in  an  exothermic  reaction,  but  the  equilibrium  concentration  
is   small   at   ambient   temperature.   However,   the   methyl   acetate   of   acetone,   2,2-­‐
dimethoxypropane   ,   was   once   made   commercially   by   reaction   with   methanol   at   low  
temperature   for   use   as   a   gasoline   additive.   Isopropenyl   methyl   ether,   useful   as   a   hydroxyl  
blocking  agent  in  methane  and  epoxy  polymer  chemistry,  is  obtained  in  good  yield  by  thermal  
pyrolysis   of   2,2-­‐dimethoxypropane.   With   other   primary,   secondary,   and   tertiary   alcohols,  
equilibrium  is  progressively  less  favorable  to  the  formation  of  totals,  in  that  order.    

  8  
However,  acetals  of  acetone  with  other  primary  and  secondary  alcohols,  and  of  other  ketones,  
can   be   made   from   2,2-­‐dimethoxypropane   by   transacetalation   procedures.   Because   they  
hydrolyze   extensively,   totals   of   primary   and   especially   secondary   alcohols   are   effective   water  
scavengers.  

Acetone   has   long   been   used   as   an   agent   to   block   the   reactivity   of   hydioxyl   groups   in   1,2   and  
1,3-­‐diols,   especially   in   carbohydrate   chemistry.   The   equilibrium   for   the   formation   of   acetals  
with   hydroxyls   in   these   compounds   is   more   favorable   because   the   products   are   five   and   six-­‐
membered   ring   compounds,   1,3-­‐dioxolanes   and   dioxanes,   respectively.   With   glycerol   the  
equilibrium  constant  for  formation  of  the  dioxolane  is  about  0.50  at  23°C  and  0.29  at  48°C  in  a  
mixture   resulting   from   acidification   of   equal   volumes   of   acetone   and   glycerol   at   ambient  
temperature.  The  equilibrium  can  be  displaced  toward  acetal  formation  by  the  use  of  a  water  
scavenger   (an   anhydrous   metal   salt   such   as   copper   slate).Acetone   undergoes   aldol   additions  
and  further  reacts  with  the  products,  forming  aldol  chemicals,  diacetone  alcohol  (4-­‐hydroxy-­‐4-­‐
methyl-­‐2-­‐pentanone),  mesityl  oxide  (4-­‐methyl-­‐3-­‐penten-­‐2-­‐one),  isophorone  (3,5,5-­‐trimethyl-­‐2-­‐
cyclohexenone),   phorone   (2,6-­‐dimethyl-­‐2,5-­‐heptadien-­‐4-­‐one),   and   mesitylene   (1,3,5-­‐
trimethylbenzene).   From   these   are   produced   the   industrial   solvent   methyl   isobutyl   ketone  
(MIBK,   4-­‐methyl-­‐2-­‐pentanone),   methylisobutylcarbinol   (MIBC,   4-­‐methyl-­‐2-­‐pentanol),   hexylene  
glycol   (2-­‐methyl-­‐2,4-­‐pentadiol),   and   others.   Acetone   enters   the   typical   nucleophilic   addition  
and   condensation   reactions   of   ketone   both   at   its   carbonyl   group   and   at   its   methyl   groups,   with  
aldehydes,   other   ketones,   and   esters.   The   Claisen   reaction   with   ethyl   acetate   gives  
acetylacetone   (2,4-­‐pentanedione).   Mannich   reaction   with   secondary   amines   gives   R2NCH2-­‐  
abstained   acetones.   And   the   Reformatzy   reaction   gives   β-­‐hydroxy   esters.   Glycidic   esters   (esters  
with  a  2-­‐epoxy  group)  can  be  made  by  condensation  of  acetone  and  chloroacetic  esters  with  a  
metal  alkoxide.  

The  para-­‐  and  ortho-­‐  positions  of  phenols  condense  at  the  carbonyl  group  of  acetone  to  make  
bisphenol,   e.g.   bisphenol-­‐A,   (4,4’-­‐1-­‐methylethylidene   bisphenol).   If   the   hydrogen   atom   is  
activated,   ClCH-­‐compounds   add   to   the   carbonyl   group   in   the   presence   of   strong   base;  
chloroform  gives  chloroethane(1,1,1-­‐trichloro-­‐2-­‐methyl-­‐2-­‐propanol).  

  9  
History  of  Acetone:  Discovery  and  Early  Mass-­‐Production  
Acetone   was   originally   observed   in   1595   as   a   product   of   the   distillation   of   sugar-­‐of-­‐lead   (aka  
lead  acetate).  In  the  nineteenth  century,  it  was  obtained  by  the  destructive  distillation  of  metal  
acetates,  wood,  and  carbohydrates  with  lime,  and  pyrolysis  of  citric  acid.  Its  composition  was  
determined  by  Liebig  and  Dumas  in  1832.  

Until   World   War   I,   acetone   was   manufactured   commercially   by   the   dry   distillation   of   calcium  
acetate   from   lime   and   pyroligneous   acid   (wood   distillate).   These   methods   were   displaced   by  
the   process   developed   for   the   bacterial   fermentation   of   carbohydrates   (corn   starch   and  
molasses)  to  acetone  and  alcohols.  At  one  time  Publicker  Industries,  Commercial  Solvents,  and  
National  Distillers  had  a  combined  biofermentation  capacity  of  22,700  metric  tons  of  acetone  
per  year.  Biofermentation  became  noncompetitive  around  1960  because  of  the  economics  of  
scale   of   the   isopropyl   alcohol   dehydrogenation   and   cumene   hydroperoxide   processes,   and  
because  some  animal-­‐rights  groups  argued  that  it  was  abusive  to  the  bacteria  involved.  

  Production  of  acetone  by  dehydrogenation  of  isopropyl  alcohol  began  in  the  early  1920s  
and  remained  the  dominant  production  method  through  the  1960s.In  the  mid-­‐1960s,  virtually  
all  the  United  States’  acetone  was  produced  from  propylene.  A  process  for  direct  oxidation  of  
propylene   to   acetone   was   developed   by   a   chemist   by   the   name   of   Wacker   Chemie,   but   is  
believed  not  to  have  been  used  in  the  United  States.  However,  by  the  mid-­‐1970s,  60%  of  United  
States  acetone  capacity  was  based  on  cumene  hydroperoxide,  which  accounted  for  about  65%  
of  the  acetone  produced.  

Acetone  was  a  co-­‐product  of  the  Shell  process  for  glycerol.  Propylene  was  hydrated  to  isopropyl  
alcohol.   Some   of   the   alcohol   was   catalytically   oxidized   to   acrolein   and   some   was   oxidized   to  
give   hydrogen   peroxide   and   acetone.   Some   more   of   the   isopropyl   alcohol   and   the   acrolein  
reacted  to  give  allyl-­‐alcohol  and  acetone.  The  allyl-­‐alcohol  was  then  treated  with  the  peroxide  
to   give   glycerol.   About   1.26   kg   of   acetone   resulted   per   kg   of   glycerol.   In   1974,   23   to   32   kilotons  
of  acetone  may  have  been  produced  by  this  method.  

Direct   oxidation   of   hydrocarbons   and   catalytic   oxidation   of   isopropyl   alcohol   have   also   been  
used  for  commercial  production  of  acetone.  

  10  
Modern  Production  Methods  (Main  Production  Methods)  
Nowadays,  acetone  is  manufactured  mainly  by  cumene  peroxidation,  catalytic  steam  reforming  
of  ethanol,  or  isopropyl-­‐alcohol  dehydrogenation  processes.  The  cumene  peroxidation  process  
produces  trace  quantities  of  benzene  as  a  by-­‐product.  

1-­‐Cumene  Hydroperoxide  Process  to  Produce  Phenol  and  Acetone  

Benzene  is  alkylated  to  cumene,  and  then  it  is  oxidized  to  cumene  hydroperoxide,  which  in  turn  
is  cleaved  to  phenol  and  acetone.    

                                                                                       C6H5CH(CH3)2  +  O2  →  C6H5OH  +  (CH3)2CO  

One  kg  of  phenol  production  results  in  0.6  kg  of  acetone  or  about  0.40–  0.45  kg  of  acetone  per  
kg  of  cumene  used.    

The  process  steps  are:  

1-­‐Oxidation  of  cumene  to  a  concentrated  hydroperoxide  

2-­‐Cleavage  of  the  hydroperoxide  

3-­‐Neutralization  of  the  cleaved  products  

4-­‐Distillation  to  recover  acetone  

The  cumene  route  is  the  preferred  technology  because  of  its  lower  costs  and  nearly  90%  of  the  
world’s  acetone  is  produced  in  this  way.  

Below  are  extracts  (abstracts,  to  be  more  accurate)  of  various  research  papers  we  have  come  
across  during  our  literature  survey.  They  show  a  number  of  production  methods  that  have  been  
industrially  tested  and  applied.  The  complete  papers  have  been  included  in  the  appropriate  Appendix  section.  

B.  Sivasankar  and  K.  Rengaraj  studied  catalytic  decomposition  of  cumene  hydroperoxide  into  
phenol  and  acetone.  The  decomposition  of  cumene  hydroperoxide  (CHP)  was  carried  out  in  a  
batch   reactor   over   supported   solid   acid   catalysts,   acid-­‐activated   montmorillonite   K10   (Mont.  
K10)  and  metal-­‐ion-­‐exchanged  (Mont.  K10),  at  30–60oC.  

The   products   were   phenol   and   acetone.   Supported   dodecatungstophosphoric   acid   (DTPA)  
showed   100%   conversion   within   5   min   at   30oC;   the   results   obtained   over   acid-­‐activated   (Mont.  
K10)   were   also   comparable.   The   type   of   acidity   and   the   strength   were   determined.   The  
correlation   of   catalytic   activity   with   acidity   revealed   that   both   Lewis   and   Bronsted   acid   sites  
promote  the  decomposition.  The  reaction  was  first-­‐order  with  respect  to  CHP.    

  11  
The   results   indicate   that   heterogeneous   catalysts   may   be   used   instead   of   sulfuric   acid   for  
selective  decomposition  of  CHP  into  phenol  and  acetone  with  100%  conversion.  

Konstantin   Yu.   Koltunov   and   Vladimir   I.   Sobolev   studied   the   efficient   cleavage   of   cumene  
hydroperoxide   over   HUSY   zeolites   and   the   role   of   Brønsted   acidity.   The   cleavage   of   cumene  
hydroperoxide   in   the   presence   of   H-­‐form   USY   zeolites   to   form   phenol   and   acetone   has   been  
examined.   For   comparison,   the   same   reaction,   catalyzed   by   Y-­‐,   ZSM-­‐5,   b-­‐zeolites,   as   well   as  
sulfuric  and  heteropolyacids  is  performed.  As  it  appeared,  HUSY  zeolites  of  high  Si/Al  ratio  (15  
and   40)   are   sufficiently   active   catalysts,   and   their   efficiency   is   comparable   to   that   of   sulfuric  
acid.  Such  outstanding  catalytic  performance  of  HUSY  should  be  attributed  to  combination  of  
favorable   porous   topology,   sorption   properties   and   relatively   strong   acidity   of   the   internal  
surface.   The   acid   strength   of   HY   and   HUSY   zeolites   is   roughly   estimated   in   terms   of   H/D  
exchange   between   de-­‐uterated   acetone   and   water   over   the   solid   acid,   while   their   sorption  
properties  are  estimated  based  on  H2O-­‐TPD  measurements.  

Dagang   Huang,   Minghan   Han,   Jinfu   Wang,   and   Yong   Jin   studied   the   Catalytic   decomposition  
process  of  cumene  hydroperoxide  using  sulfonic  resins  as  catalyst.  A  new  catalytic  process  for  
cumene  hydroperoxide  (CHP)  decomposition  using  sulfonic  resins  is  developed.  A  macro-­‐porous  
sulfonic  resin  entitled  TH-­‐02  is  selected  as  the  catalyst.  A  novel  three-­‐phase  circulating  fluidized  
bed  (TPCFB)  reactor  in  which  the  geometry  and  the  particular  flow  regime  resolve  the  conflict  
between  heat  transfer  and  resin  fragmentation  is  used  for  this  process.  RTD  results  show  that  
this  reactor  approximates  a  CSTR,  and  solids  and  liquid  are  distributed  uniformly  in  it.  Under  the  
optimal   reaction   conditions,   which   are   a   volumetric   ratio   of   CHP   to   acetone   1:2–1:3,  
temperature   75–85  ̊C   preferably   80  ̊C,   solid   holdup   1–1.5   wt.%   and   WHSV   of   CHP   30–40   h−1,  
the  conversion  and  product  selectivity  of  CHP  can  be  over  99  and  98%,  respectively.  

Qing-­‐Cai   Zhu,   Ben-­‐Xian   Shen,   Hao   Ling,   and   Rong   Gu   studied   the   Cumene   hydroperoxide  
hydrogenation   over   Pd/C   catalysts.   Pd/C   catalysts   were   prepared   by   wet   impregnation   using  
K2PdCl4  as  precursor  and  their  performance  in  hydrogenation  of  cumene  hydroperoxide  (CHP)  
was   investigated.   The   catalytic   activity   was   examined   on   the   formaldehyde-­‐reduced   and   on   the  
hydrogen-­‐reduced   Pd/C   catalysts.   Results   from   XRD,   TEM   and   CO   chemisorption   showed   that  
reduction   methods   have   a   significant   impact   on   the   palladium   particles   size   of   resulting  
catalysts.   Formaldehyde-­‐reduced   Pd/C   catalyst   has   larger   palladium   particles   than   hydrogen-­‐
reduced  Pd/C  catalyst.  Consequently,  higher  activity  but  lower  selectivity  to  cumyl-­‐alcohol(CA)  
was   obtained   on   formaldehyde-­‐reduced   Pd/C   catalyst.   Moreover,   hydrogenation   of   CHP   over  
hydrogen-­‐reduced  Pd/C  catalyst  can  give  similar  CA  selectivity  to  Na2SO3  reduction  process,  an  
industrial   process   for   CA   production.   High   rate   of   CHP   conversion   and   CA   selectivity   can   be  
obtained  at  an  elevated  temperature  and  H2  pressure.    

  12  
Ganapati  D.  Yadav  and  Navinchandra  S.  Asthana  studied  Selective  decomposition  of  cumene  
hydroperoxide  into  phenol  and  acetone  by  a  novel  cesium  substituted  heteropolyacid  on  clay.  
Phenol   is   industrially   produced   by   the   Hock   process   starting   from   benzene   and   propylene   to  
yield  cumene,  which  is  subsequently  oxidized  with  oxygen  to  generate  cumene  hydroperoxide  
(CHP)   which   is   then   decomposed   with   sulfuric   acid   to   obtain   equimolar   phenol   and   acetone.  
Both  phenol  and  acetone  are  important  bulk  chemicals  having  separate  as  well  as  interrelated  
markets.  The  last  step  of  the  Hock  process  is  polluting  and  results  in  loss  of  selectivity  leading  to  
formation   of   by-­‐products   beside   the   desired   products   phenol   and   acetone.   The   current   work  
reports   the   decomposition   of   CHP   by   using   K-­‐10   clay   supported   catalysts   such   as   20%   (w/w)  
dodecatungstophosphoric   acid   (DTPA)/K-­‐10,   20%   (w/w)   Cs2.5H0.5PW12O40/K-­‐10,   20%   (w/w)  
ZnCl2/K-­‐10   and   K-­‐10,   and   also   sulfated   zirconia   at   40oC.   For   the   first   time,   the   synthesis   of  
Cs2.5H0.5PW12O40   supported   on   K-­‐10   clay   has   been   reported   with   complete   intact   Keggin  
anion  structure.  This  catalyst  has  been  found  to  exhibit  excellent  activity  for  decomposition  of  
cumene   hydroperoxide   exclusively   into   phenol   and   acetone.   Various   kinetic   parameters   were  
studied   over   20%   Cs2.5H0.5PW12O40/K-­‐10.   The   reaction   follows   the   first   order   kinetics.   The  
catalyst  is  stable  and  reusable  giving  100%  conversion  with  exclusive  selectivity  to  100%  phenol  
and  acetone  during  all  the  runs.  

2-­‐Dehydrogenation  of  Isopropyl  Alcohol  

This  method  is  used  to  produce  about  4%  of  the  acetone  demand  in  the  USA,  and  about  19%  of  
the   demand   in   Western   Europe.   Isopropyl   alcohol   is   dehydrogenated   in   an   endothermic  
reaction:  

                                                                       CH3CHOHCH3  +  66.5  kJ/mol@327oC  à  CH3COCH3  +  H2  

The  equilibrium  is  more  favorable  to  acetone  at  higher  temperatures.  At  325oC,  97%  conversion  
is  theoretically  possible.  A  large  number  of  catalysts  have  been  investigated,  including  copper,  
silver,   platinum,   and   palladium   metals,   as   well   as   sulfides   of   transition   metals   of   groups   4,   5,  
and  6  of  the  periodic  table.  These  catalysts  are  made  with  inert  supports  and  are  used  at  400-­‐
600oC.   Lower   temperature   reactions   have   been   successfully   conducted   using   zinc   oxide-­‐
zirconium   oxide   combinations,   and   combinations   of   copper-­‐chromium   oxide   and   copper   silicon  
dioxide.  

It  is  usual  practice  to  raise  the  temperature  of  the  reactor  as  time  progresses  to  compensate  for  
the   loss   of   catalyst   activity.   When   brass   spelter   is   used   as   a   catalyst,   the   catalyst   must   be  
removed   at   intervals   of   500-­‐1000   hours   and   treated   with   mineral   acid   to   regenerate   the  
catalytically-­‐active  surfaces.  When  6-­‐12%  zirconium  oxide  is  added  to  a  zinc  oxide  catalyst  and  
the   reaction   temperatures   are   not   excessive,   the   catalyst   life   is   said   to   be   a   minimum   of   3  
months.  The  dehydrogenation  is  carried  out  in  a  tubular  reactor.    

  13  
Conversions   are   in   the   range   of   77-­‐95   mol%.   A   process   described   by   Shell   International  
Research  is  a  useful  two-­‐stage  reaction  to  attain  high  conversion,  with  lower  energy  cost  and  
lower  capital  cost.  The  first  stage  uses  a  tubular  reactor  at  420-­‐550oC  to  convert  up  to  70%  of  
the  alcohol  to  acetone.  The  second  stage  employs  an  unheated  fixed-­‐bed  reactor  with  the  same  
catalyst  used  in  the  tube  reaction  to  complete  the  conversion  at  about  85%.  

Although   the   selectivity   of   the   conversion   of   isopropyl   alcohol   to   acetone   via   vapor-­‐phase  
dehydrogenation   is   high,   there   are   a   number   of   by-­‐products   that   must   be   removed   from   the  
acetone.   The   hot   reactor   effluent   contains   acetone,   unconverted   isopropyl   alcohol,   and  
hydrogen,   and   may   also   contain   propylene,   polypropylene,   mesityl   oxide,   di-­‐isopropyl   ether,  
acetaldehyde,  propionaldehyde,  and  many  oter  hydrocarbons  and  carbon  oxides.  

The   mixture   is   cooled   and   noncondensable   gases   are   scrubbed   with   water.   Some   of   the  
resultant  gas  stream,  mainly  hydrogen,  may  be  recycled  to  control  catalyst  fouling.  The  liquids  
are   fractionally   distilled,   taking   acetone   overhead   and   a   mixture   of   isopropyl   alcohol   and   water  
as   bottoms.   A   caustic   treatment   may   be   used   to   remove   minor   aldehyde   contaminants   prior   to  
this   distillation.   In   another   fractionating   column,   the   aqueous   isopropyl   alcohol   is   concentrated  
to  about  88%  for  recycle  to  the  reactor.  

A   yield   of   about   95%   of   theoretical   is   achieved   using   this   process.   Depending   on   the   process  
technology   and   catalyst   system,   co-­‐products   such   as   methyl   isobutyl   ketone   and   di-­‐isobutyl  
ketone  can  be  produced  with  acetone.  

  14  
Applications  of  Acetone  
Acetone  is  used   mainly  as  a   solvent   and   serves  as  an   important  solvent  in   its   own   right,   usually  
as  the  solvent  of  choice  for  cleaning  purposes  in  the  laboratory  and  intermediate  in  chemical  
production.   Major   uses   are   in   the   production   of   methyl   methacrylate,   methacrylic   acid   and  
higher   methacrylates,   bisphenol-­‐A,   methyl   isobutyl   ketone,   drug   and   pharmaceutical  
applications,  and  as  a  solvent  for  coatings  and  for  cellulose  acetate.  There  are  also  food  uses  as  
an   extraction   solvent   for   fats   and   oils,   and   as   a   precipitation   agent   in   sugar   and   starch  
purification.  

About   half   of   the   world's   production   of   acetone   is   utilized   as   a   precursor   to   methyl  


methacrylate.  This  application  begins  with  the  initial  conversion  of  acetone  to  its  cyanohydrins:  

(CH3)2CO  +  HCN  →  (CH3)2C(OH)CN  

In  a  subsequent  step,  the  nitrile  is  hydrolyzed  to  the  unsaturated  amide,  which  is  esterified:  

(CH3)2C(OH)CN  +  CH3OH  →  CH2=(CH3)CCO2CH3  +  NH3  

The  second  major  use  of  acetone  entails  its  condensation  with  phenol  to  give  bisphenol-­‐A:  

(CH3)2CO  +  2  C6H5OH  →  (CH3)2C(C6H4OH)2  +  H2O  

Bisphenol-­‐A   is   a   component   of   many   polymers   such   as  polycarbonates,   polyurethanes,  


and  epoxy  resins.  

1-­‐As  a  solvent:  

Acetone   is   a   good   solvent   for   most   plastics   and   synthetic   fibers   including   those   used   in  
laboratory   bottles   made   of  polystyrene,  polycarbonate  and   some   types   of  polypropylene.   It   is  
ideal   for   thinning  fiberglass  resin,   cleaning   fiberglass   tools   and   dissolving   two-­‐
part  epoxies  and  superglue  before   hardening.   It   is   used   as   a   volatile   component   of  
some  paints  and  varnishes.   As   a   heavy-­‐duty   degreaser,   it   is   useful   in   the   preparation   of   metal  
prior  to  painting;  it  also  thins  polyester  resins,  vinyl  and  adhesives.  

Many  millions  of  kilograms  of  acetone  are  consumed  in  the  production  of  the  solvents  methyl  
isobutyl   alcohol   and  methyl   isobutyl   ketone.   These   products   arise   via   an   initial  aldol  
condensation  to  give  diacetone  alcohol.    

Acetone  is  also  used  as  a  solvent  by  the  pharmaceutical  industry  and  as  a  denaturation  agent  in  
denatured  alcohol.  

  15  
2-­‐In  Medicine  and  Cosmetics:  

Acetone   is   used   in   a   variety   of   general   medical   and   cosmetic   applications   and   is   also   listed   as   a  
component  in  food  additives  and  food  packaging.  

Acetone  is  commonly  used  in  the  skin  rejuvenation  process  in  medical  offices  and  medical  spas.  
Since  the  days  of  ancient  Egypt,  people  have  been  using  chemexfoliation  methods,  also  known  
as   chemical   peeling,   to   rejuvenate   skin.   Common   agents   used   today   for   chemical   peels   are  
salicylic  acid,  glycolic  acid,  30%  salicylic  acid  in  ethanol,  and  trichloroacetic  acid  (TCA).  Prior  to  
chemexfoliation,  the  skin  should  be  cleansed  properly  and  excess  fat  removed.  This  process  is  
known  as  de-­‐fatting.  Acetone,  Septisol,  or  a  combination  of  these  agents  is  commonly  used  in  
this  process.  

3-­‐In  Laboratories:  

In   the   laboratory,   acetone   is   used   as   a  polar  aprotic   solvent  in   a   variety   of  organic   reactions,  
such   as  SN2   reactions   (also   known   as   bimolecular   nucleophilic   substitution   or   as   “backside  
attack”).   The   use   of   acetone   solvent   is   also   critical   for   the  Jones   oxidation.   It   is   a   common  
solvent   for   rinsing  laboratory   glassware  because   of   its   low   cost   and   volatility,   yet   it   does   not  
form   an  azeotrope  with   water.  Despite   its   common   use   as   a   supposed  drying   agent,   it   is   not  
effective  except  by  bulk  displacement  and  dilution.  Acetone  can  be  cooled  with  dry  ice  to  −78  
°C   without   freezing;   acetone/dry   ice   baths   are   commonly   used   to   conduct   reactions   at   low  
temperatures.   Acetone   is   fluorescent   under   ultraviolet   light,   and   its   vapor   may   be   used   as   a  
fluorescent  tracer  in  fluid  flow  experiments.    

4-­‐Domestic  and  Other  Niche  Applications:  

Acetone  is  often  the  primary  component  in  cleaning  agents  such  as  nail  polish  remover.  Ethyl  
acetate,   another   organic   solvent,   is   sometimes   used   as   well.   Acetone   is   a   component  
of  superglue  remover  and  it  easily  removes  residues  from  glass  and  porcelain.  

Make-­‐up   artists   use   acetone   to   remove   skin   adhesive   from   the   netting   of   wigs   and   moustaches  
by  immersing  the  item  in  an  acetone  bath,  then  removing  the  softened  glue  residue  with  a  stiff  
brush.  

  16  
Storage  and  Handling  
Storage  Recommendations  

Carbon   steel   tanks   of   welded   construction,   as   specified   in   the   API   Standard   650   are  
recommended  for  acetone  service.  The  design  should  be  positive-­‐pressure,  plus  6"  water.  

Recommended  gaskets  include  316  stainless  steel  perforated  tang  reinforcement  encapsulated  
in   pure   graphite   sheet   such   as   Durabla   FGT   316   gasket   laminates,   Grafoil   GHE   gasket   laminates  
from  UCAR  Carbon  Company  Inc.  or  Graph-­‐Lock  3125TC  gasket  laminates  from  Garlock.  

Additional  design  considerations  are  regulated  by  the  National  Fire  Prevention  Association  Code  
30.   These   considerations   include   location,   method   of   sizing,   emergency   relief   valve   system,  
type  of  drainage  dikes  and  additional  fire  protection  considerations.    

It   has   been   the   experience   of   The   Dow   Chemical   Company   that   acetone   can   be   stored  
satisfactorily   in   unlined   carbon   steel   tanks.   However,   in   cases   where   the   purity   of   acetone   is   to  
be  optimized,  an  inorganic  zinc  lining  is  recommended.  

Acetone   should   be   stored   under   an   inert   gas   pad   such   as   Nitrogen.   Carbon   dioxide   is   not  
recommended.   A   blanketing   or   pad/depad   system   is   recommended   to   maintain   the   inert  
atmosphere.   The   associated   tank   venting   system   is   discussed   in   the   section   on   accessory  
equipment  below.  

Storage  tanks  containing  acetone  should  be  properly  grounded.  Pumps  utilized  for  both  filling  
and   removal   of   material   from   the   tank   should   share   a   common   ground   with   the   tank.Pumps  
should  be    located  outside  the  tank-­‐dike  area.    

To   minimize   the   possibility   of   static   charge   build-­‐up   during   filling   of   the   tank,   the   following  
additional  construction  design  is  recommended.    

The  tank  inlet  nozzle  should  be  at  the  bottom  of  the  vessel  with  provisions  to  block  and  to  drain  
piping.  If  the  tank  inlet  nozzle  is  installed  at  the  top  of  the  tank  side  wall,  a  carbon  steel  tube  
located  in  the  tank  interior  and  directed  to  the  tank  bottom  should  be  connected  to  the  inlet  
nozzle.  The  carbon  steel  tube  should  then  extend  from  the  inlet  nozzle  to  near  the  tank  bottom,  
resting  on  supports  on-­‐but  not  welded  to-­‐  the  tank  bottom.  Acetone  pumped  into  inlet  nozzle  
will   then   flow   through   the   interior   tube   and   enters   the   tank   contents   at   the   tank   bottom.   A  
small   hole   should   be   drilled   in   the   tube   near   the   inlet   nozzle   to   prevent   possible   siphoning  
effect.   The   tank   exterior   should   be   painted   a   light,   reflective   color,   such   as   white.  
 

  17  
Materials  for  Construction  

Carbon  steel  or  stainless  steel  are  the  preferred  materials  for  construction  of  tanks,  pumps,  and  
piping   components.   If   diacetone   alcohol   or   mesityl   oxide   are   of   concern,   stainless   steel   is  
preferred.  Gaskets  may  be  made  of  expanded  TFE  or  TFE-­‐gylon  3510.  Aluminum  can  be  used  as  
the  floating  roof  material.  TFE  wrapped  urethane  foam  inserted  with  polypropylene  fingers  that  
bolt  to  the  floating  roof  provide  an  effective  perimeter  seal  for  the  roof.  

NOTE:  Acetone   is   a   solvent   for   many   elastomers.   Therefore,   the   sealing   material   for   a   floatiang  
roof  closure  must  be  selected  carefully.  It  is  recommended  that  all  construction  materials  used  
for  equipment  or  containers  be  checked  for  acetone  compatibility.  

Recommendations  for  Storage  Systems  

For  the  safe  storage  of  acetone,  portable  tanks  not  exceeding  660  gallons  and  containers  not  
exceeding   60   gallons   must   comply   with   National   Fire   Protection   Association   (NFPA)   Code   30,  
Chapter  4  and  the  Occupational  Safety  and  Health  Administration  (OSHA)  regulation  1910.106.  
Leaks  are  difficult  to  detect  in  underground  tanks  but  if  it  is  necessary  to  use  such  tanks,  they  
must  also  conform  to  the  above  mentioned  codes  and  all  federal,  state  and  local  regulations.  

Acetone  is  a  Class  1  flammable  liquid.  Bulk  storage  tanks  are  not  to  be  located  inside  buildings  
unless  built  in  accordance  with  the  process  tank  provisions  of  the  NFPA  code.  

The  design  of  storage  tanks  must  conform  to  the  principles  of  good  engineering  practice.  Tanks  
can   be   either   horizontal   or   vertical   and   in   any   shape   consistent   with   good   design   principles.  
Acetone  can  be  stored  in  tanks  designed  for  the  following  pressure  ranges  and  standard:  

Type   Pressure  Range   Industry  Standard  

Atmospheric   0  -­‐  0.5  PSIG   API  650  

Low  Pressure   0.5  -­‐  15  PSIG   API  620  

Pressure  Vessel   >15  PSIG   ASME  Boiler  &  Pressure  Vessel  


Code  for  Unfired  Pressure  
 
Vessels  Sec.  VIII,  Div.  1  

Floating  Roof   N/A   API  650  

  18  
Pressure  tanks  built  according  to  ASME  code  are  preferred  over  atmospheric  tanks  if  acetone  is  
to  be  stored  at  or  near  its  boiling  point  (56.2°C).  In  the  case  of  atmospheric  tanks,  provisions  
must  be  made  for  inbreathing  (vacuum  relief)  and  outbreathing  (pressure  relief)  in  the  form  of  
a  combination  pressure/vacuum  relief  valve  whose  size  is  based  on  the  vent  rates  established  
by  NFPA  30,  Flammable  &  Combustible  Liquids  Code.  Tanks  should  not  have  steam  coils.  

Open   vents   should   not   be   used   with   acetone   since   its   flash   point   is   below   100°F.   When  
designing   vents,   the   minimum   for   venting   that   should   be   used   is   contained   in   NFPA   30,  
Flammable  &  Combustible  Liquid  Code.  For  inbreathing,  vacuum  relief  API  2000  should  be  used.  

Note:  The  inbreathing  sizing  as  called  for  in  API  2000  is  not  adequate  for  the  situation  where  a  
steam   tank   is   subject   to   sudden   cooling.   For   most   tanks,   emergency   vents   are   required   to  
protect  against  fire  exposure.  Although  protection  can  be  achieved  by  the  use  of  additional  P/V  
valves,   a   gauge   hatch   or   manhole   cover   that   lifts   when   exposed   to   abnormal   pressure   is  
normally  used.  Again,  tanks  used  for  acetone  storage  will  not  usually  have  steam  coils.  

It   is   recommended   that   tanks   larger   than   10,000   gallons   be   equipped   with   either   an   internal   or  
an  external  floating  roof  to  prevent  the  accumulation  and  loss  of  vapor.  

Because   of   the   high   vapor   pressure   of   acetone   (2.5   PSIA   at   20°C)   federal   regulations   require  
that  tanks  larger  than  20,000  gallons  which  were  constructed,  reconstructed  or  modified  after  
July  23,  1984  have  a  floating  roof  or  have  a  vapor  recovery  system  to  minimize  emissions.  

Note:Floating   roof   tanks   need   a   double   closure   seal   to   eliminate   the   space   between   the   roof  
edge  and  wall.  The  design  of  floating  roof  tanks  is  covered  by  API  Standard  650.  

Acetone   storage   tanks   may   be   painted   white   to   minimize   radiational   heating   by   sunlight.   Tanks  
should   also   not   be   filled   to   the   top   as   acetone   will   expand   as   temperatures   rise   in   warmer  
weather.  

Auxiliary  Equipment  and  Instrumentation  

All  storage  tank  systems  should  be  equipped  with  instrumentation  to  monitor  temperature  and  
level,  as  well  as  a  high-­‐level  alarm  if  possible.  Centrifugal  pumps  are  preferred  for  transferring  
acetone.   Avoid   using   positive   displacement   type   pumps   since   acetone   provides   minimum  
lubrication  to  the  internal  parts.  Fire  safe  valves,  which  can  be  plug,  gate,  ball,  or  other  types  
capable  of  providing  tight  shut-­‐off  consistent  with  ANSI  Standard  B31.3  or  ANSI  B31.4l,  could  be  
used.   Plastic   valves   should   not   be   used   since   they   typically   do   not   provide   adequate   fire  
protection  and  may  not  be  compatible  with  acetone.  Sufficient  valves  are  required  to  control  
flow  into  and  discharge  from  the  tank  under  normal  and  emergency  conditions.  

  19  
A  water  spray  system  may  be  installed  consistent  with  NFPA  12  since  acetone/water  mixtures  
are  flammable.  All  tanks  should  have  connections  for  the  introduction  of  polar  solvent  (alcohol)  
type  foam.  Floating  roof  tanks  need  connections  near  the  seal  area.  

Electrical  equipment  used  should  meet  the  requirements  of  the  NEC  (NFPA  70)  Class  I,  Group  D.  
Additional  information  can  be  found  in  NFPA  30,  The  Flammable  &  Combustible  Liquids  Code  
and  NFPA  497A  Recommended  Locations  for  Electrical  Installations  in  Chemical  Process  Areas,  
which  give  the  minimum  requirements  for  proper  classification.  

In   dealing   with   static   electricity   problems   refer   to   NFPA   77,   Recommended   Practice   on   Static  
Electricity,  and  NFPA  780,  Lighting  Protection  Code.  

In  order  to  minimize  problems  from  static  electricity  arising  from  the  loading  and  unloading  of  
acetone,  grounding  and  bonding  procedures  should  be  used.  (Refer  to  NFPA  77).  

Location   of   tanks   with   respect   to   each   other   and   property   lines   need   to   conform   to   NFPA  
Standard  30.  

Provisions   for   containment   of   spills   from   tanks   must   also   be   made   in   accordance   with   this  
standard.  An  approved  fire  alarm  system  is  required  and  a  public  alarm  box  is  recommended.  
The   number   of   portable   fire   extinguishers   on   hand   should   be   consistent   with   the   particular  
hazard.  

Accessory  Equipment  

Pumps,  motors  and  switch  gear  used  for  acetone  service  should  conform  to  the  specifications  
outlined   in   the   National   Electric   Code,   Class   I,   Division   I,   Group   D,   paragraphs   500   and   501.  
 
The  tank  venting  system  should  allow  for  compliance  with  local  vapor  emission  standards  and  
conform   to   National   Fire   Prevention   Association   recommendations.   Sizing   of   pressure   relief  
valves,  vacuum  relief  valves,  and  emergency  relief  valves  is  outlined  in  the  American  Petroleum  
Institute   Standard   2000   (1973   Edition).   Factors   such   as   "pumping-­‐in"   rate,   thermal   out-­‐
breathing,  and  potential  "slug-­‐in"  of  gas  during  tank  loading  should  be  considered  in  design  of  
the   relief   valve.   A   flame   arrester   should   be   included   in   the   venting   system.   A   mechanical   or  
electronic  tank  leveling  gauge  is  recommended.  

  20  
TRANSPORTATION  INFORMATION  

US  DOT  Hazardous  Class:   Class  3  -­‐  Flammable  Liquid,  Appendix  A  (171.101)  

US  DOT  ID  Number:   UN  1090  

Proper  Shipping  Description:   Acetone,  3,  UN  1090,  PG  II,  (RQ  5000)  

 
HANDLING  BULK  DELIVERIES  

Loading  and  unloading  facilities  should  be  at  least  25  feet  from  other  buildings  and  warehouses.  
When   loading   acetone   into   rail   cars   or   tank   cars,   install   a   vapor   recovery   system   to   minimize  
emissions.   In   addition,   provide   grounding   and   bonding   facilities   for   protection   from   static  
sparks  while  loading  and  unloading.  

Before  loading  or  unloading  a  bulk  delivery  always  check  the  storage  tank  to  insure  that  it  has  
sufficient  available  space.  Monitor  the  tank  level  at  all  times  during  filling  and  be  prepared  to  
stop  the  flow  immediately  if  necessary.  High  level  alarms  and  shutdown  may  be  installed.  

Samples  should  not  be  taken  through  the  dome  immediately  after  filling.  

MAINTENANCE  AND  INSPECTIONS  

The  volatile  property  of  acetone  makes  maintenance  and  inspection  procedures  especially  
critical.  Personnel  should  routinely  observe  for  possible  leaks  from  valves,  pump  fittings,  and  
storage  tanks.  Inspect  all  atmospheric  tanks  internally  every  10  years  or  when  operational  
problems  arise.  Floating  roofs  should  be  inspected  every  5  years.  Annually  compare  ultrasonic  
measurements  or  tank  material  thickness  to  monitor  the  corrosion  rate  of  the  tank  walls.  It  is  
instructive  to  conduct  a  visual  inspection  of  all  welds  at  this  time  as  well.  If  potential  problem  
areas  are  observed,  tests  and/or  an  X-­‐ray  inspection  should  follow  with  repairs  made  
accordingly.  

  21  
General  Safety  Precautions  

Protect   against   physical   damage.   Store   in   a   cool,   dry   well-­‐ventilated   location,   away   from   any  
area   where   the   fire   hazard   may   be  acute.   Outside   or   detached   storage   is   preferred.   Separate  
from   incompatibles.   Containers   should   be   bonded   and   grounded   for   transfers   to   avoid   static  
sparks.   Storage   and   use   areas   should   be   No   Smoking   areas.   Use   non-­‐sparking   type   tools   and  
equipment,   including   explosion   proof   (EX)   ventilation.   Containers   of   this   material   may   be  
hazardous  when  empty  since  they  retain  product  residues  (vapors,  liquid);  observe  all  warnings  
and  precautions  listed  for  the  product.  

Acetone   should   always   be   handled,   stored,   and   used   with   precautions   against   fire   and  
explosion.   Acetone   is   a   flammable   liquid   with   flammable   limits   of   2.6   to   12.8   vol%   at  
25°C.     Solutions  of  acetone  and  water  can  be  flammable.  Since  acetone  vapors  travel  with  air  
currents,  they  can  be  ignited  by  flames  and  sparks  at  locations  remote  from  the  site  at  which  
the   material   is   being   handled.   Smoking   should   be   prohibited   since   prolonged   exposure   to  
acetone  may  cause  the  chemical  to  remain  on  clothing  articles.  

Appropriate   safety   gear   should   always   be   worn   when   handling   acetone.   This   includes   safety  
glasses   with   cup-­‐type   side   shields   or   chemical   goggles,   safety   shoes,   natural   rubber,   or  
neoprene  gloves,  and  hard  hat.  In  unusual  or  emergency  situations  when  contact  with  the  liquid  
is   necessary   or   likely,   the   handler   should   wear   full   protective   equipment   and   clothing.   All  
contaminated  clothing  must  be  washed  before  reuse.  Protective  equipment  and  clothing  should  
be  decontaminated  or  disposed  of  according  to  the  manufacturer’s  instructions.  

Exposure  Control  Measures  and  Personal  Protection  Guidelines  

Ventilation  System:    

A  system  of  local  and/or  general  exhaust  is  recommended  to  keep  employee  exposures  below  
the   Airborne   Exposure   Limits.   Local   exhaust   ventilation   is   generally   preferred   because   it   can  
control   the   emissions   of   the   contaminant   at   its   source,   preventing   dispersion   of   it   into   the  
general  work  area.    

 
 

  22  
Personal  Respirators:  

If  the  exposure  limit  is  exceeded  and  engineering  controls  are  not  feasible,  a  half-­‐face  organic  
vapor   respirator   may   be   worn   for   up   to   ten   times   the   exposure   limit,   or   the   maximum   use  
concentration  specified  by  the  appropriate  regulatory  agency  or  respirator  supplier,  whichever  
is  lowest.  A  full-­‐face  piece  organic  vapor  respirator  may  be  worn  up  to  50  times  the  exposure  
limit,   or   the   maximum   use   concentration   specified   by   the   appropriate   regulatory   agency   or  
respirator   supplier,   whichever   is   lowest.   For   emergencies   or   instances   where   the   exposure  
levels  are  not  known,  use  a  full-­‐face  piece  positive-­‐pressure,  air-­‐supplied  respirator.    

   
Skin  Protection:    

Wear   impervious   protective   clothing,   including   boots,   gloves,   lab   coat,   apron   or   coveralls,   as  
appropriate,  to  prevent  skin  contact.    

 
Eye  Protection:  

Use  chemical  safety  goggles  and/or  a  full  face  shield  where  splashing  is  possible.  Maintain  eye  
wash  fountain  and  quick-­‐drench  facilities  in  work  area.  

In   case   of   eye   contact   with   acetone,   wash   with   copious   amounts   of   water   for   at   least   15  
minutes,   occasionally   lifting   the   lower   and   upper   lids.   Obtain   medical   attention   promptly.   In  
case   of   skin   contact,   wash   with   water   for   at   least   15   minutes.   If   inhaled,   remove   the   patient  
from   contaminated   atmosphere   to   fresh   air.   If   not   breathing,   give   artificial   respiration,  
preferably  mouth-­‐to-­‐mouth.  If  breathing  is  difficult,  give  oxygen  which  is  administered  only  by  
trained  personnel.  Get  prompt  medical  attention.  

Emissions  and  Environmental  Effects  


 Acetone  released  to  the  atmosphere  is  degraded  by  a  combination  of  photolysis  and  reaction  
with   hydroxyl   radicals.   The   average   half-­‐life   for   acetone   degradation   in   the   atmosphere   is  
approximately   30   days.   Acetone   can   be   physically   removed   from   air   by   wet   deposition.   The  
dominant  degradation  process  for  acetone  in  soil  and  water  is  biodegradation,  and  acetone  is  
readily   biodegradable.   Volatilization   of   acetone   from   the   aquatic   environment   can   be   a  
significant   transport   process.   Acetone   is   a   volatile   compound   that   will   evaporate   from   dry  
surfaces.  Since  acetone  is  miscible  in  water,  it  can  leach  readily  in  most  types  of  soil.  Concurrent  
biodegradation  may  diminish  the  general  significance  of  leaching  if  biodegradation  occurs  fast  
enough.  

  23  
Sources  of  Emission:  

Into  Air  

Atmospheric  emissions  are  likely  from  the  many  consumer  products  containing  acetone.  Such  
products  include  nail  polish  removers,  particle  board,  carpet  backing,  some  paint  removers,  a  
number   of   liquid/paste   waxes   or   polishes,   some   detergents/cleansers,   adhesives,   and  
carburetor   and   choke   cleaners.   Atmospheric   emissions   from   the   phenol/acetone   production  
process  are  approximately  0.44  g  per  kg  of  acetone  produced.  

Into  Water  

Acetone  is  released  into  surface  water  as  wastewater  from  certain  chemical  manufacturing  
industries.  It  is  also  released  in  water  from  energy-­‐related  industries,  such  as  coal-­‐gasification  
and  oil  shale  processing.  Acetone  was  found  in  27  of  63  effluent  water  samples  from  a  wide  
range  of  chemical  industries  in  the  USA.  It  has  been  detected  in  effluents  from  various  industrial  
production  processes  including  paper,  plastic,  pharmaceutical,  specialty  cleaning  and  polishing  
products,  paint  and  allied  products,  gum  and  wood  chemicals,  cyclic  intermediates,  industrial  
organic  chemicals,  gypsum  products,  and  paper  board  products.  

Acetone  can  be  released  to  groundwater  as  a  result  of  leaching  from  municipal  and  industrial  
landfills.  It  may  also  leach  from  solvent  cement  used  in  joining  polyethylene  and  other  plastic  
pipes  used  in  drinking-­‐water  distribution  and  domestic  plumbing.  One  of  the  sources  of  acetone  
in  seawater  is  the  sensitized  photoreaction  of  dissolved  organic  matter.  

Into  Soil  

Acetone  leaches  readily  in  soil.  The  US  Agency  for  Toxic  Substances  and  Disease  Registry  found  
the  amount  of  acetone  released  into  soil  from  landfills  in  the  USA  accounted  for  approximately  
0.1%  of  the  total  environmental  release  of  acetone.  Sources  of  acetone  release  into  soil  include  
disposal  of  agricultural  and  food  waste,  animal  wastes,  and  atmospheric  wet  deposition.  
Acetone  was  detected  in  43%  of  the  soil  from  designated  waste  disposal  sites  tested  for  
acetone.  Household  septic  tank  effluents  are  another  source  of  acetone  in  soil.  

  24  
Effect  on  Human  Beings    

Acetone   is   relatively   less   toxic   than   many   other   industrial   solvents;   however,   at   high  
concentrations,  acetone  vapor  can  cause  CNS  depression,  cardio-­‐respiratory  failure  and  death.  
Acute   exposures   of   humans   to   atmospheric   concentrations   as   high   as   approx.   4750   mg/m3        
(approx.   2000   ppm)   have   been   reported   to   produce   either   no   gross   toxic   effects   or   minor  
transient  effects,  such  as  eye  irritation.  More  severe  transient  effects  (including  vomiting  and  
fainting)  were  reported  by  workers  exposed  to  acetone  vapor  concentrations  >25  500  mg/m3  
(>12  000  ppm)  for  approximately  4  hours.  Acute  exposures  to  acetone  have  also  been  reported  
to   alter   performance   in   neurobehavioral   tests   in   humans   at   595   mg/m3   (250   ppm).   Females  
exposed   to   atmospheric   concentrations   of   2370   mg/m3   (1000   ppm)   were   reported   to   suffer  
menstrual  irregularities.    

   

  25  
Specifications,  Standards,  and  Quality  Control  
 

The  ASTM  Standard  Specifications  for  Acetone  (ASTM  D329)  requires  99.5%  grade  acetone  to  
conform  to  the  following:    

apparent  specific  gravity  (20/20oC):  0.795  to  0.7930  


color:  not  more  than  No.5  on  the  platinum-­‐cobalt  scale  (ASTM  D1209)  
distillation  range:  1.0oC  which  shall  include  56.1oC  
nonvolatile  matter:  not  more  than  5mg/100  mL  (D1353)  
odor:  characteristic  nonresidual  (ASTM  D1296)  
water:  not  more  than  0.5wt%  (ASTM  D1364)  
acidity  (as  free  acetic  acid):  not  more  than  0.002  wt%,  equivalent  to  0.019  mg  of  KOH  per  gram  
(ASTM  D1613)  
water  miscibility:  no  turbidity  or  cloudiness  at  1:10  dilution  with  water  (ASTM  D1722)  
alkalinity  (as  ammonia):  not  more  than  0.001  wt%  (ASTM  D1614)  
permanganate  time:  color  of  added  KMnO4  must  be  retained  at  least  30  minutes  at  25oC  in  the  
dark  (ASTM  D1363).  
 

Higher  or  lower  quality  at  more  or  less  cost  will  meet  the  needs  of  some  consumers.  Acetone  is  
often  produced  under  contract  to  meet  customer  specifications  which  are  different  than  those  
of   ASTM   D329.   Some   specialty   grades   are   analyzed   reagent,   isotopically   labeled,   clean   room,  
liquid   chromatography,   spectroscopic,   ACS   reagent,   semiconductor   (low   metals),   and   Federal  
Specification  O-­‐A-­‐51G.  

Specification  tests  are  performed  on  plant  streams  once  or  twice  per  worker  shift,  or  even  more  
often  if  necessary,  to  assure  the  continuing  quality  of  the  product.  The  tests  are  also  performed  
on  a  sample  from  an  outgoing  shipment,  and  a  sample  of  the  shipment  is  usually  retained  for  
checking   on   possible   subsequent   contamination.   Tests   on   specialty   types   of   acetone   may  
require  sophisticated  instruments,  e.g.  Mass  spectrometry  for  isotopically  labeled  acetone.  

Analytical  and  Test  Methods  

In   current   industrial   practice   gas   chromatographic   analysis   is   used   for   quality   control.   The  
impurities,   mainly   a   small   amount   of   water   and   some   organic   trace   constituents,   are  
determined  quantitatively.  Compliance  to  specified  ranges  of  individual  impurities  can  also  be  
assured   by   this   analysis.   The   gas   chromatographic   method   is   accurately   correlated   to   any   other  
tests   specified   for   the   assay   of   acetone   in   the   product.   Contract   specifications   tests   are  
performed  on  product  to  be  shipped.  Typical  wet  methods  for  the  determination  of  acetone  are  
acidimetry,   titration   of   the   liberated   hydrochloric   acid   after   treating   the   acetone   with  
hydroxylamine   hydrochloride,   and   iodimetry,   which   is   titrating   the   excess   of   iodine   after  
treating  the  acetone  with  iodine  and  base  (iodoform  reaction).  

  26  
Carbon   steel   tanks   of   welded   construction,   as   specified   in   the   American   Petroleum   Institute  
Standard   650,   are   recommended   for   acetone   storage.   Gaskets   should   be   ethylene-­‐propylene  
rubber  or  Viton  rubber.  An  inert  gas  pad  should  be  used.  Provisions  should  be  made  to  prevent  
static   charge   buildup   during   filling.   Design   considerations   of   the   National   Fire   Prevention  
Association   Code   30   and   local   fire   codes   should   be   followed.   Tank   venting   systems   should  
comply   with   local   vapor   emission   standards   and   conform   to   NFPA   recommendations.   For   the  
purity  of  acetone  to  be  optimized,  an  inorganic  zinc  lining  is  recommended.  One  such  lining  is  
Carbonzinc-­‐11:  metallic  zinc  in  an  ethyl  silicate  binder.  

   

  27  
 

References:  
1-­‐ http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6WHJ-­‐4G82Y68-­‐1-­‐
54&_cdi=6852&_user=739499&_pii=S0021951705001661&_origin=search&_coverDate=07%2F
01%2F2005&_sk=997669998&view=c&wchp=dGLbVzb-­‐
zSkzS&md5=bd31c9004613fa22b6a185b8c59063e0&ie=/sdarticle.pdf  

2-­‐ http://www.scribd.com/doc/30132557/Acetone  

3-­‐ http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TF5-­‐47T281R-­‐3-­‐
3X&_cdi=5217&_user=739499&_pii=S0926860X02006051&_origin=search&_coverDate=05%2F
15%2F2003&_sk=997559997&view=c&wchp=dGLbVlW-­‐
zSkzS&md5=7cbe8ea99208169b058ae50c12ae9ad9&ie=/sdarticle.pdf  

4-­‐ http://www.owlnet.rice.edu/~ceng403/gr1998/acetone.html  

5-­‐ http://www.scribd.com/doc/44694278/Acetone-­‐All-­‐Ethopian-­‐Project  

6-­‐ http://www.springerlink.com/content/7722l0020387126l/  

7-­‐ http://www.inchem.org/documents/ehc/ehc/ehc207.htm#SectionNumber:1.1  

8-­‐ http://www.sciencelab.com  

9-­‐ http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TF5-­‐43WTFSD-­‐G-­‐
B&_cdi=5217&_user=739499&_pii=S0926860X01006743&_origin=search&_coverDate=10%2F0
5%2F2001&_sk=997809998&view=c&wchp=dGLbVzW-­‐
zSkWb&md5=9a0f9572c2fd47a0073a934d4008e51d&ie=/sdarticle.pdf  

10-­‐ http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TF5-­‐4PGGP1W-­‐1-­‐
F&_cdi=5217&_user=739499&_pii=S0926860X07005108&_origin=search&_coverDate=03%2F0
1%2F2008&_sk=996639998&view=c&wchp=dGLbVlz-­‐
zSkzk&md5=799a801e451b0844470d814106b8ad0f&ie=/sdarticle.pdf  

11-­‐ http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TFJ-­‐454HMBB-­‐1-­‐
21&_cdi=5228&_user=739499&_pii=S1385894702000037&_origin=search&_coverDate=09%2F
28%2F2002&_sk=999119998&view=c&wchp=dGLbVtz-­‐
zSkWb&md5=361d2ab0751b253f4c1779a46a13b7a2&ie=/sdarticle.pdf  

12-­‐ http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TGF-­‐4XJG5RF-­‐3-­‐
5&_cdi=5253&_user=739499&_pii=S0304389409017087&_origin=search&_coverDate=03%2F1
5%2F2010&_sk=998249998&view=c&wchp=dGLbVzb-­‐
zSkzk&md5=bc1850301d9f308b3093c2e86a34ebcd&ie=/sdarticle.pdf  

13-­‐ http://en.wikipedia.org/wiki/Acetone  

14-­‐ Kirk-­‐Othmer  Encyclopedia  of  Chemical  Technology  

15-­‐ Chemicals  of  Commerce-­‐Foster  Dee  and  Cornelia  T.Seull-­‐2nd  Edition  

  28  
16-­‐ Analysis  of  Drugs-­‐N.Evers  and  G.D.  ElsDorv  

17-­‐ Condensed  Chemical  Dictionary-­‐Gessner  G.Hawley  

18-­‐ Uses  and  Applications  of  Chemicals  and  Related  Materials-­‐  G.Gregory  

19-­‐ The  Technology  of  Solvents  and  Plasticizers-­‐Doolittle  

20-­‐ http://www.chemical.net/home/handling.htm  

  29  
Conclusion  
 

So  how  will  such  an  outstanding  report  such  as  the  one  in  your  hands  conclude  its  findings?  

We  did  NOT  come  up  with  any  original  ideas,  we  did  NOT  discover  anything  new.  

We  simply  compiled  freely  available  information  into  a  nice-­‐looking  “report”.  

Conclusions  are  drawn  when  we  have  RESULTS  and/or  theories,  or  predictions  at  the  very  least,  
which  we  DON’T.  

This  concludes  our  report  for  today.  We  hope  to  see  you  again  in  the  very  near  future.  

Signed:  

Informant  #1  

Informant  #2  

Informant  #3  

Informant  #4  

Informant#5  

Informant#6  

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