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I take this opportunity to express my profound gratitude and deep regards to my guide Mr.
PANKAJ PADHIYAR (HOD Of Chemical engineering department) for his exemplary guidance,
monitoring and constant encouragement throughout the course of my project, ‘CRESOL’. The
blessing, help and guidance given by him time to time shall carry me a long way in this journey
of life on which I am about to embark.
I also take this opportunity to express a deep sense of gratitude to Mr. JIMIT KANSARA for
their cordial support, valuable information and guidance which helped me in completing this
project through various stages.
Lastly, I thank to my parents and my classmates for their constant encouragement without which,
this Project would not have been possible.
ABSTRACT
Cresols are found in many foods and in wood and tobacco, smoke, crude oil, coal tar, and in
chemical mixtures used as wood preservatives. Small organisms in soil and water produce
cresols when they break down materials in the environment. It is a partially lyophilic moiety
which strongly binds to plasma protein (close to 100%) under normal conditions. p-Cresol is
metabolized through conjugation, mainly sulphation and glucuronization, but removal of the
unconjugated p-cresol is, at least in part, via the urine. Therefore, it is not surprising that this
compound, together with several other phenols, is retained when the kidneys fail. P-Cresol is an
end-product of protein breakdown, and an increase of the nutritional protein load in healthy
individuals results in enhanced generation and urinary excretion. The serum p-cresol
concentration in uremic patients can be decreased by changing to a low-protein diet. p-Cresol is
one of the metabolites of the amino acid tyrosin, and to a certain extent also of phenylamine
which are converted to 43-hydroxyphenylacetic acid by intestinal bacteria, before being
decarboxylated to p-cresol. As phenol derivatives, cresols can be used in phenol-formaldehyde
resins. m-Cresol is also used in making photographic developer and explosives. p-Cresol can be
converted to butylated hydroxytoluene (BHT), an important antioxidant in foods. The cresols are
strong germicides, and in low concentrations they are effective disinfectants and antiseptics.
Methods of production are 1) Manufacturing of cresol from hydrolysis by fusion of toluene
sulfonic acid which is simple in nature and production it contains 99 % yield and purity of 99%
is achieved 2) p-cresol is systematically prepare methylation of phenol which contains 43%
yield. It is difficult in handling and the method of manufacturing is complex.
INDEX
CHAPTER CHAPTER PAGE
NO. NO.
1. Introduction and History 1-2
1.1 Introduction and History of Cresol 2
2. Literature survey 3-4
2.1 Top Manufacturing Industries of Cresol 4
3. Properties of Cresol 5-6
3.1 Physical Properties of Cresol 6
4. Methods of Production 7-8
4.1 Methods of Production 8
5. Preparation Method 9-12
5.1 Raw Material 10
5.2 Chemical Reaction 10
5.3 Process Flow Diagram 11
5.4 Process Description 12
6. Details of Selected Process 13-14
6.1 detail of selected process 14
7. Material Balance 15-18
7.1 Material Balance for Acidification 16
8. Utilities Required for Selecting Process 19-21
8.1 Power Supply System 20
8.2 Steam 20
8.3 Process Water 20
8.4 Cooling Tower 21
9. Plant Location and Layout 21-23
9.1 Plant Location and Layout 23
10. Cost Estimation 24-30
10.1 The Capital Investment for The Year 2007-08 25
10.2 Estimation of Capital Investment Cost 25
10.3 Total Capital Investment (TCI) 27
10.4 Estimation of Total Product Cost 27
10.5 Plant Overhead Cost 28
10.6 Rate of Return 30
11. Important Aspect of Safety Pollution control 31-35
11.1 Hazard Summary 32
11.2 Ways of reducing exposure 32
11.3 Health & Hazard summary 32
11.4 Personal Protective Equipment 33
11.5 Hazard & Storage 35
12. MSDS of Product 36-41
12.1 composition and information of cresol 37
12.2 Hazard identification 37
12.3 First aid measures 37
12.4 Fire and explosion data 38
12.5 Accidental Release Measure 39
12.6 Handling and storage 39
12.7 Personal protection 40
12.8 physical and chemical properties 40
12.9 Stability and reactivity data 40
12.10 toxicological information 41
12.11 ecological information 41
12.12 Transport Information 41
12.13 Other regulatory Information 41
13. Solid Waste treatment 42-43
13.1 Sodium sulphate Recovery 43
13.2 Process Description 43
14. Conclusion 45
15. Reference 47
TABLE INDEX
SR.NO. TABLE PAGE NO.
1 6.1 Material Balance Chart 15
CHAPTER: -1
INTRODUCTION AND HISTORY OF CRESOL
1
1.1 INTRODUCTION AND HISTORY OF CRESOL
CRESOL is a speciality chemical that is primarily employed in the synthesis of antioxidant such
as butylated hydro-oxytoluene and in the preparation of thermosetting resins such as Resols and
Novosols. Through cresols can be obtained directly from naphtha fractions of coal and oil.
In its chemical structure, a molecule of cresol has methyl group substituted onto the ring of
phenol. There are three forms that differ slightly in their chemical structure:
1. Ortho-CRESOL
2. Para-CRESOL
3. Meta-CRESOL
About half of the world’s supply of cresol are extracted from coal-tar. Cresol is a Derivatives of
❖ Xylenols
❖ Bromo-cresol
❖ Phenol
The mixtures of cresols obtained from coal tar is called Cresylic acid. And the cresols are mainly
used in the disinfectants and synthetic resins.
2
CHAPTER: -2
LITERATURE SURVEY
3
2.1 TOP MANUFACTURING INDUSTRIES OF CRESOL
• SABIC, Bangalore
4
CHAPTER: -3
PROPERTIES OF CRESOL
5
3.1 PHYSICAL PROPERTIES OF CRESOL
➢ Molecular Formula:- C7 H8 O
➢ Molecular weight - 108
➢ Systematic Name :- METHYLPHENOL
➢ Melting Point:-
• O-Cresol=29.8 °C
• P-Cresol=11.8 °C
• M-CRESOL=35.5 °C
➢ Boiling Point:-
• O-Cresol=191 °C
• P-Cresol=202 °C
• M-Cresol=201.9 °C
➢ Density:-
• O-Cresol=1.05gm/cm3
• P-Cresol=1.03gm/cm3
• M-Cresol=1.02gm/cm3
➢ Appearance:-
• O-Cresol= Colourless crystals
• P-Cresol=Thicker liquid
• M-Cresol= Greasy looking solid
➢ Solubility:-
• O-Cresol=2.5gm/ml
• P-Cresol=2.4gm/ml
• M-Cresol=1.9gm/ml
➢ Flash Point:-
• O-Cresol=81 °C
• P-Cresol=86 °C
• M-Cresol=86 °C
6
CHAPTER: -4
METHODS OF PRODUCTION
7
4.1 METHODS OF PRODUCTION
➢ By methylation of phenol
▪ 43% Yield
▪ Difficult in handled
▪ Complex method
8
CHAPTER: -5
PREPARATION METHOD
9
5.1 RAW MATERIAL
▪ Toluene
▪ Liquid SO 3
▪ SO 2 gas
▪ Acetic acid(CH3 COOH)
10
5.3 PROCESS FLOW DIAGRAM
SULFONATION
SODIFICATION
FUSION
QUENCHING
ACIDIFICATION
DISTILLATION
CRESOL
11
5.4 PROCESS DESCRIPTION
5.4.1 Sulfonation:
Liquid SO3 is used as the sulfonating agent in sulfonation of Toluene, which is kept in a special
type of storage tank in a room maintained at a temperature just above the freezing point of SO3
Mixtures of Toluene and SO3 are sent to the plug flow reactor for sulfonation reaction.
Sulphonated mass is kept under a solvent to keep in a flowable conditions. The sulfonation of
toluene is carried out at low temperature & toluene sulfonic acid is formed. Temperature is
controlled by the chilled brine.
After sulfonation step, TSA is then sent for sodiation.
5.4.2 Sodiation:
The sodiation process involves the neutralization of toluene sulfonic acid by adding NaOH
where pH becomes slightly basic, to form NaTSA.
NaTSA is then stored in the storage tanks. From these tanks, it is fed to the fusion pots in the
fusion unit.
5.4.3 Fusion:
In fusion section NaTSA is fused with a concentrated solution of NaOH which is produced by
the evaporation of 48% NaOH solution in the evaporator. The moisture comes out from the
evaporator is condensed out with cold water to produce process hot water. Fusion is very high
temp reaction . At first caustic is fed to the fusion reaction pot & NaTSA is then slowly charged,
with continuous starring. Entire water vapour is taken out from the system by an ejector system.
This is a very critical operation as far as fusion is concerned.
5.4.5 Acidification:
The acidifier is a CSTR type reactor in which H2SO4 is added with Na-Cresolate oil. This is an
exothermic reaction. After acidification reaction crude Cresols & Na2SO4 is formed. Here the
crude cresols and Na2SO4 form two different phases. It is separated by a continuous decanter.
The bottom part containing Na2SO4, The upper organic part (crude cresols) is pumped into a
storage tank and is sent for distillation.
5.4.6 Distillation:
Crude cresols are fed to a continuous fractionation system where p-cresol is separated as 99%
pure product.
12
CHAPTER: - 6
DETAIL OF SELECTED PROCESS
13
6.1 DETAIL OF SELECTED PROCESS
➢ By fusion of toluene sulfonic acid
▪ 99% Yield
▪ Easiest method
▪ 99% Purity achieved
14
CHAPTER: -7
MATERIAL BALANCE
15
7.1 MATERIAL BALANCE FOR ACIDIFICATION
𝟐𝑪𝑯𝟕 𝑶𝑵𝒂 + 𝑯𝟐 𝑺𝑶𝟒 → 𝟐𝑪𝟕 𝑯𝟖𝑶 + 𝑵𝒂𝟐 𝑺𝑶𝟒
16000
= 108
=148.14 kmol
From Reaction
=149.63kmol
=149.63*130kg
=19451.9kg
=19.45Ton
16
𝐻2 𝑆𝑂4 = moles * molecular weight
= 74.815* 98
= 7331.87 kg
=7.3 ton
= 74.815 kmol
= 74.815 * 142
= 10623.73
= 10.63 ton
= 100 - 0.99
= 0.195 ton
= 0.148 ton
INPUT OUTPUT
Na-Cresolate = 19.454 Cresol =16
H2SO4 = 733.87 𝑵𝒂𝟐 𝑺𝑶𝟒= 10.62
Unreacted 𝑯𝟐 𝑺𝑶𝟒= 0.148
Unreacted Na cresolate= 0.195
= 26.781 =26.963
Table 6.1
17
𝑖𝑛𝑝𝑢𝑡
Yield=
𝑜𝑢𝑡𝑝𝑢𝑡
26.781
=26.963
=99.32%
18
CHAPTER:- 8
UTILITIES REQUIRED FOR SELECTING PROCESS
19
➢ UTILITIES REQUIRED FOR SELECTING PROCESS
• Power
• Steam
• Water
• Instrument Air
As the plant generates electrical power & steam, that’s why the plant is called Co-generation
plant (COGEN). The plant requires 59760KWH /day for continuous production.
There are three types of sources of power supply in the plant.
Captive Power plant ( CPP)
Gujarat electricity board (GEB)
Diesel generator (DG)
8.2 STEAM
Each day around 400 MT steam is required to run all the processes in the plant. There are mainly
two types of steam which are used in this plant.
Low-pressure steam
Medium pressure steam
For production of saturated steam three boilers is running. All the boilers are having 3 passes,
fire tube dual firing type, as they can handle natural gas and furnace oil as fuel. Out of these
three, two boilers are having capacity of 12 ton/hr and another one is of 16 ton/hr. Pressure of the
LPS and MPS are 2.5 kg/cm2 and 12kg/cm2 respectively.
20
Co-gen plant produces steam of 8kg/cm2 pressure which is totally converted into low pressure
steam.
Each day 290 m3 DM water and some raw water (<50 m3) is required for steam generation.
Supplied raw water from G.I.D.C has a TDS of 80-90ppm.The soft water is first deaerator by
heating up to 105º C and some amount of steam is injected to remove all the dissolved oxygen
and send to economizer to preheat up to 127o C. The furnace oil is pre-heated up to 120º C by a
electrical Preheater & a steam Preheater
Gear pump is used to pump the furnace oil to bring it to the burner. Multistage centrifugal pump,
operating at 25 Kg /cm², is used to feed the water in the boiler chamber. There are two pressure
releasing valve operating at 13.5 &14.5 Kg /cm² respective ly.
A huge amount of water required daily for this plant. Three types of water are utilized in the
plant: -
1) Raw water
2) Soft water
3) De-mineralized water.
Total consumption of water in the plant is ~1000 m3./day. Raw water is used mainly for washing
purpose.
21
CHAPTER:- 9
22
9.1 PLANT LAYOUT & LOCATION
MATERIAL
GATE
ASSEMBLY
POINT 2
MEE
PLANT
FUSION
PLANT ASSEMBLY
POINT 1
PAA
PARA-CRESOL
PLANT
PLANT
PLANT
CANTEEN
24
10.1 THE CAPITAL INVESTMENT FOR THE YEAR 2007-08
The capital investment for the 16 TPD cresol plant was found to be 290.8 crore in year of 2007-
08.
=290.8*1125/551
=591.7*107
Material and labor involved in actual installation of complete facility (70-80%) of fixed
capital investment
(50-60% of FCI)
= 148.4*107
(b) Installation including insulation and painting
40% of 148.7*107
=59.36*107
25% of 148.4*107
=37.175*107
25
(B) Building process and auxiliary (10-70% PEC)
Expenses which are not directly Involved with material and labour factual installation of
complete facility (15-30% of FCI )
=0.1*(7.42*107 )
=0.742*107
=8.162*107
=8.162-107 +1.2243*107
=9.992*107
1. Mfg. cost = Direct production cost+ fixed charge+ plant overhead cost
I. Depreciation: (depends on life period salvage value and method of calculation about
13 % of FCI for machinery and equipment & 2-3 % for Building value)
Consider Depreciation = 10 % of FCI or machinery & Equipment & 3% for building value for
building.
= 0.8162*107
= 0.12243*107
=0.007*(8.162*107 )
=0.057134*107
Rent=0.1(59.36*107 +7.42*107 )
Fixed charge=678*107
𝐹𝐶
Total production Charges= 0.15
=0.60*OL*DS*DL*M&R
28
=0.10*TDC
=4.452*107
(about 3 % of TPC)
=0.03*(44.52*107 )
=1.3356*107
= 10.1036+(1.3356*107 )
= 14.4392*107
1. Gross Earnings/Income
Rs.=230Rs.
=230*(16 TPD)*(330days/year)
= 121.44*107
= (121.44*107 ) – (9.992*107 )
=111.4*107
=0.4*111.4
=445.76 *107
Taxes=495.14
= 111.4*(1-3.96)
29
= 668.64*107
668 .64∗107
= 9.992∗107 ∗ 100
= 66.9% = 70%
30
CHAPTER 11
IMPORTANT ASPECT OF SAFTEY POLLUTION CONTROL
31
11.1 HAZARD SUMMARY
• Cresols can affect you when breathed in and by passing through your skin.
• Cresols are corrosive chemicals and contact can severely irritate and burn the skin and eyes
with possible eye damage.
• Breathing Cresols can irritate the nose, throat and lungs.
• High exposure to Cresols can cause collapse and death within minutes.
• Cresols may cause a skin allergy. If allergy develops, very low future exposure can cause
itching and a skin rash.
• Cresols may damage the liver and kidneys.
• Long-term exposure can lead to chronic poisoning, with trouble swallowing, loss of appetite,
vomiting, diarrhea, headache and dizziness.
32
The following chronic (long-term) health effects can occur at some time after exposure to
Cresols and can last for months or years:
• While Cresols have not been identified as carcinogens, three specific isomers have been
determined to be human carcinogens. Cresols should be handled with extreme caution.
• While Cresols have been tested, they are not classifiable as to their potential to cause
reproductive harm.
• Cresols may cause a skin allergy. If allergy develops, very low future exposure can cause
itching and a skin rash.
• Cresols may damage the liver and kidneys.
• Long-term exposure can lead to chronic poisoning, with trouble swallowing, loss of appetite,
vomiting, diarrhea, headache and dizziness.
11.4.1 Clothing
• Avoid skin contact with Cresols. Wear protective gloves and clothing. Safety equipment
suppliers/manufacturers can provide recommendations on the most protective glove/clothing
material for your operation.
• Safety equipment manufacturers recommend Butyl Rubber; Neoprene; and Viton® for
gloves, and DuPont Responder® and DuPont Tychem® BR/LV, SL and TK for protective
clothing.
• All protective clothing (suits, gloves, footwear, headgear) should be clean, available each
day, and put on before work.
• For solid Cresols wear eye protection with side shields or goggles.
• Wear indirect-vent, impact and splash resistant goggles when working with liquids.
33
• Wear a face shield along with goggles when working with corrosive, highly irritating or toxic
substances.
• Contact lenses should not be worn when working with this substance.
34
And Potassium Hydroxide); Metals (Such As Potassium, Sodium, Magnesium And Zinc);
Amines; And Amides.
• Store in Tightly Closed Containers In A Cool, Well-Ventilated Area Away From Light
And High Temperatures.
• Sources of ignition, such as smoking and open flames, are prohibited where Cresols is
used, handled, or stored in a manner that could create a potential fire or explosion hazard.
35
CHAPTER: - 12
MSDS OF CRESOL
36
12.1 COMPOSITION AND INFORMATION ON INGREDIENTS
Composition:
Name- Cresol
CAS # -106-44-5
% by Weight- 100
Para-Cresol: ORAL (LD50): Acute: 207 mg/kg [Rat]. 344 mg/kg [Mouse]. DERMAL
(LD50): Acute: 301 mg/kg [Rabbit]. VAPOR (LC50): Acute: 355.5 ppm 4 hour(s) [Rat].
Very hazardous in case of skin contact (corrosive, irritant), of ingestion. Hazardous in case of
skin contact (sensitizer, permeator), of eye contact (irritant), of inhalation. The amount of tissue
damage depends on length of contact. Eye contact can result in corneal damage or blindness.
Skin contact can produce inflammation and blistering. Inhalation of dust will produce irritation
to gastro-intestinal or respiratory tract, characterized by burning, sneezing and coughing. Severe
over-exposure can produce lung damage, choking, unconsciousness or death.
37
Check for and remove any contact lenses. Immediately flush eyes with running water for at least
15 minutes, keeping eyelids open. Cold water may be used. Do not use an eye ointment. Seek
medical attention.
12.3.2 Skin Contact:
If the chemical got onto the clothed portion of the body, remove the contaminated clothes as
quickly as possible, protecting your own hands and body. Place the victim under a deluge
shower. If the chemical got on the victim's exposed skin, such as the hand: Gently and
thoroughly wash the contaminated skin with running water and non-abrasive soap. Be
particularly careful to clean folds, crevices, creases and groin. Cold water may be used. If
irritation persists, seek medical attention. Wash contaminated clothing before reusing.
12.3.4 Ingestion:
Do not induce vomiting. Examine the lips and mouth to ascertain whether the tissues are
damaged, a possible indication that the toxic material was ingested; the absence of such signs,
however, is not conclusive. Loosen tight clothing such as a collar, tie, belt or waistband. If the
victim is not breathing, perform mouth-to-mouth resuscitation. Seek immediate medical
attention.
38
12.4.1 Explosion Hazards in Presence of Various Substances:
Risks of explosion of the product in presence of mechanical impact: Not available. Risks of
explosion of the product in presence of static discharge: Not available.
12.4.2 Fire Fighting Media and Instructions:
SMALL FIRE: Use DRY chemical powder. LARGE FIRE: Use water spray, fog or foam. Do
not use water jet.
39
12.7 EXPOSURE CONTROLS/PERSONAL PROTECTION
12.7.1 Engineering Controls:
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne
levels below recommended exposure limits. If user operations generate dust, fume or mist, use
ventilation to keep exposure to airborne contaminants below the exposure limit.
12.7.2 Personal Protection:
Splash goggles. Lab coat. Vapor and dust respirator. Be sure to use an approved/certified
respirator or equivalent Gloves.
12.7.3 Personal Protection in Case of a Large Spill:
Splash goggles. Full suit. Vapor and dust respirator. Boots. Gloves. A self contained breathing
apparatus should be used to avoid inhalation of the product. Suggested protective clothing might
not be sufficient; consult a specialist Before handling this product.
41
CHAPTER: - 13
SOLID WASTE TREATEMENT
42
13.1 WASTE RECOVERY PLANT
Waste recovery plant involves the recovery of waste ,that is further saleable in the market.
Previously the waste obtained from cresol plant was sent to the effluent treatment plant and
finally disposed off, But in the recent years some modifications have been done where the waste
generated in the cresol plant is recovered and selled in the market instead of disposing off.
At present, the waste containing 28% sodium sulphite is treated with 98% concentrated sulphuric
acid in a reactor. Sodium sulphate along with sulphur dioxide and water is produced. The sodium
sulphate thus obtained undergoes neutralization with caustic soda in another reactor before it is
fed to MEE plant. The sulphur dioxide and water generated in this reaction is used for
acidification of sodium cresolate.
43
CHAPTER: - 14
CONCLUSION
44
CONCLUSION
According to my research, the alkylphenols like cresols are important fine chemicals widely
employed as intermediates for resins, dyes, anti-oxidants, pharmaceuticals and agrochemicals,
etc. O-cresol together with 2,6 xylenols are produce through the high temperature gas phase
alkylation of phenol with methanol, at 400-500 C. M-cresol, they are normally synthesized by
complicated and environmental unfavorable processes ex: - toluene dehydration for P-cresol and
alkaline chlorotoulene hydrolysis. Facing the urgency of sustainable develop it is not desirable to
develop energy saving and ecofriendly synthesis routes. As an alternative, especially for the
production of o-cresol and p-cresol because they can be complicate to separating through
distillation in the absence of m-cresol.
45
CHAPTER:- 15
REFERENCE
46
REFERENCE
• www.chemdating.com
• https://pubchem.ncbi.nlm.nih.gov
• https://en.m.wikipedia.org
• www.sigmaaldrich.com
• www.webbook.nist.gov>cgi>cbook
• www.epu.gov
• www.medicinescomplete.com
• www.merckmillipore.com
• www.chemspider.com
• www.chemicalland21.com
47