Glycerol monostearate

From Wikipedia, the free encyclopedia

Not to be confused with glycol monostearate.

Glycerol monostearate

Names

IUPAC name

2,3-Dihydroxypropyl octadecanoate

Other names

Glyceryl monostearate

Glycerin monostearate

Monostearin

Identifiers

CAS Number 123-94-4

Abbreviations GMS

ChEMBL ChEMBL255696

ChemSpider 23095

ECHA InfoCard 100.004.242

Jmol 3D model Interactive image

KEGG D01947
 PubChem 24699

InChI[show]

SMILES[show]

Properties

Chemical formula C21H42O4

Molar mass 358.56 gmol1

Appearance White to yellowish solid

Density 0.97 g/cm3

Melting point 58 to 59 C (136 to 138 F; 331 to

332 K)

Boiling point 238 to 239 C (460 to 462 F; 511 to

512 K)

Solubility in water Insoluble

Hazards

Flash point 230 C (446 F) (open cup)

Except where otherwise noted, data are given for materials in

their standard state (at 25 C [77 F], 100 kPa).

verify (what is ?)

Infobox references

Glycerol monostearate, commonly known as GMS, is an organic molecule used as an emulsifier.

[1]
GMS is a white, odorless, and sweet-tasting flaky powder that is hygroscopic. It is
a glycerol ester of stearic acid. It occurs naturally in the body as a product of the breakdown of fats
by pancreatic lipase, and is also found in fatty foods.
 GMS is a food additive used as a thickening, emulsifying, anti-caking, and preservative agent; an
emulsifying agent for oils, waxes, and solvents; a protective coating for hygroscopic powders; a
solidifier and control release agent in pharmaceuticals; and a resin lubricant. It is also used in
cosmetics and hair care products.[2]
GMS is largely used in baking preparations to add "body" to the food. It is responsible for giving ice
cream and whipped cream its smooth texture. It is sometimes used as an anti-staling agent in bread.

Compendial status[edit]
British Pharmacopoeia [3]

References[edit]
1. Jump up^ Jens Birk Lauridsen (1976). "Food emulsifiers: Surface activity, edibility,
manufacture, composition, and application". Journal of the American Oil Chemists' Society. 53 (6):
400407. doi:10.1007/BF02605731.

2. Jump up^ Glycerol monostearate Cheminfo

3. Jump up^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009"(PDF). Archived
from the original (PDF) on 11 April 2009. Retrieved18 March 2010.
Categories:
Food additives
Stearates
Diols
Fatty acid esters
Non-ionic surfactants

Issue 41, 2016, Issue in Progress

Previous Article | Next Article

Paper

Preparation of glycerol monostearate from glycerol carbonate and

stearic acid
Li Hana and Tao Wang*a
Hide Affiliations
*
Corresponding authors
a

State Key Laboratory of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing,
China
 E-mail: taowang@tsinghua.edu.cn
Fax: +86 10 62784877
Tel: +86 10 62784877
RSC Adv., 2016,6, 34137-34145

DOI: 10.1039/C6RA02912D
Received 01 Feb 2016, Accepted 28 Mar 2016
First published online 30 Mar 2016

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Abstract
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The chemical equilibrium for the preparation of glycerol monostearate (GMS) from glycerol carbonate (GC) and
stearic acid (SA) was investigated. The chemical equilibrium constant K of the base-catalyzed synthesis of GMS from
GC and SA was much smaller than that of the acid-catalyzed synthesis of (2-oxo-1,3-dioxolan-4-yl) methyl stearate
(ODOMS) from GC and SA. In other words, it was thermodynamically difficult to obtain GMS with a high yield from
GC and SA catalysed by basic catalysts. To prove this argument, we used magnesium oxide (MgO) as a catalyst to
synthesize GMS from GC and SA. As expected, the yield of GMS was quite low. To increase the yield of GMS, a two-
step procedure was proposed. First, pure ODOMS was synthesized by the esterification of GC with SA using
copper p-toluenesulfonate (CPTS) as the catalyst. The conversion of SA reached 96.14% under the following
conditions: reaction temperature, 140 C; catalyst amount, 3% CPTS (based on the SA weight); reaction time, 3 h;
GC-to-SA molar ratio, 1.5 : 1. Second, GMS was produced at a yield of 64.4% by the hydrolysis of ODOMS in the
presence of triethylamine. The syntheses of ODOMS and GMS were confirmed by 1H- and 13C-NMR, FTIR and LC-
MS analysis.

ZSM-5
From Wikipedia, the free encyclopedia

The molecular structure of MFI zeolite, showing well defined pores and channels in the zeolite. Yellow balls are
Si and red balls are O atoms.
 Electron micrograph of MFI zeolite with the above model overlaid in the right-bottom part. [1]

ZSM-5, Zeolite Socony Mobil5 (framework type MFI from ZSM-5 (five)), is
analuminosilicate zeolite belonging to the pentasil family of zeolites. Its chemical formula is
NanAlnSi96nO19216H2O (0<n<27). Patented by Mobil Oil Company in 1975, it is widely used in
the petroleum industry as a heterogeneous catalyst forhydrocarbon isomerization reactions.

Contents
[hide]

1Structure

2Background of the invention

3Synthesis

4Uses

5References

6External links

Structure[edit]

The pentasil unit of ZSM-5

ZSM-5 is composed of several pentasil units linked together by oxygen bridges to form pentasil
chains. A pentasil unit consists of eight five-membered rings. In these rings, the vertices
are Al or Si and an O is assumed to be bonded between the vertices. The pentasil chains are
interconnected by oxygen bridges to form corrugated sheets with 10-ring holes. Like the pentasil
units, each 10-ring hole has Al or Si as vertices with an O assumed to be bonded between each
vertex. Each corrugated sheet is connected by oxygen bridges to form a structure with "straight 10-
ring channels running parallel to the corrugations and sinusoidal 10-ring channels perpendicular to
the sheets."[2] Adjacent layers of the sheets are related by an inversion point. The estimated pore
size of the channel running parallel with the corrugations is 5.45.6 . [3] The crystallographic unit cell
of ZSM-5 has 96 T sites (Si or Al), 192 O sites, and a number of compensating cations depending on
the Si/Al ratio, which ranges from 12 to infinity. The structure is orthorhombic (space group Pnma) at
high temperatures, but a phase transition to the monoclinic space group P2 1/n.1.13 occurs on
cooling below a transition temperature, located between 300 and 350 K. [4][5]
ZSM-5 catalyst was first synthesized by Argauer and Landolt in 1969. [6] It is a medium pore zeolite
with channels defined by ten-membered rings. The synthesis involves three different solutions. The
first solution is the source of alumina, sodium ions, and hydroxide ions; in the presence of excess
base the alumina will form soluble Al(OH)4 ions. The second solution has the tetrapropylammonium
cation that acts as a templating agent. The third solution is the source of silica, one of the basic
building blocks for the framework structure of a zeolite. Mixing the three solutions produces
supersaturated tetrapropylammonium ZSM-5, which can be heated to recrystallize and produce a
solid.

Background of the invention[edit]

Pentasil-zeolites are defined by their structure type, and more specifically by their X-ray
diffraction patterns. ZSM-5 is the trade name of a pentasil-zeolite.
As early as 1967, Argauer and Landolt worked out parameters for the synthesis of pentasilzeolites,
particularly those relating to the following molar ratios: OH/SiO2 = 0.0710, SiO2/Al2O3 = 5100,
H2O/SiO2 = 1240.[6] However, the Argauer and Landolt procedure succeeded in synthesizing a
reasonably pure phase ZSM-5 zeolite only if organic amines with a structure-giving function (i.e.
template function), such as tetrapropyleneammonium compounds were used. Subsequent
publications have disclosed methods of conducting the synthesis of pentasil-zeolites without
requiring the very expensive, toxic and easily inflammable organic amine templates. Still other
subsequent publications have disclosed substitutes for these amines. In addition to their expense,
toxicity and flammability, such amines are disfavored because they are subject to thermal
decomposition which can destroy the zeolite structure. Further publications have disclosed
modifications of the Argauer and Landolt process directed towards improving the reactivity of the
SiO2 and Al2O3 starting materials.

Synthesis[edit]
ZSM-5 is a synthetic zeolite, closely related to ZSM-11. There are many ways to synthesize ZSM-5,
a common method is as follows:[7]
SiO2 + NaAlO2 + NaOH + N(CH2CH2CH3)4Br + H2O ZSM-5 + analcime + alpha-quartz
ZSM-5 is typically prepared at high temperature and high pressure in a Teflon-
coated autoclave and can be prepared using varying ratios of SiO2 and Al containing
compounds.

Uses[edit]
ZSM-5 has a high silicon to aluminum ratio. Whenever an Al3+ cation replaces a Si4+ cation, an
additional positive charge is required to keep the material charge-neutral. With proton (H+) as the
cation, the material becomes very acidic. Thus the acidity is proportional to the Al content. The
very regular 3-D structure and the acidity of ZSM-5 can be utilized for acid-
catalyzed reactions such as hydrocarbon isomerization and the alkylation of hydrocarbons. One
such reaction is the isomerization of meta-xylene to para-xylene. Within the pores of the ZSM-5
zeolite, para-xylene has a much higher diffusion coefficient than meta-xylene. When the
isomerization reaction is allowed to occur within the pores of ZSM-5, para-xylene is able to
traverse along the pores of the zeolite, diffusing out of the catalyst very quickly. This size-
selectivity allows the isomerization reaction to occur quickly in high yield. [8]
Isomerisation of meta-xylene topara-xylene on passing through a ZSM-5 catalyst.
ZSM-5 has been used as a support material for catalysis. In one such example, copper is
deposited on the zeolite and a stream of ethanol is passed through at temperatures of 240 to
320 C as a vapour stream, which causes the ethanol tooxidize to acetaldehyde; two hydrogens
are lost by the ethanol as hydrogen gas. It appears that the specific pore size of ZSM-5 is of
benefit to this process, which also functions for other alcohols and oxidations. The copper is
occasionally combined with other metals, such as chromium, to fine tune the diversity and
specificity of the products, as there is likely to be more than one. Acetic acid is an example of
one possible byproduct from hot copper oxidation.It is used to convert alcohols directly into
gasoline.

References[edit]
1. Jump up^ Kumar, Prashant; Agrawal, Kumar Varoon; Tsapatsis, Michael; Mkhoyan, K. Andre
(2015). "Quantification of thickness and wrinkling of exfoliated two-dimensional zeolite
nanosheets". Nature Communications. 6: 7128.doi:10.1038/ncomms8128. PMC 4432588
.PMID 25958985.

2. Jump up^ Zeolites and Ordered Mesoporous Materials: Progress and Prospects. (2005) Vol
157. Ed: J. ejka, H. van Bekkum.ISBN 0-444-52066-X

3. Jump up^ Modeling of Structure and Reactivity in Zeolites (1992). Ed: C.R.A. Catlow.
Academic Press, Ltd.: London. ISBN 0-12-164140-6

4. Jump up^ Hay, D.G.; G. W. West (1985). "Examination of the monoclinic/orthorhombic

transition in silicalite using XRD and silicon NMR". Journal of Physical Chemistry. 89 (7): 1070
1072. doi:10.1021/j100253a005.

5. Jump up^ Grau-Crespo, R; Acuay E; Ruiz-Salvador A.R. (2002). "A free energy minimisation
study of the monoclinicorthorhombic transition in MFI zeolite". Chemical Communications (21):
25442545.doi:10.1039/B208064H.

6. ^ Jump up to:a b Argauer, Robert J and Landolt, George R (1972) "Crystalline zeolite zsm-5
and method of preparing the same"U.S. Patent 3,702,886

7. Jump up^ Lermer, H.; Draeger, M.; Steffen, J.; Unger, K.K. (1985). "Synthesis and structure
refinement of ZSM5 single crystals". Zeolites. 5 (3): 131134. doi:10.1016/0144-
2449(85)90019-3.

8. Jump up^ Dyer, Alan (1988). An Introduction to Zeolite Molecular Sieves. John Wiley &
Sons. ISBN 0-471-91981-0

External links[edit]
ZEOMICS Zeolite Pore Characterization of MFI (ZSM-5)
 Categories:
Zeolites