CN106365991A - Glyceryl monostearate preparation method - Google Patents
Glyceryl monostearate preparation method Download PDFInfo
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- CN106365991A CN106365991A CN201610762149.2A CN201610762149A CN106365991A CN 106365991 A CN106365991 A CN 106365991A CN 201610762149 A CN201610762149 A CN 201610762149A CN 106365991 A CN106365991 A CN 106365991A
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- glyceryl monostearate
- preparation
- petroleum ether
- lower sediment
- mass ratio
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
Abstract
The invention belongs to the technical field of chemical synthesis, and relates to a glyceryl monostearate preparation method. Raw materials including stearic acid and glycerol carbonate are subjected to esterification reaction under the action of esterification catalysts and subjected to washing, reflux and chromatography to obtain intermediate products. The intermediate products and water are subjected to basic hydrolysis reaction under the action of hydrolysis catalysts and subjected to reflux, chromatography and decompression drying to obtain glyceryl monostearate. Compared with the prior art, the preparation method has the advantages that the purity of the obtained glyceryl monostearate can reach 93% or more, and the yield of the glyceryl monostearate can reach 90% or more under the condition of the preparation process superior to a traditional preparation process. Moreover, the production process is simple, the chemical principle is reliable, reaction conditions are mild, production equipment is simple, operation conditions are simple, product quality is good, the yield is high, investment cost is low, economic benefits are good, the whole production process is high in controllability, and industrial production is easily realized.
Description
Technical field:
The invention belongs to chemosynthesis technical field, it is related to a kind of preparation method of alcohol system nonionic surfactant, special
It is not a kind of preparation method of glyceryl monostearate.
Background technology:
Glyceryl monostearate, abbreviation monoglyceride (gms), there are a chain alkyl and two hydrophilic hydroxyls in molecular structure
Base, has good surface activity, is a kind of surfactant of nonionic, has two kinds of isomers of α and β.It has emulsifying,
Foaming, complexation, lubrication, the anti-fog, multifrequency nature such as cerium sulphate crystal, froth breaking, and safe, gentle, non-stimulated, it is widely used in eating
In the products such as product, pharmaceutical products, cosmetics, plastics and lubricant.The PRODUCTION TRAITS of glyceryl monostearate started from for 19th century
Mid-term, nineteen twenty-nine starts industrialized production at first in the U.S., and nineteen forty-three starts to purify glycerol monostearate with molecularly distilled
The crude product of ester is so as to purity reaches more than 90%.At present the global consumption of glyceryl monostearate reached 200,000 tons with
On, and still increased with annual 2%~3% speed, domestic consumption glyceryl monostearate is about 40,000 tons.With China's day
Change, the fast development of food service industry, the demand of glyceryl monostearate is increasing, wherein the list of high-purity (more than 90%)
Tristerin consumption figure increases year by year, and market prospect is considerable.
In prior art, the industrialized production of glyceryl monostearate mainly has following methods:
1) direct esterification: fatty acid and glycerol, directly there is esterification under acid or base catalyst effect, obtain list
The mixture of tristerin, distearin, glycerol and oils and fatss.
General esterification technique is: stearic acid is 1:1.5 with the mol ratio of glycerol, with p-methyl benzenesulfonic acid, sodium hydroxide, hydrogen-oxygen
Change calcium etc. as catalyst, reaction temperature is 180~200 DEG C, and the response time is 2.5~3h, is passed through nitrogen in course of reaction
Prevent the oxidation of oils and fatss, can also constantly remove generated water simultaneously.Direct esterification is except there being glyceryl monostearate
Generate, with the carrying out of reaction, also have distearin and glyceryl tristearate generates.The list of the method preparation is hard
Glycerol content generally 40%~60%, needs just to obtain content by further refining molecularly distilled such as
More than 90% glyceryl monostearate.
2) ester-interchange method: glycerol and oils and fatss or methyl stearate carry out the exchange distribution of ester under base catalysis, generate
The mixture such as glyceryl monostearate, distearin, have oils and fatss glyceryl alcohol solution and two kinds of methyl ester glyceryl alcohol solution.Oil
Fat glyceryl alcohol solution is to prepare the most important commercial run of glyceryl monostearate, and in oils and fatss alcoholysis reaction, fatty acyl group exists
Rearrange between the dissociative glycerin molecule of grease molecules and addition, generate glyceryl monostearate and distearin.
Distearin and methyl stearate react generation glyceryl tristearate again.Generally reaction condition is: glycerol and Hard Fat
Sour methyl ester, under base catalyst such as sodium hydroxide, potassium hydroxide, Feldalat NM effect, carries out reacting 2~4h at 180~250 DEG C,
Reaction is passed through nitrogen to prevent product color too deep.Thick ester product is that glyceryl monostearate, distearin and three are hard
The mixture of glycerol, obtains high-purity (90%) glyceryl monostearate through molecular distillation purification.Methyl ester glyceryl alcohol
Solution is with the rate of charge of 1:2~1:10 by methyl stearate and glycerol, adds the alkali such as potassium hydroxide to make catalyst, at 200 DEG C
Left and right reaction 0.5h, can obtain the glyceryl monostearate that content is 50%~60%.Obtain through molecular distillation Methods For Purification
To high pure monostearin.
In order to improve glyceryl monostearate product yield, Chinese invention patent cn102964245b discloses a kind of high-quality
The preparation method of amount glyceryl monostearate, it reacts into ester with glycerol using raw material hydrogenated palm oil, so under strong base catalyst
By Four-stage distillation, obtain glyceryl monostearate;Chinese invention patent cn102876464a discloses a kind of high-purity and divides again
The preparation technology of sub- Distilled glycerin monostearate, it is anti-that this invention carries out ester exchange under the high temperature conditions using hydrogenated oil and fat and glycerol
Should, and obtaining glyceryl monostearate through three-stage distillation so that complicated process of preparation, distillation equipment operating condition required
Height, energy consumption increases.
Sum it up, existing production technology is using long-chain fatty acid or oils and fatss and glycerine reaction, react products therefrom
Containing glyceryl monostearate, distearin and glyceryl tristearate, the wherein content of glyceryl monostearate not
More than 60%.The product of low-purity is carried out purification through molecular distillation and obtains high-purity (more than 90%) glycerol monostearate by needs
Ester.This not only makes the low yield of product it is often more important that molecular distillation equipment investment is huge, and operating condition has high demands, energy
Consumption is high, and the production technology defect of existing glyceryl monostearate makes production high cost.Exist in prior art
Problem, the technical program is totally different from the production technology of the glyceryl monostearate of prior art, by feed change and
Synthetic route, carries out reacting the glyceryl monostearate obtaining that yield reaches more than 90% with carbonic acid glyceride and stearic acid for raw material
Crude product, such that it is able to remove molecular distillation step, simplifies separating-purifying step.
Content of the invention:
Present invention aim to overcome that the shortcoming that prior art exists, seek to provide a kind of preparation of glyceryl monostearate
Method, by feed change and synthetic route, carries out reaction with carbonic acid glyceride and stearic acid for raw material and obtains yield reaching 90%
Above glyceryl monostearate crude product, under the conditions of changing existing process, molecular distillation equipment investment is huge, operates bar
Part has high demands, high energy consumption, leads to the present situation that production cost is too high.
To achieve these goals, the concrete technology of the present invention comprises the steps:
(1) esterification
Stearic acid and esterification catalyst a are added and has magnetic stir bar, thermometer and the constant voltage leakage equipped with carbonic acid glyceride
Heat in the there-necked flask of bucket;Under continuous mechanical agitation, reach when design temperature t is 158~162 DEG C whne temperature and slowly drip
Plus carbonic acid glyceride, carry out reacting by heating under steady temperature (160 DEG C), after question response 5h, be cooled to 70 DEG C;With 45~55ml
Hot saturated aqueous common salt washing, is subsequently adding 90~110ml petroleum ether, and flow back at 70 DEG C 20~45min, stratification, while hot
It is decanted off the supernatant, cooling separates out lower sediment;Pour out upper strata petroleum ether, lower sediment uses petroleum ether dissolution, standing again
Layering, merges the supernatant, Distillation recovery petroleum ether at ambient pressure;The lower sediment separating out puts into drying under reduced pressure case, steams few
The petroleum ether of amount, you can obtain intermediate product, determination intermediate product quality of weighing;
Wherein, described esterification catalyst a is selected from one kind of p-methyl benzenesulfonic acid, sodium hydroxide, calcium hydroxide, preferably hydrogen-oxygen
Change sodium;
Described esterification catalyst a and stearic mass ratio are (5~8): 100, preferably 6:100;
Described stearic acid is 1:(1.3~1.6 with the mol ratio of carbonic acid glyceride), preferably 1:1.5.
(2) macromolecule alkali for hydrolysis
Intermediate product, water and hydrolyst b are placed in the there-necked flask of magnetic stir bar.In 80~90 DEG C of oil baths
In pot, heating hydrolysis 3h, is subsequently adding 50~70ml petroleum ether, and flow back 25~30min, and stratification is decanted off upper strata clear while hot
Liquid, cooling separates out lower sediment, the lower sediment of precipitation is put in drying under reduced pressure case and steams after a small amount of petroleum ether, you can obtain
Glyceryl monostearate, sample analysis product purity after weighing.
Wherein, described hydrolyst b is Calcium Carbonate or sodium carbonate, preferably Calcium Carbonate;
The mass ratio of described hydrolyst b and water is (10~15): 100, preferably 12:100;
Described intermediate product is 1:(18~22 with the mass ratio of water), preferably 1:20.
The present invention compared with prior art, under conditions of preparation technology is better than conventional preparation techniques, obtains monostearate
Up to more than 93%, yield reaches more than 90% to the purity of glyceride.And simple production process, the principles of chemistry are reliable, reaction
Mild condition, production equipment is simple, and operating condition is simple, good product quality, high income, and cost of investment is low, good in economic efficiency, whole
Individual production procedure controllability high it is easy to industrialized production.
Specific embodiment:
Below by embodiment, the present invention is described further.
Embodiment 1:
A kind of technological process of the preparation method of glyceryl monostearate that the present embodiment is related to is:
(1) esterification: 14.2g stearic acid and 0.8g sodium hydroxide are added have magnetic stir bar, thermometer and equipped with
Heat in the there-necked flask of the constant pressure funnel of 7.7g carbonic acid glyceride;Under continuous mechanical agitation, when temperature reaches 158 DEG C
It is slowly added dropwise carbonic acid glyceride, carry out reacting by heating under steady temperature (160 DEG C), after question response 5h, be cooled to 70 DEG C;With
The hot saturated aqueous common salt of 50ml is washed, and is subsequently adding 100ml petroleum ether, and flow back at 70 DEG C 30min, and stratification is decanted while hot
Go out the supernatant, cooling separates out lower sediment;Pour out upper strata petroleum ether, lower sediment again use petroleum ether dissolution, stratification,
Merge the supernatant, Distillation recovery petroleum ether at ambient pressure;The lower sediment separating out puts into drying under reduced pressure case, steams a small amount of stone
Oily ether, you can obtain intermediate product.
(2) macromolecule alkali for hydrolysis: 2g intermediate product, 38g water and 4g Calcium Carbonate are placed in the there-necked flask of magnetic stir bar
In;In 85 DEG C of oil bath pans, heating hydrolysis 3h, is subsequently adding 60ml petroleum ether, and flow back 30min, and stratification is decanted off while hot
The supernatant, cooling separates out lower sediment, the lower sediment of precipitation is put into and steams after a small amount of petroleum ether in drying under reduced pressure case, that is,
Can get glyceryl monostearate.
In the present embodiment, glyceryl monostearate product purity is 93.1%, and yield is 89%.
Embodiment 2:
A kind of technological process of the preparation method of glyceryl monostearate that the present embodiment is related to is:
(1) esterification: 14.2g stearic acid and 0.85g calcium hydroxide are added have magnetic stir bar, thermometer and equipped with
Heat in the there-necked flask of the constant pressure funnel of 9.4g carbonic acid glyceride;Under continuous mechanical agitation, when temperature reaches 159 DEG C
It is slowly added dropwise carbonic acid glyceride, carry out reacting by heating under steady temperature (160 DEG C), after question response 5h, be cooled to 70 DEG C;With
The hot saturated aqueous common salt of 50ml is washed, and is subsequently adding 100ml petroleum ether, and flow back at 70 DEG C 35min, and stratification is decanted while hot
Go out the supernatant, cooling separates out lower sediment;Pour out upper strata petroleum ether, lower sediment again use petroleum ether dissolution, stratification,
Merge the supernatant, Distillation recovery petroleum ether at ambient pressure;The lower sediment separating out puts into drying under reduced pressure case, steams a small amount of stone
Oily ether, you can obtain intermediate product.
(2) macromolecule alkali for hydrolysis: the sodium carbonate of 2g intermediate product, 36g water and 5.4g is placed in three mouthfuls of magnetic stir bar
In flask;In 85 DEG C of oil bath pans, heating hydrolysis 3h, is subsequently adding 60ml petroleum ether, and flow back 30min, and stratification inclines while hot
Separate out the supernatant, cooling separates out lower sediment, the lower sediment of precipitation put into and steams a small amount of petroleum ether in drying under reduced pressure case
Afterwards, you can obtain glyceryl monostearate.
In the present embodiment, glyceryl monostearate product purity is 94.2%, and yield is 91%.
Embodiment 3:
A kind of technological process of the preparation method of glyceryl monostearate that the present embodiment is related to is:
(1) esterification: the sodium hydroxide of 14.2g stearic acid and 0.85g is added magnetic stir bar, thermometer and dress
There is heating in the there-necked flask of constant pressure funnel of 8.85g carbonic acid glyceride;Under continuous mechanical agitation, treat that temperature reaches 160
DEG C when be slowly added dropwise carbonic acid glyceride, carry out reacting by heating under steady temperature (160 DEG C), after question response 5h, be cooled to 70 DEG C;
With the washing of 50ml hot saturated aqueous common salt, it is subsequently adding 100ml petroleum ether, flow back at 70 DEG C 40min, stratification inclines while hot
Separate out the supernatant, cooling separates out lower sediment;Pour out upper strata petroleum ether, lower sediment uses petroleum ether dissolution, standing point again
Layer, merges the supernatant, Distillation recovery petroleum ether at ambient pressure;The lower sediment separating out puts into drying under reduced pressure case, steams a small amount of
Petroleum ether, you can obtain intermediate product.
(2) macromolecule alkali for hydrolysis: 2g intermediate product, 40g water and 4.8g Calcium Carbonate are placed in three mouthfuls of burnings of magnetic stir bar
In bottle;In 85 DEG C of oil bath pans, heating hydrolysis 3h, is subsequently adding 60ml petroleum ether, and flow back 30min, and stratification is decanted while hot
Go out the supernatant, cooling separates out lower sediment, the lower sediment of precipitation put into and steams after a small amount of petroleum ether in drying under reduced pressure case,
Can get glyceryl monostearate.
In the present embodiment, glyceryl monostearate product purity is 93.2%, and yield is 91.3%.
Embodiment 4:
A kind of technological process of the preparation method of glyceryl monostearate that the present embodiment is related to is:
(1) esterification: 14.2g stearic acid and 0.85g p-methyl benzenesulfonic acid are added magnetic stir bar, thermometer and dress
There is heating in the there-necked flask of constant pressure funnel of 8.5g carbonic acid glyceride;Under continuous mechanical agitation, treat that temperature reaches 160 DEG C
When be slowly added dropwise carbonic acid glyceride, carry out reacting by heating under steady temperature (160 DEG C), after question response 5h, be cooled to 70 DEG C.With
The hot saturated aqueous common salt of 50ml is washed, and is subsequently adding 100ml petroleum ether, and flow back at 70 DEG C 30min, and stratification is decanted while hot
Go out the supernatant, cooling separates out lower sediment;Pour out upper strata petroleum ether, lower sediment again use petroleum ether dissolution, stratification,
Merge the supernatant, Distillation recovery petroleum ether at ambient pressure;The lower sediment separating out puts into drying under reduced pressure case, steams a small amount of stone
Oily ether, you can obtain intermediate product.
(2) macromolecule alkali for hydrolysis: 2g intermediate product, 42g water and 5g Calcium Carbonate are placed in the there-necked flask of magnetic stir bar
In;In 85 DEG C of oil bath pans, heating hydrolysis 3h, is subsequently adding 60ml petroleum ether, and flow back 30min, and stratification is decanted off while hot
The supernatant, cooling separates out lower sediment, the lower sediment of precipitation is put into and steams after a small amount of petroleum ether in drying under reduced pressure case, that is,
Can get glyceryl monostearate.
In the present embodiment, glyceryl monostearate product purity is 93.5%, and yield is 90.5%.
Claims (6)
1. a kind of preparation method of glyceryl monostearate is it is characterised in that concrete technology comprises the steps:
(1) esterification
Stearic acid and esterification catalyst a added and has magnetic stir bar, thermometer and the constant pressure funnel equipped with carbonic acid glyceride
Heat in there-necked flask;Under continuous mechanical agitation, reach when design temperature t is 158~162 DEG C whne temperature and be slowly added dropwise carbon
Acid glyceride, carries out reacting by heating under steady temperature (160 DEG C), after question response 5h, is cooled to 70 DEG C;Full with 45~55ml heat
With saline solution washing, it is subsequently adding 90~110ml petroleum ether, flow back at 70 DEG C 20~45min, stratification is decanted while hot
Go out the supernatant, cooling separates out lower sediment;Pour out upper strata petroleum ether, lower sediment again use petroleum ether dissolution, stratification,
Merge the supernatant, Distillation recovery petroleum ether at ambient pressure;The lower sediment separating out puts into drying under reduced pressure case, steams a small amount of stone
Oily ether, you can obtain intermediate product, determination intermediate product quality of weighing;
Wherein, described esterification catalyst a is selected from one kind of p-methyl benzenesulfonic acid, sodium hydroxide, calcium hydroxide;
Described esterification catalyst a and stearic mass ratio are (5~8): 100;
Described stearic acid is 1:(1.3~1.6 with the mol ratio of carbonic acid glyceride);
(2) macromolecule alkali for hydrolysis
Intermediate product, water and hydrolyst b are placed in the there-necked flask of magnetic stir bar;In 80~90 DEG C of oil bath pans
Heating hydrolysis 3h, is subsequently adding 50~70ml petroleum ether, and flow back 25~30min, and stratification is decanted off the supernatant while hot,
Cooling separates out lower sediment, the lower sediment of precipitation is put in drying under reduced pressure case and steams after a small amount of petroleum ether, you can obtain list
Tristerin, sample analysis product purity after weighing;
Wherein, described hydrolyst b is Calcium Carbonate or calcium bicarbonate;
The mass ratio of described hydrolyst b and water is (10~15): 100;
Described intermediate product is 1:(18~22 with the mass ratio of water).
2. the preparation method of glyceryl monostearate according to claim 1 is it is characterised in that described esterification catalyst a is
Sodium hydroxide.
3. glyceryl monostearate according to claim 1 preparation method it is characterised in that described esterification catalyst a and
Stearic mass ratio is 6:100.
4. the preparation method of glyceryl monostearate according to claim 1 is it is characterised in that described hydrolyst b is
Calcium Carbonate.
5. glyceryl monostearate according to claim 1 preparation method it is characterised in that described hydrolyst b and
The mass ratio of water is 12:100.
6. the preparation method of glyceryl monostearate according to claim 1 is it is characterised in that described intermediate product and water
Mass ratio be 1:20.
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111187174A (en) * | 2020-01-16 | 2020-05-22 | 广东丽臣奥威实业有限公司 | Production and purification method of fatty acyl glycinate or fatty derivative acyl glycinate |
CN115403466A (en) * | 2022-08-25 | 2022-11-29 | 浙江工业大学 | Synthesis process of monoglyceride |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3937116A1 (en) * | 1989-11-03 | 1991-05-08 | Dainippon Ink & Chemicals | Cyclo-carbonate-contg. ester(s) - by reaction of corresp. cyclo-carbonate-alcohol(s) with mono- or di-carboxylic acids in the presence of acid catalyst and solvent |
CN104672084A (en) * | 2013-11-29 | 2015-06-03 | 时宏 | Preparation method of acetylated fatty acid monoglyceride |
-
2016
- 2016-08-30 CN CN201610762149.2A patent/CN106365991A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3937116A1 (en) * | 1989-11-03 | 1991-05-08 | Dainippon Ink & Chemicals | Cyclo-carbonate-contg. ester(s) - by reaction of corresp. cyclo-carbonate-alcohol(s) with mono- or di-carboxylic acids in the presence of acid catalyst and solvent |
CN104672084A (en) * | 2013-11-29 | 2015-06-03 | 时宏 | Preparation method of acetylated fatty acid monoglyceride |
Non-Patent Citations (2)
Title |
---|
LI HAN ET AL.: ""Preparation of glycerol monostearate from glycerol carbonate and stearic acid"", 《RSC ADV.》 * |
MOJGAN KARGAR ET AL.: ""Use of Glycerol Carbonate in an Efficient, One-Pot and Solvent Free Synthesis of 1,3-sn-Diglycerides"", 《J AM OIL CHEM SOC》 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111187174A (en) * | 2020-01-16 | 2020-05-22 | 广东丽臣奥威实业有限公司 | Production and purification method of fatty acyl glycinate or fatty derivative acyl glycinate |
CN115403466A (en) * | 2022-08-25 | 2022-11-29 | 浙江工业大学 | Synthesis process of monoglyceride |
CN115403466B (en) * | 2022-08-25 | 2024-01-30 | 浙江工业大学 | Synthesis process of monoglyceride |
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