CN110845330A - Triglycerol monostearate and preparation method and application thereof - Google Patents
Triglycerol monostearate and preparation method and application thereof Download PDFInfo
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- CN110845330A CN110845330A CN201911164098.3A CN201911164098A CN110845330A CN 110845330 A CN110845330 A CN 110845330A CN 201911164098 A CN201911164098 A CN 201911164098A CN 110845330 A CN110845330 A CN 110845330A
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- triglycerol
- monostearate
- alkaline catalyst
- mixed alkaline
- triglycerol monostearate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Abstract
The invention discloses triglycerol monostearate and a preparation method and application thereof, and particularly relates to a preparation method of triglycerol monostearate synthesized by taking recovered ditriester as a raw material. The preparation method comprises S1Mixing and heating glycerol and a compound mixed alkaline catalyst, and concentrating and dehydrating to obtain triglycerol; s2Step S is configured according to a certain proportion1The trimeric glycerol, the triglyceride and the compound mixed alkaline catalyst; s3Adding the triglycerin and the compound mixed alkaline catalyst into a reaction kettle, uniformly mixing, and heating; s4Continuously introducing nitrogen into the reaction kettle, and adding the ditriester into the step S2The mixture of the medium triglycerol and the compound mixed alkaline catalyst is heated and stirred, and then cooled after esterification reaction to obtain solid triglycerolPolyglycerol monostearate. The invention solves the problem of high production cost of the traditional process for many years, has simple process and easily-controlled conditions, and can be widely popularized and applied in industry.
Description
Technical Field
The invention belongs to the field of food additives, and particularly relates to triglycerol monostearate synthesized by taking recovered ditriester as a raw material, and a preparation method and application thereof.
Background
Triglycerol monostearate (PGFE) is a nonionic surfactant with a structure ofIs the order of eyesThe food additive has the functions of emulsifying, thickening, preserving, delaying food ageing, etc. and has HLB value of 5-8, and may be prepared into O/W and W/O emulsion.
Triglycerol monostearate is an important food emulsifier and additive, and has wide application in the industries of food, pharmacy, plastics, textile, cosmetics, detergents and the like.
At present, one of the preparation methods of triglycerol monostearate is to prepare glycerol as a raw material:
the preparation method comprises the following specific steps:
(1) glycerol polymerization: alkali is used as a catalyst, glycerol is condensed and dehydrated to be triglycerol at about 260 ℃ under the protection of nitrogen, and the reaction formula is as follows:
(2) trimerization glycerol alcoholization: alkali is used as a catalyst, the triglycerin and the stearic acid are directly esterified under the protection of nitrogen at the temperature of about 230 ℃, and the reaction formula is as follows:
in this process, about 4% of the total amount of material is produced (i.e. the total product yield is reduced by about 4%), wherein the water is removed with energy consumption (already removed during the chemical reaction), and stearic acid is expensive, thus increasing the production cost. Some manufacturers also use hardened oil and triglycerol as raw materials to prepare the triglycerol monostearate, but the problem of high cost cannot be solved.
Disclosure of Invention
In order to overcome the defects and shortcomings in the prior art, the invention aims to provide the preparation method of the triglycerol monostearate, a byproduct ditriester generated in the process of producing the distilled monoglyceride by a molecular distillation monoglyceride manufacturer is used as a reaction raw material, and the production cost of the triglycerol monostearate can be effectively reduced.
The purpose of the invention is realized by the following technical scheme:
a preparation method of triglycerol monostearate comprises the following steps:
S1mixing and heating glycerol and a compound mixed alkaline catalyst accounting for 0.4-1.2 percent of the weight of the glycerol to 250-260 ℃ under the pressure of-0.09-0.02 MPa, and concentrating and dehydrating to obtain triglycerol;
S2the weight ratio of (0.6-1.0): 0.005 to 0.02 mol ratio of the catalyst1Triglycerol of (1): di-tri-ester: compounding a mixed alkaline catalyst;
S3adding the triglycerin and the compound mixed alkaline catalyst into a reaction kettle under the pressure of-0.09 MPa to 0.02MPa, uniformly mixing, and heating to 60 to 160 ℃;
S4introducing nitrogen into the reaction kettle, and adding the ditriester into the step S2And heating a mixture of the medium triglycerol and the compound mixed alkaline catalyst to 200-260 ℃, stirring, carrying out esterification reaction for 1-6 hours, cooling, and cooling to normal temperature to obtain the solid triglycerol monostearate.
Preferably, the compound mixed alkaline catalyst is Na2CO3NaOH, and Ca (OH)2With NaH2PO2The compounded mixture of (1).
As a preferred scheme, the compound mixed alkaline catalyst is NaOH and NaH2PO2The compounded mixture of (1).
As another preferable scheme, the compound mixed alkaline catalyst is Ca (OH)2And NaH2PO2The compounded mixture of (1).
Preferably, the ditriester is at least one of tristearate or tripalmitin.
Preferably, said step S4The medium nitrogen gas needs to be continuously replaced.
It is a second object of the present invention to provide a triglycerol monostearate prepared as above.
The third object of the present invention is to provide a use of triglycerol monostearate prepared by the above method in food additives.
Preferably, the triglycerol monostearate is applied to an emulsion composition, the emulsion composition is composed of triglycerol monostearate and propylene glycol monostearate, and the mass ratio of the triglycerol monostearate to the propylene glycol monostearate is (3-5): (5-3). The emulsified composition can be applied to cakes, and the adding proportion of the emulsified composition is 0.02-0.04% of the weight of flour.
Preferably, the emulsion composition can effectively improve the quality of cakes, and has better effect than that of the single use of the triglycerol monostearate or the propylene glycol monostearate, wherein the mass ratio of the triglycerol monostearate to the propylene glycol monostearate is 1:1 the best effect is obtained after compounding.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the invention solves the problem of high production cost of the traditional process for many years, and provides the method for preparing the triglycerol monostearate by taking the by-product ditriester and triglycerol generated when a distilled monoglyceride manufacturer produces the distilled monoglyceride as raw materials, wherein the price of the used ditriester is only about 57 percent of stearic acid and about 85.7 percent of hardened oil, and the preparation method can effectively reduce the production cost of the triglycerol monostearate, has simple process and easily-controlled conditions, and can industrially produce the high-quality triglycerol monostearate in large batch.
(2) According to the method, the triglycerin and the ditriester (the triglycerin monostearate is prepared by the esterification reaction at high temperature, and the alkali is used as the catalyst, so that about 4% less moisture is generated compared with the traditional process, the production energy consumption is reduced, and the requirements of environmental protection are met.
(3) In the reaction process, nitrogen is used as protective gas and a reducing agent NaH in a compound mixed alkaline catalyst2PO2Or NaH2PO2·H2O, effectively prevents the decomposition of saturated fatty acid and the darkening of color at high temperature, and reduces the peculiar smell and the stink smell of the product。
(4) The emulsified composition is obtained by compounding the triglycerol monostearate and the propylene glycol monostearate, and can obviously improve the cake quality and increase the cake volume when being applied to cakes, so that the cakes are fine and smooth in tissue and fluffy and soft.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
In the embodiment of the invention, the ditriester is purchased from Kaiwen food Co., Ltd, the triglycerol is purchased from Kaiwen food Co., Ltd, the glycerol is purchased from Hualong glycerol product Co., Ltd, the hydrogenated oil and the stearic acid are purchased from Kaita chemical technology Co., Ltd, and the used catalyst is purchased from Tianjin chemical reagent II.
Example 1
The preparation process of the triglycerol monostearate in the embodiment specifically comprises the following steps:
(1) under the pressure of-0.09 MPa, glycerin and a compound mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1) accounting for 0.4 percent of the weight of the glycerin are mixed2PO2Mixture) is mixed and heated to 250 ℃, and after concentration and dehydration, triglycerol is obtained;
(2) under the pressure of-0.09 MPaa, 10mol of triglycerin and 0.1mol of mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1) are compounded and mixed2PO2Mixture) is added into a reaction kettle, evenly mixed and heated to 60 ℃;
(3) and (3) introducing nitrogen into the reaction kettle, adding 6mol of recovered tristearate into the mixture of the triglycerol and the compound mixed alkaline catalyst in the step (2), heating to 200 ℃, stirring, carrying out esterification reaction for 6 hours, cooling, and cooling to normal temperature to obtain the solid triglycerol monostearate.
The nitrogen gas needs to be continuously replaced throughout the reaction.
Example 2
The preparation process of the triglycerol monostearate in the embodiment specifically comprises the following steps:
(1) under the pressure of 0.01MPa, glycerin and a compound mixed alkaline catalyst (NaOH and NaH in a mass ratio of 1: 1) accounting for 0.8 percent of the weight of the glycerin are mixed2PO2Mixture) is mixed and heated to 255 ℃, and after concentration and dehydration, triglycerol is obtained;
(2) under the pressure of 0.01MPa, 10mol of triglycerin and 0.12mol of mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1) are compounded and mixed2PO2Mixture) is added into a reaction kettle, evenly mixed and heated to 100 ℃;
(3) and (3) introducing nitrogen into the reaction kettle, adding 8mol of recovered tristearate into the mixture of the triglycerol and the compound mixed alkaline catalyst in the step (2), heating to 220 ℃, stirring, carrying out esterification reaction for 4 hours, cooling, and cooling to normal temperature to obtain the solid triglycerol monostearate.
The nitrogen gas needs to be continuously replaced throughout the reaction.
Example 3
The preparation process of the triglycerol monostearate in the embodiment specifically comprises the following steps:
(1) under the pressure of 0.02MPa, glycerin and a compound mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1) accounting for 1.2 percent of the weight of the glycerin are mixed2PO2Mixture) is mixed and heated to 260 ℃, and after concentration and dehydration, triglycerol is obtained;
(2) under the pressure of 0.02MPa, 10mol of triglycerin and 0.15mol of compound mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1)2PO2Mixture) is added into a reaction kettle, evenly mixed and heated to 160 ℃;
(3) and (3) introducing nitrogen into the reaction kettle, adding 10mol of recovered tristearate into the mixture of the triglycerol and the compound mixed alkaline catalyst in the step (2), heating to 260 ℃, stirring, carrying out esterification reaction for 3 hours, cooling, and cooling to normal temperature to obtain the solid triglycerol monostearate.
The nitrogen gas needs to be continuously replaced throughout the reaction.
Example 4 emulsified compositions according to the invention
Consisting of 9kg of the triglycerol monostearate obtained in example 1 and 15kg of propylene glycol monostearate.
Example 5 emulsified compositions according to the invention
15kg of the triglycerol monostearate prepared in example 1 and 9kg of propylene glycol monostearate were mixed together.
Example 6 emulsified compositions according to the invention
The composition was prepared by mixing 12kg of the glyceryl monostearate obtained in example 1 and 12kg of propylene glycol monostearate.
Comparative example 1
The preparation process of the triglycerol monostearate in the comparative example comprises the following specific steps:
(1) under the pressure of 0.02MPa, glycerin and a compound mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1) accounting for 1.2 percent of the weight of the glycerin are mixed2PO2Mixture) is mixed and heated to 260 ℃, and after concentration and dehydration, triglycerol is obtained;
(2) under the pressure of 0.02MPa, 10mol of triglycerin and 0.15mol of compound mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1)2PO2Mixture) is added into a reaction kettle, evenly mixed and heated to 160 ℃;
(3) and (3) introducing nitrogen into a reaction kettle, adding 10mol of hydrogenated oil into the mixture of the triglycerol and the compound mixed alkaline catalyst in the step (2), heating to 260 ℃, stirring, carrying out esterification reaction for 3 hours, cooling, and cooling to normal temperature to obtain the solid triglycerol monostearate.
The nitrogen gas needs to be continuously replaced throughout the reaction.
Comparative example 2
The preparation process of the triglycerol monostearate in the comparative example comprises the following specific steps:
(1) under the pressure of 0.02MPa, glycerin and a compound mixed alkaline catalyst (NaOH and NaH with the mass ratio of 1: 1) accounting for 1.2 percent of the weight of the glycerin are mixed2PO2Mixture) is mixed and heated to 260 ℃, and after concentration and dehydration, triglycerol is obtained;
(2) under the pressure of 0.02MPa, 10mol of triglycerol and 0.15mol is compounded with mixed alkaline catalyst (NaOH and NaH in a mass ratio of 1: 1)2PO2Mixture) is added into a reaction kettle, evenly mixed and heated to 160 ℃;
(3) and (3) introducing nitrogen into a reaction kettle, adding 10mol of stearic acid into the mixture of the triglycerol and the compound mixed alkaline catalyst in the step (2), heating to 260 ℃, stirring, carrying out esterification reaction for 3 hours, cooling, and cooling to normal temperature to obtain the solid triglycerol monostearate.
The nitrogen gas needs to be continuously replaced throughout the reaction.
Test example 1
The content of monoesters in the primary products of triglycerol monostearate obtained in examples 1 to 3 and comparative examples 1 to 2 was determined (according to GB 1886.178-2016).
Test example 2
The indexes of the primary products of triglycerol monostearate prepared in examples 1 to 3 and comparative examples 1 to 2 were examined.
From the above experimental results of examples 1 to 3 and comparative examples 1 to 2, it is understood that the quality of the triglycerol monostearate prepared using the recovered ditriester (tristearate) of the present invention is similar to the color, smell, acid value, iodine value, saponification value, etc. of the triglycerol monostearate prepared using stearic acid or hydrogenated oil, but the production cost of the whole product is reduced by about 50%, and the method has significant economic benefits and meets the industrial production requirements.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A preparation method of triglycerol monostearate is characterized by comprising the following steps:
S1mixing and heating glycerol and a compound mixed alkaline catalyst accounting for 0.4-1.2 percent of the weight of the glycerol to 250-260 ℃ under the pressure of-0.09-0.02 MPa, and concentrating and dehydrating to obtain triglycerol;
S2the weight ratio of (0.6-1.0): 0.005 to 0.02 mol ratio of the catalyst1Triglycerol of (1): di-tri-ester: compounding a mixed alkaline catalyst;
S3adding the triglycerin and the compound mixed alkaline catalyst into a reaction kettle under the pressure of-0.09 MPa to 0.02MPa, uniformly mixing, and heating to 60 to 160 ℃;
S4introducing nitrogen into the reaction kettle, and adding the ditriester into the step S2And heating a mixture of the medium triglycerol and the compound mixed alkaline catalyst to 200-260 ℃, stirring, carrying out esterification reaction for 1-6 hours, cooling, and cooling to normal temperature to obtain the solid triglycerol monostearate.
2. The method of claim 1, wherein the compounded mixed alkaline catalyst is Na2CO3NaOH, and Ca (OH)2With NaH2PO2The compounded mixture of (1).
3. The method of claim 2, wherein the compounded mixed alkaline catalyst is NaOH and NaH2PO2The compounded mixture of (1).
4. The method for preparing triglycerol monostearate according to claim 2, wherein the mixed alkaline catalyst is Ca (OH)2And NaH2PO2The compounded mixture of (1).
5. The method of claim 1, wherein the ditriester is at least one of tristearate or tripalmitin.
6. Process for the preparation of triglycerol monostearate according to any of claims 1 to 5, characterized in that step S4The medium nitrogen gas needs to be continuously replaced.
7. A triglycerol monostearate prepared according to the process of any one of claims 1 to 6.
8. Use of the triglycerol monostearate according to claim 7 in an emulsifying composition.
9. Use of triglycerol monostearate according to claim 8 in an emulsifying composition characterized in that it consists of triglycerol monostearate and propylene glycol monostearate in a mass ratio (3-5): (5-3).
10. Use of triglycerol monostearate according to claim 9 in an emulsifying composition characterized in that the mass ratio of triglycerol monostearate to propylene glycol monostearate is 1: 1.
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Cited By (1)
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| CN115581966A (en) * | 2022-10-13 | 2023-01-10 | 广东凯闻生物科技有限公司 | Production process and application of triglycerol monostearate |
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Application publication date: 20200228 |