CN116751236A - Preparation method of sucrose fatty acid diester - Google Patents
Preparation method of sucrose fatty acid diester Download PDFInfo
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- CN116751236A CN116751236A CN202310655596.8A CN202310655596A CN116751236A CN 116751236 A CN116751236 A CN 116751236A CN 202310655596 A CN202310655596 A CN 202310655596A CN 116751236 A CN116751236 A CN 116751236A
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- fatty acid
- sucrose fatty
- sucrose
- acid diester
- crude product
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- 229930006000 Sucrose Natural products 0.000 title claims abstract description 124
- 239000005720 sucrose Substances 0.000 title claims abstract description 124
- -1 sucrose fatty acid diester Chemical class 0.000 title claims abstract description 80
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 76
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 76
- 239000000194 fatty acid Substances 0.000 title claims abstract description 76
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 45
- 239000012043 crude product Substances 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 57
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims description 32
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 30
- 239000012267 brine Substances 0.000 claims description 26
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- 239000012074 organic phase Substances 0.000 claims description 16
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 10
- 238000001953 recrystallisation Methods 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000000746 purification Methods 0.000 abstract description 9
- 150000005690 diesters Chemical class 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 238000001914 filtration Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000005303 weighing Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229940114930 potassium stearate Drugs 0.000 description 4
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
Abstract
The application discloses a preparation method of sucrose fatty acid diester, and relates to the technical field of preparation of sucrose fatty acid ester. The method comprises the following steps: (1) Adding sucrose, fatty acid methyl ester and a catalyst into a solvent, and carrying out transesterification under the condition of reduced pressure to obtain a sucrose fatty acid ester crude product; (2) Concentrating, purifying and separating the sucrose fatty acid ester crude product to obtain the sucrose fatty acid diester. The method can improve the content of the diester in the crude product by controlling the reaction condition, and can stabilize the content of the diester by more than 90 percent and even up to 95 percent by adding a special purification means.
Description
Technical Field
The application relates to the technical field of preparation of sucrose fatty acid esters, in particular to a preparation method of sucrose fatty acid diester.
Background
Sucrose fatty acid ester is a kind of edible surfactant with safe use and excellent performance, and is widely applied to food industry, pharmaceutical industry, daily chemical industry and other industrial and agricultural departments.
At present, the industrialized production of sucrose fatty acid ester mainly adopts an ester exchange method, for example, the patent with publication number of CN86106683A discloses a method for synthesizing sucrose fatty acid ester by using a solvent method, and fatty acid ester is mainly obtained by esterification reaction of fatty acid and lower alcohol; then carrying out transesterification reaction with sucrose in propylene glycol solvent under certain conditions and in the presence of a catalyst, separating the solvent, and removing impurities and unreacted reactants in the product by using sodium chloride solution. The publication No. CN102850413A discloses a method for preparing sucrose fatty acid ester, which comprises the following steps: (1) Taking fatty acid methyl ester and sucrose as raw materials, taking potassium carbonate as a catalyst, taking potassium stearate as an emulsifier, adding a three-phase transfer catalyst, and synthesizing sucrose ester under the conditions of normal pressure or reduced pressure at the reaction temperature of 80-145 ℃; (2) Stopping reacting for 2-10 hours, adding mixed solvent for extraction, filtering and washing to obtain a phase transfer catalyst, decompressing and desolventizing, and drying to obtain a sucrose ester product.
However, at present, the methods mainly produce sucrose monoester, and synthesis and purification of sucrose diester are reported; in the process of purifying sucrose fatty acid ester in the prior art, the purifying method is complex, for example, the patent with publication number of CN106854226A discloses a refining method of sucrose fatty acid ester, and the method comprises the following steps: adding water into the sucrose fatty acid ester crude product, heating, regulating pH value, carrying out solid-liquid separation after semisolid precipitation, collecting semisolid substances, washing with hot water to obtain semisolid mixture, adding organic solvent, heating, stirring, standing for layering, cooling the organic layer substance to room temperature to obtain semitransparent congealing mixture, and conveying to sucrose fatty acid ester extraction equipment for differential contact countercurrent extraction. The technology adopts differential contact type countercurrent extraction equipment for extraction, has higher equipment requirement and complex purification method.
Therefore, the present application provides a preparation method which is simple and can improve the diester content and the total diester yield in sucrose fatty acid ester, and the technical problem to be solved in the present application is urgent.
Disclosure of Invention
Aiming at the defects of the prior art, one of the purposes of the application is to provide a preparation method of sucrose fatty acid diester, wherein the content of the sucrose fatty acid diester prepared by the method and the total yield of the diester are high.
In order to achieve the technical purpose, the application mainly adopts the following technical scheme:
a method for preparing sucrose fatty acid diester, comprising the following steps:
(1) Adding sucrose, fatty acid methyl ester and a catalyst into a solvent, and carrying out transesterification under the condition of reduced pressure to obtain a sucrose fatty acid ester crude product;
(2) Concentrating, purifying and separating the sucrose fatty acid ester crude product to obtain the sucrose fatty acid diester.
In a preferred embodiment of the present application, in step (1), the fatty acid methyl ester is selected from any one of methyl laurate or methyl palmitate; the catalyst is selected from any one of potassium carbonate or potassium hydroxide; the solvent is selected from N, N-dimethylformamide, dimethyl sulfoxide, a mixture of N, N-dimethylformamide and toluene or a mixture of N, N-dimethylformamide and tetrahydrofuran.
In a preferred embodiment of the present application, in step (1), the transesterification is carried out at a pressure of 0.2 to 0.8kPa, the transesterification temperature is 70 to 120℃and the reaction time is 6 to 18 hours.
In a preferred embodiment of the present application, in the step (1), the amount of the fatty acid methyl ester added is 2 to 6 times the amount of the sucrose added, the amount of the catalyst added is 1 to 10% of the amount of the sucrose added, and 4 to 8L of the solvent is used for every 1kg of sucrose.
In another preferred embodiment of the present application, in the step (2), the purification method is to extract the sucrose fatty acid ester crude product, collect the organic phase, and then recrystallize the extracted organic phase.
Further, when the sucrose fatty acid ester crude product is extracted, the extraction solvent is ethyl acetate/brine mixture, and the volume ratio of ethyl acetate to brine in the extraction solvent is ethyl acetate to brine=4-10:1.
Further, when the extract is subjected to extractive recrystallization, the recrystallization solvent used is an 80% n-butanol-water solution.
Further, the separation method is to filter the recrystallized product to obtain an upper layer solid, and then to dry the upper layer solid to obtain the sucrose fatty acid diester.
Compared with the prior art, the application has the following beneficial effects:
the method can improve the content of the diester in the crude product by controlling the reaction conditions, and can stabilize the content of the diester by more than 90 percent, even up to 95 percent by adding a special purification means;
the method has the advantages of mild reaction conditions, simple purification, low cost and stable process, and is easy for industrialized mass production.
Detailed Description
Hereinafter, embodiments of the present application will be described in detail. It should be noted that the technical features or combinations of technical features described in the following embodiments should not be regarded as being isolated, and they may be combined with each other and with each other to achieve a better technical effect.
Example 1
A method for preparing sucrose fatty acid diester, comprising the following steps:
(1) Weighing sucrose, methyl laurate and potassium carbonate according to a proportion, adding into N, N-dimethylformamide, and carrying out transesterification under the pressure condition of 0.2kPa, wherein the transesterification temperature is 80 ℃, and the reaction time is 8 hours, so as to obtain a sucrose fatty acid ester crude product;
wherein, the adding amount of methyl laurate is 3 times of the adding amount of the sucrose, the adding amount of the catalyst is 5 percent of the adding amount of the sucrose, and 6L of N, N-dimethylformamide is correspondingly used for every 1kg of sucrose.
(2) Concentrating the sucrose fatty acid ester crude product by adopting a reduced pressure distillation mode, extracting by utilizing an ethyl acetate/brine mixture (the volume ratio of ethyl acetate to brine is ethyl acetate to brine=7:1), collecting an organic phase, dissolving the organic phase in 80% of n-butanol aqueous solution for recrystallization, filtering, and drying the upper solid obtained by filtering to obtain the sucrose fatty acid diester.
Example 2
A method for preparing sucrose fatty acid diester, comprising the following steps:
(1) Weighing sucrose, methyl palmitate and potassium hydroxide according to a proportion, adding into dimethyl sulfoxide, and carrying out transesterification under the pressure condition of 0.4kPa, wherein the transesterification temperature is 70 ℃ and the reaction time is 18 hours, thus obtaining a sucrose fatty acid ester crude product;
wherein, the addition amount of the methyl palmitate is 6 times of the addition amount of the sucrose, the addition amount of the catalyst is 10 percent of the addition amount of the sucrose, and 8L of dimethyl sulfoxide is correspondingly used for every 1kg of sucrose.
(2) Concentrating the sucrose fatty acid ester crude product by adopting a reduced pressure distillation mode, extracting by utilizing an ethyl acetate/brine mixture (the volume ratio of ethyl acetate to brine is ethyl acetate to brine=4:1), collecting an organic phase, dissolving the organic phase in 80% of n-butanol-water solution for recrystallization, filtering, and drying the upper solid obtained by filtering to obtain sucrose fatty acid diester.
Example 3
A method for preparing sucrose fatty acid diester, comprising the following steps:
(1) Weighing sucrose, methyl laurate and potassium carbonate according to a proportion, adding into N, N-dimethylformamide, and carrying out transesterification under the pressure condition of 0.8kPa, wherein the transesterification temperature is 120 ℃, and the reaction time is 6 hours, so as to obtain a sucrose fatty acid ester crude product;
wherein, the adding amount of methyl laurate is 2 times of the adding amount of the sucrose, the adding amount of the catalyst is 1% of the adding amount of the sucrose, and 4L dimethyl sulfoxide is correspondingly used for every 1kg of sucrose.
(2) Concentrating the sucrose fatty acid ester crude product in a vacuum drying mode, extracting by using an ethyl acetate/brine mixture (the volume ratio of ethyl acetate to brine is ethyl acetate: brine=10:1), collecting an organic phase, dissolving the organic phase in 80% of n-butanol-water solution for recrystallization, filtering, and drying the upper solid obtained by filtering to obtain sucrose fatty acid diester.
Comparative example 1
Substantially the same as in example 1, the main difference is that: potassium stearate is also added into the reaction system.
A method for preparing sucrose fatty acid diester, comprising the following steps:
(1) Weighing sucrose, methyl laurate, potassium carbonate and potassium stearate according to a proportion, adding into N, N-dimethylformamide, and carrying out transesterification under the pressure condition of 0.2kPa, wherein the transesterification temperature is 80 ℃ and the reaction time is 8 hours, thus obtaining a sucrose fatty acid ester crude product;
wherein, the adding amount of methyl laurate is 3 times of the adding amount of sucrose, the adding amount of catalyst potassium carbonate is 5% of the adding amount of sucrose, the adding amount of potassium stearate is 5% of the adding amount of sucrose, and 6L of N, N-dimethylformamide is correspondingly used for every 1kg of sucrose.
(2) Concentrating the sucrose fatty acid ester crude product by adopting a reduced pressure distillation mode, extracting by utilizing an ethyl acetate/brine mixture (the volume ratio of ethyl acetate to brine is ethyl acetate to brine=7:1), collecting an organic phase, dissolving the organic phase in 80% of n-butanol-water solution for recrystallization, filtering, and drying the upper solid obtained by filtering to obtain sucrose fatty acid diester.
Comparative example 2
Substantially the same as in example 1, the main difference is that: the pressure (vacuum) of the reaction.
(1) Weighing sucrose, methyl laurate and potassium carbonate according to a proportion, adding into N, N-dimethylformamide, and carrying out transesterification under the pressure condition of 5kPa, wherein the transesterification temperature is 80 ℃, and the reaction time is 8 hours, so as to obtain a sucrose fatty acid ester crude product;
wherein, the adding amount of methyl laurate is 3 times of the adding amount of the sucrose, the adding amount of the catalyst potassium carbonate is 5% of the adding amount of the sucrose, and 6L of N, N-dimethylformamide is correspondingly used for every 1kg of sucrose.
(2) Concentrating the sucrose fatty acid ester crude product by adopting a reduced pressure distillation mode, extracting by utilizing an ethyl acetate/brine mixture (the volume ratio of ethyl acetate to brine is ethyl acetate to brine=7:1), collecting an organic phase, dissolving the organic phase in 80% of n-butanol aqueous solution for recrystallization, filtering, and drying the upper solid obtained by filtering to obtain the sucrose fatty acid diester.
Comparative example 3
Substantially the same as in example 1, the main difference is that: the purification process of the sucrose fatty acid ester crude product is different.
(1) Weighing sucrose, methyl laurate and potassium carbonate according to a proportion, adding into N, N-dimethylformamide, and carrying out transesterification under the pressure condition of 0.2kPa, wherein the transesterification temperature is 80 ℃, and the reaction time is 8 hours, so as to obtain a sucrose fatty acid ester crude product;
wherein, the adding amount of methyl laurate is 3 times of the adding amount of the sucrose, the adding amount of the catalyst potassium carbonate is 5% of the adding amount of the sucrose, and 6L of N, N-dimethylformamide is correspondingly used for every 1kg of sucrose.
(2) After mixing the sucrose fatty acid ester crude product with ethanol (2L ethanol is used for each 1kg of sucrose fatty acid ester crude product), the mixture is neutralized with glacial acetic acid, and the pH is adjusted to 7. Heating to boiling, standing, layering, collecting upper solution, vacuumizing (below 7 mmHg) and heating to 105deg.C, evaporating to obtain oily sucrose ester, and cooling to room temperature to become waxy. And wrapping the waxy solid obtained by the reaction with filter cloth at a constant temperature of 35 ℃, and squeezing by a squeezer to obtain massive sucrose ester. And co-dissolving the block products with 3-10% absolute ethyl alcohol at 70 ℃, then keeping the temperature between 18 and 25 ℃, wrapping with filter cloth, squeezing, and collecting diester products.
Comparative example 4
Substantially the same as in example 1, the main difference is that: the purification process of the sucrose fatty acid ester crude product is different.
(1) Weighing sucrose, methyl laurate and potassium carbonate according to a proportion, adding into N, N-dimethylformamide, and carrying out transesterification under the pressure condition of 0.2kPa, wherein the transesterification temperature is 80 ℃, and the reaction time is 8 hours, so as to obtain a sucrose fatty acid ester crude product;
wherein, the adding amount of methyl laurate is 3 times of the adding amount of the sucrose, the adding amount of the catalyst potassium carbonate is 5% of the adding amount of the sucrose, and 6L of N, N-dimethylformamide is correspondingly used for every 1kg of sucrose.
(2) Concentrating the sucrose fatty acid ester crude product by adopting a reduced pressure distillation mode, dissolving the concentrated solution in 80% of n-butanol-water solution for recrystallization, filtering, extracting the upper layer solid obtained by filtering by using an ethyl acetate/brine mixture (the volume ratio of ethyl acetate to brine is ethyl acetate: brine=7:1), collecting an organic phase, concentrating and drying to obtain the sucrose fatty acid diester.
Comparative example 5
Substantially the same as in example 1, the main difference is that: the purification process of the sucrose fatty acid ester crude product is different.
(1) Weighing sucrose, methyl laurate and potassium carbonate according to a proportion, adding into N, N-dimethylformamide, and carrying out transesterification under the pressure condition of 0.2kPa, wherein the transesterification temperature is 80 ℃, and the reaction time is 8 hours, so as to obtain a sucrose fatty acid ester crude product;
wherein, the adding amount of methyl laurate is 3 times of the adding amount of the sucrose, the adding amount of the catalyst potassium carbonate is 5% of the adding amount of the sucrose, and 6L of N, N-dimethylformamide is correspondingly used for every 1kg of sucrose.
(2) Concentrating the sucrose fatty acid ester crude product by adopting a reduced pressure distillation mode, extracting by utilizing an ethyl acetate/brine mixture (the volume ratio of ethyl acetate to brine is equal to 7:1), collecting an organic phase, cooling to room temperature, carrying out differential contact type countercurrent extraction in extraction equipment, concentrating the material discharged from a discharge port in vacuum, and drying to obtain sucrose fatty acid diester.
The sucrose fatty acid diester content, monoester content, and total ester content obtained in examples 1 to 3 and comparative examples 1 to 4 of the present application were measured, and the results are shown in Table 1 below.
TABLE 1
Wherein, the content represents the weight of each component in the collected sucrose fatty acid diester to the total product: yield represents the ratio of the weight of sucrose fatty acid diester actually produced during the preparation to the weight of sucrose fatty acid diester theoretically produced.
Although a few embodiments of the present application have been described herein, those skilled in the art will appreciate that changes can be made to the embodiments herein without departing from the spirit of the application. The above-described embodiments are exemplary only, and should not be taken as limiting the scope of the claims herein.
Claims (8)
1. The preparation method of the sucrose fatty acid diester is characterized by comprising the following steps:
(1) Adding sucrose, fatty acid methyl ester and a catalyst into a solvent, and carrying out transesterification under the condition of reduced pressure to obtain a sucrose fatty acid ester crude product;
(2) Concentrating, purifying and separating the sucrose fatty acid ester crude product to obtain the sucrose fatty acid diester.
2. The method for producing sucrose fatty acid diester according to claim 1, wherein in the step (1), the fatty acid methyl ester is selected from any one of methyl laurate and methyl palmitate; the catalyst is selected from any one of potassium carbonate or potassium hydroxide; the solvent is selected from N, N-dimethylformamide, dimethyl sulfoxide, a mixture of N, N-dimethylformamide and toluene or a mixture of N, N-dimethylformamide and tetrahydrofuran.
3. The method for producing sucrose fatty acid diester according to claim 1, wherein in step (1), the transesterification reaction is carried out under a pressure of 0.2 to 0.8kPa, the transesterification reaction temperature is 70 to 120 ℃, and the reaction time is 6 to 18 hours.
4. The method for producing a sucrose fatty acid diester according to claim 1, wherein in the step (1), the fatty acid methyl ester is added in an amount of 2 to 6 times the amount of sucrose added, the catalyst is added in an amount of 1 to 10% of the amount of sucrose added, and 4 to 8L of the solvent is used for every 1kg of sucrose.
5. The method for producing sucrose fatty acid diester according to claim 1, wherein in the step (2), the crude sucrose fatty acid ester is extracted, the organic phase is collected, and the extracted organic phase is recrystallized.
6. The method according to claim 5, wherein the extraction solvent used in extracting the sucrose fatty acid ester crude product is ethyl acetate/brine mixture, and the volume ratio of ethyl acetate to brine in the extraction solvent is ethyl acetate/brine=4-10:1.
7. The method according to claim 5, wherein the recrystallization solvent used in the extractive recrystallization is 80% n-butanol-water solution.
8. The method for preparing sucrose fatty acid diester according to claim 7, wherein the separation method is to filter the recrystallized product to obtain an upper solid, and then dry the upper solid to obtain sucrose fatty acid diester.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310655596.8A CN116751236A (en) | 2023-06-02 | 2023-06-02 | Preparation method of sucrose fatty acid diester |
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| CN202310655596.8A CN116751236A (en) | 2023-06-02 | 2023-06-02 | Preparation method of sucrose fatty acid diester |
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| CN202310655596.8A Pending CN116751236A (en) | 2023-06-02 | 2023-06-02 | Preparation method of sucrose fatty acid diester |
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| Country | Link |
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- 2023-06-02 CN CN202310655596.8A patent/CN116751236A/en active Pending
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