CN112940054B - Preparation method of sucrose ester with high monoester content - Google Patents
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Abstract
The invention belongs to the field of food, and particularly relates to a preparation method of sucrose ester with high monoester content. Adding dried cane sugar, fatty acid, cheap alkali metal carbonate catalyst and surfactant into the organic solvent after water removal, heating and stirring under a reduced pressure condition to perform esterification reaction for a certain time to generate a crude product of sucrose ester; then extracting and recrystallizing for purification to obtain the final product with high monoester content and obtain the sucrose ester byproduct with low monoester content. The invention is suitable for large-scale preparation, the content of monoester in the obtained final product can reach 95 percent at most, and the high-end requirement on sucrose ester on the market is met; the recycling of byproducts and organic solvents is highlighted, three wastes are not generated in the whole process, the cost of raw materials for production is greatly reduced, the pollution caused by solvent emission is avoided, the requirements of green chemistry are met, and the ecological environment protection is facilitated.
Description
Technical Field
The invention belongs to the field of food, and particularly relates to a preparation method of sucrose ester with high monoester content, which is suitable for large-scale green production.
Background
Sucrose fatty acid esters, commonly referred to as sucrose esters (SE for short), are amphiphilic molecules that can be divided into a hydrophilic sucrose moiety and a lipophilic (hydrophobic) fatty acid chain moiety, which are surfactants. Since the hydrophilic-lipophilic property of sucrose esters can be adjusted by the length of their fatty acid chains and the degree of esterification, they have a rather broad hydrophilic-lipophilic balance (HLB) value. The sucrose ester has the advantages of environmental protection, no toxicity, no irritation, biodegradability and the like, so the sucrose ester is widely applied to the industries of food, medicine, cosmetics, detergents, adhesives, agriculture and the like. Since sucrose molecules contain up to 8 hydroxyl groups, there can be varying degrees of esterification, resulting in mono-substituted monoesters, di-substituted diesters, or even polyesters; in addition, the lipophilic fatty acid moiety bound to sucrose may have various chain lengths, and commonly include short chain fatty acids such as acetic acid and butyric acid, or medium chain fatty acids such as caprylic acid and capric acid, and long chain fatty acids such as myristic acid, palmitic acid, stearic acid, and oleic acid. Among these sucrose esters, the long-chain fatty acid monoester has better water solubility, the most extensive application and the most market prospect. Sucrose ester products with extremely high monoester content are required in the fields of medicine, cosmetics, luxury foods, etc. to ensure safety of application and quality stability of the products.
The chemical preparation method of sucrose ester mainly comprises an ester exchange method, an acid anhydride method, an acyl chloride method and the like. The acid anhydride method firstly needs to prepare the acid anhydride corresponding to the fatty acid, and due to the limitation of cost and preparation difficulty, only short-chain fatty acid, especially acetic acid anhydride is usually used for preparing sucrose ester, and the acid anhydride is excessively active and highly corrosive, so the application of the acid anhydride method is greatly limited and is usually only used in a laboratory. The acyl chloride method requires that the carboxyl of the fatty acid is converted into a corresponding acyl chloride group, and then the high reactivity of the acyl chloride is utilized to react with sucrose, so that sucrose ester is generated. Although the method can ensure the reaction, the steps are complicated, and the reaction degree is not easy to control due to the active reaction of acyl chloride. Therefore, the mainstream industrial preparation of sucrose ester is an ester exchange method at present, sucrose ester is generated by carrying out ester exchange reaction on sucrose and fatty acid low-carbon alcohol (usually methanol) ester, and the method has the advantages of simple steps, easy regulation and control of reaction and the like, but the method needs to prepare fatty acid alcohol ester independently as a reaction raw material, so that the preparation cost is increased.
Chinese patent publication No. CN1389450A discloses a method for producing sucrose fatty acid ester by one-step method and its application, in which sucrose, vegetable oil and alkali metal catalyst are put into a reaction kettle together, stirred for solid-liquid reaction, and then discharged and packaged. The obtained product can be used as a defoaming agent to be applied to sugar boiling process, papermaking and wastewater purification engineering. The method avoids using polar solvent, has simple production process and low cost, but because the vegetable oil is used as the source of the fatty acid, the final product necessarily has glyceride by-products besides sucrose ester, thereby not only reducing the purity of the sucrose ester, but also deteriorating the originally possessed emulsifying property of the sucrose ester, and further greatly limiting the application range of the sucrose ester, especially the application in the food field (for example, the sucrose ester can not be used as a foaming agent and a foaming agent for foods such as cakes and the like).
Chinese patent publication No. CN111094312A discloses a preparation method of sucrose ester. In the patent, hydrogenated palm oil and sucrose are subjected to ester exchange reaction under the action of a catalyst (preferably potassium carbonate) by a solvent-free method to obtain a sucrose ester crude product. When the emulsifier (preferably Mitsubishi S-570 sucrose ester) is still present in the reaction system, the yield of the obtained sucrose ester can reach 40.49 percent. However, the use of hydrogenated palm oil (essentially triglycerides) necessarily results in the final product containing glyceride by-products, thus limiting the purity and monoester content of sucrose esters, and still severely limiting its range of application.
Chinese patent application No. CN102850413A discloses a method for preparing sucrose fatty acid ester, which uses fatty acid ester and sucrose as raw materials, and the catalyst used is a three-phase transfer catalyst obtained by bonding emulsifier, quaternary ammonium salt or quaternary phosphonium salt, polyethylene glycol, and crown ether on macromolecular high polymer, and generates sucrose ester by catalysis and transesterification. The yield of the method is as high as 85%, and the catalyst can be reused, however, the preparation of the three-phase transfer catalyst is too complex, so that the production cost is high, and the feasibility of implementing industrial production is lacked. This patent application was eventually rejected.
Chinese patent publication No. CN103396460B discloses a preparation method of sucrose ester. The method uses the common alkaline earth metal oxide (namely calcium oxide) in industry as a solid catalyst to catalyze the ester exchange reaction of fatty acid methyl ester and sucrose to generate sucrose ester. The solid catalyst used in the method can not remain in the product and can be reused, the purity of the sucrose ester can reach more than 98 percent, but the content of the monoester in the product is not clear, and evidence suitable for large-scale stable production is lacked.
Chinese patent publication No. CN103087118B discloses a purification method of sucrose ester. Dissolving a sucrose ester crude product in an organic solvent (ethyl acetate, butanone or n-butyl ketone) immiscible with water to obtain a sucrose ester crude product solution, and then dropwise adding a salt water solution of alkaline earth metal/alkaline earth metal oxides (such as calcium chloride, magnesium chloride, barium chloride/calcium oxide, magnesium oxide, barium oxide and the like) under stirring to generate fatty acid alkaline earth metal salts insoluble in the organic solvent from fatty acid soaps in the sucrose ester crude product solution and remove the fatty acid alkaline earth metal salts; adding saline water (sodium chloride, potassium chloride, sodium sulfate or potassium sulfate aqueous solution), stirring for extraction, standing for separating the lower water layer, stirring the supernatant, cooling to 0-40 deg.C to crystallize sucrose ester, collecting the crystal, and drying to obtain sucrose ester product. The method utilizes a cooling crystallization process to remove unreacted raw materials such as fatty acid methyl ester and the like, further improves the total ester content to 98 percent, but according to the provided implementation example, the content of monoester in the product is only 19.6 to 71.4 percent, and is yet to be improved.
Chinese patent publication No. CN104004033B discloses a method for purification and separation of sucrose ester, which comprises dispersing and dissolving a sucrose fatty acid ester crude product in an organic solvent a (which may be ethyl acetate, butanone or n-butanol, or a combination thereof), filtering and recovering sucrose to obtain a sucrose ester crude product solution, adding an alkaline earth metal salt (magnesium sulfate, calcium chloride, barium chloride, or a combination thereof) into the solution at 25-80 ℃ under stirring to perform a double decomposition reaction, and then performing solid-liquid separation at 5-80 ℃ to obtain a filtrate a and a solid B; washing the filtrate A with water, distilling to recover the solvent, and drying to obtain a sucrose ester product A; adding an organic solvent B into the solid B, extracting at 50-80 ℃, washing the obtained extract, distilling to recover the solvent, and drying to obtain a sucrose ester product B. The method has the advantages of high product content and recovery rate, and separation of sucrose monoester and diester is completed to obtain products with different sucrose monoester contents, and the monoester content of sucrose fatty acid ester is only 75.2% at most according to the embodiment provided by the patent. This indicates that the content of monoester in the product cannot be increased substantially by improving the purification process alone without combining a better preparation process.
Chinese patent application No. CN110891962a discloses sucrose fatty acid ester, and a preparation method, a quantitative analysis method and use thereof. Adding sucrose, fatty acid methyl ester, a catalyst (preferably potassium carbonate) and a surfactant (preferably potassium stearate or Japan Trapa S-570 sucrose ester) into a solvent (preferably N, N-dimethylformamide, namely DMF) to perform ester exchange reaction to obtain a crude product; the obtained crude product is purified and separated through extraction and recrystallization to obtain a sucrose fatty acid ester product, and the monoester content of the product can reach 84-91 percent at most. However, the method uses a starting material of fatty acid methyl ester which is prepared in advance, and therefore, the cost of the starting material is higher than that of the method using fatty acid or fatty acid glyceride (i.e., animal and vegetable oil). Meanwhile, the method does not consider the requirement of industrial mass production, particularly does not consider the recovery and subsequent treatment of organic solvent used for reaction and purification, thereby not only causing toxic solvent to be leaked into the environment, but also causing a great deal of waste of the solvent and reducing the preparation economy. The method does not involve the recovery and further utilization of various byproducts, so that the method is only suitable for small-scale preparation in a laboratory and cannot be applied to pilot plant test and large-scale industrial production.
In summary, the development of a new method for preparing and purifying sucrose fatty acid ester in the field is awaited, so that sucrose ester with higher monoester content can be obtained at lower production cost, the requirements of fields such as high-grade food, cosmetics, medicine and agriculture can be met, and pilot scale and industrial large-scale production can be realized in a green and economic manner.
Disclosure of Invention
In order to solve the defects and shortcomings of the prior art, the invention provides a preparation method of sucrose ester with high monoester content, which is suitable for large-scale green production. The content of the monoester in the sucrose fatty acid ester prepared by the method (the highest content is 95%) is higher than that of the existing method, and the method is green, environment-friendly and economical, and is suitable for pilot plant test and industrial large-scale production.
The purpose of the invention is realized by the following technical scheme:
a preparation method of sucrose ester with high monoester content comprises the following steps:
(1) Adding dried sucrose, fatty acid, catalyst and surfactant into the organic solvent after water removal, heating and stirring under reduced pressure to perform esterification reaction for a certain time, and continuously evaporating and removing water generated by the reaction due to higher reaction temperature and reduced pressure; concentrating the obtained reaction product to obtain a sucrose ester crude product; recovering the organic solvent obtained by concentration, and returning the organic solvent to the esterification reaction of the next batch for reuse;
(2) Extracting the obtained sucrose ester crude product by an organic solvent/water, and separating an aqueous phase and an organic phase; concentrating and drying the water phase to obtain unreacted cane sugar, and returning to the step (1) for recycling; concentrating and drying the organic phase, purifying the obtained solid in the next step, and recovering the obtained organic solvent for reuse in the extraction operation of the next batch;
(3) Collecting the solid precipitated in the organic phase obtained in the step (2), dissolving the solid in an organic solvent, recrystallizing, and carrying out solid-liquid separation; collecting the solid and fully drying to obtain a sucrose ester final product (with high monoester content), and returning the organic solvent obtained in the drying process to the step (2) for recycling; and concentrating and drying the liquid to obtain a sucrose ester byproduct (low monoester content), and condensing the organic solvent obtained by concentrating and drying and recycling the organic solvent for recrystallization.
Preferably, the lower alcohol ester of fatty acid in step (1) comprises medium or long chain fatty acids (C8-22, including saturated and/or unsaturated fatty acids), typically produced by hydrolysis of animal and vegetable oils, in an amount of 40-70% of the mass of sucrose added; further preferably, the fatty acid is stearic acid, and the addition amount is preferably 55% of the addition mass of the sucrose.
The catalyst in the step (1) is carbonate of alkali metal, and the addition amount of the catalyst is 1-7% of the addition amount of the sucrose; preferably, the catalyst is potassium carbonate, and the addition amount of the catalyst is 5% of the addition mass of the sucrose.
The surfactant in the step (1) comprises ionic or nonionic surfactant, and the addition amount of the surfactant is 0.5-3% of the addition amount of the sucrose; the surfactant is preferably potassium stearate, and the addition amount of the surfactant is 1% of the added mass of the sucrose.
The organic solvent in step (1) is an anhydrous polar organic solvent capable of dissolving or partially dissolving the reaction substrates (sucrose and fatty acid) simultaneously, such as N, N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), etc., and a mixture of these solvents, and the water in these solvents has been removed by various methods (e.g., absorption using a molecular sieve, reaction with calcium hydride, etc.) before being put into reaction; the ratio of the adding volume of the organic solvent to the adding mass of the sucrose is 1:1-5:1; further preferably, the solvent is anhydrous DMF and the ratio of the added volume to the mass of sucrose addition is 2:1 (kg/L).
The reduced pressure condition in the step (1) is 5 to 20kPa, preferably 10kPa.
The reaction temperature of the esterification reaction in the step (1) is 70 to 130 ℃, preferably 105 ℃.
The reaction time of the esterification reaction in the step (1) is 1-5h, preferably 2.5h.
In the extraction in the step (2), the used organic solvent is a low-boiling-point organic solvent which can be fully dissolved and allows the sucrose ester to be separated out, and the volume ratio of the organic solvent to water is 1:1-3:1; butanone is preferred, and the volume ratio of butanone to water is 1.5.
The organic solvent for recrystallization in step (3) is a low-boiling point organic solvent, preferably edible alcohol, which is sufficiently soluble and allows the sucrose ester to be precipitated.
The separation method in step (3) may be any method or combination thereof capable of achieving sufficient solid-liquid separation, such as filtration, centrifugation, decantation, etc.
The concentration or concentration drying in the steps (1) to (3) may be a method of sufficiently removing the solvent contained in the solution, such as reduced pressure distillation or vacuum drying, and the generated solvent vapor is condensed and then recovered, thereby realizing the recycling of the solvent.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) The invention uses cheap and easily-obtained alkali carbonate (such as potassium carbonate is the main component of plant ash) to catalyze sucrose to react with fatty acid by a chemical esterification method to obtain a sucrose ester crude product with higher monoester content, thereby avoiding the use of expensive and volatile enzyme catalysts reported in Chinese and foreign literatures and greatly reducing the reaction cost.
(2) The invention obtains the sucrose ester final product with high monoester content (the highest sucrose monoester content can reach 95 percent) by simple and easy extraction and recrystallization of the sucrose ester crude product, has higher water solubility, low impurity, low ash content and low solvent residue, and can meet the high-end requirement of sucrose ester on the market; meanwhile, a sucrose ester byproduct with low monoester content is obtained, has better oil solubility and can be used in middle and low-end occasions, thereby having higher economic benefit.
(3) The invention particularly highlights the recovery and utilization of byproducts and organic solvents in the production process, and the whole process has no three wastes, thereby not only greatly reducing the cost of production raw materials, but also avoiding the pollution caused by solvent discharge, meeting the requirements of green chemistry and being beneficial to ecological environment protection.
Drawings
FIG. 1 is a process flow diagram of the present invention.
FIG. 2 is an evaporative light liquid chromatography (ELSD-HPLC) chart of a sucrose ester final product (high monoester content) obtained in example 1.
FIG. 3 is a NMR chart of a final sucrose ester (high monoester content) obtained in example 1.
FIG. 4 is an evaporative light liquid chromatography (ELSD-HPLC) chart of a sucrose ester by-product (low monoester content) obtained in example 1.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the embodiments of the present invention are not limited thereto. The raw materials related to the invention can be directly purchased from the market. For process parameters not specifically noted, reference may be made to conventional techniques.
Example 1
(1) 100kg of sucrose, 53kg of stearic acid, 5kg of potassium carbonate and 1kg of potassium stearate, which have been sufficiently dried, are charged into a reaction vessel already filled with 200L of anhydrous DMF, and are heated to 105 ℃ with stirring under reduced pressure to 10kPa, so that esterification reaction occurs. Maintaining the reaction for 2.5h, cooling the obtained reaction product after the reaction is finished, and concentrating by reduced pressure distillation to obtain a crude product of sucrose ester.
(2) The crude sucrose ester obtained was extracted with butanone/water in a volume ratio of 1.5, and the aqueous and organic phases were separated. Concentrating and drying the water phase to obtain unreacted sucrose; after the organic phase is concentrated and dried, the obtained solid is subjected to the next purification.
(3) And (3) collecting the solid precipitated in the organic phase obtained in the step (2), dissolving the solid in edible alcohol for recrystallization, and filtering and separating the obtained solid and the solution. Collecting the solid and drying under reduced pressure to obtain a sucrose ester final product; and concentrating and drying the solution part by reduced pressure distillation to obtain a sucrose ester by-product (low monoester content). Both products were checked for their monoester content by evaporative light liquid chromatography (ELSD-HPLC), the former having a sucrose monoester content of up to 95% and the latter having a monoester content of 30%.
Example 2
This example is identical to the procedure used in example 1, but with the emphasis on verifying the feasibility of recovering the by-products and the solvent, the specific differences are as follows:
(1) Esterification the starting sucrose for the preparation of crude sucrose ester was obtained from multiple runs of unreacted sucrose produced in step (2) of example 1. The organic solvent used for the reaction was DMF recovered from step (1) of example 1.
(2) The butanone used was extracted, resulting from the recovery of the butanone obtained after the step (2) in example 1.
(3) The ethanol used for recrystallization was obtained from the edible alcohol recovered after the step (3) in example 1 was carried out.
The sucrose ester end product and the sucrose ester by-product obtained were checked for their monoester contents by evaporative light liquid chromatography (ELSD-HPLC), the former having a sucrose monoester content of 94% and the latter having a monoester content of 31%, comparable to example 1, verifying that the by-product and solvent recovery in this application is completely feasible.
Example 3
(1) 100kg of sucrose, 40kg of octanoic acid, 1kg of potassium carbonate and 3kg of potassium stearate, which have been sufficiently dried, are charged into a reaction vessel containing 100L of anhydrous DMF, and stirred and heated to 70 ℃ under reduced pressure to 20kPa, so that esterification reaction occurs. Maintaining the reaction for 1h, cooling the obtained reaction product after the reaction is finished, and concentrating by reduced pressure distillation to obtain a sucrose ester crude product.
(2) The crude sucrose ester obtained was extracted with butanone/water in a volume ratio of 1:1 and the aqueous and organic phases were separated. Concentrating and drying the water phase to obtain unreacted sucrose; after the organic phase was concentrated and dried, the obtained solid was subjected to the next purification.
(3) And (3) collecting the solid precipitated in the organic phase obtained in the step (2), dissolving the solid in edible alcohol for recrystallization, and filtering and separating the obtained solid and the solution. Collecting the solid and drying under reduced pressure to obtain a sucrose ester final product; and concentrating and drying the solution part by reduced pressure distillation to obtain a sucrose ester by-product (low monoester content). Both products were checked for their monoester content by evaporative light liquid chromatography (ELSD-HPLC), the former having a sucrose monoester content of 70% and the latter having a monoester content of 20%.
Example 4
(1) 100kg of fully dried sucrose, 70kg of behenic acid, 7kg of potassium carbonate and 0.5kg of potassium stearate are added into a reaction kettle filled with 500L of anhydrous DMF, and the mixture is stirred and heated to 130 ℃ under the condition of reducing the pressure to 5kPa, so that esterification reaction is carried out. Maintaining the reaction for 5 hours, cooling the obtained reaction product after the reaction is finished, and concentrating the reaction product through reduced pressure distillation to obtain a sucrose ester crude product.
(2) The crude sucrose ester obtained is extracted with butanone/water in a volume ratio of 3:1 and the aqueous and organic phases are separated. Concentrating and drying the water phase to obtain unreacted sucrose; after the organic phase is concentrated and dried, the obtained solid is subjected to the next purification.
(3) And (3) collecting the solid precipitated in the organic phase obtained in the step (2), dissolving the solid in edible alcohol for recrystallization, and centrifuging the obtained solid and solution. Collecting the solid and drying under reduced pressure to obtain a sucrose ester final product; and concentrating and drying the solution part by reduced pressure distillation to obtain a sucrose ester by-product (low monoester content). Both products were checked for their monoester content by evaporative light liquid chromatography (ELSD-HPLC), the former having a sucrose monoester content of 80% and the latter having a monoester content of 25%.
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 (8)
1. A preparation method of sucrose ester with high monoester content is characterized by comprising the following steps:
(1) Adding dried sucrose, fatty acid, catalyst and surfactant into the organic solvent after dewatering, heating and stirring under reduced pressure for esterification reaction for a certain time, and concentrating the obtained reaction product to obtain a sucrose ester crude product; recovering the organic solvent obtained by concentration, and returning the organic solvent to the esterification reaction of the next batch for reuse; the catalyst is carbonate of alkali metal;
(2) Extracting the obtained sucrose ester crude product by an organic solvent/water extraction, and separating a water phase and an organic phase; concentrating and drying the water phase to obtain unreacted sucrose, and returning to the step (1) for recycling; concentrating and drying the organic phase, purifying the obtained solid in the next step, and recovering the obtained organic solvent and returning the recovered organic solvent to the extraction operation of the next batch for reuse;
(3) Collecting the solid precipitated in the organic phase obtained in the step (2), dissolving the solid in an organic solvent, recrystallizing, and carrying out solid-liquid separation; collecting the solid and fully drying to obtain a sucrose ester final product, and returning the organic solvent obtained in the drying process to the step (2) for recycling; the liquid is concentrated and dried to obtain a sucrose ester byproduct, and the organic solvent obtained by concentration and drying is condensed and then recycled for recrystallization;
in the step (1), the fatty acid is medium-chain or long-chain fatty acid, the addition amount is 40-70% of the mass of the added sucrose, the organic solvent is anhydrous N, N-dimethylformamide, the decompression condition in the step (1) is 5-20kPa, and the reaction temperature of the esterification reaction is 70-130 ℃;
the catalyst in the step (1) is potassium carbonate, the addition amount of the potassium carbonate is 1-7% of the addition mass of the sucrose, the surfactant is an ionic or non-ionic surfactant, and the addition amount of the surfactant is 0.5-3% of the addition mass of the sucrose.
2. The method for preparing sucrose ester with high monoester content in claim 1, wherein the addition amount of the fatty acid in the step (1) is 55% of the addition amount of the sucrose.
3. The method for preparing sucrose ester with high monoester content in claim 1, wherein the ratio of the addition volume of the organic solvent to the addition mass of sucrose in step (1) is 1:1-5:1.
4. The process for producing a sucrose ester with a high monoester content of claim 1, wherein the reduced pressure in step (1) is 10kPa;
the reaction temperature of the esterification reaction in the step (1) is 105 ℃;
the reaction time of the esterification reaction in the step (1) is 1-5h.
5. The method for preparing sucrose ester with high monoester content in claim 1, wherein the organic solvent used in the extraction in step (2) is a low boiling point organic solvent which can fully dissolve and allow sucrose ester to be separated out, and the volume ratio of the organic solvent to water is 1:1-3:1.
6. The method for preparing sucrose ester with high monoester content of claim 1, wherein the organic solvent for recrystallization in step (3) is a low boiling point organic solvent that is sufficiently soluble to allow the sucrose ester to precipitate.
7. The method for preparing sucrose ester with high monoester content as claimed in claim 1, wherein the separation method in step (3) is one or a combination of filtration, centrifugation or decantation.
8. The method for preparing sucrose ester with high monoester content in claim 1, wherein the concentration or concentration drying in steps (1) - (3) is distillation under reduced pressure or vacuum drying.
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| CN112940054A (en) | 2021-06-11 |
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