CN1323086C - Method for synthesizing fatty ester of maltose - Google Patents
Method for synthesizing fatty ester of maltose Download PDFInfo
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- CN1323086C CN1323086C CNB2005100132590A CN200510013259A CN1323086C CN 1323086 C CN1323086 C CN 1323086C CN B2005100132590 A CNB2005100132590 A CN B2005100132590A CN 200510013259 A CN200510013259 A CN 200510013259A CN 1323086 C CN1323086 C CN 1323086C
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Abstract
The present invention provides a method for synthesizing the fatty acid ester of maltose. 60 to 100% of malt syrup with the weight unit of 300 to 500 is mixed with alcohol with the volume unit of 100 to 300 or methanol. Soap salt with the weight unit of 200 to 500 and fatty acid ester with the substance amount of one to three times mole number than maltose are added. By oil bath heating, dissolution and decompression of 60 to 80 DEG C /0.1 to 10kPa, a small number of solvents and moisture contents are removed. Alkaline substances with the weight unit of 2 to 10 are added, and reflux is continued for 1 to 3 hours. By vacuum distillation and cooling, a sodium salt solution is added. Solid and liquid are delaminated and separated by adjusting the pH value of 3 to 5 by acid. A separated substance is soaked and washed by a butanone-sodium salt aqueous solution. By the recovery of butanone, wash by purified water and pressure reduction drying, a maltose fatty acid ester solid is obtained. The product of the present invention has the advantage of sucrose ester and has certain oxidation resistance. In addition, an isomer is simple in the product and is convenient for purification and separation. Simultaneously, maltose is a hydrolysate product stemmed from the starches of various farm crops. Raw materials of the maltose can be stored for a long time, and resources are abundant and can be continuously used.
Description
[technical field]: the synthetic method that the invention belongs to the emulsifying agent of the oligomeric sugar esters of lipid acid or the preparing technical field of dispersion agent, particularly fatty ester of maltose.
[background technology]: fatty ester of maltose belongs to lipid acid oligose Ester (comprising sucrose ester, glucose ester, lactose ester etc.), sucrose fatty acid ester class material is that a kind of HLB (hydrophilic-lipophilic balance) codomain is wide, effective, safe, the emulsifying agent of applied range, adds use as auxiliary usually in the process for processing of Chemicals, cosmetics of everyday use, food and medicine.Owing to add structural form, stability, visual appearance and effect that emulsifying agent can improve many products, therefore be the hot-sale products in the similar auxiliary always.Only have both at home and abroad at present that sucrose fatty ester is a kind of is singing only angle, for fatty ester of maltose academic report is only arranged abroad, so far product-free listing still as the emulsifying agent of the oligomeric sugar esters of lipid acid.In recent years, the U.S., Canadian scientist be research by experiment again, finds that fatty ester of maltose also has the effect that suppresses tumour cell, and aspect treatment cancer, the enhance immunity power unique effect (CA1120399 is being arranged; US6525044; US5550225).In view of this, no matter fatty ester of maltose as the emulsifying agent of food, medicine, daily use chemicals product or as pharmaceutical preparation, all has very big practical potential, it synthesizes with use also will cause bigger concern.
The production of sucrose fatty acid ester at present mainly is to synthesize representative (other sugar esters also product-free and producer can follow) with sucrose fatty ester, its synthesis mechanism utilizes alcohol fatty acid ester and cane sugar powder to carry out transesterification reaction under certain condition substantially and finishes, and this type of production method mainly contains solvent method (as using dimethyl formamide, pyridine, dimethyl sulfoxide (DMSO) equal solvent); Scorification (solventless method); (US3141012 such as micro emulsion method; BL696700; CN94119201.6; US2997492; US3138463; US3558579; US3644333).These methods are when being applied to fatty ester of maltose synthetic, and not only the aftertreatments such as separation and purification to finished product bring difficulty, and influence the quality and the range of application of the finished product.Higher and have certain toxicity as the solvent dimethyl formamide, pyridine, the dimethyl sulfoxide (DMSO) boiling point that use in the solvent method, its residual meeting in product directly influences the quality of finished product and in the use (present many countries have given strict restriction) of food, prescription face; The high temperature that scorification adopt to surpass 160 degree Celsius carry out processing treatment, make that raw material is as easy as rolling off a log in the course of processing charing to occur, and this not only influences the purity and the color and luster of product, and can make productive rate occur descending; Though the micro emulsion method, comprises measures such as avoiding using noxious solvent and high-temperature fusion processing for the consideration to the problems referred to above, a large amount of soap salt that use are not processed, feasible isolation and purification to the finished product has increased difficulty; Do not utilize in addition only remove with some organic solvent, so not only can increase tooling cost, and can bring dissolvent residual and pollution problem equally, in addition because the finished product of maltose mostly is the underflow (making the solid cost can be higher) that contains certain moisture and high condensed state greatly, when utilizing aforesaid method to produce, also be difficult to obtain ideal and prepare effect.
[summary of the invention]: the objective of the invention is to solve the vacancy of Fructus Hordei Germinatus sugar ester product and the deficiency of existing related preparation technology, a kind of synthetic method of fatty ester of maltose is provided.
The synthetic method of fatty ester of maltose provided by the invention comprises:
1), prepare fatty ester of maltose by transesterification reaction: take by weighing 300～500 weight unit, 60%～100% malt syrup (synthesis material is moisture or moisture free maltose) and 100～300 volume unit ethanol or methanol mixed, add 200～500 weight unit soap salt, and amount is the fatty acid ester of 1～3 times of mole number of maltose, (60～80 ℃/0.1～10kPa) removes a small amount of solvent and moisture, adds the alkaline matter (sodium hydroxide of 2～10 weight unit through the also decompression of oil bath heating for dissolving, potassium hydroxide, sodium alkoxide, potassium alcoholate, yellow soda ash, salt of wormwood, calcium oxide, magnesium oxide, a kind of or several mixtures in the materials such as soap salt); Continue the 1～3hr that refluxes; Wherein wt/volume unit is g/mL;
2), 80～110 ℃/0.1～10kPa of underpressure distillation, the reaction 1～3hr;
3), be cooled to 70 ℃, the sodium salt solution (can be sodium-chlor or metabisulfite solution) that to add 2～4 times of volumes, concentration be 100～150g/L, and to transfer pH with acid (can be acetate, hydrochloric acid, sulfuric acid, phosphoric acid, citric acid) be 3～5, makes the solid-liquid layering;
4), obtain the transesterify solid product after filtration;
5), embathe isolate, and collect the butanone phase with the butanone-sodium-salt aqueous solution (sodium-salt aqueous solution can be sodium-chlor or metabisulfite solution) that is lower than 10 ℃;
6), suction filtration is removed butanone, the water purification washing; And recovery butanone and lipid acid;
7), through drying under reduced pressure 40～60 ℃/0.1～10kPa, obtain the fatty ester of maltose solid.
By product lipid acid during the present invention specially will react reclaims 6), not only can be used for producing fatty acid ester, and can make soap salt to drop into building-up process once more, also can reduce terminal quantity discharged simultaneously.
Wherein soap salt preparation: promptly use the lipid acid and 50～150 weight unit alkaline matters of 200～300 weight unit, mix and add 50～100 volume unit ethanol or methyl alcohol after, backflow soapmaking salt in water-bath.
Fatty acid ester preparation: the lipid acid that promptly uses 250～300 weight unit, with 2000 volume unit second absolute alcohol or methyl alcohol, add 2～8 weight unit an acidic catalysts, behind backflow 4～6h, reclaim ethanol or methyl alcohol, leave standstill more than the 4h being lower than under 10 ℃, wash with water, obtain synthetic mesophase product fatty acid ester through after being lower than 60 ℃ of following drying under reduced pressure to neutrality.
1) fatty acid ester in the step can be Stearic ethyl stearate or methyl stearate, or soft-ethyl ester or soft-methyl ester, or plam oil hydrolysis acetoacetic ester or methyl esters or butter hydrolysis acetoacetic ester or methyl esters or other carbon numbers are 12～24 fatty-acid ethyl ester or methyl esters.
The synthetic of fatty ester of maltose of the present invention (hereinafter to be referred as the Fructus Hordei Germinatus sugar ester) is (hereinafter to be referred as fatty acid ester from the lipid acid low-carbon-ester; Lower alcohol nail alcohol or ethanol) preparation begin, lipid acid can adopt oil prodution industry product stearic acid or Palmiticacid, but if select to be lower than the lipid acid of 12 carbon, its corresponding sugar ester emulsifier effect bad (the HLB codomain is narrow), preferably 16 carbon fatty acids (Palmiticacid) or 18 carbon fatty acids (stearic acid).And select the suitable building-up reactions of carrying out of corresponding saturated fatty acid.Because the building-up process at the Fructus Hordei Germinatus sugar ester has a certain amount of fatty acid by-products to need to recycle, so the preparation of lipid acid low-carbon-ester (as Stearic ethyl stearate) is incorporated in the synthetic content of Fructus Hordei Germinatus sugar ester.Under sulfuric acid catalysis, carry out esterification by stearic acid (or Palmiticacid) with ethanol (or methyl alcohol), after reaction finishes through reclaiming ethanol (or methyl alcohol), cooling, treatment steps such as separation, washing can obtain corresponding stearic acid (or Palmiticacid) ethyl ester (or methyl esters) intermediate material.The preparation feedback of stearic acid (or Palmiticacid) ethyl ester (or methyl esters) is:
Fructus Hordei Germinatus sugar ester synthetic is to use maltose (M-OH) to carry out transesterify with fatty acid ester (R-COOR ') under alkaline condition, finally generates corresponding fatty ester of maltose.Reaction formula as:
Building-up process refluxes with alkaline matter and adequate amount of ethanol (or methyl alcohol), lipid acid earlier, makes it be converted into corresponding sodium alkoxide (or potassium, calcium, magnesium) and soap salt (or soap); Malt syrup then uses small amount of ethanol (or methyl alcohol) and an amount of fatty acid ester to dilute mixing, the 1～3h that refluxes after all components are mixed, and reducing pressure subsequently steams residual solvent.Reactant carries out acidifying (pH=3～5) processing after being cooled to normal temperature, make the layering of reaction product solid-liquid, and unnecessary waste water is done in the vacuum filter, again by butanone and water washing separate solid, can obtain the pure product of fatty ester of maltose through drying under reduced pressure.Lipid acid behind the recovery butanone can repeat to make fatty acid ester and soap salt.Whole process of preparation can promptly be the preparation flow figure of example with stearic acid, ethanol, sulfuric acid system with reference to Fig. 1.Preparation process comprises the preparation of feedstock fat acetoacetic ester (or methyl esters); Synthesizing of Fructus Hordei Germinatus sugar ester; Separating agent, acid, alcohol, brinish recycle.
Use alkaline matter to make catalyzer in the transesterification reaction of Fructus Hordei Germinatus sugar ester and can select materials such as sodium hydroxide or potassium hydroxide, sodium alkoxide, potassium alcoholate, yellow soda ash, salt of wormwood, calcium oxide, magnesium oxide, soap salt, the reaction system of finding to contain sodium alkoxide or potassium alcoholate in the experiment is the productive rate height not only, and excellent catalytic effect.
Separating agent can have certain dissolving to product when selecting butanone or butanols, amylalcohol and organosilane ester solvent, therefore when containing a spot of lipid acid in or the permission product less demanding to product purity, can not use or on a small quantity with an organic solvent.
The salt solution product separation helps improving the quality of products and productive rate, can select salt or calcium chloride solution, and the latter helps water treatment.Make its solution loss few with hypothermic saline (less than 10 ℃) washing Fructus Hordei Germinatus sugar ester, be beneficial to the Fructus Hordei Germinatus sugar ester enter butanone mutually in, can remove residual sugar and burnt color substance simultaneously.Also can adopt neutral water to handle during product separation, the water after using thus then contains a certain amount of soap.
Ethanol (or methyl alcohol) should use dehydrated alcohol (or anhydrous methanol), otherwise can influence esterification yield when being used to prepare fatty-acid ethyl ester (or methyl esters); And aqueous ethanol (or methyl alcohol) can be used for diluting malt syrup and handles basic catalyst, but can not be excessive otherwise cause breakdown of emulsion and influence transesterify.When reclaiming ethanol, can require to handle respectively, to reduce energy expenditure according to difference.
The certain vacuum tightness of control not only is beneficial to the volatilization of moisture and alcohol in the transesterify process, and can reduce contacting of reactant and air, reduce the degree of reactant oxidation, coking, brown stain, be the effective ways that improve Fructus Hordei Germinatus sugar ester quality product and productive rate, so the transesterify process is to be advisable below the 5kpa in vacuum tightness.
The speed of reaction temperatures affect reaction, improve temperature and can accelerate the speed of transesterify, can increase the content of maltose diester simultaneously, but also cause the coking and the brown stain of reactant easily, therefore distill that excessive solvent is appropriate to the occasion should to keep proper amount of solvent, in 120 ℃ heating environment, also can keep the optimal temperature of reaction system like this.Cause the coking of reactant to increase the weight of to avoid temperature of reaction to occur too high.
Reaction times influences the transformation efficiency of transesterification reaction and the productive rate of Fructus Hordei Germinatus sugar ester, finds in the experiment, and after carrying out same reaction and carrying out the transesterification reaction of 1h, its transformation efficiency is less than 40% also, therefore essentially guarantees that whole backflow-distillatory time is more than 3h.
Advantage of the present invention and positively effect: the fatty ester of maltose that the present invention produces is the emulsifying agent that does not occur as yet on the market, and it has certain oxidation resistant performance (containing the free carbonyl in the structure) in addition except that all advantages with sucrose ester; Raw material maltose only has two primary alconols in addition, and this makes that isomer is simple in the esterified prod, the purifies and separates of being more convenient for; Simultaneously maltose is the hydrolysate that comes from all kinds of starch crops, and its raw material anti-deposited, the characteristics of abundant resource and sustainable use are that other emulsifying agents can't be compared.The present invention is to use moisture syrup and lipid acid is basic raw material, has so not only solved the difficulty of the synthetic sugar ester of Aquo System, and sustainable utilization by product lipid acid wherein, make that tooling cost and discharge index all obtain descending; In conjunction with refluxing and the distillation link is finished transesterification reaction, can avoid high-temperature operation at synthetic reaction process, cut down the consumption of energy and improved the efficient of building-up reactions; The invention still further relates in addition employed auxiliary material, solvent in the maltose ester production process are carried out circular treatment and use, this also feasible operation of founding the factory is convenient feasible.That other synthetic methods of whole process of preparation comparison have is simple to operate, raw materials cost is low, non-pollution discharge, the therefore Fructus Hordei Germinatus sugar ester product purity height that obtains, and edible safety is good, and multiclass products such as suitable food, medicine use.
[description of drawings]:
Fig. 1 is to be the reference process flow diagram of the preparation maltose stearate of example with stearic acid, ethanol, sulfuric acid system.
[embodiment]:
Embodiment 1, preparation Stearic ethyl stearate and maltose stearate
(1) preparation Stearic ethyl stearate and soap salt
In round-bottomed flask, add 30 gram stearic acid and 200 milliliters of dehydrated alcohols, after adding 5 gram sulfuric acid, refluxing, underpressure distillation goes out ethanol (recovery) after 4～6 hours, leave standstill under 10 ℃ more than 4 hours to solidifying being lower than, wash with water again to neutrality, through being lower than 60 ℃ of following drying under reduced pressure, obtain white near-transparent waxy Stearic ethyl stearate solid;
Use 35 gram stearic acid, after 8 gram potassium hydroxide mix and add 100 milliliters of ethanol, obtain corresponding soap salt after the dissolving that in water-bath, refluxes.
(2) preparation maltose stearate
Taking by weighing 45 gram malt syrups (sugared content 75%) stirs in flask with after 20 milliliters of ethanol mix, its dilution is disperseed, and add 45 gram Stearic ethyl stearates (about 0.15mol) and 30 and restrain soap salt (or make by lipid acid and alkali substance reaction), (80 ℃/0.1～10kPa) steams and adds 5 gram salt of wormwood (or yellow soda ash, calcium oxide, magnesium oxide, sodium hydroxide, potassium hydroxide etc.), backflow 1hr behind about 10 ml solns to use slightly heating and decompression of oil bath.(80～110 ℃/0.1～10kPa) keeps reaction 2hr in underpressure distillation, add 3 times of volume sodium salt (sodium-chlor or sodium sulfate) solution (150g/L) when stopping heating and being cooled to below 70 ℃, and to transfer pH with dilute acid soln (acetate, hydrochloric acid, sulfuric acid, phosphoric acid, citric acid all can) be 4～5, make ester exchange offspring, assemble come-up, obtain the transesterify solid product after filtration and use twice of 2 times of volume water (below 10 ℃), butanone washing by soaking respectively, tell the butanone filtration and obtain the Fructus Hordei Germinatus sugar ester, the recovery butanone gets lipid acid and utilizes.At last product is carried out drying under reduced pressure (60 ℃/0.1～10kPa), and obtain white maltose stearate powdery solid.
Embodiment 2, preparation soft-ethyl ester and maltose palmitate
(1) preparation soft-methyl ester and soap salt
In round-bottomed flask, add 256 gram Palmiticacid and 2000 ml methanol, add 50 restrain sulfuric acid after, reaction conditions obtains synthetic mesophase product soft-methyl ester with (1) in the example 1;
Use 32 gram Palmiticacid, after 8 gram potassium hydroxide mix and add 100 ml methanol, obtain corresponding soap salt after the dissolving that in water-bath, refluxes.
(2) preparation maltose palmitate
Taking by weighing 40 gram malt syrups (solid substance is 85%) mixes with 20 ml methanol and dispersed with stirring.Add 40 gram Palmiticacid soap salt and 50 gram soft-methyl ester reflux, add 5 gram salt of wormwood (or yellow soda ash, calcium oxide, magnesium oxide etc.) and continue backflow 1hr.(80～110 ℃/0.1～10kPa) keeps reaction 2hr to stop to heat and being cooled to below 70 ℃, and remaining operation is with (2) in the example 1 in underpressure distillation.Obtain the maltose palmitate solid of white at last.
The malt syrup of embodiment 3, use high-moisture prepares the maltose stearate
Take by weighing 50 gram malt syrups (solid substance is less than 70%) and mix, disperse through stirring with 20 ml methanol.(80 ℃/0.1～10kPa) adds 5 gram alkaline matters after steaming about 20 ml solns, and remaining operation is with (2) in the example 1 to add slightly heating and the decompression of 30 gram stearate soap salt and 50 gram methyl stearates.Obtain same Fructus Hordei Germinatus sugar ester solid.
Embodiment 4, use maltitol powder prepare the maltose stearate
Take by weighing 40 gram maltitol powders in flask with 20 milliliters of ethanol with stir after 5 ml waters mix, it is dissolved fully, and add 50 gram Stearic ethyl stearates and 35 gram soap salt [with embodiment 1, (1) in], (80 ℃/0.1～10kPa) adds 5 gram salt of wormwood, backflow 1hr after steaming about 8 ml solns to use slightly heating and decompression of oil bath.Remaining operation is with (2) in the example 1.Obtain same maltose stearate solid.
Embodiment 5, use butter hydrolysis acetoacetic ester prepare maltose resin acid ester
(1) preparation butter hydrolysis acid
Add the refining butter of 100 grams and 200 milliliters of ethanolic solns in flask, 20 gram potassium hydroxide (or sodium hydroxide) refluxed 3～5 hours.Steam ethanol and obtain solid butter hydrolysis acid through acidifying, filtration, washing, drying.
(2) preparation butter hydrolysis acetoacetic ester and soap salt
In flask, add 40 gram butter hydrolysis acid and 200 milliliters of dehydrated alcohols, add 6 gram sulfuric acid after, refluxed 4 hours.Remaining operation is with (1) in the example 1.Obtain butter hydrolysis acetoacetic ester solid;
After using 50 gram butter hydrolysis acid and 15 gram potassium hydroxide mixing and add 100 milliliters of ethanol, obtain corresponding soap salt after the dissolving that in water-bath, refluxes.
(3) preparation maltose butter hydrolysis acid esters
Take by weighing 50 gram malt syrups and stir in flask with after 20 milliliters of ethanol mix, its dilution is disperseed, and add 55 gram butter hydrolysis acetoacetic esters and 40 gram soap salt, remaining operation is with (2) in the example 1.Obtain maltose butter hydrolysis acid esters solid at last.
Claims (6)
1, a kind of synthetic method of fatty ester of maltose is characterized in that this method comprises:
1), prepares fatty ester of maltose: take by weighing 300～500 weight unit, 60%～100% malt syrup and 100～300 volume unit ethanol or methanol mixed by transesterification reaction, add 200～500 weight unit soap salt, and amount is the fatty acid ester of 1～3 times of mole number of maltose, through the oil bath heating for dissolving and 60～80 ℃/0.1～10kPa that reduces pressure, remove a small amount of solvent and moisture, the alkaline matter that adds 2～10 weight unit, continue the 1～3hr that refluxes, wherein wt unit/volume unit is g/mL;
2), 80～110 ℃/0.1～10kPa of underpressure distillation, the reaction 1～3hr;
3), be cooled to 70 ℃, adding 2～4 times of volumes, concentration is the sodium salt solution of 100～150g/L, and to transfer pH with acid be 3～5, makes the solid-liquid layering;
4), obtain the transesterify solid product after filtration;
5), embathe isolate with the butanone-sodium-salt aqueous solution that is lower than 10 ℃, collection butanone phase;
6), suction filtration is removed butanone, the water purification washing; And recovery butanone and lipid acid;
7), through drying under reduced pressure 40～60 ℃/0.1～10kPa, obtain the fatty ester of maltose solid.
2, the synthetic method of fatty ester of maltose according to claim 1, it is characterized in that with the lipid acid that reclaims be feedstock production soap salt: the lipid acid that promptly uses 200～300 weight unit, with 50～150 weight unit alkaline matters, after mixing and adding 50～100 volume unit ethanol or methyl alcohol, backflow soapmaking salt in water-bath.
3, the synthetic method of fatty ester of maltose according to claim 1, it is characterized in that with the lipid acid that reclaims be the feedstock production fatty acid ester: promptly use 250～300 weight unit lipid acid, with 2000 volume unit ethanol or methyl alcohol, add 2～8 weight unit an acidic catalysts, reflux behind 4～6h, reclaim ethanol or methyl alcohol, leave standstill more than the 4h being lower than under 10 ℃, wash with water to neutrality, obtain synthetic mesophase product fatty acid ester through after being lower than 60 ℃ of following drying under reduced pressure.
4, the synthetic method of fatty ester of maltose according to claim 1, it is characterized in that 1) step in fatty acid ester be Stearic ethyl stearate or methyl stearate, or soft-ethyl ester or soft-methyl ester, or plam oil hydrolysis acetoacetic ester or methyl esters or butter hydrolysis acetoacetic ester or methyl esters or other carbon numbers are 12～24 fatty-acid ethyl ester or methyl esters.
5, the synthetic method of fatty ester of maltose according to claim 1 and 2 is characterized in that 1) alkaline matter in the step is a kind of or several mixtures in sodium hydroxide, potassium hydroxide, sodium alkoxide, potassium alcoholate, yellow soda ash, salt of wormwood, calcium oxide, magnesium oxide, the soap salt material.
6, according to the synthetic method of claim 1 or 3 described fatty ester of maltose, it is characterized in that 3) step is with 5) sodium-salt aqueous solution in the step is sodium-chlor or metabisulfite solution.
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| CN103396460B (en) * | 2013-07-29 | 2016-04-27 | 柳州爱格富食品科技股份有限公司 | The preparation method of sucrose ester |
| CN111171088B (en) * | 2020-01-07 | 2021-05-04 | 广东省石油与精细化工研究院 | Catalytic selective synthesis method of fatty acid oligosaccharide monoester |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86106683A (en) * | 1986-09-26 | 1988-04-06 | 广西壮族自治区化工研究所 | method for synthesizing sucrose fatty acid ester |
| WO1994014823A1 (en) * | 1992-12-21 | 1994-07-07 | University Of Iowa Research Foundation | Sugar-based polymers |
| US5550225A (en) * | 1992-03-30 | 1996-08-27 | L'oreal | Process for preparing monoesters predominantly in the 6 position of d-maltose, their use in cosmetic, buccal-dental, pharmaceutical and food compositions |
| CN1167770A (en) * | 1996-04-02 | 1997-12-17 | 三菱化学株式会社 | Method for producing sucrose fatty acid ester |
| CN1232036A (en) * | 1999-02-10 | 1999-10-20 | 中国科学院上海有机化学研究所 | Production of sucrose ester by homogeneous solventless process |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86106683A (en) * | 1986-09-26 | 1988-04-06 | 广西壮族自治区化工研究所 | method for synthesizing sucrose fatty acid ester |
| US5550225A (en) * | 1992-03-30 | 1996-08-27 | L'oreal | Process for preparing monoesters predominantly in the 6 position of d-maltose, their use in cosmetic, buccal-dental, pharmaceutical and food compositions |
| WO1994014823A1 (en) * | 1992-12-21 | 1994-07-07 | University Of Iowa Research Foundation | Sugar-based polymers |
| CN1167770A (en) * | 1996-04-02 | 1997-12-17 | 三菱化学株式会社 | Method for producing sucrose fatty acid ester |
| CN1232036A (en) * | 1999-02-10 | 1999-10-20 | 中国科学院上海有机化学研究所 | Production of sucrose ester by homogeneous solventless process |
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