CN101514218B - Raw materials formula for synthetic sucrose fatty ester and synthetic method thereof - Google Patents
Raw materials formula for synthetic sucrose fatty ester and synthetic method thereof Download PDFInfo
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Abstract
The invention discloses a raw materials formula for synthetic sucrose fatty ester and a synthetic method thereof, belonging to the chemical field. The raw materials formula includes, based on the weight part, 50 to 100 parts of sucrose, 20 to 80 parts of fatty acid methyl ester or ethyl ester, 0.2 to 8 parts of catalyst, 5 to 50 parts of fatty acid cationic soap salt, 1 to 20 parts of modified phospholipids, 0 to 8 parts of sucrose ester (HLB is 5 to 15) and 0 to 6 parts of sodium lactate. In the invention, the method that the composite catalyst is added in the system for synthesizing sucroseester by the solvent-free method is adopted. The modified phospholipids are added so that the reaction in the system for synthesizing sucrose ester is more uniform, the congruent melting can reach rapidly, thus effectively improving the conversion rate of the sucrose ester and the content of the sucrose monoesters and total esters in the products.
Description
Technical field
The present invention relates to a kind of composition of raw materials and compound method thereof of synthetic sucrose fatty ester, belong to chemical field.
Background technology
It is a kind of excellent property and foolproof non-ionics that sucrose fatty ester is called for short sucrose ester (Sucrose Fatty Acid Esters is called for short SE); It is as a kind of The World Health Organization (WHO), United Nations's grain tissue (FAO), the European Community and Japan; China; The foodstuff additive of the equal approveds of state such as the U.S. can be as emulsifying agent, stablizer, lubricant, regulator and antiseptic-germicide in food, in medicine as medicine and assistant agent; In makeup and washing composition,, in agricultural, help into agent as fruit antistaling agent, inert ingredient and plant-growth as emulsifying agent and wetting Agent for Printing Inks.Because sucrose ester nontoxicity and having wide range of applications, therefore, its synthetic and applied research enjoy people to pay close attention to.
At present, the industriallization compound method of sucrose ester, mostly adopt ester exchange method.The transesterify synthesis of sucrose ester can be divided into solvent method and solventless method two big classes again in the industry.Use the solventless method synthesis of sucrose ester; Though nontoxicity, the time is short, cost is low; But sucrose in the reaction system and fatty acid methyl ester (or ethyl ester) are difficult to reach congruent melting under the effect of single fat acid soap body, cause that the building-up reactions system is inhomogeneous, and difficulty reaches the homogeneous phase level; Cause in the reaction product sucrose monoester and sucrose ester total ester content not high, transformation efficiency is lower.And that the high sucrose ester product of monoester content is used in many fields such as food, medicine is very wide, and the market requirement is maximum, so greatly limited applying of solvent-free synthesis method.
Summary of the invention
Technical problem to be solved by this invention provides that a kind of composition of raw materials is ingenious, and formulation content is reasonable, and the product monoester content is high, the composition of raw materials of the synthetic sucrose fatty ester that product yield is high.
It is advanced that another technical problem to be solved by this invention provides a kind of technological design, and process step is reasonable, and the content of product yield height, sucrose monoester and total ester is high, the synthetic process of the sucrose fatty ester of applied range.
The present invention solves the problems of the technologies described above the composition of raw materials that the technical scheme that is adopted is a kind of synthetic sucrose fatty ester, and the kind of its prescription and consumption are:
Sucrose: 50--200 weight part, fatty acid methyl ester or ethyl ester: 20--80 weight part, catalyzer: 0.2--8 weight part; Lipid acid cationic soap salt: 5--50 weight part; Modified phospholipid compounds: 1-20 weight part; Sucrose ester (HLB 5-15): 0-8 weight part; Sodium.alpha.-hydroxypropionate: 0-6 weight part.
As preferably; Described modified phospholipid compounds is one or more in modified soy bean lipoid, modified corn phosphatide, modification egg phosphatide, modification cottonseed phosphatide, modification vegetable seed phosphatide, the modification peanut phosphatide, and the method that described modification is adopted is one or more in hydroxylation modification, hydrogenation modification, acylation modification, the modification of enzymatic hydrolysis.
As preferably, described lipid acid cationic soap salt is potassium stearate and/or Magnesium Stearate and/or lithium stearate.
As preferably, described modified phospholipid compounds is the hydroxylation modified soy bean lipoid.
As preferably, described catalyzer is one or more in carbonate, quicklime, Pottasium Hydroxide, the phosphoric acid salt.The present invention solves the problems of the technologies described above the synthetic process that the technical scheme that is adopted still is a kind of sucrose fatty ester, and its process step is:
A, with fatty acid methyl ester or ethyl ester with oil bath or be steam heated to 70-110 ℃;
B, under agitation add lipid acid cationic soap salt then, add catalyzer and modified phospholipid compounds then, stir, add the sucrose powder again;
C, rising temperature of reaction maintain vacuum tightness 1000-5500Pa simultaneously to 120-180 ℃, under agitation react 10-480 minute, obtain the thick product of sucrose ester;
D, with the thick product of sucrose ester through washing, organic solvent extraction and remove soap body and impurity such as catalyzer, obtain the sucrose ester purified product.
As preferably, described oil bath or steam-heated TR are 90-100 ℃.
As preferably, among the described step c, the rising temperature of reaction is to 140-160 ℃.
As preferably, among the described step c, maintain vacuum tightness 2000-4000Pa.
As preferably, among the described step b, when adding lipid acid cationic soap salt, add sucrose ester, when adding catalyzer and modified phospholipid compounds, add Sodium.alpha.-hydroxypropionate.
The present invention compares with prior art and has the following advantages and effect: 1, the present invention has adopted numerous emulsifiers to come the catalysis synthetic sucrose fatty ester; Make the sucrose fatty ester synthetic system thinning, become homogeneous phase; Increase the contact area of reaction molecular, improved the content of sucrose monoester and the transformation efficiency of sucrose ester reaction.2, the present invention adopts fatty acid soaps salt and the phospholipids compounds that adds different amounts.Make the sucrose in the synthetic system produce congruent melting, make the sucrose ester synthetic system become homogeneous phase, increased the contact area of reaction molecular, improved the content of product sucrose monoester, accelerated the interesterification synthesis of sucrose ester with total ester.
Embodiment
Below in conjunction with embodiment the present invention is done further detailed description, following examples are to explanation of the present invention and the present invention is not limited to following examples.
Embodiment 1:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry, add fatty acid methyl ester 35 grams, oil bath is heated to 80-100 ℃, and under agitation adds promotor sucrose ester (HLB11) 3 grams, and potassium stearate 30 grams add magnesiumcarbonate 1.5 grams and quicklime 2 grams again.After stirring, add hydroxylation modified soy bean lipoid 8 grams.After waiting to stir, add sucrose powder 160 grams at last.Elevated temperature is kept vacuum tightness 1500Pa simultaneously to 140-142 ℃, and stirring reaction 65 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 137.25 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 69.32%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 57.82%, and the sucrose total ester content is 95.76%.
Embodiment 2:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 40 grams, oil bath is heated to 90-100 ℃, and under agitation adds promotor sucrose ester (HLB 15) 5 grams; Potassium stearate 20 grams add yellow soda ash 1.5 grams, potassium hydrogenphosphate 2 grams again.After stirring, add hydroxylation modified soy bean lipoid 6 grams, stir after 1-5 minute, add sucrose powder 140 grams at last, elevated temperature is to 143-145 ℃, and vacuum tightness maintains 3800Pa, and stirring reaction 165 minutes obtains the thick product of sucrose ester.Use the method for prior art then; Promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996); Obtain sucrose ester purified product 151.7 grams, productive rate is 82.0%, through efficient liquid phase chromatographic analysis; The content of its sucrose monoester is 49.27%, and the sucrose total ester content is 96.82%.
Embodiment 3:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty-acid ethyl ester 38 grams, oil bath is heated to 80-100 ℃, and under agitation adds promotor sucrose ester (HLB 13) 5 grams; Each 15 gram of potassium stearate and lithium stearate add Na2HPO412H2O 2 grams and salt of wormwood 1.5 grams again.After stirring, add hydrogenation modified corn phosphatidase 11 0 gram.Behind the restir 1 to 5 minute, add sucrose powder 166 grams at last, elevated temperature is kept vacuum tightness 1350Pa simultaneously to 138-140 ℃, and stirring reaction 70 minutes obtains the thick product of sucrose ester.Use the method for prior art then, promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996), obtain sucrose ester purified product 149.15 grams, productive rate is 71.36%.Through efficient liquid phase chromatographic analysis, its sucrose monoester content is 58.27%, and the sucrose total ester content is 94.96%.
Embodiment 4:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 35 grams, oil bath is heated to 80-100 ℃, and under agitation adds promotor sucrose ester (HLB 7) 5 grams; Potassium stearate 20 grams; Magnesium Stearate 15 grams add quicklime 3.5 grams and Pottasium Hydroxide 1 gram again, add modification of enzymatic hydrolysis cottonseed phosphatidase 11 2 grams.After stirring, add sucrose powder 165 grams at last.Elevated temperature is kept vacuum tightness 3450Pa simultaneously to 140-160 ℃, and stirring reaction 55 minutes obtains the thick product of sucrose ester.Use the method for prior art then, promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996), obtain sucrose ester purified product 135.69 grams, productive rate is 66.19%.Through efficient liquid phase chromatographic analysis, its sucrose monoester content is 63.15%, and the sucrose total ester content is 96.03%.
Embodiment 5:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 60 grams, oil bath is heated to 70-90 ℃, and under agitation adds potassium stearate 50 grams; After stirring; Add salt of wormwood 5 grams, hydroxylation modification egg phosphatidase 15 gram and Sodium.alpha.-hydroxypropionate 5 grams, continue to stir after 1-5 minute, add sucrose powder 140 grams again.The temperature that raises is kept vacuum tightness 2100Pa simultaneously to 148-150 ℃, and stirring reaction 200 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 159.72 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 79.86%.Through efficient liquid phase chromatographic analysis, its sucrose monoester content is 45%, and the sucrose total ester content is 95.28%.
Embodiment 6:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry, add fatty acid methyl ester 32 grams, oil bath is heated to 80-100 ℃; And under agitation add promotor potassium stearate 15 grams, Magnesium Stearate 10 grams, quicklime 5 grams, salt of wormwood 3 grams and acylation modification egg phosphatidase 11 2 grams; After continuing to stir, add sucrose powder 168 grams at last, elevated temperature is to 150-152 ℃; Vacuum tightness maintains 4500Pa simultaneously, and stirring reaction 50 minutes obtains sucrose ester and reacts thick product.Use the method for prior art then; Promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996); Obtain sucrose ester purified product 136.38 grams, productive rate is 68.19%, through efficient liquid phase chromatographic analysis; The content of its sucrose monoester is 62.27%, and the sucrose total ester content is 96.17%.
Embodiment 7:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 20 grams; Oil bath is heated to 80-100 ℃; And under agitation adding promotor sucrose ester (HLB14) 2 grams, potassium stearate 25 grams add quicklime 0.2 gram, hydroxylation modified soy bean lipoid 2.5 grams and Sodium.alpha.-hydroxypropionate 1 gram again.After waiting to stir, add sucrose powder 50 grams at last.Elevated temperature is kept vacuum tightness 5500Pa simultaneously to 120-140 ℃, and stirring reaction 100 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 43.72 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 60.72%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 62.08%, and the sucrose total ester content is 96.72%.
Embodiment 8:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 80 grams; Oil bath is heated to 70-100 ℃; And under agitation adding promotor sucrose ester (HLB5) 1 gram, potassium stearate 35 grams add Pottasium Hydroxide 0.3 gram, modification of enzymatic hydrolysis vegetable seed phosphatidase 11 gram and Sodium.alpha.-hydroxypropionate 0.5 gram again.After waiting to stir, add sucrose powder 130 grams at last.Elevated temperature is kept vacuum tightness 4000Pa simultaneously to 150-180 ℃, and stirring reaction 460 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 168.78 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 83.55%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 45.23%, and the sucrose total ester content is 96.75%.
Embodiment 9:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 25 grams; Oil bath is heated to 70-110 ℃; And under agitation adding promotor sucrose ester (HLB6) 4 grams, potassium stearate 18 grams add Pottasium Hydroxide 0.5 gram, Sodium phosphate, dibasic 1.2 grams, hydroxylation modification peanut phosphatide 3 grams and Sodium.alpha.-hydroxypropionate 3 grams again.After waiting to stir, add sucrose powder 75 grams at last.Elevated temperature is kept vacuum tightness 1000Pa simultaneously to 120-150 ℃, and stirring reaction 480 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 77.98 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 74.98%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 60.87%, and the sucrose total ester content is 97.82%.
Embodiment 10:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 30 grams; Oil bath is heated to 80-110 ℃; And under agitation adding promotor sucrose ester (HLB10) 3 grams, Magnesium Stearate 15 grams add quicklime 4.5 grams, salt of wormwood 3.5 grams, hydrogenation modified soy bean lipoid 20 grams and Sodium.alpha.-hydroxypropionate 4 grams again.After waiting to stir, add sucrose powder 100 grams at last.Elevated temperature is kept vacuum tightness 2000Pa simultaneously to 160-180 ℃, and stirring reaction 10 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 79.96 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 60.12%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 65.12%, and the sucrose total ester content is 96.25%.
Embodiment 11:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 55 grams; Oil bath is heated to 90-110 ℃, and under agitation adds promotor sucrose ester (HLB13) 8 grams, Magnesium Stearate 20 grams; Potassium stearate 20 grams add quicklime 3 grams, Pottasium Hydroxide 2 grams, sodium hydrogen phosphate 3 grams, acylation modification soybean phospholipid 20 grams and Sodium.alpha.-hydroxypropionate 6 grams again.After waiting to stir, add sucrose powder 185 grams at last.Elevated temperature is kept vacuum tightness 5000Pa simultaneously to 150-170 ℃, and stirring reaction 400 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 168.04 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 80.79%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 45.29%, and the sucrose total ester content is 96.83%.
Embodiment 12:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 28 grams; Oil bath is heated to 70-90 ℃, and under agitation adds promotor sucrose ester (HLB9) 7 grams, lithium stearate 5 grams; Magnesium Stearate 5 grams add yellow soda ash 3.5 grams, potassium hydrogenphosphate 3.5 grams, modification of enzymatic hydrolysis vegetable seed phosphatidase 11 8 grams and Sodium.alpha.-hydroxypropionate 5 grams again.After waiting to stir, add sucrose powder 200 grams at last.Elevated temperature is kept vacuum tightness 5300Pa simultaneously to 130-160 ℃, and stirring reaction 20 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 144.55 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 59.00%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 62.89%, and the sucrose total ester content is 96.38%.
Embodiment 13:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 48 grams, oil bath is heated to 80-100 ℃, and under agitation adds promotor sucrose ester (HLB6) 6 grams; Potassium stearate 5 grams add magnesiumcarbonate 5 grams, hydroxylation modified soy bean lipoid 14 grams and Sodium.alpha.-hydroxypropionate 2 grams again.After waiting to stir, add sucrose powder 152 grams at last.Elevated temperature is kept vacuum tightness 2500Pa simultaneously to 125-145 ℃, and stirring reaction 360 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 161.9 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 78.59%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 56.10%, and the sucrose total ester content is 97.12%.
Embodiment 14:
In the 1000ml three-necked bottle that has stirring rod and froth breaking slurry; Add fatty acid methyl ester 35 grams; Oil bath is heated to 90-100 ℃; And under agitation adding promotor sucrose ester (HLB13) 4 grams, Magnesium Stearate 25 grams add lime carbonate 2.5 grams, Pottasium Hydroxide 1.5 grams, hydrogenation modified corn phosphatidase 11 6 grams and Sodium.alpha.-hydroxypropionate 3.5 grams again.After waiting to stir, add sucrose powder 125 grams at last.Elevated temperature is kept vacuum tightness 1200Pa simultaneously to 145-175 ℃, and stirring reaction 280 minutes obtains the thick product of sucrose ester.Use the method for prior art then,, obtain sucrose ester purified product 116.10 grams promptly through organic solvent extraction and quicklime purification process (with reference to European patent EP 0448996).Productive rate is 70.79%, and through efficient liquid phase chromatographic analysis, its sucrose monoester content is 62.93%, and the sucrose total ester content is 99.12%.
In the present invention, the applicant has adopted in solventless method synthesis of sucrose ester system through a large amount of tests, adds the method for composite catalyst.Except more alkaline organic catalysts such as carbonate or quicklime, also contain three (or a plurality of) components such as modified phospholipid compounds and lipid acid cationic soap salt and form in this composite catalyst.Wherein the interpolation of modified phospholipid compounds can make sucrose ester synthetic system reaction more even, can reach the congruent melting state quickly, thereby improves the content of sucrose monoester and total ester in transformation efficiency and the product of reaction product sucrose ester effectively.
The productive rate of sucrose ester can reach 60-82% in the reaction product.The total ester content of sucrose ester product reaches 90-99% behind the purifying, and sucrose monoester content can reach 45-65%, meets internal and international industrial sucrose ester product standard.This invention technology the lab scale successful development and in Hangzhou auspicious continuous heavy rain chemical company obtains the suitability for industrialized production achievement, on probation through among a small circle obtained the very high evaluation of client.The purified processing of product meets the sucrose ester national standard of China, the U.S. and Japan, has broad application prospects and market outlook.
The technology of the thick purifying products of sucrose ester of the present invention is prior art, no longer tired stating.
Though the present invention with embodiment openly as above; But it is not in order to limit protection scope of the present invention; Any technician who is familiar with this technology, change and the retouching in not breaking away from design of the present invention and scope, done all should belong to protection scope of the present invention.
Claims (8)
1. the feedstock composition of a synthetic sucrose fatty ester, the kind of its composition and consumption are:
Sucrose: 50-200 weight part, fatty acid methyl ester or ethyl ester: 20-80 weight part, catalyzer: 0.2-8 weight part; Lipid acid cationic soap salt: 5-50 weight part; Modified phospholipid compounds: 1-20 weight part; The HLB value is the sucrose ester of 5-15: the 0-8 weight part; Sodium.alpha.-hydroxypropionate: 0-6 weight part; Described modified phospholipid compounds is one or more in modified soy bean lipoid, modified corn phosphatide, modification egg phosphatide, modification cottonseed phosphatide, modification vegetable seed phosphatide, the modification peanut phosphatide, and the method that described modification is adopted is one or more in hydroxylation modification, hydrogenation modification, acylation modification, the modification of enzymatic hydrolysis.
2. the feedstock composition of synthetic sucrose fatty ester according to claim 1, it is characterized in that: described lipid acid cationic soap salt is potassium stearate and/or Magnesium Stearate and/or lithium stearate.
3. the feedstock composition of synthetic sucrose fatty ester according to claim 1, it is characterized in that: described modified phospholipid compounds is the hydroxylation modified soy bean lipoid.
4. according to the feedstock composition of claim 1 or 3 described synthetic sucrose fatty esters, it is characterized in that: described catalyzer is one or more in carbonate, quicklime, Pottasium Hydroxide, the phosphoric acid salt.
5. method that adopts any described raw material synthetic sucrose fatty ester among the claim 1-4, its process step is:
A, with 20-80 weight part fatty acid methyl ester or ethyl ester with oil bath or be steam heated to 70-110 ℃;
B, under agitation add 5-50 weight part lipid acid cationic soap salt then, add 0.2-8 weight part catalyzer and 1-20 weight part modified phospholipid compounds then, stir, add 50-200 weight part sucrose powder again; When adding lipid acid cationic soap salt, adding 0-8 weight part HLB value is the sucrose ester of 5-15, when adding catalyzer and modified phospholipid compounds, adds 0-6 weight part Sodium.alpha.-hydroxypropionate;
C, rising temperature of reaction maintain vacuum tightness 1000-5500Pa simultaneously to 120-180 ℃, under agitation react 10-480 minute, obtain the thick product of sucrose ester;
D, with the thick product of sucrose ester through washing, organic solvent extraction and remove soap body and catalyst impurities, obtain the sucrose ester purified product.
6. PROCESS FOR SYNTHESIZING SUCROSE ESTERS OF FATTY ACIDS according to claim 5 is characterized in that: described oil bath or steam-heated TR are 90-100 ℃.
7. PROCESS FOR SYNTHESIZING SUCROSE ESTERS OF FATTY ACIDS according to claim 5 is characterized in that: among the described step c, the rising temperature of reaction is to 140-160 ℃.
8. PROCESS FOR SYNTHESIZING SUCROSE ESTERS OF FATTY ACIDS according to claim 5 is characterized in that: among the described step c, maintain vacuum tightness 2000-4000Pa.
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| CN108067160A (en) * | 2016-11-18 | 2018-05-25 | 广西高通食品科技有限公司 | A kind of method that misting cooling prepares sucrose fatty ester particle |
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| 张卫等.无溶剂法合成蔗糖酯的工艺研究.《食品科技》.2003,(第4期),68-70. * |
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Assignee: Hangzhou Rui Lin Chemical Co., Ltd. Assignor: Yuan Changgui Contract record no.: 2012330000101 Denomination of invention: Raw materials formula for synthetic sucrose fatty ester and synthetic method thereof Granted publication date: 20120111 License type: Exclusive License Open date: 20090826 Record date: 20120323 |
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Effective date of registration: 20200713 Address after: 311500 No. 279, Yang Tang Road, Tonglu County, Hangzhou, Zhejiang Patentee after: Hangzhou Rui Lin Chemical Co.,Ltd. Address before: 311500 Hangzhou Rui Lin Chemical Co., Ltd., No. 279, Tang Yang Road, Tonglu County, Hangzhou, Zhejiang Patentee before: Yuan Changgui |