CN101705257B - Method for catalytic synthesis of sucrose ester by lipase in two phases of water and organic solvent - Google Patents
Method for catalytic synthesis of sucrose ester by lipase in two phases of water and organic solvent Download PDFInfo
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- CN101705257B CN101705257B CN2009101545955A CN200910154595A CN101705257B CN 101705257 B CN101705257 B CN 101705257B CN 2009101545955 A CN2009101545955 A CN 2009101545955A CN 200910154595 A CN200910154595 A CN 200910154595A CN 101705257 B CN101705257 B CN 101705257B
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Abstract
The invention discloses a method for catalytic synthesis of sucrose ester by lipase in two phases of water and organic solvent. The method comprises the following steps of: preparing buffer solution with a pH value of between 7.8 and 8.8 by using water as a solvent, and adding the obtained buffer solution to an organic solvent, which is lightly poisonous and mutually insoluble in water, to form atwo-phase system of water and organic solvent, wherein the volume percentage of the buffer solution in the two-phase system is 40 to 70 percent; and adding sucrose and vinyl acetate to the two-phase system for reaction under an action of candida lipase to prepare the sucrose ester. By the method, the safety of using the sucrose ester for food processing is greatly improved, simultaneously the synthetic efficiency of the sucrose ester is greatly improved, and the production cost is obviously lowered, so that the method is a novel method for improving product safety and production benefits.
Description
One, technical field
The present invention relates to a kind of method of catalytic synthesis of sucrose ester by lipase.
Two, background technology
Sucrose ester is as a kind of non-ionics, and it is partly to be that hydrophilic radical, one or more lipid acid are the compounds that the hydrophobic group forms with sucrose.Through the kind of control degree of esterification and acry radical donor, can synthesize the wide region hydrophile-lypophile balance number and get sucrose ester.Sucrose ester is not only a kind of excellent surfactant, and its antitumor, antibiotic and insecticidal activity also is in the news.So the sucrose ester of different degree of substitution has been widely used in the industries such as food, medicine, daily use chemicals and agricultural.
The compound method of sucrose ester has chemical method and enzyme process, and chemical preparation adopts basic catalyzer at high temperature to react usually at present, poor selectivity, and can generate coloured by product.The employing enzyme then can be at comparatively gentle reaction conditions lower area selectively synthesizing sucrose ester as catalyzer.In enzymatic reaction, its regioselectivity of different enzymes is different.Numerous scholars have carried out a large amount of research to this, find that proteolytic enzyme, lypase, abzyme all can be used for synthesis of sucrose ester.The following points characteristic of conclude: 1. from the regioselectivity of the proteolytic enzyme of Bacillus subtilus be embodied in 1 of sucrose '-OH, also have other several kinds of proteolytic enzyme to show selectivity in addition to 2-OH.But proteolytic enzyme do not accept usually long-chain (＞C12) lipid acid is as acry radical donor, therefore limited proteolytic enzyme in the suitability of tensio-active agent aspect preparing.2. compare with proteolytic enzyme, but the fatty acid cane sugar ester of lypase catalysis wide region is synthetic, its acidylate generally occurs in 6-0H. and discovers recently that 3. abzyme also can catalytic synthesis of sucrose ester, has increased the kind of the enzyme of synthesis of sucrose ester.
Wherein, be that a kind of research is more with lipase-catalyzed synthetic all kinds of sucrose esters, existing certain application, its outstanding advantage be can be on the different hydroxyls of sucrose molecules selective esterification, thereby application prospect ideal.But existing lipase-catalyzed synthetic all kinds of sucrose ester technology are all reacted in organic solvent, in order to improve the solvability of sucrose in organic solvent; Need allocate the N of 20% above volume ratio into, N-dimethylformamide, and N; The N-dimethylformamide is a high toxic material, and is after the use, not only bigger to environment and producers' healthy effect; And the sucrose ester product of being produced is as the midbody of foodstuff additive or additive, and there is serious hidden danger in security.
So for fear of using noxious solvent, some scholars have carried out new trial.Trend towards at present using such as the very little organic solvent of this type of trimethyl carbinol toxicity.But because sucrose solubleness therein is lower, so be difficult to obtain the ideal productive rate.
Three, summary of the invention
The technical problem that the present invention will solve is to provide a kind of method of new catalytic synthesis of sucrose ester by lipase; To improve the security of sucrose ester as foodstuff additive; Improve the selectivity of the different hydroxy esterifications of lipase-catalyzed sucrose; Improve the combined coefficient of sucrose ester, reduce the production cost of lypase synthesis of sucrose ester.
For solving the problems of the technologies described above, the present invention adopts following technical scheme:
A kind of method of catalytic synthesis of sucrose ester by lipase, described method is carried out according to following steps:
(1) with water is the buffered soln of solvent preparation pH 7.8～8.8; Toward low toxicity, with the immiscible organic solvent of water in allocate the buffered soln that obtains of preparation into and form water and organic solvent two-phase system, the volume percent of buffered soln is 40%～70% in the gained two-phase system;
(2) in the two-phase system that step (1) preparation obtains, allocate sucrose into, the charging capacity of sucrose is 160～240mmol/50ml, stirs and makes sucrose dissolved.2～6 times the amount of pressing the sucrose mole number adds vinyl-acetic ester; Amount by 40～120 enzyme activity units of every gram sucrose adds lipase from candida sp again; Changeing～120 at PM 70 changes under the stirring, keeps 40～50 ℃ of temperature, pH 7.8～8.8, reacts 2～8 hours; After reaction stopped, static, two phase stratification was isolated organic phase, and organic solvent is reclaimed in vacuum distilling, promptly gets the sucrose ethyl ester.
Further specify in the face of technique scheme down.
In the step of the present invention (1), described low toxicity, with the immiscible organic solvent of water be preferably the tertiary amyl alcohol or the trimethyl carbinol, more preferably tertiary amyl alcohol.The buffered soln of said pH 7.8～8.8 can adopt the Veronal sodium-hydrochloride buffer liquid system of pH 7.8～8.8 or the boric acid-borate buffer solution system of pH8.0～8.8; Preferably use Veronal sodium-hydrochloride buffer liquid system of pH 7.8～8.8, more preferably use Veronal sodium-hydrochloride buffer of pH 8.4.The volume percent of buffered soln preferred 70% in the gained two-phase system.
In the step of the present invention (2), the dosage of sucrose is preferably 180～200mmol/50ml, most preferably is 200mmol/50ml.Described vinyl-acetic ester preferably adds according to 4～5 times amount of sucrose mole number, and most preferably 4 times amount according to the sucrose mole number adds.Described lipase from candida sp preferably adds according to the amount of 100～120 enzyme activity units of every gram sucrose, and most preferably the amount according to 120 enzyme activity units of every gram sucrose adds.Reaction conditions in the step (2) is preferably following: keep 45 ℃ of temperature, pH 8.4, stirring reaction 6 hours.
Compared with prior art, beneficial effect of the present invention is:
The present invention adopts water and organic solvent two-phase system as the reaction medium that catalytic synthesis of sucrose ester by lipase reacts, and in reaction medium, has the water of 40%～70% volume ratio, makes sucrose dissolved good, need not allocate highly toxic N into, the N-dimethylformamide.The organic solvent of selecting for use in the reaction medium only requires not dissolve each other with water, thereby can select the organic solvent of low toxicity, makes the product sucrose ester be used for the food-processing security and improves greatly.Simultaneously, the solubleness of sucrose in reaction medium is higher than pure organic solvent reaction system far away, has increased substantially the sucrose ester combined coefficient, and production cost is obviously reduced, and is a kind of novel method that improves Product Safety and productivity effect.
Four, embodiment
With specific embodiment technical scheme of the present invention is further specified below, but protection scope of the present invention is not limited thereto:
Embodiment 1
With deionized water preparation 0.04mol/L Veronal sodium solution, with the hydrochloric acid adjust pH 8.4 of 0.2mol/L.Mix with tertiary amyl alcohol in 7: 3 ratios, altogether 50ml allocates 200mmol sucrose (68.4 gram) into, allocates the lipase from candida sp that enzyme activity is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 100 units.Add the several 4 times vinyl-acetic ester of sucrose mol, keeps 45 ℃ of temperature,, reacted 6 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 8.4 with 100 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery tertiary amyl alcohols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 54.7%.
Embodiment 2
With deionized water preparation 0.04mol/L Veronal sodium solution, with the hydrochloric acid adjust pH 7.8 of 0.2mol/L.Mix with tertiary amyl alcohol in 4: 6 ratios, altogether 50ml allocates 160mmol sucrose (54.7 gram) into, allocates the lipase from candida sp that enzyme activity is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 40 units.Add the several 5 times vinyl-acetic ester of sucrose mol, keeps 40 ℃ of temperature,, reacted 2 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 7.8 with 120 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery tertiary amyl alcohols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 52.3%.
Embodiment 3
With deionized water preparation 0.04mol/L Veronal sodium solution, with the hydrochloric acid adjust pH 8.2 of 0.2mol/L.Mix with tertiary amyl alcohol in 5: 5 ratios, altogether 50ml allocates 240mmol sucrose (82.1 gram) into, allocates the lipase from candida sp that enzyme activity is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 120 units.Add the several 3 times vinyl-acetic ester of sucrose mol, keeps 50 ℃ of temperature,, reacted 8 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 8.2 with 70 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery tertiary amyl alcohols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 55.8%.
Embodiment 4
With deionized water preparation 0.04mol/L Veronal sodium solution, with the hydrochloric acid adjust pH 8.8 of 0.2mol/L.Mix with tertiary amyl alcohol in 6: 4 ratios, altogether 50ml allocates 180mmol sucrose (61.6 gram) into, allocates the lipase from candida sp that vigor is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 80 units.Add the several 2 times vinyl-acetic ester of sucrose mol, keeps 45 ℃ of temperature,, reacted 4 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 8.8 with 90 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery tertiary amyl alcohols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 53.5%.
Embodiment 5
With deionized water preparation 0.04mol/L Veronal sodium solution, with the hydrochloric acid adjust pH 8.0 of 0.2mol/L.Mix with tertiary amyl alcohol in 6: 4 ratios, altogether 50ml allocates 220mmol sucrose (75.2 gram) into, allocates the lipase from candida sp that enzyme activity is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 80 units.Add the several 6 times vinyl-acetic ester of sucrose mol, keeps 40 ℃ of temperature,, reacted 5 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 8.0 with 110 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery tertiary amyl alcohols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 56.2%.
Embodiment 6
With deionized water preparation 0.04mol/L Veronal sodium solution, with the hydrochloric acid adjust pH 8.5 of 0.2mol/L.Mix with the trimethyl carbinol in 7: 3 ratios, altogether 50ml allocates 200mmol sucrose (68.4 gram) into, allocates the lipase from candida sp that enzyme activity is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 100 units.Add the several 5 times vinyl-acetic ester of sucrose mol, keeps 45 ℃ of temperature,, reacted 8 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 8.5 with 100 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery trimethyl carbinols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 52.5%.
Embodiment 7
With deionized water preparation 0.2mol/L BAS, and the borax soln of 0.2mol/L, intermingling is to pH value 8.4.Mix with tertiary amyl alcohol in 7: 3 ratios, altogether 50ml allocates 200mmol sucrose (68.4 gram) into, allocates the lipase from candida sp that enzyme activity is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 120 units.Add the several 4 times vinyl-acetic ester of sucrose mol, keeps 45 ℃ of temperature,, reacted 6 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 8.4 with 100 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery tertiary amyl alcohols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 50.4%.
Embodiment 8
With deionized water preparation 0.04mol/L Veronal sodium solution, with the hydrochloric acid adjust pH 8.4 of 0.2mol/L.Mix with tertiary amyl alcohol in 7: 3 ratios, altogether 50ml allocates 200mmol sucrose (68.4 gram) into, allocates the lipase from candida sp that enzyme activity is 10000 units/gram (company of Wuxi City snow plum zymin Science and Technology Ltd. produces) into by the amount of every gram sucrose 120 units.Add the several 4 times vinyl-acetic ester of sucrose mol, keeps 45 ℃ of temperature,, reacted 6 hours, from reacting initial every interval 1.5 hours, with the pH of the aqueous sodium hydroxide solution conditioned reaction medium of 0.2mol/L, maintenance pH value 8.4 with 100 rev/mins of stirrings.It is static that reaction finishes the back, treat organic solvent and water stratification after, isolate organic solvent, the following 80 ℃ of insulation recovery tertiary amyl alcohols of 0.01Mpa vacuum tightness promptly get the sucrose ethyl ester.By the sucrose quality of allocating into, the yield of sucrose ethyl ester is 57.2%.
Claims (6)
1. the method for a catalytic synthesis of sucrose ester by lipase, described method is carried out according to following steps:
(1) with water is the buffered soln of solvent preparation pH 7.8～8.8; Toward low toxicity, with the immiscible organic solvent of water in allocate the buffered soln that obtains of preparation into and form water and organic solvent two-phase system, the volume percent of buffered soln is 40%～70% in the gained two-phase system; Described low toxicity, with the immiscible organic solvent of water be tertiary amyl alcohol;
(2) in the two-phase system that step (1) preparation obtains, allocate sucrose into; The charging capacity of sucrose is 160～240mmol/50ml; 2～6 times the amount of pressing the sucrose mole number adds vinyl-acetic ester, and the amount by 40～120 enzyme activity units of every gram sucrose adds lipase from candida sp again, under PM 70 commentaries on classics～120 commentaries on classics are stirred; Keep 40～50 ℃ of temperature, pH 7.8～8.8, reacted 2～8 hours; After reaction stopped, static, two phase stratification was isolated organic phase, and organic solvent is reclaimed in vacuum distilling, promptly gets the sucrose ethyl ester.
2. the method for catalytic synthesis of sucrose ester by lipase as claimed in claim 1 is characterized in that the buffered soln of the said pH 7.8～8.8 of step (1) adopts the Veronal sodium-hydrochloride buffer liquid system of pH 7.8～8.8 or the boric acid-borate buffer solution system of pH8.0～8.8.
3. the method for catalytic synthesis of sucrose ester by lipase as claimed in claim 1 is characterized in that the dosage of sucrose in the step (2) is 180～200mmol/50ml.
4. the method for catalytic synthesis of sucrose ester by lipase as claimed in claim 1 is characterized in that the vinyl-acetic ester described in the step (2) adds according to 4～5 times amount of sucrose mole number.
5. the method for catalytic synthesis of sucrose ester by lipase as claimed in claim 1 is characterized in that the lipase from candida sp described in the step (2) adds according to the amount of 100～120 enzyme activity units of every gram sucrose.
6. the method for catalytic synthesis of sucrose ester by lipase as claimed in claim 1 is characterized in that the reaction conditions in the said step (2) is following: keep 45 ℃ of temperature, pH 8.4, stirring reaction 6 hours.
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| CN106086095A (en) * | 2016-08-26 | 2016-11-09 | 浙江工业大学 | A kind of method of enzyme law catalysis synthesis sorbate |
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| CN101928738B (en) * | 2010-08-23 | 2012-08-22 | 浙江工业大学 | Method for synthesizing cane sugar-6-acetic ester by using lipase for catalyzing |
| CN111763703B (en) * | 2020-07-02 | 2022-07-19 | 浙江工业大学 | Method for synthesizing sucrose-6-ethyl ester by enzyme method in organic solvent |
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| CN1733927A (en) * | 2005-08-02 | 2006-02-15 | 山东轻工业学院 | Enzyme catalysis for producing sucrose fatty acid ester |
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| CN1733927A (en) * | 2005-08-02 | 2006-02-15 | 山东轻工业学院 | Enzyme catalysis for producing sucrose fatty acid ester |
Non-Patent Citations (3)
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| 刘荣莉等.有机相酶法合成己二酸单乙烯蔗糖酯的研究.《日用化学工业》.2008,第38卷(第4期),205-209. * |
| 毛多斌等.酶催化选择性酯化在蔗糖酯合成中的应用研究进展.《日用化学工业》.2006,第36卷(第6期),369-373. * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106086095A (en) * | 2016-08-26 | 2016-11-09 | 浙江工业大学 | A kind of method of enzyme law catalysis synthesis sorbate |
| CN106086095B (en) * | 2016-08-26 | 2019-11-29 | 浙江工业大学 | A kind of method of enzyme law catalysis synthesis sorbate |
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