CN114107411A - Method for synthesizing sucrose-6-acetate in non-aqueous phase system - Google Patents
Method for synthesizing sucrose-6-acetate in non-aqueous phase system Download PDFInfo
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- CN114107411A CN114107411A CN202111393579.9A CN202111393579A CN114107411A CN 114107411 A CN114107411 A CN 114107411A CN 202111393579 A CN202111393579 A CN 202111393579A CN 114107411 A CN114107411 A CN 114107411A
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Abstract
The invention relates to a method for synthesizing sucrose-6-acetate in a non-aqueous phase system, which is characterized by comprising the following steps: uniformly mixing DMF and tert-amyl alcohol according to the volume ratio of 1:3-5 to form a non-aqueous phase system, and adding sucrose, vinyl acetate and lipase into the non-aqueous phase system, wherein the mixed solution is as follows: sucrose: vinyl acetate: the mass ratio of the lipase is 50: 1: 5: 4, carrying out heat preservation reaction at 30-35 ℃ for 8-24h, controlling the rotating speed at 150-250rpm, and after the reaction is finished, filtering by a filter press to remove lipase in the reaction system to obtain a supernatant. The invention has the advantages that: the method has the advantages of simple operation, mild reaction conditions, strong catalytic selectivity, good product safety and the like; filtering the supernatant with 0.22 μm filter membrane to liquid phase small bottle, and analyzing by high performance liquid chromatography with conversion rate of 90-94%.
Description
Technical Field
The invention belongs to the technical field of chemical production, relates to the field of sucralose production, and particularly relates to a method for synthesizing sucrose-6-acetate in a non-aqueous phase system.
Background
Sucralose is a novel sweetener, which is developed by the company of England and university of London and applied for patent in 1976, and is the only functional sweetener using sucrose as raw material. The sucralose has the effect of desalting sour and salty tastes, has the effect of covering up unpleasant tastes such as astringent taste, bitter taste, alcoholic taste and the like, has the synergistic effect on the spicy taste and the milk taste, and has a very wide application range. Therefore, the product is the most ideal intense sweetener at present, can be eaten by children, teenagers, adolescents, middle-aged people, old people and patients with various diseases, and has no any nutritional doubt.
The method for synthesizing sucrose-6-acetate is mainly the traditional chemical method, such as acetic anhydride esterification method, organic metal synthesis method, orthoester method, etc., but the chemical synthesis reaction condition is generally harsh, the synthesized product has darker color, and because of the poor selectivity, the by-product is easy to generate; enzymatic synthesis is also reported, but in an enzymatic synthesis reaction system, water content causes an enzymatic reaction to proceed in a reverse direction, and a diester as a byproduct is generated; in the prior art, a system for lipase reaction is used, so that the molecular structure of the lipase is damaged due to too strong polarity of a non-aqueous phase, or the solubility of sucrose is not high due to too weak polarity.
Disclosure of Invention
The invention aims to solve the problems of over-strong polarity and over-weak polarity of a non-aqueous phase in the process of synthesizing sucrose-6-acetate in an aqueous phase system, and provides a method for synthesizing sucrose-6-acetate in the non-aqueous phase system.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a method for synthesizing sucrose-6-acetate in a non-aqueous phase system, which is characterized by comprising the following steps:
uniformly mixing DMF and tert-amyl alcohol according to the volume ratio of 1:3-5 to form a non-aqueous phase system, and adding sucrose, vinyl acetate (acyl donor) and lipase into the non-aqueous phase system, wherein the mixed solution is as follows: sucrose: vinyl acetate: the mass ratio of the lipase is 50: 1: 5: 4, carrying out heat preservation reaction at 30-35 ℃ for 8-24h, controlling the rotating speed at 150-250rpm, and after the reaction is finished, filtering by a filter press to remove lipase in the reaction system to obtain a supernatant, wherein the non-aqueous phase system is any one of DMF/tert-amyl alcohol, DMF/tert-butyl alcohol and DMSO/tert-amyl alcohol; the lipase is one of bacillus subtilis lipase and L1754 lipase.
Further, the volume ratio of DMF to tertiary amyl alcohol is 1: 3-5; the volume ratio of DMF to tert-butanol is 1: 3-5; the volume ratio of DMSO to tertiary amyl alcohol is 1: 3-5.
Further, the concentration of the lipase is 6-60 mg/mL.
Further, the concentration of the sucrose is 10-20 g/L.
The invention adopts vinyl acetate as an acyl donor, utilizes the characteristics that tert-butyl alcohol or tert-amyl alcohol can improve the solubility of lipase and greatly reduce the inactivation of the lipase, further enables the lipase to be combined with the vinyl acetate into an intermediate compound, and can efficiently and specifically act on the hydroxyl at the 6 th position of sucrose to carry out transesterification. The combination of lipase and vinyl acetate not only facilitates the correct positioning of a combined group and a catalytic group, but also performs early preparation work for the next step of lipase to perform transesterification on the hydroxyl at the 6 th position of sucrose, and reduces the activation energy required by sucrose molecules to reach an activated state.
Compared with the prior art, the invention has the following advantages:
1. the method has simple operation process, avoids the generation of isomers, and also avoids the low-efficiency transesterification reaction with poor selectivity;
2. the synthesis of the sucrose-6-acetate in a non-aqueous phase system has the advantages of mild reaction conditions, strong catalytic selectivity, good product safety and the like;
3. filtering the supernatant with 0.22 μm filter membrane to liquid phase small bottle, and analyzing by high performance liquid chromatography with conversion rate of 90-94%.
Detailed description of the preferred embodiments
A method for synthesizing sucrose-6-acetate in a non-aqueous phase system comprises the following specific implementation steps:
example 1:
a. preparing a mixed organic solution (non-aqueous phase system): according to the formula of DMF: carrying out dry labor and high-speed transformation on the obtained tert-amyl alcohol according to the volume ratio of 1:4 and the total volume of the obtained tert-amyl alcohol is 6m, pumping the tert-amyl alcohol with the volume ratio of 4.8m and the obtained tert-amyl alcohol into the reaction kettle, pumping the DMF for carrying out thin film transformation at 1.2m, and starting stirring;
b. putting 123kg (0.06 moL/L) of sucrose into a reaction kettle, pumping 310kg (0.6 moL/L) of vinyl acetate into the reaction kettle with the length of 6m after starting stirring and completely dissolving, then putting 480kg of bacillus subtilis lipase into the reaction kettle, carrying out heat preservation reaction at the temperature of 30 ℃, carrying out reaction at the stirring speed of 200 rpm for 9 hours, filtering by a filter press to remove the bacillus subtilis lipase in a reaction system after the reaction is finished, and standing at room temperature;
c. and filtering part of the supernatant after filter pressing by using a 0.22 um filter membrane to a liquid phase small bottle, and carrying out HPLC quantitative analysis, wherein the conversion rate is 93.2% as shown by a high performance liquid chromatography result.
Example 2:
a. preparing a mixed organic solution (non-aqueous phase system): according to DMSO: carrying out dry bulb and thin film transformation on the obtained t-amyl alcohol according to the volume ratio of 6:4 and the total volume of 6m, pumping 3.6m of DMSO for flowering in the reaction kettle, pumping 2.4m of t-amyl alcohol for flowering, and starting stirring;
b. putting 184.5kg (0.09 moL/L) of sucrose into a reaction kettle, pumping 775kg (1.5 moL/L) of vinyl acetate into the reaction kettle for 6m high-speed cultivation after starting stirring and completely dissolving, then putting 360kg of L1754 lipase into the reaction kettle, carrying out heat preservation reaction at 30 ℃, carrying out reaction at the stirring speed of 200 rpm for 15 hours, filtering by a filter press after the reaction is finished to remove the L1754 lipase in the reaction system, and standing at room temperature;
c. and filtering part of the supernatant after pressure filtration by using a 0.22 um filter membrane to a liquid phase small bottle, and carrying out HPLC quantitative analysis, wherein the conversion rate is 90.71% as shown by a high performance liquid chromatography result.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the invention in any manner; those skilled in the art can make numerous possible variations and modifications to the present teachings, or modify equivalent embodiments to equivalent variations, without departing from the scope of the present teachings, using the methods and techniques disclosed above. Therefore, any simple modification, equivalent replacement, equivalent change and modification made to the above embodiments according to the technical essence of the present invention are still within the scope of the protection of the technical solution of the present invention.
Claims (6)
1. A method for synthesizing sucrose-6-acetate in a non-aqueous phase system, which is characterized by comprising the following steps:
uniformly mixing DMF and tert-amyl alcohol according to the volume ratio of 1:3-5 to form a non-aqueous phase system, and adding sucrose, vinyl acetate and lipase into the non-aqueous phase system, wherein the mixed solution is as follows: sucrose: vinyl acetate: the mass ratio of the lipase is 50: 1: 5: 4, carrying out heat preservation reaction at 30-35 ℃ for 8-24h, controlling the rotating speed at 150-250rpm, and after the reaction is finished, filtering by a filter press to remove lipase in the reaction system to obtain a supernatant, wherein the non-aqueous phase system is any one of DMF/tert-amyl alcohol, DMF/tert-butyl alcohol and DMSO/tert-amyl alcohol; the lipase is one of bacillus subtilis lipase and L1754 lipase.
2. The method for synthesizing sucrose-6-acetate in a non-aqueous system as claimed in claim 1, wherein: the volume ratio of DMF to tertiary amyl alcohol is 1: 3-5.
3. The method for synthesizing sucrose-6-acetate in a non-aqueous system as claimed in claim 1, wherein: the volume ratio of DMF to tertiary butanol is 1: 3-5.
4. The method for synthesizing sucrose-6-acetate in a non-aqueous system as claimed in claim 1, wherein: the volume ratio of the DMSO to the tertiary amyl alcohol is 1: 3-5.
5. A process for the synthesis of sucrose-6-acetate in a non-aqueous system according to any of claims 1 to 4, characterized in that: the concentration of the lipase is 6-60 mg/mL.
6. A process for the synthesis of sucrose-6-acetate in a non-aqueous system according to any of claims 1 to 4, characterized in that: the concentration of the sucrose is 10-20 g/L.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101886100A (en) * | 2010-07-12 | 2010-11-17 | 江南大学 | Method for preparing sucrose-6-acetic ester by enzymatic method |
| CN103184257A (en) * | 2011-12-31 | 2013-07-03 | 浙江工业大学 | Method for on-line synthesizing sucrose-6-acetate catalyzed by lipase |
| CN106047744A (en) * | 2016-05-06 | 2016-10-26 | 杭州鑫富科技有限公司 | Bacillus amyloliquefaciens and applications thereof |
| CN111575327A (en) * | 2020-05-25 | 2020-08-25 | 安徽金禾实业股份有限公司 | Method for synthesizing sucrose-6-acetate by using rhizomucor miehei lipase as catalyst |
| CN111763703A (en) * | 2020-07-02 | 2020-10-13 | 浙江工业大学 | Method for synthesizing sucrose-6-ethyl ester by enzyme method in organic solvent |
| CN113121621A (en) * | 2021-04-26 | 2021-07-16 | 南通市常海食品添加剂有限公司 | Method for preparing sucralose-6-acetate by enzymatic synthesis of sucrose-6-acetate |
| CN113151374A (en) * | 2021-04-26 | 2021-07-23 | 南通市常海食品添加剂有限公司 | Method for improving yield of sucrose-6-acetate synthesized by enzyme method |
-
2021
- 2021-11-23 CN CN202111393579.9A patent/CN114107411A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101886100A (en) * | 2010-07-12 | 2010-11-17 | 江南大学 | Method for preparing sucrose-6-acetic ester by enzymatic method |
| CN103184257A (en) * | 2011-12-31 | 2013-07-03 | 浙江工业大学 | Method for on-line synthesizing sucrose-6-acetate catalyzed by lipase |
| CN106047744A (en) * | 2016-05-06 | 2016-10-26 | 杭州鑫富科技有限公司 | Bacillus amyloliquefaciens and applications thereof |
| CN111575327A (en) * | 2020-05-25 | 2020-08-25 | 安徽金禾实业股份有限公司 | Method for synthesizing sucrose-6-acetate by using rhizomucor miehei lipase as catalyst |
| CN111763703A (en) * | 2020-07-02 | 2020-10-13 | 浙江工业大学 | Method for synthesizing sucrose-6-ethyl ester by enzyme method in organic solvent |
| CN113121621A (en) * | 2021-04-26 | 2021-07-16 | 南通市常海食品添加剂有限公司 | Method for preparing sucralose-6-acetate by enzymatic synthesis of sucrose-6-acetate |
| CN113151374A (en) * | 2021-04-26 | 2021-07-23 | 南通市常海食品添加剂有限公司 | Method for improving yield of sucrose-6-acetate synthesized by enzyme method |
Non-Patent Citations (2)
| Title |
|---|
| 王勍;郑璞;倪晔;孙志浩: "非水介质中脂肪酶催化合成蔗糖-6-乙酸酯", 食品与发酵工业, vol. 036, no. 012, pages 20 - 24 * |
| 钱海均;罗旭;: "叔戊醇/水两相体系脂肪酶催化合成蔗糖酯", 浙江化工, no. 12, pages 30 - 34 * |
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