CN103184257B - Method for on-line synthesizing sucrose-6-acetate catalyzed by lipase - Google Patents

Method for on-line synthesizing sucrose-6-acetate catalyzed by lipase Download PDF

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CN103184257B
CN103184257B CN201110457507.6A CN201110457507A CN103184257B CN 103184257 B CN103184257 B CN 103184257B CN 201110457507 A CN201110457507 A CN 201110457507A CN 103184257 B CN103184257 B CN 103184257B
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reaction
acetic ester
channel
lipase
sucrose
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CN103184257A (en
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杜理华
罗锡平
顾生妹
张航诚
胡玉婷
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Zhejiang University of Technology ZJUT
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Abstract

The invention discloses a method for on-line synthesizing sucrose-6-acetate catalyzed by lipase. According to the method, sucrose and vinyl acetate with a molar ratio being 1 : 15-20 are used as raw materials; 0.5-1.0 g of the lipase (Lipozyme TLIM) is used as a catalyst and a mixed solvent formed by tert-amyl alcohol and DMSO is used as a reaction solvent. The lipase (Lipozyme TLIM) is uniformly filled in a reaction channel of a microfluidic channel reactor, wherein the inner diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4 mm, and the length of the reaction channel is 0.5-1.0 m; the raw materials and the reaction solvent are continuously introduced into the reaction channel for an acylation reaction, wherein the temperature of the acylation reaction is controlled at 40-55 DEG C and the time of the acylation reaction is 20-40 min; a reaction liquid is collected on-line; and the sucrose-6-acetate is obtained after the reaction liquid is subjected to conventional post-treatment. The method provided by the invention has the advantages of short reaction time, high selectivity and high yield.

Description

A kind of method of lipase-catalyzed online synthesizing cane sugar-6-acetic ester
(1) technical field
The present invention relates to a kind of method of lipase-catalyzed online controlled selectively synthesizing sucrose-6-acetic ester.
(2) background technology
Micro-fluidic (Microfluidics) is that manipulation is received and risen to skin and rises technology and the science of volume fluid in micron order structure, is the new cross discipline of emergence rapidly nearly ten years.Current, the development of micro-fluidic has surmounted the original object that is mainly analytical chemistry service greatly, and is becoming the important technological platform of whole chemistry subject, life science, instrumental science and even information science new round innovation research.
Delivered after the document of first section synthetic compound in micro-fluidic chip microreactor from Harrison seminar in 1997, micro-fluidic chip reactor has been successfully used to multiple organic synthesis, and has shown application prospect widely.Along with the development of micro-mixing, micro-reaction technology in micro-fluidic chip, in chip, carry out building-up reactions and become one of the study hotspot in micro-fluidic chip field.
Compare with conventional chemical reactor, micro passage reaction not only has the diffusion length making between reactant to be shortened greatly, and mass transfer velocity is fast; The easy control of reaction conditions such as reactant ratio, temperature, reaction times and flow velocity, side reaction is less; Need reactant consumption very micro-, not only can reduce the consumption of costliness, poisonous, adverse reaction thing, the environmental pollutant that produce in reaction process are also few, are the technology of a kind of environmental friendliness, study on the synthesis novel substance.
Sucrose fatty ester is as a kind of sucrose derivative, is a kind of safe, nontoxic, free from extraneous odour of excellent property, pollution-free, polyol-based non-ionic surfactant to human body non-stimulated, good stability without any side effects, fully biodegradable.It can reduce the surface tension of water effectively, has good performance at aspects such as wetting power, dispersion force, lyotropy, foaming power, emulsifying power, detersive poweies.Meanwhile, also there is killing pests and suppressing bacteria performance.Therefore, its strong adaptability, applied range.The fields such as foodstuffs industry, daily-use chemical industry, medicine industry, weaving, agriculture and animal husbandry are widely used at present, in particular as emulsifying agent, dispersion agent, pore forming material, wetting agent and sanitising agent in foodstuffs industry; Makeup, washing composition etc. in daily-use chemical industry.
Sucrose ester is generally white powdery, bulk or waxy solid, and also or arborescens liquid form thick with colourless or micro-yellow exists sometimes, nontoxic, not skin irritation and mucous membrane.Eat in human body, hydrolyzable is edible fat acid and sucrose, has nutritive value, participates in the metabolism of human body, there is emulsification, dispersion, wetting, foaming, viscosity adjustment, prevent aging and prevent the performances such as partial crystallization, be soluble in the organic solvents such as ethanol, propyl alcohol, chloroform, propylene glycol, without sharp melting point, start above fusing at 50 DEG C, in warm water, disperse or dissolve, solubleness in cold water is less, stable under weak acid and weak base, under strong acid and strong base, is easily hydrolyzed.
So far sucrose ester synthetic has solvent method, mini-emulsion process, water solvent method, enzyme process and solventless method etc.But existing method exists defect more or less.
Mini-emulsion process and water solvent method all need a large amount of soaps to make emulsifying agent, product purification difficulty, and color and luster is darker, and water solvent method also has the shortcoming that productive rate is low.Although the solventless method reaction times is short, do not use any solvent, meet the demand for development of Green Chemistry, due to the low conversion rate of the synthetic fatty acid ester of solventless method, the monoester content of sucrose ester is low, and product cost is high, has limited their application.Solvent method is because solvent DMSO, DMF etc. are inflammable, poisonous, and purifying products is more difficult, therefore should not be applied to the production of food grade sucrose ester.Therefore the synthetic method of developing efficient sucrose ester has very important practical significance.
At present, there is more Chinese scholars to be studied the enzyme catalysis of sucrose ester in organic medium is synthetic, successively reported the esterification of lipase-catalyzed multiple disaccharides in trimethyl carbinol system and the trimethyl carbinol and DMSO mixed solvent system (4: 1).Compared with traditional solvent method, mixed solvent system adopts tertiary amyl alcohol nontoxic or that toxicity is less as reaction medium, has greatly reduced the use of noxious solvent, is applicable to develop the various sucrose ester products with using value.But the method often needs the reaction times (24h) of growing, and transformation efficiency and the selectivity of reaction are not high, later separation difficulty.Therefore we have studied the method for lipase-catalyzed selectively synthesizing sucrose-6-acetic ester in microfluidic channel reactor.
(3) summary of the invention
The technical problem to be solved in the present invention is to provide the novel process of lipase-catalyzed selectively synthesizing sucrose-6-acetic ester in a kind of microfluidic channel reactor, has advantages of that the reaction times is short, selectivity is high and productive rate is high.
For solving the problems of the technologies described above, the present invention adopts following technical scheme:
A kind of method of lipase-catalyzed online synthesizing cane sugar-6-acetic ester, described method adopts microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in syringe pump, be connected with reaction channel entrance by an interface, described product collector is connected with reaction channel outlet by an interface, and described reaction channel internal diameter is 0.8~2.4mm, and reaction channel length is 0.5~1.0m, described method comprises: taking mol ratio as 1: the sucrose of 15-20 and vinyl-acetic ester are raw material, taking 0.5-1.0g Lipozyme TLIM as catalyzer, taking the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide (DMSO) as reaction solvent, raw material and reaction solvent are placed in to syringe, by Lipozyme TLIM uniform filling in reaction channel, under the promotion of syringe pump, make raw material and reaction solvent carry out acylation reaction in passing into reaction channel continuously, controlling acylation reaction temperature is 40-55 DEG C, the acylation reaction time is 20-40min, collect online reaction solution by product collector, reaction solution obtains cane sugar-6-acetic ester through conventional aftertreatment.
In the microfluidic channel reactor that the present invention adopts, described syringe number can be one or more, depending on concrete reaction requirement.Such as, in the time using two syringes, can adopt T-shaped or Y type interface that different reactants is introduced from two entrances, conflux and enter public reaction channel, middle reactant molecule contact by microchannel increases with probability of collision, makes two strands of reaction solution streams in public reaction channel, mix and react.
Described microfluidic channel reactor also comprises thermostat container, and described reaction channel is placed in thermostat container, can effectively control temperature of reaction with this.Described thermostat container can require to select voluntarily according to temperature of reaction, such as constant temperature water bath case etc.
The present invention does not limit for the material of reaction channel, the material of recommendation green, environmental protection, for example silicone tube; Shape for reaction channel is preferably curved shape, can ensure at the uniform velocity stable the passing through of reaction solution.
The present invention in implementation process, can be first with the mixed solvent of tertiary amyl alcohol and DMSO (tertiary amyl alcohol: DMSO=4: 1) dissolving saccharose, its consumption is as long as ensure that sucrose can fully dissolve, and is loaded in syringe for subsequent use; Only dissolve vinyl-acetic ester with nontoxic tertiary amyl alcohol, be loaded in another syringe for subsequent use; Then for example, under promoting, syringe pump (PHD2000 syringe pump) make raw material and reaction solvent react in passing into reaction channel.Therefore, in the reaction solvent that the present invention uses, the volume ratio of tertiary amyl alcohol and DMSO is greater than 4: 1, than conventional shaking table reaction, can the usage quantity of poisonous DMSO is down to minimum.
In the present invention, the commodity that described Lipozyme TLIM uses letter (novozymes) company of Novi to produce, its be a kind of by microorganism prepare, 1,3 position-specific, the preparation of food-grade lipase (EC3.11.3) on particle silica gel.It obtains, produces through submerged fermentation with a kind of gene modification aspergillus oryzae (Aspergillus oryzae) microorganism from Thermomyces lanuginosus.
Further, the mol ratio of described sucrose and vinyl-acetic ester is preferably 1: 18~and 20, most preferably be 1: 18.
Further, described acylation reaction temperature is preferably 50~55 DEG C, most preferably is 52 DEG C.
Further, the described acylation reaction time is preferably 25~40min, most preferably is 30min.
Reaction product of the present invention can be collected online, and gained reaction solution can obtain cane sugar-6-acetic ester by conventional post-treating method.Described conventional post-treating method can be: the underpressure distillation of gained reaction solution is except desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol: water=65: 25: 1 (volume ratio), wet method upper prop after sample dissolves with a small amount of elution reagent, collect elutriant, TLC follows the tracks of wash-out process simultaneously, and the elutriant that contains single product obtaining is merged to evaporate to dryness, can obtain white monoesters crystal, be cane sugar-6-acetic ester.
In the present invention, although there are 8 hydroxyls that performance is close in sucrose, but lipase-catalyzed selectively synthesizing sucrose-6-acetic ester has higher transformation efficiency and selectivity in micro-fluidic micro passage reaction, the transformation efficiency of diester is very low, almost do not have, the content of the monoesters obtaining by column chromatography for separation can reach 98%.The structure warp of product 1h NMR confirmation.This shows that the enzymatic selectivity of cane sugar-6-acetic ester in micro-fluidic micro passage reaction is synthetic and has good reaction conversion ratio and selectivity, can realize high monoesters rate.
Compared with prior art, beneficial effect of the present invention is: selectively synthesizing sucrose-6-acetic ester in microfluidic channel reactor of the present invention, and this method has not only shortened the reaction times widely, and has high transformation efficiency and reaction preference; The usage quantity that has simultaneously reduced DMSO, has environment-friendly advantage.
(4) brief description of the drawings
Fig. 1 is the structural representation of the microfluidic channel reactor that adopts of embodiment.
(5) embodiment
With specific embodiment, protection scope of the present invention is described further below, but protection scope of the present invention is not limited to this:
The structure of the microfluidic channel reactor that the embodiment of the present invention is used is with reference to figure 1, comprise a syringe pump (not shown), two syringes 1 and 2, reaction channel 3, constant temperature water bath case (5, only show its floor map) and product collector 4; Two syringes 1 and 2 are installed in syringe pump, be connected with reaction channel 3 entrances by a Y type interface, described reaction channel 3 is placed in constant temperature water bath case 5, control temperature of reaction by constant temperature water bath case 5, the internal diameter 2.4mm of described reaction channel 3, the long 1m of reaction channel, described reaction channel 3 exports by an interface and is connected with product collector 4.
Embodiment 1: cane sugar-6-acetic ester synthetic
With reference to figure 1, sucrose (0.4mmol) is dissolved in the mixed solvent of 10mL (tertiary amyl alcohol: DMSO=4: 1 (v/v)), vinyl-acetic ester (7.2mmol) is dissolved in 10mL tertiary amyl alcohol, is then loaded on respectively in 10mL syringe for subsequent use.0.87g Lipozyme TLIM uniform filling is in the reaction channel of microfluidic channel reactor, and under PHD2000 syringe pump promotes, two-way reaction solution is respectively with 10.4 μ Lmin -1flow velocity enter in reaction channel and react by " Y " joint, control 52 DEG C of temperature of reactor, reaction solution is continuous flow reaction 30min in reaction channel, collects online reaction solution by product collector, and underpressure distillation is except desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol: water=65: 25: 1, and the high 35cm of post, column diameter 4.5cm, wet method upper prop after sample dissolves with a small amount of elution reagent, elutriant is collected flow velocity 2mLmin -1, TLC follows the tracks of wash-out process simultaneously, and the elutriant that contains single product obtaining is merged to evaporate to dryness, can obtain white monoesters crystal, is cane sugar-6-acetic ester.HPLC measures sucrose inversion rate 96%, and the selectivity (total content of the sugar ester of cane sugar-6-acetic ester content/generation) of cane sugar-6-acetic ester is 98%.
Nuclear-magnetism characterization result is as follows:
Cane sugar-6-acetic ester: 1h-NMR (DMSO-d6, δ, ppm): 5.18-5.14 (m, 3H, the 2 β-OH of sucrose, the 3 α-OH of sucrose and the 4 β-OH of sucrose), 5.03 (d, 1H, J=5.5Hz, 3 ' β-the OH of sucrose), 4.90 (s, 1H, 4 ' α-the OH of sucrose), 4.83-4.80 (t, 1H, J=6.5Hz, 5 ' β-the OH of sucrose), 4.58 (d, 1H, J=8.0Hz, 1 ' β-the OH of sucrose), 4.41-4.39 (t, 1H, J=5.0Hz, the H of sucrose α-6 α), 4.24 (d, 1H, J=10.5Hz, the H of sucrose b-6 α), 4.04-3.99 (m, 1H, the H-5 β of sucrose), 3.92-3.86 (m, 2H, the H-5 ' α of sucrose and H α-1 ' α), 3.73 (d, 1H, J=6.0Hz, the H of sucrose b-1 ' α), 3.60-3.47 (m, 4H, the H-3 ' α of sucrose, H-4 ' β, H a-6 ' β and H b-6 ' β), 3.35 (m, 1H, the H-3 β of sucrose), 3.22-3.19 (m, 1H, the H-2 β of sucrose), 3.09-3.04 (m, 1H, the H-4 β of sucrose), 2.02 (s, 3H, CH 3).
Embodiment 2-5
The temperature that changes microfluidic channel reactor is 40 DEG C (embodiment 2), 45 DEG C (embodiment 3), 50 DEG C (embodiment 4), 55 DEG C (embodiment 5), and other are with embodiment 1, and reaction result is as shown in table 1:
Table 1: the impact of temperature on reaction
The result of table 1 shows, when flow velocity is 10.4 μ Lmin -1reaction times is while being 30min, reaction is with the rising of temperature, transformation efficiency also obviously raises, and in the time that temperature of reaction reaches 52 DEG C, the transformation efficiency of reaction and selectivity are all best, heat up if now continued, will cause the reduction of enzymic activity, thereby cause transformation efficiency and the selectivity of reaction to decrease, so the optimal reaction temperature of synthesizing cane sugar-6-acetic ester is 52 DEG C in microfluidic channel reactor.
Embodiment 6-10
Changing the substrate mol ratio of vinyl-acetic ester and sucrose in micro-fluidic micro passage reaction is 15: 1 (embodiment 6), 16: 1 (embodiment 7), 17: 1 (embodiment 8), 19: 1 (embodiment 9), 20: 1 (embodiment 10), other are with embodiment 1, and result is as shown in table 2.
Table 2: sucrose is compared the impact of reacting with vinyl-acetic ester substrate
Embodiment Vinyl-acetic ester: sucrose Transformation efficiency [%] Selectivity [%]
6 15∶1 68 100
7 16∶1 78 100
8 17∶1 90 92
1 18∶1 96 98
9 19∶1 95 95
10 20∶1 91 100
The result of table 2 shows, along with the increase of reactant vinyl-acetic ester, the transformation efficiency of reaction is also along with increase, and in the time that substrate ratio is 18: 1, the transformation efficiency of reaction and selectivity are comprehensively optimum.If now continue to increase the consumption of reactant vinyl-acetic ester, will cause transformation efficiency and/or the elective reduction of reaction, thereby best substrate ratio is 18: 1.
Embodiment 11-14
Changing the reaction times in micro-fluidic micro passage reaction is 20min (embodiment 11), 25min (embodiment 12), 35min (embodiment 13), 40min (embodiment 14), other are with embodiment 1, and result is as shown in table 3.
Table 3: the reaction times is on reaction conversion ratio and optionally impact
Embodiment Reaction times [min] Transformation efficiency [%] Selectivity [%]
11 20 64 100
12 25 88 99
1 30 96 98
13 35 95 93
14 40 87 99
The result of table 3 shows, along with the increase in reaction times, the transformation efficiency of reaction and selectivity also increase gradually, in the time that 30min is carried out in reaction, transformation efficiency and the selectivity optimum of reaction, if now continue to extend the reaction times, will cause cane sugar-6-acetic ester selectivity and/or transformation efficiency to reduce, thereby the Best Times of synthesizing cane sugar-6-acetic ester is 30min in microfluidic channel reactor.

Claims (6)

1. the method for a lipase-catalyzed online synthesizing cane sugar-6-acetic ester, it is characterized in that: described method adopts microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in syringe pump, be connected with reaction channel entrance by an interface, described product collector is connected with reaction channel outlet by an interface, described reaction channel internal diameter is 0.8~2.4mm, and reaction channel length is 0.5~1.0m, described method comprises: taking mol ratio as 1: the sucrose of 15-20 and vinyl-acetic ester are raw material, taking 0.5-1.0g Lipozyme TLIM as catalyzer, taking the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide as reaction solvent, raw material and reaction solvent are placed in to syringe, by Lipozyme TLIM uniform filling in reaction channel, under the promotion of syringe pump, make raw material and reaction solvent carry out acylation reaction in passing into reaction channel continuously, controlling acylation reaction temperature is 40-55 DEG C, the acylation reaction time is 20-40min, collect online reaction solution by product collector, reaction solution obtains cane sugar-6-acetic ester through conventional aftertreatment.
2. the method for lipase-catalyzed online synthesizing cane sugar-6-acetic ester as claimed in claim 1, it is characterized in that: the tertiary amyl alcohol that it is first 4: 1 by volume ratio that described method comprises the following steps: and the mixed solvent dissolving saccharose of DMSO, be loaded in syringe for subsequent use; Dissolve vinyl-acetic ester with tertiary amyl alcohol, be loaded in another syringe for subsequent use; Then under promoting, syringe pump make raw material and reaction solvent react in passing into reaction channel.
3. the method for lipase-catalyzed online synthesizing cane sugar-6-acetic ester as claimed in claim 1, is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
4. the method for lipase-catalyzed online synthesizing cane sugar-6-acetic ester as claimed in claim 2, is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel is placed in thermostat container.
5. the method for the lipase-catalyzed online synthesizing cane sugar-6-acetic ester as described in one of claim 1~4; it is characterized in that: the mol ratio of described sucrose and vinyl-acetic ester is 1: 18-20; described acylation reaction temperature is 50-55 DEG C, and the described acylation reaction time is 25-40min.
6. the method for the lipase-catalyzed online synthesizing cane sugar-6-acetic ester as described in one of claim 1~4; it is characterized in that: the mol ratio of described sucrose and vinyl-acetic ester is 1: 18; described acylation reaction temperature is 52 DEG C, and the described acylation reaction time is 30min.
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