CN103184256B - Method for on-line synthesizing saccharose-6-laurate by lipase catalysis - Google Patents
Method for on-line synthesizing saccharose-6-laurate by lipase catalysis Download PDFInfo
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Abstract
The invention provides a method for on-line synthesizing saccharose-6-laurate by lipase catalysis, comprising: using saccharose and vinyl laurate, with a mol ratio of 1:8-12, as raw materials, using 0.5-10g of Lipozyme TLIM as a catalyst, and using a mixed solvent of tertiary amyl alcohol and DMSO as a reaction solvent, uniformly filling Lipozyme TLIM in a reaction channel of a microfluidic channel reactor, wherein the internal diameter of the reaction channel of the microfluidic channel reactor is 0.8-2.4mm, and the length of the reaction channel is 0.5-1.0m; continuously introducing the raw materials and the reaction solvent into the reaction channel to perform acylation reaction under 40-55 DEG C for 20-35min, on-line collecting the reaction solution, and then obtaining the saccharose-6-laurate after conventional post-treatment on the reaction solution. The method of the invention has advantages of short reaction time, high selectivity and high yield.
Description
(1) technical field
The present invention relates to the method for lipase-catalyzed online controlled selectively synthesizing sucrose-6-laurate in a kind of microfluidic channel reactor, belong to the nonionic surface active agent technical fields such as microflow control technique and biocatalysis selectively synthesizing sucrose ester.
(2) background technology
Micro-fluidic (Microfluidics) is in micron order structure, to control to receive to rise to technology and the science that skin rises volume fluid, is the new cross discipline emerging 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.
From Harrison seminar in 1997, delivered after the document of first piece of writing synthetic compound in micro-fluidic chip microreactor, 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.
With conventional chemical reactor, compare, 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, the 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, at aspects such as wetting power, dispersion force, lyotropy, foaming power, emulsifying power, detersive poweies, has good performance.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 have been widely used at present, in particular as emulsifying agent, dispersion agent, pore forming material, wetting agent and the sanitising agent in foodstuffs industry; Makeup in daily-use chemical industry, washing composition etc.
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, at 50 ℃, start above fusing, 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).Compare 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-laurate 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-laurate 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 synthesis of sucrose-6-laurate, 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, by an interface, be connected with reaction channel entrance, 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: take mol ratio as 1: the sucrose of 8-12 and vinyl laurate are raw material, the 0.5-1.0g Lipozyme TLIM of take is catalyzer, the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide (DMSO) of take is reaction solvent, raw material and reaction solvent are placed in to syringe, by Lipozyme TLIM uniform filling in reaction channel, under promoting, 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 ℃, the acylation reaction time is 20-35min, by product collector, collect online reaction solution, reaction solution obtains sucrose-6-laurate 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, when 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, with this, can effectively control temperature of reaction.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, and recommendation is green, the material of environmental protection, as silicone tube; Shape for reaction channel is preferably curved shape, can guarantee 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 guarantee that sucrose can fully dissolve, and is loaded in syringe standby; Only with nontoxic tertiary amyl alcohol, dissolve vinyl laurate, be loaded in another syringe standby; For example, in then under syringe pump (PHD2000 syringe pump) promotes, reaction raw materials being mixed in proportion to pass into reaction channel, react.Therefore, the present invention, than conventional shaking table reaction, can be down to minimum by the usage quantity of poisonous DMSO.
In the present invention, the commodity that described Lipozyme TLIM is used 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 (EC3.1.1.3) on particle silica gel.It obtains, with a kind of gene modification aspergillus oryzae (Aspergillus oryzae) microorganism, through submerged fermentation, produces from Thermomyces lanuginosus.
Further, the mol ratio of described sucrose and vinyl laurate is preferably 1: 9～and 11, most preferably be 1: 11.
Further, described acylation reaction temperature is preferably 50～55 ℃, most preferably is 52 ℃.
Further, the described acylation reaction time is preferably 25～30min, most preferably is 30min.
Reaction product of the present invention can be collected online, and gained reaction solution can obtain sucrose-6-laurate 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=10: 1, 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 sucrose-6-laurate.
In the present invention, although there are 8 hydroxyls that performance is close in sucrose, but lipase-catalyzed selectively synthesizing sucrose-6-laurate 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 sucrose-6-laurate 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-laurate 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) accompanying drawing explanation
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, comprises 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, by a Y type interface, be connected with reaction channel 3 entrances, described reaction channel 3 is placed in constant temperature water bath case 5, by constant temperature water bath case 5, control temperature of reaction, the internal diameter 2.4mm of described reaction channel 3, pipe range 1m, described reaction channel 3 outlets are connected with product collector 4 by an interface.
Embodiment 1: sucrose-6-laurate synthetic
With reference to Fig. 1, sucrose (0.4mmol) is dissolved in to 10mL (tertiary amyl alcohol: DMSO=4: in mixed solvent 1 (v/v)), vinyl laurate (4.4mmol) is dissolved in 10mL tertiary amyl alcohol, is then loaded on respectively in 10mL syringe standby.0.87g Lipozyme TLIM uniform filling is in reaction channel, and under PHD2000 syringe pump promotes, two-way reaction solution is respectively with 10.4 μ Lmin
-1flow velocity by " Y " joint, enter and in reaction channel, carry out acylation reaction; by constant temperature water bath case, control temperature of reactor at 52 ℃; reaction solution is continuous flow reaction 30min in reaction channel, by product collector, collects online reaction solution, and underpressure distillation is except desolventizing; with 200-300 order silica gel wet method dress post; elutriant is chloroform: methyl alcohol=10: 1, and the high 35cm of post, column diameter 4.5cm; wet method upper prop after sample dissolves with a small amount of eluent, elutriant is collected flow velocity 2mL/min
-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 crystal.By HPLC, measure transformation efficiency and selectivity of product, result is: sucrose inversion rate is 92%, and sucrose-6-laurate selectivity (the sucrose ester total content of sucrose-6-laurate content/generation) is 98%.
Nuclear-magnetism characterization result is as follows:
Sucrose-6-laurate:
1h-NMR (DMSO-d6, δ, ppm): 5.18-5.14 (m, 3H, the 2 β-OH of sucrose, 3 α-OH and 4 β-OH), 5.03 (d, 1H, J=5.5Hz, 3 ' β-the OH of sucrose), 4.90 (s, 1H, the 4 ' α-OH of sucrose), 4.83-4.80 (t, 1H, J=6.5Hz, the 5 ' β-OH of sucrose), 4.58 (d, 1H, J=8.0Hz, the 1 ' β-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), 2.31-2.29 (m, 2H, a-CH
2), 1.52-1.50 (t, 2H, J=7.0Hz, β-CH
2), 1.25 (m, 16H, n-CH
2), 0.86 (t, 3H, J=7.0Hz, CH
3).
Embodiment 2-5
The temperature that changes microfluidic channel reactor, other are with embodiment 1, and reaction result is as shown in table 1:
Table 1: the impact of temperature on reaction
[a]: transformation efficiency is measured by HPLC; [b]: the content of sucrose-6-laurate in total sucrose ester product
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 when temperature of reaction reaches 52 ℃, the transformation efficiency of reaction and selectivity are all best, if now continued, heat up, will cause the reduction of enzymic activity, thereby cause transformation efficiency and the selectivity of reaction to decrease, so the optimal reaction temperature of sucrose-6-laurate is 52 ℃ in microfluidic channel reactor.
Embodiment 6-9
Changing the substrate mol ratio of vinyl laurate and sucrose in micro-fluidic micro passage reaction is 8: 1 (embodiment 6), 9: 1 (embodiment 7), 10: 1 (embodiment 8), 12: 1 (embodiment 9), other are with embodiment 1, and result is as shown in table 2.
Table 2: sucrose is compared the impact of reacting with vinyl laurate substrate
[a]: transformation efficiency is measured by HPLC; [b]: in total sucrose ester product, the result containing scale 2 of sucrose-6-laurate shows, along with the increase of reactant vinyl laurate, the transformation efficiency of reaction is also along with increase, and when substrate ratio is 11: 1, the transformation efficiency of reaction and selectivity are optimum.If now continue to increase the consumption of reactant vinyl laurate, will cause the elective reduction of reaction, thereby the best substrate ratio of this reaction is 11: 1.
Embodiment 10-14
Changing the reaction times in micro-fluidic micro passage reaction is 15min (embodiment 10), 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 impact of reaction times on reaction
[a]: transformation efficiency is measured by HPLC; [b]: the content of sucrose-6-laurate in total sucrose ester product
The result of table 3 shows, increase along with the reaction times, the transformation efficiency of reaction and selectivity also increase gradually, and when 30min is carried out in reaction, the transformation efficiency of reaction and selectivity are optimum, if now continued, extend the reaction times, will cause sucrose-6-laurate transformation efficiency to reduce, the transformation efficiency of sucrose lauric acid diester increases, and reaction preference reduces, thereby the synthetic Best Times of sucrose-6-laurate is 30min in microfluidic channel reactor.
Claims (6)
1. the method for lipase-catalyzed online synthesis of sucrose-6-laurate, 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, by an interface, be connected with reaction channel entrance, 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: the sucrose that the mol ratio of take is 1:8-12 and vinyl laurate are raw material, the 0.5-1.0g Lipozyme TLIM of take is catalyzer, the mixed solvent of tertiary amyl alcohol and methyl-sulphoxide of take is reaction solvent, raw material and reaction solvent are placed in to syringe, by Lipozyme TLIM uniform filling in reaction channel, under promoting, 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 ℃, the acylation reaction time is 20-35min, by product collector, collect online reaction solution, reaction solution obtains sucrose-6-laurate through conventional aftertreatment.
2. the method for lipase-catalyzed online synthesis of sucrose-6-laurate 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 standby; With tertiary amyl alcohol, dissolve vinyl laurate, be loaded in another syringe standby; Then under syringe pump promotes, reaction raw materials being mixed in proportion to pass into reaction channel, react.
3. the method for lipase-catalyzed online synthesis of sucrose-6-laurate 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 synthesis of sucrose-6-laurate 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 synthesis of sucrose-6-laurate as described in one of claim 1～4; it is characterized in that: the mol ratio of described sucrose and vinyl laurate is 1:9～11; described acylation reaction temperature is 50～55 ℃, and the described acylation reaction time is 25～30min.
6. the method for the lipase-catalyzed online synthesis of sucrose-6-laurate as described in one of claim 1～4; it is characterized in that: the mol ratio of described sucrose and vinyl laurate is 1:11; described acylation reaction temperature is 52 ℃, and the described acylation reaction time is 30min.
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| CN103667396B (en) * | 2013-09-02 | 2015-10-07 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis 6 " method of-O-lauroyl-naringin dihydrochalcone ester |
| CN103667402B (en) * | 2013-09-02 | 2016-03-02 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis 6 " method of-O-lauroyl-naringin ester |
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| CN107488690A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 glucose ester valeryl) mexiletine |
| CN107418989A (en) * | 2017-08-21 | 2017-12-01 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 sucrose ester valeryl) metoprolol |
| CN107488683A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis N（5 vinyl acetate valeryls）The method of mexiletine |
| CN107955822A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis S-（4- methyl-benzyls）The method of laurate thioesters |
| CN111560408B (en) * | 2020-02-29 | 2022-11-25 | 浙江工业大学 | Method for synthesizing coumarin-3-carboxylic acid sugar ester derivative on line based on flow chemistry enzymatic catalysis |
| CN111455005B (en) * | 2020-02-29 | 2023-05-05 | 浙江农林大学 | Method for synthesizing coumarin-3-carboxylic acid-6' -O-D-sucrose ester derivative on line enzymatically based on flow chemistry |
| CN114160054B (en) * | 2022-02-14 | 2022-04-26 | 南京禾勤生物医药科技有限公司 | Continuous flow hydrogenation reaction device and selective reduction method of unsaturated aldehyde ketone |
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