CN103184256A - 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 nonionic surface active agent technical fields such as microflow control technique and biocatalysis selectively synthesizing sucrose ester.
(2) background technology
Micro-fluidic (Microfluidics) is to control to receive in the micron order structure to rise to technology and the science that skin rises the volume fluid, is the new cross discipline that emerges rapidly over past ten years.Current, the development of micro-fluidic has surmounted the original purpose that is mainly the 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.
After Harrison seminar in 1997 had delivered the document of first piece of writing synthetic compound in the micro-fluidic chip microreactor, the micro-fluidic chip reactor had been successfully used to multiple organic synthesis, and has showed application prospect widely.Along with the development of little mixing, little reaction technology in the micro-fluidic chip, in chip, carry out building-up reactions and become one of the research focus in micro-fluidic chip field.
Compare with the conventional chemical reactor, micro passage reaction not only has the diffusion length that makes between reactant to be shortened greatly, and mass transfer velocity is fast; Easy control of reaction conditions such as reactant ratio, temperature, reaction times and flow velocity, side reaction is less; Need the reactant consumption very little, not only can reduce the consumption of costliness, poisonous, adverse reaction thing, the environmental pollutant that produce in the 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, be a kind of excellent property safe, nontoxic, free from extraneous odour, pollution-free, to the polyol-based non-ionic surfactant of 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.Simultaneously, also has the killing pests and suppressing bacteria performance.Therefore, its adaptability is strong, applied range.Fields such as foodstuffs industry, daily-use chemical industry, medicine industry, weaving, agriculture and animal husbandry have been widely used at present, emulsifying agent, dispersion agent, pore forming material, wetting agent and sanitising agent in the foodstuffs industry; Makeup in the daily-use chemical industry, washing composition etc.
Sucrose ester is generally white powdery, bulk or waxy solid, and also thick or arborescens liquid form exists with colourless or little yellow sometimes, nontoxic, not skin irritation and mucous membrane.Eat in the human body, hydrolyzable is edible fat acid and sucrose, has nutritive value, participates in the metabolism of human body, have emulsification, dispersion, wetting, foaming, viscosity adjustment, prevent aging and prevent performance such as partial crystallization, be soluble in the organic solvents such as ethanol, propyl alcohol, chloroform, propylene glycol, no sharp melting point is namely beginning fusing more than 50 ℃, in warm water, disperse or dissolve, solubleness in cold water is less, and is stable under weak acid and weak base, and hydrolysis easily takes place under strong acid and strong base.
So far sucrose ester synthetic has solvent method, mini-emulsion process, water solvent method, enzyme process and solventless method etc.But existing method exists defective more or less.
Mini-emulsion process and water solvent method all need a large amount of soaps to make emulsifying agent, the product purification difficulty, and color and luster is darker, and the water solvent method also has the low shortcoming of productive rate.Though the solventless method reaction times is short, does not use any solvent, meets the demand for development of Green Chemistry, because the transformation efficiency of the fatty acid ester that solventless method synthesizes is low, the monoester content of sucrose ester is low, and the product cost height has limited their application.Solvent method is because solvent DMSO, DMF etc. are inflammable, poisonous, and purifying products is difficult, therefore should not be applied to the production of food grade sucrose ester.Therefore developing efficiently, the synthetic method of sucrose ester has very important and practical meanings.
At present, there is more Chinese scholars to study the enzyme catalysis of sucrose ester in the organic medium is synthetic, successively reported the esterification of lipase-catalyzed multiple disaccharides in trimethyl carbinol system and the trimethyl carbinol and the 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 significantly reduced the use of noxious solvent, is applicable to the various sucrose ester products with using value of exploitation.But this method often needs the long reaction times (24h), and transformation efficiency and the selectivity of reaction are not high, the later separation difficulty.Therefore we have studied the method for lipase-catalyzed selectively synthesizing sucrose-6-laurate in the microfluidic channel reactor.
(3) summary of the invention
The technical problem to be solved in the present invention provides the novel process of lipase-catalyzed selectively synthesizing sucrose-6-laurate in a kind of microfluidic channel reactor, has the advantage 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:
The method of a kind of lipase-catalyzed online synthesis of sucrose-6-laurate, described method adopts the microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in the syringe pump, be connected with the reaction channel entrance by an interface, described product collector is connected with the 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: be 1 with mol ratio: the sucrose of 8-12 and vinyl laurate are raw material; be catalyzer with 0.5-1.0g lipase Lipozyme TLIM; mixed solvent with tertiary amyl alcohol and methyl-sulphoxide (DMSO) is reaction solvent; raw material and reaction solvent are placed syringe; evenly be filled in lipase Lipozyme TLIM in the reaction channel; under syringe pump promotes, raw material and reaction solvent are fed continuously and carry out acylation reaction in the reaction channel; control acylation reaction temperature is 40-55 ℃; the acylation reaction time is 20-35min; by the online collection reaction solution of product collector, 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, decides on concrete reaction requirement.Such as, when using two syringes, can adopt T type or Y type interface that different reactants is introduced from two entrances, conflux and enter public reaction channel, middle reactant molecule contact by the microchannel increases with probability of collision, two strands of reaction solutions streams are mixed in public reaction channel and reacts.
Described microfluidic channel reactor also comprises thermostat container, and described reaction channel places 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 the constant temperature water bath case etc.
The present invention does not limit for the material of reaction channel, recommends to use material green, 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 earlier (tertiary amyl alcohol: DMSO=4: 1) dissolving saccharose, its consumption be as long as guarantee that sucrose can fully dissolve, and be loaded in the syringe standby with the mixed solvent of tertiary amyl alcohol and DMSO; Only with nontoxic tertiary amyl alcohol dissolving vinyl laurate, be loaded in another syringe standby; Making reaction raw materials be mixed in proportion to feed in the reaction channel then under syringe pump (for example PHD2000 syringe pump) promotes reacts.Therefore, the present invention can be down to the usage quantity of poisonous DMSO minimum than the shaking table reaction of routine.
Among the present invention, the commodity that described lipase Lipozyme TLIM uses letter (novozymes) company of Novi to produce, it is a kind of by microorganism preparation, 1,3 position-specific, the preparation of food-grade lipase (EC3.1.1.3) 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 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 onlinely be collected, and the gained reaction solution can obtain sucrose-6-laurate by conventional post-treating method.Described conventional post-treating method can be: gained reaction solution underpressure distillation desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol=10: 1, sample dissolves back wet method upper prop with a small amount of elution reagent, collect elutriant, TLC follows the tracks of the wash-out process simultaneously, and the elutriant that contains single product that obtains is merged evaporate to dryness, can obtain the monoesters crystal of white, be sucrose-6-laurate.
Among the present invention, though 8 hydroxyls that performance is close are arranged in the 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 that obtains by column chromatography for separation can reach 98%.The structure warp of product
1H NMR conclusive evidence.This shows that the enzymatic selectivity of sucrose in the micro-fluidic micro passage reaction-6-laurate is synthetic and has good reaction conversion ratio and selectivity, can realize high mono-esterification rate.
Compared with prior art, beneficial effect of the present invention is: selectively synthesizing sucrose in the microfluidic channel reactor of the present invention-6-laurate, and this method has not only shortened the reaction times widely, and has high transformation efficiency and reaction preference; Reduce the usage quantity of DMSO simultaneously, had environment-friendly advantage.
(4) description of drawings
Fig. 1 is the structural representation of the microfluidic channel reactor of embodiment employing.
(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 thereto:
The structure of the microfluidic channel reactor that the embodiment of the 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 the syringe pump, be connected with reaction channel 3 entrances by a Y type interface, described reaction channel 3 places 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 10mL, and (tertiary amyl alcohol: DMSO=4: in the mixed solvent 1 (v/v)), vinyl laurate (4.4mmol) is dissolved in the 10mL tertiary amyl alcohol, is loaded in the 10mL syringe standby then respectively.0.87g lipase Lipozyme TLIM evenly is filled in the reaction channel, under the PHD2000 syringe pump promoted, the two-way reaction solution was respectively with 10.4 μ Lmin
-1Flow velocity enter by " Y " joint and carry out acylation reaction in the reaction channel; control temperature of reactor at 52 ℃ by the constant temperature water bath case; reaction solution is continuous flow reaction 30min in reaction channel, by the online collection reaction solution of product collector, underpressure distillation desolventizing; with 200-300 order silica gel wet method dress post; elutriant is chloroform: methyl alcohol=10: 1, the high 35cm of post, column diameter 4.5cm; sample dissolves back wet method upper prop with a small amount of eluent, and elutriant is collected flow velocity 2mL/min
-1, TLC follows the tracks of the wash-out process simultaneously, and the elutriant that contains single product that obtains is merged evaporate to dryness, can obtain the crystal of white.Measure transformation efficiency and selectivity of product by HPLC, the result is: the sucrose inversion rate is 92%, and sucrose-6-laurate selectivity (the sucrose ester total content of sucrose-6-laurate content/generation) is 98%.
The nuclear-magnetism characterization result is as follows:
Sucrose-6-laurate:
1H-NMR (DMSO-d6, δ, ppm): 5.18-5.14 (m, 3H, 2 β of sucrose-OH, 3 α-OH and 4 β-OH), 5.03 (d, 1H, J=5.5Hz, 3 ' β of sucrose-OH), 4.90 (s, 1H, 4 ' α of sucrose-OH), 4.83-4.80 (t, 1H, J=6.5Hz, 5 ' β of sucrose-OH), 4.58 (d, 1H, J=8.0Hz, 1 ' β of sucrose-OH), 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
Change the temperature of microfluidic channel reactor, other are with embodiment 1, and reaction result is as shown in table 1:
Table 1: temperature is to the influence of 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 when being 30min, reaction is with the rising of temperature, transformation efficiency also obviously raises, and when temperature of reaction reached 52 ℃, the transformation efficiency of reaction and selectivity were all best, heat up if continue this moment, 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 in the microfluidic channel reactor-6-laurate is 52 ℃.
Embodiment 6-9
Change that the substrate mol ratio of vinyl laurate and sucrose is 8: 1 (embodiment 6), 9: 1 (embodiment 7), 10: 1 (embodiment 8), 12: 1 (embodiment 9) in the micro-fluidic micro passage reaction, other are with embodiment 1, and the result is as shown in table 2.
Table 2: the influence of sucrose and vinyl laurate substrate comparison reaction
[a]: transformation efficiency is measured by HPLC; [b]: the result who contains scale 2 of sucrose-6-laurate shows in total sucrose ester product, and along with the increase of reactant vinyl laurate, the transformation efficiency of reaction is also along with increase, when the substrate ratio is 11: 1, and the transformation efficiency of reaction and selectivity optimum.If continue to increase the consumption of reactant vinyl laurate this moment, the selectivity that will cause reacting reduces, thereby the best substrate ratio of this reaction is 11: 1.
Embodiment 10-14
Change that the reaction times is 15min (embodiment 10), 20min (embodiment 11), 25min (embodiment 12), 35min (embodiment 13), 40min (embodiment 14) in the micro-fluidic micro passage reaction, other are with embodiment 1, and the result is as shown in table 3.
Table 3: the reaction times is to the influence of 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, when 30min is carried out in reaction, and the transformation efficiency of reaction and selectivity optimum, prolong the reaction times if continue this moment, 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 in the microfluidic channel reactor-6-laurate is 30min.
Claims (6)
1. the method for lipase-catalyzed online synthesis of sucrose-6-laurate, it is characterized in that described method adopts the microfluidic channel reactor, described microfluidic channel reactor comprises syringe pump, syringe, reaction channel and product collector, described syringe is installed in the syringe pump, be connected with the reaction channel entrance by an interface, described product collector is connected with the 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: be 1 with mol ratio: the sucrose of 8-12 and vinyl laurate are raw material; be catalyzer with 0.5-1.0g lipase Lipozyme TLIM; mixed solvent with tertiary amyl alcohol and methyl-sulphoxide is reaction solvent; raw material and reaction solvent are placed syringe; evenly be filled in lipase Lipozyme TLIM in the reaction channel; under syringe pump promotes, raw material and reaction solvent are fed continuously and carry out acylation reaction in the reaction channel; control acylation reaction temperature is 40-55 ℃; the acylation reaction time is 20-35min; by the online collection reaction solution of product collector, reaction solution obtains sucrose-6-laurate through conventional aftertreatment.
2. the method for lipase-catalyzed online synthesis of sucrose as claimed in claim 1-6-laurate, it is characterized in that: described method comprises the following steps: to be 4: 1 tertiary amyl alcohol and the mixed solvent dissolving saccharose of DMSO with volume ratio earlier, is loaded in the syringe standby; Dissolve vinyl laurate with tertiary amyl alcohol, be loaded in another syringe standby; Making reaction raw materials be mixed in proportion to feed in the reaction channel then under syringe pump promotes reacts.
3. the method for lipase-catalyzed online synthesis of sucrose as claimed in claim 1-6-laurate, it is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel places thermostat container.
4. the method for lipase-catalyzed online synthesis of sucrose as claimed in claim 2-6-laurate, it is characterized in that: described microfluidic channel reactor comprises thermostat container, and described reaction channel places thermostat container.
5. as the method for the described lipase-catalyzed online synthesis of sucrose of one of claim 1～4-6-laurate; it is characterized in that: the mol ratio of described sucrose and vinyl laurate is 9～11: 1; described acylation reaction temperature is 50～55 ℃, and the described acylation reaction time is 25～30min.
6. as the method for the described lipase-catalyzed online synthesis of sucrose of one of claim 1～4-6-laurate; it is characterized in that: the mol ratio of described sucrose and vinyl laurate is 11: 1; described acylation reaction temperature is 52 ℃, and the described acylation reaction time is 30min.
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| CN103667402A (en) * | 2013-09-02 | 2014-03-26 | 浙江工业大学 | Method for synthesizing 6''-O-lauroyl-naringin ester on line by using lipase as catalyst |
| 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 |
| CN107475330A (en) * | 2017-08-21 | 2017-12-15 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 glucose ester valeryl) metoprolol |
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| 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 |
| CN112921060A (en) * | 2021-03-16 | 2021-06-08 | 浙江工业大学 | Method for catalytically synthesizing sucrose fatty acid ester by using lipase in organic solvent |
| CN114160054A (en) * | 2022-02-14 | 2022-03-11 | 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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