CN103184251B - Method for on-line synthesizing glucose-6-acetate catalyzed by lipase - Google Patents
Method for on-line synthesizing glucose-6-acetate catalyzed by lipase Download PDFInfo
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- 108090001060 Lipase Proteins 0.000 title abstract description 5
- 239000004367 Lipase Substances 0.000 title abstract description 5
- 102000004882 Lipase Human genes 0.000 title abstract description 5
- 235000019421 lipase Nutrition 0.000 title abstract description 5
- VFPUCPVAZOMVLI-LXGUWJNJSA-N [(2r,3r,4s,5r)-2,3,4,5-tetrahydroxy-6-oxohexyl] acetate Chemical compound CC(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O VFPUCPVAZOMVLI-LXGUWJNJSA-N 0.000 title abstract description 4
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 93
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 32
- 239000008103 glucose Substances 0.000 claims abstract description 25
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000005917 acylation reaction Methods 0.000 claims abstract description 16
- 230000035484 reaction time Effects 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 13
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- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012046 mixed solvent Substances 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 38
- 239000000047 product Substances 0.000 claims description 18
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- 230000001737 promoting effect Effects 0.000 claims description 4
- 238000011049 filling Methods 0.000 claims description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract description 22
- 230000008901 benefit Effects 0.000 abstract description 5
- 239000012295 chemical reaction liquid Substances 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000009466 transformation Effects 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 8
- -1 sucrose ester Chemical class 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- VJHCJDRQFCCTHL-BTVCFUMJSA-N acetic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O VJHCJDRQFCCTHL-BTVCFUMJSA-N 0.000 description 3
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical class Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
Abstract
The invention discloses a method for on-line synthesizing glucose-6-acetate catalyzed by lipase. According to the method, glucose and vinyl acetate with a molar ratio being 1 : 16-22 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 15-35 min; a reaction liquid is collected on-line; and the glucose-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
(1) technical field
The present invention relates to the method for the synthetic glucose-6-acetic ester of a kind of lipase-catalyzed online controlled selectivity.
(2) background technology
Sugar ester is a kind of good nonionogenic tenside, and the natural reproducible resource sugar that adopts nature extensively to exist is raw material, has vast potential for future development.The future development of current Surfactant Industry forward Green Chemistry, requires product toxicological harmless, renewableization of reaction raw materials, reaction process greenization gradually.Sugar ester, as a kind of good natural surface active agent, meet product toxicological harmless and the large requirement of renewableization of reaction raw materials two of Green Chemistry, but its reaction process still needs further greenization.
The sugar ester of commercially producing both at home and abroad at present is all synthesized by chemical method, there are many deficiencies in chemical method, mainly comprise: reaction process conditional fierceness, the side reaction such as sugared carbonization easily occurs and lactonize, and due to the poor selectivity of chemosynthesis reaction to ester bond position, ester bond quantity is restive, the isomer that generation product is multiple ester and the mixture of byproduct, the shortcomings such as product is difficult to separation and purification, and product color is darker.Production by Enzymes has reaction conditions gentleness and good region and regioselectivity, and obvious stereospecificity, and product purity is high, lighter color, the advantages such as the easy separation and purification of product.Production by Enzymes not only meets the requirement of green reaction process, and has solved the shortcomings that chemical method is produced, and is more and more subject to people's attention.
At present both at home and abroad research is more and realize being still taking sucrose ester as two main sugar esters of suitability for industrialized production, and relatively less to the research of the monose esters such as glucose ester, fructose ester.Adopt glucose production sugar ester to have many advantages compared with sucrose, as glucose contains less hydroxyl, Production by Enzymes glucose ester reaction process is simpler, less side products, monoesters transformation efficiency is higher, product separation purifying is simpler etc., in addition, the research of glucose ester is solved to the single problem of the domestic sugar ester product of China by being conducive to, be conducive to realize the seriation of sugar ester HLB value.
Therefore the synthetic method of developing efficient glucose ester has very important practical significance.
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.
At present, there is more Chinese scholars to be studied the enzyme catalysis of glucose ester in organic medium is synthetic, but the method often needs the reaction times (24h) of growing, and transformation efficiency and the selectivity of reaction are not high, therefore we have studied the method for the synthetic glucose-6-acetic ester of lipase-catalyzed selectivity in micro passage reaction, are intended to the online controlled method for selective synthesis of glucose-6-acetic acid monoesters of finding a kind of high-efficiency environment friendly.
(3) summary of the invention
The technical problem to be solved in the present invention is to provide the novel process of the synthetic glucose-6-acetic ester of lipase-catalyzed selectivity 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 glucose-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: the glucose taking mol ratio as 1:16 ~ 22 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 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 DEG C, the acylation reaction time is 15 ~ 35min, collect online reaction solution by product collector, reaction solution obtains glucose-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, and the material of recommendation green, environmental protection, as 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 first be dissolved glucose with the mixed solvent (tertiary amyl alcohol: DMSO=4:1) of tertiary amyl alcohol and DMSO, and its consumption needs only and ensures that glucose 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 present invention, in reaction solvent, tertiary amyl alcohol and DMSO volume ratio are greater than 4:1, than conventional shaking table reaction, can the usage quantity of poisonous DMSO are 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 (EC3.1.1.3) 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 glucose and vinyl-acetic ester is preferably 1:20 ~ 22, most preferably is 1:20.
Further, described acylation reaction temperature is preferably 52 ~ 55 DEG C, most preferably is 52 DEG C.
Further, the described acylation reaction time is preferably 25 ~ 35min, most preferably is 30min.
Reaction product of the present invention can be collected online, and gained reaction solution can obtain glucose-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=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 glucose-6-acetic ester.
In the present invention, although there are 5 hydroxyls that performance is close in glucose, but the synthetic glucose acetate of lipase-catalyzed selectivity has higher transformation efficiency and selectivity in micro-fluidic micro passage reaction, the transformation efficiency of diester is very low, almost there is no the content 100% of the monoesters obtaining by column chromatography for separation.The structure warp of product
1h NMR confirmation.This shows that the enzymatic selectivity of glucose acetate in microfluidic channel reactor 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: the synthetic glucose-6-acetic ester of selectivity 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 of embodiment of the present invention 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 to this:
The structure of 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, 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: glucose-6-acetic ester synthetic
Install with reference to figure 1: glucose (0.4mmol) is dissolved in the mixed solvent of 10mL tertiary amyl alcohol: DMSO=4:1 (v/v), and vinyl-acetic ester (8.0mmol) 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, by constant temperature water bath case control temperature of reactor, at 52 DEG C, reaction solution is continuous flow reaction 30min in reaction channel, reaction result is followed the tracks of and is detected by thin-layer chromatography TLC.
Collect online reaction solution by product collector, underpressure distillation is except desolventizing, with 200-300 order silica gel wet method dress post, elution reagent is chloroform: methyl alcohol=10:1, 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
-1tLC follows the tracks of wash-out process simultaneously, the elutriant that contains single product obtaining is merged to evaporate to dryness, obtain white monoesters crystal, obtain glucose-6-acetic ester, HPLC measures inversion rate of glucose 99%, and glucose-6-acetic ester selectivity (the glucose ester total content of glucose-6-acetate content/generation) is 100%.
Nuclear-magnetism characterization result is as follows:
1h-NMR (DMSO-d6, δ, ppm): glucose-6-acetic ester:
1h-NMR (DMSO-d6, δ, ppm): 6.71 (d, 0.5H, J=6.5Hz, the 1-OH of β-D-Glucose), 6.36 (d, 0.5H, J=4.5Hz, the 1-OH of alpha-D-glucose), 5.15-4.57 (br m, other OH of D-Glucose), 4.32 (m, 1.5H, the H-6 (1H) of D-Glucose and β H-1 (0.5H)), 4.0 (m, 1H, the H-6 ' of D-Glucose), 3.77 (m, 0.5H, the α H-5 of D-Glucose), 3.39-3.30, 3.13, 3.03 (br m, other α of D-Glucose or β H), 2.90 (0.5H, m, the β H-2 of D-Glucose), 2.00 (3H, s, 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
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, thus in the present invention in micro-fluidic micro passage reaction the optimal reaction temperature of glucose acetate be 52 DEG C.
Embodiment 6-10
Changing the substrate mol ratio of vinyl-acetic ester and glucose in micro-fluidic micro passage reaction is 16:1(embodiment 6), 17:1(embodiment 7), 18:1(embodiment 8), 19:1(embodiment 9), 21:1(embodiment 10), 22:1(embodiment 11), other are with embodiment 1, and result is as shown in table 2.
Table 2: glucose is compared the impact of reacting with vinyl-acetic ester substrate
| Embodiment | Vinyl-acetic ester: glucose | Transformation efficiency [%] | Selectivity [%] |
| 6 | 16:1 | 65 | 100 |
| 7 | 17:1 | 75 | 100 |
| 8 | 18:1 | 84 | 100 |
| 9 | 19:1 | 90 | 100 |
| 1 | 20:1 | 99 | 100 |
| 10 | 21:1 | 98 | 99 |
| 11 | 22:1 | 98 | 98 |
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, when substrate is when for 20:1, and the transformation efficiency of reaction and selectivity optimum, glucose has substantially quantitatively transformed completely for glucose-6-acetic ester.If now continue to increase the consumption of reactant vinyl-acetic ester, will cause transformation efficiency and the elective reduction of reaction, thereby the best substrate of this reaction is than being 20:1, under this reaction conditions, glucose substantially quantitatively transforms the acetic ester for glucose-6-completely.
Embodiment 12-15
Changing the reaction times in micro-fluidic micro passage reaction is 15min(embodiment 12), 20min(embodiment 13), 25min(embodiment 14), 35min(embodiment 15), other are with embodiment 1, result as shown in Figure 3.
Table 3: the reaction times is on reaction conversion ratio and optionally impact
| Embodiment | Reaction times [min] | Transformation efficiency [%] | Selectivity [%] |
| 12 | 15 | 65 | 100 |
| 13 | 20 | 86 | 100 |
| 14 | 25 | 93 | 100 |
| 1 | 30 | 99 | 100 |
| 15 | 35 | 98 | 99 |
The result of table 3 shows, reaction is carried out 15min and can be obtained glucose-6-acetic acid monoesters of 65%, and selectivity is now 100%, and glucose is to be converted into glucose-6-acetic acid monoesters completely substantially.Along with the increase in reaction times, the transformation efficiency of reaction increases gradually, in the time that 30min is carried out in reaction, and the transformation efficiency of reaction and selectivity optimum, glucose-6-acetic acid monoesters transforms substantially completely, and reaction preference also can reach 100%.If now continue to extend the reaction times, can cause on the contrary reaction conversion ratio and optionally reduce, thereby in microfluidic channel reactor, the synthetic Best Times of glucose-6-acetic ester is 30min.
Claims (6)
1. the method for lipase-catalyzed online synthesis of glucose-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: the glucose taking mol ratio as 1: 16～22 and vinyl-acetic ester are as 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 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 DEG C, the acylation reaction time is 15～35min, collect online reaction solution by product collector, reaction solution obtains glucose-6-acetic ester through conventional aftertreatment.
2. the method for lipase-catalyzed online synthesis of glucose-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 of DMSO dissolve glucose, are 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 carry out acylation reaction in passing into reaction channel.
3. the method for lipase-catalyzed online synthesis of glucose-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 synthesis of glucose-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 synthesis of glucose-6-acetic ester as described in one of claim 1～4; it is characterized in that: the mol ratio of described glucose and vinyl-acetic ester is 1: 20～22; described acylation reaction temperature is 52～55 DEG C, and the described acylation reaction time is 25～35min.
6. the method for the lipase-catalyzed online synthesis of glucose-6-acetic ester as described in one of claim 1～4; it is characterized in that: the mol ratio of described glucose and vinyl-acetic ester is 1: 20; described acylation reaction temperature is 52 DEG C, and the described acylation reaction time is 30min.
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| 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 |
| CN107502629A (en) * | 2017-08-21 | 2017-12-22 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis N（5 vinyl acetate valeryls）The method of metoprolol |
| CN107475329A (en) * | 2017-08-21 | 2017-12-15 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 sucrose ester valeryl) mexiletine |
| 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 |
| 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 |
| CN107488691A (en) * | 2017-08-21 | 2017-12-19 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis N (5 lauroyl mannoses valeryl) metoprolol |
| 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 |
| CN107988279A (en) * | 2017-12-21 | 2018-05-04 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis 6- ((4- chlorobenzyls) sulfenyl) -6- oxo vinyl caproates |
| CN107955824A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of lipase-catalyzed online synthesis S-（4- chlorobenzyls）The method of laurate thioesters |
| CN107988278B (en) * | 2017-12-21 | 2021-06-04 | 浙江农林大学 | Method for synthesizing S-benzyl lauric acid thioester on line by lipase catalysis |
| CN107988277B (en) * | 2017-12-21 | 2021-06-08 | 浙江农林大学 | Method for synthesizing S-benzylpalmitic acid thioester on line under catalysis of lipase |
| CN108060184A (en) * | 2017-12-21 | 2018-05-22 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis S- thioacetic acid benzyl esters |
| CN108060185A (en) * | 2017-12-21 | 2018-05-22 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis S- (4- methylbenzyls) thiacetate |
| 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 |
| CN107955823A (en) * | 2017-12-21 | 2018-04-24 | 浙江工业大学 | A kind of method of lipase-catalyzed online synthesis 6- ((4- methyl-benzyls) sulfenyl) -6- oxo vinyl caproates |
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