CN109943482A - A method of extraction preparation r-4- chloro-3-hydroxyl ethyl butyrate is coupled using enzyme mebrane reactor - Google Patents
A method of extraction preparation r-4- chloro-3-hydroxyl ethyl butyrate is coupled using enzyme mebrane reactor Download PDFInfo
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Abstract
The present invention relates to a kind of methods for preparing r-4- chloro-3-hydroxyl ethyl butyrate using enzyme mebrane reactor coupling extraction, including enzyme mebrane reactor, organic solvent barrel and substrate barrel, filter membrane is distributed in the inside of the enzyme mebrane reactor, and the upper end side of enzyme mebrane reactor is connected with material liquid outlet, the side of the enzyme mebrane reactor is provided with organic solvent outlet, and the lower end side of enzyme mebrane reactor is connected with liquor inlet, the other side of the enzyme mebrane reactor is equipped with organic solution import.This method simple process; reduce the emulsion in reaction and extraction process; yield is improved, reduces the loss of organic solvent, and multiple without extraction; it is simple to operate; be conducive to scale industrial production, can endlessly collect product, releases inhibition of the product to enzyme or the murder by poisoning to cell; molar yield is improved, and is more conducive to industrialized production.
Description
Technical field
It is specially a kind of chloro- using enzyme mebrane reactor coupling extraction preparation r-4- the present invention relates to technical field of enzyme engineering
The method of ethyl 3-hydroxybutanoate.
Background technique
R-4- chloro-3-hydroxyl ethyl butyrate is that synthetic l-carnitine is also to synthesize big lactim A and (R)-gamma-amino-
The important intermediate of the chipal compounds such as beta-hydroxy-butanoic acid (GABOB), market demand are very big.
Preparation r-4- chloro-3-hydroxyl ethyl butyrate mainly uses biological method, and the method being commonly used is using micro-
Bioanalysis prepares r- carbonyl reductase and regenerating coenzyme system, then utilizes the two enzymes biocatalysis 4- chloroacetyl acetacetic ester
R-4- chloro-3-hydroxyl ethyl butyrate is synthesized, since r-4- chloro-3-hydroxyl ethyl butyrate is not soluble in water, and is had to cell/enzyme larger
Toxicity, therefore generally generally use the reaction of water/organic solvent two-phase system, product can be made to keep low concentration to subtract in water phase
Its few toxic action to cell.
Due to the presence of enzyme or cell, can make organic solvent and water that emulsification occur becomes homogeneous phase, to subsequent extraction
Technique produces difficulty, reduces yield, and there is presently no documents or patent report how to eliminate emulsion, only patent
Document CN104651292A discloses a kind of utilization macroporous absorbent resin original position and removes the chloro- 3- hydroxyl of substrate COBE and product s-4-
The method that base ethyl butyrate inhibits, but such method with a large amount of eluant, eluent and need to need resin regeneration, can generate a large amount of
Waste water and solid waste, cumbersome, cost is also larger.
Summary of the invention
Enzyme mebrane reactor coupling extraction preparation r-4- chloro-3-hydroxyl butyric acid second is utilized the purpose of the present invention is to provide a kind of
The method of ester can be such that organic solvent and water occurs to solve the presence mentioned above in the background art due to enzyme or cell
Emulsification becomes homogeneous phase, produces difficulty to subsequent extraction process, reduces yield.There is presently no document or patent reports
How road eliminates emulsion, and only patent document CN104651292A discloses a kind of utilization macroporous absorbent resin removal in situ
The method that substrate COBE and product s-4- chloro-3-hydroxyl ethyl butyrate inhibit, but such method need to use a large amount of eluant, eluent
And resin regeneration is needed, a large amount of waste water and solid waste can be generated, cumbersome, cost also larger problem.
To achieve the above object, the invention provides the following technical scheme: a kind of utilize enzyme mebrane reactor coupling extraction preparation
The method of r-4- chloro-3-hydroxyl ethyl butyrate, including enzyme mebrane reactor, organic solvent barrel and substrate barrel, the enzyme membrane are anti-
The inside of device is answered to be distributed with filter membrane, and the upper end side of enzyme mebrane reactor is connected with material liquid outlet, the one of the enzyme mebrane reactor
Side is provided with organic solvent outlet, and the lower end side of enzyme mebrane reactor is connected with liquor inlet, the enzyme mebrane reactor it is another
Side is equipped with organic solution import, and the machine solution inlet port and organic solvent export respectively through pipeline and organic solvent barrel
It is connected, and the pipeline that connect with machine solution inlet port of solvent barrel is distributed with force (forcing) pump, in the inside of the solvent barrel
Portion is through there is agitating paddle, and the material liquid outlet passes through pipeline with liquor inlet respectively and is connected with substrate barrel, and substrate barrel
Outer wall be fitted with insulation jacket, fenestra is distributed on the inside of the filter membrane, wherein.
Preferably, the material of the filter membrane can be ceramic membrane, composite fibre ester miillpore filter, nitrocellulose filter,
Kynoar filter membrane, cellulose acetate sheets, regenerated cellulose filter membrane, polyamide filter membrane, teflon membrane filter and poly-
The modification composite membrane of vinyl chloride filter membrane and above-mentioned material.
Preferably, the retention precision of filter membrane described in the right 1 and right 2 is 1kD-100kD.
Preferably, s- carbonyl reductase and glucose dehydrogenase used in the step can be enzyme powder, enzyme solution, gene
One of engineering bacteria is a variety of.
Preferably, fixer used in the step can be glutaraldehyde, epoxychloropropane, hexamethylene diamine, maleic two
Acid, bisazo benzene.
Preferably, organic solvent described in the step can be ethyl acetate, butyl acetate, toluene, dimethylbenzene, pungent
One of alcohol, chloroform, isopropanol, n-hexane, hexamethylene, n-butanol, isobutanol, dibutyl phthalate or two kinds.
Gas chromatograph used in the present invention is FULI9790 gas chromatograph, chemical purity testing conditions are as follows: detection
Device: fid detector, chromatographic column: SE-54 capillary chromatographic column (30m*0.32mm*0.5 μm), 2.0 μ L of sample volume vaporize room temperature
250 DEG C of degree, takes temperature-programmed mode: 130 DEG C of holding 5min by 260 DEG C of detector temperature, and 5 DEG C of heating, is warming up to per minute
10min is kept at 240 DEG C, optical purity testing conditions are as follows: detector: fid detector, chromatographic column: GC/CP-Chirasil-
DexCB, 10 μ L of sample volume, 280 DEG C of detector temperature, takes temperature-programmed mode: 110 DEG C of holdings by 280 DEG C of temperature of vaporization chamber
2min, 2 DEG C of heating, keeps 2min when being warming up to 160 DEG C per minute.
Compared with prior art, the beneficial effects of the present invention are:
(1) using enzyme mebrane reactor coupling extraction preparation r-4- chloro-3-hydroxyl ethyl butyrate, production can endlessly be collected
Object, releases inhibition of the product to enzyme or the murder by poisoning to cell, molar yield are improved, and is more conducive to industrial metaplasia
It produces.
(2) emulsion in reaction and extraction process is reduced, yield is improved, reduces the loss of organic solvent, and
It is simple to operate without extracting repeatedly, be conducive to scale industrial production.
Detailed description of the invention
Fig. 1 is a kind of enzyme membrane that r-4- chloro-3-hydroxyl ethyl butyrate is prepared using enzyme mebrane reactor coupling extraction of the present invention
Reactor assembly schematic diagram；
Fig. 2 is a kind of filter for the method that r-4- chloro-3-hydroxyl ethyl butyrate is prepared using enzyme mebrane reactor coupling extraction of the present invention
Film cross section structure schematic diagram；
In figure: 1, enzyme mebrane reactor；2, filter membrane；3, material liquid outlet；4, organic solvent exports；5, liquor inlet；6, force (forcing) pump；7,
Organic solvent barrel；8, agitating paddle；9, substrate barrel；10, insulation jacket；11, fenestra；12, organic solution import.
Specific embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, it is obtained by those of ordinary skill in the art without making creative efforts every other
Embodiment shall fall within the protection scope of the present invention.
The present invention provides a kind of technical solution referring to FIG. 1-2: a kind of to utilize enzyme mebrane reactor coupling extraction preparation r-4-
The method of chloro-3-hydroxyl ethyl butyrate, including enzyme mebrane reactor 1, filter membrane 2, material liquid outlet 3, organic solvent outlet 4, feed liquid into
Mouth 5, force (forcing) pump 6, organic solvent barrel 7, agitating paddle 8, substrate barrel 9, insulation jacket 10, fenestra 11 and organic solution import
12, filter membrane 2 is distributed in the inside of the enzyme mebrane reactor 1, and the upper end side of enzyme mebrane reactor 1 is connected with material liquid outlet 3, institute
The side for stating enzyme mebrane reactor 1 is provided with organic solvent outlet 4, and the lower end side of enzyme mebrane reactor 1 is connected with liquor inlet
5, the other side of the enzyme mebrane reactor 1 is equipped with organic solution import 12, the machine solution inlet port 12 and organic solvent outlet 4
It is connected respectively by pipeline with organic solvent barrel 7, and the pipeline that solvent barrel 7 is connect with machine solution inlet port 12 is distributed with
Force (forcing) pump 6, through there is agitating paddle 8, the material liquid outlet 3 leads to the middle inside of the solvent barrel 7 respectively with liquor inlet 5
Piping is connected with substrate barrel 9, and the outer wall of substrate barrel 9 is fitted with insulation jacket 10, the inside distribution of the filter membrane 2
There is fenestra 11, wherein
It is described method includes the following steps:
1) fixer is imported in enzyme mebrane reactor 1 by force (forcing) pump 6, recycles 30min-3h at 20 DEG C.
2) r- carbonyl reductase and glucose dehydrogenase are dissolved in the phosphate buffer of pH7.0, make the two enzyme activity all
It for 5ku/L-50ku/L, is then imported in enzyme mebrane reactor 1 by force (forcing) pump 6, and recycles 1h-3h at 10-20 DEG C.
3) by be 5%-30% containing concentration 4- chloroacetyl acetacetic ester, concentration be 50-300g/L glucose, concentration be
The organic solvent mixed solution of 0%-70% imports enzyme mebrane reactor 1 by force (forcing) pump 6, and is recycled.Temperature control is 20-40
DEG C, pH is controlled in 5.0-8.0.The enzyme reaction time is 3-24h.
4) after enzymic catalytic reaction starts 3-24h, the identical organic solvent in the other side of filter membrane 2 is passed through and reacts,
And it is recycled.Temperature control is 20-40 DEG C, and 2 pressure difference controls of filter membrane are in 0.02-0.5Mpa.To be free of in enzyme mebrane reactor 1
When having product, entire technical process terminates.
A method of extraction preparation r-4- chloro-3-hydroxyl ethyl butyrate being coupled using enzyme mebrane reactor, this method includes
Following steps:
(1) glutaraldehyde is led in enzyme mebrane reactor 1 by force (forcing) pump 6, recycles 30min at 20 DEG C；
(2) r- carbonyl reductase and glucose dehydrogenase are dissolved in the phosphate buffer of pH7.0, both make the enzyme activity all be
50ku/L is then led in enzyme mebrane reactor 1 by force (forcing) pump 6, and recycles 2h at 20 DEG C, and used film is the hollow fibre of PVDF
Film is tieed up, retention precision is 1kD；
(3) by be 15% containing concentration 4- chloroacetyl acetacetic ester, concentration be 150g/L glucose, concentration be 30% acetic acid
Ethyl ester mixed solution leads enzyme mebrane reactor 1 by force (forcing) pump 6, and is recycled, and temperature control is 30 DEG C, and pH control is 7.0, enzyme
Reaction time is for 24 hours；
(4) after enzymic catalytic reaction starts for 24 hours, it is passed through ethyl acetate in the other side of film, and recycled, temperature control is 30
DEG C, pressure difference control after extraction, detects the purity and content of product, and calculate in 0.5Mpa, extraction time 8h between film
Yield, the chemical purity of final products are 99.5%, and optical purity is 99.9%, yield 99.5%.
Although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art,
It is still possible to modify the technical solutions described in the foregoing embodiments, or part of technical characteristic is carried out etc.
With replacement, all within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in this
Within the protection scope of invention.
Claims (6)
1. a kind of method for preparing r-4- chloro-3-hydroxyl ethyl butyrate using enzyme mebrane reactor coupling extraction, including including enzyme membrane
Reactor (1), organic solvent barrel (7) and substrate barrel (9), it is characterised in that: the inside of the enzyme mebrane reactor (1) is distributed
Have filter membrane (2), and the upper end side of enzyme mebrane reactor (1) is connected with material liquid outlet (3), the side of the enzyme mebrane reactor (1)
It is provided with organic solvent outlet (4), and the lower end side of enzyme mebrane reactor (1) is connected with liquor inlet (5), the enzyme membrane reaction
The other side of device (1) is equipped with organic solution import (12), and the machine solution inlet port (12) is led to respectively with organic solvent outlet (4)
Piping is connected with organic solvent barrel (7), and the pipeline that solvent barrel (7) is connect with machine solution inlet port (12) is distributed with
Force (forcing) pump (6), the middle inside of the solvent barrel (7) through having agitating paddle (8), the material liquid outlet (3) and feed liquid into
Mouth (5) is connected by pipeline with substrate barrel (9) respectively, and the outer wall of substrate barrel (9) is fitted with insulation jacket (10), institute
It states and fenestra (11) is distributed on the inside of filter membrane (2), wherein
It is described method includes the following steps:
1) fixer is imported in enzyme mebrane reactor (1) by force (forcing) pump (6), recycles 30min-3h at 20 DEG C；
2) r- carbonyl reductase and glucose dehydrogenase are dissolved in the phosphate buffer of pH7.0, both make the enzyme activity all be
5ku/L-50ku/L is then imported in enzyme mebrane reactor (1) by force (forcing) pump (6), and is recycled 1h-3h at 10-20 DEG C；
3) by be 5%-30% containing concentration 4- chloroacetyl acetacetic ester, concentration be 50-300g/L glucose, concentration 0%-
70% organic solvent mixed solution imports enzyme mebrane reactor (1) by force (forcing) pump (6), and is recycled；
Temperature control is 20-40 DEG C, and pH is controlled in 5.0-8.0；
The enzyme reaction time is 3-24h；
4) after enzymic catalytic reaction starts 3-24h, the identical organic solvent in the other side of filter membrane (2) is passed through and reacts, and
It is recycled；
Temperature control is 20-40 DEG C, and pressure difference control is in 0.02-0.5Mpa between filter membrane (2)；
When not containing product in enzyme mebrane reactor (1), entire technical process terminates.
2. a kind of extracted using enzyme mebrane reactor coupling according to claim 1 prepares r-4- chloro-3-hydroxyl ethyl butyrate
Method, it is characterised in that: the material of the filter membrane (2) can be ceramic membrane, composite fibre ester miillpore filter, nitrocellulose
Filter membrane, Kynoar filter membrane, cellulose acetate sheets, regenerated cellulose filter membrane, polyamide filter membrane, teflon membrane filter with
And the modification composite membrane of polyvinyl chloride filter membrane and above-mentioned material.
3. a kind of extracted using enzyme mebrane reactor coupling according to claim 1 prepares r-4- chloro-3-hydroxyl ethyl butyrate
Method, it is characterised in that: the retention precision of filter membrane (2) described in the right 1 and right 2 be 1kD-100kD.
4. a kind of extracted using enzyme mebrane reactor coupling according to claim 1 prepares r-4- chloro-3-hydroxyl ethyl butyrate
Method, it is characterised in that: s- carbonyl reductase used in the step (2) and glucose dehydrogenase can be enzyme powder, enzyme
One of liquid, genetic engineering bacterium are a variety of.
5. a kind of extracted using enzyme mebrane reactor coupling according to claim 1 prepares r-4- chloro-3-hydroxyl ethyl butyrate
Method, it is characterised in that: fixer used in the step (1) can be glutaraldehyde, epoxychloropropane, hexamethylene diamine, suitable
Butene dioic acid, bisazo benzene.
6. a kind of extracted using enzyme mebrane reactor coupling according to claim 1 prepares r-4- chloro-3-hydroxyl ethyl butyrate
Method, it is characterised in that: organic solvent described in the step (3) can be ethyl acetate, butyl acetate, toluene, diformazan
One of benzene, octanol, chloroform, isopropanol, n-hexane, hexamethylene, n-butanol, isobutanol, dibutyl phthalate or
Two kinds.
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| CN201910166157.4A CN109943482B (en) | 2019-03-06 | 2019-03-06 | Method for preparing ethyl r-4-chloro-3-hydroxybutyrate by coupling extraction of enzyme membrane reactor |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113528588A (en) * | 2021-06-15 | 2021-10-22 | 海南卓科制药有限公司 | Preparation method of levocarnitine |
| CN114456928A (en) * | 2022-03-22 | 2022-05-10 | 合肥学院 | Immobilized enzyme reactor and reaction system |
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| CN113528588A (en) * | 2021-06-15 | 2021-10-22 | 海南卓科制药有限公司 | Preparation method of levocarnitine |
| CN114456928A (en) * | 2022-03-22 | 2022-05-10 | 合肥学院 | Immobilized enzyme reactor and reaction system |
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| CN109943482B (en) | 2022-03-29 |
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Address after: 225300 Gao Yong Industrial Park, Yongan Chau Town, Taizhou, Jiangsu Applicant after: Jiangsu Huili Biotechnology Co., Ltd Address before: 225300 Gaoyong Industrial Park, Yonganzhou Town, Gaogang District, Taizhou City, Jiangsu Province Applicant before: Taizhou Huili Biotechnology Co., Ltd. |
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