CN109517156A - A kind of purification process of polyhydroxyalkanoate - Google Patents
A kind of purification process of polyhydroxyalkanoate Download PDFInfo
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- CN109517156A CN109517156A CN201910001260.3A CN201910001260A CN109517156A CN 109517156 A CN109517156 A CN 109517156A CN 201910001260 A CN201910001260 A CN 201910001260A CN 109517156 A CN109517156 A CN 109517156A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
The invention discloses a kind of purification process of polyhydroxyalkanoate.The purification process includes the following steps: that PHA crude product is dissolved in organic solvent by (1), heats up and is centrifuged after stirring cooling simultaneously；The organic solvent is miscible with water；(2) water is added into the solution after the separation, precipitate is collected after centrifugation；(3) it adopts and washes with water the precipitate, that is, realize the purifying to the polyhydroxyalkanoate.Purification process of the present invention, which has the advantages that, to be avoided substantially increasing production security using halogenated solvent and water-insoluble organic solvent.Using the relatively more preferable and moderate solvability N-Methyl pyrrolidone of biocompatibility, N- methyl caprolactam equal solvent, cytotoxicity and immunological rejection are greatly reduced.Solvent is precipitated and does not use ethyl alcohol or methanol, and PHA is precipitated using water, on the one hand reducing organic solvent uses, on the other hand the more easy cleaning such as some fragments soluble easily in water, improves the purity of PHA.
Description
Technical field
The present invention relates to a kind of purification process of polyhydroxyalkanoate, belong to biotechnology and biological chemical field.
Background technique
With the continuous not reproducible limitation of consumption of petroleum, environmental protection dynamics is continued to increase, in world wide
Start to tend to the non-petroleum base material of use environment friendly, i.e. biodegradable material, green material or ecomaterial.
And the polyhydroxyalkanoate (PHA) obtained by microbial fermentation exactly belongs to such a kind of biodegradable material, and because
This is increasingly included the concern and attention of medical profession by industry.And the PHA material being mass produced at present is due to containing
There are the impurity such as a small amount of cell fragment, protein, it is easy to lead to body inflammatory, to greatly limit it in medical treatment & health
The large-scale application of industry.
PHA is a kind of high molecular material family comprising a variety of polyester, is mainly produced by plant or microbial fermentation
It arrives, general formula of the chemical structure is as shown in Equation 1, and structure has had the PHA quilt of more than 100 kinds of different structures because of R group difference at present
Identification and report come out.According to the difference of carbon atom number, PHA can be divided into short chain PHA (carbon atom number is 3-5) and
Medium chain length PHA (carbon atom number is at 6 or more) two major classes；According to the repeat type of monomeric building blocks, it is segmented into homopolymerization
Object, dimer, trimer etc..Additionally, due to structure difference, difference is also presented in the PHA molecular weight that microbial fermentation obtains, from several
Ten thousand dalton (Da) arrive millions of dalton (Da), and this also produces very big influence to its physical and chemical properties, thus
Imparting PHA has certain application value in every field.In addition the catabolite of PHA is mostly hydroxy fatty acid, is being cured
There is particularly important application in terms of medicine and energy fuel.And wherein especially with 3-hydroxybutyrate in field of medicaments most study and
Most extensively.In short, whether PHA or its derivative products all have great industrial application value and medical applications prospect.
There is very wide development prospect in medical treatment & health field at present, especially body implanting material field.It is implanted into material master
If macromolecule polymer material, and it is divided into biodegradable material and biological non-degradable material.In the implantation that early period uses
Material is mostly biological non-degradable material, such as polyethylene, polyvinyl chloride can generate one after these materials are implanted directly into vivo
Serial adverse reaction, it is sometimes desirable to which second operation takes out.And biodegradable material includes as the more of implantation material
Copolymer, the polyhydroxyalkanoate of polyglycolic acid, polylactic acid, polylactic acid and polyglycolic acid.But compared with PHA, other are several
The degradation speed of kind biodegradable material is too fast, and application prospect is subject to certain restrictions in some fields.And PHA is in bio-compatible
Property, cell adhesion and degradation speed have and can be adjusted by molecular weight and monomer structure.But since PHA is
It is produced by microbial fermentation, this would have to consider the adverse reaction whether its purity can cause body.So in order to
Expand PHA in the application range of medical treatment & health industry, purifying obtains high-purity PHA and is particularly important and urgently.
There is the side for much isolating and purifying PHA from biomass or thallus based on organic solvent or other technologies
Method.It is chloroform (U.S.Pat.No.3,275,610) that the most common solvent of PHA is wherein extracted from bacterium, this is also current
It is known that best solvent is dissolved to PHA.In addition U.S.Pat.No.4562245,4324907 and 4310684 also illustrate other one
PHA is isolated and purified out by a little chlorinated solvents such as methylene chloride, dichloroethanes and dichloropropane from thallus.But these contain
There are potential carcinogenicities to human body for halogen solvent, so be not good purification solvent.U.S.Pat.No.5942597 description
A kind of method for isolating and purifying out from biomass by PHA using a variety of non-halogenated solvent.Solvent mainly wraps in this method
It includes: the one of which such as acetone, acetonitrile, ethyl acetate or the mixing of several solvents, but one side solvent is to PHA in this method
Solvability it is all relatively weak, on the other hand also without the PHA purity that finally obtains of displaying.These solvents are required by adding
Enter ethyl alcohol or methanol to separate out the PHA of dissolution, then with ethyl alcohol or methanol the PHA washes clean of precipitation.Solvent and non-solvent
All it is expensive not environmentally.
In addition to this, there is presently no slightly mentioning in PHA and purifying again from what is obtained, so that the other PHA of pharmaceutical grade is obtained, this
Also the emphasis that should be exactly paid close attention to using PHA at present.Still further aspect finds novel green solvent as the good molten of PHA
The medical treatment & health that agent also will be enlarged by high-purity PHA is especially implanted into the application range of Material Field.
Summary of the invention
The object of the present invention is to provide it is a kind of because biofermentation reason and purity be not achieved medical material national standard or
Polyhydroxyalkanoate (PHA) purification process of the problems such as adverse reaction occurs for person's living organism, and this method can overcome above-mentioned
There are the problem of, while used device structure is simple, purification step is simple, easy to operate, environmental pollution is smaller, purifying
Step and solvent can be recycled.In addition, this method purification capacity is stronger, it is higher can to obtain purity for good impurity removing effect
PHA material.
The purification process of polyhydroxyalkanoate provided by the present invention, includes the following steps:
(1) PHA crude product is dissolved in organic solvent, heats up and is centrifuged after stirring cooling simultaneously；
The organic solvent is miscible with water；
(2) water is added into the solution after the separation, precipitate is collected after centrifugation；
(3) it adopts and washes with water the precipitate, that is, realize the purifying to the polyhydroxyalkanoate.
PHA of the present invention, i.e. polyhydroxyalkanoate can be divided into homopolymer and copolymerization according to monomer composition
Object.According to the carbon atom number of monomer, PHA can be short chain PHA (carbon atom number is at 3~5) or medium chain length PHA (carbon original
Subnumber mesh is at 6~24), but not limited to this.
In certain embodiments of the present invention, PHA can be homopolymer, including but not limited to poly- 3- hydroxy propionate
(P3HP), poly 3-hydroxy butyrate (PHB), poly- 3- hydroxyl valerate (PHBV) etc..
In certain embodiments of the present invention, PHA can be copolymer such as dimer, trimer etc., but not limited to this.
For example, PHA can be poly 3-hydroxy butyrate (PHB), poly- (3-hydroxybutyrate ester-co-4- hydroxyl fourth in embodiment of the present invention
Acid esters) (P34HB), poly- (3-hydroxybutyrate ester-co-3- hydroxyl valerate) (PHBV), poly- (3-hydroxybutyrate ester-co-3- hydroxyl
Capronate) (PHBHHx) or combinations thereof etc..
The PHA crude product refers to purity in 95 weight % (wt%) and below produces to obtain by microbial fermentation culture
PHA.More preferably purity 80~90wt% PHA, for example including purity 80~90wt% poly- (3-hydroxybutyrate
Ester) (PHB), poly- (3-hydroxybutyrate ester-co-4- butyric ester) (P34HB), poly- (3-hydroxybutyrate ester-co-3- hydroxyl penta
Sour rouge) (PHBV), poly- (3-hydroxybutyrate ester-co-3- hydroxycaproic ester) (PHBHHx) etc., but be not restricted to that such PHA.
In above-mentioned purification process, the PHA crude product can exist in the form of cell inclusion, can also be containing more thin
Half broken form of born of the same parents' fragment or pigment exists, and can more exist in the form of impure PHA.
When the PHA crude product contains more cell fragment or pigment, carry out needing successively to use water before step (1)
And PHA crude product described in ethanol elution.
In above-mentioned purification process, the organic solvent can be nitrogenous cricoid organic matter；
Concretely organic solvent is 2-Pyrrolidone, N-Methyl pyrrolidone, N- second to the nitrogenous cricoid organic matter
Base -2-Pyrrolidone or N- methyl caprolactam.
In above-mentioned purification process, in step (1), temperature after the heating is 70~150 DEG C, and the time of the stirring is
2~10 hours；
The dosage of the organic solvent are as follows: PHA crude product described in 1g: organic solvent described in 30~50mL, PHA is thick as described in 1g
Product: organic solvent described in 40mL.
In above-mentioned purification process, in step (1), the temperature after the cooling is 25~40 DEG C, such as 35 DEG C；
The revolving speed of the centrifugation is 3000~4000rpm, reaches separation insoluble matter with this and has dissolved the solution of PHA.
In above-mentioned purification process, in step (1), the PHA crude product and the organic solvent mix in a container；
The container is to seal stirred tank or the compression resistance stirred tank with pressurization and heating function.
In above-mentioned purification process, in step (2), the water is ultrapure water；
The purity of the ultrapure water is 98%~99.99%；
The additional amount of the water is 2~6 times of the organic solvent；
It is stirred 30~60 minutes after the water is added；
The centrifugation is carried out under conditions of revolving speed is not less than 5000rpm, such as 8000~10000rpm；
The time of the centrifugation is 30~60 minutes.
In above-mentioned purification process, in step (3), the water is ultrapure water；
The additional amount of the water is 2~6 times of the organic solvent, such as 5 times；
The number of the cleaning is 1~4 time.
In above-mentioned purification process, the method also includes recycling to make after filtering to the organic solvent in step (1)
The step of using.
Purification process of the present invention has the advantages that
(1) it avoids substantially increasing production security using halogenated solvent and water-insoluble organic solvent.
(2) using biocompatibility is relatively more preferable and solvability is moderate N-Methyl pyrrolidone, N- methyl in oneself
Amide equal solvent greatly reduces cytotoxicity and immunological rejection.
(3) solvent is precipitated and does not use ethyl alcohol or methanol, and PHA is precipitated using water, on the one hand reduces organic solvent
It uses, on the other hand the more easy cleaning such as some fragments soluble easily in water, improves the purity of PHA.
(4) NMP boiling point is higher, and when heating for dissolving will not generate the air pressure of elevated pressures, and production security is higher.
(5) purifying process is simple and environmentally-friendly, easily operated, and good impurity removing effect.
Detailed description of the invention
Fig. 1 is the flow diagram of purification process of the invention.
Specific embodiment
The purification process in the present invention is explained further below in conjunction with specific embodiment, it should be noted that arrive, these
Embodiment does not limit in any form the present invention, only helps to describe and understand this hair in a manner of specific embodiment
It is bright.
The materials, reagents and the like used in the following examples is commercially available unless otherwise specified.
In addition to this, in the following embodiments unless otherwise indicated, the PHA purity representation method as unit of wt%
It is to be measured by gas-chromatography (GC), the method for specifically detecting PHA content is as follows:
Furnace temperature is set first as 80 DEG C, and sample injector temperature is 200 DEG C, and detector temperature is 220 DEG C, and column head pressure is
0.25MPa, temperature programming condition are as follows: 80 DEG C are kept for 1.5 minutes, 140 DEG C are warming up to the speed of 30 DEG C/min, then with 40
DEG C/speed of min is warming up to 220 DEG C and kept for 0.5 minute in this temperature.The sample volume of sample is 1 μ l, gas phase liquid chromatogram type
Number be Shimadzu GC 2014.
Purity PHA preparation of samples to be measured: the PHA sample after taking 30-40mg dry adds 2ml chloroform, 2ml in esterification pipe
Make interior target esterifying liquid comprising pure methanol, the concentrated sulfuric acid of 3% (v/v) and 2g/L benzoic acid, it is small to be placed in heating reaction 4 at 100 DEG C
When.It takes out after cooling and 1ml distilled water is added, sufficiently stood after oscillation, after chloroform phase and water phase are layered completely, take lower layer's chlorine
Imitative phase 1ml sets instrument according to default step in GC sample injection bottle.Other operate the specification according to gas chromatograph
Operate gas chromatograph.
Standard sample prepares: taking the standard sample of 10~20mg in esterification pipe, other are identical as above-mentioned processing step.
Interpretation of result: being control with standard sample, if purity PHA sample (sample to be tested) to be measured has correspondence at standard specimen
Then appearance can then be calculated according to the mass fraction of each monomer of calculated by peak area according to the mass fraction of each monomer
Molar ratio；The purity of PHA sample to be measured can be calculated according to the sample size of addition.
Embodiment 1: high-purity P34HB is prepared by solvent of N-Methyl pyrrolidone
The P34HB (initial purity 79.27wt%) for weighing 1.0g, is dissolved in the N-Methyl pyrrolidone of 40ml, is added to
It in the pressure bottle of 250ml, is heated at 100 DEG C, with 500rpm revolving speed stirring 4 hours.After solution to be mixed is cooled to 35 DEG C, protect
It holds and is centrifuged with 4000rpm revolving speed at a temperature of this, after removing insoluble matter, is stirred with 500rpm revolving speed, and constantly to it
The middle ultrapure water that about 200ml is added, and this revolving speed is kept persistently to stir 40 minutes.Then, this suspension is turned with 9000rpm
Speed is centrifuged, and precipitating is retained.Then obtained P34HB is resuspended with ultrapure water again and that stir about 1 in stirred tank is added is small
When, it is centrifuged again with 9000rpm revolving speed, obtains P34HB solid.It repeats this water-washing process at least 3 times, is then removed
Water, it is dry.
According to said determination Purity, the purity for measuring first time circulatory purification P34HB is 86.5wt%.Constantly circulation
This purification process, second of circulation purity of measurement are 95.76wt%, and it is 97.23wt%, the 4th circulation that third time, which recycles purity,
Purity is 99.13wt%.
Embodiment 2: high-purity PHBV is prepared by solvent of N-Methyl pyrrolidone
The PHBV (initial purity 88.63wt%) for weighing 1.0g, is dissolved in the N-Methyl pyrrolidone of 40ml, is added to
It in the pressure bottle of 250ml, is heated at 100 DEG C, with 500rpm revolving speed stirring 4 hours.After solution to be mixed is cooled to 35 DEG C, protect
It holds and is centrifuged with 4000rpm revolving speed at a temperature of this, after removing insoluble matter, is stirred with 500rpm revolving speed, and constantly to it
The middle ultrapure water that about 200ml is added, and this revolving speed is kept persistently to stir 40 minutes.Then, this suspension is turned with 9000rpm
Speed is centrifuged, and precipitating is retained.Then obtained PHBV is resuspended with ultrapure water again and that stir about 1 in stirred tank is added is small
When, it is centrifuged again with 9000rpm revolving speed, obtains PHBV solid.It repeats this water-washing process at least 3 times, is then removed water,
It is dry.
According to said determination Purity, the purity for measuring first time circulatory purification PHBV is 91.84wt%.Constantly circulation
This purification process, second of circulation purity of measurement are 94.91wt%, and it is 99.17wt%, the 4th circulation that third time, which recycles purity,
Purity is 99.68%.
Embodiment 3: high-purity P34HB is prepared by solvent of N- methyl caprolactam
The P34HB (initial purity 79.27wt%) for weighing 1.0g is dissolved in the N- methyl caprolactam of 40ml, is added to
It in the pressure bottle of 250ml, is heated at 100 DEG C, with 500rpm revolving speed stirring 4 hours.After solution to be mixed is cooled to 35 DEG C, protect
It holds and is centrifuged with 4000rpm revolving speed at a temperature of this, after removing insoluble matter, is stirred with 500rpm revolving speed, and constantly to it
The middle ultrapure water that about 200ml is added, and this revolving speed is kept persistently to stir 40 minutes.Then, this suspension is turned with 9000rpm
Speed is centrifuged, and precipitating is retained.Then obtained P34HB is resuspended with ultrapure water again and that stir about 1 in stirred tank is added is small
When, it is centrifuged again with 9000rpm revolving speed, obtains P34HB solid.It repeats this water-washing process at least 3 times, is then removed
Water, it is dry.
According to said determination Purity, the purity for measuring first time circulatory purification P34HB is 89.3wt%.Constantly circulation
This purification process, second of circulation purity of measurement are 94.63wt%, and it is 96.71wt%, the 4th circulation that third time, which recycles purity,
Purity is 98.93wt%.
Embodiment 4: high-purity PHBV is prepared by solvent of N- methyl caprolactam
The PHBV (initial purity 88.63wt%) for weighing 1.0g is dissolved in the N- methyl caprolactam of 40ml, is added to
It in the pressure bottle of 250ml, is heated at 100 DEG C, with 500rpm revolving speed stirring 4 hours.After solution to be mixed is cooled to 35 DEG C, protect
It holds and is centrifuged with 4000rpm revolving speed at a temperature of this, after removing insoluble matter, is stirred with 500rpm revolving speed, and constantly to it
The middle ultrapure water that about 200ml is added, and this revolving speed is kept persistently to stir 40 minutes.Then, this suspension is turned with 9000rpm
Speed is centrifuged, and precipitating is retained.Then obtained PHBV is resuspended with ultrapure water again and that stir about 1 in stirred tank is added is small
When, it is centrifuged again with 9000rpm revolving speed, obtains PHBV solid.It repeats this water-washing process at least 3 times, is then removed water,
It is dry.
According to said determination Purity, the purity for measuring first time circulatory purification PHBV is 91.86wt%.Constantly circulation
This purification process, second of circulation purity of measurement are 95.93wt%, and it is 98.91wt%, the 4th circulation that third time, which recycles purity,
Purity afterwards is 99.51%.
The purification effect of embodiment 1-4 is separately listed in Table 1 below.
The purification effect of 1 embodiment 1-4 of table
Claims (10)
1. a kind of purification process of polyhydroxyalkanoate, includes the following steps:
(1) PHA crude product is dissolved in organic solvent, heats up and is centrifuged after stirring cooling simultaneously；
The organic solvent is miscible with water；
(2) water is added into the solution after the separation, precipitate is collected after centrifugation；
(3) it adopts and washes with water the precipitate, that is, realize the purifying to the polyhydroxyalkanoate.
2. purification process according to claim 1, it is characterised in that: the PHA is that carbon atom number is 3~5 short
The medium chain length PHA that chain PHA or carbon atom number are 6~24.
3. purification process according to claim 1 or 2, it is characterised in that: the organic solvent is nitrogenous cricoid organic
Object.
4. purification process according to claim 3, it is characterised in that: the organic solvent is 2-Pyrrolidone, N- methyl
Pyrrolidones, N- ethyl-2-pyrrolidone or N- methyl caprolactam.
5. purification process described in any one of -4 according to claim 1, it is characterised in that: in step (1), after the heating
Temperature is 70~150 DEG C, and the time of the stirring is 2~10 hours；
The dosage of the organic solvent are as follows: PHA crude product described in 1g: organic solvent described in 30~50mL.
6. purification process according to any one of claims 1-5, it is characterised in that: in step (1), after the cooling
Temperature is 25~40 DEG C；
The revolving speed of the centrifugation is 3000~4000rpm.
7. purification process according to claim 1 to 6, it is characterised in that: in step (1), the PHA crude product
It is mixed in a container with the organic solvent；
The container is to seal stirred tank or the compression resistance stirred tank with pressurization and heating function.
8. purification process described in any one of -7 according to claim 1, it is characterised in that: in step (2), the water is ultrapure
Water；
The additional amount of the water is 2~6 times of the organic solvent；
It is stirred 30~60 minutes after the water is added；
The centrifugation is carried out under conditions of revolving speed is not less than 5000rpm；
The time of the centrifugation is 30~60 minutes.
9. purification process according to claim 1 to 8, it is characterised in that: in step (3), the water is ultrapure
Water；
The additional amount of the water is 2~6 times of the organic solvent；
The number of the cleaning is 1~4 time.
10. purification process according to claim 1 to 9, it is characterised in that: the method also includes to step
(1) the step of organic solvent in is recycled after filtering.
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| CN111647151A (en) * | 2020-06-10 | 2020-09-11 | 珠海麦得发生物科技股份有限公司 | Efficient full-automatic secondary PHA purification process |
| CN112608463A (en) * | 2020-11-25 | 2021-04-06 | 珠海麦得发生物科技股份有限公司 | Method for regulating and controlling molecular weight of aliphatic polyester |
| CN113292713A (en) * | 2021-06-08 | 2021-08-24 | 中山大学附属第六医院 | Molecular weight grading and purifying method of polyhydroxyalkanoate |
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| CN114591499A (en) * | 2022-03-17 | 2022-06-07 | 珠海麦得发生物科技股份有限公司 | Preparation method and application of poly (R) -3-hydroxybutyrate |
| CN114768564A (en) * | 2022-04-07 | 2022-07-22 | 珠海麦得发生物科技股份有限公司 | PHA purification device and purification method |
| CN114891196A (en) * | 2022-05-12 | 2022-08-12 | 珠海麦得发生物科技股份有限公司 | Injectable gel polyhydroxyalkanoate and preparation method and application thereof |
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| CN114591499A (en) * | 2022-03-17 | 2022-06-07 | 珠海麦得发生物科技股份有限公司 | Preparation method and application of poly (R) -3-hydroxybutyrate |
| CN114591499B (en) * | 2022-03-17 | 2023-06-13 | 珠海麦得发生物科技股份有限公司 | Preparation method and application of poly (R) -3-hydroxybutyrate |
| CN114768564A (en) * | 2022-04-07 | 2022-07-22 | 珠海麦得发生物科技股份有限公司 | PHA purification device and purification method |
| CN114768564B (en) * | 2022-04-07 | 2024-05-28 | 珠海麦得发生物科技股份有限公司 | PHA (polyhydroxyalkanoate) purification device and purification method |
| CN114891196A (en) * | 2022-05-12 | 2022-08-12 | 珠海麦得发生物科技股份有限公司 | Injectable gel polyhydroxyalkanoate and preparation method and application thereof |
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