CN112479848A - Purification method for synthesizing coenzyme Q10 by biological fermentation method - Google Patents

Purification method for synthesizing coenzyme Q10 by biological fermentation method Download PDF

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CN112479848A
CN112479848A CN202011421616.8A CN202011421616A CN112479848A CN 112479848 A CN112479848 A CN 112479848A CN 202011421616 A CN202011421616 A CN 202011421616A CN 112479848 A CN112479848 A CN 112479848A
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coenzyme
silica gel
biological fermentation
extraction
carbon dioxide
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程终发
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Shandong Taihe Water Treatment Technologies Co Ltd
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Shandong Taihe Water Treatment Technologies Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/10—Separation; Purification; Stabilisation; Use of additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention discloses a purification method for synthesizing coenzyme Q10 by a biological fermentation method. Specifically, coenzyme Q obtained by drying biological fermentation10Crushing the raw materials until the particle size ranges from 100 meshes to 200 meshes, performing carbon dioxide supercritical extraction, and using absolute ethyl alcohol as a solvent to enable the flowing paste to be prepared into the paste according to the following formula (1-5): 1, adsorbing and uniformly mixing by silica gel, and separating by using a supercritical mixed elution method, thereby realizing coenzyme Q10And (4) purifying. The method utilizes the elution of a mixed system of supercritical carbon dioxide and an organic solvent to carry out biological fermentation to synthesize coenzyme Q10The separation and purification of the method has the advantages of good separation effect, high utilization rate of carbon dioxide, low usage amount of organic solvent, safety, environmental protection and the like, the purity of the product can reach more than 99 percent, and meanwhile, the reuse of silica gel and the solvent can be realized, thereby being beneficial to the implementation of large-scale production.

Description

Purification method for synthesizing coenzyme Q10 by biological fermentation method
Technical Field
The invention relates to the technical field of separation and purification, in particular to a purification method for preparing coenzyme Q10 by a biological fermentation method.
Background
Coenzyme Q10Is a fat-soluble quinone substance existing in human body cell, exists in combined or free form in organism mitochondrial inner membrane, and combines with protein in vivo to exert bioactivity, and its molecular formula is C59H90O4It is widely found in the body of the organism having a respiratory action in the natural world and is therefore also called ubiquinone.
Coenzyme Q has been disclosed10The preparation technology mainly comprises an animal and plant tissue extraction method, a chemical synthesis method and a microbial fermentation method. Coenzyme Q10The earliest industrial production methods were extracted from animals and processed, and the products obtained by using the methods had large raw material amount, low yield and high production cost. All-grass of MandeliaCoenzyme Q preparation by using nitol as raw material10The (semi) synthesis method of (2) has relatively low yield, the product is a mixture of cis-trans isomers, the activity is not strong, and chiral separation and purification are required. Currently, coenzyme Q is produced by microbial fermentation10Because of the advantages of low production cost, high active ingredient content and relatively simple production process, the method is considered as the most promising production process technical route at home and abroad. However, regardless of the process route adopted for the production of coenzyme Q10Finally, the crude product obtained from the raw material needs to be subjected to the process treatment steps of extraction, separation, purification and the like to obtain the coenzyme Q meeting the requirements10The product, so the high-efficiency separation and purification process for developing the product is coenzyme Q10Key technology for product industrialization. Production of coenzyme Q by Song Asia Qin et al microbial fermentation method10Coenzyme Q is reviewed in the research progress on extraction methods10The extraction method mainly comprises saponification extraction, organic solvent stirring and cell disruption extraction, grinding cell disruption extraction, ultrasonic cell disruption extraction, etc. Chinese patent CN107673958A discloses a coenzyme Q10The separation and purification method comprises removing solvent from concentrated solution obtained by treating with multi-stage serial nanofiltration device, and crystallizing with ethanol to obtain coenzyme Q with content of more than 99%10And (7) fine products. Chinese patent publication No. CN107337593A describes a method for preparing coenzyme Q10The fermentation liquor is microfiltered by ceramic membrane and spray dried to obtain crude product, which is extracted by acetone, split-phase and decompressed and concentrated to obtain coenzyme Q10Extracting the concentrated solution, and then obtaining coenzyme Q by the processes of petroleum ether extraction, silica gel column chromatography, reduced pressure distillation and concentration of eluent, crystallization and drying10And (7) fine products. Chinese patent CN108047014B discloses a method for separating coenzyme Q by using ionic liquid10The method of (1), with coenzyme Q10The crude product of (A) is taken as a raw material, a nonpolar organic solvent is taken as a raw material solvent and a detergent, and an ionic liquid or a binary mixed solvent consisting of the ionic liquid and the polar organic solvent is taken as an extracting agent to obtain the coenzyme Q with high purity10Compared with the traditional organic solvent, the method has the advantages that the extracting agent has better thermal stability and selectivity, but the problem of using a large amount of extracting agent, detergent and the like is still not solved, and finally more extracting agent, detergent and the like are generatedOrganic solvent waste liquid. In Chinese patent CN108218681A, coenzyme Q10Dissolving the crude extract in acetone/methanol mixed solution, adsorbing and eluting with organic hydrocarbon bonded silica gel or organic hydrocarbon bonded silica gel containing polar organic functional group to remove impurities to obtain high purity coenzyme Q10A monomer. CN105886562A introduces a microbial fermentation method for preparing coenzyme Q10The purification step of (1) is to use silica gel adsorption column, firstly wash the crude product with petroleum ether, then elute with petroleum ether/ether mixed solution, and distill the eluent under reduced pressure to prepare yellow oily crystal. CN103819326B discloses a 38-42 ℃ silica gel column adsorption method, and then a method for preparing coenzyme Q by using one or more of methanol, ethanol, ethylene glycol, isopropanol, n-butanol, ethyl acetate, petroleum ether and chloroform as a combined solvent for eluent purification and separation and microorganism fermentation10The method of (1). The CN101987815B patent discloses the preparation of high purity coenzyme Q10The purification process of (1), comprising subjecting coenzyme Q to10Pretreating the crude extract with adsorption resin, concentrating, crystallizing, recrystallizing, and separating and purifying with petroleum ether/diethyl ether or ethyl acetate/n-hexane mixed solvent as eluent by silica gel column to obtain refined coenzyme Q10. The patent publication No. CN101111465A is directed to separating coenzyme Q at 20-40 deg.C by normal phase chromatography10The mixture of (a) produces a pure product.
With coenzyme Q10The research of the application field is continuously deep, and the domestic and foreign consumption markets are about the coenzyme Q10Is also increasingly in demand, but coenzyme Q10The separation and purification technology still has various technical problems of low yield, large organic solvent consumption, high purification cost and the like, and the prior coenzyme Q is urgently needed to be solved10The column separation method using silica gel as an adsorption matrix for separation and purification has the problems of high regeneration cost and low cyclic utilization rate of silica gel and pollution to the environment to a certain extent. Thus, coenzyme Q is to be realized10Especially the industrial production of the microbial fermentation process, a new technical method should be explored and developed from the refining processes of crude product extraction, separation, purification and the like.
Disclosure of Invention
The invention aims to provide a purification method for preparing coenzyme Q10 by a biological fermentation method, and aims to solve the problem of the existing coenzyme Q1010The invention provides a mixed elution mode of supercritical fluid and organic solvent, which realizes the preparation of coenzyme Q by a biological fermentation method10And (4) purifying. The method utilizes the elution of a mixed system of supercritical carbon dioxide and an organic solvent to carry out biological fermentation to synthesize coenzyme Q10The separation and purification of the method has the advantages of good separation effect, high utilization rate of carbon dioxide, low usage amount of organic solvent, safety, environmental protection and the like, the purity of the product can reach more than 99 percent, and meanwhile, the reuse of silica gel and the solvent can be realized, thereby being beneficial to the implementation of large-scale production.
In order to achieve the purpose, the invention adopts the following technical scheme:
a purification method for synthesizing coenzyme Q10 by a biological fermentation method comprises the following steps:
1) coenzyme Q prepared by microbial fermentation method10Performing supercritical carbon dioxide extraction separation primary extraction treatment on the mushroom residues under the conditions that the pressure is 42MPa, the extraction and separation temperature is 40-45 ℃, the flow rate of carbon dioxide is controlled to be 30-50L/h, and the cyclic extraction time is 1-4 h to obtain the coenzyme Q with the mass percentage content of 50-60%10Crude extract;
2) the coenzyme Q obtained in step (1)10Mixing the crude extract with absolute ethyl alcohol according to the proportion of 1: (1-5), heating to 45-50 ℃, and stirring to form a uniform liquid mixed system;
3) continuously keeping the system temperature of 45-50 ℃, adding silica gel powder with the particle size of 100-200 meshes according to the mass ratio of (1-3) to 1 to the mixed solution obtained in the step (2), and fully stirring to enable the material to be uniformly adsorbed on the silica gel to form a sample preparation;
4) spreading the sample obtained in the step (3) at the lower end of the extraction kettle, adding the blank silica gel powder with the same specification in the step (3) above the sample, fully compacting to enable the upper end of the extraction kettle to reserve a space of 2-3 cm, eluting and separating by using supercritical and organic eluent, distilling and drying to obtain yellow coenzyme Q10Product, recovered solvent can be recycledThe ring is utilized.
As a further scheme of the invention, the coenzyme Q in the mushroom dregs in the step (1)10The content is 2-3%.
As a further embodiment of the present invention, the coenzyme Q in the step (1)10The impurity component in the crude extract with the mass percent content of about 50-60 percent is mainly 5-demethoxyl coenzyme Q10Coenzyme Q9、Q11Isovalent system and reduced coenzyme Q9And a minor amount of menadione 8.
As a further scheme of the invention, in the step (4), the supercritical and organic eluent are synchronously injected into an extraction kettle to carry out chromatographic separation on the silica gel sample.
As a further scheme of the invention, the organic eluent is injected from an agent carrying inlet of the supercritical extraction device at a flow rate set according to actual requirements.
As a further scheme of the invention, the organic eluent is selected from any two or three of absolute ethyl alcohol, petroleum ether, ethyl acetate, chloroform, acetone, n-hexane and the like which are mixed according to any suitable proportion.
As a further scheme of the invention, the control range of the circulating flow rate of the supercritical carbon dioxide in the step (4) is 10-20L/h, the control range of the flow rate of the organic eluent is 0.1-1L/h, and the elution separation time is 1-3 h.
As a further scheme of the invention, the silica gel powder can be recycled after being repeatedly extracted by supercritical carbon dioxide, and the organic solvent eluent can be recycled after being distilled.
The invention has the beneficial effects that: the invention adopts the methods of supercritical fluid extraction crude extraction, silica gel adsorption crude extract and supercritical fluid + organic mixed solvent elution silica gel adsorption system again, thereby realizing the synthesis of coenzyme Q by a biological fermentation method10The method has high separation efficiency, short period, high product purity up to more than 99 percent, and easy realization of the cyclic utilization of the adsorption silica gel and the mixed solvent; the method effectively avoids coenzyme Q10In the existing purification technologies of silica gel chromatographic separation, solvent recrystallization and the likeThe technical problem of generating a large amount of organic waste liquid, greatly reduces the generation of solid waste and organic waste liquid, and is beneficial to environmental safety.
Detailed Description
The technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Coenzyme Q prepared by microbial fermentation method10500g of mushroom dregs (wherein: coenzyme Q)102.97 percent) is subjected to supercritical carbon dioxide extraction separation primary extraction treatment with the pressure of 42MPa, the extraction and separation temperature range of 45 ℃, the carbon dioxide flow rate of 30L/h and the circulation extraction time of 3h to obtain the coenzyme Q with the mass percent of 57 percent1025.82g of crude extract; adding coenzyme Q obtained above10Adding 10g of absolute ethyl alcohol into 5g of the crude extract, heating to 45 ℃, stirring to form a uniform liquid mixed system, adding 15g of silica gel powder with the particle size of 100-200 meshes, and fully stirring and uniformly mixing to form a silica gel sample; preparing a silica gel sample, paving the silica gel sample at the bottom of an extraction kettle of a supercritical extraction device, adding blank silica gel powder with the particle size of 100-200 meshes, and fully compacting to enable the upper end of the extraction kettle to reserve 2-3 cm of space; controlling the pressure of the supercritical fluid at 30MPa and the flow rate at 10L/h, the temperature in the extraction kettle at 45 +/-1 ℃, and simultaneously, controlling the pressure V at 0.3L/hEthyl acetate:VPetroleum etherDriving organic mixed elution solvent of =1:15 into the separation tank from the carrier inlet at a constant speed, consuming 409.5g organic eluent together when circularly eluting for 2.1h, and receiving coenzyme Q together from the discharge hole of the separation tank10The total amount of the mixed liquid with the liquid chromatography purity of more than 99 percent is 307g, and yellow coenzyme Q is obtained by distillation and drying102.47g of solid, which is detected and analyzed by high performance liquid chromatography to obtain: coenzyme Q10The content of the impurity is 99.65 percent and the impurity component is coenzyme Q9Content of 0.27%, coenzyme Q11Content of 0.08%, coenzyme Q10The recovery was 86.67%.
Example 2
Taking coenzyme Q prepared in example 110Adding 5g of crude extract into 15g of absolute ethyl alcohol, heating to 48 ℃ to form a uniform mixed liquid flowing system, and then adding 25g of silica gel powder with the particle size of 100-200 meshes, fully stirring and uniformly mixing to form a silica gel sample; preparing a silica gel sample, paving the silica gel sample at the bottom of an extraction kettle of a supercritical extraction device, adding blank silica gel powder with the particle size of 100-200 meshes, and fully compacting to enable the upper end of the extraction kettle to reserve 2-3 cm of space; controlling the pressure of the supercritical fluid at 35MPa and the flow rate at 20L/h, the temperature in the extraction kettle at 45 +/-1 ℃, and simultaneously, controlling the pressure V at 0.5L/hN-hexane:VPetroleum etherThe mixed organic elution solvent with the ratio of 1:20 is injected from the carrier inlet at a constant speed, 812.5g of organic eluent is consumed altogether when the mixed organic elution solvent is circularly eluted for 2.5 hours, and coenzyme Q is received from the discharge hole of the separation tank10624g mixed liquid with liquid chromatogram purity more than 99 percent, and yellow coenzyme Q is obtained by distillation and drying102.53g of solid, detected and analyzed by high performance liquid chromatography to obtain: coenzyme Q1099.33% of coenzyme Q as impurity component9Reduced coenzyme Q content 0.19%9Content of 0.08%, coenzyme Q11Content of 0.39%, coenzyme Q10The recovery was 88.77%.
Example 3
Recycling silica gel powder and organic eluent;
the coenzymes Q separated in the above examples 1-2 were each10And continuously and circularly eluting the residual materials by the carbon dioxide supercritical fluid until all the silica gel adsorption substances in the extraction kettle flow out, taking out the colorless to dark gray silica gel powder, and drying. Coenzyme Q was treated with the above-mentioned recovered silica gel powder according to the process parameters and the operation method of example 110And (3) purifying and separating the crude extract, wherein 282g of solvent distilled from the separation receptor in example 1 is mixed in the mixed solvent pumped into a separation system from a carrying tank to obtain 2.44g of yellow product, and the yellow product is obtained by high performance liquid chromatography detection analysis: coenzyme Q10The content of the impurity is 99.19%, and the impurity component is coenzyme Q9Content of 0.81%, coenzyme Q10The recovery was 85.61%.
Comparative example
Separating and purifying by column chromatography;
taking coenzyme Q prepared in example 110Adding 10g of absolute ethyl alcohol into 5g of crude extract according to the operation method described in the embodiment 1, heating to 45 ℃, stirring to form a uniform liquid mixed system, adding 15g of silica gel powder with the particle size of 100-200 meshes, fully stirring and uniformly mixing to form a silica gel sample, taking a silica gel column with the particle size of 100-200 meshes and the height ratio of 1:14 as an adsorption medium, and taking V as a VEthyl acetate:VPetroleum etherContinuously eluting for 3 hours by using the eluent as the ratio of 1:10, consuming 1950g of the eluent together, and collecting coenzyme Q10723g of mixed liquid with the liquid chromatography purity of more than 99 percent in total is obtained, and yellow coenzyme Q is obtained by distillation and drying101.89g of solid, which is detected and analyzed by high performance liquid chromatography to obtain: coenzyme Q1099.29% of coenzyme Q as impurity component9Reduced coenzyme Q content of 0.44%9Content of 0.06%, coenzyme Q11Content of 0.21%, coenzyme Q10The recovery was 66.32%.
The method has high separation efficiency, short period and product purity of over 99 percent, and is easy to realize the cyclic utilization of the adsorption silica gel and the mixed solvent; the method effectively avoids coenzyme Q10The method has the advantages of solving the technical problem of generating a large amount of organic waste liquid in the existing purification technologies such as silica gel chromatographic separation, solvent recrystallization and the like, greatly reducing the generation of solid waste and organic waste liquid, and being beneficial to environmental safety.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.

Claims (8)

1. A method for purifying coenzyme Q10 synthesized by a biological fermentation method is characterized by comprising the following steps:
coenzyme Q prepared by microbial fermentation method10The pressure of the mushroom dregs is 42MPa, the extraction and separation temperature is 40-45 ℃, the flow rate of carbon dioxide is controlled to be 30-50L/h, and the time of circulating extraction is selected to be 1-4 hPerforming supercritical carbon dioxide extraction separation primary extraction treatment to obtain coenzyme Q with the mass percentage content of 50-60%10Crude extract;
adding coenzyme Q obtained in step (1)10Mixing the crude extract with absolute ethyl alcohol according to the proportion of 1: (1-5), heating to 45-50 ℃, and stirring to form a uniform liquid mixed system;
continuously keeping the system temperature at 45-50 ℃, adding silica gel powder with the particle size of 100-200 meshes according to the mass ratio of (1-3) to 1 to the mixed solution obtained in the step (2), and fully stirring to enable the material to be uniformly adsorbed on the silica gel to form a sample preparation;
spreading the sample obtained in the step (3) at the lower end of the extraction kettle, adding the blank silica gel powder with the same specification in the step (3) above the sample, fully compacting to ensure that the space of 2-3 cm is reserved at the upper end of the extraction kettle, eluting and separating by using supercritical and organic eluent, distilling and drying to obtain yellow coenzyme Q10The product and the recovered solvent can be recycled.
2. The method for purifying coenzyme Q10 by using biological fermentation method according to claim 1, wherein the coenzyme Q10 is obtained from the mushroom dregs in step (1)10The content is 2-3%.
3. The method for purifying coenzyme Q10 by biological fermentation according to claim 1, wherein the coenzyme Q10 is obtained in step (1)10The impurity component in the crude extract with the mass percent content of 50-60% is mainly 5-demethoxyl coenzyme Q10Coenzyme Q9Coenzyme Q11And reduced coenzyme Q9And a minor amount of menadione 8.
4. The method for purifying coenzyme Q10 by biological fermentation according to claim 1, wherein the supercritical and organic eluents in step (4) are synchronously injected into an extraction kettle to perform chromatographic separation on silica gel samples.
5. The method for purifying coenzyme Q10 by biological fermentation according to claim 1, wherein the organic eluent is injected from an agent-carrying inlet of a supercritical extraction apparatus at a flow rate set according to actual requirements.
6. The method for purifying coenzyme Q10 by biological fermentation method according to claim 5, wherein the organic eluent is selected from any two or three of absolute ethyl alcohol, petroleum ether, ethyl acetate, chloroform, acetone, n-hexane, etc. which are mixed in any suitable ratio.
7. The method for purifying coenzyme Q10 synthesized by biological fermentation method according to claims 1-6, wherein the circulating flow rate of supercritical carbon dioxide in step (4) is controlled within the range of 10-20L/h, the flow rate of organic eluent is controlled within the range of 0.1-1L/h, and the elution separation time is 1-3 h.
8. The method for purifying coenzyme Q10 by biological fermentation according to claim 7, wherein the silica gel powder can be recycled after repeated extraction treatment by supercritical carbon dioxide, and the organic solvent eluent can be recycled by distillation.
CN202011421616.8A 2020-12-08 2020-12-08 Purification method for synthesizing coenzyme Q10 by biological fermentation method Pending CN112479848A (en)

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Citations (3)

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Publication number Priority date Publication date Assignee Title
CN102391092A (en) * 2011-11-22 2012-03-28 杭州华东医药集团康润制药有限公司 Method for preparing high-purity coenzyme Q10 in large scale
CN109535053A (en) * 2017-09-21 2019-03-29 江苏汉邦科技有限公司 A method of calciferol is prepared using supercritical fluid chromatography
CN111487356A (en) * 2020-05-21 2020-08-04 内蒙古金达威药业有限公司 Method for separating coenzyme Q10 by using supercritical fluid chromatography system

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102391092A (en) * 2011-11-22 2012-03-28 杭州华东医药集团康润制药有限公司 Method for preparing high-purity coenzyme Q10 in large scale
CN109535053A (en) * 2017-09-21 2019-03-29 江苏汉邦科技有限公司 A method of calciferol is prepared using supercritical fluid chromatography
CN111487356A (en) * 2020-05-21 2020-08-04 内蒙古金达威药业有限公司 Method for separating coenzyme Q10 by using supercritical fluid chromatography system

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