CN115991637A - Method for extracting quebrachitol and quebrachitol - Google Patents
Method for extracting quebrachitol and quebrachitol Download PDFInfo
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- CN115991637A CN115991637A CN202211251310.1A CN202211251310A CN115991637A CN 115991637 A CN115991637 A CN 115991637A CN 202211251310 A CN202211251310 A CN 202211251310A CN 115991637 A CN115991637 A CN 115991637A
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- quebrachitol
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- inositol
- flocculation
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- DSCFFEYYQKSRSV-FIZWYUIZSA-N (-)-Quebrachitol Chemical compound CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]1O DSCFFEYYQKSRSV-FIZWYUIZSA-N 0.000 title claims abstract description 104
- DSCFFEYYQKSRSV-UHFFFAOYSA-N 1L-O1-methyl-muco-inositol Natural products COC1C(O)C(O)C(O)C(O)C1O DSCFFEYYQKSRSV-UHFFFAOYSA-N 0.000 title claims abstract description 104
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- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 claims abstract description 49
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims abstract description 49
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for extracting quebrachitol and quebrachitol. The extraction method comprises the following steps: adding inositol into the residual liquid obtained after the electric flocculation of the natural rubber latex, stirring for full dissolution, standing for crystallization, filtering and drying to obtain a crude crystallization product, and then recrystallizing for further purification to obtain a crystallized product of the quebrachitol and inositol; the inositol used for inducing the precipitation of the quebrachitol is low in price, the extraction technical method for extracting the quebrachitol is simple, complex impurity removal steps are avoided, the cost is low, the inositol in the obtained product is nontoxic and harmless to human bodies, the use of the quebrachitol is not affected, and the quebrachitol can be directly used as raw materials of foods and medicines.
Description
Technical Field
The invention relates to the technical field of compounds, in particular to a method for extracting quebrachitol and quebrachitol.
Background
Inositol and its derivatives play an important role in the transmission of cellular information, quebrachitol as a member of the family of myo-alcohols and their derivatives, is considered to be a universal building block naturally occurring and having life activity due to its specific left-hand optical properties. As a chiral agent and an auxiliary raw material, a number of valuable optically active inositol derivatives and other chiral compounds can be synthesized with ease and used as an insecticide, a degerming agent, etc. Currently, scientists are tightly researching the synthesis of novel drugs with optical structures including saccharides, antibiotics, enzyme inhibitors, stereoisomer inositol, inositol phosphates and derivatives thereof by using quebrachitol, and the drugs are used for treating gastric injury, neurodegenerative diseases, cancers, diabetes, AIDS and other diseases.
Natural rubber is produced from natural latex cut from rubber trees, and conventionally, natural latex flocculation is carried out by a positive flocculation method and a reverse flocculation method. The positive flocculation method is to add flocculation-assisting substances into natural latex, has simple process, but takes longer time, has unstable dry glue quality, is difficult to realize industrialization due to the difficulty in realizing continuous production, corroding equipment, and difficult wastewater treatment and polluting the environment. The inverse flocculation method is to add natural latex into flocculation assisting substances, and most of the flocculation assisting substances are synthetic rubber, so that the operation is simple, but the flocculation assisting substances are used, so that the flocculation cost is very high, and the wastewater treatment cost is difficult to treat and pollutes the environment. The domestic rubber industry is also continuously developing, the traditional natural rubber processing production factory is small in scale, and the production technology is lagged behind. At present, the natural latex is coagulated mainly by acid flocculation, and a large amount of wastewater is difficult to post-treat due to the addition of flocculation-assisting substances such as acid, and processing equipment is corroded, so that the quality of the product is difficult to guarantee and insufficient to meet the demands of the current market. The electrophoresis flocculation process can not add other components in the gel process, so that the natural rubber components are reserved maximally, the quality of raw rubber is guaranteed, and meanwhile, compared with the acid flocculation process with the widest application at present, the method can not damage small molecular non-rubber components in the natural latex, and a huge space and convenience are reserved for the subsequent study of the small molecular non-rubber components.
The electric flocculation method is characterized in that the latex is flocculated under the action of an electric field by the characteristic of electrification of rubber particles in the natural latex to obtain the natural rubber. Compared with the traditional flocculation method, the electric flocculation method does not introduce substances outside the original components of the latex, and the flocculation residual liquid can be concentrated to improve the content of quebrachitol due to the phenomenon of water electrolysis of the latex in an electric field and the evaporation of water in the drying process, which is more beneficial to the subsequent extraction process.
The natural latex consists of water, rubber particles and non-rubber components, wherein the non-rubber components have complex components, besides two major types of proteins and phospholipids, various small molecular alcohols, ketones, ethers and other organic matters, and the small molecular organic matters are harmful to human bodies, so that the small molecular organic matters need to be removed as impurities in the extraction process of quebrachitol, and the method is the most important step in the whole extraction process. The natural rubber biological source extraction work of quebrachitol starts in the recent decades in China, but comprehensive existing researches find that the research is concentrated on the removal of impurities in the whole system, the complete analysis of whey components is needed, and the process is complicated. Chinese patent No. CN113092600a discloses a chromatographic purification method of quebrachitol, which comprises pretreating the gel wastewater containing quebrachitol, eluting with an activated carbon chromatographic column, adsorbing with macroporous resin, performing silica gel column chromatography, and recrystallizing the eluate for multiple times to obtain quebrachitol. The above method wastes a lot of energy in the impurity removal step, and is relatively complicated in steps, namely chromatography and membrane filtration methods.
The prior art has the defects of complex process, low yield, high cost and inapplicability to the subsequent industrialized production by utilizing methods such as chromatography purification, filter membrane purification, concentration crystallization purification and the like.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a method for extracting quebrachitol and quebrachitol.
Myoinositol similar to quebrachitol in structure is added into the residual liquid obtained by electric flocculation of natural rubber latex to break the dissolution balance, so that quebrachitol crystallization co-precipitation is induced, and a myoinositol and quebrachitol mixed product is obtained.
The gel process of the method is different from the traditional gel process, a flocculating agent is not used, the balance among rubber particles in latex is broken through by the action of electrophoresis, the rubber particles are coagulated and aggregated, and a simple method for extracting quebrachitol from electric flocculation gel wastewater is designed.
The quebrachitol is a methyl ether derivative of inositol, the two substances are cyclic alcohols, the dissolution mechanism in water is similar, six groups on the inositol are hydroxyl groups and can form hydrogen bonds with water, compared with the quebrachitol with one substituent being methyl ether, the quebrachitol has better solubility in water, so that the dissolution balance of the quebrachitol in water can be destroyed by adding the inositol, and the crystallization is induced.
According to the invention, inositol is utilized to induce the crystallization precipitation of quebrachitol, the obtained product is a mixture of inositol and quebrachitol, and the inositol is harmless to human bodies, so that the product can be directly used together with quebrachitol as a protective agent, a complex process is not needed, the cost is extremely low, the dissolution balance of other small molecules in a system is not influenced, the purification step is simplified to the greatest extent, the method is simpler and more convenient, the time and the labor are saved, and the industrialized popularization is facilitated.
The residual liquid obtained by using the electric flocculation natural rubber latex ensures the maximum retention of quebrachitol in the latex component because other substances are not introduced for flocculation, and meanwhile, the gel residual liquid can be further concentrated in the water electrolysis process of the electric flocculation method and the drying process of the rubber, so that the content of the quebrachitol in the gel residual liquid is improved and is obviously higher than that of the gel waste water flocculated by adding a flocculating agent.
Inositol is a naturally occurring small molecule substance that does not adversely affect the acquisition of human body without excessive amounts. The final product of the invention is the mixture of inositol and quebrachitol, based on the characteristic that the inositol is harmless to human body, the mixture can be directly used as raw materials of food and medicine, and the application effect of quebrachitol is not affected by the presence of the inositol.
The gel process has high degree of continuity and high efficiency, the method for extracting the quebrachitol is simple, the whole cost is low, the application prospect of the quebrachitol is wide, and the comprehensive utilization level of the rubber industry is improved.
It is an object of the present invention to provide a method for extracting quebrachitol, comprising:
(1) Flocculating the concentrated latex or the fresh latex, flocculating in electric flocculation equipment, separating to obtain flocculated residual liquid, and cooling and filtering to obtain flocculated clear liquid;
(2) And (3) adding inositol into the flocculation clear liquid obtained in the step (1), and filtering and separating precipitated crystals to obtain the quebrachitol.
The method of electroflocculation of natural rubber latex may employ the electroflocculation method disclosed in the prior art, and the following method is preferably referred to: chinese patent No. CN107629150a (entitled "a method for extracting latex by using a very high electric field roller"), chinese patent No. CN110256610a (entitled "a method for extracting latex by using a very high electric field roller"), chinese patent No. CN109503734A (entitled "a method for continuously extracting latex by using a very high electric field), chinese patent No. CN110256609A (entitled" a device for extracting latex by using a very high electric field "), chinese patent No. CN110317285A (entitled" a method for extracting latex by using a very high electric field deformable roller "), chinese patent No. CN109369825A (entitled" a method for extracting latex by using an electric field roller "), chinese patent No. CN109280099A (entitled" a method for extracting latex by using an electric field ").
In a preferred embodiment of the present invention,
step (1),
the concentrated latex or the fresh latex is natural rubber latex;
cooling to 0-20 ℃.
In a preferred embodiment of the present invention,
step (2),
adding inositol into the flocculation clear liquid, stirring for full dissolution, standing for crystallization precipitation, filtering to obtain a crystallization crude product, and then recrystallizing for further purification to obtain a crystallization product of the quebrachitol and the inositol;
preferably, the number of recrystallisation is from 2 to 3.
In a preferred embodiment of the present invention,
the flocculation residual liquid is a flocculation residual liquid containing a small amount of rubber components, which is obtained after the natural latex is flocculated into rubber by electric flocculation equipment; and/or the number of the groups of groups,
the dissolution temperature is 10-50 ℃; and/or the number of the groups of groups,
the dissolution time is 10-20 min; and/or the number of the groups of groups,
standing for 24-72 h; and/or the number of the groups of groups,
the stirring speed is 20-60 r/min.
In a preferred embodiment of the present invention,
the residual rubber content of the flocculation residual liquid is less than or equal to 0.3 percent;
the content of quebrachitol in the flocculation residual liquid is more than or equal to 0.3 percent.
In a preferred embodiment of the present invention,
the mass of inositol is 10% -50% of the mass of the flocculation clear liquid, and is preferably 10% -30%.
In a preferred embodiment of the present invention,
the crystallization temperature is 0-20 ℃; standing the flocculation clear solution fully dissolved after inositol is added at 0-20 ℃, separating out quebrachitol and inositol into crystals under the induction of inositol, and filtering to remove the supernatant to obtain a crystal crude product;
and the recrystallization is to dissolve the crude crystallization product and then recrystallize, further remove impurities and purify the product by repeated recrystallization, and wash and dry the product obtained after the recrystallization to obtain the final quebrachitol product.
In a preferred embodiment of the present invention,
the recrystallization process is to dissolve the crude crystallization product into ethanol to saturation, cool to-10 ℃ at 2-3 ℃/h for crystallization precipitation, and separate solid-liquid by a suction filtration device, wherein the solid phase is the crystallization product of quebrachitol and inositol.
The second object of the invention is to provide a quebrachitol product extracted by the method.
The quebrachitol product comprises quebrachitol and inositol.
In a preferred embodiment of the present invention,
the mass fraction of quebrachitol is 0.3-15%; preferably 2 to 15%;
the mass fraction of inositol is 85-99.7%; preferably 85 to 98%.
The invention also aims to provide the application of the quebrachitol product in biological and food raw materials.
Compared with the prior art, the invention has the beneficial effects that:
the flocculation process does not introduce impurities outside the original components of the latex, and has a concentration phenomenon in the electrolytic and drying processes, so that the obtained flocculation residual liquid has higher quebrachitol content;
the technical method for extracting quebrachitol is simple, and the inositol is added to induce the quebrachitol to be crystallized and separated out, so that the complex impurity removal process is not involved;
the extract product extracted by the method is a mixture of quebrachitol and inositol, wherein the inositol is harmless to human body, and can be used as food and medicine raw materials together with the quebrachitol without affecting the efficacy of the quebrachitol.
Detailed Description
The present invention is described in detail below with reference to specific embodiments, and it should be noted that the following embodiments are only for further description of the present invention and should not be construed as limiting the scope of the present invention, and some insubstantial modifications and adjustments of the present invention by those skilled in the art from the present disclosure are still within the scope of the present invention.
The starting materials used in the examples were all conventional commercially available.
And (3) testing:
the content can be directly measured by HPLC, and the residual natural rubber content can be obtained by comparing the actual obtained rubber quality with the theoretical value of the solid content of the latex.
Example 1
Electric flocculation: the electroflocculation residual liquid of the natural latex obtained in example 3 of Chinese patent No. CN110256610A (entitled "method for extracting latex by extremely high electric field roller"). The residual natural rubber content in the residual liquid is 0.01%, and the quebrachitol content is 0.45%;
cooling the electric flocculation residual liquid to 1 ℃, and filtering to obtain flocculation clear liquid;
taking 1kg of flocculation clear liquid, adding 300g of inositol into the electric flocculation residual liquid at 50 ℃, stirring for 20min to fully dissolve, wherein the stirring speed is 60r/min;
the temperature in the crystallization process is controlled to be 20 ℃, the condition is kept stand for 72 hours, the myoethanol and the quebrachitol are induced to be crystallized and separated out together, and the crude crystallization product is obtained after filtration by a suction filtration device and is recrystallized for 2 times.
And (3) dissolving the crude product of the crystallization to a saturated state by using an ethanol solvent at normal temperature during recrystallization, cooling to-10 ℃ at 2-3 ℃/min until crystallization is separated out, and filtering to separate the crystallization and the solvent, thus repeating the steps twice.
The crystallized product was naturally dried at normal temperature to obtain 238g of a mixed product of quebrachitol and inositol.
The quebrachitol accounts for 2% of the mass of the mixture, and the extraction rate of quebrachitol in the residual liquid is 98%.
Example 2
Electric flocculation: the electroflocculation residual liquid of the natural latex obtained in example 2 of Chinese patent No. CN110317285A (entitled "method for extracting latex by using extremely high electric field deformable roller"). The residual natural rubber content in the raffinate was found to be 0.01% and quebrachitol content was found to be 0.72%.
Cooling the electric flocculation residual liquid to 15 ℃, and filtering to obtain flocculation clear liquid;
taking 1kg of flocculation clear liquid, adding 200g of inositol into the electric flocculation residual liquid at 40 ℃, stirring for 20min to fully dissolve, wherein the stirring speed is 40r/min;
the crystallization process temperature was controlled at 15 ℃, the conditions were kept still for 48 hours, the crystallization of myoethanol and quebrachitol was induced to co-precipitate, the crude product was obtained after filtration by a suction filtration device and was recrystallized 2 times, the recrystallization method was the same as in example 1, and the crystallized product was naturally dried at normal temperature to obtain 141g of a mixture
The quebrachitol accounts for 4.9% of the mass of the mixture, and the extraction rate of the quebrachitol in the residual liquid is 96%.
Example 3
Electric flocculation: the electroflocculation residual liquid of the natural latex obtained in example 1 of chinese patent No. CN110256609A (entitled "a device for extracting latex with extremely strong electric field"). The residual natural rubber content in the residual liquid was found to be 0.01% and quebrachitol content was found to be 0.8%.
Cooling the electric flocculation residual liquid to 20 ℃, and filtering to obtain flocculation clear liquid;
taking 1kg of flocculation clear liquid, adding 150g of inositol into the electric flocculation residual liquid at 30 ℃, keeping the condition for standing for 48 hours, stirring for 15min to fully dissolve, and stirring at a speed of 40r/min;
the crystallization process temperature is controlled to be 10 ℃, the myoethanol and the quebrachitol are induced to crystallize and co-precipitate, the crude crystallization product is obtained after filtration by a suction filtration device, then 2 times of recrystallization are carried out, the recrystallization method is the same as that of example 1, and the crystallized product is naturally dried at normal temperature, thus obtaining 94g of mixture.
The quebrachitol accounts for 5.2% of the mass of the mixture, and the extraction rate of the quebrachitol in the residual liquid is 95%.
Example 4
The electric flocculation method comprises the following steps: the electroflocculation raffinate of natural latex obtained in example 1 of chinese patent CN109280099a (entitled "method of electroextraction of latex"). The residual natural rubber content in the raffinate was found to be 0.01% and quebrachitol content was found to be 0.61%.
Cooling the electric flocculation residual liquid to 20 ℃, and filtering to obtain flocculation clear liquid;
taking 1kg of flocculation clear liquid, adding 100g of inositol into the electric flocculation residual liquid at 20 ℃, stirring for 10min to fully dissolve, wherein the stirring speed is 20r/min;
the crystallization process temperature is controlled to be 1 ℃, the conditions are kept stand for 24 hours, the myoethanol and the quebrachitol are induced to be crystallized and separated out together, the crude crystallization product is obtained after filtration by a suction filtration device, then the crude crystallization product is recrystallized for 2 times, the recrystallization method is the same as that of the example 1, and the crystallized product is naturally dried at normal temperature, thus obtaining the mixture with the mass of 42g.
The quebrachitol accounts for 13% of the mass of the mixture, and the extraction rate of quebrachitol in the residual liquid is 94%.
Comparative example 1
Flocculation clear liquid is the same as in example 2;
adding activated carbon into the flocculated clear liquid for decoloring, then carrying out rotary evaporation under the condition of 65 ℃ and 0.09MPa, concentrating to 5% of the original volume, adding 10 times of ethanol, filtering out residual rubber separated out after adding the ethanol, and cooling the obtained residual liquid to-20 ℃ at 5 ℃/h until crystallization is separated out. The obtained crude crystal product has complex components and needs impurity removal treatment. Dissolving the crude product, sequentially passing through a microfiltration membrane and a nanofiltration membrane, and repeating the concentration step, adding methanol, and carrying out repeated recrystallization and purification. Finally, 2.1g of quebrachitol is obtained, and the extraction rate is 30%.
Comparative example 2
4 groups of db/db mice (type II diabetic mice) were set, 3 experimental groups and one blank group, respectively. The experimental groups were fed quebrachitol, inositol and quebrachitol/inositol mixtures (molar ratio 1:9) respectively, at doses of 50mg/kgbw, dissolved in 5ml of water, once daily, with pure water for the blank group and the four remaining groups were all identical. Mice fed quebrachitol and quebrachitol/inositol mixtures were found to have reduced food intake, increased body weight, increased fasting plasma insulin levels, while mice fed inositol and the blank group had no significant changes.
Examples 1 to 4 the electro-flocculated residual solutions of natural latex obtained by different methods were subjected to quebrachitol purification with an extraction rate of 94 to 98%, whereas comparative example 1 was subjected to acid flocculation with a gel wastewater purification with an extraction rate of 30%.
The flocculation processes of examples 1 to 4 did not introduce impurities other than the original components of the latex, and the flocculation process had a concentration phenomenon by electrolysis and drying processes, and the obtained flocculated residual liquid had a higher quebrachitol content; the extracted product is quebrachitol and inositol mixture, wherein inositol is harmless to human body, and can be used together with quebrachitol as food and medicinal raw material without affecting the efficacy of quebrachitol.
The technical method for extracting quebrachitol is simple, and the inositol is added to induce the quebrachitol to be crystallized and separated out, so that the complex impurity removal process is not involved.
Claims (10)
1. A method of extracting quebrachitol, the method comprising:
(1) Flocculating the concentrated latex or the fresh latex, flocculating in electric flocculation equipment, separating to obtain flocculated residual liquid, and cooling and filtering to obtain flocculated clear liquid;
(2) And (3) adding inositol into the flocculation clear liquid obtained in the step (1), and filtering and separating precipitated crystals to obtain the quebrachitol.
2. The method for extracting quebrachitol according to claim 1, wherein:
step (1),
the concentrated latex or the fresh latex is natural rubber latex; and/or the number of the groups of groups,
cooling to 0-20 ℃.
3. The method for extracting quebrachitol according to claim 1, wherein:
step (2),
adding inositol into the flocculation clear liquid, stirring for full dissolution, standing for crystallization precipitation, filtering to obtain a crystallization crude product, and then recrystallizing for further purification to obtain a crystallization product of quebrachitol and inositol;
preferably, the number of recrystallisation is from 2 to 3.
4. A method of extracting quebrachitol according to claim 3, wherein:
the flocculation residual liquid is a flocculation residual liquid containing a small amount of rubber components, which is obtained after the natural latex is flocculated into rubber by electric flocculation equipment; and/or the number of the groups of groups,
the dissolution temperature is 10-50 ℃; and/or the number of the groups of groups,
the dissolution time is 10-20 min; and/or the number of the groups of groups,
standing for 24-72 h; and/or the number of the groups of groups,
the stirring speed is 20-60 r/min.
5. The method for extracting quebrachitol according to claim 1, wherein:
the residual rubber content of the flocculation residual liquid is less than or equal to 0.3 percent; and/or the number of the groups of groups,
the content of quebrachitol in the flocculation residual liquid is more than or equal to 0.3 percent.
6. The method for extracting quebrachitol according to claim 1, wherein:
the mass of inositol is 10-50% of the mass of the flocculation clear liquid, preferably 10-30%.
7. A method of extracting quebrachitol according to claim 3, wherein:
the crystallization temperature is 0-20 ℃; the recrystallization is to dissolve the crude crystallization product and then recrystallize; preferably, the recrystallization process is to dissolve the crude crystallization product into ethanol to saturation, cool to-10 ℃ at 2-3 ℃/h for crystallization precipitation, and obtain the crystallization product of quebrachitol and inositol after solid-liquid separation.
8. A quebrachitol product extracted by the method of any one of claims 1-7, the quebrachitol product comprising quebrachitol and inositol.
9. The quebrachitol product of claim 8, wherein:
the mass fraction of the quebrachitol is 0.3-15%, preferably 2-15%; and/or the number of the groups of groups,
the mass fraction of inositol is 85-99.7%, preferably 85-98%.
10. Use of a quebrachitol product according to claim 8 or 9 in biological and food raw materials.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| CN202111214189 | 2021-10-19 | ||
| CN2021112141890 | 2021-10-19 |
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| CN115991637B CN115991637B (en) | 2024-06-25 |
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Non-Patent Citations (1)
| Title |
|---|
| 孙思佳: "电泳法絮凝橡胶机理研究及产业化应用", 中国优秀硕士学位论文全文数据库工程科技Ⅰ辑, no. 2, pages 016 - 1332 * |
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