CN105152982A - Method for synthesizing L-citrulline from walnut kernel - Google Patents
Method for synthesizing L-citrulline from walnut kernel Download PDFInfo
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- CN105152982A CN105152982A CN201510687472.3A CN201510687472A CN105152982A CN 105152982 A CN105152982 A CN 105152982A CN 201510687472 A CN201510687472 A CN 201510687472A CN 105152982 A CN105152982 A CN 105152982A
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Abstract
The invention discloses a method for synthesizing L-citrulline from walnut kernel, belonging to the field of chemical synthesis. The method comprises the following steps: extracting walnut kernel, filtering, adding urea, dichlorotetraammonia complexed copper and sodium carbonate into the filtrate, carrying out seal protection by using a gas mixture, carrying out centrifugal filtration, adding a hydrochloric acid solution into the filtration substance, stirring, adding ferrous sulfide, carrying out microwave stirring, adding diatomite, filtering, regulating the pH value, carrying out exchange adsorption by using an anion exchange resin, eluting with ammonia water, distilling the eluate under reduced pressure, and washing the crystal with ethanol. By adopting the ion-exchange process and crystalprecipitation process, the purity of the synthesized L-citrulline is 98% or above, and the yield is up to 89% or above. The production process can not generate wastewater to pollute the environment, is green and environment-friendly, and has the advantages of simple production technique and low cost.
Description
Technical field
The invention discloses a kind of method utilizing walnut kernel to synthesize Cit, belong to chemical industry synthesis field.
Background technology
Cit is a kind of non-protein amino acid, molecular formula C
6h
13n
3o
3, molecular weight 175.19, fusing point 216 ~ 218 DEG C, be colourless column crystallization, can be water-soluble, be insoluble to methyl alcohol and ethanol.Citrulline is extract from watermelon, so called after citrulline at first.Cit has much important physiological function as scavenging free radicals, allosome repelling effect indicator, vasorelaxation action, stabilizing blood pressure and diagnostics classes rheumatic arthritis, anti-oxidant etc.; In addition, it also has regaining one's vigor of highly significant and improves the effect of body immunity.Cit more and more comes into one's own in fields such as food, makeup and medicines in recent years, has development prospect widely.
The production method of current Cit mainly contains plant extraction method, enzyme transforming process, fermentation method and chemical synthesis.
Plant extraction method is lower due to the content of citrulline in plant, and is subject to the impact of the factor such as season, the place of production, and the cost extracting citrulline is higher, is unfavorable for extensive development; Chemical synthesis is hydrolyzed L-arginine in the basic conditions to obtain Cit, and containing optically active enantiomorph D-citrulline in product, it affects quality product, produces a large amount of waste water, contaminate environment in production process; Fermentation method is raw material with glucose, utilizes microorganism strains fermentative production Cit, raw material sources are extensive, production cost is low, product purity is high feature that it has, but the seed selection of superior strain also requires further study; Enzyme transforming process utilizes the arginine deiminase catalysis L-arginine in microbial cells to transform to generate Cit, and the method production technique is simple, production concentration is high, is a kind of most important method of producing citrulline.In the production cost of Cit is formed, the cost of the lower procedures such as separation and purification occupies sizable ratio, therefore, how to adopt efficient isolation technique to be the technical issues that need to address during current Cit is produced.
Summary of the invention
The technical problem that the present invention mainly solves: be hydrolyzed L-arginine in the basic conditions to obtain Cit for current chemosynthesis Cit, containing optically active enantiomorph D-citrulline in product, it affects quality product, a large amount of waste water is produced in production process, the problem of contaminate environment, provide a kind of method utilizing walnut kernel to synthesize Cit, walnut kernel is carried out extraction and filters by the present invention, urea is added in filtered liquid, dichloro four ammonia complexing copper and sodium carbonate, seal protection is carried out with mixed gas, centrifuging adds hydrochloric acid soln in filtrate, Iron sulfuret is added after stirring, microwave adds diatomite after stirring and filters, anionite-exchange resin exchange adsorption is used after adjust ph, use ammoniacal liquor wash-out, elutriant underpressure distillation, washing with alcohol crystallization, the present invention is with adopting ion exchange method and crystalline deposit method, the purity of the Cit of synthesis is more than 98%, yield reaches more than 89%, and production process can not produce contaminated wastewater environment, environmental protection, production technique is simple, cost is low.
In order to solve the problems of the technologies described above, the technical solution adopted in the present invention is:
(1) get 200 ~ 300g walnut kernel to be placed in pulverizer and to pulverize, to sieve to obtain 120 ~ 160 object particulate matter, gained can be put into container, add the alcohol solution dipping particulate matter that massfraction is 60 ~ 70% wherein, functional quality mark be 45% sodium hydroxide regulate pH be 8.0 ~ 9.0, at temperature is 45 ~ 60 DEG C, filter after stirring 1 ~ 2h, collect filtered liquid, so walnut kernel powder is extracted 1 ~ 3 time, merge filtered liquid;
(2) filtered liquid of above-mentioned gained is put into purpose ceramic-film filter to filter, collect filtrate, the filtrate of gained is put into container, add 10 ~ 20g urea, 20 ~ 25g dichloro four ammonia complexing copper and 12 ~ 18g sodium carbonate wherein respectively, mixed gas is used to carry out seal protection to container, at temperature is 50 ~ 60 DEG C, stir until produce without precipitation, then put into whizzer and carry out centrifugation, collect centrifugal thing, described mixed gas be neon, helium and nitrogen by volume 1:1:8 mix;
(3) filtrate of above-mentioned gained is put into container, the massfraction adding 110 ~ 150mL is wherein the hydrochloric acid soln of 5%, stirring makes filtrate dissolve completely, and then add the Iron sulfuret of 10 ~ 15g wherein, under container being placed in the microwave of 280 ~ 350W, after stirring 20 ~ 40min, add 20 ~ 40g100 ~ 120 object diatomite wherein, after leaving standstill 20 ~ 30min, filter;
(4) filtered liquid after above-mentioned filtration is collected, interception 500 ~ 1000 nanofiltration membrane is used to filter, collect permeate and put into container, functional quality mark is the hydrochloric acid soln adjustment 4.0 ~ 5.0 of 30%, at 15 ~ 20 DEG C, carry out anionite-exchange resin absorption, use deionized water to carry out washing resin, collect washings, and then functional quality mark be 25% ammoniacal liquor carry out wash-out, collect elutriant;
(5) container put into by the elutriant merged collected by above-mentioned twice, by being evaporated to 1/3 of effluent volume, then functional quality mark is the sodium hydroxide solution adjustment pH of 60% is 9.0 ~ 10.0, at temperature is 0 ~ 3 DEG C, leave standstill 20 ~ 24h, collecting by filtration filter, functional quality mark be 30% ethanolic soln rinse 2 ~ 3 times, filtrate is put into air dryer air-dry.
Application method of the present invention: can be applied in the fields such as food, makeup and medicine by the Cit that the present invention synthesizes, has scavenging free radicals, allosome repelling effect indicator, vasorelaxation action, stabilizing blood pressure and diagnostics classes rheumatic arthritis, the effect such as anti-oxidant; The purity of the Cit of the present invention's synthesis is 98 ~ 99%, and yield reaches more than 89%.
The invention has the beneficial effects as follows:
(1) the present invention is with adopting ion exchange method and crystalline deposit method, and the purity of the Cit of synthesis is more than 98%, yield reaches more than 89%;
(2) production process of the present invention can not produce contaminated wastewater environment, environmental protection, and production technique is simple, and cost is low.
Embodiment
First get 200 ~ 300g walnut kernel to be placed in pulverizer and to pulverize, to sieve to obtain 120 ~ 160 object particulate matter, gained can be put into container, add the alcohol solution dipping particulate matter that massfraction is 60 ~ 70% wherein, functional quality mark be 45% sodium hydroxide regulate pH be 8.0 ~ 9.0, at temperature is 45 ~ 60 DEG C, filter after stirring 1 ~ 2h, collect filtered liquid, so walnut kernel powder is extracted 1 ~ 3 time, merge filtered liquid; The filtered liquid of gained is put into purpose ceramic-film filter filter, collect filtrate, the filtrate of gained is put into container, add 10 ~ 20g urea, 20 ~ 25g dichloro four ammonia complexing copper and 12 ~ 18g sodium carbonate wherein respectively, mixed gas is used to carry out seal protection to container, at temperature is 50 ~ 60 DEG C, stir until produce without precipitation, then put into whizzer and carry out centrifugation, collect centrifugal thing, described mixed gas be neon, helium and nitrogen by volume 1:1:8 mix; The filtrate of gained is put into container, the massfraction adding 110 ~ 150mL is wherein the hydrochloric acid soln of 5%, stirring makes filtrate dissolve completely, and then add the Iron sulfuret of 10 ~ 15g wherein, under container being placed in the microwave of 280 ~ 350W, after stirring 20 ~ 40min, add 20 ~ 40g100 ~ 120 object diatomite wherein, after leaving standstill 20 ~ 30min, filter; Collect the filtered liquid after filtering, interception 500 ~ 1000 nanofiltration membrane is used to filter, collect permeate and put into container, functional quality mark is the hydrochloric acid soln adjustment 4.0 ~ 5.0 of 30%, at 15 ~ 20 DEG C, carry out anionite-exchange resin absorption, use deionized water to carry out washing resin, collect washings, and then functional quality mark be 25% ammoniacal liquor carry out wash-out, collect elutriant; Container put into by the elutriant merged collected by twice, by being evaporated to 1/3 of effluent volume, then functional quality mark is the sodium hydroxide solution adjustment pH of 60% is 9.0 ~ 10.0, at temperature is 0 ~ 3 DEG C, leave standstill 20 ~ 24h, collecting by filtration filter, functional quality mark be 30% ethanolic soln rinse 2 ~ 3 times, filtrate is put into air dryer air-dry.
Example 1
First get 200g walnut kernel to be placed in pulverizer and to pulverize, to sieve to obtain 120 object particulate matter, gained can be put into container, add the alcohol solution dipping particulate matter that massfraction is 60% wherein, functional quality mark be 45% sodium hydroxide regulate pH be 8.0, at temperature is 45 DEG C, filter after stirring 1h, collect filtered liquid, so 1 time is extracted to walnut kernel powder, merge filtered liquid; The filtered liquid of gained is put into purpose ceramic-film filter filter, collect filtrate, the filtrate of gained is put into container, add 10g urea, 20g dichloro four ammonia complexing copper and 12g sodium carbonate wherein respectively, use mixed gas to carry out seal protection to container, at temperature is 50 DEG C, stir until produce without precipitation, then put into whizzer and carry out centrifugation, collect centrifugal thing, described mixed gas be neon, helium and nitrogen by volume 1:1:8 mix; The filtrate of gained is put into container, the massfraction adding 110mL is wherein the hydrochloric acid soln of 5%, stirring makes filtrate dissolve completely, and then add the Iron sulfuret of 10g wherein, under container being placed in the microwave of 280W, after stirring 20min, add 20g100 object diatomite wherein, after leaving standstill 20min, filter; Collect the filtered liquid after filtering, interception 500 nanofiltration membrane is used to filter, collect permeate and put into container, functional quality mark is the hydrochloric acid soln adjustment 4.0 of 30%, at 15 DEG C, carry out anionite-exchange resin absorption, use deionized water to carry out washing resin, collect washings, and then functional quality mark be 25% ammoniacal liquor carry out wash-out, collect elutriant; Container put into by the elutriant merged collected by twice, by being evaporated to 1/3 of effluent volume, then functional quality mark is the sodium hydroxide solution adjustment pH of 60% is 9.0, at temperature is 0 DEG C, leave standstill 20h, collecting by filtration filter, functional quality mark be 30% ethanolic soln rinse 2 times, filtrate is put into air dryer air-dry.
Application method of the present invention: can be applied in the fields such as food, makeup and medicine by the Cit that the present invention synthesizes, has scavenging free radicals, allosome repelling effect indicator, vasorelaxation action, stabilizing blood pressure and diagnostics classes rheumatic arthritis, the effect such as anti-oxidant; The purity of the Cit of the present invention's synthesis is 98%, and yield reaches 90%.
Example 2
First get 250g walnut kernel to be placed in pulverizer and to pulverize, to sieve to obtain 140 object particulate matter, gained can be put into container, add the alcohol solution dipping particulate matter that massfraction is 65% wherein, functional quality mark be 45% sodium hydroxide regulate pH be 8.5, at temperature is 52 DEG C, filter after stirring 1.5h, collect filtered liquid, so 2 times are extracted to walnut kernel powder, merge filtered liquid; The filtered liquid of gained is put into purpose ceramic-film filter filter, collect filtrate, the filtrate of gained is put into container, add 15g urea, 23g dichloro four ammonia complexing copper and 16g sodium carbonate wherein respectively, use mixed gas to carry out seal protection to container, at temperature is 55 DEG C, stir until produce without precipitation, then put into whizzer and carry out centrifugation, collect centrifugal thing, described mixed gas be neon, helium and nitrogen by volume 1:1:8 mix; The filtrate of gained is put into container, the massfraction adding 130mL is wherein the hydrochloric acid soln of 5%, stirring makes filtrate dissolve completely, and then add the Iron sulfuret of 13g wherein, under container being placed in the microwave of 310W, after stirring 30min, add 30g110 object diatomite wherein, after leaving standstill 25min, filter; Collect the filtered liquid after filtering, interception 750 nanofiltration membrane is used to filter, collect permeate and put into container, functional quality mark is the hydrochloric acid soln adjustment 4.5 of 30%, at 18 DEG C, carry out anionite-exchange resin absorption, use deionized water to carry out washing resin, collect washings, and then functional quality mark be 25% ammoniacal liquor carry out wash-out, collect elutriant; Container put into by the elutriant merged collected by twice, by being evaporated to 1/3 of effluent volume, then functional quality mark is the sodium hydroxide solution adjustment pH of 60% is 9.5, at temperature is 2 DEG C, leave standstill 22h, collecting by filtration filter, functional quality mark be 30% ethanolic soln rinse 2 times, filtrate is put into air dryer air-dry.
Application method of the present invention: can be applied in the fields such as food, makeup and medicine by the Cit that the present invention synthesizes, has scavenging free radicals, allosome repelling effect indicator, vasorelaxation action, stabilizing blood pressure and diagnostics classes rheumatic arthritis, the effect such as anti-oxidant; The purity of the Cit of the present invention's synthesis is 98.5%, and yield reaches 89.5%.
Example 3
First get 300g walnut kernel to be placed in pulverizer and to pulverize, to sieve to obtain 160 object particulate matter, gained can be put into container, add the alcohol solution dipping particulate matter that massfraction is 70% wherein, functional quality mark be 45% sodium hydroxide regulate pH be 9.0, at temperature is 60 DEG C, filter after stirring 2h, collect filtered liquid, so 3 times are extracted to walnut kernel powder, merge filtered liquid; The filtered liquid of gained is put into purpose ceramic-film filter filter, collect filtrate, the filtrate of gained is put into container, add 20g urea, 25g dichloro four ammonia complexing copper and 18g sodium carbonate wherein respectively, use mixed gas to carry out seal protection to container, at temperature is 60 DEG C, stir until produce without precipitation, then put into whizzer and carry out centrifugation, collect centrifugal thing, described mixed gas be neon, helium and nitrogen by volume 1:1:8 mix; The filtrate of gained is put into container, the massfraction adding 150mL is wherein the hydrochloric acid soln of 5%, stirring makes filtrate dissolve completely, and then add the Iron sulfuret of 15g wherein, under container being placed in the microwave of 350W, after stirring 40min, add 40g120 object diatomite wherein, after leaving standstill 30min, filter; Collect the filtered liquid after filtering, interception 1000 nanofiltration membrane is used to filter, collect permeate and put into container, functional quality mark is the hydrochloric acid soln adjustment 5.0 of 30%, at 20 DEG C, carry out anionite-exchange resin absorption, use deionized water to carry out washing resin, collect washings, and then functional quality mark be 25% ammoniacal liquor carry out wash-out, collect elutriant; Container put into by the elutriant merged collected by twice, by being evaporated to 1/3 of effluent volume, then functional quality mark is the sodium hydroxide solution adjustment pH of 60% is 10.0, at temperature is 3 DEG C, leave standstill 24h, collecting by filtration filter, functional quality mark be 30% ethanolic soln rinse 3 times, filtrate is put into air dryer air-dry.
Application method of the present invention: can be applied in the fields such as food, makeup and medicine by the Cit that the present invention synthesizes, has scavenging free radicals, allosome repelling effect indicator, vasorelaxation action, stabilizing blood pressure and diagnostics classes rheumatic arthritis, the effect such as anti-oxidant; The purity of the Cit of the present invention's synthesis is 99%, and yield reaches 92%.
Claims (1)
1. utilize walnut kernel to synthesize a method for Cit, it is characterized in that concrete synthesis step is:
(1) get 200 ~ 300g walnut kernel to be placed in pulverizer and to pulverize, to sieve to obtain 120 ~ 160 object particulate matter, gained can be put into container, add the alcohol solution dipping particulate matter that massfraction is 60 ~ 70% wherein, functional quality mark be 45% sodium hydroxide regulate pH be 8.0 ~ 9.0, at temperature is 45 ~ 60 DEG C, filter after stirring 1 ~ 2h, collect filtered liquid, so walnut kernel powder is extracted 1 ~ 3 time, merge filtered liquid;
(2) filtered liquid of above-mentioned gained is put into purpose ceramic-film filter to filter, collect filtrate, the filtrate of gained is put into container, add 10 ~ 20g urea, 20 ~ 25g dichloro four ammonia complexing copper and 12 ~ 18g sodium carbonate wherein respectively, mixed gas is used to carry out seal protection to container, at temperature is 50 ~ 60 DEG C, stir until produce without precipitation, then put into whizzer and carry out centrifugation, collect centrifugal thing, described mixed gas be neon, helium and nitrogen by volume 1:1:8 mix;
(3) filtrate of above-mentioned gained is put into container, the massfraction adding 110 ~ 150mL is wherein the hydrochloric acid soln of 5%, stirring makes filtrate dissolve completely, and then add the Iron sulfuret of 10 ~ 15g wherein, under container being placed in the microwave of 280 ~ 350W, after stirring 20 ~ 40min, add 20 ~ 40g100 ~ 120 object diatomite wherein, after leaving standstill 20 ~ 30min, filter;
(4) filtered liquid after above-mentioned filtration is collected, interception 500 ~ 1000 nanofiltration membrane is used to filter, collect permeate and put into container, functional quality mark is the hydrochloric acid soln adjustment 4.0 ~ 5.0 of 30%, at 15 ~ 20 DEG C, carry out anionite-exchange resin absorption, use deionized water to carry out washing resin, collect washings, and then functional quality mark be 25% ammoniacal liquor carry out wash-out, collect elutriant;
(5) container put into by the elutriant merged collected by above-mentioned twice, by being evaporated to 1/3 of effluent volume, then functional quality mark is the sodium hydroxide solution adjustment pH of 60% is 9.0 ~ 10.0, at temperature is 0 ~ 3 DEG C, leave standstill 20 ~ 24h, collecting by filtration filter, functional quality mark be 30% ethanolic soln rinse 2 ~ 3 times, filtrate is put into air dryer air-dry.
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| CN101049435A (en) * | 2006-04-03 | 2007-10-10 | 蹇在金 | Method of preparing nutriment for preventing brain dementia of middle-aged persons and elderly persons |
| CN101372465A (en) * | 2007-08-24 | 2009-02-25 | 北京健健康康生物技术有限公司 | Industrial method for extracting natural L-citrulline from water melon or smacking watermelon and other plant tissues |
| CN101863801A (en) * | 2010-06-12 | 2010-10-20 | 徐州医学院 | Preparation method of optical activity citrulline or homocitrulline |
| CN101880245A (en) * | 2010-04-27 | 2010-11-10 | 南京泽朗农业发展有限公司 | Method for purifying citrulline from watermelon |
| CN103141662A (en) * | 2013-03-22 | 2013-06-12 | 丸永贸易（上海）有限公司 | Method for extracting amino acid from fat-extracted walnut protein and composition containing amino acid |
-
2015
- 2015-10-22 CN CN201510687472.3A patent/CN105152982A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101049435A (en) * | 2006-04-03 | 2007-10-10 | 蹇在金 | Method of preparing nutriment for preventing brain dementia of middle-aged persons and elderly persons |
| CN101372465A (en) * | 2007-08-24 | 2009-02-25 | 北京健健康康生物技术有限公司 | Industrial method for extracting natural L-citrulline from water melon or smacking watermelon and other plant tissues |
| CN101880245A (en) * | 2010-04-27 | 2010-11-10 | 南京泽朗农业发展有限公司 | Method for purifying citrulline from watermelon |
| CN101863801A (en) * | 2010-06-12 | 2010-10-20 | 徐州医学院 | Preparation method of optical activity citrulline or homocitrulline |
| CN103141662A (en) * | 2013-03-22 | 2013-06-12 | 丸永贸易（上海）有限公司 | Method for extracting amino acid from fat-extracted walnut protein and composition containing amino acid |
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| Title |
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| 方亮 等: "不同加工工艺对薄壳山核桃饼粕理化性质的影响", 《江西农业学报》 * |
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