CN1724514B - Preparation method of L-homoarginine hydrochloride - Google Patents
Preparation method of L-homoarginine hydrochloride Download PDFInfo
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- CN1724514B CN1724514B CN 200410052953 CN200410052953A CN1724514B CN 1724514 B CN1724514 B CN 1724514B CN 200410052953 CN200410052953 CN 200410052953 CN 200410052953 A CN200410052953 A CN 200410052953A CN 1724514 B CN1724514 B CN 1724514B
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Abstract
The invention provides a process for preparing L-homoarginine hydrochloride through chemosynthesis, which comprises dissolving L-lysine hydrochlorate and copper oxide into water, heating, cooling down, filtering, mixing and stirring with water-dissolved oxymethylisothiourea and barium hydroxide, adjusting pH, heating, heat preserving, cooling down, charging anhydrous alcohol, stewing, filtering, thus obtaining crystalline L-homoarginine cuprate composition, then dissolving the compound with water, elevating temperature, letting in hydrogen sulfide till the end of the reaction, cooling down and charging activated charcoal, agitating, filtering, adjusting pH, stabilizing, eliminating moisture, cooling down, charging anhydrous alcohol again and stewing, finally filtering and purifying.
Description
Technical field:
The preparation method, the especially chemical synthesis that the present invention relates to a kind of L-homoarginine hydrochloride prepare the preparation method of L-homoarginine hydrochloride.
Background technology:
The existing method for preparing L-homoarginine hydrochloride, described as U.S.'s journal of biological chemistry 183139 (1950) is starting raw material with the L lysine HCL, under boiling state, generate the mantoquita mixture with cupric oxide, after filtering, mantoquita mixture and oxygen methyl-isothiourea and sodium hydroxide at room temperature reacted 12 hours, generate L-homoarginine mantoquita mixture, this solution is placed on 24 hours after-filtration in the refrigerator, wash with frozen water again.Add the reaction of oxygen methyl-isothiourea with washings after the washing and filtrate, and repeat above step.The L-homoarginine mantoquita mixture that generates makes it be reduced into the homoarginine hydrochloride with hydrogen sulfide and hydrochloric acid again.With resulting solution after removing moisture under the negative pressure, the oily matter that obtains crystallization in 95% alcohol and aniline can obtain L-homoarginine hydrochloride raw product, and this raw product is put into the alcohol recrystallization, and drying obtains white powder crystalline solid, i.e. finished product.Adopt the deficiency of aforesaid method to be: product purity is not high, yield only about 40%, and used harmful aniline, handle to the three wastes and brought difficulty.
Summary of the invention:
The preparation method who the purpose of this invention is to provide L-homoarginine hydrochloride, this preparation method do not use harmful aniline in preparation process, and can improve product yield and purity, shortened process, and step simplifies the operation.
The present invention is achieved in that with the L lysine HCL of 1: 0.78～0.8 weight ratio and cupric oxide and is dissolved under whipped state in 2～3 times the water, is heated to boiling and keeps 2 hours, and cool to room temperature removes by filter unreacted cupric oxide then.Get oxygen methyl-isothiourea and hydrated barta by weight 1: 1.75～1.8, be dissolved in the less water respectively, and mix stirring with above-mentioned reaction solution, after in mixing stirring, splashing into 4N sodium hydroxide accent pH value to 10～11, be heated to 55 °～60 ℃, kept this thermotonus 12 to 15 hours, be cooled to room temperature then, adding an amount of raw spirit left standstill 12～15 hours, make the material sufficient crystallising, at room temperature obtain xln L-homoarginine mantoquita mixture after filtration, this mixture is with 10 times water dissolution, be warmed up to 50 °～55 ℃, slowly feed hydrogen sulfide to reaction end, make its mantoquita of sloughing and impurity, after cooling, adsorb with proper amount of active carbon again, stir, filter, after filtrate is washed with suitable quantity of water, washings and filtered liquid are mixed, dripping hydrochloric acid is regulated PH to 2～3 under whipped state, under 60 °～65 ℃ negative pressure, removes the moisture content in the feed liquid, be cooled to room temperature, add raw spirit, left standstill 12～15 hours, make the material sufficient crystallising, obtain the white powder xln more after filtration, this xln gets final product through purifying.
The present invention has saved harmful aniline owing to adopt above-mentioned preparation method, can significantly reduce the processing of the three wastes, for the suitability for industrialized production of product provides convenience.Owing to used hydrated barta, can omit freezing and ion-exchange two big steps in original technology again, compare with former technology have work simplification, with short production cycle, advantage that energy consumption is low.The present invention can bring up to 58～61% through testing its yield, dry product content 〉=99%, specific rotatory power [α]
D 20+ 19 ± 1 °.
Embodiment:
Embodiment 1:
1, under whipped state, L lysine HCL 180 grams and cupric oxide 140 grams are added in 750 ml waters, after being heated to boiling and keeping 2 hours, be cooled to room temperature, filter, remove unreacted cupric oxide.
2, get 200 the gram oxygen methyl-isothioureas and 350 the gram hydrated bartas be dissolved in respectively in the suitable quantity of water, mix stirring with above-mentioned filtrate again, under whipped state, splash into 4N sodium hydroxide.After regulating pH value to 10～11, slowly be heated to 55 °～60 ℃, insulation reaction 12 hours.To be cooled to room temperature, add raw spirit, left standstill 12～15 hours, treat material sufficient crystallising after-filtration.Filtrate is placed after 12 hours and is refiltered, and the xln that obtains is a L-homoarginine mantoquita mixture.
3, above-mentioned mixture is warming up to 50 °～55 ℃ by weight with after 10 times the water dissolution, slowly feeds hydrogen sulfide then to reaction end, and promptly pH value is 6, and the time is 3.5～4.5 hours.After the question response liquid cooling but, add by weight being the gac of reaction solution 15%, stir one hour after-filtration, filtrate is washed with suitable quantity of water, and washings and filtrate merge, and under whipped state, dripping hydrochloric acid is regulated pH value to 2～2.5, stablizes 30 minutes.
4, under 60 °～65 ℃, vacuumize and form negative pressure and remove moisture content in the above-mentioned feed liquid to doing.The raw spirit that adds 1.5 times behind the cool to room temperature left standstill 12～15 hours, made the material sufficient crystallising.The white powder crystalline solid that obtains after filtration is L-homoarginine hydrochloride raw product.This raw product is added the suitable quantity of water dissolving, recrystallization in alcohol, repeatable operation twice, drying obtains finished product, and its yield is 59%, dry product content 99.6%, specific rotatory power [α]
D 20+ 18.5.
Embodiment 2:
Preparation technology is identical with embodiment 1, and concrete parameter is as follows:
1. add L-lysine hydrochloric acid 200 grams, cupric oxide 160 grams;
2. the hydrated barta add-on is 360 grams, and insulation reaction is increased to 15 hours;
3. the gac additional proportion is increased to 20%, is increased to 60 minutes steady time;
The products therefrom yield is 61%, dry product content 99.8%, specific rotatory power [α]
D 20+ 19.01 °.
Claims (2)
1. the preparation method of a L-homoarginine hydrochloride, it comprises: in the water that is dissolved in 2～3 times with the L lysine HCL and the cupric oxide of 1: 0.78～0.8 weight ratio under whipped state, be heated to the boiling and kept 2 hours, cool to room temperature filters then, it is characterized in that: get by weight 1: 1.75～1.80 oxygen methyl-isothiourea and hydrated barta soluble in water respectively, and mix stirring with above-mentioned reaction solution, after in mixing stirring, splashing into 4N sodium hydroxide accent pH value to 10～11, be heated to 55 °～60 ℃, insulation reaction 12～15 hours, be cooled to room temperature then, adding raw spirit left standstill 12～15 hours, obtain xln L-homoarginine mantoquita mixture after filtration, this mixture is with 10 times water dissolution, be warmed up to 50 °～55 ℃, feed hydrogen sulfide to reaction end, after cooling, adding by weight is the gac of reaction solution 15～20%, then through stirring, filter, after its filtrate is washed with suitable quantity of water, washings and filtered liquid are mixed, dripping hydrochloric acid is regulated PH to 2～3 under whipped state, stablizes 30～60 minutes, under 60 °～65 ℃ negative pressure, the moisture of removing in the feed liquid is extremely done, be cooled to room temperature again, add raw spirit, left standstill 12～15 hours, filter and obtain the white powder xln, this xln gets final product through purifying.
2. the preparation method of a kind of L-homoarginine hydrochloride as claimed in claim 1 is characterized in that: oxygen methyl-isothiourea and hydrated barta weight ratio are 1: 1.8, and insulation reaction is 15 hours, and the gac additional proportion is 20%, and be 60 minutes steady time.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410052953 CN1724514B (en) | 2004-07-19 | 2004-07-19 | Preparation method of L-homoarginine hydrochloride |
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| Application Number | Priority Date | Filing Date | Title |
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| CN 200410052953 CN1724514B (en) | 2004-07-19 | 2004-07-19 | Preparation method of L-homoarginine hydrochloride |
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| Publication Number | Publication Date |
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| CN1724514A CN1724514A (en) | 2006-01-25 |
| CN1724514B true CN1724514B (en) | 2010-06-09 |
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| CN 200410052953 Expired - Fee Related CN1724514B (en) | 2004-07-19 | 2004-07-19 | Preparation method of L-homoarginine hydrochloride |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102675156B (en) * | 2012-01-15 | 2013-11-27 | 河南科技大学 | Preparation method of L-homoarginine hydrochloride |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1087624A (en) * | 1992-07-24 | 1994-06-08 | 惠尔康基金会集团公司 | Arginine derivative |
| US5965538A (en) * | 1994-03-17 | 1999-10-12 | Fujirebio Inc. | Azapeptide derivative |
| CN1441055A (en) * | 2003-02-25 | 2003-09-10 | 江南大学 | L-arginine producing strain and its mutation method and usage in producing L-arginine |
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2004
- 2004-07-19 CN CN 200410052953 patent/CN1724514B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1087624A (en) * | 1992-07-24 | 1994-06-08 | 惠尔康基金会集团公司 | Arginine derivative |
| US5965538A (en) * | 1994-03-17 | 1999-10-12 | Fujirebio Inc. | Azapeptide derivative |
| CN1441055A (en) * | 2003-02-25 | 2003-09-10 | 江南大学 | L-arginine producing strain and its mutation method and usage in producing L-arginine |
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| CN1724514A (en) | 2006-01-25 |
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Granted publication date: 20100609 Termination date: 20100719 |