CN1526698A - Production process of high-purity DL-lysine - Google Patents
Production process of high-purity DL-lysine Download PDFInfo
- Publication number
- CN1526698A CN1526698A CNA031174078A CN03117407A CN1526698A CN 1526698 A CN1526698 A CN 1526698A CN A031174078 A CNA031174078 A CN A031174078A CN 03117407 A CN03117407 A CN 03117407A CN 1526698 A CN1526698 A CN 1526698A
- Authority
- CN
- China
- Prior art keywords
- lysine
- methionin
- purity
- salt
- production process
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention is production process of high-purity DL-lysine in medicine chemical technology. The production process with salt of lysine as material includes neutralization with inorganic alkali to obtain mixture of lysine and corresponding salt, setting the mixture in organic acid and catalyzing with salicylic acid to racemize lysine therein, ion exchange to eliminate salt and refining to obtain DL-lysine. The present invention has the advantages of easy-to-obtain material, low cost, easy operation, less pollution, product yield as high as 90 % and product purity as high as 99 %, and may be applied in large-scale production.
Description
Technical field
The present invention relates to a kind of production method of high purity DL-lysine.Belong to pharmaceutical chemistry technical field.
Background technology
DL-Methionin (D-Lys) is used in medicine widely, is widely used in the drug manufacture, as acetylsalicylic acid-DL-Methionin (medicine is called di-lysine-aspirin).DL-Methionin is again the raw material that splits preparation D-Methionin (D-Lys) simultaneously.Existing preparation method has: 1). and be raw material with the hexanolactam, hydrolysis prepares the method [Gaudry, R., Can J Research, 25B, 387 (1948)] of DL-Methionin (DL-Lys).2). with L-Lys (D-Lys) is raw material, method (Lu, Tianci, the CN86107049 of racemization preparation (DL-Lys); Oono, Takae, et al, JPO1045349A2).The former yield is low, often contains other unnecessary impurity such as by product hexanolactam class, diketopiperazines, dipeptide; It is raw material that then a kind of method needs free L-Methionin.Because free L-Methionin less stable, price is more expensive, so this method is that raw material is restricted with free L-Methionin directly.Because post processing mode is the problem that the purifying mode falls behind, the amino caprolactam of racemization by product is often arranged simultaneously, the diketopiperazines by product, product purity is difficult to guarantee.
Summary of the invention
The objective of the invention is to overcome the above-mentioned shortcoming that prior art exists, provide a kind of raw material to be easy to get, technology is simple, the production method of the high purity DL-lysine that yield is high.
The production method of high purity DL-lysine of the present invention is: be raw material with the lysine salt, with in the mineral alkali and after, get the mixture of Methionin and corresponding salt, said mixture is put into organic acid salicylic aldehyde catalysis, direct racemization Methionin wherein, adopt ion-exchange demineralization, the refining DL-Methionin (DL-Lys) that promptly obtains.
Described lysine salt raw material can be the lysine acetate of L configuration or D configuration, lysine hydrochloride, lysine sulfate etc.Mineral alkali can be a salt of wormwood, sodium hydroxide etc., and organic acid can be selected acetic acid or propionic acid etc. for use, and except that with the salicylic aldehyde, also available its derivative all can be obtained similar effects to nitrosalicylaldehyde.
Compare with aforementioned existing method, advantage of the present invention is: the lysine salt raw material is easy to get, and is cheap; Acetylize by product and other racemization production of by-products have been avoided; Technology is simple, and is workable, and production process is polluted little.Can realize scale production.Product yield is up to more than 90%, and purity can reach more than 99%.
Content of the present invention further illustrates with the following Examples, but content of the present invention is not limited only to content related among the embodiment.
Embodiment
Below be the concrete implementation step of the inventive method:
1. in reactor, add entry 100kg, L lysine HCL (L-Lys.HCl) 50kg, yellow soda ash (Na
2CO
3) 14.5kg, be stirred to dissolving and finish,
2. solution is concentrated under vacuum 0.075～0.085MPa condition and separates out white solid 55～75 ℃ of temperature in " 1. ",
3. in aforesaid reaction vessel, add acetic acid (HAc) 355kg, to nitrosalicylaldehyde (p-NO
2-O-OH-phCHO) 0.5kg, steam heating is warming up to that insulation racemization to racemization finishes under 100～105 ℃ of conditions,
4. solution concentrates acetic acid (HAc) in " 3. " under 50～70 ℃ of temperature, vacuum 0.075～0.085MPa condition, separates out to solid, adds 150Kg water and gets dilute solution, treats upper prop,
5. ion exchange resin column on the dilute solution of gained in will " 4. ", the washing decon gets the ammoniacal liquor elutriant with 2～4 normal ammoniacal liquor wash-outs again,
6. the ammoniacal liquor elutriant of gained adds in the reactor in will " 5. ", adds alkaline activated carbon 2kg again, and reflux 0.5 hour is reduced to 50 ℃ then, the solid-liquid separation solution after handling that must decolour.
7. the solution that will go up the step gained adds in the reactor, under vacuum 0.08～0.09MPa, 55～75 ℃ of conditions of temperature, be concentrated into and separate out white solid, add dehydrated alcohol 25kg, airtight stirring 15 minutes, add dehydrated alcohol 100kg again, be heated to 60～65 ℃ of insulations, stirred 1 hour fast, centrifugation, the gained white solid is DL-Methionin crude product, adds dehydrated alcohol 25kg and soaks centrifugation again, with the forced air drying 3～4 hours under 75～80 ℃ of conditions of its solid, product DL-Methionin (DL-Lys) 37.7Kg.Yield 94.2%, product appearance: off-white powder; Purity: more than 99.0% (titrimetry); [α]
D 20:+0.05 ° of (c=2.0, H
2O); M.p.:168.5～170.3 ℃.
Claims (1)
1, a kind of production method of high purity DL-lysine, it is characterized in that described production method is: be raw material with the lysine salt, with in the mineral alkali and after, get the mixture of Methionin and corresponding salt, said mixture is put into organic acid salicylic aldehyde catalysis, directly racemization Methionin wherein adopts ion-exchange demineralization, the refining DL-Methionin (DL-Lys) that promptly obtains.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03117407 CN1310873C (en) | 2003-03-06 | 2003-03-06 | Production process of high-purity DL-lysine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03117407 CN1310873C (en) | 2003-03-06 | 2003-03-06 | Production process of high-purity DL-lysine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1526698A true CN1526698A (en) | 2004-09-08 |
| CN1310873C CN1310873C (en) | 2007-04-18 |
Family
ID=34284711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 03117407 Expired - Fee Related CN1310873C (en) | 2003-03-06 | 2003-03-06 | Production process of high-purity DL-lysine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1310873C (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101130504B (en) * | 2006-08-25 | 2010-07-28 | 苏州雅本化学股份有限公司 | Synthesis, split and racemization method for preparing chirality medicament levetiracetam midbody (S)-(+)-2-amido butyramide hydrochlorate |
| CN101560132B (en) * | 2009-05-14 | 2011-12-14 | 浙江普洛医药科技有限公司 | Method for racemizing chiral amino acid or derivatives of chiral amino acid |
| CN102392061A (en) * | 2011-09-29 | 2012-03-28 | 重庆邮电大学 | Chemical-enzyme method for preparing D-basic amino acid hydrochloride |
| CN104478746A (en) * | 2014-12-16 | 2015-04-01 | 武汉大学 | Preparation method of DL-lysine |
| CN105713194A (en) * | 2016-03-30 | 2016-06-29 | 浙江新银象生物工程有限公司 | Method for purifying epsilon-PL (epsilon-polylysine) |
| CN111886220A (en) * | 2020-06-18 | 2020-11-03 | 苏州园方生物科技有限公司 | Preparation method of DL-lysine |
-
2003
- 2003-03-06 CN CN 03117407 patent/CN1310873C/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101130504B (en) * | 2006-08-25 | 2010-07-28 | 苏州雅本化学股份有限公司 | Synthesis, split and racemization method for preparing chirality medicament levetiracetam midbody (S)-(+)-2-amido butyramide hydrochlorate |
| CN101560132B (en) * | 2009-05-14 | 2011-12-14 | 浙江普洛医药科技有限公司 | Method for racemizing chiral amino acid or derivatives of chiral amino acid |
| CN102392061A (en) * | 2011-09-29 | 2012-03-28 | 重庆邮电大学 | Chemical-enzyme method for preparing D-basic amino acid hydrochloride |
| CN104478746A (en) * | 2014-12-16 | 2015-04-01 | 武汉大学 | Preparation method of DL-lysine |
| CN105713194A (en) * | 2016-03-30 | 2016-06-29 | 浙江新银象生物工程有限公司 | Method for purifying epsilon-PL (epsilon-polylysine) |
| CN105713194B (en) * | 2016-03-30 | 2018-04-24 | 浙江新银象生物工程有限公司 | A kind of method for purifying epsilon-polylysine |
| CN111886220A (en) * | 2020-06-18 | 2020-11-03 | 苏州园方生物科技有限公司 | Preparation method of DL-lysine |
| WO2021253305A1 (en) * | 2020-06-18 | 2021-12-23 | 苏州园方生物科技有限公司 | Preparation method for dl-lysine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1310873C (en) | 2007-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101492367A (en) | Method for fine purification of lactic acid | |
| CN1310873C (en) | Production process of high-purity DL-lysine | |
| CN101723772A (en) | Method for preparing N-acetylamino acid | |
| CN101624351A (en) | Preparation method of DL-lysine | |
| CN111848535B (en) | Process for synthesizing 1H-tetrazole acetic acid | |
| CN101723773B (en) | Method for preparing high purity N-acetyl-DL-amino acid | |
| CN101781264B (en) | Production method of 1-methyl-5-mercapto-1,2,3,4-tetrazole | |
| CN1052511C (en) | Technology for preparation of gallic acid by using enzyme process | |
| CN113372190B (en) | Method for preparing 1, 3-adamantanediol from 3-amino-1-adamantanol | |
| CN111100025A (en) | Method for preparing aminocaproic acid | |
| CN1900053A (en) | Process for preparing D-alpha-amino isovaleric acid | |
| CN1199961C (en) | Spliting method for DL-pantoyl internal ester | |
| CN111574387A (en) | P-aminomethyl benzoic acid and preparation method thereof | |
| CN107778160B (en) | Preparation method of 3,4,5, 6-tetrafluorophthalic acid | |
| AU754030B2 (en) | Method for pressureless production of alpha,alpha-dimethylphenyl acetic acid from alpha,alpha-dimethyl benzyl cyanide | |
| CN1132832C (en) | Prepn process of 3-methyl-4 [(3-methoxy) propoxy]2-radical-methyl-thio-benzimidazole | |
| CN109796333A (en) | A method of the extraction purification pravastatin sodium from fermentation liquid | |
| CN101054366B (en) | Method of synthesizing 1-methyl hydantoin | |
| CN110606802A (en) | Method for recovering tartaric acid from calcium tartrate by using interfacial reaction | |
| CN112521269B (en) | Preparation method of magnesium succinate | |
| CN113402402B (en) | Method for recycling trans-p-aminocyclohexanol from low-concentration waste liquid | |
| CN109400468B (en) | Preparation method of L-dibenzoyl dimethyl tartrate | |
| CN106946765B (en) | The extraction separating method of L- nipecotic acid in recombination bacillus coli tunning | |
| CN114163438A (en) | Preparation method of 2-methyl-3-carbonyl pyrazolo [4,3-c ] pyridine-7-carboxylic acid hydrochloride | |
| CN118812381A (en) | Method for synthesizing alpha-methyl-D-propargylglycine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Effective date of registration: 20090114 Pledge (preservation): Pledge |
|
| EE01 | Entry into force of recordation of patent licensing contract |
Assignee: SICHUAN SHIFANG SANGAO BIOCHEMISTRY INDUSTRIAL CO., LTD. Assignor: Sichuan Sangao Biochemical Co., Ltd. Contract fulfillment period: 2007.10.18 to 2023.3.18 Contract record no.: 2009510000137 Denomination of invention: Production process of high-purity DL-lysine Granted publication date: 20070418 License type: General permission Record date: 20091030 |
|
| LIC | Patent licence contract for exploitation submitted for record |
Free format text: COMMON LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2007.10.18 TO 2023.3.18; CHANGE OF CONTRACT Name of requester: SICHUAN SHIFANG CITY SANGAO BIOCHEMICAL INDUSTRY C Effective date: 20091030 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20120615 Granted publication date: 20070418 Pledgee: Chengdu Productivity Promotion Center Pledgor: Sichuan Sangao Biochemical Co., Ltd. Registration number: 2009510000510 |
|
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20070418 Termination date: 20120306 |