CN103102294A - Production method carboxymethyl cysteine - Google Patents
Production method carboxymethyl cysteine Download PDFInfo
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- CN103102294A CN103102294A CN2012100850420A CN201210085042A CN103102294A CN 103102294 A CN103102294 A CN 103102294A CN 2012100850420 A CN2012100850420 A CN 2012100850420A CN 201210085042 A CN201210085042 A CN 201210085042A CN 103102294 A CN103102294 A CN 103102294A
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- carbocisteine
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- production method
- reactor
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- JJVXHDTWVIPRBZ-VKHMYHEASA-N (2r)-2-[carboxy(methyl)amino]-3-sulfanylpropanoic acid Chemical compound OC(=O)N(C)[C@@H](CS)C(O)=O JJVXHDTWVIPRBZ-VKHMYHEASA-N 0.000 title abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000001035 drying Methods 0.000 claims abstract description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 19
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229960001305 cysteine hydrochloride Drugs 0.000 claims abstract description 16
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000919 ceramic Substances 0.000 claims abstract description 14
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 6
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 claims description 39
- 229960004399 carbocisteine Drugs 0.000 claims description 39
- 238000007670 refining Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 9
- 238000003556 assay Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 239000011229 interlayer Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000012856 packing Methods 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 abstract description 8
- 239000000463 material Substances 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 229940024606 amino acid Drugs 0.000 abstract description 2
- 235000001014 amino acid Nutrition 0.000 abstract description 2
- 150000001413 amino acids Chemical class 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 230000020477 pH reduction Effects 0.000 abstract 1
- 206010036790 Productive cough Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010014561 Emphysema Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010044302 Tracheitis Diseases 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 2
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 210000003802 sputum Anatomy 0.000 description 2
- 208000024794 sputum Diseases 0.000 description 2
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000003255 anti-acne Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 239000003172 expectorant agent Substances 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a production method of carboxymethyl cysteine. The product belongs to the field of manufacturing of amino acids. According to the invention, cysteine hydrochloride monohydrate is used as a main raw material, chloroacetic acid, liquid ammonia, activated carbon and refined hydrochloric acid are used as auxiliary materials, a ceramic reaction kettle, a filtering machine, a centrifugal machine and a vacuum drier are used as apparatuses, and acidification reaction, decolorizing filtration, centrifugal separation, drying and other steps are utilized to prepare the carboxymethyl cysteine. Compared with the prior art, the production method disclosed by the invention has the advantages of simple technique, fewer general-purpose apparatuses, no discharge of three wastes, no high-temperature high-pressure reaction, low production cost, high yield, high product quality and the like, is easy for production operation, and can implement mass production of high-quality carboxymethyl cysteine.
Description
Technical field
The invention belongs to amino acid and make the field, relate in particular to a kind of method of producing Carbocisteine take cysteine hydrochloride monohydrate as raw material in batches.
Background technology
Carbocisteine, have another name called vinegar sulphur L-Ala, the peace bromohydrin, NA-872, Ambroxl, molecular weight is 179.1943, molecular formula is C5H9NO4S, molecular weight is 179.1943, specific optical rotation is-32.5 ℃-36.0 ℃, the pH value is 2.80-2.95, clarity of solution transmittance 〉=95.0%, halfcystine≤0.05%, muriate≤0.15%, weight loss on drying≤0.5%, residue on ignition≤0.2%, molysite≤0.001%, heavy metal≤0.002%, outward appearance is white crystalline powder, be insoluble to cold water and ethanol, acetone and other organic solvent, be soluble in acidity and alkaline aqueous solution.Carbocisteine is of many uses: 1. pharmaceutically as expectorant, bronchial mucus secretion is reduced, the viscosity of phlegm descends and is easy to expectoration, thereby can be used for being used for the treatment of the not congruent patient of thick sputum, dys-expectoration, pulmonary ventilation function that chronic tracheitis, pulmonary emphysema, pulmonary tuberculosis, bronchial asthma etc. cause; 2. can be used for the synthesizing of multi-medicament, be a kind of important medicine intermediate and industrial chemicals; 3. in daily life as hair finishing composition and conditioning agent, also can be used as anti-acne drug use.When being used for the treatment of the thick sputum that chronic tracheitis, pulmonary emphysema, pulmonary tuberculosis, bronchial asthma etc. cause, adult's consumption is 500 milligrams of every days, and minute 3-4 time oral.The technique of producing Carbocisteine is more, can make final product by different routes with different raw materials, the present invention is produce this Product Process a kind of, take cysteine hydrochloride monohydrate as main raw material, take Mono Chloro Acetic Acid, liquefied ammonia, gac, refining hydrochloric acid as auxiliary material, take ceramic reactor, filter, whizzer, Vacuumdrier as equipment, make Carbocisteine by adding the operations such as acid-respons, decolorization filtering, centrifugation, oven dry.This production method compared to the prior art, have technique simple, use general-purpose equipment and number of devices is few, three-waste free discharge, without high-temperature high-voltage reaction, be easy to production operation, the series of advantages such as production cost is low and productive rate is high, good product quality, can be mass, can produce high-quality Carbocisteine.
Summary of the invention
the problem that the present invention mainly solves is to provide a kind of production method of Carbocisteine, the method is take cysteine hydrochloride monohydrate as main raw material, with Mono Chloro Acetic Acid, liquefied ammonia, gac, refining hydrochloric acid is auxiliary material, by adding acid-respons, decolorization filtering, centrifugation, the operations such as oven dry make finished product, the raw material that the present invention uses is: 300 kilograms of cysteine hydrochloride monohydrates, 1000 liters of Mono Chloro Acetic Acids, liquefied ammonia is appropriate, 6 kilograms of gacs, refining hydrochloric acid 9.5-10.5 equivalent, the equipment that uses is 2 tons of ceramic reactors, strainer, whizzer, Vacuumdrier.
The present invention can be achieved through the following technical solutions:
A kind of production method of Carbocisteine is characterized in that being made of following steps:
(1) send into after the assay was approved 300 kilograms of cysteine hydrochloride monohydrates in ceramic reactor, add 1000 liters of Mono Chloro Acetic Acids, start agitator, rotating speed is 20 rev/mins, cysteine hydrochloride monohydrate and Mono Chloro Acetic Acid are mixed into thick liquid, add appropriate liquefied ammonia, adjust pH reaches between 9.5-10.5, stirring reaction adds the gac of 6 kilograms after 2 hours, simultaneously sending into steam to the reactor interlayer heats, transfer reactor temperature to 58 ℃-62 ℃, reaction decolouring 0.5 hour, then reactant being sent into filter filters, after filtering, filtrate is sent into ceramic reactor again, the refining hydrochloric acid that adds the 9.5-10.5 equivalent, adjust pH is 2.8-3.2, then the stirred crystallization while lowering the temperature, obtain the Carbocisteine solid.
(2) the Carbocisteine solid is sent into whizzer and carry out solid-liquid separation, obtain the Carbocisteine xln.
(3) the Carbocisteine xln is sent into Vacuumdrier and carry out drying, under 78 ℃-82 ℃ dry 3.8-4.2 hour, the parallel operation dry blending that can sieve, the packing warehouse-in namely obtains the Carbocisteine finished product.
Temperature of reaction in step (1) in reactor is 58 ℃, 60 ℃, 62 ℃; The addition of refining hydrochloric acid is respectively 9.5 equivalents, 10 equivalents, 10.5 equivalents.
When in step (3), the drying temperature of drying machine is 78 ℃, be 4.2 hours corresponding time of drying; Be 4 hours time of drying that is 80 ℃ of correspondences; When being 82 ℃, be 3.8 hours corresponding time of drying.
The invention has the beneficial effects as follows: a kind of method of producing Carbocisteine in batches is provided, this production method have technique simple, use general-purpose equipment and number of devices is few, three-waste free discharge, without high-temperature high-voltage reaction, be easy to production operation, the series of advantages such as production cost is low and productive rate is high, good product quality, can be mass, can produce high-quality Carbocisteine.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
Embodiment 1
send into after the assay was approved 300 kilograms of cysteine hydrochloride monohydrates in ceramic reactor, add 1000 liters of Mono Chloro Acetic Acids, start agitator, rotating speed is 20 rev/mins, cysteine hydrochloride monohydrate and Mono Chloro Acetic Acid are mixed into thick liquid, add appropriate liquefied ammonia, adjust pH reaches between 9.5-10.5, stirring reaction adds the gac of 6 kilograms after 2 hours, simultaneously sending into steam to the reactor interlayer heats, transfer reactor temperature to 58 ℃, reaction decolouring 0.5 hour, then reactant being sent into filter filters, after filtering, filtrate is sent into ceramic reactor again, the refining hydrochloric acid that adds 9.5 equivalents, adjust pH is 3.2, then the stirred crystallization while lowering the temperature, obtain the Carbocisteine solid, Carbocisteine solid body is sent into whizzer carry out solid-liquid separation, obtain the Carbocisteine xln, the Carbocisteine xln is sent into Vacuumdrier carry out drying, drying is 4.2 hours under 78 ℃, the parallel operation dry blending that can sieve, and the packing warehouse-in namely obtains the Carbocisteine finished product.
Embodiment 2
send into after the assay was approved 300 kilograms of cysteine hydrochloride monohydrates in ceramic reactor, add 1000 liters of Mono Chloro Acetic Acids, start agitator, rotating speed is 20 rev/mins, cysteine hydrochloride monohydrate and Mono Chloro Acetic Acid are mixed into thick liquid, add appropriate liquefied ammonia, adjust pH reaches between 9.5-10.5, stirring reaction adds the gac of 6 kilograms after 2 hours, simultaneously sending into steam to the reactor interlayer heats, transfer reactor temperature to 60 ℃, reaction decolouring 0.5 hour, then reactant being sent into filter filters, after filtering, filtrate is sent into ceramic reactor again, the refining hydrochloric acid that adds 10 equivalents, adjust pH is 3, then the stirred crystallization while lowering the temperature, obtain the Carbocisteine solid, Carbocisteine solid body is sent into whizzer carry out solid-liquid separation, obtain the Carbocisteine xln, the Carbocisteine xln is sent into Vacuumdrier carry out drying, drying is 4 hours under 80 ℃, the parallel operation dry blending that can sieve, and the packing warehouse-in namely obtains the Carbocisteine finished product.
Embodiment 3
send into after the assay was approved 300 kilograms of cysteine hydrochloride monohydrates in ceramic reactor, add 1000 liters of Mono Chloro Acetic Acids, start agitator, rotating speed is 20 rev/mins, cysteine hydrochloride monohydrate and Mono Chloro Acetic Acid are mixed into thick liquid, add appropriate liquefied ammonia, adjust pH reaches between 9.5-10.5, stirring reaction adds the gac of 6 kilograms after 2 hours, simultaneously sending into steam to the reactor interlayer heats, transfer reactor temperature to 62 ℃, reaction decolouring 0.5 hour, then reactant being sent into filter filters, after filtering, filtrate is sent into ceramic reactor again, the refining hydrochloric acid that adds 10.5 equivalents, adjust pH is 2.8, then the stirred crystallization while lowering the temperature, obtain the Carbocisteine solid, Carbocisteine solid body is sent into whizzer carry out solid-liquid separation, obtain the Carbocisteine xln, the Carbocisteine xln is sent into Vacuumdrier carry out drying, drying is 3.8 hours under 82 ℃, the parallel operation dry blending that can sieve, and the packing warehouse-in namely obtains the Carbocisteine finished product.
Claims (3)
1. the production method of a Carbocisteine, the proportioning raw materials of using is: 300 kilograms of cysteine hydrochloride monohydrates, 1000 liters of Mono Chloro Acetic Acids, liquefied ammonia are appropriate, 6 kilograms of gacs, refining hydrochloric acid 9.5-10.5 equivalent, and the equipment of use is 2 tons of ceramic reactors, strainer, whizzer, Vacuumdrier, it is characterized in that: step (1) is sent into 300 kilograms of cysteine hydrochloride monohydrates in ceramic reactor after the assay was approved, add 1000 liters of Mono Chloro Acetic Acids, start agitator, rotating speed is 20 rev/mins, cysteine hydrochloride monohydrate and Mono Chloro Acetic Acid are mixed into thick liquid, add appropriate liquefied ammonia, adjust pH reaches between 9.5-10.5, stirring reaction adds the gac of 6 kilograms after 2 hours, simultaneously sending into steam to the reactor interlayer heats, transfer reactor temperature to 58 ℃-62 ℃, reaction decolouring 0.5 hour, then reactant being sent into filter filters, after filtering, filtrate is sent into ceramic reactor again, the refining hydrochloric acid that adds the 9.5-10.5 equivalent, adjust pH is 2.8-3.2, then the stirred crystallization while lowering the temperature, obtain the Carbocisteine solid, step (2) is sent the Carbocisteine solid into whizzer and is carried out solid-liquid separation, obtains the Carbocisteine xln, step (3) is sent the Carbocisteine xln into Vacuumdrier and is carried out drying, and under 78 ℃-82 ℃ dry 3.8-4.2 hour, the parallel operation dry blending that can sieve, the packing warehouse-in namely obtains the Carbocisteine finished product.
2. the production method of a kind of Carbocisteine according to claim 1, the feature of its step (1) is: the temperature of reaction in described reactor is 58 ℃, 60 ℃, 62 ℃; The addition of refining hydrochloric acid is respectively 9.5 equivalents, 10 equivalents, 10.5 equivalents.
3. the production method of a kind of Carbocisteine according to claim 1, the feature of its step (3) is: the drying temperature in described drying machine when being 78 ℃ corresponding time of drying be 4.2 hours; Be 4 hours time of drying that is 80 ℃ of correspondences; When being 82 ℃, be 3.8 hours corresponding time of drying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100850420A CN103102294A (en) | 2012-03-28 | 2012-03-28 | Production method carboxymethyl cysteine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100850420A CN103102294A (en) | 2012-03-28 | 2012-03-28 | Production method carboxymethyl cysteine |
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| Publication Number | Publication Date |
|---|---|
| CN103102294A true CN103102294A (en) | 2013-05-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012100850420A Pending CN103102294A (en) | 2012-03-28 | 2012-03-28 | Production method carboxymethyl cysteine |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418471A (en) * | 2015-12-24 | 2016-03-23 | 宜昌三峡制药有限公司 | Synthetic method of carbocisteine |
| CN106083673A (en) * | 2016-06-29 | 2016-11-09 | 罗江晨明生物制品有限公司 | A kind of preparation technology of carbocisteine |
| CN106435933A (en) * | 2016-09-28 | 2017-02-22 | 佛山慧创正元新材料科技有限公司 | Infant cotton and hemp pinafore fabric structure |
| CN106565565A (en) * | 2016-10-19 | 2017-04-19 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN108752250A (en) * | 2018-04-23 | 2018-11-06 | 浙江国邦药业有限公司 | A kind of synthetic method of high-purity Fudosteine |
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
| CN116143674A (en) * | 2022-12-20 | 2023-05-23 | 云鹏医药集团有限公司 | Synthesis method of high-purity carbocisteine |
-
2012
- 2012-03-28 CN CN2012100850420A patent/CN103102294A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418471A (en) * | 2015-12-24 | 2016-03-23 | 宜昌三峡制药有限公司 | Synthetic method of carbocisteine |
| CN105418471B (en) * | 2015-12-24 | 2017-09-05 | 宜昌三峡制药有限公司 | A kind of synthetic method of carbocisteine |
| CN106083673B (en) * | 2016-06-29 | 2017-11-03 | 罗江晨明生物制品有限公司 | A kind of preparation technology of carbocisteine |
| CN106083673A (en) * | 2016-06-29 | 2016-11-09 | 罗江晨明生物制品有限公司 | A kind of preparation technology of carbocisteine |
| CN106435933A (en) * | 2016-09-28 | 2017-02-22 | 佛山慧创正元新材料科技有限公司 | Infant cotton and hemp pinafore fabric structure |
| CN106565565B (en) * | 2016-10-19 | 2018-08-03 | 武汉远大弘元股份有限公司 | A kind of preparation method of carbocisteine |
| CN106565565A (en) * | 2016-10-19 | 2017-04-19 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN108752250A (en) * | 2018-04-23 | 2018-11-06 | 浙江国邦药业有限公司 | A kind of synthetic method of high-purity Fudosteine |
| CN108752250B (en) * | 2018-04-23 | 2022-06-14 | 浙江国邦药业有限公司 | Synthesis method of high-purity fudosteine |
| WO2021102918A1 (en) * | 2019-11-29 | 2021-06-03 | 武汉远大弘元股份有限公司 | Method for preparing carbocisteine |
| CN114746399A (en) * | 2019-11-29 | 2022-07-12 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN114746399B (en) * | 2019-11-29 | 2024-05-24 | 武汉远大弘元股份有限公司 | Preparation method of carbocisteine |
| CN116143674A (en) * | 2022-12-20 | 2023-05-23 | 云鹏医药集团有限公司 | Synthesis method of high-purity carbocisteine |
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Application publication date: 20130515 |