CN106831446B - 一种改进的药用级苯扎氯铵单体生产方法 - Google Patents
一种改进的药用级苯扎氯铵单体生产方法 Download PDFInfo
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- CN106831446B CN106831446B CN201710182321.1A CN201710182321A CN106831446B CN 106831446 B CN106831446 B CN 106831446B CN 201710182321 A CN201710182321 A CN 201710182321A CN 106831446 B CN106831446 B CN 106831446B
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- Prior art keywords
- benzalkonium chloride
- production method
- organic solvent
- chloride monomer
- pharmaceutical grade
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- 229960000686 benzalkonium chloride Drugs 0.000 title claims abstract description 40
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 35
- 239000000178 monomer Substances 0.000 title claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- 239000013078 crystal Substances 0.000 claims abstract description 31
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 alkyl dimethyl tertiary amine Chemical class 0.000 claims abstract description 22
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229940073608 benzyl chloride Drugs 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000000498 cooling water Substances 0.000 claims abstract description 6
- 238000002425 crystallisation Methods 0.000 claims abstract description 6
- 230000008025 crystallization Effects 0.000 claims abstract description 6
- 238000010907 mechanical stirring Methods 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000011521 glass Substances 0.000 claims abstract 3
- 238000001953 recrystallisation Methods 0.000 claims abstract 2
- 238000000967 suction filtration Methods 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000009413 insulation Methods 0.000 claims description 8
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 8
- 235000019441 ethanol Nutrition 0.000 claims description 6
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical group CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 5
- BVWCFOXBDSMXEP-UHFFFAOYSA-N 1-(5-acetyl-2-methoxyphenyl)-3-methylbutan-1-one Chemical compound COC1=CC=C(C(C)=O)C=C1C(=O)CC(C)C BVWCFOXBDSMXEP-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 claims description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- PQXRVHVVXKJMDC-UHFFFAOYSA-N azane;benzene Chemical compound N.C1=CC=CC=C1 PQXRVHVVXKJMDC-UHFFFAOYSA-N 0.000 claims 1
- 150000002191 fatty alcohols Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 238000001816 cooling Methods 0.000 abstract description 2
- 238000007670 refining Methods 0.000 abstract description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000005086 pumping Methods 0.000 abstract 1
- 238000003828 vacuum filtration Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- YXUPZGKORWTXID-UHFFFAOYSA-N domiphen Chemical compound CCCCCCCCCCCC[N+](C)(C)CCOC1=CC=CC=C1 YXUPZGKORWTXID-UHFFFAOYSA-N 0.000 description 3
- 229960000629 domiphen Drugs 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 241000195493 Cryptophyta Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
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CN201710182321.1A CN106831446B (zh) | 2017-03-24 | 2017-03-24 | 一种改进的药用级苯扎氯铵单体生产方法 |
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CN201710182321.1A CN106831446B (zh) | 2017-03-24 | 2017-03-24 | 一种改进的药用级苯扎氯铵单体生产方法 |
Publications (2)
Publication Number | Publication Date |
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CN106831446A CN106831446A (zh) | 2017-06-13 |
CN106831446B true CN106831446B (zh) | 2019-02-19 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112400874A (zh) * | 2020-09-24 | 2021-02-26 | 福建省梦娇兰日用化学品有限公司 | 含苯扎氯铵杀菌剂的家用消毒液及其制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1986007237A1 (en) * | 1985-06-05 | 1986-12-18 | Mém Növényvédelmi És Agrokémiai Központ | Plant growth regulating compositions and process for regulating plant growth |
CN1287021A (zh) * | 2000-07-05 | 2001-03-14 | 北京清华紫光英力化工技术有限责任公司 | β-羟基结构的季铵盐复合相转移催化剂及其制备 |
WO2003091197A1 (fr) * | 2002-04-24 | 2003-11-06 | Nedd Marketing Sa | Procede de fabrication de chlorures d'alkyldimethyl-benzilammonium |
CN101050182A (zh) * | 2006-04-06 | 2007-10-10 | 浙江华特实业集团华特化工有限公司 | 一种季铵盐的制备方法 |
CN101525295A (zh) * | 2009-03-20 | 2009-09-09 | 孙玉明 | 一种固体季铵盐的生产工艺 |
CN105646238A (zh) * | 2016-01-08 | 2016-06-08 | 广东工业大学 | 季铵盐(十四烷基-二甲基-苄基氯化铵)的合成方法及其应用 |
-
2017
- 2017-03-24 CN CN201710182321.1A patent/CN106831446B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1986007237A1 (en) * | 1985-06-05 | 1986-12-18 | Mém Növényvédelmi És Agrokémiai Központ | Plant growth regulating compositions and process for regulating plant growth |
CN1287021A (zh) * | 2000-07-05 | 2001-03-14 | 北京清华紫光英力化工技术有限责任公司 | β-羟基结构的季铵盐复合相转移催化剂及其制备 |
WO2003091197A1 (fr) * | 2002-04-24 | 2003-11-06 | Nedd Marketing Sa | Procede de fabrication de chlorures d'alkyldimethyl-benzilammonium |
CN101050182A (zh) * | 2006-04-06 | 2007-10-10 | 浙江华特实业集团华特化工有限公司 | 一种季铵盐的制备方法 |
CN101525295A (zh) * | 2009-03-20 | 2009-09-09 | 孙玉明 | 一种固体季铵盐的生产工艺 |
CN105646238A (zh) * | 2016-01-08 | 2016-06-08 | 广东工业大学 | 季铵盐(十四烷基-二甲基-苄基氯化铵)的合成方法及其应用 |
Non-Patent Citations (1)
Title |
---|
十四烷基二甲基苄基氯化铵的合成及晶体结构;王瑛等;《南京理工大学学报(自然科学版)》;20051031;第29卷(第5期);第590-593页 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112400874A (zh) * | 2020-09-24 | 2021-02-26 | 福建省梦娇兰日用化学品有限公司 | 含苯扎氯铵杀菌剂的家用消毒液及其制备方法 |
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CN106831446A (zh) | 2017-06-13 |
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Legal Events
Date | Code | Title | Description |
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PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20180706 Address after: 515000 block B, Chengde Square, Shantou Free Trade Zone, Shantou, Guangdong. Applicant after: Guangdong loest Pharmaceutical Co. Ltd. Address before: 515000 Shantou City, Guangdong province free trade zone Applicant before: Wu Lian |
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TA01 | Transfer of patent application right | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CP02 | Change in the address of a patent holder |
Address after: 515000 one of the second floor of building 0003, block e08-4, Shantou Free Trade Zone, Shantou City, Guangdong Province Patentee after: Guangdong loest Pharmaceutical Co.,Ltd. Address before: 515000 block B, Chengde Square, Shantou Free Trade Zone, Shantou, Guangdong. Patentee before: Guangdong loest Pharmaceutical Co.,Ltd. |
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CP02 | Change in the address of a patent holder | ||
CP02 | Change in the address of a patent holder |
Address after: 515000 one of the second floor of building 0001, block e08-4, Shantou Free Trade Zone, Shantou City, Guangdong Province Patentee after: Guangdong loest Pharmaceutical Co.,Ltd. Address before: 515000 one of the second floor of building 0003, block e08-4, Shantou Free Trade Zone, Shantou City, Guangdong Province Patentee before: Guangdong loest Pharmaceutical Co.,Ltd. |
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CP02 | Change in the address of a patent holder |