CS231971B2 - Purification method for mercaptobenzothiazole - Google Patents

Purification method for mercaptobenzothiazole Download PDF

Info

Publication number: CS231971B2
Authority: CS; Czechoslovakia
Prior art keywords: aniline; mercaptobenzothiazole; liquid phase; reaction; impurities
Prior art date: 1979-03-06

Application number

CS801493A

Other languages

Czech (cs)

English (en)

Other versions

CS149380A2 (en

Inventor

Michal Alicot

Adrien Tignel

Original Assignee

Ugine Kuhlmann

Priority date (The priority date 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 date listed.)

1979-03-06

Filing date

1980-03-04

Publication date

1985-01-16

1980-03-04 Application filed by Ugine Kuhlmann filed Critical Ugine Kuhlmann

1984-01-16 Publication of CS149380A2 publication Critical patent/CS149380A2/cs

1985-01-16 Publication of CS231971B2 publication Critical patent/CS231971B2/cs

Links

YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 title claims description 78
238000000034 method Methods 0.000 title claims description 37
238000000746 purification Methods 0.000 title description 14
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 88
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 31
239000012535 impurity Substances 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 12
239000007791 liquid phase Substances 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
239000007795 chemical reaction product Substances 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
230000015572 biosynthetic process Effects 0.000 claims description 8
239000012043 crude product Substances 0.000 claims description 5
239000012065 filter cake Substances 0.000 claims description 5
238000003786 synthesis reaction Methods 0.000 claims description 5
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 4
238000004140 cleaning Methods 0.000 claims description 3
238000004821 distillation Methods 0.000 claims description 3
238000001704 evaporation Methods 0.000 claims description 3
230000008020 evaporation Effects 0.000 claims description 3
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 6
239000002245 particle Substances 0.000 description 6
239000002609 medium Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000005406 washing Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000356 contaminant Substances 0.000 description 3
230000001804 emulsifying effect Effects 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000002699 waste material Substances 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000007710 freezing Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004073 vulcanization Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000002144 chemical decomposition reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011810 insulating material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000007003 mineral medium Substances 0.000 description 1
QDTDFSFRIDFTCF-UHFFFAOYSA-N n-phenyl-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=CC=C2SC=1NC1=CC=CC=C1 QDTDFSFRIDFTCF-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/72—2-Mercaptobenzothiazole

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS801493A 1979-03-06 1980-03-04 Purification method for mercaptobenzothiazole CS231971B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7905710A FR2450828A1 (fr)	1979-03-06	1979-03-06	Procede de purification du mercaptobenzothiazole

Publications (2)

Publication Number	Publication Date
CS149380A2 CS149380A2 (en)	1984-01-16
CS231971B2 true CS231971B2 (en)	1985-01-16

Family

ID=9222794

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS801493A CS231971B2 (en)	1979-03-06	1980-03-04	Purification method for mercaptobenzothiazole

Country Status (13)

Country	Link
US (1)	US4371698A (de)
EP (1)	EP0015802B1 (de)
JP (1)	JPS55143979A (de)
AU (1)	AU519597B2 (de)
BR (1)	BR8001318A (de)
CA (1)	CA1151180A (de)
CS (1)	CS231971B2 (de)
DD (1)	DD149364A5 (de)
DE (1)	DE3067992D1 (de)
DK (1)	DK145909C (de)
ES (1)	ES489230A1 (de)
FR (1)	FR2450828A1 (de)
YU (1)	YU61380A (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3257090A (en) *	1964-07-06	1966-06-21	Tabco	Combination bag holding bracket and drawstring threading means
US4515957A (en) *	1982-08-20	1985-05-07	The B. F. Goodrich Company	Purification of mercaptobenzothiazole
FR2565977B1 (fr) *	1984-06-15	1986-08-29	Atochem	Procede de purification du mercaptobenzothiazole
DE4028473A1 (de) *	1990-09-07	1992-03-12	Akzo Gmbh	Verfahren zur herstellung von 2-mercapto-benzothiazol
SK286026B6 (sk) *	2003-12-23	2008-01-07	Duslo, A. S.	Spôsob získavania 2-merkaptobenztiazolu
CN102675242A (zh) *	2012-05-08	2012-09-19	中国石油化工股份有限公司	一种硫化促进剂m的精制方法
CN113912564B (zh) *	2021-10-27	2023-01-31	河南省化工研究所有限责任公司	一种金属卟啉温和催化氧化制备2-巯基苯并噻唑的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2090233A (en) *	1935-11-01	1937-08-17	Wingfoot Corp	Process for manufacture of mercapto aryl thiazoles
US2161741A (en) *	1937-05-27	1939-06-06	Wingfoot Corp	Manufacture of mercaptothiazoles
FR2397409A1 (fr)	1977-07-12	1979-02-09	Ugine Kuhlmann	Procede de purification de mercaptobenzothiazole

1979
- 1979-03-06 FR FR7905710A patent/FR2450828A1/fr active Granted
1980
- 1980-02-14 US US06/121,570 patent/US4371698A/en not_active Expired - Lifetime
- 1980-02-19 DE DE8080400231T patent/DE3067992D1/de not_active Expired
- 1980-02-19 EP EP80400231A patent/EP0015802B1/de not_active Expired
- 1980-03-03 DK DK90080A patent/DK145909C/da not_active IP Right Cessation
- 1980-03-03 DD DD80219411A patent/DD149364A5/de unknown
- 1980-03-03 AU AU56074/80A patent/AU519597B2/en not_active Ceased
- 1980-03-04 CS CS801493A patent/CS231971B2/cs unknown
- 1980-03-05 ES ES489230A patent/ES489230A1/es not_active Expired
- 1980-03-05 YU YU00613/80A patent/YU61380A/xx unknown
- 1980-03-05 BR BR8001318A patent/BR8001318A/pt unknown
- 1980-03-05 CA CA000347047A patent/CA1151180A/fr not_active Expired
- 1980-03-05 JP JP2785380A patent/JPS55143979A/ja active Pending

Also Published As

Publication number	Publication date
BR8001318A (pt)	1980-11-04
CA1151180A (fr)	1983-08-02
JPS55143979A (en)	1980-11-10
US4371698A (en)	1983-02-01
EP0015802B1 (de)	1984-05-30
DD149364A5 (de)	1981-07-08
YU61380A (en)	1984-02-29
AU5607480A (en)	1980-09-11
ES489230A1 (es)	1980-08-16
FR2450828B1 (de)	1981-03-27
DK90080A (da)	1980-09-07
AU519597B2 (en)	1981-12-10
FR2450828A1 (fr)	1980-10-03
CS149380A2 (en)	1984-01-16
DK145909C (da)	1983-09-19
DK145909B (da)	1983-04-11
EP0015802A1 (de)	1980-09-17
DE3067992D1 (en)	1984-07-05

Publication	Publication Date	Title
JP3932757B2 (ja)	2007-06-20	２−ヒドロキシ−４−メチルチオブタン酸の製造方法
CS231971B2 (en)	1985-01-16	Purification method for mercaptobenzothiazole
RU2348621C2 (ru)	2009-03-10	Способ получения 2-меркаптобензотиазола
US3681371A (en)	1972-08-01	Process for purification of crude 2-mercaptobenzothiazole
US4061646A (en)	1977-12-06	Process for purification of crude 2-mercaptobenzothiazole
US4192804A (en)	1980-03-11	Process for the purification of mercaptobenzothiazole
US5116997A (en)	1992-05-26	Purification of indigo
WO2012024839A1 (zh)	2012-03-01	二环己基二硫化物的制造方法
US4647669A (en)	1987-03-03	Process for the purification of mercaptobenzothizaole
KR100582334B1 (ko)	2006-05-23	설펜이미드의 제조방법
US4246180A (en)	1981-01-20	Process for separating off 1-amino-4-bromoanthraquinone-2-sulphonic acid
US3390190A (en)	1968-06-25	Process for purification of 4, 4'-dihydroxydiphenyl sulfide
WO2002008181A1 (en)	2002-01-31	Process for producing 2-hydroxy-4-methylthiobutanoic acid
MC2410A1 (fr)	1996-12-02	Procédé amélioré de fabrication de méthylène-bis (dibutyl-dithiocarbamate) ayant une coloration astm inférieure à 2
CN111635419B (zh)	2022-05-24	一种头孢地尼精制母液的处理方法
EP0035759B1 (de)	1985-07-10	Verfahren zur Herstellung von Dithioniten
JPS5858348B2 (ja)	1983-12-24	粗２−メルカプト．ベンゾ．チアゾ−ルの精製方法
JP4759828B2 (ja)	2011-08-31	２−ヒドロキシ−４−メチルチオブタン酸の製造方法
US5399783A (en)	1995-03-21	Preparation of 6,6'-dihydroxy-3,3,3',3'-tetramethyl-1,1'-spirobiindane
US7157583B2 (en)	2007-01-02	Process for producing high-purity 2,3-pyridinedicarboxylic acid
JP2000211905A (ja)	2000-08-02	フリーヒドロキシルアミン水溶液の製造方法
JPS59141531A (ja)	1984-08-14	４−ヒドロキシジフエニルと４，４′−ジヒドロキシジフエニルとを同時に回収する方法
JP2770512B2 (ja)	1998-07-02	アミノエチルスルホン酸アルカリ金属塩類の精製方法
JPH0324039A (ja)	1991-02-01	トリメチルアミン・三酸化イオウ錯体の製造方法及びトリメチルアミンの回収方法
JPS5824576A (ja)	1983-02-14	２−メルカプトベンゾチアゾ−ルの製造方法