JPS5839831B2 - ２−メルカプトベンゾチアゾ−ルまたは２−メルカプトベンズイミダゾ−ルの亜鉛塩の製造方法 - Google Patents

２−メルカプトベンゾチアゾ−ルまたは２−メルカプトベンズイミダゾ−ルの亜鉛塩の製造方法

Info

Publication number: JPS5839831B2
Authority: JP; Japan
Prior art keywords: mercaptobenzothiazole; mercaptobenzimidazole; zinc salt; zinc; weight
Prior art date: 1973-04-18
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.): Expired

Application number

JP49042359A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5012081A (fr

Inventor

デイ−タ− バルニケルカ−ル

フリ−ドリツヒアドルフ

カシエリカ− ダツタトラヤ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

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.)

1973-04-18

Filing date

1974-04-17

Publication date

1983-09-01

1974-04-17 Application filed by Bayer AG filed Critical Bayer AG

1975-02-07 Publication of JPS5012081A publication Critical patent/JPS5012081A/ja

1983-09-01 Publication of JPS5839831B2 publication Critical patent/JPS5839831B2/ja

Status Expired legal-status Critical Current

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 37
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 title claims description 17
150000003751 zinc Chemical class 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title claims description 7
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 14
239000011787 zinc oxide Substances 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 4
229940007718 zinc hydroxide Drugs 0.000 claims description 4
229910021511 zinc hydroxide Inorganic materials 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
-1 alkaline earth metal salt Chemical class 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 7
238000000034 method Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000001447 alkali salts Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
239000006057 Non-nutritive feed additive Substances 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
238000013021 overheating Methods 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
PGNWIWKMXVDXHP-UHFFFAOYSA-L zinc;1,3-benzothiazole-2-thiolate Chemical compound [Zn+2].C1=CC=C2SC([S-])=NC2=C1.C1=CC=C2SC([S-])=NC2=C1 PGNWIWKMXVDXHP-UHFFFAOYSA-L 0.000 description 1
IIKINNWGZZVUPY-UHFFFAOYSA-N zinc;1,3-dihydrobenzimidazole-2-thione Chemical compound [Zn+2].C1=CC=C2NC(=S)NC2=C1 IIKINNWGZZVUPY-UHFFFAOYSA-N 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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
- C07D235/28—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP49042359A 1973-04-18 1974-04-17 ２−メルカプトベンゾチアゾ−ルまたは２−メルカプトベンズイミダゾ−ルの亜鉛塩の製造方法 Expired JPS5839831B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2319634A DE2319634C3 (de)	1973-04-18	1973-04-18	Verfahren zur Herstellung eines Zinksalzes des 2-Merkaptobenzothiazols oder des 2-Merkaptobenzimidazols
DE2319634		1973-04-18

Publications (2)

Publication Number	Publication Date
JPS5012081A JPS5012081A (fr)	1975-02-07
JPS5839831B2 true JPS5839831B2 (ja)	1983-09-01

Family

ID=5878504

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP49042359A Expired JPS5839831B2 (ja)	1973-04-18	1974-04-17	２−メルカプトベンゾチアゾ−ルまたは２−メルカプトベンズイミダゾ−ルの亜鉛塩の製造方法

Country Status (10)

Country	Link
JP (1)	JPS5839831B2 (fr)
BE (1)	BE813817A (fr)
BR (1)	BR7403072D0 (fr)
DE (1)	DE2319634C3 (fr)
ES (1)	ES425468A1 (fr)
FR (1)	FR2226404B1 (fr)
GB (1)	GB1396498A (fr)
IN (1)	IN139576B (fr)
IT (1)	IT1011242B (fr)
ZA (1)	ZA742452B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4017458A (en) *	1976-02-26	1977-04-12	The Firestone Tire & Rubber Company	Stabilization of poly(phosphazenes)
CN116789602A (zh) *	2023-06-20	2023-09-22	鹤壁中昊新材料科技有限公司	一种用杂环化合物制备含氮、硫苯并杂环有机锌盐的方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2754303A (en) *	1954-04-07	1956-07-10	Monsanto Chemicals	Process of producing normal zinc mercaptobenzothiazole
GB894337A (en) *	1959-02-10	1962-04-18	Monsanto Chemicals	Production of salts of mercaptothiazoles

1973
- 1973-04-18 DE DE2319634A patent/DE2319634C3/de not_active Expired
1974
- 1974-03-22 IN IN625/CAL/74A patent/IN139576B/en unknown
- 1974-04-16 IT IT50407/74A patent/IT1011242B/it active
- 1974-04-17 BR BR3072/74A patent/BR7403072D0/pt unknown
- 1974-04-17 ZA ZA00742452A patent/ZA742452B/xx unknown
- 1974-04-17 JP JP49042359A patent/JPS5839831B2/ja not_active Expired
- 1974-04-17 BE BE143285A patent/BE813817A/fr unknown
- 1974-04-17 GB GB1672774A patent/GB1396498A/en not_active Expired
- 1974-04-18 ES ES425468A patent/ES425468A1/es not_active Expired
- 1974-04-18 FR FR7413576A patent/FR2226404B1/fr not_active Expired

Also Published As

Publication number	Publication date
FR2226404B1 (fr)	1977-10-14
ES425468A1 (es)	1976-07-01
GB1396498A (en)	1975-06-04
DE2319634B2 (de)	1981-04-16
IN139576B (fr)	1976-07-03
ZA742452B (en)	1975-04-30
JPS5012081A (fr)	1975-02-07
FR2226404A1 (fr)	1974-11-15
BR7403072D0 (pt)	1974-12-03
IT1011242B (it)	1977-01-20
DE2319634C3 (de)	1982-04-01
DE2319634A1 (de)	1974-11-14
BE813817A (fr)	1974-10-17

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