DE1187627B - Verfahren zur Herstellung von N-Trifluormethylarylamin-N-sulfensaeurehalogeniden - Google Patents
Verfahren zur Herstellung von N-Trifluormethylarylamin-N-sulfensaeurehalogenidenInfo
- Publication number
- DE1187627B DE1187627B DEF38508A DEF0038508A DE1187627B DE 1187627 B DE1187627 B DE 1187627B DE F38508 A DEF38508 A DE F38508A DE F0038508 A DEF0038508 A DE F0038508A DE 1187627 B DE1187627 B DE 1187627B
- Authority
- DE
- Germany
- Prior art keywords
- chlorine
- trifluoromethylarylamine
- bromine
- preparation
- trifluoromethyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title 1
- 150000004820 halides Chemical class 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LQLJKDWVUKGWJR-UHFFFAOYSA-N 4-chloro-n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=C(Cl)C=C1 LQLJKDWVUKGWJR-UHFFFAOYSA-N 0.000 description 2
- ODBBDTBHSXVMJM-UHFFFAOYSA-N FC(F)(F)NC1=C(C=CC(=C1)Cl)Cl Chemical compound FC(F)(F)NC1=C(C=CC(=C1)Cl)Cl ODBBDTBHSXVMJM-UHFFFAOYSA-N 0.000 description 2
- -1 amine salt Chemical class 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- XRTWYFMTEIOUBW-UHFFFAOYSA-N 2,4-dichloro-N-(trifluoromethyl)aniline Chemical compound FC(NC1=C(C=C(C=C1)Cl)Cl)(F)F XRTWYFMTEIOUBW-UHFFFAOYSA-N 0.000 description 1
- ARTHYKTZDDSONA-UHFFFAOYSA-N FC(N(C1=CC=C(C=C1)Cl)SCl)(F)F Chemical compound FC(N(C1=CC=C(C=C1)Cl)SCl)(F)F ARTHYKTZDDSONA-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- QQEOVNFTLNNSHW-UHFFFAOYSA-N [2,5-dichloro-N-(trifluoromethyl)anilino] thiohypobromite Chemical compound FC(N(SBr)C1=C(C=CC(=C1)Cl)Cl)(F)F QQEOVNFTLNNSHW-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/272—Unsaturated compounds containing sulfur atoms
- D06M13/278—Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL301285D NL301285A (en:Method) | 1962-12-10 | ||
| DEF38508A DE1187627B (de) | 1962-12-10 | 1962-12-10 | Verfahren zur Herstellung von N-Trifluormethylarylamin-N-sulfensaeurehalogeniden |
| CH1188663A CH426778A (de) | 1962-12-10 | 1963-09-26 | Verfahren zur Herstellung von N-Aryl-N-trifluormethylsulfen-säurehalogeniden |
| AT830763A AT241433B (de) | 1962-12-10 | 1963-10-17 | Verfahren zur Herstellung von N-Trifluormethyl-N-aryl-aminosulfensäurehalogeniden |
| US319691A US3360542A (en) | 1962-12-10 | 1963-10-29 | Trifluoromethyl-amino-sulfenyl halides |
| GB42899/63A GB1022758A (en) | 1962-12-10 | 1963-10-30 | New chemical compounds and process for the production thereof |
| BE640471D BE640471A (en:Method) | 1962-12-10 | 1963-11-27 | |
| FR955149A FR1382390A (fr) | 1962-12-10 | 1963-11-27 | Halogénures de n-aryl-n-trifluorométhylsulfényle, et procédé pour les fabriquer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF38508A DE1187627B (de) | 1962-12-10 | 1962-12-10 | Verfahren zur Herstellung von N-Trifluormethylarylamin-N-sulfensaeurehalogeniden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1187627B true DE1187627B (de) | 1965-02-25 |
Family
ID=7097375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF38508A Pending DE1187627B (de) | 1962-12-10 | 1962-12-10 | Verfahren zur Herstellung von N-Trifluormethylarylamin-N-sulfensaeurehalogeniden |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3360542A (en:Method) |
| AT (1) | AT241433B (en:Method) |
| BE (1) | BE640471A (en:Method) |
| CH (1) | CH426778A (en:Method) |
| DE (1) | DE1187627B (en:Method) |
| GB (1) | GB1022758A (en:Method) |
| NL (1) | NL301285A (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2330241C3 (de) * | 1973-06-14 | 1980-10-09 | Bayer Ag, 5090 Leverkusen | Chlorthio-N-phthalimid, Verfahren zu seiner Herstellung und seine Verwendung |
| US4992583A (en) * | 1989-01-06 | 1991-02-12 | The Goodyear Tire & Rubber Company | Process for synthesizing N-chlorothio-sulfonamides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1064524B (de) * | 1955-01-29 | 1959-09-03 | Bayer Ag | Verfahren zur Herstellung von Aminsulfenhalogeniden |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB790021A (en) * | 1954-11-10 | 1958-01-29 | Bayer Ag | Aminosulphene halides and a process for theií¡í¡tion |
-
0
- NL NL301285D patent/NL301285A/xx unknown
-
1962
- 1962-12-10 DE DEF38508A patent/DE1187627B/de active Pending
-
1963
- 1963-09-26 CH CH1188663A patent/CH426778A/de unknown
- 1963-10-17 AT AT830763A patent/AT241433B/de active
- 1963-10-29 US US319691A patent/US3360542A/en not_active Expired - Lifetime
- 1963-10-30 GB GB42899/63A patent/GB1022758A/en not_active Expired
- 1963-11-27 BE BE640471D patent/BE640471A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1064524B (de) * | 1955-01-29 | 1959-09-03 | Bayer Ag | Verfahren zur Herstellung von Aminsulfenhalogeniden |
Also Published As
| Publication number | Publication date |
|---|---|
| NL301285A (en:Method) | |
| GB1022758A (en) | 1966-03-16 |
| AT241433B (de) | 1965-07-26 |
| US3360542A (en) | 1967-12-26 |
| CH426778A (de) | 1966-12-31 |
| BE640471A (en:Method) | 1964-03-16 |
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