DE1170414B - Verfahren zur Herstellung von N-Trifluormethylaminen - Google Patents
Verfahren zur Herstellung von N-TrifluormethylaminenInfo
- Publication number
- DE1170414B DE1170414B DEF36806A DEF0036806A DE1170414B DE 1170414 B DE1170414 B DE 1170414B DE F36806 A DEF36806 A DE F36806A DE F0036806 A DEF0036806 A DE F0036806A DE 1170414 B DE1170414 B DE 1170414B
- Authority
- DE
- Germany
- Prior art keywords
- isocyanide
- hydrofluoric acid
- trifluoromethylamines
- isocyanide dichloride
- dichloride
- 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 8
- MYMLGBAVNHFRJS-UHFFFAOYSA-N trifluoromethanamine Chemical class NC(F)(F)F MYMLGBAVNHFRJS-UHFFFAOYSA-N 0.000 title claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 26
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QPPCIPBFKQOIMT-UHFFFAOYSA-N 1-chloro-4-isocyanobenzene Chemical compound ClC1=CC=C([N+]#[C-])C=C1 QPPCIPBFKQOIMT-UHFFFAOYSA-N 0.000 description 2
- ZNGHGSVYBZGDJE-UHFFFAOYSA-N 2-isocyano-1-methyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]#[C-] ZNGHGSVYBZGDJE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- WSONBZIRAKRENO-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-6-isocyanobenzene Chemical compound ClC1=C(Cl)C(Cl)=C([N+]#[C-])C(Cl)=C1Cl WSONBZIRAKRENO-UHFFFAOYSA-N 0.000 description 1
- DWCQFBKQRUHVIV-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5,6-diisocyanobenzene Chemical compound ClC1=C(Cl)C(Cl)=C([N+]#[C-])C([N+]#[C-])=C1Cl DWCQFBKQRUHVIV-UHFFFAOYSA-N 0.000 description 1
- FXJGRGSNBWBJRZ-UHFFFAOYSA-N 1,3,5-trichloro-2-isocyanobenzene Chemical compound ClC1=CC(Cl)=C([N+]#[C-])C(Cl)=C1 FXJGRGSNBWBJRZ-UHFFFAOYSA-N 0.000 description 1
- XWTFRFDJAYBRHE-UHFFFAOYSA-N 1,4-dichloro-2-isocyanobenzene Chemical compound ClC1=CC=C(Cl)C([N+]#[C-])=C1 XWTFRFDJAYBRHE-UHFFFAOYSA-N 0.000 description 1
- YIIXVYUXPQFHIO-UHFFFAOYSA-N 1-chloro-2-isocyano-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C([N+]#[C-])=C1 YIIXVYUXPQFHIO-UHFFFAOYSA-N 0.000 description 1
- -1 2,4-dichloro-5-methylphenyl isocyanide Chemical compound 0.000 description 1
- MFKDULOUZDAXOD-UHFFFAOYSA-N 2-methyl-5-nitro-N-(trifluoromethyl)aniline Chemical compound FC(NC1=C(C=CC(=C1)[N+](=O)[O-])C)(F)F MFKDULOUZDAXOD-UHFFFAOYSA-N 0.000 description 1
- BEWBGNAWQZLVMP-UHFFFAOYSA-N 3-isocyanobenzonitrile Chemical compound [C-]#[N+]C1=CC=CC(C#N)=C1 BEWBGNAWQZLVMP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PPQBGGLGUHCGRC-UHFFFAOYSA-N 4-methyl-n-(trifluoromethyl)aniline Chemical compound CC1=CC=C(NC(F)(F)F)C=C1 PPQBGGLGUHCGRC-UHFFFAOYSA-N 0.000 description 1
- PCHGCYDBHXTQPP-UHFFFAOYSA-N ClC1=NC(=NC(=N1)[N+]#[C-])Cl Chemical compound ClC1=NC(=NC(=N1)[N+]#[C-])Cl PCHGCYDBHXTQPP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- YDKPKFUKZKHQHZ-UHFFFAOYSA-N [C-]#N.F.F Chemical compound [C-]#N.F.F YDKPKFUKZKHQHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- CFMGUIWIJXYCCS-UHFFFAOYSA-N methyl 4-isocyanobenzoate Chemical compound COC(=O)C1=CC=C([N+]#[C-])C=C1 CFMGUIWIJXYCCS-UHFFFAOYSA-N 0.000 description 1
- 239000008164 mustard oil Substances 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
- 239000004476 plant protection product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A01N47/08—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 the carbon atom having one or more single bonds to nitrogen atoms
-
- 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
- C07C209/74—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 by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL137818D NL137818C (en]) | 1962-05-15 | ||
| BE632365D BE632365A (en]) | 1962-05-15 | ||
| NL292722D NL292722A (en]) | 1962-05-15 | ||
| DEF36806A DE1170414B (de) | 1962-05-15 | 1962-05-15 | Verfahren zur Herstellung von N-Trifluormethylaminen |
| CH484163A CH428750A (de) | 1962-05-15 | 1963-04-18 | Verfahren zur Herstellung von N-Trifluormethylaminen |
| GB1838463A GB959881A (en) | 1962-05-15 | 1963-05-09 | N-trifluoromethylamines |
| FR934862A FR1357926A (fr) | 1962-05-15 | 1963-05-15 | Nouveaux agents fongicides et herbicides et procédé pour les préparer |
| US491015A US3355454A (en) | 1962-05-15 | 1965-09-28 | Nu-trifluoromethylamines and process for their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF36806A DE1170414B (de) | 1962-05-15 | 1962-05-15 | Verfahren zur Herstellung von N-Trifluormethylaminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1170414B true DE1170414B (de) | 1964-05-21 |
Family
ID=7096615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF36806A Pending DE1170414B (de) | 1962-05-15 | 1962-05-15 | Verfahren zur Herstellung von N-Trifluormethylaminen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE632365A (en]) |
| CH (1) | CH428750A (en]) |
| DE (1) | DE1170414B (en]) |
| GB (1) | GB959881A (en]) |
| NL (2) | NL292722A (en]) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3218966A1 (de) * | 1981-08-29 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Fluorhaltige 4,6-diamino-s-triazine, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
-
0
- NL NL137818D patent/NL137818C/xx active
- BE BE632365D patent/BE632365A/xx unknown
- NL NL292722D patent/NL292722A/xx unknown
-
1962
- 1962-05-15 DE DEF36806A patent/DE1170414B/de active Pending
-
1963
- 1963-04-18 CH CH484163A patent/CH428750A/de unknown
- 1963-05-09 GB GB1838463A patent/GB959881A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL292722A (en]) | |
| GB959881A (en) | 1964-06-03 |
| NL137818C (en]) | |
| CH428750A (de) | 1967-01-31 |
| BE632365A (en]) |
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