DE2032565A1 - Verfahren zur Herstellung von 3 Difluorchlormethylanihn - Google Patents
Verfahren zur Herstellung von 3 DifluorchlormethylanihnInfo
- Publication number
- DE2032565A1 DE2032565A1 DE19702032565 DE2032565A DE2032565A1 DE 2032565 A1 DE2032565 A1 DE 2032565A1 DE 19702032565 DE19702032565 DE 19702032565 DE 2032565 A DE2032565 A DE 2032565A DE 2032565 A1 DE2032565 A1 DE 2032565A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- hydrochloride
- nitro
- catalyst
- water
- 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 description 4
- 238000002360 preparation method Methods 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 9
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 claims 1
- 150000001722 carbon compounds Chemical class 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GOKFUVWRHMMRFK-UHFFFAOYSA-N 1-(chloromethyl)-2,4-difluoro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=C(F)C=CC(CCl)=C1F GOKFUVWRHMMRFK-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OVUKQQRPTLPXTD-UHFFFAOYSA-N 1-(chloromethyl)-2,3-difluorobenzene Chemical compound FC1=CC=CC(CCl)=C1F OVUKQQRPTLPXTD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- -1 difluorochloromethylnitrobenzene Chemical compound 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702032565 DE2032565A1 (de) | 1970-07-01 | 1970-07-01 | Verfahren zur Herstellung von 3 Difluorchlormethylanihn |
| NL7108812A NL7108812A (enExample) | 1970-07-01 | 1971-06-25 | |
| BE769220A BE769220A (fr) | 1970-07-01 | 1971-06-29 | Procede de preparation de 3-difluorochloromethylaniline |
| IL37182A IL37182A0 (en) | 1970-07-01 | 1971-06-29 | Process for the preparation of 3-difluoro-chloro-methyl aniline |
| GB3068971A GB1314755A (en) | 1970-07-01 | 1971-06-30 | Process for the preparation of 3-difluoro-chloro-methyl aniline |
| FR7124078A FR2100107A5 (enExample) | 1970-07-01 | 1971-07-01 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702032565 DE2032565A1 (de) | 1970-07-01 | 1970-07-01 | Verfahren zur Herstellung von 3 Difluorchlormethylanihn |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2032565A1 true DE2032565A1 (de) | 1972-01-05 |
Family
ID=5775491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702032565 Pending DE2032565A1 (de) | 1970-07-01 | 1970-07-01 | Verfahren zur Herstellung von 3 Difluorchlormethylanihn |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE769220A (enExample) |
| DE (1) | DE2032565A1 (enExample) |
| FR (1) | FR2100107A5 (enExample) |
| GB (1) | GB1314755A (enExample) |
| IL (1) | IL37182A0 (enExample) |
| NL (1) | NL7108812A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002802A1 (de) * | 1977-12-24 | 1979-07-11 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Halogenanilinen |
| DE3003960A1 (de) * | 1979-02-15 | 1980-08-28 | Rhone Poulenc Agrochimie | Verfahren zur herstellung m-chlorsubstituierter aniline |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5068436A (en) * | 1989-03-10 | 1991-11-26 | E. I. Du Pont De Nemours And Company | Hydrogenation of halonitrobenzenes without dehalogenation |
| CN117229151A (zh) * | 2023-09-28 | 2023-12-15 | 老河口华辰化学有限公司 | 一种催化加氢制备4氯3甲基苯胺的方法 |
-
1970
- 1970-07-01 DE DE19702032565 patent/DE2032565A1/de active Pending
-
1971
- 1971-06-25 NL NL7108812A patent/NL7108812A/xx unknown
- 1971-06-29 BE BE769220A patent/BE769220A/xx unknown
- 1971-06-29 IL IL37182A patent/IL37182A0/xx unknown
- 1971-06-30 GB GB3068971A patent/GB1314755A/en not_active Expired
- 1971-07-01 FR FR7124078A patent/FR2100107A5/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002802A1 (de) * | 1977-12-24 | 1979-07-11 | BASF Aktiengesellschaft | Verfahren zur Herstellung von Halogenanilinen |
| DE3003960A1 (de) * | 1979-02-15 | 1980-08-28 | Rhone Poulenc Agrochimie | Verfahren zur herstellung m-chlorsubstituierter aniline |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2100107A5 (enExample) | 1972-03-17 |
| IL37182A0 (en) | 1971-08-25 |
| GB1314755A (en) | 1973-04-26 |
| NL7108812A (enExample) | 1972-01-04 |
| BE769220A (fr) | 1971-12-29 |
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