DE2221109C2 - Verfahren zur Herstellung von a-Anilincarbonsäurenitrilen - Google Patents
Verfahren zur Herstellung von a-AnilincarbonsäurenitrilenInfo
- Publication number
- DE2221109C2 DE2221109C2 DE19722221109 DE2221109A DE2221109C2 DE 2221109 C2 DE2221109 C2 DE 2221109C2 DE 19722221109 DE19722221109 DE 19722221109 DE 2221109 A DE2221109 A DE 2221109A DE 2221109 C2 DE2221109 C2 DE 2221109C2
- Authority
- DE
- Germany
- Prior art keywords
- mol
- chlorine
- aniline
- chloro
- preparation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 26
- 150000002825 nitriles Chemical class 0.000 title claims description 15
- 239000002253 acid Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 cyano compound Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 5
- 150000001448 anilines Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- ACMJJQYSPUPMPN-UHFFFAOYSA-N 4-chloro-3-fluoroaniline Chemical compound NC1=CC=C(Cl)C(F)=C1 ACMJJQYSPUPMPN-UHFFFAOYSA-N 0.000 description 2
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical class NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 1
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical class [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical class COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- FPSTYXLUOFPGNZ-UHFFFAOYSA-N n-chloro-n-fluoroaniline Chemical class FN(Cl)C1=CC=CC=C1 FPSTYXLUOFPGNZ-UHFFFAOYSA-N 0.000 description 1
- AAFUAKIIYDTUJU-UHFFFAOYSA-N n-chloro-n-methoxyaniline Chemical class CON(Cl)C1=CC=CC=C1 AAFUAKIIYDTUJU-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1241071 | 1971-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2221109A1 DE2221109A1 (de) | 1972-11-16 |
| DE2221109C2 true DE2221109C2 (de) | 1983-10-06 |
Family
ID=10004092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722221109 Expired DE2221109C2 (de) | 1971-04-30 | 1972-04-28 | Verfahren zur Herstellung von a-Anilincarbonsäurenitrilen |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1547758A (en) * | 1975-07-29 | 1979-06-27 | Shell Int Research | Herbicidal composition |
| GB1577662A (en) * | 1976-05-08 | 1980-10-29 | Basf Ag | Manufacture of glycinonitriles |
| US4318920A (en) * | 1979-02-08 | 1982-03-09 | Abbott Laboratories | Ovicides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE151538C (enrdf_load_stackoverflow) * | ||||
| NL136594C (enrdf_load_stackoverflow) * | 1965-10-22 | |||
| US3463805A (en) * | 1967-05-08 | 1969-08-26 | Grace W R & Co | Production of aminonitriles under adiabatic conditions |
| GB1307978A (en) * | 1969-02-28 | 1973-02-21 | Wellcome Found | Amidines processes for their preparation and pharmaceutical compo sitions incorporating the same |
-
1971
- 1971-04-30 GB GB1327294D patent/GB1327294A/en not_active Expired
-
1972
- 1972-04-25 BE BE782595A patent/BE782595A/nl not_active IP Right Cessation
- 1972-04-27 NL NL7205688A patent/NL175173C/xx not_active IP Right Cessation
- 1972-04-27 DK DK212772A patent/DK153472C/da not_active IP Right Cessation
- 1972-04-28 DE DE19722221109 patent/DE2221109C2/de not_active Expired
- 1972-04-28 PL PL15504972A patent/PL83652B1/pl unknown
- 1972-04-28 CH CH639572A patent/CH589049A5/xx not_active IP Right Cessation
- 1972-04-28 ES ES402224A patent/ES402224A1/es not_active Expired
- 1972-04-28 FR FR7215325A patent/FR2139847B1/fr not_active Expired
- 1972-04-28 CA CA140,875A patent/CA982141A/en not_active Expired
- 1972-04-28 JP JP47042319A patent/JPS5749537B1/ja active Pending
- 1972-04-28 IT IT2369672A patent/IT953845B/it active
- 1972-04-28 RO RO7073672A patent/RO62750A/ro unknown
- 1972-04-28 CS CS289572A patent/CS195255B2/cs unknown
- 1972-04-28 SU SU1778332A patent/SU461492A3/ru active
- 1972-04-28 HU HUSE001623 patent/HU164835B/hu not_active IP Right Cessation
- 1972-04-28 DD DD16264872A patent/DD101889A5/xx unknown
- 1972-05-03 YU YU115772A patent/YU39269B/xx unknown
-
1980
- 1980-07-30 JP JP10378180A patent/JPS5639057A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL175173B (nl) | 1984-05-01 |
| GB1327294A (en) | 1973-08-22 |
| IT953845B (it) | 1973-08-10 |
| FR2139847A1 (enrdf_load_stackoverflow) | 1973-01-12 |
| YU39269B (en) | 1984-10-31 |
| CA982141A (en) | 1976-01-20 |
| FR2139847B1 (enrdf_load_stackoverflow) | 1973-12-07 |
| DD101889A5 (enrdf_load_stackoverflow) | 1973-11-20 |
| CS195255B2 (en) | 1980-01-31 |
| PL83652B1 (enrdf_load_stackoverflow) | 1975-12-31 |
| NL175173C (nl) | 1984-10-01 |
| YU115772A (en) | 1982-05-31 |
| SU461492A3 (ru) | 1975-02-25 |
| JPS5639057A (en) | 1981-04-14 |
| HU164835B (enrdf_load_stackoverflow) | 1974-04-11 |
| RO62750A (fr) | 1977-10-15 |
| AU4168072A (en) | 1973-11-01 |
| BE782595A (nl) | 1972-10-25 |
| NL7205688A (enrdf_load_stackoverflow) | 1972-11-01 |
| ES402224A1 (es) | 1976-01-01 |
| CH589049A5 (enrdf_load_stackoverflow) | 1977-06-30 |
| DK153472B (da) | 1988-07-18 |
| DE2221109A1 (de) | 1972-11-16 |
| JPS5736274B2 (enrdf_load_stackoverflow) | 1982-08-03 |
| DK153472C (da) | 1988-11-21 |
| JPS5749537B1 (enrdf_load_stackoverflow) | 1982-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C07C121/43 |
|
| 8181 | Inventor (new situation) |
Free format text: MONTIJN, PAULUS PIETER HELDEN, ROBERT VAN, AMSTERDAM, NL HADDOCK, ERNEST, SHEERNESS, SHEPPEY, KENT,GB |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |