DE2503321C2 - Verfahren zur Herstellung von 1,4- Naphthodinitril - Google Patents
Verfahren zur Herstellung von 1,4- NaphthodinitrilInfo
- Publication number
- DE2503321C2 DE2503321C2 DE2503321A DE2503321A DE2503321C2 DE 2503321 C2 DE2503321 C2 DE 2503321C2 DE 2503321 A DE2503321 A DE 2503321A DE 2503321 A DE2503321 A DE 2503321A DE 2503321 C2 DE2503321 C2 DE 2503321C2
- Authority
- DE
- Germany
- Prior art keywords
- naphthodinitrile
- amino
- reaction
- mol
- 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 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229940015043 glyoxal Drugs 0.000 claims description 3
- FWPFXBANOKKNBR-UHFFFAOYSA-N 2-[2-(cyanomethyl)phenyl]acetonitrile Chemical compound N#CCC1=CC=CC=C1CC#N FWPFXBANOKKNBR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N o-phenylene-diaceto-nitrile Natural products N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000004705 aldimines Chemical class 0.000 description 3
- -1 aliphatic aldimines Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- BXUKAXFDABMVND-UHFFFAOYSA-L disodium;1,2-dihydroxyethane-1,2-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C(O)C(O)S([O-])(=O)=O BXUKAXFDABMVND-UHFFFAOYSA-L 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2503321A DE2503321C2 (de) | 1975-01-28 | 1975-01-28 | Verfahren zur Herstellung von 1,4- Naphthodinitril |
| ES444540A ES444540A1 (es) | 1975-01-28 | 1976-01-22 | Procedimiento para la preparacion de 1,4-naftodinitrilo. |
| US05/651,699 US4025543A (en) | 1975-01-28 | 1976-01-23 | Process for the preparation of 1,4-naphthodinitrile |
| NL7600712A NL7600712A (nl) | 1975-01-28 | 1976-01-23 | Werkwijze voor de bereiding van 1,4-naftodinitrile. |
| LU74243A LU74243A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-28 | 1976-01-26 | |
| SE7600764A SE426318B (sv) | 1975-01-28 | 1976-01-26 | Forfarande for framstellning av 1,4-naftodinitril |
| IT19602/76A IT1054499B (it) | 1975-01-28 | 1976-01-26 | Processo per la preparazione di 1.4 naftodinitrile |
| CH91576A CH598203A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-01-28 | 1976-01-26 | |
| DK31676*#A DK31676A (da) | 1975-01-28 | 1976-01-27 | Fremgangsmade til fremstilling af 1,4-naphthodinitril |
| JP51007185A JPS5933583B2 (ja) | 1975-01-28 | 1976-01-27 | １，４−ナフトジニトリルの製法 |
| AU10574/76A AU489840B2 (en) | 1975-01-28 | 1976-01-27 | Process forthe preparation of 1, 4-naphthodinitrile |
| CA244,300A CA1056400A (en) | 1975-01-28 | 1976-01-27 | Process for the preparation of 1,4-naphthodinitrile |
| BR7600478A BR7600478A (pt) | 1975-01-28 | 1976-01-27 | Processo para a obtencao de 1,4-naftodinitrila |
| GB3305/76A GB1521803A (en) | 1975-01-28 | 1976-01-28 | Preparation of aromatic 1,4-dinitriles |
| FR7602251A FR2299316A1 (fr) | 1975-01-28 | 1976-01-28 | Procede de preparation du dicyano-1,4 naphtalene |
| BE163864A BE837989A (fr) | 1975-01-28 | 1976-01-28 | Procede de preparation du dicyano-1,4 naphtalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2503321A DE2503321C2 (de) | 1975-01-28 | 1975-01-28 | Verfahren zur Herstellung von 1,4- Naphthodinitril |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2503321A1 DE2503321A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-08 |
| DE2503321B1 DE2503321B1 (de) | 1976-07-08 |
| DE2503321C2 true DE2503321C2 (de) | 1984-05-30 |
Family
ID=5937457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2503321A Expired DE2503321C2 (de) | 1975-01-28 | 1975-01-28 | Verfahren zur Herstellung von 1,4- Naphthodinitril |
Country Status (15)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1519019A (en) * | 1974-11-14 | 1978-07-26 | Ciba Geigy Ag | Process for the manufacture of 1,4-disubstituted bicyclic or tricyclic compounds and 1,4-disubstituted bicyclic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3501470A (en) * | 1966-09-30 | 1970-03-17 | Standard Oil Co | Diguanamines |
-
1975
- 1975-01-28 DE DE2503321A patent/DE2503321C2/de not_active Expired
-
1976
- 1976-01-22 ES ES444540A patent/ES444540A1/es not_active Expired
- 1976-01-23 US US05/651,699 patent/US4025543A/en not_active Expired - Lifetime
- 1976-01-23 NL NL7600712A patent/NL7600712A/xx not_active Application Discontinuation
- 1976-01-26 CH CH91576A patent/CH598203A5/xx not_active IP Right Cessation
- 1976-01-26 IT IT19602/76A patent/IT1054499B/it active
- 1976-01-26 LU LU74243A patent/LU74243A1/xx unknown
- 1976-01-26 SE SE7600764A patent/SE426318B/xx unknown
- 1976-01-27 CA CA244,300A patent/CA1056400A/en not_active Expired
- 1976-01-27 BR BR7600478A patent/BR7600478A/pt unknown
- 1976-01-27 DK DK31676*#A patent/DK31676A/da not_active Application Discontinuation
- 1976-01-27 JP JP51007185A patent/JPS5933583B2/ja not_active Expired
- 1976-01-28 GB GB3305/76A patent/GB1521803A/en not_active Expired
- 1976-01-28 BE BE163864A patent/BE837989A/xx not_active IP Right Cessation
- 1976-01-28 FR FR7602251A patent/FR2299316A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| LU74243A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-12-31 |
| CH598203A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-04-28 |
| DK31676A (da) | 1976-07-29 |
| ES444540A1 (es) | 1977-06-01 |
| GB1521803A (en) | 1978-08-16 |
| IT1054499B (it) | 1981-11-10 |
| JPS51100052A (en) | 1976-09-03 |
| DE2503321A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-08 |
| US4025543A (en) | 1977-05-24 |
| FR2299316B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-18 |
| FR2299316A1 (fr) | 1976-08-27 |
| JPS5933583B2 (ja) | 1984-08-16 |
| BE837989A (fr) | 1976-07-28 |
| CA1056400A (en) | 1979-06-12 |
| SE426318B (sv) | 1982-12-27 |
| AU1057476A (en) | 1977-08-04 |
| NL7600712A (nl) | 1976-07-30 |
| DE2503321B1 (de) | 1976-07-08 |
| SE7600764L (sv) | 1976-07-29 |
| BR7600478A (pt) | 1976-09-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8281 | Inventor (new situation) |
Free format text: HEISS, LORENZ, DIPL.-CHEM. DR., 6238 HOFHEIM, DE UHL, KLAUS, DIPL.-CHEM. DR., 6231 NEUENHAIN, DE |
|
| 8339 | Ceased/non-payment of the annual fee |