DE2207020A1 - Alpha-phenyl-beta,beta-pentamethylenglutarsaeuredinitrile und verfahren zu ihrer herstellung - Google Patents
Alpha-phenyl-beta,beta-pentamethylenglutarsaeuredinitrile und verfahren zu ihrer herstellungInfo
- Publication number
- DE2207020A1 DE2207020A1 DE19722207020 DE2207020A DE2207020A1 DE 2207020 A1 DE2207020 A1 DE 2207020A1 DE 19722207020 DE19722207020 DE 19722207020 DE 2207020 A DE2207020 A DE 2207020A DE 2207020 A1 DE2207020 A1 DE 2207020A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- beta
- glutaric acid
- acid dinitrile
- alpha
- 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 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 10
- VLRQRRQHXZCEDL-UHFFFAOYSA-N 2-cyclohexylideneacetonitrile Chemical compound N#CC=C1CCCCC1 VLRQRRQHXZCEDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000007962 benzene acetonitriles Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- -1 Phenyl- Chemical group 0.000 description 5
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 1
- RNHKXHKUKJXLAU-UHFFFAOYSA-N 2-(4-methylphenyl)acetonitrile Chemical compound CC1=CC=C(CC#N)C=C1 RNHKXHKUKJXLAU-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE795483D BE795483A (fr) | 1972-02-15 | Glutaronitriles substitues | |
| DE19722207020 DE2207020A1 (de) | 1972-02-15 | 1972-02-15 | Alpha-phenyl-beta,beta-pentamethylenglutarsaeuredinitrile und verfahren zu ihrer herstellung |
| CA162,942A CA1009253A (en) | 1972-02-15 | 1973-01-30 | .alpha.-PHENYL-.beta.,.beta.-PENTAMETHYLENE-GLUTARIC ACID DINITRILES AND PROCESS FOR THEIR PREPARATION |
| NL7301868A NL7301868A (enExample) | 1972-02-15 | 1973-02-09 | |
| CH137673A CH574916A5 (enExample) | 1972-02-15 | 1973-02-12 | |
| IT2035073A IT1051354B (it) | 1972-02-15 | 1973-02-13 | Dinitrili alfa fenil beta beta pentametilenglutarici e proocesso per la loro preparazione |
| JP1714473A JPS4886852A (enExample) | 1972-02-15 | 1973-02-13 | |
| FR7305141A FR2172204B1 (enExample) | 1972-02-15 | 1973-02-14 | |
| GB721973A GB1389188A (en) | 1972-02-15 | 1973-02-14 | Alpha-phenyl-beta,beta-pentamethylene-glutaric acid dinitriles and process for their preparation |
| US353319A US3890366A (en) | 1972-02-15 | 1973-04-23 | {60 -Phenyl-{62 ,{62 -pentamethylene-glutaric acid dinitriles and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722207020 DE2207020A1 (de) | 1972-02-15 | 1972-02-15 | Alpha-phenyl-beta,beta-pentamethylenglutarsaeuredinitrile und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2207020A1 true DE2207020A1 (de) | 1973-08-23 |
Family
ID=5835985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722207020 Pending DE2207020A1 (de) | 1972-02-15 | 1972-02-15 | Alpha-phenyl-beta,beta-pentamethylenglutarsaeuredinitrile und verfahren zu ihrer herstellung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4886852A (enExample) |
| BE (1) | BE795483A (enExample) |
| CA (1) | CA1009253A (enExample) |
| CH (1) | CH574916A5 (enExample) |
| DE (1) | DE2207020A1 (enExample) |
| FR (1) | FR2172204B1 (enExample) |
| GB (1) | GB1389188A (enExample) |
| IT (1) | IT1051354B (enExample) |
| NL (1) | NL7301868A (enExample) |
-
0
- BE BE795483D patent/BE795483A/xx unknown
-
1972
- 1972-02-15 DE DE19722207020 patent/DE2207020A1/de active Pending
-
1973
- 1973-01-30 CA CA162,942A patent/CA1009253A/en not_active Expired
- 1973-02-09 NL NL7301868A patent/NL7301868A/xx unknown
- 1973-02-12 CH CH137673A patent/CH574916A5/xx not_active IP Right Cessation
- 1973-02-13 JP JP1714473A patent/JPS4886852A/ja active Pending
- 1973-02-13 IT IT2035073A patent/IT1051354B/it active
- 1973-02-14 FR FR7305141A patent/FR2172204B1/fr not_active Expired
- 1973-02-14 GB GB721973A patent/GB1389188A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4886852A (enExample) | 1973-11-15 |
| FR2172204B1 (enExample) | 1976-11-05 |
| IT1051354B (it) | 1981-04-21 |
| NL7301868A (enExample) | 1973-08-17 |
| BE795483A (fr) | 1973-08-16 |
| CH574916A5 (enExample) | 1976-04-30 |
| FR2172204A1 (enExample) | 1973-09-28 |
| CA1009253A (en) | 1977-04-26 |
| GB1389188A (en) | 1975-04-03 |
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