DE1203749B - Verfahren zur Herstellung von ª-Cyancapronsaeure - Google Patents
Verfahren zur Herstellung von ª-CyancapronsaeureInfo
- Publication number
- DE1203749B DE1203749B DEB75332A DEB0075332A DE1203749B DE 1203749 B DE1203749 B DE 1203749B DE B75332 A DEB75332 A DE B75332A DE B0075332 A DEB0075332 A DE B0075332A DE 1203749 B DE1203749 B DE 1203749B
- Authority
- DE
- Germany
- Prior art keywords
- alkali
- acid
- glycolate
- glycol
- cyanocaproic
- 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 13
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000002253 acid Substances 0.000 title description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- INHNHRQXVDVIDZ-UHFFFAOYSA-N 6-cyanohexanoic acid Chemical compound OC(=O)CCCCCC#N INHNHRQXVDVIDZ-UHFFFAOYSA-N 0.000 claims description 10
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- RWMVCOUKVCLWIC-UHFFFAOYSA-N 2-oxocyclohexane-1-carbonitrile Chemical compound O=C1CCCCC1C#N RWMVCOUKVCLWIC-UHFFFAOYSA-N 0.000 claims description 5
- 238000003776 cleavage reaction Methods 0.000 claims description 5
- 230000007017 scission Effects 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- -1 alkali metal cyanide Chemical class 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- BTHAMQXVHRXABJ-UHFFFAOYSA-M [K+].C=C.C=C.OCC([O-])=O Chemical compound [K+].C=C.C=C.OCC([O-])=O BTHAMQXVHRXABJ-UHFFFAOYSA-M 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB75332A DE1203749B (de) | 1964-02-07 | 1964-02-07 | Verfahren zur Herstellung von ª-Cyancapronsaeure |
| US429885A US3346618A (en) | 1964-02-07 | 1965-02-02 | Production of epsilon-cyanocaproic acid |
| FR4601A FR1423579A (fr) | 1964-02-07 | 1965-02-05 | Procédé pour la production d'acide epsilon-cyanocaproïque |
| GB5052/65A GB1087603A (en) | 1964-02-07 | 1965-02-05 | Production of ª-cyanocaproic acid |
| BE659344D BE659344A (en, 2012) | 1964-02-07 | 1965-02-05 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB75332A DE1203749B (de) | 1964-02-07 | 1964-02-07 | Verfahren zur Herstellung von ª-Cyancapronsaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1203749B true DE1203749B (de) | 1965-10-28 |
Family
ID=6978614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB75332A Pending DE1203749B (de) | 1964-02-07 | 1964-02-07 | Verfahren zur Herstellung von ª-Cyancapronsaeure |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3346618A (en, 2012) |
| BE (1) | BE659344A (en, 2012) |
| DE (1) | DE1203749B (en, 2012) |
| FR (1) | FR1423579A (en, 2012) |
| GB (1) | GB1087603A (en, 2012) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3050547A (en) * | 1959-07-02 | 1962-08-21 | Dow Chemical Co | 1-2 ring cleavage of 2-cyanocyclo-alkanones |
-
1964
- 1964-02-07 DE DEB75332A patent/DE1203749B/de active Pending
-
1965
- 1965-02-02 US US429885A patent/US3346618A/en not_active Expired - Lifetime
- 1965-02-05 FR FR4601A patent/FR1423579A/fr not_active Expired
- 1965-02-05 GB GB5052/65A patent/GB1087603A/en not_active Expired
- 1965-02-05 BE BE659344D patent/BE659344A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1423579A (fr) | 1966-01-03 |
| US3346618A (en) | 1967-10-10 |
| BE659344A (en, 2012) | 1965-08-05 |
| GB1087603A (en) | 1967-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1226560B (de) | Verfahren zur Herstellung von Butylenglykoldiacetaten | |
| DE1468932B2 (de) | Verfahren zur kontinuierlichen herstellung von niedermolekularen aliphatischen acrylsaeureestern | |
| DE2248337A1 (de) | Verfahren zur herstellung von 3,4,5trimethoxybenzaldehyd | |
| DE1518517C (en, 2012) | ||
| EP0266690B1 (de) | Verfahren zur Herstellung von 2,2-disubstituierten 3-Chlorpropionsäureestern | |
| DE1203749B (de) | Verfahren zur Herstellung von ª-Cyancapronsaeure | |
| DE1518572A1 (de) | Verfahren zur kontinuierlichen Herstellung von Monoestern zweiwertiger Alkohole | |
| DE574838C (de) | Verfahren zur Darstellung von cyclischen Glykolen und ihren Derivaten bzw. von Ketonen | |
| DE907171C (de) | Verfahren zur Abtrennung sauerstoffhaltiger Verbindungen aus Produkten der katalytrischen Kohlenoxydhydrierung | |
| EP0171046B1 (de) | Verfahren zur Herstellung von Pantolacton | |
| DE960813C (de) | Verfahren zur Herstellung von ungesaettigten ª†- und ª€-Laktonen | |
| DE69806244T2 (de) | Fettsäuren-oligomere | |
| DE1099520B (de) | Verfahren zur Herstellung von Monoglyceriden von Fettsaeuren mit 8 bis 22 Kohlenstoffatomen | |
| DE2217529C3 (de) | Verfahren zur Herstellung von Sorbinsäure | |
| DE1189975B (de) | Verfahren zur Herstellung von beta, beta'-Dicyandiaethylaether | |
| DE1255650B (de) | Verfahren zur Herstellung von 1, 6-Hexandiolen | |
| DE954060C (de) | Verfahren zur Herstellung von Dialkylestern der Cyclohexa-1, 4-dien-1, 4-dicarbonsaeure durch Wasserabspaltung in fluessigem Zustand | |
| DE912810C (de) | Verfahren zur Herstellung von monomeren Vinylestern | |
| DE931226C (de) | Verfahren zur Herstellung von 3, 3-Di-(chlormethyl)-cyclooxabutan | |
| DE2263881A1 (de) | Verfahren zur herstellung von carvon | |
| DE875193C (de) | Verfahren zur Herstellung organischer sauerstoffhaltiger Verbindungen | |
| DE2300327A1 (de) | Verfahren zur herstellung von 3-fluorsalicylaldehyd | |
| DE1155774B (de) | Verfahren zur Herstellung von Cyanformimidoestern | |
| DE1518572C (de) | Verfahren zur Herstellung der Acryl saure und Methacrylsauremonoester von Alkandiolen | |
| DE3050795C2 (de) | Halogensubstituierte Tetrahydro-α-pyrone und Verfahren zu ihrer Herstellung |