NO125816B - - Google Patents
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- Publication number
- NO125816B NO125816B NO2611/68A NO261168A NO125816B NO 125816 B NO125816 B NO 125816B NO 2611/68 A NO2611/68 A NO 2611/68A NO 261168 A NO261168 A NO 261168A NO 125816 B NO125816 B NO 125816B
- Authority
- NO
- Norway
- Prior art keywords
- cyano
- atoms
- ketonitriles
- dimethyl
- unsaturated
- Prior art date
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 5
- -1 phenyl-(3,3-dimethyl-5-cyano-penten-1-yl)-ketone Chemical compound 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZLKUKJGDRJMIEA-UHFFFAOYSA-N 4,4-dimethyl-5-(2-oxocyclohexylidene)pentanenitrile Chemical compound CC(C=C1C(CCCC1)=O)(CCC#N)C ZLKUKJGDRJMIEA-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RHLVCLIPMVJYKS-UHFFFAOYSA-N ethyl n-pentyl ketone Natural products CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0053487 | 1967-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125816B true NO125816B (xx) | 1972-11-06 |
Family
ID=7055017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2611/68A NO125816B (xx) | 1967-06-30 | 1968-06-29 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3632625A (xx) |
| AT (1) | AT277964B (xx) |
| BE (1) | BE717306A (xx) |
| BR (1) | BR6800229D0 (xx) |
| CH (1) | CH502993A (xx) |
| CS (1) | CS153464B2 (xx) |
| DK (1) | DK119307B (xx) |
| ES (1) | ES355603A1 (xx) |
| FI (1) | FI48723C (xx) |
| FR (1) | FR1586868A (xx) |
| GB (1) | GB1207756A (xx) |
| IL (1) | IL30267A (xx) |
| NL (1) | NL6809168A (xx) |
| NO (1) | NO125816B (xx) |
| SE (1) | SE360073B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3898265A (en) * | 1970-08-26 | 1975-08-05 | Hoffmann La Roche | Steriod total synthesis process utilizing a cyanoalkyl A-ring precursor |
| US4288625A (en) * | 1974-08-22 | 1981-09-08 | Phillips Petroleum Co. | Dinitriles, diamines, and polyamides |
| US4324738A (en) * | 1976-08-23 | 1982-04-13 | Phillips Petroleum Company | Dinitriles and their preparation |
| US4137267A (en) * | 1977-02-22 | 1979-01-30 | Texaco Inc. | Catalytic hydrogenation process |
| US4329498A (en) * | 1979-09-11 | 1982-05-11 | Allied Corporation | Preparation of 6-aminocaproic acid via muconic acid mononitrile |
| US4408037A (en) * | 1980-04-09 | 1983-10-04 | Phillips Petroleum Company | Polyamide from cycloaliphatic substituted nonane diamine |
| US4465824A (en) * | 1981-11-30 | 1984-08-14 | Phillips Petroleum Company | Polyamide resin from aralkylene diamine |
| US4495344A (en) * | 1981-11-30 | 1985-01-22 | Phillips Petroleum Company | Copolyamide from cycloaliphatic substituted nonane diamine |
| US4465822A (en) * | 1981-11-30 | 1984-08-14 | Phillips Petroleum Company | Polyamide from aralkylene diamine, dicarboxylic acid and tricarboxylic acid |
-
1968
- 1968-06-25 CH CH941168A patent/CH502993A/de not_active IP Right Cessation
- 1968-06-25 CS CS467868A patent/CS153464B2/cs unknown
- 1968-06-27 IL IL30267A patent/IL30267A/xx unknown
- 1968-06-28 FR FR1586868D patent/FR1586868A/fr not_active Expired
- 1968-06-28 GB GB31128/68A patent/GB1207756A/en not_active Expired
- 1968-06-28 BE BE717306D patent/BE717306A/xx unknown
- 1968-06-28 FI FI681863A patent/FI48723C/fi active
- 1968-06-28 SE SE08907/68A patent/SE360073B/xx unknown
- 1968-06-28 AT AT623068A patent/AT277964B/de not_active IP Right Cessation
- 1968-06-28 ES ES355603A patent/ES355603A1/es not_active Expired
- 1968-06-28 BR BR200229/68A patent/BR6800229D0/pt unknown
- 1968-06-28 NL NL6809168A patent/NL6809168A/xx not_active Application Discontinuation
- 1968-06-28 DK DK319468AA patent/DK119307B/da unknown
- 1968-06-29 NO NO2611/68A patent/NO125816B/no unknown
- 1968-07-01 US US743583A patent/US3632625A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI48723C (fi) | 1974-12-10 |
| FI48723B (xx) | 1974-09-02 |
| BE717306A (xx) | 1968-12-02 |
| FR1586868A (xx) | 1970-03-06 |
| BR6800229D0 (pt) | 1973-06-07 |
| CS153464B2 (xx) | 1974-02-25 |
| US3632625A (en) | 1972-01-04 |
| SE360073B (xx) | 1973-09-17 |
| AT277964B (de) | 1970-01-12 |
| CH502993A (de) | 1971-02-15 |
| IL30267A (en) | 1972-06-28 |
| ES355603A1 (es) | 1970-01-01 |
| IL30267A0 (en) | 1968-08-22 |
| GB1207756A (en) | 1970-10-07 |
| NL6809168A (xx) | 1968-12-31 |
| DE1618295A1 (de) | 1971-03-11 |
| DK119307B (da) | 1970-12-14 |
| DE1618295B2 (de) | 1975-11-06 |
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