GB1063497A - Reductive dimerisation of olefinic compounds - Google Patents
Reductive dimerisation of olefinic compoundsInfo
- Publication number
- GB1063497A GB1063497A GB14325/65A GB1432565A GB1063497A GB 1063497 A GB1063497 A GB 1063497A GB 14325/65 A GB14325/65 A GB 14325/65A GB 1432565 A GB1432565 A GB 1432565A GB 1063497 A GB1063497 A GB 1063497A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amalgam
- acrylonitrile
- ester
- alkyl
- dimethyl
- 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
- 150000001875 compounds Chemical class 0.000 title 1
- 230000002829 reductive effect Effects 0.000 title 1
- 229910000497 Amalgam Inorganic materials 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 239000012429 reaction media Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- NYLFUQXGUXOFBY-UHFFFAOYSA-N 3,4-dimethylhexanedinitrile Chemical compound N#CCC(C)C(C)CC#N NYLFUQXGUXOFBY-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 abstract 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000008360 acrylonitriles Chemical class 0.000 abstract 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 abstract 1
- 239000011636 chromium(III) chloride Substances 0.000 abstract 1
- 235000007831 chromium(III) chloride Nutrition 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/44—Adipic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An a ,b -olefinically unsaturated nitrile or ester is reductively dimerized by bringing an alkali metal or alkaline earth metal amalgam into interaction with a reaction medium containing the nitrile or ester, a salt that provides alkylated cations in the reaction medium, and an agent such as water or an alcohol that can donate active hydrogen and co-operates with the amalgam to provide an amalgam reduction system. Suitable starting materials are acrylonitrile and alkyl - substituted acrylonitriles ("alkyl" having up to 4 carbon atoms and including alkenyl and alkynyl with the unsaturation not adjacent to the acrylonitrile double bond), and mono- and di-carboxylate esters. The salts used may be alkylated ammonium, phosphonium or sulphonium salts. Inorganic salts such as CrCl3 or Na2CrO4 may be added as promoters. Polar solvents, such as dioxane, acetone, dimethylformamide or ethylene glycol, and polymerization inhibitors, such as N1N-dimethyl p-nitrosoaniline, may be present. When using alkali metal amalgams the constant addition of an acid or CO2 is required. Ambient temperature is preferred. Examples prepare adiponitrile, 3,4-dimethyl adiponitrile and diethyl adipate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU43311/64A AU279319B2 (en) | 1964-04-16 | ||
| AU48630/64A AU292745B2 (en) | 1964-08-27 | Amalgam hydrodimerisation process of olefinic nitriles and esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1063497A true GB1063497A (en) | 1967-03-30 |
Family
ID=25626316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14325/65A Expired GB1063497A (en) | 1964-04-16 | 1965-04-05 | Reductive dimerisation of olefinic compounds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3489789A (en) |
| BE (1) | BE662661A (en) |
| CH (1) | CH504401A (en) |
| DE (1) | DE1543062B1 (en) |
| GB (1) | GB1063497A (en) |
| NL (1) | NL140514B (en) |
| SE (1) | SE329839B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1157443A (en) * | 1965-06-30 | 1969-07-09 | Ici Ltd | Reductive Dimerisation of Unsaturated Esters and Nitriles |
| US3855269A (en) * | 1972-07-27 | 1974-12-17 | Phillips Petroleum Co | Apparatus and method for separating tetraalkylammonium salt |
| US9678901B2 (en) | 2015-11-16 | 2017-06-13 | International Business Machines Corporation | Techniques for indicating a preferred virtual processor thread to service an interrupt in a data processing system |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3193480A (en) * | 1963-02-01 | 1965-07-06 | Monsanto Co | Adiponitrile process |
| FR1289071A (en) * | 1961-05-04 | 1962-03-30 | Process for preparing adiponitrile by dimerization of acrylonitrile | |
| US3140276A (en) * | 1961-07-11 | 1964-07-07 | Exxon Research Engineering Co | Continuous electrolytic polymerization process |
| BE631302A (en) * | 1962-04-20 | |||
| FR1325977A (en) * | 1962-05-23 | 1963-05-03 | Knapsack Ag | Process for the preparation of aliphatic dicarboxylic acid derivatives |
| US3245889A (en) * | 1963-02-25 | 1966-04-12 | Monsanto Co | Electrolytic method for preparing low weight polymers of acrylonitrile |
| FR1366081A (en) * | 1963-05-24 | 1964-07-10 | Rhone Poulenc Sa | Dicyano-2, 4 butene-1 |
| US3225083A (en) * | 1963-08-15 | 1965-12-21 | Shell Oil Co | Dimerization process of preparing 1,4-dicyano-1-butene from acrylonitrile |
| US3250690A (en) * | 1963-12-23 | 1966-05-10 | Monsanto Co | Electrolytic reductive coupling of cyano compounds |
| FR1472033A (en) * | 1965-03-18 | 1967-03-10 | Rhone Poulenc Sa | Acrylonitrile linear dimerization process |
-
0
- BE BE662661D patent/BE662661A/xx unknown
-
1965
- 1965-04-05 GB GB14325/65A patent/GB1063497A/en not_active Expired
- 1965-04-07 US US446430A patent/US3489789A/en not_active Expired - Lifetime
- 1965-04-13 SE SE04820/65A patent/SE329839B/xx unknown
- 1965-04-15 CH CH531865A patent/CH504401A/en not_active IP Right Cessation
- 1965-04-15 NL NL656504863A patent/NL140514B/en unknown
- 1965-04-17 DE DE19651543062 patent/DE1543062B1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US3489789A (en) | 1970-01-13 |
| BE662661A (en) | |
| CH504401A (en) | 1971-03-15 |
| SE329839B (en) | 1970-10-26 |
| NL6504863A (en) | 1965-10-18 |
| DE1543062B1 (en) | 1972-11-16 |
| NL140514B (en) | 1973-12-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ATE5734T1 (en) | ANTI-CORROSION AGENTS AND COMPOSITIONS CONTAINING THEM. | |
| GB1255408A (en) | Heat-absorbent hygroscopic brines | |
| GB987631A (en) | Improvements in photographic coating formulation | |
| ES444478A1 (en) | Process for the sequestration of oxygen dissolved in water and compositions useful for such purpose | |
| ES296135A1 (en) | Improvements in and relating to corrosion inhibitors | |
| ES471659A1 (en) | Foam extinguishing agent | |
| GB1063497A (en) | Reductive dimerisation of olefinic compounds | |
| DK153850C (en) | APPLICATION OF ALKYL MONOPHOSPHONIC ACIDS AS CORROSION INHIBITORS FOR ACID SOLUTIONS | |
| ES437541A1 (en) | Drift reducing agricultural compositions | |
| GB1092962A (en) | 3,5-dialkylhydantoins | |
| GB1435200A (en) | Fire-fighting foam compositions and method of fire-fighting | |
| ES362990A1 (en) | Improvements in or relating to liquid cutting compositions | |
| ES420665A1 (en) | 7alpha-cyano-17-hydroxy-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid ypsilon-lactone and related compounds | |
| GB596716A (en) | Improvements in and relating to adhesives | |
| GB1157446A (en) | Reductive Dimerisation of Organic Compounds | |
| ATE3055T1 (en) | ANTIFREEZE. | |
| GB1316034A (en) | Imidazole-ribosyl cyclophosphates | |
| US2085806A (en) | Embalming fluid | |
| GB1257270A (en) | ||
| GB841735A (en) | Improvements in herbicidal compositions | |
| GB1157444A (en) | Reductive Dimerisation of Unsaturated Esters and Nitriles | |
| GB998264A (en) | Herbicidal compositions | |
| ES309647A1 (en) | Procedure for obtaining a means to combat aquatic herbs. (Machine-translation by Google Translate, not legally binding) | |
| GB1033260A (en) | Stabilization of aqueous n,n-dialkylhydroxylamine solutions | |
| NL88445C (en) |