CH514536A - Verfahren zur reduktiven Dimerisation von a,B-ungesättigten Estern, Nitrilen oder Säureamiden - Google Patents
Verfahren zur reduktiven Dimerisation von a,B-ungesättigten Estern, Nitrilen oder SäureamidenInfo
- Publication number
- CH514536A CH514536A CH1094466A CH1094466A CH514536A CH 514536 A CH514536 A CH 514536A CH 1094466 A CH1094466 A CH 1094466A CH 1094466 A CH1094466 A CH 1094466A CH 514536 A CH514536 A CH 514536A
- Authority
- CH
- Switzerland
- Prior art keywords
- amide
- olefinically unsaturated
- nitrile
- organic
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000001408 amides Chemical class 0.000 title claims abstract description 7
- 150000002148 esters Chemical class 0.000 title claims abstract description 7
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 6
- 239000000178 monomer Substances 0.000 title claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 title claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 title claims abstract description 4
- 230000002829 reductive effect Effects 0.000 title abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 229910000497 Amalgam Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 33
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 6
- 238000006456 reductive dimerization reaction Methods 0.000 claims description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 239000012430 organic reaction media Substances 0.000 claims 2
- 239000001361 adipic acid Substances 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- 230000000447 dimerizing effect Effects 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 abstract 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 acrylonitrile nitrile nitrile Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
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 |
|---|---|---|---|
| GB3270265A GB1157444A (en) | 1965-07-30 | 1965-07-30 | Reductive Dimerisation of Unsaturated Esters and Nitriles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH514536A true CH514536A (de) | 1971-10-31 |
Family
ID=10342746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1094466A CH514536A (de) | 1965-07-30 | 1966-07-28 | Verfahren zur reduktiven Dimerisation von a,B-ungesättigten Estern, Nitrilen oder Säureamiden |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE684829A (enrdf_load_stackoverflow) |
| CH (1) | CH514536A (enrdf_load_stackoverflow) |
| DE (1) | DE1568860A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1157444A (enrdf_load_stackoverflow) |
| NL (1) | NL6610715A (enrdf_load_stackoverflow) |
| SE (1) | SE332628B (enrdf_load_stackoverflow) |
-
1965
- 1965-07-30 GB GB3270265A patent/GB1157444A/en not_active Expired
-
1966
- 1966-07-28 CH CH1094466A patent/CH514536A/de unknown
- 1966-07-28 SE SE1029666A patent/SE332628B/xx unknown
- 1966-07-29 DE DE19661568860 patent/DE1568860A1/de active Pending
- 1966-07-29 NL NL6610715A patent/NL6610715A/xx unknown
- 1966-07-29 BE BE684829D patent/BE684829A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE684829A (enrdf_load_stackoverflow) | 1967-01-30 |
| GB1157444A (en) | 1969-07-09 |
| SE332628B (enrdf_load_stackoverflow) | 1971-02-15 |
| NL6610715A (enrdf_load_stackoverflow) | 1967-01-31 |
| DE1568860A1 (de) | 1970-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0566974A1 (de) | Reinigung von fluorierten Carbonsäuren | |
| DE849109C (de) | Verfahren zur Herstellung aliphatischer Azoverbindungen | |
| DE69205713T2 (de) | Verfahren zur Herstellung gereinigter Alkansulfonsäuren. | |
| CH514536A (de) | Verfahren zur reduktiven Dimerisation von a,B-ungesättigten Estern, Nitrilen oder Säureamiden | |
| EP0143218A2 (de) | Verfahren zur Hydrolyse von 5-(beta-Methylmercapto-ethyl)-hydantoin | |
| DE1770827C3 (de) | Verfahren zur Herstellung von Cyanursäure | |
| DE2645544A1 (de) | Herstellung von alpha-amino-gamma- methylmerkaptobutyronitril | |
| DE2158562A1 (de) | Verfahren zur Herstellung von Gluta minsaure gamma methylester | |
| DE1232127B (de) | Verfahren zur Herstellung von gesaettigten aliphatischen oder aromatischen Nitrilen | |
| DE10307138A1 (de) | Verfahren zur Herstellung von Lagerstabilen Benzthiazolylsulfenamiden | |
| DE2009216C3 (de) | Verfahren zur Polymerisation von Vinylchlorid | |
| EP0275470A1 (de) | N-substituierte, Estergruppen enthaltende Acrylamide | |
| DE1173906B (de) | Verfahren zur Herstellung von 3-Aminopropan-sulfonsaeure-(1) | |
| DE1804833B2 (de) | Verfahren zur Herstellung von Methallylsulfonsäure und deren Salzen | |
| DE2453174A1 (de) | Verfahren zur herstellung von acetonin | |
| DE1296142B (de) | Verfahren zur Herstellung von ª‡-Aminobenzylpenicillin | |
| DE1668927C3 (de) | Verfahren zur Herstellung von Alkalisalzen von Aminopolycarbonsäuren | |
| AT222101B (de) | Verfahren zur Herstellung von neuen α-Nitro-ω-Lactamen | |
| DE2313548C3 (de) | N-N'-Dichlor-terephthalsäurediamid sowie ein Verfahren zur Herstellung von N,N'-Dichlor-terephthalsäurediamid und von N, N '-Dichlor-isophthalsäurediamid | |
| AT252892B (de) | Verfahren zur Herstellung von ω-Lactamen | |
| EP0043520B1 (de) | Verfahren zur Herstellung von 4-Amino-3-methyl-phenol | |
| DE3504073A1 (de) | Verfahren zur herstellung von 2-arylamino-4,6-dichlor-s-triazinen | |
| DE1944754C3 (de) | Verfahren zur kontinuierlichen Herstellung von gereinigtem alpha-Hydroxyisobuttersäurenitril | |
| DE2308941C3 (de) | Verfahren zur Herstellung von Oxamid | |
| AT258877B (de) | Verfahren zur Herstellung von Asparaginderivaten |