DE1668815A1 - Verfahren zur Hydrodimerisation von Acrylsaeurederivaten - Google Patents
Verfahren zur Hydrodimerisation von AcrylsaeurederivatenInfo
- Publication number
- DE1668815A1 DE1668815A1 DE19681668815 DE1668815A DE1668815A1 DE 1668815 A1 DE1668815 A1 DE 1668815A1 DE 19681668815 DE19681668815 DE 19681668815 DE 1668815 A DE1668815 A DE 1668815A DE 1668815 A1 DE1668815 A1 DE 1668815A1
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- acid derivatives
- hydrodimerization
- hydrodimerized
- phenol
- 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 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 title claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 229910000497 Amalgam Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 5
- 229910001023 sodium amalgam Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- GBRNFMUKXFZFRJ-UHFFFAOYSA-N 2,2-dimethylhexanedinitrile Chemical compound N#CC(C)(C)CCCC#N GBRNFMUKXFZFRJ-UHFFFAOYSA-N 0.000 description 3
- 150000001278 adipic acid derivatives Chemical class 0.000 description 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 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
- 239000004952 Polyamide Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- XABJJJZIQNZSIM-UHFFFAOYSA-N azane;phenol Chemical compound [NH4+].[O-]C1=CC=CC=C1 XABJJJZIQNZSIM-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005734 heterodimerization reaction Methods 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/03—Mononitriles
-
- 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
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/04—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton containing two cyano groups bound to the carbon skeleton
-
- 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
- C07C255/06—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and unsaturated carbon skeleton
- C07C255/07—Mononitriles
- C07C255/08—Acrylonitrile; Methacrylonitrile
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2874667 | 1967-10-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1668815A1 true DE1668815A1 (de) | 1971-09-30 |
Family
ID=11044276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681668815 Pending DE1668815A1 (de) | 1967-10-11 | 1968-03-09 | Verfahren zur Hydrodimerisation von Acrylsaeurederivaten |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3547975A (en:Method) |
| AT (1) | AT278737B (en:Method) |
| BE (1) | BE711860A (en:Method) |
| BR (1) | BR6897641D0 (en:Method) |
| CS (1) | CS149416B4 (en:Method) |
| DE (1) | DE1668815A1 (en:Method) |
| GB (1) | GB1166414A (en:Method) |
| LU (1) | LU55674A1 (en:Method) |
| NL (1) | NL6803625A (en:Method) |
| NO (1) | NO124030B (en:Method) |
| SE (1) | SE352624B (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4299976A (en) * | 1979-09-28 | 1981-11-10 | Atlantic Richfield Company | Preparation of unsaturated diester precursor for sebacic acid |
| US5449807A (en) * | 1994-11-18 | 1995-09-12 | E. I. Du Pont De Nemours And Company | Catalyzed vapor phase hydrocyanation of diolefinic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3193574A (en) * | 1960-05-08 | 1965-07-06 | Katchalsky Aharon | Process for the preparation of adiponitrile by dimerization of acrylonitrile |
-
1968
- 1968-03-08 BE BE711860D patent/BE711860A/xx unknown
- 1968-03-08 GB GB01344/68A patent/GB1166414A/en not_active Expired
- 1968-03-09 DE DE19681668815 patent/DE1668815A1/de active Pending
- 1968-03-11 US US711852A patent/US3547975A/en not_active Expired - Lifetime
- 1968-03-13 LU LU55674D patent/LU55674A1/xx unknown
- 1968-03-13 SE SE03331/68A patent/SE352624B/xx unknown
- 1968-03-13 AT AT247368A patent/AT278737B/de not_active IP Right Cessation
- 1968-03-13 CS CS1963A patent/CS149416B4/cs unknown
- 1968-03-14 NO NO0980/68A patent/NO124030B/no unknown
- 1968-03-14 BR BR197641/68A patent/BR6897641D0/pt unknown
- 1968-03-14 NL NL6803625A patent/NL6803625A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3547975A (en) | 1970-12-15 |
| BE711860A (en:Method) | 1968-09-09 |
| NO124030B (en:Method) | 1972-02-21 |
| GB1166414A (en) | 1969-10-08 |
| LU55674A1 (en:Method) | 1968-12-05 |
| CS149416B4 (en:Method) | 1973-07-05 |
| SE352624B (en:Method) | 1973-01-08 |
| BR6897641D0 (pt) | 1973-01-11 |
| NL6803625A (en:Method) | 1969-04-15 |
| AT278737B (de) | 1970-02-10 |
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