GB879052A - Improvements in and relating to the production of acrylic acid esters - Google Patents
Improvements in and relating to the production of acrylic acid estersInfo
- Publication number
- GB879052A GB879052A GB9377/60A GB937760A GB879052A GB 879052 A GB879052 A GB 879052A GB 9377/60 A GB9377/60 A GB 9377/60A GB 937760 A GB937760 A GB 937760A GB 879052 A GB879052 A GB 879052A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitroso
- methyl
- quinolinol
- conh2
- naphthol
- 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
- 125000005396 acrylic acid ester group Chemical group 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 4
- -1 nickel halide Chemical class 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 2
- YXAOOTNFFAQIPZ-UHFFFAOYSA-N 1-nitrosonaphthalen-2-ol Chemical compound C1=CC=CC2=C(N=O)C(O)=CC=C21 YXAOOTNFFAQIPZ-UHFFFAOYSA-N 0.000 abstract 2
- JHKKTXXMAQLGJB-UHFFFAOYSA-N 2-(methylamino)phenol Chemical compound CNC1=CC=CC=C1O JHKKTXXMAQLGJB-UHFFFAOYSA-N 0.000 abstract 2
- STOVYWBRBMYHPC-KAVGSWPWSA-N 2-[(E)-[(E)-(2-hydroxyphenyl)methylidenehydrazinylidene]methyl]phenol Chemical compound OC1=CC=CC=C1\C=N\N=C\C1=CC=CC=C1O STOVYWBRBMYHPC-KAVGSWPWSA-N 0.000 abstract 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 2
- ZVNOVIBCAIDQOE-UHFFFAOYSA-N 4-nitrosonaphthalen-1-ol Chemical class C1=CC=C2C(O)=CC=C(N=O)C2=C1 ZVNOVIBCAIDQOE-UHFFFAOYSA-N 0.000 abstract 2
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 abstract 2
- NMMQOSCYONGFGP-UHFFFAOYSA-N 6-methyl-1-nitrosonaphthalen-2-ol Chemical compound O=NC1=C(O)C=CC2=CC(C)=CC=C21 NMMQOSCYONGFGP-UHFFFAOYSA-N 0.000 abstract 2
- AIBOXZCUYYHFTM-UHFFFAOYSA-N 6-methylquinolin-8-ol Chemical compound N1=CC=CC2=CC(C)=CC(O)=C21 AIBOXZCUYYHFTM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 229910052759 nickel Inorganic materials 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- 229960003540 oxyquinoline Drugs 0.000 abstract 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract 2
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 abstract 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acrylic acid esters are produced from C2H2, CO and an alcohol in presence of a complex of a nickel halide and a N-containing hydroxyl compound of formula <FORM:0879052/IV (b)/1> <FORM:0879052/IV (b)/2> <FORM:0879052/IV (b)/3> <FORM:0879052/IV (b)/4> wherein R=H, or C1-6 alkyl, X=NO, NH2, CHNOH, CONH2 or a C1-6 alkyl substituted NH2 or CONH2. Specified such compounds are 2-, 3-and 4-aminophenols, 2-amino-4-ethyl and -6-butyl-phenols, p-nitrosophenol, 2-methylaminophenol, 2- and 4-nitroso-1-naphthols and 1-nitroso-2- naphthol, 6-methyl-1- nitroso-2-naphthol, salicylaldazine and 4 : 41-diethylsalicylaldazine, 8-quinolinol and 6-methyl-8-quinolinol, salicyl-aldoxime and -amide. Alcohols used in examples are ethanol and 2-ethylhexanol, those otherwise specified being isopropanol, t-butanol, pentanol, dodecanol and the mono methyl, ethyl and butyl ethers of ethylene glycol.ALSO:Acrylic acid esters are produced from C2H2, CO and an alcohol in presence of a complex of a nickel halide and a N-containing hydroxyl compound of formula I, II, III or IV <FORM:0879052/III/1> wherein R = H or C1-C6 alkyl, and X = NO, NH2, CHNOH, CONH2 or a C1-C6 alkyl-substituted NH2 or CONH2. Specified such compounds are 2-, 3- and 4-aminophenols, 2-amino-4-ethyl- and -6-butyl-phenols, p-nitrosophenol, 2-methylaminophenol, 2- and 4-nitroso-1-naphthols and 1-nitroso-2-naphthol, 6-methyl-1-nitroso-2-naphthol, salicylaldazine and 4,41-diethylsalicylaldazine, 8-quinolinol and 6-methyl-8-quinolinol, salicyl-aldoxine and -amide. Alcohols used in examples are ethanol and 2-ethylhexanol, those otherwise specified being isopropanol, t - butanol, pentanol, dodecanol and the mono methyl, ethyl and butyl ethers of ethylene glycol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US879052XA | 1959-03-23 | 1959-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB879052A true GB879052A (en) | 1961-10-04 |
Family
ID=22207954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9377/60A Expired GB879052A (en) | 1959-03-23 | 1960-03-17 | Improvements in and relating to the production of acrylic acid esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB879052A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1292648B (en) * | 1964-07-01 | 1969-04-17 | Wnii Nefte Khim Prozessow | Process for the production of pentene or heptic acid |
-
1960
- 1960-03-17 GB GB9377/60A patent/GB879052A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1292648B (en) * | 1964-07-01 | 1969-04-17 | Wnii Nefte Khim Prozessow | Process for the production of pentene or heptic acid |
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