GB885039A - 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
- GB885039A GB885039A GB10270/59A GB1027059A GB885039A GB 885039 A GB885039 A GB 885039A GB 10270/59 A GB10270/59 A GB 10270/59A GB 1027059 A GB1027059 A GB 1027059A GB 885039 A GB885039 A GB 885039A
- Authority
- GB
- United Kingdom
- Prior art keywords
- disulphide
- radical
- formula
- acid
- phosphorus
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Acrylic acid esters are obtained by reacting acetylene with carbon monoxide and an alcohol at elevated temperature and pressure in the presence as catalyst of a complex combination of a nickel halide and a disulphide of an organic sulphur-phosphorus-containing acid compound containing the disulphide radical <FORM:0885039/IV (b)/1> Specified types of disulphide compounds are those having the formula <FORM:0885039/IV (b)/2> the formula <FORM:0885039/IV (b)/3> and the formula <FORM:0885039/IV (b)/4> wherein R and R1 represent an unsubstituted or substituted alkyl radical containing up to 22 carbon atoms, an unsubstituted or substituted aryl radical or a trihydrocarbylsilanyl radical and Z is an oxygen atom or an amido (-NH or -NR11- radical wherein R11 is an alkyl radical containing up to 22 carbon atoms) or RZ and R1Z taken together can represent a cyclic dioxa nucleus of the formula <FORM:0885039/IV (b)/5> wherein the two oxygen atoms (Z) are connected to the phosphorus atom of the group >P(S)-S-and wherein the carbon atoms of the dioxa nucleus have their other valencies satisfied by hydrogen atoms or other radicals. Specified alcohols include ethanol, pentanol, 2-ethyl-hexanol, dodecanol, 3-ethyl-2-pentanol, and ethylene glycol monomethyl (or monoethyl) ether. Suitable reaction temperatures are from 90 DEG C. to 250 DEG C. and it is preferred to operate at pressures above 100 p.s.i.g., e.g. at from 400 p.s.i.g. to 500 p.s.i.g. The nickel halide and the phosphorus-containing disulphide are preferably used in equimolar proportions and the reaction can be carried out batchwise or in a continuous manner. Examples are given for the production of ethyl acrylate from acetylene, carbon monoxide, and ethanol using a complex combination of nickel bromide and the disulphide of either (a) O,O1-dicresyldithiophosphoric acid, (b) di-(2-ethylhexyl) dithiophosphoric acid, (c) 5,5-diethyl-2-mercapto-2-thiono-1,3,2-dioxaphosphorinane or (d) diphenyl dithiophosphinic acid, respectively, as catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US885039XA | 1958-04-01 | 1958-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB885039A true GB885039A (en) | 1961-12-20 |
Family
ID=22211754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10270/59A Expired GB885039A (en) | 1958-04-01 | 1959-03-25 | Improvements in and relating to the production of acrylic acid esters |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1229844A (en) |
| GB (1) | GB885039A (en) |
-
1959
- 1959-03-20 FR FR790000A patent/FR1229844A/en not_active Expired
- 1959-03-25 GB GB10270/59A patent/GB885039A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1229844A (en) | 1960-09-09 |
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