GB714659A - Improvements in the production of carboxylic acid esters - Google Patents

Improvements in the production of carboxylic acid esters

Info

Publication number
GB714659A
GB714659A GB22332/52A GB2233252A GB714659A GB 714659 A GB714659 A GB 714659A GB 22332/52 A GB22332/52 A GB 22332/52A GB 2233252 A GB2233252 A GB 2233252A GB 714659 A GB714659 A GB 714659A
Authority
GB
United Kingdom
Prior art keywords
nickel
cyanide
ammonium
carbon monoxide
esters
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
Application number
GB22332/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB714659A publication Critical patent/GB714659A/en
Expired legal-status Critical Current

Links

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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • 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
    • B01J27/24—Nitrogen compounds
    • B01J27/26—Cyanides
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/20—Carbonyls
    • 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
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/847—Nickel

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Carboxylic acid esters are produced by the interaction of olefinic hydrocarbons with carbon monoxide and aliphatic alcohols in a liquid medium in which is dissolved as catalyst a complex cobalt or nickel cyanide of the general formula [NX4]2[Me(CN)4] in which Me is cobalt or nickel and in which at least one, preferably three, of the four X's stands for an alkyl radical, the other(s) being hydrogen, or in the presence of a cobalt or nickel carbonyl in combination with alkali metal or ammonium cyanides. Suitable catalysts are, for example, triethyl ammonium nickel cyanide, trimethyl butyl ammonium nickel cyanide, tetraethyl ammonium nickel cyanide, triethyl butyl ammonium nickel cyanide and the corresponding cobalt cyanides. A mixture of the components of the complex cyanides may be used, e.g. a mixture of triethyl amine or any other trialkyl amine, hydrogen cyanide and nickel carbonyl which will form triethyl ammonium nickel cyanide. Suitable carbonyls for use in combination with the alkali metal or ammonium cyanide are for example, nickel carbonyl and triaryl phosphine substituted nickel carbonyls. Best results are obtained with catalysts in which the ratio between the numbers of cobalt or nickel ions and of the cyanide anions is at least 1 : 4. Preferred temperatures are between 80 DEG and 200 DEG C. and pressures above 50 atmospheres are used. The preferred olefin is ethylene used in an amount equal in volume to that of the carbon monoxide. In the examples: (a) a mixture of methanol, nickel carbonyl, potassium cyanide and water is treated with a mixture of ethylene and carbon monoxide to give mainly methyl propionate with some propionyl propionic acid methyl ester, diketo-pelargonic acid methyl ester, esters of higher polyketo-carboxylic acids and diethyl ketone; (b) a solution of nickel carbonyl and potassium cyanide in methyl propionate, methanol and water are treated with ethylene and carbon monoxide to give additional methyl propionate, propionyl propionic acid methyl ester, esters of higher polyketocarboxylic acids and a small amount of diethyl ketone; (c) potassium cyanide and nickel carbonate are dissolved in ethanol and water and the solution is treated with ethylene and carbon monoxide to give ethyl propionate, propionyl propionic acid ethyl ester and esters of higher polyketo-carboxylic acids; (d) a mixture of di-(triethyl-ammonium) nickel tetracyanide, [(C2H5)3NH]2.Ni(CN)4, methanol and water is treated with ethylene and carbon monoxide to give methyl propionate, propionyl propionic acid methyl ester, diketopelargonic acid methyl ester and esters of higher polyketo-carboxylic acids.
GB22332/52A 1951-09-08 1952-09-05 Improvements in the production of carboxylic acid esters Expired GB714659A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE714659X 1951-09-08

Publications (1)

Publication Number Publication Date
GB714659A true GB714659A (en) 1954-09-01

Family

ID=6625660

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22332/52A Expired GB714659A (en) 1951-09-08 1952-09-05 Improvements in the production of carboxylic acid esters

Country Status (1)

Country Link
GB (1) GB714659A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115870007A (en) * 2022-11-30 2023-03-31 东南大学 Composite catalyst for synthesizing propionate through ethylene carbonylation and using method thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115870007A (en) * 2022-11-30 2023-03-31 东南大学 Composite catalyst for synthesizing propionate through ethylene carbonylation and using method thereof
CN115870007B (en) * 2022-11-30 2024-03-15 东南大学 Composite catalyst for synthesizing propionate by ethylene carbonylation and application method thereof

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