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United States Patent Office Patented Mar 2,738,364 United States Patent Office Patented Mar. 13, 1956 2 examples of the type of catalyst, we refer to N-butyl - 2,738,364 pyridinium nickel bromide of the formula PRODUCTION OF ACRYLIC ACID ESTERs IC5H5N.C4H9)2(NiBral Walter Reppe and Walter Schweckendiek, Ludwigshafen (Rhine), and Herbert Friederich, Worms, Germany, as 5 or dimethyl phenyl ethyl ammonium nickel chloride of signors to Badische Anilin- & Soda-Fabrik Aktiengesel the formula (CH3)2. (CoHs). (C2H5)Ni2. (NiCl4). We schaft, Ludwigshafen am Rhine, Germany may also use salts containing in the molecule a tertiary amine in addition to an ammonium radical, e. g. a com No Drawing. Application May 17, 1952, pound of the composition Serial No. 288,534 O Claims priority, application Germany June 5, 1951 (C5H5N.C4H9). (C5H5N1.INiBral In the compounds listed above the pyridine radical 16 Claims. (Cl. 260-486) may be replaced by other heterocyclic nitrogen compounds or by other tertiary amines of the types referred to The present invention relates to the production of 5 above. The chlorine and bromine radicals may be re acrylic acid esters and, more particularly, to the synthesis placed by iodine or cyanide or rhodanide. of acrylic esters by the interaction of acetylene, carbon The novel catalysts may be used in combination with ofmonoxide carbonylation and alcohols catalysts. in the presence of a novel type complex tertiary phosphine nickel salts, e.g. with triphenyl It is known that acrylic acid and its functional deriva 20 phosphine nickel bromide (C6H5)3P)2.NiBr2 or with tives may be prepared by the interaction of acetylen and quaternary phosphonium compounds derived therefrom, carbon monoxide with compounds having a replaceable e.g. triphenyl methyl phosphonium nickel chloride hydrogen atom, such as water, alcohols, carboxylic acids, mercaptains, ammonia and amines. The carbon mon I(CoH5)3(CH3)P2. INiCl4]. oxide taking part in the carbonylation may be brought 25 We may also used mixed complex salts, containing simul into the reaction in the form of metal carbonyls. This taneously radicals of amines and phosphines. Such a type of carbonylation is called the stoichiometric method. compound is for example the triphenyl butyl phospho The process may also be carried out catalytically while nium pyridine nickel bromide of the formula using carbon monoxide as such. In this case a catalyst has to be present. It has already been proposed to use 30 complex triphenyl phosphine-nickel halide compounds as and the triphenyl butyl phosphine pyridinium nickel bro catalysts. (See Walter Reppe, “Neue Entwicklungen auf mide of the formula dem Gebiet der Chemie des. Acetylens und Kohlenoxyds,” Springer-Verlag, 1949.) - It is an object of our invention to improve the car 35 e. bonylation of acetylene to acrylic acid derivatives accord The complex nickel salts used as catalysts in our in ing to the catalytic method. A further object of our in vention may be prepared in the manner described in vention is to provide novel catalysts for this reaction. our copending application Ser. No. 286,802 and now These catalysts allow to carry out the carbonylation with abandoned "Complex Nitrogen-Containing Metal Salts.' better yields and under less energetic conditions than 40 This process consists in simultaneously or subsequently were hitherto necessary. heating together in the liquid phase the components form We have found, and this constitutes the object of our ing the various radicals of the complex salts. The salts invention, that such complex nickel compounds are very are generally well crystallized, stable compounds which efficient catalysts for the carbonylation of acetylene to are soluble in organic solvents, such as alcohols, esters, acrylic acid compounds as contain the nickel in complex 45 lactones, ethers and the like. They may be charged to combination with an organic ammonium compound con the reaction mixture in the form of their solutions in taining at most one hydrogen atom attached to the nitro such solvents, and they may be recovered from the re gen atom. action product in the form of such solutions. Conse Suitable catalysts of this type are available according quently, it is very simple to use the catalysts again and 50 again in the acrylic ester synthesis. to the processes described in our copending application It is also possible to produce the catalysts in situ which "Complex Nitrogen-Containing Metal Salts," Ser. No. means that we charge the reaction vessel to be used 286,802, filed May 8, 1952, and now abandoned. We in the carbonylation with the ingredients necessary for prefer to use as catalysts such compounds which are de forming the catalyst and producing it within the reac rived from heterocyclic tertiary amines, such as pyridine, 55 tion vessel. homologues of pyridine, and quinolines. We may also The starting materials for our invention are acetylene use catalysts derived from tertiary aliphatic, cyclo-ali and carbon monoxide. Among the alcohols we prefer phatic, araliphatic or aromatic amines, or amines having to use aliphatic saturated monovalent alcohols contain a substituent belonging to more than one of the above ing not more than 18 carbon atoms, such as ethanol, mentioned classes. 60 isobutanol, 2-ethyl hexanol, dodecanol, ethylene glycol The complex salts used as catalysts should contain at monomethyl or ethyl ether and the homologues of these least one of these organic bases in the form of an am compounds. monium radical. The ammonium radical may be tertiary, The reaction runs smoothly and successfully with the as it is in the case of ammonium compounds prepared aid of our catalysts at temperatures exceeding 80 C., preferably between 80° and 250 C. To facilitate the by the addition of a hydrogen halide to a tertiary amine. 65 reaction, we work under increased pressure, preferably The ammonium radical may, however, as well be de at pressures exceeding 5 atmospheres and, for safety rea rived from a quaternary ammonium compound as they sons, at pressures between 5 and 30 atmospheres. We are obtained by the addition of organic halogen com may use higher pressures, provided that the acetylene is pounds to tertiary amines, strongly diluted by other gases, for example when work The catalysts preferably contain the salt of nickel O ing with a carbon monoxide-acetylene mixture contain with a hydrogen halide or pseudo-halide. To list a few ing a substantial excess of carbon monoxide. The partial 2,788,864 3 4. pressure of acetylene under the reaction conditions should Example 4 not be lower than 5 atmospheres. To a mixture of 50 parts of butanol and 50 parts of We may carry out the reaction discontinuously in the ty-butyrolactone with 3 parts of a butylene-1.4-dipyri conventional high pressure autoclaves, lined with suit dinium nickel tetra chloride DC5H5N-CH2CH2-2NiCl4 able material. We may also carry out the reaction in a 5 (M. P.=260° C.) a mixture of equal parts of acetylene continuous manner according to the various methods and carbon monoxide under 30 atmospheres is pressed known in the art. In both cases we may apply the cata at 160° C. After 50 hours the weight has increased lysts in dissolved or suspended state or rigidly arranged. by 50 parts. The reaction mixture is then distilled In a continuous operation we may allow the reaction yielding 86 parts of 100 per cent of butyl acrylate. The liquid to flow downwards through a vertical high pres 0. distillation residue contains ?y-butyrolactone. When half sure vessel which is charged with a catalyst or filler of this is distilled off the catalyst precipitates in the bodies or similar installations so that the liquid trickles form of greenish-blue crystals which may be recovered over the catalyst or the filler bodies while the gas is and used again. led in direct or countercurrent to the liquid. We may We claim: also lead the liquid through such a vessel upwards to 5 1. In the manufacture of an acrylic acid ester by the gether with the gas and provide the catalyst in a dis interaction of acetylene with carbon monoxide and an solved or solid state so that it is continuously led through alcohol at elevated temperature and under increased the reaction zone together with the starting materials. pressure, the step which comprises carrying out the re The carbon monoxide and the acetylene may be used action in the presence of a compound containing in as circulating gas. 20 complex combination nickel, a quaternary ammonium Suitable solvents for the process are preferably the radical and a member selected from the group consist liquid starting materials themselves, for example the ing of halide, cyanide and rhodanide radicals. alcohols. We may use also other solvents, such as 2. In the manufacture of an acrylic acid ester by hydrocarbons, ethers, lactones or the reaction products, the interaction of acetylene with carbon monoxide and but the use of the alcohols is preferred. 2 5 an alcohol at elevated temperature and under increased The following examples will further illustrate how pressure, the step which comprises carrying out the our invention may be carried out. reaction in the presence of a complex nickel compound The parts are by weight. of the general formula Example 1 30 Al2. Nix4 An autoclave made from stainless steel is charged with wherein A is a quaternary ammonium radical and X 50 parts of methanol and 3 parts of a catalyst contain is selected from the group consisting of halide, cyanide ing 1 part of triphenyl butyl phosphonium bromide, 1 and rhodanide radicals. part of pyridinium butyl bromide and 2 parts of nickel 3. In the manufacture of an acrylic acid ester by bromide. After having added 3 parts of pyridine and the interaction of acetylene with carbon monoxide and replaced the air by nitrogen the autoclave is heated to an alcohol at elevated temperature and under increased 160 C., and a mixture of equal parts by volume of pressure, the step which comprises carrying out the re carbon monoxide and acetylene, having a total pressure action in the presence of a complex nickel compound of 30 atmospheres is pressed in.
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