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United States Patent (19) 11 Patent Number: 4,931,573 Wada Et Al

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United States Patent (19) 11 Patent Number: 4,931,573 Wada Et Al United States Patent (19) 11 Patent Number: 4,931,573 Wada et al. 45 Date of Patent: Jun. 5, 1990 54 METHOD FOR PRODUCING ALACTONE FOREIGN PATENT DOCUMENTS 75) Inventors: Keisuke Wada, Yokohama; Yoshinori 2195374 8/1987 Japan ................................... 549/325 Hara, Machida; Koushi Sasaki, Primary Examiner-Glennon H. Hollrah Kawasaki, all of Japan Assistant Examiner-Susan P. Treanor 73) Assignee: Mitsubishi Kasei Corporation, Attorney, Agent, or Firm-Oblon, Spivak, McClelland, Tokyo, Japan Maier & Neustadt 57 ABSTRACT 21 Appl. No.: 177,363 A method for producing a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or 22 Filed: Apr. 4, 1988 a dicarboxylic acid ester in the presence of a catalyst, wherein the hydrogenation reaction is conducted in the 30 Foreign Application Priority Data liquid phase in the presence of (1) ruthenium, (2) an Apr. 18, 1987 JP Japan .................................. 62-95682 organic phosphine and (3) a compound of a metal se lected from the group consisting of Groups IVA, VA 511 Int. Cli............................................ COTD 307/28 and IIIB in the Periodic Table. 52 U.S. C. .................................... 549/325; 549/326; According to the present invention, for the production 502/213 of a lactone by hydrogenating a dicarboxylic acid, a 58 Field of Search ................. 549/325, 326; 502/213 dicarboxylic acid anhydride and/or a dicarboxylic es ter, the reaction is conducted in a homogeneous liquid 56) References Cited phase reaction by using the ruthenium, organic phos U.S. PATENT DOCUMENTS phine and compound of a metal selected from the group 3,312,7i8 4/1967 Woskow ............................. 549/325 consisting of Groups IVA, VA and IIIB, of the present 3,957,827 5/1976 Lyons .................................. 549/325 invention as the catalyst, whereby the desired lactone 3,997,569 12/1976 Powell ... ... 549/273 product can be obtained at high selectivity under a mild 4,268,689 5/1981 Knifton ............................... 502/213 condition as compared with the conventional methods. 4,415,740 1 1/1983 Kaufman ............................. 549/325 4,620,017 10/1986 Drake................................. 549/325 20 Claims, No Drawings 4,931,573 1 2 METHOD FOR PRODUCING ALACTONE DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS FIELD OF THE INVENTION Now, the present invention will be described in de The present invention relates to a method for produc 5 tail. ing a lactone by hydrogenating a dicarboxylic acid, a The dicarboxylic acid, the dicarboxylic anhydride dicarboxylic acid anhydride and/or a dicarboxylic acid and/or a dicarboxylic acid ester used as a starting mate rial of the present invention, is a saturated or unsatu ester. rated dicarboxylic acid having from 3 to 7 carbon atoms DISCUSSION OF BACKGROUND 10 and/or its derivative. Specific examples of the dicarboxylic acid include A method for producing a lactone by hydrogenating succinic acid, fumaric acid, maleic acid, glutaric acid a dicarboxylic acid, dicarboxylic acid anhydride and/or and methylsuccinic acid. The dicarboxylic acid anhy a dicarboxylic acid ester, has been studied since long dride includes succinic anhydride, maleic anhydride, ago, and various catalysts have been found. 15 glutaric anhydride and methylsuccinic anhydride. As For example, many proposals have been made on a the dicarboxylic acid ester, an alkyl ester is preferred, process for producing a lactone by a fixed bed or liquid and particularly preferred is a dicarboxylic acid deriva phase or suspension phase hydrogenation reaction sys tive having 4 carbon atoms. For example, dimethyl tem by using e.g. a nickel-type catalyst (e.g. Japanese maleate, diethyl fumarate and di-n-butyl succinate, may Examined Patent Publication No. 6947/1968), a cobalt 20 be mentioned. type catalyst (e.g. Japanese Unexamined Patent Publi The catalyst used in the method of the present inven cation No. 95057/1976), a copper-chromium-type cata tion is a catalyst comprising (1) ruthenium, (2) an or lyst (e.g. Japanese Examined Patent Publication No. ganic phosphine and (3) a compound of a metal selected 20119/1963) and a copper-zine-type catalyst (e.g. Japa from the group consisting of Groups IVA, VA, and nese Examined Patent Publication No. 14463/1967). On 25 IIIB of the Periodic Table. the other hand, it is also known to produce a lactone by Here, the ruthenium may be used in the form of metal conducting the above-mentioned hydrogenation reac ruthenium or a ruthenium compound. As the ruthenium tion by using a ruthenium catalyst for a homogeneous compound, an oxide, hydroxide, inorganic acid salt, system. For example, U.S. Pat. No. 3,957,827 discloses a organic acid salt or complex compound of ruthenium hydrogenation reaction under a condition of from 40 to 30 may be used. Specifically, there may be mentioned 400 psi by using a catalyst of RuX(PRR2R3 type. ruthenium dioxide, ruthenium tetraoxide, ruthenium U.S. Pat. No. 4,485,246 discloses that a hydrogenation dihydroxide, ruthenium chloride, ruthenium bromide, reaction by means of a similar catalyst is conducted in ruthenium iodide, ruthenium nitrate, ruthenium acetate, the presence of an organic amine. tris(acetylacetone)ruthenium, sodium hexachlororuthe However, such conventional methods wherein the 35 nate, dipotassium tetracarbonylruthenate, pentacar nickel-type catalyst, the cobalt-type catalyst, the cop bonylruthenium, cyclopentadienyldicarbonylru per-chromium-type catalyst and the copper-zinc-type thenium, dibromotricarbonylruthenium, chlorotris(tri catalyst was used, all had a problem that it was neces phenylphosphine)hydridoruthenium, bis(tri-n-butyl sary to employ a severe condition of few tens atm. or phosphine)tricarbonylruthenium, dodecacarbonyltriru higher. On the other hand, the conventional method thenium, tetrahydridedecacarbonyltetraruthenium, wherein a ruthenium catalyst for a homogeneous system dicesium octadecacarbonylhexaruthenate, tetraphenyl was used, had not only a drawback that the catalytic phosphonium, undecacarbonylhydridetriruthenate. activity was slightly low, but also fatal problems that Such metal ruthenium of ruthenium compound is the catalytically useful life was extremely short, and the used in an amount such that the concentration in the reactor was likely to be corroded by the use of halogen, 45 reaction solution will be 0.0001 to 100 mol, preferably although the method has a feature that the hydrogena from 0.001 to 10 mol, as ruthenium in one liter of the tion reaction proceeds under a relatively mild condi reaction solution. tion. In the method of the present invention, it is necessary SUMMARY OF THE INVENTION to use the organic phosphine together with the ruthe 50 nium. The organic phosphine is considered to contrib It is an object of the present invention to overcome ute to the control of the electron state of ruthenium of the above-mentioned conventional problems and to the the stabilization of the activity of ruthenium. Spe provide a method for producing a lactone whereby a cific examples of such an organic phosphine include a dicarboxylic acid, a dicarboxylic acid anhydride and/or trialkylphosphine such as tri-n-butylphosphine or di a dicarboxylic acid ester can be hydrogenated industri 55 methyl-n-octylphosphine, a tricycloalkylphosphine ally more advantageously than ever. such astricyclohexylphosphine, a triarylphosphine such The present inventors have conducted extensive re as triphenylphosphine, an alkylarylphoshine such as search to accomplish the above object, and as a result, dimethylphenylphosphine, and a polyfunctional phos have found that in a method for producing a lactone by phine such as 1,2-bis(diphenylphosphino)ethane. hydrogenating a dicarboxylic acid, a dicarboxylic acid Such as organic phosphine is used in an amount anhydride and/or a dicarboxylic acid ester, if a catalyst within a range of from 0.1 to 1,000 mol, preferably from comprising (1) ruthenium, (2) an organic phosphine and 1 to 100 mol, per mol of ruthenium. The organic phos (3) a compound of a metal selected from the group phine may be supplied to the reaction system by itself or consisting of Groups IVA, VA, and IIIB, is used as the in the form of a composite with ruthenium. catalyst, not only the catalytic activity for hydrogena 65 By using a compound of a metal selected from the tion increases, but also the stability in the activity of the group consisting of Groups IVA, VA and IIIB of the catalyst can be improved. The present invention has Periodic Table as an additional accelerator for the ru been accomplished on the basis of this discovery. thenium constituting the main catalyst for the hydroge 4,931,573 3 4. nation reaction of the present invention, it is possible to thallium, trimethyl thallium, thallium hydroxide, thal have the hydrogenation reaction proceeded under a lium carbonate, thallium acetate, methylthallium diace relatively mild condition by utilizing the merits of the tate, triethoxy thallium, butoxydimethyl thallium, die ruthenium as the main component, and it is also possible thylaminodimethyl thallium or dimethyl thallium ace to improve the catalytic activity for hydrogenation and tylacetonate. Such a metal compound is used in an to improve the stability of the activity and the selectiv amount within a range of from 0.01 to 1000 mols, prefer ity for the desired product. ably from 0.1 to 100 mols, more preferably from 0.5 to The metal selected from the group consisting of 20 mols, per mol of ruthenium in the main catalyst. Groups
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