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US5359094.Pdf |||||||||||||I|| US005359094A United States Patent 19 11 Patent Number: 5,359,094 Teles et al. 45) Date of Patent: Oct. 25, 1994 (54) PREPARATION OF GLYCERYL 3,379,693 4/1968 Hostettler et al. .................. 549/229 CARBONATE 4,231,937 1/1980 Kao et al. ............ ... 549/229 4,314,945 2/1982 McMullen et al. ... 549/229 75 Inventors: Joaquim H. Teles, Ludwigshafen; 4,344,881 8/1982 Strege et al. ..... ... 549/229 Norbert Rieber, Mannheim; 4,483,994 11/1984 Jacobson ...... ... 549/229 Wolfgang Harder, Weinheim, all of 4,658,041 4/1987 Renga .......... ... 549/229 Fed. Rep. of Germany 4,835,289 5/1989 Brindapke ... ... 549/229 73) Assignee: BASF Aktiengesellschaft, 5,091,543 2/1992 Grey .................... ... 549/229 Ludwigshafen, Fed. Rep. of 5, 18,818, 6/1992 Delledonine et al. ............... 549/229 Germany FOREIGN PATENT DOCUMENTS (21) Appl. No.: 99,142 2222488 11/1972 Fed. Rep. of Germany. 2265228 12/1976 Fed. Rep. of Germany . 22 Filed: Jul. 29, 1993 1382313 1/1975 United Kingdom . 30 Foreign Application Priority Data Primary Examiner-Cecilia Tsang Aug. 5, 1992 (DE Fed. Rep. of Germany ....... 4225870 Attorney, Agent, or Firm-Keil & Weinkauf 51 Int. Cl. ............................................ CO7D 317/36 (57) ABSTRACT 52 U.S. C. .................................... 549/228; 549/229; 549/230 A process for the preparation of glyceryl carbonate by 58) Field of Search ........................ 549/228, 229, 230 causing glycerol to react with carbon monoxide and oxygen in the presence of a Group Ib, Group IIb, or (56) References Cited Group VIIIb catalyst as per the Periodic Table attem U.S. PATENT DOCUMENTS peratures ranging from 0 to 180° C. 2,856,413 10/1958 Malkemas et al. .................. 549/228 3,153,051 10/1964 Kormendy et al. ................. 549/229 4 Claims, No Drawings 5,359,094 1. 2 dium, palladium, osmium, iridium and/or platinum and PREPARATION OF GLYCERYL CARBONATE preferably salts of the elements copper, silver, mercury, iron, cobalt and/or nickel and more preferably salts of The present invention relates to a process for the the elements copper and/or mercury. preparation of glyceryl carbonate by the reaction of Suitable salts are sulfates, chlorides, bromides and glycerol with carbon monoxide and oxygen in the pres trifluoroacetates and preferably chlorides, bromides ence of Group Ib, Group IIb, and Group VIIIb cata and trifluoroacetates. Suitable copper catalysts for use lysts as per the Periodic Table and the conversion in the process of the invention are generally simple thereof to glycidol at elevated temperatures over alkali copper salts such as copper halides, copper(I) sulfate, metal salts and/or alkaline earth metal salts. O copper (alkoxy)halides and copper(I) trifluoroacetate DE-A 2,222,488 and DE-A 2,265,228 describe pro and preferably copper(I) halides such as copper(I) chlo cesses for the preparation of ethylene carbonates from ride and copper(I) bromide and copper(I) sulfate and glycols using CO/O2 in the presence of Group Ib, copper(I) trifluoroacetate. Group IIb, and Group VIIIb catalysts. Suitable inert solvents are tertiary amines such as U.S. Pat. No. 2,856,413 describes the dissociation of 15 C3-C20tertiary amines, e.g., trimethylamine, pyridine, glyceryl carbonate to produce glycidol over phos quinoline, Cl-, 3-, and y-picolines and preferably pyri phates, pyrophosphates, chlorides, bromides, acetates, dine and y-picoline, nitriles such as acetonitrile, propio bicarbonates, and carbonates of alkali metals and alka nitrile and benzonitrile, nitro compounds such as nitro line earth metals. benzene and preferably benzonitrile or esters such as It is thus an object of the present invention to provide 20 C2-C20alkyl carboxylates, e.g., methyl acetate, ethyl a process which makes it possible to prepare glyceryl acetate, ethyl benzoate and preferably ethyl benzoate carbonate starting from glycerol and to find means for and lactones such as butyrolactone, ureas such as tetra the conversion thereof to glycidol. methyl urea and carbonates such as propylene carbon Accordingly, we have found a novel and improved ate. process for the preparation of glyceryl carbonate, 25 The conversion of the glyceryl carbonate to glycidol wherein glycerol is caused to react with carbon monox can be carried out at temperatures ranging from 100 to ide and oxygen in the presence of a Group Ib, IIb, or 300 C. and preferably from 125 to 275 C. and more VIIIb catalyst as per the Periodic Table attemperatures preferably from 210 to 250° C. and pressures of from ranging from 0 to 150° C. and the conversion thereof to 0.001 to 5 bar and preferably from 0.005 to 2 bar and glycidol by reaction at temperatures ranging from 80' 30 more preferably from 0.01 to 1 bar over alkali metal to 300 C. and pressures of from 0.001 to 5 bar over salts and/or alkaline earth metal salts, for example, in alkali metal salts and/or alkaline earth metal salts. distillation apparatus. The process of the invention may be carried out as Suitable salts of alkali metals and alkaline earth metals follows: are halides such as fluorides, chlorides, bromides, and The reaction can be started by feeding a gaseous 35 iodides, phosphates, monohydrogenphosphates, dihy mixture of carbon monoxide and oxygen into the reac drogen phosphates, pyrophosphates, sulfates, borates, tion mixture. The composition of the gas mixture can be acetates, carbonates and bicarbonates and preferably varied as desired within wide limits. Air can be used fluorides, iodides, and sulfates and more preferably instead of oxygen if desired, for example, or the gas fluorides, sulfates and borates. Specific examples mixture can be diluted, if desired, with an inert gas such thereof are: as nitrogen, argon or carbon dioxide. Generally speak lithium fluoride, sodium fluoride, potassium fluoride, ing, a CO:O2 molar ratio of from 100:1 to 0.5:1 and rubidium fluoride, cesium fluoride, beryllium fluo preferably from 50:1 to 1:1 and more preferably from ride, magnesium fluoride, calcium fluoride, stron 20:1 to 1.5:1 is used. tium fluoride, barium fluoride, lithium chloride, The reaction gases carbon monoxide and oxygen are 45 sodium chloride, potassium chloride, rubidium introduced into the liquid present in the reactor. To chloride, cesium chloride, beryllium chloride, mag ensure better intermixing and dispersion of the reaction nesium chloride, calcium chloride, strontium chlo gases in the reactor, it is preferred to use additional ride, barium chloride, lithium bromide, sodium mechanical stirring means. Suitable types of reactor are bromide, potassium bromide, rubidium bromide, stirred boilers or stirred autoclaves or bubble reactors 50 cesium bromide, beryllium bromide, magnesium which are advantageously capable of being heated and bromide, calcium bromide, strontium bromide, which may also be equipped with stirring means, if barium bromide, lithium iodide, sodium iodide, desired. potassium iodide, rubidium iodide, cesium iodide, The reaction can be advantageously carried out beryllium iodide, magnesium iodide, calcium io under elevated pressure, generally under a pressure of 55 dide, strontium iodide, barium iodide, lithium sul from 1 to 100 bar and preferably from 2 to 10 bar and fate, sodium sulfate, potassium sulfate, rubidium more preferably from 2.5 to 5 bar, optionally in the sulfate, cesium sulfate, beryllium sulfate, magne presence of an inert solvent. The reaction temperature sium sulfate, calcium sulfate, strontium sulfate, generally ranges from 0 to 180° C. and preferably from barium sulfate, lithium borate, sodium borate, po 80' to 150° C. and more preferably from 100 to 140° C. 60 tassium borate, rubidium borate, cesium borate, The reaction may be carried out continuously or beryllium borate, magnesium borate, calcium bo batchwise. In the preferred continuous mode of opera rate, strontium borate, barium borate, lithium ace tion, the reaction gases are usually used in excess and tate, sodium acetate, potassium acetate, rubidium the unconverted gas is circulated. acetate, cesium acetate, berylium acetate, magne Suitable catalysts are those containing elements in 65 sium acetate, calcium acetate, strontium acetate, Groups Ib, IIb, and VIIIb in the Periodic Table such as barium acetate, lithium carbonate, sodium carbon salts of the elements copper, silver, gold, zinc, cad ate, potassium carbonate, rubidium carbonate, ce mium, mercury, iron, cobalt, nickel, ruthenium, rho sium carbonate, beryllium carbonate, magnesium 5,359,094 3 4. carbonate, calcium carbonate, strontium carbonate, rupted and the effluent subjected to GC analysis. The barium carbonate, lithium phosphate, sodium phos conversion was 96%, and glyceryl carbonate was the phate, potassium phosphate, rubidium phosphate, only detectable product. Comparable results would be cesium phosphate, beryllium phosphate, magnesium possible using butyrolactone, tetramethyl urea, N,N- phosphate, calcium phosphate, strontium phos dimethylimidazol-2-one, or propylene carbonate as sol phate, and barium phosphate and preferably lith vent. ium fluoride, sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, beryllium fluo EXAMPLE 3 ride, magnesium fluoride, calcium fluoride, stron Preparation of Glycidol tium fluoride, barium fluoride, lithium iodide, so 10 dium iodide, potassium iodide, rubidium iodide, 15g of glyceryl carbonate and 1.5g of catalyst were cesium iodide, berylium iodide, magnesium iodide, placed in a small-size distillation unit and evacuated to calcium iodide, strontium iodide, barium
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