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Method for Making Organic Carbonates

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Method for Making Organic Carbonates Office europeen des brevets (fi) Publication number : 0 507 546 A2 @ EUROPEAN PATENT APPLICATION @ Application number : 92302826.0 © Int. CI.5 : C07C 69/96, C07C 68/00 (22) Date of filing : 31.03.92 (30) Priority: 01.04.91 US 678411 @ Inventor: King, Joseph Anthony, Jr. 927 Vrooman Avenue Schenectady, New York 12309 (US) @ Date of publication of application : Inventor : Faler, Gary Ray 07.10.92 Bulletin 92/41 34 St. Stephens Lane Scotia, New York 12302 (US) Inventor : Krafft, Terry Edward (S) Designated Contracting States : 7456 Parklane Road DE ES FR GB IT NL Longmont, Colorado 80503 (US) © Applicant : GENERAL ELECTRIC COMPANY @ Representative : Pratt, Richard Wilson et al 1 River Road London Patent Operation G.E. Technical Schenectady, NY 12345 (US) Services Co. Inc. Essex House 12/13 Essex Street London WC2R 3AA (GB) (54) Method for making organic carbonates. (57) A method for making diphenyl carbonate free of color bodies is provided by reacting an organic hydroxy compound, such as phenol with carbon monoxide and oxygen in the pre- sence of an effective amount of a palladium catalyst, in the form of a palladium material which is used in combination with a quaternary ammonium salt, an inorganic cocatalyst, such as cobalt diacetate and an organic cocatalyst such as benzophenone or 1,10-phenanthroline. Recycling of catalyst values is also provided. CM < CO 10 h- o 10 LU Jouve, 18, rue Saint-Denis, 75001 PARIS 1 EP 0 507 546 A2 2 Reference to Copending Applications Although the aforementioned methods for making organic carbonates are of interest because they do Reference is made to copending applications of not require the use of phosgene which is a toxic and T.C.T. Chang, serial number 07/607,773, filed irritating gas, experience has shown that recycling of 10/31/90 which is a continuation of serial number 5 catalyst values and/or recovery of the organic carbo- 217,257, filed 7/11/88; serial number 07/609,122, nate free of color bodies is often not feasible. It is be- filed 11/5/90 which is a continuation of serial number lieved that the use of quinones such as 217,248, filed 7/11/88; and copending application se- hydroquinones causes catalyst deactivation. At- rial number 07/503,404, filed 4/2/90. tempts to recycle catalyst values free of impurities af- ro ter separation of organic carbonate is rendered Background of the Invention difficult because of the quinone breakdown during carbonylation. It would be desirable therefore to pro- The present invention relates to a method for vide a method for making organic carbonates without making organic carbonates by reacting an organic the use of phosgene, while permitting a recycling of hydroxy compound, such as phenol, with carbon 15 catalyst values, along with a simplified recovery of monoxide and oxygen in the presence of a palladium product free of color bodies. catalyst, a quaternary ammonium salt, and a cocatal- yst of a metallic material, such as a cobalt salt, and an Summary of the Invention organic material such as benzophenone. More par- ticularly, the present invention relates to a method for 20 The present invention is based on the discovery making diphenyl carbonate which provides a means that if in the palladium catalyzed oxidation of organic for recycling catalyst values and minimizes the pro- hydroxy compounds to organic carbonates, quinones, duction of color bodies resulting from the decomposi- such as benzoquinone or hydroquinone which tion of particular organic cocatalyst components. mediate oxidative-reductive electron transport, are re- J.E. Backvall, et al, show in their publication, 25 placed by ketones, such as benzophenone, or methyl Biomimetic Aerobic 1 ,4-Oxidation of 1,3-Dienes phenyl ketone, or aromatic polycyclic coal tar hyd- Catalyzed by Cobalt Tetraphenylporphyrin-Hydro- rocarbons, such as anthracene, that the carbonylation quinone-Palladium (II), An Example of Triple of organic hydroxy compound can be satisfactorily Catalysis, J. Am. Chem. Soc. 1987, 109, 4750-4752, achieved along with the recycling of catalyst values, the use of macrocyclic metal complexes employing p- 30 and the recovery of the organic carbonate substan- benzoquinone-hydroquinone as a catalytic electron tially free of color bodies. carrier in oxidation reactions and palladium catalyzed oxidations of conjugated dienes. There also is shown Statement of the Invention by T.C.T. Chang, copending application serial 07/607,773, a method for making organic carbonates 35 There is provided by the present invention, a utilizing an organic hydroxy compound with carbon method for making an organic carbonate which com- monoxide and oxygen and a catalyst in the form of prises, elemental or chemically combined palladium, cobalt, (1) contacting an organic hydroxy compound with tetraalkylammonium halide and at least one quinone, a mixture of carbon monoxide and oxygen at a an aromatic diol reduction product or mixture thereof. 40 temperature of from about 50°C to about 170°C In T.C.T. Chang copending application serial number and at a pressure from about 100 psi to about 217,248, filed 7/11/88, there is shown a method of 5000 psi in the presence of an amount of a pal- making organic carbonates utilizing a similar pro- ladium catalyst which is effective as a carbony- cedure as serial number 07/607,773 except that in lation catalyst comprising, place of chemically combined cobalt, there is utilized 45 (a) palladium material, divalent or trivalent manganese. (b) a quaternary ammonium salt, In copending application 07/503,404, filed 4/2/90, (c) a metallic cocatalyst material selected from there is shown a method for making organic carbo- a class of metals or compounds of metals con- nates employing an organic hydroxy compound, such sisting of cobalt, iron, cerium, manganese, as phenol, carbon monoxide and oxygen in the pre- so molybdenium, samarium, vanadium, chromium sence of an effective amount of a palladium catalyst and copper, and, and carbon dioxide as a desiccant. As taught in (d) an organic cocatalyst selected from a class 07/503,404, there can be used in combination with the of materials consisting of aromatic ketones, palladium catalyst, such as palladium(ll) acetate, a aliphatic ketones and aromatic polycyclic coal tetraalkylammonium halide and at least one quinone 55 tar hydrocarbons, and aromatic diol formed by the reduction of said (2) distilling the mixture of (1) at a temperature of quinone or a mixture thereof. In addition, a mangan- at least about 45°C and at a pressure of at least ese or cobalt cocatalyst also can be used. about 1 torr to effect the removal of the organic 2 3 EP 0 507 546 A2 4 hydroxy compound, for example, cobalt or manganese can be used at ab- (3) distilling the mixture of (2) at a temperature of out 0.1-5 g-atoms of metallic cocatalyst, per g-atom at least about 120°C and at a pressure of at least of palladian. The tetraalkylammonium halide can be about 1 torr to effect the recovery of organic car- used in the carbonylation mixture in an amount suffi- bonate free of color bodies, and 5 cient to provide about 0.01-100 moles of tetraalkylam- (4) recovering palladium cocatalyst system monium halide, per g-atom of palladium. The organic values from the residue of (3). cocatalyst, such as benzophenone, can be used in an The palladium material or catalyst useful in the amount sufficient to provide from 0.01-50 moles of practice of the present invention can be in elemental organic cocatalyst, per g-atom of palladium. form, or it can be employed as a palladium compound. 10 In addition to the aforementioned ingredients, Accordingly, palladium black, metallic or amorphous there can be utilized desiccants such as carbon palladium, or palladium compounds deposited on an dioxide which can be employed in an amount suffi- inert support such as carbon can be used as well as cient to provide from about 0.01 to about 50 moles of palladium compounds, for example, halides, nitrates, carbon dioxide, per mole of organo hydroxy com- carboxylates, and complexes of palladium involving 15 pound. In addition to carbon dioxide, molecular sieves such compounds-as carbon monoxide, amines, phos- also can be used as a drying agent. phines or olefins. The preferred palladium com- In the practice of the preferred form of the inven- pounds are palladium (II) salts of organic acids tion, the reactants, such as the organo hydroxy com- including carboxylates with C2_6 aliphatic acids. Pal- pound, carbon monoxide, and oxygen containing gas, ladium (II) acetate is particularly preferred. The tet- 20 for example, air or oxygen, and the catalyst compo- raalkylammonium halides which can be used are the nents, for example, the palladium catalyst material, chlorides and bromides and preferably the bromides. the quaternary ammonium salt, metallic cocatalyst The alkyl groups of the alkylammonium halides can be and organic cocatalyst along with or without a suitable primary and secondary alkyl and have from 1-8 car- desiccant, can be initially introduced into the reactor. bon atoms. Tetra-n-butylammonium bromide, tet- 25 Contact between the various components can be ef- ramethylammonium bromide and tetraethylammonium fected under high pressure and temperature as pre- bromide are particularly preferred. viously defined. The partial pressures of carbon The metallic cocatalyst materials which can be monoxide and oxygen can at least be about 50 psi to used include cobalt and manganese compounds. 3000 psi with a preferred partial pressure being in the These compounds can be divalent or trivalent, and in- 30 range of about 500 to 2000 and about 50 psi to 300 clude salts, such as halides and carboxylates and psi, respectively.
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