JP2000063333A - Production of aromatic carbonate ester - Google Patents

Abstract

PROBLEM TO BE SOLVED: To efficiently obtain an aromatic carbonate ester useful as an intermediate for synthesizing organic compounds from an aromatic hydroxy compound in one step and in a high yield by using a specific multi-nuclear metal complex compound and a redox catalyst as catalysts. SOLUTION: This method for producing an aromatic carbonate ester (for example, diphenyl carbonate) comprises reacting (A) an aromatic hydroxy compound (for example, phenol) with (B) carbon monoxide and (C) oxygen in the presence of (D) a multi-nuclear metal complex compound having plural Pd atoms as the metal center for example, dichlorobis[methylenebis(diphenylphosphine)]dipalladium] and (E) a redox catalyst [for example, Mn (2,2,6,6-tetramethyl-3,5-heptanedionate)3]. The component D is preferably used in an amount of 1×10-8 to 0. 5 mole as Pd per mole of the component A, and the component E is also preferably used in an amount of 0.1-100 moles per mole of the Pd of the component A.

Description

Description: BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an aromatic carbonate, and more particularly, to an intermediate for the synthesis of various organic compounds such as the synthesis of polycarbonate by a transesterification method. The present invention also relates to a method for efficiently producing an aromatic carbonate compound useful as a polycarbonate resin or the like from an aromatic hydroxy compound. [0002] Aromatic carbonate is a useful compound as a raw material for producing polycarbonate by a transesterification method or as an intermediate raw material for various organic syntheses. As a method for producing an aromatic carbonate, there is generally a method in which an aromatic hydroxy compound and phosgene are reacted in the presence of an alkali. In this method, toxic phosgene is used, and a stoichiometric amount of an alkali salt is used. There are some problems such as by-products. Therefore, many methods for producing aromatic carbonates without using phosgene have been proposed. As a general method for producing an aromatic carbonate, a method using an oxidative carbonylation reaction of reacting an aromatic hydroxy compound to be esterified with carbon monoxide and oxygen in the presence of a catalyst has been proposed. I have. In this method, typical catalysts to be used include a catalyst obtained by combining a palladium compound with a copper compound and a base (JP-B-61-8816, JP-B-61-43338), a palladium compound, and a cocatalyst. And catalysts comprising a quinone and a tetraalkylammonium halide or an alkali metal halide or an alkaline earth metal halide (JP-A-54-135743, JP-A-54-13).
5744, JP-A-2-104564, JP-A-2-142754, JP-A-6-9505, JP-A-6-172268, JP-A-6-172
269, JP-A-6-271506, JP-A-6-271509, JP-B-6-57678, JP-A-8-89810, JP-A-8-1930
No. 56 and U.S. Pat. No. 4,349,485), a catalyst comprising a palladium compound, an alkali metal or alkaline earth metal, an iodide or onium iodide compound, and a zeolite (JP-A-1-165551);
A catalyst comprising a palladium compound, an alkali metal halide or an alkaline earth metal halide, and activated carbon (JP-A-8-92168) has been proposed. In any case, the reaction rate of the oxidative carbonylation reaction is economical. In addition, it is not sufficient from a practical point of view, and it is necessary to use a large amount of a halogen-containing compound such as an ammonium bromide as a base. Further, a method using a palladium compound, a copper compound or a lanthanoid compound, 2-hydroxypyridine, and an aprotic polar solvent (JP-A-9-110804)
However, this method is economical in that the reaction rate is sufficient in terms of economy, but an aprotic polar solvent is essential and a solvent recovery step is required. On the other hand, as a production method using no carbonyl oxidation reaction, a production method using a transesterification reaction between dimethyl carbonate and an aromatic hydroxy compound (JP-A-9-176)
No. 094) has been proposed, but this method requires a process for producing dimethyl carbonate as a raw material, and is not necessarily an economical method. Furthermore, a production method by a carbon monoxide removal reaction from diphenyl oxalate (Japanese Patent Application Laid-open No.
In order to produce an aromatic carbonate, it is necessary to carry out a carbonylation reaction using carbon monoxide and methanol as raw materials and a transesterification reaction between dimethyl oxalate and an aromatic hydroxy compound. And the process becomes complicated and not economical. SUMMARY OF THE INVENTION [0004] The present invention solves the above-mentioned problems of the conventional method for producing an aromatic carbonate, and provides an aromatic hydroxy compound in one step and in a high yield. It is an object of the present invention to provide a method for efficiently producing a carbonate ester. [0005] In view of the above situation, the present inventors have solved the problems of the prior art and have been able to efficiently convert aromatic carbonates from aromatic hydroxy compounds in one step with high yield. We worked diligently to develop a good manufacturing method. As a result, they have found that the object of the present invention can be achieved by using (a) a polynuclear metal complex compound having a plurality of palladium atoms as a metal center and (b) a redox catalyst as catalysts. The present invention has been completed based on such findings. That is, in the present invention, an aromatic hydroxy compound, carbon monoxide and oxygen are reacted in the presence of a catalyst comprising (a) a polynuclear metal complex compound having a plurality of palladium compounds as metal centers and (b) a redox catalyst. It is intended to provide a method for producing an aromatic carbonate ester characterized by the above-mentioned. DETAILED DESCRIPTION OF THE INVENTION In the production method of the present invention, as the aromatic hydroxy compound, various conventionally known aromatic hydroxy compounds can be used and can be appropriately selected depending on the kind of the desired aromatic carbonate. For example, aromatic hydroxy compounds selected from aromatic monohydroxy compounds and aromatic dihydroxy compounds can be mentioned. As the aromatic monohydroxy compound, a compound represented by the following general formula (I): [Wherein, n represents an integer of 1 to 3;
Represents a hydrogen atom, a halogen atom (for example, chlorine, bromine, fluorine, iodine) or an alkyl group having 1 to 4 carbon atoms, an alkoxyl group, a cyano group or an ester group;
It may be in any of the m- or p-position. And an aromatic monohydroxy compound having 6 to 18 carbon atoms (monohydric phenol). Specific examples include phenols such as phenol, cresol, p-methylphenol, t-butylphenol (pt-butylphenol, etc.), 4-cumylphenol, methoxyphenol, chlorophenol, cyanophenol and the like. The aromatic dihydroxy compound is represented by the general formula (II) HO-Ar-OH (II) wherein Ar represents an arylene group. Aromatic dihydroxy compounds (dihydric phenols) represented by the formula: Specific examples include catechol, hydroquinone, resorcin and phenols which are substituted derivatives thereof. The aromatic dihydroxy compound is represented by the general formula (III): [Wherein, R is a hydrogen atom, a halogen atom (for example, chlorine, bromine, fluorine, iodine) or an alkyl group having 1 to 8 carbon atoms. A and b may each be an integer of 1 to 4. And Y is a single bond, an alkylene group having 1 to 8 carbon atoms, and 2 to 2 carbon atoms.
8 alkylidene group, a cycloalkylene group having 5 to 15 carbon atoms, a cycloalkylidene group having 5 to 15 carbon atoms or-
S—, —SO—, —SO ₂ —, —O—, —CO— bond or general formula (IV) [0013] The bond represented by ] It is a C12-C27 aromatic dihydroxy compound (dihydric phenol) represented by these. Here, there are various dihydric phenols represented by the above general formula (III).
-Bis (4-hydroxyphenyl) propane [bisphenol A] is preferred. The dihydric phenols other than bisphenol A include 1,1-bis (4-hydroxyphenyl) methane; 1,1-bis (4-hydroxyphenyl) ethane; hydroquinone; 4,4′-dihydroxydiphenyl; (Hydroxyphenyl) cycloalkane; bis (4-hydroxyphenyl) sulfide;
Bis (4-hydroxyphenyl) sulfone; bis (4-
Bis (4-hydroxyphenyl) ether; bis (4-hydroxyphenyl) ether; bis (4-hydroxyphenyl) compound other than bisphenol A such as bis (4-hydroxyphenyl) ketone or bis (3,5-dibromo-4-hydroxyphenyl) Propane; bis (3,5-
Halogenated bisphenols such as dichloro-4-hydroxyphenyl) propane; When these phenols have an alkyl group as a substituent,
As the alkyl group, an alkyl group having 1 to 6 carbon atoms, particularly an alkyl group having 1 to 4 carbon atoms is preferable. The carbon monoxide to be reacted with the aromatic hydroxy compound may be a simple substance, but may be diluted with an inert gas or a mixed gas with hydrogen. Further, oxygen to be reacted with the aromatic hydroxy compound is
Although it may be pure oxygen, it may be generally diluted with an inert gas, for example, an oxygen-containing gas such as air. The catalyst used in the production method of the present invention is composed of the component (a) and the component (b) as described above. As the polynuclear metal complex compound having a plurality of palladium atoms as a metal center, which is the component (a), any compound may be used as long as it is a metal complex compound having a plurality of palladium atoms in one polynuclear metal compound. Good. Specific examples of such polynuclear metal complex compounds include difluorobis [methylenebis (diphenylphosphine)] dipalladium, dichlorobis [methylenebis (diphenylphosphine)] dipalladium, dibromobis [methylenebis (diphenylphosphine)] dipalladium, diiodobis [methylenebis (Diphenylphosphine)] dipalladium, dinitrite bis [methylenebis (diphenylphosphine)] dipalladium, diazidobis [methylenebis (diphenylphosphine)] dipalladium, diisothiocyanatobis [methylenebis (diphenylphosphine)] dipalladium, dithiocy Anatobis [methylenebis (diphenylphosphine)] dipalladium, dicyanatobis [methylenebis (diphenylphosphine)] dipalladium, Chlorobis [methylenebis (diphenylarsine)] dipalladium, dibromobis [methylenebis (diphenylarsine)] dipalladium, diiodobis [methylenebis (diphenylarsine)] dipalladium, dinitrite bis [methylenebis (diphenylarsine)] dipalladium, diazidobis [methylenebis (diphenylarsine)] Dipalladium, diisothiocyanatobis [methylenebis (diphenylarsine)] dipalladium, dithiocyanatobis [methylenebis (diphenylarsine)] dipalladium, dicyanatobis [methylenebis (diphenylarsine)]
Dipalladium, dichlorobis [methylenebis (diphenylphosphine)] (μ-CO) dipalladium, dinitrite bis [methylenebis (diphenylphosphine)]
(Μ-CO) dipalladium, diazidobis [methylenebis (diphenylphosphine)] (μ-CO) dipalladium, dithiocyanatobis [methylenebis (diphenylphosphine)] (μ-CO) dipalladium, dicyanatobis [methylenebis (diphenylphosphine) ] (Μ-C
O) Dipalladium, dichlorobis [methylenebis (diphenylphosphine)] (μ-methylisocyanide) dipalladium, dinitrite bis [methylenebis (diphenylphosphine)] (μ-methylisocyanide) dipalladium, diazidobis [methylenebis (diphenylphosphine)] (Μ-methyl isocyanide) dipalladium,
Dithiocyanatobis [methylenebis (diphenylphosphine)] (μ-methylisocyanide) dipalladium, dicyanatobis [methylenebis (diphenylphosphine)] (μ-methylisocyanide) dipalladium, dichlorobis [methylenebis (diphenylphosphine)]
(Μ-phenylisocyanide) dipalladium, dinitrite bis [methylenebis (diphenylphosphine)]
(Μ-phenylisocyanide) dipalladium, diazidobis [methylenebis (diphenylphosphine)] (μ-
Phenylisocyanide) dipalladium, dithiocyanatobis [methylenebis (diphenylphosphine)] (μ-
Phenylisocyanide) dipalladium, dicyanatobis [methylenebis (diphenylphosphine)] (μ-phenylisocyanide) dipalladium, tetrakis (triphenylphosphine) tripalladiumbis (tetrafluoroborate), bis (triphenylphosphine) hexa (methylisocyanide) tri Palladium bis (hexafluorophosphate) and the like can be mentioned. In the present invention, the polynuclear metal complex compound of the component (a) may be used alone or in combination of two or more. Further, a compound having a plurality of or one palladium atom, which can be a precursor of these complex compounds, and a polynuclear metal complex compound as the component (a) may be used alone or in a physically mixed form. There may be. In addition, these polynuclear metal complex compounds may be appropriately combined with a ligand such as alkyl phosphine or aromatic phosphine, a phosphite, a phosphate, or a nitrile ligand such as acetonitrile, as long as the reaction is not hindered. Is also good. In the production method of the present invention, a redox catalyst is used as the component (b). The redox catalyst is selected from the group consisting of lanthanoid compounds, Group V transition metal compounds of the periodic table, Group VI transition metal compounds, Group VII transition metal compounds, iron compounds, cobalt compounds, nickel compounds and copper compounds. At least one kind is used, and these may be in any form of an organic complex, an organic salt and an inorganic salt. Specific examples include a cerium compound, a vanadium compound, a chromium compound, a manganese compound, an iron compound, a cobalt compound, a copper compound and the like, and preferably a cerium compound and a manganese compound. Particularly preferred redox catalysts include C
e (TMHD) ₄ , Mn (TMHD) ₃ , Ce (Tro
p) ₄ , Mn (Trop) ₃ [where TMHD represents 2,2,6,6-tetramethyl-3,5-heptanedionate ion and Trop represents tropolonate ion. And the like. In the catalyst used in the method of the present invention, an appropriate amount of a co-catalyst such as an onium halide compound can be added, if necessary, in addition to the components (a) and (b). Examples of the onium halide compound include a compound represented by the following formula (V). R ¹ R ² R ³ R ⁴ ZA (V) wherein Z is a nitrogen atom or a phosphorus atom;
Represents a halogen atom such as fluorine, chlorine, bromine and iodine.
R ^{1 to} R ⁴ are an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms, and specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group Octyl group, cyclohexyl group, phenyl group, tolyl group, xylyl group, naphthyl group and the like. R ^{1 to} R ⁴ may be the same or different. R ¹ and R ² , R ³ and R ⁴ are taken together to form a divalent group represented by — (CH ₂ ) _n —, wherein n is an integer of 2 to 7. May be. Further, bis (triphenylphosphoranylidene) ammonium halides other than the compound represented by the formula (V) can also be used as the onium halide compound.
Specific examples thereof include tetra-n-butylammonium bromide, tetraphenylphosphonium bromide, and bis (triphenylphosphoranylidene) ammonium bromide. In the production method of the present invention, the amount of the catalyst used is not particularly limited, and a normal amount of the catalyst may be used.
For example, the component (a) is used in an amount of 1 × 10 ^{−8 to} 0.5 mol, preferably 1 × 10 ⁻⁶ , as palladium, per mol of the aromatic hydroxy compound as a raw material.
It is 1 × 10 ^-2 mol. If the amount used is less than 1 × 10 ⁻⁸ , the reaction rate may be too low to be practical. On the other hand, 0.
If the amount exceeds 5 moles, the corresponding effect is not recognized and it is economically disadvantageous. The amount of component (b) used is
(A) 0.1 to 10 moles per mole of the palladium component
0 mol, preferably 0.5 to 50 mol. If the amount is less than 0.1 mol, the reaction rate may be low, which is not practical. If it exceeds 100 mol, the oxidative decomposition reaction of the aromatic carbonate produced by the component (b) proceeds, which is economically disadvantageous. It is. In the production method of the present invention, the reaction proceeds in the absence of a solvent or in a solvent. In general, it is economically advantageous to carry out the method of the present invention in the absence of a solvent, but if necessary for reasons such as the production process of an aromatic carbonate, the method may be carried out in a solvent. Here, examples of the solvent that can be used include aliphatic hydrocarbons, cycloaliphatic hydrocarbons, halogenated hydrocarbons, ethers, esters, nitrogen-containing solvents, sulfur-containing solvents, and the like, and a catalyst used in the production method of the present invention. Can be selected as appropriate depending on the type and combination of. In the present invention, the reaction temperature is not particularly limited, but is usually 50 to 200 ° C., preferably 70 to 1 ° C.
It is in the range of 50 ° C. If the temperature is higher than the above range, side reactions such as a decomposition reaction increase, and if the temperature is lower than the above range, the reaction rate is reduced and is not practical. Further, the reaction pressure is generally set to a pressurized state because a gaseous raw material such as carbon monoxide or oxygen is used.
× 10 ^{-2 to} 20 MPa, preferably 1 × 10 ^{-2 to} 10 M
Within the range of Pa, the oxygen partial pressure is 1 × 10 ^{−2 to} 10 MPa,
Preferably, it should be in the range of 1 × 10 ^{−2 to 5} MPa. In particular, the oxygen partial pressure is desirably adjusted so that the gas composition in the reaction system is out of the explosion range. When the reaction pressure is too low, the reaction speed is reduced. Expensive and economically disadvantageous. When using an inert gas, hydrogen, or the like, the partial pressure is not particularly limited, but may be appropriately used within a practical pressure range. The reaction system can be batch, semi-continuous or continuous. Here, the state of the reaction system is one of a liquid phase state, a mixed state of a liquid phase and a gas phase, and a mixed state of a liquid phase, a gas phase and a solid phase. Further, the state of the catalyst in the reaction system may be homogeneous or heterogeneous, and can be selected by appropriately selecting the catalyst. The raw material component and the catalyst may be diluted as necessary.As a diluent, an inert solvent such as a saturated hydrocarbon is used in a liquid phase, and nitrogen, argon, ethane, or a gaseous phase is used.
An inert gas such as propane is used. The production method of the present invention is to produce an aromatic carbonate by reacting an aromatic hydroxy compound, carbon monoxide and oxygen as raw materials in the presence of the above-mentioned specific catalyst. There are various aromatic carbonates (that is, carbonates of aromatic hydroxy compounds) which are the target products obtained by this reaction. For example, when an aromatic monohydroxy compound is used as a raw material, a compound represented by the general formula (VI): [Wherein, X and n are the same as those in the general formula (I). ] The aromatic carbonate represented by the formula: Further, when an aromatic dihydroxy compound is used as a raw material, a compound represented by the general formula (VII): [Wherein, R, a, b, and Y are the same as defined in the general formula (II)
Same as I). m depends on the molecular weight of the product and is an integer of 1 or more. In addition, the terminal structure of the molecule is not particularly defined. ] The aromatic carbonate represented by the formula: The present invention will now be described with reference to Examples and Comparative Examples.
As will be described in more detail, the present invention is not limited by these examples. The catalysts and reagents used in the following examples are commercially available products or those prepared according to the method described in the literature. Example 1 In a 30 ml autoclave, 3.02 g (32 mmol) of phenol and 6.3 m of dichlorobis [methylenebis (diphenylphosphine)] dipalladium were added.
g (6 micromol, 12 micromol as Pd),
Mn (2,2,6,6-tetramethyl-3,5-heptanedionate) ₃ was encapsulated in 14.5 mg (24 μmol). By pressurizing and depressurizing with carbon monoxide, the inside of the autoclave was replaced with carbon monoxide. Then 2
Carbon monoxide was pressurized so as to be 0.50 MPa in terms of 5 ° C., and air was further pressurized so that the whole pressure was 0.75 MPa. This was heated to 100 ° C. and reacted for 3 hours. After cooling and depressurizing, 20 ml of methylene chloride was added to obtain a dark brown homogeneous reaction solution. As a result of analyzing the reaction solutions by gas chromatography, 0.206 mmol of diphenyl carbonate (DPC) was produced. (Yield 1.28%). The reaction conditions of Example 1 were changed to the first
Table 2 shows the production amount, yield, and production rate of the product obtained in Example 1 in Table 2. In addition, the yield of DPC is shown by% on the basis of phenol.
The amount of DPC generated per unit palladium catalyst amount is calculated as TOF
(Mol-DPC / mol-Pd · time). Comparative Example 1 In Example 1, PdBr ₂ was used instead of dichlorobis [methylenebis (diphenylphosphine)] dipalladium.
The same operation as in Example 1 was carried out except that 3.2 mg (12 μmol) was used. Table 1 shows the reaction conditions.
Table 2 shows the amount, yield, and rate of production of PC. Comparative Example 2 In Comparative Example 1, (Ph ₃ P =) ₂ NBr [bis (triphenylphosphoranylidene) ammonium bromide]
The same operation as in Comparative Example 1 was carried out except that 0.15 g (0.24 mmol) was added. Table 1 shows the reaction conditions.
Table 2 shows the amount, yield, and rate of production of PC. Example 2 In Example 1, (Ph ₃ P =) ₂ NBr [bis (triphenylphosphoranylidene) ammonium bromide]
Example 1 was repeated, except that 0.15 g (0.24 mmol) was added. Table 1 shows the reaction conditions.
Table 2 shows the amount, yield, and rate of production of PC. Example 3 In Example 1, 6.8 mg (6 μmol, 12 μmol as Pd) of dibromobis [methylenebis (diphenylphosphine)] dipalladium was used instead of dichlorobis [methylenebis (diphenylphosphine)] dipalladium. Except for the above, the procedure was the same as in Example 1.
The reaction conditions are shown in Table 1, and the amount of DPC obtained, the yield,
The production rates are shown in Table 2. Example 4 In Example 2, 6.8 mg (6 μmol, 12 μmol as Pd) of dibromobis [methylenebis (diphenylphosphine)] dipalladium was used instead of dichlorobis [methylenebis (diphenylphosphine)] dipalladium. Other than that, it carried out similarly to Example 2.
The reaction conditions are shown in Table 1, and the amount of DPC obtained, the yield,
The production rates are shown in Table 2. Example 5 In Example 2, 6.4 mg (6 μmol, 12 μmol as Pd) of dicyanatobis [methylenebis (diphenylphosphine)] dipalladium was used in place of dichlorobis [methylenebis (diphenylphosphine)] dipalladium. Other than that, it carried out similarly to Example 2. Table 1 shows the reaction conditions, and Table 2 shows the amount, yield, and production rate of the obtained DPC. Example 6 In Example 2, 6.4 mg of dinitrite bis [methylenebis (diphenylphosphine)] dipalladium instead of dichlorobis [methylenebis (diphenylphosphine)] dipalladium (6 μmol, 12% as Pd)
(Micromolar), except that was used. Table 1 shows the reaction conditions, and the amount of DPC produced
Table 2 shows the yield and the production rate. Example 7 Instead of dichlorobis [methylenebis (diphenylphosphine) dipalladium in Example 2, tetrakis (triphenylphosphine) tripalladiumbis (tetrafluoroborate) 6.2 mg (4 μmol, Pd
Was carried out in the same manner as in Example 2 except that 12 μmol) was used. Table 1 shows the reaction conditions of Example 7 and Table 2 shows the amount, yield, and rate of production of DPC obtained in Example 7.
It is shown in the table. [Table 1] Pd ₂ (dpm) ₂ Cl ₂ : dichlorobis [methylenebis (diphenylphosphine)] dipalladium Pd ₂ (dpm) ₂ Br ₂ : dibromobis [methylenebis (diphenylphosphine)] dipalladium Pd ₂ (dpm) ₂ (NCO) _2: Jishianatobisu [methylenebis (diphenylphosphine)] dipalladium Pd ₂ (dpm) ₂ (NO _{2) 2:} di-nitrite-bis [methylenebis (diphenylphosphine)] dipalladium _{[Pd 3 (PPh 3) 4} ] (BF 4) ₂ : tetrakis (triphenylphosphine) tripalladium bis (tetrafluoroborate) TMHD: 2,2,6,6-tetramethyl-3,5-heptanedionate (Ph ₃ P =) ₂ NBr: bis (triphenylphospho) (Ranylidene) ammonium bromide 2] As described above, according to the production method of the present invention, aromatic carbonate esters useful as intermediates for synthesis of various organic compounds such as synthesis of polycarbonate by transesterification, and as polycarbonate resins and the like. The compound can be efficiently produced from the aromatic hydroxy compound in one step and in a high yield. Therefore, as a method for efficiently producing an aromatic carbonate compound, its utility value is particularly high in the field of polycarbonate production.

Continuation of front page    (72) Inventor Hirohisa Ishii             1-1, Higashi 1-chome, Tsukuba City, Ibaraki Prefecture             Material Engineering and Industrial Technology Research Institute             In the same research body (72) Inventor Mitsuru Ueda             1-1, Higashi 1-chome, Tsukuba City, Ibaraki Prefecture             Inside the Materials Technology Institute (72) Inventor Kazuhiko Takeuchi             1-1, Higashi 1-chome, Tsukuba City, Ibaraki Prefecture             Inside the Materials Technology Institute (72) Inventor Michihiko Asai             1-1, Higashi 1-chome, Tsukuba City, Ibaraki Prefecture             Inside the Materials Technology Institute F term (reference) 4H006 AA02 AC48 BA08 BA16 BA25                       BA43 BA44 BA45 BA48 BA51                       BA53 BE30 BE40 KA60                 4H039 CA66 CL00

Claims (1)

Claims: 1. A catalyst comprising: (a) a polynuclear metal complex compound having a plurality of aromatic hydroxy compounds, carbon monoxide and oxygen with a plurality of palladium atoms as metal centers, and (b) a redox catalyst. A method for producing an aromatic carbonate characterized by reacting in the presence.