JPH11171840A - Production of aromatic carbonic ester - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound in high yield through a simple process by reaction between an aromatic hydroxy compound, carbon monoxide and oxygen in the presence of a specific catalyst. SOLUTION: This compound is obtained by reaction between an aromatic hydroxy compound [pref. 2,2-bis(4-hydroxyphenyl)propane (bisphenel A) or the like], carbon monoxide and oxygen in the presence of a catalyst composed of (A) a polyuclear metal complex compound with a Lewis acidity-manifesting atom and palladium atom as the metallic center and (B) a redox catalyst; wherein the component A is e.g. bis(disphenylphosphinomethane) (trichlorotin) dipalladium chloride, while the component B is pref. Mn(tropolonato ion)3 or the like; and it is preferable that the molar ratios: A/aromatic hydroxy compound and B/A are 10-6 to 10-2 on a pd basis and 0.5-50 on a pd basis, respectively.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a method for producing an aromatic carbonate. More specifically, the present invention provides an aromatic hydroxy ester useful as a raw material for producing a polycarbonate by a transesterification reaction, an intermediate raw material for various organic syntheses, and the like as a polycarbonate resin by using a specific catalyst to obtain an aromatic hydroxy ester. The present invention relates to a method for efficiently producing a compound.

[0002]

2. Description of the Related Art Aromatic carbonates are compounds useful as raw materials for producing polycarbonate by transesterification, as intermediate materials for various organic syntheses, and as polycarbonate resins. As a general method for producing the aromatic carbonate, there is a method in which an aromatic hydroxy compound is reacted with phosgene in the presence of an alkali. There is a problem that a stoichiometric amount of an alkali salt is by-produced. Therefore, many methods for producing aromatic carbonates without using phosgene have been proposed.

As a general method for producing aromatic carbonates without using phosgene, there is a method using an oxidative carbonylation reaction in which a corresponding aromatic hydroxy compound is reacted with carbon monoxide and oxygen in the presence of a catalyst. Are known. Representative catalysts used in this reaction include, for example, a system in which a palladium compound and a copper compound are combined with a base (JP-B-61-8816, JP-B-61-1986).
No. 43338), a method using quinones and a tetraalkylammonium halide or an alkali metal halide or an alkaline earth metal halide in addition to a palladium compound and a cocatalyst (Japanese Patent Application Laid-Open Nos. 54-135743 and 54-135). JP-A-135744, JP-A-2-104564
JP, JP-A-2-142754, JP-A-6-9
505, JP-A-6-172268, JP-A-6-172269, JP-A-6-271506, JP-A-6-271509, JP-A-6-576
No. 78, JP-A-8-89810, JP-A-8-98810
No. 193056 and U.S. Pat. No. 4,349,485), a method using a catalyst comprising a palladium compound, an alkali metal or alkaline earth metal, an iodide or onium iodide compound, and a zeolite (JP-A-1-165).
551), a method using a catalyst comprising a palladium compound, an alkali metal halide or an alkaline earth metal halide, and activated carbon (Japanese Patent Application Laid-Open No. 8-92168).

[0004] However, all of these methods are not sufficiently economical because the reaction rate of the oxidative carbonylation reaction is not sufficiently high, and require the use of a large amount of a halogen-containing compound such as an ammonium bromide salt as a base. There are also problems such as corrosion of the reactor and loss of raw materials due to halogenation of the aromatic hydroxy compound. In addition, a method has been proposed in which a palladium compound, a copper compound or a lanthanoid compound, 2-hydroxypyridine, and an aprotic polar solvent are combined (Japanese Patent Application Laid-Open No. Hei 9-110804).
However, this method does not require a halogen-containing compound, but requires an aprotic polar solvent, and requires a solvent recovery step, which is not economical.

On the other hand, as a production method not using an oxidative carbonylation reaction, for example, a production method by a transesterification reaction of dimethyl carbonate with an aromatic hydroxy compound (JP-A-9-176094) has been proposed. A process for producing dimethyl carbonate, which is a raw material, is required, and is not necessarily an economical method. Further, a production method by a carbon monoxide removal reaction from diphenyl oxalate (Japanese Patent Laid-Open No.
In this method, an carbonylation reaction using carbon monoxide and methanol as raw materials and an ester of dimethyl oxalate with an aromatic hydroxy compound are used to produce an aromatic carbonate. It is necessary to carry out an exchange reaction, which requires complicated steps, and is not economical.

[0006]

DISCLOSURE OF THE INVENTION The present invention overcomes the drawbacks of the conventional method for producing an aromatic carbonate and provides an aromatic carbonate from an aromatic hydroxy compound in a simple process with a high yield. It is intended to provide an industrially advantageous method that can be manufactured.

[0007]

Means for Solving the Problems The present inventors have made intensive studies to achieve the above object, and as a result, have found that a specific catalyst system is used to react an aromatic hydroxy compound, carbon monoxide and oxygen. As a result, it has been found that an aromatic carbonate can be obtained in one step with a high yield, and the object can be achieved. The present invention has been completed based on such findings. That is, the present invention provides an aromatic hydroxy compound, a (b) redox catalyst in the presence of (a) a polynuclear metal complex compound having at least one atom exhibiting Lewis acidity and a palladium atom as a metal center, and (b) a redox catalyst. An object of the present invention is to provide a method for producing an aromatic carbonate characterized by reacting carbon oxide and oxygen.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION In the method of the present invention, there are various kinds of aromatic hydroxy compounds used as raw materials, and they may be appropriately selected according to the kind of a desired aromatic carbonate. As the aromatic hydroxy compound, an aromatic monohydroxy compound and an aromatic dihydroxy compound are usually used. Examples of the aromatic monohydroxy compound include compounds represented by general formula (I)

[0009]

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(Wherein X represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a cyano group or an ester group, and n represents an integer of 1 to 3) ) Can be exemplified by an aromatic monohydroxy compound having 6 to 18 carbon atoms. Formula (I)
In the above, the halogen atom in X is a chlorine atom, a bromine atom, a fluorine atom and an iodine atom, and the alkyl group having 1 to 4 carbon atoms includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group and an n- Butyl group, isobutyl group,
Examples include a sec-butyl group and a tert-butyl group. Examples of the alkoxyl group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group. When there are a plurality of Xs, each X may be the same or different, and the bonding position of X is not particularly limited.

Examples of the aromatic monohydroxy compound represented by the general formula (I) include phenol, cresol, p-methylphenol, t-butylphenol (p-butylphenol).
-T-butylphenol), phenols such as 4-cumylphenol, methoxyphenol, chlorophenol and cyanophenol. On the other hand, examples of the aromatic dihydroxy compound include, for example, general formula (II) HO—Ar—OH (II) (wherein Ar is an arylene which may have a suitable substituent introduced on an aromatic ring) Which represents a group). Examples of the arylene group represented by Ar in the general formula (II) include a phenylene group and a naphthylene group. Suitable substituents that may be introduced on the aromatic ring include, for example, a halogen atom, Examples thereof include lower alkyl groups, alkoxyl groups, cyano groups, and ester groups. Examples of the aromatic dydoxy compound represented by the general formula (II) include catechol, hydroquinone, resorcin and substituted derivatives thereof. Further, as the aromatic dihydroxy compound, a compound represented by the general formula (III)

[0012]

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A compound having 12 to 27 carbon atoms represented by the following formula: In the above general formula (III), R ¹ and R ² each represent a hydrogen atom, a halogen atom of fluorine, chlorine, bromine or iodine or an alkyl group having 1 to 8 carbon atoms, for example, a methyl group, an ethyl group, an n-propyl group. Isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl and the like. R ¹ and R ² may be the same or different.
The plurality of R ¹ is when R ¹ are a plurality may be the same or different, a plurality of R ² if R ² there are a plurality, may be the same or different. a and b are each 1 to
4 is an integer. And Y is a single bond, an alkylene group having 1 to 8 carbon atoms, an alkylidene group having 2 to 8 carbon atoms, 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 formula (IV)

[0014]

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[0015] The bond represented by Examples of the alkylene group having 1 to 8 carbon atoms and the alkylidene group having 2 to 8 carbon atoms include:
Examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, an ethylidene group, an isopropylidene group and the like. As a cycloalkylene group having 5 to 15 carbon atoms and a cycloalkylidene group having 5 to 15 carbon atoms, Examples thereof include a cyclopentylene group, a cyclohexylene group, a cyclopentylidene group, and a cyclohexylidene group. Examples of the aromatic dihydroxy compound represented by the general formula (III) include various compounds, and 2,2-bis (4-hydroxyphenyl) propane [bisphenol A] is particularly preferable. As aromatic dihydroxy compounds other than bisphenol A, 1,1-
Bis (4-hydroxyphenyl) methane; 1,1-bis (4-hydroxyphenyl) ethane; 4,4-dihydroxydiphenyl; bis (4-hydroxyphenyl) cycloalkane; bis (4-hydroxyphenyl) sulfide; bis ( 4- (hydroxyphenyl) sulfone; bis (4-hydroxyphenyl) sulfoxide; bis (4-
Hydroxyphenyl) ether; bis (4-hydroxyphenyl) ketone, or 2,2-bis (3,5
-Dibromo-4-hydroxyphenyl) propane; 2,
Halogenated bisphenols such as 2-bis (3,5-dichloro-4-hydroxyphenyl) propane; When these phenols have an alkyl group on the aromatic ring as a substituent, an alkyl group having 1 to 6 carbon atoms, particularly an alkyl group having 1 to 4 carbon atoms is preferable.

In the method of the present invention, the carbon monoxide to be reacted with the aromatic hydroxy compound may be diluted with an inert gas or may be a mixed gas with hydrogen. The oxygen to be reacted with the aromatic hydroxy compound may be pure oxygen. Generally, oxygen diluted with an inert gas, for example, an oxygen-containing gas such as air is preferably used.

On the other hand, the catalyst used in the method of the present invention comprises the components (a) and (b) as described above. Here, as the polynuclear metal complex compound having at least one of the Lewis acid-expressing atoms and the palladium atom as the metal center, which is the component (a), one polynuclear metal complex compound contains one of the Lewis acid-expressing atoms. Any compound having at least one compound and a palladium atom may be used. Specifically, bis (diphenylphosphinomethane) (trichlorotin) dipalladium chloride, bis (diphenylphosphinomethane) bis (trichlorotin) dipalladium, bis (diphenylphosphinomethane) (trichlorotitanium) dipalladium chloride, Bis (diphenylphosphinomethane) bis (trichlorotitanium) dipalladium, bis (diphenylphosphinomethane) (dichloroiron)
Dipalladium chloride, bis (diphenylphosphinomethane) bis (dichloroiron) dipalladium, bis (diphenylphosphinomethane) (trichlorotin)
(Trichlorotitanium) dipalladium, bis (diphenylphosphinomethane) (trichlorotin) (dichloroiron) dipalladium, bis (diphenylphosphinomethane) (trichlorotitanium) (dichloroiron) dipalladium, π-allyl (triphenylphosphine) ) (Trichlorotin) palladium, π-allyl (triphenylphosphine) (trichlorotitanium) palladium, π-allyl (triphenylphosphine) (dichloroiron) palladium, bis (trichlorotin) palladium, bis (trichlorotitanium) palladium, bis (Dichloroiron) palladium and the like. Further, at least one compound having a Lewis acid and a compound having a palladium atom, which are precursors for synthesizing these polynuclear metal complex compounds, may be used alone and physically mixed. These polynuclear metal complex compounds may be appropriately combined with a ligand such as an alkyl phosphine and an aromatic phosphine, a phosphite or a phosphate, or a nitrile ligand such as acetonitrile, as long as the reaction is not hindered. You may.

The polynuclear metal complex compound of component (a) may be used alone or in combination of two or more. The redox catalyst as the component (b) includes:
A compound having the ability to regenerate component (a), which is reduced as the reaction proceeds, and having the property that component (b) itself reduced as component (a) is regenerated with oxygen or an oxygen-containing gas Is appropriately selected from the following. Such a compound may be in any form of an organic complex, an organic salt and an inorganic salt. Specifically, cerium compounds, vanadium compounds, chromium compounds, manganese compounds, iron compounds,
Examples thereof include a cobalt compound and a copper compound. Among these, a cerium compound and a manganese compound are preferred, and a particularly preferred redox catalyst is Ce (TMHD)
₄ , Mn (TMHD) ₃ , Ce (Trop) ₄ , Mn
(Trop) ₃ [where, Trop is tropolonate ion, TMHD is 2,2,6,6-tetramethyl-3,
5 shows the 5-heptane dionate ion. And the like. The redox catalyst of the component (b) may be used alone or in combination of two or more.

The amount of the catalyst used in the method of the present invention is not particularly limited, and may be usually a catalytic amount.
The component (a) is usually 10 ^{-8 to} 0.5 mol, as Pd, per mol of the aromatic hydroxy compound as a raw material.
Preferably it is in the range of 10 ^-6 to 10 ^-2 mol. If this amount is less than 10 ^-8 mol, the reaction rate is slow and impractical,
If the amount exceeds 5 moles, no improvement in the effect is recognized for the amount, but it is economically disadvantageous. The amount of at least one type of atom exhibiting Lewis acidity is usually in the range of 10 ^-2 to 50 mol, preferably 0.1 to 10 mol, per 1 mol of Pd. When the amount is less than 10 ^-2 mol, the effect of improving the catalytic activity by forming a polynuclear complex is not observed.
If it exceeds 0 mol, a side reaction using an atom expressing Lewis acid as an active species may proceed. Further, the amount of the component (b) is usually 0.1 with respect to 1 mol of Pd of the component (a).
To 100 mol, preferably 0.5 to 50 mol. If the amount of the component (b) is less than 0.1 mol, the reaction rate is slow and impractical.
The oxidative decomposition reaction of the aromatic carbonate generated by the component may proceed, which may be economically disadvantageous.

The process of the present invention proceeds similarly in the absence or presence of 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 the aromatic carbonate, the method may be carried out in a solvent. Here, examples of the solvent include aliphatic hydrocarbons, cycloaliphatic hydrocarbons, halogenated hydrocarbons,
Examples include ethers, esters, nitrogen-containing solvents, sulfur-containing solvents, and the like. However, a suitable solvent cannot be unconditionally defined because an appropriate solvent varies depending on the type and combination of the catalyst used in the method of the present invention. In the method of the present invention,
The reaction temperature is not particularly limited and is usually selected in the range of 50 to 200C, preferably 70 to 150C. If the temperature is lower than 50 ° C., the reaction rate is too slow to be practical, and if it is higher than 200 ° C., many side reactions such as a decomposition reaction occur. Further, the reaction pressure is generally set to a pressurized state because a gaseous raw material such as carbon monoxide or oxygen is used. The carbon monoxide partial pressure is usually 10 ^{−2 to} 20M.
Pa, preferably in the range of 10 ^-2 to 10 MPa, whereas the oxygen partial pressure, typically 10 ^-2 to 10 MPa, preferably in the range of 10 ^-2 to 5 MPa. The oxygen partial pressure is preferably adjusted so that the gas composition in the reaction system is out of the explosion range. On the other hand, if the pressure is too low, the reaction rate will decrease. If the pressure is too high, the reactor will be large and the equipment cost will be high, which is economically disadvantageous. When using an inert gas, hydrogen, or the like, the partial pressure is not particularly limited, but may be used within a practical pressure range. The reaction method is batch,
Both semi-continuous and continuous are possible. Here, the state of the reaction system is either a liquid phase or a mixed state of a liquid phase and a gas phase. Further, the state of the catalyst in the reaction system may be uniform or non-uniform, and the catalyst may be appropriately selected. The raw material components 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 an inert solvent such as nitrogen, argon, ethane, and propane is used in a gas phase. An active gas is used.

In the method of the present invention, an aromatic hydroxy compound, carbon monoxide and oxygen are used as raw materials and are reacted in the presence of the catalyst to produce an aromatic carbonate. There are various aromatic carbonates (that is, carbonates of aromatic hydroxy compounds) which are the target products obtained by this reaction. For example, when a monohydroxy compound is used, the compound represented by the general formula (V)

[0022]

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(Where X and n are the same as described above)
And an aromatic carbonate represented by the formula: further,
When a dihydroxy compound is used, the general formula (VI)

[0024]

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(In the formula, R ¹ , R ² , a, b and Y are the same as described above, and m differs depending on the molecular weight and is an integer of 1 or more. The terminal structure of the molecule is not particularly defined.)
And an aromatic carbonate represented by the formula: In this case, a polycarbonate resin having a large m can be obtained by appropriately selecting a catalyst and reaction conditions. Examples of by-products obtained at the same time in this reaction include salicylic esters and diphenols. Specific examples of these by-products include phenyl salicylate, 4,4'-diphenol, 2,2'-
Diphenol and the like. The separation of the target substance and the by-product may be performed by a conventional method such as distillation or extraction.

[0026]

Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to 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, phenol was added.
3.02 g (32 mmol), 7.5 mg of Pd ₂ [bis (diphenylphosphino) methane] ₂ (SnCl ₃ ) Cl
(6 micromol, 12 micromol as Pd), M
14.5 mg (24 micromol) of n (2,2,6,6-tetramethyl-3,5-heptanedionato) ₃ was charged. Next, the inside of the autoclave was replaced with carbon monoxide by pressurizing and depressurizing with carbon monoxide. Thereafter, carbon monoxide was pressurized so as to obtain 0.50 MPa in terms of 25 ° C., and air was further pressurized such that the entire pressure became 0.75 MPa. This was heated to 100 ° C. and reacted for 3 hours. After cooling and depressurizing, methylene chloride 20
Milliliter was added to obtain a dark brown homogeneous reaction solution. As a result of analyzing the reaction solution by gas chromatography, 0.278 mmol of diphenyl carbonate (DPC) was produced (1.70% yield). In addition, 0.011 mmol of phenyl salicylate (PS) was produced as a by-product (yield 0.07%). Table 1 shows the reaction conditions, and Table 2 shows the amount, yield, rate of production, and amount and yield of by-products obtained. In addition, the yield of DPC and PS indicates the yield based on phenol in%, and the DPC generation rate indicates the amount of DPC generated per unit time and the amount of palladium catalyst in mol-DPC / mol-Pd · hour.

Example 2 In the same manner as in Example 1 except that Mn (tropolonate) ₃ was used instead of Mn (2,2,6,6-tetramethyl-3,5-heptanedionato) _3. Carried out. Table 1 shows the reaction conditions, the amount of DPC produced,
Table 2 shows the yield, production rate, PS production amount, and yield. Example 3 In Example 1, 6.7 mg of Mn (2,2,6,6-tetramethyl-3,5-heptanedionato) ₃ was added.
(11 micromoles), except that it was carried out in the same manner as in Example 1. Table 1 shows the reaction conditions, and Table 2 shows the amount, yield, and production rate of the obtained DPC, and the amount and yield of PS. Example 4 Example 3 was carried out in the same manner as in Example 3 except that Mn (tropolonate) ₃ was used instead of Mn (2,2,6,6-tetramethyl-3,5-heptanedionato) ₃ . Table 1 shows the reaction conditions, the amount of DPC produced,
Table 2 shows the yield, production rate, PS production amount, and yield. Example 5 Example 5 was carried out in the same manner as in Example 1, except that the reaction time was changed to 1 hour. Table 1 shows the reaction conditions, and Table 2 shows the amount, yield, and production rate of the obtained DPC, and the amount and yield of PS. Example 6 Example 6 was carried out in the same manner as in Example 4, except that the reaction time was changed to 1 hour. Table 1 shows the reaction conditions, and Table 2 shows the amount, yield, and production rate of the obtained DPC, and the amount and yield of PS.

Example 7 Pd ₂ [bis (diphenylphosphino) methane] ₂ (SnCl ₃ ) Cl was replaced with Pd in Example 1.
₂ [Bis (diphenylphosphino) methane] ₂ Cl ₂ 6.
The procedure was performed in the same manner as in Example 1 except that 3 mg (6 μmol, 12 μmol as Pd) and 1.1 mg (6 μmol) of SnCl ₂ were used. Table 1 shows the reaction conditions, and Table 2 shows the amount of DPC produced, the yield, the production rate, the amount of PS produced, and the yield of the obtained product. Examples 8 to 10 Example 3 was repeated except that the redox catalyst shown in Table 1 was used in place of Mn (2,2,6,6-tetramethyl-3,5-heptanedionato) ₃ in Example 3. The same was done. Table 1 shows the reaction conditions, and Table 2 shows the amount, yield, and production rate of the obtained DPC, and the amount and yield of PS. In Example 11 Example 7, TiCl ₃ 0 instead of SnCl _2.
The same operation as in Example 7 was performed except that 9 mg (6 μmol) was used. Table 1 shows the reaction conditions.
Amount, yield, production rate, PS generation amount and yield
It is shown in the table. Example 12 In Example 7, FeCl ₂ .0 was used instead of SnCl ₂ .
The same operation as in Example 7 was performed except that 8 mg (6 μmol) was used. Table 1 shows the reaction conditions.
Amount, yield, production rate, PS generation amount and yield
It is shown in the table.

Comparative Example 1 In Example 1, PdBr was used instead of Pd ₂ [bis (diphenylphosphino) methane] ₂ (SnCl ₃ ) Cl.
_{The same} operation as in Example 1 was carried out except that 23.2 mg (12 μmol) was used. Table 1 shows the reaction conditions, and Table 2 shows the amount, yield, and production rate of the obtained DPC, and the amount and yield of PS. Comparative Examples 2 to 5 In Comparative Example 1, 11 micromoles of each of the redox catalysts shown in Table 1 was used instead of Mn (2,2,6,6-tetramethyl-3,5-heptanedionato) ₃ . (Ph ₃ P =) ₂ NBr [bis (triphenylphosphoranylidene) ammonium bromide] 0.15
The same operation as in Comparative Example 1 was carried out except that g (0.24 mmol) was added. Table 1 shows the reaction conditions, and Table 2 shows the amount of DPC produced, the yield production rate, the amount of PS produced, and the yield. Comparative Example 6 In Comparative Example 1, [PdClC was used instead of PdBr _2.
6.4 mg (6 μmol, 12 μmol as Pd) of u (hp) ₃ C ₂ H ₅ OH] ₂ (hp: 2-hydroxypyridine anion),
Comparative Example 1 was carried out in the same manner as in Comparative Example 1, except that 3.7 milligrams (11 micromoles) of Ce (acetate) ₃ was used instead of 2,6,6-tetramethyl-3,5-heptanedionato) ₃ . Table 1 shows the reaction conditions, and Table 2 shows the amount of DPC produced, the yield production rate, the amount of PS produced, and the yield.

[0030]

[Table 1]

[0031]

[Table 2]

[0032]

According to the method of the present invention, an aromatic carbonate useful as a raw material for producing a polycarbonate by a transesterification reaction, an intermediate raw material for various organic syntheses, or a polycarbonate resin can be obtained by converting an aromatic hydroxy compound from an aromatic hydroxy compound. It can be produced industrially and advantageously with a simple process in good yield.

 ──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Mitsuru Ueda 1-1 1-1 Higashi Higashi, Tsukuba City, Ibaraki Pref. Institute of Materials Science and Technology (72) Inventor Kazuhiko Takeuchi 1-1-1 Higashi 1-City Tsukuba City, Ibaraki Pref. (72) Inventor Michihiko Asai 1-1-1 Higashi, Tsukuba, Ibaraki Pref.

Claims (1)

[Claims] 1. An aromatic hydroxy compound and monoxide in the presence of a catalyst comprising (a) a polynuclear metal complex compound having at least one atom exhibiting Lewis acidity and a palladium atom as a metal center, and (b) a redox catalyst. A method for producing an aromatic carbonate, comprising reacting carbon and oxygen.