NL7908991A - PROCESS FOR PREPARING AROMATIC CARBONATES. - Google Patents

PROCESS FOR PREPARING AROMATIC CARBONATES. Download PDF

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NL7908991A
NL7908991A NL7908991A NL7908991A NL7908991A NL 7908991 A NL7908991 A NL 7908991A NL 7908991 A NL7908991 A NL 7908991A NL 7908991 A NL7908991 A NL 7908991A NL 7908991 A NL7908991 A NL 7908991A
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mmol
carbon monoxide
carbonate
aromatic carbonates
palladium
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NL7908991A
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Gen Electric
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • B01J31/30—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids
    • C07C68/01—Preparation of esters of carbonic or haloformic acids from carbon monoxide and oxygen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72—Manganese
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

* S 2348-989 · ^ P & c ^* S 2348-989 ^ P & c ^

Werkwijze ter bereiding van aromatische carbonaten.Process for the preparation of aromatic carbonates.

De uitvinding heeft betrekkking op een werkwijze ter bereiding van aromatische carbonaten. Het Amerikaanse octrooischrift 3.846.468 beschrijft de bereiding van koolzuuresters door omzetting van een alifatische en aromatische alcohol met koolmonoxide en zuurstof in aanwezigheid van een complex 5 van koper met een organisch molecuul.The invention relates to a process for the preparation of aromatic carbonates. U.S. Pat. No. 3,846,468 describes the preparation of carbonic acid esters by reacting an aliphatic and aromatic alcohol with carbon monoxide and oxygen in the presence of a complex of copper with an organic molecule.

De uitvinding verschaft een werkwijze ter bereiding van aromatische carbonaten, volgens welke werkwijze men een alkanol, een fenol en koolmonoxide in aanwezigheid van een base en een palladium bevattende katalysator met elkaar in kontakt brengt. De fenolverbinding heeft de formule R -(OH), 10 waarin R een aromatische groep voorstelt. De als reaktiecomponent toege-The invention provides a process for the preparation of aromatic carbonates, by which an alkanol, a phenol and carbon monoxide are contacted in the presence of a base and a palladium-containing catalyst. The phenolic compound has the formula R - (OH), wherein R represents an aromatic group. The additive added as reaction component

cLcL

paste alkanol bezit de algemene formule cnH2n+l°H' n een 9e^eel· 9©“ tal met een waarde van 1-10 voorstelt. Voorbeelden van deze alkanolen zijn methanol, ethanol, 1-propanol, 1-hexanol, 2-ethyl-l-hexanol en 1-decanol.paste alkanol has the general formula cnH2n + 1 ° H 'n represents a 9th part 9 © number having a value of 1-10. Examples of these alkanols are methanol, ethanol, 1-propanol, 1-hexanol, 2-ethyl-1-hexanol and 1-decanol.

De palladium bevattende katalysator wordt toegepast in de vorm van een ver-15 binding of complex.The palladium-containing catalyst is used in the form of a compound or complex.

De base kan een tertiair amine of een alkalimetaal- of aardalkali-metaalhydroxxdê,· -carbonaat, -acetaat of -benzoaat zijn of een mengsel van 2 of meer van deze verbindingen.The base may be a tertiary amine, or an alkali metal or alkaline earth metal hydroxide, carbonate, acetate or benzoate or a mixture of 2 or more of these compounds.

Men kan in het reaktiemengsel ook een fase-overdrachtsmiddel toepas-20 sen, bij voorkeur oniumhalogeniden, in het bijzonder chloriden en bromiden, zoals tetrabutylammoniumbromide en tetrabutylfosfoniumbromide.It is also possible to use a phase transfer agent in the reaction mixture, preferably onium halides, in particular chlorides and bromides, such as tetrabutyl ammonium bromide and tetrabutylphosphonium bromide.

De reaktie wordt bij voorkeur uitgevoerd onder watervrije omstandigheden. Hiertoe worden in het reaktiemengsel bij voorkeur een droogmiddel toegepast, zoals een moleculaire zeef.The reaction is preferably carried out under anhydrous conditions. For this purpose, a drying agent, such as a molecular sieve, is preferably used in the reaction mixture.

25 Het verdient de voorkeur om in kombinatie met de palladium bevatten de katalysator een mangaan bevattende redox-cokatalysator van een a-diketon of β-diketon of een mengsel hiervan, zoals acetylaceton, te gebruiken, bij voorbeeümangaan (II)bis(acetylacetonaat).It is preferable to use, in combination with the palladium-containing catalyst, a manganese-containing redox cocatalyst of an α-diketone or β-diketone or a mixture thereof, such as acetylacetone, for example, manganese (II) bis (acetylacetonate).

In de onderstaande voorbeelden zijn alle genoemde delen gew.dln.; 30 de structuur van de reaktieprodukten werd bevestigd door het infrarood-spectrum, het 0-13 kernmagnetisch resonantiespectrum en het massaspectrum.In the examples below, all parts mentioned are parts by weight. The structure of the reaction products was confirmed by the infrared spectrum, the 0-13 nuclear magnetic resonance spectrum and the mass spectrum.

VOORBEELD IEXAMPLE I

In een rondbodemkolf van 50 ml., die voorzien was van koolmonoxide-en gasinlaten en een gasuitlaat, bracht men een magnetische roerstaaf, 35 2,12 g (10,0 mmol) p.cumylfenol, 046 g (10,0 mmol) ethanol, 2,0 g molecu laire zeven Linde 3A, die waren geaktiveerd door verhitting gedurende 24 uren op 200° C in een stroom droge stikstof, 0,23 g (1,5 mmol) 2,2,6,6,N-pentamethylpiperidine, 0,025 g (0,1 mmol) palladiumdibromide en 0,105 g 7908991A magnetic stir bar, 2.12 g (10.0 mmol) of p-cumylphenol, 046 g (10.0 mmol) of ethanol, was placed in a 50 ml round bottom flask fitted with carbon monoxide and gas inlets and a gas outlet. 2.0 g molecular sieves Linde 3A, which were activated by heating for 24 hours at 200 ° C in a stream of dry nitrogen, 0.23 g (1.5 mmol) 2,2,6,6, N-pentamethylpiperidine , 0.025 g (0.1 mmol) palladium dibromide and 0.105 g 7908991

*Y* Y

- 2 - (0,3 mmol) mangaan-bis(acetylacetonaat). Hieraan werden 0,100 g bibenzyl, 0,050 g tolueen en 25 ml dichloormethaan toegevoegd. Men liet koolmonoxide en lucht gedurende 16 uren onder roeren bij kamertemperatuur door de oplossing borrelen. Het mengsel werd geanalyseerd door vloeistofchromatografie 5 en dampfasechromatografie; uit deze analyse bleek de aanwezigheid van de volgende produkten: 0,710 g (2,5 mmol) p.cumylfenyl(ethyl)carbonaat, 0,047 g (0,39 mmol) diethylcarbonaat en 0,308 g (0,69 mmol) bis(p.cumylfenyl)carbonaat.2 (0.3 mmol) manganese bis (acetylacetonate). 0.100 g of bibenzyl, 0.050 g of toluene and 25 ml of dichloromethane were added to this. Carbon monoxide and air were bubbled through the solution at room temperature for 16 hours with stirring. The mixture was analyzed by liquid chromatography and vapor phase chromatography; this analysis revealed the presence of the following products: 0.710 g (2.5 mmol) p.cumylphenyl (ethyl) carbonate, 0.047 g (0.39 mmol) diethyl carbonate and 0.308 g (0.69 mmol) bis (p.cumylphenyl carbonate.

Tabel A ^ 0-0-0-C-OEt Et2C0j (0~C|)2 °r7l° S· 0T047 g. 0,308 g.Table A ^ 0-0-0-C-OEt Et2C0j (0 ~ C |) 2 ° r7l ° S0T047 g. 0.308 g.

15 VOORBEELD IIEXAMPLE II

In een rondbodemkolf van 50 ml, die voorzien was van koolmonoxide-en luchtinlaten en een gasuitlaat, bracht men een magnetische roerstaaf, o,94 g (10,0 mmol) ‘fenol, 0,32 g (10,0 mol) methanol 2,0 g moleculaire zeven Linde 3A, die geaktiveerd waren door gedurende 24 uren op 200° C te 20 verhitten in een stroom droge stikstof, 0,23 g (1,5 mmol) 1,2,2,6,6-penta- methylpiperidine, 0,025 g (0,1 mmol) palladiumdibromide en 0,075 g (0,3 mmol) mangaan-bis(acetylacetonaat). Hieraan voegde men 0,100 g bibenzyl, 0,050 g tolueen en 25 ml dichloormethaan toe. Men liet koolmonoxide en lucht gedurende 16 uren onder roeren bij kamertemperatuur door de oplossing borrelen.Into a 50 ml round bottom flask equipped with carbon monoxide and air inlets and a gas outlet, a magnetic stir bar, 0.94 g (10.0 mmol) of phenol, 0.32 g (10.0 mol) of methanol 2 was placed. .0 g molecular sieves Linde 3A, which were activated by heating in a stream of dry nitrogen at 200 ° C for 24 hours, 0.23 g (1.5 mmol) 1,2,2,6,6-penta- methylpiperidine, 0.025 g (0.1 mmol) palladium dibromide and 0.075 g (0.3 mmol) manganese bis (acetylacetonate). 0.100 g of bibenzyl, 0.050 g of toluene and 25 ml of dichloromethane were added to this. Carbon monoxide and air were bubbled through the solution at room temperature for 16 hours with stirring.

25 Vervolgens werd het mengsel geanalyseerd door vloeistofchromatografie en dampfasechromatografie; uit deze analyse bleek dat de volgende produkten waren verkregen: 0,22 g (1,4 mmol) fenyl(meth$i)carbonaat, 0,15 g (1,67 mmol) dimethylcarbonaat en 0,12 g (0,69 mmol) difenylcarbonaat.Then the mixture was analyzed by liquid chromatography and vapor phase chromatography; this analysis showed that the following products were obtained: 0.22 g (1.4 mmol) phenyl (meth $ i) carbonate, 0.15 g (1.67 mmol) dimethyl carbonate and 0.12 g (0.69 mmol) ) diphenyl carbonate.

Tabel BTable B

30 0 _ r- s30 0 _ r- s

McO-O-C-O-Q) Me2C03 (Q) C03 0,22 g. 0,15 g. 0,12 g.McO-O-C-O-Q) Me 2 CO 3 (Q) CO 3 0.22 g. 0.15 g. 0.12 g.

35 VOORBEELD IIIEXAMPLE III

In een rondbodemkolf van 50 ml, die voorzien was van koolmonoxide-en luchtinlaten en een gasuitlaat, bracht men een magnetische roerstaaf,A magnetic stir bar was placed in a 50 ml round bottom flask fitted with carbon monoxide and air inlets and a gas outlet,

2,12 g (10,0 mmol) p.cumylfenol, 0,46 g (10,0 mmol) ethanol, 2,0 g moleculaire zeven Linde 3A, die geaktiveerd waren door 24 uren verhitten op 200° G2.12 g (10.0 mmol) p.cumylphenol, 0.46 g (10.0 mmol) ethanol, 2.0 g molecular sieves Linde 3A, which were activated by heating at 200 ° G for 24 hours

/908991 - 3 - in een stroom droge stikstof, 0,23 g (1,5 mmol) 1,2,2,6,6,-pentamethylpipe-ridine, 0,025 g (0,1 mmol) palladiumdibromide en 0,105 g (0,3 mmol) mangaan-bis(acetylacetonaat). Hieraan voegde men 0,100 g bibenzyl, 0,050 g tolueen en 25 ml dichloormethaan toe. Men liet gedurende 16 uren koolmonoxide en 5 lucht onder roeren bij kamertemperatuur door de oplossing borrelen. Vervolgens werd het mengsel geanalyseerd door vloeistofchromatografie en dampfase-chromatografie; blijkens deze analyse waren de volgende produkten verkregen: 0,374 g (1,3 mmol) p.cumylfenyl(ethyl)carbonaat, 0,057 g-(0,48 mmol) diethyl-carbonaat en 0,265 g (0,59 mmol) bis(p.cumylfenyl)carbonaat./ 908991-3 - in a stream of dry nitrogen, 0.23g (1.5mmol) 1,2,2,6,6-pentamethylpiperidine, 0.025g (0.1mmol) palladium dibromide and 0.105g (0 .3 mmol) manganese bis (acetylacetonate). 0.100 g of bibenzyl, 0.050 g of toluene and 25 ml of dichloromethane were added to this. Carbon monoxide and air were bubbled through the solution at room temperature for 16 hours. The mixture was then analyzed by liquid chromatography and vapor phase chromatography; According to this analysis, the following products were obtained: 0.374 g (1.3 mmol) p-cumylphenyl (ethyl) carbonate, 0.057 g (0.48 mmol) diethyl carbonate and 0.265 g (0.59 mmol) bis (p. cumylphenyl) carbonate.

10 VOORBEELD IVEXAMPLE IV

In een rondbodemkolf van 50 ml, die voorzien was van koolmonoxide-en luchtinlaten en een gasuitlaat, bracht men een magnetische roerstaaf, 0,94 g (10,0 mmol) p.cumylfenol, 0,82 g (10,0 mmol) methanol, 2,0 g moleculaire zeven Linde 3A, -die geaktiveerd waren door 24 uren verhitten op 200° C 15 in een stroom droge stikstof, 0,52 g (1,6 mmol) tetrabutylammoniumbromide, 0,10 g (1,3 mmol) 50 %'s waterige loog, 0,025 g (0,1 mmol) palladiumdibro-mide en 0,075 g (0,3 mmol) mangaan-bis(acetylacetonaat). Hieraan voegde men 0,100 g bibenzyl, 0,050 g tolueen en 25 ml dichloormethaan toe. Men liet gedurende 16 uren koolmonoxide en lucht onder roeren bij kamertempera-20 tuur door de oplossing borrelen. Het mengsel werd vervolgens door vloeistofchromatografie en dampfasechromatografie geanalyseerd; blijkens deze analyse waren de volgende produkten verkregen: 0,14 g (0,9 mmol) fenyl(methyl)carbonaat, o,15 g (1,67 mmol) dimethylcarbonaat en 0,02 g (0,09 mmol) difenyl-carbonaat.A magnetic stir bar, 0.94 g (10.0 mmol) of p-cumylphenol, 0.82 g (10.0 mmol) of methanol was placed in a 50 ml round bottom flask equipped with carbon monoxide and air inlets and a gas outlet. 2.0 g molecular sieves Linde 3A, which were activated by heating at 200 ° C in a stream of dry nitrogen for 24 hours, 0.52 g (1.6 mmol) tetrabutylammonium bromide, 0.10 g (1.3 mmol 50% aqueous caustic, 0.025 g (0.1 mmol) palladium dibromide and 0.075 g (0.3 mmol) manganese bis (acetylacetonate). 0.100 g of bibenzyl, 0.050 g of toluene and 25 ml of dichloromethane were added to this. Carbon monoxide and air were bubbled through the solution at room temperature for 16 hours with stirring. The mixture was then analyzed by liquid chromatography and vapor phase chromatography; according to this analysis, the following products were obtained: 0.14 g (0.9 mmol) phenyl (methyl) carbonate, 0.15 g (1.67 mmol) dimethyl carbonate and 0.02 g (0.09 mmol) diphenyl carbonate .

25 VOORBEELD VEXAMPLE V

In een autoclaaf van 1 1 bracht men 0,90 g (9,6 mmol) fenol, 0,53 g (1,2 mmol) di(triethylfosfien)palladiumcarbomethoxychloride, 0,97 g (9,6 mmol) triethylamine, 150 ml chloorbenzeen en voldoende koolmonoxide om de druk in het vat op circa 11.030 kpa (overdruk) te brengen. Bij verhitten 30 van het systeem op 100° C nam de overdruk toe tot circa 13.960 kPa. Na 1 uur werden de reaktieprodukten af gekoeld tot 28° C. Uit analyse van het verkregen produkt bleek de aanwezigheid van fenyl(methyl)carbonaat.Into a 1 L autoclave, 0.90 g (9.6 mmol) of phenol, 0.53 g (1.2 mmol) of di (triethylphosphine) palladium carbomethoxy chloride, 0.97 g (9.6 mmol) of triethylamine, 150 ml chlorobenzene and enough carbon monoxide to bring the pressure in the vessel to approximately 11,030 kpa (gauge pressure). When the system was heated to 100 ° C, the overpressure increased to approximately 13,960 kPa. After 1 hour, the reaction products were cooled to 28 ° C. Analysis of the product obtained revealed the presence of phenyl (methyl) carbonate.

79089917908991

Claims (5)

1. Werkwijze ter bereiding van aromatische carbonaten, met het kenmerk dat men een alkanol met 1-10 koolstofatomen, een fenol en koolmonoxide in aanwezigheid van een base en een palladium bevattende katalysator met elkaar omzet.Process for the preparation of aromatic carbonates, characterized in that an alkanol of 1-10 carbon atoms, a phenol and carbon monoxide are reacted in the presence of a base and a palladium-containing catalyst. 2. Werkwijze volgens conclusie 1, met het kenmerk dat men in het reaktie-mengsel verder een mangaan bevattende redox-cokatalysator toepast.2. Process according to claim 1, characterized in that a manganese-containing redox cocatalyst is further used in the reaction mixture. 3. Werkwijze volgens conclusie 1 of 2, met het kenmerk dat men verder een fase-overdrachtmiddel toepast.Method according to claim 1 or 2, characterized in that a phase transfer agent is further used. 4. Werkwijze volgens conclusies 1-3, met het kenmerk dat men verder een droogmiddel toepast.4. Process according to claims 1-3, characterized in that a drying agent is further used. 5. Werkwijze volgens conclusie 4, met het kenmerk dat men als droogmiddel een moleculaire zeef gebruikt. 7908981Process according to claim 4, characterized in that a molecular sieve is used as the drying agent. 7908981
NL7908991A 1978-12-14 1979-12-13 PROCESS FOR PREPARING AROMATIC CARBONATES. NL7908991A (en)

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CA (1) CA1137102A (en)
DE (1) DE2949936A1 (en)
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GB (1) GB2038321B (en)
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* Cited by examiner, † Cited by third party
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DE3203190A1 (en) * 1982-01-30 1983-08-04 Bayer Ag, 5090 Leverkusen Preparation of dialkyl carbonates and diaryl carbonates
JPH0780817B2 (en) * 1987-07-04 1995-08-30 ダイセル化学工業株式会社 Method for producing carbonate ester
EP0350697A3 (en) * 1988-07-11 1991-07-31 General Electric Company Preparation of organic carbonates by oxidative carbonylation using palladium-manganese catalyst
JPH0539247A (en) * 1991-03-14 1993-02-19 Idemitsu Kosan Co Ltd Production of organic carbonate
JPH04312554A (en) * 1991-04-11 1992-11-04 Idemitsu Kosan Co Ltd Production of organic carbonate
DE19859290A1 (en) * 1998-12-22 2000-06-29 Bayer Ag Process for the preparation of diaryl carbonates
JP4892853B2 (en) * 2005-04-07 2012-03-07 Ｊｎｃ株式会社 Liquid crystal compound having carbonate bond group, liquid crystal composition containing this compound, and liquid crystal display device containing this liquid crystal composition

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US4096168A (en) * 1976-10-12 1978-06-20 General Electric Company Aromatic carbonates
IN148495B (en) * 1976-10-12 1981-03-14 Gen Electric
IN148600B (en) * 1976-10-12 1981-04-11 Gen Electric
FR2422622A2 (en) * 1978-04-10 1979-11-09 Gen Electric Aromatic carbonate(s) prodn. from phenol and carbon mon:oxide - by reacting a phenol, carbon mon:oxide, a base, a Gp=VIIIB cpd., an oxidising agent and a co-catalyst complex in the presence of an organic

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JPS55102539A (en) 1980-08-05
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FR2444024A1 (en) 1980-07-11
IT1126409B (en) 1986-05-21
CA1137102A (en) 1982-12-07
IT7927636A0 (en) 1979-11-28
GB2038321B (en) 1983-04-13

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