Mitsubishi Gas Chemical Company, Inc.

Susumu Fujiyama

Minoru Takagawa

Takehiko Takahashi

Shunichi Matsumoto

Shiro Kajiyama

Makoto Komatsu

Mitsuharu Kitamura

Isao Mochida

Koichi Kida

Hiroyuki Otsuka

Yukio Sakai

Yuji Takamizawa

Shigeki Ozao

Toyomi Kasahara

Shigeki Kozao

A process for producing a 4-formyl-4'-methylbiphenyl from a biphenyl which comprises conducting the carbonylation of the biphenyl with carbon monoxide in the presence of a HF-BF.sub.3 catalyst in a carbonylation reactor to obtain the resulting reaction product solution containing a 4-formylbiphenyl, separating the 4-formylbiphenyl from the reaction product solution, hydrogenating the separated 4-formylbiphenyl to obtain a 4-methylbiphenyl, recycling the 4-methylbiphenyl to the carbonylation reactor, and then conducting both the carbonylation of the biphenyl with carbon monoxide to obtain a formylbiphenyl and the carbonylation of the 4-methylbiphenyl with carbon monoxide to obtain a 4-formyl-4'-methylbiphenyl simultaneously in the presence of the HF-BF.sub.3 catalyst in the carbonylation reactor.

Process for producing 4-formyl-4'-methylbiphenyl from biphenyl

A process for producing pitch useful as a starting material for the manufacture of a carbon material is provided. The pitch is produced by polymerizing a condensed nuclear aromatic compound or a material containing the same. The polymerization is carried out in the presence of a hydrogen fluoride/boron trifluoride catalyst system. The condensed nuclear aromatic compounds which may be used in this process are naphthalene, anthracene, phenanthrene, acenaphthene, acenaphthylene, pyrene and mixtures thereof.

Process for producing pitch used as starting material for the making of

Alkylbenzaldehyde is continuously produced in high yield from alkylbenzene by formylation with carbon monoxide in the presence of HF--BF.sub.3, where the alkylbenzene, HF--BF.sub.3 and carbon monoxide under a carbon monoxide partial pressure of at least 5 kg/cm.sup.2 absolute are introduced into the reactor to continuously carry out complexing of the alkylbenzene with HF--BF.sub.3 and formylation with the carbon monoxide successively in one and same reactor.

Process for continuous production of alkylbenzaldehydes

A xylene mixture containing at least one of m-xylene and o-xylene is formylated by carbon monoxide in the presence of hydrogen fluoride and boron trifluoride at a molar ratio of boron trifluoride to sum total of m-xylene and o-xylene in the xylene mixture of not more than 1.5 to selectively and correspondingly produce at least one of 2,4-dimethylbenzaldehyde and 3,4-dimethylbenzaldehyde.

Process for formylating xylene mixture

This invention relates to a two-step method for decomposing an aromatic aldehyde-hydrogen fluoride-boron trifluoride complex in the presence of benzene as a diluent to obtain an aromatic aldehyde, hydrogen fluoride and boron trifluoride separately without causing any change in the quality of the aromatic aldehyde or without forming undesirable byproducts.

Method for decomposing an aromatic aldehyde-hydrogen fluoride-boron

A method for decomposing an aromatic aldehyde-hydrogen fluoride-boron trifluoride complex in the presence of a decomposing agent represented by the formula ##SPC1## Wherein n is integer of 1-6, inclusive, and m is integer of 0-5, inclusive, and a total of n and m is 6 or less, to obtain an aromatic aldehyde, hydrogen fluoride and boron trifluoride separately without causing any change in the quality of the aromatic aldehyde or without forming undesirable byproducts is disclosed.

P-Tolualdehyde is separated with a high purify from a mixture of tolualdehyde isomers having a mole fraction of p-tolualdehyde of at least 0.27, on the basis of total tolualdehyde isomers by cooling the mixture to a crystallization temperature of -6.degree. to -60.degree.C, thereby crystallizing p-tolualdehyde, and separating the resulting p-tolualdehyde crystals from mother liquor. A solvent such as an aliphatic hydrocarbon having 1 to 9 carbon atoms or an alicyclic hydrocarbon having 3 to 9 carbon atoms can be added to the mixture before cooling to improve the crystallization conditions. The resulting crystals can be washed with a washing agent, such as said solvent, to remove the other isomers adhering to the crystals.

Process for purifying p-tolualdehyde

This invention relates to a two step process for producing p-tolualdehyde which comprises reacting toluene with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride, characterized by mixing all of the toluene, all of the hydrogen fluoride and only part of the boron trifluoride necessary to convert a substantial amount of toluene to p-tolualdehyde, thereby forming a toluene-hydrogen fluoride-boron trifluoride complex and reacting the toluene in the reaction system with carbon monoxide, thereby converting a portion of the toluene to p-tolualdehyde, and then adding the remainder of the boron trifluoride to the reaction product and reacting the remainder of the toluene with carbon oxide.

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Niigata, Japan

Susumu Fujiyama