The invention relates to a production process for di- and polyamines of the diphenylmethane series by the rearrangement of a condensation product of aniline and a methylene group-supplying agent preferably selected from the group consisting of aqueous formaldehyde solution, gaseous formaldehyde, para-formaldehyde, trioxane and mixtures thereof, wherein said condensation product is reacted in the presence of at least one silica-alumina catalyst, said catalyst having a surface area as determined by the BET method carried out according to ASTM D3663-03 (2015) of from 200 m.sup.2/g to 520 m.sup.2/g, preferably of from 350 m.sup.2/g to 495 m.sup.2/g, particularly preferably of from 400 m.sup.2/g to 490 m.sup.2/g, a molar ratio of silica/alumina on the catalyst surface of A, an overall (bulk) molar ratio of silica/alumina of C, and a quotient B=A/C;
said catalyst being characterised in that “low” A values (i.e. equal to or lower than 8.0) are combined with “high” B values (i.e. of from 1.50 to 3.00), and “high” A values (i.e. larger than 8.00, especially equal to or larger than 8.50) are combined with “low” B values (i.e. of from 0.15 to 1.40).

The invention relates to a production process for di- and polyamines of the diphenylmethane series by the rearrangement of a condensation product of aniline and a methylene group-supplying agent preferably selected from the group consisting of aqueous formaldehyde solution, gaseous formaldehyde, para-formaldehyde, trioxane and mixtures thereof, wherein said condensation product is reacted in the presence of at least one silica-alumina catalyst, said catalyst having a surface area as determined by the BET method carried out according to ASTM D3663-03 (2015) of from 200 m.sup.2/g to 520 m.sup.2/g, preferably of from 350 m.sup.2/g to 495 m.sup.2/g, particularly preferably of from 400 m.sup.2/g to 490 m.sup.2/g, a molar ratio of silica/alumina on the catalyst surface of A, an overall (bulk) molar ratio of silica/alumina of C, and a quotient B=A/C;
said catalyst being characterised in that “low” A values (i.e. equal to or lower than 8.0) are combined with “high” B values (i.e. of from 1.50 to 3.00), and “high” A values (i.e. larger than 8.00, especially equal to or larger than 8.50) are combined with “low” B values (i.e. of from 0.15 to 1.40).

The object of the present invention is to provide a method which provides a diaminobiphenyl compound in a high yield and in a short period of time by a benzidine rearrangement reaction of a hydrazobenzene having a bulky substituent group at the meta position. Specifically, the present invention provides a method for preparing a diaminobiphenyl compound represented by the following formula (1):

##STR00001##

wherein, X.sub.1 and X.sub.2 are, independently of each other, a group selected from the group consisting of a trifluoromethyl group and, optionally fluorinated, isopropyl, isobutyl, sec-butyl, tert-butyl and neopentyl groups, comprising a step of subjecting a diphenylhydrazine compound represented by the following formula (2)

##STR00002##

wherein X.sub.1 and X.sub.2 are as defined above,
to a benzidine rearrangement reaction in the presence of an organic solvent and an inorganic acid at a temperature of from −70° C. to −11° C.
to obtain the diaminobiphenyl compound represented by the formula (1).

The object of the present invention is to provide a method which provides a diaminobiphenyl compound in a high yield and in a short period of time by a benzidine rearrangement reaction of a hydrazobenzene having a bulky substituent group at the meta position. Specifically, the present invention provides a method for preparing a diaminobiphenyl compound represented by the following formula (1):

##STR00001##

wherein, X.sub.1 and X.sub.2 are, independently of each other, a group selected from the group consisting of a trifluoromethyl group and, optionally fluorinated, isopropyl, isobutyl, sec-butyl, tert-butyl and neopentyl groups, comprising a step of subjecting a diphenylhydrazine compound represented by the following formula (2)

##STR00002##

wherein X.sub.1 and X.sub.2 are as defined above,
to a benzidine rearrangement reaction in the presence of an organic solvent and an inorganic acid at a temperature of from −70° C. to −11° C.
to obtain the diaminobiphenyl compound represented by the formula (1).

The object of the present invention is to provide a method which provides a diaminobiphenyl compound in a high yield and in a short period of time by a benzidine rearrangement reaction of a hydrazobenzene having a bulky substituent group at the meta position. Specifically, the present invention provides a method for preparing a diaminobiphenyl compound represented by the following formula (1):

##STR00001##

wherein, X.sub.1 and X.sub.2 are, independently of each other, a group selected from the group consisting of a trifluoromethyl group and, optionally fluorinated, isopropyl, isobutyl, sec-butyl, tert-butyl and neopentyl groups, comprising a step of subjecting a diphenylhydrazine compound represented by the following formula (2)

##STR00002##

wherein X.sub.1 and X.sub.2 are as defined above,
to a benzidine rearrangement reaction in the presence of an organic solvent and an inorganic acid at a temperature of from −70° C. to −11° C.
to obtain the diaminobiphenyl compound represented by the formula (1).

A compound represented by the following formula (1) (wherein the symbols are as defined in the description), an organic electroluminescent device containing the compound, and an electronic device including the organic electroluminescent device.

##STR00001##

A compound represented by the following formula (1) (wherein the symbols are as defined in the description), an organic electroluminescent device containing the compound, and an electronic device including the organic electroluminescent device.

##STR00001##

The present invention primarily relates to a process for producing certain substituted 2-allylanilines of the hereinbelow-defined formula (I) and their use in a process for producing substituted 4-aminoindane derivatives of the hereinbelow-defined formula (V). The present invention further relates to a process for producing fungicidal indanyl carboxamides. In particular, the present invention relates to a process for producing 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-2,3-dihydro-1H-inden-4-yl)nicotinamide and/or 3-(difluoromethyl)-N-[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazole-4-carboxamide.

The present invention primarily relates to a process for producing certain substituted 2-allylanilines of the hereinbelow-defined formula (I) and their use in a process for producing substituted 4-aminoindane derivatives of the hereinbelow-defined formula (V). The present invention further relates to a process for producing fungicidal indanyl carboxamides. In particular, the present invention relates to a process for producing 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-2,3-dihydro-1H-inden-4-yl)nicotinamide and/or 3-(difluoromethyl)-N-[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazole-4-carboxamide.

The present invention primarily relates to a process for producing certain substituted 2-allylanilines of the hereinbelow-defined formula (I) and their use in a process for producing substituted 4-aminoindane derivatives of the hereinbelow-defined formula (V). The present invention further relates to a process for producing fungicidal indanyl carboxamides. In particular, the present invention relates to a process for producing 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-2,3-dihydro-1H-inden-4-yl)nicotinamide and/or 3-(difluoromethyl)-N-[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazole-4-carboxamide.