A description is given of a process for preparing 1-indanols and 1-indanamines by palladium-catalyzed arylation and of the use thereof as intermediates for the synthesis of fine chemicals and of active agrochemical ingredients.

Disclosed is a methanol and sulfuric acid co-production system capable of producing methanol and sulfuric acid in equal equivalents. Specifically, the system includes an oxidation reaction unit configured to produce methyl bisulfate (CH.sub.3OSO.sub.3H) by reacting methane gas with an acid solution in the presence of a catalyst, a reactive distillation unit disposed downstream of the oxidation reaction unit and configured to esterify methyl bisulfate (CH.sub.3OSO.sub.3H) supplied from the oxidation reaction unit with trifluoroacetic acid (CF.sub.3COOH) to obtain a product and to separate the product into methyl trifluoroacetate (CF.sub.3COOCH.sub.3) and sulfuric acid (H.sub.2SO.sub.4) through thermal distillation, and a hydrolysis reaction unit disposed downstream of the reactive distillation unit and configured to produce methanol by hydrolyzing methyl trifluoroacetate (CF.sub.3COOCH.sub.3) supplied from the reactive distillation unit, in which the reactive distillation unit recirculates the sulfuric acid resulting from separation to the oxidation reaction unit.

Disclosed is a methanol and sulfuric acid co-production system capable of producing methanol and sulfuric acid in equal equivalents. Specifically, the system includes an oxidation reaction unit configured to produce methyl bisulfate (CH.sub.3OSO.sub.3H) by reacting methane gas with an acid solution in the presence of a catalyst, a reactive distillation unit disposed downstream of the oxidation reaction unit and configured to esterify methyl bisulfate (CH.sub.3OSO.sub.3H) supplied from the oxidation reaction unit with trifluoroacetic acid (CF.sub.3COOH) to obtain a product and to separate the product into methyl trifluoroacetate (CF.sub.3COOCH.sub.3) and sulfuric acid (H.sub.2SO.sub.4) through thermal distillation, and a hydrolysis reaction unit disposed downstream of the reactive distillation unit and configured to produce methanol by hydrolyzing methyl trifluoroacetate (CF.sub.3COOCH.sub.3) supplied from the reactive distillation unit, in which the reactive distillation unit recirculates the sulfuric acid resulting from separation to the oxidation reaction unit.

A polyfluoroalkyl allyl compound represented by the general formula:

CF.sub.3(CF.sub.2).sub.n(CH.sub.2CF.sub.2).sub.a(CF.sub.2CF.sub.2).sub.bCH.sub.2CH═CH.sub.2  [I]

(n: 0 to 5, a: 1 or 2, b: 0 to 3). The polyfluoroalkyl allyl compound is produced by reacting a carboxylic acid allyl adduct represented by the general formula:

CF.sub.3(CF.sub.2).sub.n(CH.sub.2CF.sub.2).sub.a(CF.sub.2CF.sub.2).sub.bCH.sub.2CHICH.sub.2OCOR′  [II]

(n, a, and b are as defined above, and R′: a C.sub.1-C.sub.3 alkyl group) with a transition metal. This method for producing provides a polyfluoroalkyl allyl compound used as a synthetic intermediate for a fluorine-containing alkylsilane compound that can remove free iodine derived from the raw material compound, before a hydrosilylation reaction is performed, without using a metal reagent having a high environmental impact, and that has excellent handling properties.

A polyfluoroalkyl allyl compound represented by the general formula:

CF.sub.3(CF.sub.2).sub.n(CH.sub.2CF.sub.2).sub.a(CF.sub.2CF.sub.2).sub.bCH.sub.2CH═CH.sub.2  [I]

(n: 0 to 5, a: 1 or 2, b: 0 to 3). The polyfluoroalkyl allyl compound is produced by reacting a carboxylic acid allyl adduct represented by the general formula:

CF.sub.3(CF.sub.2).sub.n(CH.sub.2CF.sub.2).sub.a(CF.sub.2CF.sub.2).sub.bCH.sub.2CHICH.sub.2OCOR′  [II]

(n, a, and b are as defined above, and R′: a C.sub.1-C.sub.3 alkyl group) with a transition metal. This method for producing provides a polyfluoroalkyl allyl compound used as a synthetic intermediate for a fluorine-containing alkylsilane compound that can remove free iodine derived from the raw material compound, before a hydrosilylation reaction is performed, without using a metal reagent having a high environmental impact, and that has excellent handling properties.

A polyfluoroalkyl allyl compound represented by the general formula:

CF.sub.3(CF.sub.2).sub.n(CH.sub.2CF.sub.2).sub.a(CF.sub.2CF.sub.2).sub.bCH.sub.2CH═CH.sub.2  [I]

(n: 0 to 5, a: 1 or 2, b: 0 to 3). The polyfluoroalkyl allyl compound is produced by reacting a carboxylic acid allyl adduct represented by the general formula:

CF.sub.3(CF.sub.2).sub.n(CH.sub.2CF.sub.2).sub.a(CF.sub.2CF.sub.2).sub.bCH.sub.2CHICH.sub.2OCOR′  [II]

(n, a, and b are as defined above, and R′: a C.sub.1-C.sub.3 alkyl group) with a transition metal. This method for producing provides a polyfluoroalkyl allyl compound used as a synthetic intermediate for a fluorine-containing alkylsilane compound that can remove free iodine derived from the raw material compound, before a hydrosilylation reaction is performed, without using a metal reagent having a high environmental impact, and that has excellent handling properties.

A method for producing at least one olefin compound selected from the group consisting of a compound of formula (51) and a compound of formula (52), the method including reacting an olefin compound of formula (21) with a olefin compound of formula (31) in the presence of at least one metal catalyst selected from the group consisting of a compound of formula (11), a compound of formula (12), a compound of formula (13), a compound of formula (14), and a compound of formula (15).

##STR00001##

A method for producing at least one olefin compound selected from the group consisting of a compound of formula (51) and a compound of formula (52), the method including reacting an olefin compound of formula (21) with a olefin compound of formula (31) in the presence of at least one metal catalyst selected from the group consisting of a compound of formula (11), a compound of formula (12), a compound of formula (13), a compound of formula (14), and a compound of formula (15).

##STR00001##

To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH.sub.2—R.sup.A—CH.sub.2OH, the compound (2) is X.sup.1C(═O)—C(R.sup.B)(R.sup.C)(R.sup.D), R.sup.A is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X.sup.1 is a halogen atom, and —C(R.sup.B)(R.sup.C)(R.sup.D) is a branched group.

To provide a process for producing a desired perfluorinated product at a high yield in a fluorination reaction of a partially fluorinated ester. A perfluorinated compound (4) is obtained by fluorinating in a liquid phase a compound (3) (wherein the fluorine content is at least 30 mass %) obtained by reacting a compound (1) and a compound (2), wherein the compound (1) is HOCH.sub.2—R.sup.A—CH.sub.2OH, the compound (2) is X.sup.1C(═O)—C(R.sup.B)(R.sup.C)(R.sup.D), R.sup.A is a bivalent saturated hydrocarbon group or the like which has no hetero atom such as an etheric oxygen atom, X.sup.1 is a halogen atom, and —C(R.sup.B)(R.sup.C)(R.sup.D) is a branched group.