Method for producing fluorine-containing alkane

Patent metadata

Field	Value
Publication number	US-9428429-B2
Application number	US-201113634047-A
Country	US
Kind code	B2
Filing date	Feb 18, 2011
Priority date	Mar 31, 2010
Publication date	Aug 30, 2016
Grant date	Aug 30, 2016

Abstract

The present invention provides a method for producing a fluorine-containing alkane, which comprises reacting at least one fluorine-containing compound selected from the group consisting of chlorine-containing fluoroalkanes and fluorine-containing alkenes with hydrogen gas in the presence of catalysts, wherein two or more catalysts having different catalytic activities are used, and the fluorine-containing compound and hydrogen gas, which are starting materials, are sequentially brought into contact with the catalysts in the order of the catalyst having a lower catalytic activity followed by the catalyst having a higher catalytic activity. According to the present invention, in the method for producing a fluorine-containing alkane by using chlorine-containing fluoroalkane or fluorine-containing alkene as a starting material, and subjection it to a reduction reaction or a hydrogen addition reaction, the objective fluorine-containing alkane can be produced with high productivity.

First claim

The invention claimed is:

1. A method for producing fluorine-containing alkane comprising reacting at least one chlorine-containing fluoroalkane with hydrogen gas in the presence of catalysts having different catalytic activities,
wherein the catalysts having different catalytic activities are:
those containing Pd supported on activated carbon with different supporting amounts; or
those made by mixing Pd supported on activated carbon with an activated carbon to dilute it in different dilution rates, and
wherein the at least one chlorine-containing fluoroalkane and hydrogen gas, which are starting materials, are sequentially contacted with a catalyst containing a smaller amount of Pd to a catalyst containing a larger amount of Pd.

2. The method according to claim 1 , wherein the reaction proceeds in a reaction apparatus in which two or more reaction tubes charged with catalysts having different catalytic activities are connected in series.

3. The method according to claim 1 , wherein the chlorine-containing fluoroalkane is at least one member selected from the group consisting of:
a compound represented by Formula (1):
R 1 —CCl 2-(n+m) H n F m —CCl 2-(o+p) H o F p —CCl 3-(q+r) H q F r

wherein R 1 is a C 1-4 alkyl group, a hydrogen atom, a fluorine atom, or a C 1-4 fluoroalkyl group that may contain a chlorine atom(s); n, m, o and p are each individually an integer of 0 to 2; q and r are each individually an integer of 0 to 3, with the proviso that n+m≦2, o+p≦2, q+r≦3, and n+m+o+p+q+r≦6; provided that when R 1 is neither a fluoroalkyl group nor a fluorine atom, the sum of m, p and r is 1 or greater; and
a compound represented by Formula (2):
CCl 3-(a+b) H a F b —CCl 3-(c+d) H c F d

wherein a, b, c and d are each individually an integer of 0 to 3, a+b≦3, c+d≦3, b+d≧1, and a+b+c+d≦5.

4. The method according to claim 1 , wherein the chlorine-containing fluoroalkane is a compound represented by Formula (1-1):
R 2 —CCl 2-(j+k) H j F k —CCl 3-(l+t) H l F t

wherein R 2 is a C 1-3 alkyl group, a hydrogen atom, or a fluorine atom, or a C 1-3 fluoroalkyl group that may contain a chlorine atom(s); j and k are each individually an integer of 0 to 2; l and t are each individually an integer of 0 to 3; j+k≦2; l+t≦3; and j+k+1+t≦4; with the proviso that when R 2 is neither a fluoroalkyl group nor a fluorine atom, the sum of k and t is 1 or greater.

Assignees

• Shiotani Yuko
• Hanabusa Kakeru
• Chaki Takehiro
• Takahashi Kazuhiro
• Daikin Ind Ltd

Inventors

• Shiotani Yuko
• Hanabusa Kakeru
• Chaki Takehiro
• Takahashi Kazuhiro

Classifications

• C07C17/354 Primary

  by hydrogenation · CPC title

• C07C17/23 Primary

  by dehalogenation · CPC title

• C07C19/08

  containing fluorine · CPC title

• C07C17/42

  Use of additives, e.g. for stabilisation · CPC title