Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
1999-06-25
2001-07-03
Killos, Paul J. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C562S863000
Reexamination Certificate
active
06255524
ABSTRACT:
This application is the national phase under 35 U.S.C. §371 of PCT International Application No. PCT/JP97/04412 which has an International filing date of Dec. 3, 1997 which designated the United States of America.
FIELD OF THE INVENTION
The present invention relates to a method for producing an acid chloride having a polyfluoroalkyl group.
RELATED ART
As a method for producing an acid chloride from a primary alcohol having a polyfluoroalkyl group and two methylene groups (R
f
CH
2
CH
2
OH, wherein R
f
is a polyfluoroalkyl group), a method via chlorination by means of light has been proposed (Japanese Patent Application Kokoku Publication No. 033014/1986).
When a primary alcohol having a polyfluoroalkyl group and one methylene group (R
f
CH
2
OH, wherein R
f
is a polyfluoroalkyl group) is chlorinated by means of light, however, it is difficult to give an acid chloride at a good yield, because the acid chloride formed reacts with the alcohol to give an ester as a by-product.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a method for industrially producing an acid chloride (R
f
COCl) from a primary alcohol having a polyfluoroalkyl group and one methylene group (R
f
CH
2
OH) at a high yield.
The present invention provides a method for producing an aldehyde represented by the formula:
R
f
CHO
wherein R
f
is a polyfluoroalkyl group, the method comprising reacting a primary alcohol represented by the formula:
R
f
CH
2
OH
wherein R
f
is a polyfluoroalkyl group,
with chlorine in the presence of a catalyst.
The present invention provides a method for producing an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group, the method comprising reacting an aldehyde represented by the formula:
R
f
CHO
wherein R
f
is a polyfluoroalkyl group, with chlorine in the presence of a catalyst.
The present invention provides a method for producing an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
the method comprising reacting a primary alcohol represented by the formula:
R
f
CH
2
OH
wherein R
f
is a polyfluoroalkyl group,
with chlorine in the presence of a catalyst.
The present invention provides a method for producing an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
the method comprising reacting a primary alcohol represented by the formula:
RCH
2
OH
wherein R
f
is a polyfluoroalkyl group,
with chlorine in the presence of a catalyst to give an aldehyde represented by the formula:
R
f
CHO
wherein R
f
is a polyfluoroalkyl group, and then reacting the aldehyde with chlorine in the presence of a catalyst to give the acid chloride.
The present invention provides a method for producing a monochloroester represented by the formula:
R
f
COOCHClR
f
wherein R
f
is a polyfluoroalkyl group,
the method comprising reacting an aldehyde represented by the formula:
R
f
CHO
wherein R
f
is a polyfluoroalkyl group,
with an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
in the presence of a catalyst.
The present invention provides a method for producing an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
the method comprising reacting a monochloroester represented by the formula:
R
f
COOCHClR
f
wherein R
f
is a polyfluoroalkyl group,
with chlorine in the presence of a catalyst.
The present invention provides a method for producing an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
the method comprising:
(a) a step of reacting a primary alcohol represented by the formula:
R
f
CH
2
OH
wherein R
f
is a polyfluoroalkyl group
with chlorine in the presence of a catalyst to give an aldehyde represented by the formula:
R
f
CHO
wherein R
f
is a polyfluoroalkyl group;
(b) a step of reacting the aldehyde with an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
in the presence of a catalyst to give a monochloroester represented by the formula:
R
f
COOCHClR
f
wherein R
f
is a polyfluoroalkyl group; and
(c) a step of reacting the monochloroester with chlorine in the presence of a catalyst to give the acid chloride.
The present invention provides a method for producing an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
the method comprising:
(a) a step of obtaining an aldehyde having the R
f
group by reacting an alcohol represented by the formula:
R
f
CH
2
OH
wherein R
f
is a polyfluoroalkyl group,
with chlorine in the presence of a catalyst to give the aldehyde represented by the formula:
R
f
CHO
wherein R
f
is a polyfluoroalkyl group,
in which step the alcohol is brought to reflux in a first reactor filled with the catalyst, and is reacted with chlorine supplied continuously, and the aldehyde formed is removed from a column top of the first reactor;
(b) a step of obtaining a monochloroester represented by the formula:
R
f
COOCHClR
f
wherein R
f
is a polyfluoroalkyl group,
by reacting the aldehyde, in the presence of a catalyst, with an acid chloride represented by the formula:
R
f
COCl
wherein R
f
is a polyfluoroalkyl group,
in which step the aldehyde and the acid chloride in their liquid states are introduced in parallel flow into a second reactor filled with the catalyst, and the monochloroester is removed in its liquid state;
(c) a step of obtaining the acid chloride by reacting the monochloroester with chlorine in the presence of a catalyst, in which step the monochloroester in its liquid state and chlorine are introduced in parallel flow or in counterflow into a third reactor filled with the catalyst, and a mixture comprising the acid chloride and the aldehyde is removed in its gas state; and
(d) a step of eliminating the aldehyde from the mixture comprising the aldehyde and the acid chloride, in which aldehyde-eliminating step the mixture liquid comprising the aldehyde and the acid chloride is introduced into a fourth reactor filled with a catalyst, and the acid chloride is removed in its liquid state.
The present invention provides a monochloroester represented by the formula:
H(CF
2
)
6
COOCHCl(CF
2
)
6
H
REFERENCES:
patent: 4124469 (1978-11-01), Bathelt
patent: 4643851 (1987-02-01), Cheminal et al.
patent: 1509110 (1978-04-01), None
patent: 59-98031 (1984-06-01), None
patent: 61-33014 (1986-07-01), None
patent: 61-33014B2 (1986-07-01), None
Kamigata K. et al. Journal of the Chemical Society, No. 3, pp. 627-633, (Mar. 1991).
Nobumasa Kamigata et al., J. Chem. Soc., Perkin Trans. 1 (1991), (3), p. 627-633.
Aoyama Hirokazu
Matsumura Shinichi
Takagi Shoji
Tanaka Yoshinori
Birch & Stewart Kolasch & Birch, LLP
Daikin Industries Ltd.
Killos Paul J.
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