Process for production of fluoroalcohol

Details Process for production of fluoroalcohol Process for production of fluoroalcohol

1999-09-01

2002-05-21

O'Sullivan, Peter (Department: 1774)

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

C568S904000, C568S913000

Reexamination Certificate

active

06392105

ABSTRACT:

TECHNICAL FIELD
The invention relates to a process for producing a fluoroalcohol of the general formula (1):
H (CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
represents F or CF
3
, when n=1; R
1
represents F, when n=2), said fluoroalcohol which is substantially impurity-free, and use of said fluoroalcohol for the manufacture of an information recording medium comprising a substrate and as built thereon a recording layer adapted for laser writing and/or reading.
BACKGROUND ART
Regarding the technology of producing H(CF
2
CF
2
)
n
CH
2
OH (n=1, 2), it is disclosed in Japanese Unexamined Patent Publication 154707/1979 and U.S. Pat. No. 2,559,628 that a mixture of telomers, i.e., H(CF
2
CF
2
)
n
CH
2
OH (n=12 at a maximum), can be produced by reacting methanol with tetrafluoroethylene in the presence of t-butyl octyl peroxide.
However, even if the telomer mixture obtained by this process is purified by distillation, the evaporation residue of the order of about a few hundreds of ppm cannot be eliminated, with the result that when it is used as a solvent in the manufacture of an information recording medium comprising a substrate and as built thereon a recording layer adapted for laser writing and/or reading, such as CD-R and DVD-R, for instance, the disadvantage is inevitable that the quality of the information recording medium is not high enough owing to the influence of said evaporation residue.
It is an object of the invention to provide a fluoroalcohol of the following general formula (1)
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein n and R1 are as defined above), which is substantially free of impurities such as an evaporation residue and UV-absorbing substances, a method for producing said fluoroalcohol, use of said fluoroalcohol as a solvent for the manufacture of an information recording medium comprising a substrate and as built thereon a recording layer adapted for laser writing and/or reading, and an information recording medium comprising a substrate and as built thereon a recording layer adapted for laser writing and/or reading.
DISCLOSURE OF THE INVENTION
The invention relates to the following 1-20.
1. A method for producing a fluoroalcohol of the following formula (1):
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
represents F or CF
3
, when n=1; R
1
represents F, when n=2) comprising reacting methanol with tetrafluoroethylene or hexafluoropropylene in the presence of a free radical source, wherein the reaction mixture is subjected to distillation either in the presence of a base or after contact of said reaction mixture with a base.
2. The process for producing a fluoroalcohol as defined in claim
1
wherein the base is a substance having a pKb value of not more than 2.
3. The process for producing a fluoroalcohol as defined in claim
1
wherein the base is an alkali metal alkoxide or an alkali metal hydroxide.
4. The process for producing a fluoroalcohol as defined in claim
1
wherein the base is at least one selected from the group consisting of sodium alkoxides, sodium hydroxide and potassium hydroxide.
5. The process for producing a fluoroalcohol as defined in claim
1
wherein the fluoroalcohol of the formula (1)
H (CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
and n are as defined above) as obtained by distillation has an evaporation residue of not more than 50 ppm.
6. The process for producing a fluoroalcohol as defined in claim
5
wherein the fluoroalcohol of the formula (1)
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
and n are as defined above) as obtained by distillation has an evaporation residue of not more than 25 ppm.
7. The process for producing a fluoroalcohol as defined in claim
5
wherein the fluoroalcohol of the formula (1)
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
and n are as defined above) as obtained by distillation has an evaporation residue of not more than 10 ppm.
8. The process for producing a fluoroalcohol as defined in claim
1
wherein the free radical source is at least one selected from the group consisting of a reaction initiator, UV and heat.
9. The process for producing a fluoroalcohol as defined in claim
8
wherein the free radical source is a reaction initiator having an half-life at the reaction temperature of about 10 hours.
10. The process for producing a fluoroalcohol as defined in claim
8
wherein the free radical source is a peroxide.
11. The process for producing a fluoroalcohol as defined in claim
8
wherein the free radical source is di-t-butylperoxide, t-butylperoxyisopropylcarbonate or t-butylperoxy-2-ethylhexanoate.
12. The process for producing a fluoroalcohol as defined in claim
1
wherein an acid acceptor is used together with the free radical source.
13. A fluoroalcohol of the following formula (1)
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
represents F or CF
3
, when n=1; R
1
represents F, when n=2) which has an evaporation residue of not more than 50 ppm.
14. The fluoroalcohol according to claim
13
, the evaporation residue of which is not more than 25 ppm.
15. The fluoroalcohol according to claim
13
, the evaporation residue of which is not more than 10 ppm.
16. The fluoroalcohol according to claim
13
, the absorbance (190-300 nm) in methanol of which is not more than 0.2 abs.
17. The fluoroalcohol according to claim
13
, the absorbance (205 nm) in methanol of which is not more than 0.1 abs.
18. The fluoroalcohol according to claim
17
, the absorbance (205 nm) in methanol of which is not more than −0.2 abs.
19. Use of the fluoroalcohol claimed in claim
13
for the manufacture of an information recording medium comprising a substrate and as built thereon a recording layer adapted for laser writing and/or reading.
20. An information recording medium comprising a substrate and as built thereon a recording layer adapted for laser writing and/or reading as fabricated using the fluoroalcohol of the following formula (1)
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
represents F or CF
3
, when n=1; R
1
represents F, when n=2) as produced by the process as defined in claim
1
or the fluoroalcohol of the following formula (1)
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein R
1
represents F or CF
3
, when n=1; R
1
represents F, when n=2) as defined in claim
13
.
In the production process according to the invention, methanol is used in excess over tetrafluoroethylene or hexafluoropropylene. The reaction temperature is about 40-140° C., the reaction time is about 3-12 hours, and the reaction pressure is about 0.2-1.2 MPa. This reaction can be conducted in a high pressure reactor such as autoclave, for instance. The reaction system is preferably subjected to an inert gas purging using nitrogen, argon or the like gas.
Upon completion of the reaction, the excess methanol is optionally distilled off and the residue is further subjected to distillation in the presence of a base. Furthermore, in the event the reaction mixture contains H(CF
2
CF
2
)
n
CH
2
OH (n≧3) or H(CF(CF
3
)CF
2
)
n
CH
2
OH (n≧2) as impurity, the impurity is preferably removed in advance by distillation. The reaction mixture containing the fluoroalcohol of the formula (1)
H(CFR
1
CF
2
)
n
CH
2
OH  (1)
(wherein n and R
1
are as defined above) is subjected to distillation either in the presence of a base or after contacting the reaction mixture with a base.
The base to be added to the above reaction mixture or contacted therewith is preferably a base with a pKb value of not more than 2, thus including alkali metal alkoxides such as sodium methoxide, sodium ethoxide, sodium propoxide, potassium t-butoxide, lithium ethoxide, etc., alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, etc., calcium hydroxide, aluminum hydroxide, barium hydroxide, magnesium hydroxide and soda lime. The proportion of the base is about 0.05-1.0 mole, preferably about 0.1-0.5 mole, per 1 kg of the reaction mixture from which methanol has been removed.
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