CN1441761A - Process for producing fluoroalcohol compound - Google Patents
Process for producing fluoroalcohol compound Download PDFInfo
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- CN1441761A CN1441761A CN 01812507 CN01812507A CN1441761A CN 1441761 A CN1441761 A CN 1441761A CN 01812507 CN01812507 CN 01812507 CN 01812507 A CN01812507 A CN 01812507A CN 1441761 A CN1441761 A CN 1441761A
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- fluorine
- containing alcohol
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
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Abstract
A process for producing a fluoroalcohol represented by the general formula (1) H(CF2CF2)nCH2OH (1) (wherein n is 1 or 2) from tetrafluoroethylene and methanol as starting materials in the presence of a free-radical generator, characterized by comprising the steps of: (i) reacting tetrafluoroethylene with methanol; and (ii) distilling the resultant crude reaction product either in the presence of a base and water or after bringing it into contact with a base and water to thereby recover the fluoroalcohol represented by the general formula (1). Thus, a fluoroalcohol can be produced which contains substantially no impurities and is suitable for use in producing information recording media (e.g., optical disks such as CD-R and DVD-R), etc.
Description
Technical field
The present invention relates to the preparation method of fluorine-containing alcohol compound.
Background technology
As H (CF
2CF
2)
nCH
2The preparation method of OH (n=1,2) opens in No. 2559628, clear 54-154707 communique and the United States Patent (USP) as the spy and to disclose, and in the presence of tertiary butyl octyl group superoxide, excessive methyl alcohol and tetrafluoroethylene is reacted, and obtains H (CF
2CF
2)
nCH
2The telomer mixture of OH (n is up to 12).
Yet, the telomer mixture of this method gained, even pass through distillation purifying, also can't remove the evaporation of residual part of hundreds of ppm, pretend solvent when being provided with the carrier of the recording layer that can information be write and/or read by laser as the substrate of CD-R or DVD-R etc. when using, exist influence can't be applicable to the shortcoming of making high-quality carrier because of the evaporation of residual part for Production Example.
In addition, known by with above-mentioned telomer mixture in the presence of the alkali or with carry out the distillatory method after alkali contacts, can obtain the few fluorine-containing alcohol of foreign matter content (No. 3029618 communique of patent).Yet, when the solvent during as manufacturing information recording medium uses, be expected to obtain impurity level fluorine-containing alcohol still less.
The announcement of invention
Main purpose of the present invention provides the method for a kind of preparation fluorine-containing alcohol free from foreign meter in fact, and this fluorine-containing alcohol compound is applicable to makes the carrier (CD of CD-R, DVD-R etc. etc.) etc. that substrate is provided with the recording layer that can information be write and/or read by laser.
The present inventor is in view of above-mentioned problem, through studying in great detail, found that the reacting coarse product that makes tetrafluoroethylene and methyl alcohol reaction gained, in the presence of alkali and water, or with alkali with distill after water contacts, in the presence of alkali or with alkali, contact back distillatory situation with this reacting coarse product and compare, can make impurity level still less, can obtain fluorine-containing alcohol free from foreign meter in fact.Finished the present invention thus.
That is, the invention provides the following method for preparing fluorine-containing alcohol.
1. a method for preparing fluorine-containing alcohol is in the presence of the free-radical generating source, is starting raw material with tetrafluoroethylene and methyl alcohol, preparation following formula (1)
H(CF
2CF
2)
nCH
2OH (1)
The method of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented is characterized in that comprising the steps that (i) is extremely (ii):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) the reacting coarse product with gained distills in the presence of alkali and water, maybe this reacting coarse product is contacted the back distillation with alkali and water, the step of the fluorine-containing alcohol of recovery type (1).
2. a method for preparing fluorine-containing alcohol is in the presence of the free-radical generating source, is starting raw material with tetrafluoroethylene and methyl alcohol, preparation following formula (1)
H(CF
2CF
2)
nCH
2OH (1)
The method of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented is characterized in that comprising the steps that (i) is extremely (iii):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) distill the reacting coarse product of gained, will turn back to the reactor from the methyl alcohol of the cat head gained of distillation tower and utilize again, reclaim step as the fluorine-containing alcohol of the formula (1) of composition gained at the bottom of the tower,
(iii) the gained fluorine-containing alcohol is distilled in the presence of alkali and water, maybe this fluorine-containing alcohol is contacted the back distillation with alkali and water, the step of the fluorine-containing alcohol of recovery type (1).
3. method for preparing fluorine-containing alcohol is in the free-radical generating source and be subjected in the presence of the sour agent, is starting raw material with tetrafluoroethylene and methyl alcohol, preparation following formula (1)
H(CF
2CF
2)
nCH
2OH (1)
The method of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented is characterized in that comprising the steps that (i) is extremely (iv):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) from the reacting coarse product of gained, remove the resultant of reaction and the unreacted step that is subjected to sour agent that are subjected to sour agent,
(iii) distill the reacting coarse product of gained, will be back to the reactor from the methyl alcohol of the cat head gained of distillation tower and utilize again, reclaim step as the fluorine-containing alcohol of the formula (1) of composition gained at the bottom of the tower,
(iv) the fluorine-containing alcohol with gained distills in the presence of alkali and water, maybe this fluorine-containing alcohol is contacted the back distillation with alkali and water, the step of the fluorine-containing alcohol of recovery type (1).
4. method for preparing fluorine-containing alcohol, be the free-radical generating source and be subjected to sour agent in the presence of, be starting raw material with tetrafluoroethylene and methyl alcohol, preparation
Formula: HCF
2CF
2CH
2OH
The method of represented fluorine-containing alcohol, it is characterized in that comprising the steps (i) to (v):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) from the reacting coarse product of gained, remove the resultant of reaction and the unreacted step that is subjected to sour agent that are subjected to sour agent,
(iii) distill the reacting coarse product of gained, will be back to the reactor from the methyl alcohol of the cat head gained of distillation tower and utilize again, reclaim formula (1) as composition gained at the bottom of the tower
H(CF
2CF
2)
nCH
2OH (1)
The step of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented,
(iv) distill the fluorine-containing alcohol of gained, separate HCF
2CF
2CH
2The step of OH,
(v) with isolating HCF
2CF
2CH
2OH distills in the presence of alkali and water, maybe this fluorine-containing alcohol is contacted the back distillation with alkali and water, reclaims HCF
2CF
2CH
2The step of OH.
5. above-mentioned the 4th method for preparing fluorine-containing alcohol, wherein step (recovery HCF v)
2CF
2CH
2The method of OH is that distillation contains the composition of HCF2CF2CH2OH and after removing low boiling point component, distills the HCF that contains as composition gained at the bottom of the tower once more
2CF
2CH
2The composition of OH reclaims HCF
2CF
2CH
2The method of OH.
In the inventive method, at first in the presence of the free-radical generating source, tetrafluoroethylene and methyl alcohol are reacted, preparation following formula (1)
H(CF
2CF
2)
nCH
2OH (1)
(in the formula, n represents 1 or 2) represented fluorine-containing alcohol.
As the free-radical generating source, can use to be selected from least a of reaction initiator, UV and heat.If when the free-radical generating source is UV, for example can use UV from the medium-pressure or high pressure mercuryvapour lamp.When the free-radical generating source is hot, under 250～300 ℃ temperature, heats and get final product.As reaction initiator, can exemplify superoxide, the transformation period that can preferably exemplify temperature of reaction is about 10 hours reaction initiator.
As preferred reaction initiator, can exemplify Perbutyl D (ditertiary butyl peroxide), Perbutyl O (t-butylperoxy-2-ethylhexanoate), Perbutyl I (t-butylperoxy sec.-propyl carbonic ether) etc.The usage quantity of this reaction initiator for per 1 mole tetrafluoroethylene, is generally 0.005 to 0.1 mole.
In the above-mentioned reaction, it is excessive that the methyl alcohol Paratetrafluoroethylene uses.Temperature of reaction is 40 to 140 ℃, and the reaction times is 3 to 12 hours, and reaction pressure is 0.2 to 1.2Mpa to get final product.Reaction for example can be carried out in autoclave.In the reaction system preferably with inert gas replacements such as nitrogen, argon gas.
The preparation feedback of fluorine-containing alcohol be subjected to sour agent in the presence of carry out.As being subjected to sour agent, can enumerate the carbonate or the supercarbonate of basic metal such as lime carbonate, magnesiumcarbonate, yellow soda ash, salt of wormwood, sodium bicarbonate, saleratus or alkaline-earth metal; Calcium oxide, calcium hydroxide, soda-lime, barium carbonate etc.Be subjected to sour agent preferably not make reactant be tied to form strong basicity, and can hold back the acid such as HF that produce when reacting.
Be subjected to the usage quantity of sour agent,, for per 1 mole tetrafluoroethylene, be 0.001 to 0.1 mole and get final product though be not particularly limited.
In the method for preparing fluorine-containing alcohol of the present invention, behind the fluorine-containing alcohol shown in the method for preparing formula (1), the reacting coarse product of gained is distilled in the presence of alkali and water, or with distill after alkali and water contact, can obtain not containing in fact the fluorine-containing alcohol of evaporation of residual composition.
As alkali, preferred pKb is the alkali below 2.As such alkali, can enumerate alkali metal alcoholates such as sodium methylate, sodium ethylate, sodium propylate, potassium tert.-butoxide, lithium ethoxide; Alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide; Calcium hydroxide, aluminium hydroxide, hydrated barta, magnesium hydroxide, soda-lime etc.Wherein, special preferred as alkali alkoxide.
For the fluorine-containing alcohol of 100 weight parts, the usage quantity of preferred bases is 0.1 to 10 weight part, more preferably 1 to 3 weight part.
In addition, for the fluorine-containing alcohol of 100 weight parts, the usage quantity of preferably water is 0.1 to 10 weight part, more preferably 1 to 3 weight part.
In the presence of alkali and water during the distillation reaction crude product, alkali and water added in the stage casing of distillation tower or the still kettle to getting final product.In addition, when distilling after alkali and water contact, set handling groove before distillation tower (alkaline purification groove) gets final product with this reacting coarse product.At this moment, though the operational condition of this alkaline purification groove is not particularly limited, generally adds the reaction of under 20 to 150 ℃, carrying out 0.5 to 3 hour behind the alkali and get final product.
Like this in the presence of alkali and water, or with distill after alkali and water contact, the Separation and Recovery fluorine-containing alcohol can obtain not containing in fact the represented fluorine-containing alcohol of above-mentioned formula (1) of evaporation of residual composition.
In addition, this distills processing, carries out also can after the distillation reaction crude product is removed superfluous methyl alcohol.Be used for removing the distillation procedure of methyl alcohol, because of the cat head from distillation tower distillates methyl alcohol, fluorine-containing alcohol is contained at the bottom of the tower in the liquid, so effectively utilize by being back to from the methyl alcohol that cat head obtains to utilize the reactor again.
And, in the methods of the invention, after tetrafluoroethylene and the methyl alcohol reaction, preferably from reacting coarse product, remove CaF
2, being subjected to sour agent resultant of reaction and unreactedly being subjected to sour agent of NaF etc.This operation is not particularly limited, and got final product by sour agent resultant of reaction and the unreacted method of sour agent that is subjected to so long as can remove solid from reacting coarse product, for example by using separating centrifuge to remove effectively.
In addition, the fluorine-containing alcohol C3-Fluoroalcohol of wishing to get n=1 in the formula (1) is during as the finished product, from reacting coarse product, remove superfluous methyl alcohol by methods such as distillations on demand, and, be after fluorine-containing alcohol more than 2 separates, for the C3-Fluoroalcohol of Separation and Recovery with the C3-Fluoroalcohol of the middle n=1 of formula (1) and n by method such as distillation, according to above-mentioned condition, in the presence of alkali and water, or with distill after alkali and water contact, reclaim C3-Fluoroalcohol and get final product.
At this moment, at C3-Fluoroalcohol that is used for separate type (1) n=1 and n is in the distillation procedure of the fluorine-containing alcohol more than 2, distillate C3-Fluoroalcohol from the cat head of distillation tower, the fluorine-containing alcohol of n 〉=2 is contained at the bottom of the tower in the composition, therefore, for C3-Fluoroalcohol, carry out distillation procedure according to aforesaid method and get final product from the cat head gained.
With C3-Fluoroalcohol in the presence of alkali and water, or with distill after alkali and water contact, can obtain C3-Fluoroalcohol free from foreign meter in fact.
When handling, can produce resultant of reaction such as alcohol or water, this resultant of reaction, water, can sneak in the C3-Fluoroalcohol as the low boiling point components such as the employed alcohol of solvent of alkali according to the kind of the alkali that uses with alkali and water.Therefore, wish to get highly purified C3-Fluoroalcohol, at first as the distillation procedure of fs, carry out from tetrafluoro alcohol, removing the distillation procedure of low boiling point component alcohol, water etc., then as subordinate phase, distillation procedure that will be by the fs as tower at the bottom of the composition that contains tetrafluoro alcohol that gets of composition distill, it is good reclaiming tetrafluoro alcohol.By such distillating method, do not sneak into alcohol or water, can obtain C3-Fluoroalcohol free from foreign meter in fact.
In addition, replace such two-stage distillation procedure, also can after low boiling point components such as alcohol, water are removed in distillation successively, reclaim tetrafluoro alcohol in the cat head or the stage casing of distillation tower, but above-mentioned two-stage distillating method can reclaim highly purified C3-Fluoroalcohol simply.
In addition, " free from foreign meter in fact " is meant, the evaporation of residual composition of fluorine-containing alcohol is below the 50ppm, be preferably below the 25ppm, more preferably below the 10ppm, in addition, as absorbancy (205nm) in the methyl alcohol of this evaporation of residual part content's index is below the 0.1abs, preferably-below the 0.1abs, more preferably-below the 0.2abs, more preferably-below the 0.4abs.
Here, the weight of its lingering section is shown the evaporation of residual component list to HCF when being determined at the down concentrated fluorine-containing alcohol of 40 ℃, 5mmHg (0.665KPa)
2CF
2CH
2The quality ppm of OH.
In addition, the absorbancy in the methyl alcohol to add 3ml methyl alcohol gained material as measuring sample in the fluorine-containing alcohol of 1ml general formula (1), uses methyl alcohol to measure as reference sample.
The C3-Fluoroalcohol free from foreign meter in fact of the inventive method gained, for example, can be suitably solvent when making substrate and be provided with the carrier of the recording layer that information can be write and/or reads by laser.
Substrate is provided with the carrier of the recording layer that information can be write and/or reads by laser and can makes by the following method: at the solvent of the C3-Fluoroalcohol that contains gained of the present invention, preferably contain in the fluorine series solvent of C3-Fluoroalcohol and dissolve pigment, the solution of gained is coated on the substrate with ordinary method, carry out methods such as drying, form the recording layer that contains pigment.As this pigment, can enumerate cyanines is that pigment, phthalocyanine are that pigment, pyrans are that pigment, sulfo-pyrans are that pigment, spiny dogfish (squalilium) are that pigment, Azulene (azurenium) are that pigment, indigo fen are that pigment, indoaniline (indoaniline) are that pigment, triphenyl methane are that pigment, quinone are that pigment, aluminium are that pigment, diimmonium (diimmonium) are that pigment, metallic complex salt are pigment etc.As substrate, can enumerate plastics such as polycarbonate, polymethylmethacrylate, Resins, epoxy, amorphous polyolefin, polyester, polyvinyl chloride, glass, pottery etc.And, to improve planarity between recording layer and substrate, increase clinging power, to prevent that the rotten etc. of recording layer from being purpose, undercoat also can be set, or on recording layer, protective layer be set.
The inventive method is compared with distillatory situation in the presence of alkali, can obtain the evaporation of residual composition still less, the fluorine-containing alcohol of formula (1) free from foreign meter in fact.
C3-Fluoroalcohol by method Separation and Recovery of the present invention, free from foreign meter in fact, be suitable as the isochronous solvents of photoreceptor such as the carrier (CD of CD-R, DVD-R etc. etc.) making substrate and be provided with the recording layer that can information be write and/or read by laser, egative film.
Description of drawings
Fig. 1 is the schema of continuous still battery step among the expression embodiment 1.1 is that reactor, 2 is that separating centrifuge, 3 is that first distillation tower, 4 is that second column, 5 is that alkaline purification groove, 6 is that alkaline distillation tower, 7 is alkaline distillation tower among the figure.
The best mode that carries out an invention
Below enumerate embodiment and illustrate in greater detail the present invention.
Embodiment 1
In autoclave, drop into methyl alcohol (2 liters), Perbutyl D (45 gram) and lime carbonate (30 gram).With behind the nitrogen replacement, the initial velocity of tetrafluoroethylene with 600 Grams Per Hours added in the reactor, controlled temperature is 125 ℃, and pressure is 0.8MPa, reacts 6 hours.
Reacting coarse product (HF:1300 quality ppm, C3-Fluoroalcohol 27% (GC analytical value), the trimethyl carbinol: 0.16% (GC analytical value)),, handle for gained with following method according to the continuous still battery step shown in the schema of Fig. 1.
At first, reacting coarse product is imported separating centrifuge 2 from reactor 1, by centrifugation with unreacted be subjected to sour agent and removed by the resultant of reaction of sour agent after, deliver to first distillation tower 3.
Then, in first distillation tower 3, methyl alcohol is distillated, and be recycled in the reactor 1.Composition is sent to second column 4 at the bottom of containing the tower of fluorine-containing alcohol, separate contain the cut of C3-Fluoroalcohol (n=1) and contain the tower of fluorine-containing alcohol of n in the formula (1) 〉=2 at the bottom of composition.
Next, isolating C3-Fluoroalcohol is delivered to alkaline purification groove 5, add 45 gram sodium methylates (28% methanol solution) and 30 gram water, import alkaline distillation tower 6 after 2 hours through 110 ℃ of following heat treated for C3-Fluoroalcohol (1 liter).
Then, distill in alkaline distillation tower 6, methyl alcohol and water distillate from cat head, will contain the tower of C3-Fluoroalcohol at the bottom of composition deliver to alkaline distillation tower 7.
Afterwards, by in alkaline distillation tower 7, distilling, obtain as the stage casing cut, the C3-Fluoroalcohol of purity more than 99.9%.Comparative experiments example 1
In the C3-Fluoroalcohol of 2200 grams by the method gained identical with embodiment 1, add 66 gram sodium methylates (28% methanol solution), distill.
Fluorine-containing alcohol cut to gained carries out the absorbancy analysis, and the absorbancy minimum value is-0.2 (abs) in 200 to 220nm absorption band.Experimental example 1
In the C3-Fluoroalcohol of 3000 grams by the method gained identical with embodiment 1, add 90 gram sodium methylates (28% methanol solution) and 62 and restrain water, distill.
Fluorine-containing alcohol cut to gained carries out the absorbancy analysis, and the absorbancy minimum value has been confirmed to compare with comparative experiments example 1 for for-0.4 (abs) in 200 to 220nm absorption band, and its absorbancy minimum value is little, and impurity level (evaporation of residual composition) is few.
Claims (5)
1. a method for preparing fluorine-containing alcohol is in the presence of the free-radical generating source, is starting raw material with tetrafluoroethylene and methyl alcohol, preparation following formula (1)
H(CF
2CF
2)
nCH
2OH (1)
The method of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented is characterized in that comprising the steps that (i) is extremely (ii):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) the reacting coarse product with gained distills in the presence of alkali and water, maybe this reacting coarse product is contacted the back distillation with alkali and water, the step of the fluorine-containing alcohol of recovery type (1).
2. a method for preparing fluorine-containing alcohol is in the presence of the free-radical generating source, is starting raw material with tetrafluoroethylene and methyl alcohol, preparation following formula (1)
H(CF
2CF
2)
nCH
2OH (1)
The method of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented is characterized in that comprising the steps that (i) is extremely (iii):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) distill the reacting coarse product of gained, will be back to the reactor from the methyl alcohol of the cat head gained of distillation tower and utilize again, reclaim step as the fluorine-containing alcohol of the formula (1) of composition gained at the bottom of the tower,
(iii) the fluorine-containing alcohol with gained distills in the presence of alkali and water, maybe this fluorine-containing alcohol is contacted the back distillation with alkali and water, the step of the fluorine-containing alcohol of recovery type (1).
3. method for preparing fluorine-containing alcohol is in the free-radical generating source and be subjected in the presence of the sour agent, is starting raw material with tetrafluoroethylene and methyl alcohol, preparation following formula (1)
H(CF
2CF
2)
nCH
2OH (1)
The method of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented is characterized in that comprising the steps that (i) is extremely (iv):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) from the reacting coarse product of gained, remove the resultant of reaction and the unreacted step that is subjected to sour agent that are subjected to sour agent,
(iii) distill the reacting coarse product of gained, will be back to the reactor from the methyl alcohol of the cat head gained of distillation tower and utilize again, reclaim step as the fluorine-containing alcohol of the formula (1) of composition gained at the bottom of the tower,
(iv) the fluorine-containing alcohol with gained distills in the presence of alkali and water, maybe this fluorine-containing alcohol is contacted the back distillation with alkali and water, the step of the fluorine-containing alcohol of recovery type (1).
4. method for preparing fluorine-containing alcohol, be the free-radical generating source and be subjected to sour agent in the presence of, be starting raw material with tetrafluoroethylene and methyl alcohol, preparation
Formula: HCF
2CF
2CH
2OH
The method of represented fluorine-containing alcohol, it is characterized in that comprising the steps (i) to (v):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) from the reacting coarse product of gained, remove the resultant of reaction and the unreacted step that is subjected to sour agent that are subjected to sour agent,
(iii) distill the reacting coarse product of gained, will be back to the reactor from the methyl alcohol of the cat head gained of distillation tower and utilize again, reclaim formula (1) as composition gained at the bottom of the tower
H(CF
2CF
2)
nCH
2OH (1)
The step of the fluorine-containing alcohol that (in the formula, n represents 1 or 2) is represented,
(iv) distill the fluorine-containing alcohol of gained, separate HCF
2CF
2CH
2The step of OH,
(v) with isolating HCF
2CF
2CH
2OH distills in the presence of alkali and water, maybe this fluorine-containing alcohol is contacted the back distillation with alkali and water, reclaims HCF
2CF
2CH
2The step of OH.
5. the method for preparing fluorine-containing alcohol of claim 4, wherein step (recovery HCF v)
2CF
2CH
2The method of OH is that distillation contains HCF
2CF
2CH
2The composition of OH and after removing low boiling point component, distill the HCF that contains once more as composition gained at the bottom of the tower
2CF
2CH
2The composition of OH reclaims HCF
2CF
2CH
2The method of OH.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP257842/2000 | 2000-08-28 | ||
| JP2000257842A JP2002069018A (en) | 2000-08-28 | 2000-08-28 | Method for producing fluorine-containing alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1441761A true CN1441761A (en) | 2003-09-10 |
| CN1203038C CN1203038C (en) | 2005-05-25 |
Family
ID=18746240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01812507 Expired - Fee Related CN1203038C (en) | 2000-08-28 | 2001-07-13 | Process for producing fluoroalcohol compound |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2002069018A (en) |
| CN (1) | CN1203038C (en) |
| TW (1) | TW572876B (en) |
| WO (1) | WO2002018307A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100412042C (en) * | 2005-03-01 | 2008-08-20 | 常熟三爱富中昊化工新材料有限公司 | Purifying method for propanol tetrafluoride |
| CN102924235A (en) * | 2012-11-26 | 2013-02-13 | 山东科技大学 | Purification method for octafluoropentyl alcohol |
| CN111825528A (en) * | 2020-06-15 | 2020-10-27 | 三明市海斯福化工有限责任公司 | Method for purifying fluorine-containing alcohol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3915759A1 (en) * | 1989-05-13 | 1990-11-15 | Hoechst Ag | METHOD FOR PRODUCING TELOMERAL ALCOHOLS |
| JP3029618B1 (en) * | 1998-12-28 | 2000-04-04 | ダイキン工業株式会社 | Manufacturing method of fluorine alcohol |
| JP3026804B1 (en) * | 1999-03-15 | 2000-03-27 | ダイキン工業株式会社 | Manufacturing method of fluorine alcohol |
-
2000
- 2000-08-28 JP JP2000257842A patent/JP2002069018A/en active Pending
-
2001
- 2001-07-13 WO PCT/JP2001/006073 patent/WO2002018307A1/en active Application Filing
- 2001-07-13 CN CN 01812507 patent/CN1203038C/en not_active Expired - Fee Related
- 2001-07-26 TW TW90118352A patent/TW572876B/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100412042C (en) * | 2005-03-01 | 2008-08-20 | 常熟三爱富中昊化工新材料有限公司 | Purifying method for propanol tetrafluoride |
| CN102924235A (en) * | 2012-11-26 | 2013-02-13 | 山东科技大学 | Purification method for octafluoropentyl alcohol |
| CN102924235B (en) * | 2012-11-26 | 2016-04-20 | 山东科技大学 | A kind of method of purification of octafluoropentanol |
| CN111825528A (en) * | 2020-06-15 | 2020-10-27 | 三明市海斯福化工有限责任公司 | Method for purifying fluorine-containing alcohol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1203038C (en) | 2005-05-25 |
| WO2002018307A1 (en) | 2002-03-07 |
| JP2002069018A (en) | 2002-03-08 |
| TW572876B (en) | 2004-01-21 |
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