CN1441763A - Process for producing fluoroalcohol - Google Patents
Process for producing fluoroalcohol Download PDFInfo
- Publication number
- CN1441763A CN1441763A CN 01812510 CN01812510A CN1441763A CN 1441763 A CN1441763 A CN 1441763A CN 01812510 CN01812510 CN 01812510 CN 01812510 A CN01812510 A CN 01812510A CN 1441763 A CN1441763 A CN 1441763A
- Authority
- CN
- China
- Prior art keywords
- fluorine
- gained
- containing alcohol
- alcohol
- tetrafluoroethylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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; (ii) contacting the resultant crude reaction product with a base and then removing the solid and tar generated; and (iii) distilling the crude reaction product treated in the step (ii) to recover the fluoroalcohol represented by the general formula (1). Thus, a fluoroalcohol containing substantially no impurities can be produced through a smooth distillation operation without clogging the piping and distillation column.
Description
Technical field
The present invention relates to prepare the method for fluorine-containing alcohol.
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, in 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, so when for example being provided with the solvent of carrier of the recording layer that can information be write and/or read by laser, exist influence can't be applicable to the shortcoming of making high-quality carrier because of the evaporation of residual part as the substrate of making CD-R or DVD-R etc.
H (the CF that contains the evaporation of residual composition as preparation hardly
2CF
2)
nCH
2The method of OH (n=1,2) discloses in No. 302918 communique of patent, the resultant of reaction of methyl alcohol and tetrafluoroethylene or R 1216 is distilled in the presence of alkali, maybe with this resultant of reaction with distill after alkali contacts.Yet, in this method, easy blocking pipe of the solids component that resultant of reaction and alkali reaction generated or distillation tower, this can hinder the carrying out of distillation procedure greatly.
The announcement of invention
Main purpose of the present invention provides a kind of not blocking pipe or distillation tower, can be by the method for the fluorine-containing alcohol free from foreign meter in fact of distillation procedure preparation smoothly.
The present inventor studies in great detail in view of above-mentioned problem, found that, with the reacting coarse product of tetrafluoroethylene and methyl alcohol reaction gained with after alkali contacts, remove the solids component and the tar ingredients such as NaF of generation from the treatment trough bottom, afterwards, when the composition that will contain fluorine-containing alcohol is supplied in distillation procedure, can blocking pipe or distillation tower, and can prepare fluorine-containing alcohol free from foreign meter in fact by distillation procedure smoothly, finish 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 (iii):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) with the reacting coarse product of gained with after alkali contacts, remove the solids component that generated and the step of tar ingredients,
(iii) distill the reacting coarse product of (ii) handling through above-mentioned steps, 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 (iv):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) distill the reacting coarse product of gained, will be back in the reactor by 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) with the fluorine-containing alcohol of gained with after alkali contacts, remove the solids component that generated and the step of tar ingredients,
(iv) distill the fluorine-containing alcohol of (iii) handling through above-mentioned steps, 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, 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 in the reactor by 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) with the fluorine-containing alcohol of gained with after alkali contacts, remove the solids component that generated and the step of tar ingredients,
(v) distill the fluorine-containing alcohol of (iv) handling through above-mentioned steps, 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 (vi):
(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 in the reactor by 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) from the fluorine-containing alcohol of gained, separate HCF
2CF
2CH
2OH step,
(v) with isolating HCF
2CF
2CH
2OH is with after alkali contacts, and removes the solids component that generated and the step of tar ingredients,
(vi) distill through above-mentioned steps (the v) HCF of Chu Liing
2CF
2CH
2OH reclaims HCF
2CF
2CH
2The step of OH.
5. according to above-mentioned the 4th method for preparing fluorine-containing alcohol, wherein step (reclaims HCF vi)
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.
In the inventive method, at first be 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.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 enumerate superoxide, the transformation period that can preferably enumerate temperature of reaction is about 10 hours reaction initiator.
As preferred reaction initiator, can enumerate 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 of basic metal such as lime carbonate, magnesiumcarbonate, yellow soda ash, salt of wormwood, sodium bicarbonate, saleratus or alkaline-earth metal or supercarbonate, calcium oxide, calcium hydroxide, soda-lime, barium carbonate etc.Preferably do not make reactant be tied to form strong basicity, and can hold back the sour agent that is subjected to of acid such as HF that when reaction produce.
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 by method for preparing formula (1), the reacting coarse product of gained is contacted with alkali.
As alkali, preferred pKb is the alkali below 2.As alkali so, can enumerate alkali metal alcoholates such as sodium methylate, sodium ethylate, sodium propylate, potassium tert.-butoxide, lithium ethoxide; Alkali-metal oxyhydroxide 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.As the usage quantity of alkali, for the C3-Fluoroalcohol of every 1kg weight, be 0.05 to 1.0 mole, be preferably 0.1 to 0.5 mole.
The alkali of operational condition when contacting with to(for) reacting coarse product is not particularly limited, and gets final product in 0.5 to 3 hour but generally react down at 20 to 150 ℃.
When reacting coarse product contacts with alkali like this, because of containing severals ppm of producing by side reaction HF in the reacting coarse product, so it is reacted solids component or tar ingredients such as generation NaF, KF with alkali in treatment trough (alkaline purification groove) to hundreds of ppm.Especially, solids component becomes the reason of blocking pipe in after this processing or distillation tower.Therefore, remove solids component and tar ingredients, to the further distillation and being purified of the composition that contains fluorine-containing alcohol from the alkaline purification trench bottom.With after alkali contacts, remove solids component and tar ingredients from the alkaline purification groove like this, the composition that will contain fluorine-containing alcohol is supplied in the distillation procedure of later step, can prevent the obstruction of pipeline and distillation tower.And, in the distillation procedure of step,,, reduce the amount of impurity in the product in the still kettle of distillation tower in the back so can reduce the generation of resolvent in the distillation procedure because of tar ingredients does not concentrate.
Then, contain composition, the Separation and Recovery fluorine-containing alcohol of fluorine-containing alcohol, can obtain not containing in fact the fluorine-containing alcohol of above-mentioned formula (1) expression of evaporation of residual composition by distillation.
In addition, the operation that reacting coarse product is contacted with alkali can be carried out remove superfluous methyl alcohol from reacting coarse product by methods such as distillations after.In this distillation procedure, distillate methyl alcohol by the cat head of distillation tower, fluorine-containing alcohol is contained at the bottom of the tower in the composition.Utilize again by turning back to by the methyl alcohol of cat head gained in the reactor, can effectively utilize.
And, in the inventive method, after tetrafluoroethylene and the methyl alcohol reaction, preferably from reacting coarse product, remove CaF
2, NaF etc. resultant of reaction that is subjected to sour agent and the unreacted residue that is subjected to sour agent.This operation is not particularly limited, got final product by sour agent resultant of reaction and the unreacted method of sour agent that is subjected to, for example, can use separating centrifuge to remove effectively so long as can from reacting coarse product, remove solid.
In addition, the fluorine-containing alcohol C3-Fluoroalcohol that obtains 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, further by methods such as distillations, with the C3-Fluoroalcohol of n=1 in the formula (1) and n is after fluorine-containing alcohol more than 2 separates, and the C3-Fluoroalcohol of Separation and Recovery is contacted with alkali get final product.
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, distillates C3-Fluoroalcohol by the cat head of distillation tower, and the fluorine-containing alcohol of n 〉=2 is contained at the bottom of the tower in the composition.Therefore,, contact with alkali according to aforesaid method for the composition that contains by the C3-Fluoroalcohol of cat head gained, from the alkaline purification groove, remove solids component and tar ingredients after, the composition that contains C3-Fluoroalcohol is carried out distillation procedure gets final product.
In the alkaline purification groove, can produce resultant of reaction such as alcohol or water, this resultant of reaction or can sneak in the C3-Fluoroalcohol as the low boiling point components such as alcohol of the solvent of alkali according to the alkali kind of using.Therefore, at first, carry out from tetrafluoro alcohol, separating the distillation procedure of removing low boiling point component alcohol, water etc., then as subordinate phase as the distillation procedure of fs, the distillation procedure of preferred distillation by the fs as tower at the bottom of the composition that contains tetrafluoro alcohol that get of composition, recovery tetrafluoro alcohol.Such distillating method can not sneaked into alcohol or water, C3-Fluoroalcohol free from foreign meter in fact.
In addition, replace such two-stage distillation procedure, can after low boiling point components such as alcohol, water are removed in distillation successively, reclaim tetrafluoro alcohol from 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 " means, the evaporation of residual composition of fluorine-containing alcohol is below the 50ppm, be preferably below the 25ppm, more preferably below the 10ppm, and, be below the 0.1abs as absorbancy (205nm) in the methyl alcohol of this evaporation of residual part content's index, preferably-below the 0.1abs, more preferably-below the 0.2abs.
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.
And the absorbancy in the methyl alcohol as measuring sample, uses methyl alcohol to measure as the reference sample with the material that adds 3ml methyl alcohol gained in general formula (1) fluorine-containing alcohol of 1ml.
The C3-Fluoroalcohol free from foreign meter in fact of the inventive method gained for example, can be suitable for use as the solvent when being manufactured on substrate and being provided with the carrier of the recording layer that can information be write and/or read by laser.
Substrate is provided with the carrier of the recording layer that can information be write and/or read by laser, can be by solvent at the C3-Fluoroalcohol that contains gained of the present invention, be preferably in the fluorine series solvent that contains C3-Fluoroalcohol and dissolve pigment, the solution of gained is coated on the substrate with ordinary method, carry out methods such as drying again, formation contains the recording layer of pigment and makes.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.In addition,, undercoat can be set also, or protective layer is set on recording layer also can to improve planarity between recording layer and substrate, increase clinging power, to prevent that the rotten etc. of recording layer from being purpose.
Preparation method of the present invention can not produce obstruction in pipeline or distillation tower, can prepare the fluorine-containing alcohol of formula free from foreign meter in fact (1).
The C3-Fluoroalcohol of institute's Separation and Recovery from the fluorine-containing alcohol of gained like this, free from foreign meter in fact, be suitable for use as the solvent of photoreceptors 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 etc.
The simple declaration of accompanying drawing
Fig. 1 represents the schema of continuous still battery step among the embodiment 1.Among the figure, 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.
The best mode that carries out an invention
Below enumerate embodiment and illustrate in greater detail the present invention.
Embodiment 1
In autoclave, add methyl alcohol (2 liters), Perbutyl D (45g) and lime carbonate (30g).Behind the nitrogen replacement reactor, with the initial velocity adding tetrafluoroethylene of 600 Grams Per Hours, controlled temperature is 125 ℃, and pressure is 0.8MPa, reacts 6 hours.
The reacting coarse product of gained (HF:1300 quality ppm, C3-Fluoroalcohol 27% (GC analytical value), the trimethyl carbinol: 0.16% (GC analytical value)),, handle with following method by the continuous still battery step shown in the schema of Fig. 1.
At first, reacting coarse product is imported separating centrifuge 2 by 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, be recycled in the reactor 1.Composition is delivered 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.
Afterwards, isolating C3-Fluoroalcohol is delivered to alkaline purification groove 5, for 1Kg C3-Fluoroalcohol interpolation 30g sodium methylate (28% methanol solution) and after stirring, remove solids component and tar ingredients from the bottom of alkaline purification groove 5, the composition that will contain C3-Fluoroalcohol imports alkaline distillation tower 6.
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 the C3-Fluoroalcohol of purity more than 99.9% as the stage casing cut.
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 (iii):
(i) step that tetrafluoroethylene and methyl alcohol are reacted,
(ii) with the reacting coarse product of gained with after alkali contacts, remove the solids component that generated and the step of tar ingredients,
(iii) distill the reacting coarse product of (ii) handling through above-mentioned steps, 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 (iv):
(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) with the fluorine-containing alcohol of gained with after alkali contacts, remove the solids component that generated and tar ingredients step,
(iv) distill the fluorine-containing alcohol of (iii) handling through above-mentioned steps, 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, 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 step as the fluorine-containing alcohol of the formula (1) of composition gained at the bottom of the tower,
(iv) with the fluorine-containing alcohol of gained with after alkali contacts, remove the solids component that generated and the step of tar ingredients,
(v) distill the fluorine-containing alcohol of (iv) handling through above-mentioned steps, 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 (vi):
(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) the fluorine-containing alcohol from gained separates HCF
2CF
2CH
2OH step,
(v) with isolating HCF
2CF
2CH
2OH is with after alkali contacts, and removes the solids component that generated and the step of tar ingredients,
(vi) distill through above-mentioned steps (the v) HCF of Chu Liing
2CF
2CH
2OH reclaims HCF
2CF
2CH
2The step of OH.
5. the method for preparing fluorine-containing alcohol of claim 4, wherein step (reclaims HCF vi)
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP257848/2000 | 2000-08-28 | ||
| JP257848/00 | 2000-08-28 | ||
| JP2000257848A JP2002069019A (en) | 2000-08-28 | 2000-08-28 | Method for producing fluorine-containing alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1441763A true CN1441763A (en) | 2003-09-10 |
| CN1242967C CN1242967C (en) | 2006-02-22 |
Family
ID=18746246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01812510 Expired - Fee Related CN1242967C (en) | 2000-08-28 | 2001-07-13 | Process for producing fluoroalcohol |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2002069019A (en) |
| CN (1) | CN1242967C (en) |
| TW (1) | TW572879B (en) |
| WO (1) | WO2002018309A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718630A (en) * | 2012-06-11 | 2012-10-10 | 中昊晨光化工研究院 | Tetrafluoropropanol rectification purifying method |
| CN103694082A (en) * | 2013-11-26 | 2014-04-02 | 浙江巨圣氟化学有限公司 | Method for purifying tetrafluoro propanol |
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 JP2000257848A patent/JP2002069019A/en active Pending
-
2001
- 2001-07-13 CN CN 01812510 patent/CN1242967C/en not_active Expired - Fee Related
- 2001-07-13 WO PCT/JP2001/006075 patent/WO2002018309A1/en active Application Filing
- 2001-08-01 TW TW90118775A patent/TW572879B/en not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718630A (en) * | 2012-06-11 | 2012-10-10 | 中昊晨光化工研究院 | Tetrafluoropropanol rectification purifying method |
| CN102718630B (en) * | 2012-06-11 | 2014-07-02 | 中昊晨光化工研究院 | Tetrafluoropropanol rectification purifying method |
| CN103694082A (en) * | 2013-11-26 | 2014-04-02 | 浙江巨圣氟化学有限公司 | Method for purifying tetrafluoro propanol |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002069019A (en) | 2002-03-08 |
| WO2002018309A1 (en) | 2002-03-07 |
| TW572879B (en) | 2004-01-21 |
| CN1242967C (en) | 2006-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101009858B1 (en) | Process for producing an organic compound | |
| JPH06116259A (en) | New fluorodioxole and its production | |
| CN1117053C (en) | Producing process for fuoro-alcohol | |
| CN1120830C (en) | Process for producing fluoroalcohol | |
| CN1242967C (en) | Process for producing fluoroalcohol | |
| CN1203038C (en) | Process for producing fluoroalcohol compound | |
| CN1305825C (en) | Purifying method for propanol tetrafluoride | |
| CN1441762A (en) | Process for producing fluoroalcohol | |
| CN1244526C (en) | Process for producing a fluorinated alcohol | |
| CN1438980A (en) | Process for producing fluoroalcohol | |
| CN1122653C (en) | Process for producing fluoroalcohol | |
| JPS5988431A (en) | Production of isobutylene | |
| CN1946667A (en) | Process for producing fluorinated (meth)acrylic ester | |
| EP1191009B1 (en) | Process for producing fluoroalkanol | |
| WO2001062694A1 (en) | Process for preparation of 2,2,3,4,4,4-hexafluoro-1-butanol and use thereof | |
| JPH0559123B2 (en) | ||
| JP2002332280A (en) | Method for producing oxetane compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20060222 Termination date: 20100713 |