CN101759613B - Preparation method for perfluoroalkyl vikane - Google Patents
Preparation method for perfluoroalkyl vikane Download PDFInfo
- Publication number
- CN101759613B CN101759613B CN 201010104474 CN201010104474A CN101759613B CN 101759613 B CN101759613 B CN 101759613B CN 201010104474 CN201010104474 CN 201010104474 CN 201010104474 A CN201010104474 A CN 201010104474A CN 101759613 B CN101759613 B CN 101759613B
- Authority
- CN
- China
- Prior art keywords
- reaction
- perfluoroalkyl
- vikane
- preparation
- water
- 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.)
- Active
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method for perfluoroalkyl vikane. The steps of the method are as follows: perfluoroiodoalkane and a deiodination reagent carry out sulfination deiodination reaction under the function of a phase transfer catalyst in a polar organic solvent, carry out chlorination reaction with chlorine in inorganic acid or a water-insoluble medium, and then carry out fluoridation reaction with a fluorinating reagent under the function of a compound catalyst with water-alcohol as a reaction medium; finally, products in the above steps are cooled and absorbed to obtain the perfluoroalkyl vikane. The preparation method has the advantages of moderate reaction condition, easy controlling of the reaction process, easy separation as well as purification of the products and high yield.
Description
Technical field
The present invention relates to the preparation method of compound, specifically refer to have general formula C
nF
2n+1SO
2The preparation method of the perfluoroalkyl vikane of F.
Background technology
Perfluoroalkyl vikane has purposes widely, can be used as a lot of activity of organic reaction intermediates and lithium ion battery electrolysis raw material.For example perfluor ethyl sulfonic acid fluoride (PESF) is the important source material of two (the perfluor ethyl sulphonyl) imine lithiums of synthesizing lithium ion electrolytic solution, be also the desirable intermediate of preparation perfluor ethylsulfonic acid and different kinds of ions liquid, or have an intermediate than high reaction activity in multiple perfluor ethyl sulfonate (as perfluor ethyl an alkali metal salt) and multiple low carbon chain perfluoroalkyl preparation process.
The electrofluorination method is that known preparation general formula is C
nF
2n+1SO
2The perfluoroalkyl vikane common method of F (wherein n is 1～3 integer), (Acta Chemical Scandinavica 1999 (53): 1110-1116) etc. the people has done detailed discussion to the method that electrofluorination prepares PESF for Fred G. Drakesmith (Electrofluorination ofOrganic compounds) and N.lgnat ' ev.US Patent No. 2,732,398 have reported the electrofluorination preparation method.Yet the electrofluorination method of the document in these early stages record can produce and comprise SO
2F
2, be difficult to separate with PESF at interior multiple by product with fluoroalkane, thereby the perfluoroalkane based compound of preparation low carbon chain is not had industrial actually operating meaning.In addition, the electrofluorination method generally all has high requirement to equipment, due to the hydrogen rolling action that electrolysis produces, need the low temperature below-78 ℃ PESF could be cooled down fully, and the yield of product is all very low.
The patent No. is 200680035898.X, and the Chinese patent that name is called perfluoroalkane potassium sulfonate and its preparation method improves the electrofluorination method, effectively by product is separated.This patent uses the aqueous solution of potassium hydroxide as gas absorption solution, the salt sedimentation that by product all forms insoluble basically gets off, in reaction process, PESF has generated sulfonate soluble in water and has been retained in the aqueous solution, after removing excessive potassium hydroxide with sulfuric acid, then concentrate by drying and can obtain comparatively pure perfluor ethylsulfonic acid an alkali metal salt.But, prepare PESF via perfluor ethylsulfonic acid an alkali metal salt, general employing phosphorus oxychloride or thionyl chloride chlorination, fluorine atom has very strong electronegativity, when with have higher reaction activity than the reaction of the fluorinated alkyl sulfonate (as perfluoro-methyl sulfonate and perfluor ethyl sulfonate) of short carbon chain, need to use under special catalyst action and just can carry out, but the catalyzer of this type of special role be yet there are no bibliographical information.The patent No. is 03809990.X, and name is called the Chinese patent for the preparation of the catalyzer of perfluor ethyl sulfonic acid fluoride and/or perfluor diethyl sulfone, has reported the method that catalyzes and synthesizes PESF.This patent uses tetrafluoroethylene and sulfurous gas to catalyze and synthesize PESF under two portions catalyst system.But because the method is gas-phase reaction, require the necessary resistance to pressure of reactor better.Because use tetrafluoroethylene (TFE) to be raw material in reactant, the as easy as rolling off a log generation radically homo of tetrafluoroethylene is being arranged under the existence of trace impurity or other initiator again.And the TFE homopolymerization is the very exothermic process and is difficult to control, and easily causes moment High Temperature High Pressure and cause security incident.
Summary of the invention
The purpose of this invention is to provide a kind of reaction conditions gentle, reaction process is easy to control, and product is easy to the preparation method of separating-purifying and the high perfluoroalkyl vikane of recovery rate.
For achieving the above object, preparation method of the present invention is with by general formula C
nF
2n+1The perfluoroalkyl iodide of I (wherein n is 1～3 integer) expression is raw material, passes through successively following reactions steps:
(1), with perfluoroalkyl iodide with take off iodine reagent and under the phase-transfer catalyst effect, inferior sulfonation reaction occurs, generate the basic metal-sulfinate;
(2), basic metal-sulfinate and chlorizating agent are carried out chlorination reaction, generation perfluoroalkane base SULPHURYL CHLORIDE;
(3), perfluoroalkane base SULPHURYL CHLORIDE and fluorizating agent are carried out fluoridation, the generation perfluoroalkyl vikane.
The present invention's technical scheme preferably is:
Described inferior sulfonation reaction is to carry out in polar organic solvent, and described polar organic solvent is a kind of in water-ethanol, formonitrile HCN, acetonitrile, methylene dichloride, acetone, dimethyl formamide, dimethyl sulfoxide (DMSO), dimethyl sulfone, Diethylene Glycol, hexamethylphosphoramide, Nitromethane 99Min., isopropyl ether or Virahol.
In described inferior sulfonation reaction, taking off iodine reagent is Na
2SO
3, Na
2S
2O
4, HOCH
2SO
2Na, (H
2N)
2C=SO
2Na, Na
2S
2O
5, NaHSO
3, K
2SO
3Or K
2S
2O
4In a kind of.
In described inferior sulfonation reaction, phase-transfer catalyst is a kind of in triethylamine, dimethyl formamide, cetyl trimethylammonium bromide or polyoxyethylene glycol.
Described chlorination reaction adopts chlorine to make chlorizating agent.
Described chlorination reaction is carried out in hydrochloric acid or sulfuric acid medium.
Described chlorination reaction is carried out in chlorobenzene, methylene dichloride, trichloromethane or chloric ethane medium.
Described fluorizating agent is KF, KHF
2, NaF, NaHF
2Or C
5H
5A kind of in NHF.
Described fluoridation is to carry out in the water-ethanol reaction medium, and in reaction medium, the weight ratio of water and ethanol is 1: 0.5～1.5, preferred 1: 1.
Added composite catalyst in described fluoridation, composite catalyst is C
mF
2m+1SO
2F and dimethyl formamide complex reagent or C
mF
2m+1SO
2A kind of in the complex reagent of F and triethylamine, described m is 4～12 integer, described C
mF
2m+1SO
2F represents perfluoroalkyl vikane.
In the present invention, the principle of the concrete operations of each reactions steps and each term restriction is as follows:
The iodine reagent that takes off in the present invention all dissolves in polar organic solvent under usual condition, but its solvability is all little, so need to add phase-transfer catalyst to promote the kinetic property of its cosolvency and reaction to reactor in the inferior sulfonation reaction step.Control temperature of reaction kettle between 0 ℃～10 ℃ by the recirculated water of the peripheral chuck of reactor, and then pass into perfluoroalkyl iodide gas in reactor, for sufficient reacting carries out, draft speed is controlled at 5～6kg/h.After perfluoroalkyl iodide gas adds, continue at room temperature to react 2～4h, namely obtain by general formula C
nF
2n+1SO
2The basic metal-sulfinate that M represents is the mixing salt of main component, and described M represents alkalimetal ion.
It is in 5%～10% inorganic acid reaction medium or non-water-soluble reaction medium that the mixing salt that obtains in inferior sulfonation reaction is dissolved in weight percent, then solution is dropped into reactor, passes into chlorine and reacts, and generates to have general formula C
nF
2n+1SO
2The perfluoroalkane base SULPHURYL CHLORIDE of Cl, wherein n is 1～3 integer.In order to occur to suppress side reaction, need to control the draft speed of chlorine in reaction, generally remain on 0.15～0.35L/h, tail gas absorbs with 5% NaOH solution.In this reaction, the exchange of halogen and alkalimetal ion is carried out rapidly, usually do not have high apparent activation energy, again because carbochain is shorter, the boiling point of the perfluoroalkyl SULPHURYL CHLORIDE that generates is lower, if too fast being difficult to of the too high speed of response of the temperature of reactor controlled, also easily cause the target product volatilization, be advisable at-5 ℃～30 ℃ so control temperature of reaction kettle when this step reacts.
After product is completed in chlorination need to carry out the separating-purifying operation.Be the material of strong hydrophobic due to the perfluoroalkyl SULPHURYL CHLORIDE, solubleness is minimum in water, can consider to use pure cold water washing reaction product, and the impurity such as inorganic salt that unreacted mineral acid and reaction generate enter water.Use oil-water separation column or other oily water separating equipments to isolate oil reservoir, repeatedly substantially impurity can be cleaned for three times with cold water washing.Reaction product perfluoroalkyl SULPHURYL CHLORIDE cryopreservation.
During fluoridation, consider that the perfluoroalkyl SULPHURYL CHLORIDE is almost insoluble in water, can adopt cheap water-ethanol can obtain better reaction effect and productive rate as reaction medium, the weight ratio of water and alcohol can select 1: 0.5～1.5 to be advisable, and can obtain comparatively desirable result in preferred 1: 1.In order to reduce the fluorine-containing impurity content that produces in reaction process, in the fluoride salt aqueous solution, the solute weight percent is controlled at 30%～50% scope usually.In order to promote perfluoroalkyl SULPHURYL CHLORIDE and the fluoride salt cosolvency in reaction medium, it is fully contacted react, can add C in fluoridation of the present invention
mF
2m+1SO
2F and dimethyl formamide complex reagent or C
mF
2m+1SO
2A kind of composite catalyst as reaction in the complex reagent of F and triethylamine, described m is 4～12 integer, described C
mF
2m+1SO
2F represents perfluoroalkyl vikane.Temperature of this step reaction is controlled at the lesser temps of-5 ℃～0 ℃, can guarantee speed of response in controlled scope, and the gasification of volatile impurity in can inhibited reaction solution.The perfluoroalkyl sulfonyl fluoride C that reaction obtains
nF
2n+1SO
2F (the wherein integer of n=1～3) steams by reactor upper end prolong, in cold-trap, the steam cooling and absorbing is got final product.
Minimum temperature in preparation method's reaction process of the present invention is controlled at-5 ℃, and within top temperature was controlled at the proper range of 30 ℃, reaction conditions gentleness and reaction process were easy to control, and the product that obtains is easy to separating-purifying.Facts have proved, utilize the perfluoroalkyl sulfonyl fluoride purity of preparation method of the present invention preparation the highest can arrive 99.99% and the content of chlorine element be controlled at below 5ppm, meet the relevant criterion of synthesizing lithium ion battery electrolytic solution.
Embodiment
Embodiment 1
Drop into 180L polar organic solvent dimethyl sulfoxide (DMSO) in the enamel reaction still that stirs to 300L band, that under agitation drops into 51kg takes off iodine reagent Na
2S
2O
4(approximately 292.68mol) and 500g phase-transfer catalyst polyoxyethylene glycol.Close the exhaust-valve of upper end of condenser, the circulating brine by the peripheral chuck layer of reactor is controlled at 0～10 ℃ with temperature in the kettle.Subsequently through a feed-pipe that is deep into below liquid level, control the gas dosing valve, pass into lentamente CF with the speed of 5～6kg per hour
3CF
2The CF of 60kg appears continuing to add after a small amount of the backflow in I gas again in reflux exchanger
3CF
2I (243.90mol), after stop passing into gas, keep 0 ℃ to continue reaction half an hour.Then change logical tap water in reacting kettle jacketing, at room temperature continue reaction 2.5～3.5h.When on reflux exchanger without oil bloom time reaction complete, obtain containing C
2F
5SO
2The mixing salt of Na.Draining the mode organic solvent that unreacted is complete by distillation and negative pressure reclaims.
It is 5～10% aqueous hydrochloric acid that mixing salt obtained in the previous step is dissolved in the 200L weight percent concentration, drops in the 300L enamel reaction still of belt stirrer.Control 0～5 ℃ of temperature in the kettle by chuck recirculated water, 0 ℃ of ice water circulation of reactor upper end employing.Pass into while stirring chlorine, remain on the generation that 0.25L/h speed passes into to suppress side reaction.Tail gas through surge tank, is 5% NaOH alkali lye circulated sprinkling tower absorption with weight concentration.The chlorination reaction time is 4～5h.Reaction solution is pumped into transparent oil-water separation column, isolate upper aqueous layer, re-use isopyknic distilled water and clean oil reservoir three times, responseless mixing salt is removed.By rectifying tower to the separation of purifying of chlorination reaction product.
The chlorizate perfluoroalkyl SULPHURYL CHLORIDE that previous step obtains is weighed, by the mole number metering, the fluorizating agent Potassium monofluoride of 1.1～1.2 times of mole numbers of chlorizate is dissolved in the water-ethanol solution of 1: 1, drop into the fluoridation still of 250L.Pass into-5～0 ℃ of brine refrigeration in the condenser of reactor upper end.While stirring chlorizate is dropped into reactor when temperature in the kettle is controlled at 0 ℃ subsequently.The C that adds at last 10～20ml
4F
9SO
2The composite catalyst of F and 300ml triethylamine.After reacting 4～5h at this temperature, the upper end condenser changes logical tap water, and target product is through-20 ℃ of cooling collections of cold-trap.
The product that obtains is analyzed, prepared perfluor ethyl sulfonic acid fluoride product cl content 0.0003%, reality is received to get perfluor ethyl sulfonic acid fluoride 45.2kg, is equivalent to 92% of theoretical amount.
Embodiment 2
According to the preparation technology of embodiment 1, wherein, during inferior sulfonation reaction, change polar organic solvent into water-ethanol, take off the Na that iodine reagent changes 293mol into
2SO
3Hydrochloric acid medium in the chlorination reaction step changes trichloromethane into; In fluoridation, in the water-ethanol reaction medium, the weight ratio of water and alcohol was selected 1: 0.5, and all the other operations are identical with embodiment 1.
The product that obtains is analyzed, prepared the cl content 0.0004% of perfluor ethyl sulfonic acid fluoride product, the product actual output is 87.1% of theoretical content.
Embodiment 3
According to the preparation technology of embodiment 1, wherein, during inferior sulfonation reaction, change polar organic solvent into Virahol, take off the K that iodine reagent changes 293mol into
2S
2O
4, phase-transfer catalyst changes cetyl trimethylammonium bromide into; In the chlorination reaction step, control 20～25 ℃ of temperature of reaction, solvent medium changes 5～10% dilute sulphuric acid into; In fluorination reaction step, in the water-ethanol reaction medium, the weight ratio of water and alcohol is 1: 1.5, and fluorination reagent changes the KHF that is equivalent to 0.5～0.6 times of perfluoroalkane base SULPHURYL CHLORIDE mole number into
2, all the other operations are identical with embodiment 1.
The product that obtains is analyzed, prepared the cl content 0.0003% of perfluor ethyl sulfonic acid fluoride product, the product actual yield is 83.4% of theoretical content.
Embodiment 4
According to the preparation technology of embodiment 1, wherein, during inferior sulfonation reaction, change polar organic solvent into acetone, take off the HOCH that iodine reagent changes 293mol into
2SO
2Na, phase-transfer catalyst changes dimethyl formamide into; In the chlorination reaction step, control 10～20 ℃ of temperature of reaction, the speed control of logical chlorine is at 0.28L/h, and dielectric solvent changes methylene dichloride into; In fluorination reaction step, fluorination reagent changes the NaHF that is equivalent to 1.1～1.2 times of perfluoroalkane base SULPHURYL CHLORIDE mole numbers into
2, all the other operations are identical with embodiment 1.
The product that obtains is analyzed, prepared the cl content 0.0005% of perfluor ethyl sulfonic acid fluoride product, the product actual yield is 85.5% of theoretical content.
Embodiment 5
According to the preparation technology of embodiment 1, wherein, with CF
3CF
2I changes CF3I into, and polar organic solvent changes isopropyl ether into, takes off the NaHSO that iodine reagent changes 293mol into
3The solvent medium of chlorination reaction is selected chloric ethane, and chlorination reaction is controlled 10-15 ℃ of temperature, and the speed control of logical chlorine is at 0.30L/h; Composite catalyst changes C into
8F
17SO
2The complex reagent of F and dimethyl formamide, in the water-ethanol reaction medium, the weight ratio of water and alcohol is 1: 0.75, all the other operations are identical with embodiment 1.
The product that obtains is analyzed, prepared the cl content 0.0005% of perfluoro-methyl sulfonic acid fluoride product, the product actual yield is 88.6% of theoretical content.
Embodiment 6
According to the preparation technology of embodiment 1, wherein, with CF
3CF
2I changes CF3I into, and polar organic solvent changes Diethylene Glycol into, takes off the K that iodine reagent changes 293mol into
2SO
3, phase-transfer catalyst changes triethylamine into, and the inferior sulfonation reaction temperature is controlled at-5 ℃, in the chlorination reaction step, controls temperature of reaction-5～0 ℃, and solvent medium changes chloric ethane into, and the speed control of logical chlorine is at 0.35L/h; In fluoridation, composite catalyst changes C into
5F
11SO
2The complex reagent of F and triethylamine, all the other are identical with embodiment 1.
The product that obtains is analyzed, and the cl content for preparing perfluoro-methyl sulfonic acid fluoride product is 0.0004%, and the product actual yield is 84.0% of theoretical content.
Embodiment 7
According to the preparation technology of embodiment 1, wherein, with CF
3CF
2I changes CF3I into, and polar organic solvent changes Nitromethane 99Min. into, takes off (the H that iodine reagent changes 293mol into
2N)
2C=SO
2Na; In chlorinating step, solvent medium changes chlorobenzene into, controls 5～10 ℃ of temperature of reaction, and the speed control of logical chlorine is at 0.15L/h; In fluoridation, in the water-ethanol reaction medium, water and pure weight ratio are 1: 1.2, and fluorination reagent changes NaF into, and composite catalyst changes C into
6F
13SO
2The complex reagent of Fy and dimethyl formamide, all the other operations are identical with embodiment 1.
The product that obtains is analyzed, and the cl content for preparing perfluoro-methyl sulfonic acid fluoride product is 0.0003%, and the product actual yield is 84.5% of theoretical content.
Embodiment 8
According to the preparation technology of embodiment 1, wherein, with CF
3CF
2I changes perfluor iodo propane into, and polar organic solvent changes acetonitrile into, takes off the Na that iodine reagent changes 293mol into
2S
2O
5Chlorinating step is controlled 25～30 ℃ of temperature of reaction, and the speed control of chlorine is at 0.20L/h, and fluorination reagent changes C into
5H
5NHF; Composite catalyst changes C into
11F
23SO
2The complex reagent of F and dimethyl formamide, all the other operations are identical with embodiment 1.
The product that obtains is analyzed, prepared the cl content 0.0005% of perfluoro propyl sulfonic acid fluoride product, the product actual yield is 88.0% of theoretical content.
Embodiment 9
According to the preparation technology of embodiment 1, wherein, with CF
3CF
2I changes perfluor iodo propane into, and polar organic solvent changes dimethyl formamide into, takes off the Na that iodine reagent changes 293mol into
2SO
3, sulfination salify step reaction temperature is controlled at 5-10 ℃; Chlorinating step is controlled 10-15 ℃ of temperature of reaction, chlorine pass into speed control at 0.20L/h; Fluorination reagent changes NaF into, and in the water-ethanol reaction medium, the weight ratio of water and alcohol is 1: 1.5, and composite catalyst changes C into
8F
17SO
2The complex reagent of F and triethylamine, all the other operations are identical with embodiment 1.
The product that obtains is analyzed, prepared the cl content 0.0003% of perfluoro propyl sulfonic acid fluoride product, the product actual yield is 87.6% of theoretical content.
Embodiment 10
According to the preparation technology of embodiment 1, wherein, with CF
3CF
2I changes perfluor iodo propane into, and polar organic solvent changes hexamethylphosphoramide into, takes off the HOCH that iodine reagent changes 293mol into
2SO
2Na, sulfination salify step reaction temperature is controlled at 5-10 ℃; Chlorinating step is controlled 10-15 ℃ of temperature of reaction; In fluoridation, fluorination reagent changes KHF into, and composite catalyst changes C into
12F
25SO
2The complex reagent of F dimethyl formamide, all the other operations are identical with embodiment 1.
The product that obtains is analyzed, prepared the cl content 0.0004% of perfluoro propyl sulfonic acid fluoride product, the product actual yield is 86.8% of theoretical content.
Claims (4)
1. the preparation method of a perfluoroalkyl vikane comprises the following steps:
(1), with perfluoroalkyl iodide with take off iodine reagent and under the phase-transfer catalyst effect, inferior sulfonation reaction occurs, generate the basic metal-sulfinate;
(2), basic metal-sulfinate and chlorizating agent are carried out chlorination reaction, generation perfluoroalkane base SULPHURYL CHLORIDE;
(3), perfluoroalkane base SULPHURYL CHLORIDE and fluorizating agent are carried out fluoridation, generate perfluoroalkyl vikane, described fluoridation is to carry out in the water-ethanol reaction medium, in reaction medium, the weight ratio of water and ethanol is 1: 0.5～1.5, added composite catalyst in described fluoridation, composite catalyst is C
mF
2m+1SO
2F and dimethyl formamide complex reagent or C
mF
2m+1SO
2A kind of in the complex reagent of F and triethylamine, described m is 4～12 integer, described C
mF
2m+1SO
2F represents perfluoroalkyl vikane; Wherein:
Taking off iodine reagent described in inferior sulfonation reaction is Na
2SO
3, Na
2S
2O
4, HOCH
2SO
2Na, (H
2N)
2C=SO
2Na, Na
2S
2O
5, NaHSO
3, K
2SO
3Or K
2S
2O
4In a kind of; Phase-transfer catalyst described in inferior sulfonation reaction is a kind of in triethylamine, dimethyl formamide, cetyl trimethylammonium bromide or polyoxyethylene glycol; Adopt chlorine as chlorizating agent in chlorination reaction; Described fluorizating agent is KF, KHF
2, NaF, NaHF
2Or C
5H
5A kind of in NHF.
2. the preparation method of perfluoroalkyl vikane according to claim 1, it is characterized in that: inferior sulfonation reaction is to carry out in polar organic solvent, and described polar organic solvent is a kind of in water-ethanol, formonitrile HCN, acetonitrile, methylene dichloride, acetone, dimethyl formamide, dimethyl sulfoxide (DMSO), dimethyl sulfone, Diethylene Glycol, hexamethylphosphoramide, Nitromethane 99Min., isopropyl ether or Virahol.
3. the preparation method of described perfluoroalkyl vikane according to claim 1 and 2, it is characterized in that: chlorination reaction is to carry out in hydrochloric acid or sulfuric acid medium.
4. the preparation method of described perfluoroalkyl vikane according to claim 1 and 2, it is characterized in that: chlorination reaction is to carry out in chlorobenzene, methylene dichloride, trichloromethane or chloric ethane medium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010104474 CN101759613B (en) | 2010-01-29 | 2010-01-29 | Preparation method for perfluoroalkyl vikane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010104474 CN101759613B (en) | 2010-01-29 | 2010-01-29 | Preparation method for perfluoroalkyl vikane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101759613A CN101759613A (en) | 2010-06-30 |
| CN101759613B true CN101759613B (en) | 2013-05-08 |
Family
ID=42491015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201010104474 Active CN101759613B (en) | 2010-01-29 | 2010-01-29 | Preparation method for perfluoroalkyl vikane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101759613B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102108057B (en) * | 2010-12-10 | 2013-07-10 | 上海博康精细化工有限公司 | Method for preparing adamantane sulfonyl chloride by using adamantane sulfinyl chloride |
| CN102992944B (en) * | 2012-11-26 | 2014-12-10 | 中国人民解放军防化学院 | Preparation method of heptadecafluorooctyl iodoalkane |
| CN105753742B (en) * | 2014-12-19 | 2018-03-09 | 山东东岳高分子材料有限公司 | A kind of method for preparing perfluoroalkene ethers sulfonyl fluoride compound |
| CN112266343A (en) * | 2020-12-02 | 2021-01-26 | 应急管理部消防产品合格评定中心 | Synthetic method of perfluorohexyl sodium ethyl sulfonate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101429664A (en) * | 2008-11-20 | 2009-05-13 | 湖北恒新化工有限公司 | Full-fluorine octyl sulfuryl fluoride production technology |
-
2010
- 2010-01-29 CN CN 201010104474 patent/CN101759613B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101429664A (en) * | 2008-11-20 | 2009-05-13 | 湖北恒新化工有限公司 | Full-fluorine octyl sulfuryl fluoride production technology |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101759613A (en) | 2010-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106316809B (en) | A method of preparing perfluorethyl isopropyl ketone | |
| US20230278862A1 (en) | Synthesis method of hexafluorophosphate | |
| CN105722820B (en) | The synthesis of fluoro trifluoromethanesulp-onyl -onyl imide | |
| CN101842348B (en) | Process for preparation of trifluoromethanesulfonyl fluoride | |
| CN106276829B (en) | A kind of synthetic method of double fluorine sulfimide lithiums | |
| CN101759613B (en) | Preparation method for perfluoroalkyl vikane | |
| CN102105444B (en) | Process for producing perfluoroalkanesulfinic acid salt | |
| CN105693561A (en) | Preparation method of trifluoromethane sulfonic acid | |
| CN107381522A (en) | A kind of preparation method of double fluorine sulfimides and the method that double fluorine sulfimide alkali metal salts are prepared using the double fluorine sulfimides prepared | |
| CN107286060A (en) | End group is the preparation method of the perfluoroalkyl vinyl ether of sulfonyl fluoride group | |
| CN103641748B (en) | A kind of recycle by-product hydrochloric acid prepares the method for methylsulphonic acid | |
| CA2984854A1 (en) | Method for preparation of bis(fluorosulfonyl)-imide | |
| JP6158328B2 (en) | Method for producing sulfonimide compound and salt thereof | |
| CN107445792A (en) | A kind of o-fluorotobuene preparation method | |
| CN109942539A (en) | A kind of preparation method of the fluoro- 1,3- propane sultone of 2- | |
| CN103288587B (en) | A kind of preparation method of perfluoro alkane | |
| CN114805288A (en) | Method for preparing 2, 4-butane sultone | |
| CN108017574B (en) | A kind of method of the chloro- 2,4,6- trifluoromethyl pyridine continuous production of fluroxypramide intermediate 3,5- bis- | |
| CN106905290B (en) | A kind of preparation method of difluoroethylene carbonate | |
| CN103360202A (en) | Preparation method of hexafluorobenzene and chloropentafluorobenzene | |
| CN105175294B (en) | Method for synthesizing sulfanilamide by using chlorobenzene as raw material | |
| JP5497799B2 (en) | Process for producing perfluorobutane sulfonate | |
| CN209537352U (en) | Hexafluoropropylene dimmer prepares the device of perfluor isobutyl ether | |
| CN105753631A (en) | Synthetic method of fluorine-containing aromatic compounds | |
| CN107739292A (en) | A kind of synthetic method of short-chain perfluoroaldyl iodine |
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 |