CN104672055B - The method of perfluoro alkyl ethylene is separated from perfluor alkyl ethyl acrylate crude product - Google Patents
The method of perfluoro alkyl ethylene is separated from perfluor alkyl ethyl acrylate crude product Download PDFInfo
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- CN104672055B CN104672055B CN201310639252.4A CN201310639252A CN104672055B CN 104672055 B CN104672055 B CN 104672055B CN 201310639252 A CN201310639252 A CN 201310639252A CN 104672055 B CN104672055 B CN 104672055B
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Abstract
A kind of method that the present invention relates to Separation and Recovery perfluoro alkyl ethylene from perfluor alkyl ethyl acrylate crude product comprises: perfluor alkyl ethyl acrylate crude product is carried out rectifying, obtains the first rectifying solution containing perfluoro alkyl ethylene; Add alkali liquid washing and activated alumina decolouring to the first rectifying solution of gained, and then carry out water, oil, solid phase three phase separation, obtain the oil phase containing perfluoro alkyl ethylene; In the oil phase of perfluoro alkyl ethylene, add a small amount of stopper, and carry out rectifying, obtain perfluoro alkyl ethylene.Perfluoro alkyl ethylene in perfluor alkyl ethyl acrylate crude product can be purified to more than 99.9% by separation method provided by the invention, can directly sell as high value-added product, improve the utilising efficiency of industrial chemicals, decrease the discharge of industrial chemicals.
Description
Technical field
The present invention relates to chemical field, be specifically related to a kind of method of Separation and Recovery perfluoro alkyl ethylene from the crude product of perfluor alkyl ethyl acrylate.
Background technology
Perfluoro alkyl ethylene (perfluoroalkyl iodides Addition on ethylene thing) is a kind of important fluorochemical surfactant intermediate, and can generate the kinds of surface promoting agents such as perfluorocarboxylic acid after peroxidation, therefore this material has the wide market space.The method of general synthesizing perfluoroalkyl ethene is that perfluoroalkyl iodides and ethene carry out addition reaction, then carries out eliminative reaction in the basic conditions and generates perfluoro alkyl ethylene.
Perfluoro alkyl ethylene acrylate is the very important fluorochemical surfactant of one, is therefore widely used as three-proof finishing agent in fields such as weaving, leathers because it has the characteristics such as special hydrophobic, oleophobic.And the main method of synthesizing perfluoroalkyl ethyl propylene acid esters is reacted under alcoholic solvent with perfluor alkyl ethide iodine and potassium acrylate exactly.Because the condition of this reaction is harsher, generally need to carry out under the high temperature of 200 DEG C, and very easily there is eliminative reaction generation perfluoro alkyl ethylene in raw material perfluor alkyl ethide iodine with this understanding.
Traditional technique by product alkene and underproof solvent is mixed to carry out burning disposal, and this treatment process not only energy consumption is high, and complex treatment process, finally can only obtain the hydrofluoric acid of about 30%.
Summary of the invention
In order to find a kind of recovery method of perfluoro alkyl ethylene, improving its recycle value, the object of this invention is to provide a kind of method of Separation and Recovery perfluoro alkyl ethylene from perfluor alkyl ethyl acrylate crude product.
The method of Separation and Recovery perfluoro alkyl ethylene from perfluor alkyl ethyl acrylate crude product provided by the invention comprises:
Perfluor alkyl ethyl acrylate crude product is carried out rectifying, obtains the first rectifying solution containing perfluoro alkyl ethylene; Add alkali liquid washing and activated alumina decolouring to the first rectifying solution of gained, and then carry out water, oil, solid phase three phase separation, obtain the oil phase containing perfluoro alkyl ethylene; In the oil phase of perfluoro alkyl ethylene, add a small amount of stopper, and carry out rectifying, obtain perfluoro alkyl ethylene.
An embodiment for the rectification step of described crude product, comprising: by the rectifying in rectifying tower of perfluor alkyl ethyl acrylate crude product, collects the main thick cut containing perfluoro alkyl ethylene.
The embodiment of the rectification step of another kind of preferred described crude product, comprise: perfluor alkyl ethyl acrylate crude product is carried out first time rectifying in rectifying tower, obtain mainly containing the different fractions of perfluoro alkyl ethylene acrylate, perfluoro alkyl ethylene and solvent respectively; Respectively the cut containing solvent, perfluor alkyl ethyl acrylate is carried out second time rectifying, and obtain the component containing perfluoro alkyl ethylene respectively further, merge all liquid phases containing perfluoro alkyl ethylene, obtain described elementary rectifying solution.
Described first time, the pressure of distillation operation was preferably 5-40Kpa, more preferably 20-40Kpa.In described first distillation operation, collect main containing solvent cut for 40-90 DEG C, collect main containing perfluoro alkyl ethylene cut for 90-110 DEG C, tower reactor material is main perfluor alkyl ethyl acrylate cut.
Described containing in the second time rectifying of solvent cut, will carry out rectifying containing solvent cut, rectifying pressure is 5-40Kpa, and be preferably 20-40Kpa, rectification temperature is 40-90 DEG C, is preferably 60-90 DEG C of tower reactor and obtains mainly containing the cut of perfluoro alkyl ethylene.
Described containing in the second time rectifying of perfluor alkyl ethyl acrylate cut, comprise and will carry out rectifying containing perfluor alkyl ethyl acrylate cut, rectifying pressure is 5-40Kpa, is preferably 20-40Kpa, rectification temperature is 90-110 DEG C, and tower top obtains mainly containing the cut of perfluoro alkyl ethylene.
Further preferably, above-mentioned perfluor alkyl ethyl acrylate crude product is carried out rectifying before, also comprise the operation that described crude product is filtered.
The method of a kind of preferred Separation and Recovery perfluoro alkyl ethylene from perfluor alkyl ethyl acrylate crude product provided by the invention, comprises the steps:
Perfluor alkyl ethyl acrylate crude product is carried out filter operation, obtains coarse filtration liquid; First time rectifying is carried out to coarse filtration liquid, obtains mainly containing the different fractions of perfluoro alkyl ethylene acrylate, perfluoro alkyl ethylene and solvent respectively; Carry out second time rectifying to main containing solvent, perfluor alkyl ethyl acrylate cut, and obtain the component containing perfluoro alkyl ethylene respectively respectively; Merge all liquid phases containing perfluoro alkyl ethylene, obtain mixed solution; In mixed solution, add basic solution, activated alumina decolours, then carries out water, oil, solid phase three phase separation, obtains the oil phase containing perfluoro alkyl ethylene; Add stopper to containing in the oil phase of perfluoro alkyl ethylene, and carry out third time rectifying, obtain perfluoro alkyl ethylene.
The rectifying pressure of described third time rectifying is 5-40Kpa, and be preferably 20-40Kpa, temperature is 90-110 DEG C, is preferably 100-110 DEG C.
In perfluoro alkyl ethylene described in the present invention, alkyl refers to the alkyl of C6-C14, it can be mixture, such as, can be the following perfluoro alkyl ethylene mixture of variant alkyl mass percent: the C6 alkyl of 20%, the C8 alkyl of 40%, C10, C12 and C14 alkyl of 40%.
The method of above-mentioned Separation and Recovery perfluoro alkyl ethylene from perfluor alkyl ethyl acrylate crude product, wherein, described alkali liquid washing step, preferably adopt mass percent concentration be 3 ~ 10% inorganic alkali solution perfluoro alkyl ethylene cut is washed, then wash with water to neutrality.
Wherein, described inorganic alkali solution is preferably one or more the basic solution in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood.
Wherein, described stopper is preferably the combination of one or more in kautschin, triethylamine or glycerol.
Perfluoro alkyl ethylene in perfluor alkyl ethyl acrylate crude product can be purified to more than 99.9% by separation method provided by the invention, directly can sell as high value-added product, improve the utilising efficiency of material, decrease the discharge of industrial chemicals.
Present invention also offers a kind of process system being applicable to above-mentioned separation method, it is formed as shown in Figure 1, in figure: 1 perfluor alkyl ethyl acrylate reactor, 2 strainers, 3 filtrate transferpumps, 4 compound rectifying tower, 5 condenser 1#, 6 solvent crude product storage tanks, 7 perfluoro alkyl ethylene crude product storage tanks, 8 tower reactor material conveying pump 1#, 9 tower reactor material conveying pump 2#, 10 solvent distillation towers, 11 condenser 2#, 12 high-purity solvent feed tanks, 13 perfluor alkyl ethyl acrylate rectifying tower, 14 condenser 3#, 15 perfluoro alkyl ethylene crude product storage tanks, 16 tower reactor material conveying pump 3#, 17 perfluoro alkyl ethylene rectifying tower, 18 condenser 4#, 19 high-purity perfluoro alkyl ethylene storage tanks, 20 tower reactor material conveying pump 3#.
The using method of this process system comprises:
1) according to diagram, each equipment is installed;
2) in 1 reactor, carry out the preparation feedback of perfluor alkyl ethyl acrylate, obtain reacted liquid phase material; Liquid phase material is flow in 2 strainers by pipeline and filters, gained filtrate is transported in 4 compound rectifying tower through 3 filtrate transferpumps carries out first time rectifying, main solvent-laden cut rectifying obtained is placed in 6 solvent crude product storage tanks, the main cut containing perfluoro alkyl ethylene is placed in 7 perfluoro alkyl ethylene crude product storage tanks, and tower reactor material is mainly containing the cut of perfluor alkyl ethyl acrylate;
3) cut in 6 solvent crude product storage tanks is carried out second time rectifying through 10 solvent distillation towers, gained solvent cut is placed in 12 high-purity solvent feed tanks, and tower reactor material is mainly containing the cut of perfluoro alkyl ethylene;
4) the tower reactor material after first time rectifying is transported to 13 perfluor alkyl ethyl acrylate rectifying tower by 8 tower reactor material conveying pump 1# and carries out second time rectifying, gained is mainly placed in 15 perfluoro alkyl ethylene crude product storage tanks containing the cut of perfluoro alkyl ethylene, and tower reactor material is mainly containing the cut of perfluor alkyl ethyl acrylate;
5) by the tower reactor material of 10 solvent distillation towers, the cut in 7 perfluoro alkyl ethylene crude product storage tanks and 15 perfluoro alkyl ethylene crude product storage tanks all needs to be transported in 17 perfluoro alkyl ethylene rectifying tower, and carry out third time rectifying, tower reactor material is high-purity perfluoro alkyl ethylene.
Optionally, described process system can also be implemented as follows step:
6) the tower reactor material of 17 is passed through 20 pump delivery to 15 perfluoro alkyl ethylene crude product storage tanks, rectifying is again carried out to the tower reactor material containing more heavy constituent, be separated the perfluor alkyl ethyl acrylate obtained wherein.Complete the internal recycling rectifying of tower reactor material, to improve the output of variant production.
Accompanying drawing explanation
Fig. 1 is the process system that separation method of the present invention uses.
Embodiment
Following examples for illustration of the present invention, but are not used for limiting the scope of the invention.If do not specialize, reagent used in embodiment is conventional commercial reagent, the conventional means that in embodiment, NM technique means is well known to those skilled in the art.
Embodiment 1
(1) by the liquid phase material in 100Kg perfluor alkyl ethyl acrylate reactor, flow in strainer by pipeline, obtained filtrate 108Kg is placed in rectifying tower, in tower, working pressure is about 20KPa, collect the thick cut 38Kg of solvent of 40-80 DEG C respectively, the 90-110 DEG C of thick cut 6Kg of cut perfluoro alkyl ethylene, tower reactor material is the thick cut 64Kg of perfluor alkyl ethyl acrylate.
(2) the thick cut of perfluoro alkyl ethylene obtained in step (1) is placed in rinse bath, with the speed of 5Kg/min add wherein mass percent concentration be 5% KOH solution carry out washing (KOH solution consumption is about 10Kg), and constantly to stir.After alkali liquid washing terminates, then add deionized water wherein with certain speed and carry out washing until be washed till neutrality (deionized water consumption is about 15Kg).
(3) disposablely in the thick cut of perfluoro alkyl ethylene obtained in step (2) active alumina powder (40 order) 50g is added.After leaving standstill system 40min, system is divided into water, oil, consolidates three layers, filters and obtains oil phase.In oil-phase product, add deionized water with certain speed again to carry out washing until be washed till neutrality (deionized water consumption is about 15Kg).
(4) disposablely in the thick cut of perfluoro alkyl ethylene obtained in step (3) stopper kautschin 20g is added.
(5) the perfluoro alkyl ethylene cut obtained in step (4) is placed in rectifying tower, in tower, working pressure is about 20KPa, and service temperature is 100 DEG C, collects tower reactor material perfluoro alkyl ethylene 4.85Kg, product purity 99.7%.
Embodiment 2
(1) by the liquid phase material in 100Kg perfluor alkyl ethyl acrylate reactor, flow in strainer 2 by pipeline, obtained filtrate 112Kg is placed in rectifying tower, in tower, working pressure is about 30KPa, collect the thick cut 45Kg of solvent of 40-60 DEG C respectively, the thick cut 6.2Kg of perfluoro alkyl ethylene of 90-100 DEG C, tower reactor material is the thick cut 60.8Kg of perfluor alkyl ethyl acrylate.
(2) the thick cut of solvent that step (1) obtains is placed in rectifying tower, in tower, working pressure is about 20KPa, collects the thick cut 42Kg of solvent of 40-60 DEG C respectively, and tower reactor material is mainly containing the thick cut 3Kg of thick cut ethyl propylene acid esters of perfluoroalkyl;
(3) the thick cut of perfluor alkyl ethyl acrylate step (1) obtained is in rectifying tower, and in tower, working pressure is about 20KPa, and rectification temperature is 90 DEG C, and it is main containing the thick cut 1.2Kg of perfluoro alkyl ethylene that collection tower top obtains;
(4) the thick cut of perfluoro alkyl ethylene obtained in step (1), (2), (3) is merged, be placed in rinse bath, with the speed of 2Kg/min add wherein mass percent concentration be 3% KOH solution carry out washing (KOH solution consumption is about 11Kg), and constantly to stir.After alkali liquid washing terminates, then add deionized water wherein with certain speed and carry out washing until be washed till neutrality (deionized water consumption is about 15Kg).
(5) disposablely in the thick cut of perfluoro alkyl ethylene obtained in step (4) active alumina powder (40 order) 50g is added.After leaving standstill system 40min, system is divided into water, oil, consolidates three layers, filters and obtains oil phase.In oil-phase product, add deionized water with certain speed again to carry out washing until be washed till neutrality (deionized water consumption is about 15Kg).
(6) stopper triethylamine 20g is added in the perfluoro alkyl ethylene oil phase obtained in step (5), be placed in rectifying tower, in tower, working pressure is about 20KPa, and service temperature is 100 DEG C, collect tower reactor material perfluoro alkyl ethylene 5.1Kg, product purity is greater than 99.9%.
Embodiment 3
(1) by the liquid phase material in 100Kg perfluor alkyl ethyl acrylate reactor, flow in strainer 2 by pipeline, obtained filtrate 110Kg is placed in rectifying tower, in tower, working pressure is about 40KPa, collect the thick cut 45Kg of solvent of 40-90 DEG C respectively, the thick cut 6.2Kg of perfluoro alkyl ethylene of 90-110 DEG C, tower reactor material is the thick cut 58.8Kg of perfluor alkyl ethyl acrylate.
(2) the thick cut of solvent that step (1) obtains is placed in rectifying tower, in tower, working pressure is about 40KPa, collects the thick cut 41.5Kg of solvent of 40-90 DEG C respectively, and tower reactor material is mainly containing the thick cut 3.5Kg of perfluor alkyl ethyl acrylate;
(3) the thick cut of perfluor alkyl ethyl acrylate step (1) obtained is in rectifying tower, and in tower, working pressure is about 40KPa, and rectification temperature is 110 DEG C, and it is main containing the thick cut 1.5Kg of perfluoro alkyl ethylene that collection tower top obtains;
(4) the thick cut of perfluoro alkyl ethylene obtained in step (1), (2), (3) is merged, be placed in rinse bath, with the speed of 2Kg/min add wherein mass percent concentration be 10% KOH solution carry out washing (KOH solution consumption is about 11Kg), and constantly to stir.After alkali liquid washing terminates, then add deionized water wherein with certain speed and carry out washing until be washed till neutrality (deionized water consumption is about 15Kg).
(5) disposablely in the thick cut of perfluoro alkyl ethylene obtained in step (4) active alumina powder (40 order) 50g is added.After leaving standstill system 40min, system is divided into water, oil, consolidates three layers, filters and obtains oil phase.In oil-phase product, add deionized water with certain speed again to carry out washing until be washed till neutrality (deionized water consumption is about 15Kg).
(6) stopper glycerol 20g is added in the perfluoro alkyl ethylene oil phase obtained in step (5), be placed in rectifying tower, in tower, working pressure is about 40KPa, and service temperature is 110 DEG C, collect tower reactor material perfluoro alkyl ethylene 4.86Kg, product purity is greater than 99.9%.
Reference examples 1
(1) by the liquid phase material in 100Kg perfluor alkyl ethyl acrylate reactor, flow in strainer 2 by pipeline, obtained filtrate 110Kg is placed in rectifying tower, in tower, working pressure is about 20KPa, collect the thick cut 44Kg of solvent of 40-90 DEG C respectively, the 90-110 DEG C of thick cut 5.2Kg of cut perfluoro alkyl ethylene, tower reactor material is the thick cut 60.8Kg of perfluor alkyl ethyl acrylate.
(2) the perfluoro alkyl ethylene cut obtained in step (1) is placed in rectifying tower, in tower, working pressure is about 15KPa, and service temperature is 100 DEG C, collects tower reactor material perfluoro alkyl ethylene 3.6Kg, product purity 92.3%.
Reference examples 2
(1) by the liquid phase material in 100Kg perfluor alkyl ethyl acrylate reactor, flow in strainer by pipeline, obtained filtrate 108Kg is placed in rectifying tower, in tower, working pressure is about 30KPa, collect the thick cut 42Kg of solvent of 40-90 DEG C respectively, the thick cut 5Kg of perfluoro alkyl ethylene of 90-110 DEG C, tower reactor material is the thick cut 61Kg of perfluor alkyl ethyl acrylate.
(2) the thick cut of solvent that step (1) obtains is placed in rectifying tower, in tower, working pressure is about 30KPa, collects the thick cut 39.5Kg of solvent of 40-90 DEG C respectively, and tower reactor material is mainly containing the thick cut 2.5Kg of perfluoro alkyl ethylene;
(3) the thick cut of perfluor alkyl ethyl acrylate step (1) obtained is in rectifying tower, and in tower, working pressure is about 30KPa, and rectification temperature is 110 DEG C, and it is main containing the thick cut of perfluoro alkyl ethylene that collection tower top obtains;
(4) the thick cut of perfluoro alkyl ethylene obtained in step (1), (2), (3) is merged, be placed in rectifying tower, in tower, working pressure is about 15KPa, and service temperature is 100 DEG C, collects tower reactor material perfluoro alkyl ethylene 3.52Kg, product purity 96.5%.
Although above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to scope of the present invention.
Claims (9)
1. the method for Separation and Recovery perfluoro alkyl ethylene from perfluor alkyl ethyl acrylate crude product, is characterized in that, comprising:
Perfluor alkyl ethyl acrylate crude product is carried out rectifying, obtains the first rectifying solution containing perfluoro alkyl ethylene; Add alkali liquid washing and activated alumina decolouring to the first rectifying solution of gained, and then carry out water, oil, solid phase three phase separation, obtain the oil phase containing perfluoro alkyl ethylene; In the oil phase of perfluoro alkyl ethylene, add a small amount of stopper, and carry out rectifying, obtain perfluoro alkyl ethylene.
2. method according to claim 1, it is characterized in that, the embodiment of the rectification step of described crude product, comprise: perfluor alkyl ethyl acrylate crude product is carried out first time rectifying in rectifying tower, obtain mainly containing the different fractions of perfluoro alkyl ethylene acrylate, perfluoro alkyl ethylene and solvent respectively; Respectively the cut containing solvent, perfluor alkyl ethyl acrylate is carried out second time rectifying, and obtain the component containing perfluoro alkyl ethylene respectively further, merge all liquid phases containing perfluoro alkyl ethylene, obtain described just rectifying solution.
3. method according to claim 1, is characterized in that, before described perfluor alkyl ethyl acrylate crude product carries out rectifying, also comprises the operation of filtering described crude product.
4. method according to claim 1, is characterized in that, comprises the steps: perfluor alkyl ethyl acrylate crude product to carry out filter operation, obtains coarse filtration liquid; First time rectifying is carried out to coarse filtration liquid, obtains mainly containing the cut of perfluoro alkyl ethylene acrylate, perfluoro alkyl ethylene and solvent respectively; Carry out second time rectifying to main containing solvent, perfluor alkyl ethyl acrylate cut, and obtain the component containing perfluoro alkyl ethylene respectively respectively; Merge all liquid phases containing perfluoro alkyl ethylene, obtain mixed solution; In mixed solution, add alkaline wash, activated alumina decolours, then carries out water, oil, solid phase three phase separation, obtains the oil phase containing perfluoro alkyl ethylene; Add stopper to containing in the oil phase of perfluoro alkyl ethylene, and carry out third time rectifying, obtain perfluoro alkyl ethylene.
5. method according to claim 4, it is characterized in that, described first time the pressure of distillation operation be 5-40Kpa, 40-90 DEG C and collect main containing solvent cut, collect main containing perfluoro alkyl ethylene cut for 90-110 DEG C, tower reactor material is main perfluor alkyl ethyl acrylate cut;
Described containing in the second time rectifying of solvent cut, will carry out rectifying containing solvent cut, rectifying pressure is 5-40Kpa, and rectification temperature is 40-90 DEG C, and tower reactor obtains mainly containing the cut of perfluoro alkyl ethylene;
Described containing in the second time rectifying of perfluor alkyl ethyl acrylate cut, comprise and carry out rectifying by containing perfluor alkyl ethyl acrylate cut, rectifying pressure is 5 ~ 40Kpa, and rectification temperature is 90-110 DEG C, and tower top obtains mainly containing the cut of perfluoro alkyl ethylene;
The rectifying pressure of described third time rectifying is 5 ~ 40Kpa, and temperature is 90 ~ 110 DEG C.
6. method according to claim 1, is characterized in that, described alkali liquid washing step adopt mass percent concentration be 3 ~ 10% inorganic alkali solution perfluoro alkyl ethylene cut is washed, then wash with water to neutrality.
7. method according to claim 6, is characterized in that, described inorganic alkali solution is preferably one or more the basic solution in sodium hydroxide, potassium hydroxide, sodium carbonate, salt of wormwood.
8. method according to claim 1, is characterized in that, described stopper is the combination of one or more in kautschin, triethylamine or glycerol.
9. the method according to any one of claim 1-5, is characterized in that, the pressure of described distillation operation is 20-40Kpa.
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Citations (3)
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|---|---|---|---|---|
| US3671574A (en) * | 1969-12-19 | 1972-06-20 | Ciba Geigy Corp | Preparation of polyfluoroalkyl esters of fumaric and other acids |
| CN1572783A (en) * | 2003-06-05 | 2005-02-02 | 旭硝子株式会社 | Process for producing a polyfluoroalkyl (meth)acrylate |
| CN102531889A (en) * | 2011-12-14 | 2012-07-04 | 太仓中化环保化工有限公司 | Preparation method for fluorine-containing acrylic ester |
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| US7579498B2 (en) * | 2005-11-29 | 2009-08-25 | E. I. Du Pont De Nemours And Company | Process for preparing fluorinated alkyl carboxylate esters |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3671574A (en) * | 1969-12-19 | 1972-06-20 | Ciba Geigy Corp | Preparation of polyfluoroalkyl esters of fumaric and other acids |
| CN1572783A (en) * | 2003-06-05 | 2005-02-02 | 旭硝子株式会社 | Process for producing a polyfluoroalkyl (meth)acrylate |
| CN102531889A (en) * | 2011-12-14 | 2012-07-04 | 太仓中化环保化工有限公司 | Preparation method for fluorine-containing acrylic ester |
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