CN108264458A - A kind of preparation method of dimerization of hexafluoropropene oxide object - Google Patents
A kind of preparation method of dimerization of hexafluoropropene oxide object Download PDFInfo
- Publication number
- CN108264458A CN108264458A CN201611258558.5A CN201611258558A CN108264458A CN 108264458 A CN108264458 A CN 108264458A CN 201611258558 A CN201611258558 A CN 201611258558A CN 108264458 A CN108264458 A CN 108264458A
- Authority
- CN
- China
- Prior art keywords
- dimerization
- preparation
- hexafluoropropene oxide
- oxide object
- object according
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides, epoxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation method of dimerization of hexafluoropropene oxide object, including：In polar aprotic solvent, using hexafluoropropylene oxide as raw material, consisting of phase-transferring agent is added in, it is reacted to obtain dimerization of hexafluoropropene oxide object using the composite catalyst system that tertiary amine and Diamines form as catalyst.The preparation method high selectivity of dimerization of hexafluoropropene oxide object provided by the invention, reaction condition is mild, and solvent, catalyst are recyclable, and operating method is simple and practicable, environmental-friendly, are easy to Industry Control, is suitble to large-scale industrial production.
Description
Technical field
The invention belongs to fluorine-containing technical field of fine, and in particular to a kind of preparation side of dimerization of hexafluoropropene oxide object
Method.
Background technology
Fluorochemical is that field of fine chemical increases one of chemicals the most rapid, in chemistry, chemical industry, material, agriculture
Medicine, medicine and other fields are widely used, and have wide development prospect and powerful vitality.Dimerization of hexafluoropropene oxide body
It is a kind of liquid of water white transparency under normal temperature state, is a kind of reactive intermediate of perfluor class, can be used to draw organic fluorin radical
Enter in organic molecule, for pesticide and pharmaceutical industry.In Material Field, dimerization of hexafluoropropene oxide body is widely used, end
Acyl fluorides active function groups can pass through the fluorine inorganic agent such as modification, the excellent fluorocarbon surfactant of processability；By to hexafluoro ring
Ethylene Oxide dimer continues to polymerize, and can prepare high-performance perfluoropolyether, is a kind of excellent lubricating oil of high temperature resistance；Hexafluoro ring
Ethylene Oxide dimer can prepare perfluoropropylvinylether (PPVE), available for fluorine resin by hydrolyzing with after decarboxylation
It synthesizes and modified.
At present, about the patent of the preparation method of dimerization of hexafluoropropene oxide body and few.German patent DE 2026669
In used silver nitrate as catalyst, dimer yield reaches as high as 86%, but silver nitrate has a light sensitivity, stability compared with
Difference, and nitrous acid gas is easily generated, processing safety is low.Using cesium fluoride as urging in Japan Patent JP 62195345
Agent, and different amounts of water or PEG are added in prepare hexafluoropropylene oxide oligomer, Hexafluoropropylene third in product in such method
Alkane dimer selectivity is not high, and needs to carry out under -20 DEG C of low temperature, and practical operation difficulty is larger.In addition, catalyst fluorine
It is expensive to change caesium, and is easy to absorb water, is unfavorable for large-scale production.Hoechst Aktiengesellschaft is in Chinese patent CN 1044092
It mentions and uses transition metal salt such as CuCl, CuCl2, CoCl2, ZnCl2Deng the catalyst system and catalyzing formed with tertiary diamine, Hexafluoropropylene third
Alkane dimer yield has used transition metal ions 80% or so in catalyst, be not easily recycled, and be easy to cause environment dirt
Dye.Tertiary amine is mentioned in Japan Patent JP 1990-259833, and either pyridine or quinoline and urea as catalyst, use certain ratio
The hexafluoropropylene oxide and hexafluoropropene gas mixture of example are as raw material, the receipts of dimerization of hexafluoropropene oxide body being similarly obtained
Rate is not high, and has gaseous by-product, increases practical operation difficulty.
Invention content
For poor catalyst stability exists in the prior art, product selectivity is low, and operation difficulty is big, and environment is unfriendly etc.
Problem, the invention discloses a kind of preparation method of simple and practicable dimerization of hexafluoropropene oxide object, including：In the non-matter of polarity
In sub- property solvent, using hexafluoropropylene oxide as raw material, consisting of phase-transferring agent, the composite catalyzing body formed with tertiary amine and tertiary diamine class are added in
Be for catalyst, it is reacted to obtain dimerization of hexafluoropropene oxide object.
Further specifically, a kind of preparation method of dimerization of hexafluoropropene oxide object, includes the following steps：
1) it is catalyst and phase transfer by the composite catalyst system of polar aprotic solvent, tertiary amine and tertiary diamine class composition
Agent is added in reaction vessel, and 0.5~1h is stirred at room temperature；
2) it is -1.0~1.0Mpa to control pressure in reaction vessel, and hexafluoropropylene oxide monomer is added in reaction vessel,
20~30 DEG C of temperature control reacts 0.5~5h；
3) reaction solution after reaction, is taken out, rectifying detaches product up to dimerization of hexafluoropropene oxide object；
4) recycling design and catalyst.
In some embodiments, the hexafluoropropylene oxide monomer feed postition for connection gas flowmeter after through reaction
Container bottom adds in, and feed rate is 1~20g/min, preferably 5~10g/min.
In some embodiments, the consisting of phase-transferring agent is quaternary ammonium fluoride salt；Further, the consisting of phase-transferring agent is tetramethyl
It is one or more in base ammonium fluoride, tetraethyl ammonium fluoride, tetrapropyl ammonium fluoride or tetrabutyl ammonium fluoride.
In some embodiments, shown in the structural formula of the tertiary amine such as following formula (I)：
Wherein, R1、R2、R3It is independently respectively C1-C12Saturated or unsaturated alkyl；
Further, R1、R2、R3It is independently respectively C1-C6Alkyl, C1-C6Cycloalkyl or phenyl.
In some embodiments, shown in the structural formula of the tertiary diamine such as following formula (II)：
Wherein, R C1-C12Saturated or unsaturated alkyl or carbonyl；R4~R7Various is independently C1-C12It is full
And/or undersaturated alkyl；Further, R, R4~R7To be independently respectively C1-C6Alkyl, C1-C6Cycloalkyl；More into
One step, R be ethyl or carbonyl, R4~R7It is independently respectively methyl or ethyl.
In some embodiments, the polar aprotic solvent for tetraethyleneglycol dimethyl ether, diethylene glycol dimethyl ether,
It is one or more in acetonitrile, propionitrile or tetrahydrofuran.
In some embodiments, the molar ratio of tertiary amine and tertiary diamine is 1~10 in the composite catalyst system:1, preferably
It is 5~10:1；A concentration of 0.5~5mol/L of the tertiary amine, preferably 1~3mol/L.
In some embodiments, the molar ratio of the tertiary amine and consisting of phase-transferring agent is 1~10:1, preferably 1~5:1.
In some embodiments, the recovered solvent after reaction and catalyst can be recycled.
The beneficial effects of the invention are as follows providing a kind of preparation method of simple and practicable dimerization of hexafluoropropene oxide body, with
Existing dimerization of hexafluoropropene oxide object synthetic technology is compared, present invention gained dimerization of hexafluoropropene oxide object high selectivity, instead
Mild condition is answered, solvent, catalyst is recyclable, and operating method is simple and practicable, environmental-friendly, is easy to industrial control
System is suitble to large-scale industrial production.
Term defines
The invention is intended to cover all replacement, modification and equivalent technical solutions, they are included in claim such as and determine
In the scope of the invention of justice.Those skilled in the art will appreciate that many and similar or equivalent method described herein and material
It can be used in the practice present invention.The present invention is not limited to method described herein and material.In document, patent and the class combined
Like one or more of material are different from the application or (term, term defined in including but not limited in the case of contradicting
Using, described technology etc.), it is subject to the application.
It will further be appreciated that certain features of the present invention, are clearly visible, are carried out in multiple independent embodiments
Description, but can also in combination be provided in single embodiment.Conversely, the various features of the present invention, for brevity,
It is described, but can also be provided individually or with any appropriate sub-portfolio in single embodiment.
Unless otherwise stated, all scientific and technical terminologies used in the present invention have with those skilled in the art of the invention's
It is generally understood identical meaning.All patents of the present invention and public publication are integrally incorporated this hair by reference
It is bright.
Unless otherwise stated, following definition used herein should be applied.For purposes of the present invention, chemical element with
Periodic table of elements CAS editions and 1994 the 75th edition《Handbook of Chemistry and Physics》Unanimously.In addition, organic chemistry General Principle can join
It examines " Organic Chemistry ", Thomas Sorrell, University Science Books, Sausalito:1999,
With " March's Advanced Organic Chemistry " by Michael B.Smith and Jerry March, John
Wiley&Sons,New York:Description in 2007, entire contents are incorporated herein by reference.
Term "comprising" or " comprising " are open language, that is, include the content specified by the present invention, but it is not precluded
Content in terms of him.
Term " room temperature " refers to that temperature range is 25 ± 5 DEG C.
In the context of the present invention, wordings such as " about " or " about " whether or not using, all numbers being disclosed that
It is approximation.The numerical value of each number is it is possible that will appear the differences such as 1%, 2% or 5%.
Specific embodiment
In order to which those skilled in the art is made to more fully understand technical scheme of the present invention, it is non-that some are disclosed further below
Limiting embodiment, the present invention is described in further detail.
Reagent used in the present invention can be bought or be prepared by method of the prior art from the market
Or it is prepared by method described in the invention.
In the present invention, h represents hour, g expressions gram, and mL represents milliliter, mmol expressions mM.
Comparative example
By N, accelerine (24.2g), tetramethylurea (4.6g) and acetonitrile (100mL) are added to 2L band condensation chucks
In reaction kettle, stirring at normal temperature 1h.Reaction kettle is evacuated to -0.1Mpa, hexafluoropropylene oxide monomer is passed through with the rate of 10g/min
It in reaction kettle, is stirred to react, constant temperature refrigeration pump is connected outside reacting kettle jacketing, it is 25 DEG C or so to maintain temperature in the kettle, leads to material hexafluoro ring
After Ethylene Oxide monomer (500g), stop logical material, stir 3h.Crude product is taken out from reaction kettle, rectifying separation product obtains six
Fluorine propylene oxide dimer (308g), yield 61.6%, GC test products purity are 98.89%.
Embodiment 1
By triethylamine (20.2g), tetramethylethylenediamine (4.6g), Methanaminium, N,N,N-trimethyl-, fluoride (9.3g) and tetrahydrofuran
(100mL) is added in 2L band condensation jacket reactors, and 1h is stirred at room temperature.Reaction kettle is evacuated to -0.1Mpa, by Hexafluoropropylene third
Alkane monomer is passed through with the rate of 10g/min in reaction kettle, is stirred to react, and reacting kettle jacketing is passed through condensed water, maintains temperature in the kettle
It is 25 DEG C or so, after leading to material hexafluoropropylene oxide monomer (500g), stops logical material, stir 3h.Crude product is taken from reaction kettle
Go out, rectifying separation product and recycling design, catalyst.Dimerization of hexafluoropropene oxide object (412g), yield 82.4% are obtained, GC is surveyed
Trial product purity is 98.85%.
Embodiment 2
By N, accelerine (24.2g), tetramethylethylenediamine (4.6g), tetraethyl ammonium fluoride (14.9g) and acetonitrile
(100mL) is added in 2L band condensation jacket reactors, stirring at normal temperature 0.5h.Reaction kettle is evacuated to -0.1Mpa, by Hexafluoropropylene
Oxide monomer is passed through with the rate of 5g/min in reaction kettle, is stirred to react, and reacting kettle jacketing is passed through condensed water, maintains temperature in the kettle
It is 25 DEG C or so, after leading to material hexafluoropropylene oxide monomer (500g), stops logical material, stir 3h.Crude product is taken from reaction kettle
Go out, rectifying separation product and recycling design, catalyst.Dimerization of hexafluoropropene oxide object (436g), yield 87.2% are obtained, GC is surveyed
Trial product purity is 99.03%.
Embodiment 3
By N, accelerine (24.2g), tetramethylurea (4.6g), Methanaminium, N,N,N-trimethyl-, fluoride (9.3g) and acetonitrile
(100mL) is added in 2L band condensation jacket reactors, stirring at normal temperature 1h.Reaction kettle is evacuated to -0.1Mpa, by Hexafluoropropylene third
Alkane monomer is passed through with the rate of 10g/min in reaction kettle, is stirred to react, and reacting kettle jacketing is passed through condensed water, maintains temperature in the kettle
It is 25 DEG C or so, after leading to material hexafluoropropylene oxide monomer (500g), stops logical material, stir 3h.Crude product is taken from reaction kettle
Go out, rectifying separation product and recycling design, catalyst.Dimerization of hexafluoropropene oxide object (453g), yield 90.6% are obtained, GC is surveyed
Trial product purity is 99.12%.
Embodiment 4
By N, N- diethylanilines (29.8g), 4-methyl-diaminopropane (5.2g), tetrabutyl ammonium fluoride (10.3g) and tetrem
Glycol dimethyl ether (100mL) is added in 2L band condensation jacket reactors, stirring at normal temperature 0.5h.Reaction kettle is evacuated to -0.1Mpa,
Hexafluoropropylene oxide monomer is passed through with the rate of 10g/min in reaction kettle, is stirred to react, reacting kettle jacketing is passed through condensed water,
It is 25 DEG C or so to maintain temperature in the kettle, after leading to material hexafluoropropylene oxide monomer (500g), stops logical material, stirs 3h.By crude product
It is taken out from reaction kettle, rectifying separation product and recycling design, catalyst.Dimerization of hexafluoropropene oxide object (377g) is obtained, is produced
Rate 75.4%, GC test products purity are 98.82%.
Embodiment 5
By N, N- diethylanilines (29.8g), tetraethylethylenediamine (6.9g), tetrapropyl ammonium fluoride (13g) and propionitrile
(100mL) is added in 2L band condensation jacket reactors, stirring at normal temperature 1h.Reaction kettle is evacuated to -0.1Mpa, by Hexafluoropropylene third
Alkane monomer is passed through with the rate of 10g/min in reaction kettle, is stirred to react, and reacting kettle jacketing is passed through condensed water, maintains temperature in the kettle
It is 25 DEG C or so, after leading to material hexafluoropropylene oxide monomer (500g), stops logical material, stir 3h.Crude product is taken from reaction kettle
Go out, rectifying separation product and recycling design, catalyst.Dimerization of hexafluoropropene oxide object (406g), yield 81.2% are obtained, GC is surveyed
Trial product purity is 99.07%.
Embodiment 6
By N, accelerine (24.2g), tetraethylethylenediamine (6.9g), Methanaminium, N,N,N-trimethyl-, fluoride (9.3g) and diethyl two
Diethylene glycol dimethyl ether (100mL) is added in 2L band condensation jacket reactors, stirring at normal temperature 1h.Reaction kettle is evacuated to -0.1Mpa, by six
Fluorine propylene oxide monomer is passed through with the rate of 10g/min in reaction kettle, is stirred to react, and reacting kettle jacketing is passed through condensed water, is maintained
Temperature in the kettle is 25 DEG C or so, after leading to material hexafluoropropylene oxide monomer (500g), stops logical material, stirs 3h.By crude product from anti-
It answers in kettle and takes out, rectifying separation product and recycling design, catalyst.Obtain dimerization of hexafluoropropene oxide object (382g), yield
76.4%, GC test product purity are 98.67%.
Embodiment 7
Recovered solvent, catalyst in embodiment 3 are mixed into about 100mL, are added to after supplementing acetonitrile (20mL) thereto
Reaction kettle is evacuated to -0.1Mpa in 2L band condensation jacket reactors, hexafluoropropylene oxide monomer is passed through with the rate of 10g/min
It in reaction kettle, is stirred to react, reacting kettle jacketing is passed through condensed water, and it is 25 DEG C or so to maintain temperature in the kettle, leads to material Hexafluoropropylene third
After alkane monomer (500g), stop logical material, stir 3h.Crude product is taken out from reaction kettle, rectifying separation product and recycling design,
Catalyst.Dimerization of hexafluoropropene oxide object (447g), yield 89.4% are obtained, GC test products purity is 99.01% (recycling profit
With rear operation reusable 7 times or more).
The method of the present invention is described by preferred embodiment, related personnel can significantly hold within the present invention,
Method described herein and application are modified or suitably changed with combining in spirit and scope, to realize and using the present invention
Technology.Those skilled in the art can use for reference present disclosure, be suitably modified technological parameter realization.In particular, it should be pointed out that institute
Have similar replacement and change it is apparent to those skilled in the art, they are considered as being included in the present invention
It is interior.
Claims (10)
1. a kind of preparation method of dimerization of hexafluoropropene oxide object, including：In polar aprotic solvent, with Hexafluoropropylene third
Alkane is raw material, adds in consisting of phase-transferring agent, and the composite catalyst system formed using tertiary amine and tertiary diamine class is reacted to obtain six as catalyst
Fluorine propylene oxide dimer.
2. the preparation method of dimerization of hexafluoropropene oxide object according to claim 1, which is characterized in that including walking as follows
Suddenly：
1) composite catalyst system of polar aprotic solvent, tertiary amine and tertiary diamine class composition is added for catalyst and consisting of phase-transferring agent
Enter in reaction vessel, 0.5~1h is stirred at room temperature；
2) it is -1.0~1.0Mpa to control pressure in reaction vessel, hexafluoropropylene oxide monomer is added in reaction vessel, temperature control
20~30 DEG C, react 0.5~5h；
3) reaction solution after reaction, is taken out, rectifying detaches product up to dimerization of hexafluoropropene oxide object；
4) recycling design and catalyst.
3. the preparation method of dimerization of hexafluoropropene oxide object according to claim 1 or 2, which is characterized in that Hexafluoropropylene
For oxide monomer feed postition to be added in after connection gas flowmeter through reaction container bottom, feed rate is 1~20g/min, excellent
Select 5~10g/min.
4. the preparation method of dimerization of hexafluoropropene oxide object according to claim 1 or 2, which is characterized in that the phase turns
Shifting agent is quaternary ammonium fluoride salt.
5. the preparation method of dimerization of hexafluoropropene oxide object according to claim 4, wherein the quaternary ammonium fluoride salt is four
It is one or more in methyl ammonium fluoride, tetraethyl ammonium fluoride, tetrapropyl ammonium fluoride or tetrabutyl ammonium fluoride.
6. the preparation method of dimerization of hexafluoropropene oxide object according to claim 1 or 2, which is characterized in that the tertiary amine
Structural formula such as following formula (I) shown in：
Wherein, R1、R2、R3It is independently respectively C1-C12Saturated or unsaturated alkyl.
7. the preparation method of dimerization of hexafluoropropene oxide object according to claim 6, which is characterized in that the R1、R2、R3
It is independently respectively C1-C6Alkyl, C1-C6Cycloalkyl or phenyl.
8. the preparation method of dimerization of hexafluoropropene oxide object according to claim 1 or 2, which is characterized in that the uncle two
Shown in the structural formula of amine such as following formula (II)：
Wherein, R C1-C12Saturated or unsaturated alkyl or carbonyl；R4~R7Various is independently C1-C12Saturation or
Undersaturated alkyl.
9. the preparation method of dimerization of hexafluoropropene oxide object according to claim 1 or 2, which is characterized in that the polarity
Non-protonic solvent is one kind or more in tetraethyleneglycol dimethyl ether, diethylene glycol dimethyl ether, acetonitrile, propionitrile or tetrahydrofuran
Kind.
10. the preparation method of dimerization of hexafluoropropene oxide object according to claim 1 or 2, which is characterized in that described compound
The molar ratio of tertiary amine and tertiary diamine is 1~10 in catalyst system and catalyzing:1；A concentration of 0.5~5mol/L of the tertiary amine；
The molar ratio of the tertiary amine and consisting of phase-transferring agent is 1~10:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611258558.5A CN108264458B (en) | 2016-12-30 | 2016-12-30 | Preparation method of hexafluoropropylene oxide dimer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611258558.5A CN108264458B (en) | 2016-12-30 | 2016-12-30 | Preparation method of hexafluoropropylene oxide dimer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108264458A true CN108264458A (en) | 2018-07-10 |
| CN108264458B CN108264458B (en) | 2022-07-08 |
Family
ID=62754648
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201611258558.5A Active CN108264458B (en) | 2016-12-30 | 2016-12-30 | Preparation method of hexafluoropropylene oxide dimer |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108264458B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109485560A (en) * | 2018-11-27 | 2019-03-19 | 湖南有色郴州氟化学有限公司 | A kind of method of selectivity synthesis hexafluoropropylene oxide oligomer |
| CN111072461A (en) * | 2019-12-19 | 2020-04-28 | 浙江巨圣氟化学有限公司 | Synthesis method of PPVE |
| CN117225476A (en) * | 2023-11-15 | 2023-12-15 | 山东华夏神舟新材料有限公司 | Supported metal catalyst and preparation and regeneration methods and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62195345A (en) * | 1986-02-21 | 1987-08-28 | Shin Etsu Chem Co Ltd | Production of hexafluoropropylene oxide oligomer |
| US4729856A (en) * | 1985-05-28 | 1988-03-08 | Ausimont S.P.A. | Process for the preparation of 2-perfluoropropoxy-perfluoropropionyl fluoride |
| CN1044092A (en) * | 1989-01-14 | 1990-07-25 | 赫彻斯特股份公司 | Process for dimerization of hexafluoropropene oxide |
| JPH04139146A (en) * | 1990-09-28 | 1992-05-13 | Nippon Mektron Ltd | Production of perfluoro(2-propoxypropionic acid) fluoride |
| CN103788363A (en) * | 2013-12-25 | 2014-05-14 | 上海艾肯化工科技有限公司 | Method for preparing perfluoropolyether with high molecular weight |
-
2016
- 2016-12-30 CN CN201611258558.5A patent/CN108264458B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4729856A (en) * | 1985-05-28 | 1988-03-08 | Ausimont S.P.A. | Process for the preparation of 2-perfluoropropoxy-perfluoropropionyl fluoride |
| JPS62195345A (en) * | 1986-02-21 | 1987-08-28 | Shin Etsu Chem Co Ltd | Production of hexafluoropropylene oxide oligomer |
| CN1044092A (en) * | 1989-01-14 | 1990-07-25 | 赫彻斯特股份公司 | Process for dimerization of hexafluoropropene oxide |
| JPH04139146A (en) * | 1990-09-28 | 1992-05-13 | Nippon Mektron Ltd | Production of perfluoro(2-propoxypropionic acid) fluoride |
| CN103788363A (en) * | 2013-12-25 | 2014-05-14 | 上海艾肯化工科技有限公司 | Method for preparing perfluoropolyether with high molecular weight |
Non-Patent Citations (1)
| Title |
|---|
| 邝生鲁等: "《现代精细化工高新技术与产品合成工艺》", 31 December 1997 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109485560A (en) * | 2018-11-27 | 2019-03-19 | 湖南有色郴州氟化学有限公司 | A kind of method of selectivity synthesis hexafluoropropylene oxide oligomer |
| CN109485560B (en) * | 2018-11-27 | 2021-07-09 | 湖南有色郴州氟化学有限公司 | Method for selectively synthesizing hexafluoropropylene oxide oligomer |
| CN111072461A (en) * | 2019-12-19 | 2020-04-28 | 浙江巨圣氟化学有限公司 | Synthesis method of PPVE |
| CN117225476A (en) * | 2023-11-15 | 2023-12-15 | 山东华夏神舟新材料有限公司 | Supported metal catalyst and preparation and regeneration methods and application thereof |
| CN117225476B (en) * | 2023-11-15 | 2024-02-20 | 山东华夏神舟新材料有限公司 | Supported metal catalyst and preparation and regeneration methods and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108264458B (en) | 2022-07-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5399718A (en) | Direct fluorination process for making perfluorinated organic substances | |
| CN103370305B (en) | The preparation of the oligopolymer of highly fluorinated-sulfinic acid and co-oligomer and their salt | |
| CN108264458A (en) | A kind of preparation method of dimerization of hexafluoropropene oxide object | |
| CN101474576B (en) | Catalytic system for synthesizing annular carbonic acid ester | |
| Kanemasa et al. | Generation of nitrile oxides through O-metalation of hydroximoyl chlorides. Chelation-controlled syn-selective cycloaddition of nitrile oxides to α-substituted allyl alcohols | |
| WO2010117029A1 (en) | Method of manufacturing a perfluoro organic peroxide | |
| CN111825568A (en) | Synthesis method of perfluoroisobutyronitrile | |
| CN108794300A (en) | The Isolation method of raw material containing ethylene glycol and 1,2- butanediols and the preparation method of epoxy butane | |
| CN108069831A (en) | A kind of method for synthesizing 2,3- dimethyl -4- fluorophenols | |
| EP1973864A1 (en) | Preparation of compounds having a perfluoroalkylcarbonyl group | |
| US20050065381A1 (en) | Process for preparation of hydroperoxides | |
| US10513478B2 (en) | Processes for preparing halogenated alkanes | |
| CN111116302B (en) | Synthesis method of halogenated butene | |
| CN107473948A (en) | A kind of synthetic method that the pentanone of 3,5 dichloro 2 is prepared by ethyl acetoacetate | |
| CN105646144B (en) | A kind of preparation method of 1,2 aliphatic glycols | |
| US7612227B2 (en) | Processes for producing 3-methyl-2-butenyl acetate | |
| EP2637995B1 (en) | Process for the preparation of difluoroacetic acid | |
| CN107867978B (en) | Synthesis method of heptafluoropropyl trifluoromethyl ether | |
| CN114933527B (en) | Method for continuously synthesizing o-methylbenzoyl chloride in micro-channel | |
| CN114634397B (en) | Method for preparing hexafluoropropylene dimer by gas phase method | |
| KR100250415B1 (en) | Preparation process of high purity 1,3-dialkyl-2-imidazolidinon | |
| CN114478264B (en) | Synthesis method of intermediate of bisamide pesticide | |
| CN111333497B (en) | Preparation method of fluorine-containing dicarboxylic acid | |
| CN112538008B (en) | Synthetic method of difluoroacetic acid | |
| CN109180441A (en) | A kind of synthetic method of triethyl orthoformate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |