CN106748676B - A method of unsaturated impurity in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product - Google Patents
A method of unsaturated impurity in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product Download PDFInfo
- Publication number
- CN106748676B CN106748676B CN201510816940.2A CN201510816940A CN106748676B CN 106748676 B CN106748676 B CN 106748676B CN 201510816940 A CN201510816940 A CN 201510816940A CN 106748676 B CN106748676 B CN 106748676B
- Authority
- CN
- China
- Prior art keywords
- hydrofluoroether
- crude product
- hexafluoro propyl
- unsaturated compound
- alkylol
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of removals 1,1,2,3, the method of unsaturated compound impurity in 3,3- hexafluoro propyl hydrofluoroether crude products, comprising: under alkylol and alkali compounds effect, 1,1,2,3, unsaturated compound in 3,3- hexafluoro propyl hydrofluoroether crude products is reacted to obtain corresponding alkylol addition product.Method reaction condition provided by the invention is mild, at low cost, risk is small low with equipment requirement.
Description
Technical field
The present invention relates to a kind of minimizing technologies of unsaturated impurity, more particularly to a kind of 1,1,2,3,3,3- hexafluoro propyl hydrogen
The minimizing technology of unsaturated impurity in fluorine ether crude product.
Background technique
1,1,2,3,3,3- hexafluoro propyl hydrofluoroether does not destroy ozone layer, and chamber effect potential value is low, is a kind of environment friend
Good type compound, can be used as the fluorochlorohydrocarbon substitute of a new generation, and be expected as cleaning agent, solvent, foaming agent, heat exchange Jie
Matter etc..
For the preparation method of 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether, the prior art has many reports, wherein most suitable
Close a kind of industrialized preparation method, such as Chinese patent CN1651378, Japan Patent JP2002201152, United States Patent (USP) US
3291844 and Journal of Fluorine Chemistry, 2008,129 (6): described in 474-477, with pure and mild hexafluoropropene
For raw material, addition reaction is carried out in the presence of alkali compounds and obtains 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether.
The preparation method of 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether disclosed in the prior art, due to can not in reaction process
Avoid having the generation of dehydrofluorination by-product, these by-products have unsaturated bond, i.e., 1,1,2,3,3,3- hexafluoro propyl again
Contain unsaturated impurity in hydrofluoroether crude product.Due to unsaturated impurity boiling point usually with target product it is very close, therefore be difficult
The unsaturated impurity in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product is removed by way of direct rectifying.
In order to remove the unsaturated impurity in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product, the prior art is made as follows
Effort:
Japan Patent JP2002201152 discloses the generation for inhibiting unsaturated impurity using aqueous solution.In fact, using
Although aqueous solution can reduce the amount that unsaturated impurity generates, the generation of unsaturated impurity can not be thoroughly avoided.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1953,282-9, which is disclosed, to be made
The unsaturated impurity in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product is removed with bromine addition unsaturation impurity.The method
Not only bromine is at high cost, but also corrosivity is big, it is desirable that equipment highly corrosion resistant, reaction are dangerous.
PCT Patent Application WO2006123563 is disclosed using chlorine addition unsaturation impurity to remove 1,1,2,3,3,3-
Unsaturated impurity in hexafluoro propyl hydrofluoroether crude product.The method chlorine corrosion is big, it is desirable that equipment highly corrosion resistant, reaction danger
Danger.
Korean Patent KR2010138245 discloses thick using n-hexylamine removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether
The method of unsaturated impurity in product.The method n-hexylamine is at high cost.
Therefore, still it is hopeful the minimizing technology to the unsaturated impurity in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product
It is further improved.
Summary of the invention
The purpose of the present invention is to provide unsaturated miscellaneous in a kind of removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product
The method of matter has the characteristics that reaction condition is mild, at low cost, risk is small low with equipment requirement.
Of the present invention 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether, structural formula CF3CHFCF2-O-CH2R, and R=-
CaHbFc.Wherein: for a and c independently selected from 0~10 integer, b is selected from the integer more than or equal to 1, and b+c=2a+1.
Unsaturated impurity, is primarily referred to as unsaturation in of the present invention 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product
Compound, structural formula CF2=CFCF2-O-CH2R and/or CF3CF=CF-O-CH2R, and R=-CaHbFc.Wherein: a and c are only
It is on the spot selected from 0~10 integer, b is selected from the integer more than or equal to 1, and b+c=2a+1.
The present invention is by the case where alkali compounds acts on, making alkylol and 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product
In unsaturated compound reaction, obtain corresponding alkylol addition product.The structure of the alkylol addition product includes following knot
Structure formula (I) and (II):
CH2R-O-CF2CHFCF2-O-CH2R——(I)
Group R wherein in structure formula (I) and (II) is as described above.
The technical solution adopted by the invention is as follows:
The method of unsaturated compound, the method packet in a kind of 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product of removal
It includes: the unsaturated compound under alkylol and alkali compounds effect, in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product
It is reacted to obtain corresponding alkylol addition product；
The alkylol is the alkylol of C1~C5；
The alkali compounds is selected from alkali metal hydroxide, alkali halide, alkaline earth metal hydroxide and alkaline earth
One of metal halide, two or three of combination of the above；
The structural formula of the 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether is CF3CHFCF2-O-CH2R；
The unsaturated compound includes CF2=CFCF2-O-CH2R and/or CF3CF=CF-O-CH2R；
The R=-CaHbFc, independently selected from 0~10 integer, b is selected from the integer more than or equal to 1, and b+c=by a and c
2a+1。
In method provided by the invention, the alkylol used is the alkylol of C1~C5.Go out from implementation result angle is improved
Hair, the alkylol are preferably selected from one of methanol, ethyl alcohol and propyl alcohol, two or three of combination of the above.
In method provided by the invention, the alkali compounds used is selected from alkali metal hydroxide, alkali halide, alkali
One of earth metal hydroxide and alkaline-earth halide, two or three of combination of the above.The alkali metal is element week
Qi Biaozhong IA race element.The alkaline-earth metal is Group IIA element in the periodic table of elements.It is excellent from raising implementation result angle
Choosing, the alkali compounds are selected from sodium hydroxide, potassium hydroxide, cesium hydroxide, magnesium hydroxide, sodium fluoride, potassium fluoride, fluorine
Change one of caesium and magnesium fluoride, two or three of combination of the above.
In method provided by the invention, described 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether, unsaturated compound CF2=
CFCF2-O-CH2R and/or CF3CF=CF-O-CH2R, substituent R=- CaHbFc, a and c independently selected from 0~10 integer,
B is selected from the integer more than or equal to 1, and b+c=2a+1.As a preferred mode, a is selected from 0~3 integer, and b, which is selected from, to be greater than
Integer equal to 1, and b+c=2a+1.As further preferred mode, a is selected from 0~2 integer.
In method provided by the invention, the dosage of the alkali compounds used, reaction can be made i.e. by theoretically meeting
It can.From raising implementation result angle, it is preferred that the molar ratio of the alkali compounds and unsaturated compound is 0.1
~3:1.It may further be preferable that the molar ratio of the alkali compounds and unsaturated compound is 1~2:1.
In method provided by the invention, the dosage of the alkylol used, theoretically meeting can be such that reaction carries out.From
It improves implementation result angle to set out, it is preferred that the molar ratio of the alkylol and unsaturated compound is 2~10:1.Into one
Step is preferably, and the molar ratio of the alkylol and unsaturated compound is 3~5:1.
In method provided by the invention, reaction temperature, which theoretically meets, can be such that reaction carries out.Preferably, instead
Answering temperature is 0~90 DEG C.It may further be preferable that reaction temperature is 30~50 DEG C.
Method provided by the invention can not only effectively remove unsaturated compound in crude product simultaneously compared with prior art
To obtain 1,1,2,3,3, the 3- hexafluoro propyl hydrofluoroether product that purity is greater than 99.9%, and reaction condition is mild, cost
It is low, risk is small low with equipment requirement, be suitble to industrial applications.
Specific embodiment
Next combined with specific embodiments below invention is further explained, but does not limit the invention to these tools
Body embodiment.One skilled in the art would recognize that present invention encompasses may include in Claims scope
All alternatives, improvement project and equivalent scheme.
The preparation of embodiment 1:1,1,2,3,3,3- hexafluoro ethyl ether crude product
In autoclave, sodium hydroxide 200g, dehydrated alcohol 460g is added, closes autoclave, air in nitrogen displacement kettle,
Cooling autoclave is passed through hexafluoropropene into kettle and amounts to 1500g, during which control hexafluoropropene rate of feeding to 0 DEG C, makes reaction temperature
Degree is no more than 40 DEG C, after being passed through specified amount hexafluoropropene, is kept stirring until reaction temperature pressure no longer changes, collection is reacted
Liquid obtains 1,1,2,3,3,3- hexafluoro ethyl ether crude product 1460g after washing.GC is analyzed the results show that 1,1,2,3,3,3-
In hexafluoro ethyl ether crude product, CF3CHFCF2-O-CH2CH3Content 77.8%, C3F5-O-CH2CH3Content 12.4%, other
Impurity content 9.8%.
The method is 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether universal method of synthesis, by changing alcohol and hexafluoropropene
The synthesis of corresponding 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether can be realized in reaction condition.
The removal of unsaturated impurity in embodiment 2:1,1,2,3,3,3- hexafluoro ethyl ether crude product
In three-necked flask with a mixing device, 1,1,2,3,3,3- prepared according to 1 the method for embodiment is added
Hexafluoro ethyl ether crude product 2850g.After tested, unsaturated impurity in described 1,1,2,3,3,3- hexafluoro ethyl ether crude product
Total content be 12.4% (about 2mol), wherein CF3CF=CF-O-CH2CH3Content is 7.9%, CF2=CFCF2-O-CH2CH3
It is 4.5%.Ethyl alcohol 322g (7mol) and sodium hydroxide 120g (3mol) is added into three-necked flask again, stirring is warming up to 50 DEG C,
Insulation reaction 4h.End of reaction filters out the insoluble solid in three-necked flask, and carries out rectifying, control rectification temperature be 80~
120 DEG C, rectifying pressure is normal pressure, and rectifying column theoretical cam curve is 10, collects 69~71 DEG C of fractions, obtains target product 1,1,2,
3,3,3- hexafluoro ethyl ether.
The GC of 1,1,2,3,3,3- hexafluoro ethyl ether crude product before and after the processing analyzes result such as the following table 1.
Table 1
The removal of unsaturated impurity in embodiment 3:1,1,2,3,3,3- hexafluoro propyl methyl ether crude product
In three-necked flask with a mixing device, 1,1,2,3,3,3- prepared according to 1 the method for embodiment is added
Hexafluoro propyl methyl ether crude product 1310g.After tested, unsaturated impurity in described 1,1,2,3,3,3- hexafluoro propyl methyl ether crude product
Total content be 8.7% (about 0.7mol), wherein CF3CF=CF-O-CH3Content is 5.7%, CF2=CFCF2-O-CH3For
3.0%.Methanol 70g (2.2mol) and sodium hydroxide 40g (1.0mol) is added into three-necked flask again, stirring is warming up to 40 DEG C,
Insulation reaction 2h.End of reaction filters out insoluble solid, and carries out rectifying, and control rectification temperature is 65~100 DEG C, rectifying pressure
Power is normal pressure, and rectifying column theoretical cam curve is 10, collects 53~55 DEG C of fractions, obtains 1,1,2,3,3,3- hexafluoro third of target product
Ylmethyl ether.
The GC of 1,1,2,3,3,3- hexafluoro propyl methyl ether crude product before and after the processing analyzes result such as the following table 2.
Table 2
The removal of unsaturated impurity in embodiment 4:1,1,2,3,3,3- hexafluoro propyl -2,2,2- trifluoroethyl ether crude product
In three-necked flask with a mixing device, 1,1,2,3,3,3- prepared according to 1 the method for embodiment is added
Hexafluoro propyl -2,2,2- trifluoroethyl ether crude product 1743g.After tested, described 1,1,2,3,3,3- hexafluoro propyl -2,2,2- trifluoro
The total content of unsaturated impurity is 5.3% (about 0.4mol) in ethylether crude product, wherein CF3CF=CF-O-CH2CF3Content is
3.4%, CF2=CFCF2-O-CH2CF3It is 1.9%.Methanol 35g (1.1mol) and sodium hydroxide is added into three-necked flask again
16g (0.4mol), stirring are warming up to 30 DEG C, insulation reaction 2h.End of reaction filters out insoluble solid, and carries out rectifying, control
Rectification temperature is 80~120 DEG C, and rectifying pressure is normal pressure, and rectifying column theoretical cam curve is 10, collects 70~72 DEG C of fractions, obtains
Target product 1,1,2,3,3,3- hexafluoro propyl -2,2,2- trifluoroethyl ether.
The GC of 1,1,2,3,3,3- hexafluoro propyl -2,2,2- trifluoroethyl ether crude product before and after the processing analyzes result such as the following table 3.
Table 3
Unsaturated impurity goes in embodiment 5:1,1,2,3,3,3- hexafluoro propyl -2,2,3,3,3- pentafluoropropyl group ether crude product
It removes
In three-necked flask with a mixing device, 1,1,2,3,3,3- prepared according to 1 the method for embodiment is added
Hexafluoro propyl -2,2,3,3,3- pentafluoropropyl group ether crude product 1420g.After tested, described 1,1,2,3,3,3- hexafluoro propyl -2,2,3,
The total content of unsaturated impurity is 7.4% (about 0.4mol) in 3,3- pentafluoropropyl group ether crude products, wherein CF3CF=CF-O-
CH2CF2CF3Content is 4.7%, CF2=CFCF2-O-CH2CF2CF3It is 2.7%.Methanol 40g is added into three-necked flask again
(1.25mol) and sodium hydroxide 24g (0.6mol), stirring are warming up to 50 DEG C, insulation reaction 3h.End of reaction filters out insoluble
Solid, and rectifying is carried out, control rectification temperature is 100~140 DEG C, and rectifying pressure is normal pressure, and rectifying column theoretical cam curve is 10,
84~86 DEG C of fractions are collected, 1,1,2,3,3,3- hexafluoro propyl -2,2 of target product, 3,3,3- pentafluoropropyl group ethers are obtained.
The GC analysis result of 1,1,2,3,3,3- hexafluoro propyl -2,2,3,3,3- pentafluoropropyl group ether crude product before and after the processing is as follows
Table 4.
Table 4
Comparative example 1: rectifying removes the unsaturated impurity in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product
1 that embodiment 2 is used, 1,2,3,3,3- hexafluoro ethyl ether crude product directly carry out distillation operation, control essence
Evaporating temperature is 80~120 DEG C, and rectifying pressure is normal pressure, and rectifying column theoretical cam curve is 10, collects 69~71 DEG C of fractions, obtains most
Finished product 1,1,2,3,3,3- hexafluoro ethyl ether.
1 that embodiment 3 is used, 1,2,3,3,3- hexafluoro propyl methyl ether crude product directly carry out distillation operation, control essence
Evaporating temperature is 65~100 DEG C, and rectifying pressure is normal pressure, and rectifying column theoretical cam curve is 10, collects 53~55 DEG C of fractions, obtains most
Finished product 1,1,2,3,3,3- hexafluoro propyl methyl ether.
The 1,1,2,3,3,3- hexafluoro propyl -2,2,2- trifluoroethyl ether crude product that embodiment 4 uses directly is subjected to rectifying
Operation, control rectification temperature are 80~120 DEG C, and rectifying pressure is normal pressure, and rectifying column theoretical cam curve is 10, collect 70~72 DEG C
Fraction obtains 1,1,2,3,3,3- hexafluoro propyl -2,2 of final products, 2- trifluoroethyl ether.
The 1,1,2,3,3,3- hexafluoro propyl -2,2,3,3,3- pentafluoropropyl group ether ether crude product that embodiment 5 is used directly into
Row distillation operation, rectification temperature processed are 100~140 DEG C, and rectifying pressure is normal pressure, and rectifying column theoretical cam curve is 10, collect 84
~86 DEG C of fractions obtain 1,1,2,3,3,3- hexafluoro propyl -2,2 of final products, 3,3,3- pentafluoropropyl group ethers.
GC after each 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product rectifying analyzes result such as the following table 5.
Table 5
Claims (9)
1. the method for unsaturated compound in a kind of 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product of removal, it is characterised in that institute
The method of stating includes: the insatiable hunger under alkylol and alkali compounds effect, in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product
With compound is reacted obtains corresponding alkylol addition product；
The alkylol is the alkylol of C1~C5；
The alkali compounds is selected from alkali metal hydroxide, alkali halide, alkaline earth metal hydroxide and alkaline-earth metal
One of halide, two or three of combination of the above；
The structural formula of the 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether is CF3CHFCF2-O-CH2R；
The unsaturated compound includes CF2=CFCF2-O-CH2R and/or CF3CF=CF-O-CH2R；
The R=-CaHbFc, independently selected from 0~10 integer, b is selected from the integer more than or equal to 1, and b+c=2a+1 by a and c.
2. the side of unsaturated compound in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product described in accordance with the claim 1
Method, it is characterised in that the alkylol is selected from one of methanol, ethyl alcohol and propyl alcohol, two or three of combination of the above.
3. the side of unsaturated compound in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product described in accordance with the claim 1
Method, it is characterised in that the alkali compounds is selected from sodium hydroxide, potassium hydroxide, cesium hydroxide, magnesium hydroxide, sodium fluoride, fluorine
Change one of potassium, cesium fluoride and magnesium fluoride, two or three of combination of the above.
4. the side of unsaturated compound in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product described in accordance with the claim 1
Method, it is characterised in that a is selected from 0~3 integer, and b is selected from the integer more than or equal to 1, and b+c=2a+1.
5. removing the side of unsaturated compound in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product according to claim 4
Method, it is characterised in that in the structural formula of described 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether, a is selected from 0~2 integer.
6. the side of unsaturated compound in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product described in accordance with the claim 1
Method, it is characterised in that the molar ratio of the alkali compounds and unsaturated compound is 0.1~3:1, the alkylol and insatiable hunger
Molar ratio with compound is 2~10:1.
7. removing the side of unsaturated compound in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product according to claim 6
Method, it is characterised in that the molar ratio of the alkali compounds and unsaturated compound is 1~2:1, the alkylol and unsaturation
The molar ratio of compound is 3~5:1.
8. the side of unsaturated compound in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product described in accordance with the claim 1
Method, it is characterised in that reaction temperature is 0~90 DEG C.
9. removing the side of unsaturated compound in 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product according to claim 8
Method, it is characterised in that reaction temperature is 30~50 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510816940.2A CN106748676B (en) | 2015-11-23 | 2015-11-23 | A method of unsaturated impurity in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510816940.2A CN106748676B (en) | 2015-11-23 | 2015-11-23 | A method of unsaturated impurity in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106748676A CN106748676A (en) | 2017-05-31 |
| CN106748676B true CN106748676B (en) | 2019-09-27 |
Family
ID=58885521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510816940.2A Active CN106748676B (en) | 2015-11-23 | 2015-11-23 | A method of unsaturated impurity in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106748676B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2815834C1 (en) * | 2020-10-21 | 2024-03-22 | Дайкин Индастриз, Лтд. | Method of producing composition containing purified fluorine-containing ether compound |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116348443A (en) * | 2020-10-21 | 2023-06-27 | 大金工业株式会社 | Method for producing composition containing purified fluoroether compound |
| CN114907192B (en) * | 2022-04-20 | 2023-11-14 | 浙江永太氟乐科技有限公司 | Preparation method of hydrofluoroether compound |
| JP2023159878A (en) * | 2022-04-20 | 2023-11-01 | ダイキン工業株式会社 | Method for producing composition including purified fluorine-containing ether compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102115428A (en) * | 2010-12-27 | 2011-07-06 | 锦州惠发天合化学有限公司 | Method for synthesizing hydrofluoro ether |
-
2015
- 2015-11-23 CN CN201510816940.2A patent/CN106748676B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102115428A (en) * | 2010-12-27 | 2011-07-06 | 锦州惠发天合化学有限公司 | Method for synthesizing hydrofluoro ether |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2815834C1 (en) * | 2020-10-21 | 2024-03-22 | Дайкин Индастриз, Лтд. | Method of producing composition containing purified fluorine-containing ether compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106748676A (en) | 2017-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106748676B (en) | A method of unsaturated impurity in removal 1,1,2,3,3,3- hexafluoro propyl hydrofluoroether crude product | |
| US9963410B2 (en) | Method for producing 1-chloro-2,3,3-trifluoropropene | |
| JP5946410B2 (en) | Process for producing 2-chloro-3,3,3-trifluoropropene | |
| US9090530B1 (en) | Method for producing 1,2-dichloro-3,3,3-trifluoropropene | |
| CN110577460A (en) | Preparation method of hexafluoropropylene tripolymer | |
| KR101332460B1 (en) | Method for producing fluorine-containing ether | |
| JP5837588B2 (en) | Method for producing chlorohydrin composition and method for producing epichlorohydrin using chlorohydrin composition produced by the method | |
| JP5837584B2 (en) | Method for producing chlorohydrin and method for producing epichlorohydrin using chlorohydrin produced by the method | |
| JP6708984B2 (en) | Method for producing fluoroolefin | |
| CN108383681B (en) | Preparation method of perfluoro-2-methyl-2-pentene | |
| EP2589586B1 (en) | Method for preparing chlorohydrins composition and method for preparing epichlorohydrin using chlorohydrins composition prepared thereby | |
| JP2010525074A (en) | Novel alkyloxy-ethers and their alkoxylates | |
| JP5837587B2 (en) | Method for producing chlorohydrin composition and method for producing epichlorohydrin using chlorohydrin composition produced by the method | |
| JP6550927B2 (en) | Method for producing alkyl iodide compound | |
| JP2006256967A (en) | Method for producing fluorine-containing compound | |
| US1730061A (en) | Ether of propylene glycol and process for making the same | |
| US20100168450A1 (en) | Novel branched alkoxylates | |
| EP2330093B1 (en) | Fluoroolefin iodide mixture and method for producing same | |
| EP2589585B1 (en) | Method for preparing chlorohydrins and method for preparing epichlorohydrin using chlorohydrins prepared thereby | |
| WO2005102983A1 (en) | Process for producing fluorinated acrylic ester | |
| JP2016074635A (en) | Method for producing (poly)propylene glycol diether | |
| KR100744834B1 (en) | Method for preparing of fluorinated alkoxysilane derivatives | |
| US9624147B2 (en) | Production of short chain perfluoroalkyl iodides from higher order telomers | |
| JP6694818B2 (en) | Improved process for producing propylene glycol | |
| KR101935182B1 (en) | Method for producing 3-chloro-2-hydroxypropyl (meth)acrylate and method for producing glycidyl (meth)acrylate |
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 |