CN105949030B - The method for preparing perfluor heptene isomer - Google Patents
The method for preparing perfluor heptene isomer Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
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Abstract
The present invention relates to a kind of methods for preparing perfluor heptene isomer, are F (CF with general formula in solvent dimethylformamide, dimethyl sulfoxide or sulfolane2)xCF=CF (CF2)yThe perfluor heptene of F (x+y=5, x=0,1,2) is raw material, in the presence of catalyst ammonium fluoride, potassium fluoride, lithium fluoride, sodium fluoride, rubidium fluoride RbF or cesium fluoride, isomerization reaction occurs and obtains F (CF2)nCF=CF (CF2)mF (m+n=5, n=0,1,2).Not only reaction condition is mild, reaction is easy to control for technical method provided by the invention, does not need anhydrous and oxygen-free operation, but also the isomer yield of perfluor heptene is higher, is easy to industrialize.
Description
Technical field
The present invention relates to a kind of methods for preparing perfluor heptene isomer, more particularly to a kind of perfluor heptene that passes through to exist
As catalyst the method that isomerization reaction prepares perfluor heptene isomer occurs for fluoride salt.
Background technique
Perfluor heptene is that a kind of ODP value is zero, the very low perfluorocarbon compound of GWP value.Its isomer mainly has entirely
Fluoro- 1- heptene, perfluor -2- heptene, perfluor -3- heptene.It is mainly used as preparing the important intermediate of methyl perfluoro heptenyl ether.By
It is zero in the ODP value of methyl perfluoro heptenyl ether, GWP value is very low, wherein E-4- methoxy-2-perfluoro -3- heptene, E-3- methoxy
Base-perfluor -3- heptene, Z-4- methoxy-2-perfluoro -3- heptene, Z-3- methoxy-2-perfluoro -3- four kinds of isomers of heptene
GWP value is followed successively by 1.1,1.2,12,30 [Environ.Sci.Technol.2014,48,4954-4962.], and all nonflammable,
Cleaning performance is superior, suitable for semiconductor chip and circuit board cleaning, goes weldering and degreasing；Methyl perfluoro heptenyl ether or good
Heat transfer fluid, can be used for high temperature heat pump etc..With the rapid development of electronics industry, to high performance cleaning agent methyl perfluoro
The demand of heptenyl ether is increasing, higher and higher to its performance requirement.However the technical threshold of methyl perfluoro heptenyl ether compared with
Height causes its production cost expensive.Its technical bottleneck is mainly the synthesis of perfluor heptene.Therefore, the synthesis of perfluor heptene is more next
More cause company of various countries and the concern of scientist.
Currently, few to the document of perfluor heptene synthesis report.Lazerte J.D. etc. [J.A.C.S., 75 (1953):
4525-4526.] it reports at 210-300 DEG C, Sodium perfluorooctanoate is pyrolyzed to obtain -1 heptene of sodium fluoride, carbon dioxide and perfluor,
The yield of -1 heptene of perfluor is 86%.
United States Patent (USP) US2926203 is reported at 620 DEG C of temperature, and perfluoro caprylic acid occurs pyrolysis and obtains perfluor -1- heptene,
Yield is 85%.
Krusic P.J. etc. [J.Fluorine Chem., 126 (2005): 1510-1516.] is reported in temperature 355-
At 385 DEG C, perfluoro caprylic acid is pyrolyzed to obtain -1 heptene of perfluor and 1-H- perfluor-normal heptane, and -1 heptene yield of perfluor is at 385 DEG C
15.2%, 1-H- perfluor-normal heptane yield are 39.5%.
Paciorek K.J.L. etc. [J.Fluorine Chem., 55 (1991): 271-282.] reports a kind of three-step approach
The method for synthesizing -1 heptene of perfluor, specific as follows: firstly, at 145-150 DEG C of temperature, the iodo- perfluoro-n-octane of 1- and chlorosulfonic acid
Reaction 20 hours, methanol is then added dropwise in ice bath, after being added dropwise, then flows back 4 hours, obtains perfluoro-n-octanoic acid methyl esters, produces
Rate is 89%；Secondly, at room temperature, perfluoro-n-octanoic acid methyl esters hydrolyzes in 10%NaOH solution and obtains perfluoro-n-octanoic acid sodium, produce
Rate is 70-75%；Finally, perfluoro-n-octanoic acid sodium occurs pyrolysis and obtains -1 heptene of perfluor, yield at 210-300 DEG C of temperature
For 85-95%.
C í ekva V. etc. [J.Fluorine Chem., 75 (1995): 87-92.] is reported at 200 DEG C of temperature, 2,5-
- 3 hexin of two (t-butylperoxy) -2,5- dimethyl is initiator, causes the tune of perfluoro-n-butyl group iodine and perfluorinated allyl base chlorine
Poly- reaction, reaction time 40h generate -1 heptene of perfluor and ICl, and the yield of -1 heptene of perfluor is 26.0%.
Krespan C.G. etc. [J.O.C., 51 (1986): 4460-4466.] reports perfluor -1- heptene and three oxidations
Sulphur, trimethyl borine react, reaction condition are as follows: react 48 hours prior to 25 DEG C, react 96 hours, synthesizing then at 100 DEG C
While principal product perfluor -2- heptenyl -1- fluoro- sulfonic acid, by-product perfluor -2- heptene is also generated, yield is about 11%,
And perfluor -2- heptene and superfluous raw material perfluor -1- heptene form azeotropic mixture, which becomes 1:1, boiling point 23-30
℃/90mmHg。
Chepik, S.D. etc. [Bulletin of the Academy of Sciences of the USSR,
Division of chemical science, 39 (1990): 1674-1680.] it reports in the presence of catalyst antimony pentafluoride
Under, 100 DEG C of reaction temperature, isomerization reaction occurs for catalysis perfluoro-n-butyl group cyclopropane, and reaction time 4h generates perfluor -2- heptan
Alkene and perfluor -3- heptene, wherein perfluor -3- heptene yield is 81%, and perfluor -2- heptene yield is 14%.
Petrov V.A. etc. [J.Fluorine Chem., 77 (1996): 139-142.] is reported to be existed in chlorofluorination aluminium
Under, 25 DEG C of reaction temperature, isomerization reaction, reaction time 90h occur for catalysis -1 heptene of perfluor, and perfluor -1- heptene conversion ratio is
100%, perfluor -2- heptene yield are 5.8% (ratio of cis-trans configurations is 0.8/5.0), and perfluor -3- heptene yield is 94.2%
(ratio of cis-trans configurations is 5.0/89.2).
The above method has the following deficiencies: firstly, perfluoro caprylic acid or Sodium Caprylate are the route of raw material using high temperature (620 DEG C)
Pyrolysis, belongs to high energy consumption, is not suitable for industrialized technology path；Secondly, the route that perfluoroalkyl iodides are raw material uses multistep anti-
It answers or telomerisation prepares perfluor heptene, expensive starting materials are not easy to obtain；Thirdly, with perfluoro-n-butyl group cyclopropane or
Perfluor -1- heptene is that the route of raw material prepares perfluor heptene, yield too low (11%) or catalyst using isomerization reaction
Antimony pentafluoride, chlorofluorination aluminium must use under the conditions of anhydrous and oxygen-free or the reaction time is very long, is up to 90 hours.
Summary of the invention
The present invention is for the deficiency in background technique, and providing one kind, not only reaction condition is mild, reaction is easy to control, is not required to
Anhydrous and oxygen-free is wanted to operate, and the isomer yield of perfluor heptene is higher, is easy to industrialized technical method.
It is a kind of prepare general formula be F (CF2)nCF=CF (CF2)mThe method of the perfluor heptene of F (m+n=5, n=0,1,2),
Be characterized in that: it is described in a solvent, be F (CF with general formula2)xCF=CF (CF2)yThe perfluor heptene of F (x+y=5, x=0,1,2)
Isomerization reaction occurs and obtains in the presence of a catalyst for raw material；
As x=0, n=1 and 2；
As x=1, n=0,1 and 2；
As x=2, n=0,1 and 2；
The catalyst is cesium fluoride, potassium fluoride, lithium fluoride, sodium fluoride, rubidium fluoride RbF or ammonium fluoride, and the solvent is diformazan
Base formamide, dimethyl sulfoxide or sulfolane.
The molar ratio of the catalyst, solvent and raw material is 0.05~1:5~20:1, and reaction temperature is -60~150 DEG C,
Reaction time is 0.01~10 hour.
It is preferred that: the molar ratio of catalyst, solvent and raw material is 0.1~0.5:10~15:1, and reaction temperature is -10~100
DEG C, the reaction time is 1~3 hour.
Preferred catalyst is cesium fluoride, and preferred solvent is dimethylformamide.
When the raw material is perfluor -1- heptene, reaction product is E- perfluor -2- heptene, Z- perfluor -2- heptene, E- perfluor -
3- heptene and Z- perfluor -3- heptene.
When the raw material is E- perfluor -2- heptene, reaction product is Z- perfluor -2- heptene, perfluor -1- heptene, E- perfluor -
3- heptene and Z- perfluor -3- heptene.
When the raw material is Z- perfluor -2- heptene, reaction product is E- perfluor -2- heptene, perfluor -1- heptene, E- perfluor -
3- heptene and Z- perfluor -3- heptene.
When the raw material is E- perfluor -3- heptene, reaction product is Z- perfluor -3- heptene, perfluor -1- heptene, E- perfluor -
2- heptene and Z- perfluor -2- heptene.
When the raw material is Z- perfluor -3- heptene, reaction product is E- perfluor -3- heptene, perfluor -1- heptene, E- perfluor -
2- heptene and Z- perfluor -2- heptene.
The present invention with E- perfluor -1- heptene or Z- perfluor -1- heptene or E- perfluor -2- heptene or Z- perfluor -2- heptene or
E- perfluor -3- heptene or Z- perfluor -3- heptene are raw material, react by liquid-phase isomerization, it is same to obtain corresponding perfluor heptene
Enantiomers.Its key reaction is as follows:
The present invention can carry out under normal pressure, can also carry out under high pressure.Due to being liquid phase reactor, be not related to phase feed or
Product, therefore, pressurization influence less reaction of the present invention, therefore, the preferred normal pressure of the present invention.
The present invention can carry out in the reactor of glass material, enamel material or polytetrafluoro material vinyl material.
The present invention provides one kind can be with the preparation method of a variety of isomers of coproduction perfluor heptene, wherein perfluor-
1- heptene can isomerization preparation E- perfluor -2- heptene, Z- perfluor -2- heptene, E- perfluor -3- heptene and Z- perfluor -3- heptene；E-
Perfluor -2- heptene can isomerization preparation Z- perfluor -2- heptene, perfluor -1- heptene, E- perfluor -3- heptene and Z- perfluor -3- heptan
Alkene；Z- perfluor -2- heptene can isomerization preparation E- perfluor -2- heptene, perfluor -1- heptene, E- perfluor -3- heptene and Z- perfluor -
3- heptene；E- perfluor -3- heptene can isomerization preparation Z- perfluor -3- heptene, perfluor -1- heptene, E- perfluor -2- heptene and Z- it is complete
Fluoro- 2- heptene；Z- perfluor -3- heptene can isomerization preparation E- perfluor -3- heptene, perfluor -1- heptene, E- perfluor -2- heptene and
Z- perfluor -2- heptene.It only needs isomerization reaction product to be carried out that phase can be obtained except the post-processing such as solvent, water removal, purification respectively
Answer product.Wherein, E- perfluor -3- heptene boiling point is 69-71 DEG C (760mmHg), and Z- perfluor -3- heptene boiling point is 72-75 DEG C
(760mmHg), E- perfluor -2- heptene are 78-82 DEG C (760mmHg), and Z- perfluor -2- heptene is 82-84 DEG C (760mmHg), entirely
Fluoro- 1- heptene boiling point is 80-82 DEG C (760mmHg).
Advantages of the present invention: not only reaction condition is mild, reaction is easy to control, does not need for technical method provided by the invention
Anhydrous and oxygen-free operation, and the isomer yield of perfluor heptene is higher, is easy to industrialize.
Specific embodiment
Analysis instrument: the glad chromatography GC-930 in Shanghai sea, hydrogen flame detector, chromatographic column are capillary column Al2O3/S“50m×
0.320mm × 0.25 μm " (manufacture of chromatographic technique research and development centre of Lanzhou Inst. of Chemical Physics, Chinese Academy of Sciences).
Gas chromatography analysis method: reaction product takes gaseous sample to carry out gas-chromatography point after washing, alkali cleaning and drying
Analysis.High Purity Nitrogen and hydrogen are used as carrier gas.Testing conditions are 250 DEG C of temperature of vaporization chamber, 250 DEG C of 2 temperature of auxiliary furnace, detector temperature
250 DEG C, 40 DEG C of column furnace initial temperature is kept for 10 minutes, 15 DEG C/min of heating rate, 230 DEG C of final temperature, is kept for 3 minutes.
It is following that the present invention is described in further detail in conjunction with the embodiments, but do not limit the scope of the invention.
Embodiment 1
Normal pressure under stirring condition, is burnt in 250 milliliters of glass equipped with condenser pipe and bubbler (making reaction in normal pressure)
In bottle, catalyst cesium fluoride, solvent dimethylformamide and raw material perfluor -1- heptene, molar ratio cesium fluoride/diformazan is added
Base formamide/perfluor -1- heptene be 0.3/12/1,50 DEG C of reaction temperature, the reaction time 3 hours.After reaction, through washing
100ml × 3 time remove solvent, and anhydrous magnesium sulfate 2.0g dries, filters to obtain organic phase, and organic phase is taken to carry out gas chromatographic analysis
The composition of organic matter, the results are shown in Table 1.
Above-mentioned organic phase is subjected to rectifying, obtains isomer perfluor -1- heptene, the E- perfluor -2- heptan of perfluor heptene
Alkene, Z- perfluor -2- heptene, E- perfluor -3- heptene and Z- perfluor -3- heptene.Wherein, E- perfluor -3- heptene boiling point is 69-71 DEG C
(760mmHg), Z- perfluor -3- heptene boiling point are 72-75 DEG C (760mmHg), and E- perfluor -2- heptene is 78-82 DEG C
(760mmHg), Z- perfluor -2- heptene are 82-84 DEG C (760mmHg), and perfluor -1- heptene boiling point is 80-82 DEG C (760mmHg).
Embodiment 2
Operation same as Example 1, except that cesium fluoride/dimethylformamide/perfluor -1- heptene molar ratio
Example is 0.05/20/1, the results are shown in Table 1.
Embodiment 3
Operation same as Example 1, except that cesium fluoride/dimethylformamide/perfluor -1- heptene molar ratio
Example is 0.1/15/1, the results are shown in Table 1.
Embodiment 4
Operation same as Example 1, except that cesium fluoride/dimethylformamide/perfluor -1- heptene molar ratio
Example is 0.5/10/1, the results are shown in Table 1.
Embodiment 5
Operation same as Example 1, except that cesium fluoride/dimethylformamide/perfluor -1- heptene molar ratio
Example is 1/5/1, the results are shown in Table 1.
Embodiment 6
Operation same as Example 1, except that -60 DEG C of reaction temperature, the reaction time 10 hours, it the results are shown in Table 1.
Embodiment 7
Operation same as Example 1, except that -25 DEG C of reaction temperature, the reaction time 6 hours, it the results are shown in Table 1.
Embodiment 8
Operation same as Example 1, except that 0 DEG C of reaction temperature, the reaction time 5 hours, it the results are shown in Table 1.
Embodiment 9
Operation same as Example 1, except that 25 DEG C of reaction temperature, the reaction time 4 hours, it the results are shown in Table 1.
Embodiment 10
Operation same as Example 1, except that 80 DEG C of reaction temperature, the reaction time 2 hours, it the results are shown in Table 1.
Embodiment 11
Operation same as Example 1, except that 110 DEG C of reaction temperature, the reaction time 1 hour, it the results are shown in Table 1.
Embodiment 12
Operation same as Example 1, except that 140 DEG C of reaction temperature, it the reaction time 0.25 hour, the results are shown in Table
1。
Embodiment 13
Operation same as Example 1, except that 150 DEG C of reaction temperature, it the reaction time 0.01 hour, the results are shown in Table
1。
Embodiment 14
Operation same as Example 1, except that perfluor -1- heptene is changed to E- perfluor -2- heptan of the amount of equal substances
Alkene the results are shown in Table 1.
Embodiment 15
Operation same as Example 1, except that perfluor -1- heptene is changed to Z- perfluor -2- heptan of the amount of equal substances
Alkene the results are shown in Table 1.
Embodiment 16
Operation same as Example 1, except that perfluor -1- heptene is changed to E- perfluor -3- heptan of the amount of equal substances
Alkene the results are shown in Table 1.
Embodiment 17
Operation same as Example 1, except that perfluor -1- heptene is changed to Z- perfluor -3- heptan of the amount of equal substances
Alkene the results are shown in Table 1.
Embodiment 18
Operation same as Example 1 the results are shown in Table 1 except that cesium fluoride changes the potassium fluoride of the amount of equal substances into.
Embodiment 19
Operation same as Example 1 the results are shown in Table 1 except that cesium fluoride changes the lithium fluoride of the amount of equal substances into.
Embodiment 20
Operation same as Example 1 the results are shown in Table 1 except that cesium fluoride changes the sodium fluoride of the amount of equal substances into.
Embodiment 21
Operation same as Example 1 the results are shown in Table 1 except that cesium fluoride changes the rubidium fluoride RbF of the amount of equal substances into.
Embodiment 22
Operation same as Example 1 the results are shown in Table 1 except that cesium fluoride changes the ammonium fluoride of the amount of equal substances into.
Table 1
Note: (1) raw material used in embodiment " 1-13 " and embodiment " 18-22 " is perfluor -1- heptene.
(2) raw material used in embodiment " 14 " is E- perfluor -2- heptene.
(1) raw material used in embodiment " 15 " is Z- perfluor -2- heptene.
(2) raw material used in embodiment " 16 " is E- perfluor -3- heptene.
(3) raw material used in embodiment " 17 " is Z- perfluor -3- heptene.
Claims (8)
1. a kind of general formula for preparing is F (CF2)nCF=CF (CF2)mThe method of the perfluor heptene isomer of F, in a solvent, with
General formula is F (CF2)xCF=CF (CF2)yThe perfluor heptene of F is raw material, in the presence of a catalyst, isomerization reaction occurs and obtains
It arrives；Wherein m+n=5, n=0,1,2；X+y=5, x=0,1,2；
As x=0, n=1 and 2；
As x=1, n=0,1 and 2；
As x=2, n=0,1 and 2；
The catalyst is cesium fluoride, potassium fluoride, lithium fluoride, sodium fluoride, rubidium fluoride RbF or ammonium fluoride, and the solvent is dimethyl methyl
Amide or dimethyl sulfoxide；
The molar ratio of the catalyst, solvent and raw material is 0.05~1:5~20:1, and reaction temperature is -60~150 DEG C, reaction
Time is 0.01~10 hour.
2. according to the method described in claim 1, the molar ratio of the catalyst, solvent and raw material is 0.1~0.5:10~15:
1, reaction temperature is -10~100 DEG C, and the reaction time is 1~3 hour.
3. the solvent is dimethylformamide according to the method described in claim 1, the catalyst is cesium fluoride.
4. according to the method described in claim 1, reaction product is E- perfluor -2- heptan when the raw material is perfluor -1- heptene
Alkene, Z- perfluor -2- heptene, E- perfluor -3- heptene and Z- perfluor -3- heptene.
5. according to the method described in claim 1, reaction product is Z- perfluor -2- heptan when the raw material is E- perfluor -2- heptene
Alkene, perfluor -1- heptene, E- perfluor -3- heptene and Z- perfluor -3- heptene.
6. according to the method described in claim 1, reaction product is E- perfluor -2- heptan when the raw material is Z- perfluor -2- heptene
Alkene, perfluor -1- heptene, E- perfluor -3- heptene and Z- perfluor -3- heptene.
7. according to the method described in claim 1, reaction product is Z- perfluor -3- heptan when the raw material is E- perfluor -3- heptene
Alkene, perfluor -1- heptene, E- perfluor -2- heptene and Z- perfluor -2- heptene.
8. according to the method described in claim 1, reaction product is E- perfluor -3- heptan when the raw material is Z- perfluor -3- heptene
Alkene, perfluor -1- heptene, E- perfluor -2- heptene and Z- perfluor -2- heptene.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093670A (en) * | 1976-03-05 | 1978-06-06 | Masahiro Ozawa | Process of isomerizing oligomers of hexafluoropropene |
| CN103483139A (en) * | 2012-06-15 | 2014-01-01 | 中化蓝天集团有限公司 | Perfluoro-2-methyl-2-pentene preparation method |
-
2016
- 2016-06-27 CN CN201610478666.7A patent/CN105949030B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093670A (en) * | 1976-03-05 | 1978-06-06 | Masahiro Ozawa | Process of isomerizing oligomers of hexafluoropropene |
| CN103483139A (en) * | 2012-06-15 | 2014-01-01 | 中化蓝天集团有限公司 | Perfluoro-2-methyl-2-pentene preparation method |
Non-Patent Citations (1)
| Title |
|---|
| Electrophilic reactions of fluorocarbons under the action of aluminum chlorofluoride, a potent Lewis acid;V.A.Petrov,et al.,;《Journal of Fluorine Chemistry》;19961231;第77卷;第139-142页 |
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