CN105330567B - The method of pressure synthesis trifluoro ethoxy propionitrile - Google Patents
The method of pressure synthesis trifluoro ethoxy propionitrile Download PDFInfo
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- CN105330567B CN105330567B CN201510907706.0A CN201510907706A CN105330567B CN 105330567 B CN105330567 B CN 105330567B CN 201510907706 A CN201510907706 A CN 201510907706A CN 105330567 B CN105330567 B CN 105330567B
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- trifluoro ethoxy
- catalyst
- acrylonitrile
- ethoxy propionitrile
- trifluoroethanol
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- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Abstract
Present invention relates particularly to a kind of method of pressure synthesis trifluoro ethoxy propionitrile, comprise the following steps：Step one, it will be placed in after trifluoroethanol, acrylonitrile and catalyst uniformly mixing in autoclave, keep hyperbaric environment；Mixture in step 2, heating autoclave, makes heating trifluoroethanol and acrylonitrile reactor synthesize trifluoro ethoxy acrylonitrile；Step 3, vacuum distillation removes low-boiling-point substance, and trifluoro ethoxy propionitrile is made.Catalyst is acetate and one or more mixtures of organic bases.The method of the pressure synthesis trifluoro ethoxy propionitrile provided compared to prior art, the present invention, trifluoroethanol, acrylonitrile and catalyst are reacted under hyperbaric environment, and trifluoro ethoxy propionitrile is made；It is short with the reaction time, the advantage of high income；And the catalyst used, it is with low cost, it can effectively reduce the production cost of trifluoro ethoxy propionitrile.
Description
Technical field
The present invention relates to lithium from battery manufacturing field, more particularly to a kind of lithium battery producer of trifluoro ethoxy propionitrile
Method.
Background technology
Trifluoro ethoxy propionitrile is a kind of higher boiling, the solvent of low viscosity, can be applied to high power lithium battery, improves its safety
Performance and cycle performance, it can be obtained by trifluoroethanol and acrylonitrile addition.And due in trifluoroethanol trifluoromethyl be located at alcohol
The α positions of hydroxyl, the acid increase of alcohol, the alkalescence decrease of conjugate base, nucleophilicity reduction, the addition for being unfavorable for unsaturated hydrocarbons and alcohol is anti-
Should.Therefore, reaction needs certain condition just to obtain product in high yield.
In the prior art, the synthesis technique of trifluoro ethoxy propionitrile mainly has following two：
The first, document Novel electrolytes for Li4Ti5O12-based high power lithium
Ion batteries with nitrile solvents, By Wang, Qing；Pechy,Peter；Zakeeruddin,
Shaik M.；Exnar,Ivan；Graetzel, Michael, described in, trifluoroethanol, acrylonitrile are in catalyst 40%
Under tritonB effects, reacted 10 hours at 110 DEG C, the reaction time of this method is long, and yield is relatively low.
Second, document Hydroamination and Alcoholysis of Acrylonitrile Promoted
By the Pincer Complex { κ P, κ C, κ P-2,6- (Ph2PO) 2C6H3 } Ni (OSO2CF3), By Salah,
Abderrahmen B.；Offenstein,Caroline；Zargarian,Davit.It is in 0.5%~1% catalyst { κP,κC,
κP-2,6-(Ph2PO)2C6H3}Ni(OSO2CF3) and triethylamine effect under, the 50 DEG C of reactions 0.5~5.5 of trifluoroethanol and acrylonitrile
Hour, yield 90~100%.The reaction time of this method is shorter, and yield is also higher, but the Catalyst Production being related to is difficult,
Production cost is too high.
The content of the invention
It is an object of the invention to provide a kind of reaction time is short, production efficiency is high, and the catalyst cost used is low
The method of honest and clean pressure synthesis trifluoro ethoxy propionitrile.
To achieve the above object, the present invention provides a kind of method of pressure synthesis trifluoro ethoxy propionitrile, including following step
Suddenly：Step one, it will be placed in after trifluoroethanol, acrylonitrile and catalyst uniformly mixing in autoclave, keep hyperbaric environment；
Mixture in step 2, heating autoclave, makes heating trifluoroethanol and acrylonitrile reactor synthesize trifluoro ethoxy
Acrylonitrile；
Step 3, vacuum distillation removes low-boiling-point substance, and trifluoro ethoxy propionitrile is made.
It is preferred that, the catalyst is acetate and one or more mixtures of organic bases.
It is preferred that, the catalyst is copper acetate or nickel acetate.
It is preferred that, the catalyst is triethylamine or pyridine.
It is preferred that, the amount ratio of trifluoroethanol and the acrylonitrile material is 1:1, the catalyst amount be 0.5%~
10%.
It is preferred that, the catalyst amount is 3%~7%.
It is preferred that, in the step one, the pressure in autoclave is 0.1MPa~4.5Mpa；In step 2, heating-up temperature
For 60 DEG C~160 DEG C；Reaction time in step 2 is 1~6 hour.
It is preferred that, in the step one, the pressure in autoclave is 0.5MPa~3.5MPa；In step 2, heating-up temperature
For 70 DEG C~150 DEG C；Reaction time in step 2 is 2~5 hours.
The beneficial effects of the invention are as follows：The method for the pressure synthesis trifluoro ethoxy propionitrile that the present invention is provided, by trifluoro second
Alcohol, acrylonitrile and catalyst react under hyperbaric environment, and trifluoro ethoxy propionitrile is made；It is short with the reaction time, high income
Advantage；And the catalyst used, it is with low cost, it can effectively reduce the production cost of trifluoro ethoxy propionitrile.
Brief description of the drawings
The process chart of the method for the pressure synthesis trifluoro ethoxy propionitrile that Fig. 1 provides for the present invention.
Embodiment
In order to more clearly state the present invention, the present invention is further described below in conjunction with the accompanying drawings.
Refering to the method for Fig. 1, the present invention pressure synthesis trifluoro ethoxy propionitrile provided, comprise the following steps：
Step one, it will be placed in after trifluoroethanol, acrylonitrile and catalyst uniformly mixing in autoclave, keep hyperbaric environment；
Mixture in step 2, heating autoclave, makes heating trifluoroethanol and acrylonitrile reactor synthesize trifluoro ethoxy
Acrylonitrile；
Step 3, vacuum distillation removes low-boiling-point substance, and trifluoro ethoxy propionitrile is made.
Wherein, catalyst is acetate and one or more mixtures of organic bases.
The method of the pressure synthesis trifluoro ethoxy propionitrile provided compared to prior art, the present invention, by trifluoroethanol, third
Alkene nitrile and catalyst react under hyperbaric environment, and trifluoro ethoxy propionitrile is made；It is short with the reaction time, the advantage of high income；
And the catalyst used, it is with low cost, it can effectively reduce the production cost of trifluoro ethoxy propionitrile.
Proved with reference to specific embodiment：
Embodiment one
By trifluoroethanol, acrylonitrile with 1:The amount of 1 material adds three second of 5% gross mass than adding in autoclave
Amine；Kettle cover is covered, 130 DEG C are warming up to, now pressure 1.2MPa, reacted 3 hours, pressure is gradually decreased.Pour out, depressurize after cooling
Distill to obtain product trifluoro ethoxy propionitrile.Measure the content of trifluoro ethoxy propionitrile, and calculated yield.
Above step is repeated several times, multigroup content value and yield value is obtained；The average value repeatedly measured is sought, show that content is
99.5%, yield is 90%.
Embodiment two
By trifluoroethanol, acrylonitrile with 1:The amount of 1 material adds the three of 2.5% gross mass than adding in autoclave
The nickel acetate of ethamine and 2.5% gross mass, is warming up to 150 DEG C, now pressure 0.5MPa, reacts 5 hours；Pressure is slow to be reduced.It is cold
But pour out afterwards, vacuum distillation obtains product trifluoro ethoxy propionitrile.Measure the content of trifluoro ethoxy propionitrile, and calculated yield.
Above step is repeated several times, multigroup content value and yield value is obtained；The average value repeatedly measured is sought, show that content is
99.6%, yield is 94%.
Embodiment three
By trifluoroethanol, acrylonitrile with 1:The amount of 1 material is equipped with return duct, the three-necked flask of thermometer than adding,
The nickel acetate of 5% gross mass is added, 60 DEG C is warming up to and reacts 7 hours, distillation, which is removed, obtains product after low-boiling-point substance.
Content is 84%, and yield is 70%.
Example IV
By trifluoroethanol, acrylonitrile with 1:The amount of 1 material adds the pyridine of 7% gross mass than adding in autoclave；
Kettle cover is covered, 160 DEG C are warming up to, now pressure 3.5MPa, reacted 6 hours, pressure is gradually decreased.Poured out after cooling, decompression is steamed
Evaporate to obtain product trifluoro ethoxy propionitrile.Measure the content of trifluoro ethoxy propionitrile, and calculated yield.
Above step is repeated several times, multigroup content value and yield value is obtained；The average value repeatedly measured is sought, show that content is
99.5%, yield is 94%.
Embodiment five
By trifluoroethanol, acrylonitrile with 1:The amount of 1 material adds the acetic acid of 3% gross mass than adding in autoclave
Copper；Kettle cover is covered, 70 DEG C are warming up to, now pressure 4.5MPa, reacted 2 hours, pressure is gradually decreased.Pour out, depressurize after cooling
Distill to obtain product trifluoro ethoxy propionitrile.Measure the content of trifluoro ethoxy propionitrile, and calculated yield.
Above step is repeated several times, multigroup content value and yield value is obtained；The average value repeatedly measured is sought, show that content is
87.4%, yield is 85%.
As can be seen from the above experimental data, the method for the pressure synthesis trifluoro ethoxy propionitrile that the present invention is provided, has
Reaction time is short, and content is high, the advantage of high income；And the catalyst used is with low cost, significantly reduces trifluoro ethoxy
The production cost of propionitrile.
It these are only the preferred embodiment of the present invention, it is noted that come for those skilled in the art
Say, without departing from the technical principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (6)
1. a kind of method of pressure synthesis trifluoro ethoxy propionitrile, it is characterised in that comprise the following steps：
Step one, it will be placed in after trifluoroethanol, acrylonitrile and catalyst uniformly mixing in autoclave, keep hyperbaric environment；
Mixture in step 2, heating autoclave, makes heating trifluoroethanol and acrylonitrile reactor synthesize trifluoro ethoxy propylene
Nitrile；
Step 3, vacuum distillation removes low-boiling-point substance, and trifluoro ethoxy propionitrile is made；
The catalyst is one or more mixtures of acetate.
2. the method for pressure synthesis trifluoro ethoxy propionitrile according to claim 1, it is characterised in that：The catalyst is
Copper acetate or nickel acetate.
3. the method for pressure synthesis trifluoro ethoxy propionitrile according to claim 1, it is characterised in that the trifluoroethanol
Amount ratio with acrylonitrile material is 1:1, the catalyst amount is 0.5%~10%.
4. the method for pressure synthesis trifluoro ethoxy propionitrile according to claim 3, it is characterised in that the catalyst is used
Measure as 3%~7%.
5. the method for the pressure synthesis trifluoro ethoxy propionitrile according to claim any one of 1-4, it is characterised in that described
In step one, the pressure in autoclave is 0.1MPa~4.5Mpa；In step 2, heating-up temperature is 60 DEG C~160 DEG C；Step 2
In reaction time be 1~6 hour.
6. the method for pressure synthesis trifluoro ethoxy propionitrile according to claim 5, it is characterised in that the step one
In, the pressure in autoclave is 0.5MPa~3.5MPa；In step 2, heating-up temperature is 70 DEG C~150 DEG C；It is anti-in step 2
It is 2~5 hours between seasonable.
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| CN201510907706.0A CN105330567B (en) | 2015-12-09 | 2015-12-09 | The method of pressure synthesis trifluoro ethoxy propionitrile |
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|---|---|---|---|
| CN201510907706.0A CN105330567B (en) | 2015-12-09 | 2015-12-09 | The method of pressure synthesis trifluoro ethoxy propionitrile |
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| CN105330567A CN105330567A (en) | 2016-02-17 |
| CN105330567B true CN105330567B (en) | 2017-11-07 |
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2015
- 2015-12-09 CN CN201510907706.0A patent/CN105330567B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| Hydroamination and Alcoholysis of Acrylonitrile Promoted by the Pincer Complex {kP,kC,kP-2,6-(Ph2PO)2C6H3}Ni(OSO2CF3);Abderrahmen B. Salah et al;《Organometallics》;20110919;5352-5364 * |
| Monomeric and Dimeric Nickel Complexes Derived from a Pincer Ligand Featuring a Secondary Amine Donor Moiety;Denis M. Spasyuk et al;《Inorganic Chemistry》;20100607;第49卷(第13期);6203-6213 * |
| Novel electrolytes for Li4Ti5O12-based high power lithium;Qing Wang et al;《Journal of Power Sources》;20050531;第146卷;813-816 * |
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| CN105330567A (en) | 2016-02-17 |
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