CN109750314A - A kind of preparation method of the double acyl fluorides of perfluoroalkyl - Google Patents
A kind of preparation method of the double acyl fluorides of perfluoroalkyl Download PDFInfo
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- CN109750314A CN109750314A CN201811653363.XA CN201811653363A CN109750314A CN 109750314 A CN109750314 A CN 109750314A CN 201811653363 A CN201811653363 A CN 201811653363A CN 109750314 A CN109750314 A CN 109750314A
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Abstract
The present invention relates to a kind of preparation methods of the double acyl fluorides of perfluoroalkyl, belong to fine technical field of fluorine chemical industry.The method of the invention is using alkyl diacid chloride as raw material, elder generation reacts in catalysis solvent with fluorization agent generates two acyl fluorides of alkyl, it is fluorinated to obtain the double acyl fluorides of perfluoroalkyl by anhydrous hydrogen fluoride electrolytic tank electrolysis again, last rectification and purification, the reagent that this method uses is simple and easy to get, preparation step is simple, safe, and the reaction time is short, is suitble to large-scale production.
Description
Technical field
The present invention relates to a kind of preparation methods of the double acyl fluorides of perfluoroalkyl, belong to fine technical field of fluorine chemical industry.
Background technique
(general formula is FOC (CF to the double acyl fluorides of perfluoroalkyl2)nIt COF) is synthesis perfluoroalkyl vinyl ether, difunctional perfluoropolyether
And difunctional fluorochemical urethane/monomer of polyamide important compound, using it as the fluorine-containing height of Material synthesis performance function
Molecular material is one of current fluorine material scientific research project.It the use of the double acyl fluorides of perfluoroalkyl is that raw material can be used to prepare entirely
Fluoride-based ether monomer Cytop and tetrafluoroethene copolymerization amorphous state optical clear polymer, perfluorocarboxylic acid type ion exchange
Resin, perfluoroelastomers etc..These polymer have unique chemical stability, rotproofness, anti-flammability, hydro-oleophobicity, prevent
Dirt etc. various features.It is all kinds of that its application has been deep into communication, military project, electronics, space flight, anti-corrosion, chemical industry, surfacecti proteon etc.
Social production, sphere of life are widely used in optical fiber, senior building, aircraft manufacturing, Precision Machining, historical relic's protection, high pressure
The industry such as insulation, ocean development, coated coating, business activity.
Due to the advance and complexity of the double acyl fluorides synthetic technologys of perfluoroalkyl, since the eighties in last century, such skill
The market of art and downstream product is monopolized by two, three Chemical Groups such as Dupont, Japan AGC always.Research and develop perfluor alkane
The novel synthesis of the double acyl fluorides of base is always the important directions of domestic and international fluorine chemistry worker.
The odd even of n number depends on synthetic method in the double acyl fluorides general formulas of perfluoroalkyl, and in contrast, n is the binary acyl of even number
Fluorine synthesis is easier to, and n is more difficult for the binary acyl fluorides synthesis of odd number, and document report synthetic method is few, and is not suitable for industrialized production.
According to the literature, the preparation method of perfluor binary acyl fluorides mainly has following five kinds at present:
(1) iodide process
The method is iodine by illumination or is thermally formed free radical, then addition reaction occurs with tetrafluoroethene and generates diiodo- four
Fluoroethane, this reaction yield is close to 100%；Diiodo- tetrafluoroethane is reacted with oleum again generates oxalyl fluorine, and yield exists
60%.
To obtain double acyl fluorides of n > 2, then diiodo- tetrafluoroethane is taken off to iodine at high temperature and is coupled, and diiodo- octafluorobutane
It is that diiodo- tetrafluoroethane high temperature takes off iodine product, seemingly with above-mentioned oxalyl fluorine class, then is aoxidized to obtain perfluor succinyl with oleum
Fluorine.
The method disadvantage is process conditions harshness, and reaction intermediate especially diiodo- tetrafluoroethane toxicity is big, and the three wastes are more.
(2) fluosulfonic acid ester process
Being reacted with double fluorosulfonyl per-compound with tetrafluoroethene is a kind of pole for preparing double fluosulfonic acid perfluoroalkyl esters
Its important method, this method are therefore radical addition polymerization reaction controls peroxide and tetrafluoro in the reaction system
Ethylene concentration is the key that n number distribution in control final product.
FSO2O-OSO2F+nC2F4→FSO2O(CF2CF2)nOSO2F
Fluosulfonic acid ester is easy to be changed into acyl fluorides under fluorine ion catalysis, and therefore, the double fluosulfonic acid esters of perfluoroalkyl are to be fluorinated
Potassium is catalytically decomposed to obtain perfluorodiacyl fluorinated, the quantitative progress of reaction.
Fluosulfonic acid ester process has the advantages that technique is simple and direct, but the adjusting polymerization technique and equipment condition difficulty ratio needed to be grasped
It is larger.
(3) fluorine gas fluoride process
To obtain the double acyl fluorides of perfluoroalkyl that n is odd number, the dilution fluorinated method of fluorine gas can be used.With malonyl fluorine
It is slowly passed through 10% fluorine nitrogen mixed gas of appropriate amount, under cryogenic fluorine in the container for filling sodium fluoride powder for raw material
Change, prepares perfluor malonyl fluorine.
Using succinyl chloride and 50% fluorine nitrogen mixed gas, is heated 4 hours under the conditions of 180 DEG C, obtain a small amount of product, yield
It is very low.
This method disadvantage is obvious, and fluorine gas oxidisability is strong, and side reaction is more, and yield reported in the literature is only 10%, uses
In preparing a small amount of product for laboratory research, be not suitable for industrial production.
(4) acyl chlorides electrofluorination
Document report is electrolysed in a cell using propionyl chloride ether compound, prepares perfluor malonyl fluorine.This method is received
Rate is very low, and by-product is more, yield only 30%, and raw material is difficult to obtain.
(5) ester group conversion method
E.I.Du Pont Company's report converts perfluor malonyl fluorine for perfluoro-propionyl fluoride methyl esters using antimony pentafluoride, and raw material five is fluorinated
Antimony is expensive, is suitable only for laboratory research.
Summary of the invention
For the deficiencies in the prior art, the purpose of the present invention is to provide a kind of preparations of the double acyl fluorides of perfluoroalkyl
Method, for this method using alkyl diacid chloride as raw material, elder generation reacts in catalysis solvent with fluorization agent generates two acyl fluorides of alkyl, then passes through
Anhydrous hydrogen fluoride electrolytic tank electrolysis is fluorinated to obtain the double acyl fluorides of perfluoroalkyl, last rectification and purification, and the reagent that this method uses is simple
It is easy to get, preparation step is simple, safe, and the reaction time is short, is suitble to large-scale production.
The purpose of the present invention is what is be achieved through the following technical solutions.
A kind of preparation method of the double acyl fluorides of perfluoroalkyl, the method comprises the following steps:
(1) by alkyl diacid chloride (ClOC (CH2)nCOCl it) is added in solvent with fluorization agent, it is anti-at -20 DEG C~50 DEG C
After 1h should being no less than, makes reaction system spontaneous recovery to room temperature, then separated, obtain two acyl fluorides crude product of alkyl；
The solvent is one of diethylene glycol dimethyl ether, tetraethyleneglycol dimethyl ether, acetonitrile, benzonitrile and tetrahydrofuran
Or two kinds, preferably diethylene glycol dimethyl ether or acetonitrile；
The fluorization agent is potassium fluoride, cesium fluoride, sodium fluoride or silver fluoride, preferred fluorinated potassium；
Further, the mole of fluorization agent is the 2 times or more of alkyl diacid chloride mole；
(2) two acyl fluorides crude product of alkyl is added in anhydrous hydrogen fluoride electrolytic cell and is electrolysed, and be lower than perfluor with temperature
The cold-trap of the double acyl fluorides boiling points of alkyl collects the gas that electrolysis generates, and carries out rectifying purifying to the liquid collected in cold-trap, obtains
The double acyl fluorides of perfluoroalkyl, are denoted as FOC (CF2)nCOF, n are 1~7；Wherein, electrolyte temperature is -20 DEG C~20 DEG C, electrode voltage
For 3V~7V.
Preferably 0 DEG C~5 DEG C of electrolyte temperature, the preferred 5V~5.5V of electrode voltage；
In electrolyte, the quality of two acyl fluorides crude product of alkyl is preferably the 1%~10% of anhydrous hydrofluoric acid quality.
It can be applied to prepare in fluoropolymer using the double acyl fluorides of the perfluoroalkyl of the method for the invention preparation, i.e., will
The double acyl fluorides of perfluoroalkyl are reacted with hexafluoropropylene oxide, are then eliminated with natrium carbonicum calcinatum, are prepared various vinyl ethers.This
A little different vinyl ethers of structure are important polymer monomer, can be used to prepare various functional polymers, such as: optical lens
Bright fluorine material, perfluorinated ionic membrane, perfluoroelastomers have extensive market application prospect.
Compared with prior art, the beneficial effects of the present invention are:
(1) for the method for the invention using alkyl diacid chloride as raw material, elder generation reacts in catalysis solvent with fluorization agent generates alkane
Two acyl fluorides of base is directly added into anhydrous hydrogen fluoride electrolytic cell without separation and carries out electrofluorination, then by the product of electrolysis by essence
Evaporate purification, perfluoroalkyl double acyl fluorides of the available purity 99% or more；And by change reaction reagent type and
Ratio, carbon chain lengths in adjustable product, to realize diversity Product formation；
(2) reagent that the method for the invention uses is simple and easy to get, and preparation step is simple, safe, and the reaction time is short, is suitble to
Large-scale production.
Specific embodiment
The present invention is further elaborated With reference to embodiment, wherein the method is equal unless otherwise instructed
For conventional method, the raw material can be gotten from open business unless otherwise instructed.
Embodiment 1
The preparation step of perfluor malonyl fluorine is as follows:
(1) 300 milliliters of benzonitriles and 50 grams of potassium fluorides are added in 1 liter of reaction kettle, and slowly instill 40 grams of malonyl
Chlorine, then reaction and reaction pressure are normal pressure at 10 DEG C, and reaction makes reaction system spontaneous recovery to room temperature after 8 hours, then into
Row separation, obtains 30 grams of malonyl fluorine crude products；
(2) directly malonyl chloride crude product is added in anhydrous hydrogen fluoride electrolytic cell (Simon electrolytic cell) and is electrolysed, and
The gas that electrolysis generates is collected using -80 DEG C of cryotraps, obtains perfluor malonyl fluorine crude product；Wherein, the temperature of electrolyte
It is 0~5 DEG C, electrode voltage is 5.5 volts, and the quality of malonyl chloride crude product is the 5% of anhydrous hydrofluoric acid quality；
(3) rectifying is carried out to perfluor malonyl fluorine crude product, obtains the perfluor malonyl fluorine that 16 grams of purity are greater than 99%.
The ir data of prepared perfluor malonyl fluorine is as follows: IR (gas): 1894cm-1, 1289cm-1,
1220cm-1, 1186cm-1, 1111cm-1, 1014cm-1, 777cm-1, 737cm-1, 681cm-1, 587 cm-1, 481cm-1；
The data of the Enantiomeric excess of prepared perfluor malonyl fluorine are as follows:19F NMR(CDC13,282 MHz):
δCF2=-111.5ppm (t,3J=10.6Hz, 2F), δCOF=+21.5ppm (t,4J=3.7Hz, 2F).
The reaction equation that perfluor malonyl fluorine is prepared in the present embodiment is as follows:
Embodiment 2
The preparation step of perfluor succinyl fluorine is as follows:
(1) 300 milliliters of diethylene glycol dimethyl ethers, 50 grams of potassium fluorides are added in 1 liter of reaction kettle, then slowly instill 61 grams of fourths
Diacid chloride, then reaction and reaction pressure are normal pressure at 10 DEG C, and reaction makes reaction system spontaneous recovery to room temperature after 12 hours,
It is separated again, obtains succinyl fluorine crude product；
(2) directly by succinyl fluorine crude product be added in anhydrous hydrogen fluoride electrolytic cell in be electrolysed, and -80 DEG C of use
Cryotrap collect electrolysis generate gas, obtain perfluor succinyl fluorine crude product；Wherein, the temperature of electrolyte is 0~5 DEG C,
Electrode voltage is 5 volts, and the quality of succinyl chloride crude product is the 3% of anhydrous hydrofluoric acid quality；
(3) rectifying is carried out to perfluor succinyl fluorine crude product, available 30 grams of purity is greater than 99.5% perfluor succinyl
Fluorine.
The ir data of prepared perfluor succinyl fluorine is as follows: IR (gas): 1886cm-1, 1296cm-1,
1234cm-1, 1205cm-1, 1132cm-1, 1066cm-1, 960cm-1, 934cm-1, 754cm-1, 696 cm-1, 624cm-1；
The data of the Enantiomeric excess of prepared perfluor succinyl fluorine are as follows:19F NMR(CDC13,282 MHz):
δCF2=-119.1ppm (t,3J=10.5Hz, 4F), δCOF=+25.3ppm (t,4J=3.6Hz, 2F).
The reaction equation that perfluor succinyl fluorine is prepared in the present embodiment is as follows:
Embodiment 3
The preparation step of perfluor glutaryl fluorine is as follows:
(1) 300 milliliters of tetrahydrofurans and 70 grams of cesium fluorides are added in 1 liter of reaction kettle, then slowly instill 24 grams of glutaryls
Chlorine, then reaction and reaction pressure are normal pressure at 20 DEG C, and reaction makes reaction system spontaneous recovery to room temperature after 12 hours, then into
Row separation, obtains glutaryl fluorine crude product；
(2) directly glutaryl fluorine crude product is added in anhydrous hydrogen fluoride electrolytic cell and is electrolysed, and -80 DEG C of use low
Warm cold-trap collects the gas that electrolysis generates, and obtains perfluor glutaryl fluorine crude product；Wherein, the temperature of electrolyte is 0~5 DEG C, electrode
Voltage is 5.3 volts, and the quality of glutaryl fluorine crude product is the 8% of anhydrous hydrofluoric acid quality；
(3) rectifying is carried out to perfluor glutaryl fluorine crude product, available 42 grams of purity is greater than 99.5% perfluor glutaryl
Fluorine.
The ir data of prepared perfluor glutaryl fluorine is as follows: IR (gas): 1901cm-1,1324cm-1,
1248cm-1,1204cm-1,1130cm-1,823cm-1,762cm-1,704cm-1,692cm-1,681cm-1。
The data of the Enantiomeric excess of prepared perfluor glutaryl fluorine are as follows:19F NMR(CDC13, 282 MHz):
δCF2=-115.3ppm (t,3J=83Hz, 2F), δCF2=-130.4ppm (t,3J=83Hz, 4F), δCOF=+47.0ppm (t,4J
=3.7Hz, 2F).
Reaction equation is as follows:
In conclusion the above is merely preferred embodiments of the present invention, being not intended to limit the scope of the present invention.
All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in of the invention
Within protection scope.
Claims (6)
1. a kind of preparation method of the double acyl fluorides of perfluoroalkyl, it is characterised in that: the method comprises the following steps:
(1) alkyl diacid chloride and fluorization agent are added in solvent, after reaction is no less than 1h at -20 DEG C~50 DEG C, make to react
System spontaneous recovery is to room temperature, then is separated, and two acyl fluorides crude product of alkyl is obtained；
(2) two acyl fluorides crude product of alkyl is added in anhydrous hydrogen fluoride electrolytic cell and is electrolysed, and be lower than perfluoroalkyl with temperature
The cold-trap of double acyl fluorides boiling points collects the gas that electrolysis generates, and carries out rectifying purifying to the liquid collected in cold-trap, obtains perfluor
The double acyl fluorides of alkyl, are denoted as FOC (CF2)nCOF, n are 1~7；
Solvent described in step (1) is in diethylene glycol dimethyl ether, tetraethyleneglycol dimethyl ether, acetonitrile, benzonitrile and tetrahydrofuran
One or two；
Fluorization agent described in step (1) is potassium fluoride, cesium fluoride, sodium fluoride or silver fluoride；
In step (2) electrolytic process, electrolyte temperature is -20 DEG C~20 DEG C, and electrode voltage is 3V~7V.
2. a kind of preparation method of the double acyl fluorides of perfluoroalkyl according to claim 1, it is characterised in that: institute in step (1)
Stating solvent is diethylene glycol dimethyl ether or acetonitrile.
3. a kind of preparation method of the double acyl fluorides of perfluoroalkyl according to claim 1, it is characterised in that: institute in step (1)
Stating fluorization agent is potassium fluoride.
4. a kind of preparation method of the double acyl fluorides of perfluoroalkyl according to claim 1, it is characterised in that: in step (1), fluorine
The mole of agent is the 2 times or more of alkyl diacid chloride mole.
5. a kind of preparation method of the double acyl fluorides of perfluoroalkyl according to claim 1, it is characterised in that: step (2) electrolysis
In the process, electrolyte temperature is 0 DEG C~5 DEG C, and electrode voltage is 5V~5.5V.
6. a kind of preparation method of the double acyl fluorides of perfluoroalkyl according to claim 1, it is characterised in that: the electricity of step (2)
It solves in liquid, the quality of two acyl fluorides crude product of alkyl is the 1%~10% of anhydrous hydrofluoric acid quality.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111153792A (en) * | 2019-12-30 | 2020-05-15 | 天津市长芦化工新材料有限公司 | Preparation device and use method of perfluoropentyl diacyl fluoride |
| CN111732500A (en) * | 2020-05-29 | 2020-10-02 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of hydrofluoroether |
| CN112174761A (en) * | 2020-09-23 | 2021-01-05 | 三明市海斯福化工有限责任公司 | Fluorination method |
| CN114478189A (en) * | 2021-12-31 | 2022-05-13 | 西安近代化学研究所 | Perfluoroalkoxy metal salt and preparation method and application thereof |
| CN115572993A (en) * | 2022-09-23 | 2023-01-06 | 天津大学 | Method for preparing perfluoroacyl fluoride by electrochemical method |
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| CN114478189A (en) * | 2021-12-31 | 2022-05-13 | 西安近代化学研究所 | Perfluoroalkoxy metal salt and preparation method and application thereof |
| CN115572993A (en) * | 2022-09-23 | 2023-01-06 | 天津大学 | Method for preparing perfluoroacyl fluoride by electrochemical method |
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