CN106188130A - A kind of preparation method of fluorine-containing phosphate ester - Google Patents
A kind of preparation method of fluorine-containing phosphate ester Download PDFInfo
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- CN106188130A CN106188130A CN201510220971.1A CN201510220971A CN106188130A CN 106188130 A CN106188130 A CN 106188130A CN 201510220971 A CN201510220971 A CN 201510220971A CN 106188130 A CN106188130 A CN 106188130A
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Abstract
The invention provides the preparation method of a kind of fluorine-containing phosphate ester, in the presence of an organic, under acid binding agent effect, fluorine-containing alcohol obtains corresponding fluorine-containing phosphate ester with phosphorus oxychloride reaction.The method that the present invention provides has the features such as method is novel, product yield is high and purity is high, operation safety.
Description
Technical field
The present invention relates to the preparation method of a kind of fluorine-containing phosphate ester, especially relate to one and can act as lithium battery electrolytes additive
The preparation method of fluorine-containing phosphate ester.
Background technology
Along with the development of twentieth century microelectric technique, the equipment of miniaturization is increasing, and power supply proposes the highest requirement.
Lithium battery enters the large-scale practical stage therewith, and it is widely used in the energy storage such as waterpower, firepower, wind-force and solar power station
Power-supply system, the uninterrupted power source of post and telecommunications, and electric tool, electric bicycle, battery-operated motor cycle, electric automobile,
Multiple field such as military equipment, Aero-Space.Lithium battery electrolytes is the carrier of battery intermediate ion transmission, typically by lithium salts and having
Machine solvent forms, and the most often adds a certain amount of additive, the addition of these additives, on the one hand improves the fire-retardant of battery
Property, on the other hand also significantly improve the performance of lithium battery.
Arthur von Cresce and Kang Xu at document Journal of The Electrochemical Society,
2011,158,3,337-342, ECS Transactions, reports three-(hexafluoro isopropyl) phosphorus in 2012,41,17-22
Acid esters is as the application of lithium-ion electrolyte additive, and discloses the preparation method of three-(hexafluoro isopropyl) phosphate esters.By six
Fluorine isopropanol is dissolved in ether at 0～5 DEG C, is initially charged LiH reaction and obtains hexafluoroisopropanol lithium, adds POCl3Reaction obtains
Three-(hexafluoro isopropyl) phosphate esters.The method is not disclosed product yield, owing to needing to use inflammable and explosive ether and produce big
, there is great potential safety hazard when industrialized production in amount hydrogen.
Li Zhanxiong etc. are in organic chemistry the 10th phase of volume 24 in 2004,1260-1261, the simplicity of three (containing fluoroalkyl) phosphate ester
Synthesis reports the preparation method of three (containing fluoroalkyl) phosphate ester, with LiCl as catalyst, with X (CF2)n CH2OH (X=F,
N=1) it is raw material, with Cl3P reaction obtains corresponding three (containing fluoroalkyl) phosphate ester.In the method, three (containing fluoroalkyl) phosphoric acid
The highest yield of ester is only 87.6%.
Therefore, still it is hopeful the preparation of fluorine-containing phosphate ester is made further improvements.
Summary of the invention
It is an object of the invention to provide the preparation method of a kind of fluorine-containing phosphate ester, there is method novelty, product yield height and purity
The features such as high, operation safety.
The present invention provides following technical scheme:
The preparation method of the fluorine-containing phosphate ester shown in a kind of structure formula (I), including in the presence of an organic, in acid binding agent effect
Under, fluorine-containing alcohol obtains corresponding by the fluorine-containing phosphate ester shown in structure formula (I) with phosphorus oxychloride reaction,
Described fluorine-containing alcohol is selected from RF 1OH、RF 2OH and RF 3One in OH, two or three, and RF 1、RF 2And RF 3Select independently
From C1～C4 containing fluoroalkyl, the fluorine-containing thiazolinyl of C2～C4 or the fluorine-containing alkynyl of C2～C4；
Described acid binding agent is selected from the one in organic base, inorganic base and alkali metal hydride, two or three combination of the above.
Phosphorus oxychloride (the POCl that the present invention uses3) it is known compound.
The raw material fluorine-containing alcohol that the present invention uses is selected from RF 1OH、RF 2OH and RF 3One in OH, two or three, both can be independent
Use RF 1OH、RF 2OH and RF 3Any one of OH, it is possible to use their mixture；When being used alone RF 1OH、RF 2OH
And RF 3During any one of OH, three substituent R in the fluorine-containing phosphate ester of preparationF 1、RF 2And RF 3Identical；When using selected from RF 1OH、
RF 2OH and RF 3During the mixture of OH, three substituent R in the fluorine-containing phosphate ester of preparationF 1、RF 2And RF 3Difference according to fluorine-containing alcohol and
Different.
The raw material fluorine-containing alcohol R that the present invention usesF 1OH、RF 2OH and RF 3In OH, RF 1、RF 2And RF 3Containing independently selected from C1～C4
Fluoroalkyl, the fluorine-containing thiazolinyl of C2～C4 or the fluorine-containing alkynyl of C2～C4；Preferably, RF 1、RF 2And RF 3Independently selected from C2～
C3 containing fluoroalkyl, the fluorine-containing thiazolinyl of C2～C3 or the fluorine-containing alkynyl of C2～C3；It may further be preferable that RF 1、RF 2And RF 3
For identical substituent group, i.e. RF 1=RF 2=RF 3。
The acid binding agent that the present invention uses is selected from the one in organic base, inorganic base and sodium hydride, two or three combination of the above, both
Can be used alone in organic base, inorganic base and sodium hydride any one, it is possible to use their mixture；When making
During with their mixture, the ratio between several materials in organic base, inorganic base and sodium hydride can use any ratio
Example.Preferably, described acid binding agent is selected from organic base and/or inorganic base, both can be used alone organic base or inorganic base, it is possible to
To use their mixture；When using their mixture, the ratio between organic base and inorganic base can use any ratio
Example.
The present invention use acid binding agent organic base in, it is preferred that organic base selected from triethylamine, triethylene diamine (DABCO),
1,8-diazabicylo 11 carbon-7-alkene (DBU), DMAP (DMAP), pyridine, N-methylmorpholine, imidazoles,
Tetramethylethylenediamine, potassium tert-butoxide, sodium tert-butoxide, n-BuLi, potassium hexamethyldisilazide (KHMDS), hexamethyl two
One in silica-based amido sodium (NaHMDS) and lithium diisopropyl amido (LDA), two or three combination of the above, both can be single
Solely use selected from triethylamine, triethylene diamine (DABCO), 1,8-diazabicylo 11 carbon-7-alkene (DBU), 4-dimethylamino
Pyridine (DMAP), pyridine, N-methylmorpholine, imidazoles, tetramethylethylenediamine, potassium tert-butoxide, sodium tert-butoxide, n-BuLi,
In potassium hexamethyldisilazide (KHMDS), sodium hexamethyldisilazide (NaHMDS) and lithium diisopropyl amido (LDA)
Any one, it is possible to use their mixture；When a mixture is used, selected from triethylamine, triethylene diamine (DABCO),
1,8-diazabicylo 11 carbon-7-alkene (DBU), DMAP (DMAP), pyridine, N-methylmorpholine, imidazoles,
Tetramethylethylenediamine, potassium tert-butoxide, sodium tert-butoxide, n-BuLi, potassium hexamethyldisilazide (KHMDS), hexamethyl two
The ratio between several materials in silica-based amido sodium (NaHMDS) and lithium diisopropyl amido (LDA) can use any ratio.
It may further be preferable that organic base is selected from triethylamine, pyridine, DMAP (DMAP), N-methylmorpholine and imidazoles
In one, two or three combination of the above, both can be used alone selected from triethylamine, pyridine, DMAP (DMAP),
Any one of N-methylmorpholine and imidazoles, it is possible to use their mixture；When a mixture is used, selected from triethylamine,
The ratio between several materials in pyridine, DMAP (DMAP), N-methylmorpholine and imidazoles can use any
Ratio.
The 1 of present invention use, 8-diazabicylo 11 carbon-7-alkene, is called for short DBU, molecular formula C9H16N2.
The DMAP that the present invention uses, is called for short DMAP, molecular formula C7H10N2.
The potassium hexamethyldisilazide that the present invention uses, is called for short KHMDS, molecular formula C6H18KNSi2。
The sodium hexamethyldisilazide that the present invention uses, is called for short NaHMDS, molecular formula C6H18NNaSi2.
The lithium diisopropyl amido that the present invention uses, is called for short LDA.
In the acid binding agent inorganic base that the present invention uses, it is preferred that described inorganic base is selected from alkali carbonate, alkali metal carbonic acid
One in hydrogen salt, alkali metal phosphate and alkali metal hydroxide, two or three combination of the above, both can be used alone choosing
Any one in alkali carbonate, alkali metal hydrogencarbonate, alkali metal phosphate and alkali metal hydroxide, it is also possible to
Use their mixture；When using their mixing, selected from alkali carbonate, alkali metal hydrogencarbonate, alkali metal phosphorus
The ratio between several materials in hydrochlorate and alkali metal hydroxide can use any ratio.It may further be preferable that it is described
Inorganic base is selected from sodium carbonate, sodium bicarbonate, potassium carbonate, the one in potassium bicarbonate and sodium hydroxide, more than two or three group
Close, both can be used alone in sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate and sodium hydroxide any one,
Their mixture can also be used；When using their mixing, selected from sodium carbonate, sodium bicarbonate, potassium carbonate, bicarbonate
The ratio between several materials in potassium and sodium hydroxide can use any ratio.
The acid binding agent alkali metal hydride that the present invention uses, preferably sodium hydride.
The present invention use organic solvent, it is preferred that described organic solvent selected from oxolane, ether, toluene, acetonitrile,
One in dichloromethane, chloroform and carbon tetrachloride, two or three combination of the above, both can be used alone selected from tetrahydrochysene
Any one in furan, ether, toluene, acetonitrile, dichloromethane, chloroform and carbon tetrachloride, it is possible to use they
Mixture；When using their mixture, selected from oxolane, ether, toluene, acetonitrile, dichloromethane, three chloromethanes
The ratio between several materials in alkane and carbon tetrachloride can use any ratio.It may further be preferable that described organic solvent
One in oxolane, ether and dichloromethane, two or three combination of the above, both can be used alone selected from tetrahydrochysene
Any one in furan, ether and dichloromethane, it is possible to use their mixture；When using their mixture,
The ratio between several materials in oxolane, ether and dichloromethane can use any ratio.
In the preparation method that the present invention provides, fluorine-containing alcohol and the mol ratio of acid binding agent, preferably 0.1:1～1:5, further
It is preferably 1:1～1:3.
In the preparation method that the present invention provides, fluorine-containing alcohol and the mol ratio of phosphorus oxychloride, preferably 1:1～10:1, further
It is preferably 2:1～4:1.
In the preparation method that the present invention provides, organic solvent and the mass ratio of fluorine-containing alcohol, preferably 1:1～1:6, the most excellent
Elect 1:2～1:4 as.
In the preparation method that the present invention provides, reaction temperature is preferably 0～120 DEG C, more preferably 30～80 DEG C.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is further described, but does not limit the invention to these and be embodied as
Mode.One skilled in the art would recognize that and present invention encompasses potentially included in Claims scope all alternative
Scheme, improvement project and equivalents.
The preparation of embodiment 1 three-(hexafluoro isopropyl) phosphate ester
To one equipped with the 500mL there-necked flask of mechanical agitation, thermometer and constant pressure funnel is separately added into 91g (0.9mol)
It is slowly added dropwise 94mL (0.9mol) hexafluoroisopropanol under triethylamine and 150ml dichloromethane, ice-water bath, drips complete continuation
Stirring, when temperature is down to 0 DEG C, is slowly added dropwise 27mL (0.3mol) phosphorus oxychloride, has a large amount of white solid to generate, dropping
After remove ice-water bath, be warming up to 45 DEG C of backflows, with gas chromatogram monitoring reaction progress, 3 react substantially completely the most afterwards,
Reacting liquor while hot filters precipitation, and filtrate decompression is distilled, and methylene chloride can recycle, and collects 50-55 DEG C/30mmHg's
Component, obtains product 141g, purity 99.95%, and moisture is less than 20ppm, yield 86.0%, (M+:548.06).The product obtained
Product are analyzed as target product three-(hexafluoro isopropyl) phosphate ester through GC-MS.
The preparation of embodiment 2 three-(trifluoroethyl) phosphate ester
To one equipped with the 3L there-necked flask of mechanical agitation, thermometer and constant pressure funnel is separately added into 510g (7.5mol)
Imidazoles and 500ml dichloromethane, drip 1065mL (15mol) trifluoroethanol under ice-water bath, drip complete continuation and stir, treat
When temperature is down to 0 DEG C, it is slowly added dropwise 448mL (5mol) phosphorus oxychloride, has a large amount of white solid to generate, drip complete recession
Removing ice-water bath, be warming up to 45 DEG C of backflows, by gas chromatogram monitoring reaction progress, 3 react substantially completely the most afterwards, reactant liquor
Filtered while hot precipitation, filtrate decompression distillation, methylene chloride can recycle, and collects the component of 43-46 DEG C/30mmHg,
Obtaining product 1600g, purity 99.97%, moisture is less than 20ppm, yield 93.2%, (M+:344.07).The product warp obtained
GC-MS analyzes as target product three-(trifluoroethyl) phosphate ester.
The preparation of embodiment 3: three-(2-trifluoromethyl pi-allyl) phosphate ester
To one equipped with the 500mL there-necked flask of mechanical agitation, thermometer and constant pressure funnel is separately added into 40g (0.5mol)
It is slowly added dropwise 76mL (0.9mol) 2-trifluoromethyl 1-propenol-3 under pyridine and 150ml dichloromethane, ice-water bath, drips
Bi Jixu stirs, and when temperature is down to 0 DEG C, is slowly added dropwise 27mL (0.3mol) phosphorus oxychloride, has a large amount of white solid raw
Becoming, drip complete recession and remove ice-water bath, be warming up to 45 DEG C of backflows, by gas chromatogram monitoring reaction progress, 3 react the most afterwards
Substantially completely, reacting liquor while hot filters precipitation, and filtrate decompression is distilled, and methylene chloride can recycle, and collects 67-69 DEG C
The component of/30mmHg, obtains product 114g, purity 99.96%, and moisture is less than 20ppm, yield 88.7%, (M+:422.03)。
The product obtained is analyzed as target product three-(2-trifluoromethyl pi-allyl) phosphate ester through GC-MS.
The preparation of embodiment 4: three-(2-trifluoromethyl-3-alkynes butyl) phosphate ester
To one equipped with the 500mL there-necked flask of mechanical agitation, thermometer and constant pressure funnel is separately added into 62g (0.5
Mol) DMAP and 150ml dichloromethane, is slowly added dropwise 69mL (0.9mol) 2-trifluoromethyl-3-alkynes butanol under ice-water bath,
Drip complete continuation to stir, when temperature is down to 0 DEG C, be slowly added dropwise 27mL (0.3mol) phosphorus oxychloride, have a large amount of white
Solid generates, and drips complete recession and removes ice-water bath, is warming up to 45 DEG C of backflows, and by gas chromatogram monitoring reaction progress, 3 as a child
Substantially completely, reacting liquor while hot filters precipitation in rear reaction, and filtrate decompression is distilled, and methylene chloride can recycle, and collects
The component of 75-77 DEG C/30mmHg, obtains product 117g, purity 99.98%, and moisture is less than 20ppm, yield 85.4%, (M+:458.03)。
The product obtained is analyzed as target product three-(2-trifluoromethyl-3-alkynes butyl) phosphate ester through GC-MS.
The preparation of embodiment 5: two fluoro ethyl trifluoroethyl hexafluoro isopropyl phosphate ester
To one equipped with the 500mL there-necked flask of mechanical agitation, thermometer and constant pressure funnel is separately added into 51g (0.5
Mol) it is slowly added dropwise under N-methylmorpholine and 150ml dichloromethane, ice-water bath by 19mL (0.3mol) difluoroethanol, 22
ML (0.3mol) trifluoroethanol and the mixed liquor of 31mL (0.3mol) hexafluoroisopropanol composition, drip complete continuation and stir, treat
When temperature is down to 0 DEG C, it is slowly added dropwise 27mL (0.3mol) phosphorus oxychloride, has a large amount of white solid to generate, after dropping
Removing ice-water bath, be warming up to 45 DEG C of backflows, by gas chromatogram monitoring reaction progress, 3 react substantially completely the most afterwards, reaction
Liquid filtered while hot precipitation, filtrate decompression rectification, methylene chloride can recycle, and collects the component of 83-86 DEG C/30mmHg,
Obtaining product 100g, purity 99.98%, moisture is less than 20ppm, yield 84.1%, (M+:393.98).The product obtained is through GC-MS
Analyze the preparation for target product two fluoro ethyl trifluoroethyl hexafluoro isopropyl phosphate ester.
The preparation of embodiment 6: three-(hexafluoro isopropyl) phosphate ester
To one equipped with the 500mL there-necked flask of mechanical agitation, thermometer and constant pressure funnel is separately added into 76g (0.9mol)
It is slowly added dropwise 94mL (0.9mol) hexafluoroisopropanol under sodium bicarbonate and 150ml dichloromethane, ice-water bath, drips complete continuing
Continuous stirring, when temperature is down to 0 DEG C, is slowly added dropwise 27mL (0.3mol) phosphorus oxychloride, has a large amount of white solid to generate, and drips
Adding complete recession and remove ice-water bath, be warming up to 45 DEG C of backflows, by gas chromatogram monitoring reaction progress, 3 react the completeest the most afterwards
Entirely, reacting liquor while hot filters precipitation, and filtrate decompression is distilled, and methylene chloride can recycle, and collects 50-55 DEG C/30mmHg
Component, obtain product 142g, purity 99.95%, moisture is less than 20ppm, yield 86.6%, (M+:548.06).Obtain
Product is analyzed as target product three-(hexafluoro isopropyl) phosphate ester through GC-MS.
Claims (13)
1. the preparation method of the fluorine-containing phosphate ester shown in a structure formula (I), it is characterised in that in the presence of an organic, tiing up acid
Under agent effect, fluorine-containing alcohol obtains corresponding by the fluorine-containing phosphate ester shown in structure formula (I) with phosphorus oxychloride reaction,
Described fluorine-containing alcohol is selected from RF 1OH、RF 2OH and RF 3One in OH, two or three, and RF 1、RF 2And RF 3Select independently
From C1～C4 containing fluoroalkyl, the fluorine-containing thiazolinyl of C2～C4 or the fluorine-containing alkynyl of C2～C4；
Described acid binding agent is selected from the one in organic base, inorganic base and alkali metal hydride, two or three combination of the above.
2. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 1, it is characterised in that described RF 1、
RF 2And RF 3Independently selected from C1～C3 containing fluoroalkyl, the fluorine-containing thiazolinyl of C2～C3 or the fluorine-containing alkynyl of C2～C3.
3. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 2, it is characterised in that described RF 1、
RF 2And RF 3For identical substituent group.
4. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 1, it is characterised in that described in tie up acid
Agent is selected from organic base and/or inorganic base.
5. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 1, it is characterised in that described organic
Alkali is selected from triethylamine, triethylene diamine, 1,8-diazabicylo 11 carbon-7-alkene, DMAP, pyridine, N-methyl
Morpholine, imidazoles, tetramethylethylenediamine, potassium tert-butoxide, sodium tert-butoxide, n-BuLi, potassium hexamethyldisilazide (KHMDS),
One in sodium hexamethyldisilazide and lithium diisopropyl amido, two or three combination of the above, described inorganic base is selected from alkali
One in metal carbonate, alkali metal hydrogencarbonate, alkali metal phosphate and alkali metal hydroxide, more than two or three
Combination, described alkali metal hydride is sodium hydride.
6. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 5, it is characterised in that described organic
Alkali is selected from the one in triethylamine, pyridine, DMAP, N-methylmorpholine and imidazoles, two or three combination of the above,
Described inorganic base is selected from sodium carbonate, sodium bicarbonate, potassium carbonate, one in potassium bicarbonate and sodium hydroxide, two or three with
Upper combination.
7. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 1, it is characterised in that described organic
Solvent one in oxolane, ether, toluene, acetonitrile, dichloromethane, chloroform and carbon tetrachloride, two kinds or
Three kinds of combination of the above.
8. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 7, it is characterised in that described organic
Solvent one in oxolane, ether and dichloromethane, two or three.
9. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 1, it is characterised in that described fluorine-containing
Alcohol is 0.1:1～1:5 with the mol ratio of acid binding agent, and described fluorine-containing alcohol is 1:1～10:1 with the mol ratio of phosphorus oxychloride, institute
The mass ratio stating organic solvent and fluorine-containing alcohol is 1:1～1:6.
10. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 9, it is characterised in that described contain
Fluorine alcohol is 1:1～1:3 with the mol ratio of acid binding agent, and described fluorine-containing alcohol is 2:1～4:1 with the mol ratio of phosphorus oxychloride, described
Organic solvent is 1:2～1:4 with the mass ratio of fluorine-containing alcohol.
11. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 1, it is characterised in that reaction temperature
It it is 0～120 DEG C.
12. according to the preparation method of the fluorine-containing phosphate ester shown in the structure formula (I) described in claim 11, it is characterised in that reaction temperature
Degree is 30～80 DEG C.
13. according to the application of the fluorine-containing phosphate ester shown in the structure formula (I) one of claim 1 to 12 Suo Shu, it is characterised in that described
Fluorine-containing phosphate ester is used as lithium battery electrolytes additive.
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| CN112239478A (en) * | 2019-07-17 | 2021-01-19 | 杉杉新材料（衢州）有限公司 | Method for synthesizing asymmetric phosphate compound |
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| CN112239478A (en) * | 2019-07-17 | 2021-01-19 | 杉杉新材料（衢州）有限公司 | Method for synthesizing asymmetric phosphate compound |
| CN112898334A (en) * | 2019-11-18 | 2021-06-04 | 石家庄圣泰化工有限公司 | Synthesis method of tris (2,2, 2-trifluoroethyl) phosphate |
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