CN104953176B - Low color ethylene glycol(Double propionitrile bases)The processing method of ether - Google Patents
Low color ethylene glycol(Double propionitrile bases)The processing method of ether Download PDFInfo
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- CN104953176B CN104953176B CN201410116369.9A CN201410116369A CN104953176B CN 104953176 B CN104953176 B CN 104953176B CN 201410116369 A CN201410116369 A CN 201410116369A CN 104953176 B CN104953176 B CN 104953176B
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- ether
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- ethylene glycol
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- propionitrile
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
- H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
- H01M10/0566—Liquid materials
- H01M10/0567—Liquid materials characterised by the additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/11—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton
- C07C255/13—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same saturated acyclic carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/058—Construction or manufacture
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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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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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
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
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- General Physics & Mathematics (AREA)
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Abstract
The invention provides a kind of low color ethylene glycol(Double propionitrile bases)The processing method of ether.By ethylene glycol(Double propionitrile bases)Ether is acidified with the concentrated sulfuric acid, in 10~80 DEG C under agitation, 0.1~3% potassium permanganate solution is added dropwise, the dosage of potassium permanganate solution is ethylene glycol(Double propionitrile bases)0.5~5 times of ether amount, stirring 0.5~5 hour, filtering, sulphite is added into filtrate and removes excessive potassium permanganate and the manganese dioxide of residual, then decompression dehydration processing is carried out at 70~100 DEG C of bath temperature, the material after dewater treatment carries out vacuum fractionation and obtains the ethylene glycol of low color number(Double propionitrile bases)Ether.
Description
Technical field
The invention belongs to chemical field, is related to a kind of low color ethylene glycol(Double propionitrile bases)The processing method of ether.
Background technology
Lithium-ion battery electrolytes have strict technical indicator, in these technical indicators, except to water content, hydrogen fluorine
Acid content, electrical conductivity also require to color number outside clearly requiring, usually require that color number within 20, within even 10.
So to control lustful number in the process for preparation of electrolyte, it otherwise will influence its sale and use.Present functional form electrolysis
Liquid, due to the addition of these additives, may cause the rise of electrolyte color number generally all added with a variety of additives, so
Also require that the color number of these additives in itself is low.
Ethylene glycol(Double propionitrile bases)Ether is a kind of lithium-ion battery electrolytes additive, can improve the high temperature circulation of lithium battery
Performance and high-temperature storage performance.In the prior art(For example, EP1170275;J.Chem.Soc.Perkin.Trans.2,1990,
321-327;US2437905;US2009112024)Report and ethylene glycol is prepared using ethylene glycol and acrylonitrile progress condensation reaction
(Double propionitrile bases)Ether.The ethylene glycol of commercialization(Double propionitrile bases)Ether is usually yellow, especially with ethylene glycol(Double propionamides)
Ethylene glycol prepared by ether dewatering(Double propionitrile bases)Ether, the color number of its product is higher, more more than 150.So high color number
Ethylene glycol(Double propionitrile bases)Ether is added in electrolyte as additive certainly will cause increasing considerably for electrolyte color number, cause to match somebody with somebody
The electrolyte color number of system is unqualified.
The content of the invention
It is an object of the invention to provide a kind of low color ethylene glycol(Double propionitrile bases)The processing method of ether, makes ethylene glycol
(Double propionitrile bases)The color number of ether reaches the requirement of lithium-ion battery electrolytes.
The present invention is achieved through the following technical solutions:
A kind of low color ethylene glycol(Double propionitrile bases)The processing method of ether, it is characterised in that methods described includes following step
Suddenly:
(1)By ethylene glycol(Double propionitrile bases)Ether is acidified with the concentrated sulfuric acid, then, potassium permanganate solution is added dropwise and decolourize instead
Should;
(2)Filtering, obtains filtrate, and the titanium dioxide that sulphite removes excessive potassium permanganate and residual is added into filtrate
Manganese;
(3)Decompression dehydration processing, then vacuum fractionation obtains the ethylene glycol of low color number(Double propionitrile bases)Ether.
Specifically, a kind of low color ethylene glycol(Double propionitrile bases)The processing method of ether, it is characterised in that methods described includes
Following steps:
(1)By ethylene glycol(Double propionitrile bases)Ether is acidified with the concentrated sulfuric acid, and at 10~80 DEG C, potassium permanganate solution is added dropwise,
Until the color of potassium permanganate is not faded;
(2)Filtering, obtains filtrate, and adding sulphite to filtrate removes excessive potassium permanganate and the manganese dioxide of residual;
(3)Then decompression dehydration processing is carried out at 70~100 DEG C of bath temperature, the material after dewater treatment is depressurized
Fractionation obtains the ethylene glycol of low color number(Double propionitrile bases)Ether.
According to the present invention, the product color number after above-mentioned decolorization is within 30, preferably within 20.
According to the present invention, step(1)In, the amount of the concentrated sulfuric acid has no particular limits, generally ethylene glycol(Double propionitrile
Base)The 0.5~5% of ether quality.
According to the present invention, step(1)In, potassium permanganate solution is preferably added dropwise under agitation and carries out decoloring reaction.Generally
Decolourize under heating faster, better, the temperature range of decoloring reaction is 10~80 DEG C, preferably 50~80 DEG C.
According to the present invention, the concentration of potassium permanganate solution is 0.1~3%, but there is no particular limitation.But, concentration
Height can reduce the addition of water, can also so reduce the follow-up workload for going water removal, more economically.
According to the present invention, the dosage of the potassium permanganate solution is ethylene glycol(Double propionitrile bases)The 0.5~5 of ether quality
Times, preferably 1~2.5 times.
In the present invention, potassium permanganate solution is dripped, the color of solution no longer changes, and is still the face of potassium permanganate
Color, illustrate that decoloring reaction is complete.
According to the present invention, the step(2)In, potassium permanganate and residual that sulphite removes excess are added into filtrate
A small amount of manganese dioxide.
Wherein, the one kind of the sulphite in sodium hydrogensulfite, potassium bisulfite, sodium sulfite or potassium sulfite
Or it is a variety of, such as can be used simultaneously with two or more.
In the present invention, it is highly acid to add and maintenance system is wanted when sulphite is reduced, such as pH is less than or equal to 2, excellent
Choosing is less than or equal to 1, so just can guarantee that the manganese dioxide of excessive potassium permanganate and residual is reduced into Mn2+.Because in
Property and alkalescence condition, potassium permanganate may only be reduced into MnO2(Mn4+).
Moreover, decolourizing after terminating, the potassium permanganate and manganese dioxide of residual will remove totally, that is, add the amount of sulphite
Ensure to make the manganese element in system to be completely reduced into Mn2+If remain Mn4+(MnO2)Or Mn7+(KMnO4)It will cause
During the vacuum fractionation then carried out, at high temperature(More than 150 DEG C), ethylene glycol(Double propionitrile bases)Ether is in MnO2Catalysis under
Decompose reaction, so that ethylene glycol(Double propionitrile bases)The yield of ether reduces, or even cannot get ethylene glycol(Double propionitrile bases)Ether.
And Mn2+Ethylene glycol will not be caused(Double propionitrile bases)The decomposition of ether at high temperature.Due to ethylene glycol(Double propionitrile bases)The boiling point of ether
Height, 358 DEG C of boiling point under 1 atmospheric pressure, even if at reduced pressure, it is also desirable to which higher temperature could be realized.So it is
Realize and obtain ethylene glycol in high yield(Double propionitrile bases)Ether, Mn4+(MnO2)Removal it is most important, the manganese element of residual is complete
Portion changes into Mn2+。
According to the present invention, step(3)In, decompression dehydration processing is carried out at 70~100 DEG C of bath temperature, removing will after water
Material is down to room temperature, filtering, obtains filtrate.
Above-mentioned filtrate is fractionated at reduced pressure, obtains the ethylene glycol of low color number(Double propionitrile bases)Ether.
The inventors discovered that the ethylene glycol without decolorization(Double propionitrile bases)More than the color number of ether more than 50, in addition it is high
Up to more than 150, after above-mentioned decolorization, its color number can be controlled within 30, within preferably 25, within more preferably 20.
The present invention also provides a kind of low color ethylene glycol(Double propionitrile bases)The application of ether, it is characterised in that its be used as lithium from
Sub- battery electrolyte additive.
According to the present invention, the low color ethylene glycol(Double propionitrile bases)Ether is prepared by the above method of the present invention.
The present invention also provides a kind of lithium-ion battery electrolytes, it is characterised in that including the low color number as additive
Ethylene glycol(Double propionitrile bases)Ether.
According to the present invention, the ethylene glycol(Double propionitrile bases)The addition of ether in the electrolytic solution is within 5%.Through above-mentioned de-
Ethylene glycol after color processing(Double propionitrile bases)Ether is added in lithium-ion battery electrolytes as additive, can make electrolyte
Color number is remained within 20.
According to the present invention, the low color ethylene glycol(Double propionitrile bases)Ether is prepared by the above method of the present invention.
Embodiment
The present invention is described in detail by the following examples.But skilled in the art realises that following embodiments are not
It is limiting the scope of the invention, any improvement and change made on the basis of the present invention, all protection in the present invention
Within the scope of.
Embodiment 1:
By 200g ethylene glycol(Double propionitrile bases)Ether(Color number 100)Add in 1000ml there-necked flasks, add the 10g concentrated sulfuric acids and carry out
Acidifying, 2% potassium permanganate solution 80ml is then added dropwise with stirring at 60 DEG C, stirring reaction 2 hours, filtering, obtains filtrate, so
4.5 grams of sodium sulfites are added in backward filtrate and remove excessive potassium permanganate and the manganese dioxide of residual, then in bath temperature
Decompression dehydration processing is carried out at 70 DEG C, material is down to room temperature after dehydration, filters, obtains filtrate.Filtrate uses the side of vacuum fractionation
Method extracts the fraction 170g of positive boiling point(180℃/8mmHg).The color number of product is 25.
Embodiment 2:
By 100g ethylene glycol(Double propionitrile bases)Ether(Color number 50)Add in 500ml there-necked flasks, add the 8g concentrated sulfuric acids and carry out acid
Change, 1% potassium permanganate solution 50ml is then added dropwise with stirring at 80 DEG C, stirring reaction 1 hour, filtering, obtains filtrate, then
Add 3 grams of potassium bisulfites and remove excessive potassium permanganate and the manganese dioxide of residual, then carried out at 100 DEG C of bath temperature
Decompression dehydration processing, room temperature is down to after dehydration by material, is filtered, is obtained filtrate.Filtrate is just being boiled using the method extraction of vacuum fractionation
The fraction 88g of point(180℃/8mmHg).The color number of product is 20.
Embodiment 3:
By 150g ethylene glycol(Double propionitrile bases)Ether(Color number 150)Add in 750ml there-necked flasks, add the 12g concentrated sulfuric acids and carry out
Acidifying, 1.5% potassium permanganate solution 75ml is then added dropwise with stirring at 30 DEG C, stirring reaction 1 hour, filtering, obtains filtrate,
Then 4.5 grams of potassium bisulfites are added and remove excessive potassium permanganate and the manganese dioxide of residual, then in 70 DEG C of bath temperature
Lower progress decompression dehydration processing, is down to room temperature by material after dehydration, filters, obtain filtrate.Filtrate is carried using the method for vacuum fractionation
Take the fraction 125g of positive boiling point(180℃/8mmHg).The color number of product is 30.
Comparative example 1:
By 200g ethylene glycol(Double propionitrile bases)Ether(Color number 100)Add in 1000ml there-necked flasks, add the 10g concentrated sulfuric acids and carry out
Acidifying, is then added dropwise 2% potassium permanganate solution 80ml, stirring reaction 2 hours, then in bath temperature with stirring at 60 DEG C
Decompression dehydration processing is carried out at 70 DEG C, last fractionation is then carried out using the method for decompression, collects 113 DEG C/40mmHg boiling points
Fraction 150g, found through nuclear-magnetism and GC analyses, the fraction is not ethylene glycol(Double propionitrile bases)Ether.
As can be seen here, the present invention is due to adding sulphite and removing potassium permanganate and manganese dioxide, so as to ensure this
Invention can obtain target product, and product meets the requirements.
Claims (18)
1. a kind of processing method of low color ethylene glycol (double propionitrile bases) ether, it is characterised in that methods described comprises the following steps:
(1) ethylene glycol (double propionitrile bases) ether is acidified with the concentrated sulfuric acid, then, potassium permanganate solution is added dropwise and carries out decoloring reaction;
(2) filter, obtain filtrate, sulphite is added into filtrate and removes excessive potassium permanganate and the manganese dioxide of residual;
(3) decompression dehydration is handled, and then vacuum fractionation obtains ethylene glycol (double propionitrile bases) ether of low color number, wherein the low color number
Refer to product color number within 30.
2. processing method according to claim 1, it is characterised in that methods described comprises the following steps:
(1) ethylene glycol (double propionitrile bases) ether is acidified with the concentrated sulfuric acid, in 10~80 DEG C under agitation, 0.1~3% permanganic acid is added dropwise
Aqueous solutions of potassium, the dosage of potassium permanganate solution are 0.5~5 times of ethylene glycol (double propionitrile bases) ether quality, and stirring 0.5~5 is small
When;
(2) filter, obtain filtrate, sulphite is added into filtrate and removes excessive potassium permanganate and the manganese dioxide of residual;
(3) decompression dehydration processing is then carried out at 70~100 DEG C of bath temperature, the material after dewater treatment carries out vacuum fractionation
Obtain ethylene glycol (double propionitrile bases) ether of low color number.
3. processing method as claimed in claim 1, it is characterised in that described sulphite is sodium hydrogensulfite, sulfurous acid
One or two or more kinds in hydrogen potassium, sodium sulfite, potassium sulfite.
4. processing method as claimed in claim 2, it is characterised in that described sulphite is sodium hydrogensulfite, sulfurous acid
One or two or more kinds in hydrogen potassium, sodium sulfite, potassium sulfite.
5. processing method as claimed in claim 1, it is characterised in that the amount of the concentrated sulfuric acid is ethylene glycol (double propionitrile bases) ether quality
0.5~5%.
6. according to any one of claim 1-5 processing method, it is characterised in that product color number after decolorization 20 with
It is interior.
7. according to any one of claim 1-5 processing method, it is characterised in that in step (1), the amount of the concentrated sulfuric acid is second
The 0.5~5% of glycol (double propionitrile bases) ether quality, the concentration of potassium permanganate solution is 0.1~3%.
8. processing method according to claim 2, it is characterised in that in step (1), the temperature range of the decoloring reaction is 50
~80 DEG C.
9. processing method according to claim 8, it is characterised in that in step (1), the dosage of the potassium permanganate solution is
1~2.5 times of ethylene glycol (double propionitrile bases) ether quality.
10. processing method according to claim 9, it is characterised in that add sulphite and want when being reduced the maintenance system to be
Highly acid.
11. processing method according to claim 10, it is characterised in that add when sulphite is reduced and want maintenance system pH
Less than or equal to 2.
12. processing method according to claim 11, it is characterised in that add when sulphite is reduced and want maintenance system small
In equal to 1.
13. according to any one of claim 1-5 processing method, it is characterised in that in step (3), in bath temperature 70~100
Decompression dehydration processing is carried out at DEG C, material is down to room temperature after removing water, filters, obtains filtrate.
14. a kind of application of low color ethylene glycol (double propionitrile bases) ether, it is characterised in that it adds as lithium-ion battery electrolytes
Add agent, low color ethylene glycol (the double propionitrile bases) ether is handled by any one of claim 1-13 method.
15. application according to claim 14, it is characterised in that the low color number refers to product color number within 20.
A kind of 16. lithium-ion battery electrolytes, it is characterised in that ethylene glycol (double propionitrile including the low color number as additive
Base) ether, wherein, low color ethylene glycol (the double propionitrile bases) ether by the method described in claim any one of 1-13 at
Reason.
17. lithium-ion battery electrolytes according to claim 16, it is characterised in that ethylene glycol (the double propionitrile bases) ether is in electricity
The addition in liquid is solved within 5%.
18. according to the lithium-ion battery electrolytes of claim 16 or 17, it is characterised in that the low color number refers to product color number
Within 20.
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