CN108033900A - A kind of discoloration method of three nitrile of 1,3,6- hexanes - Google Patents
A kind of discoloration method of three nitrile of 1,3,6- hexanes Download PDFInfo
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- CN108033900A CN108033900A CN201711425466.6A CN201711425466A CN108033900A CN 108033900 A CN108033900 A CN 108033900A CN 201711425466 A CN201711425466 A CN 201711425466A CN 108033900 A CN108033900 A CN 108033900A
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- nitrile
- hexane
- discoloration method
- activated carbon
- hexanes
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- 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
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Abstract
The invention discloses a kind of discoloration method of three nitrile of 1,3,6 hexane, the discoloration method comprises the following steps：S1, the pretreatment of 1,3,6 hexane, three nitrile；S2, Activated Carbon Pretreatment；S3, decolorization；S4, is concentrated and dried, up to low colourity, the 1 of low free acid content, 3,6 hexane, three nitrile.The present invention provides a kind of efficient decolorizing, reduces by 1,3,6 hexane, the three nitrile discoloration method of free acid content, processing step is simple, has the value of popularization and application.
Description
Technical field
The present invention relates to lithium-ion battery electrolytes additive decoloration field, and especially a kind of three nitrile of 1,3,6- hexane is de-
Color method.
Background technology
Three nitrile of 1,3,6- hexanes has the excellent spies such as wider electrochemical window, high anode stability, low-viscosity and higher boiling
Property, it has been widely used as lithium-ion battery electrolytes additive.Three nitrile of 1,3,6- hexanes as electrolysis additive must possess
The requirement of high-purity, low colourity.
The prior art is prepared 1,3,6- hexane of electron level, three nitrile and is first handled using vacuum distillation, obtains orange-yellow liquid, will
Orange-yellow liquid is dissolved with ethyl acetate, strong oxidizer is then added, when stirring 6~24 is small；Then filtered, and acetic acid second
Ester washs filter cake, collects filtrate, and filtrate is carried out liquid separation processing, obtains water phase and organic phase, organic phase is washed once laggard
Row drying process, then carries out concentration, obtains light yellow oil, but products obtained therefrom colourity it is higher be extremely difficult to lithium from
The chromaticity requirements of sub- battery electrolyte additive（25% dimethyl carbonate solution≤60Hazen）, and extend colourity with the holding time
Increase is obvious, and electrolyte colourity can be caused exceeded.
For above-mentioned technical problem, there is provided one kind prepares low colourity, low free acid content, simple and practicable and effective 1,3,
Three nitrile discoloration method of 6- hexanes is technical problem in the urgent need to address at present.
The content of the invention
The technical problem to be solved is that inclined for three nitrile colourity of 1,3,6- hexanes made from the prior art for the invention
Height, the holding time extends and colourity substantially increases, and is unfavorable for being used in the situation of lithium battery electrolytes production, proposes a kind of letter
Three nitrile additive of electron level 1,3,6- hexanes that is single easy and fast and effeciently obtaining qualification.
To reach above-mentioned purpose, the discoloration method of 1,3,6- of one kind hexanes, three nitrile, the discoloration method comprises the following steps：
S1, the pretreatment of 1,3,6- hexane, three nitrile：Ethanol is added to 1,3,6- hexane, three nitrile, is configured to 1,3,6- hexane, three nitrile ethanol
Solution；1,3,6- hexane, three nitrile has good solubility in ethanol, dilutes 1,3,6- hexane, three nitrile by ethanol, makes 1,3,6-
Three nitrile of hexane was easier column.
S2, Activated Carbon Pretreatment：Activated carbon is filled into column, alkaline solution immersion is added, when standing at least 2 is small, then uses water
Wash after being in alkalescent to outflow water, then moisture≤1% with ethanol rinse to efflux, up to activated-charcoal column；Use alkaline solution
Activated carbon, and being developed lye with water, avoid remaining lye in activated carbon excessively made after column 1,3,6- oneself
Three nitrile band of alkane alkalescence, causes turbidity unqualified, and solution can effectively neutralize 1,3,6- hexane, three nitrile in alkalescent in activated carbon
Free acid, reduces free acid content, then moisture≤1% with ethanol rinse to efflux, avoids moisture is excessive from causing 1,3,
Three nitrile of 6- hexanes separates out during column is crossed, and reduces the rate of recovery.
S3, decolorization：1,3,6- hexane described in step S1, three nitrile ethanol solution upper prop is decolourized, up to 1,3,6- hexanes
Three nitrile destainers；Decolourized using the suction-operated of activated carbon to three nitrile of 1,3,6- hexanes.
S4, is concentrated and dried：Three nitrile destainer of 1,3,6- hexanes described in step S3 is concentrated under reduced pressure into and is produced without obvious bubble
After life, temperature is improved to 100 DEG C~120 DEG C, freeze-day with constant temperature at least 2h, up to 1,3,6- hexane, three nitrile that decolourizes.It is concentrated under reduced pressure 1,
3,6- hexane, three nitrile destainer is extremely substantially completely evaporated without obvious bubble, that is, ethanol, raising temperature to 100 DEG C~120 DEG C quickenings 1,
3,6- hexane, three nitrile rate of drying, drying temperature then increase drying time less than 100 DEG C, reduce efficiency, and drying temperature is higher than 120
DEG C then it is easy to cause the discoloration of three nitrile of 1,3,6- hexanes.
Further, in step S1, the ethanol is absolute ethyl alcohol, and the amount of alcohol added is 1,3,6- hexane, three nitrile weight
The 10%~50% of amount.Bringing into for moisture is reduced using absolute ethyl alcohol, ensures that 1,3,6- hexanes, three nitrile fully dissolves, amount of alcohol added
If 10% less than 1,3,6- hexane, three nitrile weight can not effectively dilute 1,3,6- hexane, three nitrile, if being higher than 1,3,6- hexanes three
50% of nitrile weight extends bleaching time and wastes solvent.
Yet further, in step S2, the activated carbon is granular activated carbon.Granular activated carbon has larger ratio surface
Product, decoloration and impurity absorption effect are good.
Yet further, in step S2, the alkaline solution is potassium hydroxide solution or sodium hydroxide solution, the alkalescence
Solution concentration is 5%~25%.Strong alkali solution is selected fully to activate activated carbon, alkaline solution concentration is less than 5% alkalescence too
Weak to activate activated carbon, alkaline solution concentration is excessive higher than remaining lye in 25% activated carbon, it is necessary to the time rinsed
It is long.
Yet further, in step S2, the outflow water pH value is 8~9.5.The activated carbon if outflow water pH value is less than 8
Alkalescence is too low, can not effectively neutralize the free acid of 1,3,6- hexane, three nitrile, the activated carbon alkalescence mistake if outflow water pH value is higher than 9.5
Height, caused 1 after column, and 3,6- hexane, three nitrile causes solution muddy in alkalescence.
Yet further, in step S3, described 1,3,6- hexane, three nitrile ethanol solution upper prop decoloration the rate of outflow be
The L/h of 10L/h~50.The rate of outflow of upper prop decoloration then reduces decolorizing efficiency less than 10L/h, and the rate of outflow is higher than 50 L/h then
1,3,6- hexane, three nitrile and activated carbon time of contact are too short, can not decolourize completely.
Yet further, in step S4, described 1, the temperature that 3,6- hexane, three nitrile destainer is concentrated under reduced pressure is 50 DEG C~70
DEG C, vacuum is -0.090MPa~-0.097MPa.Since the solvent of 1,3,6- hexane, three nitrile destainer is ethanol, low boiling point,
Evaporation of the solvent can be done under lower temperature conditions using heating, vacuum distillation, realize rapid concentration.
Compared with prior art, the advantageous effects of the invention：
Firstth, efficient decolorizing.1,3,6- hexane, the three nitrile color that tradition is prepared is deep, colourity is higher be extremely difficult to lithium from
The chromaticity requirements of sub- battery electrolyte additive, and extend colourity increase substantially with the holding time, cause electrolyte colourity exceeded.
The present invention provides a kind of processing method of efficient decolorizing, and 1,3,6- hexane, three nitrile is dissolved in after ethanol by activated carbon adsorption 1,3,
The foreign pigment of three nitrile of 6- hexanes, efficient decolorizing, the compound lithium ion battery electrolysis of the colourity of 1,3,6- hexane, three nitrile after decoloration
The chromaticity requirements of solution additive.
Secondth, free acid content is reduced.The present invention uses alkaline solution activated carbon, activated carbon is in alkaline environment,
The free acid contained by 1,3,6- hexane, three nitrile can be neutralized, reduces the free acid content of 1,3,6- hexanes, three nitrile, improves stable quality
Property.
3rd, processing step is simple, has application value.The present invention is by using the activated carbon pair after lye activates
1,3,6- hexane, three nitrile carries out adsorption treatment, the synchronous effect realized decoloration and neutralize free acid, and processing obtains low colourity, low trip
From the electron level lithium ion battery additive of acid content, processing step is simple, has application value.
Embodiment
Technical scheme is more fully understood for ease of those skilled in the art, in conjunction with embodiment to this
Invention is described further.
Embodiment 1
S1, the pretreatment of 1,3,6- hexane, three nitrile：To 1,3,6- hexane, three nitrile add absolute ethyl alcohol, the absolute ethyl alcohol addition 1,
The 10% of 3,6- hexane, three nitrile weight, is configured to 1,3,6- hexane, three nitrile ethanol solution；
S2, Activated Carbon Pretreatment：Granular activated carbon is filled into column, the sodium hydroxide solution that concentration is 5% is added and soaks, it is small to stand 3
When, outflow water pH value is then washed with water to as after 8, then with the moisture of ethanol rinse to efflux be 0.5%, up to activated carbon
Column；
S3, decolorization：1,3,6- hexane described in step S1, three nitrile ethanol solution upper prop is decolourized, and controls the rate of outflow to be
10L/h, up to 1,3,6- hexane, three nitrile destainer；
S4, is concentrated and dried：By 1 described in step S3,3,6- hexane, three nitrile destainer is 50 DEG C in temperature, vacuum pressure for-
It is concentrated under reduced pressure under the conditions of 0.090MPa after being produced without obvious bubble, improves temperature to 100 DEG C, freeze-day with constant temperature 2h, up to decolourizes
Three nitrile of 1,3,6- hexanes.
Embodiment 2
S1, the pretreatment of 1,3,6- hexane, three nitrile：To 1,3,6- hexane, three nitrile add absolute ethyl alcohol, the absolute ethyl alcohol addition 1,
The 30% of 3,6- hexane, three nitrile weight, is configured to 1,3,6- hexane, three nitrile ethanol solution；
S2, Activated Carbon Pretreatment：Granular activated carbon is filled into column, the potassium hydroxide solution that concentration is 15% is added and soaks, it is small to stand 2
When, outflow water pH value is then washed with water to as after 9, then with the moisture of ethanol rinse to efflux be 1%, up to activated-charcoal column；
S3, decolorization：1,3,6- hexane described in step S1, three nitrile ethanol solution upper prop is decolourized, and controls the rate of outflow to be
25L/h, up to 1,3,6- hexane, three nitrile destainer；
S4, is concentrated and dried：By 1 described in step S3,3,6- hexane, three nitrile destainer is 60 DEG C in temperature, vacuum pressure for-
It is concentrated under reduced pressure under the conditions of 0.095MPa after being produced without obvious bubble, temperature is improved to 110 DEG C, freeze-day with constant temperature 2.5h, up to de-
Three nitrile of color 1,3,6- hexanes.
Embodiment 3
S1, the pretreatment of 1,3,6- hexane, three nitrile：To 1,3,6- hexane, three nitrile add absolute ethyl alcohol, the absolute ethyl alcohol addition 1,
The 50% of 3,6- hexane, three nitrile weight, is configured to 1,3,6- hexane, three nitrile ethanol solution；
S2, Activated Carbon Pretreatment：Granular activated carbon is filled into column, the sodium hydroxide solution that concentration is 25% is added and soaks, stand 2.5
Hour, outflow water pH value is then washed with water to as after 9.5, then with the moisture of ethanol rinse to efflux be 0.4%, up to living
Property charcoal post；
S3, decolorization：1,3,6- hexane described in step S1, three nitrile ethanol solution upper prop is decolourized, and controls the rate of outflow to be
50L/h, up to 1,3,6- hexane, three nitrile destainer；
S4, is concentrated and dried：By 1 described in step S3,3,6- hexane, three nitrile destainer is 70 DEG C in temperature, vacuum pressure for-
It is concentrated under reduced pressure under the conditions of 0.097MPa after being produced without obvious bubble, improves temperature to 120 DEG C, freeze-day with constant temperature 3h, up to decolourizes
Three nitrile of 1,3,6- hexanes.
Take 1,3,6- hexane, three nitrile of the gained of above-described embodiment 1 to 3, using platinum-cobalt method test gained 1,3,6- oneself
The colourity of three nitrile of alkane, testing result are as shown in table 1.
Table 1, three nitrile colorimetric detection result of 1,3,6- hexanes
| Detection project | Standard limits | Embodiment 1 | Embodiment 2 | Embodiment 3 |
| Colourity | ≤60 | 20 | 25 | 35 |
Summary testing result is understood, is decolourized using the present invention to 1,3,6- hexane, three nitrile and neutralizes free acid treatment
Afterwards, obtained 1, the colourity and free acid content of 3,6- hexane, three nitrile meet the quality of lithium-ion battery electrolytes additive
It is required that.
The foregoing is only a preferred embodiment of the present invention, not makees limitation in any form to the present invention；It is all
The those of ordinary skill of the industry can swimmingly implement the present invention by described above；But all it is familiar with this professional technology people
Member without departing from the scope of the present invention, a little change, the modification made using disclosed above technology contents
It is equivalent embodiment of the invention with the equivalent variations of differentiation；Meanwhile all substantial technologicals according to the present invention are implemented to more than
Variation, modification and evolution of any equivalent variations for being made of example etc., still fall within technical scheme protection domain it
It is interior.
Claims (7)
1. one kind 1,3, the discoloration method of three nitrile of 6- hexanes, it is characterised in that the discoloration method comprises the following steps：
S1, the pretreatment of 1,3,6- hexane, three nitrile：Ethanol is added to 1,3,6- hexane, three nitrile, is configured to 1,3,6- hexane, three nitrile ethanol
Solution；
S2, Activated Carbon Pretreatment：Activated carbon is filled into column, alkaline solution immersion is added, when standing at least 2 is small, is then washed with water
After being in alkalescent to outflow water, then moisture≤1% with ethanol rinse to efflux, up to activated-charcoal column；
S3, decolorization：1,3,6- hexane described in step S1, three nitrile ethanol solution upper prop is decolourized, up to 1,3,6- hexane, three nitrile
Destainer；
S4, is concentrated and dried：By 1 described in step S3,3,6- hexane, three nitrile destainer be concentrated under reduced pressure into without obvious bubble produce after,
Temperature is improved to 100 DEG C~120 DEG C, freeze-day with constant temperature at least 2h, up to 1,3,6- hexane, three nitrile that decolourizes.
2. according to claim 11, the discoloration method of 3,6- hexane, three nitrile, it is characterised in that：In step S1, the second
Alcohol is absolute ethyl alcohol, and the amount of alcohol added is the 10%~50% of 1,3,6- hexane, three nitrile weight.
3. according to claim 11, the discoloration method of 3,6- hexane, three nitrile, it is characterised in that：In step S2, the work
Property charcoal is granular activated carbon.
4. according to claim 11, the discoloration method of 3,6- hexane, three nitrile, it is characterised in that：In step S2, the alkali
Property solution be potassium hydroxide solution or sodium hydroxide solution, the alkaline solution concentration is 5%~25%.
5. according to claim 11, the discoloration method of 3,6- hexane, three nitrile, it is characterised in that：In step S2, the stream
Water outlet pH value is 8~9.5.
6. according to claim 11, the discoloration method of 3,6- hexane, three nitrile, it is characterised in that：In step S3, described 1,
The rate of outflow of three nitrile ethanol solution upper prop of 3,6- hexanes decoloration is the L/h of 10L/h~50.
7. according to claim 11, the discoloration method of 3,6- hexane, three nitrile, it is characterised in that：In step S4, described 1,
The temperature that 3,6- hexane, three nitrile destainer is concentrated under reduced pressure is 50 DEG C~70 DEG C, and vacuum is -0.090MPa~-0.097MPa.
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| CN201711425466.6A CN108033900A (en) | 2017-12-25 | 2017-12-25 | A kind of discoloration method of three nitrile of 1,3,6- hexanes |
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| CN201711425466.6A CN108033900A (en) | 2017-12-25 | 2017-12-25 | A kind of discoloration method of three nitrile of 1,3,6- hexanes |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111517986A (en) * | 2020-06-12 | 2020-08-11 | 上海如鲲新材料有限公司 | Novel method for preparing aliphatic trinitrile and aliphatic trinitrile prepared by using same |
| CN111961029A (en) * | 2020-08-31 | 2020-11-20 | 常熟聚和化学有限公司 | Method for reducing free acid of electronic propane sultone |
| CN112825371A (en) * | 2019-11-20 | 2021-05-21 | 珠海冠宇电池股份有限公司 | Electrolyte for high-voltage lithium ion battery and lithium ion battery comprising same |
| CN112825373A (en) * | 2019-11-20 | 2021-05-21 | 珠海冠宇电池股份有限公司 | Non-aqueous electrolyte and lithium secondary battery comprising same |
| CN112825372A (en) * | 2019-11-20 | 2021-05-21 | 珠海冠宇电池股份有限公司 | Electrolyte and electrochemical device containing same |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112825371A (en) * | 2019-11-20 | 2021-05-21 | 珠海冠宇电池股份有限公司 | Electrolyte for high-voltage lithium ion battery and lithium ion battery comprising same |
| CN112825373A (en) * | 2019-11-20 | 2021-05-21 | 珠海冠宇电池股份有限公司 | Non-aqueous electrolyte and lithium secondary battery comprising same |
| CN112825372A (en) * | 2019-11-20 | 2021-05-21 | 珠海冠宇电池股份有限公司 | Electrolyte and electrochemical device containing same |
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