CN109503543B - Composite stabilizer for chlorinated ethylene carbonate - Google Patents
Composite stabilizer for chlorinated ethylene carbonate Download PDFInfo
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- CN109503543B CN109503543B CN201811557931.6A CN201811557931A CN109503543B CN 109503543 B CN109503543 B CN 109503543B CN 201811557931 A CN201811557931 A CN 201811557931A CN 109503543 B CN109503543 B CN 109503543B
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- ethylene carbonate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/42—Halogen atoms or nitro radicals
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Abstract
The invention discloses a composite stabilizer for chlorinated ethylene carbonate, which comprises 1-10% of organic tin and 50-99% of epoxide by mass percent, wherein the sum of the organic tin and the epoxide by mass percent is 100%. The composite stabilizer for chlorinated ethylene carbonate can obviously improve the thermal stability and the normal-temperature storage stability of the chlorinated ethylene carbonate through the selection and proportioning design of raw materials; the organic silicon compound is added into the chloroethylene carbonate for common storage, so that the decomposition of the chloroethylene carbonate is effectively inhibited, the discoloration of the chloroethylene carbonate is slowed down, and the effect is obvious.
Description
Technical Field
The invention relates to the technical field of stabilizers, in particular to a composite stabilizer for chlorinated ethylene carbonate.
Background
Chloroethylene carbonate is an important raw material for preparing lithium battery electrolyte additives, namely fluoroethylene carbonate (FEC) and Vinylene Carbonate (VC). Tests show that the chloroethylene carbonate is easy to decompose during storage, particularly when being heated, so that chloroacetaldehyde, Vinylene Carbonate (VC), hydrogen chloride, carbon dioxide gas and the like are generated. Vinylene Carbonate (VC) is more unstable, prone to discoloration and polymerization, and hydrogen chloride can be more strongly decomposed. Therefore, the chlorinated ethylene carbonate product can be gradually deepened when being stored for a long time or heated, the purity is greatly reduced, the service performance is influenced, and potential safety hazards are brought to storage and use.
Disclosure of Invention
The invention mainly solves the technical problem of providing a composite stabilizer for chlorinated ethylene carbonate, which can solve the problem of decomposition of the chlorinated ethylene carbonate under the conditions of storage or heating.
In order to solve the technical problems, the invention adopts a technical scheme that: the composite stabilizer for chlorinated ethylene carbonate comprises 1-10% of organic tin and 50-99% of epoxide by mass percent, wherein the sum of the organic tin and the epoxide by mass percent is 100%.
In a preferred embodiment of the invention, the composite stabilizer further comprises 0-30% by mass of phosphite ester; the sum of the mass percentages of the organotin, epoxide and phosphite ester is 100 percent.
In a preferred embodiment of the invention, the composite stabilizer further comprises 0-5% by mass of an ultraviolet absorber; the sum of the mass percentages of the organic tin, the epoxide, the phosphite ester and the ultraviolet absorbent is 100 percent.
In a preferred embodiment of the invention, the composite stabilizer further comprises an antioxidant with a mass percentage of 0-5%; the sum of the mass percentages of the organotin, epoxide, phosphite ester, ultraviolet absorbent and antioxidant is 100 percent.
In a preferred embodiment of the present invention, the organic tin is one or more of tetramethyltin, methyltin mercaptide, dibutyltin bis (monobutylsumate), di-n-octyltin maleate, dibutyltin dilaurate, di-n-octyltin dilaurate, dibutyltin acetate, monobutyltin oxide, stannous octoate, or di-n-octyltin bis (isobutyl thioglycolate).
In a preferred embodiment of the present invention, the epoxide is one or more selected from ethylene glycol diglycidyl ether, epoxidized soybean oil, epoxidized castor oil, epoxidized linseed oil, epoxidized tall oil, epoxidized sunflower oil, epoxy oleate, epoxy butyl stearate, alkylene glycidyl ether, butyl glycidyl ether, 1, 4-butanediol diglycidyl ether, phenyl glycidyl ether, polypropylene glycol diglycidyl ether, C12-C14 fatty glycidyl ether, benzyl glycidyl ether, 1, 6-hexanediol diglycidyl ether, o-tolyl glycidyl ether, neopentyl glycol diglycidyl ether, and epoxy octyl stearate.
In a preferred embodiment of the invention, the phosphite is one or more of triphenyl phosphite, triisooctyl phosphite, triisodecyl phosphite, trilauryl phosphite, phenyl diisodecyl phosphite, diphenyl isodecyl phosphite, 2-ethylhexyl diphenyl phosphite, poly (dipropylene glycol) phenyl phosphite, alkyl (C10-C15) bisphenol A phosphite, tris (nonylphenyl) phosphite, tris (2, 4-di-tert-butylphenyl) phosphite, dioctadecyl pentaerythrityl diphosphite or tetrakis (2, 4-di-tert-butylphenyl) 4,4' -biphenylene diphosphate.
In a preferred embodiment of the present invention, the ultraviolet light absorber is phenyl ortho-hydroxybenzoate, resorcinol monobenzoate, 2, 4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2- (2 ' -hydroxy-3 ', 5 ' -di-tert-phenyl) -5-chlorobenzotriazole, 2- (2 ' -hydroxy-5 ' -methylphenyl) benzotriazol, 2- (2-hydroxy-3, 5 bis (a, a-dimethylbenzyl) phenyl) benzotriazole, tris (1, 2,2, 6, 6-pentamethylpiperidinyl) phosphite, 4-benzoyloxy-2, 2,6, 6-tetramethylpiperidine, 2, 6-tetramethylpiperidine, p-toluenesulfonate, 2,4, 6-tris (2 '-n-butoxyphenyl) -1,3, 5-triazine, hexamethylphosphoric triamide, 2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -5-chlorobenzotriazole (UV-326), 2- (2' -hydroxy-3 ', 5' -di-tert-phenyl) -5-chlorobenzotriazole, 2- (2-hydroxy-3, 5-ditert-pentylphenyl) benzotriazole, 2- (2 '-hydroxy-4' -benzoyloxyphenyl) -5-chloro-2H-benzotriazole, 2- (4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazin-2-yl) -5-octyloxyphenol or 2- (4, 6-diphenyl-1, 3, 5-triazine-2-yl) -5-hexyloxy-phenol.
In a preferred embodiment of the present invention, the antioxidant is 2-tert-butyl-4-methoxyphenol, 2, 6-di-tert-butyl-4-methylphenol, di-tert-butylhydroquinone, p-methoxyphenol, bisphenol A, nonylphenol, 2 '-methylenebis (4-ethyl-6-tert-butylphenol), 1,3, 5-tris (3, 5-tert-butyl-4-hydroxybenzyl) trimethylbenzene, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxyphenyl) isocyanate, 4-hydroxydodecanoic acid anilide, 4-hydroxyoctadecanoic acid anilide, 4' -thiobis (3-methyl-6-tert-butylphenol), 2,2 '-methylene bis (4-methyl-6-tert-butylphenol), 4' -di-tert-octyldiphenylamine, 1, 6-hexamethylene bis (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, n-octadecyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 1, 3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane or 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene.
In order to solve the technical problem, the invention adopts another technical scheme that: the application of the composite stabilizer in chlorinated ethylene carbonate is provided, wherein the composite stabilizer accounting for 0.1-3% of the mass of the chlorinated ethylene carbonate is added into the chlorinated ethylene carbonate and stored together.
The invention has the beneficial effects that: the composite stabilizer for chlorinated ethylene carbonate can obviously improve the thermal stability and the normal-temperature storage stability of the chlorinated ethylene carbonate through the selection and proportioning design of raw materials; the organic silicon compound is added into the chloroethylene carbonate for common storage, so that the decomposition of the chloroethylene carbonate is effectively inhibited, the discoloration of the chloroethylene carbonate is slowed down, and the effect is obvious.
Detailed Description
The following detailed description of the preferred embodiments of the present invention is provided to enable those skilled in the art to more readily understand the advantages and features of the present invention, and to clearly and unequivocally define the scope of the present invention.
The embodiment of the invention comprises the following steps:
at present, few reports on the research and use of the composite stabilizer for the chloroethylene carbonate exist. The invention is matched with ultraviolet absorbent, antioxidant and the like to prepare the high-efficiency composite stabilizer so as to improve the thermal stability and the light stability of the chlorinated ethylene carbonate.
The invention discloses a composite stabilizer for chlorinated ethylene carbonate, which comprises 1-10% of organic tin and 50-99% of epoxide by mass percent, wherein the sum of the organic tin and the epoxide by mass percent is 100%.
Preferably, the composite stabilizer further comprises 0-30% by mass of phosphite ester; the sum of the mass percentages of the organotin, epoxide and phosphite ester is 100 percent.
Preferably, the composite stabilizer further comprises an ultraviolet absorber with the mass percentage of 0-5%; the sum of the mass percentages of the organic tin, the epoxide, the phosphite ester and the ultraviolet absorbent is 100 percent.
Preferably, the composite stabilizer further comprises an antioxidant with the mass percentage of 0-5%; the sum of the mass percentages of the organotin, epoxide, phosphite ester, ultraviolet absorbent and antioxidant is 100 percent.
In each of the above schemes, the organotin is one or more of tetramethyltin, methyltin mercaptide, dibutyltin bis (monobutylal maleate), di-n-octyltin maleate, dibutyltin dilaurate, di-n-octyltin dilaurate, dibutyltin acetate, monobutyltin oxide, stannous octoate, or di-n-octyltin bis (isobutyl thioglycolate).
The epoxide is one or more of ethylene glycol diglycidyl ether, epoxidized soybean oil, epoxidized castor oil, epoxidized linseed oil, epoxidized tall oil, epoxidized sunflower oil, epoxy oleate, epoxy butyl stearate, alkylene glycidyl ether, butyl glycidyl ether, 1, 4-butanediol diglycidyl ether, phenyl glycidyl ether, polypropylene glycol diglycidyl ether, C12-C14 fatty glycidyl ether, benzyl glycidyl ether, 1, 6-hexanediol diglycidyl ether, o-tolyl glycidyl ether, neopentyl glycol diglycidyl ether or epoxy octyl stearate.
The phosphite ester is one or more of triphenyl phosphite, triisooctyl phosphite, triisodecyl phosphite, trilauryl phosphite, phenyl diisodecyl phosphite, diphenyl isodecyl phosphite, 2-ethylhexyl diphenyl phosphite, poly (dipropylene glycol) phenyl phosphite, alkyl (C10-C15) bisphenol A phosphite, tri (nonylphenyl) phosphite, tri (2, 4-di-tert-butylphenyl) phosphite, dioctadecyl pentaerythrityl diphosphite or tetra (2, 4-di-tert-butylphenyl) 4,4' -biphenylene diphosphate.
The ultraviolet absorbent is phenyl ortho-hydroxybenzoate, resorcinol monobenzoate, 2, 4-dihydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxybenzophenone, 2- (2 '-hydroxy-3', 5 '-di-tert-phenyl) -5-chlorobenzotriazole, 2- (2' -hydroxy-5 '-methylphenyl) benzotriazole, 2- (2-hydroxy-3, 5 bis (a, a-dimethylbenzyl) phenyl) benzotriazole, tris (1, 2,2, 6, 6-pentamethylpiperidinyl) phosphite, 4-benzoyloxy-2, 2,6, 6-tetramethylpiperidine, 2,4, 6-tris (2' -n-butoxyphenyl) -1,3, 5-triazine, hexamethylphosphoric triamide, 2- (2-hydroxy-3-tert-butyl-5-methylphenyl) -5-chlorobenzotriazole, 2- (2 ' -hydroxy-3 ', 5 ' -di-tert-phenyl) -5-chlorobenzotriazole (UV-327), 2- (2-hydroxy-3, 5-ditert-pentylphenyl) benzotriazole, 2- (2 ' -hydroxy-4 ' -benzoyloxyphenyl) -5-chloro-2H-benzotriazole, 2- (4, 6-bis (2, 4-dimethylphenyl) -1,3, 5-triazin-2-yl) -5-octyloxyphenol or 2- (4, 6-diphenyl-1, 3, 5-triazine-2-yl) -5-hexyloxy-phenol.
The antioxidant is 2-tert-butyl-4-methoxyphenol, 2, 6-di-tert-butyl-4-methylphenol, di-tert-butylhydroquinone, p-methoxyphenol, bisphenol A, nonylphenol, 2' -methylenebis (4-ethyl-6-tert-butylphenol), 1,3, 5-tris (3, 5-tert-butyl-4-hydroxybenzyl) trimethylbenzene, 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxyphenyl) isocyanate, 4-hydroxydodecanoic acid acyl substituted aniline, 4-hydroxyoctadecanoic acid substituted aniline, 4' -thiobis (3-methyl-6-tert-butylphenol), 2' -methylenebis (4-methyl-6-tert-butylphenol), 4,4' -di-tert-octyldiphenylamine, 1, 6-hexamethylene bis (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, n-octadecyl beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 1, 3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane or 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene.
The application of the composite stabilizer in the chloroethylene carbonate is as follows: weighing the components according to a formula, uniformly mixing the components by using ultrasonic waves, adding the mixture into chloroethylene carbonate for co-storage, wherein the addition amount of the composite stabilizer accounts for 0.1-3% of the mass of the chloroethylene carbonate.
Example 1
And (3) adding 99g of epoxidized soybean oil and 1g of tetramethyl tin into the reaction bottle, and carrying out ultrasonic treatment for 5 minutes to obtain the composite stabilizer.
Example 2
Adding 75g of ethylene glycol diglycidyl ether and 2g of 2, 6-di-tert-butyl-4-methylphenol into a reaction bottle, dissolving the mixture by ultrasonic waves for 5 minutes, adding 5g of methyl tin mercaptide, 8g of tris (2, 4-di-tert-butylphenyl) phosphite and 10g of diphenyl isodecyl phosphite, and performing ultrasonic waves for 5 minutes to obtain the composite stabilizer.
Example 3
20g of epoxy oleate, 30g of 1, 6-hexanediol diglycidyl ether, 5g of UV-9 and 5g of p-methoxyphenol are added into a reaction bottle, dissolved by ultrasonic waves for 5 minutes, 10g of di-n-octyl tin dilaurate and 30g of triphenyl phosphite are added, and the composite stabilizer is obtained by ultrasonic waves for 5 minutes.
Example 4
And adding 75g of epoxy tall oil, 2g of UV-531 and 5g of nonylphenol into a reaction bottle, dissolving by ultrasonic waves for 5 minutes, adding 10g of dibutyltin maleate, 4g of triphenyl phosphite and 4g of diphenyl isodecyl phosphite, and performing ultrasonic waves for 5 minutes to obtain the composite stabilizer.
Test example 1
0.2g of the composite stabilizer prepared in example 1 was added to 200g of vinyl chlorocarbonate and stored at 25 ℃ for 30 days.
Comparative example 1
The conditions of test example 1 were the same, but no composite stabilizer was added.
Test example 2
1g of the composite stabilizer prepared in example 2 was added to 200g of vinyl chlorocarbonate, and the mixture was left at 80 ℃ for 4 hours.
Comparative example 2
The conditions of test example 2 were the same, but no composite stabilizer was added.
Test example 3
3g of the composite stabilizer prepared in example 3 was added to 200g of vinyl chlorocarbonate and left at 120 ℃ for 4 hours.
Comparative example 3
The conditions of test example 3 were the same, but no composite stabilizer was added.
Test example 4
6g of the composite stabilizer prepared in example 4 was added to 200g of vinyl chlorocarbonate, and the mixture was left at 150 ℃ for 4 hours.
Comparative example 4
The conditions of test example 4 were the same, but no composite stabilizer was added.
The test results of the above test are shown in the following table:
the data show that the composite stabilizer for chlorinated ethylene carbonate can effectively reduce the decomposition of chlorinated ethylene carbonate, and has obvious effect on the stability of the purity of chlorinated ethylene carbonate. The composite stabilizer has outstanding advantages as a stabilizer for chlorinated ethylene carbonate, and mainly shows that the retention rate of purity and chromaticity at normal temperature is high and the variation of purity at high temperature is small.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (4)
1. A composite stabilizer for vinyl chlorocarbonate is characterized by comprising 75g of ethylene glycol diglycidyl ether, 2g of 2, 6-di-tert-butyl-4-methylphenol, 5g of methyl tin mercaptide, 8g of tris (2, 4-di-tert-butylphenyl) phosphite and 10g of diphenylisodecyl phosphite.
2. The composite stabilizer for the chlorinated ethylene carbonate is characterized by comprising 20g of epoxy oleate, 30g of 1, 6-hexanediol diglycidyl ether, 5g of UV-9, 5g of p-methoxyphenol, 10g of di-n-octyl tin dilaurate and 30g of triphenyl phosphite.
3. The composite stabilizer for the ethylene chlorocarbonate is characterized by comprising 75g of epoxy tall oil, 2g of UV-531, 5g of nonylphenol, 10g of dibutyltin maleate, 4g of triphenyl phosphite and 4g of diphenyl isodecyl phosphite.
4. Use of the composite stabilizer according to any one of claims 1 to 3 in chlorinated ethylene carbonate, wherein 0.1 to 3% by mass of the composite stabilizer is added to the chlorinated ethylene carbonate and stored together.
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| CN201811557931.6A CN109503543B (en) | 2018-12-19 | 2018-12-19 | Composite stabilizer for chlorinated ethylene carbonate |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112480060B (en) * | 2020-11-30 | 2022-04-01 | 苏州华一新能源科技股份有限公司 | Storage method of vinyl ethylene carbonate |
| CN112457523A (en) * | 2020-12-18 | 2021-03-09 | 威海市正旺塑业有限公司 | High-stability and high-plasticity composite PVC (polyvinyl chloride) processing aid and preparation method thereof |
| CN115572279B (en) * | 2022-11-22 | 2023-04-07 | 山东孚日新能源材料有限公司 | Method for preparing chlorinated ethylene carbonate by forced external circulation |
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| CN104449580A (en) * | 2013-09-24 | 2015-03-25 | 中化蓝天集团有限公司 | Composition containing HFC-161 and stabilizer |
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