CN103351301A - Synthetic method for high-purity quaternary ammonium salt - Google Patents
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- CN103351301A CN103351301A CN2013102715023A CN201310271502A CN103351301A CN 103351301 A CN103351301 A CN 103351301A CN 2013102715023 A CN2013102715023 A CN 2013102715023A CN 201310271502 A CN201310271502 A CN 201310271502A CN 103351301 A CN103351301 A CN 103351301A
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- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 50
- 238000010189 synthetic method Methods 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 10
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 230000002152 alkylating effect Effects 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 dimethyl tertiary amide Chemical class 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 3
- AXGOJXQBKJZYTD-UHFFFAOYSA-N C(Cl)(Br)C(F)(F)F.[S].[P] Chemical compound C(Cl)(Br)C(F)(F)F.[S].[P] AXGOJXQBKJZYTD-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 230000035484 reaction time Effects 0.000 abstract description 2
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 238000005119 centrifugation Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 7
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
- 238000004445 quantitative analysis Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229940050176 methyl chloride Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 2
- GBZJANXKLIMDMO-UHFFFAOYSA-M [Cl-].[NH4+].C(CCC)[P+](C)(CCCC)CCCC.[Cl-] Chemical compound [Cl-].[NH4+].C(CCC)[P+](C)(CCCC)CCCC.[Cl-] GBZJANXKLIMDMO-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- XMGCJZBZVMGBQN-UHFFFAOYSA-N 2-[3-[3-[2,2-diphenylethyl-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]amino]propoxy]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(OCCCN(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC=2C=C(C(F)=CC=2)C(F)(F)F)=C1 XMGCJZBZVMGBQN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthetic method for a quaternary ammonium salt, especially to a synthetic method for a high-purity quaternary ammonium salt. The synthetic method comprises the following steps: adding a certain amount of a solvent, tertiary amine and an alkylation reagent into a reaction vessel with reaction temperature being 20 to 105 DEG C and reaction time being 2 to 24 h; and after a reaction is ended, carrying out direct cooling, centrifugation and drying so as to obtain the high-purity quaternary ammonium salt. The solvent used in the method can be used indiscriminately and repeatedly, so production cost is reduced, and the method has a high industrial practical value.
Description
Technical field
The present invention relates generally to the synthetic field of quaternary ammonium salt, relates in particular to the synthetic field of a kind of high-purity quaternary ammonium salt.
Background technology
Quaternary ammonium salt has been widely used in the fields such as chemical industry, medicine, mining, printing and dyeing, building, plastic working, oil production as a kind of important industrial chemicals.
Along with the development of science and technology, the Application Areas of quaternary ammonium salt constantly enlarges, and is more and more higher to the requirement of quaternary ammonium salt purity.For example, as the quaternary ammonium salt that ionic liquid electrolyte uses, wherein content of halogen requires to be lower than 10ppm; Quaternary ammonium salt and derived product thereof, as the clean agent of microelectronic industry, unhindered amina content requirement wherein is lower than 0.03%, metal ion content even be less than 1ppb.
Quaternary ammonium salt generally makes by alkylated reaction, and impurity wherein mainly is completely unhindered amina and halogen etc. of unreacted, and these impurity are introduced in the production building-up process.If obtain high-purity quaternary ammonium salt, need to realize by purifying.A small amount of quaternary ammonium salt can pass through column chromatogram chromatography, ion-exchange column purification.A large amount of quaternary ammonium salts, the Methods For Purifications such as normal operation recrystallization.About synthesizing of quaternary ammonium salt, numerous by the synthetic method of the disclosed quaternary ammonium salt of Chinese patent, for example:
The patent No. is a kind of quaternary ammonium salt of 200510023182.5 and preparation method thereof.The method is with C
10～C
22Monohydroxy-alcohol be reaction medium, halohydrocarbon is joined in the tertiary amine, 10～140 ℃ of lower reactions 8～240 hours, obtain 5%～90% quaternary ammonium salt product, as the C of reaction medium
10～C
22Monohydroxy-alcohol is not separated from product.
The patent No. is the synthetic method of 200510061094.4 quaternary ammonium salt.This method under ionic liquid [EMIm] Br catalysis, has been synthesized the quaternary ammonium salt that contains multiple different negative ions take carbonic ether (fat) and amine (ammonia) salt as raw material, and catalyzer wherein is difficult to separate, and yield is not high.
The patent No. is 200710008626.7 novel technique for synthesizing quaternary ammonium salt.This method is that the synthetic method of 200510061094.4 quaternary ammonium salt has been made significant improvement to the patent No., take carbonic ether (fat) and amine (ammonia) salt as raw material, does not use catalyzer, has directly synthesized the quaternary ammonium salt that contains different negative ions with higher yield.But the quality of quaternary ammonium salt fails to reach the high purity rank.
The preparation method of a kind of quaternary ammonium salt of the patent No. 200610050213.0.This method is with C
12～C
18Alkyl dimethyl tertiary amide, alkylating reagent (C
1～C
8Halohydrocarbon) be raw material, water is reaction medium, in 50～105 ℃ of lower reactions, has prepared the quaternary ammonium salt aqueous solution that contains the halogen negative ion.This method technique environmental protection, but being of limited application of product must could enlarge its Application Areas by a series of aftertreatments.
The synthetic method of a kind of ester based quaternary ammonium salt of the patent No. 200610096264.7.This method is take long-chain carboxylic acid's ester group tertiary amine and alkylating reagent as raw material, and an acidic catalyst is used in nitrogen protection, has synthesized ester based quaternary ammonium salt under solvent-free.The unresolved catalyzer of this method and product separation problem, product purity is not high.
In existing quaternary ammonium salt synthetic method, there is following problem:
1, the general synthetic middle catalyzer that uses and solvent and quaternary ammonium salt are not easily separated, cause purity not high, and product yield is low.2, temperature of reaction is higher, the time is long, causes energy consumption large.3, the raw material tertiary amine of synthetic quaternary ammonium salt and the poorly water-soluble of alkylating reagent, water solvent can not provide good reaction media, and productive rate is not high.If obtain high-purity quaternary ammonium salt, need to realize by methods such as recrystallizations toward contact.Like this, product causes yield to reduce because being dissolved in the solvent, and complex operation and reduce production capacity.
Summary of the invention
The objective of the invention is for the existing shortcoming that the existing yield of quaternary ammonium salt synthetic method is low, purity is not high, production capacity is low, a kind of high yield, high purity, efficient quaternary ammonium salt synthetic method are provided.
The synthetic method of high-purity quaternary ammonium salt of the present invention comprises the steps:
Tertiary amine and the alkylating reagent of certain proportioning are put into reactor, directly synthetic in solvent, after reaction finishes, crystallisation by cooling, directly centrifugal drying can obtain highly purified quaternary ammonium salt product.
Described tertiary amine is NR
1R
2R
3, R wherein
1, R
2, R
3Be contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group or-CR
4R
5R
6, R in the base
4, R
5, R
6Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane, be preferably C
10～C
18Alkyl dimethyl tertiary amide.
Described alkylating reagent is C
1～C
8Halohydrocarbon or carbonic ether, sulfuric ester, phosphoric acid ester, barkite etc., be preferably C
1～C
2Halohydrocarbon, methylcarbonate, methyl-sulfate.。
Described direct synthesis method is to carry out under the condition of catalyzer not having.
Described solvent is water, C
1～C
6The mixture of one or more solvents in Organic Alcohol, ketone, the ester is preferably methyl alcohol, ethanol, Virahol, ethyl acetate, acetone, butanone.
The equivalence ratio of described tertiary amine and alkylating reagent is 1:0.95～1.5, is preferably 1:1.15.
The weight ratio of described solvent and tertiary amine is 0.3～7:1, is preferably 1.5:1.
Described synthesis temperature is 20～105 ℃, is preferably 50～70 ℃.
Described generated time is 2～24 hours, is preferably 4 hours.
Beneficial effect of the present invention:
The synthetic method of high-purity quaternary ammonium salt of the present invention is compared with the synthetic method of existing quaternary ammonium salt, and its characteristics are: 1, operational path is succinct, does not need to use any catalyzer; 2, poorly soluble in this solvent of the good and product of reaction raw materials solvability in solvent can guarantee in process of production, and realization response and crystallization are carried out simultaneously; 3, unreacted raw material then is present in the solvent, can continue reaction when again applying mechanically solvent, and the reaction times shortens like this, production capacity improves, cost of labor reduces, and whole production cost greatly reduces.
Embodiment
Below in conjunction with embodiment the present invention is made further and to specify, but the present invention is not limited to these embodiment.
Embodiment 1
Take by weighing 300g octadecyl dimethyl tertiary amine, join in the small-sized reactor that fills 550g acetone, in still, add the 61g methyl chloride again, keep 70 ℃ of temperature in the kettle, stirring reaction 4 hours, reaction naturally cools to room temperature after finishing.Suction filtration obtains octadecyl trimethyl ammonium chloride 321g, yield 91.5%, and quantitative analysis octadecyl trimethyl ammonium chloride content is 99.6%.
Embodiment 2
Take by weighing 320g hexadecyldimethyl benzyl ammonium tertiary amine, join in the small-sized reactor that fills the 600g Virahol, in still, add the 66g methyl chloride again, keep 60 ℃ of temperature in the kettle, stirring reaction 4.5 hours, reaction naturally cools to room temperature after finishing.Suction filtration obtains palmityl trimethyl ammonium chloride 352g, yield 92.6%, and quantitative analysis palmityl trimethyl ammonium chloride content is 99.8%.
Embodiment 3
Take by weighing 300g hexadecyldimethyl benzyl ammonium tertiary amine, join and fill in the 600g acetone small-sized reactor of (containing 10% ethyl acetate), in still, add the 111g monobromethane again, keep 55 ℃ of temperature in the kettle, stirring reaction 4 hours, reaction naturally cools to room temperature after finishing.Suction filtration obtains cetyl trimethylammonium bromide 369g, yield 91%, and quantitative analysis cetyl trimethylammonium bromide content is 99.7%.
Embodiment 4
Take by weighing the two dodecyl methyl tertiary amines of 250g, join in the small-sized reactor that fills the 500g ethyl acetate, in still, add the 72g monobromethane again, keep 60 ℃ of temperature in the kettle, stirring reaction 6 hours, reaction naturally cools to room temperature after finishing.Suction filtration obtains didodecyldimethylammbromide bromide 291g, yield 92.3%, and quantitative analysis didodecyldimethylammbromide bromide content is 99.9%.
Embodiment 5
Take by weighing the 380g Tributylamine, join in the small-sized reactor that fills 350g ethanol, in still, add the 114g methyl chloride again, keep 55 ℃ of temperature in the kettle, stirring reaction 3 hours, cooling and centrifugal drying after reaction finishes obtain tributyl-methyl phosphonium ammonium chloride 444g, yield 92%, quantitative analysis tributyl-methyl phosphonium ammonium chloride content is 99.7%.
Embodiment 6
Take by weighing the 214g Dodecyl Dimethyl Amine, join in the small-sized reactor that fills the 150g Virahol, in still, add the 75g methylcarbonate again, keep 75 ℃ of temperature in the kettle, stirring reaction 8 hours, reaction naturally cools to room temperature after finishing.Suction filtration obtains dodecyl trimethylammonium volatile salt 233g, yield 90%, and the content of quantitative analysis dodecyl trimethylammonium volatile salt is 99.1%.
Claims (9)
1. the synthetic method of a high-purity quaternary ammonium salt is characterized in that, tertiary amine and the alkylating reagent of certain proportioning are put into reactor, and is directly synthetic in solvent, and after reaction finished, cooling off also directly, centrifugal drying can obtain highly purified quaternary ammonium salt product.
2. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, described tertiary amine is NR
1R
2R
3, R wherein
1, R
2, R
3Be contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain hydrocarbon oxynitride phosphor sulphur Halothane organic group or-CR
4R
5R
6, R in the base
4, R
5, R
6Be hydrogen, contain hydrocarbon alkyl, thiazolinyl, alkynyl, phenyl, aryl, contain the organic group of hydrocarbon oxynitride phosphor sulphur Halothane, be preferably C
10～C
18Alkyl dimethyl tertiary amide.
3. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, described alkylating reagent is C
1～C
8Halohydrocarbon or carbonic ether, sulfuric ester, phosphoric acid ester, barkite etc. be preferably C
1～C
2Halohydrocarbon, methylcarbonate, methyl-sulfate.
4. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, described direct synthesis method is to carry out under the condition of catalyzer not having.
5. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, described solvent is water, C
1～C
6The mixture of one or more solvents in Organic Alcohol, ketone, the ester is preferably methyl alcohol, ethanol, Virahol, ethyl acetate, acetone, butanone; After reaction was finished, solvent for use can be used by time.
6. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, the equivalence ratio of described tertiary amine and alkylating reagent is 1:0.95～1.5, is preferably 1:1.15.
7. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, the weight ratio of described solvent and tertiary amine is 0.3～7:1, is preferably 1.5:1.
8. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, described synthesis temperature is 20～105 ℃, is preferably 50～70 ℃.
9. the synthetic method of high-purity quaternary ammonium salt according to claim 1 is characterized in that, described generated time is 2～24 hours, is preferably 4 hours.
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104163763A (en) * | 2014-07-14 | 2014-11-26 | 安徽奔马先端科技有限公司 | New synthesis method of high purity quaternary ammonium salt |
| CN104193510A (en) * | 2014-08-19 | 2014-12-10 | 湖北富邦科技股份有限公司 | Quaternary ammonium salt anticaking agent, and preparation method and application of quaternary ammonium salt |
| CN106757467A (en) * | 2016-11-23 | 2017-05-31 | 上海斯瑞科技有限公司 | A kind of superhigh molecular weight polyethylene fibers and preparation method thereof |
| CN106916071A (en) * | 2017-03-24 | 2017-07-04 | 吴琏 | The synthetic method of benzalkonium chloride mixture |
| CN106916068A (en) * | 2017-03-24 | 2017-07-04 | 吴琏 | A kind of simple and convenient benzalkonium chloride production method |
| CN106946716A (en) * | 2017-03-24 | 2017-07-14 | 吴琏 | A kind of benzalkonium chloride monomer synthesis technique |
| CN109053469A (en) * | 2018-09-04 | 2018-12-21 | 涟水新源生物科技有限公司 | A kind of preparation process of high stability octadecyltrimethylammonium chloride |
| CN109553539A (en) * | 2017-09-27 | 2019-04-02 | 湖北葛店人福药用辅料有限责任公司 | A kind of preparation method of benzalkonium chloride |
| CN109553536A (en) * | 2017-09-27 | 2019-04-02 | 湖北葛店人福药用辅料有限责任公司 | A kind of synthetic method of fatty alkyl dimethylbenzyl based quaternary ammonium salt |
| CN110754482A (en) * | 2019-10-29 | 2020-02-07 | 广西五行材料科技有限公司 | Bactericidal disinfectant for preventing avian influenza and preparation method thereof |
| CN111635663A (en) * | 2020-06-10 | 2020-09-08 | 暨南大学 | A kind of preparation method of superhydrophobic composite material |
| CN111647291A (en) * | 2020-06-10 | 2020-09-11 | 暨南大学 | Super-hydrophobic composite material and application thereof |
| CN111718614A (en) * | 2020-06-10 | 2020-09-29 | 暨南大学 | A kind of superhydrophobic composite material additive and preparation method thereof |
| CN112939789A (en) * | 2021-02-02 | 2021-06-11 | 浙江肯特催化材料科技有限公司 | Preparation method of methyl tributyl ammonium chloride |
| CN113501760A (en) * | 2021-07-16 | 2021-10-15 | 万华化学集团股份有限公司 | Low-cost synthesis method of long-carbon-chain cationic quaternary ammonium salt |
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Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN104193510A (en) * | 2014-08-19 | 2014-12-10 | 湖北富邦科技股份有限公司 | Quaternary ammonium salt anticaking agent, and preparation method and application of quaternary ammonium salt |
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