CN105294455A - Method for preparing aqueous tetrabutylammonium hydroxide solvent by anion exchange - Google Patents
Method for preparing aqueous tetrabutylammonium hydroxide solvent by anion exchange Download PDFInfo
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- CN105294455A CN105294455A CN201510649824.6A CN201510649824A CN105294455A CN 105294455 A CN105294455 A CN 105294455A CN 201510649824 A CN201510649824 A CN 201510649824A CN 105294455 A CN105294455 A CN 105294455A
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- 238000000034 method Methods 0.000 title claims abstract description 86
- 239000002904 solvent Substances 0.000 title claims abstract description 9
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 title claims abstract 10
- 238000005349 anion exchange Methods 0.000 title abstract description 6
- 239000011347 resin Substances 0.000 claims abstract description 84
- 229920005989 resin Polymers 0.000 claims abstract description 84
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000005342 ion exchange Methods 0.000 claims abstract description 10
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 51
- 230000008569 process Effects 0.000 claims description 43
- 239000007864 aqueous solution Substances 0.000 claims description 35
- 239000012530 fluid Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 19
- 239000008367 deionised water Substances 0.000 claims description 17
- 229910021641 deionized water Inorganic materials 0.000 claims description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 6
- 238000002203 pretreatment Methods 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- 101710134784 Agnoprotein Proteins 0.000 claims description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 3
- 238000003556 assay Methods 0.000 claims description 3
- 230000004907 flux Effects 0.000 claims description 2
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 230000001105 regulatory effect Effects 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000008929 regeneration Effects 0.000 abstract 1
- 238000011069 regeneration method Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 241001550224 Apha Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Treatment Of Water By Ion Exchange (AREA)
Abstract
The invention relates to a method for preparing an aqueous tetrabutylammonium hydroxide solvent by anion exchange. Firstly, strongly alkaline anion exchange resin is loaded into an ion exchange column with an external circulation apparatus, and is completely changed into an OH-type by pretreatment; then, flow is regulated, an aqueous tetrabutylammonium bromide solvent is filled into the exchange column to carry out an exchange reaction with the resin, meanwhile, the temperature of the exchange reaction is regulated by external circulation, and after the reaction, the aqueous tetrabutylammonium hydroxide solvent is obtained. The invention breaks through the technique for preparing the aqueous tetrabutylammonium hydroxide solvent with the mass concentration of 25 to 30 percent by an anion resin exchange method, the resin can be recycled by regeneration, the method greatly reduces the production cost in comparison with an electrolytic method, the energy consumption is little, no pollution is generated, and the method is a green, low-carbon, environment-friendly and economic preparation method.
Description
Technical field
The present invention relates to a kind of method that the TBAH aqueous solution is prepared in anionresin.
Background technology
TBAH (TBAOH) is a kind of organic alkali, is commonly used for stratographic analysis agent, electronic industry washing composition, phase-transfer catalyst, tensio-active agent, template etc.Wherein high-purity TBAH is mainly used for cleaning and the corrosion of chip, and its purity and cleanliness factor have very important impact to the yield rate of unicircuit, electrical property and reliability.TBAH, as stratographic analysis agent, has purposes very widely at industry, scientific research field.Its ammonium salt, namely 4-butyl ammonium have efficiently, the feature such as low toxicity, be commonly used for sterilant, be widely used in industries such as medicine, health.The production method of this product mainly contains following several: 1, silver suboxide method; 2, electrolytic process; 3, potassium hydroxide method; 4, the ion exchange method of strongly basic anion exchange resin and Tetrabutyl amonium bromide; 5, organic acid TBuA salt brine solution Current Decomposition method; 6, ionic membrane method.Can find that in silver suboxide method, electrolytic process and potassium hydroxide method, foreign ion is difficult to remove through contrast, stock Product separating difficulty is large, the shortcomings such as equipment cost and production cost height; Organic acid TBuA salt brine solution Current Decomposition method equipment cost and energy consumption cost high; Ionic membrane method exchange velocity is slow, and exchange efficiency is low, cannot meet the requirement that industrial production obtains large-tonnage product; The ion exchange method of strongly basic anion exchange resin and Tetrabutyl amonium bromide is cheap, low for equipment requirements, and technique is simple, workable.At present, what the production of China's TBAH mainly adopted is membrane electrolysis, although the method product purity is high, energy consumption is high.
Summary of the invention
The object of the invention is to increase product purity and content, cost-saving, reduce energy consumption, and provide a kind of anionresin to prepare the method for the TBAH aqueous solution.
Technical scheme of the present invention is: the method for the TBAH aqueous solution is prepared in anionresin, concrete preparation process is as follows: first, strongly basic anion exchange resin is filled in the ion exchange column with external circulating device, convert OH to completely through pre-treatment
-type; Then, tetrabutyl phosphonium bromide aqueous ammonium passes in exchange column by adjust flux, carries out permutoid reaction with resin, regulates permutoid reaction temperature simultaneously, namely obtain the TBAH aqueous solution of mass concentration 25%-30% after reaction by outer circulation.Ion exchange resin can regenerate through NaOH solution, recycles.
The model of preferred described anionite-exchange resin is the one in 201*4 type, 201*7 type, D290 type or D210 type.
Preferably above-mentioned strongly basic anion exchange resin pretreatment process is:
(1) with 2 ~ 3 times of resin volumes, temperature 20 ~ 50 DEG C, mass concentration is the NaCl aqueous solution process resin of 1% ~ 15%, and being washed till fluid through deionized water is colourless solution;
(2) with 2 ~ 3 times of resin volumes, mass concentration be 0.5 ~ 5% the NaOH aqueous solution continue to process the resin that process through step (1), being washed till fluid through deionized water is neutrality;
(3) with 0.5 ~ 1 times of resin volume, mass concentration be 0.5% ~ 4% solvent continue to process the resin that process through step (2), being washed till fluid through deionized water is neutrality;
(4) through 1 ~ 2 times of resin volume, mass concentration is the resin that the process of 1% ~ 10%HCl aqueous solution processed through step (3), is washed to fluid neutrality;
(5) by temperature 20 ~ 50 DEG C, mass concentration be 2% ~ 15% the NaOH aqueous solution continue to process the resin processed through step (4), convert OH to completely to resin
-type; Again washed resin to fluid through AgNO
3without precipitation after aqueous assay; Stand-by after resin centrifugal removing surface-bonded water.
Solvent described in preferred steps (3) is the one in S-WAT, EDTA or tartrate.
The mass concentration of preferably described tetrabutyl phosphonium bromide aqueous ammonium is 25 ~ 55%.
Preferred permutoid reaction temperature is 15 ~ 40 DEG C.The feed rate of preferred Tetrabutyl amonium bromide is 0.1L/h ~ 10L/h.
Beneficial effect:
The product TBAH aqueous solution of the present invention by analysis mass concentration can reach 25% ~ 30%, and bromide ion concentration is less than or equal to 500ppm, and liquid colourity is less than 20 (APHA).Can meet the technical need in market, ion exchange technique of the present invention can improve economic benefit and the social benefit of enterprise, overcomes the many disadvantages of other preparation methods, have simple to operate, security is high, equipment requirements is low, and pollution-free, the advantages such as environmental protection.
Embodiment
Below by embodiment, illustrate outstanding feature of the present invention and marked improvement further, be only this patent is described and does not limit this patent.
[example 1] anionite-exchange resin pretreatment process
Select 201*4 type strongly basic anion exchange resin, its pretreatment process divides five steps, is specially:
(1) with 2 times of resin volumes, temperature T
0be 50 DEG C, mass concentration is 1%NaCl aqueous solution process resin, and being washed till fluid through deionized water is colourless solution.
(2) with 3 times of resin volumes, the NaOH aqueous solution of mass concentration 0.5% continues the above-mentioned resin of process, is washed till fluid for neutral (pH is 7) through deionized water.
(3) with 0.5 times of resin volume, the sodium sulfite aqueous solution of mass concentration 0.5% continues the above-mentioned resin of process, is washed till fluid for neutral (pH is 7) through deionized water.
(4) through 2 times of resin volumes, the above-mentioned resin of mass concentration 5%HCl aqueous solution process, is washed to fluid neutrality (pH is 7).
(5) temperature T is used
1be 20 DEG C, mass concentration is the above-mentioned resin of NaOH aqueous solution continuation process of 15%, converts OH to completely to resin
-type.Again washed resin to fluid through AgNO
3without precipitation after aqueous assay.Stand-by after resin centrifugal removing surface-bonded water.
[example 2] anionite-exchange resin pretreatment process
Select 201*7 type strongly basic anion exchange resin, its pretreatment process divides five steps, is specially:
(1) with 3 times of resin volumes, temperature T
0be 20 DEG C, mass concentration is 15%NaCl aqueous solution process resin, and being washed till fluid through deionized water is colourless solution.
(2) with 2 times of resin volumes, mass concentration is the above-mentioned resin of NaOH aqueous solution continuation process of 1%, is washed till fluid for neutral through deionized water.
(3) with 1 times of resin volume, the EDTA of mass concentration 1% continues the above-mentioned resin of process, is washed till fluid for neutral through deionized water.
(4) through 1 times of resin volume, mass concentration is the above-mentioned resin of HCl solution-treated of 10%, is washed to fluid neutrality.
(5) temperature T is used
1be 50 DEG C, mass concentration is the above-mentioned resin of NaOH continuation process of 2%, converts OH to completely to resin
-type.Be washed to fluid through 2mol/LAgNO
3without precipitation after solution detects.Stand-by after resin centrifugal removing surface-bonded water.
[example 3] anionite-exchange resin pretreatment process
Select D290 type strongly basic anion exchange resin, its pretreatment process divides five steps, is specially:
(1) with 2 times of resin volumes, temperature T
0be 30 DEG C, mass concentration is the NaCl aqueous solution process resin of 8%, and being washed till fluid through deionized water is colourless solution.
(2) with 2 times of resin volumes, mass concentration is the above-mentioned resin of NaOH aqueous solution continuation process of 5%, is washed till fluid for neutral through deionized water.
(3) with 0.7 times of resin volume, mass concentration is the above-mentioned resin of tartrate continuation process of 4%, is washed till fluid for neutral through deionized water.
(4) through 2 times of resin volumes, mass concentration is the above-mentioned resin of HCl solution-treated of 1%, is washed to fluid neutrality.
(5) temperature T is used
1be 30 DEG C, mass concentration is the above-mentioned resin of NaOH continuation process of 7%, converts OH to completely to resin
-type.Be washed to fluid through 2mol/LAgNO
3without precipitation after solution detects.Stand-by after resin centrifugal removing surface-bonded water.
[example 4] anionite-exchange resin pretreatment process
Select D210 type strongly basic anion exchange resin, its pretreatment process divides five steps, is specially:
(1) with 3 times of resin volumes, 40 DEG C of mass concentrations are 10%NaCl aqueous solution process resin, and being washed till fluid through deionized water is colourless solution.
(2) with 3 times of resin volumes, mass concentration is the above-mentioned resin of NaOH aqueous solution continuation process of 3%, is washed till fluid for neutral through deionized water.
(3) with 0.6 times of resin volume, mass concentration is the above-mentioned resin of tartrate continuation process of 3%, is washed to fluid neutrality.
(4) through 2 times of resin volumes, mass concentration is the above-mentioned resin of HCl solution-treated of 8%, is washed to fluid neutrality.
(5) temperature T is used
1be 40 DEG C, mass concentration is the above-mentioned resin of NaOH continuation process of 12%, converts OH to completely to resin
-type.Be washed to fluid through 2mol/LAgNO
3without precipitation after solution detects.Stand-by after resin centrifugal removing surface-bonded water.
[example 5] anion exchange method prepares the method for the TBAH aqueous solution
Fill in the ion exchange column with external circulating device by 201*4 type strongly basic anion exchange resin, the method pre-treatment through [example 1] converts OH to completely
-type.Then, pass in exchange column with the tetrabutyl phosphonium bromide aqueous ammonium that mass concentration is 25% by the flow of 10L/h, can obtain the TBAH aqueous solution after carrying out permutoid reaction with resin at 15 DEG C, this identified as samples is designated as Y1.Sample technical indicator analytical results is as table 1.Ion exchange resin can regenerate through NaOH solution, recycles.
[example 6] anion exchange method prepares the method for the TBAH aqueous solution
Filled in by strongly basic anion exchange resin in the ion exchange column with external circulating device, the method pre-treatment respectively through [example 1], [example 2], [example 3], [example 4] converts OH to completely
-type.Then, pass in exchange column with the tetrabutyl phosphonium bromide aqueous ammonium that mass concentration is 45% by the flow of 5L/h, after carrying out permutoid reaction with resin at 30 DEG C, the TBAH aqueous solution can be obtained.Gained sample is labeled as Y2 respectively, Y3, Y4, Y5.Sample technical indicator analytical results is as table 1.Ion exchange resin can regenerate through NaOH solution, recycles.
[example 7] anion exchange method prepares the method for the TBAH aqueous solution
Fill in the ion exchange column with external circulating device by 201*7 type strongly basic anion exchange resin, the method pre-treatment through [example 2] converts OH to completely
-type.Then, pass in exchange column with the tetrabutyl phosphonium bromide aqueous ammonium that mass concentration is 35% by the flow of 1L/h, can obtain the TBAH aqueous solution after carrying out permutoid reaction with resin at 40 DEG C, gained sample is labeled as Y6 respectively.Sample technical indicator analytical results is as table 1.Ion exchange resin can regenerate through NaOH solution, recycles.
[example 8] anion exchange method prepares the method for the TBAH aqueous solution
Fill in the ion exchange column with external circulating device by D290 type strongly basic anion exchange resin, the method pre-treatment through [example 3] converts OH to completely
-type.Then, pass in exchange column with the tetrabutyl phosphonium bromide aqueous ammonium that mass concentration is 55% by the flow of 0.5L/h, can obtain the TBAH aqueous solution after carrying out permutoid reaction with resin at 25 DEG C, gained sample is labeled as Y7 respectively.Sample technical indicator analytical results is as table 1.Ion exchange resin can regenerate through NaOH solution, recycles.
The common technology index of table 1 each sample
| Sample number into spectrum | Y1 | Y2 | Y3 | Y4 | Y5 | Y6 | Y7 |
| Colourity (APHA) | 12 | 10 | 11 | 13 | 10 | 9 | 10 |
| Content (%) | 26.12 | 25.46 | 28.78 | 27.51 | 25.48 | 29.83 | 27.21 |
| Bromide anion (ppm) | 398 | 260 | 220 | 150 | 50 | 80 | 110 |
Claims (7)
1. the method for the TBAH aqueous solution is prepared in anionresin, and concrete preparation process is as follows: first, is filled in by strongly basic anion exchange resin in the ion exchange column with external circulating device, converts OH to completely through pre-treatment
-type; Then, tetrabutyl phosphonium bromide aqueous ammonium passes in exchange column by adjust flux, carries out permutoid reaction with resin, regulates permutoid reaction temperature simultaneously, namely obtain the TBAH aqueous solution of mass concentration 25%-30% after reaction by outer circulation.
2. method according to claim 1, is characterized in that the model of described anionite-exchange resin is the one in 201*4 type, 201*7 type, D290 type or D210 type.
3. method according to claim 1, is characterized in that described strongly basic anion exchange resin pretreatment process is:
(1) with 2 ~ 3 times of resin volumes, temperature 20 ~ 50 DEG C, mass concentration is the NaCl aqueous solution process resin of 1% ~ 15%, and being washed till fluid through deionized water is colourless solution;
(2) with 2 ~ 3 times of resin volumes, mass concentration be 0.5 ~ 5% the NaOH aqueous solution continue to process the resin that process through step (1), being washed till fluid through deionized water is neutrality;
(3) with 0.5 ~ 1 times of resin volume, mass concentration be 0.5% ~ 4% solvent continue to process the resin that process through step (2), being washed till fluid through deionized water is neutrality;
(4) through 1 ~ 2 times of resin volume, mass concentration is the resin that the process of 1% ~ 10%HCl aqueous solution processed through step (3), is washed to fluid neutrality;
(5) by temperature 20 ~ 50 DEG C, mass concentration be 2% ~ 15% the NaOH aqueous solution continue to process the resin processed through step (4), convert OH to completely to resin
-type; Again washed resin to fluid through AgNO
3without precipitation after aqueous assay; Stand-by after resin centrifugal removing surface-bonded water.
4. method according to claim 3, is characterized in that solvent described in step (3) is the one in S-WAT, EDTA or tartrate.
5. method according to claim 1, is characterized in that the mass concentration of described tetrabutyl phosphonium bromide aqueous ammonium is 25 ~ 55%.
6. method according to claim 1, is characterized in that permutoid reaction temperature is 15 ~ 40 DEG C.
7. method according to claim 1, is characterized in that the feed rate of Tetrabutyl amonium bromide is 0.1L/h ~ 10L/h.
Priority Applications (1)
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|---|---|---|---|
| CN201510649824.6A CN105294455B (en) | 2015-10-09 | 2015-10-09 | The method that anion exchange prepares the TBAH aqueous solution |
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|---|---|---|---|
| CN201510649824.6A CN105294455B (en) | 2015-10-09 | 2015-10-09 | The method that anion exchange prepares the TBAH aqueous solution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105294455A true CN105294455A (en) | 2016-02-03 |
| CN105294455B CN105294455B (en) | 2017-10-27 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111635303A (en) * | 2020-06-03 | 2020-09-08 | 辽宁大学 | Double-acid ionic liquid and preparation method and application thereof |
| CN114085164A (en) * | 2021-11-30 | 2022-02-25 | 上海应用技术大学 | Method for preparing hydroxypropionitrile by catalyzing acrylonitrile by adopting strongly basic ion exchange resin |
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| CN1347872A (en) * | 2000-10-11 | 2002-05-08 | 中国石化集团长岭炼油化工有限责任公司 | Prepn of tetraethyl ammonium hydroxide |
| CN1946673A (en) * | 2004-03-26 | 2007-04-11 | 雅宝公司 | Method of exchanging anions of tetraalkylammonium salts |
| CN102030665A (en) * | 2009-09-28 | 2011-04-27 | 天津市化学试剂研究所 | Method for preparing tetrabutylammonium hydroxide |
| CN102120589A (en) * | 2010-12-30 | 2011-07-13 | 中国天辰工程有限公司 | S-1 full-silicon molecular sieve and preparation method thereof as well as application of S-1 full-silicon molecular sieve in caprolactam preparation |
| JP2012030208A (en) * | 2010-08-03 | 2012-02-16 | Tokuyama Corp | Method for producing tetraalkylammonium salt aqueous solution |
| CN102510853A (en) * | 2009-09-24 | 2012-06-20 | 株式会社德山 | Process for production of tetraalkylammonium hydroxide |
| CN104278288A (en) * | 2014-09-30 | 2015-01-14 | 赵文洲 | Method for preparing high-purity tetrabutyl ammonium hydroxide by continuous electrolysis |
-
2015
- 2015-10-09 CN CN201510649824.6A patent/CN105294455B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1347872A (en) * | 2000-10-11 | 2002-05-08 | 中国石化集团长岭炼油化工有限责任公司 | Prepn of tetraethyl ammonium hydroxide |
| CN1946673A (en) * | 2004-03-26 | 2007-04-11 | 雅宝公司 | Method of exchanging anions of tetraalkylammonium salts |
| CN102510853A (en) * | 2009-09-24 | 2012-06-20 | 株式会社德山 | Process for production of tetraalkylammonium hydroxide |
| CN102030665A (en) * | 2009-09-28 | 2011-04-27 | 天津市化学试剂研究所 | Method for preparing tetrabutylammonium hydroxide |
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| CN104278288A (en) * | 2014-09-30 | 2015-01-14 | 赵文洲 | Method for preparing high-purity tetrabutyl ammonium hydroxide by continuous electrolysis |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111635303A (en) * | 2020-06-03 | 2020-09-08 | 辽宁大学 | Double-acid ionic liquid and preparation method and application thereof |
| CN114085164A (en) * | 2021-11-30 | 2022-02-25 | 上海应用技术大学 | Method for preparing hydroxypropionitrile by catalyzing acrylonitrile by adopting strongly basic ion exchange resin |
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| Publication number | Publication date |
|---|---|
| CN105294455B (en) | 2017-10-27 |
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