JP2007530592A5 - - Google Patents
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- Publication number
- JP2007530592A5 JP2007530592A5 JP2007505237A JP2007505237A JP2007530592A5 JP 2007530592 A5 JP2007530592 A5 JP 2007530592A5 JP 2007505237 A JP2007505237 A JP 2007505237A JP 2007505237 A JP2007505237 A JP 2007505237A JP 2007530592 A5 JP2007530592 A5 JP 2007530592A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- hydroxide
- bromide
- tetraalkylammonium
- quaternary
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 claims description 68
- -1 tetraalkylammonium bromide salt Chemical class 0.000 claims description 47
- 150000001450 anions Chemical class 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 25
- 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 claims description 22
- 239000003456 ion exchange resin Substances 0.000 claims description 22
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- 150000005621 tetraalkylammonium salts Chemical group 0.000 claims description 20
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005270 trialkylamine group Chemical group 0.000 claims description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 9
- 239000006184 cosolvent Substances 0.000 claims description 8
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims description 8
- 150000001347 alkyl bromides Chemical class 0.000 claims description 7
- 239000001569 carbon dioxide Substances 0.000 claims description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 7
- 150000005622 tetraalkylammonium hydroxides Chemical group 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- 238000005342 ion exchange Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 150000004679 hydroxides Chemical class 0.000 claims description 4
- 230000001172 regenerating effect Effects 0.000 claims description 4
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
- JIUIIWVYHWSFAZ-UHFFFAOYSA-N ac1o0v2m Chemical group O.O.O.O.O JIUIIWVYHWSFAZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical group CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- TXOJCSIIFFMREV-UHFFFAOYSA-L didecyl(dimethyl)azanium;carbonate Chemical compound [O-]C([O-])=O.CCCCCCCCCC[N+](C)(C)CCCCCCCCCC.CCCCCCCCCC[N+](C)(C)CCCCCCCCCC TXOJCSIIFFMREV-UHFFFAOYSA-L 0.000 description 3
- MVTVVKOMNZGDGD-UHFFFAOYSA-M didecyl(dimethyl)azanium;hydron;carbonate Chemical compound OC([O-])=O.CCCCCCCCCC[N+](C)(C)CCCCCCCCCC MVTVVKOMNZGDGD-UHFFFAOYSA-M 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- FAEUZVNNXJDELC-UHFFFAOYSA-M didecyl(dimethyl)azanium;hydroxide Chemical group [OH-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC FAEUZVNNXJDELC-UHFFFAOYSA-M 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical group CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000000066 reactive distillation Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- UMGXUWVIJIQANV-UHFFFAOYSA-M didecyl(dimethyl)azanium;bromide Chemical group [Br-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC UMGXUWVIJIQANV-UHFFFAOYSA-M 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55710604P | 2004-03-26 | 2004-03-26 | |
| PCT/US2005/010162 WO2005097729A2 (en) | 2004-03-26 | 2005-03-25 | Method for the synthesis of quaternary ammonium compounds and compositions thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007530592A JP2007530592A (ja) | 2007-11-01 |
| JP2007530592A5 true JP2007530592A5 (https=) | 2007-12-20 |
Family
ID=35125662
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007505238A Pending JP2007530593A (ja) | 2004-03-26 | 2005-03-25 | テトラアルキルアンモニウム塩のアニオンを交換する方法 |
| JP2007505237A Pending JP2007530592A (ja) | 2004-03-26 | 2005-03-25 | 第四級アンモニウム化合物の合成方法およびその組成物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007505238A Pending JP2007530593A (ja) | 2004-03-26 | 2005-03-25 | テトラアルキルアンモニウム塩のアニオンを交換する方法 |
Country Status (6)
| Country | Link |
|---|---|
| EP (2) | EP1730098A4 (https=) |
| JP (2) | JP2007530593A (https=) |
| CN (2) | CN1946674B (https=) |
| AU (2) | AU2005230872A1 (https=) |
| BR (2) | BRPI0509531A (https=) |
| WO (2) | WO2005097730A2 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0509531A (pt) * | 2004-03-26 | 2007-12-18 | Albemarle Corp | método de conversão de um sal de tetraalquilamÈnio de um primeiro ánion para um sal de tetraalquilamÈnio de um segundo ánion |
| US20070155840A1 (en) * | 2005-12-20 | 2007-07-05 | Albemarle Corporation | Use of quaternary ammonium compounds in the prevention of mold, mildew, and funguses in new and/or existing construction |
| US20070148431A1 (en) * | 2005-12-20 | 2007-06-28 | Albemarle Corporation | Quaternary ammonium compounds with novel mode of action for protection of wood structures |
| US20070142630A1 (en) * | 2005-12-20 | 2007-06-21 | Albemarle Corporation | Quaternary ammonium betaines for protection of wood structures |
| US20070149402A1 (en) * | 2005-12-20 | 2007-06-28 | Albemarle Corporation | Quaternary ammonium borate compositions and substrate preservative solutions containing them |
| US20070167407A1 (en) * | 2005-12-20 | 2007-07-19 | Albemarle Corporation | Quaternary ammonium borate compositions and substrate preservative solutions containing them |
| RU2313516C9 (ru) * | 2006-04-03 | 2008-03-20 | Открытое акционерное общество "Аурат" | Способ получения дидецилдиметиламмония бромида |
| WO2007127692A1 (en) * | 2006-04-28 | 2007-11-08 | Albemarle Corporation | Coatings, coating formulations, and compositions containing quaternary ammonium compounds |
| WO2008058052A1 (en) * | 2006-11-03 | 2008-05-15 | Albemarle Corporation | The use of quaternary ammonium compounds in the remediation of mold, mildew, and funguses |
| WO2008079417A2 (en) * | 2006-12-20 | 2008-07-03 | Albemarle Corporation | The use of quaternary ammonium betaines in the prevention of mold, mildew, and funguses in new and/or existing construction |
| WO2008112534A2 (en) * | 2007-03-09 | 2008-09-18 | Albemarle Corporation | The use of quaternary ammonium borates as anti-fungal, anti-mildew, anti-mold biocides for pulp and paper processing |
| KR100958876B1 (ko) | 2008-04-02 | 2010-05-20 | 삼성엔지니어링 주식회사 | 다양한 극성/비극성 용매 혼화성 이온성 액체 및 그의제조방법 |
| US8227391B2 (en) | 2008-10-17 | 2012-07-24 | Afton Chemical Corporation | Lubricating composition with good oxidative stability and reduced deposit formation |
| JP2011057936A (ja) * | 2009-09-14 | 2011-03-24 | Sony Corp | 硬化促進剤、エポキシ樹脂成型物、エポキシ樹脂系接着剤、硬化剤及び固形結晶体 |
| CN102510853A (zh) * | 2009-09-24 | 2012-06-20 | 株式会社德山 | 四烷基氢氧化铵的制造方法 |
| WO2012123411A1 (de) | 2011-03-15 | 2012-09-20 | Basf Se | Verfahren zum abreichern von säuren aus zusammensetzungen, welche ionische flüssigkeiten enthalten |
| AU2012271273B2 (en) | 2011-06-17 | 2017-06-08 | Fluidic, Inc. | Metal-air cell with ion exchange material |
| JP6235470B2 (ja) * | 2011-06-17 | 2017-11-22 | フルイディック, インク.Fluidic, Inc. | ジアルキルカーボネートの四級化を利用するヘテロイオン化合物の合成 |
| ES2702487T3 (es) | 2011-06-17 | 2019-03-01 | Nantenergy Inc | Líquido iónico que contiene iones sulfonato |
| CN103794368A (zh) * | 2012-10-29 | 2014-05-14 | 中国科学院长春应用化学研究所 | 电容器用电解质、其制备方法及不对称型电化学电容器 |
| US9287597B2 (en) | 2012-11-14 | 2016-03-15 | Fluidic, Inc. | Ionic liquid containing hydroxamate and N-alkyl sulfamate ions |
| CN105294455B (zh) * | 2015-10-09 | 2017-10-27 | 南京工业大学 | 阴离子交换制备四丁基氢氧化铵水溶液的方法 |
| WO2017137343A1 (en) * | 2016-02-11 | 2017-08-17 | Covestro Deutschland Ag | Sustainable synthesis of carbamate compounds |
| US11424484B2 (en) | 2019-01-24 | 2022-08-23 | Octet Scientific, Inc. | Zinc battery electrolyte additive |
| ES2797556B2 (es) * | 2020-09-14 | 2021-04-20 | Univ Santiago Compostela | Fluido supramolecular |
| WO2023053977A1 (ja) * | 2021-09-28 | 2023-04-06 | 富士フイルム株式会社 | 塩の製造方法、感活性光線性又は感放射線性樹脂組成物の製造方法、パターン形成方法、及び電子デバイスの製造方法 |
| CN114570307A (zh) * | 2022-03-18 | 2022-06-03 | 西安吉利电子新材料股份有限公司 | 一种从碳酸二甲酯直接生产电子级四甲基氢氧化铵制备系统及方法 |
| CN116217313A (zh) * | 2023-03-07 | 2023-06-06 | 中国工程物理研究院化工材料研究所 | 一种室温溶解富氢键材料组合溶剂的制备方法 |
| CN117567291A (zh) * | 2023-11-16 | 2024-02-20 | 中国工程物理研究院化工材料研究所 | 一种无水四正烷基氟化铵的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61170588A (ja) | 1985-01-25 | 1986-08-01 | Tama Kagaku Kogyo Kk | 水酸化第四アンモニウム水溶液の製造方法 |
| US4776929A (en) | 1986-11-25 | 1988-10-11 | Mitsubishi Gas Chemical Company, Inc. | Process for production of quaternary ammonium hydroxides |
| JPH03167160A (ja) * | 1989-11-22 | 1991-07-19 | Sumitomo Chem Co Ltd | 水酸化第四級アンモニウム水溶液の精製方法 |
| US5438034A (en) * | 1993-06-09 | 1995-08-01 | Lonza, Inc. | Quaternary ammonium carbonate compositions and preparation thereof |
| US5599990A (en) * | 1995-03-21 | 1997-02-04 | Albemarle Corporation | Process for preparing quaternary ammonium compounds |
| US5705696A (en) * | 1996-08-01 | 1998-01-06 | General Electric Company | Extractive method for the preparation of quaternary salts |
| DE19644997C1 (de) * | 1996-10-30 | 1997-12-04 | Schuetz Dishman Biotech Pvt Lt | Verfahren zur Herstellung von hochreinen, kurzkettig alkylierten, quartären Ammoniumhydroxiden und ihre Verwendung zur Herstellung von Zeolithen oder als Phasen-Transfer-Katalysator |
| US6586632B2 (en) * | 2001-03-28 | 2003-07-01 | Cognis Corporation | Preparation of quaternary ammonium compounds |
| KR100516044B1 (ko) * | 2002-08-01 | 2005-09-26 | 김홍두 | 계면활성제형 고분자 겔 및 이를 이용한 이온성 또는수용성 물질의 용해 및 분리 방법 |
| JP4300407B2 (ja) * | 2003-04-11 | 2009-07-22 | 三菱瓦斯化学株式会社 | 水酸化テトラアルキルアンモニウムの製造方法 |
| BRPI0509531A (pt) * | 2004-03-26 | 2007-12-18 | Albemarle Corp | método de conversão de um sal de tetraalquilamÈnio de um primeiro ánion para um sal de tetraalquilamÈnio de um segundo ánion |
-
2005
- 2005-03-25 BR BRPI0509531-0A patent/BRPI0509531A/pt not_active IP Right Cessation
- 2005-03-25 AU AU2005230872A patent/AU2005230872A1/en not_active Withdrawn
- 2005-03-25 CN CN2005800133125A patent/CN1946674B/zh not_active Expired - Fee Related
- 2005-03-25 WO PCT/US2005/010168 patent/WO2005097730A2/en not_active Ceased
- 2005-03-25 EP EP05731237A patent/EP1730098A4/en not_active Withdrawn
- 2005-03-25 AU AU2005230871A patent/AU2005230871A1/en not_active Abandoned
- 2005-03-25 CN CNA2005800133040A patent/CN1946673A/zh active Pending
- 2005-03-25 JP JP2007505238A patent/JP2007530593A/ja active Pending
- 2005-03-25 JP JP2007505237A patent/JP2007530592A/ja active Pending
- 2005-03-25 BR BRPI0509546-8A patent/BRPI0509546A/pt not_active Application Discontinuation
- 2005-03-25 WO PCT/US2005/010162 patent/WO2005097729A2/en not_active Ceased
- 2005-03-25 EP EP05729187.4A patent/EP1732878B1/en not_active Expired - Lifetime
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