JPH0291089A - 水酸化第四級ホスホニウムの製造方法 - Google Patents
水酸化第四級ホスホニウムの製造方法Info
- Publication number
- JPH0291089A JPH0291089A JP63242373A JP24237388A JPH0291089A JP H0291089 A JPH0291089 A JP H0291089A JP 63242373 A JP63242373 A JP 63242373A JP 24237388 A JP24237388 A JP 24237388A JP H0291089 A JPH0291089 A JP H0291089A
- Authority
- JP
- Japan
- Prior art keywords
- quaternary phosphonium
- ion exchange
- column
- aqueous solution
- hydroxide
- 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.)
- Granted
Links
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical group O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 32
- 238000005342 ion exchange Methods 0.000 claims description 26
- 239000003456 ion exchange resin Substances 0.000 claims description 20
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 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 18
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 9
- 230000008929 regeneration Effects 0.000 claims description 9
- 238000011069 regeneration method Methods 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 5
- 125000005496 phosphonium group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- LIXPXSXEKKHIRR-UHFFFAOYSA-M tetraethylphosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC LIXPXSXEKKHIRR-UHFFFAOYSA-M 0.000 claims description 3
- YQJITQZWAOVOKV-UHFFFAOYSA-M C(C)OS(=O)(=O)[O-].C(C)[P+](CC)(CC)CC Chemical compound C(C)OS(=O)(=O)[O-].C(C)[P+](CC)(CC)CC YQJITQZWAOVOKV-UHFFFAOYSA-M 0.000 claims description 2
- 239000003957 anion exchange resin Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 239000012670 alkaline solution Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000000034 method Methods 0.000 description 20
- 239000002994 raw material Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- -1 polysiloxanes Polymers 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 150000004714 phosphonium salts Chemical group 0.000 description 4
- 230000001172 regenerating effect Effects 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZOMVKCHODRHQEV-UHFFFAOYSA-M tetraethylphosphanium;hydroxide Chemical compound [OH-].CC[P+](CC)(CC)CC ZOMVKCHODRHQEV-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012492 regenerant Substances 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000011001 backwashing Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 description 1
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical compound [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63242373A JPH0291089A (ja) | 1988-09-29 | 1988-09-29 | 水酸化第四級ホスホニウムの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63242373A JPH0291089A (ja) | 1988-09-29 | 1988-09-29 | 水酸化第四級ホスホニウムの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0291089A true JPH0291089A (ja) | 1990-03-30 |
| JPH0544957B2 JPH0544957B2 (enrdf_load_stackoverflow) | 1993-07-07 |
Family
ID=17088208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63242373A Granted JPH0291089A (ja) | 1988-09-29 | 1988-09-29 | 水酸化第四級ホスホニウムの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0291089A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5230220A (en) * | 1991-05-23 | 1993-07-27 | Samsung Electronics Co., Ltd. | Sterilizing/deodorizing apparatus for use in a refrigerator |
| EP1337470A4 (en) * | 2000-10-20 | 2004-11-24 | Sachem Inc | PROCESS FOR RECOVERING ONIUM HYDROXIDES FROM SOLUTIONS CONTAINING ONIUM COMPONENTS |
| JP2016128529A (ja) * | 2015-01-09 | 2016-07-14 | サンアプロ株式会社 | エポキシ樹脂硬化促進剤、および半導体封止用エポキシ樹脂組成物 |
-
1988
- 1988-09-29 JP JP63242373A patent/JPH0291089A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5230220A (en) * | 1991-05-23 | 1993-07-27 | Samsung Electronics Co., Ltd. | Sterilizing/deodorizing apparatus for use in a refrigerator |
| EP1337470A4 (en) * | 2000-10-20 | 2004-11-24 | Sachem Inc | PROCESS FOR RECOVERING ONIUM HYDROXIDES FROM SOLUTIONS CONTAINING ONIUM COMPONENTS |
| JP2016128529A (ja) * | 2015-01-09 | 2016-07-14 | サンアプロ株式会社 | エポキシ樹脂硬化促進剤、および半導体封止用エポキシ樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0544957B2 (enrdf_load_stackoverflow) | 1993-07-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4788023B2 (ja) | 液相酸化反応母液からの触媒成分の回収方法 | |
| US4560813A (en) | Processes for the production of alkylene glycol in the presence of organometalate | |
| US5466876A (en) | Process for the removal of corrosion metal contaminants from liquid compositions | |
| RU2185374C2 (ru) | Способ очистки лактамов | |
| US3941837A (en) | Method of treating an aqueous solution of acrylamide | |
| US6508940B1 (en) | Process for recovering onium hydroxides from solutions containing onium compounds | |
| JPS61501630A (ja) | メタレ−ト含有固形物を使用するアルキレングリコ−ルの製造方法 | |
| CN101475490A (zh) | 从鎓碱和鎓盐溶液中除去金属离子的方法 | |
| JPH0291089A (ja) | 水酸化第四級ホスホニウムの製造方法 | |
| JPS63153229A (ja) | 貴金属回収に有用な反応性樹脂 | |
| EP0483518B1 (de) | Verfahren zur Entfernung metallischer Korrosionsprodukte aus wasserfrei betriebenen Carbonylierungsreaktionen | |
| US2993916A (en) | Purification of ethylene oxide | |
| JPS5855233B2 (ja) | セバシン酸ジメチルエステルの製造方法 | |
| US2695875A (en) | Purification of hydrochloric acid solutions | |
| US4579983A (en) | Process for the hydrolysis of alkylene oxides using organometalates | |
| JP4397144B2 (ja) | ω−アミノアルキルスルホン酸の製造方法 | |
| US4450287A (en) | Butenyl acetate production | |
| KR100384917B1 (ko) | 트리옥산의제조방법 | |
| US4450289A (en) | Butenyl acetate production | |
| US4237317A (en) | Process for producing sebacic acid | |
| CN1980737A (zh) | 改性离子交换树脂和双酚类的制造方法 | |
| CN110124755B (zh) | 链烷酸的制造方法 | |
| JP3476226B2 (ja) | メタクリルアミド水溶液の精製方法 | |
| JPS5836680B2 (ja) | セバシン酸ジエステルの製造方法 | |
| JPH04277001A (ja) | 液状重合反応用希釈剤の回収 |