JPH0149352B2 - - Google Patents
Info
- Publication number
- JPH0149352B2 JPH0149352B2 JP59059035A JP5903584A JPH0149352B2 JP H0149352 B2 JPH0149352 B2 JP H0149352B2 JP 59059035 A JP59059035 A JP 59059035A JP 5903584 A JP5903584 A JP 5903584A JP H0149352 B2 JPH0149352 B2 JP H0149352B2
- Authority
- JP
- Japan
- Prior art keywords
- crown
- substituted
- formula
- ions
- lithium ion
- 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.)
- Expired
Links
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 38
- 229910001416 lithium ion Inorganic materials 0.000 claims description 38
- 239000012528 membrane Substances 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 11
- 239000004800 polyvinyl chloride Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 9
- 150000003987 14-crown-4 derivatives Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229920002379 silicone rubber Polymers 0.000 claims description 4
- 239000004945 silicone rubber Substances 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- -1 ammonium ions Chemical class 0.000 description 28
- 150000002500 ions Chemical class 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 12
- 239000004014 plasticizer Substances 0.000 description 11
- 229910001415 sodium ion Inorganic materials 0.000 description 10
- FFNGVBGKKHTWMS-UHFFFAOYSA-N 2-dodecyl-2-methylpropane-1,3-diol Chemical compound CCCCCCCCCCCCC(C)(CO)CO FFNGVBGKKHTWMS-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- UZINTXLDYLUUJS-UHFFFAOYSA-N 2,5,9,12-tetraoxabicyclo[11.4.0]heptadeca-1(17),13,15-triene Chemical compound O1CCOCCCOCCOC2=CC=CC=C21 UZINTXLDYLUUJS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000003983 crown ethers Chemical class 0.000 description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 4
- 229910001414 potassium ion Inorganic materials 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NBQXYAJLUDQSNV-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1CN1C(=O)CC(C(O)=O)C1 NBQXYAJLUDQSNV-UHFFFAOYSA-N 0.000 description 3
- SVJYFWHFQPBIOY-UHFFFAOYSA-N 7,8,16,17-tetrahydro-6h,15h-dibenzo[b,i][1,4,8,11]tetraoxacyclotetradecine Chemical compound O1CCCOC2=CC=CC=C2OCCCOC2=CC=CC=C21 SVJYFWHFQPBIOY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002452 interceptive effect Effects 0.000 description 3
- OAJNZFCPJVBYHB-UHFFFAOYSA-N 2,5,8,11-tetraoxabicyclo[10.4.0]hexadeca-1(16),12,14-triene Chemical compound O1CCOCCOCCOC2=CC=CC=C21 OAJNZFCPJVBYHB-UHFFFAOYSA-N 0.000 description 2
- YBTDSZAHFSIJBW-UHFFFAOYSA-N 2-dodecylpropane-1,3-diol Chemical compound CCCCCCCCCCCCC(CO)CO YBTDSZAHFSIJBW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 2
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- IOQSSIPMPIYMDF-UHFFFAOYSA-N 1,3-diethoxypropane Chemical compound CCOCCCOCC IOQSSIPMPIYMDF-UHFFFAOYSA-N 0.000 description 1
- PVDDBYSFGBWICV-UHFFFAOYSA-N 1,4,8,11-tetraoxacyclotetradecane Chemical class C1COCCOCCCOCCOC1 PVDDBYSFGBWICV-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- NFPNQEAEXIXGNY-UHFFFAOYSA-N 2,2-dioctylpropane-1,3-diol Chemical compound CCCCCCCCC(CO)(CO)CCCCCCCC NFPNQEAEXIXGNY-UHFFFAOYSA-N 0.000 description 1
- BXEQXVMQIWFRPR-UHFFFAOYSA-N 2-methyl-2-octylpropane-1,3-diol Chemical compound CCCCCCCCC(C)(CO)CO BXEQXVMQIWFRPR-UHFFFAOYSA-N 0.000 description 1
- HUHIKZFEXLRXRB-UHFFFAOYSA-N 2-octadecylpropane-1,3-diol Chemical compound CCCCCCCCCCCCCCCCCCC(CO)CO HUHIKZFEXLRXRB-UHFFFAOYSA-N 0.000 description 1
- ZZJCWGKTESNSGK-UHFFFAOYSA-N 2-octylpropane-1,3-diol Chemical compound CCCCCCCCC(CO)CO ZZJCWGKTESNSGK-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XPSAAFFCAJIBSC-UHFFFAOYSA-M lithium;2,4,6-trinitrophenolate Chemical compound [Li+].[O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O XPSAAFFCAJIBSC-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- UGJRMHXEWBBMMN-UHFFFAOYSA-N pentadecane-1,3-diol Chemical compound CCCCCCCCCCCCC(O)CCO UGJRMHXEWBBMMN-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 1
- CSFUNXXUTSRHPN-UHFFFAOYSA-N undecane-1,3-diol Chemical compound CCCCCCCCC(O)CCO CSFUNXXUTSRHPN-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59059035A JPS60202875A (ja) | 1984-03-26 | 1984-03-26 | アルキル置換１４−クラウン−４誘導体とその用途 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59059035A JPS60202875A (ja) | 1984-03-26 | 1984-03-26 | アルキル置換１４−クラウン−４誘導体とその用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60202875A JPS60202875A (ja) | 1985-10-14 |
| JPH0149352B2 true JPH0149352B2 (enrdf_load_stackoverflow) | 1989-10-24 |
Family
ID=13101632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59059035A Granted JPS60202875A (ja) | 1984-03-26 | 1984-03-26 | アルキル置換１４−クラウン−４誘導体とその用途 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60202875A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5132436A (en) * | 1991-05-28 | 1992-07-21 | Eastman Kodak Company | Intermediates for making 14-crown-4-ether derivatives |
| US7105095B2 (en) * | 2003-04-17 | 2006-09-12 | Organo Corporation | Method and apparatus for controlling concentration of water treatment chemicals |
-
1984
- 1984-03-26 JP JP59059035A patent/JPS60202875A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60202875A (ja) | 1985-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |