AT405462B - Verfahren zur bestimmung eines alkaliions - Google Patents
Verfahren zur bestimmung eines alkaliions Download PDFInfo
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- AT405462B AT405462B AT0093097A AT93097A AT405462B AT 405462 B AT405462 B AT 405462B AT 0093097 A AT0093097 A AT 0093097A AT 93097 A AT93097 A AT 93097A AT 405462 B AT405462 B AT 405462B
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- 238000000034 method Methods 0.000 title claims description 23
- 239000002739 cryptand Substances 0.000 claims description 40
- 150000003983 crown ethers Chemical class 0.000 claims description 39
- 230000000236 ionophoric effect Effects 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 25
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 claims description 22
- 150000002500 ions Chemical class 0.000 claims description 18
- 238000004020 luminiscence type Methods 0.000 claims description 17
- 239000003513 alkali Substances 0.000 claims description 15
- 239000002555 ionophore Substances 0.000 claims description 14
- 229910001415 sodium ion Inorganic materials 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 9
- 238000010168 coupling process Methods 0.000 claims description 9
- 238000005859 coupling reaction Methods 0.000 claims description 9
- 229910001414 potassium ion Inorganic materials 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000000872 buffer Substances 0.000 claims description 4
- 229910001416 lithium ion Inorganic materials 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 240000008168 Ficus benjamina Species 0.000 claims 1
- 240000001973 Ficus microcarpa Species 0.000 claims 1
- 229910019213 POCl3 Inorganic materials 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 239000000047 product Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- -1 Aryl nitrogen Chemical compound 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 235000015320 potassium carbonate Nutrition 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- BJUOQSZSDIHZNP-UHFFFAOYSA-N 1,4,7,10-tetraoxa-13-azacyclopentadecane Chemical compound C1COCCOCCOCCOCCN1 BJUOQSZSDIHZNP-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- HCSXGHIWQVZBJK-UHFFFAOYSA-N 4-aminobenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)C3=C2C1=CC=C3N HCSXGHIWQVZBJK-UHFFFAOYSA-N 0.000 description 4
- PFNUDUPCMCKPRD-UHFFFAOYSA-N 6-chlorobenzo[de]isoquinoline-1,3-dione Chemical class O=C1NC(=O)C2=CC=CC3=C2C1=CC=C3Cl PFNUDUPCMCKPRD-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000017 hydrogel Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- UNJDMWQMPZNWOT-UHFFFAOYSA-N 2-(2-aminophenoxy)ethanol Chemical compound NC1=CC=CC=C1OCCO UNJDMWQMPZNWOT-UHFFFAOYSA-N 0.000 description 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- NHFJDXPINIIUQG-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 NHFJDXPINIIUQG-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XSXGXXVKGKLHRM-UHFFFAOYSA-N 2-(2-ethoxyethoxymethyl)propanedioyl dichloride Chemical compound CCOCCOCC(C(Cl)=O)C(Cl)=O XSXGXXVKGKLHRM-UHFFFAOYSA-N 0.000 description 2
- LGCYTDJJYLJYOB-UHFFFAOYSA-N 2-(2-nitrophenoxy)ethanol Chemical compound OCCOC1=CC=CC=C1[N+]([O-])=O LGCYTDJJYLJYOB-UHFFFAOYSA-N 0.000 description 2
- CZQAYLCRCDCHMQ-UHFFFAOYSA-N 2-(ethoxymethyl)propanedioyl dichloride Chemical compound CCOCC(C(Cl)=O)C(Cl)=O CZQAYLCRCDCHMQ-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 2
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- AESFGSJWSUZRGW-UHFFFAOYSA-N (3,4-diacetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=C(OC(C)=O)C(OC(C)=O)=C1 AESFGSJWSUZRGW-UHFFFAOYSA-N 0.000 description 1
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 1
- GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 1
- LECMBPWEOVZHKN-UHFFFAOYSA-N 2-(2-chloroethoxy)ethanol Chemical compound OCCOCCCl LECMBPWEOVZHKN-UHFFFAOYSA-N 0.000 description 1
- CWDMDQXDGXFQFX-UHFFFAOYSA-N 2-(2-methoxyanilino)ethanol Chemical compound COC1=CC=CC=C1NCCO CWDMDQXDGXFQFX-UHFFFAOYSA-N 0.000 description 1
- IJEGLZCNYJZMRH-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)anilino]ethoxy]ethanol Chemical compound OCCOCCNC1=CC=CC=C1OCCO IJEGLZCNYJZMRH-UHFFFAOYSA-N 0.000 description 1
- AWOPBKCLTDTTKZ-UHFFFAOYSA-N 2-[[2-(ethylamino)ethylamino]methyl]propanedioyl dichloride Chemical compound CCNCCNCC(C(Cl)=O)C(Cl)=O AWOPBKCLTDTTKZ-UHFFFAOYSA-N 0.000 description 1
- 125000006012 2-chloroethoxy group Chemical group 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 1
- UJEUBSWHCGDJQU-UHFFFAOYSA-N 4-chloro-1,8-naphthalic anhydride Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3Cl UJEUBSWHCGDJQU-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- JAXYGFPHFDPRKW-UHFFFAOYSA-N OS(=O)(=O)Cc1ccccc1.OS(=O)(=O)Cc1ccccc1.Cc1ccc(cc1)S(=O)(=O)N(CCO)CCO Chemical compound OS(=O)(=O)Cc1ccccc1.OS(=O)(=O)Cc1ccccc1.Cc1ccc(cc1)S(=O)(=O)N(CCO)CCO JAXYGFPHFDPRKW-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 101150050048 SNCB gene Proteins 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QCTBMLYLENLHLA-UHFFFAOYSA-N aminomethylbenzoic acid Chemical compound NCC1=CC=C(C(O)=O)C=C1 QCTBMLYLENLHLA-UHFFFAOYSA-N 0.000 description 1
- 229960003375 aminomethylbenzoic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 239000003269 fluorescent indicator Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-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
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
- G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0093097A AT405462B (de) | 1997-05-30 | 1997-05-30 | Verfahren zur bestimmung eines alkaliions |
| US09/085,807 US6124135A (en) | 1997-05-30 | 1998-05-27 | Method of determining an alkali ion |
| US09/085,218 US5952491A (en) | 1997-05-30 | 1998-05-27 | Method of determining an alkali ion |
| EP98890164A EP0881487B1 (de) | 1997-05-30 | 1998-05-28 | Verfahren zur Bestimmung eines Alkaliions |
| EP98890165A EP0881488A3 (de) | 1997-05-30 | 1998-05-28 | Verfahren zur Bestimmung eines Alkaliions |
| DE59814098T DE59814098D1 (de) | 1997-05-30 | 1998-05-28 | Verfahren zur Bestimmung eines Alkaliions |
| JP10151737A JPH10332591A (ja) | 1997-05-30 | 1998-06-01 | アルカリイオンの定量方法およびジアザ−クリプタンド |
| JP15173898A JP4065053B2 (ja) | 1997-05-30 | 1998-06-01 | アルカリイオンの定量方法およびモノアザ−クラウンエーテル |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0093097A AT405462B (de) | 1997-05-30 | 1997-05-30 | Verfahren zur bestimmung eines alkaliions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA93097A ATA93097A (de) | 1998-12-15 |
| AT405462B true AT405462B (de) | 1999-08-25 |
Family
ID=3503128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0093097A AT405462B (de) | 1997-05-30 | 1997-05-30 | Verfahren zur bestimmung eines alkaliions |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6124135A (cg-RX-API-DMAC7.html) |
| EP (2) | EP0881487B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JPH10332591A (cg-RX-API-DMAC7.html) |
| AT (1) | AT405462B (cg-RX-API-DMAC7.html) |
| DE (1) | DE59814098D1 (cg-RX-API-DMAC7.html) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6211359B1 (en) | 1999-08-17 | 2001-04-03 | Avl Medical Instruments | Triaza-cryptand and method of determining an alkali ion |
| US6673352B1 (en) * | 1999-09-14 | 2004-01-06 | The General Hospital Corporation | Use of Mullerian inhibiting substance for treating excess androgen states |
| US7579463B2 (en) | 2000-12-20 | 2009-08-25 | Life Technologies Corporation | Crown ether derivatives |
| US6962992B2 (en) * | 2000-12-20 | 2005-11-08 | Molecullar Probes, Inc. | Crown ether derivatives |
| US7129346B2 (en) * | 2000-12-20 | 2006-10-31 | Molecular Probes, Inc. | Crown ether derivatives |
| AT410601B (de) * | 2000-12-29 | 2003-06-25 | Hoffmann La Roche | Sensor zur lumineszenz-optischen bestimmung eines analyten sowie reagens, das nach dem fret-prinzip arbeitet |
| US20030211011A1 (en) * | 2001-06-08 | 2003-11-13 | Phillips Terry E. | Ph sensor system and method for using same |
| US7229835B2 (en) * | 2001-10-25 | 2007-06-12 | The University Of Maryland, Baltimore County | Amine detection method and materials |
| US20050118603A1 (en) * | 2002-10-11 | 2005-06-02 | Ahram Biosystems Inc. | Target detection system having a conformationally sensitive probe comprising a nucleic acid based signal transducer |
| JP4310616B2 (ja) * | 2002-10-16 | 2009-08-12 | 泰三 山本 | 扁平錠剤の外観検査機 |
| US20040175821A1 (en) * | 2003-03-07 | 2004-09-09 | Ehman Michael F. | Integrated photodetector for heavy metals and biological activity analysis |
| WO2006023231A2 (en) | 2004-07-27 | 2006-03-02 | Molecular Probes, Inc. | Fluorescent metal ion indicators with large stokes shift |
| US20060121547A1 (en) * | 2004-12-03 | 2006-06-08 | Mcintire Mark | Diffusion layer for an enzyme-based sensor application |
| US8097725B2 (en) * | 2004-12-03 | 2012-01-17 | Roche Diagnostics Operations, Inc. | Luminescent indicator dye and optical sensor |
| RU2288289C1 (ru) * | 2005-04-11 | 2006-11-27 | Российская Федерация, от имени которой выступает государственный заказчик Федеральное агентство по атомной энергии | Способ количественного определения лития в сплаве |
| WO2007131054A2 (en) * | 2006-05-03 | 2007-11-15 | Opti Medical Systems | Chromoionophore and method of determining sodium ions |
| US8158259B2 (en) * | 2006-12-08 | 2012-04-17 | Opti Medical Systems | Spreading layer and humidity control layer for enhancing sensor performance |
| EP2683714B1 (en) | 2011-03-09 | 2019-01-09 | Universität Potsdam | Ii (pi)-conjugated fluoroionophores and method for determining an alkali ion |
| WO2013090407A2 (en) | 2011-12-12 | 2013-06-20 | Step Ahead Innovations, Inc. | Aquatic environment monitoring and dosing systems and apparatuses, and methods and software relating thereto |
| US9360474B2 (en) | 2012-11-29 | 2016-06-07 | Opti Medical Systems, Inc. | Multi-layer device for selectively determining magnesium ion |
| US8874063B2 (en) | 2013-03-08 | 2014-10-28 | Qualcomm Incorporated | Simultaneous signal receiver with interspersed frequency allocation |
| US9784686B2 (en) | 2013-06-19 | 2017-10-10 | Step Ahead Innovations, Inc. | Aquatic environment water parameter testing systems and methods |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8528804D0 (en) * | 1985-11-22 | 1985-12-24 | Amersham Int Plc | Compounds |
| US5162525A (en) * | 1987-07-31 | 1992-11-10 | Allied-Signal Inc. | Fluorogenic and chromogenic three-dimensional ionophores as selective reagents for detecting ions in biological fluids |
| US4774339A (en) * | 1987-08-10 | 1988-09-27 | Molecular Probes, Inc. | Chemically reactive dipyrrometheneboron difluoride dyes |
| EP0369733B1 (en) * | 1988-11-14 | 1996-02-21 | The Regents Of The University Of California | Fluorescent indicator dyes for alkali metal cations, their preparation and use |
| US5474743A (en) * | 1993-10-21 | 1995-12-12 | Minnesota Mining And Manufacturing Company | Cation-sensing composite structure and compounds for use therein |
| US5516911A (en) * | 1993-12-30 | 1996-05-14 | The United States Of America As Represented By The Department Of Health And Human Services | Fluorescent intracellular calcium indicators |
| AT405461B (de) * | 1997-05-30 | 1999-08-25 | Avl List Gmbh | Lumineszenzindikator |
-
1997
- 1997-05-30 AT AT0093097A patent/AT405462B/de not_active IP Right Cessation
-
1998
- 1998-05-27 US US09/085,807 patent/US6124135A/en not_active Expired - Lifetime
- 1998-05-27 US US09/085,218 patent/US5952491A/en not_active Expired - Lifetime
- 1998-05-28 EP EP98890164A patent/EP0881487B1/de not_active Expired - Lifetime
- 1998-05-28 DE DE59814098T patent/DE59814098D1/de not_active Expired - Lifetime
- 1998-05-28 EP EP98890165A patent/EP0881488A3/de not_active Withdrawn
- 1998-06-01 JP JP10151737A patent/JPH10332591A/ja active Pending
- 1998-06-01 JP JP15173898A patent/JP4065053B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0881487B1 (de) | 2007-09-26 |
| DE59814098D1 (de) | 2007-11-08 |
| EP0881487A9 (de) | 2002-08-07 |
| US6124135A (en) | 2000-09-26 |
| US5952491A (en) | 1999-09-14 |
| JPH10332591A (ja) | 1998-12-18 |
| JPH1114545A (ja) | 1999-01-22 |
| EP0881487A3 (de) | 1999-12-29 |
| EP0881488A2 (de) | 1998-12-02 |
| JP4065053B2 (ja) | 2008-03-19 |
| ATA93097A (de) | 1998-12-15 |
| EP0881488A3 (de) | 1999-12-29 |
| EP0881487A2 (de) | 1998-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EIH | Change in the person of patent owner | ||
| MM01 | Lapse because of not paying annual fees |
Effective date: 20121215 |