SU1051094A1 - Triethyl(nonamethylcyclopentasiloxymethylene) ammonium iodide as electrode-active compound for iodide-selective membranes - Google Patents
Triethyl(nonamethylcyclopentasiloxymethylene) ammonium iodide as electrode-active compound for iodide-selective membranes Download PDFInfo
- Publication number
- SU1051094A1 SU1051094A1 SU823460666A SU3460666A SU1051094A1 SU 1051094 A1 SU1051094 A1 SU 1051094A1 SU 823460666 A SU823460666 A SU 823460666A SU 3460666 A SU3460666 A SU 3460666A SU 1051094 A1 SU1051094 A1 SU 1051094A1
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- SU
- USSR - Soviet Union
- Prior art keywords
- iodide
- selective membranes
- active compound
- electrode
- nonamethylcyclopentasiloxymethylene
- Prior art date
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- 239000012528 membrane Substances 0.000 title claims abstract description 15
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 title claims abstract description 9
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 title description 3
- 229940107816 ammonium iodide Drugs 0.000 title description 3
- 150000003839 salts Chemical class 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical class [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 diethylamine chlorine hydrate Chemical compound 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Abstract
Триэтилнонаметилциклопентасилоксиметиленаммоний йодид формулы в качестве электродноактивного соединени дл иодид-с.елективных мембран .Triethylnonamethylcyclopentasyloxymethylammonium iodide of the formula as an electrode active compound for iodide-selective membranes.
Description
соwith
4 Изобретение относитс к новым химическим соединени м, в частности соли кремнийсодержащёго четвертичного аммониевого основани , а именн триэтилнонаметилциклопентасилоксиметилен аммоний Яодиду формулы который может примен тьс в качестве электродноактивного срединени дл иодид-селективных мембран в ана литической химии. Известны электродноактивные соед нени (ЭАС) дл иодид-селективных мембран, которые представл ют собой схэли четвертичных аммониевых f| ил фосфониевых 2 оснований. Наиболее близким к предлагаемому по.строению и свойствам вл етс трикаприлметиламмонийиодид з . Однако иодид-селективные мембран изготовленные на его основе, облада ют невысокой селективностью к таким анионам, как S0|, С1, Вг, МО, что ограничивает их применение дл авал за растворов сложного солевого сост ва. Цель изобретени - синтез соедине ниЯр используемого дл получени иодид-селективных мембран с повышен ной селективностью. Поставленна цель достигаетс использованием триэтилнонаметилциклопентасилоксиметиленаммоний иодида формулы I в качестве электродноактивного соединени дл иодид-селективных мембран. Синтез указанного соединени про вод т путем взаимодействи хлордека метилциклопентаоилоксана с диэтилакотном ,при 50с с последующей обработкой полученного кремнийсодержа щего амина йодистым-зтилом. Получение триэтилнонаметилциклопвнтасилоксиметиленаммоний иодида . Смесь 40,45 г (0,1 моль) С40 HjijO Sl CI и 18,5 г (0,25 моль) диэтиламина переманивают 30 ч при . ОбразуквдИйс осадок хлор гидрата диэтиламина удал ют по мере накоплени . По окончании реакции отгон ют избыток дизтиламина, а затем при пониженном давлении кремнийсодержащий амин (CjH5)5N(C,o Н79 ) {т.кип.125 С при 9 мм Нд ). К 4,41 г (0,01 моль) выделенного кремнийсодержащего амина приливают 1,56 г (0,01 моль)иодистого этила. Реакци быстро протекает при комнатной температуре. : Полученную четвертичную соль ( ) ( Н 0 S ij- )N 3 очищают двойной перекристаллизацией из спирта . Т.пл. очищенной соли не определен - вещество разлагаетс при Т - 280°С. В ИК-спектрах соли идентифицируют характеристические полосы, отвечающие колебани м св зей в силоксановом цикле, см 1075()S i-0-S i);. 1гб5( S i (СН),); 81ф5(СН)5 , а также полосы, соответствующие колебани м св зей в этильных радикалах . Состав полученного соединени подтверждс1етс результатами элементного анализа.Найдено , вес.%: С 32,20, Н 7,44, Si 23,42, N 2,33. Вычислено, вес.%: С 32,44, Н 7,42, Si 23,49, N 2,34. Жидка мембрана представл ет собой 510.М раствор полученной соли в пол рном органическом растворителе в данном случае в О-нитротолуоле. Определение коэффициентов селективности провод т при посто нной активности мешсшщих ионов и переменной определ емых ионов. В качестве фоновых электролитов используют 10 М водные растворы солей типа NaAn, гд Ап - мешающий анион, т.е. S04 ; Ct ; В г ; NOj, Изменени мембранных потенциалов провод т в электрохимической чейке вида: Pt, Hg Hci2S04 Жидка мембрана на приборе рН-121. Растворы термостатируют при 20+0,. Коэффициенты селективности вычисл ютс по формуле: ь/« , где - активность мацающего аниона (фоновый электролит, М)f a-j - активность J/ HOHOB в точке перегиба функции. Чем ниже значение коэффициента селективности, тем меньше вли ние оказывают посторонние анионы па работу мембраны и тем выше селективность мембраны. В таблице приведены характеристики иодид-селективных мембран на основе предлагаемой соли кремнийсоержащего четвертичного аммониевогоосновани формулы 1 из известного трикаприлметиламлюний иодиа f 3J . Коэффициенты селективМембрана „ „ нести к .анионам На t/CHO J -CJi-L Bj:l - L. 104 1 2;о.1(И5дГ1 а,.1о|5 g Ii3j l0 l,,0jltf4, Как видно из таблицы, соединение 1 существенно повышает селективность иодидных мембран и делает их пригодными дл анализа растворов ;.. содержа:цих одновременно S0, ci , Вг ( JO,4 The invention relates to new chemical compounds, in particular salts of silicon-containing quaternary ammonium base, and specifically triethylnonamethyl cyclopentasyloxy ammonium ammonium formula which can be used as an electrode active center for iodide selective membranes in analytical chemistry. Electroactive compounds (EAS) are known for iodide selective membranes which are quaternary ammonium shells f | silt phosphonium 2 bases. Closest to the proposed structure and properties is tricaprylmethylammonium iodide. However, iodide-selective membranes made on its basis have a low selectivity for such anions as S0 |, C1, Br, MO, which limits their use for avalanges for solutions of complex salt composition. The purpose of the invention is to synthesize the compound used to produce iodide-selective membranes with increased selectivity. This goal is achieved by using triethylnonamethylcyclopentasyloxymethylene ammonium iodide of the formula I as the electrode active compound for iodide selective membranes. The synthesis of this compound was carried out by reacting chlorodec methylcyclopentaoyloxane with diethyl carcinoma, at 50 ° C, followed by treating the resulting silicon-containing amine with ethyl itilide. Preparation of triethylnonamethylcyclopvntasyloxymethylene ammonium iodide. A mixture of 40.45 g (0.1 mol) of C40 HjijO Sl CI and 18.5 g (0.25 mol) of diethylamine was entangled for 30 h at. The precipitate of diethylamine chlorine hydrate is removed as it accumulates. At the end of the reaction, the excess dithylamine is distilled off, and then the silicon-containing amine (CjH5) 5N (C, o H79) {bp.125 C at 9 mm Nd) under reduced pressure. 1.56 g (0.01 mol) of ethyl iodide are added to 4.41 g (0.01 mol) of the isolated silicon-containing amine. The reaction proceeds rapidly at room temperature. : The obtained quaternary salt () (Н 0 S ij-) N 3 is purified by double recrystallization from alcohol. M.p. no purified salt is determined - the substance decomposes at T = 280 ° C. In the IR spectra of salts, characteristic bands corresponding to the vibrations of bonds in the siloxane cycle are identified, see 1075 () S i-0-S i) ;. 1gb5 (Si (CH),); 81f5 (CH) 5, as well as bands corresponding to vibrations of bonds in ethyl radicals. The composition of the obtained compound is confirmed by the results of elemental analysis. Found, wt.%: C 32.20, H 7.44, Si 23.42, N 2.33. Calculated, wt.%: C 32.44, H 7.42, Si 23.49, N 2.34. The liquid membrane is 510.M solution of the obtained salt in a polar organic solvent in this case in O-nitrotoluene. The determination of the selectivity coefficients is carried out at a constant activity of the mixing ions and a variable of the detected ions. As background electrolytes, 10 M aqueous solutions of NaAn type salts are used, where An is an interfering anion, i.e. S04; Ct; In g; NOj, Changes in membrane potentials are carried out in an electrochemical cell of the form: Pt, Hg Hci2S04 Liquid membrane on a pH 121 device. Solutions thermostatic at 20 + 0 ,. The selectivity coefficients are calculated according to the formula: L / ", where is the activity of the scorching anion (background electrolyte, M) f a-j is the activity of J / HOHOB at the inflection point of the function. The lower the value of the selectivity coefficient, the less the influence of extraneous anions on the membrane operation and the higher the selectivity of the membrane. The table shows the characteristics of iodide-selective membranes based on the proposed silicon-containing quaternary ammonium salt of the formula 1 of the known tricaprylmethyl aluminum iodine f 3J. Selectivity coefficientsMembrane „„ carry to .anions On t / CHO J –CJi-L Bj: l - L. 104 1 2; a.1 (I5dG1 a, .1о | 5 g Ii3j l0 l ,, 0jltf4, As can be seen from the table , compound 1 significantly increases the selectivity of iodide membranes and makes them suitable for the analysis of solutions; .. containing: cx simultaneously S0, ci, Br (JO,
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU823460666A SU1051094A1 (en) | 1982-06-29 | 1982-06-29 | Triethyl(nonamethylcyclopentasiloxymethylene) ammonium iodide as electrode-active compound for iodide-selective membranes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU823460666A SU1051094A1 (en) | 1982-06-29 | 1982-06-29 | Triethyl(nonamethylcyclopentasiloxymethylene) ammonium iodide as electrode-active compound for iodide-selective membranes |
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| Publication Number | Publication Date |
|---|---|
| SU1051094A1 true SU1051094A1 (en) | 1983-10-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| SU823460666A SU1051094A1 (en) | 1982-06-29 | 1982-06-29 | Triethyl(nonamethylcyclopentasiloxymethylene) ammonium iodide as electrode-active compound for iodide-selective membranes |
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| SU (1) | SU1051094A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2123006C1 (en) * | 1994-11-17 | 1998-12-10 | Л'Ореаль | Diorganosiloxane or triorganosilane derivatives, cosmetic composition for protection from uv-radiation and a method of skin and/or hair protection from uv-radiation |
| RU2126010C1 (en) * | 1994-11-17 | 1999-02-10 | Л'Ореаль | New di- and triorganosiloxanes, light-protection cosmetic composition, and method of protecting skin and/or hair against uv radiation |
-
1982
- 1982-06-29 SU SU823460666A patent/SU1051094A1/en active
Non-Patent Citations (1)
| Title |
|---|
| 1. Грекович А.Л. и др. Специфичный к иодидным ионам электрод на основе жидкого ионообменника. Электрохими , 1971, т. 7, с. 436. 2. Сырчеиков А.Я. и др. Разработка и исследование селективных мембранных электродов. - журнал аналитической химии, 1974, т. 29, с. 584. 3.Coetjee С.;) . ,Frei ser H.Lignidlignid membrane electrodes.based on ./Jonassoci at i on extraction systems.. Chem. 1969, 41, p. 1128. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2123006C1 (en) * | 1994-11-17 | 1998-12-10 | Л'Ореаль | Diorganosiloxane or triorganosilane derivatives, cosmetic composition for protection from uv-radiation and a method of skin and/or hair protection from uv-radiation |
| RU2126010C1 (en) * | 1994-11-17 | 1999-02-10 | Л'Ореаль | New di- and triorganosiloxanes, light-protection cosmetic composition, and method of protecting skin and/or hair against uv radiation |
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