JPH0533225B2 - - Google Patents
Info
- Publication number
- JPH0533225B2 JPH0533225B2 JP59032971A JP3297184A JPH0533225B2 JP H0533225 B2 JPH0533225 B2 JP H0533225B2 JP 59032971 A JP59032971 A JP 59032971A JP 3297184 A JP3297184 A JP 3297184A JP H0533225 B2 JPH0533225 B2 JP H0533225B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- solution
- resin
- water
- formula
- 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 - Lifetime
Links
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 22
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000013522 chelant Substances 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- -1 more specifically Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
【発明の詳細な説明】
本発明は新規なチアジアゾール誘導体、更に詳
しくは、式（）
（式中M1及びM2は各々独立してアルカリ金属
原子（但し、ナトリウム原子は除く）またはアル
カリ土類金属原子を意味する。）で示される５−
メルカプト−３−スルホフエニル−２−チオ−
１，３，４−チアジアゾール及びその塩に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel thiadiazole derivatives, more specifically, compounds of the formula () (In the formula, M 1 and M 2 each independently mean an alkali metal atom (however, excluding a sodium atom) or an alkaline earth metal atom.)
Mercapto-3-sulfophenyl-2-thio-
This invention relates to 1,3,4-thiadiazole and its salts.
本発明の式（）の化合物はキレート化剤とし
て極めて有用な化合物である。例えば、式（）
の化合物は各種金属イオン、例えばAg（），Al
（），As（），Bi（），Cd（），Co（），Cu
（），Fe（），Hg（），Ni（），Pb（），Pd
（），Sb（），Se（），Sn（），Te（）など
と反応し、キレート化合物を形成する。 The compound of formula () of the present invention is an extremely useful compound as a chelating agent. For example, the expression ()
The compound contains various metal ions, such as Ag(), Al
(), As(), Bi(), Cd(), Co(), Cu
(), Fe (), Hg (), Ni (), Pb (), Pd
(), Sb (), Se (), Sn (), Te (), etc. to form chelate compounds.
更に述べれば、本発明の化合物（）はスルホ
ン酸基を有しているため水にきわめて溶け易く、
かつ重金属イオンやSe（）などとの反応速度が
大きい。このことは化合物（）を単に水溶液と
して用いる場合に有利であるばかりでなく、アニ
オン交換樹脂上に固定化して用いる場合に特に有
利である。即ち、化合物（）はイオン交換反応
と物理吸着により樹脂上に固定されるので、その
調製に要する時間は短かく、かつ固定化された化
合物（）は例えば0.5M程度の食塩溶液のよう
な電解質溶液中でも安定に樹脂に担持され、その
担持樹脂は広いPH範囲でキレート生成樹脂として
機能する。従つて化合物（）担持アニオン交換
樹脂を調製後、前記重金属イオンなどとキレート
化合物を形成させることができる。また化合物
（）の水溶液と重金属イオンならびにSe（）
などと反応させたのちにその生成物をアニオン交
換樹脂に吸着、捕集することもできる。従つて公
害関連の重金属イオンやSe（）の除去やそれら
の環境試料、生体試料中の分析に必要な前濃縮、
銀などの有価元素の回収にきわめて有用である。 Furthermore, since the compound () of the present invention has a sulfonic acid group, it is extremely soluble in water;
It also has a high reaction rate with heavy metal ions and Se(). This is not only advantageous when the compound () is used simply as an aqueous solution, but also particularly advantageous when it is used immobilized on an anion exchange resin. In other words, the compound () is immobilized on the resin by ion exchange reaction and physical adsorption, so the time required for its preparation is short, and the immobilized compound () can be mixed with an electrolyte such as a 0.5M salt solution. It is stably supported on a resin even in solution, and the supported resin functions as a chelate-forming resin over a wide pH range. Therefore, after preparing the anion exchange resin supporting the compound (), a chelate compound can be formed with the heavy metal ions and the like. Also, an aqueous solution of the compound () and heavy metal ions as well as Se ()
The product can also be adsorbed and collected on an anion exchange resin after reacting with the like. Therefore, the preconcentration necessary for the removal of pollution-related heavy metal ions and Se () and their analysis in environmental samples and biological samples,
It is extremely useful for recovering valuable elements such as silver.
以上記した如く、本発明化合物はキレート化剤
として有用な化合物であるが、その優れたキレー
ト化能とともに従来の近縁化学構造を有する物
質、即ち、５−メルカプト−３−フエニル−２−
チオ−１，３，４−チアジアゾールのカリウム塩
と比べても下記の点で特徴を有するものである。 As described above, the compound of the present invention is a compound useful as a chelating agent, but in addition to its excellent chelating ability, it is also a substance having a related chemical structure, that is, 5-mercapto-3-phenyl-2-
Compared to the potassium salt of thio-1,3,4-thiadiazole, it has the following characteristics.
即ち、前記公知化合物と金属イオンとのキレー
ト化合物は酸性溶液中で不安定であり、酸性条件
下で分解し、イオウを脱離し易く、その場合錯生
成能を失なう。また、その酸化成績体であるジス
ルフイド体は水に不溶性で分析への応用に不都合
である。 That is, chelate compounds of the above-mentioned known compounds and metal ions are unstable in acidic solutions, decompose under acidic conditions, and tend to eliminate sulfur, in which case they lose their ability to form complexes. In addition, its oxidized product, disulfide, is insoluble in water and is inconvenient for analytical applications.
一方、本発明の式（）の化合物によるキレー
ト体はかかる欠陥がない。本発明の化合物を製す
るには、フエニルヒドラチンスルホン酸を水酸化
アルカリ、例えば苛性ソーダ、苛性カリ等の水溶
液に溶解した溶液に二硫化炭素を加え加熱還流す
ればほぼ定量的収率にて目的物が得られる。 On the other hand, the chelate of the compound of formula () of the present invention does not have such defects. To produce the compound of the present invention, carbon disulfide is added to a solution of phenylhydratine sulfonic acid dissolved in an aqueous solution of an alkali hydroxide, such as caustic soda or caustic potash, and the mixture is heated to reflux. You can get things.
以下実施例及び試験例で本発明を説明する。 The present invention will be explained below with reference to Examples and Test Examples.
実施例
フエニルヒドラチン−４−スルホン酸５ｇ及び
水酸化カリウム（85％）８ｇを水100mlに溶解し
た後、二硫化炭素20ｇを加えて80℃水浴中で７時
間還流加熱する。反応後、未反応の二硫化炭素を
除去し、減圧にて濃縮乾固する。残渣をメタノー
ルまたはメタノールと２−プロパノール混液から
再結して５−メルカプト−３−（４−スルホフエ
ニル）−２−チオ−１，３，４−チアジアゾール
の２カリウム塩（以下化合物と略称す）が得ら
れる。さらに再結晶を行ない、110〜120℃にて
P2O5上真空乾燥すれば淡黄色微針状晶７ｇが得
られた。（融点約270℃（分解））
元素分析値 C8H4N2O3S4K2
理論値 C25.12％，H1.05％，N7.32％
実験値 C25.14％，H1.18％，N7.43％
化合物１のスペクトルデータ
・ 紫外部吸収スペクトル（水溶液）：224nm
（18800），265nm（11500），339nm（9200）。（ ）
は分子吸光度を示す。Example 5 g of phenylhydratin-4-sulfonic acid and 8 g of potassium hydroxide (85%) are dissolved in 100 ml of water, and then 20 g of carbon disulfide is added and heated under reflux in a water bath at 80° C. for 7 hours. After the reaction, unreacted carbon disulfide is removed and the mixture is concentrated to dryness under reduced pressure. The residue was reconsolidated from methanol or a mixture of methanol and 2-propanol to obtain the dipotassium salt of 5-mercapto-3-(4-sulfophenyl)-2-thio-1,3,4-thiadiazole (hereinafter abbreviated as the compound). can get. Further recrystallization is performed at 110-120℃.
Vacuum drying over P 2 O 5 gave 7 g of pale yellow microacicular crystals. (Melting point approximately 270℃ (decomposition)) Elemental analysis value C 8 H 4 N 2 O 3 S 4 K 2 Theoretical value C25.12%, H1.05%, N7.32% Experimental value C25.14%, H1.18 %, N7.43% Spectral data of compound 1 Ultraviolet absorption spectrum (aqueous solution): 224 nm
(18800), 265nm (11500), 339nm (9200). ( )
indicates molecular absorbance.
・ プロトンNMR（重水中）：7.56p.p.m.シング
レツト（フエニルプロトン４個分）
・ IRスペクトル（KBr錠剤）：1200，1045cm-1
試験例１ （ジスムチオールスルホン酸カリウ
ム担持樹脂の調製法）
アンバーライトIRA400（100〜200メツシユ）５
ｇを化合物410.78mg、精製水20mlよりなる溶液
に加え、約２時間振り混ぜ、濾取、乾燥すると化
合物担持樹脂（0.2ｍmole／ｇ）が得られる。・ Proton NMR (in heavy water): 7.56 ppm singlet (4 phenyl protons) ・ IR spectrum (KBr tablet): 1200, 1045 cm -1 Test Example 1 (Preparation method of potassium dismuthiolsulfonate supported resin) Amberlite IRA400 (100-200 mesh) 5
g is added to a solution consisting of 410.78 mg of the compound and 20 ml of purified water, shaken for about 2 hours, filtered, and dried to obtain a compound-supported resin (0.2 mmole/g).
試験例 ２
Cu2+，Cd2+またはHg2+（各々0.1ｍmole）を含
む水溶液１にそれぞれ化合物0.15ｍmoleを
加え、10分間攪拌後濾過し、濾液中のCu2+，
Cd2+またはHg2+をそれぞれ原子吸光法で測定し
て除去率を求めた結果、Cu2+，Cd2+またはHg2+
は100％除去されていることを確認した。Test Example 2 0.15 mmole of each compound was added to aqueous solution 1 containing Cu 2+ , Cd 2+ or Hg 2+ (0.1 mmole each), stirred for 10 minutes, filtered, and Cu 2+ in the filtrate,
As a result of measuring Cd 2+ or Hg 2+ by atomic absorption spectrometry and determining the removal rate, Cu 2+ , Cd 2+ or Hg 2+
confirmed that it was 100% removed.
試験例 ３
チオ硫酸ナトリウム５水晶248ｇ、亜硫酸ナト
リウム15ｇを水に溶解して１とした溶液Ａを調
製する。本溶液10mlに水30ml、硝酸銀１ｍmole
含有溶液10mlを加え、写真処理モデル廃液50mlを
調製した。Test Example 3 Prepare solution A by dissolving 248 g of sodium thiosulfate 5 crystals and 15 g of sodium sulfite in water. 10ml of this solution, 30ml of water, 1mmole of silver nitrate
10 ml of the containing solution was added to prepare 50 ml of photographic processing model waste liquid.
化合物1.5ｍmole／ｇ担持樹脂100mgをこの
モデル廃液50mlに加え、室温で１時間振り混ぜ、
上澄液中の銀濃度を原子吸光法によつて測定後、
除去率を求めると97.0％であつた。 Add 100 mg of compound 1.5 mmole/g supported resin to 50 ml of this model waste solution, shake and mix at room temperature for 1 hour.
After measuring the silver concentration in the supernatant liquid by atomic absorption method,
The removal rate was 97.0%.
試験例 ４
SeO3 -2１ｍmole含有溶液（HCl酸性）10mlを
化合物１ｍmole／ｇ担持樹脂５ｇ充填カラム
を通過させ（所要時間約10分）、カラムを水洗後
その水洗液を先の通過液と合併してその中のSe
濃度を原子吸光法によつて測定後除去率を求める
と97％であつた。Test Example 4 10 ml of a solution containing 1 mmole of SeO 3 -2 (acidic HCl) was passed through a column packed with 5 g of resin supporting 1 mmole/g of the compound (about 10 minutes), and after washing the column with water, the washing liquid was combined with the previous passing liquid. and Se in it
After measuring the concentration by atomic absorption spectrometry, the removal rate was found to be 97%.
Claims (1)
原子（但し、ナトリウム原子は除く）またはアル
カリ土類金属原子を意味する。）で示される１，
３，４−チアジアゾール誘導体。[Claims] 1 formula (In the formula, M 1 and M 2 each independently mean an alkali metal atom (however, excluding a sodium atom) or an alkaline earth metal atom.) 1,
3,4-thiadiazole derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59032971A JPS60178871A (en) | 1984-02-23 | 1984-02-23 | Thiadiazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59032971A JPS60178871A (en) | 1984-02-23 | 1984-02-23 | Thiadiazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60178871A JPS60178871A (en) | 1985-09-12 |
| JPH0533225B2 true JPH0533225B2 (en) | 1993-05-19 |
Family
ID=12373783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59032971A Granted JPS60178871A (en) | 1984-02-23 | 1984-02-23 | Thiadiazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60178871A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610483A (en) * | 2015-02-05 | 2015-05-13 | 浙江工商大学 | Preparation method of chelating functional resin with selective adsorption to Hg(II) |
-
1984
- 1984-02-23 JP JP59032971A patent/JPS60178871A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS=1966 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60178871A (en) | 1985-09-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Giandomenico et al. | Carboxylation of kinetically inert platinum (IV) hydroxy complexes. An entr. acte. ee into orally active platinum (IV) antitumor agents | |
| KR100400085B1 (en) | Water- and organic-soluble cucurbituril derivatives, their preparation methods, their separation methods and uses | |
| US8101084B2 (en) | Perchlorate ion trapping agent | |
| US4497737A (en) | Metal cage complexes and production thereof | |
| JP4091135B2 (en) | Process for producing substituted 3- (phenylimino) -3H-phenothiazines and phenoxazines | |
| RU2345085C2 (en) | Oxaliplatin with low content of accompanying admixtures and method of obtaining it | |
| JPH0533225B2 (en) | ||
| Hadjiliadis et al. | Complexes of mercury (II) with thiamine | |
| Qureshi et al. | Synthesis, ion-exchange behaviour and composition of tin (IV) hexacyanoferrate (II) | |
| Chan et al. | 178. Preparation and properties of cyanobisethylenediaminecobalt (III) complexes, and the role of cyanide as a substituting agent | |
| US4076745A (en) | Process for calcium salts α-ketocarboxylic acids | |
| JP2007512318A (en) | Platinum (II) complex and process and use of the complex | |
| US4025523A (en) | Cyclic tetra-oxyethylene complexes with ionic compounds | |
| Hansen Jr et al. | The thioalkoxyalkylation of sulfides and other nucleophiles | |
| Gowda et al. | Determination of thiosemicarbazide alone and in its metal complexes with arylhalosulfonamides | |
| Fischer et al. | Syntheses of cellulose exchangers carrying chelating anchor groups for selective separation of uranyl ions | |
| DeMember et al. | Silver (I) chemistry in aqueous alkaline media. 2. Study of the interaction of silver (I) with. beta.-disulfone carbanions in aqueous alkaline media | |
| JPH0675673B2 (en) | Uranium adsorbent | |
| Bottomley et al. | Electrophilic behaviour of co-ordinated nitrogen mono-oxide: preparation and reactions of halogenonitrosylbis [o-phenylenebis (dimethylarsine)] osmium complexes | |
| JPH1112664A (en) | Noble metal separating and recovering agent | |
| Mikhailov | Mild template synthesis in the ternary system Co (II)-dithiooxamide-acetone in gelatin-immobilized Co 2 [Fe (CN) 6] matrix implantates | |
| Bhattacharyya et al. | Reductive nitrosylation of tetraoxometallates—XI. Molybdate hydroxylamine reaction in the presence of cyanide: Synthesis of mono-and dinitrosyl cyan | |
| JPS6236969B2 (en) | ||
| GB2108106A (en) | Novel macrocyclic compounds and salts thereof useful for dissolving barium sulphate scale | |
| Gowda et al. | Sodium N-chloro-p-nitrobenzenesulfonamide (chloramine-N) as a new redox titrant: I. The status of chloramine-N as a titrimetric reagent |