JPH0541629B2 - - Google Patents
Info
- Publication number
- JPH0541629B2 JPH0541629B2 JP63277633A JP27763388A JPH0541629B2 JP H0541629 B2 JPH0541629 B2 JP H0541629B2 JP 63277633 A JP63277633 A JP 63277633A JP 27763388 A JP27763388 A JP 27763388A JP H0541629 B2 JPH0541629 B2 JP H0541629B2
- Authority
- JP
- Japan
- Prior art keywords
- arene
- water
- silver
- tetrahydrofuran
- compound
- 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
- 238000000605 extraction Methods 0.000 claims description 9
- -1 silver ions Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052709 silver Inorganic materials 0.000 claims description 7
- 239000004332 silver Substances 0.000 claims description 7
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 150000003983 crown ethers Chemical class 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 2
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 241001120493 Arene Species 0.000 description 1
- 241001164374 Calyx Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- MMYYTPYDNCIFJU-UHFFFAOYSA-N calix[6]arene Chemical compound C1C(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC2=CC=CC1=C2 MMYYTPYDNCIFJU-UHFFFAOYSA-N 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 230000006210 debutylation Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- UKJFVOWPUXSBOM-UHFFFAOYSA-N hexane;oxolane Chemical compound C1CCOC1.CCCCCC UKJFVOWPUXSBOM-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、銀イオン抽出法に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a silver ion extraction method.
地球環境の保護、資源の効率的利用のため、重
金属イオン類の回収が急務となつている。
In order to protect the global environment and use resources efficiently, recovery of heavy metal ions has become an urgent need.
従来の金属イオン抽出剤としては、四級アンモ
ニウム塩、クラウンエーテル類が公知である。 As conventional metal ion extractants, quaternary ammonium salts and crown ethers are known.
しかし、四級アンモニウム塩は、高価であると
ともに選択性がない。一方、クラウンエーテル類
は高価であるとともに毒性が強い等の欠点があ
る。 However, quaternary ammonium salts are expensive and lack selectivity. On the other hand, crown ethers have drawbacks such as being expensive and highly toxic.
その他金属イオン吸着剤として、イオン交換樹
脂、キレート樹脂等もあるが、選択性に劣るとと
もに高価である。 Other metal ion adsorbents include ion exchange resins and chelate resins, but these have poor selectivity and are expensive.
本発明は、このような事情に鑑みて、安価で銀
イオンを選択的に回収できる新規な銀イオン抽出
法を提供することを目的としている。
In view of these circumstances, the present invention aims to provide a novel silver ion extraction method that can selectively recover silver ions at low cost.
カリツクスアレーンは、杯（カリツクス）に似
た構造の芳香族炭化水素（アレーン）であること
から、Gutscheによつて命名された化合物で、骨
格をなす芳香環の数(n)によつてカリツクス［ｎ］
アレーンと呼ばれ、パラ置換フエノールとホルマ
リンの縮合によつて得られる化合物で原料が安価
で反応も一段階で環サイズの異なるものが得られ
る。
Calyxarene is a compound named by Gutsche because it is an aromatic hydrocarbon (arene) with a structure similar to a calyx. [n]
It is called an arene, and is a compound obtained by condensation of para-substituted phenol and formalin.Its raw materials are inexpensive, and compounds with different ring sizes can be obtained in one step.
これらカリツクスアレーン類は、シクロデキス
トリンやクラウンエーテルにまさる環状ホスト分
子として注目され、人工酵素としての可能性が示
唆されている（C.D.Gutsche，Top.Curr.Chem.，
123，１（1984））。また、水溶性を付与したカリツ
クスアレーン−Ｐ−スルホン酸の水溶性ホスト化
合物の合成がある（特開昭61−83156）。さらに、
耐熱性に優れた重金属イオンの選択的吸着剤とし
て有効なＰ−フエニルカリツクスアレーン類の合
成がある（特開昭59−104331、特開昭59−
104332、特開昭59−104333）。 These calytuxarenes have attracted attention as cyclic host molecules superior to cyclodextrins and crown ethers, and their potential as artificial enzymes has been suggested (CDGutsche, Top.Curr.Chem.,
123, 1 (1984)). There is also the synthesis of a water-soluble host compound of calixarene-P-sulfonic acid that has been imparted with water solubility (Japanese Patent Laid-Open No. 61-83156). moreover,
There is a synthesis of P-phenylcalixarenes which are effective as selective adsorbents for heavy metal ions with excellent heat resistance (Japanese Patent Application Laid-open No. 104331-1989,
104332, Japanese Unexamined Patent Publication No. 59-104333).
本発明の発明者等は、カリツクスアレーンとア
ゾ化合物の重金属イオンに対する鎖体形成能力に
着目し、アゾ基を有するカリツクスアレーンを重
金属イオンの選択的抽出剤として用いることがで
きないかと考え、鋭意検討を行つた結果この発明
を完成するに到つた。 The inventors of the present invention focused on the ability of calixarene and azo compounds to form a chain with heavy metal ions, and thought that calixarene having an azo group could be used as a selective extractant for heavy metal ions. As a result of our studies, we have completed this invention.
したがつて、本発明にかかる銀イオン抽出法
は、水溶液中から銀イオンを抽出するにあたり、
下記式
の化合物を抽出剤として用いることを特徴として
いる。 Therefore, in the silver ion extraction method according to the present invention, in extracting silver ions from an aqueous solution,
The following formula It is characterized by using a compound as an extractant.
本発明にかかる銀イオン抽出法は、Ｐ−フエニ
ルアゾカリツクス［６］アレーンが分子中に銀イ
オンを選択的に配位させて銀イオンのみを抽出す
ることができる。
In the silver ion extraction method according to the present invention, only silver ions can be extracted by selectively coordinating silver ions in the molecule of P-phenylazocalycus [6]arene.
以下に、本発明を、その実施例を参照しつつ詳
しく説明する。
The present invention will be explained in detail below with reference to examples thereof.
本発明に用いる原料のカリツク［６］アレーン
は文献記載の方法により得ることができる。 Calic[6]arene, the raw material used in the present invention, can be obtained by methods described in literature.
すなわち、Ｐ−tert−ブチルフエノールとホル
ムアルデヒドのアルカリ金属塩存在下での縮合に
より得られるＰ−tert−ブチルカリツクス［ｎ］
アレーン（ｎは３以上の整数）をトルエン内で塩
化アルミニウムを使用させ脱ブチル化することに
よつて得ることができる。 That is, P-tert-butyl calix [n] obtained by condensation of P-tert-butylphenol and formaldehyde in the presence of an alkali metal salt.
Arenes (n is an integer greater than or equal to 3) can be obtained by debutylation using aluminum chloride in toluene.
上記によつて得たカリツクス［ｎ］アレーン
（ｎは３以上の整数）を水に分散させるか、又は
有機溶媒に溶解させ、アルカリ存在下、所定温度
で、下記一般式、
（式中Ｘはハロゲン）で示されるベンゼンジア
ゾニウム塩を反応させることにより目的物を得る
ことができる。なお、ベンゼンジアゾニウム塩
は、たとえば、文献記載の常法により合成したも
のを用いることができる。反応に用いる溶媒は、
水あるいはクロロホルム、ベンゼン、Ｎ，Ｎ−ジ
メチルホルムアミドなどの有機溶媒が使用できる
が、溶解性が比較的よく、反応後の生成物の分離
のしやすさを考慮すればテトラヒドロフランの使
用が特に好ましい。すなわち、原料のカリツクス
［ｎ］アレーン（ｎは３以上の整数）は比較的少
量のテトラヒドロフラン溶解し、反応終了後、水
を加えることによつて生成物が沈澱し、ろ別する
ことにより極めて簡単に生成物を取り出すことが
できる。 The calix[n]arene obtained above (n is an integer of 3 or more) is dispersed in water or dissolved in an organic solvent, and the following general formula The desired product can be obtained by reacting a benzenediazonium salt represented by the formula (wherein X is halogen). Note that the benzenediazonium salt can be synthesized, for example, by a conventional method described in literature. The solvent used for the reaction is
Although water or organic solvents such as chloroform, benzene, and N,N-dimethylformamide can be used, tetrahydrofuran is particularly preferred in view of its relatively good solubility and ease of separation of the product after the reaction. That is, the raw material calix[n]arene (n is an integer of 3 or more) is dissolved in a relatively small amount of tetrahydrofuran, and after the reaction is complete, water is added to precipitate the product, which is very easily separated by filtration. The product can be taken out.
上記反応は１時間程度の非常に短時間で済ませ
ることができる。 The above reaction can be completed in a very short time of about 1 hour.
実施例 １
カリツクス［６］アレーン300mg（0.0028mol）
を10mlのテトラヒドロフランに溶解し、２mlの水
に溶解した0.1ｇの水酸化ナトリウムとともに100
mlの撹拌器付三ツ口フラスコに入れ、０℃に保ち
つつ撹拌した。さらに、別途調整したベンゼンジ
アゾニウムクロリド水溶液（0.0034molのベンゼ
ンジアゾニウムクロリドを含む）５mlを滴下ロー
トから徐々に滴下し、０℃で３時間撹拌を続け
た。その後、生成物が沈澱するまで水を加え、ロ
過、水洗、乾燥し、590mgの固体を得た（収率96
％）。さらに、テトラヒドロフラン−水、テトラ
ヒドロフラン−ｎ−ヘキサンによつて再沈澱によ
る精製を繰り返し、150℃で24時間以上真空乾燥
を行つた。この物質の分析結果は次のとおりであ
つた。Example 1 Calix [6] arene 300 mg (0.0028 mol)
was dissolved in 10 ml of tetrahydrofuran and mixed with 0.1 g of sodium hydroxide dissolved in 2 ml of water.
The mixture was placed in a 3-neck flask with a stirrer and stirred while maintaining the temperature at 0°C. Furthermore, 5 ml of a separately prepared benzenediazonium chloride aqueous solution (containing 0.0034 mol of benzenediazonium chloride) was gradually added dropwise from the dropping funnel, and stirring was continued at 0° C. for 3 hours. Then, water was added until the product precipitated, filtered, washed with water, and dried to obtain 590 mg of solid (yield: 96
%). Further, purification by reprecipitation using tetrahydrofuran-water and tetrahydrofuran-n-hexane was repeated, followed by vacuum drying at 150°C for 24 hours or more. The analysis results of this substance were as follows.
融点 300℃以上（融解せず）
赤外吸収スペクトル（KBr錠剤法）
690cm-1 770cm-1（モノ置換ベンゼン）
1520cm-1（アゾ基）
核磁気共鳴スペクトル（D6−DMSO，TMS基
準）
1H δ4付近 （ブロードな単一ピーク、−CH2-
およびH2O）
δ7.5〜7.9 （シヤープな多重ピーク、芳香環
Ｈ）
13C δ32.2 （−CH2−）
δ121.9，124.1，128.9，129.2，130.5，
144.5，152.1，158.4（芳香環）
元素分析 炭素72.15％、水素4.83％、窒素12.5
％
〔予想組成式（C78H60O6N12）（2H2O）
計算値：炭素72.14％、水素5.14％、窒素
12.96％〕
以上より得たれた物質は、下記の構造式を有し
ていることが分かつた。 Melting point 300℃ or higher (not melted) Infrared absorption spectrum (KBr tablet method) 690cm -1 770cm -1 (monosubstituted benzene) 1520cm -1 (azo group) Nuclear magnetic resonance spectrum (D 6 -DMSO, TMS standard) 1 Around H δ4 (broad single peak, −CH 2-
and H2O ) δ7.5-7.9 (sharp multiple peaks, aromatic ring H) 13C δ32.2 ( -CH2- ) δ121.9, 124.1, 128.9, 129.2, 130.5,
144.5, 152.1, 158.4 (aromatic ring) Elemental analysis Carbon 72.15%, hydrogen 4.83%, nitrogen 12.5
% [Predicted composition formula (C 78 H 60 O 6 N 12 ) (2H 2 O) Calculated values: Carbon 72.14%, Hydrogen 5.14%, Nitrogen
12.96%] The substance obtained above was found to have the following structural formula.
実施例 ２
溶媒としてのテトラヒドロフランに代え、Ｎ，
Ｎ−ジメチルホルムアルドを100mlを用い、実施
例１と同様な操作を行い、実施例１で記載した構
造式を有する化合物を収率71％で得た。 Example 2 Instead of tetrahydrofuran as a solvent, N,
The same operation as in Example 1 was performed using 100 ml of N-dimethyl formalde to obtain a compound having the structural formula described in Example 1 in a yield of 71%.
実施例 ３
硝酸銀（10-2M）をピクリン酸（２×10-5M）
水溶液中に溶解し、この水溶液に実施例１で得た
Ｐ−フエニルアゾカリツクス［６］アレーン
（10-3M）のクロロホルム溶液を添加し、25℃で
24時間振とうさせた後、水相中のピリクン酸の濃
度を吸光度の減少から測定し、銀イオンの抽出率
を測定したところ、22％であつた。Example 3 Silver nitrate (10 -2 M) was mixed with picric acid (2 x 10 -5 M)
A chloroform solution of P-phenylazocalycus [6]arene (10 -3 M) obtained in Example 1 was added to this aqueous solution, and the mixture was heated at 25°C.
After shaking for 24 hours, the concentration of pyricic acid in the aqueous phase was determined from the decrease in absorbance, and the extraction rate of silver ions was determined to be 22%.
（比較例）
ナトリウム、カリウム、銅、亜鉛、カドミウ
ム、バリウム、鉛、アルミニウムの各金属塩につ
いて実施例３と同様にして各金属イオンの抽出率
を測定したところ、抽出率はすべて０％であつ
た。(Comparative example) When the extraction rate of each metal ion was measured in the same manner as in Example 3 for each metal salt of sodium, potassium, copper, zinc, cadmium, barium, lead, and aluminum, the extraction rate was all 0%. Ta.
（発明の効果）
本発明にかかる銀イオン抽出法は、以上のよう
に、安価に得ることができるＰ−フエニルアゾカ
リツクス［６］アレーンを用いるようにしたの
で、銀イオンを高選択的にかつ安価に抽出するこ
とができる。(Effects of the Invention) As described above, the silver ion extraction method according to the present invention uses P-phenylazocalycus [6]arene, which can be obtained at low cost, so silver ions can be extracted with high selectivity. It can be extracted quickly and inexpensively.
Claims (1)
下記式 の化合物を抽出剤として用いることを特徴とする
銀イオンの抽出法。[Claims] 1. In extracting silver ions from an aqueous solution,
The following formula A silver ion extraction method characterized by using a compound of as an extractant.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27763388A JPH02124863A (en) | 1988-11-01 | 1988-11-01 | P-arylazocalix(n)arene, production thereof and method for extracting silver ion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27763388A JPH02124863A (en) | 1988-11-01 | 1988-11-01 | P-arylazocalix(n)arene, production thereof and method for extracting silver ion |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02124863A JPH02124863A (en) | 1990-05-14 |
| JPH0541629B2 true JPH0541629B2 (en) | 1993-06-24 |
Family
ID=17586147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27763388A Granted JPH02124863A (en) | 1988-11-01 | 1988-11-01 | P-arylazocalix(n)arene, production thereof and method for extracting silver ion |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02124863A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07314368A (en) * | 1994-05-23 | 1995-12-05 | Ondo Kosakusho:Kk | Connection device for attaching and detaching tool |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5434208A (en) * | 1992-07-10 | 1995-07-18 | Akzo Nobel N.V. | Optically non-linear active waveguiding material comprising a dopant having multiple donor-n-acceptor systems |
| CN103242193B (en) * | 2013-05-17 | 2015-04-01 | 南华大学 | Preparation and use of hydroxyl oximated calix[6]arene efficient uranium extractant |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0215040A (en) * | 1988-07-01 | 1990-01-18 | Yutaka Morita | Novel calixarene derivative |
-
1988
- 1988-11-01 JP JP27763388A patent/JPH02124863A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0215040A (en) * | 1988-07-01 | 1990-01-18 | Yutaka Morita | Novel calixarene derivative |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07314368A (en) * | 1994-05-23 | 1995-12-05 | Ondo Kosakusho:Kk | Connection device for attaching and detaching tool |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02124863A (en) | 1990-05-14 |
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