JPS5924856B2 - Method for producing heat-resistant chelating material adsorbent carbon - Google Patents
Method for producing heat-resistant chelating material adsorbent carbonInfo
- Publication number
- JPS5924856B2 JPS5924856B2 JP56071870A JP7187081A JPS5924856B2 JP S5924856 B2 JPS5924856 B2 JP S5924856B2 JP 56071870 A JP56071870 A JP 56071870A JP 7187081 A JP7187081 A JP 7187081A JP S5924856 B2 JPS5924856 B2 JP S5924856B2
- Authority
- JP
- Japan
- Prior art keywords
- oxyquinoline
- chelating material
- heat
- carbon
- activated carbon
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims description 45
- 229910052799 carbon Inorganic materials 0.000 title claims description 11
- 239000000463 material Substances 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000003463 adsorbent Substances 0.000 title claims description 6
- ZBSGNEYIENETRW-UHFFFAOYSA-N 2,3-bis(hydroxymethyl)phenol Chemical class OCC1=CC=CC(O)=C1CO ZBSGNEYIENETRW-UHFFFAOYSA-N 0.000 claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical class OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 229920001568 phenolic resin Polymers 0.000 claims 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002738 chelating agent Substances 0.000 description 5
- 229910000365 copper sulfate Inorganic materials 0.000 description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910001431 copper ion Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- -1 methylol compound Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- XOUAQPDUNFWPEM-UHFFFAOYSA-N 2,3,4-tris(hydroxymethyl)phenol Chemical compound OCC1=CC=C(O)C(CO)=C1CO XOUAQPDUNFWPEM-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Carbon And Carbon Compounds (AREA)
Description
【発明の詳細な説明】 本発明は耐熱性キレート材吸着炭の製造方法に関する。[Detailed description of the invention] The present invention relates to a method for producing a heat-resistant chelating material adsorbed carbon.
微量の金属を補集したり微量の金属類を含有する溶液か
ら金属を除去して純度の高い溶液を得ようとする目的で
キレート材を使用することは有効である。It is effective to use a chelating agent for the purpose of collecting trace amounts of metals or removing metals from solutions containing trace amounts of metals to obtain highly pure solutions.
キレート材として８−オキシキノリンはキレート能が大
きく更にこの８−オキシキノリンを活性炭に吸着させた
ものを使用することは、その取扱い上からも一層実用的
である。As a chelating agent, 8-oxyquinoline has a large chelating ability, and it is more practical to use activated carbon adsorbed with 8-oxyquinoline from the viewpoint of handling.
しかし８−オキシキノリンは融点が７５〜７６℃と低く
融点以上での使用はそのキレート能がいちぢるしく低下
する欠点をもっていた。However, 8-oxyquinoline has a low melting point of 75 to 76 DEG C., and its chelating ability is significantly reduced when used above the melting point.
本発明はこれらの欠点を補う目的でなされたものである
。The present invention has been made to compensate for these drawbacks.
以下にその詳細について述べる。The details are described below.
８−オキシキノリンはホルマリンと加熱するとメチロー
ル体を生じ更に高温で加熱し脱水すると硬化し樹脂状固
型物となる。When 8-oxyquinoline is heated with formalin, it produces a methylol compound, and when it is further heated at a high temperature and dehydrated, it hardens into a resinous solid.
この固型物は不溶不融で３００〜３５０℃で分解する。This solid substance is insoluble and infusible and decomposes at 300 to 350°C.
しかし反応は極めておそく収率も高くない。However, the reaction is extremely slow and the yield is not high.
一方８−オキシキノリンとホルマリンとフェノールを混
合して加熱すると液状の初期縮合物となり更に高温で加
熱を続は脱水すると硬化し樹脂状固型物となる。On the other hand, when 8-oxyquinoline, formalin, and phenol are mixed and heated, the mixture becomes a liquid initial condensate, and when further heated at a high temperature and then dehydrated, it hardens and becomes a resinous solid.
この固型物も不溶不融で２００〜３００℃で分解する。This solid substance is also insoluble and infusible and decomposes at 200 to 300°C.
この固型物の生成に際しては脱水と同時に８−オキシキ
ノリンの揮散が大きく、フェノールホルマリン樹脂にわ
ずかに８−オキシキノリンが組込まれた固型物となって
いる。When this solid material is produced, 8-oxyquinoline is largely volatilized at the same time as dehydration, resulting in a solid material in which a small amount of 8-oxyquinoline is incorporated into the phenol-formalin resin.
これは８−オキシキノリンに比べてフェノールの反応性
が極めて高いためと推定できる。This can be presumed to be due to the extremely high reactivity of phenol compared to 8-oxyquinoline.
本発明者は、これらの反応を詳細に調べた結果５．７ジ
メチロールー８−オキシキノリンとメチロールフェノー
ルの縮合反応活性が最も高く、未反応の８−オキシキノ
リンや未反応のフェノールが少いこと、またこれらの七
ツマ−は、活性炭への吸着も高分子物と異って極めて容
易であり、吸着されたモノマーは加熱により活性炭中で
脱ホルマリン縮合を起して融点の高い耐熱性のある化合
物になることを見い出し本発明にいたった。The present inventor investigated these reactions in detail and found that the condensation reaction activity of 5.7 dimethylol-8-oxyquinoline and methylolphenol was the highest, and that unreacted 8-oxyquinoline and unreacted phenol were small. In addition, unlike polymers, these monomers are extremely easily adsorbed onto activated carbon, and when heated, the adsorbed monomers undergo deformalization condensation in the activated carbon to form a heat-resistant compound with a high melting point. This discovery led to the present invention.
本発明は５．７−シメチロールー８−オキシキノリンと
モノメチロールフェノール類とジメチロールフェノール
類を活性炭に吸着させたのち加熱縮合反応を起こさぜる
ことを特徴とする耐熱キレート材吸着炭の製造方法に関
し、新規な融点の高い耐熱性のあるキレート材吸着炭を
提供するものである。The present invention relates to a method for producing a heat-resistant chelating material adsorbed carbon, which comprises adsorbing 5,7-dimethylol-8-oxyquinoline, monomethylolphenols, and dimethylolphenols onto activated carbon and then causing a heating condensation reaction. The present invention provides a novel adsorbent chelating material with a high melting point and heat resistance.
ジメチロールオキシキノリンと、ジメチロールフェノー
ル類は当モルであることが望ましいが実際にはその比が
１ ： ０．８〜１：１．２以内であればよい。It is desirable that the dimethyloloxyquinoline and dimethylolphenol be in equimolar amounts, but in reality, the ratio may be within 1:0.8 to 1:1.2.
またモノメチロールフェノール類とジメチロールフェノ
ール類の配合比（成分比）により生成物の熱分解温度や
平均分子量は当然変化するものであるが、２５０℃以上
の熱分解温度をもつオキシキノリン誘導体を得るために
はモノメチロールフェノール類とジメチロールフェノー
ル類のモル比は０．９：０．１から０．１：０．９とす
ることが好ましい。Although the thermal decomposition temperature and average molecular weight of the product naturally change depending on the blending ratio (component ratio) of monomethylolphenols and dimethylolphenols, it is possible to obtain an oxyquinoline derivative with a thermal decomposition temperature of 250°C or higher. In order to achieve this, the molar ratio of monomethylolphenols to dimethylolphenols is preferably from 0.9:0.1 to 0.1:0.9.
フェノール類としてはフェノール、クレゾール、キシレ
ノール、ブチルフェノールなどのアルキルフェノール類
あるいはビスフェノール類が用いられる。As the phenols, alkylphenols such as phenol, cresol, xylenol, and butylphenol, or bisphenols are used.
本発明においてはこれらの原料をそのまま活性炭に吸着
させたり、メタノール等の溶剤に溶かして活性炭に加え
てその後溶剤を除去する方法等により、原料を活性炭に
吸着させ、これを３０℃〜２００℃好ましくは１２０〜
１６０℃で０．１時間〜２．０時間、加熱縮合反応させ
る。In the present invention, these raw materials are adsorbed on activated carbon as they are, or are dissolved in a solvent such as methanol and added to activated carbon, and then the solvent is removed. is 120~
A heating condensation reaction is carried out at 160° C. for 0.1 to 2.0 hours.
この際、反応は無触媒で行ってもよいし、また酸性、ア
ルカリ性触媒を用いてもよい。At this time, the reaction may be carried out without a catalyst or with an acidic or alkaline catalyst.
オキシキノリン誘導体は活性炭に対しては１０〜３０重
量％、好ましくは１５〜２５重量％付着するようにする
。The oxyquinoline derivative is attached to the activated carbon in an amount of 10 to 30% by weight, preferably 15 to 25% by weight.
以下本発明を実施例に基いて説明する。The present invention will be explained below based on examples.
〔実施例 １〕
５．７−シメチロールー８−オキシキノリン１ｏ、２５
ｇ（ｏ、ｏ５モル）とＯ−メチロールフェノール６．２
ｇ（０，０５モル）と０−０７−ジメチロールフェノー
ル７．７ｇ（０，０５モル）とをメタノールにとかして
やし殻炭２５０ｇに加え十分振とうしたのち加温してメ
タノールを除去した。[Example 1] 5.7-Simethylol-8-oxyquinoline 1o, 25
g (o, o5 mol) and O-methylolphenol 6.2
g (0.05 mol) and 7.7 g (0.05 mol) of 0-07-dimethylolphenol were dissolved in methanol, added to 250 g of coconut shell charcoal, thoroughly shaken, and heated to remove methanol.
この添着活性炭を１５０℃３０分加熱炉で熱処理してキ
レート材吸着炭を製造した。This impregnated activated carbon was heat treated in a heating furnace at 150° C. for 30 minutes to produce a chelating agent adsorbed carbon.
このキレート材吸着炭１０ｇを１％硫酸銅水溶液と共に
圧力容器に入れ１８５℃に昇温内圧７ｋｇ／ｄとしたの
ち冷却した所、硫酸銅溶液は無色となり銅イオンは見出
されなかった。When 10 g of this chelating material adsorbed carbon was placed in a pressure vessel together with a 1% aqueous copper sulfate solution, the temperature was raised to 185° C., the internal pressure was set to 7 kg/d, and then cooled, the copper sulfate solution became colorless and no copper ions were found.
〔参考例 １〕
８−オキシキノリン１０ｇをメタノールにとかし活性炭
１００ｇに吸着させ加温してメタノールを除き、オキシ
ン添着活性炭をえた。[Reference Example 1] 10 g of 8-oxyquinoline was dissolved in methanol, adsorbed onto 100 g of activated carbon, and heated to remove methanol to obtain oxine-impregnated activated carbon.
この添着活性炭１０ｇを常温で１％硫酸銅溶液１００Ｃ
Ｃに加えたところ銅イオンの色は５分后に消失した。Add 10g of this impregnated activated carbon to a 1% copper sulfate solution at 100C at room temperature.
When added to C, the color of copper ions disappeared after 5 minutes.
次に新しい８−オキシキノリン添着活性炭１０ｇを実施
例１と同様に硫酸銅溶液と高温高圧処理したところ柳銅
液の銅イオンはややうずくなった程度で銅はほとんどキ
レート化されていなかつｊも
〔実施例 ２〕
フェノール１４．４ ｇ（０，１５モル）と３０％ホル
マリン２４ｇ（０，２４モル）と加えて４０ ’Ｃ２４
時間放置した。Next, 10 g of new 8-oxyquinoline-impregnated activated carbon was treated with a copper sulfate solution at high temperature and high pressure in the same manner as in Example 1. The copper ions in the Yanagi copper solution were only a little tingling, and the copper was hardly chelated. Example 2] 14.4 g (0.15 mol) of phenol and 24 g (0.24 mol) of 30% formalin were added to 40'C24
I left it for a while.
この液を２００ ＯＡのポリスチレンゲルカラム装置の
日立高速液クロロ３５型により分析した新来反応フェノ
ール１２％、モノメチロールフェノール４５％、ジメチ
ロールフェノール３０％、２．４ジメチロールフエノー
ルとトリメチロールフェノール１０％、三核体フェノー
ル３％の混合物であった。This solution was analyzed using a Hitachi high performance liquid chloroform type 35 using a 200 OA polystyrene gel column device.New reaction phenol: 12%, monomethylolphenol: 45%, dimethylolphenol: 30%, 2.4 dimethylolphenol and trimethylolphenol: 10% %, a mixture of 3% trinuclear phenol.
この混合物に５．７−シメチロールー８−オキシキノリ
ン１０．２５ｇを加え更に活性炭２５０ｇを加えて攪拌
し濾過した活性炭を乾燥し２７０ｇの添着活性炭を得た
。To this mixture, 10.25 g of 5,7-dimethylol-8-oxyquinoline was added, and further 250 g of activated carbon was added, stirred, and the filtered activated carbon was dried to obtain 270 g of impregnated activated carbon.
この活性炭を１３０°Ｃ６０分加熱処理しキレート材吸
着炭とした。This activated carbon was heat-treated at 130°C for 60 minutes to obtain chelating agent adsorption carbon.
このものは実施例１と同様硫酸銅液の銅イオン色を脱色
した。This product decolorized the copper ion color of the copper sulfate solution as in Example 1.
以上に説明したように本願発明により耐熱性及びキレー
ト能に優れたキレート材吸着炭が得られた。As explained above, according to the present invention, a chelating agent adsorbent carbon having excellent heat resistance and chelating ability was obtained.
Claims (1)
チロールフェノール類とジメチロールフェノール類を活
性炭に吸着させたのち加熱縮合反応を起させることを特
徴とする耐熱キレート材吸着炭の製造方法。 ２５．７−シメチロールー８−オキシキノリンとジメチ
ロールフェノール類のモル比がに〇、８から１：１．２
である特許請求の範囲第１項記載の耐熱性キレート材吸
着炭の製造方法。 ３ モノメチロールフェノール類とジメチロールフェノ
ール類の含量が８０重量％以上であるフェノールホルム
アルデヒド初期縮合物を用いる特許請求の範囲第１項又
は第２項記載の耐熱性キレート材吸着炭の製造方法。 ４ モノメチロールフェノール類、ジメチロールフェノ
ール類のフェノール類かフェノール、クレゾール又はキ
シレノールである特許請求範囲第１項、第２項又は第３
項記載の耐熱性キレート材吸着炭の製造方法。[Claims] 15. Production of heat-resistant chelating material adsorbed carbon, characterized by adsorbing 7-dimethylol-8-oxyquinoline, monomethylolphenols, and dimethylolphenols onto activated carbon, and then causing a heating condensation reaction. Method. 25. The molar ratio of 7-dimethylol-8-oxyquinoline and dimethylolphenol is from 8 to 1:1.2.
A method for producing a heat-resistant chelating material adsorbent carbon according to claim 1. 3. A method for producing a heat-resistant chelating material adsorbent carbon according to claim 1 or 2, which uses a phenol-formaldehyde initial condensate having a content of monomethylolphenols and dimethylolphenols of 80% by weight or more. 4. Claims 1, 2 or 3 which are monomethylolphenols, dimethylolphenols, phenol, cresol or xylenol
A method for producing a heat-resistant chelating material adsorbent carbon as described in 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56071870A JPS5924856B2 (en) | 1981-05-12 | 1981-05-12 | Method for producing heat-resistant chelating material adsorbent carbon |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56071870A JPS5924856B2 (en) | 1981-05-12 | 1981-05-12 | Method for producing heat-resistant chelating material adsorbent carbon |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57187041A JPS57187041A (en) | 1982-11-17 |
| JPS5924856B2 true JPS5924856B2 (en) | 1984-06-12 |
Family
ID=13472977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56071870A Expired JPS5924856B2 (en) | 1981-05-12 | 1981-05-12 | Method for producing heat-resistant chelating material adsorbent carbon |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5924856B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4847194B2 (en) * | 2006-04-21 | 2011-12-28 | 三菱農機株式会社 | Combine cutter unit |
-
1981
- 1981-05-12 JP JP56071870A patent/JPS5924856B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57187041A (en) | 1982-11-17 |
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