JP2000264902A - Thiourea derivative of chitosan - Google Patents

Thiourea derivative of chitosan

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Publication number
JP2000264902A
JP2000264902A JP11068200A JP6820099A JP2000264902A JP 2000264902 A JP2000264902 A JP 2000264902A JP 11068200 A JP11068200 A JP 11068200A JP 6820099 A JP6820099 A JP 6820099A JP 2000264902 A JP2000264902 A JP 2000264902A
Authority
JP
Japan
Prior art keywords
chitosan
derivative
metal
chitosan derivative
metal ion
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.)
Pending
Application number
JP11068200A
Other languages
Japanese (ja)
Inventor
Yoshinari Baba
由成 馬場
Hiroshi Noma
比呂志 野間
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Miyazaki NUC
Original Assignee
University of Miyazaki NUC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by University of Miyazaki NUC filed Critical University of Miyazaki NUC
Priority to JP11068200A priority Critical patent/JP2000264902A/en
Publication of JP2000264902A publication Critical patent/JP2000264902A/en
Pending legal-status Critical Current

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Classifications

    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P10/00—Technologies related to metal processing
    • Y02P10/20—Recycling

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  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Treatment Of Water By Ion Exchange (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Manufacture And Refinement Of Metals (AREA)

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound retaining excellent adsorption ability to a metal due to not being subjected to crosslinking treatment, being insoluble even in an acidic solution, useful as a metal adsorbent, containing thiourea as a ligand. SOLUTION: This chitosan derivative is expressed by the formula (R is methyl, ethyl or phenyl). The compound of the formula is obtained, in the case of a methylthiourea derivative in which R is methyl group, by treating an amino group bonded to the C2 position of chitosan with methyl isothiocyanate, in the case of an ethylthiourea derivative in which R is ethyl group, by treating an amino group bonded to the C2 position of chitosan with ethyl isothiocyanate and, in the case of a phenylthiourea derivative in which R is phenyl group, by treating an amino group bonded to the C2 of chitosan with phenyl isothiocyanate. The chitosan derivative can be used for industrially recovering a metal such as gold, platinum, palladium, mercury, or the like.

Description

【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION

【０００１】[0001]

【発明の属する技術分野】本発明は、チオ尿素を配位子
として有するキトサン誘導体、該キトサン誘導体を具備
する金属吸着剤、及び該キトサン誘導体を用いた金属の
選択的回収法に関する。The present invention relates to a chitosan derivative having thiourea as a ligand, a metal adsorbent comprising the chitosan derivative, and a method for selectively recovering a metal using the chitosan derivative.

【０００２】[0002]

【従来の技術】水溶液から金属イオンを分離・回収する
方法としては、油溶性の捕集剤を溶解した有機溶媒と液
-液接触させる溶媒抽出法、及びイオン交換樹脂や活性
炭等を用いて固-液接触させる吸着法があり、特に後者
は希薄溶液の処理に適している。2. Description of the Related Art As a method for separating and recovering metal ions from an aqueous solution, an organic solvent in which an oil-soluble collecting agent is dissolved and a liquid are used.
There are a solvent extraction method in which liquid contact is made, and an adsorption method in which solid-liquid contact is made using an ion exchange resin or activated carbon, and the latter is particularly suitable for treating a dilute solution.

【０００３】現在まで選択性の高いキレート樹脂の開発
が活発に進められており、多くのキレート樹脂が市販さ
れている。Up to now, chelate resins having high selectivity have been actively developed, and many chelate resins are commercially available.

【０００４】しかしながら、これらのキレート樹脂は比
較的高価であるが、特定の金属イオンに対する選択性は
それほど高くないものが多く、安価で且つ選択性の高い
吸着剤の開発がなお望まれている。However, although these chelating resins are relatively expensive, many of them do not have high selectivity to specific metal ions, and there is still a need for the development of an inexpensive and highly selective adsorbent.

【０００５】この点、キトサンは、優れた金属イオン吸
着能を有する物質として以前から知られており、また蟹
や海老の殻から得ることができるため価格も安価であ
る。[0005] In this respect, chitosan has been known as a substance having an excellent metal ion-adsorbing ability, and can be obtained from crab or shrimp shells, so that its cost is low.

【０００６】しかし、修飾されていないキトサンは、酢
酸や蟻酸等の有機酸には全ての濃度範囲にわたって常温
で溶解し、塩酸や硝酸等の無機酸には0.05〜1規定の濃
度範囲において常温で溶解してしまう。However, unmodified chitosan is soluble in organic acids such as acetic acid and formic acid at room temperature over the entire concentration range, and is soluble in inorganic acids such as hydrochloric acid and nitric acid at room temperature in a concentration range of 0.05 to 1N. Will dissolve.

【０００７】そのため、キトサンを酸性溶液中で用いる
場合には、エピクロロヒドリン等で架橋処理を施す必要
があるが、該架橋処理によって、キトサン中のアミノ基
まで架橋されてしまい、金属の吸着量が低下するという
欠点があった。[0007] Therefore, when chitosan is used in an acidic solution, it is necessary to carry out a cross-linking treatment with epichlorohydrin or the like. However, the cross-linking treatment causes cross-linking up to the amino groups in the chitosan, resulting in metal adsorption. There was a disadvantage that the amount was reduced.

【０００８】[0008]

【発明が解決しようとする課題】本発明は、従来技術に
存するこのような欠点を克服するためになされたもので
あり、架橋処理が施されていないために、金属に対する
優れた吸着能が保持されており、且つ酸性溶液中におい
ても不溶性であるキトサン誘導体を提供することを目的
とする。SUMMARY OF THE INVENTION The present invention has been made to overcome such disadvantages in the prior art, and has no excellent cross-linking treatment. It is an object of the present invention to provide a chitosan derivative which has been prepared and is insoluble even in an acidic solution.

【０００９】また、該キトサン誘導体を具備する金属吸
着剤、該キトサン誘導体を用いて、水溶液中から金属イ
オンを選択的に回収する方法を提供することも本発明の
目的である。It is another object of the present invention to provide a metal adsorbent comprising the chitosan derivative and a method for selectively recovering metal ions from an aqueous solution using the chitosan derivative.

【００１０】[0010]

【課題を解決するための手段】上記課題を解決するため
に、本発明は、以下の構造：In order to solve the above problems, the present invention provides the following structure:

【００１１】[0011]

【化２】 Embedded image

【００１２】（ここで、Rはメチル、エチル、及びフェ
ニルのうちの何れか）を有するキトサン誘導体を提供す
る。A chitosan derivative having (where R is any one of methyl, ethyl and phenyl) is provided.

【００１３】[0013]

【発明の実施の形態】以下、本発明の実施例を説明す
る。Embodiments of the present invention will be described below.

【００１４】実施例１ 本実施例では、以下の構造：Embodiment 1 This embodiment has the following structure:

【００１５】[0015]

【化３】 Embedded image

【００１６】（ここでR＝メチル基）を有する化合物
（キトサンのメチルチオ尿素誘導体、以下MTUC）を用い
た金属イオンの吸着試験について記載する。A metal ion adsorption test using a compound having (here, R = methyl group) (a methylthiourea derivative of chitosan, hereinafter referred to as MTUC) will be described.

【００１７】MTUCは、キトサンのC2位に結合したアミノ
基にイソチオシアン酸メチルを作用させることによっ
て、合成した。MTUC was synthesized by allowing methyl isothiocyanate to act on the amino group bonded to the C 2 position of chitosan.

【００１８】本実施例において、吸着実験は全てバッチ
法で行った。In this example, all the adsorption experiments were performed by a batch method.

【００１９】0.01〜3Nの塩酸を含有する溶液に、1mmol/
dm3の各金属イオンをそれぞれ溶解し、硝酸とアンモニ
アを用いて、該水溶液のpHを調整した。In a solution containing 0.01 to 3N hydrochloric acid, 1 mmol /
Each metal ion of dm 3 was dissolved, and the pH of the aqueous solution was adjusted using nitric acid and ammonia.

【００２０】該水溶液15mLに対して、MTUC樹脂50mgを加
えて、30℃で恒温槽中において24時間振盪した。次い
で、MTUC樹脂をろ過、遠心分離により除去した後、水溶
液中に残存している各金属濃度を原子吸光光度計によっ
て求めた。この測定値を、MTUC樹脂に吸着された各金属
イオンの吸着率に換算し、その結果を図１に示した。To 15 mL of the aqueous solution, 50 mg of MTUC resin was added, and the mixture was shaken at 30 ° C. in a thermostat for 24 hours. Next, after removing the MTUC resin by filtration and centrifugation, the concentration of each metal remaining in the aqueous solution was determined by an atomic absorption spectrophotometer. This measured value was converted to the adsorption rate of each metal ion adsorbed on the MTUC resin, and the result is shown in FIG.

【００２１】図１から明らかなように、MTUCは、何れの
塩酸濃度においても、金、白金、パラジウムイオンをほ
ぼ100%吸着することが実証された。As apparent from FIG. 1, it was demonstrated that MTUC adsorbs almost 100% of gold, platinum and palladium ions at any hydrochloric acid concentration.

【００２２】また、MTUCは、全ての塩酸濃度において、
水銀イオンもほぼ100%吸着した。Further, MTUC is obtained at all hydrochloric acid concentrations.
Almost 100% of mercury ions were also adsorbed.

【００２３】実施例２ 本実施例では、以下の構造：Embodiment 2 In this embodiment, the following structure is used:

【００２４】[0024]

【化４】 Embedded image

【００２５】（ここでR＝エチル基）を有する化合物
（キトサンのエチルチオ尿素誘導体、以下ETUC）を用い
た金属イオンの吸着試験について記載する。A metal ion adsorption test using a compound having (here, R = ethyl group) (ethylthiourea derivative of chitosan, hereinafter ETUC) will be described.

【００２６】ETUCは、キトサンのC2位に結合したアミノ
基にイソチオシアン酸エチルを作用させることによっ
て、合成した。ETUC was synthesized by reacting ethyl isothiocyanate on the amino group bonded to the C 2 position of chitosan.

【００２７】実験条件は、実施例１と同じである。The experimental conditions are the same as in Example 1.

【００２８】図２に示されているように、ETUCは、塩酸
濃度に依存せずに、金、白金、パラジウムをほぼ100%吸
着することが実証された。As shown in FIG. 2, it was demonstrated that ETUC adsorbs almost 100% of gold, platinum and palladium independently of hydrochloric acid concentration.

【００２９】実施例３ 本実施例では、以下の構造：Embodiment 3 In this embodiment, the following structure is used:

【００３０】[0030]

【化５】 Embedded image

【００３１】（ここでR＝フェニル基）を有する化合物
（キトサンのフェニルチオ尿素誘導体、以下PTUC）を用
いた金属イオンの吸着試験について記載する。A metal ion adsorption test using a compound having (here, R = phenyl group) (phenylthiourea derivative of chitosan, hereinafter PTUC) will be described.

【００３２】PTUCは、キトサンのC2位に結合したアミノ
基にイソチオシアン酸フェニルを作用させることによっ
て、合成した。PTUC was synthesized by allowing phenyl isothiocyanate to act on the amino group bonded to the C 2 position of chitosan.

【００３３】実験条件は、実施例１及び２と同じであ
る。The experimental conditions are the same as in Examples 1 and 2.

【００３４】図３から明らかなように、PTUCは、何れの
塩酸濃度においても、銅、ニッケル、鉄、コバルト、亜
鉛等の卑金属を全く吸着しなかった。これに対して、パ
ラジウムは、0.1規定の塩酸濃度で70%吸着された。As is apparent from FIG. 3, PTUC did not adsorb any base metals such as copper, nickel, iron, cobalt, and zinc at any concentration of hydrochloric acid. On the other hand, palladium was adsorbed by 70% at 0.1 N hydrochloric acid concentration.

【００３５】従って、PTUCは、銅を含有する溶液から、
パラジウムを選択的に抽出するのに適している。Accordingly, PTUC is obtained from a solution containing copper by
Suitable for selectively extracting palladium.

【００３６】実施例４ 本実施例では、ETUCを用いた一回のバッチ法におけるパ
ラジウムの溶離回収について記載する。Example 4 This example describes the elution and recovery of palladium in a single batch process using ETUC.

【００３７】パラジウムを吸着させたETUCに、下表１に
記載の各溶離剤を添加して、溶離率を調べた。結果を表
１に示す。Each of the eluents shown in Table 1 below was added to the palladium-adsorbed ETUC, and the elution rate was examined. Table 1 shows the results.

【００３８】[0038]

【００３９】[0039]

【表１】 [Table 1]

【００４０】表１に示されているように、様々な濃度の
塩酸存在下において、1Nのチオ尿素により、パラジウム
を80〜90%溶離できることが明らかとなった。また、同
様の条件で、白金も約30%溶離し得ることが示された。As shown in Table 1, it was found that 80% to 90% of palladium can be eluted with 1N thiourea in the presence of various concentrations of hydrochloric acid. It was also shown that under the same conditions, about 30% of platinum could be eluted.

【００４１】本実施例によって、0.01〜5規定の塩酸と1
規定のチオ尿素により、パラジウム及び白金を溶離回収
し得ること、及びキトサン誘導体を再利用できることが
実証された。According to the present example, 0.01 to 5N hydrochloric acid and 1
It was demonstrated that palladium and platinum could be eluted and recovered with the defined thiourea, and that the chitosan derivative could be reused.

【００４２】[0042]

【発明の効果】本発明のキトサン誘導体は、架橋処理が
なされていないために、高い金属吸着能を保持してい
る。As described above, the chitosan derivative of the present invention has a high metal-adsorbing ability because it is not crosslinked.

【００４３】さらに、本発明のキトサン誘導体は、塩酸
等の無機酸にも、酢酸等の有機酸にも溶解しないという
未修飾のキトサンには見られない特性を有する。Furthermore, the chitosan derivative of the present invention has a property not found in unmodified chitosan, which does not dissolve in inorganic acids such as hydrochloric acid or organic acids such as acetic acid.

【００４４】また、本発明のキトサン誘導体に結合した
金属は、塩酸存在下でチオ尿素を用いることによって溶
離される。それ故、本発明のキトサン誘導体を用いる
と、金属を簡便に回収することができ、且つキトサン誘
導体を再利用することも可能である。The metal bound to the chitosan derivative of the present invention is eluted by using thiourea in the presence of hydrochloric acid. Therefore, when the chitosan derivative of the present invention is used, metals can be easily recovered, and the chitosan derivative can be reused.

【００４５】従来キトサンを工業的に利用することは困
難であったが、本発明のキトサン誘導体は、以上のよう
な特性を有するため、金、白金、パラジウム、水銀等の
金属を工業的に回収するために用いることができる。Conventionally, it has been difficult to industrially use chitosan. However, the chitosan derivative of the present invention has the above-mentioned properties, and therefore, industrially recovers metals such as gold, platinum, palladium and mercury. Can be used to

【００４６】加えて、本発明のキトサン誘導体は、他の
イオン交換樹脂に比べて、焼却が極めて容易であるとい
う顕著な効果をも有する。In addition, the chitosan derivative of the present invention has a remarkable effect that incineration is extremely easy as compared with other ion exchange resins.

【図面の簡単な説明】[Brief description of the drawings]

【図１】 本発明によるメチルチオ尿素型のキトサン誘
導体を用いて行った、塩酸溶液からの金属イオンの吸着
試験の結果を表す図。FIG. 1 is a diagram showing the results of a metal ion adsorption test from a hydrochloric acid solution performed using a methylthiourea-type chitosan derivative according to the present invention.

【図２】 本発明によるエチルチオ尿素型のキトサン誘
導体を用いて行った、塩酸溶液からの金属イオンの吸着
試験の結果を表す図。FIG. 2 is a diagram showing the results of an adsorption test of metal ions from a hydrochloric acid solution performed using an ethylthiourea-type chitosan derivative according to the present invention.

【図３】本発明によるフェニルチオ尿素型のキトサン誘
導体を用いて行った、塩酸溶液からの金属イオンの吸着
試験の結果を表す図。FIG. 3 is a graph showing the results of a metal ion adsorption test from a hydrochloric acid solution performed using a phenylthiourea-type chitosan derivative according to the present invention.

───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ テーマコート゛(参考） Ｃ２２Ｂ 3/24 Ｃ２２Ｂ 3/00 Ｌ 11/00 11/04 Ｆターム(参考） 4C090 AA02 AA08 BA47 BB62 BB63 BB98 DA05 DA21 4D025 AA09 AB27 AB29 BA17 4G066 AB13D AB15D AC01B AD11B CA46 CA47 GA11 4K001 AA41 BA19 DB02 DB17 DB36──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. 7 Identification symbol FI Theme coat ゛ (Reference) C22B 3/24 C22B 3/00 L 11/00 11/04 F term (Reference) 4C090 AA02 AA08 BA47 BB62 BB63 BB98 DA05 DA21 4D025 AA09 AB27 AB29 BA17 4G066 AB13D AB15D AC01B AD11B CA46 CA47 GA11 4K001 AA41 BA19 DB02 DB17 DB36

Claims (6)

【特許請求の範囲】[Claims] 【請求項１】 以下の構造： 【化１】 （ここで、Rはメチル、エチル、及びフェニルのうちの
何れか）を有するキトサン誘導体。1. The following structure: (Where R is any one of methyl, ethyl and phenyl). 【請求項２】 請求項１のキトサン誘導体を具備する金
属吸着剤。2. A metal adsorbent comprising the chitosan derivative according to claim 1. 【請求項３】 請求項１に記載のキトサン誘導体を用い
て金属イオンを選択的に回収する方法であって、 （１）金属イオンを含有する溶液に、前記キトサン誘導
体を添加して、該キトサン誘導体に前記金属イオンを吸
着させるステップ、 （２）前記金属イオンが吸着した前記キトサン誘導体を
回収するステップ、 （３）該回収したキトサン誘導体から金属イオンを溶離
せしめるステップを具備する金属イオンを選択的に回収
する方法。3. A method for selectively recovering a metal ion using the chitosan derivative according to claim 1, wherein (1) adding the chitosan derivative to a solution containing the metal ion, Selectively adsorbing the metal ion to a derivative; (2) recovering the chitosan derivative to which the metal ion has been adsorbed; and (3) eluting the metal ion from the collected chitosan derivative. How to recover. 【請求項４】 前記金属イオンが、金イオン、白金イオ
ン、パラジウムイオン、水銀イオンのうちの少なくとも
一つから選択されることを特徴とする請求項３に記載の
方法。4. The method according to claim 3, wherein the metal ions are selected from at least one of gold ions, platinum ions, palladium ions, and mercury ions. 【請求項５】 前記金属イオンを含有する溶液が、酸性
であることを特徴とする請求項３又は４に記載の方法。5. The method according to claim 3, wherein the solution containing the metal ions is acidic. 【請求項６】 0.01〜5規定の酸と１規定のチオ尿素に
よって、金属イオンを溶離せしめることを特徴とする請
求項３〜５の何れか1項に記載の方法。6. The method according to claim 3, wherein the metal ion is eluted with 0.01 to 5 normal acid and 1 normal thiourea.
JP11068200A 1999-03-15 1999-03-15 Thiourea derivative of chitosan Pending JP2000264902A (en)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003020771A1 (en) * 2001-08-31 2003-03-13 Mucobiomer Biotechnologische Forschungs- Und Entwicklungs Gesmbh Chitosan-thio-amidine conjugates and their cosmetic as well as pharmaceutic use
JP2007050333A (en) * 2005-08-17 2007-03-01 Univ Of Miyazaki Adsorbent and production method thereof
RU2405047C2 (en) * 2008-12-15 2010-11-27 Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук Method of extracting gold from acid solutions
CN103275244A (en) * 2013-06-09 2013-09-04 中南大学 Chitosan-ester-based thiourea resin as well as preparation method and application thereof
CN103980385A (en) * 2014-04-28 2014-08-13 华南理工大学 O-quaternary-N-thiourea chitosan, preparation method and application thereof
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RU2405047C2 (en) * 2008-12-15 2010-11-27 Институт органического синтеза им. И.Я. Постовского Уральского отделения Российской академии наук Method of extracting gold from acid solutions
CN103275244A (en) * 2013-06-09 2013-09-04 中南大学 Chitosan-ester-based thiourea resin as well as preparation method and application thereof
CN103980385A (en) * 2014-04-28 2014-08-13 华南理工大学 O-quaternary-N-thiourea chitosan, preparation method and application thereof
CN104045734A (en) * 2014-07-08 2014-09-17 中国海洋大学 Preparation method of resin having high-efficiency adsorption effect on patulin
CN109824799A (en) * 2019-01-25 2019-05-31 佛山市海力盈生物科技有限公司 A kind of chitosan derivatives and preparation method thereof of sulfur-bearing urea structure
JP2020143322A (en) * 2019-03-05 2020-09-10 国立大学法人 宮崎大学 Precious metal separation and recovery method and precious metal fine particles recovered by that method
JP7217872B2 (en) 2019-03-05 2023-02-06 国立大学法人 宮崎大学 Noble metal separation and recovery method and precious metal fine particles recovered by the method
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CN113891899A (en) * 2019-05-30 2022-01-04 株式会社大赛璐 Chitosan compound and separating agent for optical isomers
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