JP7399498B2 - 標的物質の流体からの除去のための収着剤として、粒子状固体支持体にグラフト化された変性ポリアミン - Google Patents
標的物質の流体からの除去のための収着剤として、粒子状固体支持体にグラフト化された変性ポリアミン Download PDFInfo
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- JP7399498B2 JP7399498B2 JP2021501108A JP2021501108A JP7399498B2 JP 7399498 B2 JP7399498 B2 JP 7399498B2 JP 2021501108 A JP2021501108 A JP 2021501108A JP 2021501108 A JP2021501108 A JP 2021501108A JP 7399498 B2 JP7399498 B2 JP 7399498B2
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- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B11/00—Obtaining noble metals
- C22B11/04—Obtaining noble metals by wet processes
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B3/00—Extraction of metal compounds from ores or concentrates by wet processes
- C22B3/20—Treatment or purification of solutions, e.g. obtained by leaching
- C22B3/22—Treatment or purification of solutions, e.g. obtained by leaching by physical processes, e.g. by filtration, by magnetic means, or by thermal decomposition
- C22B3/24—Treatment or purification of solutions, e.g. obtained by leaching by physical processes, e.g. by filtration, by magnetic means, or by thermal decomposition by adsorption on solid substances, e.g. by extraction with solid resins
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- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
- C22B59/00—Obtaining rare earth metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
- B01J2220/4825—Polysaccharides or cellulose materials, e.g. starch, chitin, sawdust, wood, straw, cotton
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/36—Organic compounds containing halogen
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Description
R1は、C2~C22の分岐、直鎖、もしくは環状アルキル、またはアリール基である。
R2は、ハライドである。
本発明の新規なカスタム顆粒状媒体(CGM)組成物は、それらの独特の構造(図1を参照されたい)に起因して、部分的に、PFASの吸着のための有意に改善された能力を実証する。この図は、ヘキサノイルクロリドとの反応を介して、複数のC6の疎水基に共有結合したポリエチレンイミン(平均分子量、25,000)に共有結合した多孔質、固体、粒子状、リグノセルロース材料を含む組成物の電子顕微鏡写真を示す。この組成物は、マイクロメートルスケールで表面粗さを示し、大量のPFASの吸着を可能にする。
本発明のCGM組成物のPFASの結合能力を、GACおよびAmberlite(登録商標)アニオン交換樹脂と比較して模擬廃水で試験した。0.05gの吸着剤顆粒を、250ppmの競合する有機酸を含有するDI水中の2.5ppmのPFOS、PFOA、PFBS、およびPFBAの40mLに浸漬させるバッチ試験を実施した。24時間後、各溶液中のPFAS濃度を、実施例1と同様にLC-MS/MSを使用して定量化した。試験結果を図3に記載する。全ての場合において、本発明の組成物であるCGMは、従来の収着剤媒体よりも優れていた。
本発明のCGM組成物を、工業または農業供給源からの廃液で遭遇する可能性があるように、酸性から塩基性条件までのpH範囲にわたる吸着性能について試験した。このアッセイによれば、0.05gの吸着剤顆粒を、2.5ppmのPFOAまたはPFHSのDI水溶液40mLに浸漬させ、pHをNaOHまたはHClで適宜調整した。24時間後、溶液中のPFAS濃度を、実施例1に従ってLC-MS/MSを使用して定量化した。結果を図4に示す。このように、PFAS吸着の高レベル(>97%)が観察され、試験された全てのpH範囲にわたって驚くほど安定したままである。
本発明のCGM組成物を、汚染物質PFHSの除去のための急速小規模カラム試験で試験した。汚染水流入液(供給)には、500ppbのPFHSが含有されており、CGM組成物および競争相手の顆粒状活性炭(GAC)の小さな充填床にポンプで送った。接触時間は22秒、線速度は7.5m/時であった。流出溶液の試料を採取し、PFHSをLC-MS/MSで定量化した。結果を図5に示す。CGM組成物は、処理されている流入溶液の20,000床体積(BV)にわたって検出不能レベルまでの標的汚染物質の除去を示した。これはGACでは達成されなかった。そこでは、従来の収着剤媒体は、約50ppbまで急速に上昇した流出物濃度を示した。
本発明のCGM組成物を、バッチ試験において、PFOA、PFBA、およびPFBSを含有する汚染溶液と混合した。CGM組成物は、材料1グラムあたり50μgの総汚染物質を吸着した(50μg/g装填)。次いで、装填されたCGM培地を、8mlの充填床に充填した。3%の水酸化アンモニウム水溶液の再生溶液を、15分の接触時間でポンプで送った。カラムを通過した総再生溶液を収集し、2床体積(8ml)ごとにサンプリングした。PFOA、PFBA、およびPFBS濃度をLC-MS/MSで定量化し、化合物の総回収量を、初期装填量に基づいて計算した。結果を図6に示す。短鎖のPFBAおよびPFBSを迅速に回収し、6床体積の再生剤溶液の後、全ての標的物質を収着剤組成物から回収し、それらは、使用済み再生剤溶液に存在する。
Claims (20)
- 標的物質を流体流から除去するための組成物であって、分岐ポリアミンおよび共有結合した疎水基を含み、前記分岐ポリアミンがセルロースを含む支持材料に共有結合しており、前記分岐ポリアミンが、アミド結合、尿素結合、チオ尿素結合、イソチオウロニウム結合およびグアニジニウム結合からなる群から選択される結合を介して、前記疎水基と結合しているPFASを除去するための組成物。
- 前記支持材料が、リグノセルロース、バクテリアセルロース、微結晶性セルロース、ミクロフィブリル化セルロースおよびセルロース誘導体からなる群のうちの1種以上から選択される材料から構成されている、請求項1に記載のPFASを除去するための組成物。
- 前記支持材料が、セルロースまたはリグノセルロースの粉末あるいはパルプを含む、請求項2に記載のPFASを除去するための組成物。
- 前記支持材料が、粒子形状であり、複数の顆粒、フレーク、ビーズ、ペレットおよびパスティルからなる群のうちの1種以上を含む、請求項1~3のいずれか1項に記載のPFASを除去するための組成物。
- 前記分岐ポリアミンが、ポリエチレンイミン(PEI)である、請求項1~4のいずれか1項に記載のPFASを除去するための組成物。
- 前記疎水基が、ブチル、ヘキシルまたはオクチル基からなる群から選択されるC2~C22アルキル基を含む、請求項1~5のいずれか1項に記載のPFASを除去するための組成物。
- 前記疎水基が、イソブチル、イソヘキシルまたはイソオクチル基からなる群から選択されるC2~C22アルキル基を含む、請求項1~5のいずれか1項に記載のPFASを除去するための組成物。
- 前記疎水基が、ポリもしくはパーフルオロアルキル基、C8パーフルオロオクタン、または6:2フルオロテロマーを含む、請求項1~7のいずれか1項に記載のPFASを除去するための組成物。
- 収着剤分子が複数の疎水基を含む、請求項1~8のいずれか1項に記載のPFASを除去するための組成物。
- 流体流を請求項1~9のいずれか1項に記載のPFASを除去するための組成物と接触させることを含む、ポリおよびパーフルオロ化アルキル物質(PFAS)を流体流から除去するためのプロセス。
- 前記流体が液体であり、前記液体が、水、有機溶媒、液体化石燃料、液体潤滑剤、イオン液体、および作動流体から任意に選択される、請求項10に記載のプロセス。
- 前記PFASが、パーフルオロブタンスルホネート(PFBS)、パーフルオロブタン酸(PFBA)、パーフルオロヘキサンスルホネート(PFHS)、パーフルオロヘキサン酸(PFHA)、パーフルオロオクタン酸(PFOA)、パーフルオロオクタンスルホネート(PFOS)、パーフルオロノナン酸(PFNA)およびパーフルオロデカン酸(PFDA)、および6:2フルオロテロマースルホン酸(6:2 FTSA)からなる群から選択される1種以上を含む、パーフルオロ化アニオン性界面活性剤化合物から選択される、請求項11に記載のプロセス。
- 前記支持材料が、膜または膜様フィルターに組み込まれているセルロースまたはリグノセルロースの粉末あるいはパルプである、請求項12に記載のプロセス。
- 前記支持材料が、多孔質、固体および粒子状であり、顆粒、フレーク、ビーズ、ペレットおよびパスティルからなる群のうちの1種以上の形態である、請求項10~12のいずれか1項に記載のプロセス。
- 前記支持材料が床または充填カラム内に含まれ、前記流体流が前記床または充填カラムを通って、またはその全域にわたって通過する、請求項10~14のいずれか1項に記載のプロセス。
- 前記プロセスが、汚染物質を前記流体流から除去した後に前記組成物を再生することをさらに含む、請求項10~15のいずれか1項に記載のプロセス。
- 前記組成物を再生することが、1種以上の水性液体洗浄剤を前記組成物に適用することを含み、前記液体洗浄剤のうちの1種以上が塩洗浄剤であり、前記塩が、塩化物、硫酸塩またはリン酸塩対イオンを有するナトリウム、カリウムまたはマグネシウム塩からなる群のうちの1種以上から任意に選択される、請求項16に記載のプロセス。
- 前記組成物を再生することが、1種以上の水性液体洗浄剤を前記組成物に適用することを含み、前記液体洗浄剤のうちの1種以上が酸性洗浄剤であり、前記酸が、塩酸、硫酸、硝酸、リン酸、エタン二酸、ヘキサン酸、またはクエン酸からなる群のうちの1種以上から任意に選択される、請求項16または17に記載のプロセス。
- 前記組成物を再生することが、1種以上の水性液体洗浄剤を前記組成物に適用することを含み、前記液体洗浄剤のうちの1種以上が塩基性洗浄剤であり、前記塩基が、水酸化アンモニウム、水酸化ナトリウムおよび水酸化カリウムからなる群のうちの1種以上から任意に選択される、請求項16~18のいずれか1項に記載のプロセス。
- 請求項1~9のいずれか1項に記載のPFASを除去するための組成物を製造する方法であって、
a.セルロースを含む支持材料を用意することと、
b.前記支持材料を、分岐ポリアミン基および共有結合した疎水基を含む汚染物質-収着剤分子に共有結合させることと、を含む、方法。
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US20220370982A1 (en) * | 2021-05-21 | 2022-11-24 | The Regents Of The University Of Michigan | Ionic-functionalized wood pulp and related methods for water treatment |
CA3225764A1 (en) * | 2021-07-12 | 2023-01-19 | Paul Charles Wegner | Method and system of removing environmental contaminants from water |
CA3239484A1 (en) * | 2021-12-16 | 2023-06-22 | Ionic Water Technologies, LLC | Regeneratable system for contaminant removal |
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CN114534155B (zh) * | 2022-01-25 | 2023-06-06 | 中国船舶重工集团公司第七一八研究所 | 一种固态二氧化碳灭火材料的制备方法 |
GB202202072D0 (en) * | 2022-02-16 | 2022-03-30 | Puraffinity Ltd | Functionalised alumina adsorbent materials for removal of contaminants from water |
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JP2013078724A (ja) | 2011-10-04 | 2013-05-02 | Kochi Prefecture | 酸素酸イオン収着材、該収着材の製造方法および該収着材を使用した処理原液の酸素酸イオン収着処理方法 |
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US12005423B2 (en) | 2024-06-11 |
KR20210005026A (ko) | 2021-01-13 |
EP3774026C0 (en) | 2024-06-05 |
EP3774026B1 (en) | 2024-06-05 |
SG11202009510UA (en) | 2020-10-29 |
CN112236225A (zh) | 2021-01-15 |
JP2024023455A (ja) | 2024-02-21 |
AU2019244402A1 (en) | 2020-10-15 |
WO2019186166A1 (en) | 2019-10-03 |
GB201805058D0 (en) | 2018-05-09 |
EP4321248A3 (en) | 2024-05-22 |
US20240181429A1 (en) | 2024-06-06 |
JP2021519211A (ja) | 2021-08-10 |
US20210008522A1 (en) | 2021-01-14 |
EP4321248A2 (en) | 2024-02-14 |
CA3095230A1 (en) | 2019-10-03 |
EP3774026A1 (en) | 2021-02-17 |
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