JP2023528572A - 有機アミン精製方法 - Google Patents
有機アミン精製方法 Download PDFInfo
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- JP2023528572A JP2023528572A JP2022561384A JP2022561384A JP2023528572A JP 2023528572 A JP2023528572 A JP 2023528572A JP 2022561384 A JP2022561384 A JP 2022561384A JP 2022561384 A JP2022561384 A JP 2022561384A JP 2023528572 A JP2023528572 A JP 2023528572A
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- JP
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- Prior art keywords
- organic amine
- polymer matrix
- resin
- liquid containing
- metal element
- 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.)
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- 150000001412 amines Chemical class 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000000746 purification Methods 0.000 title claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 33
- 239000002184 metal Substances 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 32
- 239000011347 resin Substances 0.000 claims abstract description 32
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 claims abstract description 21
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007788 liquid Substances 0.000 claims abstract description 21
- 239000011159 matrix material Substances 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 18
- -1 amino compound Chemical class 0.000 claims abstract description 4
- 239000003456 ion exchange resin Substances 0.000 claims description 10
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 10
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 239000011324 bead Substances 0.000 claims description 4
- 239000011148 porous material Substances 0.000 claims description 4
- 239000012508 resin bead Substances 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043237 diethanolamine Drugs 0.000 claims description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940043276 diisopropanolamine Drugs 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 229940102253 isopropanolamine Drugs 0.000 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- 229960004418 trolamine Drugs 0.000 claims description 2
- 229920001429 chelating resin Polymers 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 9
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- 229910021645 metal ion Inorganic materials 0.000 description 7
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000012535 impurity Substances 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment Of Water By Ion Exchange (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
有機アミンは、金属イオンの良好な配位子であり、したがって、有機アミンを生成する場合、金属不純物は、一般的な問題である。現在、有機アミンから金属不純物を除去する信頼性のある方法は存在しない。水性及び/又は無機液体から金属不純物を除去するために存在する方法では、処理された液体中にかなりの金属イオンが残る。この一例は、水性及び/又は無機ブラインを処理する際のキレート化樹脂の使用である。キレート化樹脂は、典型的には、これらの液体から遷移金属又は貴金属を選択的に除去するために使用され、一般的ではあるが、処理された液体中にかなりの量(例えば、百万分率で検出可能な量)の金属が残る。加えて、これらのプロセスは、廃水、無機ブラインなどの処理にのみ好適であり、有機アミンを処理するためのそのようなプロセスは、現在利用可能ではない。
この実施例では、有機アミンである、N-メチルエタノールアミンを、制御試験下で、イミノ二酢酸を埋め込んだ樹脂(Puroliteから供給されるPuromet(登録商標)MTS9300)の使用を介して精製した。Puromet(登録商標)MTS9300は、廃水処理である。現在、これは有機アミン用の潜在的な処理として認識されておらず、廃水処理と有機アミン処理との間には、金属の種類の数、金属濃度、金属形態、pH値、液体粘度、適合性などを含む大きい違いが存在する。
Claims (10)
- 有機アミンの精製のための方法であって、
少なくとも1つの金属元素に結合した少なくとも1つの有機アミンを含有する液体に、樹脂ポリマーマトリックスを導入することを含み、
前記樹脂ポリマーマトリックスが、イミノ二酢酸、アミノメチルホスホン酸、又はそれらの組み合わせからなる群から選択されるアミノ化合物を埋め込んでおり、
埋め込んだ前記樹脂ポリマーマトリックスが、前記少なくとも1つの金属元素に結合し、
前記少なくとも1つの金属元素が、前記有機アミンから除去される、方法。 - 前記樹脂ポリマーマトリックスが、ポリアクリレート又はポリスチレン-ジビニルベンゼンを含む、請求項1に記載の方法。
- 前記樹脂ポリマーマトリックスの細孔径が、ガス吸着による固体の比表面積によって決定される、1~2,000nmの範囲である、請求項1に記載の方法。
- 前記樹脂ポリマーマトリックスが、樹脂ビーズとして、前記有機アミンを含有する液体に導入され、前記ビーズの粒径が、100~2000μmのサイズの範囲である、請求項1に記載の方法。
- アニオンイオン交換樹脂もまた、前記液体に導入される、請求項1に記載の方法。
- 前記液体の温度が、凍結~70℃の範囲である、請求項1に記載の方法。
- 前記液体の流量が、1~30BV/時間の範囲である、請求項1に記載の方法。
- 前記金属元素の80%超が、少なくとも1つの金属元素に結合した少なくとも1つの有機アミンを含有する液体から除去される、請求項1に記載の方法。
- 少なくとも1つの金属元素に結合した少なくとも1つの有機アミンを含有する液体に樹脂ポリマーマトリックスを導入した後、少なくとも1つの有機アミンを含有する前記液体中の金属元素の濃度が、1百万分率未満である、請求項1に記載の方法。
- 前記有機アミンが、高度に濃縮されたモノエタノールアミン、ジエタノールアミン、トリエタノールアミン、イソプロパノールアミン、ジイソプロパノールアミン、トリイソプロパノールアミン、N-メチルジエタノールアミン、又はアミノエチレンエタノールアミンを含む、請求項1に記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2020/083624 WO2021203255A1 (en) | 2020-04-08 | 2020-04-08 | Organic amine purification method |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2023528572A true JP2023528572A (ja) | 2023-07-05 |
Family
ID=78024063
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2022561384A Pending JP2023528572A (ja) | 2020-04-08 | 2020-04-08 | 有機アミン精製方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20230117989A1 (ja) |
EP (1) | EP4132903A4 (ja) |
JP (1) | JP2023528572A (ja) |
KR (1) | KR20230034935A (ja) |
CN (1) | CN115427392A (ja) |
WO (1) | WO2021203255A1 (ja) |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19806578A1 (de) * | 1998-02-17 | 1999-08-19 | Basf Ag | Verfahren zur Herstellung wäßriger, im wesentlichen metallionenfreier Hydroxylaminlösungen |
US20030155301A1 (en) * | 2002-01-04 | 2003-08-21 | General Electric Company | Method of purifying brine |
JP2005215627A (ja) * | 2004-02-02 | 2005-08-11 | Japan Organo Co Ltd | レジスト剥離廃液の再生処理方法及び装置 |
JP2006082288A (ja) * | 2004-09-14 | 2006-03-30 | Fuji Xerox Co Ltd | インクジェット用液体廃棄処理方法およびインクジェット記録装置 |
US7572379B2 (en) * | 2005-09-02 | 2009-08-11 | Sachem, Inc. | Removal of metal ions from onium hydroxides and onium salt solutions |
WO2007079944A1 (en) * | 2006-01-11 | 2007-07-19 | Dsm Ip Assets B.V. | Process for isolation of an organic amine |
CN101993387A (zh) * | 2010-11-03 | 2011-03-30 | 天津大学 | 电子级的n,n-二甲基甲酰胺的提纯方法 |
EP2935201A4 (en) * | 2012-12-21 | 2016-08-03 | Rhodia Operations | PROCESS FOR FORMATION OF PRIMARY, SECONDARY OR TERTIARY AMINE BY DIRECT AMINATION REACTION |
CN103102273B (zh) * | 2012-12-29 | 2016-04-27 | 上海新阳半导体材料股份有限公司 | 一种有机胺类电镀添加剂的纯化方法 |
CN103102279B (zh) * | 2012-12-29 | 2015-03-04 | 上海新阳半导体材料股份有限公司 | 一种单乙醇胺的纯化方法 |
-
2020
- 2020-04-08 JP JP2022561384A patent/JP2023528572A/ja active Pending
- 2020-04-08 CN CN202080100024.8A patent/CN115427392A/zh active Pending
- 2020-04-08 WO PCT/CN2020/083624 patent/WO2021203255A1/en active Application Filing
- 2020-04-08 US US17/905,877 patent/US20230117989A1/en active Pending
- 2020-04-08 KR KR1020227038411A patent/KR20230034935A/ko unknown
- 2020-04-08 EP EP20930126.6A patent/EP4132903A4/en active Pending
Also Published As
Publication number | Publication date |
---|---|
EP4132903A4 (en) | 2024-01-17 |
US20230117989A1 (en) | 2023-04-20 |
WO2021203255A1 (en) | 2021-10-14 |
EP4132903A1 (en) | 2023-02-15 |
KR20230034935A (ko) | 2023-03-10 |
CN115427392A (zh) | 2022-12-02 |
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