CN116940403A - 通过使用超吸附剂吸附来纯化胺 - Google Patents
通过使用超吸附剂吸附来纯化胺 Download PDFInfo
- Publication number
- CN116940403A CN116940403A CN202280016821.7A CN202280016821A CN116940403A CN 116940403 A CN116940403 A CN 116940403A CN 202280016821 A CN202280016821 A CN 202280016821A CN 116940403 A CN116940403 A CN 116940403A
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- CN
- China
- Prior art keywords
- adsorbent
- mixture
- polyethylenimine
- silica
- amine
- 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
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- 150000001412 amines Chemical class 0.000 title claims abstract description 42
- 238000001179 sorption measurement Methods 0.000 title description 13
- 238000000746 purification Methods 0.000 title description 2
- 239000003463 adsorbent Substances 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 229920002873 Polyethylenimine Polymers 0.000 claims abstract description 30
- 229910052751 metal Inorganic materials 0.000 claims abstract description 25
- 239000002184 metal Substances 0.000 claims abstract description 25
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 25
- 229910021645 metal ion Inorganic materials 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 239000000356 contaminant Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- -1 polyethylene Polymers 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 4
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 4
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 229960002887 deanol Drugs 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 4
- 229940043276 diisopropanolamine Drugs 0.000 claims description 4
- 239000012972 dimethylethanolamine Substances 0.000 claims description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 3
- 230000008014 freezing Effects 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000412 dendrimer Substances 0.000 claims 1
- 229920000736 dendritic polymer Polymers 0.000 claims 1
- 150000002739 metals Chemical class 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 description 15
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 6
- 229910052761 rare earth metal Inorganic materials 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 229940001587 tarka Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910052692 Dysprosium Inorganic materials 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 239000010842 industrial wastewater Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 2
- 239000006199 nebulizer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 229910021654 trace metal Inorganic materials 0.000 description 2
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000002133 sample digestion Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/60—Use in several different columns
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- 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
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/60—Use in several different columns
- B01J2220/603—Use in several different columns serially disposed columns
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- 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
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/60—Use in several different columns
- B01J2220/606—Use in several different columns parallel disposed columns
Abstract
本发明描述了一种用以去除包含一种或多种有机胺的混合物中存在的金属的方法,该方法包括使所述混合物与二氧化硅‑聚乙烯亚胺吸附剂接触的步骤。
Description
对于许多应用,诸如电子和药物生产工艺,需要高纯度胺。在一些应用中,希望金属离子杂质少于十亿分之10。然而,很少报道用于从诸如胺的有机溶液中去除金属离子的方法。相反,大多数可获得的文献通常集中于从水性溶液中去除金属离子。离子交换树脂的使用是用于去除金属离子的最常研究的方法,包括使用具有不同官能团的螯合树脂。然而,由于金属离子与胺之间的强键合亲和力或此类树脂与胺之间的不相容性问题,使用此类技术从胺溶液中去除金属离子是一个挑战。
本发明公开了利用特殊种类的超吸附剂从胺中去除痕量金属杂质。这种吸附剂是基于用支化聚乙烯亚胺改性的二氧化硅颗粒的。所述方法提供了对有机胺中存在的大多数金属杂质的高吸附容量。
具体实施方式
本发明描述了一种用以去除包含一种或多种有机胺的混合物中存在的金属的方法,该方法包括使所述混合物与二氧化硅-聚乙烯亚胺吸附剂接触的步骤。
从理论上讲,胺与金属离子杂质的任何溶液均可以受益于本发明,因为所有溶液均具有胺官能团,这使得金属去除在通常用于去除金属杂质的大多数技术中成为问题。胺可以是烷基胺和/或芳族胺。胺可以是伯胺、仲胺、叔胺、环胺或它们的组合。这包括单乙醇胺(MEA)、二乙醇胺(DEA)、三乙醇胺(TEA)、单异丙醇胺(MIPA)、二异丙醇胺(DIPA)、三异丙醇胺(TIPA)、n-甲基二乙醇胺(MDEA)、n-甲基乙醇胺(NMEA)、乙二胺(EDA)、哌嗪(PIP)、二亚乙基三胺(DETA)、氨基乙基乙醇胺(AEEA)、氨基乙基哌嗪(AEP)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、二甲基乙醇胺(DMEA)、聚乙烯多胺和五亚乙基六胺混合物。
这些胺材料可以是纯的或包含在与这些材料中的两种或更多种的混合物中,单独或在溶剂中。该溶剂可以是水或与胺相容的任何有机溶剂(以它们的组合)。该有机溶剂可以有利地是醇、苯或醚。
该方法包括使纯胺或胺混合物与二氧化硅-聚乙烯亚胺吸附剂接触的步骤。合适的二氧化硅-聚乙烯亚胺吸附剂描述于以下参考文献中:US 2021/0016246A1;US2021/0017047;“用于从水源中回收稀土元素的新型聚乙烯亚胺-丙烯酰胺/SiO2杂化水凝胶吸附剂”,Qiuming Wang,Walter C.Wilfong,Brian W.Kail,Yang Yu和McMahan L.Gray,“ACS可持续化学与工程”,2017年9月14日;“用多孔胺-环氧基网络从水性溶液中回收稀土元素”,Walter Christopher Wilfong,Brian W.Kail,Tracy L.Bank,Bret H.Howard和McMahanL.Gray,“ACS应用材料与界面”,2017年5月12日;“用于从水性溶液中选择性回收重稀土元素(镝、镱)的胺吸附剂”,Qiuming Wang,Brian W.Kail,Walter C.Wilfong,Fan Shi,Thomas J.Tarka和McMahan L.Gray,“化学与化学”,2020,85 130-136;和“用于从工业废水中去除重金属和REE的稳定固定化胺吸附剂”,Walter Christopher Wilfong,Brianw.Kail,Qiuming Wang,Fan Shi,Greg Shipley,Thomas J.Tarka和McMahan L.Gray,“环境科学:水研究技术”,2020,6,1286。
二氧化硅-聚乙烯亚胺吸附剂是聚乙烯亚胺改性的二氧化硅颗粒,其包含二氧化硅载体、结合到二氧化硅载体的交联剂和结合到交联剂的聚乙烯亚胺。聚乙烯亚胺可以是直链、支链或树枝状的形式。优选地,聚乙烯亚胺为支链或树枝状的形式。理论上,亚胺官能团比胺对金属离子具有更高的亲和力,并且高度支化的材料将具有不同类型和潜在的更多官能团,因此对金属离子的亲和力甚至更高。直链聚乙烯亚胺全部含有仲胺。支链聚乙烯亚胺可含有伯、仲和叔氨基。树枝状聚乙烯亚胺含有伯氨基和叔氨基。聚乙烯亚胺的重均分子量范围为500Da,优选800Da、5,000Da或甚至10,000Da至50,000Da、75,000Da、90,000Da或甚至1,000,000Da。
二氧化硅-聚乙烯亚胺-改性的二氧化硅载体可优选使用本领域通常已知的交联剂制备。该交联剂可包含环氧硅烷连接基、三环氧化物连接基或丙烯酰胺基连接基。优选的交联剂包括2-(3,4-环氧环己基)乙基三甲氧基硅烷(ECTMS)、二苯基A二缩水甘油醚、N-N-二缩水甘油基-4-缩水甘油基氧基苯胺(E3)或4,4'-亚甲基双(N,N-二缩水甘油基苯胺)、丙烯酰胺、N,N'-亚甲基双丙烯酰胺或它们的混合物。
可以以任何合适的方式使二氧化硅-聚乙烯亚胺吸附剂与含胺混合物接触。例如,其可在分批方法中进行,其中将二氧化硅-聚乙烯亚胺吸附剂添加到含胺混合物中,优选伴随搅拌、摇动或一些其它工艺以增加吸附剂与胺中的金属杂质之间的接触。通常,在这种分批方法中,杂质的去除速率和由此产生的残留在含胺混合物中的杂质水平将是特定吸附剂的功效、吸附剂的量相对于含胺混合物的量、搅拌速率以及允许继续接触的时间的函数,如本领域普通技术人员所理解的。
还可以具有使胺或含胺混合物与吸附剂接触的连续方法。这可以方便地通过使含胺混合物通过二氧化硅-聚乙烯亚胺吸附剂的固定床来进行。床体积(或BV)可以根据起始材料中存在的污染物水平和最终产物的期望纯度水平来配置,其中较大的床体积通常能够在较短的时间段内去除较大量的污染物。
从固定床中去除杂质的效率也是混合物通过固定床的流速的函数。混合物通过床的流速可有利地被调节至1BV/小时至30BV/小时的范围内,更优选地1BV/小时至10BV/小时的范围内,其中BV是床的体积。例如,如果吸附剂的床体积为1升,则流速可被有利地设定为1升/小时至30升/小时的速率,更优选1升/小时至10升/小时的范围内。如本领域普通技术人员将理解的,对于给定的系统,较慢的流速导致更多的杂质被去除,但是增加了方法的时间。
在一些实施方案中,可使混合物通过二氧化硅-聚乙烯亚胺吸附剂的两个或更多个固定床。那些额外的床可以并联或串联布置,或者如果使用至少三个床,则是并联和串联配置的组合。
使含胺混合物与二氧化硅-聚乙烯亚胺吸附剂接触的方法(无论是以分批方法还是以连续方法)可在从混合物的凝固点至略低于混合物的沸点范围内的任何温度下进行。
在与混合物接触之前,可有利地用水或其它溶剂洗涤二氧化硅-聚乙烯亚胺吸附剂,以从吸附剂材料中去除可能的污染物杂质,并因此延长寿命并提高吸附剂的金属去除效率。优选地,该洗涤可以进行两次或更多次,以便从新鲜吸附剂中去除甚至更多的污染物杂质。
在使用期间,从胺中去除的金属杂质将随时间积聚在吸附剂上。因此,可能希望周期性地再生吸附剂。这可以方便地通过使吸收剂与弱酸液体或弱酸水性溶液在从液体的凝固点至略低于液体的沸点范围内的任何温度下接触来实现。弱酸是在水性溶液或水中部分解离成其离子的酸。例如,所述弱酸包括乙酸、甲酸、氢氰酸、氢氟酸、硫化氢、三氯乙酸或它们的混合物。这种弱酸液体或弱酸水性溶液的pH范围为2至7。还可以使用金属离子对其具有更高亲和力的其他材料(诸如氨,氨是更强的胺(与吸附剂相比))来再生吸附剂。
本发明的方法可用于将含胺混合物中的金属杂质水平降低至小于10ppb、或甚至小于5ppb的金属污染物水平。
实验
材料:将未洗涤的支链聚乙烯亚胺改性的二氧化硅吸附剂用作以下各实施例的吸附剂。该吸附剂是在以下参考文献中描述的种类:US 2021/0016246A1;US2021/0017047;“用于从含水源再回收稀土元素的新型聚乙烯亚胺-丙烯酰胺/SiO2杂化水凝胶吸附剂,Qiuming Wang,Walter C.Wilfong,Brian W.Kail,Yang Yu和McMahan L.Gray,“ACS可持续化学与工程”,2017年9月14日;“用多孔胺-环氧基网络从水性溶液中回收稀土元素”,Walter Christopher Wilfong,Brian W.Kail,Tracy L.Bank,Bret H.Howard和McMahanL.Gray,“ACS应用材料与界面”,2017年5月12日;“用于从水性溶液中选择性回收重稀土元素(镝、镱)的胺吸附剂”,Qiuming Wang,Brian W.Kail,Walter C.Wilfong,Fan Shi,Thomas J.Tarka和McMahan L.Gray,“化学与化学”,2020,85 130-136;和“用于从工业废水中去除重金属和REE的稳定固定化胺吸附剂”,Walter Christopher Wilfong,Brianw.Kail,Qiuming Wang,Fan Shi,Greg Shipley,Thomas J.Tarka和McMahan L.Gray,“环境科学:水研究技术”,2020,6,1286。将n-甲基乙醇胺(NMEA)样品(可从Dow ChemicalCompany商购获得,>99%NMEA纯胺液体)用作这些实施例中的每一个实施例的待纯化的目标胺液体。
金属浓度分析通过ICP-MS进行。Agilent 7900x ICP-MS仪器配备有惰性聚四氟乙烯(PFA)微流喷雾器、PFA喷雾室和石英样品引入系统,以便消除来自有机基质、运载气体等的干扰。7900ICP-MS仪器配备有Octopole反应池(ORC)、He和H2池气体管线。该系统可以利用碰撞/反应单元(CRC)技术去除多原子干扰。ICP-MS仪器是配备有ISO 100级清洁罩的ISO100级清洁室。样品制备(包括称重、消化和分析)在清洁化学之后进行。在Agilent 7900xICP-MS上进行分析。该仪器配备有200μL自吸PFA微流喷雾器、具有1.5mm内径注射器的PFA喷雾室和铂界面(采样器锥和分流器锥)。为了达到高灵敏度和低背景并减少任何多原子干扰,在无气体、H2反应和氦碰撞模式下用1ppb调谐溶液调谐ICP-MS仪器。
用于ICP-MS分析的化学品和试剂包括:硝酸、多元素标准品和ICP-MS调谐溶液。硝酸是超痕量金属级或最佳级。它们用于样品消化和用于制备校准标准品和调整溶液。在N2气、H2气和He气的模式下调节和校准该仪器。使用在5%硝酸中配制的0、0.25、1、5和10ng/mL校准标准品(SPEX CertiPrep,多元素标准品)在0ng/mL-10ng/mL的范围内校准仪器。
为了通过ICP-MS分析金属,需要去除胺样品中的有机物。这通常可以通过在氮气吹扫下在热块中在低于沸点的温度下蒸发至干来进行。然后将残余物重新溶解在硝酸中并用水稀释。使用电感耦合等离子体质谱(ICP-MS),使用如上所述的Agilent 7900ICP-MS分析所制备的溶液。
实施例1:分批法
如表1所示,将五种不同量的相同吸附剂分别加入到五个塑料瓶中。将大约相同量的NMEA添加到每个瓶中。在加入NMEA溶液后,将五个瓶置于机械摇动器上摇动过夜,以加速吸附平衡。振荡后,使吸附剂在瓶中沉淀下来,取液体样品进行金属分析。还分析原始未处理的NMEA样品的金属含量作为对照。
表1显示了实验结果。如该表所示,原始NMEA对照样品具有浓度分别为97、9、47ppb的Fe、Cu和Zn离子。对于测试1至5,NMEA胺液体量几乎相同,每次测试的吸附剂剂量从测试1增加至测试5。表1表明,施加的吸附剂越多,从液体NMEA中去除的金属离子越多。例如,对于Fe3+金属离子,在测试5中,在施加0.816克吸附剂之后,在NMEA中仅剩下4ppb Fe3+处于平衡。对于另一个实施例,对于Zn2+,即使在测试4中仅施加0.405克吸附剂之后,在平衡时在NMEA中仅留下3ppb Zn2+。对于第三实施例,对于Cu2+,在测试5中施加0.816克吸附剂后,在NMEA中剩余2ppb Cu2+达到平衡。
如可以看出,当适当设计时,使用这类吸附剂的吸附器可以提供超过95%的主要金属污染物(诸如Fe和Zn)的去除效率,以及良好的操作寿命。
表1在使用不同量的NETL吸附剂的测试中的金属浓度
实施例2:固定床吸附实验
吸附柱由聚丙烯制成,其中聚丙烯玻璃料作为吸附介质的载体。填充到柱中的超吸附剂的量为0.985g,并且吸附剂床的体积为2.85mL。NMEA由购自Alltech的液相色谱泵(型号626)泵送。泵由不含金属的PEEK材料构成。在整个吸附实验时间期间保持1.0ml/min(21床体积(“BV”)/小时)的流速。在之前和之后收集对照样品以确保没有来自泵配件和管的污染。以规则的间隔,在柱的出口处收集约1-2ml样品用于分析测量。来自该固定床吸附实验的结果示于表2中。
表2固定床吸附穿透实验-在不同量的处理的NMEA下的流出物金属浓度
固定床吸附结果显示出NMEA(对照)中存在的基本上所有金属杂质都被超吸附剂吸附至一定程度。金属浓度的一些波动最可能是由于分析或实验误差。以Fe3+金属离子为例,当140BV的NMEA通过吸附剂柱进料时,流出物中的Fe3+浓度为26ppb,从NMEA进料(对照)中的84ppb下降。以Cu2+作为另一个实施例,当140BV的NMEA通过吸附剂柱进料时,其在流出物中的浓度为2ppb,从NMEA进料(对照)中的16ppb下降。以Zn2+作为第三个实施例,当42BV的NMEA通过吸附剂柱进料时,其在流出物中的浓度为3ppb,从NMEA进料(对照)中的158ppb下降。在将42BV的NMEA进料到柱中之后,更多的Zn2+开始缓慢地穿过吸附床,如随着更多的NMEA通过柱进料到Zn2+浓度缓慢增加所证明的。超吸附剂对不同的金属具有不同的吸附能力。因此,每种金属在固定床吸附塔中的穿透时间将是不同的。注意,所讨论的实施例结果是在21BV/小时的进料流速下进行的。当进料流速较低时,特别是在1-10BV/小时的优选范围内时,金属去除效率将较高并且流出物中的金属浓度将较低。
Claims (18)
1.一种用以去除包含一种或多种有机胺的混合物中存在的金属离子的方法,所述方法包括使所述混合物与二氧化硅-聚乙烯亚胺吸附剂接触的步骤。
2.根据权利要求1,其中所述聚乙烯亚胺是直链、支链或树枝状体。
3.根据权利要求1所述的方法,其中,所述待去除的金属离子包括Fe、Zn、Cr、Mn、Co、Ni、Cu、Cd、Li、Na、K、Mg、Ca、Sr、Ba、Al、Pb和Sb中的至少一种。
4.根据权利要求1所述的方法,其中所述有机胺选自由以下项组成的组:单乙醇胺(MEA)、二乙醇胺(DEA)、三乙醇胺(TEA)、单异丙醇胺(MIPA)、二异丙醇胺(DIPA)、三异丙醇胺(TIPA)、N-甲基二乙醇胺(MDEA)、N-甲基乙醇胺(NMEA)、乙二胺(EDA)、哌嗪(PIP)、二亚乙基三胺(DETA)、氨基乙基乙醇胺(AEEA)、氨基乙基哌嗪(AEP)、三亚乙基四胺(TETA)、四亚乙基五胺(TEPA)、二甲基乙醇胺(DMEA)、聚乙烯多胺、五亚乙基六胺混合物、以及它们的组合。
5.根据权利要求1所述的方法,其中使所述混合物通过二氧化硅-聚乙烯亚胺吸附剂的固定床。
6.根据权利要求5所述的方法,其中所述混合物通过所述床的流速在1BV/小时至30BV/小时的范围内,其中BV是所述床的体积。
7.根据权利要求6所述的方法,其中所述混合物通过所述床的所述流速在1BV/小时至10BV/小时的范围内。
8.根据权利要求5所述的方法,其中使所述混合物通过两个或更多个二氧化硅-聚乙烯亚胺吸附剂的固定床,其中所述两个或更多个床以并联、串联或并联和串联回路的组合布置。
9.根据权利要求8所述的方法,其中所述两个或更多个床以并联回路布置。
10.根据权利要求1所述的方法,其中将所述二氧化硅-聚乙烯亚胺吸附剂加入到所述混合物中并混合。
11.根据权利要求1所述的方法,其中使所述混合物与所述二氧化硅-聚乙烯亚胺吸附剂在从所述混合物的凝固点至略低于所述混合物的沸点范围内的温度下接触。
12.根据权利要求1所述的方法,其中在接触所述混合物之前,用水或其它溶剂洗涤所述二氧化硅-聚乙烯亚胺吸附剂。
13.根据权利要求12所述的方法,其中用水或其它溶剂洗涤所述二氧化硅-聚乙烯亚胺吸附剂两次或更多次。
14.根据权利要求1所述的方法,其中通过使所述吸附剂与所述金属离子对其具有更高亲和力的材料,诸如弱酸或弱酸水性溶液或相对较强的胺接触来周期性地再生所述二氧化硅-聚乙烯亚胺吸附剂。
15.根据权利要求14所述的方法,其中所述接触材料是弱酸并且包括乙酸、甲酸、氢氰酸、氢氟酸、硫化氢、三氯乙酸或它们的混合物。
16.根据权利要求14所述的方法,其中所述接触材料是氨。
17.根据权利要求7所述的方法,其中所述床的体积被配置为在给定期望流速的情况下将特定金属污染物的量降低至期望水平。
18.根据权利要求17所述的方法,其中所述金属污染物的期望水平小于10ppb。
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