JP6956529B2 - 高純度イミダゾリウム塩の製造方法 - Google Patents
高純度イミダゾリウム塩の製造方法 Download PDFInfo
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- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 150000004693 imidazolium salts Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 239000012043 crude product Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002608 ionic liquid Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000004378 air conditioning Methods 0.000 description 6
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 carboxylic acid ion Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 231100000694 OECD Guidelines for the Testing of Chemicals Toxicity 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000007791 dehumidification Methods 0.000 description 2
- HQWOEDCLDNFWEV-UHFFFAOYSA-M diethyl phosphate;1-ethyl-3-methylimidazol-3-ium Chemical compound CC[N+]=1C=CN(C)C=1.CCOP([O-])(=O)OCC HQWOEDCLDNFWEV-UHFFFAOYSA-M 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Description
建物又は乗用車の換気及び空気調整のための空調システムでは、空気は一般的に冷却するだけではなく、除湿しなければならない。冷却すべき空気は、所望の温度への冷却に際して、露点を下回るほど湿度が高いからである。このため慣用の空調システムにおいては、空気の除湿が、電力消費の大部分を占める。
意外なことに上記問題は、本明細書に記載する方法によって解決される。
前記式中、Q+は、
a)式(II)の化合物を、式(III)の化合物と反応させる工程、ここで(II)及び(III)は、
b)工程a)からの式(I)の粗製生成物に水を添加する工程、これによって式(I)の化合物を含有する希釈された粗製生成物が得られ、
c)30〜180℃の範囲にある温度T1において、温度T1における化合物(III)の飽和蒸気圧よりも低い圧力p1で、前記希釈された粗製生成物を蒸留することによって、工程b)で添加した水を、前記希釈された粗製生成物から、少なくとも部分的に除去する工程、これによって、式(I)の高純度化合物が得られる、
を含み、
前記式中、
R1、R2、R3はそれぞれ独立して、水素であるか、又は1〜4個の炭素原子のアルキルであり、
R4、R5、R6、R7はそれぞれ独立して、1〜4個の炭素原子のアルキルである。
好ましい実施形態において、圧力p1はまた、化合物(I)の飽和蒸気圧よりも高く、さらにより好ましくは、化合物(I):水が99:1、さらにより好ましくは98:2、さらにより好ましくは97:3である混合物の飽和蒸気圧よりも高い。
材料
以下の実施例において、N−メチルイミダゾール(CAS No.616-47-7)、及びトリエチルホスフェート(CAS No.: 78-40-0)は、Sigma Aldrich社から購入したものである。
飽和蒸気圧は、OECD Guidelines for the Testing of Chemicals(化学物質の試験のためのガイドライン) (1981): Test No. 104, items 14〜19“Static Method”(2006年3月23日採用)に記載された方法に従って測定した。
トリフェニルホスフェート(929g、5.0mol)を、N−メチルイミダゾール(411g、5.0mol)を有する反応槽に滴加した。その後、反応混合物を最大150℃に加熱し、還流下で14時間、撹拌した。それからこの混合物を、(出発材料のトリエチルホスフェートと、N−メチルイミダゾールの合計質量に対して)20質量%の水で希釈し、以下の表にまとめたように、様々な圧力で水を留去した。
Claims (7)
- 式(I)Q+A-の高純度化合物の製造方法であって、
ここでQ+は、
前記製造方法は、
a)式(II)の化合物を、式(III)の化合物と反応させる工程、ここで、(II)及び(III)は、
b)工程a)からの式(I)の粗製生成物に水を添加する工程、これによって式(I)の化合物を含有する希釈された粗製生成物が得られ、
c)30〜180℃の範囲にある温度T1において、温度T1における化合物(III)の飽和蒸気圧よりも低い圧力p1で、前記希釈された粗製生成物を蒸留することによって、工程b)で添加した水を、前記希釈された粗製生成物から、少なくとも部分的に除去する工程、これによって、式(I)の高純度化合物が得られる、
を含み、
前記式中、
R1、R2、R3はそれぞれ独立して、水素であるか、又は1〜4個の炭素原子のアルキルであり、
R4、R5、R6、R7はそれぞれ独立して、1〜4個の炭素原子のアルキルであり、
圧力p1が、温度T1における化合物(III)の飽和蒸気圧よりも低く、温度T1における(I)の飽和蒸気圧よりも高く、且つ、工程a)を、溶媒の存在下で行う、
前記製造方法。 - 前記式中、R1=R2=R3=水素であり、R4、R5、R6、R7はそれぞれ独立して、メチル又はエチルである、請求項1に記載の製造方法。
- 前記式中、R1=R2=R3=水素であり、R5=メチルであり、R4、R6、R7はそれぞれ独立して、メチル又はエチルである、請求項2に記載の製造方法。
- 前記溶媒を、工程a)と、b)との間で少なくとも部分的に除去する、請求項1に記載の製造方法。
- 工程b)において、工程a)で使用する化合物(II)及び(III)の量に対して、少なくとも1質量%の量で水を添加する、請求項1から4までのいずれか1項に記載の製造方法。
- 工程c)における「部分的な除去」が、工程b)で添加された水の少なくとも50%の除去を意味する、請求項1から5までのいずれか1項に記載の製造方法。
- 工程b)及びc)を少なくとも2回行い、ここで工程b)を、直前の工程c)で得られた式(I)の高純度化合物を用いて行う、請求項1から6までのいずれか1項に記載の製造方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP16174303.4 | 2016-06-14 | ||
EP16174303.4A EP3257843A1 (en) | 2016-06-14 | 2016-06-14 | Method of preparing a high purity imidazolium salt |
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JP2017222657A JP2017222657A (ja) | 2017-12-21 |
JP6956529B2 true JP6956529B2 (ja) | 2021-11-02 |
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US (1) | US9840473B1 (ja) |
EP (1) | EP3257843A1 (ja) |
JP (1) | JP6956529B2 (ja) |
CN (1) | CN107501186A (ja) |
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DE102015212749A1 (de) | 2015-07-08 | 2017-01-12 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
DE102016210478A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
DE102016210484A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren zur Entfeuchtung von feuchten Gasgemischen |
DE102016210481B3 (de) | 2016-06-14 | 2017-06-08 | Evonik Degussa Gmbh | Verfahren zum Reinigen einer ionischen Flüssigkeit |
EP3257568B1 (de) | 2016-06-14 | 2019-09-18 | Evonik Degussa GmbH | Verfahren zur entfeuchtung von feuchten gasgemischen mit ionischen flüssigkeiten |
DE102016210483A1 (de) | 2016-06-14 | 2017-12-14 | Evonik Degussa Gmbh | Verfahren und Absorptionsmittel zur Entfeuchtung von feuchten Gasgemischen |
US11217828B2 (en) * | 2016-12-05 | 2022-01-04 | Massachusetts Institute Of Technology | Flame-retardant, non-toxic phosphate ester ionic liquid electrolytes and method of making |
EP4282890A1 (de) | 2022-05-25 | 2023-11-29 | Evonik Operations GmbH | Herstellung von polyurethanschaum unter verwendung von ionischen flüssigkeiten |
EP4282892A1 (de) | 2022-05-25 | 2023-11-29 | Evonik Operations GmbH | Herstellung von polyurethanschaum unter verwendung von katalysatoren auf basis ionischer flüssigkeiten |
CN116217620A (zh) * | 2023-01-10 | 2023-06-06 | 合肥学院 | 一种含磷卟啉及其制备方法与应用 |
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EP3257843A1 (en) | 2017-12-20 |
US20170355680A1 (en) | 2017-12-14 |
JP2017222657A (ja) | 2017-12-21 |
CN107501186A (zh) | 2017-12-22 |
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