JP6059140B2 - 電気化学セル - Google Patents
電気化学セル Download PDFInfo
- Publication number
- JP6059140B2 JP6059140B2 JP2013518759A JP2013518759A JP6059140B2 JP 6059140 B2 JP6059140 B2 JP 6059140B2 JP 2013518759 A JP2013518759 A JP 2013518759A JP 2013518759 A JP2013518759 A JP 2013518759A JP 6059140 B2 JP6059140 B2 JP 6059140B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- reaction
- catalyst
- choline
- cocatalyst
- 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.)
- Expired - Fee Related
Links
- 238000006243 chemical reaction Methods 0.000 claims description 177
- 239000001257 hydrogen Substances 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 111
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 110
- 229910052763 palladium Inorganic materials 0.000 claims description 34
- 229910052697 platinum Inorganic materials 0.000 claims description 31
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 30
- 229910052759 nickel Inorganic materials 0.000 claims description 16
- 229910052718 tin Inorganic materials 0.000 claims description 16
- 239000001569 carbon dioxide Substances 0.000 claims description 15
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 12
- 229960001231 choline Drugs 0.000 claims description 11
- 229910052804 chromium Inorganic materials 0.000 claims description 11
- 150000003248 quinolines Chemical class 0.000 claims description 11
- 229910052707 ruthenium Inorganic materials 0.000 claims description 11
- 229910052709 silver Inorganic materials 0.000 claims description 11
- 229910052793 cadmium Inorganic materials 0.000 claims description 10
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 229910052787 antimony Inorganic materials 0.000 claims description 9
- 229910052797 bismuth Inorganic materials 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- 229910052745 lead Inorganic materials 0.000 claims description 9
- 229910052721 tungsten Inorganic materials 0.000 claims description 9
- 229910052726 zirconium Inorganic materials 0.000 claims description 9
- 229910052684 Cerium Inorganic materials 0.000 claims description 8
- 229910052772 Samarium Inorganic materials 0.000 claims description 8
- 229910052771 Terbium Inorganic materials 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 8
- 229910052735 hafnium Inorganic materials 0.000 claims description 8
- 229910052738 indium Inorganic materials 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- 229910052746 lanthanum Inorganic materials 0.000 claims description 8
- 229910052748 manganese Inorganic materials 0.000 claims description 8
- 229910052750 molybdenum Inorganic materials 0.000 claims description 8
- 229910052758 niobium Inorganic materials 0.000 claims description 8
- 229910052702 rhenium Inorganic materials 0.000 claims description 8
- 229910052703 rhodium Inorganic materials 0.000 claims description 8
- 229910052715 tantalum Inorganic materials 0.000 claims description 8
- 229910052716 thallium Inorganic materials 0.000 claims description 8
- 229910052720 vanadium Inorganic materials 0.000 claims description 8
- 229910052779 Neodymium Inorganic materials 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 155
- 229910002091 carbon monoxide Inorganic materials 0.000 description 155
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 106
- 239000003054 catalyst Substances 0.000 description 73
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 63
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 63
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 53
- 235000019253 formic acid Nutrition 0.000 description 53
- 239000000203 mixture Substances 0.000 description 53
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 49
- 229960003178 choline chloride Drugs 0.000 description 49
- 235000019743 Choline chloride Nutrition 0.000 description 45
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 45
- 238000000034 method Methods 0.000 description 43
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 32
- 239000003792 electrolyte Substances 0.000 description 31
- 229910052737 gold Inorganic materials 0.000 description 31
- 239000010931 gold Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 239000000446 fuel Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 19
- 230000008569 process Effects 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- -1 carboxylic acid ions Chemical class 0.000 description 17
- 238000002484 cyclic voltammetry Methods 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 238000006722 reduction reaction Methods 0.000 description 16
- 238000012552 review Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- 239000011135 tin Substances 0.000 description 15
- 238000005259 measurement Methods 0.000 description 14
- 230000009467 reduction Effects 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 125000004122 cyclic group Chemical group 0.000 description 13
- 238000006056 electrooxidation reaction Methods 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 230000001629 suppression Effects 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- 238000001179 sorption measurement Methods 0.000 description 12
- 150000001412 amines Chemical group 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 238000006555 catalytic reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000011651 chromium Substances 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000007086 side reaction Methods 0.000 description 10
- FNPBHXSBDADRBT-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)CCO FNPBHXSBDADRBT-UHFFFAOYSA-M 0.000 description 9
- 239000003426 co-catalyst Substances 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- 230000006870 function Effects 0.000 description 9
- 239000002608 ionic liquid Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 238000003795 desorption Methods 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000002441 reversible effect Effects 0.000 description 7
- 239000004381 Choline salt Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910021607 Silver chloride Inorganic materials 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 235000019417 choline salt Nutrition 0.000 description 6
- 238000000970 chrono-amperometry Methods 0.000 description 6
- 230000005518 electrochemistry Effects 0.000 description 6
- 238000005868 electrolysis reaction Methods 0.000 description 6
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 6
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 125000005496 phosphonium group Chemical group 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 238000003487 electrochemical reaction Methods 0.000 description 4
- 230000005496 eutectics Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000013580 millipore water Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- KYCQOKLOSUBEJK-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;bromide Chemical compound [Br-].CCCCN1C=C[N+](C)=C1 KYCQOKLOSUBEJK-UHFFFAOYSA-M 0.000 description 3
- WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000004328 sodium tetraborate Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- CSPHGSFZFWKVDL-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CCl CSPHGSFZFWKVDL-UHFFFAOYSA-M 0.000 description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 2
- VCOBYGVZILHVOO-UHFFFAOYSA-M 2-butanoyloxyethyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCC(=O)OCC[N+](C)(C)C VCOBYGVZILHVOO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002848 electrochemical method Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- LPPJNZJBKFSQGA-UHFFFAOYSA-M hydron;2-hydroxyethyl(trimethyl)azanium;phosphate Chemical compound OP(O)([O-])=O.C[N+](C)(C)CCO LPPJNZJBKFSQGA-UHFFFAOYSA-M 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
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- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
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- 239000002245 particle Substances 0.000 description 2
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- 229940112042 peripherally acting choline derivative muscle relaxants Drugs 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
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- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- KXCVJPJCRAEILX-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.CCCCN1C=C[N+](C)=C1 KXCVJPJCRAEILX-UHFFFAOYSA-M 0.000 description 1
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- JJCWKVUUIFLXNZ-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCO JJCWKVUUIFLXNZ-UHFFFAOYSA-M 0.000 description 1
- FHCUSSBEGLCCHQ-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;fluoride Chemical compound [F-].C[N+](C)(C)CCO FHCUSSBEGLCCHQ-UHFFFAOYSA-M 0.000 description 1
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002000 Electrolyte additive Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 229910017835 Sb—Sn Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002156 adsorbate Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
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Images
Classifications
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Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10173169B2 (en) | 2010-03-26 | 2019-01-08 | Dioxide Materials, Inc | Devices for electrocatalytic conversion of carbon dioxide |
| US8956990B2 (en) | 2010-03-26 | 2015-02-17 | Dioxide Materials, Inc. | Catalyst mixtures |
| US9012345B2 (en) * | 2010-03-26 | 2015-04-21 | Dioxide Materials, Inc. | Electrocatalysts for carbon dioxide conversion |
| US9957624B2 (en) | 2010-03-26 | 2018-05-01 | Dioxide Materials, Inc. | Electrochemical devices comprising novel catalyst mixtures |
| US9790161B2 (en) | 2010-03-26 | 2017-10-17 | Dioxide Materials, Inc | Process for the sustainable production of acrylic acid |
| US20110237830A1 (en) | 2010-03-26 | 2011-09-29 | Dioxide Materials Inc | Novel catalyst mixtures |
| US9815021B2 (en) * | 2010-03-26 | 2017-11-14 | Dioxide Materials, Inc. | Electrocatalytic process for carbon dioxide conversion |
| CN104822861B (zh) * | 2012-09-24 | 2017-03-08 | 二氧化碳材料公司 | 用于将二氧化碳转化为有用燃料和化学品的装置和方法 |
| ITMI20121909A1 (it) * | 2012-11-09 | 2014-05-10 | Industrie De Nora Spa | Cella elettrolitica dotata di microelettrodi |
| US10647652B2 (en) | 2013-02-24 | 2020-05-12 | Dioxide Materials, Inc. | Process for the sustainable production of acrylic acid |
| AU2014271702A1 (en) | 2013-05-29 | 2015-12-17 | Kabushiki Kaisha Toshiba | Reduction catalyst and chemical reactor |
| CN105493340B (zh) * | 2013-06-27 | 2020-06-16 | 伊利诺伊大学董事会 | 用于二氧化碳转化的催化剂 |
| RU2016106910A (ru) * | 2013-07-31 | 2017-08-31 | Аквахайдрекс Пти Лтд | Композитные трехмерные электроды и способы их изготовления |
| US10570524B2 (en) | 2014-09-08 | 2020-02-25 | 3M Innovative Properties Company | Ionic polymer membrane for a carbon dioxide electrolyzer |
| US10724142B2 (en) | 2014-10-21 | 2020-07-28 | Dioxide Materials, Inc. | Water electrolyzers employing anion exchange membranes |
| US10774431B2 (en) | 2014-10-21 | 2020-09-15 | Dioxide Materials, Inc. | Ion-conducting membranes |
| US10975480B2 (en) | 2015-02-03 | 2021-04-13 | Dioxide Materials, Inc. | Electrocatalytic process for carbon dioxide conversion |
| JP6548954B2 (ja) | 2015-05-21 | 2019-07-24 | 株式会社東芝 | 還元触媒及び化学反応装置 |
| AR106069A1 (es) * | 2015-09-25 | 2017-12-06 | Akzo Nobel Chemicals Int Bv | Electrodo y proceso para su manufactura |
| US12286714B2 (en) * | 2015-10-09 | 2025-04-29 | Rutgers, The State University Of New Jersey | Nickel phosphide catalysts for direct electrochemical CO2 reduction to hydrocarbons |
| WO2017176600A1 (en) | 2016-04-04 | 2017-10-12 | Dioxide Materials, Inc. | Electrocatalytic process for carbon dioxide conversion |
| AU2016401931B2 (en) * | 2016-04-04 | 2019-03-07 | Dioxide Materials, Inc. | Catalyst layers and electrolyzers |
| CN115198294A (zh) | 2016-05-03 | 2022-10-18 | 欧普斯12公司 | 用于二氧化碳、一氧化碳和其他化学化合物的电化学反应的具有先进架构的反应器 |
| US12359325B2 (en) | 2016-05-03 | 2025-07-15 | Twelve Benefit Corporation | Membrane electrode assembly for COx reduction |
| US11680328B2 (en) | 2019-11-25 | 2023-06-20 | Twelve Benefit Corporation | Membrane electrode assembly for COx reduction |
| JP6758586B2 (ja) * | 2016-06-09 | 2020-09-23 | 国立大学法人秋田大学 | 大規模な二酸化炭素排出源(火力発電所等)で貯留した二酸化炭素の電解還元・メタノール同時合成のための二酸化炭素電解処理システム |
| DE102016217730A1 (de) | 2016-09-16 | 2018-03-22 | Siemens Aktiengesellschaft | CO2-Elektrolyseverfahren |
| CN107871875B (zh) * | 2016-09-26 | 2021-05-07 | 中国科学院大连化学物理研究所 | 一种析氧反应电催化剂、其制备方法及应用 |
| US10774430B2 (en) | 2016-10-04 | 2020-09-15 | Johna Leddy | Carbon dioxide reduction and carbon compound electrochemistry in the presence of lanthanides |
| JP6649293B2 (ja) | 2017-01-25 | 2020-02-19 | 株式会社東芝 | 還元触媒、ならびにそれを用いた化学反応装置、還元方法、および還元物生産システム |
| JP6949641B2 (ja) * | 2017-09-27 | 2021-10-13 | 積水化学工業株式会社 | 二酸化炭素還元装置 |
| CN117926298A (zh) | 2018-01-22 | 2024-04-26 | 十二益公司 | 用于二氧化碳反应器控制的系统和方法 |
| US12320022B2 (en) | 2018-01-22 | 2025-06-03 | Twelve Benefit Corporation | System and method for carbon dioxide reactor control |
| CN110055556B (zh) * | 2018-04-28 | 2021-03-30 | 南方科技大学 | 析氢反应催化剂及其制备方法和应用 |
| EP3887578A1 (en) | 2018-11-28 | 2021-10-06 | Opus 12 Incorporated | Electrolyzer and method of use |
| WO2020132064A1 (en) | 2018-12-18 | 2020-06-25 | Opus 12 Inc. | Electrolyzer and method of use |
| CN109860638B (zh) * | 2019-01-07 | 2021-12-03 | 湖南大学 | 一种纳米多孔Ag2Al材料、制备方法及应用 |
| KR20210132024A (ko) | 2019-01-07 | 2021-11-03 | 오푸스-12 인코포레이티드 | 메탄 제조를 위한 시스템 및 방법 |
| US11746426B2 (en) | 2019-07-10 | 2023-09-05 | California Institute Of Technology | Stabilization of a co-bound intermediate via molecular tuning promotes CO2-to-ethylene conversion |
| CN111389459B (zh) * | 2020-02-20 | 2021-04-13 | 嘉兴学院 | 一种用于催化还原二氧化碳或碳水化合物的组合物、及方法 |
| KR20230010203A (ko) | 2020-05-14 | 2023-01-18 | 닛토덴코 가부시키가이샤 | 이산화탄소 포착 처리 시스템 및 co2 네거티브 이미션 공장 |
| KR20230092977A (ko) | 2020-10-20 | 2023-06-26 | 트웰브 베네핏 코포레이션 | 이온성 중합체 및 공중합체 |
| CA3196179A1 (en) | 2020-10-20 | 2022-04-28 | Lihui Wang | Semi-interpenetrating and crosslinked polymers and membranes thereof |
| CN113737217B (zh) * | 2021-09-29 | 2024-06-11 | 天津理工大学 | 一种高负载量金属Co单原子催化剂及其制备方法和应用 |
| EP4569156A1 (en) | 2022-08-12 | 2025-06-18 | Twelve Benefit Corporation | Acetic acid production |
| US12463265B2 (en) * | 2022-12-01 | 2025-11-04 | GM Global Technology Operations LLC | Battery monitoring system for measuring carbon dioxide to detect imbalance in a group of parallel lithium-ion battery cells |
| JPWO2024135202A1 (enExample) * | 2022-12-22 | 2024-06-27 | ||
| US12460310B2 (en) | 2023-04-04 | 2025-11-04 | Twelve Benefit Corporation | Integrated systems employing carbon oxide electrolysis in aluminum production |
Family Cites Families (115)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE183856C (enExample) | ||||
| US1919850A (en) | 1933-07-25 | Emil luscher | ||
| US2511198A (en) | 1948-01-02 | 1950-06-13 | Allied Chem & Dye Corp | Preparation of concentrated formic acid |
| US2996359A (en) | 1957-11-26 | 1961-08-15 | Matheson Company Inc | Method for continuous manufacture of carbon monoxide |
| JPS4848409A (enExample) * | 1971-10-18 | 1973-07-09 | ||
| BE791653A (fr) * | 1971-12-28 | 1973-05-21 | Texaco Development Corp | Procede electrolytique de preparation de l'acide |
| US4299891A (en) | 1972-10-27 | 1981-11-10 | The Richardson Company | Method for forming battery terminals and terminals produced thereby |
| US3959094A (en) | 1975-03-13 | 1976-05-25 | The United States Of America As Represented By The United States Energy Research And Development Administration | Electrolytic synthesis of methanol from CO2 |
| US4207151A (en) | 1976-06-04 | 1980-06-10 | Monsanto Company | Electrohydrodimerization process improvement and improved electrolyte recovery process |
| US4115433A (en) * | 1977-10-11 | 1978-09-19 | Union Carbide Corporation | Catalyst and process for producing polyhydric alcohols and derivatives |
| JPS54138502A (en) * | 1978-04-17 | 1979-10-27 | Toyo Soda Mfg Co Ltd | Electrolytic reduction of organic and inorganic compounds |
| DE2849065A1 (de) | 1978-11-11 | 1980-05-22 | Basf Ag | Verwendung von quartaeren ammoniumsalzen als leitsalze |
| US4240882A (en) | 1979-11-08 | 1980-12-23 | Institute Of Gas Technology | Gas fixation solar cell using gas diffusion semiconductor electrode |
| US4315753A (en) | 1980-08-14 | 1982-02-16 | The United States Of America As Represented By The Secretary Of The Interior | Electrochemical apparatus for simultaneously monitoring two gases |
| DE81982T1 (de) | 1981-12-11 | 1983-09-29 | The British Petroleum Co. P.L.C., Sunbury-On-Thames, Middlesex | Elektrochemische organische synthese. |
| JPS59219485A (ja) | 1983-05-26 | 1984-12-10 | Asahi Chem Ind Co Ltd | 2,5−ジメチルヘキサンジニトリルの製法 |
| GB8401005D0 (en) | 1984-01-14 | 1984-02-15 | Bp Chem Int Ltd | Formate salts |
| US4523981A (en) * | 1984-03-27 | 1985-06-18 | Texaco Inc. | Means and method for reducing carbon dioxide to provide a product |
| US4545872A (en) | 1984-03-27 | 1985-10-08 | Texaco Inc. | Method for reducing carbon dioxide to provide a product |
| US4609451A (en) | 1984-03-27 | 1986-09-02 | Texaco Inc. | Means for reducing carbon dioxide to provide a product |
| DE3417790A1 (de) | 1984-05-14 | 1985-11-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von ameisensaeure |
| US4595465A (en) | 1984-12-24 | 1986-06-17 | Texaco Inc. | Means and method for reducing carbn dioxide to provide an oxalate product |
| US4620906A (en) | 1985-01-31 | 1986-11-04 | Texaco Inc. | Means and method for reducing carbon dioxide to provide formic acid |
| US4673473A (en) | 1985-06-06 | 1987-06-16 | Peter G. Pa Ang | Means and method for reducing carbon dioxide to a product |
| US4608132A (en) | 1985-06-06 | 1986-08-26 | Texaco Inc. | Means and method for the electrochemical reduction of carbon dioxide to provide a product |
| US4608133A (en) | 1985-06-10 | 1986-08-26 | Texaco Inc. | Means and method for the electrochemical reduction of carbon dioxide to provide a product |
| US4609440A (en) | 1985-12-18 | 1986-09-02 | Gas Research Institute | Electrochemical synthesis of methane |
| US4609441A (en) | 1985-12-18 | 1986-09-02 | Gas Research Institute | Electrochemical reduction of aqueous carbon dioxide to methanol |
| CA1272180A (fr) | 1986-03-20 | 1990-07-31 | Andre Mortreux | Systeme catalytique, son procede de preparation et son application a la fabrication d'aldehydes |
| US4756807A (en) | 1986-10-09 | 1988-07-12 | Gas Research Institute | Chemically modified electrodes for the catalytic reduction of CO2 |
| US4711708A (en) | 1986-10-09 | 1987-12-08 | Gas Research Institute | Chemically modified electrodes for the catalytic reduction of CO2 |
| US4668349A (en) | 1986-10-24 | 1987-05-26 | The Standard Oil Company | Acid promoted electrocatalytic reduction of carbon dioxide by square planar transition metal complexes |
| JPS63111193A (ja) | 1986-10-30 | 1988-05-16 | Asahi Chem Ind Co Ltd | アジポニトリルの製法 |
| IT1216929B (it) | 1987-04-16 | 1990-03-14 | Enichem Sintesi | Procedimento per la sintesi di acidi 2-aril-propionici. |
| GB8712582D0 (en) * | 1987-05-28 | 1987-07-01 | Neotronics Ltd | Acidic gas sensors |
| US4818353A (en) | 1987-07-07 | 1989-04-04 | Langer Stanley H | Method for modifying electrocatalyst material, electrochemical cells and electrodes containing this modified material, and synthesis methods utilizing the cells |
| FR2624884B1 (fr) | 1987-12-18 | 1990-04-20 | Poudres & Explosifs Ste Nale | Procede de synthese electrochimique de cetones alpha saturees |
| US4771708A (en) | 1988-01-11 | 1988-09-20 | Douglass Jr Edward T | Incinerator and heat recovery system for drying wood poles |
| US4968393A (en) * | 1988-04-18 | 1990-11-06 | A. L. Sandpiper Corporation | Membrane divided aqueous-nonaqueous system for electrochemical cells |
| FR2646441B1 (fr) | 1989-04-28 | 1991-07-12 | Poudres & Explosifs Ste Nale | Procede d'electrosynthese d'un ester beta gamma insature |
| US5064733A (en) | 1989-09-27 | 1991-11-12 | Gas Research Institute | Electrochemical conversion of CO2 and CH4 to C2 hydrocarbons in a single cell |
| JP3009703B2 (ja) | 1990-05-02 | 2000-02-14 | 正道 藤平 | 二酸化炭素ガス還元用電極触媒 |
| DE4016063A1 (de) | 1990-05-18 | 1991-11-21 | Hoechst Ag | Verfahren zur teilweisen elektrolytischen enthalogenierung von di- und trichloressigsaeure sowie elektrolyseloesung |
| DE4211141A1 (de) | 1992-04-03 | 1993-10-07 | Basf Ag | Verfahren zur Herstellung von Ameisensäure durch thermische Spaltung von quartären Ammoniumformiaten |
| DE4227394A1 (de) | 1992-08-19 | 1994-02-24 | Basf Ag | Verfahren zur Herstellung von Ameisensäure aus Kohlenmonoxid und Wasser |
| JP3360850B2 (ja) | 1992-09-21 | 2003-01-07 | 株式会社日立製作所 | 銅系酸化触媒とその用途 |
| EP0652202B1 (en) | 1993-11-04 | 1997-06-04 | Research Development Corporation Of Japan | A method for producing formic acid or its derivatives |
| KR0169188B1 (ko) | 1995-07-31 | 1999-03-20 | 강박광 | 탄화수소의 제조방법 |
| DE19544671A1 (de) | 1995-11-30 | 1997-06-05 | Bayer Ag | Urethan(meth)acrylate mit cyclischen Carbonatgruppen |
| GB9603754D0 (en) * | 1996-02-22 | 1996-04-24 | Bp Chem Int Ltd | Lubricating oils |
| FR2745297B1 (fr) | 1996-02-26 | 1998-05-22 | Lesaffre Dev | Utilisation d'une souche bacterienne pour la fabrication de l'acide formique ou du formiate et procede de fermentation utilisant cette souche |
| FR2747694B1 (fr) | 1996-04-18 | 1998-06-05 | France Etat | Cathode pour la reduction de dioxyde de carbone et procede de fabrication d'une telle cathode |
| US5709789A (en) | 1996-10-23 | 1998-01-20 | Sachem, Inc. | Electrochemical conversion of nitrogen containing gas to hydroxylamine and hydroxylammonium salts |
| US6660680B1 (en) | 1997-02-24 | 2003-12-09 | Superior Micropowders, Llc | Electrocatalyst powders, methods for producing powders and devices fabricated from same |
| US5928806A (en) | 1997-05-07 | 1999-07-27 | Olah; George A. | Recycling of carbon dioxide into methyl alcohol and related oxygenates for hydrocarbons |
| US6024855A (en) | 1997-08-15 | 2000-02-15 | Sachem, Inc. | Electrosynthesis of hydroxylammonium salts and hydroxylamine using a mediator |
| DE19754304A1 (de) * | 1997-12-08 | 1999-06-10 | Hoechst Ag | Polybetain-stabilisierte Platin-Nanopartikel, Verfahren zu ihrer Herstellung und Verwendung für Elektrokatalysatoren in Brennstoffzellen |
| US6099990A (en) * | 1998-03-26 | 2000-08-08 | Motorola, Inc. | Carbon electrode material for electrochemical cells and method of making same |
| FI107528B (fi) | 1998-12-23 | 2001-08-31 | Kemira Chemicals Oy | Menetelmä muurahaishapon valmistamiseksi |
| DE19953832A1 (de) | 1999-11-09 | 2001-05-10 | Basf Ag | Verfahren zur Herstellung von Ameisensäure |
| KR100351625B1 (ko) | 1999-11-11 | 2002-09-11 | 한국화학연구원 | 탄화수소 제조용 촉매 |
| DE10002794A1 (de) | 2000-01-24 | 2001-07-26 | Basf Ag | Abwasserreinigung beim Verfahren zur Herstellung von wasserfreier Ameisensäure |
| DE10002795A1 (de) | 2000-01-24 | 2001-08-02 | Basf Ag | Werkstoff für eine Anlage zur Herstellung von wasserfreier Ameisensäure |
| DE10002791A1 (de) | 2000-01-24 | 2001-07-26 | Basf Ag | Verfahren zur Gewinnung von wasserfreier Ameisensäure |
| FR2804622B1 (fr) | 2000-02-04 | 2002-04-05 | Inst Francais Du Petrole | Composition catalytique pour la dimerisation, la codimerisation et l'oligomerisation des olefines |
| CN1275915C (zh) | 2000-02-25 | 2006-09-20 | 新日本制铁株式会社 | 甲酸酯或甲醇的生产方法及其合成催化剂 |
| FI117633B (fi) | 2000-12-29 | 2006-12-29 | Chempolis Oy | Kemikaalien talteenotto ja valmistus massan valmistuksen yhteydessä |
| US6963909B1 (en) | 2001-07-24 | 2005-11-08 | Cisco Technology, Inc. | Controlling the response domain of a bootP/DHCP server by using network physical topology information |
| DE10138778A1 (de) | 2001-08-07 | 2003-02-20 | Basf Ag | Flexibles Verfahren zur gemeinsamen Herstellung von Ameisensäure sowie einer Carbonsäure mit mindestens zwei Kohlenstoffatomen und/oder deren Derivaten |
| WO2003043967A1 (en) | 2001-11-08 | 2003-05-30 | Mks Marmara Entegre Kimya San. A.S. | Production of potassium formate |
| CA2464762A1 (en) | 2001-11-09 | 2003-05-15 | Basf Aktiengesellschaft | Method for production of formic acid formates |
| DE60301288T2 (de) * | 2002-03-22 | 2006-06-01 | Haldor Topsoe A/S | Verfahren zur Paraffinisomerisierung und dafür geeignete katalytische Zusammensetzung, enthaltend eine ionische Flüssigkeit und ein Metallsalz-Additiv |
| GB0215384D0 (en) | 2002-07-04 | 2002-08-14 | Johnson Matthey Plc | Improvements in metal salts |
| DE10237379A1 (de) | 2002-08-12 | 2004-02-19 | Basf Ag | Verfahren und Vorrichtung zur Herstellung von ameisensauren Formiaten und deren Verwendung |
| DE10237380A1 (de) | 2002-08-12 | 2004-02-19 | Basf Ag | Verfahren und Vorrichtung zur Herstellung von ameisensauren Formlaten und deren Verwendung |
| US6939453B2 (en) | 2002-08-14 | 2005-09-06 | Large Scale Proteomics Corporation | Electrophoresis process using ionic liquids |
| DE10249928A1 (de) | 2002-10-26 | 2004-05-06 | Basf Ag | Flexibles Verfahren zur gemeinsamen Herstellung von (i) Ameisensäure, (ii) einer Carbonsäure mit mindestens zwei Kohlenstoffatomen und/oder deren Derivate und (iii) eines -Carbonsäureanhydrids |
| CA2539174C (en) | 2003-09-17 | 2009-12-08 | Japan Science And Technology Agency | Process for reduction of carbon dioxide with organometallic complex |
| US6987134B1 (en) | 2004-07-01 | 2006-01-17 | Robert Gagnon | How to convert carbon dioxide into synthetic hydrocarbon through a process of catalytic hydrogenation called CO2hydrocarbonation |
| CN1290215C (zh) * | 2004-08-06 | 2006-12-13 | 重庆大学 | 电沉积法制备质子交换膜燃料电池电极时抑制析氢的方法 |
| DE102004040789A1 (de) | 2004-08-23 | 2006-03-02 | Basf Ag | Verfahren zur Herstellung von Ameisensäure |
| ES2263346B1 (es) | 2004-08-25 | 2007-12-16 | Consejo Superior De Investigaciones Cientificas | Uso de una composicion catalitica en la insercion de dioxido de carbo no en acetales, ortoesteres y epoxidos. |
| US7618725B2 (en) | 2004-09-21 | 2009-11-17 | The Board Of Trustees Of The University Of Illinois | Low contaminant formic acid fuel for direct liquid fuel cell |
| US7811433B2 (en) | 2004-10-15 | 2010-10-12 | Giner, Inc. | Electrochemical carbon dioxide sensor |
| US7748976B2 (en) | 2005-03-17 | 2010-07-06 | Southwest Research Institute | Use of recirculated exhaust gas in a burner-based exhaust generation system for reduced fuel consumption and for cooling |
| US7608743B2 (en) | 2005-04-15 | 2009-10-27 | University Of Southern California | Efficient and selective chemical recycling of carbon dioxide to methanol, dimethyl ether and derived products |
| EP1871731B1 (en) | 2005-04-15 | 2012-12-26 | University Of Southern California | Efficient and selective conversion of carbon dioxide to methanol, dimethyl ether and derived products |
| DE102005020890A1 (de) | 2005-05-04 | 2006-11-09 | Basf Ag | Herstellung von Natriumformiat |
| US20070187247A1 (en) | 2005-07-20 | 2007-08-16 | Lackner Klaus S | Electrochemical methods and processes for carbon dioxide recovery from alkaline solvents for carbon dioxide capture from air |
| JP2009506213A (ja) | 2005-08-25 | 2009-02-12 | セラマテック・インク | 空気および水を使用して合成ガスを製造するための電気化学的セル |
| JPWO2007037337A1 (ja) | 2005-09-29 | 2009-04-09 | 三洋化成工業株式会社 | 電気化学素子用電解液及びこれを用いた電気化学素子 |
| WO2007041872A1 (en) | 2005-10-13 | 2007-04-19 | Mantra Energy Alternatives Ltd. | Continuous co-current electrochemical reduction of carbon dioxide |
| US7378561B2 (en) | 2006-08-10 | 2008-05-27 | University Of Southern California | Method for producing methanol, dimethyl ether, derived synthetic hydrocarbons and their products from carbon dioxide and water (moisture) of the air as sole source material |
| GB0704972D0 (en) * | 2007-03-15 | 2007-04-25 | Varney Mark S | Neoteric room temperature ionic liquid gas sensor |
| JP2008288079A (ja) * | 2007-05-18 | 2008-11-27 | Panasonic Corp | 無水銀アルカリ乾電池 |
| US20090016948A1 (en) | 2007-07-12 | 2009-01-15 | Young Edgar D | Carbon and fuel production from atmospheric CO2 and H2O by artificial photosynthesis and method of operation thereof |
| US8138380B2 (en) | 2007-07-13 | 2012-03-20 | University Of Southern California | Electrolysis of carbon dioxide in aqueous media to carbon monoxide and hydrogen for production of methanol |
| WO2009012154A2 (en) | 2007-07-13 | 2009-01-22 | University Of Southern California | Electrolysis of carbon dioxide in aqueous media to carbon monoxide and hydrogen for production of methanol |
| NZ564691A (en) | 2007-12-21 | 2010-03-26 | Nz Inst Plant & Food Res Ltd | Glycosyltransferases, polynucleotides encoding these and methods of use |
| WO2009086460A1 (en) | 2007-12-28 | 2009-07-09 | Calera Corporation | Methods of sequestering co2 |
| US20100137457A1 (en) | 2008-07-01 | 2010-06-03 | Kaplan Thomas Proger | Method for conversion of atmospheric carbon dioxide into useful materials |
| WO2010007602A1 (en) | 2008-07-18 | 2010-01-21 | Ffgf Limited | The production of hydrogen, oxygen and hydrocarbons |
| CA2730712A1 (en) * | 2008-07-30 | 2010-02-04 | Blacklight Power, Inc. | Heterogeneous hydrogen-catalyst reactor |
| CN102227629B (zh) * | 2008-12-01 | 2015-09-23 | Msa奥尔有限责任公司 | 具有离子液体电解质系统的电化学气体传感器 |
| EP2382174A4 (en) | 2009-01-29 | 2013-10-30 | Trustees Of The University Of Princeton | CONVERSION OF CARBON DIOXIDE IN ORGANIC PRODUCTS |
| US8366894B2 (en) | 2009-02-20 | 2013-02-05 | Giner, Inc. | Multi-gas microsensor assembly |
| US20110114502A1 (en) | 2009-12-21 | 2011-05-19 | Emily Barton Cole | Reducing carbon dioxide to products |
| US8845877B2 (en) | 2010-03-19 | 2014-09-30 | Liquid Light, Inc. | Heterocycle catalyzed electrochemical process |
| US8500987B2 (en) | 2010-03-19 | 2013-08-06 | Liquid Light, Inc. | Purification of carbon dioxide from a mixture of gases |
| US8721866B2 (en) | 2010-03-19 | 2014-05-13 | Liquid Light, Inc. | Electrochemical production of synthesis gas from carbon dioxide |
| US20110237830A1 (en) * | 2010-03-26 | 2011-09-29 | Dioxide Materials Inc | Novel catalyst mixtures |
| JP5591606B2 (ja) | 2010-07-08 | 2014-09-17 | 三井造船株式会社 | 二酸化炭素の還元,固定方法 |
| US8524066B2 (en) | 2010-07-29 | 2013-09-03 | Liquid Light, Inc. | Electrochemical production of urea from NOx and carbon dioxide |
| EP2655310B1 (de) | 2010-12-21 | 2014-11-05 | Basf Se | Verfahren zur herstellung von ameisensäure durch umsetzung von kohlendioxid mit wasserstoff |
| WO2013006711A1 (en) | 2011-07-06 | 2013-01-10 | Liquid Light, Inc. | Reduction of carbon dioxide to carboxylic acids, glycols, and carboxylates |
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| CA2802893C (en) | 2018-08-28 |
| JP6449839B2 (ja) | 2019-01-09 |
| JP2017082334A (ja) | 2017-05-18 |
| KR101801659B1 (ko) | 2017-11-27 |
| US9566574B2 (en) | 2017-02-14 |
| BR112013000261A2 (pt) | 2017-05-16 |
| JP2013538285A (ja) | 2013-10-10 |
| AU2011276362A1 (en) | 2013-02-21 |
| US20120308903A1 (en) | 2012-12-06 |
| AU2011276362B2 (en) | 2016-03-17 |
| CN102971451A (zh) | 2013-03-13 |
| CN102971451B (zh) | 2016-09-14 |
| WO2012006240A1 (en) | 2012-01-12 |
| WO2012006240A4 (en) | 2012-02-02 |
| CA2802893A1 (en) | 2012-01-12 |
| KR20130043178A (ko) | 2013-04-29 |
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