JP2013519615A - ホスフィンオキシド触媒を用いた、水素キャリアとしてのシリル化誘導体からの水素の製造方法 - Google Patents
ホスフィンオキシド触媒を用いた、水素キャリアとしてのシリル化誘導体からの水素の製造方法 Download PDFInfo
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- JP2013519615A JP2013519615A JP2012552428A JP2012552428A JP2013519615A JP 2013519615 A JP2013519615 A JP 2013519615A JP 2012552428 A JP2012552428 A JP 2012552428A JP 2012552428 A JP2012552428 A JP 2012552428A JP 2013519615 A JP2013519615 A JP 2013519615A
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- Prior art keywords
- alkyl
- compound
- hydrogen
- aryl
- catalyst
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 69
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 239000001257 hydrogen Substances 0.000 title claims abstract description 61
- 239000003054 catalyst Substances 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000006227 byproduct Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 18
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011574 phosphorus Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical group CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 238000004064 recycling Methods 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 229910052987 metal hydride Inorganic materials 0.000 claims description 7
- 150000004681 metal hydrides Chemical class 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 150000001266 acyl halides Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 230000001172 regenerating effect Effects 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 239000000446 fuel Substances 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
- -1 lithium aluminum hydride Chemical compound 0.000 description 17
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 15
- 150000004678 hydrides Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IVSPVXKJEGPQJP-UHFFFAOYSA-N 2-silylethylsilane Chemical compound [SiH3]CC[SiH3] IVSPVXKJEGPQJP-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229910000365 copper sulfate Inorganic materials 0.000 description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JBANFLSTOJPTFW-UHFFFAOYSA-N azane;boron Chemical compound [B].N JBANFLSTOJPTFW-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- MFJCPDOGFAYSTF-UHFFFAOYSA-N 1H-isochromene Chemical compound C1=CC=C2COC=CC2=C1 MFJCPDOGFAYSTF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 0 CC(O*(c1ccccc1)OC(C)=O)=O Chemical compound CC(O*(c1ccccc1)OC(C)=O)=O 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZKTFNWPPVIAFDC-UHFFFAOYSA-N OB(O)O.P.P.P Chemical class OB(O)O.P.P.P ZKTFNWPPVIAFDC-UHFFFAOYSA-N 0.000 description 1
- NBADVBNRRHVIAO-UHFFFAOYSA-N OSc1ccccc1 Chemical compound OSc1ccccc1 NBADVBNRRHVIAO-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 description 1
- RLVUPLZDJPNQPJ-UHFFFAOYSA-N [SH3]c1ccccc1 Chemical compound [SH3]c1ccccc1 RLVUPLZDJPNQPJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000006278 bromobenzyl group Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- ADTGAVILDBXARD-UHFFFAOYSA-N diethylamino(dimethyl)silicon Chemical compound CCN(CC)[Si](C)C ADTGAVILDBXARD-UHFFFAOYSA-N 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- WYLQARGYFXBZMD-UHFFFAOYSA-N n-[chloro(dimethylamino)phosphoryl]-n-methylmethanamine Chemical compound CN(C)P(Cl)(=O)N(C)C WYLQARGYFXBZMD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000005306 thianaphthenyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- VIPCDVWYAADTGR-UHFFFAOYSA-N trimethyl(methylsilyl)silane Chemical compound C[SiH2][Si](C)(C)C VIPCDVWYAADTGR-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/06—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of inorganic compounds containing electro-positively bound hydrogen, e.g. water, acids, bases, ammonia, with inorganic reducing agents
- C01B3/065—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of inorganic compounds containing electro-positively bound hydrogen, e.g. water, acids, bases, ammonia, with inorganic reducing agents from a hydride
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- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
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- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
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- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/06—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of inorganic compounds containing electro-positively bound hydrogen, e.g. water, acids, bases, ammonia, with inorganic reducing agents
- C01B3/061—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of inorganic compounds containing electro-positively bound hydrogen, e.g. water, acids, bases, ammonia, with inorganic reducing agents by reaction of metal oxides with water
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- C—CHEMISTRY; METALLURGY
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- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/22—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of gaseous or liquid organic compounds
- C01B3/24—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of gaseous or liquid organic compounds of hydrocarbons
- C01B3/26—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of gaseous or liquid organic compounds of hydrocarbons using catalysts
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
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Abstract
【選択図】なし
Description
i) 溶媒としての水中にある塩基の存在下で、1以上のSi−H基を有する化合物を、リン系触媒と接触させて、水素及び副生成物(C1)を生成する工程であって、上記リン系触媒が、以下から選択される工程:
−X1X2X3P(=O)の式の化合物
(式中、
X1、X2、X3は、それぞれ独立にC1〜C6アルキル、C1〜C6アルコキシ、NRaRb、C6〜C10アリール、アラルキル、5員〜7員のヘテロアリールから選択され、ここで上記アルキル基又はアリール基は、1〜3のRcで置換されていてもよく;又は
X1及びX2は、それらが結合している上記リン原子と共に、Rdで置換されていてもよい3員〜10員のヘテロシクロアルキルを形成し、かつX3は、上で定義したものと同じである;又は
X3は、−L−P(=O)X1X2で、ここでLは、C1〜C6アルキレン若しくはC6〜C10アリーレンであり、かつX1、X2は、上で定義したものと同じである、
ここで、
Ra及びRbは、C1〜C6アルキル、C6〜C10アリールから選択され、又はそれらが結合している上記リン原子と共に、1〜3のReで置換されていてもよいヘテロシクリルを形成し;
Rc、Rd及びReは、それぞれ独立にCl、Br、I、F、OH、C1〜C6アルキル、C1〜C6アルコキシ、NO2、NH2、CN、COOHから選択される)、及び
−1以上のRa及びRb(P=O)−基を有するポリマー担持触媒(RaRbは、上で定義したものと同じである);及び
ii)得られた水素を回収する工程。
Rは、結合、C1〜C6アルキレン又は(C1〜C4アルキレン)m−Z−(C1〜C4アルキレン)qであり;
Zは、O、NR10、S(O)y、CR10=CR10、C≡C、C6〜C10アリーレン、5員〜10員のヘテロアリーレン、又はC3〜C6のシクロアルキレンであり;
R1及びR2は、それぞれ独立にH、ハロゲン、C1〜C10アルキル、C3〜C10シクロアルキル、C6〜C12アリール、アラルキル、5員〜10員のヘテロアリール、OR3、NR4R5、又はSiR6R7R8から選択され、ここで上記アリール基は、1〜3のR9基で置換されていてもよく;
R3は、H、C1〜C6アルキル、C6〜C10アリール、又はアラルキルであり;
R4及びR5は、それぞれ独立にH、C1〜C6アルキル、C6〜C10アリール、又はアラルキルから選択され;
R6、R7及びR8は、それぞれ独立にH、OR3、C1〜C6アルキル、C6〜C10アリール、又はアラルキルから選択され;
R9は、ハロゲン、C1〜C10アルキル、OR10、NO2、NR11R12、CN、C(=O)R10、C(=O)OR10、又はS(=O)CH3から選択され、上記アルキル基は、1以上のハロゲンで置換されていてもよく;
R10は、H又はC1〜C3アルキルであり;
R11及びR12は、それぞれ独立にH又はC1〜C10アルキルから選択され;
m及びqは、0又は1であり;
yは、0、1又は2であり;かつ
n及びpは、繰返し単位の数をそれぞれ表す整数で、nは1以上、かつpは0又は1である)。
c)上記副生成物(C1)を、ハロゲン化アシルと接触させる工程;
d)得られた生成物を、金属水素化物と接触させて、それにより化合物(C)を再生する工程。
i)化合物(C)から水素を製造する工程;及び
ii)工程i)で得られる副生成物(C1)をリサイクルする工程。
i.溶媒としての水に化合物(C)と塩基を含有する反応混合物の入口;
ii.水素出口;
iii.副生成物コレクター;及び
iv.上述のポリマー担持触媒でコーティングされている、上記混合物と接触させることを意図した表面。
v.外周部;
vi.上記チャンバーを、次の2つの異なる区画に仕切る内壁:
1.上記反応チャンバーに導入する上記反応混合物を収容する、第一の区画;及び
2.上記反応チャンバーから収集された上記副生成物(C1)を収容する、第二の区画;
3.上記第一の区画及び上記第二の区画は、上記反応チャンバーにそれぞれ接続されている;及び
vii.各区画のそれぞれの容積を変えるための、上記外周部に対して内壁を移動させるための手段。
ポリマーベンジルアミン触媒(ポリスチレンAM−NH2、Ref 81553−10G、Aldrich)250mg(0.4〜1.2×10−3モル)及び新たなCDCl3(5ml)を、乾燥したバイアル瓶に添加した。この混合物を、室温でゆっくりと攪拌し、そしてK2CO3(310mg)、DMAP(15mg)、Et3N(0.6ml)を添加した。最後に、テトラメチルジアミドリン酸クロリド(tetramethylphosphorodiamidic chloride)(1.85mmol、316mg、10〜11当量)を、上記混合物に添加した。この反応混合物を、5日間攪拌した。このポリマー樹脂を、最終的に濾過し、CHCl3で5回洗浄し、減圧下で乾燥させ、そして茶色の固体として室温で貯蔵した。
Claims (22)
- 以下の工程を含む、水素の製造方法:
i) 溶媒としての水中にある塩基の存在下で、1以上のSi−H基を有する化合物(C)を、リン系触媒と接触させて、水素及び副生成物(C1)を生成する工程であって、前記リン系触媒が、下記から選択される工程:
−X1X2X3P(=O)の式の化合物
(式中、
X1、X2、X3は、それぞれ独立に、C1〜C6アルキル、C1〜C6アルコキシ、NRaRb、C6〜C10アリール、アラルキル、5員〜7員のヘテロアリールから、選択され、ここで前記アルキル基又は前記アリール基は、1〜3のRcで置換されていてもよく;又は
X1及びX2は、それらが結合している前記リン原子と共に、Rdで随意に置換されている3員〜10員のヘテロシクロアルキルを形成し、かつX3は、前記定義と同じであり;又は
X3は、−L−P(=O)X1X2で、ここでLは、C1〜C6アルキレン若しくはC6〜C10アリーレンであり、かつX1、X2は、上で定義したものと同じであり、
ここで、
Ra及びRbは、それぞれ独立に、C1〜C6アルキル、C6〜C10アリールから選択され、又はそれらが結合している前記リン原子と共に、1〜3のReで置換されてもよいヘテロシクリルを形成し;
Rc、Rd及びReは、それぞれ独立に、Cl、Br、I、F、OH、C1〜C6アルキル、C1〜C6アルコキシ、NO2、NH2、CN、COOHから選択される)、
及び
−1以上のRaRb(P=O)−基を有するポリマー担持触媒
(式中、Ra及びRbは、前記定義と同じである);及び
ii)得られた前記水素を回収する工程。 - X1、X2、X3の1つが、NRaRbである、請求項1に記載の方法。
- Ra及び/又はRbが、C1〜C6アルキルである、請求項1又は2に記載の方法。
- 前記リン系触媒が、ヘキサメチルホスホルアミド(HMPA)である、請求項1〜3のいずれか一項に記載の方法。
- 前記触媒を担持するポリマーが、(アミノメチル)ポリスチレンである、請求項1〜4のいずれか一項に記載の方法。
- 前記化合物(C)に対する前記リン系触媒のモル比は、0.01〜0.1当量の範囲である、請求項1〜5のいずれか一項に記載の方法。
- 前記化合物(C)は、次の式(A)のモノマー単位を1つ以上有する、請求項1〜6のいずれか一項に記載の方法:
Rは、結合、C1〜C6アルキレン、又は(C1〜C4アルキレン)m−Z−(C1〜C4アルキレン)qであり;
Zは、O、NR10、S(O)y、CR10=CR10、C≡C、C6〜C10アリーレン、5員〜10員のヘテロアリーレン、又はC3〜C6のシクロアルキレンであり;
R1及びR2は、それぞれ独立にH、ハロゲン、C1〜C10アルキル、C3〜C10シクロアルキル、C6〜C12アリール、アラルキル、5員〜10員のヘテロアリール、OR3、NR4R5、又はSiR6R7R8から選択され、ここでこのアリール基は、1〜3のR9基で置換されていてもよく;
R3は、H、C1〜C6アルキル、C6〜C10アリール、アラルキルであり;
R4及びR5は、それぞれ独立にH、C1〜C6アルキル、C6〜C10アリール、アラルキルから選択され;
R6、R7及びR8は、それぞれ独立にH、OR3、C1〜C6アルキル、C6〜C10アリール、アラルキルから選択され;
R9は、ハロゲン、C1〜C10アルキル、OR10、NO2、NR11R12、CN、C(=O)R10、C(=O)OR10、S(=O)CH3から選択され、このアルキル基は、1以上のハロゲンで置換されていてもよく;
R10は、H又はC1〜C3アルキルであり;
R11及びR12は、それぞれ独立にH又はC1〜C10アルキルから選択され;
m及びqは、0又は1であり;
yは、0、1又は2であり;かつ
n及びpは、繰返し単位の数をそれぞれ表す整数で、nは1以上、かつpは0又は1である)。 - pは0である、請求項7に記載の方法。
- 式(Ib)のモノマー単位を有する前記化合物(C)は、PhSiH3である、請求項9に記載の方法。
- 式(Ib)のモノマー単位を有する前記化合物(C)は、C(SiH3)4である、請求項9に記載の方法。
- pは1である、請求項7に記載の方法。
- 式(Ic)のモノマー単位を有する前記化合物(C)は、H3Si(CH2)2SiH3である、請求項13に記載の方法。
- 前記塩基は、アルカリ金属水酸化物、アルカリ土類金属水酸化物、又はベンジルアミンである、請求項1〜14のいずれか一項に記載の方法。
- 以下の続くリサイクル工程をさらに有する、請求項1〜15のいずれか一項に記載の方法:
a)前記副生成物(C1)を、ハロゲン化アシルと接触させる工程;
b)得られた生成物を、金属水素化物と接触させて、それにより化合物(C)を再生する工程。 - 請求項1〜16のいずれか一項に規定した、化合物(C)、リン系触媒、塩基及び溶媒としての水を含有する、組成物。
- 水素を製造するための請求項17に記載の組成物の使用。
- 以下を具備する反応チャンバーを有する、請求項1〜16のいずれか一項に記載の方法によって水素を製造するための装置:
i.溶媒としての水に化合物(C)と塩基を含有する反応混合物の入口;
ii.水素出口;
iii.副生成物コレクター;及び
iv.請求項1に記載のポリマー担持触媒でコーティングされている、前記混合物と接触させることを意図した表面。 - 前記化合物(C)を溶媒としての水中で前記塩基と混合するための混合チャンバーであって、前記反応チャンバーに接続されている混合チャンバーをさらに具備する、請求項19に記載の装置。
- 前記反応チャンバーに接続されている副生成物収集チャンバーをさらに具備する、請求項19又は20に記載の装置。
- 以下を具備する第二のチャンバーをさらに有する、請求項19に記載の装置:
v.外周部;
vi.前記チャンバーを、次の2つの異なる区画に仕切る内壁:
1.前記反応チャンバーに導入する前記反応混合物を収容する、第一の区画;及び
2.前記反応チャンバーから収集される前記副生成物(C1)を収容する、第二の区画;
3.前記第一の区画及び前記第二の区画は、前記反応チャンバーにそれぞれ接続されている;及び
vii.各区画のそれぞれの容積を変えるための、前記外周部に対して前記内壁を移動させるための手段。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30459510P | 2010-02-15 | 2010-02-15 | |
US61/304,595 | 2010-02-15 | ||
PCT/EP2011/052192 WO2011098614A1 (en) | 2010-02-15 | 2011-02-15 | Phosphine-oxide catalyzed process of production of hydrogen from silylated derivatives as hydrogen carrier |
Publications (2)
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JP2013519615A true JP2013519615A (ja) | 2013-05-30 |
JP5678102B2 JP5678102B2 (ja) | 2015-02-25 |
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ES2651161B2 (es) * | 2017-07-11 | 2018-08-13 | Universitat Jaume I | Procedimiento para la producción y almacenamiento de hidrógeno mediante deshidrogenación catalítica, y uso de un catalizador de un metal de transición anclado sobre un soporte de un material de carbono para la obtención de hidrógeno mediante reacciones de deshidrogenación catalítica |
KR20210003200A (ko) * | 2018-05-02 | 2021-01-11 | 하이실랩스 에스에이에스 | 수소 운반체 화합물의 제조 및 재생 방법 |
EP3659964A1 (en) * | 2018-11-28 | 2020-06-03 | Hysilabs, SAS | Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds |
ES2949013T3 (es) | 2019-10-31 | 2023-09-25 | Hysilabs Sas | Procedimiento para producir y regenerar compuestos portadores de hidrógeno |
JP2023501177A (ja) * | 2019-10-31 | 2023-01-18 | イシラブズ サス | 水素担体化合物 |
CA3154917A1 (en) | 2019-10-31 | 2021-05-06 | Benjamin BURCHER | Process for producing and regenerating hydrogen carrier compounds |
EP3991833A1 (en) | 2020-10-30 | 2022-05-04 | Hysilabs, SAS | System for on-demand production of hydrogen from a carrier fluid and disposal of solid byproducts |
EP4074412A1 (en) | 2021-04-13 | 2022-10-19 | Hysilabs, SAS | Device for controlled production of a gas from two fluid reagents deposited on a surface |
EP4108630A1 (en) | 2021-06-25 | 2022-12-28 | Hysilabs, SAS | Hydrogen carrier compounds |
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JPS5927901A (ja) * | 1982-07-01 | 1984-02-14 | ザ・フアイヤ−スト−ン・タイヤ・アンド・ラバ−・カンパニ− | 1,3‐ジエンモノマーの重合又は共重合用触媒 |
JPS5945901A (ja) * | 1982-09-03 | 1984-03-15 | Meidensha Electric Mfg Co Ltd | 水素吸蔵物質の水素放出方法および装置 |
JPH05140173A (ja) * | 1991-11-20 | 1993-06-08 | Shin Etsu Chem Co Ltd | 有機ケイ素化合物及びその製造方法 |
JP2001068138A (ja) * | 1999-08-30 | 2001-03-16 | Toyota Autom Loom Works Ltd | 燃料電池用水素供給システム、燃料リサイクル方法、液体運搬用移動体、給油設備及び燃料リサイクルシステム |
JP2009545842A (ja) * | 2006-08-03 | 2009-12-24 | アールイーヴィー・リニューアブル・エナジー・ベンチャーズ・インコーポレイテッド | シラン又はポリシランを用いて燃料電池に水素を供給するための方法 |
WO2008094840A2 (en) * | 2007-02-01 | 2008-08-07 | Hydrogen Solutions International | Hydrogen generation processes using silicon compounds |
WO2008148988A2 (fr) * | 2007-05-04 | 2008-12-11 | Centre National De La Recherche Scientifique (C.N.R.S) | Procédé pour la fourniture du dihydrogène à partir de silicium hydrogéné |
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Publication number | Publication date |
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ES2531531T3 (es) | 2015-03-17 |
RS53853B1 (en) | 2015-08-31 |
HRP20150240T1 (hr) | 2015-06-05 |
PT2536658E (pt) | 2015-03-03 |
CA2789844C (en) | 2016-10-18 |
WO2011098614A1 (en) | 2011-08-18 |
US20130189183A1 (en) | 2013-07-25 |
EP2536658A1 (en) | 2012-12-26 |
CN103025650A (zh) | 2013-04-03 |
EP2536658B1 (en) | 2014-12-03 |
JP5678102B2 (ja) | 2015-02-25 |
SMT201500111B (it) | 2015-07-09 |
KR20130051434A (ko) | 2013-05-20 |
CA2789844A1 (en) | 2011-08-18 |
DK2536658T3 (en) | 2015-03-09 |
SI2536658T1 (sl) | 2015-04-30 |
KR101830448B1 (ko) | 2018-02-20 |
US8642003B2 (en) | 2014-02-04 |
PL2536658T3 (pl) | 2015-04-30 |
CN103025650B (zh) | 2015-09-09 |
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