DK2536658T3 - Phosphinoxid katalyseret proces til fremstilling af hydrogen fra silylerede derivater som hydrogenbærer - Google Patents

Phosphinoxid katalyseret proces til fremstilling af hydrogen fra silylerede derivater som hydrogenbærer Download PDF

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DK2536658T3
DK2536658T3 DK11703460T DK11703460T DK2536658T3 DK 2536658 T3 DK2536658 T3 DK 2536658T3 DK 11703460 T DK11703460 T DK 11703460T DK 11703460 T DK11703460 T DK 11703460T DK 2536658 T3 DK2536658 T3 DK 2536658T3
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hydrogen
alkyl
compound
aryl
independently selected
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DK11703460T
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Jean-Michel Brunel
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Université D Aix Marseille
Centre Nat Rech Scient
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • 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
    • C01B3/065—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
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • 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
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • 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
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • 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
    • C01B3/22—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of gaseous or liquid organic compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • 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
    • C01B3/22—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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • 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
    • Y02E60/30—Hydrogen technology
    • Y02E60/32—Hydrogen storage
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • 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
    • Y02E60/30—Hydrogen technology
    • Y02E60/36—Hydrogen production from non-carbon containing sources, e.g. by water electrolysis

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Combustion & Propulsion (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silicon Polymers (AREA)

Claims (18)

1. Fremgangsmåde til fremstilling af hydrogen omfattende trinene, at: i) bringe en forbindelse (C), der omfatter en eller flere Si-H-grupper, i kontakt med en phosphorbaseret katalysator i nærvær af en base i vand som opløsningsmiddel, hvorved der dannes hydrogen og et biprodukt (C1); hvori nævnte phosphorbaserede katalysator er valgt fra: - en forbindelse med formlen X1X2X3P(=0), hvori: X1, X2, X3 hver især uafhængigt er valgt blandt CrC6 alkyl, CrC6 alkoxy, NRaRb, C6-C10 aryl, aralkyl, 5- til 7-leddet heteroaryl; hvori nævnte alkyl- eller arylgrupper valgfrit er substitueret med et til tre Rc; eller X1 og X2 sammen med det phosphoratom, hvortil de er bundet, danner en 3- til 10-leddet heterocycloalkyl, der valgfrit er substitueret med Rd; og X3 er som defineret ovenfor; eller X3 er -L-P (=0) X1X2, hvori L er Ci-C6 alkylen eller C6-C10 arylen, og X1, X2 er som defineret ovenfor; Ra og Rb hver uafhængigt er valgt fra CrC6 alkyl, C6-C10 aryl eller sammen med det phosphoratom, hvortil de er bundet, danner en heterocyclyl valgfrit substitueret med et til tre Re; Rc, Rd og Re hver uafhængigt er valgt fra Cl, Br, I, F, OH, CrC6 alkyl, Cr C6 alkoxy, N02, NH2, CN, COOH; - en polymerbåret katalysator bærende en eller flere grupper RaRb(P=0)-, RaRb er som defineret her ovenfor; ii) genvinde det opnåede hydrogen.
2. Fremgangsmåde ifølge krav 1, hvori en af X1, X2, X3 er NRaRb.
3. Fremgangsmåde ifølge krav 1 eller 2, hvori Ra og/eller Rb er CrC6 alkyl.
4. Fremgangsmåde ifølge ethvert af kravene 1 til 3, hvori den phosphorbaserede katalysator er hexamethylphosphoramid (HMPA).
5. Fremgangsmåde ifølge ethvert af kravene 1 til 4, hvori polymeren, der bærer katalysatoren er (aminomethyl)polystyren.
6. Fremgangsmåde ifølge ethvert af kravene 1 til 5, hvori forbindelsen (C) omfatter en eller flere monomerenheder med formlen:
hvori: R er en binding, CrC6 alkylen, (CrC4 alkylen)m-Z-(Ci-C4 alkylen)q; Z er O, NR10, S(0)y, CR10= CR10, ΟξΟ, C6-C10 arylen, 5-1 O-leddet heteroarylen eller C3-C6 cycloalkylen; R1, R2 hver uafhængigt er valgt fra H, halogen, CrCi0 alkyl, C3-Ci0 cycloalkyl, C6-C12 aryl, aralkyl, 5- til 10-leddet heteroaryl, OR3, NR4R5, SiR6R7R8, hvori nævnte arylgrupper valgfrit er substitueret med et til tre R9 grupper; R3 er H, CrC6 alkyl, C6-Ci0 aryl, aralkyl; R4, R5 hver uafhængigt er valgt fra H, CrC6 alkyl, C6-Ci0 aryl, aralkyl; R6, R7, R8 hver uafhængigt er valgt fra H, OR3, CrC6 alkyl, C6-Ci0 aryl, aralkyl; R9 er valgt blandt halogen, CrCi0 alkyl, OR10, N02, NR11R12, CN, C(=0)R1°, C(=0)0R1°, S(=0)CH3, hvori nævnte alkylgruppe valgfrit er substitueret med et eller flere halogen; R10 er H eller CrC3 alkyl; R11, R12 hver uafhængigt er valgt fra H eller C1-C10 alkyl; m, q er 0 eller 1; y er 0, 1 eller 2; n, p er heltal hver repræsenterende antallet af gentagende enheder hvor n er større eller lig med 1, og p er 0 eller 1.
7. Fremgangsmåde ifølge krav 6, hvori den monomere enhed har formlen:
hvori R er CrC6 alkylen.
8. Fremgangsmåde ifølge krav 6, hvori den monomere enhed har formlen:
9. Fremgangsmåde ifølge ethvert af kravene 6 til 8, hvori forbindelsen (C) er H3Si(CH2)2SiH3 eller PhSiH3.
10. Fremgangsmåde ifølge ethvert af kravene 1 til 5, hvori forbindelsen (C) er C(SiH3)4.
11. Fremgangsmåde ifølge ethvert af kravene 1 til 10, hvori basen er et alkalisk eller jordalkalisk metalhydroxid, eller benzylamin.
12. Fremgangsmåde ifølge ethvert af kravene 1 til 11, yderligere omfattende følgende efterfølgende recirkuleringstrin, at: a) bringe biproduktet (C1) i kontakt med et acylhalogenid; b) bringe det opnåede produkt i kontakt med et metalhydrid, hvorved forbindelsen (C) regeneres.
13. Sammensætning, der omfatter en forbindelse (C), en phosphorbaseret katalysator, en base og vand som opløsningsmiddel som defineret i ethvert af kravene 1 til 12.
14. Anvendelse af en sammensætning ifølge krav 13 til fremstilling af hydrogen.
15. Indretning til fremstilling af hydrogen ifølge fremgangsmåden ifølge ethvert af kravene 1 til 14, nævnte indretning omfatter et reaktionskammer omfattende: i. et reaktionsblandingsindløb, nævnte blanding omfatter en forbindelse (C), en base i vand som et opløsningsmiddel; ii. et hydrogenudløb; iii. en biproduktopsamler; og iv. en overflade, der er beregnet til at være i kontakt med nævnte blanding, er coatet med en polymerbåret katalysator som defineret i krav 1.
16. Indretning ifølge krav 15 yderligere omfattende et blandekammer til blanding af forbindelsen (C) med basen i vand som et opløsningsmiddel, hvori blandekammeret er forbundet med reaktionskammeret.
17. Indretning ifølge ethvert af kravene 15 eller 16, yderligere omfattende et biproduktopsamlingskammer, hvori opsamlingskammeret er forbundet med reaktionskammeret.
18. Indretning ifølge krav 15 yderligere omfattende et andet kammer omfattende: v. en ydre kappe; vi. en indre væg adskillende nævnte kammer i to særskilte rum, nemlig: 1. et første rum indeholdende reaktionsblandingen, der skal indføres i reaktionskammeret; og 2. et anden rum indeholdende biproduktet (C1) opsamlet fra reaktionskammeret; 3. det første og andet rum er hver forbundet til reaktionskammeret; og vii. midler til at bevæge den indre væg i forhold til den ydre kappe , således at hvert rums respektive volumener varierer.
DK11703460T 2010-02-15 2011-02-15 Phosphinoxid katalyseret proces til fremstilling af hydrogen fra silylerede derivater som hydrogenbærer DK2536658T3 (da)

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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

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JP (1) JP5678102B2 (da)
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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
EP3788003A1 (en) * 2018-05-02 2021-03-10 Hysilabs, SAS Process for producing and regenerating hydrogen carrier compounds
EP3659964A1 (en) 2018-11-28 2020-06-03 Hysilabs, SAS Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds
EP3816204B1 (en) 2019-10-31 2023-06-07 Hysilabs, SAS Process for producing and regenerating hydrogen carrier compounds
CA3154904A1 (en) 2019-10-31 2021-05-06 Benjamin BURCHER Hydrogen carrier compounds
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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US4473661A (en) * 1982-07-01 1984-09-25 The Firestone Tire & Rubber Company Polymerization catalyst system containing organolithium, dialkyl magnesium and/or trialkyl aluminum, and a phosphine oxide
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
JP2541060B2 (ja) * 1991-11-20 1996-10-09 信越化学工業株式会社 有機ケイ素化合物の製造方法
JP3915334B2 (ja) * 1999-08-30 2007-05-16 株式会社豊田自動織機 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
WO2005037421A2 (en) * 2003-10-14 2005-04-28 Advanced Technology Materials, Inc. Hydrogen generation
CA2617742A1 (en) * 2005-08-03 2007-02-15 The University Of Alabama Silanes as a source of hydrogen
DE102006030798B4 (de) * 2006-06-30 2009-04-02 Christoph Mennel Verwendung von Silanen als chemische Wasserstoffspeicher und silanbetriebenes Brennstoffzellensystem
DE102006039869A1 (de) * 2006-08-03 2008-02-21 Daimler Ag Verfahren zur Versorgung einer Brennstoffzelle mit Wasserstoff mittels Silanen oder Polysilanen
WO2008094840A2 (en) * 2007-02-01 2008-08-07 Hydrogen Solutions International Hydrogen generation processes using silicon compounds
FR2915742B1 (fr) * 2007-05-04 2014-02-07 Centre Nat Rech Scient Procede pour la fourniture du dihydrogene a partir de silicium hydrogene

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CN103025650A (zh) 2013-04-03
KR20130051434A (ko) 2013-05-20
RS53853B1 (en) 2015-08-31
JP5678102B2 (ja) 2015-02-25
SMT201500111B (it) 2015-07-09
WO2011098614A1 (en) 2011-08-18
CA2789844C (en) 2016-10-18
PL2536658T3 (pl) 2015-04-30
CA2789844A1 (en) 2011-08-18
JP2013519615A (ja) 2013-05-30
EP2536658B1 (en) 2014-12-03
ES2531531T3 (es) 2015-03-17
US8642003B2 (en) 2014-02-04
KR101830448B1 (ko) 2018-02-20
PT2536658E (pt) 2015-03-03
HRP20150240T1 (hr) 2015-06-05
EP2536658A1 (en) 2012-12-26
US20130189183A1 (en) 2013-07-25
CN103025650B (zh) 2015-09-09

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