JP2020533265A - 水素貯蔵の新しい方法 - Google Patents
水素貯蔵の新しい方法 Download PDFInfo
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- alkoxyamine
- borane complex
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- borane
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- 239000001257 hydrogen Substances 0.000 title claims abstract description 43
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000003860 storage Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 27
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims abstract description 59
- 229910000085 borane Inorganic materials 0.000 claims abstract description 57
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 101150003085 Pdcl gene Proteins 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000010586 diagram Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- NRPJNSNRIFSGCC-UHFFFAOYSA-N B.CON Chemical compound B.CON NRPJNSNRIFSGCC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000007689 inspection Methods 0.000 description 4
- 239000011995 wilkinson's catalyst Substances 0.000 description 4
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 4
- -1 1 Chemical compound 0.000 description 3
- 125000005262 alkoxyamine group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 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 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000011943 nanocatalyst Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004964 aerogel Substances 0.000 description 1
- TVJORGWKNPGCDW-UHFFFAOYSA-N aminoboron Chemical compound N[B] TVJORGWKNPGCDW-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
- LNLSXDSWJBUPHM-UHFFFAOYSA-N iminoborane Chemical compound N=B LNLSXDSWJBUPHM-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZBDXGNXNXXPKJI-UHFFFAOYSA-N o-tert-butylhydroxylamine;hydrochloride Chemical compound Cl.CC(C)(C)ON ZBDXGNXNXXPKJI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013341 scale-up Methods 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
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- 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
- C01B3/0005—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes
- C01B3/001—Reversible uptake of hydrogen by an appropriate medium, i.e. based on physical or chemical sorption phenomena or on reversible chemical reactions, e.g. for hydrogen storage purposes ; Reversible gettering of hydrogen; Reversible uptake of hydrogen by electrodes characterised by the uptaking medium; Treatment thereof
- C01B3/0015—Organic compounds; Solutions thereof
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B6/00—Hydrides of metals including fully or partially hydrided metals, alloys or intermetallic compounds ; Compounds containing at least one metal-hydrogen bond, e.g. (GeH3)2S, SiH GeH; Monoborane or diborane; Addition complexes thereof
- C01B6/06—Hydrides of aluminium, gallium, indium, thallium, germanium, tin, lead, arsenic, antimony, bismuth or polonium; Monoborane; Diborane; Addition complexes thereof
- C01B6/10—Monoborane; Diborane; Addition complexes thereof
- C01B6/13—Addition complexes of monoborane or diborane, e.g. with phosphine, arsine or hydrazine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Hydrogen, Water And Hydrids (AREA)
Abstract
Description
この化合物は1958年(Parry et al. JACS 1958, 80, 1549;. Parry et al. JACS 1958, 80, 1868)から遡って2つの記事にのみ記載されている。
物理的な貯蔵についての技術は現在、高度に先進的であり、350〜700バールで運転される液体水素タンクがあり、この運転温度はマイナス120℃のオーダーである。
発明の意味において「アルコキシアミン‐ボラン錯体」とはアルコキシアミンとボランとの反応で形成された錯体という意味である。
本発明の意味において「水素貯蔵」とは水素を保存して、使用する際には放出する方法という意味である。
本発明の意味において「水素の放出」とは水素の放出ができる科学的ステップという意味である。
上に記載した0.5mmolのアルコキシアミン‐ボラン錯体の1つから出発する水素放出反応は5cm3〜25cm3の気体を生成する。
のヒドロキシルアミンまたはこれらの塩、例えば塩酸塩をNaBH4、および鉱酸、好ましくはH2SO4またはHClと合わせるステップを含む、式(I)のアルコキシアミン‐ボラン錯体の調製法に関し、この方法では精製ステップは必要としない。
実施例1
THF中におけるNaBH4のみの存在下で、N,O-ジメチルヒドロキシルアミンからアルコキシアミン‐ボラン錯体を合成するために発明者らが実施した試験は2時間の間に77%の良い収率を得た。
アルコキシアミン‐ボラン錯体(2)はTHF中における水素化ホウ素ナトリウムの存在下でO-tert-ブチルヒドロキシルアミン塩酸塩を用いて上の記載と同じ条件下で合成された(表2)。この合成は小さな規模で開始され(CF39)、その後は大きな規模で(CF452)実施された。
上に記載の合成とは異なり、アルコキシアミン‐ボラン錯体(3)および(4)は非商業的な、つまり事前に合成して準備した塩酸塩(表3、4、5)から調製された。
合成された最後のアルコキシアミン‐ボラン錯体はTHF中において、NaBH4の存在下で市販のO-メチルヒドロキシルアミン塩酸塩からのO-メチルヒドロキシルアミン‐ボラン(5)である。別の開始材料とは異なり、この塩酸塩は多くの溶媒中で低溶解性を持つ。この合成においてO-メチルヒドロキシルアミン塩酸塩の溶解性を向上させるために、条件の最適化に係る膨大な試験がなされた(表5)。
アルコキシアミン‐ボラン錯体(1)、(2)、(5)については多くの実験がなされてきた。これらの実験はホウ素-窒素供与結合の興味のある特性の同定を可能にした。これらの実験の目標は一部の反応において、例えば脱水素化によるアミノボランの形成における前駆体としての化合物の有用性を確立することであった。
加えてアルコキシアミン‐ボラン錯体は水素の高密度状態により水素貯蔵での応用において高い可能性を示す。
遷移金属触媒の存在下における上に記載のアルコキシアミン‐ボラン錯体の脱水素化を示す。
最も効果的な触媒は1当量の水素がそれぞれのアルコキシアミン‐ボラン錯体から放出される、Wilkinson触媒(RhCl(PPh3)3)およびNiCl2(PPh3)2であると認められた(表6、7、8)。
錯体(1)、(2)、(5)は脱水素化速度が異なるので、これらの錯体のいずれかを使用することで脱水素化の速度を調節できる。
Wilkinson触媒(RhCl(PPh3)3)、NiCl2(PPh3)2および相応するナノ触媒を使用してO-メチルヒドロキシルアミン‐ボラン錯体(5)について追加的試験を50℃の温度で実施した(表9)。
2つのナノ触媒がO-メチルヒドロキシルアミン‐ボラン(5)の脱水素化反応において効果的であった。
Claims (13)
- 水素貯蔵用のアルコキシアミン‐ボラン錯体の使用。
- 水素貯蔵用であり、続く水素放出のステップのためのアルコキシアミン‐ボラン錯体の、請求項1に記載の使用。
- 錯体が式(I)
のアルコキシアミン‐ボランの錯体である、請求項1に記載のアルコキシアミン‐ボラン錯体の使用。 - アルコキシアミン‐ボラン錯体の脱水素化ステップを含むアルコキシアミン‐ボラン錯体からの水素放出方法。
- 少なくとも1つのアルコキシアミン‐ボラン錯体を触媒に接触させるステップか、上に記載のアルコキシアミン‐ボラン錯体の熱的加熱ステップかを含む、請求項4に記載の水素放出方法。
- 少なくとも1つのアルコキシアミン‐ボラン錯体をロジウム、プラチナ、パラジウム、金、またはニッケル錯体、特にRhCl(PPh3)3、NiCl2(PPh3)2、Rh@TBABおよびNi@TBAB、Pd(OH)2/C、PtCl2、PdCl2、KAuCl4、Pt(PPh3)4から選択される錯体に接触させるステップを含む、請求項4に記載の水素放出方法。
- アルコキシアミン‐ボラン錯体をRhCl(PPh3)3に接触させるステップを含む、請求項4に記載の水素放出方法。
- アルコキシアミン‐ボラン錯体をNiCl2(PPh3)2に接触させるステップを含む、請求項4に記載の水素放出方法。
- アルコキシアミン‐ボラン錯体をRh@TBABに接触させるステップを含む、請求項4に記載の水素放出方法。
- アルコキシアミン‐ボラン錯体をNi@TBABに接触させるステップを含む、請求項4に記載の水素放出方法。
- 80℃を超えて、好ましくは120℃を超えた温度で上に記載のアルコキシアミン‐ボラン錯体の熱的加熱のステップを含む、請求項4に記載の水素放出方法。
- 式(II)
のヒドロキシルアミン、またはこれらの塩、例えば塩酸塩とNaBH4、および鉱酸、好ましくはH2SO4またはHClとを合わせるステップを含み、この方法では精製ステップは必要としない、式(I)のアルコキシアミン‐ボラン錯体の調製法 - 下に記載のアルコキシアミン‐ボラン錯体:
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Application Number | Priority Date | Filing Date | Title |
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FR1758543A FR3070974A1 (fr) | 2017-09-14 | 2017-09-14 | Nouveau procede de stockage de l'hydrogene |
FR1758543 | 2017-09-14 | ||
PCT/FR2018/052250 WO2019053382A1 (fr) | 2017-09-14 | 2018-09-13 | Nouveau procede de stockage de l'hydrogene |
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JP2020533265A true JP2020533265A (ja) | 2020-11-19 |
JP2020533265A5 JP2020533265A5 (ja) | 2021-10-21 |
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US (1) | US20200255289A1 (ja) |
EP (1) | EP3681841A1 (ja) |
JP (1) | JP2020533265A (ja) |
CA (1) | CA3075501A1 (ja) |
FR (1) | FR3070974A1 (ja) |
WO (1) | WO2019053382A1 (ja) |
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D.H.CAMPBELL ET AL.: "The Reaction of Hydroxylamine and its N-Methyl Derivatives with Diborane", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 80, no. 7, JPN7022002119, 5 April 1958 (1958-04-05), US, pages 1549 - 1552, XP055472599, ISSN: 0004931876, DOI: 10.1021/ja01540a010 * |
T.C. BISSOT ET AL.: "The Reaction of O-Methylhydroxylamine and its N-Methyl Derivatives with Diborane", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 80, no. 8, JPN7022002120, 20 April 1958 (1958-04-20), US, pages 1868 - 1874, XP055472591, ISSN: 0004931875, DOI: 10.1021/ja01541a022 * |
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US20200255289A1 (en) | 2020-08-13 |
CA3075501A1 (fr) | 2019-03-21 |
WO2019053382A1 (fr) | 2019-03-21 |
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