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EA201992191A1 - Способ получения дейтерированного этанола из d - Google Patents

Способ получения дейтерированного этанола из d

Info

Publication number
EA201992191A1
EA201992191A1 EA201992191A EA201992191A EA201992191A1 EA 201992191 A1 EA201992191 A1 EA 201992191A1 EA 201992191 A EA201992191 A EA 201992191A EA 201992191 A EA201992191 A EA 201992191A EA 201992191 A1 EA201992191 A1 EA 201992191A1
Authority
EA
Eurasian Patent Office
Prior art keywords
producing
ethanol
deutered
amide
acetate
Prior art date
Application number
EA201992191A
Other languages
English (en)
Other versions
EA039766B1 (ru
Inventor
Лоран Лефор
Майк Шмиткамп
Original Assignee
Дьютерия Бевериджес, Ллс
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Дьютерия Бевериджес, Ллс filed Critical Дьютерия Бевериджес, Ллс
Publication of EA201992191A1 publication Critical patent/EA201992191A1/ru
Publication of EA039766B1 publication Critical patent/EA039766B1/ru

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001—Acyclic or carbocyclic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/189—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms containing both nitrogen and phosphorus as complexing atoms, including e.g. phosphino moieties, in one at least bidentate or bridging ligand
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/08—Ethanol
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0258—Flexible ligands, e.g. mainly sp3-carbon framework as exemplified by the "tedicyp" ligand, i.e. cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/827—Iridium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
    • C07C29/90—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound using hydrogen only
    • 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00—Chemistry of hydrocarbon compounds
    • Y10S585/929—Special chemical considerations
    • Y10S585/941—Isotope exchange process

Landscapes

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

Abstract

Настоящее изобретение относится к способу получения дейтерированного этанола из уксусной кислоты, ацетата или амида путем реакции с Dв присутствии катализатора на основе переходного металла.
EA201992191A 2017-04-27 2018-04-26 Способ получения дейтерированного этанола из d2 EA039766B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762491181P 2017-04-27 2017-04-27
PCT/US2018/029660 WO2018200882A1 (en) 2017-04-27 2018-04-26 Process for the preparation of deuterated ethanol from d2

Publications (2)

Publication Number Publication Date
EA201992191A1 true EA201992191A1 (ru) 2020-04-16
EA039766B1 EA039766B1 (ru) 2022-03-11

Family

ID=63915897

Family Applications (1)

Application Number Title Priority Date Filing Date
EA201992191A EA039766B1 (ru) 2017-04-27 2018-04-26 Способ получения дейтерированного этанола из d2

Country Status (12)

Country Link
US (2) US10343955B2 (ru)
EP (1) EP3615205A4 (ru)
JP (1) JP7109471B2 (ru)
KR (1) KR20200004827A (ru)
CN (1) CN110545911B (ru)
AU (1) AU2018260728B2 (ru)
BR (1) BR112019022269A2 (ru)
CA (1) CA3059761A1 (ru)
EA (1) EA039766B1 (ru)
IL (1) IL270177B (ru)
WO (1) WO2018200882A1 (ru)
ZA (1) ZA201906621B (ru)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112019022276A2 (pt) 2017-04-27 2020-05-19 Deuteria Beverages Llc processo para a preparação de etanol deuterado a partir de d2o
CN112321388A (zh) * 2020-11-16 2021-02-05 徐州亚兴医疗科技有限公司 一种高转化率的氘代甲醇的制备方法
CN114904518B (zh) * 2022-05-07 2023-11-10 南京凝氘生物科技有限公司 一种由氘气合成氘代乙醇-d6的催化剂、其制备方法及其应用
CN114768803B (zh) * 2022-05-07 2023-11-10 南京凝氘生物科技有限公司 一种合成全氘代甲醇的催化剂、其制备方法及其应用
EP4357325A1 (de) * 2022-10-21 2024-04-24 Evonik Operations GmbH Verfahren zur herstellung eines mehrfach deuterierten alkohols mittels kupfer-katalysators

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200404054A (en) * 2002-07-26 2004-03-16 Wako Pure Chem Ind Ltd Method for deuteration of aromatic ring
EP1707548A4 (en) * 2004-01-23 2007-08-15 Wako Pure Chem Ind Ltd DEUTERIZATION PROCEDURE USING A MIXED CATALYST
US20080145303A1 (en) * 2005-01-28 2008-06-19 Wako Pure Chemical Indussries, Ltd. Method for Producing Deuterium Gas and Catalytic Deuteration Method Using Deuterium Gas Obtained Thereby
ATE481373T1 (de) 2007-04-03 2010-10-15 Firmenich & Cie 1,4-hydrierung von sorbol mit ru-komplexen
US8658236B2 (en) 2009-08-21 2014-02-25 Deuteria Beverages, Llc Alcoholic compositions having a lowered risk of acetaldehydemia
JP5671456B2 (ja) 2009-10-23 2015-02-18 高砂香料工業株式会社 ３座配位子を有する新規ルテニウムカルボニル錯体、並びにその製造法及び用途
JP5849710B2 (ja) 2011-02-03 2016-02-03 セントラル硝子株式会社 β−フルオロアルコール類の製造方法
WO2012160015A1 (en) * 2011-05-23 2012-11-29 Sanofi Process for the preparation of deuterated compounds containing n-alkyl groups
CN103772142B (zh) 2012-10-19 2018-04-27 中国科学院上海有机化学研究所 钌络合物及制备甲醇和二醇的方法
BR112015022807A2 (pt) 2013-03-15 2017-07-18 Firmenich & Cie hidrogenação seletiva de aldeídos com complexos de ligantes de ru/bidentados
CN104692992B (zh) * 2015-03-13 2016-08-17 武汉众宇动力系统科技有限公司 氘代乙烯制备方法
CN105237342B (zh) 2015-11-06 2018-06-26 河北师范大学 一种催化氢化羧酸酯还原制备醇的方法

Also Published As

Publication number Publication date
JP2020518577A (ja) 2020-06-25
EA039766B1 (ru) 2022-03-11
US20200189991A1 (en) 2020-06-18
CN110545911B (zh) 2022-12-27
US20180312454A1 (en) 2018-11-01
WO2018200882A1 (en) 2018-11-01
US10899681B2 (en) 2021-01-26
US10343955B2 (en) 2019-07-09
CN110545911A (zh) 2019-12-06
AU2018260728B2 (en) 2022-07-21
CA3059761A1 (en) 2018-11-01
JP7109471B2 (ja) 2022-07-29
AU2018260728A1 (en) 2019-10-31
EP3615205A1 (en) 2020-03-04
EP3615205A4 (en) 2020-12-09
BR112019022269A2 (pt) 2020-05-19
ZA201906621B (en) 2020-09-30
IL270177B (en) 2021-10-31
KR20200004827A (ko) 2020-01-14

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