ES2863542T3 - Proceso para la hidrogenación de cetonas en presencia de catalizadores de Ru (II) - Google Patents

Proceso para la hidrogenación de cetonas en presencia de catalizadores de Ru (II) Download PDF

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Publication number
ES2863542T3
ES2863542T3 ES14171583T ES14171583T ES2863542T3 ES 2863542 T3 ES2863542 T3 ES 2863542T3 ES 14171583 T ES14171583 T ES 14171583T ES 14171583 T ES14171583 T ES 14171583T ES 2863542 T3 ES2863542 T3 ES 2863542T3
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Spain
Prior art keywords
optionally substituted
branched
cyclic
linear
formula
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Active
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ES14171583T
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English (en)
Spanish (es)
Inventor
Alan Dyke
Damian Grainger
Jonathan Medlock
Hans Nedden
Paih Jacques Jean-Marie Le
Stephen James Roseblade
Andreas Seger
Vilvanathan Sivakumar
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Johnson Matthey PLC
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Johnson Matthey PLC
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Priority claimed from GB0904553A external-priority patent/GB0904553D0/en
Priority claimed from GB0913166A external-priority patent/GB0913166D0/en
Application filed by Johnson Matthey PLC filed Critical Johnson Matthey PLC
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    • 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
    • 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
    • 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
    • C07C29/143—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 ketones
    • C07C29/145—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 ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/07—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium compounds without a metal-carbon linkage
    • 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
    • B01J2531/0213—Complexes without C-metal linkages
    • 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
    • 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
    • B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
ES14171583T 2009-03-17 2010-03-17 Proceso para la hidrogenación de cetonas en presencia de catalizadores de Ru (II) Active ES2863542T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0904553A GB0904553D0 (en) 2009-03-17 2009-03-17 Process
US22169009P 2009-06-30 2009-06-30
GB0913166A GB0913166D0 (en) 2009-07-29 2009-07-29 Process

Publications (1)

Publication Number Publication Date
ES2863542T3 true ES2863542T3 (es) 2021-10-11

Family

ID=42629538

Family Applications (2)

Application Number Title Priority Date Filing Date
ES14171583T Active ES2863542T3 (es) 2009-03-17 2010-03-17 Proceso para la hidrogenación de cetonas en presencia de catalizadores de Ru (II)
ES10710411.9T Active ES2628755T3 (es) 2009-03-17 2010-03-17 Procesos para fabricar catalizadores de Ru (II)

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES10710411.9T Active ES2628755T3 (es) 2009-03-17 2010-03-17 Procesos para fabricar catalizadores de Ru (II)

Country Status (7)

Country Link
US (4) US9416100B2 (enExample)
EP (2) EP2408557B1 (enExample)
JP (3) JP5721695B2 (enExample)
CN (3) CN102395427B (enExample)
ES (2) ES2863542T3 (enExample)
SI (2) SI2805765T1 (enExample)
WO (1) WO2010106364A2 (enExample)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2863542T3 (es) * 2009-03-17 2021-10-11 Johnson Matthey Plc Proceso para la hidrogenación de cetonas en presencia de catalizadores de Ru (II)
WO2012026201A1 (en) 2010-08-26 2012-03-01 Takasago International Corporation Ruthenium-diamine complexes and method for producing optically active compounds
CN103502208B (zh) * 2011-04-28 2016-01-13 高砂香料工业株式会社 二胺化合物的制造方法
CA2832994A1 (en) * 2011-05-06 2012-11-15 Takasago International Corporation Ruthenium-diamine complex and method for producing optically active compound
EP2773611B1 (en) * 2011-10-31 2017-01-11 Takasago International Corporation Method for producing optically active -hydroxy- -aminocarboxylic acid ester
GB201219716D0 (en) 2012-11-02 2012-12-12 Univ Warwick Catalyst and process for synthesising the same
MY195032A (en) * 2012-12-18 2023-01-04 Dsm Ip Assets Bv (6R,10R)-6,10,14-Trimetylpentadecan-2-One Prepared From (R)-6,10,14-Trimetylpentadec-5-en-2-One
CN103408597B (zh) * 2013-06-06 2015-12-09 温州大学 一种芳烃钌配合物及其合成方法
WO2015063790A1 (en) * 2013-11-01 2015-05-07 Council Of Scientific And Industrial Research Catalyst for asymmetric transfer hydrogenation of ketones and imines
GB201416628D0 (en) 2014-09-19 2014-11-05 Johnson Matthey Plc Complexes and methods for their preparation
WO2016056669A1 (ja) * 2014-10-10 2016-04-14 高砂香料工業株式会社 固相担持ルテニウム－ジアミン錯体及び光学活性化合物の製造方法
WO2017060922A1 (en) 2015-10-07 2017-04-13 Council Of Scientific & Industrial Research An eco-friendly process for hydrogenation or/and hydrodeoxygenation of organic compound using hydrous ruthenium oxide catalyst
CN105618143B (zh) * 2016-03-09 2017-11-03 山西大学 一种七元氮杂镁金属催化剂及其制备方法和应用
GB201818113D0 (en) 2018-11-06 2018-12-19 Syngenta Participations Ag Process

Family Cites Families (18)

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DE3431591A1 (de) * 1984-08-28 1986-03-13 Diamalt AG, 8000 München Verfahren zur herstellung von aminoverbindungen aus hydroxylverbindungen
JP3410120B2 (ja) * 1991-08-30 2003-05-26 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ アルコールの製造方法
GB9118603D0 (en) 1991-08-30 1991-10-16 Shell Int Research Process for the preparation of alcohols
DK0553778T3 (da) * 1992-01-31 2002-04-08 Hoffmann La Roche Asymmetrisk hydrogenering
DE19725643A1 (de) * 1997-06-18 1998-12-24 Basf Ag Optisch aktive Diphosphinliganden
US6187961B1 (en) * 1997-11-06 2001-02-13 Roche Vitamins Inc. Process for the preparation of trans-(R,R)-actinol
GB0029356D0 (en) * 2000-12-01 2001-01-17 Avecia Ltd Transfer hydrogenation
PL199412B1 (pl) * 2002-10-15 2008-09-30 Boehringer Ingelheim Int Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania
US7446236B2 (en) 2002-12-02 2008-11-04 Solvias Ag Catalytic hydrogenation of carbon-heteroatom double bonds
JP4437648B2 (ja) * 2003-07-18 2010-03-24 セントラル硝子株式会社 光学活性１−（２−トリフルオロメチルフェニル）エチルアミンの製造方法
WO2005092825A1 (ja) * 2004-03-29 2005-10-06 Nagoya Industrial Science Research Institute 光学活性アルコールの製法
US7754889B2 (en) 2004-03-29 2010-07-13 Takasago International Corporation Optically active transition metal-diamine compound and process for producing optically active alcohol with the same
GB0425320D0 (en) * 2004-11-17 2004-12-22 Johnson Matthey Plc Diamines
WO2008012240A1 (en) * 2006-07-27 2008-01-31 F. Hoffmann-La Roche Ag Asymmetric hydrogenation of 1,1,1-trifluoroacetone
CN102046602A (zh) * 2008-04-25 2011-05-04 斯索恩有限公司 制备孟鲁司特中间体的方法
WO2010021505A2 (ko) 2008-08-20 2010-02-25 (주)Lg화학 점착제
ES2863542T3 (es) 2009-03-17 2021-10-11 Johnson Matthey Plc Proceso para la hidrogenación de cetonas en presencia de catalizadores de Ru (II)
JP2015061022A (ja) * 2013-09-20 2015-03-30 凸版印刷株式会社 電子モジュール及びその製造方法

Also Published As

Publication number Publication date
SI2805765T1 (sl) 2021-04-30
EP2408557A2 (en) 2012-01-25
EP2805765B1 (en) 2020-12-23
EP2805765A1 (en) 2014-11-26
JP2012520865A (ja) 2012-09-10
CN106466641B (zh) 2020-06-09
ES2628755T3 (es) 2017-08-03
CN102395427B (zh) 2016-03-16
WO2010106364A3 (en) 2011-06-30
JP5721695B2 (ja) 2015-05-20
CN104030950A (zh) 2014-09-10
JP2015157819A (ja) 2015-09-03
CN102395427A (zh) 2012-03-28
US20160271599A1 (en) 2016-09-22
US20140357903A1 (en) 2014-12-04
JP2018048135A (ja) 2018-03-29
JP6510848B2 (ja) 2019-05-08
WO2010106364A2 (en) 2010-09-23
CN106466641A (zh) 2017-03-01
EP2408557B1 (en) 2017-03-15
US20120123142A1 (en) 2012-05-17
SI2408557T1 (sl) 2017-05-31
US9416100B2 (en) 2016-08-16
CN104030950B (zh) 2017-01-04
US20180290133A1 (en) 2018-10-11
US10406514B2 (en) 2019-09-10

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