JP6312609B2 - 水素化プロセスのための金属粉末状触媒 - Google Patents
水素化プロセスのための金属粉末状触媒 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims description 91
- 239000000843 powder Substances 0.000 title description 12
- 238000005984 hydrogenation reaction Methods 0.000 title description 11
- 229910001092 metal group alloy Inorganic materials 0.000 claims description 38
- 229910044991 metal oxide Inorganic materials 0.000 claims description 24
- 150000004706 metal oxides Chemical class 0.000 claims description 24
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 17
- 229910052804 chromium Inorganic materials 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 229910052748 manganese Inorganic materials 0.000 claims description 11
- 239000002105 nanoparticle Substances 0.000 claims description 11
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910001240 Maraging steel Inorganic materials 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 239000010935 stainless steel Substances 0.000 claims description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 230000002378 acidificating effect Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000001371 (5E)-3,5-dimethylocta-1,5,7-trien-3-ol Substances 0.000 description 3
- MULUCORRSAVKOA-UHFFFAOYSA-N 3,7,11,15-tetramethylhexadec-1-yn-3-ol Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)C#C MULUCORRSAVKOA-UHFFFAOYSA-N 0.000 description 3
- ZJIQIJIQBTVTDY-SREVYHEPSA-N dehydrolinalool Chemical compound CC(=C)\C=C/CC(C)(O)C=C ZJIQIJIQBTVTDY-SREVYHEPSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 101150003085 Pdcl gene Proteins 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- JQKZSMVJERVJHO-UHFFFAOYSA-N CCCNC(CCCC(CCCC(C#N)(N)O)N[I](=C)=C)CCCC(N)NC(C)=[IH] Chemical compound CCCNC(CCCC(CCCC(C#N)(N)O)N[I](=C)=C)CCCC(N)NC(C)=[IH] JQKZSMVJERVJHO-UHFFFAOYSA-N 0.000 description 1
- 229910000531 Co alloy Inorganic materials 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 229910001182 Mo alloy Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000001994 activation Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
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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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/8993—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with chromium, molybdenum or tungsten
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/60—Platinum group metals with zinc, cadmium or mercury
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
- B01J35/393—Metal or metal oxide crystallite size
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0207—Pretreatment of the support
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0215—Coating
- B01J37/0225—Coating of metal substrates
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0215—Coating
- B01J37/0225—Coating of metal substrates
- B01J37/0226—Oxidation of the substrate, e.g. anodisation
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Crystallography & Structural Chemistry (AREA)
Description
(i)金属合金の総重量に基づいて45重量%〜75重量%のFeと、
(ii)金属合金の総重量に基づいて15重量%〜30重量%のNiと、
(iii)金属合金の総重量に基づいて5重量%〜20重量%のCoと、
(iv)金属合金の総重量に基づいて3重量%〜8重量%のMoと、
を含む金属合金担体を含み、この場合に、前記金属合金は、金属酸化物層によって被覆され、且つ、Pdで含浸される、粉末状触媒系(I)に関する。
・触媒は、反応の後、容易に再利用(及び除去)される。これは、例えば濾過によって行われることができる。
・触媒は、2回以上使用可能である(再利用可能)。
・触媒は、そのままで、非常に安定な系である。例えば、酸、並びに、水に対して安定である。
・触媒は、容易に生成される。
・触媒は、容易に処理される。
・水素化は、いかなる溶媒をも用いることなく実行可能である。
・触媒は、鉛を含まない。
・触媒は、水素化反応において高い選択性を示す。
(i)金属合金の総重量に基づいて60重量%〜70重量%のFeと、
(ii)金属合金の総重量に基づいて15重量%〜25重量%のNiと、
(iii)金属合金の総重量に基づいて5重量%〜15重量%のCoと、
(iv)金属合金の総重量に基づいて3.5重量%〜7重量%のMoと、
を含む金属合金担体を含み、この場合に、前記金属合金は、金属酸化物層によって被覆され、且つ、Pdで含浸される、粉末状触媒系(II)に関する。
(式中、R1は、直鎖型又は分岐型のC5〜C35アルキル、又は、直鎖型又は分岐型のC5〜C35アルケニル部位であり、炭素鎖は置換されることができ、且つ、R2は、直鎖型又は分岐型のC1〜C4アルキルであり、炭素鎖は置換されることができる)の化合物を、触媒(I)、(II)、(III)、(III’)、(III’’)、(IV)、(IV’)、(IV’’)、(V)、(VI)、(VII)、(VII’)、(VIII)及び/又は(IX)の存在下にて、水素と反応させる方法に関する。
[実施例1:触媒の合成(Al2O3/ZnO及びPdの沈積によって被覆されたマルエージング鋼)]
[ステップ1:熱による前処理]
ステンレス鋼の粉末(EOS GmbH、独国より市販のEOS Maraging Steel MS1(登録商標))に対して、450℃で3時間、熱による前処理を実施した。
100mlフラスコに、Al(NO3)39H2O20.0g(53.3ミリモル)及び水70mlを加えた。Al(NO3)3・9H2Oが完全に溶解するまで、混合物を撹拌した。溶液を95℃まで加熱した。次いで、ZnOの粉末4.34g(53.3ミリモル)を反応溶液にゆっくりと加えた。ZnOが完全に溶解するまで、加熱及び撹拌を維持した。次いで、溶液を室温まで冷却し、メンブランフィルターを通して濾過した。
モリブデン酸ナトリウム二水和物318mg(1.31ミリモル)と無水パラジウム(II)塩化物212mg(1.20ミリモル)を、加熱下にて(約95℃)、脱イオン水60mlに加えた。混合物を撹拌した。水が完全に蒸発するまで、加熱及び撹拌を継続した(固体の残渣が形成した)。その後、脱イオン水60mlを、攪拌下にて残渣に加えた。蒸発−溶解のサイクルは、PdCl2を完全に溶解させるために、2回繰り返した。最後に、熱水100mlを、固体の残渣に加えた。濃い茶色の溶液を室温まで冷却し、濾紙を通して濾過した。前駆体溶液の最終的な量が120mLになるまで、フィルターを水で洗浄した。
ステップ3から得られた粉末触媒に対して、H2−Ar気流下にて、300℃で4時間、温度処理を実施した。次いで、同じH2−Ar気流下にて、室温まで冷却した。
Claims (14)
- 金属合金担体を含む粉末状選択的接触水素化用触媒であって、前記金属合金担体は、
(i)前記金属合金の総重量に基づいて45重量%〜75重量%のFeと、
(ii)前記金属合金の総重量に基づいて15重量%〜30重量%のNiと、
(iii)前記金属合金の総重量に基づいて5重量%〜20重量%のCoと、
(iv)前記金属合金の総重量に基づいて3重量%〜8重量%のMoと、
を含み、前記金属合金は、金属酸化物層によって被覆され、且つ、Pd−ナノ粒子で含浸される、粉末状選択的接触水素化用触媒。 - 前記金属合金はマルエージング鋼である、請求項1に記載の選択的接触水素化用触媒。
- 前記金属合金は更なる金属を含む、請求項1又は2に記載の選択的接触水素化用触媒。
- 前記金属合金は炭素を含む、請求項1〜3のいずれか一項に記載の選択的接触水素化用触媒。
- 前記金属合金はステンレス鋼であって、前記ステンレス鋼は、
(i)前記金属合金の総重量に基づいて60重量%〜70重量%のFeと、
(ii)前記金属合金の総重量に基づいて15重量%〜25重量%のNiと、
(iii)前記金属合金の総重量に基づいて5重量%〜15重量%のCoと、
(iv)前記金属合金の総重量に基づいて3.5重量%〜7重量%のMoと、
を含み、前記金属合金は、金属酸化物層によって被覆され、且つ、Pd−ナノ粒子で含浸される、請求項1〜4のいずれか一項に記載の選択的接触水素化用触媒。 - 前記金属酸化物層は、塩基性又は両性である、請求項1〜5のいずれか一項に記載の選択的接触水素化用触媒。
- 前記金属酸化物層は、Zn、Cr、Mn、Cu、及び/又はAlを含む、請求項1〜6のいずれか一項に記載の選択的接触水素化用触媒。
- 前記金属酸化物層は、ZnOと、場合により、Cr、Mn、Mg、Cu、及びAlからなる群から選択される少なくとも1つの更なる金属酸化物とを含む、請求項1〜7のいずれか一項に記載の選択的接触水素化用触媒。
- 前記金属酸化物層は、ZnO及びAl2O3を含む、請求項1〜8のいずれか一項に記載の選択的接触水素化用触媒。
- 前記触媒の総重量に基づいて0.1重量%〜50重量%の前記金属酸化物層を含む、請求項1〜9のいずれか一項に記載の選択的接触水素化用触媒。
- 前記金属酸化物は、2:1〜1:2の比におけるZnOとAl2O3の混合物である、請求項1〜10のいずれか一項に記載の選択的接触水素化用触媒。
- 前記Pd−ナノ粒子は、0.5〜20nmの平均粒径を有する、請求項1〜11のいずれか一項に記載の選択的接触水素化用触媒。
- 前記触媒は、前記触媒の総重量に基づいて0.001重量%〜5重量%の前記Pd−ナノ粒子を含む、請求項1〜12のいずれか一項に記載の選択的接触水素化用触媒。
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EP12156823 | 2012-02-24 | ||
EP12156823.2 | 2012-02-24 | ||
PCT/EP2013/053512 WO2013124392A1 (en) | 2012-02-24 | 2013-02-22 | Metal powderdous catalyst for hydrogenation processes |
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JP6312609B2 true JP6312609B2 (ja) | 2018-04-18 |
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US (1) | US9238218B2 (ja) |
EP (1) | EP2817093B1 (ja) |
JP (1) | JP6312609B2 (ja) |
KR (1) | KR102096118B1 (ja) |
CN (2) | CN108246288A (ja) |
BR (1) | BR112014020919B1 (ja) |
IN (1) | IN2014DN07057A (ja) |
WO (1) | WO2013124392A1 (ja) |
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CN104245112B (zh) * | 2012-04-18 | 2019-05-07 | 帝斯曼知识产权资产管理有限公司 | 适用于氢化反应(iii)的装置 |
JP6360037B2 (ja) * | 2012-04-18 | 2018-07-18 | ディーエスエム アイピー アセッツ ビー.ブイ. | 水素化反応に有用な装置の使用 |
CN106391044A (zh) * | 2015-07-28 | 2017-02-15 | 江苏吉华化工有限公司 | 一种催化剂 |
PL3618956T3 (pl) * | 2017-05-01 | 2024-02-19 | Dsm Ip Assets B.V. | Sproszkowany katalizator metalowy do sposobów uwodorniania |
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GB1578122A (en) * | 1976-02-11 | 1980-11-05 | Johnson Matthey Co Ltd | Catalytic hydrogenation of fatty oils |
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JP2000510042A (ja) * | 1996-05-14 | 2000-08-08 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 耐火性担体上にナノ微粒子状金属を有する触媒組成物 |
US20070053784A1 (en) * | 2005-09-06 | 2007-03-08 | Crucible Materials Corp. | Maraging steel article and method of manufacture |
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EP2817093A1 (en) | 2014-12-31 |
WO2013124392A1 (en) | 2013-08-29 |
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US9238218B2 (en) | 2016-01-19 |
EP2817093B1 (en) | 2020-03-25 |
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