RU2014152878A - Катализатор для получения высших спиртов - Google Patents
Катализатор для получения высших спиртов Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract 6
- 150000001298 alcohols Chemical class 0.000 title claims 2
- 238000000034 method Methods 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract 4
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 claims abstract 4
- 150000001450 anions Chemical class 0.000 claims abstract 4
- 238000000975 co-precipitation Methods 0.000 claims abstract 4
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical group [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims abstract 4
- 229960001545 hydrotalcite Drugs 0.000 claims abstract 4
- 229910001701 hydrotalcite Inorganic materials 0.000 claims abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract 4
- 238000005470 impregnation Methods 0.000 claims abstract 4
- 229910052742 iron Inorganic materials 0.000 claims abstract 4
- 229910052748 manganese Inorganic materials 0.000 claims abstract 4
- 229910052751 metal Inorganic materials 0.000 claims abstract 4
- 239000002184 metal Substances 0.000 claims abstract 4
- 229910052759 nickel Inorganic materials 0.000 claims abstract 4
- 238000005979 thermal decomposition reaction Methods 0.000 claims abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910002651 NO3 Inorganic materials 0.000 claims abstract 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910019142 PO4 Inorganic materials 0.000 claims abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract 2
- 150000004703 alkoxides Chemical class 0.000 claims abstract 2
- 229910052782 aluminium Inorganic materials 0.000 claims abstract 2
- 238000000137 annealing Methods 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052791 calcium Inorganic materials 0.000 claims abstract 2
- 229910052804 chromium Inorganic materials 0.000 claims abstract 2
- 229910052802 copper Inorganic materials 0.000 claims abstract 2
- YAGKRVSRTSUGEY-UHFFFAOYSA-N ferricyanide Chemical compound [Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] YAGKRVSRTSUGEY-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052733 gallium Inorganic materials 0.000 claims abstract 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract 2
- UETZVSHORCDDTH-UHFFFAOYSA-N iron(2+);hexacyanide Chemical compound [Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] UETZVSHORCDDTH-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052746 lanthanum Inorganic materials 0.000 claims abstract 2
- 229910052749 magnesium Inorganic materials 0.000 claims abstract 2
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract 2
- 150000004706 metal oxides Chemical class 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract 2
- 239000010452 phosphate Substances 0.000 claims abstract 2
- 239000012265 solid product Substances 0.000 claims abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052725 zinc Inorganic materials 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 238000000151 deposition Methods 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- -1 perchlora t Chemical compound 0.000 abstract 1
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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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/825—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with gallium, indium or thallium
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/007—Mixed salts
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/08—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of gallium, indium or thallium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- 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
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
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- C07C29/34—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups by condensation involving hydroxy groups or the mineral ester groups derived therefrom, e.g. Guerbet reaction
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Abstract
1. Способ получения катализатора, который включает следующие стадии:а) термическое разложение гидроталькита, имеющего формулудля получения оксида металла, при этом:M1 обозначает по меньшей мере один двухвалентный металл, выбранный из группы, включающей Mg, Zn, Cu, Со, Mn, Fe, Ni и Са,М2 обозначает по меньшей мере один трехвалентный металл, выбранный из группы, включающей Al, La, Fe, Cr, Mn, Co, Ni,М3 обозначает трехвалентный галлий (Ga),А обозначает по меньшей мере один анион, выбранный из группы, включающей: гидроксид, хлорид, фторид, бромид, йодид, нитрат, перхлорат, хлорат, бикарбонат, ацетат, бензоат, метансульфонат, п-толуолсульфонат, феноксид, алкоксид, карбонат, сульфат, терефталат, фосфат, гексацианоферрат (III) и гексацианоферрат (II),х обозначает число между 0.1 и 0.5; у обозначает величину между 0.00001 и 0.49; m обозначает целое число между 1 и 4; и n больше 0,б) добавление Pd к твердому продукту, полученному на стадии (а); причем гидроталькит получают путем соосаждения соединений Ml, М2 и М3.2. Способ по п. 1, в котором соосаждение проводят, добавляя раствор по меньшей мере одного соединения, выбранного из группы, включающей карбонат, бикарбонат и гидроксид, к раствору соединений M1, М2 и М3.3. Способ по любому из пп. 1-2, в котором термическое разложение на стадии (а) представляет собой прокаливание в атмосфере кислорода, азота или любой их смеси при температуре в диапазоне от 250°C до 650°C, предпочтительно, в диапазоне от 350°C до 550°C.4. Способ по любому из пп. 1-2, в котором добавление Pd на стадии (б) проводят методом влажной пропитки, пропитки по влагоемкости или методом отложения-осаждения.5. Способ по любому из пп. 1-2, в котором M1 обозначает Mg.6. Способ по любому из пп. 1-2, в котором М2 обозначает Al.7. Способ по любому из пп. 1-2, в котором А обозначает по меньшей мере один анион, выбранный из
Claims (12)
1. Способ получения катализатора, который включает следующие стадии:
а) термическое разложение гидроталькита, имеющего формулу 
для получения оксида металла, при этом:
M1 обозначает по меньшей мере один двухвалентный металл, выбранный из группы, включающей Mg, Zn, Cu, Со, Mn, Fe, Ni и Са,
М2 обозначает по меньшей мере один трехвалентный металл, выбранный из группы, включающей Al, La, Fe, Cr, Mn, Co, Ni,
М3 обозначает трехвалентный галлий (Ga),
А обозначает по меньшей мере один анион, выбранный из группы, включающей: гидроксид, хлорид, фторид, бромид, йодид, нитрат, перхлорат, хлорат, бикарбонат, ацетат, бензоат, метансульфонат, п-толуолсульфонат, феноксид, алкоксид, карбонат, сульфат, терефталат, фосфат, гексацианоферрат (III) и гексацианоферрат (II),
х обозначает число между 0.1 и 0.5; у обозначает величину между 0.00001 и 0.49; m обозначает целое число между 1 и 4; и n больше 0,
б) добавление Pd к твердому продукту, полученному на стадии (а); причем гидроталькит получают путем соосаждения соединений Ml, М2 и М3.
2. Способ по п. 1, в котором соосаждение проводят, добавляя раствор по меньшей мере одного соединения, выбранного из группы, включающей карбонат, бикарбонат и гидроксид, к раствору соединений M1, М2 и М3.
3. Способ по любому из пп. 1-2, в котором термическое разложение на стадии (а) представляет собой прокаливание в атмосфере кислорода, азота или любой их смеси при температуре в диапазоне от 250°C до 650°C, предпочтительно, в диапазоне от 350°C до 550°C.
4. Способ по любому из пп. 1-2, в котором добавление Pd на стадии (б) проводят методом влажной пропитки, пропитки по влагоемкости или методом отложения-осаждения.
5. Способ по любому из пп. 1-2, в котором M1 обозначает Mg.
6. Способ по любому из пп. 1-2, в котором М2 обозначает Al.
7. Способ по любому из пп. 1-2, в котором А обозначает по меньшей мере один анион, выбранный из группы, включающей 
и ОН-.
8. Способ по любому из пп. 1-2, который после стадии (б) дополнительно включает стадию (в), где продукт, полученный на стадии (б), подвергается прокаливанию.
9. Способ по п. 8, который после стадии (в) дополнительно включает стадию восстановления (г).
10. Катализатор, полученный способом по любому из пп. 1-9.
11. Применение катализатора по п. 10 для получения С3-С15 высших спиртов.
12. Применение катализатора по п. 11, где высший спирт обозначает спирт С4, предпочтительно, н-бутанол.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12382262.9 | 2012-06-29 | ||
| EP12382262.9A EP2679303B1 (en) | 2012-06-29 | 2012-06-29 | Catalyst and its preparation process for obtaining higher alcohols |
| PCT/ES2013/070442 WO2014001595A1 (es) | 2012-06-29 | 2013-06-28 | Catalizador para la obtención de alcoholes superiores |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014152878A true RU2014152878A (ru) | 2016-08-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014152878A RU2014152878A (ru) | 2012-06-29 | 2013-06-28 | Катализатор для получения высших спиртов |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9266096B2 (ru) |
| EP (1) | EP2679303B1 (ru) |
| KR (1) | KR102113105B1 (ru) |
| CN (1) | CN104736238B (ru) |
| BR (1) | BR112014032469B1 (ru) |
| CA (1) | CA2877970C (ru) |
| ES (1) | ES2855323T3 (ru) |
| HU (1) | HUE053582T2 (ru) |
| IN (1) | IN2014MN02642A (ru) |
| MX (1) | MX357222B (ru) |
| RU (1) | RU2014152878A (ru) |
| WO (1) | WO2014001595A1 (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112015019704B1 (pt) * | 2013-02-19 | 2021-09-14 | Rescurve, Llc | Método e sistema de destilação reativa |
| US10081588B2 (en) | 2013-12-04 | 2018-09-25 | Rescurve, Llc | Production of butyl acetate from ethanol |
| US10301241B2 (en) | 2013-12-27 | 2019-05-28 | Abengoa Bioenergia Nuevas Tecnologias, S.A. | Process for the preparation of higher alcohols from lower alcohols by Guerbet condensation |
| ES2570231B1 (es) * | 2014-11-14 | 2017-04-19 | Abengoa Bioenergia Nuevas Tecnologias, S.A. | Proceso para la preparación de alcoholes superiores a partir de etanol y n-hexanol mediante condensación de guerbet |
| WO2016075531A1 (en) | 2014-11-14 | 2016-05-19 | Abengoa Bioenergia Nuevas Tecnologias, S.A. | Process for the preparation of higher alcohols from ethanol and n-hexanol by guerbet condensation |
| ES2570233B1 (es) | 2014-11-14 | 2017-02-22 | Abengoa Bioenergía Nuevas Tecnologías, S.A. | Procedimiento de obtención de 1-octanol |
| ES2570227B1 (es) * | 2014-11-14 | 2017-04-19 | Abengoa Bioenergia Nuevas Tecnologias, S.A. | Proceso para la preparación de alcoholes superiores a partir de etanol y n-hexanol mediante condensación de guerbet |
| MY187509A (en) * | 2015-08-19 | 2021-09-24 | Rescurve Llc | Composition of catalysts for conversion of ethanol to n-butanol and higher alcohols |
| WO2017093473A1 (en) | 2015-12-02 | 2017-06-08 | Universiteit Gent | Guerbet condensation reaction |
| ES2647963B1 (es) * | 2016-05-26 | 2018-10-03 | Abengoa Bioenergía Nuevas Tecnologías, S.A. | Procedimiento de obtención de 1-octanol |
| CN107983356B (zh) * | 2017-12-07 | 2020-12-25 | 中国科学院山西煤炭化学研究所 | 一种合成高级支链醇的催化剂及制备方法和应用 |
| CN111604056B (zh) * | 2020-06-03 | 2023-05-12 | 中国科学院山西煤炭化学研究所 | 一种负载型金属氧化物催化剂及其制备方法和应用 |
| CN112619654A (zh) * | 2020-11-06 | 2021-04-09 | 上海簇睿低碳能源技术有限公司 | 一种甲烷二氧化碳重整制合成气的催化剂及其制备方法 |
| CN112827483B (zh) * | 2020-12-29 | 2022-10-25 | 宁波申江科技股份有限公司 | 一种制氢催化剂及其制备方法和应用 |
| CN112916010B (zh) * | 2021-01-26 | 2022-09-16 | 北京化工大学 | 一种炔烃选择性加氢用Cuy/MMgOx催化剂及其制备方法 |
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| DE8600273U1 (de) * | 1986-01-08 | 1986-03-06 | Paul Hellermann Gmbh, 2080 Pinneberg | Spannband, insbesondere zum Binden von langgestreckten Gegenständen |
| US5219816A (en) * | 1991-12-20 | 1993-06-15 | Exxon Research & Engineering Company | Dehydrogenation catalysts and process for preparing the catalysts |
| US5300695A (en) | 1992-12-07 | 1994-04-05 | Amoco Corporation | Process for preparing alcohols |
| US5387570A (en) | 1993-05-07 | 1995-02-07 | Exxon Research & Engineering Co. | Catalysts for iso-alcohol synthesis from CO + H2 |
| NO312126B1 (no) * | 1998-12-23 | 2002-03-25 | Norske Stats Oljeselskap | Forbedret fremgangsmåte for fremstilling av katalysatorer bestående av metaller på hydrotalcitt-baserte b¶rermaterialer |
| KR20070085516A (ko) | 2004-12-03 | 2007-08-27 | 가부시키가이샤 상기 | 고분자 알코올의 합성방법 |
| US7700810B2 (en) * | 2007-08-22 | 2010-04-20 | E.I. Du Pont De Nemours And Company | Catalytic conversion of ethanol to a 1-butanol-containing reaction product using a thermally decomposed hydrotalcite catalyst |
| US7700811B2 (en) | 2007-08-22 | 2010-04-20 | E.I. Du Pont De Namours And Company | Catalytic conversion of ethanol to a 1-butanol-containing reaction product using a thermally decomposed hydrotalcite/metal carbonate |
| US8071823B2 (en) | 2008-01-28 | 2011-12-06 | E.I. Du Pont De Nemours And Company | Catalytic conversion of ethanol and hydrogen to a 1-butanol-containing reaction product using a thermally decomposed hydrotalcite/metal carbonate |
| WO2009097310A1 (en) | 2008-01-28 | 2009-08-06 | E. I. Du Pont De Nemours And Company | Catalytic conversion of ethanol and hydrogen to a 1-butanol-containing reaction product using a thermally decomposed hydrotalcite containing the anion of ethylenediaminetetraacetic acid |
| US8318989B2 (en) | 2008-12-22 | 2012-11-27 | E I Du Pont De Nemours And Company | Process for producing guerbet alcohols using water tolerant basic catalysts |
| EP2366664A1 (en) * | 2010-03-09 | 2011-09-21 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Palladium-modified hydrotalcites and their use as catalyst precursors |
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2012
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- 2012-06-29 EP EP12382262.9A patent/EP2679303B1/en active Active
- 2012-06-29 ES ES12382262T patent/ES2855323T3/es active Active
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- 2013-06-28 BR BR112014032469-7A patent/BR112014032469B1/pt active IP Right Grant
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|---|---|
| KR102113105B1 (ko) | 2020-05-21 |
| EP2679303B1 (en) | 2020-11-11 |
| BR112014032469B1 (pt) | 2021-02-09 |
| US9266096B2 (en) | 2016-02-23 |
| MX2015000225A (es) | 2015-08-12 |
| WO2014001595A1 (es) | 2014-01-03 |
| EP2679303A1 (en) | 2014-01-01 |
| CA2877970C (en) | 2020-11-17 |
| CN104736238B (zh) | 2017-09-08 |
| KR20150090019A (ko) | 2015-08-05 |
| IN2014MN02642A (ru) | 2015-10-16 |
| BR112014032469A2 (pt) | 2017-06-27 |
| ES2855323T3 (es) | 2021-09-23 |
| CA2877970A1 (en) | 2014-01-03 |
| MX357222B (es) | 2018-06-28 |
| CN104736238A (zh) | 2015-06-24 |
| HUE053582T2 (hu) | 2021-07-28 |
| US20150148569A1 (en) | 2015-05-28 |
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