HRP20180263T1 - Jednostupanjski ("one-pot") postupak za pripravu smjesa biodizela i glicerol-etera korisnih kao biogoriva - Google Patents

Jednostupanjski ("one-pot") postupak za pripravu smjesa biodizela i glicerol-etera korisnih kao biogoriva Download PDF

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HRP20180263T1
HRP20180263T1 HRP20180263TT HRP20180263T HRP20180263T1 HR P20180263 T1 HRP20180263 T1 HR P20180263T1 HR P20180263T T HRP20180263T T HR P20180263TT HR P20180263 T HRP20180263 T HR P20180263T HR P20180263 T1 HRP20180263 T1 HR P20180263T1
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Croatia
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oil
formula
acids
group
methyl
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HRP20180263TT
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English (en)
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Giovanni Nicolosi
Carmelo Drago
Leonarda Francesca Liotta
Valeria LA PAROLA
Maria Luisa Testa
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Consiglio Nazionale Delle Ricerche
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    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/02Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/026Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/10Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing sonic or ultrasonic vibrations
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B01J19/122Incoherent waves
    • B01J19/126Microwaves
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B01J19/122Incoherent waves
    • B01J19/129Radiofrequency
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/09Preparation of ethers by dehydration of compounds containing hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01Preparation of ethers
    • C07C41/14Preparation of ethers by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/24Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/28Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/297Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/185Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852Ethers; Acetals; Ketals; Orthoesters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11CFATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00Components of fuel compositions
    • C10L2200/02Inorganic or organic compounds containing atoms other than C, H or O, e.g. organic compounds containing heteroatoms or metal organic complexes
    • C10L2200/0254Oxygen containing compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00Components of fuel compositions
    • C10L2200/04Organic compounds
    • C10L2200/0461Fractions defined by their origin
    • C10L2200/0469Renewables or materials of biological origin
    • C10L2200/0476Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2270/00Specifically adapted fuels
    • C10L2270/02Specifically adapted fuels for internal combustion engines
    • C10L2270/026Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2290/00Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/34Applying ultrasonic energy
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2290/00Fuel preparation or upgrading, processes or apparatus therefore, comprising specific process steps or apparatus units
    • C10L2290/36Applying radiation such as microwave, IR, UV
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00Technologies for the production of fuel of non-fossil origin
    • Y02E50/10Biofuels, e.g. bio-diesel

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Claims (11)

1. Postupak za pretvorbu sirovine koja sadrži jedan ili više triglicerida masnih kiselina u smjesu koja sadrži jedan ili više alkil-estera masnih kiselina i t-alkilglicerola, koji obuhvaća reakciju rečene sirovine sa spojem formule (I): R–O–R' (I) u kojoj: R' je alkil, alkenil ili alkinil koji ima 1-18 ugljikovih atoma; R je H ili tercijarna alkilna skupina formule (II): [image] u kojoj RIII, RIV i RV neovisno jesu ravni ili razgranati alkil, alkenil ili alkinilna skupina koja ima 1 do 6 ugljikovih atoma; u kojoj je rečena reakcija provedena u prisutnosti kiselog katalizatora za transesterifikaciju ozračavanjem s mikrovalovima i/ili ultrazvukom i/ili radiovalovima, s tim da kada R jest H, dodaje se alkohol formule R-OH, u kojoj R jest kao što je gore definirano, u ekvimolarnoj količini prema RI-OH.
2. Postupak prema patentnom zahtjevu 1, naznačeno time da su RIII, RIV i RV u formuli (II) odabrani iz skupine koju čine metil, etil, propil, izopropil, butil, t-butil, etenil, propenil, izopropenil, butenil, izobutenil, heksenil, etinil, propinil i butinil.
3. Postupak prema patentnom zahtjevu 2, naznačeno time da RIII, RIV i RV u formuli (II) jesu metil.
4. Postupak prema bilo kojem od patentnih zahtjeva 1 do 3, naznačeno time da je RI u formuli (I) odabran iz skupine koju čine metil, etil, propil, izopropil i butil.
5. Postupak prema patentnom zahtjevu 4, naznačeno time da RI u formuli (I) jest metil.
6. Postupak prema bilo kojem od patentnih zahtjeva 1 do 5, naznačeno time da spoj formule (I) jest tert-butil-metil-eter.
7. Postupak prema bilo kojem od patentnih zahtjeva 1 do 6, naznačeno time da je sirovina odabrana iz skupine koju čine: ‒ biljna ulja kao što je kokosovo ulje, kukuruzno ulje, ulje sjemenki pamuka, maslinovo ulje, palmino ulje, ulje kikirikija, ulje sjemenki uljane repice, ulje uljane repice, ulje šafranike, ulje sezama, sojino ulje, suncokretovo ulje, bademovo ulje, ulje sjemenki bukve, ulje Anacardium occidentale, ulje lješnjaka, ulje makadamije, ulje pinjola, ulje pistacija, ulje oraha, ulja citrusa, ulje sjemenki grejpa, ulje limuna, ulje naranče, ricinusovo ulje, ulje konoplje, ulje gorušice, ulje rotkvice, ulje zrna riže, ulje caklenjače, ulje jatrofine, ulje jojobe, ulje sjemenki lana, ulje maka, ulje Sapium sebirefum, ulje voćke, ulje artičoke, ulje sjemenki mrkve, ulje manga te ulje morske pasjakovine; – životinjske masti kao što je goveđi loj, mast, mast peradi te riblja ulja; – otpadna ulja i masti iz raznih izvora, kao što su ulja i masti korištene u restoranima i u ugostiteljstvu općenito, a prisutni su u otpadu od industrija poljoprivrednih i morskih proizvoda.
8. Metoda prema bilo kojem od patentnih zahtjeva 1 do 7, naznačeno time da se ozračavanje odvija samo s jednom vrstom elektromagnetske frekvencije odabranom od mikrovalova, ultrazvuka ili radiovalova ili s različitim vrstama rečenih elektromagnetskih frekvencija, istodobno ili jedan iza drugog.
9. Metoda prema bilo kojem od patentnih zahtjeva 1 do 8, naznačeno time da kiseli katalizator korišten u reakciji može biti katalizator sa slobodnom kiselinom ili nanesen na nosač.
10. Postupak prema patentnom zahtjevu 9, naznačeno time da je kiseli katalizator odabran iz skupine koju čine: – jake mineralne kiseline i organske kiseline; – zeoliti, molekulska sita, fosfati, cirkonati, kaoliniti, montmoriloniti, porozne gline, hidrotalciti i smole za kiselu ionsku izmjenu; – čvrsta kiselina ili pogodni materijali funkcionalizirani u kiseline kao što su perfluorirani oksidi i/ili polimeri; silicijevi dioksidi i silicijevi dioksidi s dodanim Al, Ti ili Zr u različitim morfološkim oblicima, heteropolikiseline, kiseline adsorbirane i/ili kovaletno vezane na metalne okside; organske sulfonske i/ili organske karboksilne kiseline nanešene na amorfni silicijev dioksid i/ili mezo i mikrostrukturirani silicijev dioksid; polioksimetalati stabilizirani na silicijevom dioksidu i/ili titanijevom dioksidu; Kegginove strukture koje sadrže niobijeve ione; niobijeve okside; ionske tekućine i/ili ugljikove nanocijevi funkcionalizirane s organskim sulfonskim kiselinama i/ili organskim karboksilnim kiselinama.
11. Postupak prema patentnom zahtjevu 10, naznačeno time kiseli katalizator jest alkilsulfonska kiselina vezana na amorfni silicijev dioksid.
HRP20180263TT 2013-02-05 2018-02-13 Jednostupanjski ("one-pot") postupak za pripravu smjesa biodizela i glicerol-etera korisnih kao biogoriva HRP20180263T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT000156A ITMI20130156A1 (it) 2013-02-05 2013-02-05 Procedimento "one-pot" per la produzione di miscele di biodiesel e eteri del glicerolo utili come biocarburanti
PCT/IB2014/058783 WO2014122579A1 (en) 2013-02-05 2014-02-04 One-pot process for the production of biodiesel and glycerol ether mixtures useful as biofuels
EP14707234.2A EP2953921B1 (en) 2013-02-05 2014-02-04 One-pot process for the production of biodiesel and glycerol ether mixtures useful as biofuels

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HRP20180263T1 true HRP20180263T1 (hr) 2018-03-23

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US (1) US9873843B2 (hr)
EP (1) EP2953921B1 (hr)
CN (1) CN105073706B (hr)
BR (1) BR112015018657B1 (hr)
CY (1) CY1119997T1 (hr)
DK (1) DK2953921T3 (hr)
EA (1) EA027246B1 (hr)
ES (1) ES2658176T3 (hr)
HR (1) HRP20180263T1 (hr)
HU (1) HUE035628T2 (hr)
IT (1) ITMI20130156A1 (hr)
LT (1) LT2953921T (hr)
MY (1) MY172168A (hr)
NO (1) NO2953921T3 (hr)
PL (1) PL2953921T3 (hr)
PT (1) PT2953921T (hr)
RS (1) RS56847B1 (hr)
SI (1) SI2953921T1 (hr)
WO (1) WO2014122579A1 (hr)

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CN108250053B (zh) * 2016-12-29 2024-01-09 中国石油化工股份有限公司 制备甘油烷基醚的方法和系统
RU2661872C1 (ru) * 2017-12-26 2018-07-20 Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Нижегородский государственный университет им. Н.И. Лобачевского" Способ непрерывного получения пластификаторов поливинилхлорида и аппарат для его осуществления
US10633318B2 (en) 2018-03-26 2020-04-28 International Flora Technologies, Ltd. Wax ethers and related methods
EP3874012A4 (en) * 2018-11-01 2022-07-20 Ariel Scientific Innovations Ltd. PRODUCTION OF BIODIESEL
LV15515A (lv) 2018-12-28 2020-07-20 Rīgas Tehniskā Universitāte Biodīzeļdegviela un tās izgatavošanas paņēmiens

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GB0112557D0 (en) * 2001-05-23 2001-07-11 Infineum Int Ltd A process for manufacturing monoesters of polyhydroxyalcohols
US20050274065A1 (en) * 2004-06-15 2005-12-15 Carnegie Mellon University Methods for producing biodiesel
EP2089347A2 (en) * 2006-12-06 2009-08-19 Southern Illinois University Carbondale Processes for the production of fatty acid alkyl esters
US8052848B2 (en) * 2007-06-26 2011-11-08 The Penn State Research Foundation Ultrasonic and microwave methods for enhancing the rate of a chemical reaction and apparatus for such methods
US8591605B2 (en) * 2007-07-26 2013-11-26 Board Of Regents Of The Nevada System Of Higher Education, On Behalf Of The University Of Nevada, Reno Methods, systems, and apparatus for obtaining biofuel from coffee and fuels produced therefrom
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ITMI20080459A1 (it) * 2008-03-18 2009-09-19 Eni Spa Processo per la produzione di una composizione utile come carburante
US8858657B1 (en) * 2010-12-22 2014-10-14 Arrowhead Center, Inc. Direct conversion of algal biomass to biofuel

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Publication number Publication date
ES2658176T3 (es) 2018-03-08
BR112015018657B1 (pt) 2021-01-12
US9873843B2 (en) 2018-01-23
WO2014122579A1 (en) 2014-08-14
EP2953921A1 (en) 2015-12-16
BR112015018657A2 (pt) 2017-07-18
NO2953921T3 (hr) 2018-04-14
LT2953921T (lt) 2018-02-26
ITMI20130156A1 (it) 2014-08-06
EA027246B1 (ru) 2017-07-31
CY1119997T1 (el) 2018-12-12
HUE035628T2 (en) 2018-05-28
SI2953921T1 (en) 2018-03-30
EA201591271A1 (ru) 2015-12-30
CN105073706A (zh) 2015-11-18
US20160024408A1 (en) 2016-01-28
PT2953921T (pt) 2018-02-07
PL2953921T3 (pl) 2018-04-30
EP2953921B1 (en) 2017-11-15
CN105073706B (zh) 2018-06-12
MY172168A (en) 2019-11-15
DK2953921T3 (en) 2018-02-12
RS56847B1 (sr) 2018-04-30

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