US20120012505A1 - Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons - Google Patents

Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons Download PDF

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Publication number
US20120012505A1
US20120012505A1 US12/835,881 US83588110A US2012012505A1 US 20120012505 A1 US20120012505 A1 US 20120012505A1 US 83588110 A US83588110 A US 83588110A US 2012012505 A1 US2012012505 A1 US 2012012505A1
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United States
Prior art keywords
bis
methylene
mercaptans
alpha
oxybis
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
US12/835,881
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English (en)
Inventor
Dennis R. Compton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ChampionX LLC
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Nalco Co LLC
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 Nalco Co LLC filed Critical Nalco Co LLC
Priority to US12/835,881 priority Critical patent/US20120012505A1/en
Assigned to NALCO COMPANY reassignment NALCO COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: COMPTON, DENNIS R.
Priority to MX2013000509A priority patent/MX2013000509A/es
Priority to EP11807420.2A priority patent/EP2593533B1/en
Priority to JP2013519781A priority patent/JP5889296B2/ja
Priority to ES11807420.2T priority patent/ES2593462T3/es
Priority to CA2805489A priority patent/CA2805489C/en
Priority to RU2013102416/04A priority patent/RU2557545C2/ru
Priority to PT118074202T priority patent/PT2593533T/pt
Priority to PCT/US2011/043778 priority patent/WO2012009390A2/en
Priority to KR1020137003669A priority patent/KR20130141438A/ko
Priority to ARP110102516A priority patent/AR082166A1/es
Priority to BR112013000892-0A priority patent/BR112013000892B1/pt
Priority to HUE11807420A priority patent/HUE030422T2/en
Priority to PL11807420.2T priority patent/PL2593533T3/pl
Priority to SG2013003009A priority patent/SG187079A1/en
Publication of US20120012505A1 publication Critical patent/US20120012505A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C07C7/152—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by forming adducts or complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/20—Use of additives, e.g. for stabilisation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/104—Light gasoline having a boiling range of about 20 - 100 °C
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1044—Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1051—Kerosene having a boiling range of about 180 - 230 °C
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1048—Middle distillates
    • C10G2300/1055—Diesel having a boiling range of about 230 - 330 °C
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P

Definitions

  • the present invention relates to the scavenging of mercaptans in hydrocarbon fluids and more particularly to the use of alpha-amino ethers as mercaptan scavengers.
  • Hydrocarbon fluids such as crude oil, crude oil emulsions, oilfield condensate, petroleum residua and refined fuels such as naphtha, kerosene, gasoline, and other purified petroleum products often contain a variety of mercaptans, including mercaptans of relatively low molecular weight.
  • choline or choline hydroxide has been found to alleviate hydrogen sulfide evolution and to scavenge mercaptans as show in U.S. Pat. Nos. 4,594,147, 4,867,865, and 5,183,560.
  • choline and choline hydroxide are not well suited for many uses and media, such as in crude oil.
  • choline and choline hydroxide might scavenge mercaptans in such media, they also form a volatile and malodorous by-product with the sulfur compounds indigenous to such media.
  • choline and choline hydroxide to control odors associated with light weight mercaptans is self-defeating in media such as crude oil.
  • European Patent Application 0 538 819 A3 describes the use of oil-soluble quaternary ammonium compounds to scavenge mercaptans from certain oils, especially high boiling, heavy residual fuels.
  • U.S. Pat. No. 5,840,177 describes using quaternary ammonium hydroxides to scavenge mercaptans from certain hydrocarbon fluids.
  • At least one embodiment of the invention is directed towards a method of reducing the amount of mercaptans in a hydrocarbon fluid.
  • the method comprises contacting the fluid with an effective amount of alpha-amino ether sufficient to convert the mercaptan into a non-volatile species.
  • the hydrocarbon fluid can be a liquid.
  • the hydrocarbon fluid can be selected from the list consisting of but not limited to diesel fuel, kerosene, and gasoline.
  • the alpha-amino ether can be selected from the list consisting of:
  • the mercaptans can be present in the hydrocarbon fluid in amounts in excess of 500 ppm.
  • the ratio of alpha-amino ether molecules to mercaptan molecules can be within the range of 1:1000 to 1000:1.
  • FIG. 1 illustrates compositions of matter useful as a mercaptan scavenger.
  • Alpha-amino ether means a molecule according to the formula:
  • R 1 , R 2 , R 3 , R 4 are carbon containing side chains containing 1-20 carbon atoms and includes cyclic and acyclic compounds.
  • the cyclic compounds can be aromatic or non-aromatic. Examples include but are not limited to, methyl, ethyl, propyl, tert-butyl, cyclopentyl, cyclohexyl, morpholino, and phenyl, and they all can be the same group or one or more different groups.
  • B is an ether group, which is either an oxygen atom or a group having an oxygen atom at both ends (such as —OCH 2 O— or —OC 2 H 4 O—).
  • Hydrocarbon fluid means a liquid or gas predominantly comprising organic material including but not limited to kerosene, crude oil, crude oil emulsions, oilfield condensate, petroleum residua, refined fuels, distillate fuels, fuel oil, heating oils, diesel fuel, gasoline, jet fuel, bunker fuel oils, and any combination thereof.
  • “Mercaptan” means a sulfur-containing organic compound with the general formula RSH where R is any alkyl, aromatic or cyclic group.
  • Examples of common mercaptans are methylmercaptan CH 3 SH, ethylmercaptan CH 3 CH 2 SH, propylmercaptan CH 3 (CH 2 ) 2 SH, isopropylmercaptan (CH 3 ) 2 CHSH, Phenylmercaptan C 5 H S SH.
  • “Scavenger” means a composition of matter, such as but not limited to alpha-amino ethers, useful in reducing the amount of or mitigating the effects of some other composition of matter, such as but not limited to mercaptans, in a fluid medium.
  • Formaldehyde equivalent means a composition of matter containing at least one group according to the formula: (CH 2 O) n in which n is an integer greater than or equal to 1, and/or a composition of matter including formaldehyde or related molecules such as paraformaldehyde, and/or s-trioxane.
  • the amount of mercaptans in a hydrocarbon fluid is reduced by the introduction of an alpha-amino ether into the fluid.
  • the alpha-amino ether scavenges mercaptan by forming stable non-volatile compounds
  • the new sulfur containing compounds are higher molecular weight and lower volatility mitigating the odor associated with volatile mercaptans.
  • the mercaptan scavenger is produced by reacting a secondary amine with formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
  • formaldehyde or other formaldehyde equivalents such as paraformaldehyde or s-trioxane.
  • the reaction product also comprises 10-25% double amine that is non-reactive to the mercaptans.
  • any of the R groups correspond to any of the R 1 , R 2 , R 3 , and R 4 , groups described in the definition of “alpha-amino ether”.
  • reaction is performed without solvent.
  • This reaction can be performed with solvents such as aromatic 150, aromatic 100, etc. to create a diluted product.
  • a scavenging formulation is used in a hydrocarbon fluid.
  • the formulation can but is not required to contain a solvent and at least one alpha-amino ether, the alpha-amino ether can be used without solvent.
  • the solvent is selected from the list consisting of water, alcohol, aromatic solvent, non-aromatic solvent and a solvent that solvates alpha-amino ethers, and any combination thereof.
  • the formulation can be introduced into the hydrocarbon fluid by mechanical means including but not limited to injection pumps or any other mechanism known in the art including but not limited to those methods described in U.S. Pat. No. 5,840,177.
  • Table 1 shows the ppm wt of sulfur in the form of sec-butyl mercaptan and n-butyl mercaptan in the untreated sample.
  • Tables 2 and 3 show the reduction in mercaptans when treated with alpha-amino ethers derived from butyl amine and morpholine respectively. The loss of n-butyl mercaptan and increase in unidentified volatile sulfur compounds indicates that the mercaptan has formed a stable compound that did not match a known standard.
  • a complex mercaptan solution of nine different mercaptans was prepared and a series of alpha amino ethers was tested for their ability to reduce the mercaptans. 1000 ppm (v/v) was added to a solution of kerosene. The kerosene was then treated with 3000 ppm (v/v) of the specified samples.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Water Supply & Treatment (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Gas Separation By Absorption (AREA)
  • Treating Waste Gases (AREA)
US12/835,881 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons Abandoned US20120012505A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
US12/835,881 US20120012505A1 (en) 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons
SG2013003009A SG187079A1 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons
RU2013102416/04A RU2557545C2 (ru) 2010-07-14 2011-07-13 Использование простых альфа-аминоэфиров для удаления меркаптанов из углеводородов
PCT/US2011/043778 WO2012009390A2 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons
JP2013519781A JP5889296B2 (ja) 2010-07-14 2011-07-13 炭化水素からメルカプタンを取り除くためのαアミノエーテルの使用
ES11807420.2T ES2593462T3 (es) 2010-07-14 2011-07-13 Uso de alfa-amino éteres para la eliminación de mercaptanos de hidrocarburos
CA2805489A CA2805489C (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons
MX2013000509A MX2013000509A (es) 2010-07-14 2011-07-13 Uso de alfa-amino eteres para eliminacion de mercaptanos de hidrocarburos.
PT118074202T PT2593533T (pt) 2010-07-14 2011-07-13 Utilização de alfa-aminoéteres para a remoção de mercaptanos de hidrocarbonetos
EP11807420.2A EP2593533B1 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons
KR1020137003669A KR20130141438A (ko) 2010-07-14 2011-07-13 탄화수소로부터 머캅탄을 제거하기 위한 알파-아미노 에테르의 용도
ARP110102516A AR082166A1 (es) 2010-07-14 2011-07-13 USO DE a-AMINO ETERES PARA ELIMINAR MERCAPTANOS DE HIDROCARBUROS
BR112013000892-0A BR112013000892B1 (pt) 2010-07-14 2011-07-13 método para reduzir a quantidade de mercaptanos em um fluido hidrocarboneto
HUE11807420A HUE030422T2 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers to remove thiols from hydrocarbons
PL11807420.2T PL2593533T3 (pl) 2010-07-14 2011-07-13 Zastosowanie alfa-amino eterów do usuwania merkaptanów z węglowodorów

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US12/835,881 US20120012505A1 (en) 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons

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US20120012505A1 true US20120012505A1 (en) 2012-01-19

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US12/835,881 Abandoned US20120012505A1 (en) 2010-07-14 2010-07-14 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons

Country Status (15)

Country Link
US (1) US20120012505A1 (enrdf_load_stackoverflow)
EP (1) EP2593533B1 (enrdf_load_stackoverflow)
JP (1) JP5889296B2 (enrdf_load_stackoverflow)
KR (1) KR20130141438A (enrdf_load_stackoverflow)
AR (1) AR082166A1 (enrdf_load_stackoverflow)
BR (1) BR112013000892B1 (enrdf_load_stackoverflow)
CA (1) CA2805489C (enrdf_load_stackoverflow)
ES (1) ES2593462T3 (enrdf_load_stackoverflow)
HU (1) HUE030422T2 (enrdf_load_stackoverflow)
MX (1) MX2013000509A (enrdf_load_stackoverflow)
PL (1) PL2593533T3 (enrdf_load_stackoverflow)
PT (1) PT2593533T (enrdf_load_stackoverflow)
RU (1) RU2557545C2 (enrdf_load_stackoverflow)
SG (1) SG187079A1 (enrdf_load_stackoverflow)
WO (1) WO2012009390A2 (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130245204A1 (en) * 2010-11-30 2013-09-19 Connora Technologies, Inc. Novel agents for reworkable epoxy resins
US10214479B2 (en) 2012-06-05 2019-02-26 Connora Technologies, Inc. Synthesis of and compositions containing diaminoacetals and diaminoketals
US10919839B2 (en) 2017-07-11 2021-02-16 Aditya Birla Chemicals (Usa) Llc Silicon-containing compositions and their methods of use
CN114159946A (zh) * 2022-02-11 2022-03-11 河北精致科技有限公司 一种用于脱除烟气中二氧化硫的吸收剂及其应用
US20240110091A1 (en) * 2022-09-21 2024-04-04 Championx Usa Inc. Compositions and methods for scavenging sulfur-containing compounds

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EP0882778A2 (en) * 1997-06-04 1998-12-09 Nalco/Exxon Energy Chemicals, L.P. Composition and method for sweetening gaseous or liquid hydrocarbons, aqueous systems and mixtures thereof

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RU2349627C2 (ru) * 2005-10-27 2009-03-20 Ахматфаиль Магсумович Фахриев Средство для удаления сероводорода и/или низкомолекулярных меркаптанов и способ его использования
BRPI0808265A2 (pt) * 2008-09-02 2019-09-24 Gen Electric "método para reduzir a quantidade de sulfeto de hidrogênio presente em óleo bruto"
US9394396B2 (en) * 2011-06-21 2016-07-19 Baker Hughes Incorporated Hydrogen sulfide scavenger for use in hydrocarbons

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US5284576A (en) * 1989-08-01 1994-02-08 Petrolite Corporation Method of scavenging hydrogen sulfide from hydrocarbons
EP0882778A2 (en) * 1997-06-04 1998-12-09 Nalco/Exxon Energy Chemicals, L.P. Composition and method for sweetening gaseous or liquid hydrocarbons, aqueous systems and mixtures thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130245204A1 (en) * 2010-11-30 2013-09-19 Connora Technologies, Inc. Novel agents for reworkable epoxy resins
US9631049B2 (en) * 2010-11-30 2017-04-25 Connora Technologies, Inc. Agents for reworkable epoxy resins
US10214479B2 (en) 2012-06-05 2019-02-26 Connora Technologies, Inc. Synthesis of and compositions containing diaminoacetals and diaminoketals
US11542224B2 (en) 2012-06-05 2023-01-03 Aditya Birla Chemicals (Usa), Inc. Synthesis of and compositions containing diaminoacetals and diaminoketals
US10919839B2 (en) 2017-07-11 2021-02-16 Aditya Birla Chemicals (Usa) Llc Silicon-containing compositions and their methods of use
US11124473B2 (en) 2017-07-11 2021-09-21 Aditya Birla Chemicals (Usa) Llc Salts of diaminoacetals and diaminoketals and their synthesis, and their transformations to diaminoacetals and diaminoketals
US11731932B2 (en) 2017-07-11 2023-08-22 Aditya Birla Chemicals (Usa), Inc. Silicon-containing compositions and their methods of use
US11905228B2 (en) 2017-07-11 2024-02-20 Aditya Birla Chemicals (Usa), Inc. Salts of diaminoacetals and diaminoketals and their synthesis, and their transformations to diaminoacetals and diaminoketals
CN114159946A (zh) * 2022-02-11 2022-03-11 河北精致科技有限公司 一种用于脱除烟气中二氧化硫的吸收剂及其应用
US20240110091A1 (en) * 2022-09-21 2024-04-04 Championx Usa Inc. Compositions and methods for scavenging sulfur-containing compounds

Also Published As

Publication number Publication date
SG187079A1 (en) 2013-02-28
WO2012009390A3 (en) 2012-04-19
EP2593533A2 (en) 2013-05-22
BR112013000892A2 (pt) 2016-05-17
BR112013000892B1 (pt) 2020-10-20
JP2013535530A (ja) 2013-09-12
RU2557545C2 (ru) 2015-07-27
HUE030422T2 (en) 2017-05-29
CA2805489C (en) 2018-05-08
ES2593462T3 (es) 2016-12-09
EP2593533A4 (en) 2014-04-23
KR20130141438A (ko) 2013-12-26
RU2013102416A (ru) 2014-08-20
MX2013000509A (es) 2013-02-27
JP5889296B2 (ja) 2016-03-22
EP2593533B1 (en) 2016-07-06
AR082166A1 (es) 2012-11-14
PL2593533T3 (pl) 2016-12-30
CA2805489A1 (en) 2012-01-19
PT2593533T (pt) 2016-07-29
WO2012009390A2 (en) 2012-01-19

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