WO2012074807A1 - Sterically hindered amines and associated methods - Google Patents

Sterically hindered amines and associated methods Download PDF

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Publication number
WO2012074807A1
WO2012074807A1 PCT/US2011/061604 US2011061604W WO2012074807A1 WO 2012074807 A1 WO2012074807 A1 WO 2012074807A1 US 2011061604 W US2011061604 W US 2011061604W WO 2012074807 A1 WO2012074807 A1 WO 2012074807A1
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WO
WIPO (PCT)
Prior art keywords
amine
sterically hindered
integer
hindered amines
present disclosure
Prior art date
Application number
PCT/US2011/061604
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English (en)
French (fr)
Inventor
Wei-Yang Su
Robert A. Grigsby, Jr.
Jingjun Zhou
Original Assignee
Huntsman Petrochemical 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
Priority to AU2011336995A priority Critical patent/AU2011336995B2/en
Priority to MX2018004065A priority patent/MX371466B/es
Priority to CA2817994A priority patent/CA2817994C/en
Priority to US13/989,137 priority patent/US9352271B2/en
Priority to EP11845094.9A priority patent/EP2646407B1/en
Priority to NO11845094A priority patent/NO2646407T3/no
Priority to MX2013005958A priority patent/MX362397B/es
Priority to JP2013542046A priority patent/JP2014505022A/ja
Priority to CN2011800581625A priority patent/CN103282341A/zh
Priority to EP17180356.2A priority patent/EP3255034B1/en
Application filed by Huntsman Petrochemical Llc filed Critical Huntsman Petrochemical Llc
Publication of WO2012074807A1 publication Critical patent/WO2012074807A1/en
Priority to US15/070,050 priority patent/US9700832B2/en
Priority to US15/425,350 priority patent/US9987588B2/en

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1493—Selection of liquid materials for use as absorbents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1456—Removing acid components
    • B01D53/1462—Removing mixtures of hydrogen sulfide and carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
    • B01D53/1456—Removing acid components
    • B01D53/1468—Removing hydrogen sulfide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/50—Ethers of hydroxy amines of undetermined structure, e.g. obtained by reactions of epoxides with hydroxy amines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/202—Alcohols or their derivatives
    • B01D2252/2023—Glycols, diols or their derivatives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/204—Amines
    • B01D2252/20405—Monoamines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/204—Amines
    • B01D2252/2041—Diamines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/204—Amines
    • B01D2252/20426—Secondary amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/20—Organic absorbents
    • B01D2252/204—Amines
    • B01D2252/20478—Alkanolamines
    • B01D2252/20484—Alkanolamines with one hydroxyl group
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/50—Combinations of absorbents
    • B01D2252/504—Mixtures of two or more absorbents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/60—Additives
    • B01D2252/606—Anticorrosion agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
    • B01D2252/60—Additives
    • B01D2252/608—Antifoaming agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2256/00—Main component in the product gas stream after treatment
    • B01D2256/16—Hydrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2256/00—Main component in the product gas stream after treatment
    • B01D2256/20—Carbon monoxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2256/00—Main component in the product gas stream after treatment
    • B01D2256/24—Hydrocarbons
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/30—Sulfur compounds
    • B01D2257/304—Hydrogen sulfide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/50—Carbon oxides
    • B01D2257/504—Carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/02—Other waste gases
    • B01D2258/0283—Flue gases
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Definitions

  • Various amine solutions have been used for the removal of acidic gases from gases and liquids.
  • Common acidic gases may include, C0 2 , H 2 S, CS 2 , HCN, COS and oxygen and sulfur derivatives of Ci to C 4 hydrocarbons.
  • the treatment of gases and liquids containing acidic gases, such as C0 2 and H 2 S, with certain amine solutions typically results in the simultaneous removal of substantial amounts of both C0 2 and H 2 S.
  • Selective removal of H 2 S results in a relatively high H 2 S/C0 2 ratio in the separated acid gas, which may aid in the conversion of H 2 S to elemental sulfur using the Claus process.
  • the present disclosure provides an amine composition comprising a mixture of at least two sterically hindered amines comprising a first amine with the formula:
  • the present disclosure provides a method of making an amine composition
  • a method of making an amine composition comprising reacting a polyethylene glycol with a tertiarybutylamine in the presence of a nickel-based hydrogenation catalyst to form an amine composition comprising a mixture of at least two sterically hindered amines, wherein the amine composition comprises at least a first amine with the formula:
  • the present disclosure provides a method comprising contacting a gaseous stream comprising sulfur-containing compounds with an amine composition comprising a mixture of at least two sterically hindered amines, wherein the amine composition comprises at least a first amine with the formula:
  • Figure 1 is a graph showing the effect of C0 2 concentration on H 2 S removal.
  • Figure 2 is a graph showing the effect of C0 2 concentration effect on C0 2 absorption.
  • Figure 3 is a graph showing the change of H 2 S in a treated gas as a function of the amine circulation rate.
  • the present disclosure generally relates to sterically hindered amines, and more specifically, to the production of sterically hindered amines from polyethylene glycol and tertiarybutylamine and their use in acidic gas removal.
  • the present disclosure is based, at least in part, on the observation that under certain conditions, such as C0 2 rich conditions and/or high bis-(tertiarybutylaminoethoxy) ethane content, certain amines for selectively removing H 2 S gas may become phase separated.
  • certain amines for selectively removing H 2 S gas may become phase separated.
  • the present disclosure addresses this problem by, among other things, reacting a higher molecular weight polyethylene glycol with a tertiarybutylamine to produce a mixture of sterically hindered amines that provides good performance without the problem of phase separation.
  • the sterically hindered amines of the present disclosure may be made without the need for a solvent, thereby simplifying their production.
  • the methods of the present disclosure may be considered more "environmentally friendly" in that they produce higher yields of desirable amine products with minimal to no production of undesirable by-products, which may also reduce the costs associated with making sterically hindered amines.
  • the present disclosure provides an amine composition comprising a mixture of at least two sterically hindered amines with the following formulas:
  • the weight ratio of a first sterically hindered amine (1) to a second sterically hindered amine (2) is about 2.5:1 to about 6: 1. In some embodiments, the weight ratio of a first sterically hindered amine (1) to a second sterically hindered amine (2) is about 4: 1.
  • an amine composition of the present disclosure may comprise a mixture of at least two sterically hindered amines, a first sterically hindered amine having the chemical formula shown in (1) wherein x is an integer ranging from 7 to 14; and a second sterically hindered amine having the chemical formula shown in (2) wherein y is an integer ranging from 7 to 14.
  • the present disclosure also provides methods of making these amine compositions comprising reacting a polyethylene glycol with a tertiarybutylamine in the presence of a nickel-based hydrogenation catalyst.
  • the polyethylene glycol suitable for use in the present disclosure generally has a molecular weight between about 180 to about 1000 grams per mole (g/mol). In some specific embodiments, the polyethylene glycol may have a molecular weight between about 180 to about 400 g/mol. In some specific embodiments, the polyethylene glycol may have a molecular weight between about 200 to about 300 g/mol.
  • Nickel-based hydrogenation catalysts suitable for use in the present disclosure may include any nickel based catalyst capable of catalyzing a reaction between polyethylene glycol and a tertiarybutyl amine.
  • a suitable hydrogenation catalyst comprises those nickel-based catalysts disclosed in U.S. Patent Nos. 7,683,007 and 7,196,033, both of which are hereby incorporated by reference in their entirety.
  • the hydrogenation catalyst may be in any suitable form, including but not limited to, pellets, tablets, extrudates, spheres, etc.
  • a suitable catalyst can either be unsupported or deposited on a support material, as is known to those skilled in the art, such as alumina, silica, etc.
  • reduction of the hydrogenation catalyst may be carried out in situ while conducting the process by the presence of hydrogen. Hydrogen, however, is not essential to conducting the process but may be employed, for example, to minimize catalyst deactivation.
  • the sterically hindered amines of the present disclosure may be made without the need for a solvent, thereby simplifying their production.
  • an inert solvent may be included in the reaction medium if desired. Examples of suitable solvents may include, but are not limited to, a cyclic or linear ether or a hydrocarbon containing compound in which the reactants will dissolve.
  • the amination process may be carried out in any suitable reactor, including, but not limited to, a fixed-bed reactor, a fluid-bed reactor, a continuous stirred reactor, or a batch reactor.
  • the reaction of polyethylene glycol with a tertiarybutylamine may be carried out in a reactor under a pressure of about 500 to about 3000 psig and a temperature of from about 160°C to about 240 °C.
  • the sterically hindered amines of the present disclosure may be placed in a liquid medium prior to use, such as water, an organic solvent and mixtures thereof.
  • the sterically hindered amines may also be used in conjunction with a wide range of additives typically employed in selective gas removal processes, such as anti-foaming agents, antioxidants, corrosion inhibitors, etc. in an effective amount.
  • the sterically hindered amines of the present disclosure may also be used in conjunction with a strong acid, such as sulfuric acid, sulfurous acid, phosphoric acid, phosphorous acid, pyrophosphoric acid, acetic acid, formic acid, adipic acid, benzoic acid, etc.
  • Acidic gas mixtures suitable for use in the present disclosure include any gas mixture that comprises an acidic gas for which acid gas removal is desired.
  • suitable acidic gas mixtures are those comprising H 2 S, and optionally other gases such as C0 2 , N 2 , CH 4 , H 2 , CO, COS, HCN, C 2 H 4 , NH 3 , etc.
  • Acidic gas mixtures may include various types of gases, including, but not limited to, combustion gases, refinery gases, town gas, natural gas, syn gas, water gas, propane, propylene, heavy hydrocarbon gases, etc.
  • the present disclosure also provides a method for removing sulfur-containing compounds from a gaseous stream comprising contacting the gaseous stream with an amine composition of the present disclosure.
  • the gaseous stream and an amine composition of the present disclosure may be brought into contact using any conventional means, such as a tower or packed vessel.
  • a gaseous stream may be fed into a lower portion of an absorption tower while an amine composition of the present disclosure is fed into an upper portion of the tower.
  • the gaseous stream and the amine composition may come into contact with each other such that sulfur- containing compounds, such as H 2 S, may be selectively absorbed by the amine composition.
  • the amine composition containing the selectively absorbed sulfur-containing compounds may then emerge near the bottom or lower portion of the tower, which the remaining normally gaseous stream, emerges from the upper portion of the tower.
  • the amine composition containing the sulfur-containing compounds may be at least partially regenerated so that it may be reused.
  • PEG-240 from Example 1 and tertiarybutylamine were each continuously fed to a tubular reactor that was charged with 250 cc of a nickel catalyst at feed rates of 120 g/hr and 300 g/hr, respectively.
  • the reactor pressure and temperature (hot oil temperature) were maintained at 2000 psig and 200°C.
  • the reactor effluent was stripped of excess tertiarybutylamine and other light materials.
  • the resulting product was analyzed to contain 4.28 meq/g of total amine.
  • Example 3 Preparation of Amine from TEG [0029] Triethylene Glycol and tertiarybutylamine were each continuously fed to a tubular reactor that was charged with 250 cc of a nickel catalyst at feed rates of 115 g/hr and 300 g/hr, respectively. The reactor pressure and temperature (hot oil temperature) were maintained at 2000 psig and 200°C. The reactor effluent was stripped of excess tertiarybutylamine and other light materials. The resulting product was analyzed to contain 5.72 meq/g of total amine.
  • Example 4 Effect of C0 2 concentration on H 2 S removal and C0 2 absorption
  • Example 5 Effect of amine circulation flow on H 2 S removal

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Gas Separation By Absorption (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Treating Waste Gases (AREA)
PCT/US2011/061604 2010-12-01 2011-11-21 Sterically hindered amines and associated methods WO2012074807A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
CN2011800581625A CN103282341A (zh) 2010-12-01 2011-11-21 空间位阻胺和相关方法
CA2817994A CA2817994C (en) 2010-12-01 2011-11-21 Sterically hindered amines and associated methods
US13/989,137 US9352271B2 (en) 2010-12-01 2011-11-21 Sterically hindered amines and associated methods
EP11845094.9A EP2646407B1 (en) 2010-12-01 2011-11-21 Sterically hindered amines and associated methods
NO11845094A NO2646407T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 2010-12-01 2011-11-21
AU2011336995A AU2011336995B2 (en) 2010-12-01 2011-11-21 Sterically hindered amines and associated methods
JP2013542046A JP2014505022A (ja) 2010-12-01 2011-11-21 立体障害型アミン及び関連する方法
MX2013005958A MX362397B (es) 2010-12-01 2011-11-21 Aminas inhibidas estericamente y metodos asociados.
EP17180356.2A EP3255034B1 (en) 2010-12-01 2011-11-21 Sterically hindered amines and associated methods
MX2018004065A MX371466B (es) 2010-12-01 2011-11-21 Aminas inhibidas estericamente y metodos asociados.
US15/070,050 US9700832B2 (en) 2010-12-01 2016-03-15 Sterically hindered amines and associated methods
US15/425,350 US9987588B2 (en) 2010-12-01 2017-02-06 Sterically hindered amines and associated methods

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US41842510P 2010-12-01 2010-12-01
US61/418,425 2010-12-01

Related Child Applications (2)

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US13/989,137 A-371-Of-International US9352271B2 (en) 2010-12-01 2011-11-21 Sterically hindered amines and associated methods
US15/070,050 Continuation US9700832B2 (en) 2010-12-01 2016-03-15 Sterically hindered amines and associated methods

Publications (1)

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WO2012074807A1 true WO2012074807A1 (en) 2012-06-07

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US (3) US9352271B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (2) EP2646407B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (2) JP2014505022A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (2) CN106631833A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU2011336995B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA2817994C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MX (2) MX362397B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MY (1) MY163068A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO2646407T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO2012074807A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

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* Cited by examiner, † Cited by third party
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WO2013082242A1 (en) * 2011-12-02 2013-06-06 Exxonmobil Research And Engineering Company Offshore gas separation process
WO2013138443A1 (en) * 2012-03-14 2013-09-19 Exxonmobil Research And Engineering Company Amine treating process for acid gas separation using blends of amines and alkyloxyamines
WO2013181242A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company An absorbent composition for the selective absorption of hydrogen sulfide
WO2013181249A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company A process for the high temperature selective absorption of hydrogen sulfide
WO2013181245A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company An absorbent composition for the selective absorption of hydrogen sulfide and a process of use thereof
WO2013181252A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company A method of improving a process for the selective absorption of hydrogen sulfide
US9987588B2 (en) 2010-12-01 2018-06-05 Huntsman Petrochemical Llc Sterically hindered amines and associated methods

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FR3014862B1 (fr) * 2013-12-17 2016-01-01 Axens Procede de purification du gaz de synthese par voie de lavage sur des solutions aqueuses d'amines
CN106540516A (zh) * 2015-09-18 2017-03-29 中国石油化工股份有限公司 一种天然气中脱除硫醇的专用脱硫剂
CN111440076A (zh) * 2019-01-17 2020-07-24 中国石油天然气集团有限公司 一种叔丁氨基三甘醇型位阻胺及其制备方法
CN117623950A (zh) * 2022-08-19 2024-03-01 中国石油天然气股份有限公司 一种用于天然气净化的空间位阻胺及其合成方法、应用
CN119488781A (zh) * 2024-11-19 2025-02-21 华中科技大学 一种用于二氧化碳捕集的低温再生非水相吸收剂

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0087856A1 (en) 1982-01-18 1983-09-07 Exxon Research And Engineering Company A process for the removal of H2S from gaseous mixtures using diaminoethers
US4405811A (en) * 1982-01-18 1983-09-20 Exxon Research And Engineering Co. Severely sterically hindered tertiary amino compounds
US4471138A (en) 1982-01-18 1984-09-11 Exxon Research And Engineering Co. Severely sterically hindered secondary aminoether alcohols
US4618481A (en) * 1985-08-30 1986-10-21 Exxon Research And Engineering Co. Absorbent composition containing a severely hindered amino compound and an amine salt and process for the absorption of H2 S using the same
US4894178A (en) 1987-10-13 1990-01-16 Exxon Research And Engineering Company Absorbent composition containing severely-hindered amine mixture for the absorption of H2 S
US20060069237A1 (en) * 1999-12-22 2006-03-30 Bentley Michael D Sterically hindered poly (ethylene glycol) alkanoic acids and derivatives thereof
US7196033B2 (en) 2001-12-14 2007-03-27 Huntsman Petrochemical Corporation Advances in amination catalysis
US20100037775A1 (en) 2005-08-09 2010-02-18 Exxon-Mobil Research And Engineering Company Alkylamino alkyloxy (alcohol) monoalkyl ether for acid gas scrubbing process

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US440581A (en) * 1890-11-11 straight
US4405582A (en) * 1982-01-18 1983-09-20 Exxon Research And Engineering Co. Process for selective removal of H2 S from mixtures containing H22 using diaminoether solutions
US4405583A (en) * 1982-01-18 1983-09-20 Exxon Research And Engineering Co. Process for selective removal of H2 S from mixtures containing H22 using di-severely sterically hindered secondary aminoethers
US4665195A (en) 1983-12-23 1987-05-12 Exxon Research And Engineering Company Process for preparing di-amino-polyalkenyl ethers
US4961873A (en) * 1987-10-13 1990-10-09 Exxon Research And Engineering Company Absorbent composition containing a severely-hindered amine mixture with amine salts and/or aminoacid additives for the absorption of H2 S
JP4655349B2 (ja) * 2000-10-18 2011-03-23 日油株式会社 経口医薬用ポリエチレングリコールおよびその製造方法
WO2008006752A1 (de) * 2006-07-14 2008-01-17 Basf Se Verfahren zur herstellung eines amins
CA2817994C (en) 2010-12-01 2019-01-22 Huntsman Petrochemical Llc Sterically hindered amines and associated methods

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0087856A1 (en) 1982-01-18 1983-09-07 Exxon Research And Engineering Company A process for the removal of H2S from gaseous mixtures using diaminoethers
US4405811A (en) * 1982-01-18 1983-09-20 Exxon Research And Engineering Co. Severely sterically hindered tertiary amino compounds
US4471138A (en) 1982-01-18 1984-09-11 Exxon Research And Engineering Co. Severely sterically hindered secondary aminoether alcohols
US4618481A (en) * 1985-08-30 1986-10-21 Exxon Research And Engineering Co. Absorbent composition containing a severely hindered amino compound and an amine salt and process for the absorption of H2 S using the same
US4894178A (en) 1987-10-13 1990-01-16 Exxon Research And Engineering Company Absorbent composition containing severely-hindered amine mixture for the absorption of H2 S
US20060069237A1 (en) * 1999-12-22 2006-03-30 Bentley Michael D Sterically hindered poly (ethylene glycol) alkanoic acids and derivatives thereof
US7196033B2 (en) 2001-12-14 2007-03-27 Huntsman Petrochemical Corporation Advances in amination catalysis
US7683007B2 (en) 2001-12-14 2010-03-23 Huntsman Petrochemicals LLC Advances in amination catalysis
US20100037775A1 (en) 2005-08-09 2010-02-18 Exxon-Mobil Research And Engineering Company Alkylamino alkyloxy (alcohol) monoalkyl ether for acid gas scrubbing process

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9987588B2 (en) 2010-12-01 2018-06-05 Huntsman Petrochemical Llc Sterically hindered amines and associated methods
WO2013082242A1 (en) * 2011-12-02 2013-06-06 Exxonmobil Research And Engineering Company Offshore gas separation process
WO2013138443A1 (en) * 2012-03-14 2013-09-19 Exxonmobil Research And Engineering Company Amine treating process for acid gas separation using blends of amines and alkyloxyamines
AU2013267524B2 (en) * 2012-05-31 2015-11-26 Huntsman Petrochemical Llc A method of improving a process for the selective absorption of hydrogen sulfide
WO2013181245A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company An absorbent composition for the selective absorption of hydrogen sulfide and a process of use thereof
WO2013181252A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company A method of improving a process for the selective absorption of hydrogen sulfide
WO2013181249A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company A process for the high temperature selective absorption of hydrogen sulfide
AU2013267521B2 (en) * 2012-05-31 2015-11-26 Huntsman Petrochemical Llc A process for the high temperature selective absorption of hydrogen sulfide
EA026972B1 (ru) * 2012-05-31 2017-06-30 Шелл Интернэшнл Рисерч Маатсхаппий Б.В. Способ высокотемпературной селективной абсорбции сероводорода
EA027025B1 (ru) * 2012-05-31 2017-06-30 Шелл Интернэшнл Рисерч Маатсхаппий Б.В. Способ улучшения процесса селективной абсорбции сероводорода
EA029139B1 (ru) * 2012-05-31 2018-02-28 Шелл Интернэшнл Рисерч Маатсхаппий Б.В. Композиция абсорбента для селективной абсорбции сероводорода
EA029106B1 (ru) * 2012-05-31 2018-02-28 Шелл Интернэшнл Рисерч Маатсхаппий Б.В. Композиция абсорбента для селективной абсорбции сероводорода и способ её использования
WO2013181242A1 (en) * 2012-05-31 2013-12-05 Shell Oil Company An absorbent composition for the selective absorption of hydrogen sulfide
US11071944B2 (en) 2012-05-31 2021-07-27 Shell Oil Company Absorbent composition for the selective absorption of hydrogen sulfide

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