WO2012009390A2 - 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
WO2012009390A2
WO2012009390A2 PCT/US2011/043778 US2011043778W WO2012009390A2 WO 2012009390 A2 WO2012009390 A2 WO 2012009390A2 US 2011043778 W US2011043778 W US 2011043778W WO 2012009390 A2 WO2012009390 A2 WO 2012009390A2
Authority
WO
WIPO (PCT)
Prior art keywords
bis
mercaptans
methylene
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.)
Ceased
Application number
PCT/US2011/043778
Other languages
English (en)
French (fr)
Other versions
WO2012009390A3 (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
Original Assignee
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 BR112013000892-0A priority Critical patent/BR112013000892B1/pt
Priority to JP2013519781A priority patent/JP5889296B2/ja
Priority to SG2013003009A priority patent/SG187079A1/en
Priority to CA2805489A priority patent/CA2805489C/en
Priority to MX2013000509A priority patent/MX2013000509A/es
Priority to EP11807420.2A priority patent/EP2593533B1/en
Priority to ES11807420.2T priority patent/ES2593462T3/es
Priority to KR1020137003669A priority patent/KR20130141438A/ko
Priority to RU2013102416/04A priority patent/RU2557545C2/ru
Publication of WO2012009390A2 publication Critical patent/WO2012009390A2/en
Publication of WO2012009390A3 publication Critical patent/WO2012009390A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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

  • Alpha-amino ether means a molecule according to the formula:
  • “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 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 US Patent 5,840, 177.
  • alpha-amino ethers as mercaptan scavengers
  • 9 different mercaptans were mixed together (Tables 4 and 5).
  • the mercaptan mixture 1000 ppm v/v) was added to kerosene and then the ppm wt of the sulfur species was measured according to ASTM D5623-94.
  • Various alpha-amino ethers (Tables 6 - 10) were used to treat the mercaptans by adding 3000 ppm v/v of various alpha-amino ethers.
  • the decrease in the individual mercaptan components and the corresponding increase in unidentified volatile sulfur species demonstrates that the mercaptans reacted with the alpha-amino ethers to from stable compounds of lower volatility.

Landscapes

  • 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)
PCT/US2011/043778 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons Ceased WO2012009390A2 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
BR112013000892-0A BR112013000892B1 (pt) 2010-07-14 2011-07-13 método para reduzir a quantidade de mercaptanos em um fluido hidrocarboneto
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
SG2013003009A SG187079A1 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons
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.
EP11807420.2A EP2593533B1 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons
ES11807420.2T ES2593462T3 (es) 2010-07-14 2011-07-13 Uso de alfa-amino éteres para la eliminación de mercaptanos de hidrocarburos
KR1020137003669A KR20130141438A (ko) 2010-07-14 2011-07-13 탄화수소로부터 머캅탄을 제거하기 위한 알파-아미노 에테르의 용도
RU2013102416/04A RU2557545C2 (ru) 2010-07-14 2011-07-13 Использование простых альфа-аминоэфиров для удаления меркаптанов из углеводородов

Applications Claiming Priority (2)

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

Publications (2)

Publication Number Publication Date
WO2012009390A2 true WO2012009390A2 (en) 2012-01-19
WO2012009390A3 WO2012009390A3 (en) 2012-04-19

Family

ID=45466086

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2011/043778 Ceased WO2012009390A2 (en) 2010-07-14 2011-07-13 Use of alpha-amino ethers for the removal of mercaptans from hydrocarbons

Country Status (15)

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

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103249712B (zh) * 2010-11-30 2016-03-02 艾达索高新材料无锡有限公司 用于合成可重复利用环氧树脂的化合物
US8785694B2 (en) 2012-06-05 2014-07-22 Connora Technologies, Inc Processes for the preparation of di-(2-aminoethyl) formal, di-(3-aminopropyl) formal, and related molecules
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
CN114159946B (zh) * 2022-02-11 2022-04-29 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

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2186398A (en) * 1939-02-07 1940-01-09 Shell Dev Process for removing acid components from hydrocarbon distillates
US3408287A (en) * 1966-04-20 1968-10-29 Universal Oil Prod Co Oxidation of mercaptans
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
US4556546A (en) * 1983-05-04 1985-12-03 Air Products And Chemicals, Inc. Bis tertiary amino alkyl derivatives as solvents for acid gas removal from gas streams
CA2017047C (en) * 1989-08-01 1999-08-17 Jerry J. Weers Method of scavenging hydrogen sulfide from hydrocarbons
EP0728033B1 (en) * 1993-11-09 1999-04-21 Union Carbide Chemicals & Plastics Technology Corporation Absorption of mercaptans
CA2148849A1 (en) * 1994-06-23 1995-12-24 Kishan Bhatia Method of treating sour gas and liquid hydrocarbons
US5698171A (en) * 1996-01-10 1997-12-16 Quaker Chemical Corporation Regenerative method for removing sulfides from gas streams
NO982505L (no) * 1997-06-04 1998-12-07 Nalco Exxon Energy Chem Lp Sammensetning og fremgangsmÕte for avsvovling av gassformige eller flytende hydrokarboner, vandige systemer og blandinger derav
US8486183B2 (en) * 2005-08-09 2013-07-16 Exxonmobil Research And Engineering Company Alkylamino alkyloxy (alcohol) monoalkyl ether for acid gas scrubbing process
RU2349627C2 (ru) * 2005-10-27 2009-03-20 Ахматфаиль Магсумович Фахриев Средство для удаления сероводорода и/или низкомолекулярных меркаптанов и способ его использования
WO2010027353A1 (en) * 2008-09-02 2010-03-11 General Electric Company Process for removing hydrogen sulfide in crude oil
US9394396B2 (en) * 2011-06-21 2016-07-19 Baker Hughes Incorporated Hydrogen sulfide scavenger for use in hydrocarbons

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP2593533A4 *

Also Published As

Publication number Publication date
PT2593533T (pt) 2016-07-29
EP2593533A2 (en) 2013-05-22
SG187079A1 (en) 2013-02-28
BR112013000892A2 (pt) 2016-05-17
AR082166A1 (es) 2012-11-14
EP2593533A4 (en) 2014-04-23
EP2593533B1 (en) 2016-07-06
US20120012505A1 (en) 2012-01-19
HUE030422T2 (en) 2017-05-29
BR112013000892B1 (pt) 2020-10-20
JP5889296B2 (ja) 2016-03-22
JP2013535530A (ja) 2013-09-12
RU2013102416A (ru) 2014-08-20
RU2557545C2 (ru) 2015-07-27
KR20130141438A (ko) 2013-12-26
MX2013000509A (es) 2013-02-27
CA2805489C (en) 2018-05-08
CA2805489A1 (en) 2012-01-19
ES2593462T3 (es) 2016-12-09
WO2012009390A3 (en) 2012-04-19
PL2593533T3 (pl) 2016-12-30

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