WO1998002501A1 - Bisoxazolidine hydrogen sulfide scavenger - Google Patents
Bisoxazolidine hydrogen sulfide scavenger Download PDFInfo
- Publication number
- WO1998002501A1 WO1998002501A1 PCT/US1997/011813 US9711813W WO9802501A1 WO 1998002501 A1 WO1998002501 A1 WO 1998002501A1 US 9711813 W US9711813 W US 9711813W WO 9802501 A1 WO9802501 A1 WO 9802501A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substrate
- bisoxazolidine
- natural gas
- crude oil
- Prior art date
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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS 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
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
Definitions
- the invention relates to chemical compositions and methods for scavenging
- sulfhydryl compounds particularly hydrogen sulfide (H 2 S), from "sour" aqueous
- the invention relates to hydrocarbon
- soluble sulfhydryl scavengers comprising preferably substantially water free
- Hydrogen sulfide is highly flammable, toxic when inhaled, and
- containing salts can deposit in and plug or corrode transmission pipes, valves,
- Hydrogen sulfide has an offensive odor, and natural gas containing H 2 S often
- the present invention provides a method for scavenging sulfhydryl
- Fig. 1 is a Table giving the results of Example 2.
- Fig. 2 is a chart of the results in Fig. 1.
- Fig. 3 is a Table giving the results of Example 3.
- the scavenging agents of the present invention may be used to treat
- H 2 S hydrogen sulfide
- organosulfur compounds having a
- sulfhydryl (-SH) group known as mercaptans, also known as thiols (R-SH, where
- R is a hydrocarbon group
- thiol carboxylic acids RCO-SH
- dithio acids RCS-
- hydrocarbon substrates can be treated using the scavenging
- hydrocarbon substrate is meant to
- unrefined and refined hydrocarbon products including natural gas, derived
- hydrocarbon substrate includes wellhead condensate as
- Hydrocarbon substrate also includes the same materials transported from those
- hydrocarbon substrate also includes product
- distillates such as gasolines, distillate fuels,
- Preferred substrates for the bisoxazolidines of the present inventions are
- Such substrates include,
- the scavenging agents of the present invention preferably have the following
- n is between about 1-2 and R 1 and R 2 independently are selected from the
- alkyl alkenyl, and alkynyl groups having between about 1- 6 carbon atoms.
- n 1 and R 1 and R 2 independently are selected from the
- alkynyl groups having between about 1- 3 carbon atoms.
- embodiment is 3,3' methylenebis-[5-methyl oxazolidine], in which n is 1 and R 1
- R 2 are methyl groups.
- R 1 and R 2 may be
- the bisoxazolidines of the present invention exhibit a high uptake capacity
- Bisoxazolidines are low cost materials. Bisoxazolidines may be made by reacting
- an alkanolamine with between about 1.1 to 2.1 equivalents, preferably 1.5
- MIPA monoisopropanolamine
- reaction formed by the reaction preferably should be removed by distillation, preferably
- the reaction takes place at ambient pressure and at a
- bisoxazolidine should contain less than about 20% water, most preferably less than
- Bisoxazolidines are commercially available in Europe as preservatives for
- the treatment may
- Preferred treatment temperatures are between ambient to
- the hydrocarbon or aqueous substrate should be treated with the
- sulfhydryls in the vapor phase to at least about 200 ppm or less.
- the amount of H 2 S in the vapor phase above the hydrocarbon may be measured.
- the bisoxazolidine may be added to the hydrocarbon in an amount equal to about
- bisoxazolidines of the present invention will be most effective if the substrate is treated at temperatures between ambient to about 200°C
- MIPA monoisopropanolamine
- GC gas chromatograph
- control bottles were designated
- the TER is defined as
- the oil was dosed to a level of 18,000 ppm H 2 S and dispensed into the serum
- Fig.l shows the results for the additives two hours after the first injection of
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Treating Waste Gases (AREA)
- Epoxy Compounds (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97933310A EP0882112B1 (en) | 1996-07-12 | 1997-07-08 | Bisoxazolidine hydrogen sulfide scavenger |
DK97933310T DK0882112T3 (en) | 1996-07-12 | 1997-07-08 | Bisoxazolidine-containing hydrogen sulfide capture |
AU36526/97A AU719046B2 (en) | 1996-07-12 | 1997-07-08 | Bisoxazolidine hydrogen sulfide scavenger |
CA002231659A CA2231659C (en) | 1996-07-12 | 1997-07-08 | Bisoxazolidine hydrogen sulfide scavenger |
NO19981090A NO317951B1 (en) | 1996-07-12 | 1998-03-12 | Process for Removing Sulfhudyl Compounds from Hydrocarbon Substrates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US67904096A | 1996-07-12 | 1996-07-12 | |
US08/679,040 | 1996-07-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998002501A1 true WO1998002501A1 (en) | 1998-01-22 |
Family
ID=24725344
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/011813 WO1998002501A1 (en) | 1996-07-12 | 1997-07-08 | Bisoxazolidine hydrogen sulfide scavenger |
Country Status (7)
Country | Link |
---|---|
US (2) | US6117310A (en) |
EP (1) | EP0882112B1 (en) |
AU (1) | AU719046B2 (en) |
CA (1) | CA2231659C (en) |
DK (1) | DK0882112T3 (en) |
NO (1) | NO317951B1 (en) |
WO (1) | WO1998002501A1 (en) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2005087899A1 (en) * | 2004-02-11 | 2005-09-22 | Baker Hughes Incorporated | Hydrocarbons having reduced levels of mercaptans and method and composition useful for preparing same |
WO2016180563A1 (en) | 2015-05-14 | 2016-11-17 | Clariant International Ltd | Composition and method for scavenging sulfides and mercaptans |
DE102015121689A1 (en) | 2015-12-14 | 2017-06-14 | Schülke & Mayr GmbH | Use of compositions containing 3,3'-methylenebis (5-methyloxazolidine) in the removal of sulfur compounds from process streams |
DE102016113930A1 (en) | 2016-07-28 | 2018-02-01 | Schülke & Mayr GmbH | Condensation product of 1-aminopropan-2-ol and formaldehyde and its use for reducing the amount of hydrogen sulfide in liquids and gases |
WO2018050567A1 (en) * | 2016-09-15 | 2018-03-22 | Schülke & Mayr GmbH | Use of compositions having a content of condensation product of 1-aminopropan-2-ol and formaldehyde in the removal of sulphur compounds from process streams |
WO2019120753A1 (en) | 2017-12-22 | 2019-06-27 | Clariant International Ltd | Synergized acetals compositions and method for scavenging sulfides and mercaptants |
WO2019120761A1 (en) | 2017-12-22 | 2019-06-27 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptants |
EP3505591A1 (en) | 2018-01-02 | 2019-07-03 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
EP3505590A1 (en) | 2018-01-02 | 2019-07-03 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
EP3578622A1 (en) | 2016-07-01 | 2019-12-11 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
WO2020115133A1 (en) | 2018-12-04 | 2020-06-11 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
WO2020115132A1 (en) | 2018-12-04 | 2020-06-11 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
WO2020115135A1 (en) | 2018-12-04 | 2020-06-11 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
WO2020115134A1 (en) | 2018-12-04 | 2020-06-11 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
US20210238068A1 (en) * | 2020-01-23 | 2021-08-05 | Championx Usa Inc. | Compositions of heterocyclic compounds and uses as sulfidogenesis inhibitors |
WO2021214151A1 (en) | 2020-04-22 | 2021-10-28 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
DE102020120287A1 (en) | 2020-07-31 | 2022-02-03 | Vink Chemicals Gmbh & Co. Kg | COMPOSITIONS AND METHODS FOR REMOVAL OF SULFUR COMPOUNDS FROM PROCESS STREAM |
WO2022122865A1 (en) | 2020-12-11 | 2022-06-16 | Totalenergies Onetech | Hydrogen sulphide and mercaptans scavenging compositions |
WO2023172708A1 (en) * | 2022-03-11 | 2023-09-14 | The Lubrizol Corporation | Method for preparing a reaction product containing 3,3'-methylenebis[5-methyloxazolidine], compositions including the reaction product, and uses of the reaction product |
EP4279566A1 (en) | 2022-05-20 | 2023-11-22 | TotalEnergies OneTech | Compounds and compositions useful for scavenging hydrogen sulphide and sulfhydryl-containing compounds |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998002501A1 (en) * | 1996-07-12 | 1998-01-22 | Baker Hughes Incorporated | Bisoxazolidine hydrogen sulfide scavenger |
CA2445422A1 (en) * | 2001-04-25 | 2002-10-31 | Clearwater International, Llc | Treatment of hydrocarbons containing sulfides |
US8562820B2 (en) * | 2001-11-09 | 2013-10-22 | Clearwater International, L.L.C. | Sulfide scavenger |
US7211665B2 (en) * | 2001-11-09 | 2007-05-01 | Clearwater International, L.L.C. | Sulfide scavenger |
US8357306B2 (en) | 2010-12-20 | 2013-01-22 | Baker Hughes Incorporated | Non-nitrogen sulfide sweeteners |
US9656237B2 (en) | 2014-07-31 | 2017-05-23 | Baker Hughes Incorporated | Method of scavenging hydrogen sulfide and mercaptans using well treatment composites |
WO2018001629A1 (en) * | 2016-07-01 | 2018-01-04 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
US11802246B2 (en) | 2021-03-11 | 2023-10-31 | Baker Hughes Oilfield Operations Llc | Synergistic effects among mercaptan scavengers |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2647118A (en) * | 1950-06-22 | 1953-07-28 | Socony Vacuum Oil Co Inc | Method for preparing bis-(substituted tetrahydro-1, 3-oxazino)-methanes |
US4166122A (en) * | 1977-03-15 | 1979-08-28 | Bayer Aktiengesellschaft | Bis-(5,5-dimethyl-1,3-oxazolidin-3-yl) methane as an antimicrobial agent |
US4978512A (en) * | 1988-12-23 | 1990-12-18 | Quaker Chemical Corporation | Composition and method for sweetening hydrocarbons |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5128049A (en) | 1991-01-22 | 1992-07-07 | Gatlin Larry W | Hydrogen sulfide removal process |
US5488103A (en) * | 1991-07-11 | 1996-01-30 | Gatlin; Larry W. | Hydrogen sulfide converter |
US5347003A (en) * | 1993-03-05 | 1994-09-13 | Quaker Chemical Corporation | Methods for regenerating a sulfur scavenging compound from a product of a sulfur scavenging reaction |
US5354453A (en) * | 1993-04-13 | 1994-10-11 | Exxon Chemical Patents Inc. | Removal of H2 S hydrocarbon liquid |
CA2148849A1 (en) * | 1994-06-23 | 1995-12-24 | Kishan Bhatia | Method of treating sour gas and liquid hydrocarbons |
WO1998002501A1 (en) * | 1996-07-12 | 1998-01-22 | Baker Hughes Incorporated | Bisoxazolidine hydrogen sulfide scavenger |
-
1997
- 1997-07-08 WO PCT/US1997/011813 patent/WO1998002501A1/en active IP Right Grant
- 1997-07-08 AU AU36526/97A patent/AU719046B2/en not_active Ceased
- 1997-07-08 EP EP97933310A patent/EP0882112B1/en not_active Expired - Lifetime
- 1997-07-08 CA CA002231659A patent/CA2231659C/en not_active Expired - Fee Related
- 1997-07-08 DK DK97933310T patent/DK0882112T3/en active
- 1997-11-14 US US08/970,669 patent/US6117310A/en not_active Expired - Fee Related
-
1998
- 1998-03-12 NO NO19981090A patent/NO317951B1/en unknown
-
2000
- 2000-08-04 US US09/632,726 patent/US6339153B1/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2647118A (en) * | 1950-06-22 | 1953-07-28 | Socony Vacuum Oil Co Inc | Method for preparing bis-(substituted tetrahydro-1, 3-oxazino)-methanes |
US4166122A (en) * | 1977-03-15 | 1979-08-28 | Bayer Aktiengesellschaft | Bis-(5,5-dimethyl-1,3-oxazolidin-3-yl) methane as an antimicrobial agent |
US4978512A (en) * | 1988-12-23 | 1990-12-18 | Quaker Chemical Corporation | Composition and method for sweetening hydrocarbons |
US4978512B1 (en) * | 1988-12-23 | 1993-06-15 | Composition and method for sweetening hydrocarbons |
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0882778A3 (en) * | 1997-06-04 | 1999-05-06 | Nalco/Exxon Energy Chemicals, L.P. | Composition and method for sweetening gaseous or liquid hydrocarbons, aqueous systems and mixtures thereof |
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 |
WO2005087899A1 (en) * | 2004-02-11 | 2005-09-22 | Baker Hughes Incorporated | Hydrocarbons having reduced levels of mercaptans and method and composition useful for preparing same |
EA010683B1 (en) * | 2004-02-11 | 2008-10-30 | Бейкер Хьюз Инкорпорейтед | Hydrocarbons having reduced levels of mercaptans and method and composition useful for preparing the same |
WO2016180563A1 (en) | 2015-05-14 | 2016-11-17 | Clariant International Ltd | Composition and method for scavenging sulfides and mercaptans |
US11155745B2 (en) | 2015-05-14 | 2021-10-26 | Clariant International Ltd. | Composition and method for scavenging sulfides and mercaptans |
DE102015121689A1 (en) | 2015-12-14 | 2017-06-14 | Schülke & Mayr GmbH | Use of compositions containing 3,3'-methylenebis (5-methyloxazolidine) in the removal of sulfur compounds from process streams |
WO2017102693A1 (en) * | 2015-12-14 | 2017-06-22 | Schülke & Mayr GmbH | Use of compositions having a content of 3,3'-methylenebis(5-methyloxazolidine) in the removal of sulphur compounds from process streams |
US10640714B2 (en) | 2015-12-14 | 2020-05-05 | Vink Chemicals Gmbh & Co. Kg | Use of compositions having a content of 3,3′-methylenebis(5-methyloxazolidine) in the removal of sulphur compounds from process streams |
EP3578622A1 (en) | 2016-07-01 | 2019-12-11 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
US11530347B2 (en) | 2016-07-01 | 2022-12-20 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
US10519144B2 (en) | 2016-07-28 | 2019-12-31 | Vink Chemicals Gmbh & Co. Kg | Condensation product of 1-amino-2-propanol and formaldehyde and the use thereof for reducing the amount of hydrogen sulphide in liquids and gases |
CN107663180B (en) * | 2016-07-28 | 2023-01-03 | 舒美有限公司 | Condensation products of 1-amino-2-propanol and formaldehyde and their use for reducing the amount of hydrogen sulphide in liquids and gases |
CN107663180A (en) * | 2016-07-28 | 2018-02-06 | 舒美有限公司 | The condensation product and its purposes in the amount of the hydrogen sulfide in reducing liquids and gases of the propyl alcohol of 1 amino 2 and formaldehyde |
DE102016113930A1 (en) | 2016-07-28 | 2018-02-01 | Schülke & Mayr GmbH | Condensation product of 1-aminopropan-2-ol and formaldehyde and its use for reducing the amount of hydrogen sulfide in liquids and gases |
WO2018050567A1 (en) * | 2016-09-15 | 2018-03-22 | Schülke & Mayr GmbH | Use of compositions having a content of condensation product of 1-aminopropan-2-ol and formaldehyde in the removal of sulphur compounds from process streams |
WO2019120761A1 (en) | 2017-12-22 | 2019-06-27 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptants |
EA039295B1 (en) * | 2017-12-22 | 2021-12-30 | Клариант Интернэшнл Лтд | Synergized acetal composition and method for scavenging sulfides and mercaptants |
WO2019120753A1 (en) | 2017-12-22 | 2019-06-27 | Clariant International Ltd | Synergized acetals compositions and method for scavenging sulfides and mercaptants |
US11603497B2 (en) | 2017-12-22 | 2023-03-14 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
US11555140B2 (en) | 2017-12-22 | 2023-01-17 | Clariant International Ltd | Synergized hemiacetals composition and method for scavenging sulfides and mercaptans |
EP3505591A1 (en) | 2018-01-02 | 2019-07-03 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
EP3505590A1 (en) | 2018-01-02 | 2019-07-03 | Clariant International Ltd | Synergized acetals composition and method for scavenging sulfides and mercaptans |
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WO2020115132A1 (en) | 2018-12-04 | 2020-06-11 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
WO2020115133A1 (en) | 2018-12-04 | 2020-06-11 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
US11945999B2 (en) * | 2018-12-04 | 2024-04-02 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
US11897796B2 (en) * | 2020-01-23 | 2024-02-13 | Championx Usa Inc. | Compositions of heterocyclic compounds and uses as sulfidogenesis inhibitors |
US20210238068A1 (en) * | 2020-01-23 | 2021-08-05 | Championx Usa Inc. | Compositions of heterocyclic compounds and uses as sulfidogenesis inhibitors |
WO2021214151A1 (en) | 2020-04-22 | 2021-10-28 | Total Marketing Services | Hydrogen sulphide and mercaptans scavenging compositions |
WO2022023565A1 (en) | 2020-07-31 | 2022-02-03 | Vink Chemicals Gmbh & Co. Kg | Compositions and methods for removing sulfur compounds from process streams |
DE102020120287A1 (en) | 2020-07-31 | 2022-02-03 | Vink Chemicals Gmbh & Co. Kg | COMPOSITIONS AND METHODS FOR REMOVAL OF SULFUR COMPOUNDS FROM PROCESS STREAM |
WO2022122865A1 (en) | 2020-12-11 | 2022-06-16 | Totalenergies Onetech | Hydrogen sulphide and mercaptans scavenging compositions |
WO2023172708A1 (en) * | 2022-03-11 | 2023-09-14 | The Lubrizol Corporation | Method for preparing a reaction product containing 3,3'-methylenebis[5-methyloxazolidine], compositions including the reaction product, and uses of the reaction product |
WO2023222538A1 (en) | 2022-05-20 | 2023-11-23 | Totalenergies Onetech | Compounds and compositions useful for scavenging hydrogen sulphide and sulfhydryl-containing compounds |
EP4279566A1 (en) | 2022-05-20 | 2023-11-22 | TotalEnergies OneTech | Compounds and compositions useful for scavenging hydrogen sulphide and sulfhydryl-containing compounds |
Also Published As
Publication number | Publication date |
---|---|
EP0882112B1 (en) | 2002-10-02 |
EP0882112A1 (en) | 1998-12-09 |
AU719046B2 (en) | 2000-05-04 |
CA2231659C (en) | 2003-12-23 |
AU3652697A (en) | 1998-02-09 |
US6117310A (en) | 2000-09-12 |
US6339153B1 (en) | 2002-01-15 |
NO317951B1 (en) | 2005-01-10 |
DK0882112T3 (en) | 2003-01-13 |
NO981090D0 (en) | 1998-03-12 |
CA2231659A1 (en) | 1998-01-22 |
NO981090L (en) | 1998-05-11 |
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