US2918426A - Sweetening of hydrocarbons containing mercaptans and/or mercaptides with a chelate and oxygen - Google Patents

Sweetening of hydrocarbons containing mercaptans and/or mercaptides with a chelate and oxygen Download PDF

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Publication number
US2918426A
US2918426A US733506A US73350658A US2918426A US 2918426 A US2918426 A US 2918426A US 733506 A US733506 A US 733506A US 73350658 A US73350658 A US 73350658A US 2918426 A US2918426 A US 2918426A
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US
United States
Prior art keywords
chelate
oxygen
mercaptides
mercaptans
temperature
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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.)
Expired - Lifetime
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US733506A
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English (en)
Inventor
Quiquerez Joseph
Weisang Edouard
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Compagnie Francaise de Raffinage SA
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Compagnie Francaise de Raffinage SA
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    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B26/00—Obtaining alkali, alkaline earth metals or magnesium
    • C22B26/20—Obtaining alkaline earth metals or magnesium
    • C22B26/22—Obtaining magnesium
    • 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
    • C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
    • C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
    • C10G27/10—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of metal-containing organic complexes, e.g. chelates, or cationic ion-exchange resins

Definitions

  • the present invention relates to the treatment of hydrocarbons and mixtures of hydrocarbons containing mercaptans and/or mercaptides, in which these compounds are converted into disulfides.
  • This invention relates to a method of oxidizing mercaptans and/or mercaptides to disulfides, by the action of oxygen or any gaseous mixture consisting essentially of oxygen, in the presence of chelate organo-metallic compounds, obtained by condensation of an iminophenol and a metal of group VIII-or of suitable compounds to form the chelate compound in situ-under determined conditions of temperature and pressure.
  • the present invention permits a very considerable increase of the speed of oxidation of the mer- Patented .Dec. 22, 1959 ICC captans and/or mercaptides to disulfides, that is, a re; duction in the time required for attaining sweetening of the sour petroleum fractions by the action of atmospheric oxygen in the presence of chelate organo-metallic compounds or of compounds suitable for forming them in situ.
  • Another considerable advantage of the method according to the invention is to effect substantial economies in the amounts used of the chelate organo-metallic compounds, or of compounds suitable for forming them in situ, while enablingsweetening of the treated products to be effected at speeds of reaction that are satisfactory from the industrial viewpoint.
  • EXAMPLE 1 In this example, specially intended to show that the method according to the invention limits, or rather prevents, the formation of compounds more oxidized than the disulfides, a known mercaptantert.-butyl mercap tan-is oxidized in solution in a defined hydrocarbon, namely benzene.
  • one advantage of the method forming the subject of the invention is the avoidance of the formation of secondary reactions and, in particular, of those liable to lead to substantial reductions of the induction periods (stability to oxidation) of the fractions treated.
  • a process for oxidizing a member of the group consisting of mercaptans and mercaptides to disulfides in which the oxidation is effected by the action of a gas containing oxygen, at a temperature of about 30 C. at least and at atmospheric pressure, in the presence of chelate organo-metallic compounds.
  • a process for oxidizing a member of the group consisting of mercaptans and mercaptides to disulfides in which the oxidation is elfected by the action of a gas containing oxygen, at a temperature of about C. at least and at atmospheric pressure, in the presence of chelate organo-metallic compounds, obtained by condensation of irninophenol and a metal of group VIII.
  • a process for sweetening petroleum distillate hydrocarbons in which they are treated with a gas consisting essentially of oxygen, at a temperature of about 30 C. at least and at atmospheric pressure, in the presence of chelate organo-metallic compounds.
  • a process for sweetening petroleum distillate hydrocarbons in which they are treated with a gas consisting essentially of oxygen, at a temperature of about 30 C. at least and at atmospheric pressure, in the presence of chelate organo-metallic compounds, obtained by condensation of an iminophenol and a metal of group VIII.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Geology (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
US733506A 1957-05-10 1958-05-07 Sweetening of hydrocarbons containing mercaptans and/or mercaptides with a chelate and oxygen Expired - Lifetime US2918426A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1174954T 1957-05-10

Publications (1)

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US2918426A true US2918426A (en) 1959-12-22

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US733506A Expired - Lifetime US2918426A (en) 1957-05-10 1958-05-07 Sweetening of hydrocarbons containing mercaptans and/or mercaptides with a chelate and oxygen

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US (1) US2918426A (en))
BE (1) BE567576A (en))
DE (1) DE1075249B (en))
FR (1) FR1174954A (en))
GB (1) GB846175A (en))
NL (1) NL103100C (en))

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125506A (en) * 1964-03-17 Chelate sweetening
US4298463A (en) * 1980-07-11 1981-11-03 Uop Inc. Method of treating a sour petroleum distillate
US4308169A (en) * 1978-12-26 1981-12-29 Uop Inc. Method of reactivating a catalytic composite of a carrier material and a mercaptan oxidation catalyst
US4318825A (en) * 1979-08-15 1982-03-09 Frame Robert R Catalytic composite, and method of manufacture
US4320029A (en) * 1980-07-17 1982-03-16 Uop Inc. Catalytic composite, method of manufacture, and process for use
US4324650A (en) * 1979-10-01 1982-04-13 Uop Inc. Catalytic composite and process for use
US4337147A (en) * 1979-11-07 1982-06-29 Uop Inc. Catalytic composite and process for use
US4360421A (en) * 1980-07-17 1982-11-23 Uop Inc. Method for treating mercaptans contained in a sour petroleum distillate
US4824818A (en) * 1988-02-05 1989-04-25 Uop Inc. Catalytic composite and process for mercaptan sweetening
US4897180A (en) * 1988-02-05 1990-01-30 Uop Catalytic composite and process for mercaptan sweetening
US4908122A (en) * 1989-05-08 1990-03-13 Uop Process for sweetening a sour hydrocarbon fraction
US4913802A (en) * 1989-05-08 1990-04-03 Uop Process for sweetening a sour hydrocarbon fraction
US4923596A (en) * 1989-05-22 1990-05-08 Uop Use of quaternary ammonium compounds in a liquid/liquid process for sweetening a sour hydrocarbon fraction
US4929340A (en) * 1989-07-31 1990-05-29 Uop Catalyst and process for sweetening a sour hydrocarbon fraction using dipolar compounds
US5039398A (en) * 1990-03-19 1991-08-13 Uop Elimination of caustic prewash in the fixed bed sweetening of high naphthenic acids hydrocarbons
US5064525A (en) * 1991-02-19 1991-11-12 Uop Combined hydrogenolysis plus oxidation process for sweetening a sour hydrocarbon fraction
US5093296A (en) * 1990-08-27 1992-03-03 Uop Caustic free liquid/liquid process for sweetening a sour hydrocarbon fraction
US5120453A (en) * 1990-12-24 1992-06-09 Uop Oxidative removal of cyanide from aqueous streams
US5180484A (en) * 1990-08-27 1993-01-19 Uop Caustic free liquid/liquid process for sweeting a sour hydrocarbon fraction
US5204306A (en) * 1990-08-27 1993-04-20 Uop Caustic free catalyst for use in a liquid/liquid process for sweetening a sour hydrocarbon fraction
US5232887A (en) * 1992-04-02 1993-08-03 Uop Catalyst for sweetening a sour hydrocarbon fraction
US5271835A (en) * 1992-05-15 1993-12-21 Uop Process for removal of trace polar contaminants from light olefin streams
US5273646A (en) * 1990-08-27 1993-12-28 Uop Process for improving the activity of a mercaptan oxidation catalyst
US5318936A (en) * 1992-09-23 1994-06-07 Uop Catalyst for sweetening a sour hydrocarbon fraction containing metal oxide solid solution and magnesium oxide
US5413701A (en) * 1993-11-15 1995-05-09 Uop Process for sweetening a sour hydrocarbon fraction using a supported metal chelate and a solid base
US5413704A (en) * 1993-11-15 1995-05-09 Uop Process for sweetening a sour hydrocarbon fraction using a mixture of a supported metal chelate and a solid base
US5424051A (en) * 1992-01-14 1995-06-13 Uop Process for the removal of carbon dioxide and mercaptans from a gas stream
US5698103A (en) * 1996-10-04 1997-12-16 Uop Extraction of water-soluble metal chelates used as catalysts in sweetening sour hydrocarbon feedstocks

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2651595A (en) * 1950-05-20 1953-09-08 Socony Vacuum Oil Co Inc Treating hydrocarbons
US2659691A (en) * 1949-08-26 1953-11-17 Raffinage Cie Francaise Process for refining petroleum products
US2744854A (en) * 1952-06-30 1956-05-08 Universal Oil Prod Co Oxidation of mercaptans
US2823173A (en) * 1952-06-19 1958-02-11 Raffinage Cie Francaise Methods of refining petroleum products

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2659691A (en) * 1949-08-26 1953-11-17 Raffinage Cie Francaise Process for refining petroleum products
US2651595A (en) * 1950-05-20 1953-09-08 Socony Vacuum Oil Co Inc Treating hydrocarbons
US2823173A (en) * 1952-06-19 1958-02-11 Raffinage Cie Francaise Methods of refining petroleum products
US2744854A (en) * 1952-06-30 1956-05-08 Universal Oil Prod Co Oxidation of mercaptans

Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125506A (en) * 1964-03-17 Chelate sweetening
US4308169A (en) * 1978-12-26 1981-12-29 Uop Inc. Method of reactivating a catalytic composite of a carrier material and a mercaptan oxidation catalyst
US4318825A (en) * 1979-08-15 1982-03-09 Frame Robert R Catalytic composite, and method of manufacture
US4324650A (en) * 1979-10-01 1982-04-13 Uop Inc. Catalytic composite and process for use
US4337147A (en) * 1979-11-07 1982-06-29 Uop Inc. Catalytic composite and process for use
US4298463A (en) * 1980-07-11 1981-11-03 Uop Inc. Method of treating a sour petroleum distillate
US4320029A (en) * 1980-07-17 1982-03-16 Uop Inc. Catalytic composite, method of manufacture, and process for use
US4360421A (en) * 1980-07-17 1982-11-23 Uop Inc. Method for treating mercaptans contained in a sour petroleum distillate
US4374042A (en) * 1980-07-21 1983-02-15 Uop Inc. Method of reactivating a catalytic composite of a carrier material and a mercaptan oxidation catalyst
US4824818A (en) * 1988-02-05 1989-04-25 Uop Inc. Catalytic composite and process for mercaptan sweetening
US4897180A (en) * 1988-02-05 1990-01-30 Uop Catalytic composite and process for mercaptan sweetening
US4908122A (en) * 1989-05-08 1990-03-13 Uop Process for sweetening a sour hydrocarbon fraction
US4913802A (en) * 1989-05-08 1990-04-03 Uop Process for sweetening a sour hydrocarbon fraction
US4923596A (en) * 1989-05-22 1990-05-08 Uop Use of quaternary ammonium compounds in a liquid/liquid process for sweetening a sour hydrocarbon fraction
US4929340A (en) * 1989-07-31 1990-05-29 Uop Catalyst and process for sweetening a sour hydrocarbon fraction using dipolar compounds
US5039398A (en) * 1990-03-19 1991-08-13 Uop Elimination of caustic prewash in the fixed bed sweetening of high naphthenic acids hydrocarbons
US5273646A (en) * 1990-08-27 1993-12-28 Uop Process for improving the activity of a mercaptan oxidation catalyst
US5180484A (en) * 1990-08-27 1993-01-19 Uop Caustic free liquid/liquid process for sweeting a sour hydrocarbon fraction
US5204306A (en) * 1990-08-27 1993-04-20 Uop Caustic free catalyst for use in a liquid/liquid process for sweetening a sour hydrocarbon fraction
US5093296A (en) * 1990-08-27 1992-03-03 Uop Caustic free liquid/liquid process for sweetening a sour hydrocarbon fraction
US5120453A (en) * 1990-12-24 1992-06-09 Uop Oxidative removal of cyanide from aqueous streams
US5238581A (en) * 1990-12-24 1993-08-24 Uop Oxidative removal of cyanide from aqueous streams abetted by ultraviolet irradiation
US5064525A (en) * 1991-02-19 1991-11-12 Uop Combined hydrogenolysis plus oxidation process for sweetening a sour hydrocarbon fraction
US5424051A (en) * 1992-01-14 1995-06-13 Uop Process for the removal of carbon dioxide and mercaptans from a gas stream
US5286372A (en) * 1992-04-02 1994-02-15 Uop Process for sweetening a sour hydrocarbon fraction using a solid base
US5232887A (en) * 1992-04-02 1993-08-03 Uop Catalyst for sweetening a sour hydrocarbon fraction
US5271835A (en) * 1992-05-15 1993-12-21 Uop Process for removal of trace polar contaminants from light olefin streams
US5318936A (en) * 1992-09-23 1994-06-07 Uop Catalyst for sweetening a sour hydrocarbon fraction containing metal oxide solid solution and magnesium oxide
US5401390A (en) * 1992-09-23 1995-03-28 Uop Catalyst for sweetening a sour hydrocarbon fraction containing metal oxide solid solution and magnesium oxide
US5413701A (en) * 1993-11-15 1995-05-09 Uop Process for sweetening a sour hydrocarbon fraction using a supported metal chelate and a solid base
US5413704A (en) * 1993-11-15 1995-05-09 Uop Process for sweetening a sour hydrocarbon fraction using a mixture of a supported metal chelate and a solid base
US5529967A (en) * 1993-11-15 1996-06-25 Uop Process for sweetening a sour hydrocarbon fraction using a supported metal chelate and a solid base
US5593932A (en) * 1993-11-15 1997-01-14 Uop Process for sweetening a sour hydrocarbon fraction using a mixture of a supported metal chelate and a solid base
US5698103A (en) * 1996-10-04 1997-12-16 Uop Extraction of water-soluble metal chelates used as catalysts in sweetening sour hydrocarbon feedstocks

Also Published As

Publication number Publication date
GB846175A (en) 1960-08-24
DE1075249B (de) 1960-02-11
NL103100C (en))
BE567576A (en))
FR1174954A (fr) 1959-03-18

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