US2886521A - Process for the sweetening of petroleum products - Google Patents

Process for the sweetening of petroleum products Download PDF

Info

Publication number
US2886521A
US2886521A US411256A US41125654A US2886521A US 2886521 A US2886521 A US 2886521A US 411256 A US411256 A US 411256A US 41125654 A US41125654 A US 41125654A US 2886521 A US2886521 A US 2886521A
Authority
US
United States
Prior art keywords
chelate
lead
cobalt
sweetening
per liter
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.)
Expired - Lifetime
Application number
US411256A
Other languages
English (en)
Inventor
Gislon Andre
Quiquerez Joseph
Maurin Jean Daniel
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.)
Compagnie Francaise de Raffinage SA
Original Assignee
Compagnie Francaise de Raffinage SA
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 Compagnie Francaise de Raffinage SA filed Critical Compagnie Francaise de Raffinage SA
Application granted granted Critical
Publication of US2886521A publication Critical patent/US2886521A/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • 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 chelates may be introduced in the fully prepared state in the petroleum prodact to be treated, or they may be formed in situ; the dia-mine which produces the Schiff base may be aliphatic, cyclic, aromatic or hydro-aromatic.
  • the chelate can be used in the presence of a solvent such as an alcohol, a ketone, a phenol, a fatty acid, etc., or in the form of an aqueous alcohol dispersion.
  • a solvent such as an alcohol, a ketone, a phenol, a fatty acid, etc.
  • the product may be put in contact with an excess of chelate in such a dispersion, which is recycled after separation.
  • nct nct to be treated in a minimum quantity just suflicient so that the product then becomes slowly sweet in the course of storage.
  • the oxygen dissolved in the products to be treated is often sufficient to permit the oxidation without it being necessary to provide for air blowing.
  • the present invention consists of operating the oxidation of mercaptans according to these techniques, which are the object of U.S. Patent No. 2,659,691 and US. patent applications Serial Numbers 340,918 and 385,274 filed respectively on March 6, 1953 (now US. Patent No. 2,823,173, granted February 11, 1958) and October 9, 1953, in the joint names of Andr Gislon and Joseph Quiquerez, in the presence of a salt of lead;
  • the petroleum product containing a lead salt may he treated with an aqueous alcoholic dispersion of chelate, which may have been produced in situv in the aqueous alcoholic medium by addition of the Sohiii base and a lead salt in a solution of a dispersion agent.
  • the process in accordance with the present invention may be applied in the form of various alternatives which differ either in the conditions under which the lead salt is added to the petroleum product or to the chelated compound, either by the process of obtaining this latter, or by a particularassociation of these two factors.
  • the lead salt may be chosen from amongst those which are soluble in the hydrocarbons: organic salt, phenolate, mercaptide, etc.
  • the lead salt may be added to the hydrocarbon to be treated together with the chelate in the presence of a solvent of the latter as circumstances may require.
  • Table 1 shows the development of the mercaptans after 24 hours in the various experiments as well as the stability of the gasolines obtained by the different treatments in comparison to the untreated (test h) and inhibited gasoline (test g).
  • hination chelate-lead resultsin a sweetening with a comsumption of chelate of 0.02 gram per liter, that is, a saving of 60% as compared with the treatment without lead.
  • EXAMPLE 2 One treats in the same manner as in Example 1, either an Iraq kerosene having a boiling range of 196 to 257" C. and a specific gravity of 0.795 or an Iraq gas oil boiling between 192 and 371 C. and'having'a specific gravity of 0.838 with 0.30 gram per liter of crcsol containing 10% bis disalicylal ethylene diimino di'cobalt and 10% of lead in the form of cresolate.
  • Table 2 shows the advantage of the use of lead which results in sweetening with an increased activity of the After sweetening the products are decolored by 1 part per thousand of active earth or by a wash with 20%- sulfuric acid. The products are substantially free of said metallic compounds.
  • EXAMPLE 3 (a) To a straight run Iraq gasoline with a boiling range of 40 to 160 C. and a specific gravity of 0.720, is added 3.0 cm. per liter of methanol containing grams per liter of salicylal propylene diimino-cobalt.
  • This example relates to the case where the cobalt chelate is formed in situ.
  • EXAMPLE 6 In a continuous operation one brings a gasoline--with a boiling range of 40 to 200 C. and a specific gravity of 0.730-in which successively are injected 7.5 grams per cubic meter of disalicylal propylene diimine-1,2 and 1.6 grams per cubic meter of cobalt in the form of acetyl acetonate, in contact in a mixer with A of its volume of 10% caustic soda in which are dissolved 3.5 grams per liter of litharge, while air is injected simultaneously.
  • the aqueous phase is separated in a settler and'irecycled to the 'mixer.
  • the gasoline obtained had a copper number of 3.
  • EXAMPLE 7 An aqueous dispersion of cobalt chelate of disalicylal propylene diimine 1,2 is prepared by adding stoichiometric quantities of caustic, of disalicylal propylene diimine 1,2 and of cobalt nitrate to a mixture of 90% by volume of water and 10% by volume of a commercial solution of a wetting agent known as Teepol. In this manner a stable aqueous dispersion containing 1% of chelate is obtained.
  • a composition for the sweetening of petroleum products which comprises a mixed solution of a lead salt and cobalt chelate of a Schitf base resulting from the condensation of an aromatic hydroxy aldehyde with a diamine.
  • a composition for the sweetening of petroleum products which comprises a mixed solution of a cobalt chelate compound of a Schifi base resulting from the condensation of an aromatic hydroxy aldehyde with a diamine and a lead salt soluble in the hydrocarbons.
  • a composition for the sweetening of petroleum products which comprises a mixed solution of a cobalt chelate compound of a Schifi" base resulting from the condensation of an aromatic hydroxy aldehyde with a diamine and a lead salt in a solvent which is miscible with the hydrocarbons and which is selected from the class consisting of alcohols, ketones, phenols and fatty acids.
  • a composition for the sweetening of petroleum products comprised of a solution, in cresol, of cresolate of lead and of chelate of cobalt of a disalicylal-diimine.
  • two solutions utilized conjointly and constituted the one by a solution of a Schiif base resulting from the condensation of an aromatic hydroxy aldehyde on a diamine, the said solution being rendered alkaline by a stoichiometric quantity of an alkaline hydroxide with two molecules of alkali per molecule of disalicylal-diimine, the other solution being a mixed solution of two salts, one of cobalt, the other of lead, both salts being soluble in the hydrocarbons.

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)
  • Liquid Carbonaceous Fuels (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
US411256A 1953-12-12 1954-02-18 Process for the sweetening of petroleum products Expired - Lifetime US2886521A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2886521X 1953-12-12
FR965795X 1953-12-19

Publications (1)

Publication Number Publication Date
US2886521A true US2886521A (en) 1959-05-12

Family

ID=32327970

Family Applications (1)

Application Number Title Priority Date Filing Date
US411256A Expired - Lifetime US2886521A (en) 1953-12-12 1954-02-18 Process for the sweetening of petroleum products

Country Status (6)

Country Link
US (1) US2886521A (is")
BE (1) BE533041A (is")
DE (1) DE965795C (is")
FR (1) FR1101183A (is")
GB (1) GB785043A (is")
NL (2) NL193111A (is")

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125506A (en) * 1964-03-17 Chelate sweetening

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1840269A (en) * 1930-03-18 1932-01-05 Lawrence L Reeves Method of refining distillates
US1904382A (en) * 1929-11-15 1933-04-18 Universal Oil Prod Co Process for sweetening hydrocarbon distillates containing mercaptans
US2278665A (en) * 1939-09-14 1942-04-07 Standard Oil Dev Co Refining petroleum oils
US2303835A (en) * 1939-05-09 1942-12-01 Roy L Gholson Method of sweetening sour petroleum distillates
US2651595A (en) * 1950-05-20 1953-09-08 Socony Vacuum Oil Co Inc Treating hydrocarbons

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1904382A (en) * 1929-11-15 1933-04-18 Universal Oil Prod Co Process for sweetening hydrocarbon distillates containing mercaptans
US1840269A (en) * 1930-03-18 1932-01-05 Lawrence L Reeves Method of refining distillates
US2303835A (en) * 1939-05-09 1942-12-01 Roy L Gholson Method of sweetening sour petroleum distillates
US2278665A (en) * 1939-09-14 1942-04-07 Standard Oil Dev Co Refining petroleum oils
US2651595A (en) * 1950-05-20 1953-09-08 Socony Vacuum Oil Co Inc Treating hydrocarbons

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3125506A (en) * 1964-03-17 Chelate sweetening

Also Published As

Publication number Publication date
BE533041A (is")
DE965795C (de) 1957-06-19
FR1101183A (fr) 1955-10-04
GB785043A (en) 1957-10-23
NL193111A (is")
NL87496C (is")

Similar Documents

Publication Publication Date Title
US2651595A (en) Treating hydrocarbons
US2659691A (en) Process for refining petroleum products
US4120865A (en) Metal complex and method for preparing
RU2472841C2 (ru) Катализаторы сульфоокисления и способы и системы их применения
US3708421A (en) Process to remove mercaptan sulfur from sour oils
GB2354024A (en) Reducing the concentration of metal soaps of partially esterified phosphates from hydrocarbon flowback fluids resulting from formation fracturing
US2552399A (en) Treating petroleum distillates
US2662859A (en) Compositions and process for emulsion breaking
CN101402877B (zh) 一种汽油的催化氧化脱硫方法
Katasonova et al. Extraction methods for removing sulfur and its compounds from crude oil and petroleum products
Guo et al. Optimization study on deep extractive oxidative desulfurization with tetrabutylammonium bromide/polyethylene glycol DES
US2948675A (en) Process for removing heavy metals from petroleum with an oil-insoluble sulfonic acid
US2886521A (en) Process for the sweetening of petroleum products
US3352777A (en) Oxidation of mercaptans
US4152396A (en) Separation and recovery of cobalt and nickel from aqueous solutions thereof
US2966452A (en) Sweetening sour hydrocarbon distillate with metal phthalocyanine catalyst in the presence of alkali air and sulfite ions
US2302352A (en) Refining mineral oils
US4243551A (en) Catalyst for oxidizing mercaptans and mercaptide compounds and method for preparing
US2574122A (en) Sweetening process
US4466906A (en) Catalyst for the oxidation of mercaptans to disulfides, process for the preparation thereof, and its use in the sweetening of petroleum distillates
US2223798A (en) Process for the removal of acid components from hydrocarbon distillates
US2862878A (en) Sweetening process and method for removing water of reaction from the sweetening reagent
US2915461A (en) Multi-stage sweetening process employing an alkaline hypochlorite solution
US2823173A (en) Methods of refining petroleum products
US2723221A (en) Use of chelating agents to improve acid treatment of hydrocarbon streams