US2882224A - Process for sweetening sour hydrocarbon distillates with metal phthalocyanine catalyst in the presence of alkali and air - Google Patents

Process for sweetening sour hydrocarbon distillates with metal phthalocyanine catalyst in the presence of alkali and air Download PDF

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US2882224A
US2882224A US714937A US71493758A US2882224A US 2882224 A US2882224 A US 2882224A US 714937 A US714937 A US 714937A US 71493758 A US71493758 A US 71493758A US 2882224 A US2882224 A US 2882224A
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sweetening
air
gasoline
phthalocyanine
distillate
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US714937A
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William K T Gleim
Urban Peter
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Universal Oil Products Co
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Universal Oil Products Co
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Priority to NL235884D priority patent/NL235884A/xx
Priority to BE575509D priority patent/BE575509A/xx
Priority to US714937A priority patent/US2882224A/en
Application filed by Universal Oil Products Co filed Critical Universal Oil Products Co
Priority to DEU5960A priority patent/DE1084861B/en
Priority to GB4396/59A priority patent/GB849998A/en
Priority to ES0247118A priority patent/ES247118A1/en
Priority to FR786323A priority patent/FR1216168A/en
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Publication of US2882224A publication Critical patent/US2882224A/en
Priority to MY196286A priority patent/MY6200086A/en
Priority to OA50640A priority patent/OA00553A/en
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    • 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

  • This invention relates to the treatment of hydrocarbon distillates and more particularly to a novel method of gaseous fractions.
  • the novel .features of the present invention may be utilized for purifying other organic fractions containing certain acidic impurities. These organic compounds include alcohols, ketones, aldehydes, etc.
  • the present invention relates to a process for sweetening a sour hydrocarbon distillate which comprises reacting said distillate with an oxidizing agent in the presence of a phthalocyanine catalyst.
  • the present invention relates to the process for sweetening sour gasoline which com. prises oxidizing mercaptans contained in said gasoline in the presence of caustic solution and cobalt phthalocyanine disulfonate.
  • the present invention may be utilized to effect sweetening of a sour distillate having a comparatively high mercaptan content, in general it is preferred to remove a major proportion of the mercaptans from the distillate.
  • removal of mercaptans from gasoline is preferred rather than conversionof the mercaptans to disulfides and subsequent retention of the disulfides in the gasoline.
  • Sulfur compounds have an unfavorable elfect on tetraethyl lead-susceptibility.
  • conventional treating methods remove fromabout 50 to about 95% of the mercaptans but leave a product still containing a minor concentration of mercaptans and accordingly a product which is still sour.
  • the final sweetening is effected by oxidizing the mercaptans in the presence of an alkaline reagent and a phthalocyanine catalyst.
  • any suitable phthalocyanine catalyst meeting the requirements of high activity and stability during use may be employed in the present invention.
  • Particularly preferred metal phthalocyanines comprise cobalt phthalocyanine and vanadium phthalocyanine.
  • the metal phthalocyanine in general is not readily soluble in aqueous solutions and, therefore, for improved operation is preferably utilized as a derivative thereof.
  • a particularly preferred derivative is the sulfonated derivative.
  • a preferred phthalocyanine catalyst comprises cobalt phthalocyanine disulfonate.
  • Another preferred catalyst comprises vanadium phthalocyanine disulfonate.
  • These compounds may be obtained from any suitable source or may be prepared in any suitable manner as, for example, by reacting cobalt or vanadium phthalocyanine with fuming sulfuric acid. While the sulfonic acid derivatives are preferred, it is understood that other suitable derivatives may be employed. Other derivatives 7 2,882,224! Patented Apr. 14, 1959;
  • carboxylated derivative which may be prepared, for example, by the action of trichloroacetic acid on the metal phthalocyanine or by the action of phosgene and aluminum chloride. In the latter re action the acid chloride is formed and may be converted to the desired carboxylated derivative by conventional hydrolysis.
  • sweetening is eifected in the presence of an alkaline reagent.
  • Any suitable alkaline reagent may be employed.
  • a preferred reagent comprises an aqueous solution of an alkaline metal hydroxide, such as sodium hydroxide solution, potassium hydroxide solution, etc., or these reagents containing a solubilizer or solutizer including, for example, alcohol such as methanol, ethanol, etc., phenols, cresols, etc., tannin, ism butyrate, etc.
  • a particularly preferred alkaline solution is an aqueous solution of from about 5 to about 50% by weight concentration of sodium hydroxide, and, when employed, a preferred solutizer is methanol which may be used in a concentration of from about 5 to about 200 volume percent of the caustic or other alkaline solution.
  • the phthalocyanine catalyst is both very active and highly stable. Because of its high activity, the catalyst is used in exceedingly small concentrations. These may range from 5 to 500 and preferably from 10 to parts per million by weight of the alkaline solution, although lower or higher concentrations may housed in some cases. The use of higher concentrations are unnecessary in most cases but may be used if desired, and thus may range up to 25% or more by weight of the alkaline solution. Be cause of its high stability, the catalyst is used for exceed ⁇ , ingly long periods of time. After a long period of use, the alkaline solution may become saturated with acidic compounds which may adversely eflect its further use, and the caustic solution either may be discarded or in some cases may be regenerated by conventional means.
  • sweetening of the sour hydrocarbon distillate is effected by oxidation of mercaptans.
  • an oxidizing agent is present in the reaction, Air is preferred, although. oxygen or other oxygencontaining gases may be utilized.
  • the sour petroleum distillate may contain entrained oxygen orair in suflicient concentration to accomplish the desired sweetening, but generally it is preferred tointroduce air into the reaction. The amount of air must'be sufficient to effect oxidation of mercaptans, although an excess thereof generally is not objectionable.
  • Sweetening of the petroleum distillate may be effected in any suitable manner and may be in batch or continuous process.
  • a batch process the sour hydrocarbon distillate is introduced into a reaction zone containing the phthalocyanine catalyst and alkaline reagent, and air is introduced therein or passed therethrough.
  • the reaction zone is equipped with suitable stirrers or other mixing devices to obtain intimate mixing.
  • the caustic solution containing phthalocyanine catalyst is passed countercurrently to an ascending stream of sour petroleum distillate in the presence of a continuous stream of air.
  • the reaction zone contains the alkaline solution and phthalocyanine catalyst, and gasoline and air are continuously passed therethrough and removed, generally from the upper portion of the reaction zone.
  • the sweetening reaction is effected at ambient temperature.
  • elevated temperature may be employed and generally will be within the range of from about 100 to about 400 F. or more, depending upon the pressure utilized therein, but usually below that at which substantial vaporization occurs.
  • final sweetening of the gasoline may be preceded by extraction of acidic components and particularly mercaptans from the gasoline in any suitable manner.
  • This pretreatment preferably comprises contacting of the gasoline with an alkaline solution, usually at ambient temperature and either in a batch or continuous process. In some cases elevated temperatures which may range up to about 200 F. may be employed.
  • the alkaline reagents and, when employed, solubilizer or solutize'r heretofore set forth generally are utilized in the pretreatment. Following this treatment, the petroleum distillate will not be sweet and is subjected to final sweetening in the presence of air and the phthalocyanine catalyst.
  • Example I The gasoline used in this example is a cracked gasoline having a mercaptan sulfur content of 0.003% by weight. It is subjected to sweetening by being passed in contact with 20 Baum caustic solution containing 50 parts per million of cobalt phthalocyanine disulfonate based on the active NaOI-I content of the caustic solution. On the basis of treating 1,000 barrels per day of cracked gasoline in a continuous process, barrels of caustic solution are used, and air is introduced at a rate of 10 cubic feet per hour into the sweetening zone. In order to efiect intimate contact in the sweetening zone, the caustic solution containing the phthalocyanine catalyst is preferably introduced into the upper portion of the sweetening zone through a suitable spray arrangement.
  • the air is introduced into the lower portion of the sweetening zone through a suitable spray arrangement, and the sour gasoline is introduced at an intermediate point in the sweetening zone.
  • the sweetening zone contains suitable contacting means such as side to side pans, bubble decks, bubble trays, etc. in order to effect intimate mixing therein.
  • the sweetening is effected at ambient temperature and the treated gasoline withdrawn from the sweetening zone will be doctor sweet.
  • Example 11 In this example sour kerosene containing 0.005% by weight of mercaptan sulfur is treated in a batch type process with a 28% potassium hydroxide aqueous solution containing 100 parts per million, based on the KOH content of the potassium hydroxide solution, of cobalt phthalocyanine disulfonate.
  • the potassium hydroxide solution containing cobalt phthalocyanine disulfonate, "sour kerosene and air are charged into the reaction zone and are intimately mixed by means of stirring blades. The sweetening is efiected at ambient temperature.
  • the kerosene is separated from the potassium hydroxide solution and cobalt phthalocyanine disulfonate.
  • the kerosene so recovered is doctor sweet.
  • Example III This example describes sweetening effected in the manner described in Example I except that 20% by volume, based on the caustic solution, of methanol is included in the reaction mixture.
  • the gasoline treated in this manner will be doctor sweet in less than 3 hours of contacting in the manner described in Example I and utilizing the same constituents except for the addition of the methanol.
  • the process for sweetening sour gasoline which comprises reacting mercaptans contained in said gasoline with air in the presence of caustic solution and cobalt phthalocyanine disulfonate.
  • the process for sweetening sour gasoline which comprises reacting mercaptans contained in said gasoline with air in the presence of caustic solution and vanadium phthalocyanine disulfonate.

Description

United States. Patent PROCESS FOR SWEETENING. SOUR HYDROCAR- BON DISTILLATES WITH METAL PHTHALO- CYANINE CATALYST IN THE PRESENCE OF ALKALI AND AIR William K. T. Gleim, Island Lake, and Peter Urban, Northbrook, Ill., assignors, by mesne assignments, to Universal Oil Products Company, Des Plaines, 111., a corporation of Delaware No Drawing. Application February 13, 1958 7 Serial No. 714,937
6 Claims. (Cl. 208206) This invention relates to the treatment of hydrocarbon distillates and more particularly to a novel method of gaseous fractions. In still another embodiment the novel .features of the present invention may be utilized for purifying other organic fractions containing certain acidic impurities. These organic compounds include alcohols, ketones, aldehydes, etc.
In one embodiment the present invention relates to a process for sweetening a sour hydrocarbon distillate which comprises reacting said distillate with an oxidizing agent in the presence of a phthalocyanine catalyst.
In a specific embodiment the present invention relates to the process for sweetening sour gasoline which com. prises oxidizing mercaptans contained in said gasoline in the presence of caustic solution and cobalt phthalocyanine disulfonate.
While the present invention may be utilized to effect sweetening of a sour distillate having a comparatively high mercaptan content, in general it is preferred to remove a major proportion of the mercaptans from the distillate. For example, removal of mercaptans from gasoline is preferred rather than conversionof the mercaptans to disulfides and subsequent retention of the disulfides in the gasoline. Sulfur compounds have an unfavorable elfect on tetraethyl lead-susceptibility. However, conventional treating methods remove fromabout 50 to about 95% of the mercaptans but leave a product still containing a minor concentration of mercaptans and accordingly a product which is still sour. In a preferred embodiment of the present invention, the final sweetening is effected by oxidizing the mercaptans in the presence of an alkaline reagent and a phthalocyanine catalyst.
Any suitable phthalocyanine catalyst meeting the requirements of high activity and stability during use may be employed in the present invention. Particularly preferred metal phthalocyanines comprise cobalt phthalocyanine and vanadium phthalocyanine. The metal phthalocyanine in general is not readily soluble in aqueous solutions and, therefore, for improved operation is preferably utilized as a derivative thereof. A particularly preferred derivative is the sulfonated derivative. Thus, a preferred phthalocyanine catalyst comprises cobalt phthalocyanine disulfonate. Another preferred catalyst comprises vanadium phthalocyanine disulfonate. These compounds may be obtained from any suitable source or may be prepared in any suitable manner as, for example, by reacting cobalt or vanadium phthalocyanine with fuming sulfuric acid. While the sulfonic acid derivatives are preferred, it is understood that other suitable derivatives may be employed. Other derivatives 7 2,882,224! Patented Apr. 14, 1959;
include particularly the carboxylated derivative which may be prepared, for example, by the action of trichloroacetic acid on the metal phthalocyanine or by the action of phosgene and aluminum chloride. In the latter re action the acid chloride is formed and may be converted to the desired carboxylated derivative by conventional hydrolysis. I
As hereinbefore set forth, sweetening is eifected in the presence of an alkaline reagent. Any suitable alkaline reagent may be employed. A preferred reagent comprises an aqueous solution of an alkaline metal hydroxide, such as sodium hydroxide solution, potassium hydroxide solution, etc., or these reagents containing a solubilizer or solutizer including, for example, alcohol such as methanol, ethanol, etc., phenols, cresols, etc., tannin, ism butyrate, etc. A particularly preferred alkaline solution is an aqueous solution of from about 5 to about 50% by weight concentration of sodium hydroxide, and, when employed, a preferred solutizer is methanol which may be used in a concentration of from about 5 to about 200 volume percent of the caustic or other alkaline solution.
The phthalocyanine catalyst is both very active and highly stable. Because of its high activity, the catalyst is used in exceedingly small concentrations. These may range from 5 to 500 and preferably from 10 to parts per million by weight of the alkaline solution, although lower or higher concentrations may housed in some cases. The use of higher concentrations are unnecessary in most cases but may be used if desired, and thus may range up to 25% or more by weight of the alkaline solution. Be cause of its high stability, the catalyst is used for exceed}, ingly long periods of time. After a long period of use, the alkaline solution may become saturated with acidic compounds which may adversely eflect its further use, and the caustic solution either may be discarded or in some cases may be regenerated by conventional means.
As hereinbefore set forth, sweetening of the sour hydrocarbon distillate is effected by oxidation of mercaptans. Accordingly, an oxidizing agent is present in the reaction, Air is preferred, although. oxygen or other oxygencontaining gases may be utilized. In some cases the sour petroleum distillate may contain entrained oxygen orair in suflicient concentration to accomplish the desired sweetening, but generally it is preferred tointroduce air into the reaction. The amount of air must'be sufficient to effect oxidation of mercaptans, although an excess thereof generally is not objectionable.
Sweetening of the petroleum distillate may be effected in any suitable manner and may be in batch or continuous process. In a batch process the sour hydrocarbon distillate is introduced into a reaction zone containing the phthalocyanine catalyst and alkaline reagent, and air is introduced therein or passed therethrough. Preferably the reaction zone is equipped with suitable stirrers or other mixing devices to obtain intimate mixing. In a continuous process the caustic solution containing phthalocyanine catalyst is passed countercurrently to an ascending stream of sour petroleum distillate in the presence of a continuous stream of air. In a mixed type process, the reaction zone contains the alkaline solution and phthalocyanine catalyst, and gasoline and air are continuously passed therethrough and removed, generally from the upper portion of the reaction zone.
In general the sweetening reaction is effected at ambient temperature. In some cases, elevated temperature may be employed and generally will be within the range of from about 100 to about 400 F. or more, depending upon the pressure utilized therein, but usually below that at which substantial vaporization occurs.
As hereinbefore set forth, final sweetening of the gasoline may be preceded by extraction of acidic components and particularly mercaptans from the gasoline in any suitable manner. This pretreatment preferably comprises contacting of the gasoline with an alkaline solution, usually at ambient temperature and either in a batch or continuous process. In some cases elevated temperatures which may range up to about 200 F. may be employed. The alkaline reagents and, when employed, solubilizer or solutize'r heretofore set forth generally are utilized in the pretreatment. Following this treatment, the petroleum distillate will not be sweet and is subjected to final sweetening in the presence of air and the phthalocyanine catalyst.
The following examples are introduced to illustrate further the novelty and utility of the present invention but not with the intention of unduly limiting the same.
Example I The gasoline used in this example is a cracked gasoline having a mercaptan sulfur content of 0.003% by weight. It is subjected to sweetening by being passed in contact with 20 Baum caustic solution containing 50 parts per million of cobalt phthalocyanine disulfonate based on the active NaOI-I content of the caustic solution. On the basis of treating 1,000 barrels per day of cracked gasoline in a continuous process, barrels of caustic solution are used, and air is introduced at a rate of 10 cubic feet per hour into the sweetening zone. In order to efiect intimate contact in the sweetening zone, the caustic solution containing the phthalocyanine catalyst is preferably introduced into the upper portion of the sweetening zone through a suitable spray arrangement. Similarly, the air is introduced into the lower portion of the sweetening zone through a suitable spray arrangement, and the sour gasoline is introduced at an intermediate point in the sweetening zone. Preferably the sweetening zone contains suitable contacting means such as side to side pans, bubble decks, bubble trays, etc. in order to effect intimate mixing therein. The sweetening is effected at ambient temperature and the treated gasoline withdrawn from the sweetening zone will be doctor sweet.
Example 11 In this example sour kerosene containing 0.005% by weight of mercaptan sulfur is treated in a batch type process with a 28% potassium hydroxide aqueous solution containing 100 parts per million, based on the KOH content of the potassium hydroxide solution, of cobalt phthalocyanine disulfonate. The potassium hydroxide solution containing cobalt phthalocyanine disulfonate, "sour kerosene and air are charged into the reaction zone and are intimately mixed by means of stirring blades. The sweetening is efiected at ambient temperature.
After treatment for 2 hours in this manner, the kerosene is separated from the potassium hydroxide solution and cobalt phthalocyanine disulfonate. The kerosene so recovered is doctor sweet.
Example III This example describes sweetening effected in the manner described in Example I except that 20% by volume, based on the caustic solution, of methanol is included in the reaction mixture. The gasoline treated in this manner will be doctor sweet in less than 3 hours of contacting in the manner described in Example I and utilizing the same constituents except for the addition of the methanol.
We claim as our invention:
1. The process for treating a sour hydrocarbon distillate which comprises reacting said distillate with an oxidizing agent in the presence of an alkaline reagent and a phthalocyanine catalyst selected from the group consisting of metal phthalocyanines and their sulfonated and carboxylated derivatives.
2. The process for treating a sour hydrocarbon distillate which comprises reacting mercaptans contained in said distillate with oxygen in the presence of an alkaline reagent and a phthalocyanine catalyst selected from the group consisting of metal phthalocyanines and their sulfonated and carboxylated derivatives.
3. The process for treating a sour hydrocarbon distillate which comprises reacting mercaptans contained in said distillate with air in the presence of an alkaline reagent and cobalt phthalocyanine disulfonate.
4. The process for treating a sour hydrocarbon distillate which comprises reacting mercaptans contained in said distillate with air in the presence of an alkaline reagent and vanadium phthalocyanine disulfonate.
5. The process for sweetening sour gasoline which comprises reacting mercaptans contained in said gasoline with air in the presence of caustic solution and cobalt phthalocyanine disulfonate.
6. The process for sweetening sour gasoline which comprises reacting mercaptans contained in said gasoline with air in the presence of caustic solution and vanadium phthalocyanine disulfonate.
References Cited in the file of this patent UNITED STATES PATENTS 1,998,863 Chaney et al. Apr. 23, 1935 2,550,091 Seebold Apr. 24, 1951 2,651,595 Moulthrop Sept. 8, 1953 2,659,691 Gibson et al Nov. 17, 1953 OTHER REFERENCES Cook: Jour. Chem. Soc. (1938), pages 1761-74 (from Chem. Abstracts, vol. 33, pages 1328-30).

Claims (1)

1. THE PROCESS FOR TREATING A SOUR HYDROCARBON DISTILLATE WHICH COMPRISES REACTING SAID DISTILLATE WITH AN OXIDIZING AGENT IN THE PRESENCE OF AN ALKALINE REAGENT AND A PHTHALOCYANINE CATALYST SELECTED FROM THE GROUP CONSISTING OF METAL PHTHALOCYANINES AND THEIR SULFONATED AND CARBOXYLATED DERIVATIVES.
US714937A 1958-02-13 1958-02-13 Process for sweetening sour hydrocarbon distillates with metal phthalocyanine catalyst in the presence of alkali and air Expired - Lifetime US2882224A (en)

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Application Number Priority Date Filing Date Title
NL120003D NL120003C (en) 1958-02-13
NL235884D NL235884A (en) 1958-02-13
BE575509D BE575509A (en) 1958-02-13
US714937A US2882224A (en) 1958-02-13 1958-02-13 Process for sweetening sour hydrocarbon distillates with metal phthalocyanine catalyst in the presence of alkali and air
DEU5960A DE1084861B (en) 1958-02-13 1959-02-06 Process for sweetening acidic hydrocarbon distillates
GB4396/59A GB849998A (en) 1958-02-13 1959-02-09 Process for sweetening sour hydrocarbon distillates
ES0247118A ES247118A1 (en) 1958-02-13 1959-02-09 Process for sweetening sour hydrocarbon distillates with metal phthalocyanine catalyst in the presence of alkali and air
FR786323A FR1216168A (en) 1958-02-13 1959-02-10 Process for softening acidic hydrocarbon distillates
MY196286A MY6200086A (en) 1958-02-13 1962-12-31 Process for sweetening sour hydrocarbon distillates
OA50640A OA00553A (en) 1958-02-13 1964-11-18 Process for softening acidic hydrocarbon distillates.

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DE (1) DE1084861B (en)
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FR (1) FR1216168A (en)
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Cited By (32)

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US2966452A (en) * 1959-02-24 1960-12-27 Universal Oil Prod Co Sweetening sour hydrocarbon distillate with metal phthalocyanine catalyst in the presence of alkali air and sulfite ions
US2976229A (en) * 1959-04-24 1961-03-21 Universal Oil Prod Co Purification of acid oils
US2988500A (en) * 1959-03-13 1961-06-13 Universal Oil Prod Co Treatment of hydrocarbon distillates
US2999806A (en) * 1959-03-13 1961-09-12 Universal Oil Prod Co Treatment of hydrocarbon distillates
US3029201A (en) * 1959-12-28 1962-04-10 Universal Oil Prod Co Water treatment
US3029202A (en) * 1960-04-19 1962-04-10 Universal Oil Prod Co Treating waste water
US3108081A (en) * 1959-07-17 1963-10-22 Universal Oil Prod Co Catalyst and manufacture thereof
US3148156A (en) * 1961-03-14 1964-09-08 Universal Oil Prod Co Phthalocyanine catalyst regeneration
US3252890A (en) * 1964-08-28 1966-05-24 Universal Oil Prod Co Oxidation of mercaptans using phthalocyanine and mercury catalyst
US3252891A (en) * 1964-08-28 1966-05-24 Universal Oil Prod Co Oxidation of mercaptans
US3260665A (en) * 1964-10-23 1966-07-12 Universal Oil Prod Co Oxidation of difficultly oxidizable mercaptans
US3410727A (en) * 1965-01-08 1968-11-12 Allis Chalmers Mfg Co Fuel cell electrodes having a metal phthalocyanine catalyst
US3413215A (en) * 1966-05-16 1968-11-26 Universal Oil Prod Co Oxidation of mercapto compounds
DE1290279B (en) * 1961-11-24 1969-03-06 Universal Oil Prod Co Process for obtaining a hydrocarbon distillate with reduced mercaptan content and improved color
US3493596A (en) * 1966-03-23 1970-02-03 Universal Oil Prod Co Synthesis of organic isocyanates
US3525683A (en) * 1968-03-21 1970-08-25 Phillips Petroleum Co Sweetening of jp-4 jet fuel with an alkali metal plumbite,phthalocyanine compound and elemental sulfur
US4003827A (en) * 1975-06-12 1977-01-18 Universal Oil Products Company Mercaptan conversion process for a petroleum distillate charge stock
US4070271A (en) * 1975-09-22 1978-01-24 Uop Inc. Catalytic oxidation of mercaptans and removal of naphthenic acids, catalyst toxins, and toxin precursors from petroleum distillates
US4087378A (en) * 1977-01-18 1978-05-02 Uop Inc. Preparation of a supported metal phthalocyanine
US4088569A (en) * 1976-02-24 1978-05-09 Uop Inc. Mercaptan oxidation in a liquid hydrocarbon with a metal phthalocyanine catalyst
US4141819A (en) * 1977-01-18 1979-02-27 Uop Inc. Process for treating a sour petroleum distillate
US4412912A (en) * 1983-03-01 1983-11-01 Uop Inc. Hydrocarbon treating process having minimum gaseous effluent
US4412913A (en) * 1982-08-05 1983-11-01 Standard Oil Company (Indiana) Use of alkanolamines in sweetening sour liquid hydrocarbon streams
US4481106A (en) * 1983-12-05 1984-11-06 Uop Inc. Hydrocarbon treating process
US4875997A (en) * 1988-11-17 1989-10-24 Montana Refining Company Process for treating hydrocarbons containing mercaptans
US4906354A (en) * 1987-09-10 1990-03-06 Mobil Oil Corporation Process for improving the thermal stability of jet fuels sweetened by oxidation
US5478541A (en) * 1994-01-27 1995-12-26 Samuels; Alvin Separately removing mercaptans and hydrogen sulfide from gas streams
US5683574A (en) * 1994-08-08 1997-11-04 Chevron U.S.A. Inc. Method for the extraction of low molecular weight mercaptans from petroleum and gas condensates
US20030052046A1 (en) * 2001-06-19 2003-03-20 Greaney Mark A. Continuous liquid hydrocarbon treatment method
US20100012553A1 (en) * 2006-12-22 2010-01-21 Griffin John M Tetra-sulfo iron-phthalocyanine and related methods
CN105085338A (en) * 2015-08-25 2015-11-25 成都德美工程技术有限公司 Production method and apparatus of dimethyl disulfide
US10005070B2 (en) 2014-08-27 2018-06-26 China National Petroleum Corporation Bimetallic mercaptan conversion catalyst for sweetening liquefied petroleum gas at low temperature

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US3408287A (en) * 1966-04-20 1968-10-29 Universal Oil Prod Co Oxidation of mercaptans

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Cited By (41)

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Publication number Priority date Publication date Assignee Title
US2966452A (en) * 1959-02-24 1960-12-27 Universal Oil Prod Co Sweetening sour hydrocarbon distillate with metal phthalocyanine catalyst in the presence of alkali air and sulfite ions
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NL235884A (en)
FR1216168A (en) 1960-04-22
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BE575509A (en)
DE1084861B (en) 1960-07-07
MY6200086A (en) 1962-12-31
ES247118A1 (en) 1959-06-01
OA00553A (en) 1966-07-15

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