US2763594A - Sweetening hydrocarbon oils - Google Patents

Sweetening hydrocarbon oils Download PDF

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US2763594A
US2763594A US415237A US41523754A US2763594A US 2763594 A US2763594 A US 2763594A US 415237 A US415237 A US 415237A US 41523754 A US41523754 A US 41523754A US 2763594 A US2763594 A US 2763594A
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alkali metal
hydrocarbon oil
mercaptans
phenolate
metal hydroxide
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US415237A
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Have Cornelis David Ten
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Shell Development Co
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Shell Development Co
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B45/00—Formation or introduction of functional groups containing sulfur
    • C07B45/06—Formation or introduction of functional groups containing sulfur of mercapto or sulfide groups

Definitions

  • This invention relates to a method for the direct sweetening of hydrocarbon oils containing acidic sulfur compounds. More particularly, it relates to a method for converting acidic and malodorous mercaptans in petroleum hydrocarbon fractions into organic disulfdes, and especially ⁇ to such a method for the treatment of petroleum hydrocarbon fractions which contain a relatively small proportion of such undesirable sulfur compounds.
  • lt is further known (cf. U. S. Patents 2,015,038 and 2,550,965) that the mercaptans present in hydrocarbon oils can be oxidized to disuldes if the hydrocarbon oil is brought into Contact, in the presence of an oxidizing agent, for example oxygen, with an alkali metal hydroxide solution containing a comparatively small amount of a special type of phenol which is active as oxidation catalyst, particularly a polyhydrlc phenol or aminophenol having the hydroxyl groups or the hydroxyl and amino groups in the ortho or para position with respect to each other.
  • the aqueous alkali metal hydroxide solution may also contain cresols and xylenols which promote the solubility of mercaptans in the aqueous alkali metal hydroxide solution.
  • the rates for the oxidation of mercaptans (mercaptides) to disullides brought about by means of oxygen in a two-phase system may be classified into two groups, namely group with low oxidation rates and a group with hi 'i oxidation rates.
  • the low oxidation rates are obtained with the phenolate-containing alkali metal hydioxide solutions having a water content of more than 54% by volume, while the high oxidation rates are ob tained with the phenolate-containing alkali metal hydroxide solutions having a water content of 54% by volume or less.
  • the alkali metal phenolates (phenates) in the present alkali metal hydroxide solutions may be derived from ui'tsubstituted phenol or from monohydric alkylphenols, such as phenol, o, mand p-cresols, the various xylenol isomers, ethylphenols, the propylphenols, and mixtures thereof, the alkyl groups of which contain no more than three carbon atoms in total; these phenols are understood to be otherwise unsubstituted.
  • monohydric alkylphenols such as phenol, o, mand p-cresols, the various xylenol isomers, ethylphenols, the propylphenols, and mixtures thereof, the alkyl groups of which contain no more than three carbon atoms in total; these phenols are understood to be otherwise unsubstituted.
  • phenolate The individual phenolates and alkylphenolates and mixtures thereof will be referred to hereinafter by the generic designation phenolate
  • phenolate The stable aqueous solutions of phenolate and alkali metal hydroxide with a maximum water content of 54% by volume, i. e. the solutions which are neither supersaturated in phenola-te nor in alkali metal hydroxide, have a high concentration of phenolate.
  • the invention therefore relates in general to a process for converting mercaptans or mercaptides into disuldes by means of oxygen, but without oxidation catalyst, in a two-phase system, one phase of which is formed by a light hydrocarbon oil, particularly gasoline or kerosene, and the other by a stable, homogeneous, ⁇ aqueous solution of an alkali metal hydroxide and a phenolate which may or may not be substituted by alkyl groups with a total quantity of not more than three carbon atoms and does not contain other substituents, the two phases being brought into intimate contact with each other, the process Vwith a water content of less than 54% by volume.
  • the aqueous solution contains at most 54% by volume of water and contains at least 2 mols per liter of free alkali metal hydroxide.
  • light hydrocarbon oil is to ybe understood a hydrocarbon oil the boiling point or end boiling point (the latter in the case of a mixture) of which does not exceed 350 C.
  • the hydrocarbon oil may therefore be gasoline, kerosene or a gas oil.
  • the invention is particularly of importance for processes in which the light hydrocarbon oil is a gasoline or kerosene.
  • Flg. I is a graph showing the small part of the total ternary. phase diagram water-potassium hydroxide-cresol which 1s employed in the practice of the invention.
  • Fig. II is a graph showing the iniluence of composition of the aqueous phase on the rates of oxidation of mercaptans 1n a two-phase system of hydrocarbon an-d the aqueous phase.
  • the denition which ,is given for the alkali metal hydroxide solutions containing the phenolate means in effect that the process is carried out with solutions which constitute only a small part of the total ternary phase diagram water-alkali metal hydroxide-phenol.
  • the area of concentrations under consideration at 20 C. is shown by shading in the graph of Fig. I for the water-potassium hydroxide-cresol system.
  • the gures along the axes relate to the percentages by weight of the various components.
  • Line AB connectlng the point of 63% KOH on the water-KOH axis with the point of 49.5% cresol on the water-cresol axis corresponds to the line separating the solutions with a water content of more than 54% by volume from the solutions
  • Line BC of the graph shows the limit between solutions which are more than 2-normal of free KOI-l and solutions which are less than Z-normal of free KOH.
  • line CDEA of the graph indicates the limit between the area of the stable homogeneous solutions to be used in the practice of the invention and the area of the unstable solutions or the area in which two or more phases occur side by side in the system under consideration.
  • the area of the concentrations suitable according to the invention is, at the same temperature of, for instance, 20 C. even more limited than in the rst system. This is due to the fact that the curve AEDC separating the area of the stable homogeneous solutions from the area .in which the solutions are supersaturated or separate solid components, is so situated that the area enclosed by the curves AEDC, AB and BC is smaller than when potassium hydroxide is used.
  • solutions containing potassium hydroxide as the alkali metal hydroxide since at normal operating temperatures these solutions allow a somewhat greater variation with respect to concentrations than solutions containing sodium hydroxide as the alkali metal hydroxide.
  • the process is preferably carried out at ordinary or slightly elevated temperatures, particularly C.45 C.
  • higher temperatures may be used, for instance, a temperature of 45 C.-80 C., or lower temperatures, for instance, a temperature of 0 C.1,0 C.,
  • the oxygen required for the process may be supplied to the two-phase system to be treated with it as such or in the form of a mixture of oxygen with another gas that is inert under the operating conditions. Airis a particularly suitable oxygen-containing mixture.
  • the oxygen may be either dissolved in the hydrocarbon oil in advance or be injected into the hydrocarbon oil vWhile the latter is being brought into contact with the aqueous solution of the alkali metal hydroxide and alkali metal phenate.
  • the quantity of oxygen should at least be equal to the quantity of mercaptans to be oxidized. It is preferred to use an excess of 50%-200% and more particularlyof %-125%, calculated on the quantity of oxygen theoretically require-d to convert the mercaptans (mercaptildes) to disuliides.
  • the process for removing mercaptans from gasoline or kerosene with a content of mercaptan sulphur not exceeding 0.04%-0.05% by weight and the gasoline or kerosene is at equilibrium with the atmosphere the quantity of oxygen present in the gasoline or kerosene is generally suiicient to effect the desired oxidation.
  • the process for removing mercaptans from gasoline and kerosene is frequently carried out shortly after the gasoline or kerosene has been produced from the crude oil and, after any other pretreatments have been carried out, with the result that it is not saturated with air. In that case it is necessary to dissolve air or another oxygencontaining gas in the hydrocarbon oil before or during contact with the caustic alkali solution.
  • the process is carried out un-der atmospheric pressure. If the process is applied for removing mercaptans from hydrocarbon oils with a comparatively high content of mercaptans, for instance a mercaptan sulphur content of 0.04%0.05% by weight or more, using air as oxygen-containing gas, it may be advisable to operate under elevated pressure in order to dissolve an adequate amount of oxygen in the hydrocarbon oil.
  • the ratio of the quantity of hydrocarbon oil to the quantity of the caustic alkali phase may vary between Wide limits.
  • the ratio of the volume of the caustic alkali phase to the volume of the hydrocarbon oil may, in general, vary from 0.05 to 5.
  • an advantage of the process is that the desired result can already be obtained by treating the hydrocarbon oil with a quantity of the alkali metal hydroxide and phenolat'e solution described which is considerably lower than the quantity of hydrocarbon oil.
  • a quantity of caustic alkali phase of 5%-50% by volume and more particularly of 10%-20% by volume, calculated on the hydrocarbon oil, is very suitable.
  • the process is applied for regenerating an alkali metal hydroxide solution containing mercaptides by treating this solution in the presence of a light hydrocarbon oil with oxygen, it is preferable to select the ratio of the volume of the caustic alkali phase to the volume of the hydrocarbon oil between 0.2 and 5 and more particularly between 0.5 and 2.
  • the process according to the invention may be carried out either continuously or batchwise.
  • the hydrocarbon oil When carrying out the pro-:ess continuously, the hydrocarbon oil may be supplied to the aqueous solution of the alkali metal hydroxide and phenolate in such a manner that the oil is in contact with the aqueous solution for a suiciently long time and the continuously discharged hydrocarbon oil passed into a separate settling vessel, in which the entrained aqueous solution separates out and is recycled to the process.
  • the process may be applied for removing mercaptans from light hydrocarbon oils, particularly gasoline and kerosene, of different origin, including gasoline or kerosene obtained by straight distillation from crude oils as well as gasoline and kerosene obtained from heavy base materials by cracking.
  • the so-called reformed gasoline may also be freed from mercaptans according to the present process.
  • oil and anti-oxidant such as an aryl amine or an alkyl phenol, and the alkyl groups of which contain a total of 4 carbon atoms or more to prevent the formation of peroxides and gum from the unsaturated components of the oil.
  • anti-oxidant such as an aryl amine or an alkyl phenol, and the alkyl groups of which contain a total of 4 carbon atoms or more to prevent the formation of peroxides and gum from the unsaturated components of the oil.
  • a quantity of 0.0001% ⁇ - 0.01% by weight of such an anti-oxidant will suice.
  • the process is primarily suitable for treating light hydrocarbon oils with a low mercaptan content, i. e. lower than 0.05% by weight and preferably lower than 0.02% by weight, calculated as mercaptan sulfur.
  • a low mercaptan content i. e. lower than 0.05% by weight and preferably lower than 0.02% by weight, calculated as mercaptan sulfur.
  • the quantity of disuliides returned into the hydrocarbonoil is also small.
  • a low content of organic disulfides does not appreciably adect its lead susceptibility.
  • the pretreatment for removing the greater part of the mercaptans may, for example, be elected by extracting (Without oxidation) the hydrocarbon oil with an aqueous alkali metal hydroxide solution containing a solutizer for mercaptans.
  • the concentration (based upon the water content) of phenolate and also that of alkali metal hydroxide in the aqueous solution used in the pretreatment for extracting mercaptans without oxidation may be somewhatlower than the concentration of phenolate and alkali metal hydroxide in the aqueous solution used in the subsequent step, in which the mercaptans still present in the hydrocarbon oil are converted into disulphides by means of oxygen.
  • a solution containing 45% by weight of water, 35 by weight of KOH and 20% by weight of cresol (which will be present at least for a considerable part in the form of n for converting mercaptans into ⁇ disulphides byrneans of oxygen has the following advantage.
  • the aqueous solution may be enriched with phenols by transfer from the hydrocarbon oil into ⁇ the aqueous solution), while moreover the aqueous solution is diluted by the water which is often present in small quantities in the treated hydrocarbon oil as well as by water which is formed by the oxidation of mercaptans (this latter cause of dilution applies to the solution used in the oxidation treatment).
  • the former solution may be reconcentrated by the addition of part of the more concentrated solution employed in the subsequent treatment.
  • This latter solution may then be reconcentrated by vthe addition of alkali metal hydroxide and, if necessary, of phenolate. More especially, the rate of adding part of the concentrated solution used in the oxidation treatment to the solution employed in the extraction treatment without oxidation will be so chosen that the total Volume of concentrated solution applied in the oxidation treatment remains constant.
  • EXAMPLE i n a mixer, which can be considered as a turbomixe'r on a laboratory scale, 8 liters of gasoline were brought into intensive contact with 800 cc. of an aqueous solution of an alkali metal ihydroxide and a phenolate at 20 C.
  • This gasoline was a debutanized Venezuelan gasoline obtained by thermal cracking with a boiling range ot 40c C.-240 C. having a mercaptan sulfur content of 0.015% by weight (calculated as elementary sulfur). It should be noted that the sulfur content of this gasoline was mainly present in the form of mercaptans which are diiicult to oxidize. This gasoline was deliberately chosen since the comparatively slow progress of the oxidation rendered it possible to ascertain the progress of this oxidation in course of time.
  • the tests were carried out by allowing the impeller of the mixer to run at a circumferential velocity of 2.1 m. per second, with Which the Vsame effect was attained as in a technical turbomixer with a capacity of 10 cubic metres, in which the irnpeller was allowed to run at a circumferential velocity of 4.5 m. per second.
  • the last column of the table shows the relative values of the oxidation rates of the mercaptans (mercaptides) measured, the greatest of the oxidation rates measured being given the gure 100.
  • Graph II relates to tests l0 to 2l inclusive, carried out with aqueous solutions of potassium hydroxide and cresolate or xylenolate.
  • the unbroken lines in the graph relate to the application of cresolate while the dotted lines relate to the use of solutions containing xylenolate.
  • composition of the aqueous solutions of alkali metal hydroxide and phenolate used in the various tests is plotted in a phase diagram, such as the one of graph I, the following will be found.
  • the aqueous alkali metal hydroxf ide solution containing the alkyl phenolate is required to fall within the region of the ternary phase system of a stable homogeneous solution.
  • the water content must be at least about 20%, corresponding approximately to the water content on the inside of the region ABCDE at the line CD.
  • the corresponding C point is at a water concentration of 25% by weight and the D point is at 30% by weight water.
  • the CD line is also displaced toward higher proportions of water in the case of the system: water-NaOH-cresol. Therefore, it is to be seen that the water content in general should be higher than 25% by weight, and preferably it should be at least about 30% by weight.
  • a process for converting mercaptans to disuldes which comprises contacting said mercaptaus with oxygen in the presence of a iirst phase comprising a light hydrocarbon oil intimately admixed with a second phase comprising an aqueous solution of potassium hydroxide and a monohydroxy phenolate which contains only C, H, and O and potassium atoms and which contains from 6 to 9 C-atoms, said aqueous solution containing no more than 54% by volume of water and at least 2 moles of free potassium hydroxide per liter thereof, separating said light hydrocarbon oil and said aqueous solution, and withdrawing an aqueous phase containing said potassium hydroxide and phenolate and an oil phase containing said light hydrocarbon oil and said disuldes.
  • a process for converting mercaptans contained in a light hydrocarbon oil into disuldes which comprises intimately contacting said light hydrocarbon oil in the V presence of oxygen with an aqueous solution of potassium hydroxide and a monohydroxy phenolate, which contains only C, H, O and potassium atoms and which contains from 6 to 9 C-atorns, said aqueous solution containing no more than 54% by volume of water and at least 2 moles of free potassium hydroxide per liter thereof, separating said light hydrocarbon oil and said aqueous solution, and withdrawing an aqueous phase containing said potassium hydroxide and phenolate and an oil phase containing said light hydrocarbon oil and said disuliides.
  • said light hydrocarbon oil has a boiling range within the boiling range of gasoline and kerosene and has a mercaptan sul- Table l Norm.
  • Mol/ Rela- Test NaOH, KOH, Cresol, Xylenol, Water, Water, NaOH liter Spec. Viscostive No. percent percent percent percent percent percent percent or Alkyl Gr. ity, Oxida- W. W. w. W. W. v. KOH Phenol es. tion rate l5 50 58. 7 0.60 3. 80 1.174 35. 7 49 19 46 55. 8 1. 84 3. 93 1. 214 76. 5 49 20 50 61. 2 2. 72 3. 40 1. 224 54.

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  • 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)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
US415237A 1953-03-12 1954-03-10 Sweetening hydrocarbon oils Expired - Lifetime US2763594A (en)

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NL775015X 1953-03-12
NL197666 1955-05-31

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US587633A Expired - Lifetime US2893951A (en) 1953-03-12 1956-05-28 Sweetening petroleum hydrocarbons and method for regenerating the treating solution
US587532A Expired - Lifetime US2862878A (en) 1953-03-12 1956-05-28 Sweetening process and method for removing water of reaction from the sweetening reagent

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US587532A Expired - Lifetime US2862878A (en) 1953-03-12 1956-05-28 Sweetening process and method for removing water of reaction from the sweetening reagent

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US (3) US2763594A (fr)
BE (3) BE527146A (fr)
DE (3) DE960918C (fr)
FR (3) FR1097348A (fr)
GB (3) GB775015A (fr)
NL (3) NL80084C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3107213A (en) * 1959-02-12 1963-10-15 Exxon Research Engineering Co Caustic treating process

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4513093A (en) * 1981-03-30 1985-04-23 Ashland Oil, Inc. Immobilization of vanadia deposited on sorbent materials during treatment of carbo-metallic oils
US7678263B2 (en) * 2006-01-30 2010-03-16 Conocophillips Company Gas stripping process for removal of sulfur-containing components from crude oil
EP2917307B1 (fr) * 2012-11-09 2019-01-09 Saudi Arabian Oil Company Procédé de désulfuration oxydative
US9643146B2 (en) 2013-11-29 2017-05-09 Uop Llc Unit for processing a liquid/gas phase mixture, mercaptan oxidation system including the same, and method of processing a liquid/gas phase mixture

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2015038A (en) * 1932-07-23 1935-09-17 Texas Co Process of sweetening petroleum hydrocarbons
US2164851A (en) * 1937-02-08 1939-07-04 Shell Dev Process of separating mercaptans contained in a hydrocarbon liquid
US2202039A (en) * 1938-06-25 1940-05-28 Shell Dev Process for the removal of mercaptans from hydrocarbon distillates
US2446507A (en) * 1945-01-26 1948-08-03 Socony Vacuum Oil Co Inc Method of removing mercaptans from a liquid mixture of hydrocarbons containing low-boiling and high-boiling mercaptans

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2556438A (en) * 1948-08-07 1951-06-12 Standard Oil Co Mercaptan extraction system
US2663674A (en) * 1950-03-17 1953-12-22 Standard Oil Co Refining sour hydrocarbon oils
BE510375A (fr) * 1950-03-17
DE886947C (de) * 1951-11-28 1953-08-20 Bataafsche Petroleum Verfahren zur Umwandlung der in Benzin oder Leuchtpetroleum enthaltenen Mercaptane in Disulfide durch Oxydation mit Sauerstoff oder einem sauerstoffhaltigen Gas

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2015038A (en) * 1932-07-23 1935-09-17 Texas Co Process of sweetening petroleum hydrocarbons
US2164851A (en) * 1937-02-08 1939-07-04 Shell Dev Process of separating mercaptans contained in a hydrocarbon liquid
US2202039A (en) * 1938-06-25 1940-05-28 Shell Dev Process for the removal of mercaptans from hydrocarbon distillates
US2446507A (en) * 1945-01-26 1948-08-03 Socony Vacuum Oil Co Inc Method of removing mercaptans from a liquid mixture of hydrocarbons containing low-boiling and high-boiling mercaptans

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3107213A (en) * 1959-02-12 1963-10-15 Exxon Research Engineering Co Caustic treating process

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NL86366C (fr)
DE1146217B (de) 1963-03-28
NL86367C (fr)
DE1167470B (de) 1964-04-09
BE548193A (fr)
FR70002E (fr) 1959-02-02
NL80084C (fr)
US2862878A (en) 1958-12-02
FR1097348A (fr) 1955-07-04
GB775015A (en) 1957-05-15
DE960918C (de) 1957-03-28
US2893951A (en) 1959-07-07
GB827385A (en) 1960-02-03
FR70001E (fr) 1959-02-02
GB827384A (en) 1960-02-03
BE527146A (fr)
BE548192A (fr)

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