US3853746A

US3853746A - Process for sweetening hydrocarbon products with sulfenamides

Info

Publication number: US3853746A
Application number: US00411979A
Authority: US
Inventors: M Gattuso
Original assignee: Universal Oil Products Co
Current assignee: Honeywell UOP LLC; Universal Oil Products Co
Priority date: 1973-11-01
Filing date: 1973-11-01
Publication date: 1974-12-10
Anticipated expiration: 1991-12-10

Abstract

Hydrocarbon products which contain mercaptans may be sweetened by treating said products with a sulfenamide which has been activated by a carbonyl or sulfonyl group contained therein, whereby the mercaptans are converted to disulfides. The process may be effected in an alkaline medium or may have an alkaline substance added in a step subsequent to the treatment step. The treatment of the hydrocarbon products with the sulfenamide is effected at temperatures ranging from ambient to about 100*C. and at pressure ranging from atmospheric to about 100 atmospheres.

Description

United States Patent Gattuso PROCESS FOR SWEETENI NG HYDROCARBON PRODUCTS WITH SULFENAMIDES Inventor: Marion J. Gattuso, Hoffman Estates, Ill.

Universal Oil Products Company, Des Plaines, lll.

Filed: NOV. 1, 1973 Appl. No.: 411,979 7 Assignee:

References Cited UNITED STATES PATENTS 6/1951 Browder et al. 208/206 5/1955 Chenicek 208/207 1 1/1955 Chenicek 208/207 Dec. 10, 1974 3,398,086 8/1968 Ros'enwald 208/207 Primary ExaminerDelbert E. Gantz Assistant Exam'iner-G. J. Crasanakis Attorney, Agent, or FirmJames R. Hoatson, Jr.; Raymond R Nelson; William H. Page, ll

[ ABSTRACT Hydrocarbon products which contain mercaptans may be sweetened by treating said products with a sulfenamide which has been activated by a carbonyl or sulfonyl group contained therein, whereby the mercaptans are converted to disulfides. The process may be effected in an alkaline medium or may have an alkaline substance added in a step subsequent to the treatment step. The treatment of the hydrocarbon products with the sulfenamide is effected at temperatures ranging from ambient to about 100C. and at pressure ranging from atmospheric to about 100 atmospheres.

13 Claims, No Drawings PROCESS FOR SWEETENING HYDROCARBON PRODUCTS WITH SULFENAMIDES BACKGROUND OF THE INVENTION Undesirable sulfur-containing compounds such as mercaptans and/or hydrogen sulfide are normally present in relatively high concentrations in refinery hydrocarbon streams. These hydrocarbon streams will include heavy hydrocarbons such as hydrocarbons having a boiling range higher than gasoline such as kerosene, jet fuel, diesel fuel, solvent oil, storage oil, range oil, burner oil, gasoline oil, fuel oil, etc.; streams boiling within the gasoline range, that is, hydrocarbons having an upper limit of from about 400 F. to about 425 F. and including cracked gasoline, straight run gasoline, natural gasoline or mixtures thereof, etc.; naphthas, etc. The presence of the mercaptans and hydrogen sulfide in these hydrocarbon streams presents a problem due to the objectionable odoriferousness of the compounds as well as the fact that the compounds are corrosive to most metals and in addition will cause swelling It is therefore an object of this invention to provide a process for removal of unwanted impurities in hydrocarbon streams.

A further object of this invention is to provide a process for removal of a major portion of unwanted impurities such as mercaptans from hydrocarbon streams thereby rendering said streams stable when subjected to long periods of storage.

In one aspect an embodiment of this invention resides in a process for the sweetening of a hydrocarbon product which comprises treating mercaptancontaining hydrocarbon products with a sulfenamide activated by a carbonyl or sulfonyl group at treating conditions whereby said mercaptans are consumed, and recovering the resultant sweetened hydrocarbon product.

A specific embodiment of this invention is found in a process for the sweetening of a hydrocarbon product which comprises treating mercaptancontaining hydroof rubber articles. The removal of the mercaptans can,

in some instances, be extremely difficultflt is known in the prior art that many methods can be utilized to effect a removal of these mercaptans including treatment with a phthalocyanine catalyst in the presence of an oxidizing agent which is the most prevalent process now in use. In many instances ordinary caustic solutions can remove a portion of the mercaptans; however, many hydrocarbon streams contain high molecular weight unreactive mercaptans which cannot be removed by this procedure. Generally speaking, the use of a phthalocyanine catalyst in an oxidation reaction will result in a removal of only a portion of the undesirable mercaptans.

As will be hereinafter shown in greater detail, I have now discovered that difficultly removable mercaptans can be converted to materials which are non-reactive in nature and will have little or no effect on storage stability, gum formation, or the general quality of the hydrocarbon product or stream in which it is used. This process will be particularly effective when complete removal of the mercaptans is not economical or feasible to effect.

This invention relates to a process for the sweetening of hydrocarbon products. More specifically the invention is concerned with a process for removing objectionable impurities such as mercaptans of hydrocarbon streams by converting said mercaptans to disulfides utilizing a sulfur and nitrogen-containing compound of a type hereinafter set forth in greater detail.

As hereinbefore set forth, I have now discovered that impurities such as mercaptanswhich are present in hydrocarbon streams such as gasoline, kerosene, jet fuel, etc., may be removed by being converted to nonreactive compounds such as disulfides utilizing certain sulfenamide compounds. By removal of a major portion of the objectionable impurities such as mercaptans, it is possible to obtain hydrocarbon streams which will not corrode metals or cause swelling of rubber articles when stored in containers made of these materials. In addition the hydrocarbon streams will have a minimal tendency to gum formation and will therefore be more stable when stored for relatively long periods of time.

carbon products with N-cyclohexylthio-N-phenylbenzenesulfenamide at a temperature in the range of about ambient to about 100 C. and a pressure in the range of from about atmospheric to about 100 atmospheres, whereby said mercaptans are consumed, and recovering the resultant sweetened hydrocarbon products.

A more specific embodiment of this invention is .found in a process for the sweetening of kerosene which comprises treating said kerosene with an oxidizing agent such as air in the presence of a phthalocyanine catalyst in an alkaline medium, recovering the treated kerosene, treating said kerosene with N-cyclohexylthiophthalimide at a temperature in the range of from about ambient to about 100 C. and a pressure in the range of from about atmospheric to about 100 atmospheres and thereafter treating the kerosene with sodium hydroxide solution, and recovering the resultant sweetened kerosene.

Other objects and embodiments will be found in the following further detailed description of the present invention.

Ashereinbefore set forth the present invention is concerned with a process for the sweetening of a hydrocarbon product by treating said hydrocarbon product which contains an unwanted or objectionable impurity with a sulfenamide activated by a carbonyl or sulfonyl group at treating conditions whereby the mercaptans which are present in the hydrocarbon product are consumed by being converted to disulfides, these latter compounds being non-reactive in nature and thus will not effect the storage stability of the hydrocarbon product inasmuch as the disulfides will not be corrosive to metal or will not cause a swelling of the rubber articles such as containers in which the hydrocarbon products may be stored.

The hydrocarbon streams or products which contain mercaptans and/or hydrogen sulfide are treated with sulfenamide compounds which are activated by a carbonyl or sulfonyl group. These sulfenamide compounds are characterized by the presence of a carbonyl or sulfonyl group adjacent to the sulfenamide nitrogen and will possess a characteristic nucleus having the following formula:

in which the dangling valence of the nitrogen may be linked to a second carbonyl group, a second sulfonyl group, an alkyl of from 1 to about 12 carbon atoms, aryl, cycloalkyl of from about 5 to about 7 carbon atoms, hydrogen, alkylene or arylene carbon radical and R is an alkyl of from 1 to about 12 carbon atoms, aryl or cycloalkyl of from about 5 to about 7 carbon atoms. Some specific examples of these compounds will include N-cyclopentylthiophthalimide, N-c'yclohexylthiophthalimide, N-cycloheptylthiophthalimide, N-phenylthiophthalamide, N-benzylthiophthalamide, N-o-tolylthiophthalamide, N-m-tolylthiophthalamide, N-p-tolylthiophthalamide, N-o-ethylphenylthiophthalamide, N-m-ethylphenylthiophthalamide, N-p-ethylphenylthiophthalamide, N-methylthiophthalamide, N-ethylthiophthalamide, N-propylthiophthalamide, N-butylthiophthalamide, N-pentylthiophthalamide, N-hexylthiophthalamide, N-heptylthiophthalamide, N-octylthiophthalamide, N-nonylthiophthalamide, N-decylthiophthalamide, N-undecylthiophthalamide, N-dodecylthiophthalamide, N- methylthiomaleimide, N-ethylthiomaleimide, N- propylthiomaleimide, N-n-butylthiomaleimide, N-tbutylthiomaleimide, N-pentylthiomaleimide, N-sec-pentylthiomaleimide, N-hexylthiomaleimide,

N-heptylthiomaleimide, N-octylthiomaleimide, N- nonylthiomaleimide, N-decylthiomale imide, N- phenylthiomaleimide, N-benzylthiomaleimide, N-ptolylthiomaleimide, N-cyclopentylthiomaleimide,

N-cyclohexylthiomaleimide, N-cycloheptylthiomaleimide, N-methylthiosuccinimide, N-ethylthiosuccinimide, N-propylthiosuccinimide, N-n-butylthiosuccinimide, N-t-butylthiosuccinimide, N-pentylthiosuccinimide, N-sec-pentylthiosuccinimide, N-hexylthiosuccinimide, N-heptylthiosuccinimide, N-octylthiosuccinimide, N-nonylthiosuccinimide, N-decylthiosuccinimide, N-phenylthiosuccinimide, N-benzylthiosuccinimide, N-p-tolylthi0succinimide, N-cyclopentylthiosuccinimide, N-cyclohexylthiosuccinimide, N-cycloheptylthiosuccinimide, N-chloromethylthiophthalimide, N- dichloromethylthiophthalamide, N-trichloromethylthiophthalamide, N-(2-chlorethyl)-thiophthalamide, N- (2,2-dichloroethyl)-thiophthalamide, N-(2,2,2- trichloroethyl)-thiophthalamide, N-(3-propylethyl)- thiophthalamide, N-(3,3-dipropylethyl)- thiophthalamide, N-( 3 ,3 3-tripropylethyl thiophthalamide, N-cyclopentylthio-N-phenylbenzenesulfenamide, N-cyclohexylthio-N-phenylbenzenesulfenamide, N-cycloheptylthio-N-phenylbenzenesulfenamide, N-methylthio-N-phenylbenzenesulfenamide, N-ethylthio-N-phenylbenzenesulfenamide,

N-propylthio-N-phenylbenzenesulfenamide, N- butylthio-N-phenylbenzenesulfenamide, N-pentylthio- N-phenylbenzenesulfenamide, N-hexylthio-N-phenylbenzenesulfenamide, N-heptylthio-N-phenylbenzenesulfenamide, N-octylthio-N-phenylbenzenesulfenamide, N-nonylthio-N-phenylbenzenesulfenamide,

N-decylthio-N-phenylbenzenesulfenamide, N- phenylthio-N-phenylbenzenesulfenamide, N- benzylthio-N-phenylbenzenesulfenamide, N- cyclopentylthio-N-methylbenzenesulfenamide, N- cyclohexylthio-N-methylbenzenesulfenamide, N- cycloheptylthio-N-methylbenzenesulfenamide, N-

ethylthio-N-methylbenzenesulfenamide, N-propylthio- N-methylbenzenesulfenamide, N-butylthio-N-methylbenzenesulfenamide, N-pentylthio-N-rnethylbenzenesulfenamide, N-phenylthio-N-methylbenzenesulfenamide, N-benzylthio-Nmethylbenzenesulfenamide.

N-cyclopentylthio-N-ethylbenzensulfenamide, N- cyclohexylthio-N-ethylbenzenesulfenamide, N- cycloheptylthio-N-ethylbenzenesulfenamide,

benzylthio-N-ethylbenzenesulfenamide, N- cyclopentylthio-N-propylbenzenesulfenamide, N- cyclohexylthio-N-propylbenzenesulfenamide, N- cycloheptylthio-N-propylbenzenesulfenamide, N-

ethylthio-N-propylbenzenesulfenamide, N-propylthio- N-propylbenzenesulfenamide, N-butylthio-N-propylbenzenesulfenamide, N-pentylthio-N-propylbem zenesulfenamide, N-phenylthio-N-propylbenzenesulfenamide, N-benzylthio-N-propylbenzenesulfenamide, etc, lt is to be understood that the aforementioned sulfenamides activated by carbonyl or sulfonyl groups are only representative of the class of agents which may be used, and that the present invention is not necessarily limited thereto.

The treatment of hydrocarbon products of the type hereinbefore set forth in greater detail such as kerosene, jet fuel, diesel fuel, gasoline, naphthas, etc. may be effected by admixing a sulfenamide of the type hereinbefore set forth with the hydrocarbon stream in an amount within the range of from about 1:1 to about 10:1 moles of sulfenamide per mole of mercaptan present in the hydrocarbon stream whereby the sulfenamide will react with the mercaptan present to form unsymmetrical disulfides which will not present problems usually associated with mercaptans.

If so desired, the hydrocarbon stream containing the sulfenamide and/or disulfides which are formed thereby may be contacted with an alkaline solution in order to catalyze the formation of the disulfides and remove any residual mercaptans which still may be present in the hydrocarbon product. Examples of alkaline solutions which may be used include sodium hydroxide, potassium hydroxide, lithium hydroxide, rubidium hydroxide, cesium hydroxide, etc. the sodium hydroxide or potassium hydroxide being preferred due to the greater availability and lower cost associated therewith.

It is also contemplated within the scope of this invention that the hydrocarbon product containing mercaptans which are subjected to treatment with a sulfenamide which has been activated by a carbonyl or sulfonyl group may be first subjected to prior treatment to remove a greater percentage of the mercaptans which are present. As an illustrative example of the pretreatment of a hydrocarbon product containing impurities such as mercaptans, the aforesaid hydrocarbon product or hydrocarbon stream is first given a pre-wash with an alkaline reagent-alcohol solution. These alkaline solutions may comprise an alkali metal hydroxide such as sodium hydroxide, potassium hydroxide, lithium hydroxide, etc., the alcoholic portion of the solution comprising methanol, ethanol, propanol, butanol, ethylene glycol, propylene glycol, butylene glycol, etc., methanol comprising the preferred alcohol due to the lower cost and greater availability thereof. Generally speaking, the alkaline reagent-alcohol solution will comprise from about 5% to about 50% by weight of the alkaline reagent and from about 5% to about 40% by weight of the alcohol, the remainder of the solution comprising water. Upon completion of the pre-wash step of the sweetening process, the hydrocarbon stream is treated with a phthalocyanine-containing catalyst. Any suitable phthalocyanine catalyst may be used and preferably comprises a metal phthalocyanine catalyst such as cobalt phthalocyanine, vanadium phthalocyanine, iron phthalocyanine, copper phthalocyanine, nickel phthalocyanine, chromium phthalocyanine, etc., the preferred metal phthalocyanines comprising cobalt phthalocyanine and vanadium phthalocyanine. Inasmuch as the metal phthalocyanine in general is not readily soluble in an aqueous solvent and therefore when used in an aqueous alkaline solution or for ease of compositing with a solid carrier, a derivative of the metal phthalocyanine is preferred. In this respect a particularly preferred derivative is a sulfonated derivative and thus an especially preferred phthalocyanine catalyst is cobalt phthalocyanine sulfonate. This catalyst is a mixture of cobalt phthalocyanine disulfonate and cobalt phthalocyanine monosulfonate. The phthalocyanine catalyst may be utilized either as a solution or suspension in a suitable alkaline medium or as a fixed bed in a reaction zone. When utilized as a solution or as a suspension in an alkaline reagent, the alkaline reagent is usually selected from those hereinbefore set forth in connection with the pre-wash treatment. In one embodiment, a preferred alkaline solution for the treatment is an aqueous solution of from about 1% to about 50% and more particularly from about 5% to about 25% by weight concentration of sodium hydroxide or potassium hydroxide. When desired, all or a portion of the alcohol which is utilized as one portion of the solution may be introduced into the alkaline solution or suspension prior to introduction into the reaction zone. However, because of the flexibility of the present process the amount of alcohol introduced into the reaction will be correlated with the amount of alcohol entrained or dissolved in the charge during the pre-wash treatment and carried thereby into the reaction zone. In general, the amount of alcohol present in the reaction zone will comprise from about 5% and preferably from about to about 30% by weight of the alkaline reagent'solution.

In another embodiment the phthalocyanine catalyst may be utilized as a fixed bed in the reaction zone. When utilizing this embodiment, the catalyst is prepared as a composite with a solid support. Any suitable support may be employed and preferably comprises activated charcoal, coke or other suitable forms of carbon. In addition, in some cases, the support may comprise silica, alumina, magnesia, etc. or mixtures thereof. The solid catalyst may be prepared in any suitable manner and in one embodiment preformed particles of the solid support are soaked in a solution containing the phthalocyanine catalyst, after which the excess solution is drained off and the catalyst is used as such or is subjected to a drying treatment, mild heating, blowing with air, hydrogen, nitrogen, etc. or successive treatments using two or more of these treatments prior to use. Other methods of the preparation of the solid composite will include spraying or pouring a solution of the phthalocyanine catalyst over the particles of the solid support or dipping, suspending, immersing or otherwise contacting the particles of the solid support with the catalyst solution. The concentration of the phthalocyanine catalyst in the composite may range from about 0.1% to about 10% by weight or more of the composite. When the catalyst is used as a fixed bed, in one embodiment, it may be pretreated with the alkaline solution which may or may not contain alcohol or in another embodiment an alkaline solution which may or may not contain alcohol is continuously or intermittently introduced into the reaction zone during processing.

Regardless of whether using a fixed bed or other type of process, the hydrocarbon product will contain dissolved alcohol, the loss of this alcohol in the treated product being economically unfeasible due to the cost of the alcohol which is lost. In order to overcome some of this disadvantage, the treated hydrocarbon product is given a post-wash with the alkaline reagent-alcohol solution used in the pre-wash, this step serving to recover at least a portion of the alcohol from the treated hydrocarbon product.

The following examples are given to illustrate the process of the present invention which examples, however, are not intended to limit the generally broad scope of the present invention in strict accordance therewith.

EXAMPLE I In this example an isooctane solution was spiked with cyclohexyl mercaptan in an amount necessary to provide a concentration of mercaptan sulfur at 91.5 ppm. To determine the mercaptan sulfur concentration, the treated isooctane solution was titrated using silver nitrate solution, said sample being titrated potentiometrically in an ammoniacal isopropyl alcohol solution using alcoholic silver nitrate as the titrant. Following this N- cyclohexylthio-N-phenylbenzenesulfenamide in a concentration of 0.14 grams per ml of isooctane was added and the solution was shaken for a period of 10 minutes at room temperature. The solutions were then analyzed for mercaptan sulfur in a manner similar to that hereinbefore set forth at an interval of 4 hours and an interval of 24 hours. The solution which did not contain the sulfenamide additive possessed a mercaptan sulfur of 91.5 ppm at the end of 24 hours. In contrast to this, the solution which contained the N- cyclohexylthio-N-phenylbenzenesulfenamide contained only 6.3 ppm mercaptan sulfur at the end of 4 hours, said sulfur level remaining constant at 24 hours.

A similar treatment of an isooctane which was spiked with cyclohexyl mercaptan using N-phenylthiophthalimide as the removal agent showed that the'mercaptan sulfur level at the end of 24 hours dropped from 91.5 ppm to 50.5 ppm.

EXAMPLE II was determined that the mercaptan sulfur level of the kerosene was 33.4 ppm.

The kerosene which still contained 33.4 ppm was then treated with N-cyclohexylthio-N-phenylbenzenesulfenamide by shaking the two components for a period of about minutes and allowing the solution to stand. At the end of 24 hours, the mercaptan sulfur level had dropped to 24.2 ppm. Following this cc of a 50% sodium hydroxide solution was added to the mixture which was thereafter shaken for a period of 15 minutes. Titration of the kerosene at the end of this period showed that only a trace of mercaptan sulfur remained, all of the mercaptan sulfur having been con verted to disulfides.

EXAMPLE Hi In this example a second raw kerosene which contained 1064.2 ppm of mercaptan sulfur was treated in a manner similar to that set forth in Example II above, the treatment comprising admixing the kerosene with a 10% potassium hydroxide solution containing 200 ppm of a sulfonated cobalt phthalocyanine catalyst in a liquid/liquid reactor for a period of 10 minutes, the kerosene and potassium hydroxide being present in a 1:1 ratio. It was determined that the mercaptan sulfur level had dropped to 540.2 ppm. A repetition of the above treatment resulted in dropping the mercaptan sulfur level to 200.3 ppm. in order to further reduce the mercaptan sulfur level, the kerosene from the above treatments was treated with a solution containing N- cyclohexylthio-N-phenylbenzenesulfenamide, the additive being present in a concentration of 4200 ppm. After shaking the solution and allowing to stand for a period of 24 hours, the mercaptan sulfur level was reduced to 81.9 ppm. At the end of the 24 hour period, the kerosene containing the additive was shaken for a period of 15 minutes with 15 cc of a 50% sodium hydroxide solution, the final concentration of mercaptan level being reduced to 18.2 ppm.

EXAMPLE IV In this example a sample of a third raw kerosene containing 4180 ppm of mercaptan sulfur was treated in a fixed bed reaction using a cobalt phthalocyanine catalyst. This treatment resulted in dropping the mercaptan sulfur level to 24.3 ppm. To the kerosene from the above treatment was added 547 ppm of N- cyclohexylthio-N-phenylbenzenesulfenamide. The kerosene was shaken for a period of 10 minutes and allowed to stand for a period of 1 hour. At the end of this time period, the mercaptan sulfur level had dropped to 15.18 ppm. Thereafter the kerosene containing the additive was shaken for a period of 15 minutes with l5 cc of a 50% sodium hydroxide solution, the final mercaptan sulfur level being 6.1 ppm.

EXAMPLE V In this example a hydrocarbon product comprising gasoline is spiked with cyclohexyl mercaptan in an amount necessary to provide a concentration of mercaptan sulfur at 91.5 ppm. The additive comprising N-cyclohexylthiophthalimide in a concentration of 0.14 grams per 100 cc of gasoline is added to the spiked gasoline and the solution is shaken for a period of 10 minutes at room temperature. The solution is allowed to stand for a period of 4 hours after which the gasoline is analyzed for mercaptan sulfur and will be found to have a relatively low mercaptan sulfur as measured in ppm. When the solution is allowed to stand for an additional 20-hour period and analyzed, it will be found that the mercaptan sulfur content will be extremely low, the remainder of the mercaptan sulfur being removed by further treatment of the gasoline with a 50% sodium hydroxide solution.

Similar results will be obtained when a gasoline which has been spiked with cyclohexyl mercaptan is treated with additives comprising N-phenylthio-N- methylbenzenesulfenamide and N-phenylthio-N- phenylbenzenesulfenamide.

I claim as my invention:

1. A process for the sweetening of a hydrocarbon product which comprises treating a mercaptancontaining hydrocarbon product with a sulfenamide activated by a carbonyl or sulfonyl group adjacent to sulfenamide nitrogen whereby said mercaptans are converted to disulfides, and recovering the resultant sweetened hydrocarbon product.

2. The process as set forth in claim 1 in which said treating conditions include a temperature in the range of from ambient to about C. and a pressure in the range of from about atmospheric to about 100 atmospheres.

3. The process as set forth in claim 1 in which said sweetening process is effected in an alkaline medium.

4. The process as set forth in claim 3 in which said alkaline medium is a sodium hydroxide solution.

5. The process as set forth in claim 3 in which said alkaline medium is a potassium hydroxide solution.

6. The process as set forth in claim 1 in which said by drocarbon product is a gasoline.

7. The process as set forth in claim 1 in which said hydrocarbon product is a kerosene.

8. The process as set forth in claim 1 in which said sulfenamide is N-cyclohexylthio-N-phenylbenzenesulfenamide.

9. The process as set forth in claim 1 in which said sulfenamide is N-phenylthiophthalimide.

10. The process as set forth in claim 1 in which said sulfenamide is N-cyclohexylthiophthalimide.

11. The process as set forth in claim 1 in which said sulfenamide is N-phenylthio-N-methylbenzenesulfenamide.

12. The process as set forth in claim 1 in which said sulfenamide is N-phenylthio-N-phenylbenzenesulfenamide.

13. The process as set forth in claim 1 further characterized in that said mercaptan-containing hydrocarbon product is treated with an oxidizing agent in the presence of a phthalocyanine-containing catalyst in an alkaline medium prior to treatment with said sulfenamide.

Claims

1. A PROCESS FOR THE SWEETENING OF A HYDROCARBON PRODUCT WHICH COMPRISES TREATING A MERCAPTAN-CONTAINING HYDROCARBON PRODUCT WITH A SULFENAMIDE ACTIVATED BY A CARBONYL OR SULFONYL GROUP ADJACENT TO SULFENAMIDE NITROGEN WHEREBY SAID MERCAPTANS ARE CONVERTED TO DISULFIDES, AND RECOVERING THE RESULTANT SWEETENED HYDROCARBON PRODUCT.

2. The process as set forth in claim 1 in which said treating conditions include a temperature in the range of from ambient to about 100* C. and a pressure in the range of from about atmospheric to about 100 atmospheres.

6. The process as set forth in claim 1 in which said hydrocarbon product is a gasoline.