US2708179A - Conversion of mercaptans - Google Patents

Conversion of mercaptans Download PDF

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US2708179A
US2708179A US410445A US41044554A US2708179A US 2708179 A US2708179 A US 2708179A US 410445 A US410445 A US 410445A US 41044554 A US41044554 A US 41044554A US 2708179 A US2708179 A US 2708179A
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ketone
beta
mercaptans
phenyl
methyl
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Joseph A Chenicek
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Universal Oil Products Co
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Universal Oil Products 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
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms
    • C10G29/22—Organic compounds not containing metal atoms containing oxygen as the only hetero atom
    • C10G29/24—Aldehydes or ketones

Definitions

  • This invention relates to the conversion of mer'captans E
  • One method utilized for the treatment of petroleum distillates to remove mercaptans entails the use of an alkaline material and particularly an alkali metal hydroxide including sodium hydroxide, potassium hydroxide, etc. Modification of this process comprises the use of a solutizer including alcohols, phenols, etc. Other methods include the copper sweetening process, doctor sweetening process, etc.
  • mercaptans are converted by reacting with a particular type of organic compound. While this method may be utilized for the conversion of mercaptans as such, it is particularly advantageous for use in the treatment of organic substances, including petroleum fractions, in which the mercaptans are present as an undesired impurity.
  • a major proportion of the mereaptans are removed from the petroleum distillate by treatment with an alkali metal hydroxide or otherwise, and the remaining small amount of mercaptans, after such treatment, are converted by means of the novel method of the present invention.
  • the major proportion of the mercaptans are readily removed in the processes of the prior art but the final sweetening of the distillate usually is much more difi'icult.
  • final sweetening is effected by converting the remaining mercaptans in the manner to be hereinafter set forth in detail.
  • the present invention relates to a method of converting a mercaptan which comprises reacting the mercaptan with a beta-dialkylamino ketone.
  • the present invention relates to a method of treating a sour petroleum distillate which comprises reacting the mercaptans contained in the distillate with a beta-dimethylamino ketone.
  • the inve'ntion relates to a method of sweetening a sour cracked gasoline which com rises reacting the mercaptans eofitained ih said gaseline with beta-diniethylaminopropiophenone.
  • the beta-dialk'ylamino ketones may be illustrated by the following general formula:
  • R1 RO-CCN II where R, R1 and R2 are hydrocarbon groups.
  • R, R1 and R2 may be the same or from 1 to 4 carbon atoms each.
  • Illustrative compounds in which R is an alkyl group include methyl beta dimethylaminoethyl ketone, ethyl beta-dimethylaminoethyl ketone, propyl beta-dimethylam'inoethyl ketone, butyl beta-dimethylaminoethyl ketone, amyl beta-dimethylaminoethyl ketone, heXyl heta-dimethylaminoethyl ketone, heptyl beta-dimethylaminoethyl ketone, octyl betadimethylaminoethyl ketone, etc., methyl beta-diethylaminoethyl ketone, methyl beta-dipropylarninoethyl ke- 1 tone, methyl beta-dibut-yla
  • Illustrative compounds in which R comprises an aryl group include phenyl beta-dimethylaminoethyl ketone (also named beta-dimethylaminopropiophenone), phenyl beta-diethylaminoethyl ketone, phenyl beta-dipropylaminoethyl ketone, phenyl beta-dibutylaminoethyl ketone, etc., phenyl beta-dimethylaminopropyl ketone, phenyl beta-diethylaminopropyl ketone, phenyl beta-dipropylaminopropyl ketone, phenyl beta-dibutylaminopropyl ketone, etc., phenyl beta-dimethylaminobutyl ketone, phenyl beta-diethylaminobutyl ketone, phenyl beta-dipropylaminobutyl ketone
  • tolyl beta-dirnethylaminoethyl ketone, tolyl beta-diethylaminoethyl ketone, tolyl beta-dipropylaminoethyl ketone, tolyl beta-dibutylaminoe'thyl ketone, etc. tolyl beta-dimethylaminopropyl ketone, tolyl beta-diethylaminopropyl e ketone, tolyl beta-dipropylaminopropyl ketone, tolyl betadibutylaminopropyl ketone, etc., tolyl beta-dirnethylarninobutyl ketone, tolyl beta-diethylarninobutyl ketone, tolyl beta dipropylaminobntyl ketone, tolyl beta-dibutylaminob'utyl ketone, etc., xylyl beta-dimethyla
  • cyclohexyl beta-diethylaminohexyl ketone, etc. cyclobutyl beta-dimethylaminoethylketone, cyclobutyl beta-di e'thylaminoethyl ketone, etc., cyclopropyl beta-dimethylaminoethyl ketone, cyclopropyl beta-diethylaminoethyl ketone, etc., other hydrocarbon groups represented by R include alkenyl, aralkyl, etc.
  • R1 and R2 may comprise carbon atoms of a cyclic group as, for example, where R1 and h are carbon'atoms of a pyridine ring, qui'noline ring,
  • R may comprise a substituted hydrocarbon group, the substituent containing oxygen, nitrogen and/or sulfur, including heterocyclic rings. However, it is understood that all of these compounds are not necessarily equivalent.
  • the novel process of the present invention is particularly applicable to the treatment of sour gasolines including cracked, straight-run and mixtures thereof, it is understood that the present process may be used for the treatment of other hydrocarbon distillates including cracked and/ or straight-run kerosene, diesel fuel, mineral oil, lubricating oil, fuel oil, etc.
  • the present invention may be utilized for thetreatment of gaseous fractions containing mercaptans.
  • the process may be utilized for the treatment of other fractions containing mercaptans and thus may include synthetic fractions formed from starting reactants containing mercaptans, either as an impurity or as the desired reactant.
  • beta-dialkylamino ketone to be 7 used will depend upon the concentration of mercaptans in the fraction being treated. At least one mol of betadialkylamino ketone should be used per mol of mercaptan to be converted. Preferably an excess of beta-dialkylamino ketone is used in order to ensure complete conversion of the mercaptans, and the excess may comprise up to 50 or more molecular proportions of beta-dialkylamino ketone per molecular proportion of mercaptan.
  • the process of the present invention may be effected in any suitable manner.
  • the beta-dialkylamino ketone iscommingled with the petroleum distillate and the mixture is subjected to refluxing, distillation, etc.
  • the distillation may be efiected atmospheric, subatmospheric or superatmospheric pressure which may be up to 1000pounds per square inch or more.
  • the beta-dialkylamino ketone is commingled with the petroleum distillate and the resultant mixture is passed through suitable mixing devices such as durion mixers, orifices,
  • the gaseous fraction may be passed through a body of the beta-dialkylamino ketone contained etc., and then introduced into a storage tank which, when in a suitable reaction vesse. It is understood that any other suitable method for efiecting reaction of the betadialkylamino ketone with mercaptans may be utilized.
  • Example I After refluxing, the portion containing beta-dimethyl aminopropiophenone had a mercaptan sulfur content of 008% by weight. The other portion, which did not contain the additive, had a mercaptan sulfur content ofv 0.02% by weight. It will be noted that the beta-dialkylamino ketone served to considerably reduce the mercaptan content of the gasoline.
  • Example 1 Topped crude oil is subjected to non-catalytic'thermal cracking by being-heated to a temperature of 940" F. in a furnace and'passed through a reaction zone and then into a flash zone wherein vapors separate from residuum.
  • the vapors are withdrawn overhead from the flash chamber and are passed into a fractionating column to separate an overhead fraction'comprising gas and gasoline.
  • Butyl beta-dimethylaminoethyl ketone is added to the vapors from the flash chamber before passing into the fractionating column.
  • the beta dialkylamino ketone will react with the mercaptans and the reaction product will be retained in the bottoms frac tion, thereby. resulting in an overhead gasoline fraction of reduced mercaptan content.
  • Example IV 7 Cracked gasoline having a m'ercaptan content of 0.03% by weight may be treated with caustic-methanol solution to reduce the mercaptan content down to about 0.003%: by weight.
  • beta-dimethylaminopropiophenone is added with intimate stirring and the mixture is sent to storage. This treatmeutjvill serve to produce a sweet gasoline.
  • a method of converting a mercaptan which comprises reacting the mercaptan with beta-dialkylamino ketone.
  • a method of treating a sour petroleum distillate which comprises reacting the mercaptans containedin said distillate with a beta-dialkyl'amino ketone.
  • a method of treating a sour petroleum distillate which comprises reacting the mercaptans contained in said distillate with a beta-diethylamino ketone.
  • a method of sweetening a sour gasoline which comprises reacting the mercaptans contained in said gasoline With a beta-diaikylamino ketone.
  • a method of sweetening a sour gasoline which comprises reacting the mercaptans contained in said gasoline with beta-dimethylaminopropiophenone.
  • a method of sweetening a sour gasoline which comprises reacting the mercaptans contained in said gasoline with an alkyl heta-dimethylaminoethyl ketone.

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

United States Patent 0 No Drawing. Application February 15, 1954, Serial N0. 410,445
10 Claims. (Cl. 196-24) This invention relates to the conversion of mer'captans E One method utilized for the treatment of petroleum distillates to remove mercaptans entails the use of an alkaline material and particularly an alkali metal hydroxide including sodium hydroxide, potassium hydroxide, etc. Modification of this process comprises the use of a solutizer including alcohols, phenols, etc. Other methods include the copper sweetening process, doctor sweetening process, etc.
In accordance with the present invention, mercaptans are converted by reacting with a particular type of organic compound. While this method may be utilized for the conversion of mercaptans as such, it is particularly advantageous for use in the treatment of organic substances, including petroleum fractions, in which the mercaptans are present as an undesired impurity.
In a preferred embodiment, a major proportion of the mereaptans are removed from the petroleum distillate by treatment with an alkali metal hydroxide or otherwise, and the remaining small amount of mercaptans, after such treatment, are converted by means of the novel method of the present invention. The major proportion of the mercaptans are readily removed in the processes of the prior art but the final sweetening of the distillate usually is much more difi'icult. In accordance with the present invention, final sweetening is effected by converting the remaining mercaptans in the manner to be hereinafter set forth in detail.
In one embodiment the present invention relates to a method of converting a mercaptan which comprises reacting the mercaptan with a beta-dialkylamino ketone.
In a specific embodiment the present invention relates to a method of treating a sour petroleum distillate which comprises reacting the mercaptans contained in the distillate with a beta-dimethylamino ketone.
In another specific embodiment the inve'ntion relates to a method of sweetening a sour cracked gasoline which com rises reacting the mercaptans eofitained ih said gaseline with beta-diniethylaminopropiophenone.
The beta-dialk'ylamino ketones may be illustrated by the following general formula:
R1 RO-CCN II where R, R1 and R2 are hydrocarbon groups.
It is understood that R, R1 and R2 may be the same or from 1 to 4 carbon atoms each. Illustrative compounds in which R is an alkyl group include methyl beta dimethylaminoethyl ketone, ethyl beta-dimethylaminoethyl ketone, propyl beta-dimethylam'inoethyl ketone, butyl beta-dimethylaminoethyl ketone, amyl beta-dimethylaminoethyl ketone, heXyl heta-dimethylaminoethyl ketone, heptyl beta-dimethylaminoethyl ketone, octyl betadimethylaminoethyl ketone, etc., methyl beta-diethylaminoethyl ketone, methyl beta-dipropylarninoethyl ke- 1 tone, methyl beta-dibut-ylaminoethyl ketone, etc., methyl beta-dimethylaminopropyl ketone, methyl beta-dimethylaminobutyl ketone, methyl beta-dimethylaminoamyl ketone, methyl beta-dimethylaminohexyl ketone, etc., methyl beta-diethylaminopropyl ketone, methyl beta di ethylaininobutyl ketone, methyl beta-diethylaminoamyl ketone, methyl beta-diethylaminohexyl ketone, etc., methyl beta-dipropylaminopropyl ketone, methyl betadipropylaminobutyl ketone, methyl beta-dipropylaminoamyl ketone, methyl beta-dipropylaminohexyl ketone, etc., methyl beta-dibutylaminopropyl ketone, methyl beta-dibutylaminobutyl ketone, methyl beta-dibutylaminoamyl ketone, methyl beta-dibutylaminohexyl ketone, etc., ethyl beta-dimethylaminopropyl ketone, ethyl beta-dimethylaminobutyl ketone, ethyl beta-dimethylaminoamyl ketone, ethyl beta-dimethylamiuohexyl ketone, etc., propyl beta-dimethylaminopropyl ketone, propyl beta-dimethylaminobutyl ketone, propyl beta-dimethylaminoamyl ketone, propyl beta-dimethylaminohexyl ketone, etc., butyl beta-dimethylaminopropyl ketone, butyl beta-dimethylaminobutyl ketone, butyl beta-dimethylaminoamyl ketone, butyl beta-dimethylaminohexyl ketone, etc., amyl betadimethylaminopropyl ketone, amyl beta-dime'thylaminobutyl ketone, amyl beta-dimethylaminoamyl ketone, amyl beta-dimethylaminohexyl ketone, etc., hexyl beta-dimethylaminopropyl ketone, hexyl beta-dimethylaminobutyl ketone, hexyl beta-dimethylaminoamyl ketone, heXyl beta-dimethy'laminohexyl ketone, etc., heptyl beta-dimethylaminopropyl ketone, heptyl beta-dimethylaminobutyl ketone, heptyl beta-dimethylaminoamyl ketone, heptyl beta-dimethylaminohexyl ketone, etc., octyl beta- 7 dimethylaminopropyl ketone, octyl beta-dimethylaminobutyl ketone, octyl beta-dimethylaminoamyl ketone, octyl beta-dimethylaminohexyl ketone, etc.
Illustrative compounds in which R comprises an aryl group include phenyl beta-dimethylaminoethyl ketone (also named beta-dimethylaminopropiophenone), phenyl beta-diethylaminoethyl ketone, phenyl beta-dipropylaminoethyl ketone, phenyl beta-dibutylaminoethyl ketone, etc., phenyl beta-dimethylaminopropyl ketone, phenyl beta-diethylaminopropyl ketone, phenyl beta-dipropylaminopropyl ketone, phenyl beta-dibutylaminopropyl ketone, etc., phenyl beta-dimethylaminobutyl ketone, phenyl beta-diethylaminobutyl ketone, phenyl beta-dipropylaminobutyl ketone, phenyl beta-dibutylaminobutyl ketone, etc., phenyl beta-dimethylaminoamyl ketone, phenyl betadiethylaminoarnyl ketone, phenyl beta-dipropylaminoamyl ketone, phenyl beta-dibutylaminoamyl ketone, etc., phenyl beta-dimethylaminohexyl ketone, phenyl beta-diethylaminahexyl ketone, phenyl beta-dipropylaminoheiryl ketone, phenyl beta-dibut'ylaminohexyl ketone, etc.,
tolyl beta-dirnethylaminoethyl ketone, tolyl beta-diethylaminoethyl ketone, tolyl beta-dipropylaminoethyl ketone, tolyl beta-dibutylaminoe'thyl ketone, etc., tolyl beta-dimethylaminopropyl ketone, tolyl beta-diethylaminopropyl e ketone, tolyl beta-dipropylaminopropyl ketone, tolyl betadibutylaminopropyl ketone, etc., tolyl beta-dirnethylarninobutyl ketone, tolyl beta-diethylarninobutyl ketone, tolyl beta dipropylaminobntyl ketone, tolyl beta-dibutylaminob'utyl ketone, etc., xylyl beta-dimethylaminoethyl ketone, Xylyl beta-dimethylaminoethyl ketone, xylyl betadipropylaminoethyl ketone, xylyl beta-dibutylaminoethyl ketone, etc., xylyl beta-dimethylaminopropyl ketone, xylyl beta-diethylaminopropyl' ketone, xylyl beta-dipropylaminopropyl ketone, xylyl beta-dibutylaminopropyl ketone, etc., xylyl beta-dimethylaminobutyl ketone, xylyl beta-diethylaminobutyl ketone, xylyl beta-dipropylaminm aminoamyl ketone, cyclohexyl beta-diethylaminoamyl ketone, etc., cyclohexyl beta-dimethylaminohexyl ketone. cyclohexyl beta-diethylaminohexyl ketone, etc., cyclobutyl beta-dimethylaminoethylketone, cyclobutyl beta-di e'thylaminoethyl ketone, etc., cyclopropyl beta-dimethylaminoethyl ketone, cyclopropyl beta-diethylaminoethyl ketone, etc., other hydrocarbon groups represented by R include alkenyl, aralkyl, etc.
While the dialkylamino compounds are preferred, it is understood that in some cases R1 and R2 may comprise carbon atoms of a cyclic group as, for example, where R1 and h are carbon'atoms of a pyridine ring, qui'noline ring,
' isoquinoline ring, quinaldine ring, etc., or a pyrrole ring,
pyrroline ring, pyrrolidine ring, etc. In still another embodiment R may comprise a substituted hydrocarbon group, the substituent containing oxygen, nitrogen and/or sulfur, including heterocyclic rings. However, it is understood that all of these compounds are not necessarily equivalent.
While the novel process of the present invention is particularly applicable to the treatment of sour gasolines including cracked, straight-run and mixtures thereof, it is understood that the present process may be used for the treatment of other hydrocarbon distillates including cracked and/ or straight-run kerosene, diesel fuel, mineral oil, lubricating oil, fuel oil, etc. In another embodiment, the present invention may be utilized for thetreatment of gaseous fractions containing mercaptans. In still another embodiment the process may be utilized for the treatment of other fractions containing mercaptans and thus may include synthetic fractions formed from starting reactants containing mercaptans, either as an impurity or as the desired reactant. J The concentrations of beta-dialkylamino ketone to be 7 used will depend upon the concentration of mercaptans in the fraction being treated. At least one mol of betadialkylamino ketone should be used per mol of mercaptan to be converted. Preferably an excess of beta-dialkylamino ketone is used in order to ensure complete conversion of the mercaptans, and the excess may comprise up to 50 or more molecular proportions of beta-dialkylamino ketone per molecular proportion of mercaptan.
The process of the present invention may be effected in any suitable manner. In 'one' method, the beta-dialkylamino ketone iscommingled with the petroleum distillate and the mixture is subjected to refluxing, distillation, etc. The temperature'will depend upon the particular fraction being distilled and may range from slightly above atmospheric to 600 F. or. more. The distillation may be efiected atatmospheric, subatmospheric or superatmospheric pressure which may be up to 1000pounds per square inch or more. In another embodiment the beta-dialkylamino ketone is commingled with the petroleum distillate and the resultant mixture is passed through suitable mixing devices such as durion mixers, orifices,
vgaseous fraction, the gaseous fraction may be passed through a body of the beta-dialkylamino ketone contained etc., and then introduced into a storage tank which, when in a suitable reaction vesse. It is understood that any other suitable method for efiecting reaction of the betadialkylamino ketone with mercaptans may be utilized.
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 After refluxing, the portion containing beta-dimethyl aminopropiophenone had a mercaptan sulfur content of 008% by weight. The other portion, which did not contain the additive, had a mercaptan sulfur content ofv 0.02% by weight. It will be noted that the beta-dialkylamino ketone served to considerably reduce the mercaptan content of the gasoline.
Example 1 1 Topped crude oil is subjected to non-catalytic'thermal cracking by being-heated to a temperature of 940" F. in a furnace and'passed through a reaction zone and then into a flash zone wherein vapors separate from residuum. The vapors are withdrawn overhead from the flash chamber and are passed into a fractionating column to separate an overhead fraction'comprising gas and gasoline. Butyl beta-dimethylaminoethyl ketone is added to the vapors from the flash chamber before passing into the fractionating column. In the fractionating column the beta dialkylamino ketone will react with the mercaptans and the reaction product will be retained in the bottoms frac tion, thereby. resulting in an overhead gasoline fraction of reduced mercaptan content.
' Example 111 Example IV 7 Cracked gasoline having a m'ercaptan content of 0.03% by weight may be treated with caustic-methanol solution to reduce the mercaptan content down to about 0.003%: by weight. To the thus treated gasoline, beta-dimethylaminopropiophenone is added with intimate stirring and the mixture is sent to storage. This treatmeutjvill serve to produce a sweet gasoline. Y
I claim as my invention: 7 I 7 l. A method of converting a mercaptan which comprises reacting the mercaptan with beta-dialkylamino ketone. Iv
2. A method of converting a mercaptan'which cornprises reacting the mercaptanwith beta-dimethylaminopropiophenone.
3. A method of treating a sour petroleum distillate which comprises reacting the mercaptans containedin said distillate with a beta-dialkyl'amino ketone. e
4-. A method of treating .a sour petroleum distillate which comprises reacting the mercaptans containedm said distillate with a beta-dimethylamino ketone.
5. A method of treating a sour petroleum distillate which comprises reacting the mercaptans contained in said distillate with a beta-diethylamino ketone.
6. A method of treating a sour petroleum; distillate which comprises reacting the mercaptans contained in said distillate witha beta-dipropylaminqketone.. V 7. A method of treating a sour petroleum distillate which comprises reacting the mercaptans contained in said distillate with a beta-dibntylamino ketone.
8. A method of sweetening a sour gasoline which comprises reacting the mercaptans contained in said gasoline With a beta-diaikylamino ketone.
9. A method of sweetening a sour gasoline which comprises reacting the mercaptans contained in said gasoline with beta-dimethylaminopropiophenone.
10. A method of sweetening a sour gasoline which comprises reacting the mercaptans contained in said gasoline with an alkyl heta-dimethylaminoethyl ketone.
References Cited in the file of this patent UNITED STATES PATENTS

Claims (1)

1. A METHOD OF CONVERTING A MERCAPTAN WHICH COMPRISES REACTING THE MERCAPTAN WITH N BETA-DIALKYLAMINO KETONE.
US410445A 1954-02-15 1954-02-15 Conversion of mercaptans Expired - Lifetime US2708179A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3853746A (en) * 1973-11-01 1974-12-10 Universal Oil Prod Co Process for sweetening hydrocarbon products with sulfenamides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1950735A (en) * 1931-03-05 1934-03-13 Universal Oil Prod Co Process for desulphurizing hydrocarbon oils
US2045057A (en) * 1934-09-06 1936-06-23 Phillips Petroleum Co Treatment of hydrocarbon oils
US2287118A (en) * 1938-04-29 1942-06-23 Standard Oil Dev Co Treating hydrocarbons
US2608519A (en) * 1949-11-29 1952-08-26 Standard Oil Co Desulfurization of olefinic naphtha

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1950735A (en) * 1931-03-05 1934-03-13 Universal Oil Prod Co Process for desulphurizing hydrocarbon oils
US2045057A (en) * 1934-09-06 1936-06-23 Phillips Petroleum Co Treatment of hydrocarbon oils
US2287118A (en) * 1938-04-29 1942-06-23 Standard Oil Dev Co Treating hydrocarbons
US2608519A (en) * 1949-11-29 1952-08-26 Standard Oil Co Desulfurization of olefinic naphtha

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3853746A (en) * 1973-11-01 1974-12-10 Universal Oil Prod Co Process for sweetening hydrocarbon products with sulfenamides

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