Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C01—INORGANIC CHEMISTRY
  • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
  • C01B25/00—Phosphorus; Compounds thereof
  • C01B25/02—Preparation of phosphorus
  • C01B25/027—Preparation of phosphorus of yellow phosphorus
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C7/00—Purification; Separation; Use of additives
  • C07C7/20—Use of additives, e.g. for stabilisation
• • 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
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
  • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
  • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
  • C10M2215/066—Arylene diamines

Definitions

• This invention relates to the chemical arts.
• it relates to the sweetening of sour, unsaturated, hydrocarbon distillates, such as, for example, sour, cracked gasoline and the like.
• the inhibitor sweetening of sour, cracked gasoline and the like is a well known process.
• the basic process is described in the US. Patent No. 2,508,817, to Devol et al.
• it comprises admixing the sour, unsaturated, hydrocarbon distillate with a p-phenylenediamine, an alkaline material such as, for example 40" B. caustic, and oxygen which is usually already present in the sour distillate.
• the mixture that results is stored preferably at 80-100 F., although higher and lower temperatures can be employed, until the desired extent of sweetening has taken place.
• the sweetened hydrocarbon distillate and alkaline material are then separated.
• the p-phenylenediamine which is soluble in the distillate, remains with it and subsequently functions to inhibit gum formation in the distillate.
• This invention is based upon the discovery that mixtures of certain N,N-di-sec-alkyl-(ortho and para)-phenylenediamines generally give substantially higher sweetening rates than p-phenylenediamines, particularly at 4080 F.
• this invention comprises an inhibitor sweetening process which comprises contacting sour, unsaturated hydrocarbon distillate with oxygen,- alkaline material and a sweetening agent consisting essentially of a mixture of at least one N,N-di-sec-alkyl-o-phenylenediamine represented by the formula and at least one N,N'-di-sec-alkyl-p-phenylenediamine represented by the formula wherein R and R" are radicals independently selected from the group consisting of methyl and ethyl radicals and R and R' are radicals independently selected from the group consisting of straight chain and branched alkyl radicals, the number of carbon atoms in R and R totaling 2-12 and the number of carbon atoms in R" and R totaling 2-12.
• the R and R radicals can be the same or different and the R and R' radicals can be the same or different.
• mixed alkyl derivatives of oand p-phenylenediamines such as N-sec-butyl-N'-isopropyl- (oand p-)-phenylenediamines and the like, can be made by various processes including the reductive alkylation of the corresponding oand p-phenylenediamine with a mixture of corresponding ketones.
• the R and R radicals include: isopropyl, secondary butyl, l-methylbutyl, l-methylpentyl, l-methylhexyl, l-methylheptyl, l-ethylpropyl, l-ethylbutyl, l-ethylpentyl, l-ethylhexyl, l-ethyl- 3-methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylpentyl, and the like.
• N,N'- di-sec-alkyl-oand p-phenylenediamines of this invention include: N,N'-di-isopropyl-oand p-phenylenediamine, N,N'-di-sec-butyl-oand p-phenylenediamine and N,N'- bis(l,4-dimethylpentyl)-oand p-phenylenediamine.
• the weight ratio of all said N,N-di-secalkyl-o-phenylenediamine to all said N,N'-di-sec-alkyl-pphenylenediamine is generally in a range from about 9:1 to about 1:9 and preferably from about 1:1 to about 1:3.
• a feature of advantage of this mixture is that in general it has a low freezing point.
• a mixture of N,N' di-sec-butyl-o-phenylenediarnine and N,N-di-secbutyl-p-phenylenediamine at a weight ratio of the o-phenylenediamine to the p-phenylenediamine of 35:65 has a freezing point of 32 F.
• Another feature of advantage of this mixture is that in the ASTM gum test it appears to have good gum inhibition activity in gasoline.
• the sweetening agent of this invention is employed in the inhibitor sweetening process by admixing it with the sour, unsaturated hydrocarbon distillate to be sweetened. It can be added as such or as a concentrate wherein it is dissolved in an appropriate solvent such as alcohol, xylene or a gasoline fraction.
• an appropriate solvent such as alcohol, xylene or a gasoline fraction.
• the quantity of sweetening agent added to the sour, unsaturated hydrocarbon distillate to be sweetened depends on the size of the R and R' radicals as Well as on the particular hydrocarbon distillate being treated.
• the sweetening agent concentration is in a range from about 0.0005 to about 0.02% by weight of the sour, unsaturated hydrocarbon distillate to give satisfactory results.
• a preferred range is about from 0.001 to about 0.01% by weight of the sour, unsaturated hydrocarbon distillate.
• the quantity of sweetening agent added to sour, unsaturated hydrocarbon distillate to give a concentration in these ranges is generally in a range from about 1.3 to about 52 pounds per 1000 barrels (U.S.) of sour, unsaturated, hydrocarbon distillate and preferably in a range from about 2.6 to about 26 pounds per 1000 barrels (U.S.) of sour, unsaturated, hydrocarbon distillate.
• Unsaturated hydrocarbon distillate under the concepts of this invention is a liquid hydrocarbon having an unsaturated hydrocarbon content. It covers an unsaturated hydrocarbon distillate boiling generally in a range from about 50 to about 750 F. and usually in a range from about 90 to about 490 F. It includes cracked gasoline including thermally cracked gasoline, catalytically cracked gasoline, reformed gasoline, polyform gasoline and the like, and substantially saturated gasoline such as, for example, straight run gasoline, natural gasoline and the like blended with olefinic or other unsaturated hydrocarbons, and cracked or blends of cracked and straight run, higher boiling distillates including jet fuel, kerosene, diesel fuel, burner oil, lubricating oil, gas oil and the like.
• Example 2 This example illustrates the outstanding efiicacy of one embodiment of the sweetening agent of this invention.
• N,N-di-sec-butyl-ophenylenediamine To one sample was added N,N-di-sec-butyl-ophenylenediamine, to another sample was added a mixture consisting essentially of N,N-di-sec-butyl-o-phenylenediamine and N,N-di-sec-butyl-p-phenylenediamine at a weight ratio of the o-phenylenediamine to the p-phenylenediamine of :65, and to the third sample was added N,N'-di-sec-butyl-p-phenylenediamine.
• the quantity of additive in each sample was about 8 pounds per 1000 barrels (U.S.) of the gasoline. This gave an additive concentration in each sample of about 0.005% by weight of the gasoline. 5% by volume of the sample of 10 B. aqueous caustic (NaOH) solution was added to each sample and each sample was shaken for one minute. Thereafter the mercaptan sulfur content of each sample was periodically determined by potentiometric titration. The results are summarized in the following tables.
• An additive composition for hydrocarbons having an unsaturated hydrocarbon content and boiling in the range of about 50 F. to about 750 F. consisting essentially of N,N-di-sec-lower-alkyl-o-phenylenediamine and 5 N,N'-di-sec-1ower-alkyl-p-phenylenediamine in the weight ratio of 25/75 to 50/50.
• N,N'-di-sec-lower alkyl-o-phenylenediamine is N,N-disec-butyl-o-phenylenediamine and the N,N-di-sec-loweralkyl-p-phenylenediamine is N,N'-di-sec-butyl-p-phenylenediamine.
• a process for stabilizing and sweetening hydrocarbons having an unsaturated hydrocarbon content and boiling in the range of about 50 F. to about 750 F. comprising admixing with said hydrocarbons from about 0.0005 to about 0.02% by weight of said hydrocarbons of the additive composition of claim 1.
• composition comprising:

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Inorganic Chemistry (AREA)
• Analytical Chemistry (AREA)
• Water Supply & Treatment (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Priority Applications (8)

Applications Claiming Priority (2)

Publications (1)

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ID=27025967

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Cited By (5)

Citations (5)

• 1965
  • 1965-12-22 IL IL24848A patent/IL24848A/en unknown
  • 1965-12-31 DE DE19651545276 patent/DE1545276A1/de active Pending
  • 1965-12-31 BE BE674604A patent/BE674604A/xx unknown
• 1966
  • 1966-01-04 NL NL6600042A patent/NL6600042A/xx unknown
  • 1966-01-04 FR FR44726A patent/FR1462763A/fr not_active Expired
  • 1966-01-04 GB GB233/66A patent/GB1127151A/en not_active Expired
  • 1966-01-04 BR BR176219/66A patent/BR6676219D0/pt unknown
• 1967
  • 1967-08-09 US US659324A patent/US3404087A/en not_active Expired - Lifetime

Patent Citations (5)

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