US2147572A - Method of improving the color of cracked hydrocarbon distillates - Google Patents

Method of improving the color of cracked hydrocarbon distillates Download PDF

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Publication number
US2147572A
US2147572A US87256A US8725636A US2147572A US 2147572 A US2147572 A US 2147572A US 87256 A US87256 A US 87256A US 8725636 A US8725636 A US 8725636A US 2147572 A US2147572 A US 2147572A
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United States
Prior art keywords
color
improving
cracked hydrocarbon
hydrocarbon distillates
distillates
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Expired - Lifetime
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US87256A
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Louis A Clarke
John R Callaway
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Texaco Inc
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Texaco Inc
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Priority to US87256A priority Critical patent/US2147572A/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
    • C10G19/00—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment
    • 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
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
    • C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
    • 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
    • C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
    • 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
    • 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
    • C10L1/2235—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 hydroxy containing
    • 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
    • C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
    • C10L1/2425—Thiocarbonic acids and derivatives thereof, e.g. xanthates; Thiocarbamic acids or derivatives thereof, e.g. dithio-carbamates; Thiurams
    • 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
    • C10L1/26—Organic compounds containing phosphorus
    • C10L1/2633—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond)
    • C10L1/2658—Organic compounds containing phosphorus phosphorus bond to oxygen (no P. C. bond) amine salts

Definitions

  • This invention relates to the treatment of cracked hydrocarbon distillates and has to do particularly with a method and means for improving the color characteristicsof such distillates.

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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)
  • Detergent Compositions (AREA)

Description

Patented Feb. 14, 1939 UNITED STATES PATENT OFFICE METHOD OF IMPROVING THE COLOR OF CRACKED HYDROCARBON DISTILLATES No Drawing. Application June 25, 1936,
Serial No. 87,256
1 Claim.
This invention relates to the treatment of cracked hydrocarbon distillates and has to do particularly with a method and means for improving the color characteristicsof such distillates.
Uracked hydrocarbon distillates of the class of gasoline and kerosene often become discolored on storage as a result of the development of color bodies therein. This discoloration may be cleared up and the original color substantially restored by subjecting the off-colored distillate to the action of a suitable bleaching agent. Bleaching agents proposed heretofore, however, have been open to the objection that they are too slow in action or are incapable of maintaining the improved color.
It is the principal object of the present invention to provide an efficient and effective means of improving the color of cracked hydrocarbon dis-.
tillates and of stabilizing the color so that the improved color may be maintained.
In accordance with the present invention, the oil to be treated is subjected to the action of a powerful bleaching agent whereby the color is quickly improved and then the oil is stabilized by providing therein a stabilizing agent which will fix and maintain the improved color. The bleaching and stabilizing agents may both be added to the oil at the same time or the oil may be first bleached and then the stabilizing agent added. In general, the order of the addition of the reagents is not important although we prefer to add the stabilizing agent last.
The bleaching agents which we use in practicing the invention are the hydroxyl amines. Hydroxyl amine itself is useful although, due to its relative insolubility in gasoline, it is advantageous to use derivatives of hydroxyl amine, such as substituted hydroxyl amines; for example the alkyl or aryl derivatives. Included within the group of substituted compounds contemplated are alphaand and beta-.
beta-methylhydroxylamine, alphaphenylhydroxylamine and diphenylhydroxylamine. We prefer to use an alkyl hydroxylamine such as alpha-methy1hydroxylamine.
The stabilizing agents comprise the class of gum inhibitors including the hydroxy benzenes, the aliphatic and aromatic amines and aminophenols. Useful compounds are cresols, xylenols, pyrogallol, hydroquinone, catechol, orthoand para-aminophenols, benzyl-aminophenol, diphenylthiourea, lecithin, substituted phenylenediamines, dl-butylamine, tri-amylamine, etc. We prefer to use a polyhydroxy benzene, such as pyrcgallol or catechol or alkyl derivatives thereof, for example amylpyrogallol and tertiary-butylcatechol. Good results are obtained with diphenylthiourea, benzylaminophenol and lecithin.
As an example of the operation of the invention, a sample of cracked gasoline which had been in storage for some time and gone off-color to about 10 Saybolt was treated with about 0.01% of beta-phenylhydroxylamine. The color was bleached in a few minutes to +19 Saybolt. The restored color in the course of a few weeks normally reverted slowly but on the addition of about 0.01% of amyl pyrogallol the color may be substantially fixed. As another example, a cracked gasoline which originally had a Saybolt color of around 20 had gone off-color in the course of a few months to yellow. To this off-color sample was added about 0.01% of alpha-methylhydroxylamine. In the course of a few hours the color was restored to approximately the original. The sample having the improved color normally tended to become slowly discolored after a few months storage. By the addition of about 0.01% of diphenylthiourea, the improved color may be substantially maintained.
The amounts of bleaching and stabilizing agents given in the above examples are not'flxed and may be varied within quite wide limits. In
general, amounts varying from about 0.005-0.10%
may be used and preferably betweenabout 0.005 and 0.05%.
The present invention has the advantage that a powerful bleaching agent may be used, thereby conserving time and improving the color to a LOUIS A. CLARKE. JOHN R. CALLAWAY.
US87256A 1936-06-25 1936-06-25 Method of improving the color of cracked hydrocarbon distillates Expired - Lifetime US2147572A (en)

Priority Applications (1)

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US87256A US2147572A (en) 1936-06-25 1936-06-25 Method of improving the color of cracked hydrocarbon distillates

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0534668A1 (en) * 1991-09-24 1993-03-31 Betz Europe, Inc. Stabilization of gasoline mixtures
WO2002068570A2 (en) * 2001-02-28 2002-09-06 The Lubrizol Corporation Combustion improvers for normally liquid fuels

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0534668A1 (en) * 1991-09-24 1993-03-31 Betz Europe, Inc. Stabilization of gasoline mixtures
WO2002068570A2 (en) * 2001-02-28 2002-09-06 The Lubrizol Corporation Combustion improvers for normally liquid fuels
WO2002068570A3 (en) * 2001-02-28 2003-10-16 Lubrizol Corp Combustion improvers for normally liquid fuels

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