US2378341A - Diesel fuel - Google Patents

Diesel fuel Download PDF

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Publication number
US2378341A
US2378341A US475215A US47521543A US2378341A US 2378341 A US2378341 A US 2378341A US 475215 A US475215 A US 475215A US 47521543 A US47521543 A US 47521543A US 2378341 A US2378341 A US 2378341A
Authority
US
United States
Prior art keywords
diesel fuel
hydrocarbon
peroxide
tertiary carbon
cetane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US475215A
Other languages
English (en)
Inventor
William E Vaughan
Frederick F Rust
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shell Development Co
Original Assignee
Shell Development Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL63850D priority Critical patent/NL63850C/xx
Application filed by Shell Development Co filed Critical Shell Development Co
Priority to US475215A priority patent/US2378341A/en
Priority to GB10061/44A priority patent/GB578170A/en
Application granted granted Critical
Publication of US2378341A publication Critical patent/US2378341A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/1811Organic compounds containing oxygen peroxides; ozonides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS 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
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen

Definitions

  • This invention relates to Diesel fuels containing a knock depressor, and more'particularly deals with such fuels containing a small amount of a peroxide of a branched chain aliphatic hydrocarbon.
  • hydrocarbon peroxides and other organic peroxides have the property, when dissolved in hydrocarbon Diesel fuels, of acting as ignition accelerators 'oi the latter, i. e., they
  • ignition accelerators 'oi the latter i. e., they
  • Our invention comprises hydrocarbon Diesel fuels of relatively high octane numbers containing an added small amount, i. e., about /;%-5%, and preferably 1%-3%, of peroxide of a hydrocarbon having an aliphatic tertiary carbon atom, wherein the percxy radical connects two tertiary carbon atoms.
  • the peroxides used in this invention are produced by slow, non-explosive. oxidation of a hydrocarbon containing at least one tertiary carbon atom of aliphatic character in the presence 01a hydrogen halide, particularly hydrogen bromide, or a compound capable of yielding such hydrogen halide under operating conditions.
  • each R represents a like or-difierent islexceedingly dangerous unless they are highly cal, two of which may together form an alicyclic ring, and which radicals may be further substituted, for instance, by the presence of one or more halogen, nitrogen or oxygen atoms which are attached to one or more of the carbon atoms of such radicals.
  • a preferred class of organic compounds which may be used as a'starting material comprises the saturated aliphatic hydrocarbons containing at least one tertiary carbon atom. Specific examples of the latter are isobutane, 2-methyl butane, 2-ethy1 butane,
  • the oxidation may be efiected in the liquid or vapor phase or both, vapor phase being preferred.
  • vapor phase being preferred.
  • some acids, ketones and aldehydes are produced; however, a: substantial portion of the reaction product consists of the peroxides employed in this invention, which, it is believed, may be represented by the formula:
  • each R again represents a like or difie'rent hydrocarbon radical which may or may not be further substituted.
  • Preferred compounds carbon atoms. These compounds are waterwhite, oil-soluble, water-insoluble liquids having ,of the polymers, or resulting from the alkylation of isobutane with butylenes, or other alkylate gasolines having relatively wide boiling ranges.
  • carbons may be oxidized to produce the peroxides useful in accordance with this invention.
  • the Diesel fuels may contain addialkyl, aryl, aralkyl, alicyclic or heterocyclic raditional additives, such as anti-oxidants,.e. e.,
  • the temperature of the oxidation is normallyare the symmetrical, saturated, di(tertiary alkyl) peroxides having not more than about 24 various alkyl phenols such as xylenols, trimethyl phenol, 2,4-dimethyl-6-tertiary butyl phenol, 4-methyl-2,6-ditertiary butyl phenol, etc; aromatic amines, preferably secondary aromatic amines, such as N ,N' dibutyl phenylene diainine, diphenylamine, phenyl alpha naphthylamine, alpha alpha, alpha beta, or beta beta.
  • various alkyl phenols such as xylenols, trimethyl phenol, 2,4-dimethyl-6-tertiary butyl phenol, 4-methyl-2,6-ditertiary butyl phenol, etc
  • aromatic amines preferably secondary aromatic amines, such as N ,N' dibutyl phenylene dia
  • dinaphthylamines amino phenols, such as benzyi' para amino phenol, etc.
  • anti-corrosive agents such as dicarboxylic acids having at least 16 carbon atoms, e. g., alkyl succinic acids
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel and a cetane improving amount of a peroxide of a hydrocarbon having at least one aliphatic tertiary carbon atom, the peroxy radical in said peroxide connecting two tertiarycarbon atoms.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel and a cetane improving amount of a peroxide of a chlorinated hydrocarbon having at least one aliphatic tertiary carbon atom, the peroxy radical in said peroxide connecting two tertiary carbon atoms.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydro-' carbon Diesel fuel containing about A;%5% of a peroxide of a hydrocarbon having atleast one aliphatic tertiary carbon atom, the peroxy radical in said peroxide connecting two tertiary carbon atoms.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel containing about 1%-3% of a peroxide of a hydrocarbon having at least one aliphatic tertiary carbon atom, the peroxy radical in said peroxide connecting two tertiary carbon atoms.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydro- The cetane number of the fuel carbon Diesel fuel and a cetane improving amount of a peroxide of a hydrocarbon having not more than 12 carbon atoms and at least one aliphatic tertiary carbon atom, the peroxy radical in said peroxide connecting two tertiary carbon atoms.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel and a cetane improving amount of a peroxide of compounds having the formula wherein the several R's represent hydrocarbon radicals, the peroxy radical of said peroxide connecting two of said compounds through their tertiary carbon atoms.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel and a cetane improving amount of a peroxide obtained by slow oxidation of a hydrocarbon containing at least one aliphatic tertiary carbon atom.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel and a cetane improving amount of'a peroxide having the formula wherein the several R's represent hydrocarbon radicals.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel and a cetane improving amount of a symmetrical peroxide having not more than 24 carbon atoms and the formula wherein the several Rs represent hydrocarbon radicals.
  • a Diesel fuel of improvedcetane number comprising a predominant amount of a hydrocarbon Diesel fuel oil and a cetane improving amount of a di-isobutane peroxide wherein the peroxy radical connects two tertiary carbon radicals.
  • a Diesel fuel of improved cetane number comprising a predominant amount of a hydrocarbon Diesel fuel oil and a cetane improving amount of di-isopentane peroxide wherein the -peroxy radical connects two tertiary carbon radicals.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (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)
  • Liquid Carbonaceous Fuels (AREA)
US475215A 1943-02-08 1943-02-08 Diesel fuel Expired - Lifetime US2378341A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
NL63850D NL63850C (US06272168-20010807-M00014.png) 1943-02-08
US475215A US2378341A (en) 1943-02-08 1943-02-08 Diesel fuel
GB10061/44A GB578170A (en) 1943-02-08 1944-05-24 Diesel fuel

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US475215A US2378341A (en) 1943-02-08 1943-02-08 Diesel fuel

Publications (1)

Publication Number Publication Date
US2378341A true US2378341A (en) 1945-06-12

Family

ID=23886670

Family Applications (1)

Application Number Title Priority Date Filing Date
US475215A Expired - Lifetime US2378341A (en) 1943-02-08 1943-02-08 Diesel fuel

Country Status (3)

Country Link
US (1) US2378341A (US06272168-20010807-M00014.png)
GB (1) GB578170A (US06272168-20010807-M00014.png)
NL (1) NL63850C (US06272168-20010807-M00014.png)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4740215A (en) * 1987-01-27 1988-04-26 Union Oil Company Of California Composition for cetane improvement of diesel fuels
US5314511A (en) * 1992-12-23 1994-05-24 Arco Chemical Technology, L.P. Diesel fuel
WO2002014456A2 (en) * 2000-08-15 2002-02-21 Akzo Nobel N.V. Use of trioxepans in ignition improved fuels

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4740215A (en) * 1987-01-27 1988-04-26 Union Oil Company Of California Composition for cetane improvement of diesel fuels
US5314511A (en) * 1992-12-23 1994-05-24 Arco Chemical Technology, L.P. Diesel fuel
WO2002014456A2 (en) * 2000-08-15 2002-02-21 Akzo Nobel N.V. Use of trioxepans in ignition improved fuels
WO2002014456A3 (en) * 2000-08-15 2003-02-27 Akzo Nobel Nv Use of trioxepans in ignition improved fuels
US6540796B2 (en) 2000-08-15 2003-04-01 Akzo Nobel N.V. Use of trioxepans in ignition improved fuels

Also Published As

Publication number Publication date
NL63850C (US06272168-20010807-M00014.png)
GB578170A (en) 1946-06-18

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