US2004094A - Hydrocarbon oil and method of making the same - Google Patents

Hydrocarbon oil and method of making the same Download PDF

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Publication number
US2004094A
US2004094A US307545A US30754528A US2004094A US 2004094 A US2004094 A US 2004094A US 307545 A US307545 A US 307545A US 30754528 A US30754528 A US 30754528A US 2004094 A US2004094 A US 2004094A
Authority
US
United States
Prior art keywords
gum
naphtha
alpha
naphthylamine
normally tending
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
US307545A
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English (en)
Inventor
Herbert G M Fischer
Clifford E Gustafson
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.)
Standard Oil Development Co
Original Assignee
Standard Oil 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
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to US307545A priority Critical patent/US2004094A/en
Priority to FR681708D priority patent/FR681708A/fr
Priority to DEST46432D priority patent/DE563375C/de
Priority to GB28445/29A priority patent/GB319363A/en
Priority to DK44671D priority patent/DK44671C/da
Application granted granted Critical
Publication of US2004094A publication Critical patent/US2004094A/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
    • C10L1/22Organic compounds containing nitrogen
    • 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
    • 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
    • C10L1/16Hydrocarbons
    • C10L1/1616Hydrocarbons fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine
    • 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
    • C10L1/182Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/22Organic compounds containing nitrogen
    • C10L1/222Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
    • C10L1/223Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom

Definitions

  • this method ured by the method No. 530.1 in the United States Bureau of Mines Technical Paper 323 B, entitled Specification for petroleum products and methods of testing, revised October 21, 1927, page 96.
  • this method consists in placing 100 cc. of the naphtha to be tested in a 3 inch diameter spun copper dish on a steam bath and evaporating oif the volatile material. The result is expressed in milligrams of gum left in the dish per- 100 cc. of naphtha.
  • aromatic hydrocarbons with condensed rings are suitable for our process such as naphthalene, anthracene, phenanthrene and the like and certain derivatives of these compounds are also useful for our purpose.
  • the substitution of certain groups, particularly those of a basic character, in the alpha position greatly increases the eflect of the addition agents, for example, alpha-naphthol appears to be better than naphthalene as also are alphanaphthylamine and phenyl alpha-naphthylamine.
  • the quantity of the addition agent is very small, not being greater in any case than 5 gr. per litre of the naphtha and generally between the approximate limits of .01 to 1.0 gr. per litre. There appears to be an optimum quantity of the agent which will give the best results and it is a simple matter to make up samples of the different strengths and empirically select the most suitable concentration. This behavior appears to be characteristic of all suitable addition agents including those disclosed in our copending application Serial No. 307,546, filed Sept. 21, 1928. As an illustration, the following example is given, alphanaphthol being added in different quantities as indicated and opposite the number of milligrams of gum per 100 cc. of naphtha is given as deter- 5 mined by the above described test.
  • the reagent may be dissolved directly in the oil or may be added in the form of a more concentrated solution in naphtha, benzol or other suitable solvents.
  • the agent should be added to the gasoline, which is preferably slightly alkaline or neutral and no treatment which will remove the agent should thereafter be given the oil.
  • mixtures-of addition agents such as alpha-naphthol and naphthylamine may be added to gasoline with good results and that volatile metal compounds such as metal carbonyls, metallo-organic substances, which are useful for their anti-detonation effects, may be present in the naphtha without any adverse action.
  • naphthalene compounds having certain substituted groups is used and by this term we wish to include the substituted naphthalene itself, and the substituted homologues, of which phenyl naphthalene may be taken as an example.
  • a composition of matter comprising a low boiling hydrocarbon oil containing unsaturated constituents of the type normally tending to form gum and produced by pyrolysis of heavy hydrocarbons, to which has been added an ciphenaphthylamine having one hydrogen oi the amino group substituted by a benzene hydrocarbon radical, in quantity sufilcient to retard such deterioration.
  • composition of matter comprising a low boiling hydrocarbon oil containing unsaturated constituents of the-type normally tending to form gum and produced by pyrolysis of heavy hydrocarbons, to which has been added a. phenyl alpha-naphthylamine in quantity suiflcient to retard such' gum formation.
  • the method of preserving low boiling hydrocarbon oils containing unsaturated constituents of the type normally tending to form gum and produced by pyrolysis of heavy hydrocarbons which comprises incorporating therein a snail amount of an alpha-naphthylamine having one hydrogen or the amino group substituted by a benzene hydrocarbon radical, in quantity sumcient to retard such deterioration.
  • the method of preserving cracked naphtha normally tending to deteriorate and form gums on storage which comprises incorporating therewith 0.1 to 5 grams per litre of phenyl alphanephthylamine.
  • a motor fuel comprising cracked gasoline normally tending to deteriorate upon storage to which has been added a phenylmpha naphthylamine in quantity suilicient to retard such deterioration.
  • a motor fuel comprising cracked gasoline normally tending to deteriorate upon storage to which has been added phenyl alpha naphthylee in quantity suiilcient to retard such deterioration.
  • a motor fuel comprising cracked gasoline normally tending to develop gum on storage to which has been added phenyl alpha naphthylamine in quantity suflicient to retard the formation of gum.
  • a cracked gasoline normally tending to develop gum to which has been added phenyl alpha naphthylamine in quantity suiiicient to retard the formation of gum.
  • a motor fuel comprising a gasoline normally tending to deteriorate upon storage to which has been added phenyl alpha naphthylamine in quantity suiiicient to retard such deterioration.
  • a compodtion of matter comprising a low boiling hydrocarbon oil of the class produced by thermal decomposition of hydrocarbon of higher molecular weight normally tending to form gum, and 0.01-5 grams per liter of phenyl alpha n'hphthylamine 12.
  • a composition of matter comprisingcracked naphtha normally tending to form gum, and 0.01-1 gram per liter of phenyl alpha naphthylamine.

Landscapes

  • 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
US307545A 1928-09-21 1928-09-21 Hydrocarbon oil and method of making the same Expired - Lifetime US2004094A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US307545A US2004094A (en) 1928-09-21 1928-09-21 Hydrocarbon oil and method of making the same
FR681708D FR681708A (fr) 1928-09-21 1929-09-12 Perfectionnements aux huiles d'hydrocarbures et procédé pour les fabriquer
DEST46432D DE563375C (de) 1928-09-21 1929-09-15 Verfahren zur Verhinderung der Harzbildung in zur Harzbildung neigenden Benzinen
GB28445/29A GB319363A (de) 1928-09-21 1929-09-19
DK44671D DK44671C (da) 1928-09-21 1929-09-21 Flydende Motorbrændsel af Kulbrinter.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US307545A US2004094A (en) 1928-09-21 1928-09-21 Hydrocarbon oil and method of making the same

Publications (1)

Publication Number Publication Date
US2004094A true US2004094A (en) 1935-06-11

Family

ID=23190209

Family Applications (1)

Application Number Title Priority Date Filing Date
US307545A Expired - Lifetime US2004094A (en) 1928-09-21 1928-09-21 Hydrocarbon oil and method of making the same

Country Status (5)

Country Link
US (1) US2004094A (de)
DE (1) DE563375C (de)
DK (1) DK44671C (de)
FR (1) FR681708A (de)
GB (1) GB319363A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1064666B (de) * 1956-06-15 1959-09-03 Exxon Research Engineering Co Schmieroel

Also Published As

Publication number Publication date
DE563375C (de) 1932-11-04
DK44671C (da) 1931-10-05
GB319363A (de) 1930-12-19
FR681708A (fr) 1930-05-19

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