US1947219A - Treatment of motor fuel - Google Patents

Treatment of motor fuel Download PDF

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Publication number
US1947219A
US1947219A US539134A US53913431A US1947219A US 1947219 A US1947219 A US 1947219A US 539134 A US539134 A US 539134A US 53913431 A US53913431 A US 53913431A US 1947219 A US1947219 A US 1947219A
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US
United States
Prior art keywords
gum
formation
diamine
gasoline
motor fuel
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Expired - Lifetime
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US539134A
Inventor
Paul I Murrill
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.)
Vanderbilt Chemicals LLC
Original Assignee
RT Vanderbilt Co Inc
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
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Priority to US539134A priority Critical patent/US1947219A/en
Application granted granted Critical
Publication of US1947219A publication Critical patent/US1947219A/en
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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
    • 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 invention relates to a new and improved treatment of motor fuel. It includes both the method of treatment and the product obtained.
  • the pure gasoline distillate contains "potential gum' which, on standing, forms actual gum.
  • This invention relates to the treatment of motor fuels to prevent or retard or inhibit the formation of gum, and particularly it relates to the treatment of motor fuels containing gum-forming unsaturated constituents produced by the cracking of petroleum compounds. More particularly the invention relates to the treatment of motor fuels containing gum-forming unsaturated constituents produced by cracking petroleum oil at a high temperature, e. g. at a temperature of at least 300 C.
  • a small amount of an aromatic di-secondari diamine is added to a freshly distilled gasoline which contains gumforming unsaturated constituents to delay or prevent the formation of objectionable amounts of gum.
  • a freshly distilled gasoline which contains gumforming unsaturated constituents to delay or prevent the formation of objectionable amounts of gum.
  • the di-secondary diamine may be used with.
  • the motor fuels of this invention may contain in addition to gasoline, benzol or other saturated compounds. anti-knock compounds, etc., and the di-secondary diamine may be added to the gasoline before or after blending with the other constituents.
  • sdiphenyl-benzidine di-secondary diamines
  • diaryl meta-arylene diamines e. g. s-diphenyl-m-phenylene diamine, s-di-beta-naphthyl-m-pheny1ene diamine, and diaryl para-arylene diamines, e. g.
  • Gasoline is prepared by a variety .of methods and the effectiveness of the various di-secondary diamine. These are more soluble than s-di-alphanaphthyl-p-phenylene diamine and s-di-beta naphthyl-p-phenylene diamine and are preferred for this reason.
  • a motor fuel comprising cracked gasoline and a diaryl arylene diamine in an amount sufficient to inhibit gum formation.
  • a motor fuel comprising cracked gasoline and a ditolyl para-phenylene diamine in an amount suflicient to inhibit gum formation.
  • a motor fuel comprising cracked gasoline which contains gum-forming. constituents produced by the cracking of petroleum compounds and a ditolyl arylene diamine in an amount sufficient to inhibit gum formation.
  • a motor fuel comprising cracked gasoline which contains gum-forming constituents produced by the cracking of petroleum compounds and a diaryl para-phenylene diamine in an amount suflicient to inhibit gum formation.
  • a motor fuel comprising cracked gasoline containing gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and a diaryl arylene diamine in an amount sufiicient to inhibit gum formation.
  • a motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds and a compound of the general formula RNH.R2NHR1 where R and R1 may be the same or different aromatic radicals and R2 is an aromatic radical, said compound being present in an amount suflicient to inhibit gum formation.
  • a motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and diorthotolyl-p-phenylene-diamine in an amount sufficient to inhibit gum formation.
  • a motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and di-paratolyl-p-phenylene-diamine in an amount sufficient to inhibit gum formation.
  • a motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and diphenylp-phenylene-diamine in an amount sufficient to inhibi" gum formation.

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)
  • Liquid Carbonaceous Fuels (AREA)

Description

Patented Feb. 13, 1934' UNITED STATES PATENT OFFICE 1,947,219 TREATMENT OF MOTOR FUEL No Drawing.
pplication May 21, 1931 Serial No. 539,134
15 Claims.
This invention relates to a new and improved treatment of motor fuel. It includes both the method of treatment and the product obtained.
Difiiculty has been experienced with the formation of gum in motor fuels. A gasoline which is pure distillate, free from non-volatile matter, may, on evaporation, form a deposit of gum. This is particularly true of cracked gasolines and more particularly of gasolines produced by cracking at high temperatures. Gasolines produced by cracking petroleum oil in the vapor phase are particularly bad from the standpoint of gum formation. The formation of gum apparently is due to the oxidation of unsaturated constituents of the gasoline. The pure gasoline distillate contains "potential gum' which, on standing, forms actual gum.
This invention relates to the treatment of motor fuels to prevent or retard or inhibit the formation of gum, and particularly it relates to the treatment of motor fuels containing gum-forming unsaturated constituents produced by the cracking of petroleum compounds. More particularly the invention relates to the treatment of motor fuels containing gum-forming unsaturated constituents produced by cracking petroleum oil at a high temperature, e. g. at a temperature of at least 300 C.
According to this invention a small amount of an aromatic di-secondari diamine is added to a freshly distilled gasoline which contains gumforming unsaturated constituents to delay or prevent the formation of objectionable amounts of gum. In general from two to ten milligrams per one hundred cubic centimeters of gasoline gives good results but larger or smaller amounts of the di-secondary diamine may be used with.-
out departing from the scope of this invention.
The motor fuels of this invention may contain in addition to gasoline, benzol or other saturated compounds. anti-knock compounds, etc., and the di-secondary diamine may be added to the gasoline before or after blending with the other constituents.
Compounds which have been found effective include the following di-secondary diamines: sdiphenyl-benzidine. and diaryl meta-arylene diamines. e. g. s-diphenyl-m-phenylene diamine, s-di-beta-naphthyl-m-pheny1ene diamine, and diaryl para-arylene diamines, e. g. s-di-alpha naphthyl-p-phenylene diamine, s-di-beta-naphthyl-m-phenylene diamine, s-diphenyl-p-phen'ylene diamine, s-diorthotolyl-p-phenylene diamine and. s-diparatolyl-p-phenylene diamine.
Gasoline is prepared by a variety .of methods and the effectiveness of the various di-secondary diamine. These are more soluble than s-di-alphanaphthyl-p-phenylene diamine and s-di-beta naphthyl-p-phenylene diamine and are preferred for this reason.
This application is in part a continuation of my application Serial No. 491,817, filed October 28, 1930.
I claim:
1. The process of treating cracked gasoline, which comprises mixing therewith before the formation of any substantial amount of gum in the gasoline, a diaryl arylene diamine in an amoun sufficient to inhibit gum formation. I
2. The process of treating cracked gasoline, which comprises mixing therewith before the formation of any substantial amount of gum in the gasoline, a ditolyl arylene diamine in an amount sufficient to inhibit gum formation.
3. .The process of treating cracked gasoline, which comprises mixing therewith before the formation of any substantial amount of gum in the gasoline, a diarylpara-phenylene diamine in an amount-sufficient to inhibit gum formation.
4. A motor fuel comprising cracked gasoline and a diaryl arylene diamine in an amount sufficient to inhibit gum formation.
5. A motor fuel comprising cracked gasoline and a ditolyl para-phenylene diamine in an amount suflicient to inhibit gum formation.
6. A motor fuel comprising cracked gasoline which contains gum-forming. constituents produced by the cracking of petroleum compounds and a ditolyl arylene diamine in an amount sufficient to inhibit gum formation.
'7. A motor fuel comprising cracked gasoline which contains gum-forming constituents produced by the cracking of petroleum compounds and a diaryl para-phenylene diamine in an amount suflicient to inhibit gum formation.
8. A motor fuel comprising cracked gasoline containing gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and a diaryl arylene diamine in an amount sufiicient to inhibit gum formation.
9. A motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds and a compound of the general formula RNH.R2NHR1 where R and R1 may be the same or different aromatic radicals and R2 is an aromatic radical, said compound being present in an amount suflicient to inhibit gum formation.
10. The process of treating cracked gasoline which comprises mixing therewith before the formation of any substantial amount of gum, diortho-tolyl-p-phenylene diamine in an amount sufficient to inhibit gum formation.
11. The process of treating cracked gasoline which comprises mixing therewith before the formation of any substantial amount of gum, dipara-tolyl-p-phenylene-diamine in an amount sumcient to inhibit gum formation.
12. The process of treating cracked gasoline which comprises mixing therewith before the formation of any substantial amount of gum, diphenyl-p-phenylene-diamine in an amount sumcient to inhibit gum formation.
13. A motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and diorthotolyl-p-phenylene-diamine in an amount sufficient to inhibit gum formation.
14. A motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and di-paratolyl-p-phenylene-diamine in an amount sufficient to inhibit gum formation.
15. A motor fuel comprising gum-forming constituents produced by the cracking of petroleum compounds at a high temperature and diphenylp-phenylene-diamine in an amount sufficient to inhibi" gum formation.
PAUL I. MURRILL.
US539134A 1931-05-21 1931-05-21 Treatment of motor fuel Expired - Lifetime US1947219A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2451642A (en) * 1944-10-23 1948-10-19 Standard Oil Co Viscous mineral oil compositions
US2456569A (en) * 1944-12-18 1948-12-14 Union Oil Co Motor fuel
US2706677A (en) * 1950-06-28 1955-04-19 Exxon Research Engineering Co Amines and amides as anti-stalling additives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2451642A (en) * 1944-10-23 1948-10-19 Standard Oil Co Viscous mineral oil compositions
US2456569A (en) * 1944-12-18 1948-12-14 Union Oil Co Motor fuel
US2706677A (en) * 1950-06-28 1955-04-19 Exxon Research Engineering Co Amines and amides as anti-stalling additives

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