EP3202875A1 - Bleifreies flugzeugbenzin - Google Patents

Bleifreies flugzeugbenzin Download PDF

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Publication number
EP3202875A1
EP3202875A1 EP16154197.4A EP16154197A EP3202875A1 EP 3202875 A1 EP3202875 A1 EP 3202875A1 EP 16154197 A EP16154197 A EP 16154197A EP 3202875 A1 EP3202875 A1 EP 3202875A1
Authority
EP
European Patent Office
Prior art keywords
toluidine
percent
methyl
weight
gasoline
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.)
Withdrawn
Application number
EP16154197.4A
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English (en)
French (fr)
Inventor
designation of the inventor has not yet been filed The
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.)
Lanxess Deutschland GmbH
Original Assignee
Lanxess Deutschland GmbH
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 Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Priority to EP16154197.4A priority Critical patent/EP3202875A1/de
Publication of EP3202875A1 publication Critical patent/EP3202875A1/de
Withdrawn legal-status Critical Current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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/04Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • C10L1/06Liquid carbonaceous fuels essentially based on blends of hydrocarbons for spark ignition
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/02Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/023Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • 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
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/10Use of additives to fuels or fires for particular purposes for improving the octane number
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2270/00Specifically adapted fuels
    • C10L2270/02Specifically adapted fuels for internal combustion engines
    • C10L2270/023Specifically adapted fuels for internal combustion engines for gasoline engines
    • 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 OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2270/00Specifically adapted fuels
    • C10L2270/04Specifically adapted fuels for turbines, planes, power generation

Definitions

  • the present invention relates to a unleaded aviation gasoline composition, its production and its use in a reciprocating spark ignition aircraft engines.
  • compositions free of lead and having both a sufficiently low freezing point and a high octane number (effective for unleaded aviation gasoline) and, moreover, which compositions also ensure large scale commercial availability for reasonable prices.
  • a high octane unleaded aviation gasoline composition comprising certain amounts of at least one unleaded gasoline base fuel, one or more alkylated benzenes; a composition of one or more of iso-pentane, n-butane, and iso-butane, in combination with aromatic amine(s), said aromatic amine(s) comprising N-methyl-p-toluidine and either or both of N-methyl-m-toluidine and m-Toluidine which are present in the ratio of between about four to one (4:1) and twelve to one (12:1) fulfill the above objectives of a high octane number and a low freezing point.
  • N-methyl-p-toluidine with either or both of N-methyl-m-toluidine and m-Toluidine in a ratio between about four to one (4:1) and twelve to one (12:1) has the particular advantage that commercial supplies are optimized.
  • Illustrative of such optimizations is the nitration of toluene resulting in nitro-toluenes, a key ingredient for various industrial intermediates.
  • toluidines from nitro-toluenes
  • the isomeric products are produced which themselves can be used in the synthesis of N-methyl-m-toluidine and N-methyl-p-toluidine.
  • an aviation gasoline composition comprising:
  • said N-methyl-p-toluidine in combination with either or both of said N-methyl-m-toluidine and m-Toluidine are present at the ratio of about four to one (4:1) up to nine to one (9:1), by weight.
  • Aviation gasoline base fuel is generally described as a gasoline possessing specific properties suitable for fueling aircraft powered by reciprocating ignition engines, e.g. as defined in ASTM D 910-13a.
  • compounds (a) include various unleaded aviation gasoline base fuels refined hydrocarbons derived from crude petroleum, a natural gasoline or blends thereof.
  • aviation gasoline base fuels are normally manufactured by distilling petroleum crude to obtain a distillate with a desired boiling range. Petroleum refining, distillates obtained directly from crude are called straight-run distillates. The hydrocarbon content of a straight-run distillate and, therefore, its octane number, is determined by the composition of the crude. Crudes containing a relatively high proportion of aromatic hydrocarbons yield straight-run gasoline distillates with higher octane numbers than paraffinic crudes.
  • the manufacturing is preferably performed so as to achieve a base fuel having an octane number between 97 and 99.9 by processes known by persons skilled in art.
  • the alkylation process can be performed by processing isobutylene with isobutane to result in the predominant isomer being 2,2,4-trimethylpentane (isooctane), which, by definition, has an octane number of 100.
  • isooctane 2,2,4-trimethylpentane
  • the isobutylene used in this process is usually not pure as the feed typically comes from the catalytic cracking process and may contain propylene, other isomers of butene, and isomers of pentene as well as isoparaffins with carbon numbers from 7 to 12, or even higher, depending on feed composition and reaction conditions.
  • the higher carbon number isoparaffins are less desirable for aviation gasoline base fuels because of their lower octane numbers and higher boiling points. So, refineries producing aviation gasoline base fuels may distill the alkylate into two cuts, namely, a light alkylate or rerun alkylate, containing isoparaffins with nine carbons or fewer for aviation gasoline base fuels blending, and a heavy alkylate.
  • aviation gasoline base fuel is a highly refined product specifically manufactured to meet the demanding performance requirements of aircraft engines. Its specifications make it difficult to meet all the requirements with a single refinery stream, even one such as light alkylate produced specially for aviation gasoline base fuels. So aviation gasoline base fuel, like motor gasoline and most other refinery products, is usually produced by blending two or more components to achieve the desired properties.
  • said unleaded gasoline base fuel (a) has a motor octane number (MON) of at about ninety-eight (98).
  • the alkylated benzenes (b) are mono- di- or trialkylated benzenes.
  • Dialkylated benzenes are preferably selected from the group of xylenes, such as mixtures of two or three of the isomers o-xylene, m-xylene and p-xylene, preferably m-xylene alone.
  • Monoalkylated benzenes are preferably selected from the group of ethyl benzene toluene or mixtures thereof.
  • Preferred examples of trialkylated benzenes are 1,3,5-trimethylbenzene.
  • alkylated benzenes (b) differ from compound (d) as they do not contain heteroatoms.
  • di-alkylated and/or tri-alkylated benzenes such as m-xylene, or 1,3,5-trimethylbenzene are used.
  • N-methyl-p-toluidine with N-methyl-m-toluidine as well as N-methyl-p-toluidine with m-toluidine is preferred.
  • d) also comprises N,N-dimethylated-p-toluidine.
  • said aromatic amine(s) comprise between about six percent (6%) and about fifteen percent (15%) by weight of said high octane unleaded gasoline.
  • aromatic amine(s) (d) comprise products from the nitration of toluene, hydrogenation of the resulting products, which thereby forms m-toluidine and p-toluidine which themselves may be further alkylated to produce N-methyl-p-toluidine and N-methyl-m-toluidine.
  • This also may comprise N,N-dimethylated-p-toluidine. If d) comprises N, N-dimethylated-p-toluidine, than the amount preferably does not exceed 5 wt. % of compound d) and in another preferred embodiment is higher than 0, 01 wt. %.
  • high octane unleaded aviation gasoline blend may have a freezing point at or below minus fifty-eight degrees centigrade (-58°C).
  • Another embodiment of the present invention is a method for the manufacture of a high octane unleaded aviation fuel composition according to the invention by blending together each of the compounds (a), (b), (c), and (d) to provide a finished high octane unleaded aviation fuel composition.
  • the compounds (a), (b), (c), and (d) can be added in various orders during the blending. It is preferred that the compounds (a), (b), (c), and (d) are mixed at temperatures below the lowest boiling point of the selected compounds (a), (b), (c) and (d). It is even more preferred to use temperatures above the melting point of m-toluidine.
  • Another objective of the present invention is the use of an aviation gasoline composition for operating a reciprocating spark ignition aircraft engine.
  • This standard fuel was used with different compounds d), such as about 11 wt. % of the mixtures of

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP16154197.4A 2016-02-04 2016-02-04 Bleifreies flugzeugbenzin Withdrawn EP3202875A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP16154197.4A EP3202875A1 (de) 2016-02-04 2016-02-04 Bleifreies flugzeugbenzin

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP16154197.4A EP3202875A1 (de) 2016-02-04 2016-02-04 Bleifreies flugzeugbenzin

Publications (1)

Publication Number Publication Date
EP3202875A1 true EP3202875A1 (de) 2017-08-09

Family

ID=55310713

Family Applications (1)

Application Number Title Priority Date Filing Date
EP16154197.4A Withdrawn EP3202875A1 (de) 2016-02-04 2016-02-04 Bleifreies flugzeugbenzin

Country Status (1)

Country Link
EP (1) EP3202875A1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11434441B2 (en) 2021-05-07 2022-09-06 John Burger Blended gasoline composition

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5470358A (en) 1993-05-04 1995-11-28 Exxon Research & Engineering Co. Unleaded aviation gasoline
US6258134B1 (en) 1996-05-24 2001-07-10 Texaco Inc. High octane unleaded aviation gasolines
US6767372B2 (en) 2000-09-01 2004-07-27 Chevron U.S.A. Inc. Aviation gasoline containing reduced amounts of tetraethyl lead
US7897034B2 (en) 2004-10-22 2011-03-01 Petroleo Brasileiro S.A.-Petrobras Aviation gasoline formulation
US8628594B1 (en) 2009-12-01 2014-01-14 George W. Braly High octane unleaded aviation fuel
US20140123548A1 (en) * 2009-12-01 2014-05-08 George W. Braly High octane unleaded aviation gasoline
US20140202069A1 (en) * 2007-07-10 2014-07-24 Afton Chemical Corporation Fuel composition comprising a nitrogen-containing compound

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5470358A (en) 1993-05-04 1995-11-28 Exxon Research & Engineering Co. Unleaded aviation gasoline
US6258134B1 (en) 1996-05-24 2001-07-10 Texaco Inc. High octane unleaded aviation gasolines
US6767372B2 (en) 2000-09-01 2004-07-27 Chevron U.S.A. Inc. Aviation gasoline containing reduced amounts of tetraethyl lead
US7897034B2 (en) 2004-10-22 2011-03-01 Petroleo Brasileiro S.A.-Petrobras Aviation gasoline formulation
US20140202069A1 (en) * 2007-07-10 2014-07-24 Afton Chemical Corporation Fuel composition comprising a nitrogen-containing compound
US8628594B1 (en) 2009-12-01 2014-01-14 George W. Braly High octane unleaded aviation fuel
US20140123548A1 (en) * 2009-12-01 2014-05-08 George W. Braly High octane unleaded aviation gasoline

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BROWN J E ET AL: "Mechanism of Aromatic Amine Antiknock Action", INDUSTRIAL AND ENGINEERING CHEMISTRY,, vol. 47, no. 10, 1955, pages 2141 - 2146, XP002539089, DOI: 10.1021/IE50550A034 *
J. E. BROWN, INDUSTRIAL AND ENGINEERING CHEMISTRY, vol. 47, no. 10, 1955, pages 2141 - 2146

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11434441B2 (en) 2021-05-07 2022-09-06 John Burger Blended gasoline composition

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