EP1274818B1 - Utilisation du di-isobutylene dans une composition de carburant - Google Patents

Utilisation du di-isobutylene dans une composition de carburant Download PDF

Info

Publication number
EP1274818B1
EP1274818B1 EP01920806A EP01920806A EP1274818B1 EP 1274818 B1 EP1274818 B1 EP 1274818B1 EP 01920806 A EP01920806 A EP 01920806A EP 01920806 A EP01920806 A EP 01920806A EP 1274818 B1 EP1274818 B1 EP 1274818B1
Authority
EP
European Patent Office
Prior art keywords
fuel
isobutylene
ene
trimethylpent
less
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
EP01920806A
Other languages
German (de)
English (en)
Other versions
EP1274818A1 (fr
Inventor
Stuart Pace
Alan Mark Schilowitz
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
ExxonMobil Research and Engineering 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 ExxonMobil Research and Engineering Co filed Critical ExxonMobil Research and Engineering Co
Publication of EP1274818A1 publication Critical patent/EP1274818A1/fr
Application granted granted Critical
Publication of EP1274818B1 publication Critical patent/EP1274818B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • C10L1/04Liquid carbonaceous fuels essentially based on blends of hydrocarbons
    • 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
    • C10L1/1608Well defined compounds, e.g. hexane, benzene

Definitions

  • This invention relates to fuel compositions comprising an anti-foam additive to reduce the time needed to break up any foam formation during the filling of a vehicle's fuel tank thereby enabling a more complete filling of the tank and at the same time reducing risk of spillage.
  • the problem of foaming of fuels due to entrainment of air during filling of fuel tanks of vehicles is well known.
  • the problem has hitherto been mitigated by adding to the fuel antifoams which are substantially non-hydrocarbonaceous.
  • An example of such a non-hydrocarbonaceous additive is a silicon containing polymer.
  • Non-hydrocarbonaceous additives usually have to undergo a rigorous testing programme with respect to their compatibility with the fuel and also environmental considerations. However, if the additive is a hydrocarbon, especially a non-aromatic hydrocarbon, the issues of compatibility and environmental considerations are not as critical.
  • JP-A-08073870 discloses gasoline compositions for two-cycle engines which contain at least 10 vol % 7-8C olefinic hydrocarbons and have a Tso of 93-105°C, a final distillation temperature of 110-150°C and an octane No. by the motor method of at least 95.
  • 11 olefins listed 2,4,4-trimethyl-1-pentene.
  • these olefins are used as a blend of several.
  • the olefins are not used as anti-foaming agents but to achieve high output and low fuel consumption and to avoid seizure even at high compression ratios.
  • gasoline used in two-cycle engines ie two-stroke engines
  • SAE Paper 950740 describes various compounds being added to a mixture of toluene (boiling point about 110°C) and isooctane (boiling point 99°C) to monitor the emissions of vehicles powered therewith.
  • One such compound added is di-isobutylene in an amount > 15% by volume. The resultant mixture is unlikely to have a final boiling point above 150°C and there is no mention of the use of di-isobutylene as an anti-foam in this document.
  • JP-A-06200263 describes a composition which contains at least 65% by volume based on the total base fuel of a high boiling component with a boiling point from 80-120°C which uses 7-8C paraffin type or olefin type hydrocarbon.
  • the abstract of this patent makes no mention of any other base fuels or specific olefins in this range and there is no mention of any of such olefins as anti-foaming agents.
  • WO 99/49003 discloses gasoline formulations which contain, inter alia, at least 5% by volume of saturated C 7 /C 8 branched chain hydrocarbons. In any event, there is no mention of the use of these as anti-foaming agents.
  • the present invention provides the use of di-isobutylene as an anti-foam for a base fuel as defined in claim 1 of the set of claims following this description.
  • Optional and/or preferred features of the invention are defined in the other claims in the set of claims following this description.
  • the base fuels may comprise mixtures of saturated, olefinic, and aromatic hydrocarbons, and these can be derived from straight run streams, thermally or catalytically cracked hydrocarbon feedstocks, hydrocracked petroleum fractions, catalytically reformed hydrocarbons, or synthetically produced hydrocarbon mixtures.
  • the present invention is particularly applicable to a broad range of petroleum fuels from the light boiling gasoline (which typically boils between 50 and 200°C) to distillate fuel (which typically boils between 150 and 400°C).
  • the most common distillate fuels suitable for use in the present invention as base fuels are selected from motor gasoline, kerosene and diesel fuels.
  • the sulfur content of the base fuel is suitably less than100 ppm by weight, preferably less than 50 ppm by weight and more preferably less than 30 ppm by weight.
  • Such low sulfur levels can be achieved in a number of ways. For instance, this may be achieved by well known methods such as, e.g., catalytic hydrodesulfurization.
  • Di-isobutylene used as an anti-foam in accordance with the use of the invention is employed in an amount greater than 2.5% by volume based on the total fuel composition, suitably up to 35% by volume, preferably less than 15% by volume, more preferably from 5.0 to less than 15% by volume, still more preferably from 7.5% to less than 15% by volume of the total fuel composition.
  • Di-isobutylene can readily be obtained by dimerization of isobutylene. It is generally prepared from a crude mixture of olefins and usually contains a mixture of various C 8 -olefin isomers but always comprises 2,4,4-trimethylpent-1-ene admixed with 2,4,4-trimethylpent-2-ene. These two isomers are suitably present in the di-isobutylene in a weight ratio of about 75% (-1-ene) to about 25% (-2-ene).
  • Di-isobutylene has an advantage over other non-hydrocarbonaceous anti-foams such as silicon based polymers in that di-isobutylene is substantially miscible with conventional fuels in all proportions.
  • Di-isobutylene has the further advantage that current plants making methyl tert-butyl ether (hereafter "MTBE") from isobutylene and methanol (MTBE having more recently fallen out of favour upon environmental considerations), can be readily switched to convert the same isobutylene feedstock to di-isobutylene.
  • MTBE methyl tert-butyl ether
  • MTBE methyl tert-butyl ether
  • MTBE methyl tert-butyl ether
  • MTBE methyl tert-butyl ether
  • MTBE methyl tert-butyl ether
  • MTBE methyl tert-butyl ether
  • MTBE methyl tert-butyl ether
  • Tests were carried out in which di-isobutylene (a mixture of 3 parts 2,4,4-trimethylpent-1-ene and 1 part 2,4,4-trimethylpent-2-ene) was added to varying quantities to a distillate fuel which was susceptible to foam formation.
  • di-isobutylene a mixture of 3 parts 2,4,4-trimethylpent-1-ene and 1 part 2,4,4-trimethylpent-2-ene

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)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Claims (10)

  1. Utilisation de diisobutylène comme agent anti-mousse pour un carburant de base ayant un point d'ébullition final supérieur à 150°C, dans laquelle le diisobutylène constitue plus de 2,5% en volume de la composition totale de carburant.
  2. Utilisation selon la revendication 1, dans laquelle le diisobutylène constitue moins de 15% en volume de la composition totale de carburant.
  3. Utilisation selon la revendication 1 ou 2, dans laquelle le düsobutylène constitue 5% à moins de 15% en volume de la composition totale de carburant.
  4. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le düsobutylène comprend un mélange de 2,4,4-triméthylpent-1-ène et de 2,4,4-triméthylpent-2-ène.
  5. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le diisobutylène comprend un mélange de 2,4,4-triméthylpent-1-ène et de 2,4,4-triméthylpent-2-ène dans un rapport d'environ 75% à environ 25% en poids.
  6. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le carburant de base comprend des mélanges d'hydrocarbures saturés, oléfiniques et aromatiques qui peuvent être tirés de courants de première distillation, de charges d'hydrocarbures craquées par voie thermique ou catalytique, de fractions de pétrole hydrocraquées, d'hydrocarbures reformés par voie catalytique ou de mélanges d'hydrocarbures produits par synthèse.
  7. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le carburant de base est un carburant de pétrole ayant une plage d'ébullition allant de l'essence (qui bout typiquement dans la plage de 50 à 200°C avec un point d'ébullition final dépassant 150°C) à un carburant de distillat (qui bout typiquement entre 150 et 400°C).
  8. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le carburant de base est un carburant de distillat courant choisi parmi l'essence de moteur, le kerosène et les carburants diesel.
  9. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le carburant de base a une teneur en soufre inférieure à 100 ppm en poids.
  10. Utilisation selon l'une quelconque des revendications précédentes, dans laquelle le carburant de base a une teneur en soufre inférieure à 50 ppm en poids.
EP01920806A 2000-02-14 2001-02-08 Utilisation du di-isobutylene dans une composition de carburant Expired - Lifetime EP1274818B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0003386 2000-02-14
GB0003386A GB2359094A (en) 2000-02-14 2000-02-14 Anti-foam fuel composition
PCT/US2001/009792 WO2001060955A1 (fr) 2000-02-14 2001-02-08 Composition de carburant

Publications (2)

Publication Number Publication Date
EP1274818A1 EP1274818A1 (fr) 2003-01-15
EP1274818B1 true EP1274818B1 (fr) 2006-05-31

Family

ID=9885576

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01920806A Expired - Lifetime EP1274818B1 (fr) 2000-02-14 2001-02-08 Utilisation du di-isobutylene dans une composition de carburant

Country Status (7)

Country Link
EP (1) EP1274818B1 (fr)
JP (1) JP5102421B2 (fr)
AT (1) ATE328052T1 (fr)
CA (1) CA2397456A1 (fr)
DE (1) DE60120146T2 (fr)
GB (1) GB2359094A (fr)
WO (1) WO2001060955A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030094397A1 (en) * 2001-08-15 2003-05-22 Fortum Oyj Clean-burning MTBE-free gasoline fuel
JP5390748B2 (ja) 2003-09-03 2014-01-15 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ 燃料組成物
WO2005021688A1 (fr) * 2003-09-03 2005-03-10 Shell Internationale Research Maatschappij B.V. Compositions de combustible comprenant un combustible derive de fischer-tropsch
US7662757B2 (en) * 2006-06-27 2010-02-16 Exxonmobil Research And Engineering Company Stable defoamant composition containing GTL fluid and/or hydrodewaxate and/or hydroisomerized/catalytic (and/or solvent) dewaxed fluid as diluent
JP5153146B2 (ja) * 2007-01-22 2013-02-27 コスモ石油株式会社 ガソリン組成物
JP5153147B2 (ja) * 2007-01-22 2013-02-27 コスモ石油株式会社 ガソリン組成物
JP2009132900A (ja) * 2007-11-01 2009-06-18 Japan Energy Corp 消泡性の良い低硫黄燃料油組成物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS649293A (en) * 1987-06-30 1989-01-12 Nippon Oil Co Ltd Clear gasoline
JPH05103995A (ja) * 1991-10-17 1993-04-27 Maruzen Petrochem Co Ltd オレフインの不均化触媒およびその触媒を用いたオレフインの不均化方法
JPH0873870A (ja) * 1994-09-05 1996-03-19 Tonen Corp 2サイクルエンジン用ガソリン組成物
JPH08109385A (ja) * 1994-10-12 1996-04-30 Jiyomo Technical Res Center:Kk ガソリン
JPH09157673A (ja) * 1995-12-08 1997-06-17 Mitsubishi Gas Chem Co Inc ポリオールエステルおよびその製造法

Also Published As

Publication number Publication date
GB2359094A (en) 2001-08-15
JP2003523453A (ja) 2003-08-05
DE60120146D1 (de) 2006-07-06
EP1274818A1 (fr) 2003-01-15
DE60120146T2 (de) 2007-03-29
CA2397456A1 (fr) 2001-08-23
JP5102421B2 (ja) 2012-12-19
GB0003386D0 (en) 2000-04-05
ATE328052T1 (de) 2006-06-15
WO2001060955A1 (fr) 2001-08-23

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