Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS 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
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/12—Use of additives to fuels or fires for particular purposes for improving the cetane number
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
  • C10L1/026—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for compression ignition
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS 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
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/18—Organic compounds containing oxygen
  • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
  • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS 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
  • C10L10/00—Use of additives to fuels or fires for particular purposes
  • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development

Definitions

• the present invention relates to a diesel fuel composition containing long-chain cyclic glycerol acetals.
• French Oil also targets diesel fuel compositions containing glycerol acetals and / or glycerol acetal ethers.
• the Examples of this patent illustrate the use of some of these acetals and glycerol acetal ethers in diesel fuel compositions at 5% content by weight, by measuring the impact on particle emission.
• the Applicant has unexpectedly discovered, with respect to the prior art, that it is possible to propose glycerol acetals having a cetane number in high mixture, and therefore able to enter substantial proportions in diesel fuel compositions making it possible to 'obtain the environmental benefits, related to the natural origin of the added compounds, and the energy performance compatible with the final application.
• the present invention relates to a diesel fuel composition containing long chain glycerol acetals.
• the invention relates to a diesel fuel composition consisting of a diesel fuel base of either petroleum origin or of vegetable origin and from 1 to 60% by weight of glycerol acetals, characterized in that the acetal of glycerol meets the following formula
• R 1 is an alkyl radical comprising from 5 to 13 carbon atoms of which at least 5 form a linear chain
• R 2 is either H or an alkyl radical of 1 to 7 carbon atoms, the total number of carbon atoms of R 1 R 2 being less than 20 and preferably less than 12.
• Preferred compositions of the invention are those in which R 1 is an n-alkyl radical of 6 carbon atoms or an isoalkyl radical of 7 carbon atoms, R2 being These two acetals come from the first of the reaction of glycerol on n-heptanal (also called heptanaldehyde), and the second of glycerol on 2-ethylhexanal. These two aldehydes are preferred because of their availability on the market and the plant origin for the first.
• the glycerol acetals of the invention are prepared by reaction of an aldehyde or a ketone with glycerol, for example by the methods described in the article by FAJ Meskens titled “Methods for the Preparation of Acetals from Alcohols or Oxiranes”. and Carbonyl Compounds »pages 501 to 522 of the journal” Synthesis "of July 1981 (Georg Thieme Verlag - Stuttgart - New York).
• the glycerol acetals according to the invention can be prepared according to various other methods: by reactive extraction between the aldehyde and a glycerol solution, the acetal produced then being less soluble in the aqueous phase can be easily extracted and separated; by reaction between the glycerol and the aldehyde simulated moving bed in order to strongly shift the equilibrium of the acetalization reactions.
• the acetals of the invention must have physical characteristics compatible with standards such as, for example, the French standard NF EN 590. Main characteristics are density, boiling point, flash point, solubility in water and cetane number.
• the long-chain glycerol acetals are particularly interesting because they have a high cetane number and a high oxygen content (14 to 25% by weight) which promotes the reduction of particulate emissions leading to a reduction of NO x .
• they can be produced from renewable raw materials, both for glycerol which is a co-product of biodiesel obtained by transesterification of triglycerides, and for heptanaldehyde, which can be obtained by thermal cracking from esterified natural oils. of castor oil.
• Cetane boosters may be added to typical diesel cuts as used in the present invention, preferably at levels of at most 1% by weight. Cetane boosters may be selected from nitro compounds and dialkyl peroxides.
• Example 1 Preparation of a mixture between a gas oil and the acetal.
• the cyclic acetal is prepared by reacting glycerol with heptanaldehyde.
• An aqueous solution of glycerol (60% by weight of glycerol, 40% by weight of water) containing 10 moles of glycerol (ie 920 g) is mixed with 10 moles of heptanaldehyde (ie 114 g) or a molar ratio of heptanaldehyde / glycerol of 1.
• a solution of 35% hydrochloric acid is added to the aqueous solution of glycerol + heptanaldehyde in a proportion of 15% relative to glycerol.
• the mixture is then heated and maintained at 40 ° C. for 5 hours. with stirring.
• the acetal obtained is then mixed with a diesel fuel base representative of Euro 2000 formulations: density of the order of 0.830 at 15 ° C., sulfur content of about 290 ppm, cetane number of 51, distillation interval 170-360 ° C.
• the acetal / fuel base ratio is 10% by weight.
• the cetane number of the mixture is then measured according to the ISO 5165 standard. This is slightly greater than 51, which makes it possible to deduce that the cetane number of the acetal in admixture is of the order of 52. 2 Comparative tests of the mixture with the diesel fuel base.
• Tests were conducted to evaluate particle emission performance of diesel fuel compositions containing 10% by weight of glycerol and heptanaldehyde acetal compared to those obtained with reference diesel fuel. .
• the tests were conducted on a diesel vehicle equipped with a direct injection engine. These tests were carried out on the cycle described in European Directive 70/220 / EC, amended by Directive 98/69 / EC (called MVEG-Hs EURO 2000 cycle). This cycle is composed of an urban phase (EUDC cycle with a length of 4,052 km), and an extra-urban phase (ECE cycle with a length of 6,955 km).
• EUDC cycle urban phase
• ECE cycle extra-urban phase

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• 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)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Liquid Carbonaceous Fuels (AREA)

Applications Claiming Priority (2)

Publications (1)

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• 2006
  • 2006-10-23 FR FR0654434A patent/FR2907460A1/fr not_active Withdrawn
• 2007
  • 2007-10-15 AU AU2007310727A patent/AU2007310727A1/en not_active Abandoned
  • 2007-10-15 EP EP07858572A patent/EP2094820A2/de not_active Withdrawn
  • 2007-10-15 WO PCT/FR2007/052145 patent/WO2008050030A2/fr not_active Ceased

Non-Patent Citations (1)

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