EP2726579B1 - Composition - Google Patents

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Publication number
EP2726579B1
EP2726579B1 EP12737237.3A EP12737237A EP2726579B1 EP 2726579 B1 EP2726579 B1 EP 2726579B1 EP 12737237 A EP12737237 A EP 12737237A EP 2726579 B1 EP2726579 B1 EP 2726579B1
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weight
amount
polyglycerols
polyglycerol
fatty acid
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German (de)
English (en)
French (fr)
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EP2726579A1 (en
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Jens Mogens Nielsen
Maja DUELUND
Allan Torben BECH
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DuPont Nutrition Biosciences ApS
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DuPont Nutrition Biosciences ApS
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    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/32—Liquid carbonaceous fuels consisting of coal-oil suspensions or aqueous emulsions or oil emulsions
    • C10L1/328—Oil emulsions containing water or any other hydrophilic phase
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/14—Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
    • C10L2250/08—Emulsion details
    • C10L2250/084—Water in oil (w/o) emulsion

Definitions

  • the present invention relates to a composition.
  • the present invention relates to fuel compositions having reduced nitrogen oxide emissions when combusted.
  • Nitrogen oxides comprise a major irritant in smog and are believed to contribute to tropospheric ozone which is a known threat to health.
  • Various methods for reducing NOx production include the use of catalytic converters, engine timing changes, exhaust recirculation, and the burning of "clean" fuels. These methods are generally too expensive and/or too complicated to be placed in widespread use.
  • the rates at which NOx are formed is related to the flame temperature; a small reduction in flame temperature can result in a large reduction in the production of nitrogen oxides.
  • Another method for introducing water into the combustion area is to use fuel emulsions in which water is emulsified into a fuel continuous phase, i.e., invert fuel emulsions.
  • invert fuel emulsions A problem with these invert fuel emulsions is obtaining and maintaining the stability of the emulsion under conventional use conditions. Gravitational phase separation (during storage) and high temperature high pressure/shear flow rate phase separation (in a working engine) of these emulsions present the major hurdle preventing their commercial use.
  • DE-A-3229918 teaches the preparation of emulsions of 25 wt. of water in diesel oil using emulsifier which are polyesters of saturated or unsaturated fatty acids having 8-22 carbon atoms.
  • the emulsifiers include polyglycerol esters, sorbitan esters or diacetyltartaric acid esters of glycerol esters of the fatty acids.
  • the emulsifiers are dosed in the fuel compositions in amounts of 0.65 to 1.6 wt.%.
  • the diesel emulsions are taught to be stable for at least 6 months and, as compared with pure diesel oil used in engines, give a better fuel economy, less coke deposition and a lower content of CO and hydrocarbons in the exhaust gas.
  • the emulsifier is potentially the most expensive component and dosage at the high levels of this document, such as at 1.6 wt.% would be expensive in use and potentially not commercially viable.
  • JP-A-2003 201485 discloses a fuel composition containing a burning temperature lowering agent, such as water, and one or more polyhydric-alcohol hydroxy-fatty acid ester, for reducing NOx emissions.
  • the present invention addresses the problems associated with the use of fuel emulsion compositions by providing a stable fuel emulsion composition with the beneficial reduction in NOx emissions using commercially viable amounts of emulsifier.
  • the present invention alleviates the problems of the prior art.
  • a fuel composition comprising:
  • a method for improving the stability of a fuel composition containing (a) fuel and (c) water comprising mixing with the fuel and water, (b) a polyglycerol ester of a fatty acid; wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptagly
  • kits for preparing a fuel composition as defined herein comprising a polyglycerol ester of a fatty acid as described herein; together with instructions for use to prepare a fuel composition containing fuel and water.
  • a polyglycerol ester of a fatty acid for improving the stability of a fuel composition containing fuel and water; wherein the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the combined weight of the polygly
  • polyglycerol composition which has predominantly one polyglycerol present, such as diglycerol or triglycerol
  • the polyglycerol composition must be present in a significantly higher amount to provide a fuel/water emulsion which is stable during storage.
  • a broad range of polyglycerols present in a polyglycerol composition and in particular the specific ranges recited herein, then a lower and therefore commercially viable amount of emulsifiers may be used while still providing a fuel and water emulsion which is stable over the period required in use, such as 3 hours.
  • the "flat" distribution of polyglycerols allows for this enhanced effect at low dosages.
  • flat distribution it is meant that the polyglycerols contain a broad range of polyglycerols chain lengths and the broad range of polyglycerols are present in an amount such that only a few polyglycerol chain lengths dominate the distribution of polyglycerols. For example in a flat distribution one or two polyglycerol chain lengths do not make up 70 or 80% of the total amount of polyglycerols.
  • a fuel composition comprising:
  • polyglycerol ester of a fatty acid is an emulsifier comprising a polyglycerol 'backbone' onto which fatty acid side chains are attached.
  • Polyglycerol esters of fatty acids are typically prepared by polymerisation of glycerol to provide one or more polyglycerols to which the fatty acids are then attached.
  • the fatty acids are generally attached by one of two routes.
  • a first route involves the direct attachment of the fatty acid to the polyglycerol.
  • the second route involves inter-esterifying a polyglycerol and a triglyceride thereby transferring fatty acids from the triglyceride to the polyglycerol.
  • the polymerisation of glycerol typically provides a mixture of polyglycerols of different degrees of polymerisation. The mixture of polyglycerols of different degrees of polymerisation is described herein as a polyglycerol composition.
  • references to a polyglycerol composition having particular polyglycerol components requires only that those components be present in the amount specified. It will be appreciated by one skilled in the art that because of the nature of polymerisation of glycerol, the polyglycerol composition may contain other polyglycerols having degrees of polymerisation not recited herein. In determining the amounts of polyglycerols in the polyglycerol composition, the total amount of all polyglycerols (irrespective of degree of polymerisation) is determined to provide the total weight of the polyglycerol composition. Materials which are not a polyglycerol do not form part of the polyglycerol composition and their weight is not considered when determining the total weight of the polyglycerol composition.
  • the combined weight of the polyglycerols encompass the total combined weight of all polyglycerols, irrespective of their chain length and irrespective of whether the polyglycerol is recited in the listing of polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of diglycerol in an amount of 11.0 to 34.0 weight% based on the combined weight of the polyglycerols; triglycerol in an amount of 9.5 to 24.5 weight% based on the combined weight of the polyglycerols; tetraglycerol in an amount of 6.0 to 21.0 weight% based on the combined weight of the polyglycerols; pentaglycerol in an amount of 3.5 to 19.0 weight% based on the combined weight of the polyglycerols; hexaglycerol in an amount of 6.0 to 13.5 weight% based on the combined weight of the polyglycerols; heptaglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols; octaglycerol in an amount of 3.0 to 12.0 weight% based on the combined weight of the polyglycerols
  • polyglycerols may be either in the form of a cyclic polyglycerol or an acyclic polyglycerol.
  • Acyclic polyglycerols are straight chain and branched chain polyglycerols, that is acyclic polyglycerols are formed entirely from glycerol groups linked such that no rings are formed. Cyclic polyglycerols contain a ring structure.
  • References in the present specification to a polyglycerol of a particular degree of polymerisation, for example triglycerol referring to a polyglycerol having a degree of polymerisation of 3, include both the polyglycerol in cyclic form and in acyclic form.
  • the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 25.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 21.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5 weight% based on the combined weight of the polyglycerols.
  • the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.5 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
  • the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
  • the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5 weight% based on the combined weight of the polyglycerols.
  • the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
  • the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
  • the diglycerol comprises acyclic diglycerol in an amount of 6.0 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 5.5 to 13.0 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 7.0 to 15.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 9.5 weight% based on the combined weight of the polyglycerols.
  • the tetraglycerol comprises acyclic tetraglycerol in an amount of 5.0 to 13.0 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
  • the pentaglycerol comprises acyclic pentaglycerol in an amount of 3.0 to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 0.5 to 8.0 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the polyglycerol composition used to form the, polyglycerol ester of a fatty acid comprises diglycerol in an amount of 15.0 to 23.5 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an amount of 13.5 to 20.5 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises tetraglycerol in an amount of 10.0 to 17.0 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in an amount of 8.0 to 14.5 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises hexaglycerol in an amount of 8.0 to 11.5 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises octaglycerol in an amount of 6.5 to 10.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in an amount of 4.0 to 8.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises decaglycerol in an amount of 1.5 to 6.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises unadecaglycerol in an amount of 0.5 to 5.0 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the diglycerol comprises acyclic diglycerol in an amount of 8.0 to 12.5 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 9.0 to 13.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 4.5 to 7.5 weight% based on the combined weight of the polyglycerols.
  • the tetraglycerol comprises acyclic tetraglycerol in an amount of 7.5 to 11.0 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 2.5 to 6.0 weight% based on the combined weight of the polyglycerols.
  • the pentaglycerol comprises acyclic pentaglycerol in an amount of 5.0 to 9.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 2.5 to 6.0 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises diglycerol in an amount of 17.6 to 21.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an amount of 15.9 to 18.1 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises tetraglycerol in an amount of 12.5 to 14.0 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in an amount of 10.5 to 12.2 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises hexaglycerol in an amount of 9.3 to 10.1 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in an amount of 8.6 to 9.9 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises octaglycerol in an amount of 7.3 to 8.9 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in an amount of 5.5 to 6.4 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises decaglycerol in an amount of 2.9 to 4.5 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises unadecaglycerol in an amount of 1.8 to 3.7 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the diglycerol comprises acyclic diglycerol in an amount of 9.1 to 11.4 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 8.5 to 9.5 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 10.0 to 11.8 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 5.9 to 6.3 weight% based on the combined weight of the polyglycerols.
  • the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.4 to 9.5 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 4.1 to 4.4 weight% based on the combined weight of the polyglycerols.
  • the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.7 to 7.6 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 3.8 to 4.6 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises diglycerol in an amount of 18.0 to 32.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an amount of 16.0 to 24.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises tetraglycerol in an amount of 12.0 to 16.0 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in an amount of 8.0 to 12.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises hexaglycerol in an amount of 7.0 to 11.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in an amount of 5.0 to 10.0 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises octaglycerol in an amount of 3.0 to 9.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in an amount of 1.5 to 7.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises decaglycerol in an amount of 0.0 to 4.5 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises unadecaglycerol in an amount of 0.0 to 4.0 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the diglycerol comprises acyclic diglycerol in an amount of 9.0 to 24.5 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 6.5 to 10.0 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 9.0 to 20.5 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 3.5 to 6.5 weight% based on the combined weight of the polyglycerols.
  • the tetraglycerol comprises acyclic tetraglycerol in an amount of 8.0 to 13.5 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 2.0 to 4.5 weight% based on the combined weight of the polyglycerols.
  • the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.0 to 9.0 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 2.0 to 5.0 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises diglycerol in an amount of 26.0 to 34.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises triglycerol in an amount of 21.0 to 25.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises tetraglycerol in an amount of 12.0 to 17.0 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises pentaglycerol in an amount of 8.0 to 12.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises hexaglycerol in an amount of 6.0 to 10.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises heptaglycerol in an amount of 4.5 to 7.5 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises octaglycerol in an amount of 2.5 to 5.5 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises nonaglycerol in an amount of 1.0 to 3.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises decaglycerol in an amount of 0.0 to 1.0 weight% based on the combined weight of the polyglycerols. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises unadecaglycerol in an amount of 0.0 to 0.5 weight% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises unadecaglycerol in an amount of 0.0 to 0.01 weight% based on the combined weight of the polyglycerols.
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the diglycerol comprises acyclic diglycerol in an amount of 20.0 to 26.0 weight% based on the combined weight of the polyglycerols, and cyclic diglycerol in an amount of 6.5 to 8.0 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 18.0 to 21.0 weight% based on the combined weight of the polyglycerols, and cyclic triglycerol in an amount of 2.5 to 5.0 weight% based on the combined weight of the polyglycerols.
  • the tetraglycerol comprises acyclic tetraglycerol in an amount of 11.0 to 14.5 weight% based on the combined weight of the polyglycerols, and cyclic tetraglycerol in an amount of 1.5 to 4.0 weight% based on the combined weight of the polyglycerols.
  • the pentaglycerol comprises acyclic pentaglycerol in an amount of 6.5 to 9.5 weight% based on the combined weight of the polyglycerols, and cyclic pentaglycerol in an amount of 1.5 to 4.0 weight% based on the combined weight of the polyglycerols.
  • the triglycerol comprises acyclic triglycerol in an amount of 18.0 to 21.0 weight% based on the combined weight of the polyglycerols,
  • polyglycerol composition used to form the polyglycerol ester of a fatty acid comprises a mixture of
  • the fatty acid side chains attached to the polyglycerol may be of any suitable length.
  • the polyglycerol ester of a fatty acid may be a polyglycerol ester of a single fatty acid, or polyglycerol ester of a mixture of fatty acids.
  • the fatty chain lengths of the fatty acids of the polyglycerol ester need not be of the same length.
  • the polyglycerol ester of a fatty acid is an ester of a fatty acid of a C12 to C22 fatty acid.
  • the polyglycerol ester of a fatty acid is an ester of a C16 or C22 fatty acid.
  • the polyglycerol ester of a fatty acid is an ester of a C16 or C18 fatty acid.
  • the polyglycerol ester of a fatty acid is an ester of a C18 fatty acid.
  • the fatty acid of the polyglycerol ester of a fatty acid may be saturated fatty acid, unsaturated fatty acid or a mixture of saturated fatty acid and unsaturated fatty acid.
  • the fatty acid of the polyglycerol ester of a fatty acid is an unsaturated fatty acid.
  • the fatty acid of the polyglycerol ester of a fatty acid may be mono- or di-unsaturated fatty acid.
  • the fatty acid of the polyglycerol ester of a fatty acid is a mono-unsaturated fatty acid.
  • a highly preferred fatty acid of the polyglycerol ester of a fatty acid is oleic acid ((9Z)-Octadec-9-enoic acid).
  • the fatty acids attached to the polyglycerol may be provided from any suitable source.
  • the polyglycerol fatty acid ester is prepared from fatty acids from oils selected from rape seed oil, high oleic rape seed oil, soy oil, high oleic sunflower oil, tall oil and mixtures thereof.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 880 to 1230 mg KOH/g. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1130 to 1230 mg KOH/g. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 880 to 1060 mg KOH/g. In a further preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 950 to 990 mg KOH/g.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50°C of from 1.4860 to 1.4925. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50°C of from 1.4895 to 1.4925. In a further preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50°C of from 1.4900 to 1.4920.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50°C of from 1.4900 to 1.4910. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 25°C of from 1.4855 to 1.4935.
  • the polyglycerol ester of a fatty acid has a viscosity of less than 700 mPa s at 20°C, such as less than 600 mPa s at 20°C, such as less than 500 mPa s at 20°C, such as less than 400 mPa s at 20°C, such as less than 350 mPa s at 20°C, such as less than 300 mPa s at 20°C, such as less than 250 mPa s at 20°C, such as less than 200 mPa s at 20°C.
  • a low viscosity such as that described above, and preferably less than 200 mPa s at 20°C, is an important factor in the preparation of an effective emulsion.
  • the viscosity the polyglycerol ester of a fatty acid may be controlled is by control of the ratio of the polyol to triglyceride source when preparing the present polyglycerol ester of a fatty acid, as well as the fatty acid profile which is described in detail herein.
  • the effect of ratio of the polyol to triglyceride source is shown in Figure 8 .
  • the polyglycerol ester of a fatty acid is prepared by reacting a polyglycerol and a fatty acid triglyceride in a ratio of polyglycerol to fatty acid triglyceride of from 1:1 to 1:10.
  • the polyglycerol ester of a fatty acid is prepared by reacting a polyglycerol and a fatty acid triglyceride in a ratio of polyglycerol to fatty acid triglyceride of from 1:1 to 1:9, such as from 1:1 to 1:8, such as from 1:1 to 1:7, such as from 1:1 to 1:6, such as from 1:1 to 1:5, such as from 1:1 to 1:4, such as from 1:2 to 1:4, such as from 1:2 to 1:3, such as approximately 1:2.8, such as from 1:4 to 1:9, such as from 1:4 to 1:8, such as from 1:4 to 1:7, such as from 1:4 to 1:6, such as from 1:4 to 1:5, such as from 1:5 to 1:7, such as from 1:6 to 1:7, such as approximately 1:6.7.
  • the polyglycerol ester may be dosed in the water and fuel composition in any suitable amount to provide an emulsion of desired stability.
  • the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of from 0.1 to 2.0 wt.% based on the total fuel composition.
  • the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of from 0.1 to 1.0 wt.% based on the total fuel composition.
  • the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of from 0.1 to 0.5 wt.% based on the total fuel composition. In a further aspect the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of less than 0.5 wt.% based on the total fuel composition. In a further aspect the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of less than 0.3 wt.% based on the total fuel composition.
  • the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of less than 0.25 wt.% based on the total fuel composition.
  • the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of less than 0.2 wt.% based on the total fuel composition.
  • the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of less than 0.15 wt.% based on the total fuel composition.
  • the fuel composition comprises a polyglycerol ester of a fatty acid prepared from a mixture of polyglycerols as described herein in an amount of less than 0.1 wt.% based on the total fuel composition.
  • the emulsifier may be used in lower amounts than required in the prior art.
  • the polyglycerol ester of a fatty acid is present in an amount of less than 0.25 wt.%.
  • the improved activity of the composition of polyglycerol esters of the present invention allows for the emulsifier to be dosed at lower amounts than had previously been required in the prior art. This is advantageous both for reasons of cost and also for storage. These materials are dosed in use and therefore must be transported by the user. Minimising the amount of material required to achieve the desired effect is important for end users.
  • the present composition allows for use at lower levels than the prior art, the present composition may be dosed at any level, for example it may be dosed at a higher level in a demanding application. It is appreciated by one skilled in the art that depending on the required use and stability time desired the polyglycerol ester of a fatty acid may be dosed at any amount.
  • the emulsifiers described allow for the preparation of an emulsion of fuel and water.
  • a fuel suitable for preparing into an emulsion but which has yet to be combined with water is hereby disclosed.
  • the fuel containing the emulsifiers is combined with water and the fuel composition comprises (c) water.
  • the fuel composition may be prepared by first dosing the polyglycerol ester of a fatty acid into the fuel, such as marine gasoil (MGO), after which water is dosed into the fuel/emulsifier blend.
  • MGO marine gasoil
  • the amount of water may be selected based on the requirements of the combustion system.
  • the fuel composition farther comprises (c) water in an amount of from 10 to 70 wt.% based on the total fuel composition.
  • the water is present in an amount of from 30 to 60 wt.% based on the total fuel composition.
  • the water is present in an amount of from 33 to 50 wt.% based on the total fuel composition.
  • composition according to the present invention may comprise one or more additives for example, to improve various aspects of the fuel to which the composition is typically added or to improve various aspects of the combustion system performance.
  • additional additives include detergents, carrier oils, anti-oxidants, corrosion inhibitors, colour stabilisers, metal deactivators, cetane number improvers, other combustion improvers, antifoams, pour point depressants, cold filter plugging point depressants, wax anti-settling additives, dispersants, deodorants, dyes, smoke suppressants, lubricity agents, and other particulate filter regeneration additives.
  • the fuel may be any fuel suitable for combustion where reduction of NOx is desired.
  • the fuel is a fuel for spark ignition engines such as a gasoline engine.
  • the fuel is a fuel for a high compression spontaneous ignition engine.
  • the fuel is selected from diesel, heavy fuel oil, marine gasoil (MGO) and kerosene.
  • the diesel may be biodiesel, low sulphur diesel and ultra-low sulphur diesel.
  • the fuel is marine gasoil.
  • the marine gasoil may be any suitable marine gasoil. In one aspect it is a fuel having a (i) a density of 0.85-0.89g/cm 3 , a cetane Number of approximately 45; and a flash point of greater than 55°C.
  • polyglycerol esters were prepared and tested. Two were broad range polyglycerol (BRPG) esters in accordance with the present invention - one based on soya bean oil and one based on oleic acid. Two were triglycerol esters prepared as a comparison - one based on soya bean oil and one based on oleic acid.
  • BRPG polyglycerol
  • triglycerol esters prepared as a comparison - one based on soya bean oil and one based on oleic acid.
  • Glycerol 1250 kg 50% NaOH in water: 9.17 kg
  • Glycerol and NaOH solution is added to the reactor. Heated to 240°C while taking care with columns and condensers not to distill off glycerol. The heating to 240°C takes about 3h. Then the pressure is lowered carefully to about 30 mbar to remove reaction water from the polymerisation of glycerol. After about 7-14 hours at 240°C samples are withdrawn from the reactor for measurement of refractive index at 50.0°C, n D 50,0 .
  • the refractive index is used to determine the termination of the reaction.
  • the refractive index should be in the interval of 1.4900-1.4920. If the refractive index is not yet in the interval, the reaction is continued for further 1 hour and another sample is withdrawn for measurement. This continues until the refractive index is within the interval. When the polyglycerol is within the stop-interval the temperature is lowered to 120°C.
  • Polyglycerol PGE 24401198 Soyabean oil: 700g Polyglycerol: 203.2g 50% NaOH in water: 3.80g
  • the polyglycerol was prepared in accordance with the above process.
  • Temperature is raised to 90°C. Pressure is lowered to about 50 mBar when the mixture reaches 90°C. Temperature is then raised to 230°C and held at that temperature for 30 min. Cooled to about 90°C. Pressure equalised with nitrogen at 90°C. The product is clear.
  • the polyglycerol was prepared in accordance with the above process.
  • Triglycerol PGE 2528 / 072 (Comparative): Soyabean oil: 700g Triglycerol: 215g 50% NaOH in water: 3.80g
  • the triglycerol was obtained from Solvay.
  • Triglycerol PGE 2526 / 159 (Comparative): Oleic acid 90%: 340g Triglycerol: 108g Glycerol: 37g 50% NaOH in water: 1.75g
  • the triglycerol was obtained from Solvay.
  • emulsifiers were tested in water-in-fuel emulsions, WIF-emulsions, with 50% water content at 55°C.
  • the emulsifiers are listed in table 1. Dosages 0.5%, 0.25% and 0.1% based on the emulsion.
  • the emulsions (200 g) were prepared by slowly adding the water phase to the fuel (MGO) during homogenization with Ultra Turrex at 20500 rpm for 64 s. Both the MGO and the water were heated to 55°C prior to emulsification.
  • the marine gasoil (diesel) used in the testing was Shell Thermo heating oil.
  • the water droplet size distribution is shown in Table 2. Note the significant increase in water droplet size at low emulsifier concentration. Table 2 Water droplet size distribution. Emulsifier Conc % Emulsion Conc % Diesel Water % Emulsion Temp °C D2.5 ⁇ m D50.0 ⁇ m 2440/198 0.50 1.00 50 55 0.6 7.7 BRPG-soy 0.25 0.50 50 55 3.3 16.6 0.10 0.20 50 55 4.2 63.0 2526/160 0.50 1.00 50 55 0.5 7.1 BRPG - oleate 0.25 0.50 50 55 3.7 18.6 0.10 0.20 50 55 6.7 47.0 2528/072 0.50 1.00 50 55 0.4 6.6 Triglycerol - soy 0.25 0.50 50 55 2.7 17.8 0.10 0.20 50 55 2.8 87.8 2526/159 0.50 1.00 50 55 0.5 7.4 Triglycerol - oleate 0.25 0.50 50 55 1.9 14.9 0.10 0.20 50 55 4.5 72.7
  • the D50.0 values are compared in Figure 1 , where the huge increase in droplet size at 0.1 % dosage level is clearly seen.
  • the graph also shows that at very stressing conditions (0.1% emulsifier dosage) PGE based on BRPG (broad range polyglycerol) results in smaller water droplets than PGE based on triglycerol.
  • PGE based on fatty acids from soy oil results in larger droplets than PGE based on pure oleic acid.
  • FIG. 3a, 3b and 3c are shown the degree of water droplet sedimentation in the emulsions during 3 hours storage at 55°C with 0.5%, 0.25% and 0.1% emulsifier addition.
  • the degree of sedimentation is expressed as the free diesel oil on top of the samples in percentage of the total samples height. The values were generated by image analysis. The difference in the degree of sedimentation between the dosage levels is to be noted. At 0.1% dosage the sedimentation is ten-fold larger than at 0.5% dosage level.
  • the ester of triglycerol and soy oil performs poorly at low concentration. Hence the performance of this emulsifier is more sensitive to dosage reduction compared to the broad range polyglycerol ester emulsifiers of the present invention.
  • polyglycerol esters based on broad range polyglycerols results in smaller water droplet and reduced water droplet sedimentation during storage as compared to polyglycerolesters based on triglycerol. This effect is seen at very low emulsifier addition (0.1%) representing stressing conditions, which most like a real life situation. Furthermore it is concluded that a fatty acids composition with high oleic acid content is superior to a composition with high linoleic acid (soy oil) based on above attributes.
  • polyglycerol esters were prepared and tested. Each was a broad range polyglycerol (BRPG) esters in accordance with the present invention and each was based on rape seed oil. Two were triglycerol esters and two were hexaglycerol esters.
  • BRPG polyglycerol
  • esters in accordance with the present invention were compared against a comparison prepared from triglycerol and soy oil (REF PGE or REF).
  • Rapeseed oil 920g Broad Range Hexaglycerol (BRHG): 138g 50% NaOH in water: 1.92g
  • the hexaglycerol was prepared by polymerisation in the same manner as described in Example 1.
  • Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear. Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The product is clear.
  • the hexaglycerol was prepared by polymerisation in the same manner as described in Example 1.
  • Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear. Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The product is clear.
  • the triglycerol was prepared by polymerisation in the same manner as described in Example 1 except the refractive index was at 25°C was changed from 1.4855 to 1.4935.
  • Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear. Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The product is clear.
  • the triglycerol was prepared by polymerisation in the same manner as described in Example 1 except the refractive index was at 25°C was changed from 1.4855 to 1.4935.
  • Pressure is lowered to 50 - 100 mBar when the mixture reaches 235°C and is clear. Temperature is raised from room temperature to 235°C in 50 min. The reaction mixture is held at 235°C for 2.5h, then cooled to 100°C and pressure equalised with nitrogen. The product is clear.
  • the polyglycerol esters synthesized are summarised in Table 4. Three types of polyglycerol were included in series, they were two triglycerols and one hexaglycerol The fatty acid source was either soy oil or rape seed oil. Table 4. BRHG / BRTG: Broad range Hexa/Tri-Glycerol Sample Polyol type Wt.

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EP2726579A1 (en) 2014-05-07

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