WO2016156302A1 - Compositions de carburant comprenant des esters de polyglycérol d'un acide gras - Google Patents

Compositions de carburant comprenant des esters de polyglycérol d'un acide gras Download PDF

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Publication number
WO2016156302A1
WO2016156302A1 PCT/EP2016/056779 EP2016056779W WO2016156302A1 WO 2016156302 A1 WO2016156302 A1 WO 2016156302A1 EP 2016056779 W EP2016056779 W EP 2016056779W WO 2016156302 A1 WO2016156302 A1 WO 2016156302A1
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Prior art keywords
polyglycerol
fatty acid
amount
polyglycerols
ester
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PCT/EP2016/056779
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English (en)
Inventor
Jens Mogens Nielsen
Allan Torben BECH
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Dupont Nutrition Biosciences Aps
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Publication of WO2016156302A1 publication Critical patent/WO2016156302A1/fr

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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
    • 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
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/198—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid
    • C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters

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.
  • WO2013/001064 teaches that many of the problems of the prior art may be overcome by selection of a polyglycerol ester formed from a polyglycerol having a particular profile of polyglycerol components. A 'broad range polyglycerol' is utilised.
  • 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.
  • the present invention provides a fuel composition comprising:
  • the fuel composition contains monoglycendes, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycendes, diglycerides and triglycerides, and the polyglycerol ester is an ester of a mixture of fatty acids present in an amount of no greater than 0.5 wt.% based on the total fuel composition.
  • the present invention provides a method for improving the stability of a fuel composition containing (a) fuel and (c) water, the method comprising mixing (b) a polyglycerol ester of a fatty acid with the fuel and water to form a fuel composition, wherein the polyglycerol ester contains monoglycendes, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol ester of a fatty acid, monoglycendes, diglycerides and triglycerides, and the polyglycerol ester is an ester of a mixture of fatty acids present in an amount of no greater than 0.5 wt.% based on the total fuel composition.
  • the present invention provides use of a polyglycerol ester of a fatty acid for improving the stability of a fuel composition containing fuel and water; wherein the polyglycerol ester contains monoglycerides, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol ester of a fatty acid, monoglycerides, diglycerides and triglycerides, and the polyglycerol ester is an ester of a mixture of fatty acids present in an amount of no greater than 0.5 wt.% based on the total fuel composition.
  • the present invention provides a kit for preparing a fuel composition comprising
  • the fuel composition contains monoglycerides, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides, and the polyglycerol ester is an ester of a mixture of fatty acids present in an amount of no greater than 0.5 wt.% based on the total fuel composition,
  • kit comprises
  • polyglycerol ester of a fatty acid wherein the polyglycerol ester contains monoglycerides, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol ester of a fatty acid, monoglycerides, diglycerides and triglycerides.
  • the prior art polyglycerol ester systems contain a high (more than 10 wt.%) of glycerides, namely monoglycerides, diglycerides and triglycerides.
  • glycerides namely monoglycerides, diglycerides and triglycerides.
  • more stable emulsions then lower and therefore commercially more attractive viable amounts 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.
  • a more stable emulsion may provide for the same dosage of emulsifier a emulsified composition which is stable over a greater period, which allows for a more 'strained' system i.e. one with a higher water content, or a combination of both.
  • the present invention provides a fuel composition comprising:
  • the fuel composition contains monoglycendes, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycendes, diglycerides and triglycerides, and the polyglycerol ester is an ester of a mixture of fatty acids present in an amount of no greater than 0.5 wt.% based on the total fuel composition.
  • the polyglycerol ester contains monoglycendes, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol ester of a fatty acid, monoglycendes, diglycerides and triglycerides.
  • the amount of polyglycerol ester of a fatty acid, amount of monoglycendes, amount of diglycerides and amount of triglycerides are added together, the combined amount of monoglycendes, diglycerides and triglycerides is less than 10% by weight.
  • the monoglycendes, diglycerides and triglycerides are present in a combined amount of less than 9 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycendes, diglycerides and triglycerides. In one aspect the monoglycendes, diglycerides and triglycerides are present in a combined amount of less than 8 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycendes, diglycerides and triglycerides.
  • the monoglycendes, diglycerides and triglycerides are present in a combined amount of less than 7 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycendes, diglycerides and triglycerides. In one aspect the monoglycendes, diglycerides and triglycerides are present in a combined amount of less than 6 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycendes, diglycerides and triglycerides.
  • the monoglycendes, diglycerides and triglycerides are present in a combined amount of less than 5 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides. In one aspect the monoglycerides, diglycerides and triglycerides are present in a combined amount of less than 4 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides.
  • the monoglycerides, diglycerides and triglycerides are present in a combined amount of less than 3 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides. In one aspect the monoglycerides, diglycerides and triglycerides are present in a combined amount of less than 2 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides.
  • the monoglycerides, diglycerides and triglycerides are present in a combined amount of less than 1 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides. In one aspect the monoglycerides, diglycerides and triglycerides are present in a combined amount of less than 0.5 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides.
  • the monoglycerides, diglycerides and triglycerides are present in a combined amount of less than 0.1 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides. In one aspect the monoglycerides, diglycerides and triglycerides are present in a combined amount of less than 0.01 wt.%, based on the total content of polyglycerol esters of a fatty acid, monoglycerides, diglycerides and triglycerides.
  • 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 esters of fatty acids are formed from any suitable single polyglycerol or any suitable mixture of polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least diglycerol.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least triglycerol.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least tetraglycerol.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least pentaglycerol.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least hexaglycerol. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least heptaglycerol. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least octaglycerol. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least nonaglycerol. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least decaglycerol.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises at least unadecaglycerol. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises diglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises tetraglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises pentaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises heptaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises octaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises nonaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises decaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises unadecaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 2 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 5 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 7 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 9 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 1 1 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 13 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 15 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 16 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 17 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 18 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 19 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of at least 20 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of no greater than 90 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of no greater than 80 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of no greater than 70 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of no greater than 60 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of no greater than 55 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of no greater than 50 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 1 to 90 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 2 to 80 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 5 to 70 wt. % based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 7 to 60 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 9 to 55 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 10 to 55 wt. % based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 10 to 50 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 12 to 50 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 14 to 50 wt. % based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 16 to 50 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 18 to 20 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises triglycerol in an amount of from 20 to 50 wt. % based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of at least 1 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of at least 2 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of at least 3 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of at least 4 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of at least 5 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of at least 6 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 20 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 19 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 18 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 17 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 16 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 15 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 14 wt.% based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of no greater than 13 wt.% based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 1 to 20 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 2 to 19 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 3 to 18 wt.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 4 to 17 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 5 to 16 wt. % based on the combined weight of the polyglycerols.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 6 to 15 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 6 to 14 wt. % based on the combined weight of the polyglycerols. In one aspect the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises hexaglycerol in an amount of from 6 to 13 wt. % based on the combined weight of the polyglycerols.
  • the polyglycerol esters of a fatty acid may be as described in WO2013/001064 e.g. a 'broad range polyglycerol' may be utilised.
  • the polyglycerol composition used to form the polyglycerol esters of a fatty acid comprises a mixture of diglycerol in an amount of 1 1 .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
  • 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 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 m on o-un saturated 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 acid composition used to form the polyglycerol ester of a fatty acid comprises oleic acid in an amount of least 50 wt. % based on the combined weight of the fatty acids. In one aspect the fatty acid composition used to form the polyglycerol ester of a fatty acid comprises oleic acid in an amount of least 60 wt. % based on the combined weight of the fatty acids. In one aspect the fatty acid composition used to form the polyglycerol ester of a fatty acid comprises oleic acid in an amount of least 70 wt. % based on the combined weight of the fatty acids.
  • the fatty acid composition used to form the polyglycerol ester of a fatty acid comprises oleic acid in an amount of least 80 wt. % based on the combined weight of the fatty acids. In one aspect the fatty acid composition used to form the polyglycerol ester of a fatty acid comprises oleic acid in an amount of least 90 wt. % based on the combined weight of the fatty acids.
  • 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 aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 900 to 1200 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 930 to 1200 mg KOH/g. In a further aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 960 to 1 170 mg KOH/g.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1 150 to 1 190 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1 155 to 1 185 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1 160 to 1 180 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1 160 to 1 175 mg KOH/g.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1 160 to 1 170 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 1 165 to 1 170 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 950 to 970 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 955 to 970 mg KOH/g.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 950 to 965 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 955 to 965 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 960 to 970 mg KOH/g. In one aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a hydroxyl value of from 960 to 965 mg KOH/g.
  • polyglycerol may be described by their degree of polymerisation. Those skilled in the art may also name a polyglycerol mixture as if it were a specific polyglycerol, such as a triglycerol, when that polyglycerol mixture has a hydroxyl number equivalent to the hydroxyl number of the specific polyglycerol, such as a triglycerol.
  • the hydroxyl number ranges of glycerol and the specific polyglycerols diglycerol to undecaglycerol are given below.
  • Triglycerol 1259-1 120mg KOH/g
  • Tetraglycerol 1 1 19-1041 mg KOH/g
  • Heptaglycerol 955-930mg KOH/g
  • a mixture of polyglycerols having a hydroxyl number of 1200mg KOH/g may be referred to as a triglycerol.
  • the polyglycerol is diglycerol. In one aspect the polyglycerol is a polyglycerol having a hydroxyl number of from 1589 to 1260mg KOH/g. In one aspect the polyglycerol is triglycerol. In one aspect the polyglycerol is a polyglycerol having a hydroxyl number of from 1259 to 1 120mg KOH/g. In one aspect the polyglycerol is tetraglycerol. In one aspect the polyglycerol is a polyglycerol having a hydroxyl number of from 1 1 19 to 1041 mg KOH/g. In one aspect the polyglycerol is pentaglycerol.
  • the polyglycerol is a polyglycerol having a hydroxyl number of from 1040 to 991 mg KOH/g. In one aspect the polyglycerol is hexaglycerol. In one aspect the polyglycerol is a polyglycerol having a hydroxyl number of from 990 to 956mg KOH/g. In one aspect the polyglycerol is heptaglycerol. In one aspect the polyglycerol is a polyglycerol having a hydroxyl number of from 955 to 930mg KOH/g. In one aspect the polyglycerol is octaglycerol.
  • the polyglycerol is a polyglycerol having a hydroxyl number of from 929 to 910mg KOH/g. In one aspect the polyglycerol is nonaglycerol. In one aspect the polyglycerol is a polyglycerol having a hydroxyl number of from 909 to 894mg KOH/g. In one aspect the polyglycerol is decaglycerol. In one aspect the polyglycerol is a polyglycerol having a hydroxyl number of from 893 to 881 mg KOH/g. In one aspect the polyglycerol is undecaglycerol.
  • polyglycerol is a polyglycerol having a hydroxyl number of from 880 to 871 mg KOH/g.
  • all references to polyglycerols are references to polyglycerols having the stated degree of polymerisation e.g. all references to triglycerol are references to polyglycerol with a degree of polymerisation of 3.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50°C of from 1 .486 to 1.492. 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 .488 to 1 .492. 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 .487 to 1.491 .
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 50°C of from 1 .488 to 1.490. 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 1.4910. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 20°C of from 1 .490 to 1.500.
  • the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 20°C of from 1 .491 to 1 .499. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 20°C of from 1.492 to 1.498. In one preferred aspect the polyglycerol composition used to form the polyglycerol ester of a fatty acid has a refractive index at 20°C of from 1.493 to 1.497.
  • the polyglycerol ester of a fatty acid is prepared by reacting a polyglycerol and fatty acids in a ratio of polyglycerol to fatty acids of from 1 :1 to 1 :10. In one aspect the polyglycerol ester of a fatty acid is prepared by reacting a polyglycerol and fatty acids in a ratio of polyglycerol to fatty acids 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.
  • the polyglycerol ester of a fatty acid is prepared by reacting a polyglycerol and fatty acids in a ratio of polyglycerol to fatty acids of 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. 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 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.
  • 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. 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 0.25 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 0.2 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. 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 0.1 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 0.5 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 encompassed within the present invention.
  • the fuel containing the emulsifiers is combined with water and the fuel composition further 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.
  • Marine gasoil may also be known as marine diesel oil
  • the amount of water may be selected based on the requirements of the combustion system.
  • the fuel composition further 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 15 to 60 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.
  • the present invention provides a method for improving the stability of a fuel composition containing (a) fuel and (c) water, the method comprising
  • the polyglycerol ester contains monoglycerides, diglycerides and triglycerides in a combined amount of less than 10 wt.%, based on the total content of polyglycerol ester of a fatty acid, monoglycerides, diglycerides and triglycerides, and the polyglycerol ester is an ester of a mixture of fatty acids present in an amount of no greater than 0.5 wt.% based on the total fuel composition.
  • the fuel, the water and the polyglycerol ester of a fatty acid may be added in any suitable order.
  • the polyglycerol ester of a fatty acid is combined with the fuel and this in turn in combined with the water. In one aspect, the polyglycerol ester of a fatty acid is combined with the water and this in turn in combined with the fuel. In one aspect, the water is combined with the fuel and this in turn in combined with the polyglycerol ester of a fatty acid. In one aspect, the water, the fuel and the polyglycerol ester of a fatty acid are combined in a single step.
  • Hexaglvcerol (PGE 20140620-009) An ester of hexaglycerol was prepared based on 32.5 wt.% hexaglycerol and 67.5 wt.% of fatty acids. The profile of the fatty acids was
  • Triglycerol 10.67 wt.%
  • An ester of triglycerol was prepared based on 33.5wt.% triglycerol and 66.5 wt.% of fatty acids.
  • the profile of the fatty acids was similar profile to the profile of the fatty acids used in the preparation of PGE 20140620-009.
  • Triglycerol Triglycerol
  • N20 refractive index measured at 20°C
  • the triglycerol had the following polyglycerol profile.
  • Mono-diglvcerides Variation in the mono, di and triglycerides content in the PGE was achieved by adding amount of a mono-diglyceride mixture (ELN 20141 106-016) to the PGE.
  • ELN 20141 106- 016 had a fatty acid profile similar to the profile of the fatty acids used in the preparation of PGE 20140620-009 and contained 39.6 wt.% monoglyceride, 47.5 wt.% diglyceride and 12.6 wt.% triglyceride .
  • 200 g of emulsion were prepared by slowly adding the water phase to marine gas oil during intensive homogenisation with an Ultra Turrex at 20000 rpm for 60 s.
  • emulsifier was dissolved in the marine gasoil prior to emulsification (except trial 10 where the emulsifier was added to the water phase). Both the gasoil and the water phase were heated to the 55°C in advance. Water content: 15%, 33% and 50%
  • Emulsifier dosage 0.1 % and 0.15% (based on the total emulsion)
  • the droplet size distribution for samples 1 to 5 is shown in Figure 1 in which the D50.0 and D97.5 results are plotted.
  • the droplet size depends linearly on the total content of mono-, di- and triglyceride in the PGE.
  • the droplet size distribution for samples 6 and 7 is shown in Figure 2 in which the D50.0 and D97.5 results are plotted.
  • the droplet size increases with the total content of mono-, di- and triglyceride in the PGE.
  • Samples 1 to 5 reveal that an increased content of mono-, di- and triglycerides in PGE reduces the emulsification power of the PGE. This is seen from the increase in water droplet size of the fuel emulsions with 50% water content and 0.15% total emulsifier dosage.
  • Samples 6, 7 and 9 provide similar results with lower water content of 33% (sample 6 and 7) and 15% (sample9) and 0.1 % total emulsifier dosage
  • the PGE in samples 1 -7and 9 are based on hexaglycerol, where the PGE in sample 8 is based on purified triglycerol resulting in very low mono-, di- and triglyceride level.
  • sample 8 is also seen very small water droplet size
  • Sample 10 is comparable with sample 1 . The difference being that the emulsifier was added to the water phase and not to the MGO as in sample 1. Sample 10 produces slightly larger water droplets, but still with an sufficient emulsion stability without expelled free water
  • WO2013/001064 was prepared from 340g Oleic acid 90%, 102g Polyglycerol, 37g Glycerol and 1 .75g 50% NaOH in water. The preparation in the presence of glycerol would result in an expected total mono-di-triglyceride content of approximately 30%.
  • Triglycerol PGE 2526/159 of WO2013/001064 was prepared from 340g Oleic acid 90%, 108g Triglycerol, and 37g Glycerol. The preparation in the presence of glycerol would result in an expected total mono-di-triglyceride content of approximately 25%

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Abstract

La présente invention concerne une composition de carburant comprenant : (a) un carburant ; et (b) un ou plusieurs esters de polyglycérol d'un acide gras ; où la composition de carburant contient des monoglycérides, des diglycérides et des triglycérides en une quantité combinée inférieure à %, sur la base de la teneur totale des esters de polyglycérol d'un acide gras, des monoglycérides, des diglycérides et des triglycérides, et l'ester de polyglycérol est un ester d'un mélange d'acides gras présents en une quantité non supérieure à 0,5 % en pds sur la base de la composition totale de carburant.
PCT/EP2016/056779 2015-03-30 2016-03-29 Compositions de carburant comprenant des esters de polyglycérol d'un acide gras WO2016156302A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3222145A (en) * 1960-12-28 1965-12-07 Gulf Research Development Co Stabilization of thermally unstable liquid hydrocarbon fuels
GB2307697A (en) * 1995-12-01 1997-06-04 Exxon Research Engineering Co Fuel economy additive
WO2010010952A1 (fr) * 2008-07-24 2010-01-28 太陽化学株式会社 Additif abaissant le point de trouble pour ester d'alkyle d'acide gras
WO2012152309A1 (fr) * 2011-05-06 2012-11-15 Oleon Agent améliorant le pouvoir lubrifiant
WO2013001064A1 (fr) * 2011-06-29 2013-01-03 Dupont Nutrition Biosciences Aps Composition
FR2987052A1 (fr) * 2012-02-17 2013-08-23 Total Raffinage Marketing Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3222145A (en) * 1960-12-28 1965-12-07 Gulf Research Development Co Stabilization of thermally unstable liquid hydrocarbon fuels
GB2307697A (en) * 1995-12-01 1997-06-04 Exxon Research Engineering Co Fuel economy additive
WO2010010952A1 (fr) * 2008-07-24 2010-01-28 太陽化学株式会社 Additif abaissant le point de trouble pour ester d'alkyle d'acide gras
WO2012152309A1 (fr) * 2011-05-06 2012-11-15 Oleon Agent améliorant le pouvoir lubrifiant
WO2013001064A1 (fr) * 2011-06-29 2013-01-03 Dupont Nutrition Biosciences Aps Composition
FR2987052A1 (fr) * 2012-02-17 2013-08-23 Total Raffinage Marketing Additifs ameliorant la resistance a l'usure et au lacquering de carburants de type gazole ou biogazole

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