WO2014020477A1

WO2014020477A1 - Compositions for use as fuels comprising derivatives of glycerol

Info

Publication number: WO2014020477A1
Application number: PCT/IB2013/055940
Authority: WO
Inventors: Alberto Renato DE ANGELIS; Giulio ASSANELLI; Paolo Pollesel; Paolo FIASCHI
Original assignee: Eni S.P.A.
Priority date: 2012-07-31
Filing date: 2013-07-19
Publication date: 2014-02-06
Also published as: ITMI20121343A1

Abstract

An object of the present invention relates to a composition that can be used as fuel comprising: at least one hydrocarbon mixture at least one compound having formula (I) X- CH(Y) -CH₂OR (I) wherein R is a C₁-C₈ alkyl X is selected from H and OCH(CH₂OR) and Y is CH₂OR or X and Y jointly correspond to the substituent =CH-OR. Said composition can be advantageously used as fuel for diesel or gasoline engines.

Description

COMPOSITIONS FOR USE AS FUELS COMPRISING DERIVATIVES OF GLYCEROL

The present invention relates to a composition comprising a hydrocarbon mixture and one or more hydrophobic derivatives of glycerol. The above composition can be advantageously used as fuel for diesel and gasoline engines. The present invention also relates to the use of said hydrophobic derivatives of glycerol as fuel component .

It is known that the emissions produced by the combustion of fuels of a fossil origin containing carbon dioxide (C0₂) , carbon monoxide (CO) , nitrogen oxides (NO_x) , sulfur oxides (SO_x) , uncombusted hydrocarbons (HC) , volatile organic compounds and particulate (PM) , are the cause of environmental problems such as, for example, the production of ozone, the greenhouse effect (in the case of nitrogen and carbon oxides) and acid rain (in the case of sulfur and nitrogen oxides) .

In recent years, the increase in the cost of crude oil and a maturing awareness with respect to the environmental problems described above, have increased the necessity for finding alternative, biodegradable and renewable energy sources .

Consequently, the progressive substitution of fuels deriving from fossil energy sources such as, for example, coal, petroleum, natural gas, with fuels deriving from alternative energy sources such as, for example, vegetable oils, animal fats, biomasses, algae, is becoming of increasing interest on a worldwide scale and efforts have therefore been made in the art to obtain new fuels from renewable energy sources.

An oxygenated compound, that can also be obtained from renewable sources, normally added to fuels, is ethanol, which however has the defect of being miscible with water, hygroscopic, and immiscible with gasoil within a wide temperature range: phase separation can therefore take place and the mixtures obtained are unstable, as described, for example, by Lapuerta et al . in the article "Stability of diesel-bioethanol blends for use in diesel engines", published in "Fuel" (2007), Vol. 86, pages 1351-1357. Another alcohol, that can also be obtained from renewable sources, which can be used as component to be added to fuels, is butanol, which has a better miscibility with gasoil with respect to that of ethanol: it is still unsatisfactory, however. At low temperatures, in fact, butanol-gasoil blends are not homogeneous. A further problem linked to the use of these alcohols is the low cetane number of the alcohol-gasoil blend which causes a high ignition delay in internal compression diesel engines.

The use is also known of biodiesel and hydrotreated vegetable oils (HVO) as such, or in a blend with gasoil, and also blends of gasoil comprising alcohols of a biological origin. Biodiesel generally comprises a blend of fatty acid alkyl esters, in particular a blend of fatty acid methyl esters (FAME) and can be produced starting from raw materials of a natural origin containing triglycerides (generally triesters of glycerol with fatty acids having a long alkyl chain) . Said raw materials as such, or the triglycerides obtained after subjecting said raw materials to separation, are subjected to a transesterification process in the presence of an alcohol, in particular, methanol, and a catalyst, in order to obtain said fatty acid alkyl esters, in particular said fatty acid methyl esters (FAME) .

The use of these fatty acid methyl esters (FAME) , however, as such, or in a mixture with gasoil, has various problems relating to the oxidation stability and also during the synthesis of FAME, there is the formation of glycerine (about 10% by weight) as byproduct, whose use is an important aspect for upgrading the production process of biodiesel.

The use is also known of hydrotreated vegetable oils (HVO) , also called green diesel, which are produced by the hydrogenation/deoxygenation of a material deriving from renewable sources, such as, for example, soybean oil, rape oil, corn oil, sunflower oil, comprising triglycerides and free fatty acids, in the presence of hydrogen and a catalyst as described, for example, by Holmgren J. et al . in the article "New developments in renewable fuels offer more choices" , published in "Hydrocarbon Processing", September 2007, pages 67-71. This article indicates the best characteristics of said hydrotreated vegetable oils (HVO) with respect to fatty acid methyl esters (FAME) , in particular, in terms of a better oxidation stability and improved cold properties. Furthermore, said hydrotreated vegetable oils (HVO) do not have the problem of greater emissions of nitrogen oxides (NO_x) . Due to the lack of oxygen atoms in said hydrotreated vegetable oils (HVO) , however, their use in diesel engines mixed with gasoil in an amount lower than 5% by volume with respect to the total volume of said mixture, does not provide significant benefits with respect to particulate emissions (PM) .

The necessity is therefore felt for finding new compositions that can be used as fuels, in which there is a component deriving from renewable energy sources . The necessity is also felt for exploiting glycerol, whose market is currently saturated, as a starting material for obtaining compounds of a biological origin which can provide high performances as fuel components.

At present, one of the possible uses of glycerol is to react it, by -means of an etherification reaction, with olefins to give the corresponding ethers, which can be used as oxygenated components for gasoline and diesel. The olefin mainly used and object of numerous patents is isobutene. The reaction with isobutene leads to the formation of tert-butyl ethers of glycerol, of which the most interesting is di-tert-butyl ether. In these ethers, however, the biological component is markedly a minority as they consist of two, or rather three, molecules of isobutene per molecule of glycerol: consequently, their contribution in reaching the quota of a biological origin is not sufficiently high.

US2007/0283619 describes a process for the production of biofuels by the transformation of triglycerides into at least two groups of biofuels containing fatty acid monoesters and soluble ethers or acetals of glycerol. Said ethers and acetals of the known art, however, have a high affinity with water and a low miscibility with the hydrocarbon phase: this is a serious limitation for their use as fuel component as significant quantities of water can dissolve in the mixture of fuels containing said acetals, with considerable damage to the engine of vehicle due to corrosion phenomena. Furthermore, the presence in gasolines of substances miscible with water leads to the formation of formaldehyde, a carcinogenic substance, in the emissions (B. Strus et al . , Fuel 87 (2008), 957-963, ELSEVIER).

The Applicant has now found that the addition of particular hydrophobic derivatives of glycerol allows a composition to be obtained, which can be advantageously used as fuel, in particular as fuel for both diesel and gasoline engines.

An object of the present invention therefore relates to compositions that can be used as fuels, or fuel components, containing:

at least one hydrocarbon mixture

at least one compound having formula (I)

wherein

R is a linear or branched Ci - C₈ alkyl

X is selected from H and OCH(CH20R) and Y is

CH₂OR or

X and Y together correspond to the substituent =CH-OR.

R is preferably selected from CH₃ , C₂H₅, C₃H₇, C₄H₉,

C₅H₁₁. More preferably R can be selected from ethyl, n- propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert- butyl, 3 -methyl -1 -butyl and 2 -methyl-1 -butyl . A particularly preferred aspect is that R is ethyl or n- butyl.

The composition of the present invention can therefore contain one or more of the following derivatives of glycerol, wherein R has the meanings described above:

RO-CH=CH-CH₂-OR (la)

RO- CH2 - CH2 - CH2-OR (lb)

(RO- CH2 ) 2 CH-O-CH ( CH2-OR) ₂ (Ic)

The derivatives of glycerol having formula (I) provide high performances as fuel components, overcoming the problems of the known glycerol ethers relating to their high affinity with water and low affinity with the remaining hydrocarbon component of the fuel. The compounds having formula (I) have high characteristics with respect to the octane (or cetane) number, a high heating power, complete miscibility with the hydrocarbon phase and a very low affinity with the aqueous phase, they are consequently not hygroscopic and therefore reduce problems linked to miscibility and corrosion of the parts of the engine due to the presence of traces of water.

The compounds having formula (I) , either individually or in a mixture with each other, can therefore be advantageously used as fuel components, in particular gasoil, especially for automotive use, and as additives for gasoline, and their addition to gasoil or gasoline allows, inter alia, a significant decrease in particulate emissions. The composition containing them is less sensitive to the presence of water and consequently there is a significant reduction in corrosion phenomena in the engines. The addition of the compounds having formula (I) , moreover, has no negative influence on the characteristics of the starting gasoil such as, for example, the cold properties, cloud point (CP) and cold filter plugging point (CFPP) , neither does it negatively influence the demulsification characteristics or lubricity properties of the composition, nor does it have a negative influence on the oxidation stability of the starting gasoil.

In particular, the compounds having formula (Ic) are new and are a particular aspect of the present invention. According to a preferred embodiment of the present invention, said compounds having formula (I) can be present in said composition in a quantity ranging from 0.5 % by volume to 15 % by volume, preferably ranging from 1% by volume to 10 % by volume, with respect to the total volume of said composition, wherein said quantities, when at least two compounds having formula (I) are present, refer to the sum of their volumes.

For the purposes of the present invention, any hydrocarbon mixture that can be used as fuel, can be adopted. In particular, the hydrocarbon mixture can be selected from gasoil, gasoline, biodiesel, green diesel and mixtures thereof.

In particular, said gasoil can be selected from gasoils falling within the specifications of gasoil for motor vehicles according to the standard EN 590:2009, and also gasoils that do not fall within these specifications. Gasoil is generally a mixture containing hydrocarbons such as, for example, paraffins, aromatic hydrocarbons and naphthenes, typically having from 9 to 30 carbon atoms. The distillation temperature of gasoil generally ranges from 160°C to 450°C. According to a preferred embodiment of the present invention, said gasoil can have a density, at 15 °C, determined according to the standard EN ISO 12185 : 1996/Cl : 2001 , ranging from 780 kg/m³ to 845 kg/m³, preferably ranging from 800 kg/m³ to 840 kg/m³. According to a further preferred embodiment of the present invention, said gasoil can have a flash point, determined according to the standard EN ISO 2719:2002, higher than or equal to 55°C, preferably higher than or equal to 65 °C. According to a preferred embodiment of the present invention, said gasoil can have a cetane number, determined according to the standard EN ISO 5165:1998, or standard ASTM D6890:2008, higher than or equal to 47, preferably higher than or equal to 51.

Gasoils that can be conveniently used in the compositions of the present invention can therefore be all known gasoils and can also derive from the mixing of diesel cuts of different origins and having varying compositions. The sulfur content in these diesel cuts preferably ranges from 2000 to 50 mg/kg, and even more preferably from 50 to 3 mg/kg.

Typical diesel cuts can be medium distillates, preferably having a boiling point ranging from 180 to 380°C. Examples of these cuts can be gasoils from primary distillation, gasoils from vacuum distillation, and from thermal or catalytic cracking, such as, for example, the desulfurized gasoil cut coming from fluid bed catalytic cracking (light cycle oil (LCO) ) , fuels from a Fischer- Topsch process or of a synthetic origin. Cuts obtained from these after hydrogenation treatment can also be conveniently used.

If the hydrocarbon mixture is a gasoline, gasolines characterized by a T95 (ASTM D86) not higher than 250 °C, preferably not higher than 240°C, can be conveniently used, wherein T95 refers to the temperature at which 95% by volume of gasoline distills. Gasolines with a T95 lower than 250°C are preferably used, in particular lower than 240°C, having a density ranging from 855 to 910 kg/m³. Gasolines that can be conveniently used are those deriving from catalytic processes, preferably deriving from fluid-bed catalytic cracking processes (FCC) , reforming processes, and mixtures thereof. In particular, HCN gasolines are therefore used, i.e. heavy gasolines (initial boiling point 150°C) from FCC as such or desulfurized, and gasolines called Heavy Reformates, i.e. heavy gasolines (initial boiling point 150°C) from reforming, or mixtures thereof.

The sulfur content of these gasoline cuts preferably ranges from 2000 to 50 mg/kg, and even more preferably from 50 to 1 mg/kg.

If the composition contains a biodiesel, as previously specified, said biodiesel comprises a mixture of fatty acid alkyl esters, in particular a mixture of fatty acid methyl esters (FAME) and can be produced starting from raw materials of a natural origin containing triglycerides (generally triesters of glycerol with fatty acids having a long alkyl chain) such as, for example, crude vegetable oils obtained by squeezing the seeds of oleaginous plants such as, for example, rape, palm, soybean, sunflower, mustard, and also from other sources of triglycerides such as, for example, algae, animal fats or used or waste vegetable oils. These raw materials as such, or the triglycerides obtained after subjecting said raw materials to separation, are subjected to a transesterification process in the presence of an alcohol, in particular methanol, and a catalyst, so as to obtain said fatty acid alkyl esters, in particular said fatty acid methyl esters (FAME) . Greater details relating to the production of biodiesel are described for example in Hanna et al . , in the review " Biodiesel production : a review" , published in "Bioresource Technology" (1999) , vol. 70, pages 1-15. Said biodiesel can preferably be selected from those falling within the specifications of biodiesel for motor vehicles according to the standard EN 14214:2008.

The composition can contain hydrotreated vegetable oils, called "green diesel" : they are produced by the hydrogenation/deoxygenation of a material deriving from renewable sources such as, for example, soybean oil, rape oil, corn oil, sunflower oil, comprising triglycerides and free fatty acids, in the presence of hydrogen and a catalyst as described, for example, by Holmgren J. et al . in the article "New developments in renewable fuels offer more choices", published in "Hydrocarbon Processing", September 2007, pages 67-71.

The compositions of the present invention are prepared by mixing the single components. Other possible additives present in the final composition can be introduced into both the final composition itself or into the hydrocarbon blend before their mixing.

The compounds having formula (I) are prepared starting from glycerol by means of a multistep process of which the first step corresponds to transforming glycerol into 1 , 3 -dialkoxy-2-propanol having formula (Ix) :

RO-CH₂-CHOH-CH₂-OR (Ix)

This etherification step can be carried out following any of the known methods for the preparation of ethers. The glycerol can be reacted, for example, in the presence of alcohol and an acid catalyst. Acid catalysts which can be conveniently used are, for example, acid exchange resins, acid zeolites, silico- aluminas, supported phosphoric acid. Solvents which can be conveniently used are preferably the same alcohols with which the corresponding ether is to be formed.

The reaction is preferably carried out at a temperature ranging from 50 to 200°C, and a pressure ranging from 1 to 20 atmospheres. The space velocity preferably ranges from 0.1 to 20 hours^"1. The alcohol/glycerol molar ratio preferably ranges from 2 to 10.

ROH alcohols which can be conveniently used for preparing the alkoxides of step (1) are alcohols in which R is a linear or branched alkyl containing from 1 to 8 carbon atoms, preferably from 2 to 5 carbon atoms. Alcohols which can be conveniently used are therefore ethanol, isopropanol, n-propanol, n-butanol, iso- butanol, sec-butanol, tert-butanol , 3 -methyl -1-butanol, 2-methyl- 1-butanol . Ethanol or n-butanol are preferred.

Alcohols which can also be obtained biologically are preferably used, i.e. that can be obtained, for example, by the fermentation of biomasses or biomass derivatives, or by the fermentation of biomasses deriving from agricultural crops rich in carbohydrates and sugars, or by the fermentation of lignocellulosic biomasses, or by the fermentation of algal biomasses. The lignocellulosic biomass can derive from agricultural crops rich in carbohydrates and sugars, such as, for example, corn, sorghum, barley, beet, sugar cane, or mixtures thereof. The lignocellulosic biomass can be selected, for example, from:

products of crops expressly cultivated for energy use (such as, for example, miscanthus, switchgrass, foxtail millet, common cane), including waste products, residues and scraps of said crops or their processing; products of agricultural cultivations, forestation and silviculture, comprising wood, plants, residues and waste products of agricultural processing, forestation and silviculture;

waste of agro-food products destined for human nutrition or zootechnics;

residues, not chemically treated, of the paper industry;

waste products coming from the differentiated collection of solid urban waste (such as, for example urban waste of a vegetable origin, paper, etc.);

or mixtures thereof.

The alcohol used can, for example, also derive from the fermentation of at least one algal biomass cultivated for energy purposes, or from the fermentation of residues or derivatives from the cultivation of said biomass.

The fermentation can be effected according to methods known in the art. The fermentation, for example, can be carried out in the presence of natural microorganisms, or microorganisms genetically modified for improving said fermentation. Any of the known methods for obtaining ethanol from biomasses is suitable for producing ethanol that can be used in the present invention. Processes for the production of ethanol from biomasses are described, for example, in US 5562777; US 2008/0044877; " Ethanol from ligninocellulosic biomass: technology, economics and process for the production of ethanol" F. Magalhaes, R.M. Vila Cha-Baptista, 4^th International Conference on Hands-on Science Development, Diversity and Inclusion in Science Education 2007; " Ethanol fermentation from biomass resources: current state and prospects" Y. Lin, S.Tanaka, Appl . Microbiol. Biotechnol . (2006) 69:627- 642; "Hydrolysis of ligninocellulosic materials for ethanol production: a review" Y. Sun, J. Cheng, Bioresource Tecnology, volume 83, Issue 1, May 2002, pages 1-11.

Another aspect of the present invention is to use propanol, preferably iso-propanol , as alkylating agent. According to a preferred aspect, in accordance with what is specified above in general for bioalcohols, propanol of a biological origin is used, preferably obtained by the fermentation of biomasses, as described, for example, in US2009/0246842.

A further aspect of the present invention is to use butanol, preferably n-butanol, as alkylating agent, in accordance with what is specified above in general for bioalcohols. According to a preferred aspect, biobutanol is used, i.e. butanol of a bio-origin, preferably prepared by the fermentation of biomasses, according to the A.B.E. (acetone/butanol/ethanol) process. The A.B.E. process uses the bacterium Clostridium acetobutylicum and was described for the first time in US 1,315,585. Acetone, butanol and ethanol are obtained from this process, which can be subsequently separated by means of consecutive distillations. Variations and improvements in the A.B.E. process are described, for example, in US 5,753,474, US 5,192,673, and in Chang-Ho Park, Biothecnol. Bioprocess Eng. 1996, 1, 1-8.

The 1, 3 -dialkoxy-2 -propanol (Ix) is then subjected to dehydration to obtain the compound having formula (la) 1 , 3 -dialkoxy-propene : the dehydration is carried out in the presence of a suitable catalyst, according to any of the known methods for the dehydration of compounds containing hydroxy1 groups. The catalyst can be selected, for example, from silica, silica-alumina, zeolites, acid exchange resins, acid clays, heteropolyacids supported on silica or activated carbon. High-boiling linear alkanes, for example hexadecane, can be conveniently used as solvents. The dehydration reaction can be carried out at a temperature ranging from 150°C to 350°C, at a pressure ranging from 0 to 2 atmospheres.

Further details relating to dehydration processes that can be used in the preparation process of the present invention are described, for example, in K. Mori, Y. Yamada, S. Sato, Appl . Catal . A, 336, 2009, 304-8.

Operating under blander dehydration conditions with respect to those described above, the compound having formula (Ic), 2 , 2 ' -oxy-bis ( 1 , 3 -dialkoxypropane) , is obtained from 1 , 3 -dialkoxy-2 -propanol (Ix) : in particular the reaction is carried out at a temperature ranging from 100°C to 200°C, and at a pressure ranging from 3 to 20 atmospheres. The catalysts and solvents are the same as those indicated above for the dehydration of (Ix) to give the compound (la) .

The compound having formula (lb), 1 , 3 -dialkoxypropane can be obtained from 1 , 3 -dialkoxy-propene (la) by hydrogenation: said hydrogenation is effected with hydrogen in the presence of a suitable catalyst, according to any of the known methods for the hydrogenation of double bonds. The 1 , 3 -dialkoxy-propene can be reacted, for example, with hydrogen in the presence of a hydrogenation catalyst; all hydrogenation catalysts known to experts in the field can be used, and the catalyst can be selected, for example, from platinum on carbon, platinum on alumina, palladium on carbon, supported metal of group VIII.

High-boiling aliphatic hydrocarbons such as, for example, hexadecane or octadecane, can be used as solvents. The hydrogenation reaction can be carried out at a temperature ranging from 25 °C to 250°C, and at a hydrogen pressure ranging from 1 to 80 atmospheres.

The fuel composition, object of the present invention, can possibly comprise conventional additives known in the art, such as, for example, flow improvers, lubricity improvers, cetane improvers, antifoam agents, detergents, antioxidants, anticorrosion agents, antistatic additives, dyes, or mixtures thereof. These additives, if present, are generally present in a quantity not higher than 0.3% by volume with respect to the total volume of said composition considered as being equal to 100.

Some illustrative and non- limiting examples are provided hereunder for a better understanding of the present invention and for its practical embodiment.

EXAMPLE 1 - Synthesis of 1 , 3 -diethoxy- 2-propanol (Ix, with R = CH₂CH₃) A catalyst consisting of a commercial acid resin (Amberlyst 36) is charged into a fixed-bed reactor heated to a temperature of 180°C and a mixture of glycerol and ethanol are fed in a molar ratio of .1/10, at a temperature of 180°C and a space velocity of 0.5 hours^"1. A conversion of glycerol equal to 85% is obtained, with a selectivity to 1, 3-diethoxy-2-propanol of 20%.

The diethoxy-propanediol thus obtained is separated by distillation from the mono-ethoxy-propanediol and non-reacted glycerol.

EXAMPLE 2 - Synthesis of 1 , 3 -diethoxy-propene (la, with R = CH₂CH₃)

A flow of the 1, 3-diethoxy-2-propanol obtained in Example 1 is fed, at a space velocity of 0.5 hours^"1, to a fixed-bed reactor filled with zeolite Y in acid form with a S1O₂/AI₂O₃ molar ratio equal to 10, previously heated to 180 °C. The samples are collected at regular time intervals and are analyzed by gaschromatography . A conversion of 1 , 3 -diethoxy-2 -propanol equal to 90% is obtained, with a selectivity to the desired product equal to 95%.

EXAMPLE 3 - Synthesis of 2 , 2 ' -oxy-bis ( 1 , 3 -diethoxy- propane) (Ic, with R = CH₂CH₃)

50 g of 1 , 3 -diethoxy-propene (la), prepared according to what is described in the previous example, are fed to a steel autoclave and 4 g of acid exchange resin Amberlyst 36 are added. The autoclave is closed and heated to 130 °C, stirring for 3 hours. At the end of this period, the autoclave is cooled to room temperature and, after opening it, the reaction products are analyzed. A conversion of 80% of the 1,3- diethoxy-propene initially present is obtained, with a selectivity to 2 , 2 ' -oxy-bis ( 1 , 3 -diethoxy-propane) equal to 85% with the complement to 100 consisting of mono- ethoxy-propanediol and 1,2,3 tri-ethoxy-propane.

The desired product 2 , 2 ' -oxy-bis (1 , 3 -diethoxy- propane) is easily separated from the reaction mixture by distillation.

Claims

1) A composition containing:

- at least one hydrocarbon mixture

- at least one compound having formula (I)

X- CH(Y) -CH₂OR (I)

wherein

R is a linear or branched Ci-C₈ alkyl

X is selected from H and OCH(CH20R) and Y is

CH₂OR or

X and Y together correspond to the substituent

=CH-OR.

2) The composition according to claim 1, containing one or more of the following compounds (I) :

RO-CH=CH-CH₂-OR (la)

RO-CH₂-CH₂-CH₂-OR^■ (lb)

(RO-CH₂)₂CH-0-CH(CH₂-OR)2 (Ic)

wherein R is a linear or branched Ci-C₈ alkyl.

3) The composition according to claim 1 or 2, wherein, in the compounds having formula (I) , R is selected from CH₃, C₂H₅, C₃H₇, C₄H₉, C₅Hn.

4) The composition according to claim 3, wherein R is selected from ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec -butyl, tert -butyl, 3 -methyl -1 -butyl and 2 -methyl -1 -butyl .

5) The composition according to claim 4, wherein R is ethyl or n-butyl.

6) The composition according to claim 1, wherein the compound having formula (I) or the compounds having formula (I) are present in a quantity ranging from 0.5% by volume to 15% by volume, with respect to the total volume of the composition.

7) The composition according to claim 6, wherein the compound having formula (I) or the compounds having formula (I) are present in a quantity ranging from 1% by volume to 10% by volume, with respect to the total volume of the composition.

8) The composition according to claim 1, wherein the hydrocarbon mixture is selected from gas oil, gasoline, biodiesel, green diesel and. mixtures thereof .

9) Use of the composition according to claim 1 as fuel or fuel component .

10) Use as fuel component of compounds having formula (I)

X- CH(Y) -CH₂OR (I) wherein

R is a linear or branched Ci - C₈ alkyl

X is selected from H and OCH(CH20R) and Y is CH₂OR or

X and Y together correspond to the substituent =CH-OR.

11) Use according to claim 9 or 10, wherein the fuel contains a hydrocarbon mixture selected from gas oil, gasoline, biodiesel, green diesel and mixtures thereof.

12) Compound having formula (Ic) :

(RO-CH₂)2CH-0-CH(CH₂-OR)2 (Ic) wherein R is a linear or branched Ci-C₈ alkyl.