CA1098699A

CA1098699A - Diesel fuel comprising methanol and a methanol- soluble polyoxyalkylene compound

Info

Publication number: CA1098699A
Application number: CA291,940A
Authority: CA
Inventors: Dke Blysing
Original assignee: Berol Kemi AB
Current assignee: Nouryon Surface Chemistry AB
Priority date: 1976-11-29
Filing date: 1977-11-29
Publication date: 1981-04-07
Also published as: IT1091508B; NL7713095A; SE7613355L; BR7707906A; GB1591398A; JPS5381504A; SE404702B; FR2372224B1; DE2753027A1; FR2372224A1; ES464891A1; JPS6140717B2

Abstract

DIESEL FUEL COMPRISING METHANOL AND METHANOL-SOLUBLE
POLYOXYALKYLENE COMPOUND

ABSTRACT OF THE DISCLOSURE

The present invention provides a diesel fuel based on methanol and containing an additive for improving cetane number comprising a methanol-soluble polyoxyalkylene compound.

Description

3~

SPECIFICArlON
The current shortage o-f petroleum oil products has considerably increased interest in synthetic liquid fuels. Particularly attractiv~ are the lower alkallols SUCII as methanol, etllallol and propanol, for use as diesel fuel.
The ignition qLIality of cliesel fuels is expressed in terrns of "cetene" or "cetane" numbers, wllicll numbers have been cleveloped Oll a basis very similar to $hat adopted for measuring the ignition ~Luality of gasoline in ter~ns of octanenumbers.
The cetene number reers to a mixture of cetene (1-hexadecene) and 01-methyl-naphthalenej the cetane number refers to a similar mixture of cetane (n-hexadecane) and o~ ~ metllylnaphthalene. The ce-tene or cetane numbers indicate volumetric percentages of cetene or cetane in the blend. Cetane is normally used because cetene is difficult to purify and is somewhat unstable in storage.
The cetane number of the lower aLkallols is, however, too low to enable the aLkanols to be used as diesel fuel unless special measures are taken.
One way to increase ease of ignition in a diesel engine is by preheating the inlet air. For methanol however the temperature of the inlet air has to he brought to not less than about 130 C, in order for the diesel engine to fire.
Another way of increasing the ignition qualities o-f the lo~ver alkanols is to add an al~yl nitrate, e. g. hexyl nitrate. While the aLkyl nitrates increase cetane number, the a~yl nitrates easily hydrolyze to form acidic compo~mds which lead to corrosion. Further, alkyl nitrcltes will increase the emissions ~` ~ of nitrogen-containing exhaust gases.
According to the present invention, a diesel fuel is provided comprising ~5 methanol and, per 100 parts by weight of ~nethanol, frol~ about 2 to about 40, preferably from about 5 to about ~5, parts by weight of a methanol-soluble pDlyoxyaLkylene compo-md containing from about 4 to about 400, preferably from about 6 to about 100 oxyalkylene units derived from ethylene oxide and/or . ` I .
.

69g propylene oxlde, the oxya].ky].ene units being at least 4~%
and preferably at least 60~ by weight of the total polyoxy-alkylene compound. Particularly preferred coMp~unds are polyoxyalkylene compounds having at least four oxyalkylene units in a straight chain.
The polyoxyalkylene compounds of the invention are defined by the formula:
Rl - [x(cnH2no)xG]m wherein:
m is a number within the range of 1 to 12;
n i9 2 or 3 or a mixture thereof;
x is a number within the range from about 4 to about 400, preferably from about 6 to about 100, and repre- :
: sents an average number of the various species present;
X is selected from the group consisting of oxygen, sulfur and (-N-Cn'H2n')r ~ , wherein n' is a number in the range of 1 to 6 and r is O to 10; . - :
20 . Rl and R2 are selected from the group consisting of hydrogen; the residue o an organic compound comprised only of atoms selected from hydrogen, carbon and oxygen~
and [O(CnH2nO~XG~; G is selected from the group consisting , .
of hydrogen and the groups R3, S03M and -P=O where R3 R4 R4 . :
; is a hydrocarbon group having from about 1 to 24 carbon atoms and R4 is selected from the group OM and the group Rl-~X(CnH2nO)XG~m_l where M is hydrogen or an inorganic or organic salt-:Eorming cation. :
These polyoxyalkylene c~ompounds can be obtained by condensing in the conventional way ethylene oxide and/or ~b/~ - 2 -....

6~
propylene oxide wi~h water, hydrogen sulfide, ~ulEuric acid, ammoni~, or organic compounds containing the reactive grouping -N-H, -C - Oll, ,O , -O-P=O , -S-H, cr -COOH. I~ desired, within the HO-S-OH O~ OH
o , ; ,' ,: :
.
, .
~ 2a -: ~ : - . . : :~: : , scope ot the inventioll, the polyo~ yalkylene adducts obtained can be further reacted witll alcohols, hali(les, acids or esters, e. ~ by etllerification or esterification, to -forr~l carl~oxyl ate, sulphate or phosphate esters. If groups reactive with ethylene oxide Ol~ propylene oxide cu e present 5 or formed, these groups can be -further alkoxylated.
The methanol base diesel fuel of the invention comprises at least 50~/c by weight, preferably at least 70~C by weight, methanol. In addition to the polyoxyalkylene compound, there can also be present other aclditives commonly used in diesel fuels, such as corrosion inhibitors, lubricants, combustion-10 promoting agents, stabilizers, agents for preventing the precipitation ofcombustion residues,agents for reducing undesirable emissions in the exhaust gases, etc. Thus, for instance, a small amount of water, suitably from 2 to about 10/C based on the weight of methanol, can be added to reduce the proportion of nitrogen oxide in the exhaust gases. However, tlle water may 15 decrease the ignition of the fuel.
The diesel fuel of the invention has a substantially lower ignition temperature than pure methanol, and the emissions are rnuch less corrosive than those of methanol fuel to which alkyl ni-trates have been added. It has a good stability when subjected to temperature and pressure changes as well as - 20 to mechanical stress. Tn addition, the polyoxyal~ylene compound has a lubricating effect, and promotes a smooth running of the engine even when the exhaust gases contain a high proportion of non~combusted organic compounds.
Examples of polyoxyalkylene compounds within the scope of the 25 invention are alkylene oxide adducts obtained by hydroxyalkylation of ammonia . . .

.
. I
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and by hydroxyalkylation of mono- or polyamines containing one or more primary or secondary nitrogen atoms.
Particularly preferred compounds within this class are the compounds of the general ~ormula:

R5-N-[Cn~l2 O] H II

n is as in I, and R5 and R6 are selected from the group consisting of alkyl having from one to about twenty-four carbon atoms, and [CnH2n]xOH; and x is a number from about 4 to about 40.
Other polyoxyalkylene compounds that advantageously can be used according to the invention are polyoxyalkylene mercaptans and polyoxyalkylene hydrogen sulphide, wherein X
in I is sulfur~ Particularly preferred compounds within said class are compounds of the general ~ormu].a:
Rl~S~[cnH2nO]x~8 III
wherein:
Rl is as in I and R8 is selected from the group consisting of hydrogen and hydrocarbon groups having ~rom one to about twenty-four carbon atoms;
n is as in I and X i6 a numher from about 4 to about 40.
Another class of preferred polyoxyalkylene compound wi.thin the scope of the invention are compounds of the general formula:
Rg r~OCnH2n]x~oH~m wherein:
Rg ~ts hydrogen or the residue oE an organic compound that is compo,sed only of atoms selected from hydrogenl carbon and oxygen which compound has from one to about : ~ jb/A`,~?, .
: : :

twelve hydrogens reactive with ethylene ox~de or propylene oxide;
m is a number from 1 to about 12, and n i9 as in I; and x'is a number from about 4 to about ~00, preferably Erom about ~ to about 100. Such compounds have -the further advantage that the fuel con~a:ins only oxygen, hydrogen and carbon, so that the fuel will comply with strick emission control standards.
The preferred class of polyoxyalkylene compounds of IV are polyalkylene glycols obtained by polymerization of ethylene oxide or propylene oxide or mixtures of these alkylene oxides. The alkylene oxides can be polymeri~ed separately or together in one or several steps.
Other examples of polyoxyalkylene compounds of IV
are reaction products of the alkylene oxides in question and acyclic or isocyclic, mono- or polyfunctional hydroxyl or carboxyl compounds containing from 1 to about 40 carbon atoms. Examples of suitable monofunctional hydroxyl and carboxyl compounds are methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, acetic acid, propionic acid, butanoic acid, hexanoic acid and 2-ethylhexanoic acid~ Examples of polyfunctional hydroxyl and carboxyl compounds are glycerol trimethylolpropane~ butylene glycol, butane-triol, hexane-triol, pentaerythritoi, sorbitol, sorbitan polysachharides such as sucrose, glucose, arabinose, fructose, mannoseS
dextrose, lactose .

~b/~jp, - 5 -and maltose, s~lccinic acid, glutaric acid, adipic acid, sebacic ~cid, phtllalic acicl, isophthalic acid, dodecane-dica~boxylic acid and resorcil-lol.
Another suitable class of polyoxyall~ylene compoullds are the surface-active polyoxyalkylene glycol etllers anù esters, including the sulfates 5 and phosphates.
The surface-acti~e compounds impart -to water a surface tension o-E
below 50 dyns/cm cat a concentl ation of 1~/c by weight at a temperature of 25C.
The surface-active compounds are compounds wherein ~l is an oxy or thio hydrocarbon group or an acyl hydrocarbon group containing ~rom about 8 to 10 about 30 ccubon atoms, the species where n is ~ cornprises at least 50/c oE
the compound, and ~ is a number Erom about 4 to about 40, preEerably from about 6 to about 25, witll reference to formula I above.
The nonionic polyoxyalkylene glycol ether and ester sur:Eactants ha~te the following general formula:
~ A--(c~lH2no)x H
where :E~ is hydrogen or a straight or branched chain satuxated or unsaturated . hydrocarbon group havillg from eight to thirty carbon atotns or an arall~l group baving a straight or branched chain saturated or unsaturated hydrocarbon grollp 20 of from six to twenty-Four carbon atoms attached to the aryl nucleus, and attached to A through the aryl nucleus;
- A is selected from the group consisting of ethereal oxygen and sulfur, carboxylic ester and thiocarboxylic ester groups, and x is a number ~rom 4 to 40.
R can, for example, be a straight or branched chain all~yl group, such as octyl, nonyl, decyl, lauryl, myris-tyl, cetyl, or stearyl, or an ,' ' ' ' , " ~ ' ",.' , ',' ' , , ~L~G95~

allcylaryl group such as oc~ylphenyl, nonyl~ enyL, decylphenyl, stearylphenyl, etc. In this formula, O~-l could also be replace~l by the grroup--O(C3H~O)mH, where rn is a number ranging froll~ 1 to 10. Exarnples of Sucll nonionic surfaciants are SUCh as have been obtained by adding ethylene oxide or 5 propylene oxide to the above mentioned alcohols or phenols.
The sulfated all~oxylated derivati~es of the ~bove have the forrnula:
, ` R- A- ( Cn~ 2 n O ) X S 0 3M
wher e M is hydrogen or an alkali metal or an organic amine cation and x, A and R are as above.
Where R is alkyl it will be evident that the wetting agent can be regarded as derived ~rorn an alcohol, mercaptan, oxy or thio fatty acid of high molecular weight, by condensation with ethylene oxide or propylene o~ide.
Typical of this type of alkyl product are the condensation products of oleyl or lauryl (dodecyl) alcohol, or mercaptan, or oleic or lauric acid, with from 8 to 17 moles of ethylene o~idea such as "Emulfor ON" Typical aLkyl esters ~re "Renex" (polyoxyethylene ester of tall oil acids) ~nd "Neutrorlyl 331" (higher fatty acid ester of polyethylene glycol).
Where R is araLkyl, the wetting agent can be derived from an alkyl phenol or thiophenol.
Another class of sur~actallts are the polyoxyalkylene phosphate esters described by the following ormula:
R--O O
\pD
/ \
R--O O~-M

~ . .............. . . .

The R's Call ~e the same or clifferent. One or both R is a r~dical containing polyoxyalkylelle etller and no more than one ~ is hydrogen. Th~ R
radical containing~ polyoxyalkylene etheL is of the form:
R, ~ O-CnII n ) x 5 in which ~ has a value greater than æero, up to about 30, and preferably is within the rang~e -from about 1 to abo-lt 10, and denotes the average numher of oxyall;ylene units in the chain. It will be unclerstood that there will be present in admixture species having x2values bo~h lligher and lower than the 10 averagevalue for 2~.
R, Dis a primary or secondary straight or branched chain saturated or unsaturated aliphatic radical having from about eight to about thirty carbo atoms, prefera~ly Irc3m about twelve to about twenty- two carbon atoms, or a mono, di, or trialkyl~substituted phenyl radical llaving from about six to 15 about t~venty-four carbon atoms~ and preEerably f~om about eight to about eighteen carbon atoms in the ~lkyl portion.
M is hydrogen or a water-soluble salt-forming cation such as all alkali metal, such as, for instance, sodium or potassium; ammonia; or an organic a~nine, such as an alkanolamine or an alkylamine radical, for -~0 exanople, tnonoethanolamine, diethanolamine, triethanolamine, butylamine,octylamine, or hexylamine.
These polyoxyalkylene phosphate esters are known compounàs and are described in U.S. patents Nos. 3,294,693 and 3,235,627 25 Additional polyoxyalkylene pliospllate esters are described in IJ.S. patent ~ ' .

., , ' ~
:: ~
.. .. . . . . . . . .

No. 3,400,1~8, at columll 17, and in the Mailew ~ Krupirl article in Soap arld Sallital-y Chemicals, April 1~62, pa(res 55 to 58, and 95.

Additional polyoxyallcylene phospl~ate ester surfac~ants are descril~ed in U. S. patent No. 3,122, 508 to Grifo, Mayllew, Stefcik and Woodwarcl, dated February 25, 1964 and in U. S. patents Nos. 3, 004, 058 and 3, 00~, 057 to Nunn and Hesse, dated October 10, 1961~
In general, the polyoxyalkylene ether phospllates are pr epared by - reaction of phosphorous pento2~ide, orthophosphoric acid, pyrophosphoric . 10 acid, or a polyphosphoric acid with a suitable nonionic surfactant base.In the course of the esterification, monoesters and diesters may both be formed, but one may be obtained in preference to the other, according to the reaction conditions aind the molar proportions of the reactants.
Phosphate esters composecl of the mi~tures of the mono and di esters in any - 16 proportion can be employed.
~Ldditional examples of suitable surace active compouncls are ethylene oxide adducts of decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, eicosyl alcohol, oleyl alcohol; cyclooctanol, cyclododecanol, cyclohe2cadecanol; octyl phenol, nonyl phenol, dodecyl phenol, hexadecyl phenol, dibutyl phenol, dioctyl phenol, dinonyl phenol, capric acid7 lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and arachidic acid. I~ desired, the free OH of the polyo~yalkylene nonionic compounds of IY can be phosphated or sulphated to the corresponding anionic surface-active co~npounds.
Preferred polyoxyalkylene compounds are polyoxyethylene glycols having a molecular weigllt within the range frolll about 400 to about 4000, and surface~active polyoxyethylene glycols as well as mixtures thereof.
The weight ratio oE the polyoxyethylene glycol to surface-active compound in such mi~tures can vary within broad limits, but usually is within the range of from 9:1 to 1:9, preerably from 5 9:1 to 1o1.
Polyo2yethylene glycols having a molecular weight below 400 provide a relatively small ignition temperature reduction~
whereas polyoxyethylene glycols having a molecular weight above 4000 have disadvantageous physical properties, such as 10 low melting point, and poor solubility l;n methanol.
The following Examples illustrate preferred embodiments of the invention.
EXAMPLES 1 to 39 , . . . ..
A number of polyo~yalkylene compounds were tested to 15 determine their effect on the ignition temperature of methanol.
The tests were car~ed out using a two-cylinder 10 HP diesel engine. ~ter filling the fuel tank with the test fuel, the tem-perature of the inlet air was gradually increased until a temperature was reached at which the en~ine ran smoothly, and 20 gave a stable emission of organic compollnds in the exhaust ga~es. Then the tempera~ure of the inlet air was decreased graduallyg and the temperatllre at which the proportion of organic compounds in the e~haust gases was 3000 ppm3 measured according to SAE J 2l5~ was noted The temperature 25 of the inlet air when this occurs is a measure of the ease of ignition of the fuel3 i. e. the cetane numher.

.

, ~,j `

The polyo~yalkylene compound added, the amount thereoï
based on the amount of methanol, and the ignition temperature decrease obtained are shown in Table I. The margin of error was --3 C.

lOa ' . , ,-TABLE I
Ignition Tem-~rnount per~ture 5 Example (% o~ decrease ~b TG ~ . rompoU__ ded to metha~ol _methanol) in ~ C__ Control 1 Ethylene glycol 5 0 Polyethylene glycol, mol. weight 200 5 7

2 Polyethylene glycol, mol. weight 300 5 13

3 Polyethylene glycol, mol. weight 400 5 17

4 Polyethylene glycol, mol. weigbt 600 5 21 Polyethylene glycol~ mol. weigh~ 600 10 26 6 Polyethylene glycol, mol. weight 600 15 42 7 Polyethylene glycol, mol. weight 600 20 70 8 Pol~rethylene gl~col, mol. weight 600 25 76 9 Polyethylene glycol, mol. weight 1000 5 20 Polyethylene glycol, mol., weight 1500 5 19 11 Polyethylene glycol, mol. weight 2000 5 23 12 Polyethylene glycol, mol. weight 4000 5 18 20 Con~rol 2 Propylene glycol .
13 Polypropylene glycol, mol. weight 400 5 6 14 PolyE~ropylene glycol, mol. weight 1200 5 14 ~5 Polypropylene glyco~, mol. weight 1800 5 11 lô Polypropylene glycol9 mol. weight 2000 5 6 17 Polypropylene gylcol, mol. weight 4000 5 4 18 Sorbitan mono- oleate ~18 moles ethyllene oxide 5 14 - 19 Sorbitall tri-oleate ~ 20 moles ethylene oxide 5 ~ 12 Sucrose ~ 9 moles ethylene oxide 5 11 ~ .

:

3i~

TABLE_II (continued) Ignition Tem-Exam- Amount pe:rature

5 ple (/0 of decrease No. Test compound added to methanol me~hanol) in " C
21 Sorbitol ~ 7 moles ethylene propylene 5 14 22 Dinonyl phenol ~ 1~ moles ethylene oxide 5 17 23 Dinonyl phenol ~ 30 moles ethylene oxide 5 17 24 Nonyl phenol ~ 20 moles ethylene oxide 5 12 Nonyl phenol ~ 40 moles ethylene oxide 5 15 26 Polypropylene glycol (mol. weight 1200 ~
5 moles ethylene oxide~ 5 11 27 Polypropylene glycol(mol. weight 1800-~
4 moles ethylene oxide) 5 13 28 Polypropylene glycol(mol. weight 1800-~
16 moles ethylene oxide) 5 13 29 2-:Ethylhexanol + 20 moles ethylene oxide 5 15 Lauric acid + 15 moles ethylene oxide 5 14 31 Polyethylene glycol, mol. weight 6007 and 10 56 - dinonyl phenol ~ 16 moles eth~lene oxide 5 32 Polyethylene glycol, mol. weight 6009 and 5 58 dinonyl phenol ~ 16 moles ethylene oxide 10 33 Coco fa~ amine -~ 15 rnoles ethylene oxide 5 21 34 NH3 ~ 23 moles ethylene oxide 5 23 . ~ 35 Oleyl amîne -~ 20 moles ethylene oxide 5 22 3 6 Cetyl mercaptan + 20 moles ethylene oxide 5 20 37 H2S ~ 20 moles ethylene oxide 5 22 38 Lauryl tetra (o~rethylene) phosphate ~
2 moles ethylene oxide 5 16 39 Lauryl tetra(oxyethylene) sulphate 5 15 3~

From Examples 1 to 12, 13 to 17 and 26 to 28 it is evident that the addition ~f polyoxyalkylene glycols to methanol makes it possible to greatly reduce the tempe:rature o-f the inlet air, whereas ethylene glycol ancl propylene glycol (Controls 1 and 2 respectively) 5 have no demonstrable e:ffect A particularly large ignition temperature decrease is sho~n by the polyethylene glycols having a molecular weight of.from 400 to 4000.
E~amples 4 to 8 show that the temperature decrease is dependent on the amount of additive, over a broad I~nge.
The several kinds of polyoxyalkylene compounds tested in Examples 18 to 25, 29 and 30, and 33 to 39 all provide significant temperature decreases.
Examples 31 and 32 illustrate mixtures of a polyo~
ethylene glycol and a sur~ace-active compound. In these 15 Examples the ignition temperature decrease is much greater than would be expected from the results obtained for the indi~idual compounds alone, E~amp~s 5 and 22, and ~ and 22.

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. . - .
,

Claims

Having regard to the foregoing disclosure, the following is claimed as the inventive and paatentable embodiments thereof:

1. A process for operating a diesel engine, which comprises running the engine on a nonpetroleum methanol-base diesel fuel comprising at least 50% by weight methanol and, per 100 parts by weight of methanol, from about 2 to about 40 parts by weight of a methanol-soluble polyoxyalkylene compound containing from about 4 to about 400 units derived from an alkylene oxide selected from the group consisting of ethylene oxide and propylene oxide, the oxyalkylene units being at least 40% by weight of the total polyoxyalkylene compound.

2. A process according to claim 1, in which the diesel fuel comprises from about 5 to about 25 parts by weight of a methanol-soluble polyoxyalkylene compound containing from about 4 to about 400 units derived from an alkylene oxide selected from the group consisting of ethylene oxide and propylene oxide, the oxyalkylene units being at least 40% by weight of the total polyoxyalkylene compound.

3. A process according to claim 1, in which the diesel fuel comprises a polyoxyalkylene compound containing from about 6 to about 100 oxyalkylene units derived from an alkylene oxide selected from the group consisting of ethylene oxide and propylene oxide.

4. A process according to claim 1, in which the diesel fuel comprises a polyoxyalkylene compound having at least four oxyalkylene units in a straight chain.

5. A process according to claim 1, in which the diesel fuel comprises a polyoxyalkylene compound having the formula:

wherein:
m is a number within the range from 1 to 12;
n is 2 or 3 or a mixture thereof;
x is a number within the range from about 4 to about 400, preferably from about 6 to about 100, and represents an average number of the various species present;
X is selected from the group consisting of oxygen, sulfur, and wherein:
n1 is a number within the range from 1 to 6 r is a number within the range from O to 10 R1 and R2 are selected from the group consisting of hydrogen; the residue of an organic compound composed only of atoms selected from hydrogen, carbon and oxygen, and [O(C?H?O)xG];
G is selected from the group consisting of hydrogen, the group OR3, the group SO3M and- where R3 is a hydrocarbon group having from one to twenty-four carbon atoms, and R4 is selected from the group consisting of OM and the group R1[X(C?H?O)xG]m-1, where M is hydrogen or an inorganic or organic salt-forming cation.

6. A process according to claim 1, in which the diesel fuel comprises water in an amount within the range from about 2 to about 10%
based on the weight of methanol.

7. A process according to claim 1, in which the diesel fuel comprises a polyoxyalkylene compound having the formula:

wherein:
n is 2 or 3 or a mixture thereof;
R5 and R6 from one to about twenty-four carbon atoms, and [CnH2nO]xH; and x is a number from about 4 to about 40.

8. A process according to claim 1, in which the diesel fuel comprises a polyoxyalkylene compound having the general formula:

R1-S-[CnH2nO]xR8 wherein:
R1 is selected from the group consisting of hydrogen, the residue of an organic compound composed only of atoms selected from hydrogen carbon and oxygen, and [O(CnH2nO)xG];

G is selected from the group consisting of hydrogen the group OR3, the group SO3M and where R3 is hydrocarbon group having from one to twenty-four carbon atoms, and R4 is selected from the group consisting of OM and the group R1[X(CnH2nO)xG]m-1, where M is hydrogen or an inorganic or organic salt-forming cation;
R? is selected from the group consisting of hydrogen and hydro-carbon groups having from one to about twenty-four carbon atoms;
n is 2 or 3 or a mixture thereof; and x is a number from about 4 to about 40.

9. A process according to claim 1, in which the diesel fuel comprises a polyoxyalkylene compound having the formula:
R9 [ OCnH2n]xOHm wherein:
R9 is hydrogen or the residue of an organic compound that is composed only of atoms selected from hydrogen, carbon and oxygen, which compound has from one to about twelve hydrogens reactive with ethylene oxide or propylene oxide;
m is a number from 1 to about 12;
n is 2 or 3, or a mixture thereof; and x is a number from about 4 to about 400, preferably from about 6 to about 100.

10. A process according to claim 9, in which R9 is hydrogen.--

11. A pxocess according to claim 1, in which the diesel fuel comprises a polyoxyalkylene compound selected from the group consisting of surface-active polyoxyalkylene glycol ethers and esters, sulfates and phosphates imparting to water a surface tension of below 50 dynes/cm at a concentration of 1% by weight at a temperature of 25°C.

12. A process according to claim 11, in which the polyoxyalkylene glycol ether and ester has the formula:

R-A-(CnH2nO)xH
where R is hydrogen or a straight or branched chain saturated or unsaturated hydrocarbon group having from eight to thirty caxbon atoms or an aralkyl group having a straight or branched chain saturated or unsaturated hydro-carbon group of from six to twenty-four carbon atoms attached to the aryl nucleus, and attached to A through the aryl nucleus;
A is selected from the group consisting of ethereal oxygen and sulfur, carboxylic ester and thiocarboxylic ester groups;
n is 2 or 3 or a mixture thereof; and x is a number from. 4 to 40.

13. A process according to claim 11, in which the polyoxyalkylene phosphate ester has the formula:
where at least one R is a radical containing polyoxyalkylene ether and no more than one R is hydrogen, the radical containing polyoxyalkylene ether having the formula:

R3-O-(CnH2nO)x-in which R3 is selected from the group consisting of aliphatic hydrocarbon radicals having from about eight to about thirty carbon atoms, and mono, di, or trialkyl-substituted phenyl radicals having from about six to about twenty-four carbon atoms, and from about eight to about eighteen carbon atoms in the alkyl portion;
M is hydrogen or a water-soluble salt-forming cation;
n is 2 or 3 or a mixture thereof; and x is a number from a to about 30, and denotes the average number of oxyalkylene units in the chain.