Fatty Acid Esters and Uses Thereof

8/17/2019 Fatty Acid Esters and Uses Thereof

1/16

Fatty acid esters and uses thereofEP 1685218 A2 (metnin alındığı doküman !"2##5#$#%12A2& 'E)

Esters formed from polyol C12-C28 branched chain fatty acid, and/or C12-C28 cyclic fatty acid are useful as a friction

modifier for lubricants. Monomer is a preferred source for these fatty acids.

*A+ )A,EP,E-. (OC metni hatalar i!erebilir"

#olyol Monomerate.

2. $he polyol Monomerate of claim 1 %herein the polyol is &lycerol.

#olyol monoMonomerate.

$he polyol monoMonomerate of claim ' %herein the polyol is &lycerol.

composition comprisin& polyol monoMonomerate and polyol diMonomerate.

). $he composition of claim * %herein the polyol is &lycerol.

+. composition comprisin& a first component selected from the &roup consistin& of monoester of polyol and

Monomer, diester of polyol and Monomer, and triester of polyol and Monomer, and a second component selected from

the &roup consistin& of monoester of polyol and Monomer, diester of polyol and Monomer, triester of polyol and

Monomer, polyol, and Monomer %here the first and second components are non-identical.

8. $he composition of claim + %herein the polyol is &lycerol.

. $he composition of claim + %herein the polyol and the Monomer are each present in the composition at

concentrations of less than 1 %ei&ht percent.

1. composition comprisin& the esterification product of a" Monomer or a reacti0e eui0alent thereof and b" polyol

or a reacti0e eui0alent thereof.

11. $he composition of claim 1 %herein the polyol is &lycerol.

12. composition comprisin& the esterification product of a" a Ci2-C28 cyclic fatty acid or reacti0e eui0alent thereof

b" a C12-C28 branched fatty acid or reacti0e eui0alent thereof and c" one or more polyols or reacti0e eui0alents

thereof.

1'. $he composition of claim 12 %herein the polyol is &lycerol.

1. $he composition of claim 12 %herein the composition comprises the esterification product of &lycerol and

pentaerythritol.

1*. $he composition of claim 12 %herein each of the C 12-C28 cyclic fatty acid and the C12-C28 branched fatty acid are

present in Monomer.

1). composition comprisin& a first ester selected from O

O3 o o 4 c a

3O32C C C32OC 2a 3O32C C C32O3 3 and 3 and a second ester selected from O3 c

2b

http://www.google.com.ph/patents/WO2005030912A2?hl=tr&cl=enhttp://www.google.com.ph/patents/WO2005030912A2?hl=tr&cl=en


2/16

3O32C- -C- -C32OC 2b 3O3,C- -C- -C32O3 3 and 3 %herein 2a is a branched C52-C28 hydrocarbon and

2b is a

cyclic C52-C28 hydrocarbon.

1+. $he composition of claim 1) %herein 1-COO3 and -COO3 are present in Monomer.

18. lubricatin& composition comprisin& a lubricatin& fluid and an ester of claim 1. . lubricatin& composition of

claim 18 %hich is a lubricatin& oil.

2. lubricatin& composition of claim 18 %hich is a metal %or6in& fluid composition.

21. method of impro0in& the friction properties of a lubricant fluid comprisin& addin& an ester of claim 1to a lubricant

fluid.

22. fuel composition comprisin& a distillate fuel ha0in& a sulfur content less than .*7 by %ei&ht and from 1 to

1, ppm of an ester of claim 1.

2'. $he fuel composition of claim 22 %herein the fuel composition is a diesel fuel composition.

2. method for impro0in& the lubricity of a distillate fuel ha0in& a sulfur content of less than .*7 by %ei&ht,comprisin& the addition thereto of the ester of claim 1.

A/0+,AA (OC metni hatalar i!erebilir"

$$9 C:; E=; O $3E :=BE=$:O= ield of the :n0ention $he present in0ention is directed to polyol esters. $his

in0ention also relates to the use of these esters in fuels, oils and lubricant pac6a&es for en&ines and in metal %or6in&

fluids, %here the esters enhance the performance properties of the composition.

;escription of the elated rt Alycerol monooleate (AMO" is %ell 6no%n to function as a friction modifier in lubricant

compositions for en&ines. .nichema (=etherlands" and

Mundelein, :, >


3/16

the Ci2-C28 cyclic fatty acid and the C52-C28 branched fatty acid is present in Monomer. :n another aspect, the present

in0ention pro0ides a composition comprisin& a first ester selected from O

O3 o - ,2a

3O3,C- -C- -C32OC r a and 3O32C- -C- -C32O3 3 3 and a second ester selected from o O3 o- - ,2b

3O3,C- -C- -C32OC- '2Fb and 3O32c- -c- -C32O3 3 3 %herein 2a is a branched C12-C28 hydrocarbon and 2b is a

cyclic C52-C28 hydrocarbon. :n a preferred embodiment, 1-COO3 and 2-COO3 are present in Monomer. :n additional

aspects, the present in0ention pro0ides a fuel composition comprisin& a distillate fuel ha0in& a sulfur content less than

.*7 by %ei&ht and from an ester or composition (or both" as described herein. nalo&ously, the present in0ention

pro0ides a method for impro0in& the lubricity of a distillate fuel ha0in& a sulfur content of less than .*7 by %ei&ht,

comprisin& the addition thereto of the ester or ester composition as described herein. $he ester or composition is

present in the fuel composition in an amount effecti0e to enhance the lubricity of the fuel, i.e., a composition of base

fuel and ester of the present in0ention displays superior lubricity properties compared to the base fuel in the absence

of the ester of the present in0ention. $his effecti0e amount is typically 1 to 1, ppm of ester. $he fuel may be, and

in one aspect of the in0ention is, a diesel fuel. Other suitable fuels include Det fuel and &asoline. :n one aspect, theester is polyol Monomerate.ln additional aspects, the present in0ention pro0ides lubricant composition comprisin& an

lubricatin& base fluid as classified in Aroups : to B by merican #etroleum :nstitute (#:" and adopted by the lubricant

industry and an ester or ester-containin& composition of the present in0ention. nalo&ously, the present in0ention also

pro0ides a method of impro0in& the friction properties of a lubricatin& base fluid comprisin& addin& an ester or ester-

containin& composition of the present in0ention to lubricatin& base fluid . :n the preferred embodiments of the

in0ention the lubricatin& fluid is a lubricatin& oil, an industrial oil, e.&., a po%er transmission fluid or a hydraulic fluid or

a lubricatin& fluid used in metal %or6in& fluids, e.&.Gfluids used for cuttin& , &rindin&, and stampin& metals. $hese and

related aspects of the present in0ention are described in further detail belo%. ;E$:E; ;E


4/16

small amounts of oleic and linoleic acids, and instead contains si&nificant amounts of branched and cyclic C- 18 acids,

both saturated and unsaturated, as %ell as elaidic acid. $he more di0erse and si&nificantly branched composition of

Monomer results from the catalytic processin& carried out on $O by the polymeriHation process Dust described. $he

art reco&niHes that the reaction of Monomer %ith other chemical substances yields uniue, identifiable deri0ati0e

substances that are chemically different from correspondin& $O deri0ati0es. Monomer has been assi&ned C<

e&istry =umber )8**-8-). suitable Monomer for the practice of the present in0ention is Century MO*L fatty acid

as a0ailable from riHona Chemical Company, ac6son0ille, lorida. :n one aspect, the present in0ention is directed to

polyol Monomerate. $he term polyol Monomerate is used herein to denote a blend of esters, %here an ester is

&enerally reco&niHed to include the chemical formula 1-O-CNO-2, and usin& this nomenclature 1-O may be

referred to as the alcohol portion of the ester %hile -CNO-2 may be referred to as the acid portion of the ester. :n the

polyol Monomerate of the present in0ention, 1 is the polyol portion %hile 2 is the Monomer portion. :n other %ords,

1 has the structure of the polyol %hile 2 has the structure of the Monomer. n alcohol is an or&anic compound

ha0in& at least one hydroyl (-O3" &roup. polyol is an alcohol ha0in& t%o or more, i.e., a plurality of, hydroyl

&roups, and accordin& may be denoted as -(O3"n, %here n denotes the number of hydroyl &roups present in the

polyol. :n 0arious literatures a polyol is sometimes referred to as a polyhydric compound. ccordin& to the present

in0ention, a polyol Monomerate has an 1 &roup as %ell as at least one ester &roup, %here each ester &roup is

attached to an 2 &roup in addition to bein& attached to the 1 &roup. $he 2 &roup of polyol Monomerate is

necessarily deri0ed from Monomer. $hat is, the 2 &roup %ill ha0e the structure of the carboylic acid components of

Monomer. $he %ord IMonomerI as used herein be&ins %ith a capital letter to denote that it is the material 6no%n in the

art as IMonomerI rather than bein& any reacti0e molecule that mi&ht be denoted as lo%er case ImonomerI. s

mentioned abo0e, polyol Monomerate contains 1, at least one ester &roup, and at least one 2 &roup deri0ed from

Monomer. :n 0arious aspects of the in0ention, the 1 &roup has 2-12 carbons, or 2-) carbons, or 2 carbons, or '

carbons, or carbons, or * carbons, or ) carbons. :n a preferred aspect, the 1 &roup contains only carbon and

optionally hydro&en, i.e., the 1 &roup is a hydrocarbyl &roup. #< -Carbon &roups -C3, -C3, -Carbon 1

&roups -C3, -C3, -C3, -C3, -C3- -C3,

-Carbon 1 &roups -C3, -C3, -C3, -C3, -C3, -C3- -C3, -C3a

C3' C3 C3 C3' C3 C32 C3 C3'

-C3, C3 C3, C3, -C3, C3 C3 C3,

*-Carbon 1 &roups

:n $able , IC I represents a bond from a carbon to either a hydroyl (-O3" or ester (--CNO" &roup. Khen a polyol

Monomerate has one ester &roup, that compound is referred to herein as a polyol monoMonomerate. i6e%ise, %hena polyol Monomerate has t%o ester &roups, that compound is referred to herein as a polyol diMonomerate. Khile a

polyol Monomerate has at least one ester &roup, it may ha0e Hero, one, or more than one hydroyl &roups. or

instance, %hen 1 has the structure


5/16

the term polyol Monomerate includes polyol monoMonomerates of either of the follo%in& t%o structures

o as %ell as polyol diMonomerates of either of the follo%in& t%o structures

and the polyol triMonomerate of the follo%in& structure

or con0enience, the 1 &roup may be identified herein by namin& the polyol from %hich it may be lo&ically deri0ed.

$hat is, the 1 &roup can and freuently %ill be identified by the name of the correspondin& polyol ha0in& a hydroyl

&roup at each open position of the 1 &roup. $his nomenclature is illustrated in $able ?, %hich essentially repeats

$able but adds the name of the polyol correspondin& to each 1 &roup.

$?E ? =ME< O EEM#9 1 AO>#


6/16

$?E ? =ME< O EEM#9 1 AO>#< -Carbon 1 &roups -C32 C32 C32 C32- -C3, C3- -C3, -C3,

1 ,-butanediol 1 ,2-butanediol

C3, -C3- -C3- -C3a C3, -C3, -C3- -C3,

2,'-butanediol 1 ,'-butanediol

-C3, -C3- -C3, -C3, -C3, C3 C3 C3,

1 ,2,-butanetriol 1 ,2,',-butanetetraol

*-Carbon 1 &roups

pentaerythritol

s mentioned abo0e, the 2 &roup in a polyol Monomerate is deri0ed from Monomer. Monomer is a commercially

a0ailable product that includes a 0ariety of or&anic carboylic acids. Monomer is typically a miture of branched-,

aromatic-, cyclic-, and strai&ht-chain fatty acids, %hich may be saturated or unsaturated. $he predominant acid in

Monomer is Iiso-oleic acidI, %here iso-oleic acid is a miture of linear, branched and cyclic C-5 8 mono-unsaturated fatty

acids. $he iso-oleic acid may be refined from Monomer by lo% temperature sol0ent separation, in order to prepare a

purified iso-oleic acid. :n one aspect, the polyol Monomerate is prepared from iso-oleic or a blend of acids includin&

iso-oleic, and accordin&ly may be referred to as polyol iso-oleate. $hus, the term polyol Monomerate refers to a blend

of esters prepared from either Monomer or a by-product of Monomer (e.&., a distillati0ely- refined Monomer, or an

esterification product of Monomer". :n one aspect, the 2 &roups in polyol Monomerate include at least a cycloaliphatic

C1+ hydrocarbyl &roup and a branched-chain C1+ hydrocarbyl &roup. :n another aspect, the 2 &roups in polyol

Monomerate include at least a cycloaliphatic C1+ hydrocarbyl &roup, a branched-chain aliphatic C1+ hydrocarbyl &roup,


7/16

and a strai&ht-chain aliphatic C1+ hydrocarbyl &roup. :n another aspect, the 2 &roups in polyol Monomerate include at

least a cycloaliphatic C1+ hydrocarbyl &roup, a branched- chain aliphatic C1+ hydrocarbyl &roup, a C1+ hydrocarbyl

&roup includin& an aromatic rin&, and a strai&ht-chain C 1+ hydrocarbyl &roup. $he term IaI as used here and

else%here in the specification refers to Ione or moreI. Elaidic acid is one of the fatty acids normally present in

Monomer. ccordin&ly, in one aspect, polyol Monomerate includes a polyol ester of elaidic acid. :n 0arious other

aspects, the present in0ention pro0ides &lycerol monoelaidate, &lycerol dielaidate, and &lycerol trielaidate. $he elaidic

ester %ill typically not be pure, but %ill be present in a composition that contains other polyol esters, %here this

composition %ill typically be deri0ed from Monomer. typical commercially a0ailable Monomer has both cyclic and

branched C18 fatty acids. typical branched C-58 fatty acid commonly found in Monomer has the follo%in& structure

Eemplary cyclic C-i8 fatty acids sometimes found in Monomer ha0e the follo%in& structures

ccordin&ly, polyol Monomerate denotes a miture of esters, %here this miture is defined by ha0in& acid portions

deri0ed from Monomer. :n other %ords, the 2 &roup in polyol Monomerate actually represents a plurality of

hydrocarbyl &roups, includin& both branched and cyclic C1+ hydrocarbyl &roups. :n one aspect of the in0ention, the

cyclic C1+ hydrocarbyl &roup is unsaturated. :n another aspect of the in0ention, the cyclic C-5 + hydrocarbyl &roup is a


8/16

miture of saturated and unsaturated C5 hydrocarbyl &roups. $he preparation of the polyol Monomerate of the

in0ention may be accomplished by 0arious means. strai&htfor%ard synthetic method is to combine Monomer %ith a

polyol ha0in& the desired 1 structure, and then heat these t%o reactants until polyol Monomerate is formed. $his

esterification reaction typically reuires ele0ated temperature in the ran&e of 1*-2*PC in order to proceed in an

economically timely fashion. $he pro&ress of the esterification reaction may be readily monitored by pullin& a sample

and subDectin& that sample to acid number analysis. relati0ely lo%er acid number indicates a relati0ely further de&ree

of esterification, since the acid number is effecti0ely a measure of the amount of unreacted Monomer present in the

reaction miture. cid number is measured by dissol0in& a 6no%n %ei&ht of sample into an or&anic sol0ent (toluene is

a typical sol0ent", and then titratin& a measured amount of methanolic potassium hydroide (@O3" solution into the

sample solution. $he titration is complete %hen a p3 of about + is attained. $he acid number of the sample is eual to

the amount of @O3, in m&, %hich %as used in the titration, di0ided by the %ei&ht of sample, in &rams, that %as titrated.

:n other %ords, acid number is eual to the m& of @O3 needed to neutraliHe 1 &ram of sample. :t is typically the case

that not all of the Monomer can be readily con0erted into an esterified form. ccordin&ly, the product polyol

Monomerate %ill typically ha0e an acid number of &reater than Hero. =e0ertheless, for performance as a lubricity aid, it

is preferred that the acid number of the product miture be relati0ely lo%, typically less than 1, more typically less

than *. :t is also typically the case that not all of the polyol can be readily con0erted into an esterified form. esidual

polyol may be remo0ed from the product miture by distillation, %here the distillation conditions %ill depend on the

identity of the polyol. #olyois %ith hi&her boilin& points %ill reuire more se0ere distillation conditions, i.e., hi&her

temperature and/or &reater 0acuum. esidual polyol may also be remo0ed by steam distillation. :n one aspect of the

in0ention, the polyol content of a composition includin& polyol Monomerate is less than 1 %ei&ht percent of the

composition, %hile in other aspects the polyol content is less than 8 %ei&ht percent, less than ) %ei&ht percent, less

than %ei&ht percent, less than 2 %ei&ht percent, or less than 1 %ei&ht percent. i6e%ise, in one aspect of the

in0ention, the Monomer content of a composition includin& polyol Monomerate is less than 1 %ei&ht percent of the

composition, %hile in other aspects the Monomer content is less than 8 %ei&ht percent, less than ) %ei&ht percent,

less than %ei&ht percent, less than 2 %ei&ht percent, or less than 1 %ei&ht percent. dditional aspects of the

in0ention pro0ide compositions includin& polyol Monomerate %herein each of the polyol and Monomer contents of the

composition are independently selected from less than 1 %ei&ht percent, less than 8 %ei&ht percent, less than )

%ei&ht percent, less than %ei&ht percent, less than 2 %ei&ht percent, and less than 1 %ei&ht percent of the

composition. :n relation to each of these aspects of the in0ention, the present in0ention pro0ides additional aspects

%herein the polyol and/or Monomer content of the composition is at least .1 , or .*, or 1. %ei&ht percent of the

composition. $o increase the rate of the esterification reaction, a catalyst for esterification reactions may be included in

the reactant miture. Esterification catalysts are %ell 6no%n in the art and include sulfuric acid, phosphoric acid and

other inor&anic acids, metal hydroides and al6oides such as tin oide and titanium isopropoide, and di0alent metal

salts such as tin or Hinc salts. preferred catalyst is a tin catalyst, e.&.,


9/16

pressure. Khile the reaction of polyol and Monomer is a con0enient approach to preparin& polyol Monomerate,

0ariations on this approach may also be used. or eample, a transesterification reaction may be used, %herein an

ester of Monomer, e.&., the methyl ester, is reacted %ith a polyol. $his approach %ill produce polyol Monomerate %ith

methanol as a by-product. $he methyl ester of Monomer is therefore a reacti0e eui0alent of Monomer in the

preparation of polyol Monomerate. $he acid chloride form of Monomer is another reacti0e eui0alent of Monomer that

could be used to prepare polyol Monomerate, ho%e0er this %ould typically raise the cost of preparin& the polyol

Monomerate, and %ould also introduce an undesirable by-product (hydro&en chloride". i6e%ise, an ester of the polyol

may be used in lieu of polyol, %here acetate ester is a suitable ester, and this ester is a reacti0e eui0alent of the

polyol. $hus, in one aspect, the present in0ention pro0ides a composition comprisin& the esterification product of (a"

Monomer or a reacti0e eui0alent thereof and (b" polyol or a reacti0e eui0alent thereof. :n a related aspect, the

present in0ention pro0ides a composition comprisin& the transesterification product of (a" polyol Monomerate and (b"

polyol or a reacti0e eui0alent thereof. :n a preferred embodiment, the polyol in these compositions is &lycerol. :n

additional aspects, the present in0ention pro0ides polyol Monomerate, %hich includes one or more of polyol

monoMonomerate, polyol diMonomerate, polyol triMonomerate, etc. dependin& on the functionality of the polyol

component. :n 0arious embodiments %ithin this aspect of the in0ention, the polyol may be a diol, e.&., ethylene &lycol,

1 ,2-propylene &lycol, 1 ,'-propylene &lycol, 1 ,2-butylene &lycol, 1 ,'-butylene &lycol, 1 ,-butanediol, 1 ,)-heanediol,

neopentyl &lycol, and 1 ,-cycloheanedimethanol or a triol, e.&., &lycerin, trimethylolpropane, or

tris(hydroylmethyl"methanol or a tetraol, e.&., pentaerythritol, or oli&omers thereof, e.&., di-pentaerythritol, and tri-

pentaerythritol. Each of these polyols may be used in the preparation of a polyol ester of the present in0ention. or

instance, in one embodiment the present in0ention pro0ides polyol monoMonomerate, e.&., &lycerol

monoMonomerate. :n another embodiment the present in0ention pro0ides polyol diMonomerate, e.&., &lycerol

diMonomerate. :n another embodiment the present in0ention pro0ides a blend that is, or comprises, polyol

monoMonomerate and polyol diMonomerate, %here the polyol and Monomerate components are the same in the

monoMonomerate and the diMonomerate. or instance, the present in0ention pro0ides a composition that is, or

comprises, a blend of &lycerol monoMonomerate and &lycerol diMonomerate. or use as a friction modifier in en&ine

oils, it is preferred to use a blend of polyol Monomerates, includin& both polyol monoMonomerate and polyol

diMonomerate.


10/16

portion of the first and second esters is not identical. Khen the alcohol portions of the first and second esters is not

identical, each of the alcohol portions may be selected from, e.&., a diol, e.&., ethylene &lycol, 1 ,2-propylene &lycol, 1 ,

'- propylene &lycol, 1 ,2-butylene &lycol, 1 ,'-butylene &lycol, 1 ,-butanediol, 1 ,)- heanediol, neopentyl &lycol, and

1 ,-cycloheanedimethanol or a triol, e.&., &lycerin, trimethylolpropane, or tris(hydroylmethyl"methanol or a tetraol,

e.&., pentaerythritol, or oT&omers thereof, e.&., di-pentaerythritol, and tri-pentaerythritol. $he first and second esters

may be monoesters, diesters, triesters, etc. or instance, in the case %here 1 is, at least formally, deri0ed from

&lycerin, the present in0ention pro0ides a composition comprisin& a first ester selected from

O3 '2a

3O32C C C32OC Ra and 3O32C C C32O3 3 3 and a second ester selected from

O3 o- - 2b

3O32C- -C- C32OC '2b; and 3O32C- -C- -C32O3 3 3 %herein

2a is a branched C-52-C28 hydrocarbon and 2b is a

cyclic Ci2-C28 hydrocarbon. 3o%e0er, in another aspect, the first ester may be deri0ed, at least formally, from &lycerin,

%hile the second ester is, at least formally, deri0ed from pentaerythritol. :n a related aspect, the present in0entionpro0ides a composition comprisin& a first component selected from the &roup consistin& of monoester of &lycerol and

branched C12-C28 fatty acid, diester of &lycerol and branched C12-C28 fatty acid, and triester of &lycerol and branched C-

52-C28 fatty acid, and a second component selected from the &roup consistin& of monoester of &lycerol and cyclic C5 2-

C28 fatty acid, diester of &lycerol and cyclic C52-C28 fatty acid, triester of &lycerol and cyclic C52-C28 fatty acid, and

&lycerol. ?ranched and cyclic C52-C28 fatty acids can be obtained from many sources. or instance, suppliers of fine

and bul6 chemicals may sell branched and cyclic C52-C28 fatty acids. @", 0ocado

esearch (ancashire >.@.", ?;3 :nc. ($oronto, Canada", ?ionet (Corn%all, >.@.", Chemser0ice :nc. (Kest Chester

#", Crescent Chemical Co. (3auppau&e =9", Eastman Or&anic Chemicals, Eastman @oda6 Company (ochester

=9", isher .@.", ancaster $", #faltH U ?auer, :nc. (Katerbury C=", #olyor&ani

(3ouston $", #ierce Chemical Co. (oc6ford :", iedel de 3aen A (3anno0er, Aermany",


11/16

fluids are classified in Aroups : to B accordin& to merican #etroleum :nstitute (#:" and adopted by the lubricant

industry. $hese are Aroup 1 (sulfur X or N .'7, saturates Y or N 7, 0iscosity inde X or N 8 and Y or N 12"

consists of sol0ent etracted mineral oil, Aroup :: (sulfur Y or N.'7, saturates X or N7, 0iscosity inde X or N8 -

Y or N12" consists of sol0ent etracted and hydrofinished mineral oils, Aroup ::: (sulfur Y or N.'7, saturates X or N

7, 0iscosity inde X or N12" consists of hydrocrac6ed mineral oils, Aroup :B ( #olyalphaolefin, #O" and Aroup B

(e0erythin& that is not included in Aroups 1-B" these include esters, al6ylated aromatics, and silicones. $he esters

and ester blends of the present in0ention are preferably used to impro0e the friction characteristics of en&ine oils. s a

primary function of en&ine oil is to pro0ide lubricity bet%een en&ine parts %here at least one of those en&ine parts is

mo0in& durin& en&ine operation, the en&ine oil should be an oil of lubricatin& 0iscosity. $he en&ine oil may be, or

include, natural or synthetic oils and mitures thereof. =atural oils include animal oils, 0e&etable oils, mineral

lubricatin& oils, sol0ent or acid treated mineral oils, and oils deri0ed from coal or shale. .


12/16

2,)**,+ 1 ,81*,22 2,11 ,8 2,))),+) 2,+21 ,8++ 2,+21 ,8+8 and ',2*,+1* and nti foam a&ents, %hich

function to reduce or pre0ent the formation of stable foam. $ypical anti foam a&ents include silicones or or&anic

polymers. $he polyol esters, includin& the polyol Monomerate of the present in0ention may be included in an en&ine

oil composition at a concentration of about .17 to 17 by %ei&ht of the composition, %here a concentration of about

.*7 to 27 by %ei&ht is typically optimal. $he oil may be formulated for 2-cycle en&ines or -cycle en&ines. $he oil

may be formulated for a &asoline-po%ered en&ine, a Det- fuel po%ered en&ine, or a diesel fuel po%ered en&ine, to

name a fe%. Khile the oil is preferably a lubricatin& oil, the esters of the present in0ention may also be used in

combination %ith any other oil %here it is desired to impro0e the friction characteristics of the oil.


13/16

$he base fuels used in formulation a fuel composition of the present in0ention include any base fuels suitable for use

in the operation of spar6-i&nition or compression-i&nition internal combustion en&ines such as diesel fuel, Det fuel,

6erosene, leaded or unleaded motor and a0iation &asolines, and so-called reformulated &asolines %hich typically

contain both hydrocarbons of the &asoline boilin& ran&e and fuel-soluble oy&enated blendin& a&ents, such as

alcohols, ethers and other suitable oy&en-containin& or&anic compounds. Oy&enates suitable for use in the present

in0ention include methanol, ethanol, /so-propanol, t- butanol, mied Ci to C* alcohols, methyl tertiary butyl ether,

tertiary amyl methyl ether, ethyl tertiary butyl ether and mied ethers. Oy&enates, %hen used, %ill normally be

present in the base fuel in an amount belo% about 2*7 by 0olume, and preferably in an amount that pro0ides an

oy&en content in the o0erall fuel in the ran&e of about .* to about * percent by 0olume. $he present in0ention %ill

no% be illustrated by the follo%in& Eample, %hich is eemplary of the in0ention and not to be construed as a

limitation thereon. $his Eample illustrates the synthesis and performance properties of a polyol ester of the present

in0ention, and additionally compares these performance properties to the properties of a commercially successful

polyol ester, i.e., &lycerol monooleate (AMM", that is used in en&ine oils.

EM#E Monomer (CE=$>9 M*L fatty acid from riHona Chemical, ac6son0ille, , >


14/16

urther performance data about the ability of the ester of the present in0ention to impro0e the friction properties of a

lubricant %as obtained by performin& a hi&h freuency reciprocatin& ri& (3" test. ?lends ha0in& 1 %t7 of AMM or

AMO in neat base oil (=?O" %ere tested and compared %ith neat base oil. $he =?O %as a hydrotreated hi&h 0iscosity

petroleum-deri0ed oil 6no%n as C:$8*L oil (C:$AO, $ulsa, O@, >


15/16

Aear Oil C, had the follo%in& composition Composition of Aear OilGC #O /Ester ?ase luid ()7 by %&t."

rylamine and #henolic ntioidants (1.*7 by %&t." Mobilad A'* Aear Oil dditi0e #ac6a&e (2.'7 by %&t." E

$he results set forth in $able * sho% that the addition of .1 %t7 AMO lo%ered the friction coefficient at ambient

temperature (relati0e to Aear Oil C alone" by 2*. 7 %hile addition of .1 %t7 AMO lo%ered the friction coefficient at

ambient temperature by '1.'+7. $he results of the in& on ;is6 test at 1PC are set forth in the follo%in& $able *.

$?E ) :C$:O= COE:C:E=$ MEEME=$ \ $ 1PC

$he results set forth in $able ) sho% that the addition of .1 %t7 AMO lo%ered the friction coefficient at ambienttemperature (relati0e to Aear Oil C alone" by 2.1 7 %hile addition of .1 %t7 AMO lo%ered the friction coefficient at

ambient temperature by +2.'+7. $he results of the hi&h freuency reciprocatin& ri& (3" test are set forth in the

follo%in& $able +.

$?E + :C$:O= COE:C:E=$ MEEME=$ ?9 3

$he results set forth in $able + sho% that the addition of .1 %t7 AMM lo%ered the friction coefficient and the Kear


16/16

-eferans

1 ] =o further rele0ant documents disclosed

2 ]

Documents

Fatty Acid Esters and Uses Thereof