CA2098995A1

CA2098995A1 - Lubricant adducts and their preparation

Info

Publication number: CA2098995A1
Application number: CA 2098995
Authority: CA
Inventors: Ross A. Kremer; Derek A. Law; G. Ali Naghipur; Carleton N. Rowe; Leslie R. Rudnick
Original assignee: Individual
Current assignee: ExxonMobil Oil Corp
Priority date: 1991-01-04
Filing date: 1992-01-03
Publication date: 1992-07-05
Also published as: EP0565624A1; JPH06504289A; EP0565624A4; WO1992012222A1

Abstract

Alkylated diphenyl ethers, alkylated diphenyl methanes, alkylated phenoxathins and alkylated diphenyl sulfides are high-temperature stable lubricant fluids having excellent low temperature viscometrics, and excellent additive solubility. These adducts may be used as such as lubricants or may be blended with other lubricant fluids or fuel compositions.

Description

W V 92/12222 2 0 9 8 9 ~ ~ PCT/US92/00035 m is invention relates to lubricant adducts and theirpreparation. More parti~larly, this invention relates to imprcved lubricant fluid oompositions comprising these ad~ucts S alone or blen~ed wit~ synthetic or mineral oil lubricant compositions; and to fuel oompo6itions comprising these addu~ts.
Aosr~dina to one aspect of the present inventicn, there is provided an adduct preparable by cat~lytically reac ~ :

i) at least one ccmpound oomprising at least one olefinic group; a hydm ~arbyl substituent: and, optionally, at least one heteroatom; with ii) a substituted or urEubstituted, fused or unfused, polynuclear, arom~tic oompound ~i*. may con~ain at le~t ore c~alcoger.
atom.

The hydrrcarbyl substituent of i) may be aliphatic or cyclic (including arccatic and alicyclic) and may be linear or branched.
Suitably, the hydrrcarbyl sukstituent ocmprises an adduct ~ccond}na to cla~m 1 w.herein the oydrrcarbyl substituent co~prises a C3 to C500 alkyl, alkenyl or alkynyl group, a C7 to C500 araIkyl or alkaryl gr w p or a C6 to C500 aryl group.
Preferably, the hydLoc~rbyl substituent oompcise~ from 6 to 50 carbcn atcms; for example, from 8 to 18 carbon atoms.
Preferably, czmçsund i) c=l}r~ses an alpha olefin. Whre co~pound i) c~pris~s a hekercatom this may'be S,N,O,P and/or F.

W O 92/12222 PCT/US9t/~003.~ ~

2~989g'~i ' In ac~o=lancs with the invention, oompound ii) preferably has the general formLla :
~l~X~13 in which :

X represents an oxygen or sulphur atom or a methylene group; an~
Y rep:esents a sulpbur atom or tWD hydrogen atcms attached to different aromatic rings.

~he aromatic rings of comçound ii) may be ~h~tituted on cne or ~ore positions of any aromatic ring. Substituticn by an 1~ alkil grcyp is p~2~2rred, esp2cially ~ith at least 0~2 aI~yl group cn each ring.
It is pref d that compound ii) oomprises an ad~uct according to claim 7 wherein ii) comprises diphenyl ether, diphenyl s~lphide, diphenylmethane or phenoxathiin.
Ihe adducts of this invention prepared over zeolite catalysts have a higher VI at a given vicrneity.
In ~cccrdance with a second aspect o~ ~h;~ invention, there is provided a process for the preparation of an adduct, which prcc~ss ccLprises catalytically reacting :

i) at least c,ne compound r -~n~cing at least one olefinic group; a hydmoarbyl substituent; and, opticnally, at least ~e he~c~ with W O 92/l2222 2 ~ 9 ~ ~ 9 ~ Pcr/us92/0003~
, . . .

ii) a substituted or unsubstituted, fused or unfused, polynuclear, aromatic compound which may contain at least one ch21ccgen atom at a ~Dm prature L,u~ ambient to 350C; a lar ratio of i) : ii) from 0.5:1.0 to 10.0:1.0; and a ratio of catalyst : ii) from lg :
1 1, preferably 5g:1 1, to 100 g: 1 mol.

This invention also pr~vides a high temperature stable lubricant fluid .uu~rising an adduct as herein descri~ed. Ihe invention further provi~s a fuel oomposition ~-~rising an adduct as herein described and a liquid hydr~carbcn or oxygenated ~uel.
This invention, in a f ~ r aspect, pruvides for the use of an adduL~ as harein described ~-, a high temperatur2 stable lubricant fluid ar a fu1 oomposition for its i~praved antiwear, high and low temperature antioxidant, antispalling, .ticqyawXin7, antifatique, antistoJnLng, ~;tive solubility, load carrying, extreme pressure, thermal and rxilative, antioorrD6ian, d_mulsifying/emLlsifying, detergent or cleanliness propertie~.
The preparation of these adducts may be by means of a thermal or catalytic adlition reaction. The exact mls~Ym kim of the reac*ion is not i~portdrt to the purpcses of this invention, so long as the hy~rcczrbyl sub6tituent beoomes attached to the oompound (ii) describPd herein.
One preferred ~d of reaction between compound i) an~
compcund ii) is the combination of these r 3ct~ntm in the prEsenoe of specific zeolite cata~vs~s: for example Octacat USY

Wo 92/122'2 PCT/US92/0003~ ~

and MCM~22. A~ditional catalysts which could be used advantageously in this invention are ZSM-12 and cther large-pore and/or relatively large pore zeolites. FCC Octacat USY is described in U.S. Patent No. 4,898,846. MKM-22 is described in U.S. Patent No. 4,983,276. miS reaction is effected at te~perat~res L~u~ ambient to 350-C, preferably L~u 100-250-C and most preferably from 180 to 240 C over a p~riod required to produce the desired conversion of re~oeants to product. m e reaction can be performed in a batch or semi-b~tch mLde by c~DtinDous or partial aA~ition of catalyst or hyd~ocartyl substit~ent to the compound ii).
me catalyst can be used at levels frcm 1 gram/ le of compound ii) to 100 grams/ le of compound ii), preferably fr3m 5 g/ le of compound ii) to 50 grams/ le of compound ii) and mLst preferably fram 10 to 30 grams catalyst/mole of compound ii).
Generally speaking, the molar ratio of c q d i) to compcund ~ rc~ 0.5:1.0 ~o 10.0:1.0 2n~ pr~ably fr~m 1.0:1.0 to 4.0:1Ø
Optionally, the adducts of this inventian can be prepared by reaction in the presence of AlC13 and other Lewis acids or in the presence of Eronsted acids, as descriked in G. A. Olah's "Friedel-Crafts and Related Reactions", Vol. I, 1963, Interscience Publishers.
The adducts of the present invention may be used as 2; liquid l bricants or in liquid lubricant compcsitions, and as solid lutricants or in solid lubricant compositians including greases, such as polyurea, lithium carboxylate or clay-thickened greases.
Ihese adducts may also be used in ~uubination with known ad~itives, for example, antioxidants, EP/antiwear agents, inhibitor~, ~etergents anl disEersants, and v;cr~city index WO 92/12222 Z ~ 9 8 Y '~ 5 PCT/US92/~.9~3~ 1l i ~ ers. Examples of antioxidants include hindered phenols and aromatic amines. Examples of EP/antiwear additives include zinc phosphorodithioates, sulfurized esters, sulfurized olefins, phcGpbonates, phosphites and phosphorothionates. Examples of inhibitors include CMrD and ~ hiæ ine. Examples of detergcnts and dispcrsants include sulfonates, p enates, and polymeric succinimides. These can be either metallic or nrrrmeeallic. Me*allic detergents can be calcium or magnesium derived and can be neutral or overbased.
m e adducts of this invention can be used alone or in combinatian with other synthetic and/or minerzl oil fluids.
hhen used in oombination with other synthetic and/or mineral oil fl~ c oils of lubricating viscosity may be llCP~, In g_neral, mineral oils, both paraffinic, na~i~henic and mixtures thereof, ~uloyed æ the lubricant, or grease vehicle, may be of any suitable lubricating visccsity range, æ for example, LL~ 45 SSU
2t lOO-F ~Jo 6000 SSU at lOO-F znd ~r_fQ~rably, rom 50 Lo 25~ SSU
at 210-F. ThÆse oils may preferably have viscnOEity indexes u.p to 95. Ihe av_rage molecular weig~ts of these oils may be from 250 to 800. ~here the lubricant is to be employed in the form of a grease, the lubricating oil is gen_rally employed in an amLunt sufficient to h~lance the tokal grease composition, after acccunting for the desired quantity of the thickening agent, and other additive CCcpanent5 to be inclu~ed in the grease formulation.
A wide variety of matQrials may be employed æ thickning or gPlling agents. Ihese may include any of the conventional metal salts or soa~s which are dis~rs~l in the lubricating vd~ le in greæe-fc~ming quantities in an a~nt to i~art to 30 the resulting grease canpoOEition the desired concist~cy. Other th~ing ag~c that may be e~loyed in the grease formui~tion may UO 92/12'~2 PCJ/l'S92/OOû3;
209899~ - 6 -comprise non-soap thickeners, such as surface-mcdified clays and silicas, aryl ureas, calcium complexes and s;~ilar materials.
In general, grease thickeners may be employed which do nck mPlt and d;~4nlve when used at the required temperature S within a parti~llar environment; however, in all cther respec$s, any material which is normally e~ployed for thic ~ or gelling hydrccorbcn fluids for foamlng grease can be used in preparing grease in accordance with the present invention.
In instanLes where synthetic oils, or synthetic oils employed as the lubricant or vehicle for the grease, are desired in preference to mineral oils, or in combination therewith, various ccmpcun~s of this type may be suooessfully utilized.
Iypi~al synthetic oils incl~ polyiscbutylene, polybutenes, hydrcgenated pol~dÆcenes, polypropylene glycol, polyethylene glycol, trimethylpropane esters, neopenkyl and pentaerythritol esters, di(2-et~yIhexyl) sebacate, di(2-ethylhexyl) adipate, d~tyl phthalzte, fluo:ocarbons, siliczte est_~s, s;lar:es, esters of phosphDrus-ccntain~ng acids, liquid ureas, ferrocene derivatives, hydrcgenated synthetic o~ls, chain-type polyphenyls, siloKanes and siliccnes (polysiloxanes), aIkyl-sukstituted diphenyl ethers typified by a butyl-substituted bis(p,phenoxy phenyl) ether, phencxy phenylethers.
~ en llC~ A;tives the adducts of the illvention have the ability to i~mve both the thennal ar~l cxidative stability 25 ac well ac the additive solubility of the oleagencus materials, i.e., synthe~ic and/or mineral oil fluids with w~ich they have ~een blended.
It ie to be m~t~, hadever, that the a~ditives useful herein for t~eir knoi.n purposes do not d#~zct frall the 30 value of the cc~pcsitions of this in~ention, rather these ma'cerialc enhance the beneficiai cha acte }~cs of the discl.cs~
;~c.

W O 92/l222~ 2 0 9 8 9 9 ~ PCT/~'S92/0003;
.. . . .

L~bricant compc-cition-c in accordance with the invention may comprise from l~cc than abcut 1 to about 100% of the adducts of the invention and/or from lesLc than about 100% to about 1~ of a synthetic or mineral oil of lubricating v;cr^city or grease prepared therefrom and fr~ll O.OOl to 20 wt% of additive materi21 based on the tctal weight of the .~u~u~ition.
Fuel coGpositiu^n_ of the invention co~pris m g the ad~u~tc herein described include bcth hydrrcarbcn fuels, inLluding ~a~nline, naphtha and diesel fuels or aloaholic fuels or muxtures of alcoholic and hydrccaI~cn fuels. Fuel oompositions can oontain 10 to l,OOO pcurdLc of additive per l,OOO barrels of fuel or, more preferably, 2S to 250 pounds per 1,000 barrels of fuel.

W O 92/12222 PC~tUS~2/00035 ~
209~9~

Ihe followLng Examples illustrate the invention.

EX~ 1 15 g of FCC Octacat USY catalyst were added to a vigorously stirred mixture of dipbenyl ether (170 g, 1.0 mole) and l-tctradbcene (196 g, 1.0 mole) in a flask fitted with ther~coouple and reflux condensur. Ihe mixture was then heated to 200-C, with stirring, for six hours. Aater oooling to rcom temperature, the muxture was filtered to remove catalyst and vacuum distilled to 170-C at 0.5-1.5 mmHg to remove unreaoted starting materials.

EX~MPLE 2 Using the pIoccdure of Example 1, diphenyl ether (170 g, 1.0 le) and l-tet=adecf~c (196 g, 1.0 le) were reacted using 30 grams of FCC Octacat USY catalyst.

Using ~he pro=ecure of FY~mple 1, diphenyl ether (120 g, 1.0 le) and l-dodeccne (168.32 g, 1.1 les) were reacted using 15 grams of FCC Octacat USY catalyst.

~X~MPLE 4 2.0 g of anbydrols AlC13 were added to a stirred mixture of l-octene, 224.2 g (2 les), and diphenyl ether, 170 g (1 le) and he2ted at reflux for six hcurs. ~he mixture was then ccoled; washed to remove incnganic materials; and dried over ~nhyinols ~S04. Gas chromato3rqphdo analysis shcwed er~3entially oomplete reaction o~ starting material. Calor of this material ~5 whereas the prcd~ct of Example 1 w~as <2Ø

~W O 92/12222 2 ~ 9 8 9 9 ~ ~'CT/US92/0003;
!

g EX~MPIE 5 Using tne prooedure in FY~rle 4, 1-deoene 168 g (1 mole) and dip enyl ether (170 g, 1 mole) were reacted with AlC13 (2 grams) at reflux for six hours. Vacuum distillation of the washed organic mixture to 170-C at 0.5-1.5 m~Hg resulted in the ~cired hydr~Yarbyl diphenyl ether product.

EX~MPIE 6 18.2 g of FCC Octacat USY catalyst were added to a vigorously stirred mixture of diphenyl methane (168.24 g, 1.0 mole) and l-tetradecene (196 g, 1.0 mole) in a flask fitted with tber~ocouple and reflux condenser. Ihe mixture was then hated to 200 C, with stirring, for six hcurs. After cooling to room temperature, the mixture was filtered to remove catalyst and vacuum distille~ to 170-C at 0.5-1.5 m~Hg to remove unreacted EX~MPLE 7 Using the proccduce of EXample 6, diphenyl methane (168.24 g, l.O mole) and 1-te*r~dboene (196 g, l.O mole) were reacted using 36.4 grams of FCC Octacat USY catalyst.

EX~MPIE 8 Us m ~ the pcooeduce of Example 6, diphenyl nethane (168.24 g, l.O mole) and 1-hex~db~ene (224.43 g, l.O ~oles) were reacted usi~g 19.6 grams of FOC octacat USY catalyst.

EX~MPIE 9 2.0 g of ~nhydm us AlC13 were added to a stirred mixture of 1-octene, 224.2 g (2 moles), ~nd diphenyl methane, 168.24 g (1 mole) and hated at reflux for s~x h~u~s. Ibe nixture w~s tben o~oled; washed to re3cve inorganic materials; and dried over ~nhyd m us Mg5O4. Gas chromatographic analysis showed e~scrtially complete reaction of starting material. Color of this material wzs ~5 whereas the pxodLct of Example 1 w <2Ø

W O 92/12222 PCT/US92/00035 ~, 2098~9~

~E 10 19.5 g of FCC octacat USY catalyst were added to a vigorcusly stirred mixture of phenoxathin (Z02 g, l.O mole) and l-te*r~d~c~ne (196 g, l.O le) in a flask fitted with S ther=cccuple and reflux oondenser. Ihe ~ e was then heated to 200-C, with stirring, for six hcurs. After cooling to room temperature, the mixture was filtered to remove catalyst and vacuum distilled to 170-C at 0.5-1.5 mmHg to remove unreacted starting materials.
EX~E 11 Using the procedure of Example 11, pbenoxathin (202 g, l.O
mole) and l-te*r~deccne (196 g, l.O mole) were reacted using 39 grams of FCC Octacat USY catalyst.
EX~MPLE 12 Using the procedure of Exa~ple 11, phenLKathin (202 g, 1.0 mole) and 1-hexadecene (224.43 g, 1.0 moles) were reacted using 42.4 g~ams of E~C 05tarat USY catalyst.
E%~ 13 2.0 g of anbycr~us AlC13 were added to a stirred mixture of 20 1-octene, 224.2 g (2 moles), and F~noxathin ~202 g, 1 mole) and heated at reflux for six hours. ~he mixt~re was then cooled;
washed to rem3ve inorganic materials: and dried over anhydrcus MgS04. Gas chromatcgraphic analysis showed esser*ially comple*e reaction of starting material. Color of this material was >5 25 whereas the product of EXample 1 was <2Ø
~2MF~E 14 19.1 g of FCC Octacat USY catalyst were added to a vigcrnusly stirred mixture of diphenyl sulfide (186.2 g, 1.0 mole) and 1-te*s~decen~ (196.4 g, 1.0 mole) in a flask fitted with thYs~occuple and reflux c=ndenser. ~he mixture was then heated to ~v~-O, ~ith stirring, for s;x hours. After cooling to ~ O 92/1222' 2 0 9 8 9 ~ ~ PCT/~S92/0003~
f~ ~

rcc~ temperature, the mixture was filtered to remove catalyst and vacuum distilled to 170-C at 0.5-1.5 mmHg to remove urre~=bed starting materials.

EX~MPLE 15 Using the procedure of Example 14, dipbenyl sulfide (186.2 g, l.O le) and l-tI*r~decrne (196.4 g, l.O mole) were reacted using 38.2 grams of FOC Octacat USY catalyst.
EX~MPLE 16 Using the procedure of Example 14, diphenyl sulfide (186.2 g, 1.0 mole) and l-hexadeceno (224.4 g, 1.0 moles) were reacted using 19.1 grams of FCC Octacat U~Y catalyst.
EX~MPIE 17 2.0 g of a ~ s AlC13 were added to a ~ mixture of 1-oc$ene, 224.2 g (2 moles), and diphenyl ~lfide (186.2 g, 1 mole) and heated at reflux for six hours. Ihe mixture was then ~led, w~L ~ed to r~move ~organic mater;~ a~d dried over anhyd:cus MgSO4. Gas chromatograpbic analysis ahcwed essentially ccnplete reac*ion of starting material. Color of this material was ~5 whereas the prodL~t of Example 1 was <2Ø
Typical properties of exemplified hydr=c~rbyl diphenyl ethers are shown in T~E~E 1.
.~E 1 ~1 C14 C10 C8 KV Q lOO-C,cSt 4.0 3.8 10.7 VI ~1 94 103 Pour Point ('C) S-54S-54 -40 Plash Point('P) - 435 475 Typical peopelties of exemplified diphenyl ~E*hanes are shcwn in lAaLE 2.

WO 92/l2222 PCTtUS92/00~3~ 1 ~S' 209~9~ - 12 -i l~ELE 2 ~1 C14 cl6 C8 ' KV QlOO-C, cSt 3.58 4.21 4.90 Vl 111 112 134 Pour P~int ( C) <-58 <-58 - 4 Flash Point (-F) 446 457 478 Typical prqperties of exemplary hydlocarbyl phencxathins are shcwn in T~ELE 3.

I~ELE 3 Nyd~l C14 C16 C8 XV @lOO-C, cSt 7.8 7.93 9.13 Vl 41.4 61.6 75.2 Pour Point ( C) -35 -35 - 30 Typical prcperties of exemplified hqarocarbyl diphenyl 15 sulfides are shown in I~BLE 4.

~IE 4 ~1 cl4 C16 C18 KV ~lO~-C, cSt 4.12 4.80 5.32 Vl 93.3 101 119 Pour PDint ( C) -58 -58 -40 Flash Point (-F) 426 480 594 .~ ' .
Ie*lzdecene aIkylated dipbenyl e~r hr~e1~ oene ~lkylated W O 92/12222 2 0 ~ 8 9 9 ~ PCT/US92/0003~

phenoxathin and both tetradecene and hexadecrne aIkylated diphenyl sulfide were campar~d with polyolefin base stock in a ~our-P~ll Wkar test. The results show that at higher load, both the alkyl diphenyl ether and sulfides and alkyl phenoxathin S produced less wear than the other base stock, without any adverse effect on ccefficient of friction (f).
The antiwe æ properties of the examples were r~valuated using the Fcur Ball Wbar lest as shown in T~ELE 5 below. Ihe results cle æly exhibit the excellent antiwear properties inherent in these cr~mp~sitions.
In the Four R~ll Test three stationary balls are plaaed in a lubricant cup; a lubricant contJ m m a the campound to be tested is added thereto; and a fourth ball is placed in a chuck mounted on a device which can be used to spin the ball at kncwn speeds and loads. The examples were tested usinq half inch stainl~cc steel balls of 5200 steel for thirty minutes under 40 hg lo~ a~ 500 and 1800 rFm ænd 200-F. If additional info~ion is d~cired ccnsNlt test me*hod ASIM D2266 an~/or U.S. Patent 4,761,482.
X, as reported in the Table, is the wear coefficient calculated from the wear volume, V, of the staticnary ball. The wear volume is calculated from the wear scar diameter D in mm ac follow_:
V = [15,5 D3 - 0.001033L~ D x 103 mm3 where L ic the m2chine load in hg. ~hic P~tion considers the elastic deformation of the steel b lls.
~kar Coefficient K

Dimensionless K is defined as K = VH
dN

W O 9~/l2222 PCT/US92/0003~
~899~

where V = wear volume, mm3 H = hardness 9725 ~ 2 for 52100 steel d = (23.3 mm~rev) (RPff x Time) N = (0.408) (LDad in hg) The Fbur-R~ll Wear Iest results dlmorstrate the excellent antiwear ~ ies of these comQo6itions when used in synthetic oils.

T~IE 5 FoUR-BALL WEAR TEST RESUIIS
(200-F/40 Kg/30 min) K f K f C14 DP~ 13.2 0.11 431 0.11 polyolef m basestcck 11.4 0.09 1300 0.09 C16 Fhenoxathin 0.617 0.094 polyolefin basestcck 1.66 0.076 W5D Ir~n -14 DES - - 0.675 .093 C16-DPS 0.486 .098 0.630 .086 Performan~e as a Lubricant with ImDroved Additive Solubility 4.0 wt~ of sulfurized isobutylene (as generally describo~
by A. G. Hor~dysky in U.S. 3,703,504) and 0.5 wt% of a hindered phenolic inhibitor obtained from Ethyl Corp. as Ethyl 702 were added to a synthetic lubricant base s*ock. The mixture of additives was m soluble in the base stock and the ~ample was cloudy. In ~eparate runs, 20 wt% C16 alkylated diphenyl mekhane;
21 wt~ Cl~ aIkylate~ diphenyl sulfide; and 21 wt~ C1~ alkyia~ed 209~9'3 ~, di~ ~ 1 ether were ad~ed to this mixtLre. The sample was niyen;
in each ca_e the ad~itives completely d;ccnlved and the ~ ~ e became clear.
Improved Thennal and Lioht Stability over Okher iubricant cl~ccpc The ~ Stability TXst Sample % Visco ity Change After 72 nrs at 288-C 72 llrc at 310-C

C14-Dæ * -1.4 C -Dæ -3 0 C14-D~M* -2.2 C16-D'AM -5 C18-D~M -5 C16 ~ athin -15 18 DPS -8.2 l; Cbcmercial Syn~etic ~br~cæ-~ -14.8 Cocnercial Synthetic iubricant -19.4 ~ cial Synthetic T I ~hricant - 38.8 C ~ erci~l Synth ~ic T~hrica~t -60.9 Ccmmercial ~ etic Lubricant -67.9 Lube ~ster -34.2 (* -DPE, -DPM and -DPS are a'~breviations for aIkylated diphenyl ether, aIkylated di~henyl .~hane and alkylated sulfide, respectively.) W O 92/12222 PCT/US92/0003~ ~

2a~9s - 16 -i ' Over Storage Tests (150~C/5 days) CDlor (Before) (After) C14-DPE (Octacat USY) 2 2.5 C14 DPE (AlC13) 5.5 Commercial Synthetic Lubricant 1 -l.S
(Sample 1) 200-Second Solvent Paraffinic Neutral }ubricating Oil 2 ~5.5 Light stability was good as no color change or precipitate was observed over tWD mLnths.

Improbed ~ ative Stability Of NGdrocartyl Dip~envl Mb*hane Over Commer~ial 9YI~b ~I~L~y~ _t Rat~r~l ~ cial Synthetic Lubricant 9-10 C16 DFM 3.5 1 Hbt IUbe OKidation Test (31S-C/16 hrs) Rating (O = clean; 10 = black, plugged) Tested as base stock coopon~rts in synthetic di~cPl engine oil formulation W O 92/12222 PCT/US92/0003~ ' ; 209839~; 1 Performance Ac A T~hricant With Imprcved Load Carrym~LPrcperties LDad-carrying prcperties were me2sured using ASTM D2596 at both rDom temperature and lOO C.
23 C lOO-C
LNS IWI W~ld LNS ~I Weld Polyolefin base stock 50 22.7 126 32 14.6 126 C16 Phenoxathin 50 23.7 160 40 20.6 160 C14 DPS 40 22.5 160 32 17.9 126 C16 DES 40 21.4 160 50 22.9 126 Ihe use of adducts of this invention as a suitable replaseme~.t fo~ CCC}rrell~C of current lubr_cant fnn~ations is highly desirable. For exa~ple, synthetic an yor mireral based lubricant compcsition containing esterC for i~proved additive solubility wauld be significantly improved by replacement with ad~ucts of this invention ~P to tlheir excellent thPrmal stability, additive solubility andJor EP/antiwear prcperties.
Adducts prepared as drfczLbed;herein pravide exLellent h~co stock pecpeltie~ and could themselves serve as the kas_ stock in formulatiRns for Yarious applications, for example, applications where high temperatures and EP are roontaoned.

Claims

1. An adduct preparable by catalytically reacting :

i) at least one compound comprising at least one olefinic group; a hydrocarbyl substituent; and, optionally, at least one heteroatom; with ii) a substituted or unsubstituted, fused or unfused, polynuclear, aromatic compound which may contain at least one chalcogen atom.

2. An adduct according to claim 1 wherein the hydrocarbyl substituent comprises a C3 to C500 alkyl, alkenyl or alkynyl group, a C7 to C500 aralkyl or alkaryl group or a C6 to C500 aryl group.

3. An adduct according to claim 1 or 2 wherein the hydrocarbyl substituent comprises from 8 to 18 carbon atoms.

4. An adduct according to any preceding claim wherein the hydrocarbyl substituent is a linear substituent.

5. An adduct according to any preceding claim wherein i) comprises an alpha olefin.

6. An adduct according to any preceding claim wherein the or each heteroatom comprises S,N,O,P,F or a mixture thereof.

7. An adduct according to any preceding claim wherein ii) has the general formula :

in which :

X represents an oxygen or sulphur atom or a methylene group; and Y represents a sulphur atom or two hydrogen atoms attached to different aromatic rings.

8. An adduct according to claim 7 wherein ii) comprises diphenyl ether, diphenyl sulphide, diphenylmethane or phenoxathiin.

9. An adduct according to any preceding claim preparable in the presence of a Lewis acid or zeolite catalyst.

10. A process for the preparation of an adduct, which process comprises catalytically reacting :

i) at least one compound comprising at least one olefinic group; a hydrocarbyl substituent; and, optionally, at least one heteroatom; with ii) a substituted or unsubstituted, fused or unfused, polynuclear, aromatic compound which may contain at least one chalcogen atom at a temperature from ambient to 350°C; a molar ratio of i) : ii) from 0.5:1.0 to 10.0:1.0; and a ratio of catalyst : ii) from 1g :
1 mol to 100 g: 1 mol.

11. A process according to claim 10 wherein i) and/or ii) are defined m any of claims 2 to 8.

12. A process according to claim 10 or 11 wherein the catalyst comprises a Lewis acid or a zeolite.

13. A process according to claim 12 wherein the catalyst comprises AlCl3, Octacat USY or MCM-22.

14. A process according to any of claims 10 to 13 wherein i) comprises octene-1, decene-1, dodecene-1 or tetradecene-1.

15. A high temperature stable lubricant fluid comprising an adduct according to any of claims 1 to 9.

16. A lubricant according to claim 15 also comprising an oil of lubricating viscosity, or grease prepared therefrom, in an amount from less than 1% to 99% by weight of the total composition.

17. A lubricant according to claim 15 or 16 wherein the oil of lubricating viscosity comprises a mineral oil, a synthetic oil, a mixture of mineral and synthetic oils, or a grease prepared therefrom.

18. A lubricant according to any of claims 15, 16 or 17 wherein the adduct comprises a relatively minor proportion of the lubricant and the oil of lubricating viscosity comprises a relatively major proportion of the lubricant.

19. A lubricant according to claim 18 wherein the adduct comprises from 0.01 to 10% by weight of the total composition.

20. A fuel composition comprising an adduct and a liquid hydrocarbon or alcoholic fuel or a mixture thereof.

21. A fuel composition according to claim 20 wherein the fuel comprises gasoline, naphtha, diesel or an oxygenated fuel.

22. A fuel composition according to claim 22 or 22 wherein the adduct comprises a relatively minor proportion of the fuel and the fuel comprises a relatively major proportion of the composition.

23. Use of an adduct according to any of claims 1 to 9 in a high temperature stable lubricant fluid or a fuel composition for its improved antiwear, high and low temperature antioxidant, antispalling, antisquawking, antifatique, antistaining, additive solubility, load carrying, extreme pressure, thermal and oxidative, anticorrosion, demulsifying/emulsifying, detergent or cleanliness properties.