US3189660A

US3189660A - Synthetic fluids as multifunctional lubricants

Info

Publication number: US3189660A
Application number: US53382A
Authority: US
Inventors: James J Pappas; Schriesheim Alan
Original assignee: Exxon Research and Engineering Co
Current assignee: ExxonMobil Technology and Engineering Co
Priority date: 1960-09-01
Filing date: 1960-09-01
Publication date: 1965-06-15
Anticipated expiration: 1982-06-15

Description

United States Patent 3,189,655 SYNTIET-EC FLUES AS MULTEUNCTIQNAL LUBRECANTS James I. Pappas, Elizabeth, and Alan Schriesheim, Berkeley Heights, N.Il., assignors to Essa Research and Engineering Company, a corporation of Belaware N0 Drawing. Filed Sept. 1, 1960, Ser. No. 53,382 10 Claims. (Cl. 269671) ous desirable natural properties of the oil and have been accomplished to a considerable extent by the incorpora tion of additives in the oil. Thus, there are additives for improving pour points, viscosityindex, oiliness, stability, in service, color and fluorescence, foaming tendencies and rust vpre 'entive characteristics.

These additives are expensive per se and there is add tional expense involved in the various process stepsnecessary to incorporate them in the final commercial blend. It is recognized that it would be most desirable to incorporate an equivalent upgrading in properties in the structure of the oil itself, thus eliminating some or all of the before-mentioned additives. The use of several additives in one oilisdisadvantageous also from the viewpoint that additives may interact with each other thereby partially or completely neutralizing the improving elfect each might exert when individually present in the oil.

or :use in reciprocating engines, particularly as a lubricant for automotive engines, a lubricating composition must meet several requirements. In order to form an elfective lubricating film and to maintain that film at low and high temperature it must have certain viscosity characteristics. At low temperatures the lubricant must be sutficiently labile to flow through the circulatory system of the equipment and allow movement of lubricated surfaces without an undue power requirement. A lubricant having an ASTM pour point below about 35 F. has sufl'icient low temperature lability to make it satisfactory in these respects for general use. At high temperatures a lubricant must have suficient body or thickness to furnish and maintain a satisfactory lubricating film. It has been found that a lubricant that is satisfactory in this respect will have a viscosity at 210 F. of between about 2 to 60 centistokes, i.e., about 32 to 280 Saybolt Seconds, Universal. To prevent undue lubricant loss, due to volatility and general molecular distintegration and to insure against explosion hazards at higher temperatures sometimes encountered, .a lubricating composition should have a flash point in excess of about 300 F.

Although the lubricants or" this invention have great utility in reciprocating engines, the properties of some of the lubricants prepared by this invention technique seem to be especially adapted to specialty uses. Thus, lubricants having relatively low boiling constituents with high viscosity indices, i.e., 105-175 and viscosities of'from 45 7O SUS at 210 F. would be particularly well suited for use as refrigerator oils or instrument oils. They would be of use, for instance, in lubricating watches, meters, ordinance fire directing equipment, aircraft instruments, and the like. Other lubricants prepared by the method of the invention have the unusual properties of very high viscosities, i.e., 300-550 SUS at 210 F. with correspondingly low pour points, i.e., +l0-+30 F. These latter 1 grease compositions.

'te'lomer. would have the added advantage of improving thedeterlubricants have unusual utility as bright stock for use in small quantities for blending crank case oils. They also are useful in the high boiling areas for steam cylinder oils where high viscosity and low volatilityare desirable lubricant characteristics.

The hydrogenated telomers as described herein may also serve as the lubricant base for grease compositions. The hydrogenated telomersarethickened to stable grease structures with conventional grease forming soaps such as lithium soaps of high molecular weight substantially saturated fatty acids, the n-acyl p-amino phenols, silica gels, treated bentonites and the like. Oxidation inhibitors, rust inhibitors, tackiness agents and other grease addition agents may be added to the "hydrogenated telomers of this invention. The soap complexes knownto the art made byusing low molecularweig'ht acid salts and high molecular Weight soaps may also be used in preparing these If desired, the hydrogenated telomers of this invention may be blended withmineral oil or other synthetic lubricants such as simple bis-'formals, complex esters, monoesters, diesters, triesters, tetraesters, phosphates, siloxanes, silicates, lphosphona'tes and'the'like. From these blends, grease compositions which incorporate the desirable characteristics of the blends may be prepared by conventional techniques.

These new hydrogenated telomer lubricating oils may "also 'be admixed with other lubricating 'oils, naturally occurring or synthetic, either as concentrates o'ras finished blends. They are compatibleand may be blended with the well-known lubricant addition agents such as viscosity index improve'rs, pour point depressors, detergents, rust inhibitors, load carrying agents, antioxidants, and the like.

Thus, it has now been found and forms 'a majo'r'fea'ture of this invention that lubricants can be synthesized having such properties as to be usable in *a wide spectrum of different lubricating uses. The primary reaction of the synthesis is believed to be a telomerization. These lubricants are characterized in'gen'e'ral by low'p'ou'r points,

high viscosityindices and oxidation stability. Inone aspect of the invention, telomers are synthesized by reacting an alkylaromatic'with diolefinssuch'as butadiene inthe presenceof an alakli metal which serves as a catalyst. In another aspect, the alkyl aromatics are 'metalated with an alkali metal prior tothe 'reaction'with the diolefi'n, and no catalyst is needed. Alkyl'aromatics which are metalated by an alkali metal on the alpha carbon atom of the alkyl substituent are preferred. By metalated it is meant that condition wherein one or more hydrogen atoms of a hydrocarbon compound'are substituted with a metalatom. in still a third aspect, an aliphatic hydrocarbon metalated with an alkali metal may be reacted with the diolefin and no catalyst is needed.

The telomerization product is unsaturated to a high degree and in order to improve its oxidation stability it is hydrogenated. In some instances, a residual unsatunation remains after hydrogenation, but this may be removed by reacting a sulfur or phosphorus and sulfurcontai'ning compound, such as H 50 or P2S ,'with'the hydrogenated Such sulfurization or 'phosphosulfurization gency of the lubricant, Additionally, it may be of im portance that a portion of the 'diolefins in the reaction have a side chain so tha'tthe resulting'telomer alkyl group also has such a chain. Thus isoprene, for instance, may

replace part of the straight chain butadiene. This appears to prevent possible increase in pour point which might be caused by the hydrogenation. The choice 'of suitable modes of operation as outlined above will be ap parent to one skilled in the art.

Telomerization, as used throughout this specification,

refers to the polymerization reaction wherein the chain dium in which to allow the reaction to occur.

is an integer greater than 1. Representative US. patents concerning telomerization and telomers are 2,440,800; 2,440,801 and 2,402,137.

In general, the reaction mechanism which the reactants of this invention undergo to form the telomer lubricant is believed to be of the following nature: a

Chain propagation:

(Ar)ZX+nR (Ar)-Z(R')nX Chain termination:

wherein R" refers to a conjugated diolefin, R to a monoolefin with the same number of carbon atoms as R", X represents an alkali metal, (Ar)-Z represents an aromatic nucleus with at least one alkyl substituent, and n is any whole number of from 1 to 30.

In order to synthesize the desired telomers, several principal, but different, approaches can be utilized. One is to start with the alkyl aromatic and diolefin, viz, butadiene as reactants in the presence of an alkali metal which serves as catalyst. Another is to start the reaction with an alkali metalated alkyl aromatic, viz., sodium beuzyl instead of the unmetalated alkyl aromatic. When the metalated alkyl aromatic is one of the initial reactants no catalyst is necessary. Still another approach is to use in place of the metalated alkyl aromatic an aliphatic hydrocarbon metalated with an alkali metal. This reaction will also proceed in the absence of a catalyst. The metalated alkyl aromatic is similar to that formed in the chain initiation portion of the reaction mechanism as previously illustrated;

A further modification of the invention is that synthesis wherein from 1-20 wt. percent of metalated alkyl aromatic together with a major portion of alkyl aromatic is reacted with a diolefin. This reaction is possible since only a trace amount of a metalated alkyl aromatic will catalyze the reaction. This process also produces telomers which when hydrogenated are good lube oils; however, in lower yields than obtained by using one of the other processes.

A feature of the invention is the technique of controlling the various degrees of branching in the telomer. For example, the ratio of 1,2- and 1,4-addition of butadiene can be controlled. In the 1,2-addi-tion, branching occurs; in the 1,4-addition no branching occurs. It is desired that equal portions of 1,4-addition and 1,2-addition products be obtained since this ratio gives reaction products which whenhydrogenated have better all-around lubricating oil properties. One means of controlling such branching so as to'obtain desirable ratios is to choose the proper me- Mediums found to be most effective are C -C tertiary amines such as .trimethylamine, triethylamine,.tri(n-propyl)amine, dirnethylamine, diethylamine, pyridine, and the like, and C C ethers such as dimethyl ether, diethyl ether, diisopropyl ether, di-n-butyl ether, tetrahydrofuran, and the like. Particularly preferred is triethylamine.-

An alternate method of controlling branching is by using the appropriate alkali metal. For instance, lithium as a catalyst or lithium metalated alkyl aromatics are effective where more 1,4-addition is desired than can be obtained using sodium or potassium. The I A-addition of dienes has a tendency to increase the viscosity index of the lube product. Another important -tory lubes by the telomerization synthesis of the invention factor in the production of satisfac is the ratio of diolefin to alkyl aromatic or diolefin to metalated hydrocarbon. It has been found, in general, that when the alkali metal is to be used as catalyst a mole ratio of 0.8:1 to 35:1, preferably 1:1 to 1.621, of diolefin to alkyl aromatic produces the highest yield of lube oil boiling range telomers with correspondingly high viscosity indices. When the metalated alkyl aromatic or aliphatic hydrocarbon is used in lieu of the catalyst type reaction, the ratios of diolefin to metalate will generally fall in the range of 4:1 to 11:1, preferably 6:1 to 8:1.

The alkali metals suitable for use in this invention are preferably sodium, lithium and potassium. If the catalyst type reaction is to be used for the alkyl aromatic and diolefin reaction, sodium is the preferred alkali metal; if the metalated alkyl aromatic type'of reaction is to be used, then potassium is the preferred metal. From 0.1 to a 3.0, e.g., 0.2 to 1.5, molar proportions of alkali metal as a catalyst is used based on the molar proportions of the initial reactants.

The reaction may be carried out in a parafiinic medium a action is between 0300 F preferably -250 F. The

time of reaction will var-ybetween /2 hour'and 7 hours,

preferably l hour and 3 hours. In general, the same re-.

action and operating conditions will prevail when using any of the various aspects and modifications of the invention except for the presence of a catalyst as previously indicated.

After the completion of the telomerization reaction, the reaction product is recovered and such recovered product is hydrogenated. The hydrogenation is preferably per:

formed in the presence of either a nickel catalyst or a palladium over charcoal catalyst; however, any catalyst known to the art may be utilized. In certain cases the hydrogenation is carried out in a C.,C paratfinic hydrocarbon solvent; The reaction temperature of hydrogenation generally will vary from 60 F. to 250 F, preferably between 70 and 215 F. The reaction time will gen-' erally vary from between /26 hours, preferably between 13 hours. The pressure will generally vary between 15- 600 p.s.i., preferably between 350-550 p.s.i. The efiect'of hydrogenation is usually to lower the viscosity index.

However, the possible disadvantages of this are over- Weighed by the compensating advantage of greatly increased stability. This stability is obtained in direct proportion to the amount of unsaturation eliminated from the telomers.

The alkyl aromatics suitable for use in the manufacture of lubricants according to the'invention are those alkyl aromatics havinga benzene, naphthalene, or anthracene nucleus with from 1 to 8 alkyl substituents of from 1 to 4 carbon atoms each. Alkyl aromatics suitable for use in this invention are exemplified by the following: toluene, ethyl benzene, isopropyl benzene, xylenes, mesitylene, propyl benzene, butyl benzene, durene, pentamethyl benzene, heX-amethyl benzene, cumene, triethyl benzene, hexa ethyl benzene, tributyl benzene, tripropyl naphthalene, tripropyl anthracene, hexabutyl anthracene, any mixture thereof, and the like. The preferred alkyl aromatics have a benzene nucleus substituted with from 1 to 6 methyl groups.

Suitable aliphatic hydrocarbons which may be metalated are those having from 1 to 20, and preferably 3 to 8, 7

+ ArCHgR (ArCHR)M -I wherein X is a halide, M is an alkali metal and ArCH R is an alkyl aromatic. This mode of preparation is described in U.S. Patent 2,914,578.

This mode of preparation is described by Morton et al.

in the Journal of Organic Chemistry, vol. 2, p. 440 (1955) Metalated alphatic hydrocarbons are prepared by the direct reaction between an alkali metal and the aliphatic chloride. The reaction is described in US. Patent 2,914,-

Diolefins suitable forms are C to C e.'g., C to C conjugated diolefins exemplified by 'butadiene, isoprene, dimethylbutadiene, any mixture thereof, and the like. These compounds may be straight chain or branched. The preferred conjugated diolefins are isoprene and butadiene.

The invention will be further understood by reference to the following examples. In these examples the sodiumon-alumina catalyst was prepared by mixing molten-sodium with alumina (AI O 'in amounts sufficie'n'tto obtain an alumina carrier having 20 wt. percent of high surface sodium thereon. The pure sodium catalyst of these examples was prepared by simply 'in'e'ltin'g'the sodium in the hexane medium and dispersing it. The preparation of these catalysts is described in detail in a publication or US. Industrial Chemicals Co., 120 Broadway, New York 5, N.Y., entitled High Surface Sodium (1953).

Example 1.--T'el0merization '07 toluene and butadieize in the presence sodium catalyst foilowed by hydrogenation of the telomer The following lubricating compositions were prepared by telomerizing butadiene with toluene in the presence of a sodium catalyst, and then *hydro'genating the reactant telomer.

COMPOSITIONS A, A-1

These compositions were prepared by charging 65 grams of butadiene into a l-liter stirred batch autoclave containing 87 grams of toluene, 264 grams of n-hexane, and 50 grams of a 20% sodium-on-alumina catalyst. The reaction was carried out in the stirred batch autoclave over a periodof about 1 /2 hours. The temperature of the reactor mixture was maintained at approximately 212 F. The pressure of the butadiene was kept at about 50 p.s.i. The reaction mixture was cooled, and unreacted butadiene was vented otf. 61.4 grams -of a telomer product were then obtained by removing the catalyst and stripping oft" the solvent and'unreacted toluene upto a temperature of about 122 F. at 1 mm. Hg pressure.

The 61.4 grams of telomer product recovered in the above process were then hydrogenated in the presence of 20 grams of a 10% palladium-over-charcoal catalyst for a period of 3 hours at a temperature of 78 F. at a pressure of 400 p.s.i. 350 grams of n-hexane were used as a solvent for the telorner and the catalyst in the reaction. The reaction took place in a l-liter, stirred batch autoclave and the hydrogen feed gas was used to maintain the pressure. The unreacted hydrogen was vented 011 The n-hexane solvent was then distilled off and 35.4 grams of a hydrogenated telomer pnoduct were obtained having a molecular weight of 336, which was labeled Composition A.

Composition A was then subjected to further distillation and that material boiling above 600 F. was collected as bottoms amounting to 61.3 wt. percent of Composition A. This material is Composition A-l.

COMPOSITIONS B, 13-1 The telomers were prepared exactly like those of Composition A except that 20 grams of a pure sodium catalyst were used. About 51 grams of telomer were re covered which were then hydrogenated under identical reaction conditions as those described in Compositions -A and A-1 except that only 250 grams of n-hexane solvent were used and the reaction time was 1 /2 'hours at a temperature of F. 42.1 grams of the hydrogenated telomer were obtained having a molecular weight of 352 which was labeled Composition B. -Composition B was subjected to further distillation in which 60.8 -wt. percent of bottoms was recovered boiling above 600 P. which was labeled Composition B l.

Example II.-Telom*erization of butadiene with benzyl potassium and benzyl sodium The following lubricating compositions were prepared by telomerizing butadiene with benzyl potassium or benzyl sodium in the absence of a catalyst and hydrogenzating the telomer product. The 'benzyl potassium prepared .according to the method of Morton et al. and the benzyl sodium was prepared according to the method of US. Patent 2,914,578.

COMPOSITIONS 0, 0-1

These compositions were prepared by charging 108 grams of butadiene into a l-liter, stirred batch autoclave having therein 25 grams of benzyl potassium in 205 grams of n-heptane solvent over a period of 3.50 hours at a butadeine pressure of about 35 p.s.i. The reaction mixture was 'ni'ainta'i'ned at about 122 F. About 50 ml. of water were added to the reaction mixture to bydrolyze the resultant telomer salt. The water layer was removed. About grams of a product having a molecul ar weight of approximately 515 were obtained by stripping the hept'a'ne and tel-omer layer to 122 F. at 1 mm. of Hg pressure.

This product was then hydrogenated in the presence of 18 grams of R-aney nickel for a period of 22 hours at a temperature of 212 F., and at a pressure of 500 p.s.i. The other reaction conditions were similar to those in the hydrogenation described in Composition A. The product obtained was labeled Composition C and had a molecular weight 'of 545. Composition C was subjected to further distillation and the bottoms at 650 F. were recovered and amounted to 97 wt. percent of Composition C. These bottoms were labeled Composition C-l.

COMPOSITIONS D, D-1 AND D2 The telom-er was prepared exactly like that of the C compositions except that 65 grams of but-adiene were used and the reaction time was 4 hours. About 68 grams of product having a molecular weight of 425 were obtained, and subjected to a hydrogenation process similar to that described for Composition B except the tempera ture was 70 F. and the time of hydrogenation was one hour. 61.2 grams of hydrogenated telomer were recovered having a molecular weight of 470. This product was labeled Composition D and was further subjected to distillation in which two separate fractions were ob.- t'a'i'ned, one boiling between 700l000 F. which was labeled Composition D-1 and one boiling at over 1000 P. which was labeled Composition D-2. The composite of D-1 and D2 was labeled Composition D-3.

COMPOSITIONS E, E-l, AND E-2 The telomer was prepared exactly like that of the D compositions except that 39 grams of triethylamine were initially present with toluene. About 66 grams of a product having a molecular weight of about 477 was recovered, which was subjected to the exact hydrogenation process of Composition D except that the temperature was 80 F. and the time was 1 /2 hours and yielded 54 grams of material labeled Composition E having a molecular weight of 411. Composition E was further distilled into 'two separate fractions, one boiling betwee 700-1000 F. which was labeled Composition E-l and the other above 1000 F. which was labeled Composition E2. The composite of E-1 and E-Z was labeled Composition E 3.

COMPOSITIONS F; F-l The telomer was prepared similarly to tha-t'of the E compositions except that 25 grams of benzyl sodium were used in place of the benzyl potassium and 75 grams of butadiene were used. The 39 grams of triethylarnine were also eliminated as part of the solvent. The reaction temperature of the telornerization was 212' F.

Fifty-six and three-tenth grams of product having a molecular Weight of 423 were recovered. The hydrogenation of this product was performed exactly like that of the E com-positions. 45.8 grams of hydrogenated telomer, which were labeled Composition F were recovered. COMPOSITIONS G, G-l

The telomers were prepared exactly like that of the E compositions except that 266 grams of tetrahydrofuran were used as solvent in lieu of the n-heptane and the reaction temperature was maintained at 212 -F. during the course of the telomer-ization reaction. 70 gramsof product having a molecular weight :of 672 were obtained and were hydrogenated exactly like the telorner in the E composition except that the temperature was 76 F.

' compositions except that amyl sodium was used in place of benzyl potassium, 91 grams of butadiene was used instead of 65 grams and the'tirne of telornerization was about '4 hours. About grams of a product was recovered and subjected to a vhydrogenation similar to that of the telomerin the G compositions except th-at the temperature was about 96 F. About 53 grams of a hydro gen-ated telomer were recovered. This product was labeled Composition H and further subjected to distillation in which the portion boiling above 700 F. was recovered and labeled Composition H-l.

The reaction conditions, products and their proper-ties are summarized in the following tables.

TABLE I Telomerization of butadiene with toluene and catalyst, benzyl potassium, benzyl sodium, and amyl sodium Compositions A B O D E F G H Feed com Benzy l b m 2s 25 25 0 0 0 Benzyl sodium O 0 Q 25 25 0 Amyl so um 25 Butadiene 65 108 65 05 75 91 Toluene 87 87 0 0 0 0 0 0 11-Honfan- 205 205 205 205 0 205 Triethy mn 0 0 39 O 0 0 Tetrahydroturan 0 0 O 0 266 0 n-Hexane 264 264 0 0 0 0 0 0 Cataylst gms.: V v 20% 'Na/AhO; 5o 0 Na 0 20 Operating conditions:

ernp., "F 212 212 122 122 122 212 122 122 Reaction time, hrs 1. 50 1, 50 3. 50 4. O0 4. 00 4. 00 4. 00 3.00 Total product:

Yield, gms 61. 4 51.0 100. 0 67. 7 65. 5 56. 3 69. 7 60.0 Molecular weight- 334 390 515 425 477 423 672 Vise. SS U 210 F 55. 5 61. 5 50. 7 71. 8 59. 8 7308. 1 156 V 162 168 147 160 134 12 7 TABLE II Hydrogenation of telomers Compositions A B C D E F G H Catal st .2

nin iii ck 1 0 0 1s 0 0 o 0 o a 10% palladium/c 20 20 0 20 20 20 20 20 Solvent, ml.: n-Hexane 350 250 0 250 250 250 250 250 O eratiu conditions:

p Temi ierature, F 78 212 70 80 78 Reaction time. Ms 3. 00 1. 50 22. 0 1. 00 1. 50 1. 50 Pressure. p 5.1 400 400 500 400 400 400 Total roduct' Yield, gmc 35. 4 42. 1 70. 0 2 54. 0 45. 8 Molecular weight--- 336 352 545 470 411 415 Viso., SSU 210 F 46. 8 57. 3 63. 6 64. 0 62.6 346. 1' V. 177 156 137 127 135 128 P10113011 t 1 1 ma eria g Wt. percent 38. 7 39. 2 3. 0 16. 3 26. 7 22. 6 10. 7 14. 9 B.P., F 600 600 650 700 700 700 700 700 Bottoms: A-l B-1 0-1 D-3 E3 F-l G-l H-l Wt. percent 61. 3 60. 8 97. 0 1 83. 7 2 73. 3 77. 4 89. 3 85. 1' 600 600 650 709 70 700 700 700 334. 0 84. 8 115. 3 121. 7 235 510. 0 131. 2 118 120 10 120 118 +30 30 10 10 +5 +10 10 1 The 700 F.-+ product consisted 0149.37 (D-l) with 13.1. 7001,000 R, 66.3 SSU 210 F., VI. 107, pour -10 F., and 50.7% (D-2) with B. P. 1,000 F., 201.3 SSU 2 The 700 F. product consisted of 52.0%

210 F., V I 109,

48.0% (E-2) with B.]?. 1,000 E, 220.7 SSU 210 F.,'V.I. 11

pour -5 F. (E-I) with B.P.77001,000 F., 76.8 SSU 210 F.,V.I. 120, and

Example IV To further illustrate the invention, Composition A is used as the sole lubricant in a wristwatch.

Example V To further illustrate the invention, Composition C-l is used as the sole lubricant in a refrigerator.

Example VI To further illustrate the invention, wt. percent of Composition E-2 is blended with 95 wt. percent of a mineral lubricating oil having a viscosity at 210 F. of 35 SUS. The resulting blend is used as the lubricant in an internal combustion engine.

What is claimed is:

1. A method of preparing a fluid useful as a lubricant which comprises reacting to'form a telomer a C to C conjugated diolefin with a material selected from the group consisting of:

(a) an alkali-metalated alkyl aromatic having from 1 to 8 alkyl substituentsof from 1 to 4 carbon atoms,

(b) an alkali-metalated C to C aliphatic hydrocarbon, and

(c) a mixture of 0.2 to 1.5 molar proportions of an alkali metal and one molar proportion of an alkyl aromatic having from 1 to 8 alkyl substituents of from 1 to 4 carbon atoms; where the mole ratio of conjugated diolefin to metalate in (a) and (b) falls in the range of 4:1 to 11:1 and the mole ratio of conjugated diolefin to alkyl aromatic in (0) falls in the range of 0.8:1 to 1.6: 1, and hydrogenating the resultant telomer at a temperature of about 60250 F., at a pressure of about 15-600 p.s.i., and for a duration of about /2 to 6 hours in the presence of a hydrogenation catalyst.

2. A method of preparing a fluid useful as a lubricant having a viscosity index of 105 to 175 and a viscosity of 45 to 550 SUS at 210 R, which comprises reacting to form a telomer 4 to 11 molar proportions of a C to C conjugated diolefin with one molar proportion of an alkali metalated alkyl aromatic having from 1 to 8 alkyl substituents of from 1 to 4 carbon atoms and hydrogenating said telomer at a temperature of about 60250 F a pressure of about 15-600 p.s.i., and for a duration of about /2 to 6 hours in the presence of a hydrogenation catalyst.

3. A method according to claim 2 wherein said conjugated diolefin has four to eight carbon atoms.

4. A method according to claim 2 wherein said conjugated diolefin is butadiene and said alkyl aromatic is toluene.

5. A fluid useful as a lubricant prepared by the method of claim 2.

6. A method of preparing a fluid useful as a lubricant having a viscosity index of 105 to 175 and a viscosity of 45 to 550 SUS at 210 E, which comprises reacting to form a telomer 0.8 to 1.6 molar proportions of a C to C conjugated diolefin with 0.2 to 1.5 molar proportions of an alkali metal with one molar proportion of an alkyl aromatic having from 1 to 8 alkyl substituents of from 1 to 4 carbon atoms and hydrogenating said telomer at a temperature of about 250 F., a pressure of about 15600 p.s.i., and for a duration of about /2 to 6 hours in the presence of a hydrogenation catalyst.

7. A method according to claim 6 wherein said conjugated diolefin is butadiene and said alkyl aromatic is toluene.

8. A fluid useful as a lubricant prepared by the method of claim 6.

9. A method of preparing a fluid useful as a lubricant having a viscosity index of to and a viscosity of 45 to 550 SUS at 210 F., which comprises reacting to form a telomer 4 to 11 molar proportions of a C to C conjugated diolefin with one molar proportion of an alkali metalated C to C aliphatic hydrocarbon and hydrogenating said telomer at a temperature of about 60250 F., a pressure of 15-600 p.s.i., and for a duration of about /2 to 6 hours in the presence of a hydrogenation catalyst.

10. A method according to claim 9 wherein said aliphatic hydrocarbon has from three to eight carbon atoms and said conjugated diolefin has four to eight carbon atoms.

References Cited by the Examiner UNITED STATES PATENTS OTHER REFERENCES Morton et al.: The Reaction of Organosodium Compounds with Butadiene, I. Am. Chem. Soc., vol. 68, pages 93-96 (1946).

DANIEL E. WYMAN, Primary Examiner.

JULIUS GREENWALD, ALPHONSO D. SULLIVAN,

Examiners,

Claims

1. A METHOD OF PREPARING A FLUID USEFUL AS A LUBRICANT WHICH COMPRISES REACTING TO FORM A TELOMER A C4 TO C20 CONJUGATED DIOLEFIN WITH A MATERIAL SELECTED FROM THE GROUP CONSISTING OF: (A) AN ALKALI-METALATED ALKYL AROMATIC HAVING FROM 1 TO 8 ALKYL SUBSTITUENTS OF FROM 1 TO 4 CARBON ATOMS, (B) AN ALKALI-METALATED C1 TO C20 ALIPHATIC HYDROCARBON, AND (C) A MIXTURE OF 0.2 TO 1.5 MOLAR PROPORTIONS OF AN ALKALI METAL AND ONE MOLAR PROPORTION OF AN ALKYL AROMATIC HAVING FROM 1 TO 8 ALKYL SUBSTITUENTS OF FROM 1 TO 4 CARBON ATOMS; WHERE THE MOLE RATIO OF CONJUGATED DIOLEFIN TO METALATE IN (A) AND (B) FALLS IN THE RANGE OF 4:1 TO 11:1 AND THE MOLE RATIO OF CONJUGATED DIOLEFIN TO ALKYL AROMATIC IN (C) FALLS IN THE RANGE OF 0.8:1 TO 1.6:1, AND HYDROGENATING THE RESULTANT TELOMER AT A TEMPERATURE OF ABOUT 60-250*F., AT A PRESSURE OF ABOUT 15-600 P.S.I., AND FOR A DURATION OF ABOUT 1/2 TO 6 HOURS IN THE PRESENCE OF A HYDROGENATION CATALYST.