BRPI0919697B1 - COMPOSITION, METHOD OF LUBRICATING A MACHINE, ENGINE OIL, TRANSMISSION FLUID, HYDRAULIC FLUID, GEAR OIL, INDUSTRIAL OIL, METAL WORKOIL, PROCESS OIL, ADHESIVE OR GRAY DUTCH, ADHESIVE Grease FLUIDITY POINT OR FUEL ADDITIVE - Google Patents

Description

(54) Title: COMPOSITION, METHOD OF LUBRICATING A MACHINE, MOTOR OIL, TRANSMISSION FLUID, HYDRAULIC FLUID, GEAR OIL, INDUSTRIAL OIL, FLUID FOR METAL WORK, PROCESS OIL, MARINE OIL OR Grease, COMPOSITE OIL, GREASE, GREASE, GREASE, GREASE, GREASE, OF LUBRICITY, FLUID POINT REDUCING ADDITIVE OR FUEL ADDITIVE (51) Int.CI .: C07C 13/18; C07C 13/20; C07C 11/21; C10L 1/16 (30) Unionist Priority: 10/10/2008 US 61/104675, 9/21/2009 US 61/244406, 23/03/2009 US 12/409437 (73) Holder (s): AMYRIS, INC .

(72) Inventor (s): KARL FISHER; FRANK X. WOOLARD “COMPOSITION, METHOD OF LUBRICATING A MACHINE, MOTOR OIL, TRANSMISSION FLUID, HYDRAULIC FLUID, GEAR OIL, INDUSTRIAL OIL, METAL WORK FLUID, PROCESS OIL, MARINE OR OIL

GREASE, COMPOUND, AND, LUBRICITY INTENSIFIER, FLUID POINT REDUCING ADDITIVE OR FUEL ADDITIVE ”

RELATED REQUESTS

This patent application claims priority for 10 US provisional patent application number 61 / 104,675, filed on October 10, 2008 and 61 / 244,406, filed on September 21, 2009, and US patent application No. 12 / 409,437, filed on March 23, 2009, whose contents are hereby incorporated by reference in full.

FIELD

Farnesene dimers and / or farnesan dimers and compositions comprising them are provided here. Methods of preparing and using farnesene dimers and / or farnesan dimers are also provided. In certain embodiments, farnesene dimers and / or farnesan dimers and compositions thereof are used as lubricants, lubricity enhancers, pour point reducers or fuel additives.

FUNDAMENTALS

Considerable efforts have been made to develop compositions for use in industrial applications associated with the automotive, tractor, overhead, highway, metal and similar industries. There is a continuous demand for cost effective compositions that present better characteristics.

SUMMARY

In one embodiment, compositions comprising farnesene dimers and / or farnesan dimers are provided herein. In one embodiment, compositions are provided here comprising:

Petition 870170067664, of 9/12/2017, p. 7/15

and one or more compounds selected from:

where, in each compound A, B, C or D, the double lines consisting of a solid and a broken line represent single or double bonds, in such a way that each given data is either completely saturated or completely unsaturated. In other words, in a given compound A, B, C or D, when a double line represents a single bond then all the double lines in this compound represent single bonds. When a double line in a given compound A, B, C or D represents a double bond then all the double lines in this compound represent double bonds.

In one embodiment, compound A is

In one embodiment, compound A is

AND THE.

In one embodiment, one or more compounds are selected from:

In another embodiment, the compositions comprise two or more compounds selected from I-A, I-B, I-C, and I-D.

In another embodiment, the compositions comprise two or more compounds selected from II-A, II-B, II-C, and II-D.

In one embodiment, compositions provided herein comprise famesene dimers of formulas I-A and I-B. In another embodiment, compositions comprise famesene dimers of formulas I4

A, I-B, I-C and I-D. In another embodiment, compositions provided herein comprise famesan dimers of formulas II-A, II-B, II-C and II-D. In one embodiment, the compositions provided herein comprise famesan dimers of formulas II-A and II-B. In another embodiment, compositions provided herein comprise famesene dimers and / or famesan dimers of formulas I-A, I-B, I-C, I-D, II-A, II-B, II-C, II-D or a mixture thereof.

In certain embodiments, a compound selected from the group consisting of I-A, I-C, I-D, II-A, II-C, and II-D is provided herein.

In certain embodiments, a composition comprising compounds I-A and I-B is provided herein. In certain embodiments, the composition still comprises compounds I-C and I-D. In certain embodiments, a composition comprising compounds II-A and II-B is provided herein. In certain embodiments, the composition still comprises compounds II-C and II-D.

In certain embodiments, said compositions are lubricating compositions. In one embodiment, the lubricating compositions provided herein comprise famesene dimers of formulas I-A and I-B. In another embodiment, the lubricating compositions comprise famesene dimers of the formulas I-A, I-B, I-C and I-D. In another embodiment, the lubricating compositions comprise famesan dimers of formulas II-A, II-B, II-C and II-D. In one embodiment, the lubricating compositions provided herein comprise famesan dimers of formulas II-A and II-B. In another embodiment, the lubricating compositions comprise famesene dimers and / or famesan dimers of formulas I-A, I-B, I-C, ID, II-A, II-B, II-C and II-D.

In certain embodiments, compositions comprising famesan dimer II-A and a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6,19,23-tetramethyl-10, 15dimethylenetetracosa-2,6, are provided herein. 11,18,22-pentaene. In one embodiment, the compositions still comprise famesan dimer II-B. In another embodiment, the compositions still comprise a compound selected from I-A, I-B, I-C, I-D, II-C and II-D.

In one embodiment, a composition provided herein comprises famesan dimer II-A or famesan dimer II-B, and a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6, 19,23 tetramethyl- 10,15-dimethylenetetracosa-2,6,1 l 1,18,22-pentaene. In one embodiment, a composition provided herein comprises famesan dimer II-A or famesan dimer II-B, and squalane. In another embodiment, a composition provided herein comprises IA, IB, IC, ID, II-A, II-B, II-C or II-D and a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6,19,23-tetramethyl-10,15-dimethylenetetracosa2,6,11,18,22-pentaene. In one embodiment, a composition provided herein comprises famesan dimer II-A and squalane.

In certain embodiments, compositions provided herein have a viscosity index greater than about 200 according to ASTM D 2270. In certain embodiments, the viscosity index is from 230 to about 240 according to ASTM D 2270. The compositions provided herein may exist as liquid compositions at room temperature.

In certain embodiments, compositions provided herein have a viscosity index of about 80 or greater according to ASTM D 2270. In certain embodiments, the viscosity index is about 90 to about 150 according to ASTM D 2270.

In certain embodiments, famesene dimers and / or famesan dimers and compositions thereof are useful as lubricity enhancers, pour point reducers and / or fuel additives. Famesene dimers and / or famesan dimers and compositions thereof can be used in a wide variety of applications including, but not limited to, applications associated with the automotive, tractor, airline and highway industries including engines, transmissions, and similar, metal-working fluids, finishing fluids, greases, crankcase lubricants, power transmission fluids, vehicle axle applications, hydraulic systems, heavy dirt gear oils, and turning machinery, such as stationary engines, pumps, gas turbines, compressors, wind turbines, and the like. Stationary engines include fuel and gas engines that are not associated with the automotive, tractor, overhead and highway industries. Also provided are methods of preparing the compounds and compositions.

In certain embodiments, compositions provided herein are readily biodegradable. In certain embodiments, compositions provided here are low in toxicity and have little or no damage to aquatic organisms or surrounding vegetation. These qualities are particularly used for applications in environmentally sensitive areas, such as marine ecosystems, and for those with a high potential to be lost to the surrounding environment. In certain embodiments, compositions provided herein may be derived from readily available, renewable materials.

In certain embodiments, a method of lubricating a machine is provided here by operating the machine in contact with a composition provided herein. The compositions can be used to lubricate any machine that needs lubrication. Exemplary machines include, but are not limited to, engines, pumps, gas turbines, compressors, wind turbines, and the like. In certain modalities, the engine is a fuel and / or gas engine associated with the automotive, tractor, overhead and highway industries. In certain embodiments, the engine is a stationary engine, including a fuel and / or gas engine that is not associated with the automotive, tractor, overhead and highway industries.

In certain embodiments, a machine comprising a composition provided herein is provided here.

DESCRIPTION OF THE DRAWINGS

Figure 1 shows the relationship of kinetic viscosity for various mixtures of squalane and famesan dimer II-A at 40 and 100 ° C.

Figure 2 shows the viscosity index for various mixtures of squalane and famesan dimer II-A.

DEFINITIONS

In the following description, all numbers described here are approximate values, regardless of whether the word "about" or "approximate" is used. Numbers can vary by 1 percent, 2 percent, 5 percent, or sometimes 10 to 20 percent. When a numerical range with a lower limit, R ^L , and an upper limit, R ^u is described, any number that falls in the range is specifically described. In particular, the following numbers in the range are specifically described: R = R ^L + k * (R ^u -R ^L ), where k is a variable ranging from 1 percent to 100 percent with an increase of 1 percent , that is, k is 1 percent, 2 percent, 3 percent, 4 percent, 5 percent, ..., 50 percent, 51 percent, 52 percent, ..., 95 percent, 96 percent, 97 percent, 98 percent, 99 percent, or 100 percent. In addition, any numerical range defined by the two R numbers, as previously defined is also specifically described.

As used herein, "β-Famesene" refers to a compound having the following formula:

or a stereoisomer of the same. In some embodiments, β-famesene comprises a substantially pure stereoisomer of β-famesene. In other embodiments, β-famesene comprises a mixture of stereoisomers, such as cis-trans isomers. In additional embodiments, the amount of each of the stereoisomers in the β-famesene mixture is independently from about 0.1% by weight to about 99.9% by weight, from about 0.5% by weight to about 99.5% by weight, from about 1% by weight to about 99% by weight, from about 5% by weight to about 95% by weight, from about 10% by weight to about 90% by weight weight, from about 20% by weight to about 80% by weight, based on the total weight of the βfamesene mixture.

As used herein, “squalane” refers to a compound having the following formula:

As used herein, "squalene" refers to a compound having the following formula:

As used herein, "dehydroesqualene" or "(6E, 11E, 18E) 2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,1 l 1,18,22-pentaene" refers to a compound having the following formula:

DESCRIPTION OF MODALITIES

In one embodiment, compositions comprising two or more farnesene dimers and / or farnesan dimers are provided herein.

In one embodiment, compositions are provided here comprising:

Β,

in such a way that in a given compound A, B, C or D, when a double line represents a single bond then all the double lines in this compound represent single bonds. When a double line in a given compound A, B, C or D represents a double bond then all the double lines in this compound represent double bonds. In other words, in each compound A, B, C or D the double lines consisting of a solid and a broken line represent a single or double bond, such that a given compound is either completely saturated or completely unsaturated.

In one embodiment, compound A is

In one embodiment, compound A is

In another embodiment, the compositions comprise two or more compounds selected from I-A, I-B, I-C and I-D.

In another embodiment, the compositions comprise two or more compounds selected from II-A, II-B, II-C and II-D.

In one embodiment, compositions provided herein comprise famesene dimers of formulas I-A and I-B. In another embodiment, compositions provided herein comprise famesene dimers of formulas I-A, I-B, I-C and I-D.

In another embodiment, compositions provided herein comprise famesan dimers of formulas II-A, II-B, II-C and II-D. In one embodiment, the compositions provided herein comprise famesan dimers of formulas II-A and II-B. In another embodiment, compositions provided herein comprise famesene dimers and / or famesan dimers of formulas I-A, I-B, I-C, I-D, II-A, II-B, II-C and II-D.

In certain embodiments, the amount of one or more famesene dimers and / or famesan dimers in the compositions is provided here at least about 0.1% based on the total weight of the composition. In certain embodiments, the amount of one or more famesene dimers and / or famesan dimers in the compositions is provided here from about 1 to about 95% based on the total weight of the composition. In certain embodiments, the amount of one or more famesene dimers and / or famesan dimers in the compositions is provided here at least about 0.1, 1, 2, 3, 4, 5, 7, 9, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90, 92, 95, 96, 97, 98, 99 or 99.5% based on the total weight of the composition.

In certain embodiments, the amount of famesene dimer of formula I-A in the compositions is provided here at least about 10% based on the total weight of the famesene dimers. In certain embodiments, the amount of famesene dimer of formula I-A in the compositions is provided here at least about 20% based on the total weight of the famesene dimers. In certain embodiments, the amount of famesene dimer of formula IA in the compositions is provided here from about 25 to about 90%, about 25 to about 80%, about 30 to about 70%, about 30 to about 60%, about 30 to about 50%, or about 30 to about 40% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula IA in the compositions is at least about 5, 10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 50, 60, 70, 75 , 80 or 90% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula IA in the compositions is at least about 25, 30, 35, 40, 50, 60, 70, 75, 80 or 90% based on the total weight of the famesene dimers in the composition .

In certain embodiments, the amount of famesene dimer of formula I-B in the compositions is provided here at least about 10% based on the total weight of the famesene dimers. In certain embodiments, the amount of famesene dimer of formula I-B in the compositions is provided here at least about 20% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula I-B in the compositions is provided here at least about 25% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula IB in the compositions is provided here from about 25 to about 90%, about 25 to about 80%, about 30 to about 70%, about 30 to about 60%, about 30 to about 50%, or about 30 to about 40% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula IB in the compositions is at least about 5, 10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 50, 60, 70, 75 , 80 or 90% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula IB in the compositions is provided here at least about 25, 30, 35, 40, 50, 60, 70, 75, 80 or 90% based on the total weight of the famesene dimers in the composition.

In certain embodiments, the amount of famesene dimer of formula I-C in the compositions is provided here at least about 1% or about 2% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula I-C in the compositions is provided here at least about 5% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of the formula IC in the compositions is provided here from about 5 to about 40%, about 5 to about 30%, about 10 to about 25% or about 10 to about 20% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of the formula IC in the compositions is provided here at least about 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15, 20, 25 , 30, 35 or 40% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of the formula IC in the compositions is provided here at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based on the total weight of the famesene dimers in the composition .

In certain embodiments, the amount of famesene dimer of formula I-D in the compositions is provided here at least about 1% or about 2% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of formula I-D in the compositions is provided here at least about 5% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of the formula ID in the compositions is provided here from about 5 to about 40%, about 5 to about 30%, about 10 to about 25% or about 10 to about 20% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of the formula ID in the compositions is provided here at least about 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15, 20, 25 , 30, 35 or 40% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesene dimer of the formula ID in the compositions is provided here at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based on the total weight of the famesene dimers in the composition .

In certain embodiments, the total amount of famesene dimers of formulas I-A and I-B in the compositions is provided here at least about 10% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers of formulas I-A and I-B in the compositions is provided here at least about 20% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers of formulas I-A and I-B in the compositions is provided here at least about 40% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers of formulas IA and IB in the compositions is provided here from about 40 to about 90%, about 50 to about 85%, about 50 to about 80% or about from 60 to about 80% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers of formulas IA and IB in the compositions is provided here at least about 5, 10, 15, 20, 25, 30, 35, 37, 40, 45, 50, 60, 70 , 75, 80 or 90% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers of formulas IA and IC in the compositions is provided here at least about 40, 50, 60, 70, 75, 80 or 90% based on the total weight of the famesene dimers in the composition .

In certain embodiments, the total amount of famesene dimers of the formulas IC and ID in the compositions is provided here at least about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9 %, 10%, 11% or 12% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers in the formulas

I-C and I-D in the compositions are provided here at least about 10% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers of the formulas IC and ID in the compositions is provided here from about 10 to about 40%, about 10 to about 30%, about 10 to about 25% or about from 10 to about 20% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesene dimers of the formulas IC and ID in the compositions is provided here at least about 10, 15, 20, 25, 30, 35 or 40% based on the total weight of the famesene dimers in the composition .

In certain embodiments, the amount of famesan dimer of formula II-A in the compositions is provided here at least about 10% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-A in the compositions is provided here at least about 20% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-A in the compositions is provided here at least about 25% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-A in the compositions is provided here from about 25 to about 90%, about 25 to about 80%, about 30 to about 70%, about 30 to about 60%, about 30 to about 50% or about 30 to about 40% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesene dimer of formula II-A in the compositions is at least about 5, 10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 45, 50, 60 , 70, 75, 80 or 90% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-A in the compositions is provided here at least about 25, 30, 35, 40, 50, 60, 70, 75, 80 or 90% based on the total weight of the famesan dimers in the composition.

In certain embodiments, the amount of famesan dimer of formula II-B in the compositions is provided here at least about 20% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-B in the compositions is provided here at least about 25% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-B in the compositions is provided here from about 25 to about 90%, about 25 to about 80%, about 30 to about 70%, about 30 to about 60%, about 30 to about 50% or about 30 to about 40% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesene dimer of formula II-B in the compositions is at least about 10, 12, 14, 15, 17, 20, 25, 30, 35, 37, 40, 45, 50, 60, 70 , 75, 80 or 90% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-B in the compositions is provided here at least about 25, 30, 35, 40, 50, 60, 70, 75, 80 or 90% based on the total weight of the famesan dimers in the composition.

In certain embodiments, the amount of famesan dimer of formula II-C in the compositions is provided here at least about 5% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-C in the compositions is provided here from about 5 to about 40%, about 5 to about 30%, about 10 to about 25% or about 10 to about 20% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesene dimer of formula II-C in the compositions is provided here at least about 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15, 20 , 25, 30, 35 or 40% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-C in the compositions is provided here at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based on the total weight of the dimers of famesan in composition.

In certain embodiments, the amount of famesan dimer of formula II-D in the compositions is provided here at least about 5% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-D in the compositions is provided here from about 5 to about 40%, about 5 to about 30%, about 10 to about 25% or about 10 to about 20% based on the total weight of the famesan dimers in the composition. In certain embodiments, the amount of famesene dimer of formula II-D in the compositions is provided here at least about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15, 20 , 25, 30, 35 or 40% based on the total weight of the famesene dimers in the composition. In certain embodiments, the amount of famesan dimer of formula II-D in the compositions is provided here at least about 5, 10, 12, 15, 20, 25, 30, 35 or 40% based on the total weight of the dimers of famesan in composition.

In certain embodiments, the total amount of famesan dimers of formula II-A and II-B in the compositions is provided here at least about 40% based on the total weight of the famesan dimers in the composition. In certain embodiments, the total amount of famesan dimers of formulas II-A and II-B in the compositions is provided here from about 40 to about 99.5%, about 50 to about 90%, about 50 to about 85% or about 60 to about 80% based on the total weight of the famesan dimers in the composition. In certain embodiments, the total amount of famesene dimers of formulas II-A and II-B in the compositions is provided here at least about 10, 15, 20, 25, 30, 35, 37, 40, 45, 50, 60 , 70, 75, 80 or 90% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesan dimers of formulas II-A and II-B in the compositions is provided here at least about 40, 50, 60, 70, 75, 80 or 90% based on the total weight of the dimers of famesano in the composition.

In certain embodiments, the total amount of famesene dimers of formulas II-C and II-D in the compositions is provided here at least about 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11% or 12% based on the total weight of the famesene dimers in the composition. In certain embodiments, the total amount of famesan dimers of formulas II-C and II-D in the compositions is provided here at least about 10% based on the total weight of the famesan dimers in the composition. In certain embodiments, the total amount of famesan dimers of formula II-C and IID in the compositions is provided here from about 10 to about 40%, about 10 to about 30%, about 10 to about 25% or about 10 to about 20% based on the total weight of the famesan dimers in the composition. In certain embodiments, the total amount of famesan dimers of formula II-C and II15 D in the compositions is provided here at least about 10, 15, 20, 25, 30, 35 or 40% based on the total weight of the dimers of famesan in composition.

In certain embodiments, compositions provided herein comprise famesene dimers of formulas I-A, I-B, I-C and I-D. In one embodiment, the amount of famesan dimer of formula IA in the compositions is provided here at least about 10%, the amount of famesene dimer of formula IB in the compositions is provided here at least about 10%, the amount of famesan dimer in the Formula IC in the compositions is provided here at least about 1% and the amount of famesene dimer of the formula ID in the compositions is provided here at least about 1% based on the total weight of the famesene dimers in the composition. In one embodiment, the amount of famesan dimer of formula IA in the compositions is provided here at least about 20%, the amount of famesene dimer of formula IB in the compositions is provided here at least about 20%, the amount of famesene dimer in the Formula IC in the compositions is provided here at least about 2% and the amount of famesene dimer of the formula ID in the compositions is provided here at least about 2% based on the total weight of the famesene dimers in the composition. In one embodiment, the amount of famesan dimer of formula IA in the compositions is provided here at least about 30%, the amount of famesene dimer of formula IB in the compositions is provided here at least about 30%, the amount of famesene dimer in the Formula IC in the compositions is provided here at least about 5% and the amount of famesene dimer of the formula ID in the compositions is provided here at least about 5% based on the total weight of the famesene dimers in the composition. In one embodiment, the amount of famesan dimer of formula IA in the compositions is provided here from about 30% to about 50%, the amount of famesene dimer of the formula IB in the compositions is provided here from about 30% to about 50%. %, the amount of famesan dimer of the formula IC in the compositions is provided here from about 5% to about 15% and the amount of famesan dimer of the formula

I-D in the compositions is provided here from about 5% to about 15% based on the total weight of the famesene dimers in the composition. In one embodiment, compositions provided herein comprise about 40% famesene dimer of formula, about 40% famesene dimer of formula, about 10% formula famesene dimer, and about ID formula famesene dimer about. 10% based on the total weight of the famesene dimers in the composition.

In certain embodiments, the compositions provided herein comprise famesan dimers of the formula II-A, II-B, II-C and II-D. In one embodiment, the amount of famesan dimer of formula II-A in the compositions is provided here at least about 10%, the amount of famesan dimer of formula II-B in the compositions is provided here at least about 10%, the amount of famesan dimer of formula II-C in the compositions is provided here at least about 1% and the amount of famesan dimer of formula II-D in the compositions is provided here at least about 1% based on the total weight of famesan dimers in the composition. In one embodiment, the amount of famesan dimer of formula II-A in the compositions is provided here at least about 20%, the amount of famesan dimer of formula II-B in the compositions is provided here at least about 20%, the amount of famesan dimer of formula II-C in the compositions is provided here at least about 2% and the amount of famesan dimer of formula II-D in the compositions is provided here at least about 2% based on the total weight of famesan dimers in the composition. In one embodiment, the amount of famesan dimer of formula II-A in the compositions is provided here at least about 30%, the amount of famesan dimer of formula II-B in the compositions is provided here at least about 30%, the amount of famesan dimer of formula II-C in the compositions is provided here at least about 5% and the amount of famesan dimer of formula II-D in the compositions is provided here at least about 5% based on the total weight of famesan dimers in the composition. In one embodiment, the amount of famesan dimer of formula II-A in the compositions is provided here from about 30% to about 50%, the amount of famesan dimer of formula II-B in the compositions is provided here about 30% to about 50%, the amount of famesan dimer of formula II-C in the compositions is provided here from about 5% to about 15% and the amount of famesan dimer of formula II-D in the compositions is here supplied from about 5% to about 15% based on the total weight of the famesan dimers in the composition. In one embodiment, the compositions provided herein comprise famesan dimer of formula II-A by about 40%, famesan dimer of formula II-B by about 40%, famesan dimer of formula II-C by about 10%, and famesan dimer of formula II-D by about 10% based on the total weight of the famesan dimers in the composition.

In certain embodiments, compositions provided herein comprise famesene dimers of the formula IA: IB: IC: ID in a 4: 4: 1: 1 ratio. In certain embodiments, compositions provided herein comprise famesan dimers of the formula II-A: II -B: II-C: II-D in a 4: 4: 1: 1 ratio.

In one embodiment, compositions comprising famesan dimer II-A and a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6,19,23-tetramethyl-10,15dimethylenetetracosa-2,6, are provided herein. 11,18,22-pentaene. In one embodiment, the compositions still comprise famesan dimer II-B. In another embodiment, the compositions still comprise a famesan dimer selected from II-C, and II-D. In another embodiment, the compositions still comprise a famesan dimer selected from I-A, I-B, I-C, and I-D.

In one embodiment, a composition provided herein comprises famesan dimer II-A or famesan dimer II-B, and a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6, 19,23 tetramethyl- 10, 15-dimethylenetetracosa-2,6, 11,18,22-pentaene.

In another embodiment, a composition provided herein comprises famesan dimer and / or famesan dimer IA, IB, IC, ID, IIA, II-B, II-C or II-D ₃ and a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6,19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene.

In one embodiment, a composition comprising famesan dimer II-A, and squalane is provided herein. In one embodiment, the composition still comprises famesan dimer II-B. In one embodiment, the composition further comprises I-A, I-B, I-C, I-D, II-C, II-D or a mixture thereof.

In certain embodiments, the amount of famesan dimer II-A in the compositions is provided here about 1% or more based on the total weight of the composition. In certain embodiments, the amount of famesan dimer II-A in the compositions is provided here from about 1 to about 95% based on the total weight of the composition. In certain embodiments, the amount of famesan dimer II-A in the compositions is provided here about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, 80, 90, or 95% or more based on the total weight of the composition.

In certain embodiments, the amount of famesan dimer 10 II-B in the compositions provided herein is about 1% or more based on the total weight of the composition. In certain embodiments, the amount of famesan dimer II-A in the compositions is provided here from about 1 to about 80% based on the total weight of the composition. In certain embodiments, the amount of famesan dimer II-A in the compositions is provided here about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, or 80% or more based on the total weight of the composition.

In certain embodiments, the total amount of famesene dimers and / or famesan dimers IA, IB, IC, ID, II-C and II-D in the compositions is provided here about 0.1% or more based on the total weight composition. In certain embodiments, the total amount of famesene dimers and / or famesan dimers IA, IB, IC, ID, II-C and II-D in the compositions is provided here about 1% or more based on the total weight of the composition . In certain embodiments, the total amount of famesene dimers and / or famesan dimers IA, IB, IC, ID, II-C and II-D in the compositions is provided here about 1 to 20% or more based on the total weight of famesene dimers. In certain embodiments, the total amount of famesene dimers and / or famesan dimers IA, IB, IC, I-D, II-C and IID in the compositions is provided here about 0.1, 1, 2, 3, 4 , 5, 6, 10, 12, 15,

17, 20, 25, 30, 35, 40 or 50% or more based on the total weight of the famesene dimers.

In certain embodiments, the total amount of squalane, squalene and dehydroesqualene in the compositions is provided here about 1% or more based on the total weight of the composition. In certain embodiments, the total amount of squalane, squalene and dehydroesqualene in the compositions is provided here from about 5 to about 90% based on the total weight of the composition. In certain embodiments, the total amount of squalane, squalene and dehydroesqualene in the compositions is provided here about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, 80 or 90% or more based on the total weight of the composition.

In certain embodiments, the amount of squalane in the compositions is provided here about 1% or more based on the total weight of the composition. In certain embodiments, the total amount of squalane in the compositions is provided here from about 1 to about 95% or 5 to about 90% or more based on the total weight of the composition. In certain embodiments, the total amount of squalane in the compositions is provided here about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, 80, or 90% or more based on the total weight of the composition.

In certain embodiments, the amount of squalene in the compositions is provided here about 1% or more based on the total weight of the composition. In certain embodiments, the total amount of squalene in the compositions is provided here from about 1 to about 90%, about 1 to about 50%, about 1 to about 30% or more based on the total weight of the composition . In certain embodiments, the total amount of squalene in the compositions is provided here about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, 80 or 90% or more based on the total weight of the composition.

In certain embodiments, the amount of dehydroesqualene in the compositions is provided here about 1% or more based on the total weight of the composition. In certain embodiments, the total amount of dehydroesqualene in the compositions is provided here from about 1 to about 90%, about 1 to about 50%, about 1 to about 30% or more based on the total weight of the composition . In certain embodiments, the total amount of dehydroesqualene in the compositions is provided here about 1, 3, 5, 7, 10, 12, 15, 17, 20, 23, 25, 27, 30, 33, 35, 37, 40, 43, 45, 47, 50, 60, 70, 80 or 90% or more based on the total weight of the composition.

In certain embodiments, the compounds and compositions provided herein have a viscosity at 100 ° C of about 5 centistokes (cSt) to about 20 cSt, about 5 centistokes (cSt) to about 15 cSt, or about 7 cSt at about 13 cSt. In certain embodiments, the compounds and compositions have a viscosity of about 10 cSt at 100 ° C. In certain embodiments, the compounds and compositions provided herein have a viscosity at 40 ° C of about 25 centistokes (cSt) to about 50 cSt, about 30 centistokes (cSt) to about 50 cSt, or about 35 cSt at about 45 cSt. In certain embodiments, the compounds and compositions have a viscosity of about 43 cSt at 40 ° C. The viscosity of the compounds and compositions described herein can be measured according to ASTM D 445.

In certain embodiments, the compounds and compositions provided herein have a viscosity index greater than about 200 according to ASTM D 2270. In certain embodiments, the viscosity index is greater than about 220 according to ASTM D 2270. In certain embodiments modalities, the viscosity index is about 220 to about 245 according to ASTM

D 2270. In certain embodiments, the viscosity index is from about 230 to about 240 according to ASTM D 2270.

In certain embodiments, the compositions provided herein have a kinetic viscosity of about 3 centistokes (cSt) or greater at 100 ° C. In certain embodiments, the compositions provided herein have a kinetic viscosity of about 4 centistokes (cSt) or greater at 100 ° C. In certain embodiments, the compositions provided herein have a kinetic viscosity of about 3 cSt to about 10 cSt, about 4 cSt to about 8 cSt, or about 4 cSt to about 6 cSt at 100 ° C. In certain embodiments, the compositions provided here have a kinetic viscosity of about 3 centistokes (cSt) to about 10 cSt, about 4 cSt to about 8 cSt, or about 4 cSt to about 6 cSt at 100 ° Ç. In certain embodiments, the compositions provided herein have a kinetic viscosity of about 4, 5, or 6 cSt at 100 ° C.

In certain embodiments, the compositions provided herein have a kinetic viscosity of about 15 cSt or greater at 40 ° C. In certain embodiments, the compositions provided herein have a kinetic viscosity of about 20 cSt or greater at 40 ° C. In certain embodiments, the compositions provided herein have a kinetic viscosity of about 15 cSt to about 40 cSt, about 20 cSt to about 40 cSt, or about 20 cSt to about 30 cSt at 40 ° C. In certain embodiments, the compositions have a kinetic viscosity of about 20, 25, 30 or 35 cSt at 40 ° C. The kinetic viscosity of the compositions described herein can be measured according to ASTM D 445.

In certain embodiments, the compositions provided herein have a dynamic viscosity of about 10 cP or greater at 40 ° C. In certain embodiments, the compositions provided herein have a dynamic viscosity of about 15 cP or greater at 40 ° C. In certain embodiments, the compositions provided herein have dynamic viscosity from about 10 cP to about 40 cP, from about 15 cP to about 30 cP, or from about 15 cP to about 25 cP at 40 ° C. In certain embodiments, the compositions provided herein have a dynamic viscosity of about 15, 17, 20, 22, or 25 cP at 40 ° C.

In certain embodiments, the compositions provided herein have a dynamic viscosity of about 2 cP or greater at 100 ° C. In certain embodiments, the compositions provided herein have a dynamic viscosity of about 3 cP or greater at 100 ° C. In certain embodiments, the compositions provided herein have dynamic viscosity of about 1 cP to about 10 cP, about 1 cP to about 7 cP, or about 2 cP to about 5 cP at 100 ° C. In certain embodiments, the compositions have a dynamic viscosity of about 2, 3, 4 or 5 cP at 100 ° C. The dynamic viscosity of the compositions described herein can be measured according to ASTM D 445.

In certain embodiments, compositions provided herein have a viscosity index of about 90 or greater according to ASTM D 2270, In certain embodiments, compositions provided here have a viscosity index of about 100 or greater according to ASTM D 2270. In certain embodiments, the viscosity index is about 90 to about 140 or about 100 to about 130 according to ASTM D 2270. In certain embodiments, the viscosity index is about 110 to about 130 according to ASTM D 2270. In certain embodiments, the viscosity index is about 100, 110, 120, 125 or about 130 according to ASTM D 2270.

In certain embodiments, the compositions provided herein have a density of about 0.700 to about 0.900 at 40 ° C. In certain embodiments, the compositions provided herein have a density of about 0.700 to about 0.850 at 40 ° C. In certain embodiments, the compositions provided herein have a density of about 0.700, 0.750, 0.800, 0.850 or 0.900 at 40 ° C. In certain embodiments, the compositions provided herein have a density of about 0.700 to about 0.800 at 100 ° C. In certain embodiments, the compositions provided herein have a density of about 0.700, 0.750, or 0.800 at 100 ° C.

In certain embodiments, the compounds and compositions provided herein are used as a lubricity enhancer. In another embodiment, lubricity enhancing compositions comprising one or more compounds of the formula I-A, I-B, I-C, I-D, II-A, IIB, II-C, and Π-D and a suitable lubricating oil additive are provided herein. In certain embodiments, lubricity enhancing compositions comprise between 0.1 and 75%, between 1 and 65%, or between 5 and 50% of the compound of the formula ΙΑ, IB, IC, ID, II-A, II-B , II-C, Π-D or a combination thereof.

In one embodiment, a composition provided herein comprises farnesan dimer II-A or farnesan dimer II-B; a compound selected from squalane, squalene, and (6E, 1 IE, 18E) -2.6, 19.23 tetramethyl-10, 15-dimethylenetetracosa-2,6, 11,18,22-pentaene; and a suitable lubricating oil additive.

Any lubricating oil additive known to one skilled in the art can be used in the lubricity enhancing compositions described here. In some embodiments, the lubricating oil additive can be selected from the group consisting of antioxidants, anti-wear agents, detergents, rust inhibitors, demulsifiers, friction modifiers, multi-functional additives, pour point reducers, foam inhibitors, deactivators metal, dispersants, corrosion inhibitors, thermal stability enhancers, dyes, markers, and combinations thereof.

In another embodiment, lubricity enhancing compositions are provided here comprising a compound of the formula IA, IB, IC, ID, II-A, II-B, II-C, II-D or a combination thereof, a suitable additive and optionally a base oil for lubrication viscosity.

In one embodiment, a composition provided herein comprises farnesan dimer II-A or farnesan dimer II-B; a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6,19,2325 tetramethyl-10,15-dimethylenetetracosa-2,6,11,18,22-pentaene; a suitable additive and optionally an oil based on lubricating viscosity.

Any base oil known to one skilled in the art can be used as the lubricating viscosity oil described herein.

Some base oils suitable for preparing lubricating compositions have been described in Mortier et ah, "Chemistry and Technology of Lubricants" 2nd Edition, London, Springer, Chapters 1 and 2 (1996); and A. Sequeria, Jr., "Lubricant base oil and wax Processing," New York, Marcei Decker, Chapter 6, (1994); and D. V. Brock, Lubrication Engineering, Vol. 43, pages 184-5, (1987), all of which are incorporated by reference. In certain embodiments, the amount of the base oil in the composition is greater than about 1% based on the total weight of the composition. In certain embodiments, the amount of the base oil in the composition is greater than about 2, 5, 15 or 20% based on the total weight of the composition. In some embodiments, the amount of the base oil in the composition is about 1-20% based on the total weight of the composition. In certain embodiments, the amount of base oil in the compositions is provided here about 1%, 5%, 7%, 10%, 13%, 15%, or 20% based on the total weight of the composition.

In certain embodiments, the base oil is or comprises any fraction of natural or synthetic lubricating base oil. Some non-limiting examples of synthetic oils include oils, such as polyalphaolefins or PAOs, prepared from the polymerization of at least one alpha-olefin, such as ethylene, or from hydrocarbon synthesis procedures using carbon monoxide and hydrogen gases, such as FisherTropsch process.

In other embodiments, the base oil is or comprises a base stock or combination of base stocks. In additional embodiments, base stocks are manufactured using a variety of different processes including, but not limited to, distillation, solvent refining, hydrogen processing, oligomerization, esterification, and refining. In some embodiments, basic inventories comprise refined inventory. In additional modalities, the refined stock is substantially free of materials introduced through manufacturing, contamination, or prior use.

In some embodiments, the base oil comprises one or more of the base stocks in one or more of the I-V groups as specified in the American Petroleum Institute (API) Publication 1509, Fourteenth edition, December 1996 (ie API Base Oil

Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Oil), which is incorporated by reference. The API guide defines a base stock as a lubricating component that can be manufactured using a variety of different processes. Basic stocks of groups I, II and III are mineral oils, each with specific ranges of saturated amounts, sulfur content and viscosity index. Group IV base stocks are polyalphaolefins (PAO). Group V base stocks include all other base stocks not included in group I, II, III, or IV.

The saturated levels, sulfur levels and viscosity indices for basic stocks of groups I, II, III, IV and V are listed in table 1 below.

Table 1,

group Saturated (as determined by ASTM D2007) Sulfur (as determined by ASTM D2207) - _r viscosity index (as determined by ASTM D4294, ASTM D4297 or ASTM D3120) I Less than 90% saturated Greater than or equal to 0.03% sulfur Greater than or equal to 80 and less than 120 II Greater than or equal to 90% saturated Less than or equal to 0.03% sulfur Greater than or equal to 80 and less than 120 III Greater than or equal to 90% saturated Less than or equal to 0.03% sulfur Greater than or equal to 120 IV Defined as polyalphaolefins (BREAD) V All other basic stocks not included in the groups I, II, III and IV

In certain embodiments, the base oil is selected from the group consisting of natural lubricating viscosity oils, synthetic lubricating viscosity oils and mixtures thereof. In some embodiments, the base oil includes base stocks obtained by isomerization of synthetic wax and coal slag wax, as well as base hydrocrack stocks produced by hydrocracking (instead of solvent extraction) of the aromatic and polar components of the crude product . In other embodiments, the base lubricating viscosity oil includes natural oils, such as animal oils, vegetable oils, mineral oils (for example, liquid petroleum oils and solvent-treated or paraffinic or paraffinic acid-treated mineral oils) (mixed naphthenic), oils derived from coal or shale, and combinations thereof. Some non-limiting examples of animal oils include bone oil, lanolin, fish oil, lard oil, dolphin oil, sea oil, shark oil, wax oil, and whale oil. Some non-limiting examples of vegetable oils include castor oil, olive oil, peanut oil, rapeseed oil, corn oil, sesame oil, cottonseed oil, soybean oil, sunflower oil, hemp, flax seed oil, tung oil, octica oil, jojoba oil and pasture foam oil. Such oils can be partially or completely hydrogenated.

In some embodiments, synthetic lubricating viscosity oils include halo-substituted hydrocarbon oils and hydrocarbon oils, such as polymerized and interpolymerized olefins, alkylbenzenes, polyphenyls, alkylated diphenyl ethers, alkylated diphenyl sulfites, and their derivatives, analogues and similar counterparts. In other embodiments, synthetic oils include alkylene oxide polymers, interpolymers, copolymers and derivatives thereof where the terminal hydroxyl groups can be modified by esterification, etherification, and the like. In additional embodiments, synthetic oils include esters of dicarboxylic acids with a variety of alcohols.

In certain embodiments, synthetic oils include esters made from C ₅ to C 12 monocarboxylic acids and polyols and polyol ethers. In additional embodiments, synthetic oils include trialkyl phosphate ester oils, such as tri-n-butyl phosphate and tri-iso-butyl phosphate.

In some embodiments, synthetic lubricating viscosity oils include silicon based oils (such as polyalkyl-, polyaryl-, polyalkoxy-, polyaryloxy-siloxane oils and silicate oils). In other embodiments, synthetic oils include liquid phosphorus-containing acid esters, polymeric tetrahydrofurans, polyalphaolefins, and the like.

r

Base oil derived from hydroisomerization of wax can also be used, either alone or in combination with the natural and / or synthetic base oil mentioned above. Such wax isomerate oil is produced by the hydroisomerization of natural or synthetic waxes or mixtures of them on a hydroisomerization catalyst.

In additional embodiments, the base oil comprises a polyalpha-olefin (PAO). In general, poly-alpha-olefins can be derived from an alpha-olefin having from about 2 to about 30, from about 4 to about 20, or from about 6 to about 16 carbon atoms. Non-limiting examples of suitable poly-alpha-olefins include those derived from octene, decene, mixtures thereof, and the like. These poly-alpha-olefins can have a viscosity of about 2 to about 15, about 3 to about 12, or about 4 to about 8 centistokes at 100 ° C. In some cases, poly-alpha-olefins can be used in conjunction with other base oils, such as mineral oils.

In additional embodiments, the base oil comprises a polyalkylene glycol or a derivative of polyalkylene glycol, where the terminal hydroxyl groups of the polyalkylene glycol can be modified by esterification, etherification, acetylation and the like. Non-limiting examples of suitable polyalkylene glycols include polyethylene glycol, polypropylene glycol, polyisopropylene glycol, and combinations thereof. Non-limiting examples of suitable polyalkylene glycols derivatives include polyalkylene glycols ethers (e.g., polyisopropylene glycol methyl ether, polyethylene glycol diphenyl ether, polypropylene glycol diphenyl ether, etc.), polyalkylene glycol mono- and polycarboxylic esters, and combinations thereof. In some cases, polyalkylene glycol or a derivative of polyalkylene glycol can be used in conjunction with other base oils, such as poly alpha-olefins and mineral oils.

In additional embodiments, the base oil comprises any of the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, submeric acid, sebacic acid, fumaric acid, adipic acid , linoleic acid dimer, malonic acid, alkyl malonic acids, alkenyl malonic acids, and the like) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethyl hexyl, ethylene glycol, diethylene glycol monoether , propylene glycol, and the like). Non-limiting examples of the same esters include dibutyl adipate, di (2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacatp, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate dieicosyl, the 2-ethylhexyl diester of linoleic acid dimer, and the like.

In additional embodiments, the base oil comprises a hydrocarbon prepared by the Fischer-Tropsch process. The Fischer-Tropsch process prepares hydrocarbons from gases containing hydrogen and carbon monoxide using a Fischer25 Tropsch catalyst. These hydrocarbons may require further processing in order to be used as a base oil. For example, hydrocarbons can be defatted, hydroisomerized and / or hydrocracked using processes known to one skilled in the art.

In additional embodiments, the base oil comprises an unrefined oil, a refined oil, a re-refined oil, or a mixture thereof. Unrefined oils are those obtained directly from a natural or synthetic source without further purification treatment. Non-limiting examples of unrefined oils include shale oils obtained directly from retort operations, petroleum oils obtained directly from primary distillation, and ester oils obtained directly from an esterification process and used without further treatment. Refined oils are similar to unrefined oils except that the former was further treated by one or more purification processes to improve one or more properties. Many purification processes like this are known to those skilled in the art, such as solvent extraction, secondary distillation, acid or base extraction, filtration, percolation, and the like. Re-refined oils are obtained by applying to refined oil processes similar to those used to obtain refined oils. Such re-refined oils are also known as re-claimed or re-processed oils and are often additionally treated by processes aimed at removing spent additives and waste oil products.

In certain embodiments, the compounds and compositions provided herein are used as additives for the pour point reducer. In another embodiment, pour point reduction additive compositions comprising a compound of the formula IA, IB, IC, I-D, II-A, II-B, II-C, II-D or a combination of and a compatible solvent. In one embodiment, additive pour point reducing fluids of pour point reducer comprising a famesan dimer Π-A or famesan dimer II-B are provided here; a compound selected from squalane, squalene, and (6E, 11E, 18E) -2,6,19,23-tetramethyl10,15-dimethylenetetracosa- 2,6,11,18,22-pentaene; and a compatible solvent.

In certain embodiments, the compounds and compositions provided herein are used in combination with one or more other additives known in the art, for example the following: detergents, particulate emission reducers, storage stabilizers, antioxidants, corrosion inhibitors, dehazers, demulsifiers , defoaming agents, catane improvers, co-solvents, packaging compatibilizers, and lubricity additives.

In certain embodiments, the additive composition of the pour point reducer comprises between 0.1 and 75%, between 1 and 65%, or between 5 and 50% of the compound of the formula IA, IB, IC, ID, II-A, II-B, II-C, II-D or a combination thereof in an oil or oil-miscible solvent. Examples of solvent are organic solvents including hydrocarbon solvents, for example, petroleum fractions, such as naphtha, kerosene, diesel oil and heater; aromatic hydrocarbons; alcohols and / or esters; and paraffinic hydrocarbons, such as hexane and pentane and isoparaffins. The solvent is selected based on its compatibility with the additive and with the oil. Examples of oils for use here include, crude oil or fuel oil. In certain embodiments, the oil is a lubricating oil, which can be an animal, vegetable or mineral oil, such as petroleum oil fractions ranging from naphtha or shaft oil to SAE 30, 40 or 50 degrees of lubricating oil, oil castor oil, fish oils, oxidized mineral oil, or biodiesel. The pour point reducing compositions provided here are used in lubricating oils as flow improvers, pour point reducers or degreasing aids.

In certain embodiments, the compounds and compositions provided herein are used as fuel additives in fuels used for, for example, internal energy combustion engines, such as alternative engines (eg gasoline engines and diesel engines), Wankel, jet engines, some rocket engines, missile engines, and gas turbine engines. The compounds and compositions provided herein can be used in combination with other fuel additives known in the art. Types of fuel additives include, but are not limited to, antioxidants, thermal stability enhancers, catane enhancers, stabilizers, cold flow enhancers, combustion enhancers, defoamers, anti-fog additives, corrosion inhibitors, lubricity enhancers, inhibitors lubricity, injector cleaning additives, smoke suppressants, resistance-reducing additives, metal deactivators, - dispersants, detergents, demulsifiers, dyes, markers, static sinks, biocides, and combinations thereof.

Preparation methods

Famesene dimers and / or famesan dimers for use in the compositions provided herein can be prepared by dimerizing β15 famesene as described in example 1. In some embodiments, βfamesene is derived from an isoprenoid starting material. In certain embodiments, the isoprenoid starting material is made by host cells converting a carbon source to the isoprenoid starting material. Exemplary methods for preparing β-famesene are described in the U.S. patent

No. 7,399,323 Bl which is incorporated herein by reference in its entirety.

In certain embodiments, compounds I-A, I-B, I-C and I-D are prepared by initiating a Diels Alder dimerization process by heating famesene at temperatures above 120 ° C. Reaction of the vinyl group of the diene with a second molecule of famesene produces compounds I-A or I-B depending on the orientation of the dienophile. Reaction of the famesene exo-methylene with the diene of a second molecule results in the formation of compounds I-C or I-D, again depending on the orientation of the dienophyte. In certain embodiments, compounds I-C and I-D appear before compounds I-A and I-B with the peak ratio in order of elution being 1.00: 1.46: 5.67: 5.02. This can vary slightly from race to race, as measured by GC / MS. GC / FID integration is slightly different in terms of GC / MS reasons. In certain modalities, the relative ratios are the same, but with slightly different magnitudes. In certain modalities, the reasons are:

1.00: 1.24: 4.51: 3.93.

In certain embodiments, methods provided herein yield compositions comprising famesene dimers of the formula I-A: I-B: IC: I-D in a 4: 4: 1: 1 ratio. In certain embodiments, methods provided herein yield compositions comprising famesan dimers of formula II-A: II-B: II-C: II-D in a 4: 4: 1: 1 ratio.

In certain embodiments, the reaction yields are quantitative except for physical losses if the crude product is filtered. In certain embodiments, the reaction is run at 150 - 240 ° C. In certain embodiments, the temperature for the reaction is between 180 - 200 ° C.

In certain embodiments, the hydrogenated dimers of the formula

II-A, II-B, II-C and II-D can be prepared by reducing the dimers of the formula

IA, IB, IC and ID in the presence of hydrogen with a catalyst, such as Pd, Pd / C, Pt, PtO ₂ , Ru (PPh ₃ ) ₂ Cl2, Raney nickel, or combinations thereof. In one embodiment, the catalyst is a Pd catalyst. In another embodiment, the catalyst is 5% Pd / C or 10% Pd / C. Alternatively, any reducing agent that can reduce a C = C bond to a CC bond can also be used. For example, hydrazine in the presence of a catalyst, such as 5-ethyl-3-methylilliflavinium percolate, in an O ₂ atmosphere can be used to give the corresponding hydrogenated products. The reduction reaction with hydrazine is described in Imada et ah, J. Am. Chem. Soc, 127, 14544-14545 (2005), which is incorporated herein by reference.

In certain embodiments, dehydroesqualene can be prepared from famesene using a suitable catalyst. Exemplary catalysts include palladium (II) acetylacetonate and triphenylphosphine, combination of [palladium (II) nitrate, sodium (2-methoxyphenoxide) or sodium phenoxide and triphenylphosphine] (see, for example, BCS Japan, v.51 (4 ), p.1156-62 (1978) and US patent No. 3,859,374) as well as the combination of [bis (cyclooctadiene) nickel and tributylphosphine] (see US patent No. 3,794,692). In certain embodiments, triphenylphosphine bound to the polymer can be used in place of soluble triphenylphosphine.

Squalane can be prepared by methods known in the art. In one embodiment, squalane can be prepared by reducing dehydroesqualene in the presence of hydrogen with a catalyst, such as Pd, Pd / C, Pt, PtO ₂ , Ru (PPh ₃ ) ₂ Cl2, Raney nickel, or combinations thereof.

The compositions described herein can be prepared by any method known to one skilled in the art for preparing lubricating oils. In some embodiments, one or more famesene dimers in the lubricating oil compositions are combined or mixed with other components, such as one or more lubricating oil additives.

In some embodiments, famesene dimers or famesan dimers are combined or mixed with squalane, squalene or dehydroesqualene to obtain a lubricating oil composition. In certain embodiments, the lubricating oil compositions are further combined or mixed with other components, such as one or more lubricating oil additives.

Exemplary lubricating oil additives are described below. Any mixing or dispersing equipment known to one skilled in the art can be used to combine, mix or solubilize the ingredients.

The following additive components are examples of some of the components that can be added to the compositions provided here.

These examples of additives are provided to illustrate the compositions, but they do not limit them.

Additions

Optionally, the composition can further comprise at least one additive or a modifier (hereinafter referred to as "additive") which can impart or improve any desirable properties of the composition. In certain embodiments, the additive is a lubricating oil additive. Any lubricating oil additive known to one skilled in the art can be used in the compositions described herein. Some suitable additives have been described in Mortier et al., “Chemistry and Technology of Lubricants“ 2nd Edition, London, Springer, (1996); and Leslie R. Rudnick, “Lubricant Additives: Chemistry and Applications“ New York, Marcel Dekker (2003), both of which are incorporated by reference. In some embodiments, the additive can be selected from the group consisting of antioxidants, anti-wear agents, detergents, rust inhibitors, demulsifiers, friction modifiers, multi-functional additives, pour point reducers, foam inhibitors, metal deactivators, dispersants, corrosion inhibitors, thermal stability improvers, dyes, markers, and combinations thereof.

In general, the concentration of each of the additives in the composition, when used, can vary from about 0.001% by weight to about 20% by weight, from about 0 ^ 01% by weight to about 10% by weight, from about 0.1% by weight to about 5% by weight or from about 0.1% by weight to about 2.5% by weight, based on the total weight of the composition. In addition, the total amount of additives in the composition can range from about 0.001% by weight to about 30% by weight, from about 0.01% by weight to about 20% by weight, from about 0.1% by weight to about 10% by weight, or from about 0.1% to about 5% by weight, based on the total weight of the composition.

Metal Detergents

In some embodiments, a composition provided herein comprises at least a neutral or metal detergent as an additive, or additive components. In certain embodiments, the metal detergent prevents the formation of deposits on the surface of an engine. In certain embodiments, the detergent has additional functions, for example, as an antioxidant. In certain respects, compositions contain metal detergents comprising both detergents and mixtures of neutral and base detergents. The term “on base” should define additives that contain a metal content in excess of that required by the stoichiometry of the particular metal and the particular organic acid used. The excess metal exists in the form of inorganic-based particles, for example, a hydroxide or carbonate, surrounded by a metal salt coating. The coating serves to keep the particles in dispersion in a liquid oil vehicle. The amount of excess metal is commonly expressed as the total metal equivalence ratio in excess of organic acid and is typically 0.1 to 30.

Some non-limiting examples of suitable metal detergents include sulfurized or non-sulfurized alkyl or alkenyl phenates, aromatic alkyl or alkenyl sulfonates, borate sulfonates, sulfurized or non-sulfurized metal salts of aromatic multi-hydroxy alkyl or alkenyl compounds, aromatic aulfonates of alkyl or alkenyl hydroxy, sulfurized or non-sulfurized alkyl or alkenyl naphthenates, metal salts of alkanoic acids, metal salts of an alkyl or alkenyl mulliacid and chemical and physical mixtures thereof.

Other non-limiting examples of suitable metal detergents include metal sulfonates, phenatis, salicylates, phosphonates, thiophosphonates and combinations thereof. The metal can be any metal suitable for preparing sulfonate, phenate, salicylate or phosphonate detergents. Non-limiting examples of suitable metals include alkali metals, alkali metals and transition metals. In some embodiments, the metal is Ca, Mg, Ba, K, Na, Li or similar. An exemplary metal detergent that can be used in the compositions includes calcium phenate.

In general, the amount of the additive metal detergent can be less than 10,000 ppm, less than 1000 ppm, less than 100 ppm, or less than 10 ppm, based on the total weight of the composition. In some embodiments, the amount of the metal detergent is from about 0.001% by weight to about 5% by weight, from about 0.05% by weight to about 3% by weight, or from about 0.1 % by weight to about 1% by weight, based on the total weight of the composition. Some suitable detergents have been described in Mortier et ah, “Chemistry and Technology of Lubricants,” 2nd edition, London, Springer, Chapter 3, pages 75-85 (1996); and Leslie R. Rudnick, “Lubricant Additives: Chemistry and Applications“ New York, Marcei Dekker, Chapter 4, pages 113-136 (2003), both of which are incorporated herein by reference.

Solubilizing agents

Solubilizing agents can be used in the compositions provided herein to increase the solubility of various components in the composition. Suitable solubilizing agents include, but are not limited to, oil-soluble esters and diesters, alkylated naphthalenes, alkylated sulfones, naphthenic base oils, aromatic base oils and alkylated benzenes. Other solubilizing agents known in the art are also contemplated herein. Esters and diesters that can be used as solubilizing agents include, for example, adipate esters and polyol esters. Exemplary diesters include adipates, azelates, and sebacates of C ₈ -C ₃ alkanols (or mixtures thereof), C ₄ -C 13 alkan phthalates (or mixtures thereof). Mixtures of two or more different types of diesters (for example, dialkyl adipates and dialkyl azelates, etc.) can also be used. Examples of such materials include n-octyl, 2-ethylexyl, isodecyl, and tridecyl diesters of adipic acid, azelaic acid, and sebacic acid, and n-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and tridecyl diesters of phthalic acid.

Anti-wear and / or extreme pressure agents

In certain embodiments, compositions described herein may further comprise anti-wear or extreme pressure agents. Wear occurs on all equipment that has moving parts in contact. Specifically, three conditions commonly lead to engine wear:

(1) surface-to-surface contact; (2) surface contact with foreign matter; and (3) erosion due to corrosion of materials. Wear resulting from surface-to-surface contact is fi ction or adhesive wear, contact with foreign matter is abrasive wear, and contact with corrosive materials is corrosive wear. Fatigue wear is an additional type of wear that is common in equipment where surfaces are not only in contact, but also experience repeated stresses for prolonged periods. Abrasive wear can be avoided by installing an efficient filtration mechanism to remove harmful debris. Corrosive wear can be addressed using additives that neutralize reactive species that can, in some way, attack metal surfaces. The control of adhesive wear requires the use of additives called anti-wear agents and extreme pressure (EP).

Under ideal conditions of speed and load, the metallic surfaces of the equipment must be effectively separated by a lubricating film. Increasing the load, decreasing the speed or otherwise deviating from such ideal conditions promotes metal-to-metal contact. This contact typically causes a temperature to rise in the contact zone due to the frictional heat which, in turn, leads to loss of lubricating viscosity and thus its ability to form a film. In certain embodiments, anti-wear additives and EP agents offer protection by a similar mechanism. In certain embodiments, EP additives require higher activation and loading temperatures than anti-wear additives.

Without being tied to any particular theory, it is believed that anti-wear and / or EP additives work by thermal decomposition and forming products that react with the metallic surface to form a solid protective layer. This solid metallic film fills the roughness of the surface and facilitates the formation of effective film, thus reducing friction and preventing welding and surface wear.

Most anti-wear and extreme pressure agents contain sulfur, chlorine, phosphorus, boron, or combinations thereof. Classes of compounds that inhibit adhesive wear include, for example, alkyl and aryl disulfites and polysulfites; dithiocarbamates; chlorinated hydrocarbons; and phosphorus compounds, such as phosphites, phosphates, dithiophosphates, and alkyl alkenylphosphonates.

Exemplary anti-wear agents that may be included in the compositions provided herein include metal salts (for example, Pb, Sb, and the like) of dithiophosphate, metal salts (for example, Pb, Sb, and the like) of dithiocarbamate, metal salts ( for example, Pb, Sb and the like) of fatty acids, boron compounds, phosphate esters, phosphite esters, amine salts of phosphoric acid esters or thiophosphoric acid esters, dicyclopentadiene and thiophosphoric acid reaction products and combinations of themselves. The amount of the anti-wear agent can vary from about 0.01% by weight to about 5% by weight, from about 0.05% by weight to about 3% by weight, or from about 0.1% by weight weight at about 1% by weight, based on the total weight of the composition. Some suitable anti-wear agents have been described in Leslie R. Rudnick, “Lubricant Additives: Chemistry and

Applications “New York, Marcei Dekker, Chapter 8, pages 223-258 (2003), which is incorporated by reference here.

In one embodiment, the sulfated ash content of the total composition is less than 5% by weight, less than 4% by weight, less than 3% by weight, less than 2% by weight, or less than 1% by weight, depending on measured according to ASTM D874.

In one embodiment, EP agents for use in the compositions provided herein include alkyl and aryl disulfites and polysulfites, dithiocarbamates, chlorinated hydrocarbons, dialkyl hydrogen phosphites and salts of alkyl phosphoric acids. Methods of preparing these EP agents are known in the art. For example, polysulfites are synthesized from olefins either by reacting with sulfur or sulfur halides, followed by dehydrogenation. Dialkyldithiocarbamates are prepared both by neutralizing dithiocarbamic acid (which can be prepared by reacting a dialkylamine and carbon disulfite at low temperature) with bases, such as antimony oxide, and by their addition to activated olefins, such as alkyl acrylates.

In certain embodiments, compositions provided herein comprise one or more EP agents. In one embodiment, the use of more than one EP agent leads to synergism. For example, synergism can be observed between sulfur and chlorine-containing EP agents. An exemplary composition provided herein includes one or more EP agents selected from: zinc dialkyldithiophosphate (primary alkyl type & secondary alkyl type), sulfurized oils, diphenyl sulfite, methyl trichlorostearate, chlorinated naphthalene, fluoralkylpolysiloxane, and lead naphthenate.

Rust inhibitors (Anti-rust agents)

Rust protection is an important consideration when formulating lubricants. Without protection, rust finally causes a loss of metal, thus decreasing the integrity of the equipment, and resulting in engine malformation. Furthermore, corrosion exposes fresh metal that can wear out at an accelerated rate, perpetuated by the metal ions that must be released into the fluid and act as oxidation promoters.

The composition described herein optionally can comprise rust inhibitor which can inhibit corrosion of metal surfaces. Any rust inhibitor known to a person skilled in the art can be used in the composition. Rust inhibitors attack metal surfaces themselves to form an impenetrable protective film, which can be physically or chemically adsorbed on the surface. Specifically, film formation occurs when additives interact with the metal surface through its polar ends and associate with the lubricant through its non-polar ends. Suitable rust inhibitors may include, for example, various non-ionic polyoxyethylene surface active agents, such as polyoxyethylene lauryl ether, polyoxyethylene upper alcohol ether, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl, polyoxyethylene octyl stearyl ether, oleo polyoxyethylene ether, polyoxyethylene sorbitol monostearate, polyoxyethylene sorbitol mono-oleate, and polyethylene glycol mono-oleate. Suitable rust inhibitors may also include other compounds, such as, for example, monocarboxylic acids (e.g., 2-ethylexanoic acid, lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, behenic acid, cerotic acid and the like), oil-soluble polycarboxylic acids (for example, those produced from wax oil fatty acids, oleic acid, linoleic acid and the like), alkenyl succinic acid in which the alkenyl group contains 10 or more carbon atoms (for example example, tetrapropenyl succinic acid, tetradecenyl succinic acid, hexadecenyl succinic acid, and the like); alpha, long chain omega dicarboxylic acids having a molecular weight in the range of 600 to 3000 daltons and combinations thereof. Additional examples of rust agents include metal soaps, fatty acid amine salts, heavy sulfonic acid metal salts, polyhydric alcohol partial carboxylic acid ester and phosphoric ester.

Demulsifiers

The composition described herein optionally can comprise a demulsifier that can promote oil-water separation in the compositions that are exposed to water or steam. Any demulsifier known to a person skilled in the art can be used in the composition. Non-limiting examples of suitable demulsifiers include anionic surfactants (eg, alkyl naphthalene sulfonates, alkyl benzene sulfonates and the like), non-ionic alkoxylated alkylphenol resins, alkylene oxide polymers (eg polyethylene oxide, polypropylene oxide, block copolymers of ethylene oxide, propylene oxide and the like), esters of oil-soluble acids, polyoxyethylene sorbitan ester and combinations thereof. In certain embodiments, demulsifiers for use herein include block copolymers of propylene oxide or ethylene oxide and initiators, such as, for example, glycerol, phenol, formaldehyde resins, soloxanes, polyamines, and polyols. In certain embodiments, the polymers contain about 20 to about 50% ethylene oxide. These materials concentrate at the water-oil interface and create areas of low viscosity, thus promoting droplet coalescence and gravity-driven phase separation. Low molecular weight materials, such as, for example, alkali metal or alkaline earth metal salts of dialkylnaphthalene sulfonic acids are also used in certain applications. The amount of the demulsifier can vary from about 0.01% by weight to about 10% by weight, from about 0.05% by weight to about 5% by weight, or from about 0.1% by weight to about 3% by weight, based on the total weight of the composition. Some suitable demulsifiers have been described in Mortier et ah, “Chemistry and Technology of Lubricants,” 2nd Edition,

London, Springer, Chapter 6, pages 190-193 (1996), which is hereby incorporated by reference.

Friction modifiers

The composition described herein optionally can comprise a friction modifier which can decrease the friction between moving parts. Any friction modifier known to one skilled in the art can be used in the composition. They are typically long-chain molecules with a polar end group and a straight non-polar hydrocarbon chain. The polar end groups both physically adsorb on the metal surface and chemically react with it, while the hydrocarbon chain extends into the lubricant. The chains associated with each other and the lubricant to form a strong lubricating film.

Non-limiting examples of suitable friction modifiers include fatty carboxylic acids; derivatives (for example, alcohol, esters, boron esters, amides, metal salts and the like) from fatty carboxylic acid; phosphoric acids or substituted mono-, di- or trialkyl phosphonic acids; derivatives (for example, esters, amides, metal salts and the like) of phosphoric acids or substituted mono-, di- or tri-alkyl phosphonic acids; mono-, di- or tri-alkyl substituted amines; substituted mono- or di-alkyl amides and combinations thereof.

In one embodiment, the friction modifier is a saturated fatty acid containing a chain of 13 to 18 carbons. The amount of the friction modifier can vary from about 0.01% by weight to about 10% by weight, from about 0.05% by weight to about 5% by weight, or from about 0.1% by weight to about 3% by weight, based on the total weight of the composition. Some suitable friction modifiers have been described in Mortier et ah, “Chemistry and Technology of Lubricants,” 2nd edition, London, Springer, Chapter 6, pages 183-187 (1996); and Leslie R. Rudnick, “Lubricant Additives: Chemistry and Applications“ New York, Marcei

Dekker, Chapters 6 and 7, pages 171-222 (2003), both of which are incorporated herein by reference.

Sealing swelling agents

Seal swelling agents can be included in the finished compositions of the modalities particularly described when compositions provided herein are used as energy transmission fluids. Suitable seal swelling agents can be selected from oil-soluble diesters, oil-soluble sulfones, silicon-containing organic compounds, and mixtures thereof. In general, most suitable diesters include Cg-C ₁₃ alkanol adipates, azelates, and sebacates (or mixtures thereof), and C4 -C13 alkanol phthalates (or mixtures thereof). Mixtures of two or more different types of diesters (for example, dialkyl adipates and dialkyl azelates, etc.) can also be used. Examples of such materials include n-octyl, 2-ethylexyl, isodecyl, and tridecyl diesters of adipic acid, azelaic acid, and sebacic acid, and n-butyl, isobutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and tridecyl diesters of phthalic acid. Other esters that can give generally equivalent performance are polyol esters.

In one embodiment, the seal swelling agents are the oil-soluble dialkyl esters of (i) adipic acid, (ii) sebacic acid, or (iii) phthalic acid.

Pour point reducers

The composition described herein can optionally comprise a pour point reducer which can decrease the pour point of the composition. Any pour point reducer known to a person skilled in the art can be used in the composition. In certain embodiments, pour point reducers have one or more structural features selected from: (1) polymeric structure; (2) waxy and non-waxy components; (3) comb structure comprising a short backbone with long hanging groups; and (4) wide molecular weight distribution. Non-limiting examples of suitable pour point reducers include polymethacrylates, alkyl acrylate polymers, alkyl methacrylate polymers, alkyl fumarate polymers, di (tetra-paraffin phenol) phthalate, tetra-paraffin phenol condensates, condensates of a phenol paraffin chlorinated with naphthalene, alkylated naphthalenes, styrene esters, oligomerized alkyl phenols, phthalic acid esters, ethylene-vinyl acetate copolymers and combinations thereof. In one embodiment, the pour point reducer is selected from tetra (long chain) alkyl silicates, phenyltristearyloxysilane, and pentaerythritol tetra stearate. In some embodiments, the pour point reducer comprises an ethylene-vinyl acetate copolymer, a condensate of chlorinated paraffin and phenol, polyalkyl styrene or the like. The amount of the pour point reducer can vary from about 0.01% by weight to about 10% by weight, from about 0.05% by weight to about 5% by weight, or from about 0, 1% by weight to about 3% by weight, based on the total weight of the composition. Some suitable pour point reducers have been described in Mortier et ah, “Chemistry and Technology of Lubricants,” 2nd edition, London, Springer, Chapter 6, pages 187-189 (1996); and Leslie R. Rudnick, 'Lubricant Additives: Chemistry and Applications;' New York, Marcei Dekker, Chapter 11, pages 329-354 (2003), both of which are incorporated herein by reference.

Foam inhibitors

The composition described herein optionally can comprise a foam inhibitor or a defoamer that can break foams in oils. Any foam inhibitor or defoamer known to one skilled in the art can be used in the composition. Non-limiting examples of suitable defoamers include silicone oils or polydimethylsiloxanes, fluorsilicones, alkoxylated aliphatic acids, polyethers (eg, polyethylene glycols), branched polyvinyl ethers, alkyl acrylate polymers, alkyl methacrylate polymers, polyalkoxymines and combinations of the same alkoxymines. . In some embodiments, the defoamer comprises glycerol monostearate, polyglycol palmitate, a trialkyl monothiophosphate, a sulfonated ricinoleic acid ester, benzoyl acetone, methyl salicylate, glycerol mono-oleate, or glycerol dioleate. The amount of the defoamer can vary from about 0.01% by weight to about 5% by weight, from about 0.05% by weight to about 3% by weight, or from about 0.1% by weight to about 1% by weight, based on the total weight of the composition. Some suitable defoamers have been described in Mortier et ah, “Chemistry and Technology of Lubricants,” 2nd edition, London, Springer, Chapter 6, pages 190-193 (1996), which is incorporated herein by reference.

Metal deactivators

In some embodiments, the composition comprises at least one metal deactivator. Some non-limiting examples of suitable metal deactivators include disalicylidene propylene diamine, triazole derivatives, thiadiazole derivatives, and mercaptobenzimidazoles. Dispersants

The composition described herein can optionally comprise a dispersant that can prevent sludge, varnish, and other deposits by keeping the suspended particles in a colloidal state. In certain modalities, dispersants perform these functions through one or more selected ways of: (1) solubilizing polar contaminants in their micelles;

(2) stabilization of colloidal dispersions in order to prevent aggregation of its particles and their separation from oil; (3) suspension of such products, if they form, in the lubricant; (4) rust modification to minimize its aggregation and oil thickening; and (5) decreased surface / interfacial energy from undesirable materials to decrease their tendency to adhere to surfaces. Undesirable materials are typically formed as a result of oxidative degradation of the lubricant, the reaction of chemically reactive species, such as carboxylic acids with metal surfaces in the engine, or the decomposition of thermally unstable lubricant additives, such as, for example, extreme pressure.

In some respects, a dispersing molecule comprises three distinct structural characteristics: (1) a hydrocarbyl group; (2) a polar group; and (3) a connection group or a bond. In certain embodiments, the hydrocarbyl group is polymeric in nature and has a molecular weight of about 2000 Daltons or above, in one embodiment, about 3000 Daltons or above, in another embodiment, in about 5000 Daltons or above of this, and in yet another modality, at about 8000 Daltons or above. A variety of olefins, such as polyisobutylene, polypropylene, polyalphaolefins, and mixtures thereof, can be used to prepare suitable polymeric dispersants. In certain embodiments, the polymeric dispersant is a dispersant derived from polyisobutylene. Typically the average molecular weight of polyisobutylene in dispersants ranges from about 500 to about 3000 Daltons, or, in some embodiments, from about 800 to about 2000 Daltons, or in additional embodiments, from about 1000 to about 2000 Daltons . In certain embodiments, the polar group in the dispersant is derived from nitrogen or oxygen. Nitrogen-based dispersants are typically derived from amines. The amines from which nitrogen-based dispersants are derived are often polyalkylene polyamines, such as, for example, diethylene triamine and trethylene tetramine. Amine-derived dispersants are also called nitrogen or amine dispersants, while alcohol derivatives are also called oxygen or ester dispersants. Oxygen-based dispersants are typically neutral, while amine-based dispersants are typically basic.

Non-limiting examples of suitable dispersants include alkenyl succinimides, alkenyl succinimides modified with other organic compounds, alkenyl succinimides modified by post-treatment with ethylene carbonate or boric acid, succinamides, succinate esters, succinate amides ester, pentaerythritols, phenate-salicylates and its post-treated analogues, alkali metal or mixed alkali metal borates, alkaline earth metal, hydrated alkali metal borate dispersions, alkaline earth metal borate dispersions, polyamide ash dispersants, benzylamines, Mannich-type dispersants, dispersants containing phosphorus and combinations thereof. The amount of the dispersant can vary from about 0.01% by weight to about 10% by weight, from about 0.05% by weight to about 7% by weight, or from about 0.1% by weight to about 4% by weight, based on the total weight of the composition. Some suitable dispersants have been described in Mortier et al., “Chemistry and Technology of Lubricants“ 2nd edition, London, Springer, Chapter 3, pages 86-90 (1996); and Leslie R. Rudnick, “Lubricant Additives: Chemistry and Applications“ New York, Marcei Dekker, Chapter 5, pages 137- 170 (2003), both of which are incorporated herein by reference.

Antioxidants

Optionally, the composition described herein can further comprise an additional antioxidant which can reduce or prevent oxidation of the base oil. Any antioxidant known to one skilled in the art can be used in the composition. Examples of antioxidants used in the compositions provided herein include, but are not limited to, phenol-like oxidation inhibitors (phenolics), such as 4.4 'methylene bis (2.6 di tertbutylphenol), 4.4' bis (2.6 di tert -butylphenol), 4.4 'bis (2 methyl 6 tert-butylphenol),

2,2 'methylene bis (4-methyl 6 tert-butylphenol), 4.4' butylidene bis (3 methyl 6 tert-butylphenol), 4.4 'isopropylidene bis (2.6 di tert-butylphenol), 2.2' methylene bis (4methyl 6 nonylphenol), 2,2 'isobutylidene bis (4,6 dimethylphenol), 2,2' 5 methylene bis (4 methyl 6 cyclohexylphenol), 2,6 di tert-butyl 4-methylphenol, 2,6 di tert - butyl 4 ethylphenol, 2,4 dimethyl 6 tert-butylphenol, 2,6 di tert-1 dimethylamino p cresol, 2,6 di tert- 4 (N ₅ N - dimethylaminomethylphenol), 4.4 'thiobis (2 methyl 6 tert -butylphenol), 2,2'-thiobis (4 methyl 6 tert-butylphenol), bis (3 methyl 4 hydroxy 5 tert-10 butylbenzyl) sulfite, and bis (3,5 di tert-butyl 4 hydroxybenzyl). Diphenylamine-type oxidation inhibitors include, but are not limited to, alkylated diphenylamine, phenyl alpha naphthylamine, and alkylated alpha naphthylamine, sulfur-based antioxidants (e.g., dilauryl-3,3'-thiodipropionate, sulfuric phenolic antioxidants and the like), antioxidants a phosphorus-based (eg phosphites and the like), zinc dithiophosphate, oil-soluble copper compounds and combinations thereof. Other types of oxidation inhibitors include metal dithiocarbamate (eg, zinc dithiocarbamate), and 15 methylenebis (dibutyldithiocarbamate). The amount of the antioxidant can vary from about 0.01% by weight to about 10% by weight, from about

0.05% by weight to about 5% by weight, or from about 0.1% by weight to about 3% by weight, based on the total weight of the composition. Some suitable antioxidants have been described in Leslie R. Rudnick, “Lubricant Additives: Chemistry and Applications,” New York, Marcel Dekker, Chapter 1, pages 1-28 (2003), which is incorporated herein by reference.

Multifunctional additives

Various additives mentioned or not mentioned here can provide a multitude of effects to the lubricating oil composition provided herein. Thus, for example, a single additive can act as a dispersant as well as an oxidative inhibitor. Multi-functional additives are well known in the technology. Other suitable multi-functional additives may include, for example, sulfurized oxy-olybdenum dithiocarbamate, sulfurized oxy-molybdenum organo phosphorus, oxy-olybdenum monoglyceride, amine-molybdenum complex compound, and sulfur-containing molybdenum complex compounds.

Agents that improve the viscosity index

In certain embodiments, the composition comprises at least one agent that improves the viscosity index. Some non-limiting examples of agents that improve the viscosity index include polymethacrylate-type polymers, ethylene-propylene copolymers, styrene-isoprene copolymers, hydrated styrene-isoprene copolymers, polyisobutylene, and agents that improve the dispersant-type viscosity index.

Conductivity Enhancers

In certain embodiments, the composition comprises at least one conductivity enhancer. Some non-limiting examples of suitable conductivity enhancers include hydrogenated lecithin and related compounds; magnesium palmitate or aluminum palmitate or stearate; diexyl phosphoric acid esters neutralized with tetramethylnonylamines or Cn-C ₄ alkylamines; mono- and diglyceride demono15 sodium phosphate derivatives composed of glyceride derivatives formed by reacting mono- and diglycerides which are derived from edible sources with phosphorus pentoxide (tetraphosphorus decoxide) followed by neutralization with sodium carbonate; phosphate derivatives of mono- and diglycerides produced in the manner described above and governed with ethanolamine and neutralized with fatty acid and sodium dodecyl sulfonate. Load carrying additives

In certain embodiments, the composition comprises one or more filler loading additives to reduce friction during processing that is functional with metal. Exemplary filler additives include, but are not limited to, fatty alcohols, dicarboxylic acids or fatty acids and esters thereof, for example, fatty acid esters, butyl stearate, butyl palmitate, tridecyl azelate and / or dioctyl sebacate.

Uses of compositions

The compositions provided here are used in a wide variety of industrial applications associated with the automotive, tractor, overhead and highway industries for use in engine oils, transmission fluids, hydraulic fluids, gear oils, absorbent motor steering energy / shock; metal-working industry for use in laminating machines or cutting metal sheets and water coolers; process oils for use in rubber and plastic processing; marine oils for use in propulsion engines; finishing fluids; greases; crankcase lubricants; vehicle axle applications; and turning machinery, such as stationary engines, pumps, gas turbines, compressors, wind turbines, and the like. Stationary engines include fuel and gas engines that are not associated with the automotive, tractor, overhead and highway industries. Exemplary automotive applications include, but are not limited to, use in engine oils, for example, internal combustion engines, natural gas engines, turbine engines, automatic and manual transmissions and marine diesel engines. In certain embodiments, compositions provided herein are used as industrial oils, such as in hydraulic oils, fire-resistant oils, industrial gear oils, highway diesel and natural gas. Furthermore, products based on the modalities described here can be used in planetary wheel axle reduction shafts, mechanical directions and transfer gearboxes in utility vehicles, such as trucks, synchronizing gearboxes, as well as gear gears. power withdrawal, limited sliding axles and planetary wheel axle reduction gearboxes.

In one embodiment, compositions provided here are used as engine lubricants. In one embodiment, a method of lubricating an engine is provided herein comprising operating the engine in contact with a composition provided herein.

In certain embodiments, a method of lubricating a machine is provided here by operating the machine in contact with a composition provided herein. The compositions can be used to lubricate any machine that needs lubrication. Exemplary machines include, but are not limited to, engines, pumps, gas turbines, compressors, wind turbines, and the like. In certain modalities, the engine is a fuel and / or gas engine associated with the automotive, tractor, overhead and highway industries. In certain embodiments, the engine is a stationary engine, including a fuel and / or gas engine that is not associated with the automotive, tractor, overhead and highway industries. In certain embodiments, a machine comprising a composition provided herein is provided here.

In one embodiment, a composition is provided here with an automatic transmission fluid (ATF). An exemplary ATF composition contains one or more famesene dimers and / or famesan dimers provided herein, a solubilizing agent, from about 0.5 to about 1.5% by weight of agent that improves the viscosity index, from about from 1.5 to about 2.5% by weight of ash dispersant, from about 0.05 to about 1% by weight of friction modifier, from about 0.01 to about 0.5% by weight of corrosion inhibitor, from about 0.1 to about 0.4% by weight of anti-wear additive, from about 0.005 to about 5% by weight of metal deactivator, from about 0.1 to about 15% by weight of metallic detergent, from about 0.25 to about 1% by weight of seal swelling agent, from about 0.01 to about 0.5% by weight of pour point reducer and optionally a base oil component.

In one embodiment, the finished composition is a manual transmission oil. An exemplary manual transmission oil lubricant formulation contains one or more famesene dimers and / or famesan dimers provided herein, a solubilizing agent, an agent that improves the viscosity index, an ash dispersant, at least one antioxidant, at least an inhibitor and optionally a base oil component.

In another embodiment of the description, the finished composition is a shaft lubricating oil. An exemplary shaft lubricating oil formulation contains a solubilizing agent, an agent that improves the viscosity index, an extreme pressure agent containing sulfur, at least one anti-wear agent containing phosphorus, at least one ash dispersant, at least one inhibitor and optionally a base oil component.

In one embodiment, compositions provided herein are used as a crankcase lubricant and may include a solubilizing agent, an agent that improves the viscosity index, a detergent, a dispersant, an anti-wear agent, a friction modifier, an antioxidant, an inhibitor of corrosion, a pour point reducer, a defoaming agent and optionally a base oil component.

The compositions described herein can also be used in finishing fluid applications to provide a slower cooling rate for hardening metals, such as steel. Finishing fluid performance can be modified by introducing one or more of the foregoing additives and / or compositions to improve wettability, cooling rate, oil stability and to reduce deposit formation trends in the finishing fluids.

Although the compounds, compositions and methods have been described with respect to a limited number of modalities, the specific characteristics of one modality should not be attributed to other modalities described herein. No single modality is representative of all aspects of the compositions or methods. In some embodiments, the compositions or methods may include numerous compounds or steps not mentioned here. In other embodiments, the compositions or methods do not include, or are substantially free, any compound or step not listed here. There are variations and modifications of the described modalities.

All publications and patent applications mentioned in this specification are hereby incorporated by reference as if each individual publication or patent application was specifically and individually indicated as incorporated by the reference. Although the foregoing has been described in some detail by way of illustration and example for the sake of clarity of understanding, it will be readily apparent to those skilled in the technology in light of the teachings here that certain changes and modifications can be made without departing from the spirit and scope of the attached claims.

EXAMPLES

The practice in question may employ, unless otherwise indicated, conventional techniques in the industry and the like known to those skilled in the technology. To the extent that such techniques are not fully described here, a broad reference to them can be found in the scientific literature.

In the following examples efforts have been made to ensure accuracy with respect to the numbers used (for example, quantities, temperature, and so on), but variation and deviation can be accommodated, and in the event of a clerical error in the numbers reported here, a verse in technologies you can deduct the correct amount in view of the description here remaining. Unless otherwise indicated, temperature is reported in degrees Celsius. All reagents, unless otherwise indicated, were obtained commercially, β-famesene used herein is prepared in the manner described in U.S. Patent No. 7,399,323 BI which is incorporated herein by the reference in its entirety. The following examples are for illustrative purposes only and do not limit the scope of the present invention in any way.

Example 1

This example describes a method for preparing famesene dimers from β-famesene.

To a 500 ml three-neck round base flask, previously rinsed with conc. and dry, equipped with a magnetic stirrer, heating blanket, thermometer, reflux condenser and nitrogen input, 204 g (1.00 mol) of βfamesene (Bedoukian, 98%) were added. The famesene was stirred and heated to 220 ° C, while monitoring the progress of the reaction by GC / MS. After two hours the colorless reaction mixture consisted almost entirely of two pairs of dimers, IA: IC in a ratio of 4: 1 and IB: ID in a ratio of 4: 1 with <2% of remaining starting material. The mixture naturally cooled to approximately 50 ° C and vacuum filtered through a 0.5 cm thick layer of Celite in a 60 ml medium porosity sintered glass funnel to provide 200 g (98.3%) of oil colorless clear. The compositions comprise compounds IA, IC, IB, and ID which has been confirmed by Ή NMR and ¹³ C.

Famesene dimers: ³ H (400 MHz, CDC1 ₃ ) d (multiplicity, coupling constant {s}, integration *), 5.71 (dd, J = 5.6 and 10.8 Hz, 0.04H), 5.65 (dd, J = 5.6 and 10.8 Hz, 0.04H), 5.37 (m, 0.60H), 5.12 (m, 3.04H), 5.01 (dt, J = 1.6 and 10.8 Hz, 0.10H), 4.89 (ddd, J = 1.6, 12.0 and 17.6 Hz, 0.06H), 4.74 (m, l, 00H), 2.09 (m, 9.28H), 1.98 (m, 5.30H), 1.68 (s, 4.24H), 1.60 (s, 7.97H) ppm.

Famesene dimers: ¹³ C (100 MHz, CDC1 ₃ ) d 154.36,

154.26, 146.14, 145.44, 145.25, 139.55, 139.04, 137.46, 137.39, 136.94,

135.87, 135.38, 135.11, 135.07, 134.94, 134.82, 134.59, 131.225, 125.01,

124.97, 124.44, 124.34, 124.23, 124.06, 122.71, 120.47, 120.37, 120.17,

119.16, 1 15.71, 1 13.02, 112.11, 1 12.01, 107.24, 107.18, 40.39, 40.25,

40.17, 40.13, 40.00, 39.74, 38.72, 38.16, 38.04, 37.87, 37.61, 34.89, 34.63,

34.55, 32.27, 31.76, 31.47, 29.10, 28.41, 28.03, 27.25, 26.77, 26.65, 26.43,

26.41, 26.34, 25.88, 25.82, 25.69, 22.73, 22.46, 22.41, 17.68, 16.05, 16.02,

15.93 ppm.

* Integration values are peak-to-peak relative areas and not absolute numbers of protons.

Example 2

This example describes a method for preparing famesan dimers from famesene dimers.

A mixture of famesene dimers (100 g, 0.245 mol) was placed in a 1 L glass Hastaloy Parr hydrogenation vessel containing 0.75 g of 5% Pd / C. Hexane (300 mL) was added and the reactor assembled. The mixture was placed under vacuum for one hour. The agitator was started (400 rpm) and the reactor was pressurized to 4.13MPa man with hydrogen. The mixture was heated to 72 ° C and the pressure naturally dropped to 2MPa man in which hydrogen was added to bring the pressure back to 4.13MPa man. This process was repeated until the consumption of hydrogen ceased. The reactor cooled naturally at 30 ° C and the contents were filtered to remove the catalyst. The removal of the solvent under reduced pressure provided 100 g (96.9%) of famesan dimers consisting of 15 isomeric compounds of molecular weight 420 (GC / MS). Celite in a sintered glass funnel of medium porosity of 60 mL to provide 200 g (98.3%) of clear colorless oil. The presence of compounds II-A, II-C,

II-B, and II-D was confirmed by Ή NMR.

Ή (400 MHz, CDCI3) d (multiplicity, coupling constant}, integration *) 1.79 - 1.55 (m, 4.08H), 1.52 (m, J = 6.8 Hz, 4.94H ), 1.59 - 1.00 (m, 53.95H), 1.05, 0.87, 0.86, 0.85, 0.85, 0.83, 0.83, 0.82, 0 , 81, 0.80, 0.79 (s, 36.01 total H).

Dimer 1,4-famesano (90% pure): H (400 MHz, CDC1 ₃ ) d (multiplicity, coupling constant}, integration *) 5.42 (m, IH), 5.12 (m, 4H), 4.75 (m, 2H), 2.10 (m, 15H), 1.98 (m, 8H), 1.682 (s, 3H), 1.680 (s, 3H), 1.60 (s, 12H) ppm.

* Integration values are peak-to-peak relative areas and not absolute numbers of protons.

Example 3

Preparation of dehydroesqualene from famesene:

Famesene (331.94 g, 1.627 mmol) was stirred in 1025 mL of

2-propanol and triphenylphosphine (9.55g, 36.4 mmol) was added after palladium (II) acetylacetonate (3.9 g, 13.0 mmol). The mixture was heated to 85 ° C for 7 hours and then cooled naturally to 25 ° C. After stirring for 17 hours, most of the 2-propanol was removed by rotary evaporation and the black residue was suspended in a liter of 5% ethyl acetate in hexanes.

The suspension was filtered through a 23 meter diameter x 23 meter high silica gel pad and the silica gel was washed with 500 ml of 5% ethyl acetate in hexanes. The combined organic solutions were concentrated by rotary evaporation to give 328.3 g of light yellow oil.

Alternative catalysts for this reaction include the combination of [palladium (II) nitrate, sodium (2-methoxyphenoxide) or sodium phenoxide and triphenylphosphine] (see, for example, BCS Japan, v.51 (4), p. 1156 -62 (1978) and US patent No. 3,859,374) as well as the combination of [bis (cyclooctadiene) nickel and tributylphosphine] (US patent No. 3,794,692). In certain embodiments, triphenylphosphine bound to the polymer can be used in place of soluble triphenylphosphine. Other catalysts that have been tried but failed to convert (<5%) include 5% Pd / C, 5%

Pd / alumina, 5% Ru / C, palladium acetate, copper (II) acetylacetonate, cobalt (II) acetylacetonate, nickel (II) acetylacetonate, palladium (II) acetylacetonate (without any phosphine binder), palladium chloride + triphenylphosphine and palladium (O) dibenzylidene acetone + triphenylphosphine.

Example 4

Preparation of squalane from dehydroesqualene

Dehydroesqualene prepared previously was placed in a 1 liter Parr pressure reactor and 1.1 g of 5% Pd / C was added. The vessel was sealed and evacuated in a vacuum for twenty minutes (ca. 2.6kPa) and then pressurized with hydrogen gas to 6.5MPa man. The reaction is initially exothermic. After the initial exothermic stage of the reaction was completed, the reaction temperature was maintained at 40 ° C by external heating and then at 60 ° C. Hydrogen gas was added as needed to maintain the rate of reaction. After 47 hours the reaction was judged complete by GCMS analysis then the crude reaction product was filtered through a 23 meter diameter x 23 meter high silica gel pad and the silica gel was washed with 550 mL of 5% ethyl acetate in hexanes. After removing the solvent by rotary evaporation the crude squalane weighed 332.6 g. The product was distilled in 3 batches using a bulb to bulb Kugelrohr apparatus to give 282.4 g squalane (83.4% yield in both steps).

Example 5

This example provides lubricating properties for the famasan dimers prepared according to example 2 and squalane prepared according to example 4.

Table 2

ASTM method skeletal Dimer thermal heat Viscosity at 40 ° C, cst D445 19.23 35.44 Viscosity at 100 ° C, cst D445 4.14 5.71 Kinematic viscosity, cst, 40 ° C D445 6109.19 39410.14 viscosity index D2270 118-132 100 Pour point ° C D97 <-60C -57 Flash point, COC, ° C D92 232 234

NOACK evaporative loss,% by weight D5800 13.2 9.1 Acid number (mgKOH / g) D974 0.056 1.25

Depending on the reaction conditions for preparing the famesene / famesan dimers (according to examples 1 and 2), some amounts of higher oligomers may also be present in the final compositions. The famesan dimers tested in this example were distilled to remove any higher oligomers that may be present.

Furthermore, thermal famesene dimers have a viscosity at 40 ° C of 17 cSt and a viscosity at 100 ° C of 5.03 cSt. The viscosity index of the thermal famesene dimers was 255.

Example 6

This example provides lubricating properties for various mixtures of famasan dimers (II-A, II-B, II-C and II-D) and squalane. This example provides lubricating properties for the famasan dimers prepared according to example 2 and squalane prepared according to example 4. The famesan dimers tested in this example were distilled to remove any oligomers that may be present.

Table 3

% of famasano dimers %in squalene D40 θιοο cP40 cSt40 cPioo cStioo SAW 0 100 0.800 0.764 14.9 18.6 3.20 4.18 132 20 80 0.801 0.763 17.2 21.6 3.48 4.54 127 20 80 0.801 0.763 17.4 21.8 3.48 4.54 125 40 60 0.797 0.767 19.3 24.1 4.56 5.76 115 80 20 0.831 0.763 25.4 30.6 4.23 5.54 119 100 0 0.825 0.792 30.1 36.5 3.60 5.71 103

dx is the density at temperature x.

cPx is the dynamic (absolute) viscosity at temperature x (in centipoises).

cStx is the kinetic viscosity at temperature x (in centistokes).

In certain embodiments, a composition provided herein may comprise combinations of famasan dimers (II-A, II-B, II-C and II-D) and squalene as described in table 4:

Table 4

% of famesan dimers % squalene 0 100 20 80 20 80 40 60 80 20 100

In certain embodiments, a composition provided herein may comprise combinations of famasan dimers (II-A, II-B, II-C and II-D) and dehydroesqualene as described in table 5:

Table 5

% of famesan dimers % in dehydroesqualene 0 100 20 80 20 80 40 60 80 20 100 O

Example 7

This example provides lubricating properties for various mixtures of famasene dimers (I-A, I-B, I-C and I-D) and squalane. This example provides lubricating properties for the famasene dimers prepared according to example 2 and squalane prepared according to example

4. The famesene dimers tested in this example were distilled to remove any oligomers that may be present.

Table 6

% of famesan dimers % squalene cSt40 cStlOO SAW 20 80 18.0 4.59 185 50 50 17.2 4.58 200 80 20 17.0 4.56 202

Since modifications will be evident to those versed in technology, it is intended that the subject claimed be limited only by the scope of the attached claims.

Claims (13)

1. Composition, characterized by the fact that it comprises: and one or more compounds selected from: wherein the double lines indicate that each of compounds A, B, C, and D is both completely saturated and completely unsaturated. 2. Composition according to claim 1, characterized by the fact that compound A is in which compound A is Petition 870170067664, of 9/12/2017, p. 8/15 Composition according to claim 2, characterized in that it comprises compounds IA and IB, preferably at least 20% of compound IA or at least 20% of compound IB based on the total weight of the composition, optionally further comprising at least at least 2% of compound IC or at least 2% of compound ID based on the total weight of the composition; or which comprises 10% of compound I-A, 10% of compound IB, 1% of compound I-C and 1% of compound I-D based on the total weight of the composition, or which comprises 20% of compound I-A, 20% of compound IB, 2% of compound IC and 2% of compound ID based on the total weight of the composition, or comprising compounds II-A and II-B, preferably at least 20% of compound II-A, or at least 20% of compound II-B based on the total weight of the composition, Petition 870170067664, of 9/12/2017, p. 9/15 or comprising 20% of compound II-A, 20% of compound II-B, 2% of compound II-C and 2% of compound II-D based on the total weight of the composition. 4. Composition, characterized by the fact that it comprises compound II-A, and a compound selected from squalane, squalene, and (6E, 11 E, 18E) -2,6,19,23-tetramethyl-10,15-dimethylenetetracous -2,6,11,18,22pentaene, where compound II-A is 5. Composition according to claim 4, characterized by the fact that it still comprises compound II-B 6. Composition according to claim 4 or 5, characterized by the fact that it still comprises a compound selected from: Petition 870170067664, of 9/12/2017, p. 10/15 claims 4 to 6, characterized by the fact that the selected compound of squalane, squalene, and (6E, 11E, 18E) -2,6,19,23-tetramethyl-10,15dimethylenetetracosa-2,6,11, 18,22-pentaene is squalane. 8. Composition according to claim 4 or 5, characterized in that compound II-A is present in 1% or more, or 20% or more, or 40% or more, or compound II-B is present 1% or more, or 20% or more, or 40% or more based on the total weight of the composition, or where squalane is present in 1% or more, 20% or more based on the total weight of the composition; or where squalene is present at 1% or more based on the total weight of the composition; or where (6E, 11E, 18E) -2,6, 19,23-tetramethyl-10,15-dimethylenetetracosa-2,6,1 l 1,18,22pentaene is present in 1% or more based on the total weight of the composition. Composition according to any one of claims 1 to 8, characterized in that it still comprises at least one additive selected from the group consisting of an antioxidant, an anti-wear agent, a detergent, a rust inhibitor, a demulsifier, a friction modifier, multi-functional additive, viscosity index enhancer, pour point reducer, foam inhibitor, metal deactivator, dispersant, corrosion inhibitor, lubricity enhancer, solubilizing agent , a sealing swelling agent and combinations thereof; or still comprises a base oil. Petition 870170067664, of 9/12/2017, p. 11/15 10. Composition according to any one of claims 1 to 9, characterized in that it is a lubricating composition, a lubricity-enhancing composition, an additive pour point reducer, or a fuel additive. 11. Method of lubricating a machine, characterized by the fact that it comprises the step of operating the machine in contact with the composition as defined in claims 1 to 9. / 12. Engine oil, transmission fluid, hydraulic fluid, gear oil, industrial oil, metal working fluid, process oil, marine oil or grease, characterized by the fact that it comprises the composition as defined in claims 1 to 9. 13. Compound, characterized by the fact that it is selected from the group consisting of Petition 870170067664, of 9/12/2017, p. 12/15 fluidity or fuel additive, characterized by the fact that it comprises a compound as defined in claim 13. 15. Composition according to claim 1, 5 characterized by the fact that it comprises the compounds: and, optionally,; or comprises compounds and optionally Petition 870170067664, of 9/12/2017, p. 13/15 II optionally further comprises squalane. Petition 870170067664, of 9/12/2017, p. 14/15 1/1% distilled famesan dimer