Epoxide compound, method for preparing the same, and use thereof

Abstract

A clean and environmentally friendly process is provided for preparing epoxide compounds in one and two steps using safe and inexpensive starting materials. The catalyst used in this reaction is low cost and recyclable and reusable. Processes for using epoxide compounds and their industrial applications are also provided.

Description

Technical Field

[0001] Cross - Reference to Related Applications This invention claims the benefit of priority to U.S. Patent Application No. 17 / 805,372, filed on June 3, 2022, which is incorporated herein by reference.

[0002] Field of the Invention Embodiments described herein generally relate to epoxide compounds. More specifically, such embodiments relate to methods for producing and using epoxide compounds and their industrial applications. Background of the Invention

[0003] Epoxides are important starting materials for a wide variety of products (Franz, G.; Sheldon, R. A. in: Elvers, B.; Hawkins, S.; Shulz, G. (Eds.), Ullmann’s Encyclopedia of Industrial Chemistry, Vol. A(18), 5th Edition, VCH, Weinheim, 1991, 261 - 311; Lutz, J. T. in: Grayson, M.; Eckroth, D.; Bushey, G. J.; Eastman, C. I.; Klingsberg, A.; Spiro, L. (Eds.), Kirk - Othmer Encyclopedia of Chemical Technology, Vol. 9, 3rd Edition, Wiley, New York, 1980, 251), and much effort has been directed towards the development of novel, efficient and selective epoxidation catalysts for processes that avoid the formation of large amounts of by - products and increase conversion and selectivity. For alkenes with three or more carbon atoms, liquid - phase epoxidation with peracids remains the most widely used method, despite the slow reaction and the formation of large amounts of carboxylic acid by - products. An alternative to avoid the formation of such carboxylic acid by - products is to use hydrogen peroxide as the oxidant in the presence of a catalyst, which results in a clean and environmentally friendly reaction since the starting materials are relatively safe and inexpensive and only water is formed as a by - product (Strukul, G. in Strukul, G. (Ed.), Catalytic Oxidation with Hydrogen Peroxide as Oxidant, Kluwer Academic Publishers, Dordrecht, 1992, 6). Epoxidation with only H2O2 is not effective.The catalysts shown for carrying out epoxidation in the presence of hydrogen peroxide include tungsten (Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831; Venturello, C.; D’Aloisio, R. J. Org. Chem. 1988, 53, 1553; Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M. J. Org. Chem. 1988, 53, 3587), manganese (Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Panyella, D.; Noyori, R. Bull. Chem. Soc. Jpn. 1997, 70, 905; Anelli, P. L.; Banfi, S.; Montanari, F.; Quici, S. Chem. Commun. 1989, 779; De Vos, D.; Bein, T. Chem. Commun. 1996, 917), and rhenium (De Vos, D. E.; Sels, B. F.; Reynaers, M.; Subba Rao, Y. V.; Jacobs, P. A. Tetrahedron Lett. 1998, 39, 3221; Sales, H. J.; Cesquini, R.; Mandelli, D.; Sato, S.; Schuchardt, U. Stud. Surf. Sci. Catal. 2000, 130, 1661; Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189)-based systems, as well as Bronsted acids such as formic acid. However, the industrial use of these systems is not straightforward because of the high cost of the catalysts and the difficulty of separating the catalysts from the products. Furthermore, acid catalysts promote the hydrolysis of epoxides to diols under aqueous acid conditions. A possible solution to this would be to use solid catalysts that have a lower tendency to cause hydrolysis. This approach would enable the design of continuous processes in addition to the current batch reactions.Nevertheless, there are few efficient solid catalysts for such reactions, i.e., Ti-silicalite (van Vliet, M.C.A.; Arends, I.W.C.E.; Sheldon, R.A. Chem. Commun. 1999, 821), vanadium-containing silicates (Sheldon, R.A. in: Cornils, B.; Herrmann W.A. (Eds.), Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1997, 421), Ti-crosslinked clays (Yang, A.; Li, C.; Wang, S.; Lu, J.; Ying, P.; Xin, Q.; Shi, W. Stud. Surf. Sci. Catal. 2000, 130, 221), hydrotalcite [(halfallah-Boudali, L.; Ghorbel, A.; Figueras, F.; Pinel, C. Stud. Surf. Sci. Catal. 2000, 130, 1643; Fraile, J.M.; Garcia, J.I.; Marco, D.; Mayoral, J.A.; Sanchez, E.; Monzon, A.; Romeo, E. Stud. Surf. Sci. Catal. 2000, 130, 1673), or some alumina catalysts (Mandelli, D.; van Vliet, M.C.A.; Sheldon, R.A.; Schuchardt, U. Appl. Catal. A: Gen. 2001, 219, 209] that result in the conversion to epoxides not exceeding 60% for alkyl chains and generally require ethyl acetate as a solvent, or the use of anhydrous hydrogen peroxide (van Vliet, M.C.A.; Mandelli, D.; Arends, I.W.C.E.; Schuchardt, U.; Sheldon, R. Green Chem. 2001, 3, 243). However, all of these solid catalyst systems are still acidic and, as a result, lead to the hydrolysis of epoxides to diols.

[0004] An aqueous H2O2 solution is the most environmentally friendly and low-cost oxygen source for these reactions but exhibits lower reactivity than the corresponding peracids. The active oxygen present in H2O2 is not highly selective but will be readily converted to selective peroxy species by an alumina-catalyzed reaction in the presence of a suitable organic acid. Thus, the inventors generate peroxycarboxylic acids that are more reactive than H2O2 for the epoxidation of non-reactive substrates such as unsubstituted long-chain internal alkenes under solvent-free conditions. Further, basic alumina is used to avoid the hydrolysis of the epoxide acid catalyst product, opening the way to the use of basic solid catalysts for the epoxidation reaction. The final system is a cascade catalyst cycle in which the active oxygen atom flows from H2O2 to alumina and then to the fatty acid to produce a selective reactive epoxidation species for unsubstituted long straight-chain internal alkene chains that would otherwise be non-reactive. The role of the fatty acid is not only to transfer the active oxygen atom to the alkene but also to homogenize the two-phase alkene-aqueous solution [S.E. Brandolin, J.A. Scilipoti, A.E. Andreatta, I. Magario, 2022, 10.1021 / acs.jced.1c00917]. Further, the fatty acid is recoverable (Mas-Balleste, R.; Que, L. Jr. J. Am. Chem. Soc. 2007, 129, 15964; Klein, J.E.M.N.; Knizia, G.; Rzepa, H.S. ChemistryOpen 2019, 8, 1244). This three-phase heterogeneous epoxidation process is different and environmentally friendly compared to conventional systems. By using the amphoteric solid catalyst alumina, which has both acidic and basic sites, catalyst design for the epoxidation reaction becomes possible, and the inventors here use slightly basic alumina to promote the formation of hydrophobic peracids and minimize diol formation by the acid catalyst. Also, alumina is readily available and cost-effective.

[0005] Therefore, a simple, more efficient, and cost-effective process for producing epoxide compounds is needed.

[0006] In light of the above, it would be desirable to develop a clean and environmentally friendly process for producing epoxide compounds. Further, it would be desirable to develop an efficient process that provides a higher conversion rate and a higher selectivity.

[0007] Accordingly, an object of the present invention is to provide a simple, more efficient and reproducible process for preparing epoxide compounds.

[0008] Another object of the present invention is to use safe and inexpensive starting materials.

[0009] Yet another object of the present invention is to use a low-cost catalyst that can be recycled and reused.

[0010] It is also an object of the present invention to avoid using organic solvents and corrosive acids during the preparation reaction.

[0011] A further object of the present invention is to provide a higher conversion rate and a higher selectivity of the epoxide compound.

[0012] These needs and other needs are met by various aspects of the present disclosure.

SUMMARY OF THE INVENTION

[0013] Methods for producing and using epoxide compounds and their industrial applications are provided.

[0014] In one embodiment, the epoxide compound is prepared in one step.

[0015] In some embodiments, the process for preparing the epoxide comprises heating a mixture of a plurality of alkenes and fatty acids from about 25 °C to about 100 °C, wherein the plurality of alkenes have the following formula (I): R-CH=CH-R’ (I) having, wherein R and R' are H or an alkyl chain having from 8 to 20 carbon atoms, heating; adding an aluminum oxide catalyst to the reaction mixture; injecting a hydrogen peroxide solution into the reaction mixture over a time period of from about 1 hour to about 48 hours; decanting water from the reaction mixture; and recovering the epoxide.

[0016] In another embodiment, the epoxide compound is prepared in two steps.

[0017] In other embodiments, the process for preparing the epoxide comprises heating a fatty acid in a tank at from about 25°C to about 100°C; adding an aluminum oxide catalyst to the reaction mixture; injecting a hydrogen peroxide solution into the reaction mixture over a time period of from about 1 hour to about 48 hours; decanting water from the reaction mixture; recovering the peroxyacid anhydride; heating the peroxyacid anhydride in the tank at about 50°C; and having the following formula (I) wherein R and R' are H or an alkyl chain having from 8 to 20 carbon atoms: R-CH=CH-R' (I) adding a plurality of alkenes having the formula (I) to the tank over a time period of from 3 hours to 48 hours; and recovering the epoxide. DETAILED DESCRIPTION OF THE INVENTION

[0018] I. DEFINITIONS The following terms are intended to have the meanings presented below and are useful in understanding the description and intended scope of the present invention.

[0019] As used in this specification and the appended claims, the singular forms "a", "an", and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, references to "a composition" or "a step" include mixtures of two or more such functional compositions, steps, and the like.

[0020] In this specification, a range can be expressed as from "about" a particular value and / or to "about" another particular value. When such a range is expressed, another aspect includes from one particular value and / or to another particular value. Similarly, when a value is expressed as an approximation by use of the antecedent "about", it is understood that the particular value forms another aspect. It is further understood that each endpoint of a range is effective whether related to or independent of the other endpoint. It is also understood that where several values are disclosed herein, each value is disclosed herein as "about" that particular value in addition to the value itself. For example, if the value "10" is disclosed, "about 10" is also disclosed. It is understood that each increment between two particular integers is also disclosed. For example, if 10 and 15 are disclosed, 11, 12, 13, and 14 are also disclosed.

[0021] References in this specification and the claims which conclude it to the parts by weight of a particular element or component in a composition indicate the weight relationship between that element or component and any other element or component in the composition or article in which the parts by weight are expressed. Thus, a compound containing 2 parts by weight of component X and 5 parts by weight of component Y has X and Y present in a weight ratio of 2:5, and present in such ratio whether or not additional components are included in the compound.

[0022] The weight percent (wt%) of a component is based on the total weight of the formulation or composition in which the component is included, unless specifically stated to the contrary.

[0023] As used herein, the term "any" or "optionally" means that the subsequently recited event or circumstance may or may not occur, and that the description includes instances where the event or circumstance occurs and instances where it does not.

[0024] As used herein, the term "effective amount" refers to an amount sufficient to achieve a desired result or to be effective against an undesirable condition.

[0025] The specific materials, compounds, compositions, and components disclosed in this specification are either commercially available or can be readily synthesized using techniques generally known to those skilled in the art. For example, the starting materials and reagents used in preparing the compounds and compositions of the present disclosure are available from commercial suppliers such as Aldrich Chemical Co. (Milwaukee, Wis.), Acros Organics (Morris Plains, N.J.), Fisher Scientific (Pittsburgh, Pa.), or Sigma (St. Louis, Mo.), or are prepared by methods known to those skilled in the art according to procedures described in references such as Fieser and Fieser’s Reagents for Organic Synthesis, Volumes 1-17 (John Wiley and Sons, 1991); Rodd’s Chemistry of Carbon Compounds, Volumes 1-5 and Supplements (Elsevier Science Publishers, 1989); Organic Reactions, Volumes 1-40 (John Wiley and Sons, 1991); March’s Advanced Organic Chemistry, (John Wiley and Sons, 4th Edition); and Larock’s Comprehensive Organic Transformations (VCH Publishers Inc., 1989).

[0026] Unless otherwise specified, none of the methods described in this specification are intended to be construed as requiring that their steps be performed in a particular order. Thus, when a method claim does not actually recite an order for the steps to follow, or when the steps are not otherwise specifically recited in the claim or the specification as being limited to a particular order, no order is intended to be indicated in any way. This holds for any possible non-explicit basis for interpretation, including logical issues regarding the arrangement of steps or the flow of operations, the obvious meaning derived from grammatical construction or punctuation, and the number or type of embodiments described in this specification.

[0027] As used herein, the term "compound" refers to salts, complexes, isomers, stereoisomers, diastereoisomers, tautomers, and isotopes of a compound, or any combination thereof.

[0028] As used herein, the term "alkyl" refers to acyclic straight-chain or branched unsaturated or saturated hydrocarbons, for example, having from 1 to 10 carbon atoms, generally from 1 to 30 carbon atoms as otherwise specified, C1-C 30 including those containing alkyl. Representative saturated straight-chain alkyls include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, etc., and representative saturated branched alkyls include isopropyl, sec-butyl, isobutyl, tert-butyl, isopentyl, etc. Unsaturated alkyls contain at least one double or triple bond between adjacent carbon atoms (referred to as "alkenyl" or "alkynyl", respectively). Representative straight-chain and branched alkenyls include ethenyl, propenyl, l-butenyl, 2-butenyl, isobutenylenyl, l-pentenyl, 2-pentenyl, 3-methyl-l-butenyl, 2-methyl-2-butenyl, 2,3-dimethyl-2-butenyl, etc., and representative straight-chain and branched alkynyls include ethynyl, propynyl, l-butynyl, 2-butynyl, l-pentynyl, 2-pentynyl, 3-methyl-l-butynyl, etc.

[0029] As used herein, the term "equivalent" refers to a unit of measure of the molar ratio of a reactive component to 1 mole of the alkene being epoxidized, for example, specifically, 0.25 moles of fatty acid per 1 mole of alkene, or 0.5 moles of aluminum oxide per 1 mole of alkene, or 4 moles of hydrogen peroxide per 1 mole of alkene.

[0030] As defined herein, a "lubricant" is a substance (usually a fluid under operating conditions) introduced between two moving surfaces to reduce friction and wear between them. The base oils used in industrial oils or motor oils are generally classified by the American Petroleum Institute as mineral oils (Groups I, II, and III) or synthetic oils (Groups IV and V). See American Petroleum Institute (API) Publication Number 1509.

[0031] The "pour point" represents the lowest temperature at which a fluid will pour or flow, as defined herein. See, for example, ASTM International Standard Test Methods D5950-96, D6892-03, and D97.

[0032] The "cloud point" represents the temperature at which a fluid begins to phase separate due to crystal formation, as defined herein. See, for example, ASTM Standard Test Methods D5773-95, D2500, D5551, and D5771.

[0033] "Centistokes", abbreviated as "cSt", is a unit of kinematic viscosity of a fluid (e.g., a lubricant), and 1 centistoke is equal to 1 square millimeter per second (1 cSt = 1 mm 2 / s). See, for example, ASTM Standard Guide and Test Methods D2270-04, D445-06, D6074, and D2983.

[0034] With respect to the description of the molecules and / or molecular fragments in this specification, "R n " (where "n" is an exponent) refers to a hydrocarbon group, and the molecule and / or molecular fragment may be linear and / or branched.

[0035] As defined herein, "C n " (where "n" is an integer) represents a hydrocarbon molecule or fragment (e.g., an alkyl group), and "n" indicates the number of carbon atoms in the fragment or molecule.

[0036] As used herein, the prefix "bio" generally refers to the association with renewable resources of biological origin, such as resources excluding fossil fuels.

[0037] The term "internal olefin", as used herein, refers to an olefin (i.e., an alkene) having a non-terminal carbon-carbon double bond (C=C). This is significantly different from an "α-olefin" having a terminal carbon-carbon double bond.

[0038] The terms "comprising" (and any form of comprising, e.g., "comprise", "comprises", and "comprised"), "having" (and any form of having, e.g., "have" and "has"), "including" (and any form of including, e.g., "includes" and "include"), or "containing" (and any form of containing, e.g., "contains" and "contain") are used in an inclusive and unrestricted non-limiting sense.

[0039] The term "effective", when used in this specification and / or the claims, means sufficient to achieve the desired, expected, or intended result.

[0040] Finally, unless stated to the contrary, all percentages provided in this specification are percentages by weight.

[0041] Throughout this specification, when publications are referenced, the entire disclosure of these publications is incorporated herein by reference to more fully describe the invention.

[0042] II.1 Preparation of Epoxide Compounds in One Step According to various aspects of the present disclosure, the present invention relates to a process for preparing an epoxide compound. In another aspect, the present invention relates to the use of an epoxide compound and its industrial applications. In one embodiment, the epoxide compound is prepared in one step.

[0043] Unexpectedly and surprisingly, as shown in Scheme 1, it has been discovered that the epoxide compound is synthesized by a simple, more efficient and cost-effective one-step process. As shown in Scheme 1, an alkene, an aluminum oxide catalyst, a hydrogen peroxide solution and a fatty acid were reacted to obtain an epoxide compound. This process was a clean and environmentally friendly process using safe and inexpensive starting materials. During the preparation reaction of the epoxide, no organic solvent and corrosive acid were used. The process of the present invention results in a higher conversion rate (>98%) and a higher selectivity (100%) of the epoxide compound. The catalyst used in this reaction is low-cost and can be recycled and reused.

Chemical formula

[0044] In some embodiments, the process for preparing the epoxide comprises the following formula (I) where R and R’ are H or an alkyl chain having from 8 to 20 carbon atoms: R-CH=CH-R’ (I) heating a mixture of a plurality of alkenes and fatty acids having the formula at a temperature from about 25°C to about 100°C; adding an aluminum oxide catalyst to the reaction mixture; injecting a hydrogen peroxide solution into the reaction mixture over a period of from about 1 hour to about 48 hours; decanting water from the reaction mixture; and recovering the epoxide.

[0045] In certain embodiments, the reaction time varies from about 1 hour to about 48 hours, preferably the reaction time varies from about 7 hours to about 15 hours, and more preferably the reaction time varies from about 0.5 hour to about 5 hours.

[0046] In a further embodiment, the reaction temperature varies from about 25°C to about 100°C, preferably the reaction temperature varies from about 50°C to about 70°C.

[0047] In one embodiment, the alkene is an unsubstituted straight-chain alkene.

[0048] In another embodiment, the alkene has a double bond at any internal position of the alkene chain.

[0049] In some embodiments, the fatty acid has the following formula (II): R”-COOH (II) wherein R” is an alkyl chain having from 5 to 30 carbon atoms.

[0050] In a further embodiment, the fatty acid may have from 5 to 30 carbon atoms, preferably the fatty acid may have from 8 to 18 carbon atoms.

[0051] In other embodiments, the amount of fatty acid varies from about 0.1 equivalent to about 2.0 equivalents, and preferably, the amount of fatty acid varies from about 0.2 equivalent to about 1.0 equivalent.

[0052] In one embodiment, the aluminum oxide is basic.

[0053] In some embodiments, the aluminum oxide may include powder, pellets, spheres, or combinations thereof.

[0054] In other embodiments, the particle size of the aluminum oxide powder varies from about 50 micrometers to about 500 micrometers.

[0055] In further embodiments, the particle size of the aluminum oxide pellets varies from about 0.5 mm to about 5.0 mm.

[0056] In certain embodiments, the amount of aluminum oxide relative to the alkene varies from about 0.1 equivalent to about 2.0 equivalents, and preferably, the amount of aluminum oxide relative to the alkene varies from about 0.25 equivalent to about 1.0 equivalent.

[0057] In alternative embodiments, the aluminum oxide catalyst is recovered from the reaction and reused. In one embodiment, the reuse of the alumina catalyst was carried out. For example, the alumina catalyst may be quantitatively recovered after filtration, washed with a polar solvent (ethyl acetate, isopropanol), and dried using heat and / or vacuum. In other embodiments, the reuse of the alumina catalyst was carried out in a continuous reactor. For example, the alumina catalyst may be quantitatively recovered after heating at about 70 °C to about 150 °C for 7 hours under a nitrogen stream.

[0058] In some embodiments, the concentration of the hydrogen peroxide solution varies from about 30% to about 70%.

[0059] In one embodiment, the concentration of the hydrogen peroxide solution is about 50%.

[0060] In other embodiments, the amount of hydrogen peroxide varies from about 1 equivalent to about 10 equivalents, and preferably, the amount of hydrogen peroxide varies from about 2 equivalents to about 6 equivalents.

[0061] In some embodiments, the process is carried out in the absence of a solvent or a corrosive acid.

[0062] In other embodiments, the process is carried out in a batch reactor.

[0063] In certain embodiments, the batch reactor has a stirring speed of from about 200 rpm to about 1000 rpm.

[0064] In further embodiments, the process is carried out in a continuous reactor.

[0065] In other embodiments, the continuous reactor has a flow rate of from about 0.05 mL / h to about 1.0 mL / h.

[0066] In certain embodiments, the lubricant composition is prepared using an epoxide.

[0067] III.2 Preparation of Epoxide Compounds in Two Steps In another embodiment, the epoxide compound was prepared in two steps.

[0068] Unexpectedly and surprisingly, it has been discovered that, as shown in Scheme 2, an epoxide compound can be synthesized by a simple, more efficient, and cost-effective two-step process. The fatty acid was heated with a hydrogen peroxide solution at from about 25 °C to about 100 °C for a time of from about 1 hour to about 48 hours in the presence of an aluminum oxide catalyst in a tank. Water was decanted from the reaction mixture and the peroxyacid anhydride was recovered. As shown in Scheme 2, the peroxyacid anhydride was heated in the tank at about 50 °C, and subsequently, the alkene was added to the tank over a period of from 3 hours to 48 hours, and the epoxide compound was recovered.

Chemical formula

[0069] In other embodiments, the process for preparing the epoxide comprises heating the fatty acid in a tank at about 25 °C to about 100 °C; adding an aluminum oxide catalyst to the reaction mixture; injecting a hydrogen peroxide solution into the reaction mixture over a period of about 1 hour to about 48 hours; decanting water from the reaction mixture; recovering the peroxyacid anhydride; heating the peroxyacid anhydride in the tank at about 50 °C; and adding a plurality of alkenes having the following formula (I) where R and R’ are H or an alkyl chain having 8 to 20 carbon atoms: R-CH=CH-R’ (I) to the tank over a period of 3 hours to 48 hours; and recovering the epoxide.

[0070] In some embodiments, the fatty acid has the following formula (II): R”-COOH (II) wherein R” is an alkyl chain having 5 to 30 carbon atoms.

[0071] In further embodiments, the fatty acid may have 5 to 30 carbon atoms, and preferably, the fatty acid may have 8 to 18 carbon atoms.

[0072] In other embodiments, the amount of the fatty acid varies from about 0.1 equivalent to about 2.0 equivalents, and preferably, the amount of the fatty acid varies from about 0.2 equivalent to about 1.0 equivalent.

[0073] In one embodiment, the peroxyacid is generated in situ.

[0074] In other embodiments, an oxygen atom moves from hydrogen peroxide to the fatty acid, thereby generating the peroxyacid.

[0075] In certain embodiments, the process is carried out using the reactants as solvents.

[0076] In a further embodiment, the fatty acid is recovered from the reaction and reused.

[0077] In other embodiments, the fatty acid may be recovered from the reaction mixture after the reaction, and subsequently reused in a second run by performing filtration, washing of the alumina, and precipitation with basic water or extraction with an organic solvent and water.

[0078] IV. Industrial Applications Unexpectedly and surprisingly, it has been discovered that epoxide compounds are synthesized in one-step and two-step processes. This process is clean, environmentally friendly, and uses safe and inexpensive starting materials. During the preparation reaction of the epoxide, no organic solvents and corrosive acids are used. This process results in a higher conversion rate (>98%) and a higher selectivity (100%) of the epoxide compound. The catalyst used in this reaction is of low cost and can be recycled and reused. Industrial applications of the epoxide compound include, but are not limited to, lubricants, personal care products, paints, coatings, plastics, and plasticizers. The epoxide can also be used as a stabilizer and an acid scavenger additive, or as an intermediate for forming esters, bio-resins, or cross-linking agents for polymer synthesis.

Examples

[0079] To provide a better understanding of the foregoing disclosure, the following non-limiting examples are provided. These examples may be directed to specific embodiments, but should not be regarded as limiting the invention in any specific respect.

[0080] Example 1: Preparation of Epoxide by Batch Reactor Process Batch reaction procedure. The corresponding amounts of Al2O3 catalyst (25 to 50 wt%), alkene (5 mmol), and fatty acid (0.25 equivalent) were placed in a 10 mL round-bottom flask equipped with a magnetic stirrer at 70 °C. Then, 35 to 50% (2 - 6 equivalents) of H2O2 was added in one pot and stirred for the required time. Thereafter, the vial was cooled to separate the phases (solid, organic, and aqueous), and after dilution with ethyl acetate, the mixture was analyzed by GC. The product was isolated by filtration to remove alumina and then by extraction of the organic phase. The conversion of the alkene to the epoxide was measured to be 98% with >99% selectivity.

[0081] Example 2: Reaction procedure for alumina reuse The alumina catalyst was recovered after filtration, washed three times with ethyl acetate, and dried overnight in vacuo. Then, the corresponding amounts of Al2O3 catalyst (25 to 50 wt%), alkene (5 mmol), and acid (0.25 equivalent) were placed in a 10 mL round-bottom flask equipped with a magnetic stirrer at 70 °C. Then, 35 to 50% (2 - 6 equivalents) of H2O2 was added in one pot and stirred for the required time. Thereafter, the vial was cooled to separate the phases (solid, organic, and aqueous), and after dilution with ethyl acetate, the mixture was analyzed by GC. The product was isolated by filtration to remove alumina and then by extraction of the organic phase. The procedure for alumina reuse was repeated three times. The conversion of the alkene to the epoxide in each case was measured to be 97 - 99% with >99% selectivity.

[0082] Example 3: Preparation of epoxide by continuous reactor process Reaction procedure for continuous reactor. 1 / 16” spherical Al2O3 was placed inside a tubular reactor and heated at 70 °C. A 4:6 stirred liquid mixture of alkene and 0.25 equivalent of acid and 30 - 50 wt% H2O2 was passed through the fixed bed of alumina at a rate varying between 0.25 ml / h and 2.0 ml / h. At a flow rate of 1.0 ml / h, the conversion of the alkene to the epoxide was measured to be 25 - 30% per pass with >99% selectivity. After multiple passes, >80% conversion can be achieved.

[0083] In the foregoing specification, the present invention has been described in relation to its specific embodiments and numerous details have been set forth for purposes of illustration. However, it will be apparent to those skilled in the art that the present invention may include additional embodiments and that the specific details described herein may be significantly modified without departing from the basic principles of the invention. Although the inventors have described preferred embodiments for carrying out the present invention, it will be understood by those skilled in the art to which this disclosure pertains that the invention may be subject to changes and additions without departing from its scope.

[0084] All references cited herein are incorporated by reference in their entirety. The present invention may be embodied in other specific forms without departing from its spirit or essential attributes, and accordingly, reference should be made to the appended claims rather than the foregoing specification to indicate the scope of the present invention.

Claims

1. A process for preparing an epoxide, said process comprising: heating a mixture of a plurality of alkenes and fatty acids from about 25 °C to about 100 °C, wherein the plurality of alkenes have the following formula (I): R-CH=CH-R' (I) where R and R' are H or an alkyl chain having 8 to 20 carbon atoms; said heating; adding an aluminum oxide catalyst to the reaction mixture; injecting a hydrogen peroxide solution into the reaction mixture over a period of about 1 hour to about 48 hours; decanting water from the reaction mixture; recovering the epoxide The process as described above.

2. The process according to claim 1, wherein the alkene is an unsubstituted straight-chain alkene chain.

3. The process according to claim 1, wherein the alkene has a double bond at any internal position of the alkene chain.

4. The fatty acid has the following formula (II): R”-COOH (II) where R” is an alkyl chain having 5 to 30 carbon atoms, the process according to claim 1.

5. The process according to claim 1, wherein the amount of fatty acid varies from about 0.1 equivalent to about 2.0 equivalents.

6. The process according to claim 1, wherein the aluminum oxide is basic.

7. The process according to claim 1, wherein the aluminum oxide comprises powder, pellets, spheres or combinations thereof.

8. The process according to claim 7, wherein the particle size of the aluminum oxide powder varies from about 50 micrometers to about 500 micrometers. **Claim 9** The process according to claim 7, wherein the particle size of the aluminum oxide pellets varies from about 0.5 mm to about 5.0 mm. **Claim 10** The process according to claim 1, wherein the amount of aluminum oxide relative to the alkene varies from about 0.1 equivalent to about 2.0 equivalents. **Claim 11** The process according to claim 1, wherein the aluminum oxide catalyst is recovered from the reaction and reused. **Claim 12** The process according to claim 1, wherein the concentration of the hydrogen peroxide solution varies from about 30% to about 70%. **Claim 13** The process according to claim 12, wherein the concentration of the hydrogen peroxide solution is about 50%. **Claim 14** The process according to claim 1, wherein the amount of hydrogen peroxide varies from about 1 equivalent to about 10 equivalents. **Claim 15** The process according to claim 1, which is carried out in the absence of a solvent or a corrosive acid. **Claim 16** The process according to claim 1, which is carried out in a batch reactor. **Claim 17** The process according to claim 16, wherein the batch reactor has a stirring speed of from about 200 rpm to about 1000 rpm. **Claim 18** The process according to claim 1, which is carried out in a continuous reactor. **Claim 19** The process according to claim 18, wherein the continuous reactor has a flow rate of from about 0.05 mL / h to about 1.0 mL / h. **Claim 20** A lubricant composition prepared using the process according to claim 1.

21. A process for preparing an epoxide, the process comprising: heating a fatty acid in a tank from about 25 °C to about 100 °C; adding an aluminum oxide catalyst to the reaction mixture; injecting a hydrogen peroxide solution into the reaction mixture over a period of about 1 hour to about 48 hours; decanting water from the reaction mixture; recovering the peroxyacid; heating the peroxyacid in the tank at about 50 °C; adding a plurality of alkenes to the tank over a period of 3 hours to 48 hours, wherein the plurality of alkenes have the following formula (I): R-CH=CH-R' (I) where R and R' are H or an alkyl chain having 8 to 20 carbon atoms, said adding; recovering the epoxide and the process.

22. The fatty acid has the following formula (II): R''-COOH (II) where R'' is an alkyl chain having 5 to 30 carbon atoms, the process according to claim 21.

23. The peroxyacid is generated in situ, the process according to claim 21.

24. An oxygen atom moves from hydrogen peroxide to the fatty acid to form a peroxyacid, the process according to claim 21.

25. The process is carried out using the reactants as a solvent, the process according to claim 10.

26. The fatty acid is recovered from the reaction and reused, the process according to claim 10.

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