A mixture of mono- and poly-branched fatty acids

Abstract

The present invention relates to compositions of branched fatty acids or esters thereof and methods for preparing such compositions, as well as methods for producing compositions of branched C10-C24 fatty acids or esters thereof having a high portion (at least 70% by weight) of mono- and hyper-branched C10-C24 fatty acids or esters thereof.

Description

[Technical field]

[0001] Background and Overview 2. Background of the Invention A. Field of the Invention The present invention relates to compositions of branched fatty acids or esters thereof and methods for preparing such compositions, as well as methods for producing compositions of branched C10-C24 fatty acids or esters thereof having a high portion (at least 70% by weight) of mono- and hyper-branched C10-C24 fatty acids or esters thereof.

[0002] More particularly, the present invention relates to a composition of branched C10-C24 fatty acids or esters thereof comprising at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acids or esters thereof, and a ratio of mono-branched / poly-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition.

[0003] Throughout the text of this specification, several documents are cited. Each of the documents herein (including any manufacturer's specifications, instructions, etc.) is incorporated herein by reference. However, no admission is made that any of the cited documents are in fact prior art to the present invention. [Background technology]

[0004] B. Description of related fields To date, branched fatty acids are industrially produced as a by-product of the thermal polymerization of unsaturated fatty acids or fatty acid esters using acid clay as a catalyst. After the reaction, a product consisting of a polymer fraction and a monomer fraction is obtained. The polymer fraction consists mainly of dimers and trimers, while branched fatty acids can be found in the monomer fraction. The current reaction products are very complex, since multiple reactions occur simultaneously, such as cis / trans isomerization, branching, aromatization, double bond shift, and hydrogen transfer. (1-3) The present mixture after treatment has a monomer fraction that usually varies around 35 wt%, since the catalyst forms mainly oligomeric compounds. Therefore, in order to obtain a product consisting mainly of branched fatty acids, several purification steps such as crystallization and distillation are necessary, which can be considered as the main drawback of this process. (4) The monomer fraction contains about 50 wt% branched fatty acids, so the overall maximum yield of the process for branched fatty acids is about 17.5 wt% in the classical process. (5) Studies on the isomerization of unsaturated fatty acids to branched fatty acids have been published in several patents and scientific journals. Despite the fact that the use of clay catalysts for the production of branched fatty acids counters several drawbacks, early patents still use clays such as montmorillonite and bentonite for the isomerization of fatty acids. In these patents, the use of cocatalysts such as dichloromethane and activated carbon is described, which should cause a higher yield of branched fatty acids. Despite this, Neuss et al. report mixtures containing only 40% and Foglia et al. report products containing only 57 wt% branched fatty acids. Furthermore, the function of these cocatalysts remains unclear. (6,7) As the obtained yields of branched fatty acids remain low, researchers are searching for new catalysts to increase the obtained yields. Commercially available zeolites have been proposed as promising catalysts for the isomerization of unsaturated fatty acids to branched fatty acids. The structure of zeolites makes it possible to obtain higher yields of branched fatty acids, since the pores are too small to form oligomeric by-products, but large enough to allow the diffusion of the branched products. In addition to this, it has been shown that zeolites can be reused multiple times. (8,9) The oldest patents using zeolites focus mainly on mordenite and other one-dimensional zeolites. In one of these patents, the use of water or small amounts of alcohol as additives is mentioned for the first time. It is believed that the addition of water when the substrate is a fatty acid, or a lower alcohol when the substrate is a fatty acid ester, suppresses the formation of anhydrides by dehydration or dealcoholization of the reagents. (8) However, the use of water or lower alcohols is countered by another patent published a year later. In this patent, a 68% yield is reached with less catalyst, lower reaction temperature, in a shorter time, and without the addition of water. (9) A few years later, attention shifted to other zeolites such as Beta. With H-Beta, conversions of up to 74% could be reached, yielding a product consisting of 46% branched fatty acids. (12) Summary of the Invention [Problem to be solved by the invention]

[0005] There is a need in the art for improved methods of producing branched fatty acids, particularly mixtures of mono- and poly-branched fatty acids. [Means for solving the problem]

[0006] SUMMARY OF THE PRESENT APPLICATION The inventors have now discovered a method for producing at least 70% by weight of mono- and hyper-branched C10-C24 fatty acids or esters thereof, and branched C10-C24 fatty acids having a ratio of mono- / hyper-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the composition, by heating a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst and in the absence of other additives. There was no need to use additives such as dichloromethane, activated carbon, water or light alcohols (methanol, ethanol), Lewis bases (e.g. triphenylphosphine, triethylenediamine, combinations of triphenylphosphine and triethylenediamine, or metalloaluminophosphate molecular sieves.

[0007] The present invention relates to a composition of branched fatty acids or esters thereof, and to a method for preparing such a composition. More particularly, the present invention relates to a composition of branched C10-C24 fatty acids or esters thereof, comprising at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acids or esters thereof, based on the total weight of the composition, and a ratio of mono-branched / poly-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight).

[0008] The present invention provides a method for obtaining a composition of branched C10-C24 fatty acids according to any one of claims 1 to 10, obtained after a process of isomerizing linear monoethylenically unsaturated C10-C24 fatty acid(s) from a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) based on the total weight of the starting material, by heating in the presence of an orthorhombic 10-ring pore one-dimensional linear channel zeolite isomerization catalyst.

[0009] The present invention provides a method for obtaining a composition of branched C10-C24 fatty acids according to any one of claims 1 to 10, obtained after a process of isomerizing linear monoethylenically unsaturated C10-C24 fatty acid(s) from a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) based on the total weight of the starting material, by heating in the presence of an orthorhombic 10-ring pore one-dimensional linear channel zeolite isomerization catalyst as a single catalyst.

[0010] The present invention provides a method for obtaining a composition of branched C10-C24 fatty acids according to any one of claims 1 to 10, obtained after a process of isomerizing linear monoethylenically unsaturated C10-C24 fatty acid(s) from a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) based on the total weight of the starting material, by heating in the presence of a single zeolite catalyst from the group of orthorhombic 10-ring pore one-dimensional linear channel zeolite isomerization catalysts.

[0011] The present invention provides a method for obtaining a composition of branched C10-C24 fatty acids according to any one of claims 1 to 10, obtained after a process of isomerizing linear monoethylenically unsaturated C10-C24 fatty acid(s) from a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) based on the total weight of the starting material, by heating in the presence of an orthorhombic 10-ring pore one-dimensional linear channel zeolite isomerization catalyst without the use of a cocatalyst.

[0012] The present invention provides a method for obtaining a composition of branched C10-C24 fatty acids according to any one of claims 1 to 10, obtained after a process of isomerizing linear monoethylenically unsaturated C10-C24 fatty acid(s) from a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) based on the total weight of the starting material, by heating in the presence of an orthorhombic 10-ring pore one-dimensional linear channel zeolite isomerization catalyst without the use of any additives such as 1) dichloromethane, 2) activated carbon, 3) water or light alcohols (methanol, ethanol), 4) Lewis base catalysts, such as Lewis base catalyst triphenylphosphine, 5) Lewis base catalyst triethylenediamine and combinations thereof.

[0013] The present invention also provides a method for obtaining a composition of branched C10-C24 fatty acids according to any one of claims 1 to 10, obtained after a process using a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s), based on the total weight of the starting material, by isomerizing the linear monoethylenically unsaturated C10-C24 fatty acid(s) from the starting material by heating in the presence of an orthorhombic (high silica) 10-ring (10MR) zeolite composed of 5, 6 and 10 rings, whereby the 10-ring channels (with 10-ring openings) are linear, unidirectional and one-dimensional (non-interconnected).

[0014] The present invention also provides a method for obtaining a composition of branched C10-C24 fatty acids according to any one of claims 1 to 10, obtained after a process using a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s), based on the total weight of the starting material, by isomerizing linear monoethylenically unsaturated C10-C24 fatty acid(s) from the starting material in the presence of an orthorhombic (high silica) 10-ring (10MR) zeolite composed of 5, 6 and 10 rings, whereby the 10-ring channels (with 10-ring openings) are linear, unidirectional and one-dimensionally non-interconnected, and in the absence of any additives.

[0015] Such zeolite catalysts do not contain interconnected channels, otherwise they have large intersection spaces of more than 6.2 Å. For example, ZSM-35 and ZSM-5. ZSM-35 has a ferrierite-type topology and a two-dimensional textured structure, with 10-membered ring channels of 5.4-4.2 Å perpendicular to 8-membered ring channels of 4.8-3.5 Å. The intersections of the two-dimensional channels provide a large space, and the maximum diameter of the sphere that can be contained is 6.31 Å, thus larger than those of ZSM-22 and ZSM-23. ZSM-5 has a three-dimensional cross-linked network structure. Perpendicular to the plane of the two-dimensional 10-membered ring sinusoidal channel, there is another straight 10-membered ring channel that passes through the plane and intersects with the sinusoidal channel. The nodes of these 10-membered ring channels have sizes of 5.6 Å-5.3 Å and 5.5 Å-5.1 Å, respectively, slightly larger than those of ZSM-35, and the maximum diameter of a sphere that can be contained is 6.36 Å, thus much larger than those of ZSM-22 and ZSM-23.

[0016] It has been demonstrated that the one-dimensional linear channel zeolites ZSM-22 and ZSM-23 are suitable isomerization catalysts for the process for producing the composition of the present invention, while ZSM-35 and ZSM-5 are not suitable for the process for producing the composition of the present invention. ZSM-22 and ZSM-23 are one-dimensional linear channel zeolites, and ZSM-5 is a three-dimensional channel zeolite containing two types of interconnected channels, namely linear channels (5.6-5.3 Å) and sinusoidal channels (5.5-5.1 Å), which can provide a wider spacing than the 10-membered ring linear channel spacing in ZSM-22.

[0017] Particularly suitable isomerization catalysts for the present invention are ZSM-22 zeolites with TON topology, ZSM-23 zeolites with MTT topology, or zeolites of the ZSM-23 / ZSM-22 group with MTT(ZSM-23) and TON(ZSM-22) frameworks.

[0018] The present invention also provides a method for producing a composition comprising at least 70% by weight of mono- and poly-branched C based on the total weight of the composition from the starting materials. 10 -C 24 Fatty acids or their esters, and mono- / multi-branched C less than 5:1 (by weight) 10-24 Branched C, including the ratio of fatty acids or their esters 10 -C 24 A method for preparing a composition of fatty acids or esters thereof is provided, comprising: 10 -C 24 The method further comprises isomerizing linear monoethylenically unsaturated C fatty acid(s) from the starting material by heating in the presence of an isomerization catalyst. 10 -C 24 The method includes isomerizing a fatty acid(s), whereby the isomerization catalyst comprises an orthorhombic 10-ring pore one-dimensional straight channel zeolite.

[0019] According to the present invention, at least 80% by weight of linear monoethylenically unsaturated C based on the total weight of the starting materials 10 -C 24 From a starting material comprising fatty acid(s), branched C according to embodiment 1 10 -C 24 Also provided is a method for preparing a composition of fatty acids, the method comprising: (i) isolating linear monoethylenically unsaturated C fatty acids from a starting material by heating in the presence of an isomerization catalyst; 10 -C 24 (ii) isomerizing the fatty acid(s); (ii) separating the monomer fraction from the oligomeric fraction formed in step (i); and (iii) purifying the monomer fraction to obtain branched C 10 -C 24 obtaining a composition of fatty acids.

[0020] Surprisingly, this composition was obtainable by heating the starting material in the presence of the isomerization catalyst of the present invention in the absence of an additive to which the isomerization catalyst is added. In the above process of the present invention, the branched C 10 -C 24The fatty acid composition is at least 80% by weight, based on the total weight of the starting material, of linear monoethylenically unsaturated C 10 -C 24 From a starting material comprising fatty acid(s), (i) isomerizing a linear monoethylenically unsaturated C 10 -C 24 (ii) isomerizing the fatty acid(s); (ii) separating the monomer fraction from the oligomeric fraction formed in step (i); and (iii) purifying the monomer fraction to obtain branched C 10 -C 24 The composition may be prepared by a process comprising obtaining a composition of fatty acids.

[0021] Suitable isomerization catalysts are orthorhombic 10-ring pore one-dimensional straight channel zeolites with no interconnecting channels, e.g., orthorhombic 10-ring pore one-dimensional straight channel zeolites with no interconnecting channels that would otherwise create an intersection spacing of more than 6.2 Å.

[0022] The isomerization catalyst suitable for the present invention is an orthorhombic high silica 10-ring (10MR) zeolite composed of 5, 6 and 10 rings, whereby the 10-ring channels (with 10-ring openings) are linear, unidirectional and one-dimensional (non-interconnected), with pore sizes of 0.44 nm to 0.56 nm x 0.51 nm to 0.59 nm, preferably 0.45 nm to 0.47 nm x 0.52 nm to 0.58 nm, and composed of 5, 6 and 10 rings. The isomerization catalyst is an orthorhombic high silica 10-ring (10MR) zeolite whereby the 10 ring channels (with 10-ring openings) are linear, unidirectional and one-dimensional (non-interconnected) with openings in the range of 5.5-5.9×4.4-4.7 Angstroms, preferably 5.6-5.8×4.5-4.7 Angstroms, and most preferably about 5.7×4.6 Angstroms. Particularly suitable isomerization catalysts are ZSM-22 zeolites with TON topology, ZSM-23 zeolites with MTT topology, or zeolites of the ZSM-23 / ZSM-22 family with MTT(ZSM-23) and TON(ZSM-22) frameworks, preferably non-mesoporous.

[0023] By using the method of the present invention, it is possible to obtain a composition having at least 70% by weight of mono- and poly-branched C, based on the total weight of the composition. 10 -C 24 fatty acids or their esters, and 2) mono- / multi-branched C less than 5:1 (by weight) 10-24 Branched C, including the ratio of fatty acids or their esters 10 -C 24 It is possible to produce compositions of fatty acids or their esters. Also, such branched fatty acid alkyl esters and fatty acid products of the present invention are particularly suitable and can be utilized in lubricants, personal care and / or home care compositions. Such lubricants can incorporate base oils, and such personal care compositions can incorporate active ingredients and / or pigments or colorants.

[0024] In another aspect of the invention, there is provided a composition of branched C10-C24 fatty acids or esters thereof, comprising: 1) at least 70% by weight of mono- and poly-branched C 10 -C 24 fatty acids or esters thereof, and 2) mono- / multi-branched C, less than 5:1 (by weight) based on the total weight of the composition, or 1.5:1 to 5:1 (by weight) based on the total weight of the composition. 10-24 The present invention provides a composition comprising or consisting essentially of a ratio of a fatty acid or ester thereof. The present invention also provides its use in a lubricant, personal care and / or home care composition for treating the same. The present invention further provides that the amount of mono-branched C10-C24 fatty acid or ester thereof in the composition is at least 45 wt.% based on the total weight of the composition. The present invention further provides that the amount of multi-branched C10-C24 fatty acid or ester thereof in the composition is at least 45 wt.% based on the total weight of the composition. 10 -C 24 It is provided that the amount of fatty acid or ester thereof is in the range of 0.1 to 30% by weight based on the total weight of the composition. In a further embodiment of the present invention, the amount of cyclic fatty acid in the composition is in the range of 0.1 to 5% by weight based on the total weight of the composition. In one embodiment of the present invention, the cyclic compound comprises alicyclic carboxylic acid(s) or ester(s) thereof, the content of which is in the range of 0.1 to 5% by weight based on the total weight of the composition. In yet another embodiment of the present invention, the amount of linear and branched lactone is in the range of 0.1 to 5% by weight based on the total weight of the composition. In yet another embodiment of the present invention, the amount of oligomer is in the range of 0.1 to 8.5% by weight based on the total weight of the composition.

[0025] In certain embodiments of the present invention, the composition has an acid number greater than 165 mg KOH / g. In a preferred embodiment of the present invention, the composition comprises, based on the total weight of the composition, 1) at least 45 wt. % of mono-branched C 10 -C 24 fatty acid or its ester, 2) 0.1 to 30% by weight of multi-branched C 10 -C 24% of fatty acids or esters thereof, 3) 0.1 to 5% by weight of cyclic compounds, 6) 0.1 to 5% by weight of linear and branched lactones, 4) 0.1 to 8.5% by weight of oligomers, and 5) an acid value of greater than 165 mg KOH / g (by weight).

[0026] Branch C of the present invention 10 -C 24 This composition of fatty acids is produced by isomerizing linear monoethylenically unsaturated C fatty acids from starting materials by heating in the presence of an isomerization catalyst and in the absence of any additives. 10 -C 24 isomerizing a fatty acid(s) to produce at least 80% by weight, based on the total weight of the starting material, of linear monoethylenically unsaturated C 10 -C 24 from a starting material comprising fatty acid(s), in particular (i) by heating in the presence of an isomerization catalyst and in the absence of any additives, linear monoethylenically unsaturated C 10 -C 24 (ii) isomerizing the fatty acid(s); (ii) separating the monomer fraction from the oligomeric fraction formed in step (i); and (iii) purifying the monomer fraction to obtain branched C 10 -C 24 The method includes obtaining a composition of fatty acids. The above process can be embodied in which the isomerization catalyst comprises an orthorhombic 10-ring pore one-dimensional linear channel zeolite, preferably the isomerization catalyst is an orthorhombic 10-ring pore one-dimensional linear channel zeolite without interconnected channels. A particular suitable isomerization catalyst has an orthorhombic 10-ring pore one-dimensional linear channel zeolite without interconnected channels that would otherwise generate an intersection space of more than 6.2 Å, for example, such an isomerization catalyst is an orthorhombic high silica 10-ring (10MR) zeolite composed of 5, 6 and 10 rings, whereby the 10-ring channels (with 10-ring openings) are linear, unidirectional and one-dimensional (non-interconnected), and have a pore size of 0.44 nm to 0.56 nm x 0.51 nm to 0.59 nm, preferably 0.45 nm to 0.47 nm x 0.52 nm to 0.58 nm.

[0027] As demonstrated by the examples, the process in which the composition of the invention advantageously comprises an isomerization catalyst is a ZSM-22 zeolite having a TON topology, a ZSM-23 zeolite having an MTT topology, or a zeolite of the ZSM-23 / ZSM-22 group having an MTT(ZSM-23) and TON(ZSM-22) framework.

[0028] Further scope of applicability of the present invention will become apparent from the detailed description given hereinafter. It should be understood, however, that the detailed description and specific examples, while indicating preferred embodiments of the present invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description. It should be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not intended to limit the invention as defined by the appended claims.

[0029] Aspects and preferred embodiments of the invention described herein may be set forth / explained in what is called a claim format, which is set forth hereinafter.

[0030] 1. A composition comprising: 1) at least 70% by weight of mono-branched and hyper-branched C10-C24 fatty acids or esters thereof, and 2) branched C10-C24 fatty acids having a ratio of mono-branched / hyper-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the composition; the composition being a reaction product of a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) based on the total weight of the starting material, the composition being heated in the presence of a microporous aluminosilicate catalyst and in the absence of a Lewis base.

[0031] 2. The composition of embodiment 1, wherein the catalyst has 10 circular linear channels with no intersecting channels.

[0032] 3. The composition of embodiment 1, wherein the catalyst has 10 ring-shaped linear channels with no interconnected channels that would otherwise create an intersecting space of more than 6.2 Angstroms.

[0033] 4. The composition of any one of embodiments 1-3, wherein the catalyst is an orthorhombic 10-ring (10MR) zeolite composed of 5, 6, and 10 rings, whereby the 10-ring channels (having 10-ring openings) are linear, unidirectional, and one-dimensional.

[0034] 5. The composition of any one of the preceding embodiments, wherein the catalyst has pore / channel openings of less than 7.5 Angstroms.

[0035] 6. The composition according to any one of the first to fifth embodiments, characterized in that the 10 ring-linear channels of the catalyst have a pore size of 0.44 nm to 0.56 nm x 0.51 nm to 0.59 nm, preferably 0.45 nm to 0.47 nm x 0.52 nm to 0.58 nm.

[0036] 7. The composition according to any one of the preceding embodiments, wherein the 10 ring linear channels of the catalyst have openings within the range of 5.5-5.9×4.4-4.7 angstroms, preferably 5.6-5.8×4.5-4.7 angstroms, and most preferably about 5.7×4.6 angstroms.

[0037] 8. The composition according to any one of the preceding claims, characterized in that the catalyst is a ZSM-22 zeolite with TON topology, a ZSM-23 zeolite with MTT topology, or a zeolite from the group of ZSM-23 / ZSM-22 with MTT(ZSM-23) and TON(ZSM-22) frameworks.

[0038] 9. The composition of any one of the preceding embodiments, wherein the starting material is heated in the absence of a catalyst having a mesoporous crystalline phase.

[0039] 10. The composition of any one of the preceding embodiments, wherein the starting material is heated in the absence of a metal-containing catalyst.

[0040] 11. The composition of any one of the preceding embodiments, wherein the starting material is heated in the absence of a catalyst containing a transition metal, a post-transition metal, an Ln series element, or an element from the group consisting of B, Ti, Ga, Zr, Ge, Va, Cr, Sb, Nb, and Y.

[0041] 12. The composition of any one of the preceding embodiments, wherein the starting material is heated in the absence of an additive or catalyst selected from the group consisting of dichloromethane, activated carbon, water or light alcohol (methanol, ethanol), Lewis base catalyzed triphenylphosphine, Lewis base catalyzed triethylenediamine, Lewis base catalyzed triphenylphosphine, Lewis base catalyzed triethylenediamine combinations and metalloaluminophosphate molecular sieves.

[0042] 13. (i) The production of linear monoethylenically unsaturated C 10 -C 24 (ii) isomerizing the fatty acid(s); (ii) separating the monomer fraction from the oligomeric fraction formed in step (i); and (iii) purifying the monomer fraction to obtain branched C 10 -C 24 13. The composition of any one of embodiments 1 to 12, which is a reaction product of obtaining a composition of fatty acids.

[0043] 14. Based on the total weight of the composition, 1) at least 70% by weight of mono- and poly-branched C 10 -C 24 fatty acids or their esters, and 2) mono- / multi-branched C less than 5:1 (by weight) 10-24 Branched C, including the ratio of fatty acids or their esters 10 -C 24 14. The composition according to any one of the preceding embodiments, characterized in that it is a composition of fatty acids or esters thereof.

[0044] 15. The composition according to any one of the preceding embodiments, wherein the ratio of mono- / multi-branched C10-24 fatty acids or esters thereof is in the range of 1.5:1 to 5:1 (by weight) based on the total weight of the composition.

[0045] 16. Single Branch C 10 -C 24 16. The composition of any one of the preceding embodiments, wherein the amount of fatty acid or ester thereof is at least 45% by weight, based on the total weight of the composition.

[0046] 17. Multi-branch C 10 -C 24 17. The composition according to any one of the preceding embodiments, wherein the amount of fatty acid or its ester is in the range of 0.1 to 30% by weight, based on the total weight of the composition.

[0047] 18. The composition according to any one of the preceding embodiments, wherein the amount of cyclic fatty acid is in the range of 0.1 to 5% by weight, based on the total weight of the composition.

[0048] 19. The composition according to any one of the preceding embodiments, wherein the cyclic compound comprises an alicyclic carboxylic acid(s) or an ester(s) thereof, the content of which is in the range of 0.1 to 5% by weight based on the total weight of the composition.

[0049] 20. The composition according to any one of the preceding embodiments, wherein the amount of linear and branched lactones is in the range of 0.1 to 5% by weight, based on the total weight of the composition.

[0050] 21. The composition according to any one of the preceding embodiments, wherein the amount of oligomer is in the range of 0.1 to 8.5% by weight, based on the total weight of the composition.

[0051] 22. The composition of any one of the preceding embodiments, wherein the acid value is greater than 165 mg KOH / g.

[0052] 23. Based on the total weight of the composition, 1) at least 45% by weight of mono-branched C 10 -C24 fatty acid or its ester, 2) 0.1 to 30% by weight of multi-branched C 10 -C 24 23. The composition according to any one of the preceding claims, further comprising a fatty acid or an ester thereof, 3) 0.1 to 5 wt. % of a cyclic compound, 6) 0.1 to 5 wt. % of a linear and branched lactone, 4) 0.1 to 8.5 wt. % of an oligomer, and 5) an acid value higher than 165 mg KOH / g (by weight). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0053] Detailed Description DETAILED DESCRIPTION OF EMBODIMENTS OF THE PRESENTINVENTION The following detailed description of the invention refers to the accompanying drawings, in which the same reference numbers in different drawings identify the same or similar elements, and the following detailed description is not intended to limit the invention. Instead, the scope of the invention is defined by the appended claims and their equivalents.

[0054] The mesoporous pore range is generally in the range of 13-200 Angstroms, while the microporous pore range of typical zeolite pore / channel openings is in the range of 3-7.5 Angstroms.

[0055] By "branched" fatty acid it is intended that the hydrocarbon chain of a monocarboxylic acid fatty acid has one or more generally short alkyl side groups.

[0056] By "short alkyl side groups" is intended a group containing less than 5 carbon atoms. More particularly, the short alkyl side groups are each linear and even more particularly selected from the group constituted by methyl, ethyl and propyl. Preferably, the short alkyl side groups are each methyl and / or ethyl, more preferably methyl.

[0057] By "branched C10-C24 fatty acid or ester thereof" is then intended, respectively, a poly-branched C10-C24 fatty acid or an ester of a poly-branched C10-C24 fatty acid, and optionally a mono-branched C10-C24 fatty acid or an ester of a mono-branched C10-C24 fatty acid.

[0058] By "singly branched" fatty acid it is intended that the linear hydrocarbon chain of the fatty acid has only one, generally short, alkyl side group.

[0059] By "multiple-branched" fatty acids it is intended that the linear hydrocarbon chain of the fatty acid has only two or more alkyl side groups, which are generally short.

[0060] "Cyclic compounds" include, but are not limited to, alicyclic carboxylic acids or esters thereof, aromatic(s), alkylcyclopentanone(s), and mixtures thereof.

[0061] The ZSM-22 and ZSM-23 zeolites suitable for the present invention are of the class of one-dimensional zeolites, more specifically one-dimensional straight channel zeolites, and even more specifically of the type of orthorhombic 10-ring pore one-dimensional straight channel zeolites with no interconnecting channels.

[0062] ZSM-23, a high silica zeolite, is in the orthorhombic space group Pmmn with lattice parameters a=5.01±0.02 Å, b=21.52±0.04 Å, and c=11.13±0.03 Å. The crystal structures of ZSM-22 and ZSM-23 are closely related in that both zeolites contain structurally identical subunits that generate non-interpenetrating one-dimensional channels defined by 10 rings parallel to a short 5 Å axis. Although there are subtle differences in the geometry of the openings, the 10-ring channel dimensions in ZSM-22 and ZSM-23 are essentially the same. The topology of the zeolite framework is composed of 5, 6, and 10 rings with no intersecting channels, and the 10-ring linear channels have a pore size of 0.45 nm × 0.52 nm.

[0063] ZSM-22, an orthorhombic high-silica zeolite (Cmcm, a=13.86±0.03 Å, b=17.41±0.04 Å, and c=5.04±0.02 Å), has a framework consisting of 5-, 6-, and 10-rings. The structure contains ferrierite sheets of the type previously found in ZSM-5, ZSM-11, and ZSM-35, and 6-ring sheets similar to those of the rare zeolite biquitite. The channel system is linear, unidirectional, and one-dimensional (non-interconnected) with 10-ring openings that are within the range of 5.5-5.9×4.4-4.7 Å, preferably 5.6-5.8×4.5-4.7 Å, and most preferably about 5.7×4.6 Å. The 10-ring channels are smaller than those previously found in ZSM-5, ZSM-11, and ZSM-35.

[0064] Examples of additives are cocatalysts such as dichloromethane and activated carbon, water and a phosphine base (triphenylphosphine). The process of the present invention does not require such additives.

[0065] Isomerized or branched fatty acids such as isostearic acid are currently produced as secondary products in the dimerization of unsaturated fatty acids. This product has proven to be heat and odor resistant, making it excellent for cosmetic formulations and lubricants. Isostearic acid has also proven to provide oxidation stability to products with long shelf life requirements. In addition, this product is known to have a very low cloud point and is easily processable. Isostearic acid is more expensive than standard quality fatty acid dimers, and the market for isostearic acid is expanding rapidly. Therefore, a mixture of high levels of branched fatty acids and small amounts, if any, of fatty acid dimers or oligomers is of great importance. Other by-products from processing, such as cyclic fatty acids or lactones, should be avoided to the greatest extent possible as well.

[0066] To date, branched fatty acids are industrially produced as a by-product of the thermal polymerization of unsaturated fatty acids or fatty acid esters using acid clay as a catalyst. After the reaction, a product consisting of a polymer fraction and a monomer fraction is obtained. The polymer fraction consists mainly of dimers and trimers, while branched fatty acids can be found in the monomer fraction. The current reaction products are very complex, since multiple reactions occur simultaneously, such as cis / trans isomerization, branching, aromatization, double bond shift, and hydrogen transfer. (1-3) The present mixture after treatment has a monomer fraction that usually varies around 35 wt%, since the catalyst forms mainly oligomeric compounds. Therefore, in order to obtain a product consisting mainly of branched fatty acids, several purification steps such as crystallization and distillation are necessary, which can be considered as the main drawback of this process. (4) The monomer fraction contains about 50 wt% branched fatty acids, so the overall maximum yield of the process for branched fatty acids is about 17.5 wt% in the classical process. (5) Studies on the isomerization of unsaturated fatty acids to branched fatty acids have been published in several patents and scientific journals. Despite the fact that the use of clay catalysts for the production of branched fatty acids counters several drawbacks, early patents still use clays such as montmorillonite and bentonite for the isomerization of fatty acids. In these patents, the use of cocatalysts such as dichloromethane and activated carbon is described, which should cause a higher yield of branched fatty acids. Despite this, Neuss et al. report mixtures containing only 40% and Foglia et al. report products containing only 57 wt% branched fatty acids. Furthermore, the function of these cocatalysts remains unclear. (6,7) As the obtained yields of branched fatty acids remain low, researchers are searching for new catalysts to increase the obtained yields. Commercially available zeolites have been proposed as promising catalysts for the isomerization of unsaturated fatty acids to branched fatty acids. The structure of zeolites makes it possible to obtain higher yields of branched fatty acids, since the pores are too small to form oligomeric by-products, but large enough to allow the diffusion of the branched products. In addition to this, it has been shown that zeolites can be reused multiple times. (8,9) The oldest patents using zeolites focus mainly on mordenite and other one-dimensional zeolites. In one of these patents, the use of water or small amounts of alcohol as additives is mentioned for the first time. It is believed that the addition of water when the substrate is a fatty acid, or a lower alcohol when the substrate is a fatty acid ester, suppresses the formation of anhydrides by dehydration or dealcoholization of the reagents. (8) However, the use of water or lower alcohols is countered by another patent published a year later. In this patent, a 68% yield is reached with less catalyst, lower reaction temperature, in a shorter time, and without the addition of water. (9) A few years later, attention shifted to other zeolites such as Beta. With H-Beta, conversions of up to 74% could be reached, yielding a product consisting of 46% branched fatty acids. (12) Thus, there remains a need for improved methods for producing mixtures of branched fatty acids, particularly mono- and poly-branched fatty acids.

[0067] Advantageously, the composition of the present invention is liquid at 0° C. due to the presence of highly branched fatty acids and fewer cyclic compounds. The composition is also stable at high temperatures and resistant to UV radiation. Advantageously, the composition of the present invention exhibits better low temperature properties.

[0068] Preferably, the cyclic compound contains from 14 to 22 carbon atoms, more preferably from 16 to 18 carbon atoms.

[0069] Preferably, the content of the cyclic compound is in the range of 0.1% to 5% by weight, more preferably 3% to 5% by weight, based on the total weight of the composition.

[0070] Preferably, the cyclic compound of the composition of the present invention comprises alicyclic carboxylic acid(s) or ester(s) thereof, the content of which is in the range of 0.1% to 5% by weight based on the total weight of the composition.

[0071] Advantageously, the content of cycloaliphatic carboxylic acid(s) or ester(s) thereof ranges from 0.1% to 5%, more preferably from 0.1% to 3.5%, even more preferably from 1% to 3.5% by weight, based on the total weight of the composition.

[0072] Preferably, the lactone content is less than 5%, more preferably less than 4.5%. Working Example Example 1: ZSM-22 35 grams of fatty acid (containing 91.3 wt% oleic acid) and 0.875 grams of H-ZSM-22 (Bonding Chemical) were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 250° C. while stirring at 600 rpm. This reaction temperature was maintained for 4 hours.

[0073] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0074] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fraction (Table I).

[0075] [Table 1]

[0076] Example 2: ZSM-22 35 grams of fatty acid (containing 91.3 wt% oleic acid) and 0.875 grams of H-ZSM-22 (Bonding Chemical) were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 250° C. while stirring at 600 rpm. This reaction temperature was maintained for 6 hours.

[0077] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0078] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 2).

[0079] [Table 2]

[0080] Example 3: Post-synthetic treated ZSM-22 35 grams of fatty acid (containing 90.1 wt% oleic acid) and 0.875 grams of H-ZSM-22 (Bonding Chemical, treated after synthesis) were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 250° C. while stirring at 600 rpm. This reaction temperature was maintained for 2 hours.

[0081] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0082] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 3).

[0083] [Table 3]

[0084] Example 4: ZSM-23 One gram of granulated H-ZSM-23 (250μm-500μm granules) was placed in a continuous fixed bed reactor. The catalyst bed was heated to 250°C, after which fatty acid (containing 87wt% oleic acid) was pumped through the catalyst bed at a flow rate of 0.05ml / min.

[0085] A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0086] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fraction.

[0087] [Table 4]

[0088] Comparative example 1: ZSM-5 35 grams of fatty acid (containing 84.0 wt% oleic acid) and 2,625 grams of H-ZSM-5 (Zeolyst, CBV2314) were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 250° C. while stirring at 600 rpm. This reaction temperature was maintained for 24 hours.

[0089] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0090] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 4).

[0091] [Table 5]

[0092] Comparative Example 2: Post-synthetic treated ZSM-5 35 grams of fatty acid (containing 88.8 wt% oleic acid) and 0.875 grams of H-ZSM-5 (Zeolyst, CBV2314, treated after synthesis) were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 250° C. while stirring at 600 rpm. This reaction temperature was maintained for 6 hours.

[0093] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0094] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 5).

[0095] [Table 6]

[0096] Comparative Example 3: MOR (Mordenite) 35 grams of fatty acid (containing 84.0 wt% oleic acid) and 1.75 grams of H-MOR (Zeolyst, CBV21A) were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 250° C. while stirring at 600 rpm. This reaction temperature was maintained for 8 hours.

[0097] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0098] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 6).

[0099] [Table 7]

[0100] Comparative Example 4: Post-synthetic treated MOR 35 grams of fatty acid (containing 89.4 wt% oleic acid) and 0.875 grams of H-MOR (Zeolyst, CBV21A, treated after synthesis) were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 250° C. while stirring at 600 rpm. This reaction temperature was maintained for 6 hours.

[0101] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0102] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 7).

[0103] [Table 8]

[0104] Comparative Example 5: FER+HO (Ferrierite) 20 grams of fatty acid (containing 83.3 wt% oleic acid), 1 gram of H-FER (Tosoh, 720NHA) and 0.4 grams of distilled water were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. 7 bar of nitrogen pressure was applied to the autoclave. The mixture was heated to 260° C. while stirring at 600 rpm. This reaction temperature was maintained for 6 hours.

[0105] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0106] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 8).

[0107] [Table 9]

[0108] Comparative example 5: FER+H2O+TPP 20 grams of fatty acid (containing 83.3 wt% oleic acid), 1 gram of H-FER (Tosoh, 720NHA), 0.4 grams of distilled water and 0.075 g of triphenylphosphine were placed together in a 50 ml Parr autoclave. The air was flushed with nitrogen three times. A pressure of 7 bar of nitrogen was applied to the autoclave. The mixture was heated to 260° C. while stirring at 600 rpm. This reaction temperature was maintained for 6 hours.

[0109] The reaction mixture was then cooled to room temperature and the gaseous components were vented. A hydrogenation step was carried out on the crude reaction mixture using 5% palladium on carbon catalyst. The product was hydrogenated at 80° C. and 20 bar hydrogen pressure for 6 hours.

[0110] To characterize the composition of the hydrogenated crude reaction mixture, the latter was esterified with methanol and subsequently analyzed by gas chromatography. GPC analysis of the hydrogenated crude reaction mixture was carried out to quantify the oligomeric fractions (Table 9).

[0111] [Table 10]

[0112] By using the method of the present invention in which a starting material that comprises, or consists essentially of, or consists of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst and in the absence of a Lewis base, it is possible to obtain a polyolefin copolymer having at least 70% by weight of mono-branched and mono-ethylenically unsaturated C10-C24 fatty acid(s), based on the total weight of the composition, 1) at least 70% by weight of mono-branched and mono-ethylenically unsaturated C10-C24 fatty acid(s). It was possible to obtain a composition comprising branched C10-C24 fatty acids having 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids; or to obtain a branched C10-C24 fatty acid having 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids.

[0113] The present invention relates to a method for obtaining a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the composition; or 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the fatty acids. A method for obtaining branched C10-C24 fatty acids having the ester ratio is provided by heating a starting material comprising, or consisting essentially of, or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst and in the absence of a Lewis base.

[0114] In another aspect, the present invention provides a method for obtaining a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition, or a composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids. The present invention provides a method for obtaining 0-C24 fatty acids by heating a starting material comprising, or consisting essentially of, or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst (the catalyst is characterized by having 10 ring linear channels with no intersecting channels) and in the absence of a Lewis base.

[0115] In another aspect, the present invention relates to a method for obtaining a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / poly-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition, or a method for obtaining a branched C10-C24 fatty acid comprising 1) at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / poly-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids. by heating a starting material comprising, or consisting essentially of, or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst (the catalyst being characterized as having 10 ring linear channels with no interconnecting channels otherwise creating intersecting spaces greater than 6.2 Angstroms) and in the absence of a Lewis base.

[0116] In another aspect, the present invention relates to a method for obtaining a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition, or a method for obtaining a branched C10-C24 fatty acid comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids, the method comprising the steps of: % linear monoethylenically unsaturated C10-C24 fatty acid(s) or consisting essentially of, or consisting of at least 80% by weight linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst (the catalyst is an orthorhombic 10-ring (10MR) zeolite made up of 5, 6 and 10 rings whereby the 10 ring channels (having 10-ring openings) are characterized as being linear, unidirectional and one-dimensional) and in the absence of a Lewis base.

[0117] In another aspect, the present invention provides a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition; or a composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids. A method for obtaining C24 fatty acids is provided by heating a starting material comprising, or consisting essentially of, or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst (the catalyst being characterized by having pore / channel openings of less than 7.5 Angstroms) and in the absence of a Lewis base.

[0118] In another aspect, the present invention relates to a method for obtaining a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition, or a method for obtaining a branched C10-C24 fatty acid comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids, the method comprising the steps of: % by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) or alternatively consisting essentially of or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s), in the presence of a microporous aluminosilicate catalyst (characterized in that the 10 ring linear channels of the catalyst have a pore size of 0,44nm to 0,56nm x 0,51nm to 0,59nm, preferably 0,45nm to 0,47nm x 0,52nm to 0,58nm) and in the absence of a Lewis base.

[0119] In another aspect, the present invention provides a method for obtaining a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / poly-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition, or a method for obtaining a branched C10-C24 fatty acid comprising 1) at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / poly-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids, the method comprising the steps of: and by heating a starting material comprising or consisting essentially of or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst (characterized in that the 10 ring linear channels of the catalyst have openings that are in the range of 5.5-5.9×4.4-4.7 Angstroms, preferably 5.6-5.8×4.5-4.7 Angstroms, most preferably about 5.7×4.6 Angstroms) and in the absence of a Lewis base.

[0120] In another aspect, the present invention provides a method for obtaining a composition comprising branched C10-C24 fatty acids, the composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition, or for obtaining a branched C10-C24 fatty acid comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the fatty acids, the method comprising the steps of: by heating a starting material comprising or consisting essentially of or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst, the catalyst being a ZSM-22 zeolite with TON topology, a ZSM-23 zeolite with MTT topology, or a zeolite of the group ZSM-23 / ZSM-22 with MTT(ZSM-23) and TON(ZSM-22) frameworks, in the absence of a Lewis base.

[0121] The present invention therefore relates to a composition comprising a branched C10-C24 fatty acid having a ratio of mono-branched / multi-branched C10-24 fatty acid or ester of less than 5:1 (by weight), based on the total weight of the composition; or a composition comprising a branched C10-C24 fatty acid having a ratio of mono-branched / multi-branched C10-24 fatty acid or ester of less than 5:1 (by weight), based on the total weight of the composition; The present invention provides the advantage that obtaining branched C10-C24 fatty acids having a ratio of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) can be obtained by heating a starting material that comprises at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) or essentially consists of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst without using a catalyst having a mesoporous crystalline phase.

[0122] The present invention therefore relates to a composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a branched C10-C24 fatty acid having a ratio of mono-branched / multi-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the composition; or a branched C10-C24 fatty acid having 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the fatty acids. It provides the advantage that the acid can be obtained by heating a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) or consisting essentially of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a catalyst having a mesoporous crystalline phase, a microporous aluminosilicate catalyst without or without added metal containing aluminosilicate catalyst.

[0123] The present invention therefore provides a composition comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a branched C10-C24 fatty acid having a ratio of mono-branched / multi-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the composition, or a branched C10-C24 fatty acid having 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters of less than 5:1 (by weight), based on the total weight of the fatty acids. It provides the advantage that it can be obtained by heating a starting material that comprises at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) or that essentially consists of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst but in the absence of a catalyst containing a transition metal, a post-transition metal, an element of the Ln series or an element of the group consisting of B, Ti, Ga, Zr, Ge, Va, Cr, Sb, Nb and Y.

[0124] The present invention therefore relates to a composition comprising a branched C10-C24 fatty acid, the branched C10-C24 fatty acid having 1) at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acid or ester thereof, and 2) a ratio of mono-branched / poly-branched C10-24 fatty acid or ester thereof of less than 5:1 (by weight), based on the total weight of the composition, or a branched C10-C24 fatty acid having 1) at least 70% by weight of mono-branched and poly-branched C10-C24 fatty acid or ester thereof, and 2) a ratio of mono-branched / poly-branched C10-24 fatty acid or ester thereof of less than 5:1 (by weight), based on the total weight of the fatty acid, comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s), or at least The present invention provides the advantage that the process can be obtained by heating a starting material consisting essentially of, or consisting of at least 80% by weight of, linear monoethylenically unsaturated C10-C24 fatty acid(s) in the presence of a microporous aluminosilicate catalyst, but in the absence of an additive or catalyst selected from the group consisting of dichloromethane, activated carbon, water or light alcohol (methanol, ethanol), Lewis base catalyst triphenylphosphine, Lewis base catalyst triethylenediamine, Lewis base catalyst triphenylphosphine, Lewis base catalyst triethylenediamine combinations and metalloaluminophosphate molecular sieves.

[0125] In one embodiment of the present invention, the composition of the present invention is the reaction product of (i) isomerizing linear monoethylenically unsaturated C10-C24 fatty acid(s) from a starting material of the present invention (consisting of, or consisting essentially of, or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s)) by heating in the presence of a catalyst of the present invention as described above, (ii) separating a monomer fraction from an oligomer fraction formed in step (i), and (iii) purifying the monomer fraction to obtain a composition of branched C10-C24 fatty acids.

[0126] Thus, the present invention provides the advantage that by simply heating a starting material comprising, or consisting essentially of, or consisting of at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s), as described herein above, in the presence of a microporous aluminosilicate catalyst and in the absence of other additives, it is possible to obtain a composition of branched C10-C24 fatty acids or esters thereof comprising 1) at least 70% by weight of mono-branched and multi-branched C10-C24 fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), based on the total weight of the composition.

[0127] In an advantageous embodiment, the composition according to the invention and the composition which is the reaction product of the method of the invention further comprises a. In an advantageous embodiment, the compositions according to the invention and the compositions which are reaction products of the methods of the invention further comprise a ratio of mono- / multi-branched C10-24 fatty acids or esters thereof in the range of 1.5:1 to 5:1 (by weight) based on the total weight of the composition.

[0128] In an advantageous embodiment, the composition according to the invention and the composition that is the reaction product of the method of the invention further comprises an amount of mono-branched C10-C24 fatty acid or ester thereof of at least 45% by weight, based on the total weight of the composition.

[0129] In an advantageous embodiment, the composition according to the invention and the composition which is the reaction product of the method of the invention further comprises an amount of poly-branched C10-C24 fatty acid or ester thereof in the range of 0.1 to 30% by weight, based on the total weight of the composition.

[0130] In an advantageous embodiment, the composition according to the invention and the composition which is the reaction product of the method of the invention further comprises an amount of cyclic fatty acid in the range of 0.1 to 5% by weight, based on the total weight of the composition.

[0131] In an advantageous embodiment, the composition according to the invention and the composition which is the reaction product of the method of the invention further comprises a cyclic compound comprising alicyclic carboxylic acid(s) or esters thereof, the content of which is in the range of 0.1 to 5% by weight, based on the total weight of the composition.

[0132] In an advantageous embodiment, the composition according to the invention and the composition which is the reaction product of the method of the invention further comprises that the amount of linear and branched lactones is in the range of 0.1 to 5% by weight, based on the total weight of the composition.

[0133] In an advantageous embodiment, the composition according to the invention and the composition which is the reaction product of the method of the invention further comprises that the amount of oligomer is in the range of 0.1 to 8.5% by weight, based on the total weight of the composition.

[0134] In an advantageous embodiment, the compositions according to the invention and the compositions that are reaction products of the methods of the invention further comprise an acid number greater than 165 mg KOH / g.

[0135] In an advantageous embodiment, the compositions according to the invention and the compositions which are reaction products of the methods of the invention further comprise, based on the total weight of the composition, 1) at least 45% by weight of mono-branched C10-C24 fatty acids or esters thereof, 2) 0.1 to 30% by weight of poly-branched C10-C24 fatty acids or esters thereof, 3) 0.1 to 5% by weight of cyclic compounds, 6) 0.1 to 5% by weight of linear and branched lactones, 4) 0.1 to 8.5% by weight of oligomers, and 5) an acid value of greater than 165 mg KOH / g (by weight).

[0136] Other embodiments of the invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. It is intended that the specification and examples be considered as exemplary only, with a true scope and spirit of the invention being indicated by the following claims.

[0137] Reference to application 1.Koster R.Solid acid catalysed conversions of oleochemicals.2003. 2. Gundstone FD, Harwood JL, Dijkstra AJ, eds. The Lipid Handbook. Third edit.;2007.doi:10.1016 / 0144-8617(88)90020-3. 3.Breuer TE.Dimer acids.In:Kirk-Othmer Encyclopedia of Chemical Technology.;2000. 4.Ngo HL, Hoh E, Foglia TA.Improved synthesis and characterization of saturated branched-chain fatty acid isomers.Eur J Lipid Sci Technol.2012;114:213-221.doi:10.1002 / ejlt.201000471. 5.Ngo HL,Nunez A,Lin W,Foglia TA.Zeolite-catalyzed isomerization of oleic acid to branched-chain isomers.Eur J Lipid Sci Technol.2007;108:214-224.doi:10.1002 / ejlt.200600246. 6. Neuss M, Eierdanz H. US5,364,949.1994. 7. Foglia TA, Perlstein T, Nakano Y, Maerker G. US4,371,469.1983. 8.Tomifuji T, Abe H, Matsumura Y, Sakuma Y.EP0683150B1.1995. 9. Hodgson WR, Lok CM, Roberts G. EP0774451B2.1996. 10.Zhang S,Zhang Z,Steichen D.US2003 / 100780A1.2003. 11.Kenneally CJ, Connor DS.EP1268386B1.2001. 12.Zhang Z,Zhang S,Steichen D.US6,831,184B2.2004.

Claims

**Claim 1** A composition comprising, based on the total weight of the composition: 1) at least 70% by weight of mono- and multi-branched C10-C24 fatty acids or esters thereof; and 2) a ratio of mono-branched to multi-branched C10-24 fatty acids or esters thereof of less than 5:1 (by weight), said composition being a reaction product of a starting material comprising at least 80% by weight of linear monoethylenically unsaturated C10-C24 fatty acid(s) based on the total weight of the starting material, said reaction product being heated in the presence of a microporous aluminosilicate catalyst and in the absence of a Lewis base. **Claim 2** The composition according to claim 1, wherein the catalyst has 10 ring-shaped channels without intersecting channels. **Claim 3** The composition according to claim 1, wherein the catalyst has 10 ring-shaped channels without interconnected channels and otherwise generates an intersecting space exceeding 6.2 angstroms. **Claim 4** The composition according to claim 1, wherein the catalyst is an orthorhombic 10-membered ring (10MR) zeolite composed of 5, 6, and 10 rings, whereby the 10 ring channels (having 10-membered ring openings) are linear, unidirectional, and one-dimensional. **Claim 5** The composition according to claim 1, wherein the catalyst has pores / channel openings of less than 7.5 angstroms. **Claim 6** The composition according to claim 1, wherein the 10 ring-shaped channels of the catalyst have a pore diameter of 0.44 nm to 0.56 nm × 0.51 nm to 0.59 nm, preferably 0.45 nm to 0.47 nm × 0.52 nm to 0.58 nm. **Claim 7** The composition according to claim 1, wherein the 10 ring-shaped channels of the catalyst have openings within the range of 5.5 - 5.9 × 4.4 - 4.7 angstroms, preferably 5.6 - 5.8 × 4.5 - 4.7 angstroms, and most preferably approximately 5.7 × 4.6 angstroms. **Claim 8** The composition according to claim 1, wherein the catalyst is a zeolite of the group consisting of ZSM-22 zeolite having a TON topology, ZSM-23 zeolite having an MTT topology, or ZSM-23 / ZSM-22 having MTT (ZSM-23) and TON (ZSM-22) frameworks. **Claim 9** The composition according to claim 1, wherein the starting material is heated in the absence of a catalyst having a mesoporous crystal phase.

10. The composition according to claim 1, wherein the starting material is heated in the absence of a metal-containing catalyst.

11. The composition according to claim 1, wherein the starting material is heated in the absence of a catalyst containing a transition metal, a post-transition metal, an Ln series element, or an element from the group consisting of B, Ti, Ga, Zr, Ge, Va, Cr, Sb, Nb, and Y.

12. The composition according to claim 1, wherein the starting material is heated in the absence of an additive or catalyst selected from the group consisting of dichloromethane, activated carbon, water, light alcohol (methanol, ethanol), Lewis base catalyst triphenylphosphine, Lewis base catalyst triethylenediamine, Lewis base catalyst triphenylphosphine, a combination of the Lewis base catalyst triethylenediamine, and metalloaluminophosphate molecular sieve.

13. (i) Isomerizing the linear monoethylenically unsaturated C １０ -C ２４ fatty acid(s) by heating in the presence of the catalyst, (ii) separating the monomer fraction from the oligomer fraction formed in step (i), and (iii) purifying the monomer fraction to obtain the composition of branched C １０ -C ２４ fatty acid, the reaction product being the composition according to claim 1.

14. Based on the total weight of the composition, 1) at least 70% by weight of mono-branched and multi-branched C １０ -C ２４ fatty acids or esters thereof, and 2) a ratio of mono-branched / multi-branched C １０ - ２４ fatty acids or esters thereof that is less than 5:1 (by weight), a composition of branched C １０ -C ２４ The composition according to claim 1, characterized in that it is a composition of fatty acids or esters thereof.

15. The composition according to claim 1, wherein the ratio of the mono-branched / multi-branched C10-24 fatty acid or its ester is in the range of 1.5:1 to 5:1 (by weight) based on the total weight of the composition.

16. Single-branched C １０ -C ２４ The composition according to claim 1, wherein the amount of the fatty acid or its ester is at least 45% by weight based on the total weight of the composition.

17. Multi-branched C １０ -C ２４ The composition according to claim 1, wherein the amount of the fatty acid or its ester is in the range of 0.1 to 30% by weight based on the total weight of the composition.

18. The composition according to claim 1, wherein the amount of the cyclic fatty acid is in the range of 0.1 to 5% by weight based on the total weight of the composition.

19. The composition according to claim 1, wherein the cyclic compound contains an alicyclic carboxylic acid(s) or its ester(s), and the content thereof is in the range of 0.1 to 5% by weight based on the total weight of the composition.

20. The composition according to claim 1, wherein the amount of the linear and branched lactones is in the range of 0.1 to 5% by weight based on the total weight of the composition.

21. The composition according to claim 1, wherein the amount of the oligomer is in the range of 0.1 to 8.5% by weight based on the total weight of the composition.

22. The composition according to claim 1, wherein the acid value is higher than 165 mg KOH / g.

23. Based on the total weight of the composition, 1) at least 45% by weight of monobranched C １０ -C ２４ fatty acids or esters thereof, 2) 0.1 to 30% by weight of multi-branched C １０ -C ２４ fatty acids or esters thereof, 3) 0.1 to 5% by weight of cyclic compounds, 6) 0.1 to 5% by weight of linear and branched lactones, 4) 0.1 to 8.5% by weight of oligomers, and 5) having an acid value higher than 165 mg KOH / g (on a weight basis), the composition according to claim 1.