Methods of making 1-pentadecanoic acid from 1-tetradecene or 1-hexadecene

Abstract

1-Pentadecanoic acid is produced by contacting a feedstock olefin composition containing 1-tetradecene with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form C15 aldehydes, and then oxidizing the C15 aldehydes to form 1-pentadecanoic acid. Additionally, 1-pentadecanoic acid is produced by subjecting a feedstock olefin composition containing 1-hexadecene to ozonolysis to form C15 aldehydes, and then oxidizing the C15 aldehydes to form 1-pentadecanoic acid.

Description

METHODS OF MAKING 1 -PENTADECANOIC ACID FROM 1 -TETRADECENE OR 1 -HEXADECENEREFERENCE TO RELATED APPLICATION

[0001] This application is being filed on January 15, 2026, as a PCT International Patent Application and claims the benefit of and priority to U.S. Provisional Patent Application No. 63 / 746,316, filed on January 17, 2025, the disclosure of which is incorporated herein by reference in its entirety.TECHNICAL FIELD

[0002] The present disclosure relates generally to methods for making 1 -pentadecanoic acid, and more particularly, relates to the synthesis of 1 -pentadecanoic acid from normal alpha olefins in high yield.BACKGROUND

[0003] The saturated odd-chain fatty' acid 1 -pentadecanoic acid, often abbreviated as Cl 5:0, is not produced by the human body. Cl 5:0 may be an essential fatty' acid, and its absence in the human diet has been linked to numerous adverse health outcomes, including metabolic syndrome (e.g., high blood pressure, inflammation, fat around the mid-section, high cholesterol, and high blood sugar). The conventional synthesis scheme to produce C15:0 is very expensive and involves extraction of Ci4 carboxylic acids from sources such as nutmeg, followed by conversion of isolated Ci4 carboxylic acids to C15:0. It would therefore be beneficial to have alternative synthesis schemes that cost effectively produce the desired 1 -pentadecanoic acid (Cl 5:0) in high yield with less by-products. Accordingly, it is to these ends that the present invention is generally directed.SUMMARY

[0004] This summary is provided to introduce a selection of concepts in a simplified form that are further described herein. This summary' is not intended to identify required or essential features of the claimed subject matter. Nor is this summary intended to be used to limit the scope of the claimed subject matter.

[0005] Processes for producing 1 -pentadecanoic acid are disclosed herein. For example, a process for producing 1 -pentadecanoic acid in accordance with one aspect of this 1118-163-344invention can comprise (i) contacting a feedstock olefin composition comprising at least 75 mol % 1 -tetradecene with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form a first composition comprising Cis aldehydes, and (ii) oxidizing (all or any portion of) the Cis aldehydes to form a second composition comprising 1 -pentadecanoic acid.

[0006] In another aspect of the present disclosure, a process for producing 1-pentadecanoic acid can comprise (a) subjecting a feedstock olefin composition comprising at least 75 mol % 1 -hexadecene to ozonolysis to form a first composition comprising Cis aldehydes, and (b) oxidizing (all or any portion of) the Cis aldehydes to form a second composition comprising 1 -pentadecanoic acid.

[0007] In yet another aspect, a process for producing 1 -pentadecanoic acid can comprise contacting a feedstock olefin composition comprising at least 75 mol % 1-tetradecene with a hydrocarboxylation catalyst system, carbon monoxide, and water to form a composition comprising 1 -pentadecanoic acid.

[0008] In still another aspect, the present disclosure encompasses a composition comprising 1 -pentadecanoic acid derived from a feedstock olefin composition comprising 1-tetradecene and / or 1 -hexadecene, and also encompasses the use of the composition as a food additive, vitamin, or dietary supplement.

[0009] Both the foregoing summary and the following detailed description provide examples and are explanatory only. Accordingly, the foregoing summary and the following detailed description should not be considered to be restrictive. Further, features or variations can be provided in addition to those set forth herein. For example, certain aspects can be directed to various feature combinations and sub-combinations described in the detailed description.DEFINITIONS

[0010] To define more clearly the terms used herein, the following definitions are provided. Unless otherwise indicated, the following definitions are applicable to this disclosure. If a term is used in this disclosure but is not specifically defined herein, the definition from the IUPAC Compendium of Chemical Terminology', 2nd Ed (1997), can be applied, as long as that definition does not conflict with any other disclosure or definition applied herein, or render indefinite or non-enabled any claim to which that definition is applied. To the extent that any definition or usage provided by any document incorporated2118-163-344herein by reference conflicts with the definition or usage provided herein, the definition or usage provided herein controls.

[0011] Herein, features of the subject matter can be described such that, within particular aspects, a combination of different features can be envisioned. For each and every aspect and / or feature disclosed herein, all combinations that do not detrimentally affect the designs, compositions, processes, and / or methods described herein are contemplated with or without explicit description of the particular combination. Additionally, unless explicitly recited otherwise, any aspect and / or feature disclosed herein can be combined to describe inventive features consistent with the present disclosure.

[0012] In this disclosure, while compositions and processes / methods are described in terms of “comprising” various materials or steps, the compositions and processes / methods also can “consist essentially of’ or “consist of’ the various materials or steps, unless stated otherwise. The terms “a,” “an,” and “the” are intended to include plural alternatives, e.g., at least one. unless otherwise specified.

[0013] The terms “contacting” and “subjecting” and “oxidizing” are used herein to describe compositions and processes / methods in which the materials or components are combined together in any order, in any manner, and for any length of time, unless otherwise specified. For example, the materials or components can be blended, mixed, slurried, dissolved, reacted, treated, impregnated, compounded, or otherwise combined in some other manner or by any suitable method or technique. Often, contacting or subjecting or oxidizing results in a reaction between two or more materials, thereby forming a reaction product or a reaction mixture.

[0014] Generally, groups of elements are indicated using the numbering scheme indicated in the version of the periodic table of elements published in Chemical and Engineering New s, 63(5), 27, 1985. In some instances, a group of elements can be indicated using a common name assigned to the group; for example, alkali metals for Group 1 elements, alkaline earth metals for Group 2 elements, transition metals for Group 3-12 elements, and halogens or halides for Group 17 elements.

[0015] For any particular compound or group disclosed herein, any name or structure presented is intended to encompass all conformational isomers, regioisomers, stereoisomers, and mixtures thereof that can arise from a particular set of substituents, unless otherwise specified. The name or structure also encompasses all enantiomers, diastereomers, and other optical isomers (if there are any), whether in enantiomeric or racemic forms, as well as 3118-163-344mixtures of stereoisomers, as would be recognized by a skilled artisan, unless otherwise specified. For example, a general reference to hexene (or hexenes) includes all linear or branched, acyclic or cyclic, hydrocarbon compounds having six carbon atoms and 1 carboncarbon double bond; a general reference to pentane includes n-pentane, 2-methyl-butane, and 2,2-dimethylpropane; and a general reference to a butyl group includes an n-butyl group, a sec-butyl group, an iso-butyl group, and a t-butyl group.

[0016] Several types of ranges are disclosed in the present invention. When a range of any type is disclosed or claimed, the intent is to disclose or claim individually each possible number that such a range could reasonably encompass, including end points of the range as well as any sub-ranges and combinations of sub-ranges encompassed therein. For example, the feedstock olefin composition in one of the disclosed processes can contain from 1 to 20 mol % of Ci4 vinylidenes. By a disclosure that the amount of vinylidenes in the feedstock olefin composition can be within a range from 1 to 20 mol %, the intent is to recite that the amount of vinylidenes can be any amount in the range and, for example, can include any range or combination of ranges from 1 to 20 mol %, such as from 2 to 18 mol %, from 2 to 12 mol %, from 3 to 20 mol %, from 3 to 12 mol %, from 3 to 8 mol %, or from 3 to 6 mol % Ci4 vinylidenes, and so forth. Likewise, all other ranges disclosed herein should be interpreted in a manner similar to this example.

[0017] In general, an amount, size, formulation, parameter, range, or other quantity’ or characteristic is "about" or “approximate” whether or not expressly stated to be such.Whether or not modified by the term “about” or “approximately,” the claims include equivalents to the quantities or characteristics.

[0018] In the processes disclosed and claimed herein, and not limited thereto, a product in one step can be used as a reactant in another step, or a material can be separated or isolated from a reaction mixture or composition. For instance, when aldehydes are produced in a first step and then utilized in a subsequent step, “all or any portion of’ the aldehydes produced in the first step can then be utilized in the subsequent step, even if not specifically stated so. Similarly, for example, when a product such as 1 -pentadecanoic acid is isolated from a reaction mixture or composition, “all or any portion of’ the pentadecanoic acid can be isolated from the reaction mixture or composition, even if not specifically stated so.Likewise, all process steps in the specification and in the claims should be interpreted in a manner similar to these examples.4118-163-344

[0019] Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the invention, the typical methods and materials are herein described.

[0020] All publications and patents mentioned herein are incorporated herein by reference in their entirety for the purpose of describing and disclosing, for example, the constructs and methodologies that are described in the publications and patents, which might be used in connection with the presently described invention.DETAILED DESCRIPTION

[0021] 1 -Pentadecanoic acid is synthesized herein using either 1 -tetradecene or 1-hexadecene as the starting material.SYNTHESIZING 1 -PENTADECANOIC ACID FROM 1 -TETRADECENE

[0022] Herein, a first process is a process for producing 1 -pentadecanoic acid from 1 -tetradecene, and this first process can comprise (or consist essentially of, or consist of) (i) contacting a feedstock olefin composition comprising at least 75 mol % 1 -tetradecene with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form a first composition comprising Cis aldehydes, and (ii) oxidizing (all or any portion of) the Cis aldehydes to form a second composition comprising 1 -pentadecanoic acid.

[0023] Generally, the features of the first process (e g., the components in the feedstock olefin composition, the amount of 1 -tetradecene, the hydroformylation catalyst system, the oxidizing step, the first composition, the second composition, and the conditions under which steps (i) and (ii) are conducted, among others) are independently described herein and these features can be combined in any combination to further describe the disclosed processes to produce 1 -pentadecanoic acid. Moreover, additional process steps can be performed before, during, and / or after any of the steps in any of the processes disclosed herein, and can be utilized without limitation and in any combination to further describe these processes, unless stated otherwise. Further, any 1 -pentadecanoic acid or product composition streams produced in accordance with the disclosed processes are within the scope of this disclosure and are encompassed herein.

[0024] The feedstock olefin composition in step (i) can contain at least 75 mol % of 1 -tetradecene. More often, the feedstock olefin composition can contain at least 80 mol % 1 -tetradecene in one aspect, at least 85 mol % 1 -tetradecene in another aspect, at least 90 mol %5118-163-3441 -tetradecene in another aspect, at least 92 mol % 1 -tetradecene in another aspect, at least 93 mol % 1 -tetradecene in another aspect, at least 95 mol % 1 -tetradecene in yet another aspect, and at least 97 mol % 1 -tetradecene in still another aspect. Maximum amounts of 1-tetradecene in the feedstock olefin compositions can be less than or equal to 99.5 mol %. less than or equal to 99 mol %, less than or equal to 98 mol %, less than or equal to 97 mol %, or less than or equal to 96 mol %, although not limited thereto. Generally, the amount of 1-tetradecene in the feedstock olefin composition can range from any minimum amount disclosed herein to any maximum amount disclosed herein. The molar amount of 1-tetradecene is based on the total molar amount of olefins in the feedstock olefin composition; therefore, non-olefinic components such as alkanes and diluents / solvents are not included.

[0025] Optionally, other Ci4 olefins - such as Ci4 vinylidenes - can be present in the feedstock olefin composition. For instance, when present, the amount of Ci4 vinylidenes in the feedstock olefin composition can range from 1 to 20 mol %, and more often, from 2 to 18 mol %, from 2 to 12 mol %, from 3 to 20 mol %, from 3 to 12 mol %, from 3 to 8 mol %, or from 3 to 6 mol % Ci4 vinylidenes, and the like. As would be recognized, in the case of branched olefins, a branch can be at the 2-position of a 1 -alkene (a vinylidene) with respect to the olefin double bond. Thus, the term “vinylidene"’ refers to a 1 -alkene having an alkyl branch at the 2-position with respect to the olefin double bond.

[0026] Additionally or alternatively, the feedstock olefin composition can further include from 0.1 to 20 mol % of Ci4 branched alpha-olefins (excluding vinylidenes). When present in the feedstock olefin composition, the amount of Ci4 branched alpha-olefins (excluding vinylidenes) typically ranges from 0.1 to 5 mol %. from 0.1 to 1 mol %, from 0.5 to 20 mol %, from 0.5 to 5 mol %, from 1 to 20 mol %, or from 2 to 10 mol % Ci4 branched alpha-olefins, and the like.

[0027] Additionally or alternatively, the feedstock olefin composition can contain internal olefins. When present, the amount of Ci4 internal olefins can range from 0.1 to 10 mol %, from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 10 mol %, from 0.5 to 5 mol %, from 1 to 10 mol %, or from 1 to 5 mol % Ci4 internal olefins, and the like.

[0028] Additionally or alternatively, C 14 alkanes can be present in the feedstock olefin composition, generally in the range from 0.1 to 20 mol %. Other suitable ranges for the amount of Ci4 alkanes in the feedstock olefin composition can include, but are not limited to, from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 20 mol %, from 0.5 to 5 mol %, from6118-163-3441 to 20 mol %, or from 2 to 10 mol %. The molar amount of the alkanes is based on the total molar amount of olefins in the feedstock olefin composition.

[0029] Step (i) of the first process disclosed herein often is referred to as the hydroformylation step, and in this step, the feedstock olefin composition is contacted with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form a first composition comprising Cis aldehydes. Thus, this hydroformylation step can convert a normal alpha olefin to a (higher carbon number) linear aldehyde. Any suitable hydroformylation catalyst systems for step (i) and any suitable conditions for the hydroformylation reaction in step (i) can be employed, as would be recognized by those skilled in the art in view of this disclosure, and for instance, Behr at al., Journal of Molecular Catalysis A: Chemical 206 (2003), 179-184; Vogl at al., Journal of Molecular Catalysis A: Chemical 232 (2005), 41-44; Jorke et al., Chemical Engineering Journal, December 12, 2016, 1-34; Peng et al.. U.S. Patent No. 7,196,230; U.S. Patent No. 3,420,898; Yan et al.. Journal of the American Chemical Society (2006), 128, 16058-16061; and Kranenburg et al., Organometallics 1995, 14, 3081-3089.

[0030] While not being limited thereto, the hydroformylation catalyst system can comprise a cobalt compound, or a rhodium compound, or both a cobalt compound and a rhodium compound. When the hydroformylation catalyst system comprises the cobalt compound, any suitable specific catalyst components and any suitable reaction conditions can be used to convert 1 -tetradecene to Cis aldehydes, as disclosed in the references noted hereinabove. While not wishing to be bound by the following theory, it is believed that cobalt catalyst systems may be less selective to linear aldehydes (e.g., 80-85 mol %, see U.S. Patent No. 3,420,898) with more by-product ketones and / or branched aldehydes.

[0031] When the hydroformylation catalyst system comprises the rhodium compound, any suitable specific catalyst components and any suitable reaction conditions can be used to convert 1-tetradecene to C15 aldehydes, as disclosed in the references noted hereinabove. While not wishing to be bound by the following theory, it is believed that rhodium catalyst systems with certain ligands - such as bidentate ligands - can produce linear aldehydes with high selectivity' (e.g., 97 mol %, see Organometallics 1995, p. 3081).

[0032] For example, in the rhodium-based catalyst system, the catalyst system can include rhodium and a phosphorus-containing ligand, and the elemental ratio of Rh:P often can range from 1 : 1 to 1 : 15, and more often, the elemental ratio of Rh: P falls within a range from 1 :2 to 1 : 10, or from 1 :2 to 1:6, and the like. The particular phosphorus-containing 7118-163-344ligand is not particularly limited, although BiPhePhos (CAS Number 121627-17-6) is well-suited for use in rhodium-based catalyst systems employed in hydroformylation reactions.

[0033] In one aspect, the molar ratio of olefins in the feedstock olefin composition (or the molar ratio of 1 -tetradecene in the feedstock olefin composition) in step (i) to rhodium (or to cobalt) in the hydroformylation catalyst system can fall within a range from 100: 1 to 500,000:1, while in another aspect, the molar ratio can range from 100:1 to 10,000:1, and in yet another aspect, the molar ratio can range from 100:1 to 1000:1. As those skilled in the art would readily recognize, the olefin (or 1 -tetradecene) to rhodium (or cobalt) molar ratio can change as the hydroformylation reaction proceeds. Accordingly, these ranges of molar ratios are meant to encompass the initial ratio as well as any molar ratio of the olefins (or 1-tetradencene) to rhodium (or cobalt) encountered as the hydroformylation reaction proceeds.

[0034] Additionally, the molar ratio of carbon monoxide to hydrogen (H2) in the hydroformylation reaction of step (i) often ranges from 5:1 to 1:5 or from 2:1 to 1:2 in some aspects, and from 1.5:1 to 1:1.5 or from 1.1:1 to 1:1.1 in other aspects. The source of carbon monoxide and hydrogen used in step (i) is not limited, but in a particular aspect of this invention, the source of carbon monoxide and hydrogen in step (i) can be Syngas. As would be recognized by those skilled in the art. Syngas is a mixture containing predominately carbon monoxide and hydrogen. Syngas also can contain carbon dioxide and methane in lesser amounts.

[0035] The temperature and pressure conditions used for the hydroformylation step are not particularly limited. Generally, however, the hydroformylation temperature can be in a range from 50 to 300 °C; alternatively, from 50 to 200 °C: or alternatively, from 70 to 150 °C. The hydroformylation pressure can be in range from 4 to 70 bar; alternatively, from 6 to 50 bar; or alternatively, from 8 to 45 bar. These temperature and pressure ranges also are meant to encompass circumstances where step (i) is conducted at a series of different temperatures and pressures instead of at a single fixed temperature and a single fixed pressure, wherein at least one temperature and pressure fall within the respective ranges.

[0036] If desired, and depending upon the compositional breakdown of the feedstock olefin composition, the hydroformylation temperature, and the hydroformylation pressure, among other considerations, the hydroformylation reaction of step (i) optionally can be performed in a diluent. Illustrative and non-limiting examples of diluents that can be used include toluene, propylene carbonate, dimethylformamide, dodecane, and the like, as well as a mixture or combination thereof (see, e.g., Stein, Molecular Catalysis 503, 2021, 111429).8118-163-344Any suitable amount of the diluent, relative to the amount of olefins (or 1 -tetradecene) in the feedback olefin composition, can be used.

[0037] Typically, using hydroformylation in step (i) can produce both linear and branched aldehydes, and optionally some by-product ketones, enals, alcohols, and / or paraffins, but primarily produces linear aldehydes. Thus, the first composition produced via the hydroformylation of step (i) can include the C15 linear aldehyde (pentadecanal), C15 branched aldehydes, and by-products (if present). Optionally, prior to step (ii), the process can further comprise a step of isomerizing the first composition comprising the C15 aldehydes prior to step (ii) to convert (all or any portion of) C15 ketones to C15 aldehydes. While not wishing to be bound by theory, it is believed that the proper selection of the hydroformylation catalyst system and reaction conditions would minimize the production of any by-products, even if the feedstock olefin composition contains significant amounts of internal olefins.

[0038] Optionally, prior to step (ii), the process can further comprise a step of isolating an aldehyde composition comprising at least 75 mol %, and more often, at least 80 mol %, at least 85 mol %, at least 90 mol %, at least 95 mol %, at least 97 mol %, or at least 99 mol % of C15 aldehydes from the first composition. Any suitable technique can be used, such as extraction, filtration, evaporation, distillation, fractional distillation, metathesis followed by distillation, and the like, as well as any combination thereof.

[0039] Referring now to step (ii) of the process, (all or any portion of) the C15 aldehydes formed in step (i) are oxidized to form a second composition comprising 1-pentadecanoic acid. Accordingly, step (ii) of the process often is referred to as the oxidation step. Thus, in step (ii), C15 aldehydes such as pentadecanal are oxidized to the corresponding acid of the same carbon number, desirably 1 -pentadecanoic acid. Any suitable oxidation reagents for step (ii) and any suitable conditions (e.g., temperature, pressure, etc.) for the oxidative conversion of aldehydes to corresponding carboxylic acids in step (ii) can be employed, as would be recognized by those skilled in the art in view of this disclosure, and for instance, Sedelmeier et al.. Organic Letters, Vol 12, No 16, 2010, 3618-3621: and Vanoye et al., Organic Process Research & Development 2022, 26, 335-346.

[0040] For instance, in one aspect, oxidizing in step (ii) can comprise contacting (reacting) the C15 aldehydes with KMnO4 and Na2HPO4 to form the second composition comprising the 1 -pentadecanoic acid. In another aspect, oxidizing in step (ii) can comprise contacting (reacting) the C15 aldehydes with molecular O2 in acetonitrile, optionally in the presence of a catalyst, to form the second composition comprising the 1 -pentadecanoic acid.9118-163-344In yet another aspect, oxidizing in step (ii) can comprise contacting (reacting) the C15 aldehydes with Na2Cr2O? / H2SO4 to form the second composition comprising the 1-pentadecanoic acid.

[0041] The second composition can be further processed to isolate or separate (all or any portion of) the 1 -pentadecanoic acid from the second composition. For example, the first process can comprise a step of purifying the second composition to isolate a product composition comprising at least 80 wt. %, and more often, at least 85 wt. %, at least 90 wt. %, at least 95 wt. %, at least 96 wt %, at least 97 wt. %, at least 98 wt. %, at least 99 wt. %, or at least 99.5 wt. % of 1 -pentadecanoic acid. The amount of 1 -pentadecanoic acid is based on the total weight of the product composition. Any suitable technique can be used, such as extraction, filtration, evaporation, distillation, fractional distillation, and the like, as well as any combination thereof.

[0042] While not wishing to be bound by theory, and depending upon the compositional breakdown of the second composition, it may be beneficial to maintain lesser amounts of branched C15 carboxylic acids in the product composition along with the 1-pentadecanoic acid.SYNTHESIZING 1 -PENTADECANOIC ACID FROM 1 -HEXADECENE

[0043] Herein, a second process is a process for producing 1 -pentadecanoic acid from 1 -hexadecene, and this second process can comprise (or consist essentially of, or consist of) (a) subjecting a feedstock olefin composition comprising at least 75 mol % 1 -hexadecene to ozonolysis to form a first composition comprising C15 aldehydes, and (b) oxidizing (all or any portion of) the C15 aldehydes to form a second composition comprising 1 -pentadecanoic acid.

[0044] Generally, the features of the second process (e.g., the components in the feedstock olefin composition, the amount of f-hexadecene, the ozonolysis step, the oxidizing step, the first composition, the second composition, and the conditions under which steps (a) and (b) are conducted, among others) are independently described herein and these features can be combined in any combination to further describe the disclosed processes to produce 1-pentadecanoic acid. Moreover, additional process steps can be performed before, during, and / or after any of the steps in any of the processes disclosed herein, and can be utilized without limitation and in any combination to further describe these processes, unless stated otherwise. Further, any 1 -pentadecanoic acid or product composition streams produced in10118-163-344accordance with the disclosed processes are within the scope of this disclosure and are encompassed herein.

[0045] The feedstock olefin composition in step (a) can contain at least 75 mol % of 1 -hexadecene. More often, the feedstock olefin composition can contain at least 80 mol % 1-hexadecene in one aspect, at least 85 mol % 1 -hexadecene in another aspect, at least 90 mol % 1 -hexadecene in another aspect, at least 92 mol % 1 -hexadecene in another aspect, at least 93 mol % 1 -hexadecene in another aspect, at least 95 mol % 1 -hexadecene in yet another aspect, and at least 97 mol % 1 -hexadecene in still another aspect. Maximum amounts of 1-hexadecene in the feedstock olefin compositions can be less than or equal to 99.5 mol %, less than or equal to 99 mol %, less than or equal to 98 mol %, less than or equal to 97 mol %, or less than or equal to 96 mol %, although not limited thereto. Generally, the amount of 1-hexadecene in the feedstock olefin composition can range from any minimum amount disclosed herein to any maximum amount disclosed herein. The molar amount of 1-hexadecene is based on the total molar amount of olefins in the feedstock olefin composition; therefore, non-olefinic components such as alkanes and diluents / solvents are not included.

[0046] Optionally, other Ci6 olefins - such as Ci6 vinylidenes - can be present in the feedstock olefin composition. For instance, when present, the amount of C16 vinylidenes in the feedstock olefin composition can range from 1 to 20 mol %, and more often, from 2 to 18 mol %, from 2 to 12 mol %, from 3 to 20 mol %, from 3 to 12 mol %, from 3 to 8 mol %, or from 3 to 6 mol % Ci6 vinylidenes, and the like. As noted above, the term '‘vinylidene” refers to a 1 -alkene having an alkyl branch at the 2-position with respect to the olefin double bond.

[0047] Additionally or alternatively, the feedstock olefin composition can further include from 0.1 to 20 mol % of Ci6 branched alpha-olefins (excluding vinylidenes). When present in the feedstock olefin composition, the amount of Ci6 branched alpha-olefins (excluding vinylidenes) typically ranges from 0.1 to 5 mol %. from 0.1 to 1 mol %, from 0.5 to 20 mol %, from 0.5 to 5 mol %, from 1 to 20 mol %, or from 2 to 10 mol % Ci6 branched alpha-olefins, and the like.

[0048] Additionally or alternatively, the feedstock olefin composition can contain internal olefins. When present, the amount of Ci6 internal olefins can range from 0.1 to 10 mol %. from 0.1 to 5 mol %. from 0.1 to 1 mol %, from 0.5 to 10 mol %. from 0.5 to 5 mol %, from 1 to 10 mol %, or from 1 to 5 mol % Ci6 internal olefins, and the like.11118-163-344

[0049] Additionally or alternatively, Ci6 alkanes can be present in the feedstock olefin composition, generally in the range from 0.1 to 20 mol %. Other suitable ranges for the amount of Ci6 alkanes in the feedstock olefin composition can include, but are not limited to, from 0.1 to 5 mol %, from 0.1 to 1 mol %. from 0.5 to 20 mol %, from 0.5 to 5 mol %, from 1 to 20 mol %, or from 2 to 10 mol %. The molar amount of the alkanes is based on the total molar amount of olefins in the feedstock olefin composition.

[0050] Step (a) of the second process disclosed herein often is referred to as the ozonolysis step, and in this step, the feedstock olefin composition is subjected to ozonolysis to form a first composition comprising Cis aldehydes. Thus, this ozonolysis step can convert a normal alpha olefin to a (lower carbon number) linear aldehyde. Any suitable ozonolysis reagents for step (a) and any suitable ozonolysis conditions (e.g., temperature, pressure, etc.) for the conversion of alpha olefins to lower carbon number aldehydes in step (a) can be employed, as would be recognized by those skilled in the art in view of this disclosure, and for instance, Fisher et al., Tetrahedron 73, 2017. 4233-4258.

[0051] For instance, in an aspect, ozonolysis in step (a) can comprise contacting (reacting) the feedstock olefin composition (comprising the 1 -hexadecene) with ozone and then with a reducing agent to form the first composition comprising the Cis aldehydes.

[0052] Typically, using ozonolysis in step (a) can produce both linear and branched aldehydes, and optionally some by-product ketones, but primarily produces linear aldehydes. Thus, the first composition produced via the ozonolysis of step (a) can include the Cis linear aldehyde (pentadecanal), Cis branched aldehydes, and Cis ketones (if present). Optionally, prior to step (b), the process can further comprise a step of isolating an aldehyde composition comprising at least 75 mol %, and more often, at least 80 mol %, at least 85 mol %, at least 90 mol %, at least 95 mol %, at least 97 mol %, or at least 99 mol % of Cis aldehydes from the first composition. Any suitable technique can be used, such as extraction, filtration, evaporation, distillation, fractional distillation, metathesis followed by distillation, and the like, as well as any combination thereof.

[0053] Referring now to step (b) of the process, (all or any portion of) the Cis aldehydes formed in step (a) are oxidized to form a second composition comprising 1-pentadecanoic acid. Accordingly, step (b) of the process often is referred to as the oxidation step. Thus, in step (b). Cis aldehydes such as pentadecanal are oxidized to the corresponding acid of the same carbon number, desirably 1 -pentadecanoic acid. Any suitable oxidation reagents for step (b) and any suitable conditions (e.g., temperature, pressure, etc.) for the 12118-163-344oxidative conversion of aldehydes to corresponding carboxylic acids in step (b) can be employed, as would be recognized by those skilled in the art in view of this disclosure, and for instance, Sedelmeier et al., Organic Letters, Vol 12, No 16, 2010, 3618-3621; and Vanoye et al.. Organic Process Research & Development 2022, 26, 335-346.

[0054] For instance, in one aspect, oxidizing in step (b) can comprise contacting (reacting) the Cis aldehydes with KMnO4 and Na2HPO4 to form the second composition comprising the 1 -pentadecanoic acid. In another aspect, oxidizing in step (b) can comprise contacting (reacting) the Cis aldehydes with molecular O2 in acetonitrile, optionally in the presence of a catalyst, to form the second composition comprising the 1 -pentadecanoic acid. In yet another aspect, oxidizing in step (b) can comprise contacting (reacting) the Cis aldehydes with Na2Cr2O? / H2SO4 to form the second composition comprising the 1-pentadecanoic acid. In still another aspect, oxidizing in step (b) can comprise contacting (reacting) the Cis aldehydes with H2O2 to form the second composition comprising the 1-pentadecanoic acid.

[0055] The second composition can be further processed to isolate or separate (all or any portion of) the 1 -pentadecanoic acid from the second composition. For example, the second process can comprise a step of purifying the second composition to isolate a product composition comprising at least 80 wt. %. and more often, at least 85 wt. %, at least 90 wt. %, at least 95 wt. %, at least 96 wt. %, at least 97 wt. %, at least 98 wt. %, at least 99 wt. %, or at least 99.5 wt. % of 1 -pentadecanoic acid. Any suitable technique can be used, such as extraction, filtration, evaporation, distillation, fractional distillation, and the like, as well as any combination thereof.

[0056] As noted above and while not wishing to be bound by theory, and depending upon the compositional breakdown of the second composition, it may be beneficial to maintain lesser amounts of branched C15 carboxylic acids in the product composition along with the 1 -pentadecanoic acid.OTHER METHODS FOR SYNTHESIZING 1 -PENTADECANOIC ACID

[0057] Another process for producing 1 -pentadecanoic acid in accordance with this invention can comprise contacting a feedstock olefin composition comprising at least 75 mol % 1 -tetradecene with a hydrocarboxylation catalyst system, carbon monoxide, and water to form a composition comprising 1 -pentadecanoic acid. Any suitable hydrocarboxylation catalyst systems and any suitable conditions for the hydrocarboxylation reaction can be 13118-163-344employed, as would be recognized by those skilled in the art in view of this disclosure, and for instance, Nature Communications (2022) 13:7584.

[0058] Also disclosed herein is a composition comprising 1 -pentadecanoic acid derived from a feedstock olefin composition comprising (e.g., at least 75 mol % of) 1-tetradecene and / or 1 -hexadecene, and also encompasses the use of the composition as a food additive, a vitamin, or a dietary supplement.USES AND BENEFITS OF 1 -PENTADECANOIC ACID

[0059] Herein, the processes to produce 1 -pentadecanoic acid can include a step of purifying the second composition to isolate a product composition comprising at least 80 wt. %, and more often, at least 85 wt. %, at least 90 wt. %, at least 95 wt. %, at least 96 wt. %, at least 97 wt. %, at least 98 wt. %, at least 99 wt. %, or at least 99.5 wt. % of 1 -pentadecanoic acid. Also encompassed herein, therefore, are the product compositions comprising the 1-pentadecanoic acid - in any suitable amount - prepared by either the first process or the second process. Further, the present disclosure also encompasses any tablet, gel, or capsule containing the product composition comprising the 1 -pentadecanoic acid, as w ell as any food additive, vitamin, or dietary supplement containing the product composition comprising the 1 -pentadecanoic acid.

[0060] A number of studies over the past several years have correlated reduced consumption of 1 -pentadecanoic acid (Cl 5:0) with poor outcomes in human health, such as can be found in the following references: Fatty 15.com; Nature.com / scientificreports (https: / / doi.org / 10.1038 / s41598-020-64960-y); Metabolites 2024. 14. 355 (https: / / doi.org / 10.3390 / metaboll4070355); Biochimie 2024 (https: / / doi.Org / 10.1016 / j.biochi.2024.10.008); and PLoS ONE 2022, 17(5) (https: / / doi.org / 10.1371 / joumal.pone.0268778). In the human diet, C15:0 is primarily consumed via dairy’ fat, and it is believed that the emphasis on consumption of low-fat dairy products for the past 50 years has contributed to these maladies.

[0061] At the forefront of these studies is Venn-Watson of Seraphina Therapeutics, who showed that dolphins that were fed a fish-based diet containing higher levels of C 15:0 exhibited lower symptoms of metabolic syndrome than a control group. Since these original studies, additional research has been conducted in vitro on multiple cell lines, and in vivo with human subjects. C15:0 has been commercialized as a product called fatty15, sold as a supplement to be taken daily in the form of a 100 mg capsule. Seraphina Therapeutics makes 14118-163-344the following assertions: (i) C 15:0 is an essential fatty acid that must be consumed by humans, and cannot be produced at appreciable levels in the human body; (ii) C15:0 deficiency contributes to Type 2 Diabetes, NASH (non-alcoholic fatty liver disease), cardiovascular disease, neurodegenerative disease (via inflammation), cellular fragility, and accelerated aging; (iii) Cl 5:0 supplementation reverses all of the markers that contribute to the above conditions; (iv) C15:0 may have anti-cancer and anti-microbial properties, and may be may be able to help treat depression and autoimmune diseases; (v) Studies in the world's five Blue Longevity Zones show elevated levels of C 15:0 in the populations, with even higher levels in the longest lived people; and (vi) Customer feedback following commercialization of fatty15has been overwhelmingly positive.

[0062] There are several patents and publications that cover the use of Cl 5:0 as part of a treatment regimen for humans, and even the composition of the fatty acid. See, for example, U.S. Patent Publication No. 2019 / 0358183 Al, U.S. Patent No. 11,116.740 B2, and U.S. Patent No. 10,307,388 B2.

[0063] Despite these encouraging results from the literature and the customers, fatty15faces some barriers to larger acceptance and usage (100-200 mg / day). Based on publicly available information, it seems likely that fatt15has been traditionally produced via the extraction of 1 -tetradecanoic acid (C14:0) from nutmeg (see Proceedings 2021, 70. 33 (https: / / doi.org / 10.3390 / foods_2020-07687)), then converted to C15:0 by “adding a carbon,’’ a process know n as homologation (see J. Org. Chem. 2001, 66, 5606-5612). Nutmeg oil contains about 75% C14:0, and this precursor acid can be converted to the C15:0 by a multi-step synthesis using expensive chemicals and unit operations. It is believed that the first process for producing 1 -pentadecanoic acid (from 1 -tetradecene) and the second process for producing 1 -pentadecanoic acid (from 1 -hexadecene) disclosed herein overcome the drawbacks of the traditional synthesis technique that utilizes nutmeg as the starting raw' material.EXAMPLES

[0064] The invention is further illustrated by the following examples, which are not to be construed in any way as imposing limitations to the scope of this invention. Various other aspects, modifications, and equivalents thereof which, after reading the description herein, can suggest themselves to one of ordinary skill in the art without departing from the spirit of the present invention or the scope of the appended claims.15118-163-344

[0065] The general reaction scheme for the synthesis of 1 -pentadecanoic acid from either 1 -tetradecene or 1 -hexadecene is shown below.C aldehyde C15carboxylic acid (C15:0)"oxidation" OHCONSTRUCTIVE EXAMPLE 1

[0066] In accordance with the first process for producing 1 -pentadecanoic acid from 1 -tetradecene disclosed herein, Constructive Example 1 demonstrates a representative and non-limiting example of the conversion of 1 -tetradecene to 1 -pentadecanoic acid.

[0067] First, a feedstock olefin composition containing 92 mol % 1 -tetradecene (and 3 mol % Ci4 vinylidenes, 3 mol % Ci4 branched alpha-olefins, and 2 mol % Ci4 internal olefins) is combined with a rhodium-BiPhePhos catalyst system in a reactor. The elemental ratio of Rh:P is 1:1.1, and the molar ratio of the 1 -tetradecene to rhodium is 10,000:1.Carbon monoxide and hydrogen (Eb) are added to the reactor at a total pressure of 30 bar and a molar ratio of carbon monoxide to hydrogen of 1 : 1. The reactor is heated to 150 °C and the reactor contents are stirred for 1 hr to produce a first composition containing 1 -pentadecanal. After cooling, an aldehyde composition containing 92 mol % 1 -pentadecanal is separated from the first composition by distillation.

[0068] The aldehyde composition containing 1 -pentadecanal is oxidized by mixing the aldehyde composition in a reactor with KMnCh and Na2HPO4 at a temperature, pressure, reaction time, and other reaction conditions known to those of skill in the art, thereby forming a second composition comprising the 1 -pentadecanoic acid. After cooling, the second composition is purified by distillation to isolate a product composition containing 94 wt. % 1-pentadecanoic acid.16118-163-344CONSTRUCTIVE EXAMPLE 2

[0069] In accordance with the second process for producing 1 -pentadecanoic acid from 1 -hexadecene disclosed herein, Constructive Example 2 demonstrates a representative and non-limiting example of the conversion of 1 -hexadecene to 1 -pentadecanoic acid.

[0070] First, a feedstock olefin composition containing 91 mol % 1-hexadecene (and 4 mol % Ci6 vinylidenes, 3 mol % Ci6 branched alpha-olefins, and 2 mol % Ci6 internal olefins) is combined with ozone (Os) and then with a reducing agent at a temperature, pressure, reaction time, and other reaction conditions known to those of skill in the art, thereby forming a first composition containing 1 -pentadecanal. After cooling, an aldehyde composition containing 94 mol % 1 -pentadecanal is separated from the first composition by distillation.

[0071] The aldehyde composition containing 1 -pentadecanal is oxidized by mixing the aldehyde composition in a reactor with Na2Cr2O? / H2SO4 at a temperature, pressure, reaction time, and other reaction conditions known to those of skill in the art, thereby forming a second composition comprising the 1 -pentadecanoic acid. After cooling, the second composition is purified by distillation to isolate a product composition containing 95 wt. % 1-pentadecanoic acid.ASPECTS OF THE DISCLOSURE

[0072] The invention is described herein with reference to numerous aspects and specific examples. Many variations will suggest themselves to those skilled in the art in light of the detailed description. All such obvious variations are within the full intended scope of the appended claims. Other aspects of the invention can include, but are not limited to, the following (aspects are described as “comprising” but, alternatively, can “consist essentially of’ or “consist of’):

[0073] Aspect 1. A process comprising (i) contacting a feedstock olefin composition comprising at least 75 mol % 1 -tetradecene with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form a first composition comprising Cis aldehydes, and (ii) oxidizing the Cis aldehydes to form a second composition comprising 1 -pentadecanoic acid.

[0074] Aspect 2. The process defined in aspect 1, wherein the feedstock olefin composition comprises at least 80 mol %, at least 85 mol %, at least 90 mol %. at least 92 mol %, at least 93 mol %, at least 95 mol %, or at least 97 mol % of the 1 -tetradecene.17118-163-344

[0075] Aspect 3. The process defined in aspect 1 or 2, wherein the feedstock olefin composition further comprises from 1 to 20 mol %, from 2 to 18 mol %, from 2 to 12 mol %, from 3 to 20 mol %, from 3 to 12 mol %, from 3 to 8 mol %, or from 3 to 6 mol % Ci4 vinylidenes.

[0076] Aspect 4. The process defined in any one of aspects 1-3, wherein the feedstock olefin composition further comprises from 0.1 to 10 mol %, from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 10 mol %, from 0.5 to 5 mol %, from 1 to 10 mol %, or from 1 to 5 mol % Ci4 internal olefins.

[0077] Aspect 5. The process defined in any one of aspects 1-4. wherein the feedstock olefin composition further comprises from 0.1 to 20 mol %, from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 20 mol %, from 0.5 to 5 mol %, from 1 to 20 mol %, or from 2 to 10 mol % Ci4 branched alpha-olefins.

[0078] Aspect 6. The process defined in any one of aspects 1-5. wherein the feedstock olefin composition further comprises from 0.1 to 20 mol %. from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 20 mol %, from 0.5 to 5 mol %, from 1 to 20 mol %, or from 2 to 10 mol % Ci4 alkanes.

[0079] Aspect 7. The process defined in any one of aspects 1-6. wherein the hydroformylation catalyst system comprises a cobalt compound, a rhodium compound, or a combination thereof.

[0080] Aspect 8. The process defined in any one of aspects 1-7, wherein the hydroformylation catalyst system comprises a cobalt compound.

[0081] Aspect 9. The process defined in any one of aspects 1-8. wherein the hydroformylation catalyst system comprises a rhodium compound.

[0082] Aspect 10. The process defined in aspect 9, wherein the hydroformylation catalyst system comprises rhodium and a phosphorus-containing ligand at an elemental ratio of Rh:P in a range from 1:1 to 1:15, from 1:2 to 1:10, or from 1:2 to 1:6.

[0083] Aspect 11. The process defined in aspect 10, wherein the phosphorus-containing ligand comprises BiPhePhos.

[0084] Aspect 12. The process defined in any one of aspects 7-11, wherein a molar ratio of olefins in the feedstock olefin composition (or the 1 -tetradecene in the feedstock olefin composition) to rhodium (or to cobalt) is in a range from 100: 1 to 500.000: 1, from 100:1 to 10,000:1, or from 100:1 to 1000:1.18118-163-344

[0085] Aspect 13. The process defined in any one of aspects 1-12, wherein a molar ratio of carbon monoxide to hydrogen in step (i) is in a range from 5: 1 to 1 :5, from 2: 1 to 1 :2, or from 1.5:1 to 1:1.5.

[0086] Aspect 14. The process defined in any one of aspects 1-13, wherein a source of carbon monoxide and hydrogen in step (i) is Syngas.

[0087] Aspect 15. The process defined in any one of aspects 1-14, wherein step (i) is conducted (or the first composition is formed) at a pressure from 5 to 70 bar, from 10 to 50 bar, or from 20 to 45 bar.

[0088] Aspect 16. The process defined in any one of aspects 1-15, wherein step (i) is conducted (or the first composition is formed) at a temperature from 50 to 300 °C, from 50 to 200 °C, or from 70 to 150 °C.

[0089] Aspect 17. The process defined in any one of aspects 1-16, wherein step (i) is conducted (or the first composition is formed) in any suitable diluent, e.g., toluene, propylene carbonate, dimethylformamide, dodecane, or a combination thereof.

[0090] Aspect 18. The process defined in any one of aspects 1-17, further comprising a step of isomerizing the first composition comprising the Cis aldehydes prior to step (ii) to convert ketones to aldehydes.

[0091] Aspect 19. The process defined in any one of aspects 1-18, further comprising a step of isolating an aldehyde composition comprising at least 75 mol %, at least 80 mol %, at least 85 mol %, at least 90 mol %, at least 95 mol %, at least 97 mol %, or at least 99 mol % of Cis aldehydes from the first composition prior to step (ii), via any suitable technique or any technique disclosed herein, e.g.. extraction, filtration, evaporation, distillation, fractional distillation, metathesis followed by distillation, or any combination thereof.

[0092] Aspect 20. The process defined in any one of aspects 1-19, wherein oxidizing in step (ii) comprises contacting (reacting) the C 15 aldehydes with KMnO-i and Na2HPO4 to form the second composition comprising the 1 -pentadecanoic acid.

[0093] Aspect 21. The process defined in any one of aspects 1-19, wherein oxidizing in step (ii) comprises contacting (reacting) the C15 aldehydes with molecular O2 in acetonitrile, optionally in the presence of a catalyst, to form the second composition comprising the 1 -pentadecanoic acid.

[0094] Aspect 22. The process defined in any one of aspects 1-21, further comprising a step of purifying the second composition to isolate a product composition comprising at least 80 wt. %, at least 85 wt. %, at least 90 wt. %, at least 95 wt. %, at least 96 wt. %, at least 19118-163-34497 wt. %, at least 98 wt. %, at least 99 wt. %, or at least 99.5 wt. % of 1 -pentadecanoic acid, via any suitable technique or any technique disclosed herein, e.g., extraction, filtration, evaporation, distillation, fractional distillation, or any combination thereof.

[0095] Aspect 23. A process comprising (a) subjecting a feedstock olefin composition comprising at least 75 mol % 1 -hexadecene to ozonolysis to form a first composition comprising Cis aldehydes, and (b) oxidizing the Cis aldehydes to form a second composition comprising 1 -pentadecanoic acid.

[0096] Aspect 24. The process defined in aspect 23, wherein the feedstock olefin composition comprises at least 80 mol %, at least 85 mol %, at least 90 mol %. at least 92 mol %, at least 93 mol %, at least 95 mol %, or at least 97 mol % of the 1 -hexadecene.

[0097] Aspect 25. The process defined in aspect 23 or 24, wherein the feedstock olefin composition further comprises from 1 to 20 mol %, from 2 to 18 mol %, from 2 to 12 mol %, from 3 to 20 mol %, from 3 to 12 mol %, from 3 to 8 mol %, or from 3 to 6 mol % Ci6 vinylidenes.

[0098] Aspect 26. The process defined in any one of aspects 23-25, wherein the feedstock olefin composition further comprises from 0.1 to 10 mol %, from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 10 mol %, from 0.5 to 5 mol %, from 1 to 10 mol %, or from 1 to 5 mol % Ci6 internal olefins.

[0099] Aspect 27. The process defined in any one of aspects 23-26, wherein the feedstock olefin composition further comprises from 0.1 to 20 mol %, from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 20 mol %, from 0.5 to 5 mol %, from 1 to 20 mol %, or from 2 to 10 mol % Ci6 branched alpha-olefins.

[0100] Aspect 28. The process defined in any one of aspects 23-27, wherein the feedstock olefin composition further comprises from 0.1 to 20 mol %, from 0.1 to 5 mol %, from 0.1 to 1 mol %, from 0.5 to 20 mol %, from 0.5 to 5 mol %, from 1 to 20 mol %, or from 2 to 10 mol % Ci6 alkanes.

[0101] Aspect 29. The process defined in any one of aspects 23-28, wherein subjecting the feedstock olefin composition to ozonolysis in step (a) comprises contacting (reacting) the feedstock olefin composition (or the 1 -hexadecene) wi th ozone and then with a reducing agent to form the first composition comprising the Cis aldehydes.

[0102] Aspect 30. The process defined in any one of aspects 23-29. further comprising a step of isolating an aldehyde composition comprising at least 85 mol %, at least 90 mol %, at least 95 mol %, at least 97 mol %, or at least 99 mol % of Cis aldehydes from 20118-163-344the first composition prior to step (b), via any suitable technique or any technique disclosed herein, e.g., extraction, filtration, evaporation, distillation, fractional distillation, metathesis followed by distillation, or any combination thereof.

[0103] Aspect 31. The process defined in any one of aspects 23-30, wherein oxidizing in step (b) comprises contacting (reacting) the Cis aldehydes with KMnCfi and NazHPCh to form the second composition comprising the 1 -pentadecanoic acid.

[0104] Aspect 32. The process defined in any one of aspects 23-30, wherein oxidizing in step (b) comprises contacting (reacting) the Cis aldehydes with molecular O2 in acetonitrile, optionally in the presence of a catalyst, to form the second composition comprising the 1 -pentadecanoic acid.

[0105] Aspect 33. The process defined in any one of aspects 23-30, wherein oxidizing in step (b) comprises contacting (reacting) the Cis aldehydes with H2O2 to form the second composition comprising the 1 -pentadecanoic acid.

[0106] Aspect 34. The process defined in any one of aspects 23-33, further comprising a step of purifying the second composition to isolate a product composition comprising at least 80 wt. %, at least 85 wt. %, at least 90 wt. %, at least 95 wt. %, at least 96 wt. %, at least 97 wt. %, at least 98 wt. %, at least 99 wt. %, or at least 99.5 wt. % of 1-pentadecanoic acid, via any suitable technique or any technique disclosed herein, e.g., extraction, filtration, evaporation, distillation, fractional distillation, or any combination thereof.

[0107] Aspect 35. The product composition comprising the 1 -pentadecanoic acid prepared by the process defined in aspect 22 or 34.

[0108] Aspect 36. A tablet, gel, or capsule containing the product composition comprising the 1 -pentadecanoic acid defined in aspect 35.

[0109] Aspect 37. A food additive, vitamin, or dietary supplement containing the product composition comprising the 1 -pentadecanoic acid defined in aspect 35.21118-163-344

Claims

CLAIMSWhat is claimed is:

1. A process comprising:(i) contacting a feedstock olefin composition comprising at least 75 mol % 1-tetradecene with a hydroformylation catalyst system, carbon monoxide, and hydrogen to form a first composition comprising Cis aldehydes; and(ii) oxidizing the Cis aldehydes to form a second composition comprising 1-pentadecanoic acid.

2. The process of claim 1, wherein the feedstock olefin composition comprises at least 85 mol % of the 1 -tetradecene.

3. The process of claim 1, wherein the feedstock olefin composition comprises at least 95 mol % of the 1 -tetradecene.

4. The process of any one of claims 1-3, wherein the feedstock olefin composition further comprises:from 1 to 20 mol % Ci4 vinylidenes;from 0.1 to 20 mol % Ci4 branched alpha-olefins;from 0.1 to 10 mol % Ci4 internal olefins; orany combination thereof.

5. The process of any one of claims 1-3, wherein the feedstock olefin composition further comprises:from 3 to 6 mol % Ci4 vinylidenes;from 2 to 10 mol % Ci4 branched alpha-olefins;from 1 to 5 mol % Ci4 internal olefins; orany combination thereof.22118-163-3446. The process of any one of claims 1-5, wherein the feedstock olefin composition further comprises from 0.1 to 20 mol % Ci4 alkanes.

7. The process of any one of claims 1-6, wherein the hydroformylation catalyst system comprises a cobalt compound.

8. The process of any one of claims 1-7, wherein the hydroformylation catalyst system comprises a rhodium compound.

9. The process of claim 7 or 8, wherein a molar ratio of olefins or 1 -tetradecene in the feedstock olefin composition to rhodium or cobalt is in a range from 100:1 to 500,000:1.

10. The process of any one of claims 1-9, wherein:a molar ratio of carbon monoxide to hydrogen in step (i) is in a range from 5: 1 to 1:5; a source of carbon monoxide and hydrogen in step (i) is Syngas; orboth.

11. The process of any one of claims 1-10, further comprising a step of isolating an aldehyde composition comprising at least 75 mol % of Cis aldehydes from the first composition prior to step (ii).

12. The process of any one of claims 1-10, further comprising a step of isolating an aldehyde composition comprising at least 95 mol % of Cis aldehydes from the first composition prior to step (ii).

13. The process of any one of claims 1-12, further comprising a step of purifying the second composition to isolate a product composition comprising at least 80 wt. % of 1-pentadecanoic acid.

14. The process of any one of claims 1-12, further comprising a step of purifying the second composition to isolate a product composition comprising at least 97 wt. % of 1-pentadecanoic acid.23118-163-34415. A process comprising:(a) subjecting a feedstock olefin composition comprising at least 75 mol % 1-hexadecene to ozonolysis to form a first composition comprising Cis aldehydes; and (b) oxidizing the Cis aldehydes to form a second composition comprising 1-pentadecanoic acid.

16. The process of claim 15, wherein the feedstock olefin composition comprises at least 85 mol % of the 1 -hexadecene.

17. The process of claim 15, wherein the feedstock olefin composition comprises at least 95 mol % of the 1 -hexadecene.

18. The process of any one of claims 15-17, wherein the feedstock olefin composition further comprises:from 1 to 20 mol % Ci6 vinylidenes;from 0.1 to 20 mol % Ci6 branched alpha-olefins;from 0.1 to 10 mol % C16 internal olefins; orany combination thereof.

19. The process of any one of claims 15-17, wherein the feedstock olefin composition further comprises:from 3 to 6 mol % Ci6 vinylidenes;from 2 to 10 mol % Ci6 branched alpha-olefins;from 1 to 5 mol % Ci6 internal olefins; orany combination thereof.

20. The process of any one of claims 15-19, wherein the feedstock olefin composition further comprises from 0.1 to 20 mol % Ci6 alkanes.

21. The process of any one of claims 15-20, wherein step (a) comprises contacting the feedstock olefin composition or the 1 -hexadecene with ozone and then with a reducing agent to form the first composition comprising the Ci 5 aldehydes.24118-163-34422. The process of any one of claims 15-21, further comprising a step of isolating an aldehyde composition comprising at least 85 mol % of Cis aldehydes from the first composition prior to step (b).

23. The process of any one of claims 15-21, further comprising a step of isolating an aldehyde composition comprising at least 97 mol % of Cis aldehydes from the first composition prior to step (b).

24. The process of any one of claims 15-23, further comprising a step of purifying the second composition to isolate a product composition comprising at least 80 wt. % of 1-pentadecanoic acid.

25. The process of any one of claims 15-23, further comprising a step of purifying the second composition to isolate a product composition comprising at least 97 wt. % of 1-pentadecanoic acid.

26. A process comprising:contacting a feedstock olefin composition comprising at least 75 mol % 1-tetradecene with a hydrocarboxylation catalyst system, carbon monoxide, and water to form a composition comprising 1 -pentadecanoic acid.

27. The process of claim 26, further comprising a step of purifying the composition to isolate a product composition comprising at least 80 wt. % of 1 -pentadecanoic acid.

28. The product composition comprising the 1 -pentadecanoic acid prepared by the process of any one of claims 13-14, 24-25, or 27.

29. A product composition comprising 1 -pentadecanoic acid derived from a feedstock olefin composition comprising 1-tetradecene and / or 1 -hexadecene.

30. A tablet, gel, or capsule containing the product composition comprising the 1-pentadecanoic acid of claim 28 or 29.25118-163-34431. A food additive, vitamin, or dietary supplement containing the product composition comprising the 1 -pentadecanoic acid of claim 28 or 29.26118-163-344

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