N-alkoxyamine markers and processes

Abstract

The present disclosure describes compositions comprising a fatty alcohol, a fatty aldehyde, and an N-alkoxyamine. The present disclosure further describes N-alkoxyamines and their use as markers for determining whether a particular process has been used.

Description

Technical Field

[0001] This disclosure describes compositions, in particular, comprising fatty alcohols, fatty aldehydes, and N-alkoxyamines. This disclosure further describes N-alkoxyamines and their use as markers for determining whether a particular process has been used. Background Technology

[0002] Integrated pest management (IPM) is playing an increasingly important role in both improving crop yields and minimizing environmental impact and achieving organic food production. IPM employs alternative pest control methods, such as using pheromones to disrupt pest mating or for mass trapping, or to attract beneficial insects.

[0003] Pheromones comprise a diverse group of compounds that insects (like other organisms) use to communicate between individuals of the same species under various conditions, including mate attraction, alarm, tracking, and aggregation. Insect pheromones associated with long-distance mate finding have been used in agricultural and forestry applications as a safe and environmentally friendly alternative to pesticides for pest monitoring and control. The bioproduction of pheromones for pest control is superior to chemical synthesis in terms of price, specificity, and environmental impact.

[0004] Pheromones and pheromone precursors can be produced by genetically engineered cell factories modified to include pathways expressing enzymes necessary to convert cellular precursor metabolites into desired pheromones and pheromone precursors, as described in WO2021078452 and WO2021123128.

[0005] Known pheromones include fatty acyl alcohols, aldehydes, and acetates with one or more double bonds at specific positions on a carbon backbone with specific Z and / or E orientations.

[0006] WO2023 / 012151 describes a convenient method for converting alcohol compositions into aldehyde compositions, particularly for converting fatty alcohols into fatty aldehydes. The method described therein utilizes relatively small amounts of solvent, is scalable to industrial scales, even to batch sizes of 100 kg or larger, and provides products of high purity, especially in the removal of catalyst compositions. However, it remains difficult to ascertain whether the proprietary method in WO2023 / 012151 or other methods have been used for alcohol oxidation when examining the final aldehyde composition. Summary of the Invention

[0007] The inventors have discovered a characteristic marker, namely, N-alkoxyamines produced by the alcohol oxidation process of WO2023 / 012151 using copper catalysis and OH-TEMPO (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxy groups. The N-alkoxyamine marker is generated by shortening the carbon chain of the fatty alcohol or fatty aldehyde to be oxidized, involving the sequential replacement of the original oxygen of the fatty alcohol with the OH-TEMPO moiety. The fatty alcohol is oxidized to provide pheromones of high bioindustrial importance, and the resulting N-alkoxyamines obtained from this process have highly characteristic analytical profiles, such as mass spectrometry profiles and / or retention times, making it possible to determine whether a specific oxidation process has been used.

[0008] Therefore, in one aspect, a method is provided for determining whether a composition comprising: a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, fatty alcohol acetates, and combinations thereof; and b) an N-alkoxyamine; wherein the process includes the following steps:

[0009] (I) A reaction mixture comprising a fatty alcohol, a catalyst comprising a copper source, and a solvent, and

[0010] (II) Oxidize fatty alcohols by adding O2 to the reaction mixture in an amount sufficient to convert more than 50% by weight of fatty alcohols into fatty aldehydes and less than 50% by weight of fatty alcohols into fatty acids.

[0011] The method includes the following steps:

[0012] A) Provide a composition for analysis;

[0013] B) subjecting a sample of the composition in A) to mass spectrometry analysis to obtain a mass spectrum, preferably analytical chromatography coupled with mass spectrometry;

[0014] C) Wherein if the mass spectrum obtained in B) contains a mass (m / z) corresponding to an N-alkoxyamine, then the composition comprising a) and b) has been obtained by the process described.

[0015] In another aspect, a composition is provided comprising: a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, fatty alcohol acetates, and combinations thereof; and b) an N-alkoxyamine.

[0016] In another aspect, N-alkoxyamines selected from the group consisting of Z10-15-A-TEMPO; Z10, Z12-15-A-TEMPO; and Z8, E10-15-A-TEMPO are added: (Z10-15-A-TEMPO);

[0017] (Z10,Z12-15-A-TEMPO);

[0018] (Z8,E10-15-A-TEMPO);

[0019] A is selected from the group consisting of: hydrogen, hydroxyl, carbonyl, alkyl, such as C. 1-6 Alkyl groups, amines, amides, such as C 1-6 -Amide, alkoxy group such as C 1-6 Alkoxy groups and esters such as C 1-6 Esters; or their ions or salts.

[0020] In another aspect, a process is provided for producing a composition comprising: a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, and combinations thereof; and b) an N-alkoxyamine; wherein the method includes the following steps:

[0021] i) Provide a reaction mixture comprising a fatty alcohol, a catalyst containing a copper source, and a solvent, and

[0022] ii) Oxidize fatty alcohols by adding O2 to the reaction mixture in an amount sufficient to convert more than 50% by weight of fatty alcohols into fatty aldehydes and less than 50% by weight of fatty alcohols into fatty acids.

[0023] In another aspect, a composition obtainable by the process disclosed herein is provided.

[0024] In another aspect, a method is provided for determining whether a composition has been prepared by the process of this disclosure, wherein the method includes the following steps:

[0025] a) Provide a composition for analysis;

[0026] b) subjecting a sample of the composition in a) to mass spectrometry to obtain a mass spectrum, preferably analytical chromatography coupled with mass spectrometry;

[0027] c) Wherein the mass spectrum obtained in b) contains a mass corresponding to an N-alkoxyamine as defined herein, the composition has been obtained by the process described herein. Attached Figure Description

[0028] Figure 1 The gas chromatography-mass spectrometry (GCMS) area, expressed as a percentage, is shown for alcohols (solid black circles), aldehydes (hollow black circles), and TEMPO adducts, namely N-alkoxyamines (solid black stars), respectively, using the conditions described in Example 1, as a function of the reaction time for alcohol oxidation.

[0029] Figure 2 shows GC-FID chromatograms of a representative sample (A) of N-alkoxyamines obtained by the oxidation process of Example 1 and a synthetic standard (B) of N-alkoxyamines obtained as described in Example 2.

[0030] Figure 3 The GC-MS chromatogram of a representative sample of N-alkoxyamines obtained by the oxidation process of Example 1 is shown.

[0031] Figure 4 The mass spectrum of a representative sample of N-alkoxyamine obtained by the oxidation process of Example 1 is shown.

[0032] Figure 5 The GC-MS chromatogram of the synthetic standard of N-alkoxyamine obtained as described in Example 2 is shown.

[0033] Figure 6 The mass spectrum of the synthetic standard of N-alkoxyamine obtained as described in Example 2 is shown.

[0034] Figure 7 The GC-FID chromatogram of a representative sample of N-alkoxyamine marker 2 obtained from the oxidation process of Example 1 is shown.

[0035] Figure 8 The GC-FID chromatogram of the synthetic standard of N-alkoxyamine (Z11-16-OH-TEMPO-2) obtained as described in Example 3 is shown.

[0036] Figure 9 shows the GC-MS chromatogram (A) and spectrum (B) of the synthetic standard of N-alkoxyamine marker 2 (Z11-16-OH-TEMPO-2) obtained as described in Example 3.

[0037] By referencing the merging

[0038] All publications, patents, and patent applications mentioned herein are incorporated by reference to the same extent that each individual publication, patent, or patent application is specifically and individually indicated to be incorporated by reference. In the event of any conflict between the terminology used herein and that in the incorporated references, the terminology used herein shall prevail. Detailed Implementation

[0039] definition

[0040] Throughout this disclosure, when referring to pheromone components or precursors (e.g., (Z,E)-9,11-hexadecadienal, which refers to an aliphatic aldehyde having a 16-carbon chain, an aldehyde group at C1, a Z-configuration double bond at C9, and an E-configuration double bond at C11), alternative terms such as Z9,11-16:Ald or (Z9,E11)-hexadecadienal may be used interchangeably. Similar nomenclature may be used for compounds from other pathways, such as the corresponding fatty acids, CoA derivatives, alcohols, acids, or acetates.

[0041] The term "saturated" refers to a compound that does not have carbon-carbon double or triple bonds.

[0042] As used herein, the term "desaturated" is interchangeable with the term "unsaturated" in relation to compounds. It refers to a compound containing one or more carbon-carbon double or triple bonds, preferably carbon-carbon double bonds. Throughout this document, the following nomenclature is used: Δi desaturated compounds, where i is an integer, refer to compounds having a carbon-carbon double or triple bond at position i of the carbon chain. Therefore, the carbon chain length is at least equal to i. For example, Δ12 desaturated compounds refer to compounds having a carbon-carbon double or triple bond at position 12 and a carbon chain length of 13 or longer. The double or triple bond can be E-configured or Z-configured. Therefore, Ei or Zi desaturated compounds would refer to compounds having a carbon-carbon double bond, respectively, at position i of the carbon chain in an E-configuration or a Z-configuration, with the carbon chain having a total length at least equal to i. For example, E11 fatty alcohols have an E-configured desaturated bond at position 11 and a carbon chain length of 12 or longer.

[0043] As used herein, the term "biobased" is used to characterize bio-based products, wherein:

[0044] (I) The total carbon content of the product is at least 30%, and

[0045] (II) The carbon content of renewable raw materials (bio-based) is at least 20%.

[0046] Both fossils and renewable raw materials are primarily composed of carbon (C). Carbon exists in several isotopes. Isotopes 14 C is radioactive and naturally present in all living organisms (plants, animals, etc.) at a fixed relative concentration, which is similar to that in the atmosphere. 14 The relative concentrations of C are almost the same. At this concentration, 14 The radioactivity level of C is 100%. Once the organism ceases to exist, this concentration, and therefore the intensity of its radioactivity, will decay over a half-life of approximately 5700 years. Therefore, the radioactivity of unknown substances... 14 C levels can help determine the age of the carbon contained in a substance.

[0047] "Young" carbon (0 to 10 years old) derived from renewable raw materials (such as plants or animals) has a relative abundance compared to carbon in the atmosphere. 14 Relative isotopes with almost identical C concentrations 14 C concentration, and therefore the radioactivity of such young carbon. 14 The C level is approximately 100%.

[0048] The isotopes derived from “old” carbon (millions of years old) of synthetic or fossil (petrified) origin. 14 C is largely depleted because the ages of such synthetic and fossil sources far exceed the isotopic age. 14 Half-life of C, isotopes 14 The half-life of carbon is approximately 5700 years. Therefore, carbon from synthetic or fossil sources has a relative isotopic content of approximately 0%. 14 C concentration, and therefore the radioactivity of this type of old carbon. 14 The C level was approximately 0%.

[0049] In one implementation, the term "radioactive" 14 "Level C" refers to the total radioactivity of a given substance, product, or composition. 14 Level C, as defined above.

[0050] isotope 14 Method C can be used to determine the concentration of young (renewable) materials by comparing it with the concentration of old (fossil) resources. The carbon content of renewable raw materials is referred to as "bio-based carbon content." The carbon content or "bio-based carbon content" of renewable raw materials can be determined as follows.

[0051] When measuring bio-based carbon content, the result can be reported as "Bio-based Carbon %". This indicates the percentage of carbon from "natural" (plant or animal by-product) sources relative to "synthetic" or "fossil" (petrified) sources. For reference, 100% bio-based carbon indicates that the material is entirely derived from plant or animal by-products, and 0% bio-based carbon indicates that the material contains no carbon from plant or animal by-products. Values ​​in between represent a mixture of natural and fossil resources.

[0052] For example: if the product has 80% radioactivity 14 A carbon (C) level means that the product consists of 80% renewable carbon and 20% fossil carbon (C). In other words, the product is 80% bio-based.

[0053] The analytical measurement can be referred to as "modern percentage carbon (pMC)". This is measured in the sample. 14C is a percentage relative to the modern reference standard (NIST 4990C). Bio-based carbon content % is based on pMC by analyzing the carbon dioxide content in the current air. 14 C is calculated using a small adjustment factor. It is important to note that all uses... 14 Internationally recognized standards for C assume that plant or biomass feedstocks are derived from the natural environment. pMC can be analyzed using standard testing methods such as "ASTM D6866".

[0054] As used herein, the term "fatty acyl compound" refers to a fatty compound having a long aliphatic chain, typically with between 12 and 28 carbon atoms, such as 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28 carbon atoms. Most naturally occurring fatty acids are unbranched. They can be saturated or desaturated. Fatty acyl compounds can include a variety of functional end groups.

[0055] As used herein, the term "fatty acyl-CoA," which may be used interchangeably with "fatty acyl-CoA ester," refers to and is specific to compounds of the general formula R-CO-SCoA, where R is a fatty carbon chain having 12 to 28 carbon atoms, with chain lengths such as 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28 carbon atoms. The fatty carbon chain is attached to the –SH group of CoA via a thioester bond. Fatty acyl-CoA may be saturated or desaturated, depending on whether the fatty acid from which it is derived is saturated or desaturated.

[0056] As used herein, the term "fatty alcohol" refers to an alcohol having a carbon chain length of 13 to 28 carbon atoms, such as 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28 carbon atoms. Fatty alcohols can be saturated or desaturated.

[0057] As used herein, the term "fatty alcohol acetate" refers to an acetate having a fatty carbon chain, that is, an aliphatic chain having between 13 and 28 carbon atoms, such as 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28 carbon atoms. Fatty acyl acetates can be saturated or desaturated.

[0058] As used herein, the term "aliphatic aldehyde" refers to an aldehyde having a carbon chain length of 13 to 28 carbon atoms, such as 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, or 28 carbon atoms. Aliphatic aldehydes can be saturated or desaturated.

[0059] As used herein, the term "functional variant" refers to a functional variant of an enzyme that retains at least some of the activity of its parent enzyme. Thus, functional variants of desaturases or other pathway enzymes catalyze reactions similar to their parent enzymes, although the efficiency and specificity of the reaction may differ, such as decreasing or increasing efficiency compared to the parent enzyme.

[0060] As used herein, the term "pheromone" refers to naturally occurring signaling compounds used in nature for chemical communication between individuals of a species. For example, Lepidoptera pheromones are represented by unbranched aliphatic chains (with between 9 and 18 carbon atoms, such as 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms) ending with an alcohol, aldehyde, or acetate functional group and containing up to three double bonds in the aliphatic backbone. Thus, desaturated fatty alcohols, desaturated fatty aldehydes, and desaturated fatty alcohol acetates are typically included in pheromones. Pheromonic compositions can be produced by chemical or biochemical methods, such as those described herein. Therefore, pheromones comprising desaturated fatty alcohols, desaturated fatty aldehydes, and / or desaturated fatty alcohol acetates can be obtained, for example, by the methods and cells described herein.

[0061] The terms “comprise” and “include” used throughout this specification, as well as subsidiary items and variations such as “comprises,” “comprising,” “includes,” and “including,” should be interpreted as inclusive. Where the context permits, these words are intended to convey that other elements or integers not specifically described may be included.

[0062] The articles “a” and “an” used in this article refer to one / one or more (i.e., one / one or at least one / at least one) of the grammatical objects of the article. For example, “an element” can mean one element or more elements.

[0063] Terms such as “preferredly,” “usually,” “particularly,” and “typically” are not used herein to limit the scope of the listed inventions, or to imply that certain features are critical, essential, or even important to the structure or function of the listed inventions. Rather, these terms are intended only to highlight alternative or additional features that may or may not be available in a particular embodiment of the invention.

[0064] All methods described herein can be performed in any suitable order of steps unless otherwise stated herein or otherwise obviously contradicted by the context. The use of any and all examples or exemplary language (e.g., “such as”) provided herein is merely intended to better illustrate the invention and is not intended to limit the scope of the invention as otherwise claimed. No language in the specification should be construed as indicating any unclaimed element essential to the practice of the invention.

[0065] Unless otherwise stated, all percentages, ratios, and proportions herein are by weight. Unless specifically stated to the contrary, the weight percentage (wt.%) of a component is based on the total weight of the composition in which that component is contained (e.g., based on the total amount of the reaction mixture).

[0066] As used herein, the terms “substantially,” “approximately,” or “about” refer to a reasonable deviation from a value or parameter such that the value or parameter does not change significantly. These terms regarding deviation from a value should be interpreted as including the deviation from that value, where such deviation does not negate the meaning of a deviation from it. For example, with respect to a reference value, the term “degree” can include a range of values ​​plus or minus 10% of that value. For example, deviation from a value can include a specified value plus or minus a certain percentage from that value, such as plus or minus 9%, 8%, 7%, 6%, 5%, 4%, 3%, 2%, or 1% of the specified value.

[0067] As used herein, the term “and / or” is intended to indicate an inclusive “or”. The words X and / or Y mean either X or Y, or both X and Y. Furthermore, the words X, Y and / or Z are intended to mean either X, Y and Z alone, or any combination of X, Y and Z.

[0068] As used herein, the term "isolated" refers to any compound that has been placed in a form or environment different from its natural form or environment through human intervention. Isolated compounds include, but are not limited to, the compounds of this disclosure, wherein the ratio of said compounds to other components associated with them in nature is increased or decreased. In an important embodiment, the amount of the compound is increased relative to other components associated with the compound in nature. In one embodiment, the compounds of this disclosure may be isolated into a pure form or a substantially pure form. In this context, a substantially pure compound means that the compound is isolated from other foreign or unwanted materials present from the beginning of the compound's production or generated during the manufacturing process. Such substantially pure compound formulations contain less than 10%, such as less than 8%, such as less than 6%, such as less than 5%, such as less than 4%, such as less than 3%, such as less than 2%, such as less than 1%, such as less than 0.5% by weight of other foreign or unwanted materials that are generally associated with the compound when it is expressed naturally or recombinantly. In one embodiment, the isolated compound is at least 90% pure by weight, such as at least 91% pure, such as at least 92% pure, such as at least 93% pure, such as at least 94% pure, such as at least 95% pure, such as at least 96% pure, such as at least 97% pure, such as at least 98% pure, such as at least 99% pure, such as at least 99.5% pure, such as 100% pure.

[0069] Composition

[0070] In some embodiments, a composition is provided comprising: a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, fatty alcohol acetates, and combinations thereof; and b) an N-alkoxyamine. The N-alkoxyamines of this disclosure have a highly characteristic analytical profile, making them suitable for detecting whether a process for producing the compositions of this disclosure has been used.

[0071] In some embodiments, a composition is provided in which at least one active ingredient is a pheromone.

[0072] Bio-based compositions

[0073] In some embodiments, the provided composition is a bio-based composition. In some embodiments, the composition is a biopesticide. In some embodiments, the composition contains at least 20% bio-based carbon, such as at least 30% bio-based carbon, such as at least 40% bio-based carbon, such as at least 50% bio-based carbon, such as at least 60% bio-based carbon, such as at least 70% bio-based carbon, such as at least 75% bio-based carbon, such as at least 80% bio-based carbon, such as at least 85% bio-based carbon, such as at least 90% bio-based carbon, such as at least 95% bio-based carbon, such as 100% bio-based carbon.

[0074] In some embodiments, the composition comprises 20% to 100% bio-based carbon, such as 30% to 100% bio-based carbon, such as 40% to 100% bio-based carbon, such as 50% to 100% bio-based carbon, such as 60% to 100% bio-based carbon, such as 70% to 100% bio-based carbon, such as 75% to 100% bio-based carbon, such as 80% to 100% bio-based carbon, such as 85% to 100% bio-based carbon, such as 90% to 100% bio-based carbon, such as 95% to 100% bio-based carbon, such as 100% bio-based carbon.

[0075] In some embodiments, at least one active ingredient of the composition comprises at least 20% bio-based carbon, such as at least 30% bio-based carbon, such as at least 40% bio-based carbon, such as at least 50% bio-based carbon, such as at least 60% bio-based carbon, such as at least 70% bio-based carbon, such as at least 75% bio-based carbon, such as at least 80% bio-based carbon, such as at least 85% bio-based carbon, such as at least 90% bio-based carbon, such as at least 95% bio-based carbon, such as 100% bio-based carbon.

[0076] In some embodiments, at least one active ingredient of the composition comprises 20% to 100% bio-based carbon, such as 30% to 100% bio-based carbon, such as 40% to 100% bio-based carbon, such as 50% to 100% bio-based carbon, such as 60% to 100% bio-based carbon, such as 70% to 100% bio-based carbon, such as 75% to 100% bio-based carbon, such as 80% to 100% bio-based carbon, such as 85% to 100% bio-based carbon, such as 90% to 100% bio-based carbon, such as 95% to 100% bio-based carbon, such as 100% bio-based carbon.

[0077] In some embodiments, the composition contains radioactivity corresponding to a percentage of bio-based carbon. 14 C level (%). In this case, for example, 50% radioactivity. 14 The C level (%) will correspond to 50% of bio-based carbon.

[0078] In some embodiments, the composition comprises at least one biologically derived substance, such as at least one substance derived from yeast cells, such as yeast cell-derived metabolites.

[0079] In some embodiments, the composition comprises at least one bio-derived substance selected from the group consisting of: hexadecane-1-ol, (Z)-9-hexadecen-1-ol, (Z)-11-hexadecen-1-ol, and (Z,E)-9,11-hexadecadien-1-ol. In some embodiments, the composition comprising these bio-derived substances is bio-based, as defined herein.

[0080] In some embodiments, the composition further comprises one or more carriers, agents, additives, stabilizers, antioxidants, UV absorbers, light stabilizers, antifreeze agents, glycols, polyols, adjuvants, and / or excipients.

[0081] In some embodiments, the compositions disclosed herein further comprise a protective agent comprising a sulfur-containing compound, optionally wherein the protective agent comprises conjugated sulfur.

[0082] In some embodiments, the composition defined herein further comprises:

[0083] a) A protective agent comprising a conjugated sulfur compound selected from the group consisting of zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-1-methylimidazole, and sodium pyrithione, which protects the target compound from conversion to an acid; and / or

[0084] b) A carrier that promotes the slow release of (Z,E)-9,11-hexadecadienal, (Z)-9-hexadecenal, (Z)-11-hexadecenal and / or hexadecaldehyde from the mixture, optionally being (i) a polymer matrix selected from plastics, wax emulsions, oil emulsions or microcapsules and / or (ii) zeolite.

[0085] fatty alcohols

[0086] In some embodiments, compositions of this disclosure are provided, wherein the fatty alcohol is a primary alcohol.

[0087] In some implementations, the fatty alcohol is a saturated fatty alcohol or a desaturated fatty alcohol.

[0088] In some implementations, the fatty alcohol is a C10 to C26 fatty alcohol.

[0089] In some implementations, the fatty alcohol is a C10 to C22 fatty alcohol.

[0090] In some implementations, the fatty alcohol is a C12 to C20 fatty alcohol.

[0091] In some implementations, the fatty alcohol is a C12 to C18 fatty alcohol.

[0092] In some implementations, the fatty alcohol is a C12, C14, C16, or C18 fatty alcohol.

[0093] In some embodiments, compositions are provided in which the desaturated fatty alcohol has a double bond at position 9, 11 or 13, or in which the desaturated fatty alcohol has a double bond at positions 9 and 11 or at positions 11 and 13.

[0094] In some embodiments, compositions of the present disclosure are provided, wherein the desaturated fatty alcohol has a double bond at position 9 or 12, or wherein the desaturated fatty alcohol has a double bond at positions 9 and 12.

[0095] In some embodiments, compositions of the present disclosure are provided, wherein the desaturated fatty alcohol has a double bond at position 8 or 10, or wherein the desaturated fatty alcohol has a double bond at positions 8 and 10.

[0096] In some embodiments, compositions of the present disclosure are provided wherein the fatty alcohol has a carbon chain length of 12, 14, or 16. In some embodiments, compositions of the present disclosure are provided wherein the fatty alcohol has a carbon chain length of 12 to 16.

[0097] In some embodiments, compositions of the present disclosure are provided, wherein the fatty alcohol is an unbranched fatty alcohol.

[0098] In some embodiments, compositions of this disclosure are provided, wherein the fatty alcohols are selected from the group consisting of:

[0099] (Z)-Δ3 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0100] (E)-Δ3 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0101] (Z)-Δ5 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0102] (E)-Δ5 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0103] (Z)-Δ6 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0104] (E)-Δ6 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0105] (Z)-Δ7 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0106] (E)-Δ7 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0107] (Z)-Δ8 desaturated fatty alcohols with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0108] (E)-Δ8 desaturated fatty alcohols with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0109] (Z)-Δ9 desaturated fatty alcohols with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0110] (E)-Δ9 desaturated fatty alcohols with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0111] (Z)-Δ10 desaturated fatty alcohols with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0112] (E)-Δ10 desaturated fatty alcohols with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0113] (Z)-Δ11 desaturated fatty alcohols with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0114] (E)-Δ11 desaturated fatty alcohols with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0115] (Z)-Δ12 desaturated fatty alcohols with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0116] (E)-Δ12 desaturated fatty alcohols with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0117] (Z)-Δ13 desaturated fatty alcohols having carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22; and

[0118] (E)-Δ13 desaturated fatty alcohols with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0119] In some embodiments, compositions of this disclosure are provided, wherein the fatty alcohols are selected from the group consisting of:

[0120] (E)7,(Z)9 desaturated fatty alcohols with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0121] (E)3,(Z)8,(Z)11 desaturated fatty alcohols with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22.

[0122] (Z)9, (E)11, (E)13 desaturated fatty alcohols with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22.

[0123] (Z)11,(Z)13 desaturated fatty alcohols with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0124] (Z)9,(E)12 desaturated fatty alcohols with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0125] (E)7 and (E)9 desaturated fatty alcohols having carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22, and

[0126] (E8, E10) desaturated fatty alcohols with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0127] In some embodiments, compositions of this disclosure are provided, wherein the fatty alcohols are selected from the group consisting of:

[0128] (E)7,(Z)9 desaturated fatty alcohols with a carbon chain length of 14

[0129] (E)3,(Z)8,(Z)11 desaturated fatty alcohols with a carbon chain length of 14

[0130] (Z)9,(E)11,(E)13 desaturated fatty alcohols with a carbon chain length of 14

[0131] (E)7,(Z)9 desaturated fatty alcohols with a carbon chain length of 12

[0132] (E)3,(Z)8,(Z)11 desaturated fatty alcohols with a carbon chain length of 12

[0133] (Z)9,(E)11,(E)13 desaturated fatty alcohols with a carbon chain length of 12

[0134] (E)8,(E)10 desaturated fatty alcohols with a carbon chain length of 12

[0135] (E)7,(E)9 desaturated fatty alcohols with a carbon chain length of 11

[0136] (Z)11,(Z)13 desaturated fatty alcohols with a carbon chain length of 16, and

[0137] (Z)9,(E)12 desaturated fatty alcohols with a carbon chain length of 14.

[0138] In some embodiments, the fatty alcohol is selected from the group consisting of: tetradecane-1-ol, pentadecane-1-ol, hexadecane-1-ol, pentadecen-1-ol, (Z)-9-hexadecen-1-ol, (Z)-11-hexadecen-1-ol, (7E,9E)-undec-7,9-dien-1-ol, (11Z,13Z)-hexadecen-1-ol, (9Z,12E)-tetradecen-1-ol and (8E,10E)-dodecen-1-ol.

[0139] Fatty aldehydes

[0140] In some embodiments, the compositions of this disclosure are provided, wherein the aliphatic aldehyde is a saturated aliphatic aldehyde. In some embodiments, the compositions of this disclosure are provided, wherein the aliphatic aldehyde is a desaturated aliphatic aldehyde. In some embodiments, the aliphatic aldehyde is a C10 to C26 aliphatic aldehyde. In some embodiments, the aliphatic aldehyde is a C10 to C22 aliphatic aldehyde. In some embodiments, the aliphatic aldehyde is a C12 to C20 aliphatic aldehyde. In some embodiments, the aliphatic aldehyde is a C12, C14, or C16 aliphatic aldehyde. In some embodiments, the aliphatic aldehyde is an unbranched aliphatic aldehyde. In some embodiments, the desaturated aliphatic aldehyde has a double bond at positions 9, 11, or 13, or wherein the desaturated aliphatic aldehyde has a double bond at positions 9 and 11 or at positions 11 and 13.

[0141] In some implementations, the desaturated aliphatic aldehyde has a double bond at position 9 or 12, or the desaturated aliphatic aldehyde has a double bond at positions 9 and 12.

[0142] In some embodiments, the desaturated aliphatic aldehyde has a double bond at position 8 or 10, or the desaturated aliphatic aldehyde has a double bond at positions 8 and 10.

[0143] In some embodiments, aliphatic aldehydes have a carbon chain length of 12, 14, or 16. In some embodiments, aliphatic aldehydes have a carbon chain length of 12 to 16.

[0144] In some implementations, the fatty aldehydes are selected from the group consisting of:

[0145] (Z)-Δ3 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0146] (E)-Δ3 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0147] (Z)-Δ5 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0148] (E)-Δ5 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0149] (Z)-Δ6 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0150] (E)-Δ6 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0151] (Z)-Δ7 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0152] (E)-Δ7 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0153] (Z)-Δ8 desaturated aliphatic aldehydes with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0154] (E)-Δ8 desaturated aliphatic aldehydes with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0155] (Z)-Δ9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0156] (E)-Δ9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0157] (Z)-Δ10 desaturated aliphatic aldehydes with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0158] (E)-Δ10 desaturated aliphatic aldehydes with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0159] (Z)-Δ11 desaturated aliphatic aldehydes with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0160] (E)-Δ11 desaturated aliphatic aldehydes with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0161] (Z)-Δ12 desaturated aliphatic aldehydes with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0162] (E)-Δ12 desaturated aliphatic aldehydes with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;

[0163] (Z)-Δ13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22; and

[0164] (E)-Δ13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0165] In some implementations, the fatty aldehydes are selected from the group consisting of:

[0166] (E)7,(Z)9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0167] (E)3, (Z)8, (Z)11 desaturated aliphatic aldehydes with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22.

[0168] (Z)9, (E)11, (E)13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22.

[0169] (Z)11,(Z)13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0170] (Z)9,(E)12 desaturated aliphatic aldehydes with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0171] (E)7 and (E)9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22, and

[0172] (E)8, (E)10 desaturated aliphatic aldehydes with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0173] In some implementations, the fatty aldehydes are selected from the group consisting of:

[0174] (E)7,(Z)9 desaturated aliphatic aldehydes with a carbon chain length of 14.

[0175] (E)3,(Z)8,(Z)11 desaturated aliphatic aldehydes with a carbon chain length of 14.

[0176] (Z)9, (E)11, (E)13 desaturated aliphatic aldehydes with a carbon chain length of 14.

[0177] (E)7,(Z)9 desaturated aliphatic aldehydes with a carbon chain length of 12.

[0178] (E)3,(Z)8,(Z)11 desaturated aliphatic aldehydes with a carbon chain length of 12.

[0179] (Z)9, (E)11, (E)13 desaturated aliphatic aldehydes with a carbon chain length of 12.

[0180] (E)8,(E)10 desaturated aliphatic aldehydes with a carbon chain length of 12.

[0181] (E)7,(E)9 desaturated aliphatic aldehydes with a carbon chain length of 11.

[0182] (Z)11,(Z)13 desaturated aliphatic aldehydes with a carbon chain length of 16, and

[0183] (Z)9,(E)12 desaturated aliphatic aldehydes with a carbon chain length of 14.

[0184] In some embodiments, the aliphatic aldehyde is selected from the group consisting of: tetradecane-1-aldehyde, pentadecane-1-aldehyde, hexadecane-1-aldehyde, pentadecene-1-aldehyde, (Z)-9-hexadecene-1-aldehyde, (Z)-11-hexadecene-1-aldehyde, (7E,9E)-undec-7,9-diene-1-aldehyde, (11Z,13Z)-hexadecene-1-aldehyde, (9Z,12E)-tetradecene-1-aldehyde and (8E,10E)-dodecene-1-aldehyde.

[0185] In some embodiments, the compositions disclosed herein further comprise:

[0186] a) at least 30% by weight of one or more fatty aldehydes, such as at least 40% by weight, 50% by weight, 55% by weight, or 60% by weight of one or more fatty aldehydes, and / or

[0187] b) At least 30% by weight of one or more fatty alcohols, such as at least 40% by weight, 50% by weight, 55% by weight, or 60% by weight of one or more fatty alcohols;

[0188] The total amount of fatty aldehydes, fatty alcohols and N-alkoxyamines shall not exceed 100% by weight.

[0189] N-alkoxyamines

[0190] In some embodiments, compositions of the present disclosure are provided, wherein the N-alkoxyamine is detectable by mass spectrometry (MS). In some embodiments, the N-alkoxyamine is ionized by mass spectrometry (MS). A person skilled in the art can readily determine whether a particular compound, such as an N-alkoxyamine, is detectable by MS by subjecting a sample of the particular compound to MS.

[0191] In some embodiments, N-alkoxyamines can be detected by an MS method selected from the group consisting of: electron ionization (EI), electrospray ionization (ESI); matrix-assisted laser desorption / ionization (MALDI); time-of-flight (TOF); quadrupole; ion trap; orbital trap; Fourier transform ion cyclotron resonance (FT-ICR). In some embodiments, more than one MS method is combined, for example, a combination of TOF and ESI, or a combination of TOF and MALDI.

[0192] In some embodiments, N-alkoxyamines can be ionized by MS methods selected from the group consisting of: electron ionization (EI), electrospray ionization (ESI); matrix-assisted laser desorption / ionization (MALDI); time-of-flight (TOF); quadrupole; ion trap; orbital trap; Fourier transform ion cyclotron resonance (FT-ICR).

[0193] In some embodiments, when measured using mass spectrometry (MS), N-alkoxyamines exhibit one or more m / z peaks, wherein the one or more peaks are selected from: 156.1, 309.3, 323.3, 337.3, 351.4, 365.4, 379.4, 393.4, 407.4, 421.4, 435.4, 449.5, 307.3, 321.3, 335.3, 349.3, 363.4, 377.4, 391.4, 405.4, 419.4, 433.4, 447.4, 172.1, 325.3, 339.3, 353.3, 367.3, 381.4, 395.4, 409.4, 423.4, 437. 4, 451.4, 465.5, 323.3, 337.3, 351.3, 365.3, 379.3, 393.4, 407.4, 421.4, 435.4, 449.4, 463.4, 140.1, 293.3, 307.3, 321.3, 335.3, 349.3, 363.4, 377 .4, 391.4, 405.4, 419.4, 433.4, 291.3, 305.3, 319.3, 333.3, 347.3, 361.3, 375.4, 389.4, 403.4, 417.4, 431.4, 166.1, 319.3, 333.3, 347.3, 361.3, 37 5.4, ​​389.4, 403.4, 417.4, 431.4, 445.4, 459.4, 317.3, 331.3, 345.3, 359.3, 373.3, 387.4, 401.4, 415.4, 429.4, 443.4, 457.4, 152.1, 305.3, 319.3, 3 33.3, 347.3, 361.3, 375.4, 389.4, 403.4, 417.4, 431.4, 445.4, 303.3, 317.3, 331.3, 345.3, 359.3, 373.3, 387.4, 401.4, 415.4, 429.4, 443.4, 186.1 339.3, 353.3, 367.3, 381.4, 395.4, 409.4, 423.4, 437.4, 451.4, 465.5, 479.5, 337.3, 351.3, 365.3, 379.3, 393.4, 407.4, 421.4, 435.4, 449.4, 463.4 477.5, 171.1, 324.3, 338.3, 352.3, 366.4, 380.4, 394.4, 408.4, 422.4, 436.4, 450.5, 464.5, 322.3, 336.3, 350.3, 364.3, 378.4, 392.4, 406.4, 420.4, 434.4, 448.4, 462.5, 213.2, 366.3, 380.3, 394.4, 408.4, 422.4, 436.4, 450.4, 464.4, 478.4, 492.5, 506.5, 364.3, 378.3, 392.3, 406.4, 420.4, 434.4, 448.4, 462.4, 476.4, 490.4, 504.5, 170.1, 323.3, 337.3, 351.3, 365.3, 379.3, 393.4, 407.4, 421.4, 435.4 The following numbers are listed: 449.4, 463.4, 321.3, 335.3, 349.3, 363.3, 377.3, 391.3, 405.4, 419.4, 433.4, 447.4, 461.4, 276.2, 429.3, 443.3, 457.4, 471.4, 485.4, 499.4, 513.4, 527.4, 541.4, 555.5, 569.5, 427.3, 441.3, 455.3, 469.4, 483.4, 497.4, 511.4, 525.4, 539.4, 553.4, and 567.5.

[0194] According to Table 1 below, the m / z values ​​or peaks provided in

[0092] correspond to one or more N-alkoxyamines:

[0195]

[0196]

[0197] Table 1: Overview of the N-alkoxyamines selected in this disclosure.

[0198] In some implementations, when measured using mass spectrometry (MS), N-alkoxyamines exhibit one or more m / z peaks, wherein one or more peaks are selected from the masses in Table 2.

[0199]

[0200]

[0201]

[0202] Table 2: Overview of other N-alkoxyamines disclosed herein.

[0203] In some embodiments, N-alkoxyamines can be detected by analytical chromatography. In the context of this invention, analytical chromatography allows for the separation of multiple compounds in a sample. The compounds can then be studied, for example, by visual inspection (using chemicals that react with the compounds to provide a colored compound) or by a detector. Preferably, the compounds are studied using a detector, such as a suitable MS detector.

[0204] In some embodiments, N-alkoxyamines can be detected by analytical chromatographic methods selected from the group consisting of: gas chromatography-MS (GC-MS), liquid chromatography-MS (LC-MS), high performance liquid chromatography-MS (HPLC-MS), ultra-high performance liquid chromatography-MS (UHPLC-MS), ion chromatography-MS (IC-MS), and size exclusion chromatography-MS (SEC-MS).

[0205] In some embodiments, the N-alkoxyamine has the formula (Z10-15-A-TEMPO):

[0206] (Z10-15-A-TEMPO), where A is selected from the group consisting of: hydrogen, hydroxyl, alkyl, such as C. 1-6 Alkyl, amine, amide, alkoxy, such as C 1-6 Alkoxy groups and esters such as C 1-6 Esters; or their ions or salts.

[0207] In some embodiments, the compositions disclosed herein comprise N-alkoxyamines selected from the group consisting of:

[0208] (Z10-15-OH-TEMPO); and

[0209] (Z10-15-TEMPO).

[0210] In some embodiments, the composition comprises at least 0.02 area% of N-alkoxyamine, as determined by analytical chromatography coupled with mass spectrometry, such as at least 0.03 area%, such as at least 0.04 area%, such as at least 0.05 area%, such as at least 0.06 area%, such as at least 0.07 area%, such as at least 0.08 area%, such as at least 0.09 area%, such as at least 0.10 area% of N-alkoxyamine.

[0211] In some embodiments, the composition comprises at least 0.01 area % of N-alkoxyamine as determined by GC MS, such as at least 0.02 area %, such as at least 0.03 area %, such as at least 0.04 area %, such as at least 0.05 area %, such as at least 0.06 area %, such as at least 0.07 area %, such as at least 0.08 area %, such as at least 0.09 area %, such as at least 0.10 area % of N-alkoxyamine as determined by GC MS.

[0212] copper

[0213] In some embodiments, the composition further comprises copper, such as copper (I) or copper (II).

[0214] In some embodiments, the composition comprises copper(II) in the form of a copper(II) salt, such as copper(II) salts selected from the group consisting of: copper(II) carboxylate, copper(II) trifluoromethanesulfonate, copper(II) tetrafluoroborate, copper(II) hexafluorophosphate, copper(II) bromide, copper(II) chloride, copper(II) iodide, and copper(II) perchlorate.

[0215] In some embodiments, the composition comprises copper(I) in the form of a copper(I) salt, such as copper(I) salts selected from the group consisting of: cuprous chloride (I), cuprous bromide (I), cuprous iodide (I), cuprous cyanide (I), cuprous oxide (I), copper trifluoromethanesulfonate (I), tetra(acetonitrile)copper tetrafluoroborate (I), tetra(acetonitrile)copper tetraphenylborate (I), tetra(acetonitrile)copper hexafluorophosphate (I), tetra(acetonitrile)copper trifluoromethanesulfonate (I), cuprous sulfide (I), thiocyanate Copper trifluoroacetate (I), Cu[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Cl, Cu[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Br, CuBr(1,10-phenanthroline)2, CuCl(1,10-phenanthroline)]2, CuI(1,10-phenanthroline)2, copper trifluoroacetate (I), [Cu(PPh3)3]Br, [Cu(PPh3)3]F, [Cu(PPh3)3]Cl, Cu(OCOR) 2 ), Cu(SR) 2 ), Cu(SR) 2 2) Br, Cu(SR) 2 2) Cl, Cu(SR) 2 2) I, Cu(OSO2R) 2 ), CuOR 2 , where R 2 Selected from the following groups: alkyl, preferably C1-C 20Alkyl groups, optionally substituted with one or more aryl, alkoxy, and aryloxy groups; and aryl groups, preferably C5-C7 aryl groups, optionally substituted with one or more alkyl, aryl, alkoxy, and aryloxy groups; and mixtures of the foregoing groups.

[0216] N-alkoxyamines themselves

[0217] In some embodiments, N-alkoxyamines of the formula selected from the group consisting of: Z10-15-A-TEMPO; Z10, Z12-15-A-TEMPO; and Z8, E10-15-A-TEMPO are provided. (Z10-15-A-TEMPO);

[0218] (Z10,Z12-15-A-TEMPO);

[0219] (Z8,E10-15-A-TEMPO);

[0220] A is selected from the group consisting of: hydrogen, hydroxyl, carbonyl, alkyl, such as C. 1-6 Alkyl groups, amines, amides, such as C 1-6 -Amide, alkoxy group such as C 1-6 Alkoxy groups and esters such as C 1-6 Esters; or their ions or salts.

[0221] In some embodiments, A is H. In some embodiments, A is OH. In some embodiments, A is an amide, such as C. 1-6 -Amide, such as C1-amide. In some embodiments, A is a carbonyl group.

[0222] In some embodiments, the N-alkoxyamine has the formula Z10-15-A-TEMPO, where A is H. In some embodiments, the N-alkoxyamine has the formula Z10-15-A-TEMPO, where A is OH. In some embodiments, the N-alkoxyamine has the formula Z10-15-A-TEMPO, where A is a C1-amide (-NHCOCH3). In some embodiments, the N-alkoxyamine has the formula Z10-15-A-TEMPO, where A is a carbonyl group.

[0223] In some embodiments, the N-alkoxyamine has the formula Z10,Z12-15-A-TEMPO, where A is H. In some embodiments, the N-alkoxyamine has the formula Z10,Z12-15-A-TEMPO, where A is OH. In some embodiments, the N-alkoxyamine has the formula Z10,Z12-15-A-TEMPO, where A is a C1-amide (-NHCOCH3). In some embodiments, the N-alkoxyamine has the formula Z10,Z12-15-A-TEMPO, where A is a carbonyl group.

[0224] In some embodiments, the N-alkoxyamine has the formula Z8,E10-15-A-TEMPO, where A is H. In some embodiments, the N-alkoxyamine has the formula Z8,E10-15-A-TEMPO, where A is OH. In some embodiments, the N-alkoxyamine has the formula Z8,E10-15-A-TEMPO, where A is a C1-amide (-NHCOCH3). In some embodiments, the N-alkoxyamine has the formula Z8,E10-15-A-TEMPO, where A is a carbonyl group.

[0225] In some embodiments, the N-alkoxyamine is selected from the group consisting of:

[0226] (Z10-15-OH-TEMPO); and

[0227] (Z10-15-TEMPO).

[0228] In some embodiments, N-alkoxyamines selected from the group consisting of: Z11-16-A-TEMPO-2; Z11,Z13-16-A-TEMPO-2; and Z9,E11-16-A-TEMPO-2 are provided.

[0229] (Z11-16-A-TEMPO-2);

[0230] (Z11,Z13-16-A-TEMPO-2); and

[0231] (Z9,E11-16-A-TEMPO-2).

[0232] A is selected from the group consisting of: hydrogen, hydroxyl, carbonyl, alkyl, such as C. 1-6 Alkyl groups, amines, amides, such as C 1-6 -Amide, alkoxy group such as C 1-6 Alkoxy groups and esters such as C 1-6 Esters; or their ions or salts.

[0233] In some embodiments, A is H. In some embodiments, A is OH. In some embodiments, A is an amide, such as C. 1-6 -Amide, such as C1-amide. In some embodiments, A is a carbonyl group.

[0234] In some embodiments, the N-alkoxyamine has the formula Z11-16-A-TEMPO-2, wherein A is H. In some embodiments, the N-alkoxyamine has the formula Z11-16-A-TEMPO-2, wherein A is OH. In some embodiments, the N-alkoxyamine has the formula Z11-16-A-TEMPO-2, wherein A is a C1-amide (-NHCOCH3). In some embodiments, the N-alkoxyamine has the formula Z11-16-A-TEMPO-2, wherein A is a carbonyl group.

[0235] In some embodiments, the N-alkoxyamine has the formula Z11,Z13-16-A-TEMPO-2, wherein A is H. In some embodiments, the N-alkoxyamine has the formula Z11,Z13-16-A-TEMPO-2, wherein A is OH. In some embodiments, the N-alkoxyamine has the formula Z11,Z13-16-A-TEMPO-2, wherein A is a C1-amide (-NHCOCH3). In some embodiments, the N-alkoxyamine has the formula Z11,Z13-16-A-TEMPO-2, wherein A is a carbonyl group.

[0236] In some embodiments, the N-alkoxyamine has the formula Z9,E11-16-A-TEMPO-2, wherein A is H. In some embodiments, the N-alkoxyamine has the formula Z9,E11-16-A-TEMPO-2, wherein A is OH. In some embodiments, the N-alkoxyamine has the formula Z9,E11-16-A-TEMPO-2, wherein A is a C1-amide (-NHCOCH3). In some embodiments, the N-alkoxyamine has the formula Z9,E11-16-A-TEMPO-2, wherein A is a carbonyl group.

[0237] In some embodiments, the N-alkoxyamine is Z11-16-OH-TEMPO-2:

[0238] (Z11-16-OH-TEMPO-2).

[0239] Process for producing the composition

[0240] In some embodiments, a process is provided for producing a composition comprising a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, and combinations thereof; and b) an N-alkoxyamine; wherein the method includes the following steps:

[0241] i) Provide a reaction mixture comprising a fatty alcohol, a catalyst containing a copper source, and a solvent, and

[0242] ii) Oxidize fatty alcohols by adding O2 to the reaction mixture in an amount sufficient to convert more than 50% by weight of fatty alcohols into fatty aldehydes and less than 50% by weight of fatty alcohols into fatty acids.

[0243] In some implementations, this process is used to convert fatty alcohols into fatty aldehydes on a large scale, and the method includes the following steps:

[0244] a) Provide a reaction mixture comprising at least 1 kg of a fatty alcohol, a catalyst containing a copper source, at least 1 kg of a solvent, and a water-absorbing or adsorbing material for absorbing or adsorbing water, and

[0245] b) By feeding a gas or liquid containing O2 into the reaction medium, at least 0.01 μmol O2 is dissolved per μmol copper per minute in the reaction mixture or at least 0.001 μmol O2 is dissolved per μmol initial fatty alcohol per minute in the reaction mixture, thereby oxidizing more than 50% by weight of fatty alcohol to fatty aldehydes and less than 50% by weight of fatty alcohol to fatty acids.

[0246] In some embodiments, the process removes carbon atoms from fatty alcohols, including hydrogen atoms covalently attached to the carbon atoms, wherein the carbon atoms are covalently bonded to oxygen atoms of the hydroxyl groups of the fatty alcohols.

[0247] In some embodiments, this disclosure provides a composition that can be obtained by a process for producing the composition as defined herein.

[0248] Catalyst composition

[0249] The process for producing the compositions of this disclosure involves the oxidation of a primary alcohol to produce the corresponding aldehyde. The oxidation of the primary alcohol to the aldehyde is catalyzed by a catalyst composition.

[0250] The catalyst composition contains a copper (I) source, such as, for example, a copper (I) salt. The copper (I) source is a substance or mixture of substances containing a copper (I) compound that can be used for desired catalysis involving copper (I). Examples particularly include cuprous chloride (I), cuprous bromide (I), cuprous iodide (I), cuprous cyanide (I), cuprous oxide (I), copper trifluoromethanesulfonate (I), tetra(acetonitrile)copper tetrafluoroborate (I), tetra(acetonitrile)copper tetraphenylborate (I), tetra(acetonitrile)copper hexafluorophosphate (I), tetra(acetonitrile)copper trifluoromethanesulfonate (I), cuprous sulfide (I), copper thiocyanate (I), Cu[1,3-bis(2,6-diisopropylbenzene)] [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Cl, Cu[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Br, CuBr(1,10-phenanthroline)2, CuCl(1,10-phenanthroline)]2, CuI(1,10-phenanthroline)2, copper trifluoroacetate (I), [Cu(PPh3)3]Br, [Cu(PPh3)3]F, [Cu(PPh3)3]Cl, Cu(OCOR) 2 ), Cu(SR) 2 ), Cu(SR) 2 2) Br, Cu(SR) 2 2) Cl, Cu(SR) 2 2) I, Cu(OSO2R) 2 ), CuOR 2 , where R 2 Selected from the following groups: alkyl, preferably C1-C 20 Alkyl groups, optionally substituted with one or more aryl, alkoxy, and aryloxy groups; and aryl groups, preferably C5-C7 aryl groups, optionally substituted with one or more alkyl, aryl, alkoxy, and aryloxy groups; and mixtures of the foregoing groups. Furthermore, the copper (I) source can be a substance or mixture of substances containing copper in any other oxidation state, provided that it can be chemically or electrochemically converted to copper in the +1 oxidation state by reduction or oxidation.

[0251] In a preferred embodiment of this disclosure, the copper (I) source comprises copper in an oxidation state of +1.

[0252] In one embodiment of this disclosure, the copper(I) source is soluble in an organic solvent. In a preferred embodiment, the organic solvent is acetonitrile. The solubility of the reagent generally improves the reaction rate. In a preferred embodiment of this disclosure, the copper(I) source is a copper(I) salt containing a counterion (i.e., a negatively charged ion) that has good solubility in an organic solvent. Examples of negatively charged ions generally considered to have good solubility in organic solvents such as acetonitrile include trifluoromethanesulfonate, tetrafluoroborate, hexafluorophosphate, and halide ions.

[0253] The copper (I) source may further comprise a ligand coordinated with copper. Exemplary monovalent copper sources with coordinated ligands include copper tetraacetonitrile trifluoromethanesulfonate (I), copper tetraacetonitrile tetrafluoroborate (I), copper tetraacetonitrile hexafluorophosphate (I), copper tetraacetonitrile halide (I), CuBr(1,10-phenanthroline)2, CuCl(1,10-phenanthroline)2, and CuI(1,10-phenanthroline)2.

[0254] In a preferred embodiment of this disclosure, the copper (I) source is selected from the group consisting of copper tetraacetonitrile trifluoromethanesulfonate (I), copper tetraacetonitrile tetrafluoroborate (I), copper tetraacetonitrile hexafluorophosphate (I), and copper tetraacetonitrile halide (I).

[0255] Copper(I) ions can be generated in situ from a copper(II) compound and a reducing agent. Therefore, in one embodiment, the copper(I) source comprises a copper(II) compound and a reducing agent. In another embodiment, the copper(I) source is a copper(II) compound and a reducing agent.

[0256] In one embodiment, the copper(II) compound is a copper(II) salt. In one embodiment, the copper(II) salt comprises a counterion soluble in an organic solvent. The counterion soluble in an organic solvent typically comprises a large organic moiety and / or a delocalizable (e.g., through resonance or induction) negative charge. In one embodiment, the copper(II) salt is selected from the group consisting of copper(II) trifluoromethanesulfonate, copper(II) tetrafluoroborate, copper(II) hexafluorophosphate, copper(II) bromide, copper(II) chloride, copper(II) iodide, and copper(II) perchlorate.

[0257] The reducing agents disclosed herein can reduce copper(II) to copper(I). The reducing agent can be an organic or inorganic reducing agent. In one embodiment of this disclosure, the reducing agent is selected from the group consisting of copper metal, zinc metal, aluminum metal, sodium bisulfite, formic acid, salts of formic acid, oxalic acid, and salts of oxalic acid. Metal-based reducing agents can advantageously be in the form of powder, granules, shavings, or otherwise finely divided. The reducing agent can advantageously be selected to produce no byproducts or to produce byproducts that are easily removed, for example, by evaporation. In one embodiment of this disclosure, the copper(I) source comprises a copper(II) salt and copper metal.

[0258] In one embodiment of this disclosure, the catalyst composition comprises a ligand. The ligand is intended to coordinate with copper (I) in the catalyst composition, thereby increasing the solubility of copper (I), stabilizing the catalyst composition, and / or enhancing the catalytic activity of the catalyst composition.

[0259] Suitable ligands include those coordinated via nitrogen, oxygen, phosphorus, or other atoms having lone pairs of electrons. In one embodiment of this disclosure, the ligand is coordinated via a portion selected from the group consisting of pyridine, triarylphosphine, diarylphosphine, amine, imidazole, pyrazole, pyrrole, triazole, tetrazolium, imine, enamine, phenol, or portions comprising any of the listed portions. In a preferred embodiment, the ligand is coordinated via a pyridine portion.

[0260] The ligand can be a monodentate or a polydentate ligand. In one embodiment of this disclosure, the ligand is a monodentate ligand. In another embodiment of this disclosure, the ligand is a bidentate ligand. In yet another embodiment, the ligand is a polydentate ligand coordinated to three or more atoms.

[0261] In one embodiment of this disclosure, the catalyst composition comprises a single type of ligand as described herein. In another embodiment of this disclosure, the catalyst composition comprises a mixture of two or more types of ligands as described herein.

[0262] In one embodiment of this disclosure, the ligand is selected from the group consisting of DETA, PMDETA, TETA, HMTETA, Me6TREN, cyclam, Me6cyclam, DMCBCy, bpy, dNbpy, 1,10-Phen, tpy, tNtpy, BPMPrA, BPMOA, BPMODA, TPMA, and TPEA. In one embodiment of this disclosure, the ligand is a secondary amine, such as a secondary amine having a bulky substituent (i.e., to reduce the nucleophilicity of the amine). In one embodiment of this disclosure, the ligand is a bidentate nitrogen ligand. In one embodiment, the ligand comprises a 2,2'-bipyridine moiety or a 2,2'-bipyrimidine moiety. In one embodiment, the ligand is selected from the group consisting of 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dimethyl-2,2'-bipyridine, 2,2'-bipyrimidine, 2,2'-bipyridine-4,4'-dicarboxylic acid or an ester thereof, and 2,2'-bipyridine-5,5'-dicarboxylic acid or an ester thereof. In a preferred embodiment of this disclosure, the ligand is 2,2'-bipyridine (bpy).

[0263] The catalyst composition used in the process of this disclosure comprises an aminoxylradical compound (2,2,6,6-tetramethylpiperidin-1-yl)oxy (TEMPO) or a derivative thereof. In one embodiment of this disclosure, the aminoxylradical compound is selected from the group consisting of: TEMPO, (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxy (4-OH-TEMPO), 4-acetamido-TEMPO, 4-hydroxy-TEMPO benzoate, 4-amino-TEMPO, 2-azaadamantane-N-oxy, 9-azabicyclo[3.3.1]nonane-N-oxy, 4-carboxyl-TEMPO, 4-maleimide-TEMPO, 4-methoxy-TEMPO, 1-methyl-2-azaadamantane-N-oxy, 4-oxo-TEMPO, and polymers functionalized with any of said aminoxylradical compounds. In a preferred embodiment of this disclosure, the aminooxy radical compound is selected from the group consisting of TEMPO or (4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxy (4-OH-TEMPO). The aminooxy radical compound is intended to be part of a catalytic cycle for the oxidation of the fatty alcohol compositions of this disclosure. It is generally accepted that TEMPO and its derivatives described herein act as catalysts for the oxidation of alcohol functional groups to aldehyde functional groups when the oxidant is O2. However, as used herein, the TEMPO and its derivatives disclosed herein are also referred to as "oxidants".

[0264] In one embodiment of this disclosure, the catalyst composition comprises a base. While some specific bases are mentioned below, many different bases are contemplated for use in carrying out this disclosure. In one embodiment of this disclosure, the base is an organic base. The use of an organic base may be advantageous because it can affect the solubility of the base in a reaction medium as disclosed herein. In one embodiment of this disclosure, the base is a nitrogen base. In one embodiment, the base is a Schiff base. In one embodiment, the base is an oxygen base. In one embodiment of this disclosure, the base is selected from the group consisting of 1-methylimidazole, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,1,3,3-tetramethylguanidine, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, and potassium tert-butoxide. In one embodiment of this disclosure, the base is selected from the group consisting of 1-methylimidazole, potassium tert-butoxide, or 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU).

[0265] In one embodiment of this disclosure, the elements of the catalyst composition as provided herein may be mixed to form the catalyst composition before the catalyst composition is added to the reaction mixture. In another embodiment, the elements of the catalyst composition may be added to the reaction mixture individually. In yet another embodiment, a subset of the elements of the catalyst composition may be mixed and added to the reaction mixture, while the remaining elements of the catalyst composition are added and / or premixed individually and then added to the reaction mixture.

[0266] Oxidation

[0267] The processes intended for producing the compositions of this disclosure can be used to oxidize a variety of primary alcohol compositions, such as those comprising primary alcohols having a chain length of at least two carbon atoms. However, the disclosed methods are particularly suitable for the oxidation of primary alcohols (i.e., fatty alcohols) having a chain length of eight or more carbon atoms, as further defined in the “Fatty Alcohols” and “Fatty Aldehydes” sections herein. Other known methods for carrying out oxidation typically produce fatty aldehyde compositions only in low yields and / or with low purity. “Over-oxidation,” i.e., the further oxidation of the aldehyde to the corresponding carboxylic acid, is often the primary cause of low reaction yields and / or purity of aldehyde compositions. Other known methods for oxidizing short primary alcohols may not be suitable for the oxidation of fatty alcohols because the oxidation may be incomplete, “over-oxidation” may occur, and / or purification of the reaction products may be impractical. Regarding a further relationship between the oxidation of fatty alcohols to fatty aldehydes, other known methods typically involve the use of relatively large volumes of solvent and / or purification of the reaction products, as outlined in the Background section. However, the methods disclosed in this invention use relatively small volumes of solvent for the oxidation reaction and relatively small amounts of solvent for the purification of the reaction products. The methods disclosed in this invention are also advantageous because they are scalable, meaning they can work both on small scales (e.g., less than 10 g of fatty alcohol composition) and on large scales (e.g., greater than 100 g of fatty alcohol composition, such as greater than 500 g of fatty alcohol composition). Other known methods for oxidizing fatty alcohols to the corresponding fatty aldehydes may work well on small scales (e.g., less than 10 g of fatty alcohol composition), but they may not be scalable, meaning they may not provide good reaction yields or product purity on large scales (e.g., greater than 100 g of fatty alcohol composition, such as greater than 500 g of fatty alcohol composition). Obtaining aldehyde compositions relatively free of byproducts such as the corresponding fatty carboxylic acids or unreacted fatty alcohols is advantageous because it eliminates the need for time-consuming or expensive purification steps such as distillation. Each of the features mentioned above (small solvent volume, scalability, and substrate range) makes the methods disclosed in this invention particularly suitable for industrial applications.

[0268] One embodiment of this disclosure provides a method for converting fatty alcohols into fatty aldehydes, the method comprising the following steps:

[0269] a. Providing a reaction mixture comprising a fatty alcohol composition containing a fatty alcohol, a catalyst composition, and a solvent;

[0270] b. Expose the reaction mixture to at least 0.25 ml of oxygen per minute per gram of fatty alcohol by bubbling a mixture of gases containing oxygen through the reaction mixture.

[0271] This results in the production of fatty aldehydes.

[0272] In one embodiment of this disclosure, a method for large-scale conversion of fatty alcohols into fatty aldehydes is provided, the method comprising the following steps:

[0273] a) Provide a reaction mixture comprising at least 1 kg of a fatty alcohol, a catalyst containing a copper source, at least 1 kg of a solvent, and a water-absorbing or adsorbing material for absorbing or adsorbing water, and

[0274] b) By feeding a gas or liquid containing O2 into the reaction medium, at least 0.01 μmol O2 is dissolved per μmol copper per minute in the reaction mixture or at least 0.001 μmol O2 is dissolved per μmol initial fatty alcohol per minute in the reaction mixture, thereby oxidizing more than 50% by weight of fatty alcohol to fatty aldehydes and less than 50% by weight of fatty alcohol to fatty acids.

[0275] The method disclosed in this invention can be carried out without any external cooling and without any external heating. However, the oxidation reaction of this invention is generally exothermic, and therefore the temperature of the reaction mixture is expected to rise during the reaction. In one embodiment of this disclosure, the reaction is carried out at 5°C to 80°C, such as 10°C to 70°C, such as 15°C to 65°C. In another embodiment of the reaction, the reaction mixture is exposed to oxygen at 5°C to 80°C, such as 10°C to 70°C, such as 15°C to 65°C.

[0276] The methods disclosed herein can be carried out at ambient pressure or at elevated pressure. In one embodiment, the exposure of the reaction mixture to oxygen is carried out at pressures of 0.5 to 40 bar, such as 0.5 to 30 bar, such as 0.6 to 20 bar, such as 0.7 to 10 bar, such as 0.8 to 5 bar. In one embodiment, the exposure of the reaction mixture to oxygen is carried out at pressures of 0.5 to 0.8 bar, 0.8 to 1.2 bar, 1.2 to 1.5 bar, 1.5 to 2 bar, 2 to 5 bar, 5 to 10 bar, 10 to 20 bar, or 20 to 30 bar. In one embodiment of this disclosure, the exposure of the reaction mixture to oxygen is carried out at pressures of 0.8 to 1.2 bar. However, it is contemplated that the methods disclosed herein can be carried out at pressures below 0.5 bar or 0.8 bar, provided that the amount of oxygen supplied to the reaction mixture is as disclosed herein. In one embodiment, the pressure disclosed herein is the pressure in the reaction vessel in which the reaction mixture is exposed to oxygen. In one embodiment, the pressure disclosed herein is the partial pressure of oxygen in the reaction vessel.

[0277] In additional or alternative embodiments, O2 is added to the reaction medium by mixing the reaction mixture with a gas (such as air) or liquid containing O2 (optionally rich in O2). This mixing can be carried out by bubbling the O2-containing gas mixture through the reaction mixture.

[0278] In some embodiments, the copper source disclosed herein comprises a copper (I) salt or a combination of copper (II) and a reducing agent.

[0279] oxygen transfer rate

[0280] The essential element of this disclosure is that the amount of oxygen supplied to the reaction mixture is higher than a certain threshold.

[0281] In one embodiment of this disclosure, the reaction mixture is exposed to at least 0.3 ml of oxygen per minute per gram of fatty alcohol composition, such as at least 0.4 ml, 0.5 ml, 0.6 ml, 0.7 ml, 0.8 ml, 0.9 ml, 1.0 ml, 1.1 ml, 1.2 ml, 1.3 ml, or 1.4 ml of oxygen per minute per gram of fatty alcohol composition, or at least 1.5 ml of oxygen per minute per gram of fatty alcohol composition. In a preferred embodiment of this disclosure, the reaction mixture is exposed to at least 1.5 ml of oxygen per minute per gram of fatty alcohol composition.

[0282] In one embodiment of this disclosure, the reaction mixture is exposed to at least 0.3 ml of oxygen per gram of fatty alcohol per minute, such as at least 0.4 ml, 0.5 ml, 0.6 ml, 0.7 ml, 0.8 ml, 0.9 ml, 1.0 ml, 1.1 ml, 1.2 ml, 1.3 ml, or 1.4 ml of oxygen per gram of fatty alcohol per minute, or such as at least 1.5 ml of oxygen per gram of fatty alcohol per minute. In a preferred embodiment of this disclosure, the reaction mixture is exposed to at least 1.5 ml of oxygen per gram of fatty alcohol per minute.

[0283] As used in this article, whenever the volume of a gas is described, it is intended to correspond to the volume of the gas at a pressure of approximately 1 bar.

[0284] In one embodiment of this disclosure, the reaction mixture is exposed to at least 60 ml of oxygen per mol of fatty alcohol per minute, such as at least 100 ml, 150 ml, 200 ml, 250 ml, 300 ml, 350 ml, or 400 ml of oxygen per mol of fatty alcohol per minute, such as at least 450 ml of oxygen per minute. In a preferred embodiment of this disclosure, the reaction mixture is exposed to at least 450 ml of oxygen per mol of fatty alcohol per minute.

[0285] In one embodiment of this disclosure, the reaction mixture is exposed to at least 10 μmol of oxygen per minute per gram of fatty alcohol, such as at least 12 μmol, 16 μmol, 20 μmol, 24 μmol, 28 μmol, 32 μmol, 36 μmol, 40 μmol, 44 μmol, 48 μmol, 52 μmol, 56 μmol, or 60 μmol of oxygen per minute per gram of fatty alcohol. In a preferred embodiment of this disclosure, the reaction mixture is exposed to at least 60 μmol of oxygen per minute per gram of fatty alcohol.

[0286] In one embodiment of this disclosure, the reaction mixture is exposed to at least 2.5 mmol of oxygen per mole of fatty alcohol per minute, such as at least 4 mmol, 6 mmol, 8 mmol, 10 mmol, 12 mmol, 14 mmol, or 16 mmol of oxygen per mole of fatty alcohol per minute, such as at least 18 mmol of oxygen. In a preferred embodiment of this disclosure, the reaction mixture is exposed to at least 18 mmol of oxygen per mole of fatty alcohol per minute.

[0287] The oxygen supplied to the reaction mixture of this disclosure may be provided as pure oxygen or as a gas mixture containing oxygen. In one embodiment of this disclosure, the gas mixture contains 5% to 100% oxygen. In another embodiment of this disclosure, the gas mixture contains 15% to 25% oxygen. In one embodiment of this disclosure, the gas mixture contains at least 90% oxygen. In one embodiment of this disclosure, the gas mixture is substantially pure oxygen. As outlined herein in the "Water Removal" section, it is advantageous if the amount of water present in the reaction mixture is minimized. Therefore, in a preferred embodiment of this disclosure, the gas mixture does not contain H2O.

[0288] Sufficient oxygen exposure to the reaction mixture is expected to be achieved partly by using an adequate oxygen supply as outlined herein, and also by ensuring a high contact surface between the supplied gas mixture and the liquid phase of the reaction mixture. A high contact surface is important for ensuring sufficient oxygen exposure to the reaction mixture, such as by ensuring sufficient oxygen solubility in the liquid phase of the reaction mixture. This can be achieved by using equipment for bubbling the gas through the liquid, such as, for example, a jetting device. Increasing the jetting of the gas mixture through the solution is expected to increase the oxygen transfer rate. Increasing the partial pressure of oxygen supplied to the reaction mixture is expected to increase the oxygen transfer rate. Stirring the reaction mixture is expected to increase the oxygen transfer rate. Therefore, stirring the reaction mixture of this disclosure is desirable. In one embodiment of this disclosure, a gas mixture containing oxygen is bubbled through the reaction mixture. In another embodiment of this disclosure, the bubbling of the gas mixture through the reaction is carried out using a jetting device. In one embodiment of this disclosure, the reaction mixture is stirred while being exposed to oxygen.

[0289] In one embodiment of this disclosure, the reaction mixture is exposed to oxygen for at least 5 minutes, such as at least 10 minutes, such as at least 20 minutes, such as at least 30 minutes, such as at least 40 minutes, such as at least 50 minutes, such as at least 60 minutes, such as at least 70 minutes, 80 minutes, 90 minutes, such as at least 100 minutes. It is anticipated that the exposure to oxygen does not need to be sustained for a continuous period as specified herein, but can be interrupted. Therefore, in one embodiment of this disclosure, the reaction mixture is exposed to oxygen for an uninterrupted period of at least 60 minutes, such as at least 70 minutes, 80 minutes, 90 minutes, such as at least 100 minutes. In another embodiment of this disclosure, the reaction mixture is exposed to oxygen for two or more time periods, wherein the combined time periods total at least 60 minutes, such as at least 70 minutes, 80 minutes, 90 minutes, such as at least 100 minutes.

[0290] In one embodiment of this disclosure, exposure to O2 is carried out in a bubble column reactor or a trickle bed reactor.

[0291] The longer reaction time is expected to result in lower conversion and / or lower yield of the disclosed aldehyde composition. This is expected to be due to, for example, excessive oxidation of the aldehyde and / or introduction of water into the reaction mixture beyond the drying capacity of the drying device. In one embodiment of this disclosure, the reaction mixture is exposed to oxygen for up to 2000 minutes, such as up to 1900 minutes, 1800 minutes, 1700 minutes, 1600 minutes, 1500 minutes, 1400 minutes, 1300 minutes, 1200 minutes, 1100 minutes, 1000 minutes, 900 minutes, 800 minutes, 700 minutes, 600 minutes, 500 minutes, 400 minutes, 350 minutes, 325 minutes, 300 minutes, 275 minutes, such as up to 250 minutes.

[0292] Importantly, the amount of oxygen added to the reaction medium is balanced with the amount and / or effectiveness of the fatty alcohols and catalyst in the reaction medium. Optimal oxygen feeding into the reaction medium for aldehyde formation may also be influenced by the amount of fatty acids in the reaction medium, as higher acid formation requires increased oxygen feed. Therefore, in additional or alternative embodiments, the process for producing the compositions described herein includes dissolving at least 0.010 μmol of copper per μmol per minute in the reaction mixture, such as at least 0.020 μmol, such as at least 0.030 μmol, such as at least 0.040 μmol, such as at least 0.049 μmol, such as at least 0.060 μmol, such as at least 0.070 μmol, such as at least 0.080 μmol, such as at least 0.090 μmol, such as at least 0.100 μmol of O2 per μmol of initial fatty alcohol per minute in the reaction mixture, such as at least 0.0010 μmol, such as at least 0.0020 μmol, such as at least 0.0025 μmol, such as at least 0.0030 μmol, such as at least 0.0050 μmol, such as at least 0.0075 μmol, such as at least 0.0100 μmol of O2 per μmol of fatty acid per minute in the reaction mixture. μmol, such as at least 0.015 μmol, such as at least 0.020 μmol, such as at least 0.025 μmol, such as at least 0.030 μmol, such as at least 0.050 μmol, such as at least 0.075 μmol, such as at least 0.100 μmol of dissolved O2.

[0293] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving at least 0.049 μmol of dissolved O2 per minute per μmol of copper in the reaction mixture.

[0294] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving at least 0.02 μmol of dissolved O2 per μmol of copper per minute in the reaction mixture, such as dissolving at least 0.03 μmol of dissolved O2 per μmol of copper per minute in the reaction mixture, such as at least 0.04 μmol of dissolved O2 per minute.

[0295] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving 0.01 to 1.00 μmol of dissolved O2 per μmol of copper per minute in the reaction mixture, such as dissolving 0.01 to 0.80 μmol per μmol of copper per minute in the reaction mixture, such as 0.01 to 0.60 μmol, such as 0.01 to 0.40 μmol, such as 0.01 to 0.20 μmol, such as 0.01 to 0.10 μmol of dissolved O2 per minute.

[0296] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving at least 0.0025 μmol of dissolved O2 per minute per μmol of initial fatty alcohol in the reaction mixture.

[0297] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving at least 0.002 μmol of dissolved O2 per minute per μmol of initial fatty alcohol in the reaction mixture, such as dissolving at least 0.003 μmol per minute per μmol of initial fatty alcohol in the reaction mixture, such as at least 0.004 μmol of dissolved O2.

[0298] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving 0.001 to 1.00 μmol of dissolved O2 per μmol of initial fatty alcohol per minute in the reaction mixture, such as dissolving 0.001 to 0.80 μmol per μmol of initial fatty alcohol per minute in the reaction mixture, such as 0.001 to 0.60 μmol, such as 0.001 to 0.40 μmol, such as 0.001 to 0.20 μmol, such as 0.001 to 0.10 μmol of dissolved O2 per minute.

[0299] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving at least 0.025 μmol of dissolved O2 per minute per μmol of fatty acid in the reaction mixture.

[0300] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving at least 0.01 μmol of dissolved O2 per μmol of fatty acid per minute in the reaction mixture, such as at least 0.02 μmol, at least 0.03 μmol, or at least 0.04 μmol of dissolved O2 per μmol of fatty acid per minute in the reaction mixture.

[0301] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving at least 10 μmol O2 per minute per gram of fatty alcohol in the reaction mixture, such as at least 20 μmol O2, at least 40 μmol O2, or at least 60 μmol O2, to obtain a fatty aldehyde, optionally wherein the fatty alcohol and the fatty aldehyde are desaturated.

[0302] In some embodiments, the process for producing the compositions of this disclosure further includes dissolving O2 in the reaction medium at a rate sufficient to maintain at least 80% O2 saturation, such as at least 85% O2 saturation, such as at least 90% O2 saturation, such as at least 95% O2 saturation, such as at least 100% O2 saturation, in the reaction medium during the oxidation reaction.

[0303] In some implementations, the gas or liquid containing O2 is air, which is optionally rich in O2.

[0304] In some embodiments, a process for producing the compositions of this disclosure is provided, wherein feeding a gas or liquid containing O2 into the reaction medium is carried out by pumping or bubbling a mixture of gas or liquid containing O2 through the reaction mixture.

[0305] Reaction conditions

[0306] This disclosure achieves the conversion of fatty alcohol compositions to fatty aldehyde compositions using a relatively small volume of solvent. In particular, previously reported methods for converting fatty alcohols to fatty aldehydes, as outlined herein, utilize relatively large volumes of solvent in the reaction mixture. Large solvent volumes are generally considered infeasible for large-scale production due to solvent costs, environmental footprint, and the potential challenges of handling large reaction volumes. Therefore, the oxidation method disclosed in this invention can be advantageously used for the large-scale production of fatty aldehyde compositions due to the need for a relatively small solvent volume. "Relatively small solvent volume" means the volume as outlined herein.

[0307] In one embodiment of this disclosure, the reaction mixture comprises a solvent. The solvent forming part of the reaction mixture may be a substantially pure solvent, or it may be a mixture of solvents. Therefore, in one embodiment, reference to the solvent in the reaction mixture may also mean a solvent mixture comprising two or more solvents.

[0308] In one embodiment of this disclosure, the solvent is selected from the group consisting of acetonitrile, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), alkanes (such as pentane, hexane, and heptane), cycloalkanes, petroleum ethers (such as heavy petroleum ether or light petroleum ether), dioxane, diethyl ether, dichloromethane, tetrahydrofuran, ethyl acetate, acetone, nitromethane, propylene carbonate, and solvent mixtures containing any of the solvents described above.

[0309] In one embodiment, the solvent is an aprotic solvent. Advantageously, the solvent is aprotic because protons, such as those derived from OH- groups or amines, can harmfully interfere with components (such as, for example, catalyst compositions), for example, by deactivating bases. In one embodiment of this disclosure, the solvent is selected from a list of the following: acetonitrile, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), alkanes (such as pentane, hexane, and heptane), cycloalkanes, petroleum ethers (such as heavy or light petroleum ethers), dioxane, diethyl ether, dichloromethane, tetrahydrofuran, ethyl acetate, acetone, nitromethane, propylene carbonate, and solvent mixtures containing any of said solvents. In a preferred embodiment, the solvent is selected from a list of the following: acetonitrile, DMSO, DMF, and solvent mixtures containing any of said solvents. In a further preferred embodiment, the solvent is acetonitrile or contains acetonitrile. In another preferred embodiment of this disclosure, the solvent is acetonitrile.

[0310] In one embodiment, the solvent is a polar solvent. Advantageously, the solvent is polar because this improves the solubility of at least some components of the reaction mixture and / or components of the gas mixture. In one embodiment of this disclosure, the solvent is selected from dichloromethane, tetrahydrofuran, ethyl acetate, acetone, dimethylformamide (DMF), acetonitrile, dimethyl sulfoxide (DMSO), nitromethane, propylene carbonate, and solvent mixtures containing any of said solvents. In a preferred embodiment, the solvent is selected from the group consisting of acetonitrile, DMSO, DMF, or solvent mixtures containing any of said solvents. In even a further preferred embodiment, the solvent is acetonitrile or a solvent mixture containing acetonitrile. In yet another preferred embodiment, the solvent is acetonitrile.

[0311] When assessing the relative amount of solvent used in a chemical reaction, the amount of solvent can be compared with the amount of reagent or one of the reagents that is converted in the chemical reaction, or the amount of product or one of the products obtained in the chemical reaction.

[0312] The amount of solvent in the reaction mixture can be compared to the amount of the fatty alcohol composition. In one embodiment of this disclosure, the weight of the solvent in the reaction mixture is 0 to 2000% of the weight of the fatty alcohol composition, such as 100% to 2000%, such as 100% to 1500%, such as 100% to 1000%, such as 100% to 500%. The fatty alcohol composition may contain other compounds besides fatty alcohols. To assess the amount of solvent, it is preferable to exclude these other compounds when calculating the amount of solvent. Furthermore, the fatty alcohol composition may contain one or more solvents, i.e., "fatty alcohol composition solvent". In a preferred embodiment of this disclosure, the fatty alcohol composition solvent is ignored when assessing the amount of the fatty alcohol composition. In one embodiment of this disclosure, the weight of the solvent corresponds to 100% to 2000% of the weight of one or more fatty alcohols in the fatty alcohol composition, such as 100% to 1500%, such as 100% to 1000%, such as 100% to 500%.

[0313] The amount of solvent in the reaction mixture can be compared with the amount of the aliphatic aldehyde composition obtained from the reaction mixture. In one embodiment of this disclosure, the weight of the solvent in the reaction mixture is 100% to 2000%, such as 100% to 1500%, such as 100% to 1000%, such as 100% to 500% of the weight of the aliphatic aldehyde composition. The aliphatic aldehyde composition may contain other compounds besides aliphatic aldehydes. To assess the amount of solvent, it is preferable to exclude these other compounds when calculating the amount of solvent. Furthermore, the aliphatic aldehyde composition may contain one or more solvents, i.e., "aliphatic aldehyde composition solvent". In a preferred embodiment of this disclosure, the aliphatic aldehyde composition solvent is ignored when assessing the amount of the aliphatic aldehyde composition. In one embodiment of this disclosure, the weight of the solvent corresponds to 100% to 2000%, such as 100% to 1500%, such as 100% to 1000%, such as 100% to 500% of the weight of one or more aliphatic aldehydes in the aliphatic aldehyde composition.

[0314] In some embodiments, the solvent is a non-halogenated solvent. In some embodiments, the solvent is selected from acetonitrile, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), pentane, hexane, heptane, cycloalkanes, petroleum ether, dioxane, diethyl ether, tetrahydrofuran, ethyl acetate, acetone, nitromethane, propylene carbonate, or combinations thereof.

[0315] Determine whether the production method has been used.

[0316] In some embodiments, a method is provided for determining whether a composition has been prepared by the process of this disclosure, wherein the method includes the following steps:

[0317] a) Provide a composition for analysis;

[0318] b) subjecting a sample of the composition in a) to mass spectrometry to obtain a mass spectrum, preferably analytical chromatography coupled with mass spectrometry;

[0319] c) Wherein the mass spectrum obtained in b) contains a mass corresponding to an N-alkoxyamine as defined herein, the composition has been obtained by the process described herein.

[0320] In some implementations, a method

[0178] is provided, wherein the mass spectrum substantially corresponds to Figure 4 The mass spectrum.

[0321] In some embodiments, methods of this disclosure are provided, wherein analysis of the sample in

[0178] b) reveals at least 0.01 area % of N-alkoxyamines, such as at least 0.02 area %, such as at least 0.03 area %, such as at least 0.04 area %, such as at least 0.05 area %, such as at least 0.06 area %, such as at least 0.07 area %, such as at least 0.08 area %, such as at least 0.09 area %, such as at least 0.10 area % of N-alkoxyamines.

[0322] In some embodiments, a method of the present disclosure is provided, wherein analysis of the sample in

[0178] b) by GC MS reveals at least 0.01 area % of N-alkoxyamines, such as at least 0.02 area %, such as at least 0.03 area %, such as at least 0.04 area %, such as at least 0.05 area %, such as at least 0.06 area %, such as at least 0.07 area %, such as at least 0.08 area %, such as at least 0.09 area %, such as at least 0.10 area % of N-alkoxyamines.

[0323] Example

[0324] Example 1: Monitoring fatty alcohol oxidation and N-alkoxyamine formation

[0325] A 1-liter bottle was equipped with an air injector connected to a flow controller, a temperature probe, and a stirring magnet. The bottle was filled with 100 g of Z11-hexadecenol oil, 3.25 g of 2,2'-bipyridine, 1.8 g of 4-hydroxyTEMPO, 1.7 g of N-methylimidazole, and 100 g of acetonitrile. A solution of 7.8 g of Cu(ACN)OTf in 100 g of acetonitrile was added to the mixture. The injector was started at an air flow rate of 2.5 L / min. Samples were taken periodically throughout the reaction process. 3 µL of the reaction mixture was diluted in 1 mL of ethyl acetate and analyzed by GC to provide... Figure 1 Conversion rate overview.

[0326] Example 2: Characterization of N-alkoxyamine markers

[0327] Characterization of N-alkoxyamine markers

[0328] N-alkoxyamines Z10-15-TEMPO derived from the oxidation of Z11-16: aldehydes were observed using two gas chromatography (GC) techniques. GC coupled with a flame ionization detector (GC-FID) confirmed the compounds in representative samples by matching the retention times with those of N-alkoxyamine Z10-15-TEMPO obtained by chemical synthesis according to the procedure of this embodiment. When compared with synthetic standards, GC coupled with a mass spectrometer (GC-MS) operating at an electron ionization source at an industrial standard of 70 eV confirmed the compounds in representative samples by retention time matching and mass spectrometric confirmation. Due to the additional confirmatory power of mass spectrometry, the N-alkoxyamines of this disclosure are ideally identified using GC-MS to confirm their presence in samples, where GC-FID is a complementary technique and can be used for quantitative purposes.

[0329] Instrumental Methods

[0330] GC-FID conditions:

[0331] GC System: Agilent 7890B

[0332] Column: Agilent (catalog number 19091S-433UI), HP-5MS, 30 m x 250 µm x 0.25 µm

[0333] Inlet temperature: 230℃

[0334] Flow split ratio: 20:1

[0335] Column flow rate: 1.5 mL / min

[0336] Carrier gas: H2

[0337] Injection volume: 1 µL

[0338] Oven: 80℃ for 1 min, 15℃ / min to 150℃ for 6 min, 5℃ / min to 200℃, 20℃ / min to 300℃ for 8 min.

[0339] Detector: FID

[0340] GC-MS conditions:

[0341] GC System: Agilent 6890

[0342] Column: Agilent (catalog number 19091S-433UI), HP-5MS, 30 m x 250 µm x 0.25 µm

[0343] Inlet temperature: 230℃

[0344] Split ratio: a variable based on sample / standard concentration.

[0345] Column flow rate: 1 mL / min

[0346] Carrier gas: He

[0347] Injection volume: 1 µL

[0348] Oven: 80℃ for 1 min, 15℃ / min to 150℃ for 7 min, 10℃ / min to 210℃, 20℃ / min to 300℃ for 5 min

[0349] Mass spectrometer: Agilent 5975 MSD

[0350] Ion source: EI at 70 eV

[0351] Acquisition type: Scan

[0352] Example 3: Characterization of the alternative N-alkoxyamine marker 2

[0353] Characterization of N-alkoxyamine markers

[0354] Two gas chromatography (GC) techniques were used to observe the TEMPO adducts of Z11-16: aldehydes. GC coupled with a flame ionization detector (GC-FID) confirmed the compounds in representative samples by matching retention times with synthetic standards. When compared with synthetic standards, GC coupled with a mass spectrometer (GC-MS) operated at an electron ionization source at the industrial standard 70 eV confirmed the compounds in representative samples by retention time matching and mass spectrometric confirmation. Due to the additional confirmatory power of mass spectrometry, GC-MS is the preferred technique for confirming the presence of adducts in future samples, with GC-FID being a complementary technique and usable for quantitative purposes. The structure of N-alkoxyamine marker 2 is shown below:

[0355] Marker 2 (4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyl)(Z)-hexadec-11-enoate

[0356]

[0357] Instrumental Methods

[0358] GC-FID conditions:

[0359] GC System: Agilent 7890B

[0360] Column: Agilent (catalog number 19091S-433UI), HP-5MS, 30 m x 250 µm x 0.25 µm

[0361] Inlet temperature: 230℃

[0362] Flow split ratio: 20:1

[0363] Column flow rate: 1.5 mL / min

[0364] Carrier gas: H2

[0365] Injection volume: 1 µL

[0366] Oven: 80℃ for 1 min, 15℃ / min to 150℃ for 6 min, 5℃ / min to 200℃, 20℃ / min to 300℃ for 8 min.

[0367] Detector: FID

[0368] GC-MS conditions:

[0369] GC System: Agilent 6890

[0370] Column: Agilent (catalog number 19091S-433UI), HP-5MS, 30 m x 250 µm x 0.25 µm

[0371] Inlet temperature: 230℃

[0372] Split ratio: a variable based on sample / standard concentration.

[0373] Column flow rate: 1 mL / min

[0374] Carrier gas: He

[0375] Injection volume: 1 µL

[0376] Oven: 80℃ for 1 min, 15℃ / min to 150℃ for 7 min, 10℃ / min to 210℃, 20℃ / min to 300℃ for 5 min

[0377] Mass spectrometer: Agilent 5975 MSD

[0378] Ion source: EI at 70 eV

[0379] Acquisition type: Scan

Claims

1. A method for determining whether a composition comprising: a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, fatty alcohol acetates, and combinations thereof; and b) an N-alkoxyamine; wherein the process comprises the following steps: i) Provide a reaction mixture comprising a fatty alcohol, a catalyst containing a copper source, and a solvent, and ii) Oxidizing the fatty alcohol by adding O2 to the reaction mixture in an amount sufficient to convert more than 50% by weight of the fatty alcohol into fatty aldehydes and less than 50% by weight of the fatty alcohol into fatty acids; The method includes the following steps: A) Provide a composition for analysis; B) subjecting a sample of the composition described in A) to mass spectrometry to obtain a mass spectrum, preferably analytical chromatography coupled with mass spectrometry; C) Wherein if the mass spectrum obtained in B) contains a mass (m / z) corresponding to an N-alkoxyamine, then the composition comprising a) and b) has been obtained by the process described.

2. The method according to claim 1, wherein the mass spectrum substantially corresponds to the mass spectrum of FIG4.

3. The method according to any one of claims 1-2, wherein: a. Analysis of the sample described in b) revealed at least 0.01 area % of the N-alkoxyamine, such as at least 0.02 area %, such as at least 0.03 area %, such as at least 0.04 area %, such as at least 0.05 area %, such as at least 0.06 area %, such as at least 0.07 area %, such as at least 0.08 area %, such as at least 0.09 area %, such as at least 0.10 area % of the N-alkoxyamine; and / or b. Analysis of the sample described in b) by GC MS revealed at least 0.01 area % of the N-alkoxyamine, such as at least 0.02 area %, such as at least 0.03 area %, such as at least 0.04 area %, such as at least 0.05 area %, such as at least 0.06 area %, such as at least 0.07 area %, such as at least 0.08 area %, such as at least 0.09 area %, such as at least 0.10 area % of the N-alkoxyamine.

4. A composition comprising: a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, fatty alcohol acetates, and combinations thereof; and b) an N-alkoxyamine.

5. The method according to any one of claims 1-3 or the composition according to claim 4, wherein the at least one active ingredient is a pheromone.

6. The method according to any one of claims 1-3 or the composition according to any one of claims 4-5, wherein the composition is a bio-based composition and / or a biopesticide.

7. The method according to any one of claims 1-3 or the composition according to any one of claims 4-6, wherein the composition comprises: a. At least 20% bio-based carbon, such as at least 30% bio-based carbon, such as at least 40% bio-based carbon, such as at least 50% bio-based carbon, such as at least 60% bio-based carbon, such as at least 70% bio-based carbon, such as at least 75% bio-based carbon, such as at least 80% bio-based carbon, such as at least 85% bio-based carbon, such as at least 90% bio-based carbon, such as at least 95% bio-based carbon, such as 100% bio-based carbon; and / or b. 20% to 100% bio-based carbon, such as 30% to 100% bio-based carbon, such as 40% to 100% bio-based carbon, such as 50% to 100% bio-based carbon, such as 60% to 100% bio-based carbon, such as 70% to 100% bio-based carbon, such as 75% to 100% bio-based carbon, such as 80% to 100% bio-based carbon, such as 85% to 100% bio-based carbon, such as 90% to 100% bio-based carbon, such as 95% to 100% bio-based carbon, such as 100% bio-based carbon.

8. The method according to any one of claims 1-3 or the composition according to any one of claims 4-7, wherein the at least one active ingredient comprises: a. At least 20% bio-based carbon, such as at least 30% bio-based carbon, such as at least 40% bio-based carbon, such as at least 50% bio-based carbon, such as at least 60% bio-based carbon, such as at least 70% bio-based carbon, such as at least 75% bio-based carbon, such as at least 80% bio-based carbon, such as at least 85% bio-based carbon, such as at least 90% bio-based carbon, such as at least 95% bio-based carbon, such as 100% bio-based carbon; and / or b. 20% to 100% bio-based carbon, such as 30% to 100% bio-based carbon, such as 40% to 100% bio-based carbon, such as 50% to 100% bio-based carbon, such as 60% to 100% bio-based carbon, such as 70% to 100% bio-based carbon, such as 75% to 100% bio-based carbon, such as 80% to 100% bio-based carbon, such as 85% to 100% bio-based carbon, such as 90% to 100% bio-based carbon, such as 95% to 100% bio-based carbon, such as 100% bio-based carbon.

9. The method according to any one of claims 1-3 or the composition according to any one of claims 4-8, wherein the composition comprises radioactivity corresponding to a percentage of bio-based carbon. 14 C level (%).

10. The method according to any one of claims 1-3 or the composition according to any one of claims 4-9, wherein the composition comprises at least one biologically derived substance, such as at least one substance derived from yeast cells, such as metabolites derived from yeast cells, such as at least one biologically derived substance selected from the group consisting of: hexadecane-1-ol, (Z)-9-hexadecen-1-ol, (Z)-11-hexadecen-1-ol, (Z,Z)-9,11-hexadecadien-1-ol and (Z,E)-9,11-hexadecadien-1-ol.

11. The method according to any one of claims 1-3 or the composition according to any one of claims 4-10, wherein the composition further comprises: a. One or more carriers, pharmaceuticals, additives, stabilizers, antioxidants, UV absorbers, light stabilizers, antifreeze agents, glycols, polyols, auxiliaries, and / or excipients; and / or b. A protective agent comprising a sulfur-containing compound, optionally wherein the protective agent comprises conjugated sulfur.

12. The method according to any one of claims 1-3 or the composition according to any one of claims 4-11, wherein the composition comprises: a) A protective agent comprising a conjugated sulfur compound selected from the group consisting of zinc pyrithione, 5-amino-1,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl-1,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-1-methylimidazole, and sodium pyrithione, which protects the target compound from conversion to an acid; and / or b) A carrier that promotes the slow release of (Z,E)-9,11-hexadecadienal, (Z)-9-hexadecenal, (Z)-11-hexadecenal and / or hexadecaldehyde from the mixture, optionally being (i) a polymer matrix selected from plastics, wax emulsions, oil emulsions or microcapsules and / or (ii) zeolite.

13. The method according to any one of claims 1-3 or the composition according to any one of claims 4-12, wherein the fatty alcohol: a. It is a primary alcohol; b. Is a saturated fatty alcohol or a desaturated fatty alcohol; and / or c. are C10 to C26 fatty alcohols, such as C10 to C22 fatty alcohols or such as C12 to C20 fatty alcohols, such as C12 to C18 fatty alcohols, for example C12, C14, C16 or C18 fatty alcohols.

14. The method according to any one of claims 1-3 or the composition according to any one of claims 4-13, wherein the fatty alcohol: a. Having a double bond at position 9, 11, or 13, or wherein the fatty alcohol has a double bond at positions 9 and 11 or at positions 11 and 13; or b. Having a double bond at position 9 or 12, or wherein the fatty alcohol has a double bond at positions 9 and 12; or c. Having a double bond at position 8 or 10, or wherein the fatty alcohol has a double bond at positions 8 and 10.

15. The method according to any one of claims 1-3 or the composition according to any one of claims 4-14, wherein the fatty alcohol has a carbon chain length of 12, 14 or 16, and / or wherein the fatty alcohol is an unbranched fatty alcohol.

16. The method according to any one of claims 1-3 or the composition according to any one of claims 4-15, wherein the fatty alcohol is selected from the group consisting of: (Z)-Δ3 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ3 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ5 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ5 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ6 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ6 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ7 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ7 desaturated fatty alcohols with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ8 desaturated fatty alcohols with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ8 desaturated fatty alcohols with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ9 desaturated fatty alcohols with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ9 desaturated fatty alcohols with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ10 desaturated fatty alcohols with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ10 desaturated fatty alcohols with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ11 desaturated fatty alcohols with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ11 desaturated fatty alcohols with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ12 desaturated fatty alcohols with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ12 desaturated fatty alcohols with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ13 desaturated fatty alcohols having carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22; and (E)-Δ13 desaturated fatty alcohols with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

17. The method according to any one of claims 1-3 or the composition according to any one of claims 4-16, wherein the fatty alcohol is selected from the group consisting of: (E)7,(Z)9 desaturated fatty alcohols with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22. (E)3,(Z)8,(Z)11 desaturated fatty alcohols with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22. (Z)9, (E)11, (E)13 desaturated fatty alcohols with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22. (Z)11,(Z)13 desaturated fatty alcohols with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22. (Z)9,(E)12 desaturated fatty alcohols with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22. (E)7 and (E)9 desaturated fatty alcohols having carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22, and (E8, E10) desaturated fatty alcohols with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

18. The method according to any one of claims 1-3 or the composition according to any one of claims 4-17, wherein the fatty alcohol is selected from the group consisting of: (E)7,(Z)9 desaturated fatty alcohols with a carbon chain length of 14 (E)3,(Z)8,(Z)11 desaturated fatty alcohols with a carbon chain length of 14 (Z)9,(E)11,(E)13 desaturated fatty alcohols with a carbon chain length of 14 (E)7,(Z)9 desaturated fatty alcohols with a carbon chain length of 12 (E)3,(Z)8,(Z)11 desaturated fatty alcohols with a carbon chain length of 12 (Z)9,(E)11,(E)13 desaturated fatty alcohols with a carbon chain length of 12 (E)8,(E)10 desaturated fatty alcohols with a carbon chain length of 12 (E)7,(E)9 desaturated fatty alcohols with a carbon chain length of 11 (Z)11,(Z)13 desaturated fatty alcohols with a carbon chain length of 16, and (Z)9,(E)12 desaturated fatty alcohols with a carbon chain length of 14.

19. The method according to any one of claims 1-3 or the composition according to any one of claims 4-18, wherein the fatty alcohol is selected from the group consisting of: tetradecane-1-ol, pentadecane-1-ol, hexadecane-1-ol, pentadecen-1-ol, (Z)-9-hexadecen-1-ol, (Z)-11-hexadecen-1-ol, (7E,9E)-undec-7,9-dien-1-ol, (11Z,13Z)-hexadecen-1-ol, (9Z,11E)-hexadecen-1-ol, (9Z,12E)-tetradecen-1-ol and (8E,10E)-dodecen-1-ol.

20. The method according to any one of claims 1-3 or the composition according to any one of claims 4-19, wherein the aliphatic aldehyde is: a. Saturated fatty aldehydes or desaturated fatty aldehydes; b. C10 to C26 aliphatic aldehydes, such as C10 to C22 aliphatic aldehydes or C12 to C20 aliphatic aldehydes, for example, C12, C14 or C16 aliphatic aldehydes; and / or c. Unbranched aliphatic aldehydes.

21. The method according to any one of claims 1-3 or the composition according to any one of claims 4-20, wherein: a. The desaturated fatty aldehyde has a double bond at position 9, 11 or 13, or the desaturated fatty aldehyde has a double bond at positions 9 and 11 or at positions 11 and 13; b. The desaturated aliphatic aldehyde has a double bond at position 9 or 12, or the desaturated aliphatic aldehyde has a double bond at positions 9 and 12; or c. The desaturated aliphatic aldehyde has a double bond at position 8 or 10, or the desaturated aliphatic aldehyde has a double bond at positions 8 and 10.

22. The method according to any one of claims 1-3 or the composition according to any one of claims 4-21, wherein the aliphatic aldehyde has a carbon chain length of 12, 14 or 16.

23. The method according to any one of claims 1-3 or the composition according to any one of claims 4-22, wherein the aliphatic aldehyde is selected from the group consisting of: (Z)-Δ3 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ3 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ5 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ5 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ6 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ6 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ7 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ7 desaturated aliphatic aldehydes with carbon chain lengths of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ8 desaturated aliphatic aldehydes with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ8 desaturated aliphatic aldehydes with carbon chain lengths of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ10 desaturated aliphatic aldehydes with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ10 desaturated aliphatic aldehydes with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ11 desaturated aliphatic aldehydes with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ11 desaturated aliphatic aldehydes with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ12 desaturated aliphatic aldehydes with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (E)-Δ12 desaturated aliphatic aldehydes with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22; (Z)-Δ13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22; and (E)-Δ13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

24. The method according to any one of claims 1-3 or the composition according to any one of claims 4-23, wherein the aliphatic aldehyde is selected from the group consisting of: (E)7,(Z)9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22. (E)3, (Z)8, (Z)11 desaturated aliphatic aldehydes with carbon chain lengths of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22. (Z)9, (E)11, (E)13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21, or 22. (Z)11,(Z)13 desaturated aliphatic aldehydes with carbon chain lengths of 14, 15, 16, 17, 18, 19, 20, 21 or 22. (Z)9,(E)12 desaturated aliphatic aldehydes with carbon chain lengths of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22. (E)7 and (E)9 desaturated aliphatic aldehydes with carbon chain lengths of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22, and (E)8, (E)10 desaturated aliphatic aldehydes with carbon chain lengths of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22.

25. The method according to any one of claims 1-3 or the composition according to any one of claims 4-24, wherein the aliphatic aldehyde is selected from the group consisting of: (E)7,(Z)9 desaturated aliphatic aldehydes with a carbon chain length of 14. (E)3,(Z)8,(Z)11 desaturated aliphatic aldehydes with a carbon chain length of 14. (Z)9, (E)11, (E)13 desaturated aliphatic aldehydes with a carbon chain length of 14. (E)7,(Z)9 desaturated aliphatic aldehydes with a carbon chain length of 12. (E)3,(Z)8,(Z)11 desaturated aliphatic aldehydes with a carbon chain length of 12. (Z)9, (E)11, (E)13 desaturated aliphatic aldehydes with a carbon chain length of 12. (E)8,(E)10 desaturated aliphatic aldehydes with a carbon chain length of 12. (E)7,(E)9 desaturated aliphatic aldehydes with a carbon chain length of 11. (Z)11,(Z)13 desaturated aliphatic aldehydes with a carbon chain length of 16, and (Z)9,(E)12 desaturated aliphatic aldehydes with a carbon chain length of 14.

26. The method according to any one of claims 1-3 or the composition according to any one of claims 4-25, wherein the aliphatic aldehyde is selected from the group consisting of: tetradecanoaldehyde, pentadecanoaldehyde, hexadecanoaldehyde, pentadecenal, (Z)-9-hexadecenal, (Z)-11-hexadecenal, (7E,9E)-undec-7,9-dienal, (11Z,13Z)-hexadecenal, (9Z,11E)-hexadecenal, (9Z,12E)-tetradecenal and (8E,10E)-dodecenal.

27. The method according to any one of claims 1-3 or the composition according to any one of claims 4-26, wherein the composition comprises: c) at least 30% by weight of one or more fatty aldehydes, such as at least 40% by weight, 50% by weight, 55% by weight, or 60% by weight of one or more fatty aldehydes, and / or d) At least 30% by weight of one or more fatty alcohols, such as at least 40% by weight, 50% by weight, 55% by weight, or 60% by weight of one or more fatty alcohols; The total amount of fatty aldehydes, fatty alcohols and the N-alkoxyamines shall not exceed 100% by weight.

28. The method according to any one of claims 1-3 or the composition according to any one of claims 4-27, wherein the N-alkoxyamine is: a. Detectable by mass spectrometry (MS); b. Can be ionized by mass spectrometry (MS); c. Detectable by MS methods, wherein the MS method is selected from the group consisting of: electron ionization (EI), electrospray ionization (ESI), matrix-assisted laser desorption / ionization (MALDI), time-of-flight (TOF), quadrupole, ion trap, orbital trap, Fourier transform ion cyclotron resonance (FT-ICR); and / or d. Ionizable by MS method, wherein the MS method is selected from the group consisting of: electron ionization (EI), electrospray ionization (ESI), matrix-assisted laser desorption / ionization (MALDI), time-of-flight (TOF), quadrupole, ion trap, orbital trap, Fourier transform ion cyclotron resonance (FT-ICR).

29. The method according to any one of claims 1-3 or the composition according to any one of claims 4-28, wherein the N-alkoxyamine exhibits one or more m / z peaks when measured using mass spectrometry (MS), wherein the one or more peaks are selected from: 156.1, 309.3, 323.3, 337.3, 351.4, 365.4, 379.4, 393.4, 407.4, 421.4, 435.4, 449.5, 307.3, 321.3, 335.3, 349.3, 363.4, 377.4, 391.4, 405.4, 419.4, 433.4, 447.4, 172.1, 325.3, 339.3, 3 53.3, 367.3, 381.4, 395.4, 409.4, 423.4, 437.4, 451.4, 465.5, 323.3, 337.3, 351.3, 365.3, 379.3, 393.4, 407.4, 421.4, 435.4, 449.4, 463.4, 140.1 293.3, 307.3, 321.3, 335.3, 349.3, 363.4, 377.4, 391.4, 405.4, 419.4, 433.4, 291.3, 305.3, 319.3, 333.3, 347.3, 361.3, 375.4, 389.4, 403.4, 417. 4, 431.4, 166.1, 319.3, 333.3, 347.3, 361.3, 375.4, 389.4, 403.4, 417.4, 431.4, 445.4, 459.4, 317.3, 331.3, 345.3, 359.3, 373.3, 387.4, 401.4, 41 5.4, ​​429.4, 443.4, 457.4, 152.1, 305.3, 319.3, 333.3, 347.3, 361.3, 375.4, 389.4, 403.4, 417.4, 431.4, 445.4, 303.3, 317.3, 331.3, 345.3, 359.3, 3 73.3, 387.4, 401.4, 415.4, 429.4, 443.4, 186.1, 339.3, 353.3, 367.3, 381.4, 395.4, 409.4, 423.4, 437.4, 451.4, 465.5, 479.5, 337.3, 351.3, 365.3 379.3, 393.4, 407.4, 421.4, 435.4, 449.4, 463.4, 477.5, 171.1, 324.3, 338.3, 352.3, 366.4, 380.4, 394.4, 408.4, 422.4, 436.4, 450.5, 464.5, 322.3, 336.3, 350.3, 364.3, 378.4, 392.4, 406.4, 420.4, 434.4, 448.4, 462.5, 213.2, 366.3, 380.3, 394.4, 408.4, 422.4, 436.4, 450.4, 464.4, 478.4, 492.5, 506.5, 364.3, 378.3, 392.3, 406.4, 420.4, 434.4, 448.4, 462.4, 476.4, 490.4, 504.5, 170.1, 323.3, 337.3, 351.3, 365.3, 379.3, 39 3.4, 407.4, 421.4, 435.4, 449.4, 463.4, 321.3, 335.3, 349.3, 363.3, 377.3, 391.3, 405.4, 419.4, 433.4, 447.4, 461.4, 276.2, 429.3, 443.3, 457.4, 471.4, 485.4, 499.4, 513.4, 527.4, 541.4, 555.5, 569.5, 427.3, 441.3, 455.3, 469.4, 483.4, 497.4, 511.4, 525.4, 539.4, 553.4, and 567.

5.

30. The method according to any one of claims 1-3 or the composition according to any one of claims 4-29, wherein the N-alkoxyamine is detectable by analytical chromatography, for example, by an analytical chromatographic method selected from the group consisting of: gas chromatography (GC-MS), liquid chromatography (LC-MS), high performance liquid chromatography (HPLC-MS), ultra-high performance liquid chromatography (UHPLC-MS), ion chromatography (IC-MS), and size exclusion chromatography (SEC-MS).

31. The method according to any one of claims 1-3 or the composition according to any one of claims 4-30, wherein the N-alkoxyamine has the formula selected from the group consisting of: Z10-15-A-TEMPO; Z10, Z12-15-A-TEMPO; and Z8, E10-15-A-TEMPO: (Z10-15-A-TEMPO); (Z10,Z12-15-A-TEMPO); (Z8,E10-15-A-TEMPO) ; A is selected from the group consisting of: hydrogen, hydroxyl, carbonyl, alkyl, such as C. 1-6 Alkyl groups, amines, amides, such as C 1-6 -Amide, alkoxy group such as C 1-6 Alkoxy groups and esters such as C 1-6 Esters; or their ions or salts.

32. The method according to any one of claims 1-3 or the composition according to claim 31, wherein the N-alkoxyamine is selected from the group consisting of: (Z10-15-OH-TEMPO); and (Z10-15-TEMPO) 33. The method according to any one of claims 1-3 or the composition according to claim 31, wherein the N-alkoxyamine has the following formula: a. Z10, Z12-15-A-TEMPO, wherein A is H or wherein A is OH; or b.Z8,E10-15-A-TEMPO, wherein A is H or A is OH.

34. The method according to any one of claims 1-3 or the composition according to any one of claims 4-33, wherein: a. The composition comprises at least 0.02 area% of the N-alkoxyamine as determined by analytical chromatography coupled with mass spectrometry, such as at least 0.03 area%, such as at least 0.04 area%, such as at least 0.05 area%, such as at least 0.06 area%, such as at least 0.07 area%, such as at least 0.08 area%, such as at least 0.09 area%, such as at least 0.10 area% of the N-alkoxyamine; and / or b. The composition comprises at least 0.01 area % of the N-alkoxyamine as determined by GC MS, such as at least 0.02 area %, such as at least 0.03 area %, such as at least 0.04 area %, such as at least 0.05 area %, such as at least 0.06 area %, such as at least 0.07 area %, such as at least 0.08 area %, such as at least 0.09 area %, such as at least 0.10 area % of the N-alkoxyamine.

35. The method according to any one of claims 1-3 or the composition according to any one of claims 4-34, wherein the composition comprises copper, such as copper (I) or copper (II), for example in the form of a copper (II) salt, such as copper (II) salts selected from the group consisting of: copper carboxylate (II), copper trifluoromethanesulfonate (II), copper tetrafluoroborate (II), copper hexafluorophosphate (II), copper bromide (II), copper chloride (II), copper iodide (II), and copper perchlorate (II); or for example in the form of a copper (I) salt, such as copper (I) salts selected from the group consisting of: cuprous chloride (I), cuprous bromide (I), cuprous iodide (I), cuprous cyanide (I), cuprous oxide. (I), Copper trifluoromethanesulfonate (I), Copper tetrafluoroborate (acetonitrile) (I), Copper tetraphenylborate (acetonitrile) (I), Copper tetrafluorophosphate (acetonitrile) (I), Copper tetrafluoromethanesulfonate (acetonitrile) (I), Cuprous sulfide (I), Copper thiocyanate (I), Cu[1,3-bis(2,6-diisopropylphenyl)imidazolium-2-ylidene]Cl, Cu[1,3-bis(2,6-diisopropylphenyl)imidazolium-2-ylidene]Br, CuBr(1,10-phenanthroline)2, CuCl(1,10-phenanthroline)]2, CuI(1,10-phenanthroline)2, Copper trifluoroacetate (I), [Cu(PPh3)3]Br, [Cu(PPh3)3]F, [Cu(PPh3)3]Cl, Cu(OCOR) 2 ), Cu(SR) 2 ), Cu(SR) 2 2) Br, Cu(SR) 2 2) Cl, Cu(SR) 2 2) I, Cu(OSO2R) 2 ), CuOR 2 , where R 2 Selected from the following groups: alkyl, preferably C1-C 20 Alkyl groups, optionally substituted with one or more aryl, alkoxy, and aryloxy groups; and aryl groups, preferably C5-C7 aryl groups, optionally substituted with one or more alkyl, aryl, alkoxy, and aryloxy groups; and mixtures of the foregoing groups.

36. An N-alkoxyamine having the formula selected from the group consisting of: Z10-15-A-TEMPO; Z10, Z12-15-A-TEMPO; and Z8, E10-15-A-TEMPO: (Z10-15-A-TEMPO); (Z10,Z12-15-A-TEMPO); (Z8,E10-15-A-TEMPO) ; A is selected from the group consisting of: hydrogen, hydroxyl, carbonyl, alkyl, such as C. 1-6 Alkyl groups, amines, amides, such as C 1-6 -Amide, alkoxy group such as C 1-6 Alkoxy groups and esters such as C 1-6 Esters; or their ions or salts.

37. The alkoxyamine of claim 36, wherein the N-alkoxyamine is selected from the group consisting of: (Z10-15-OH-TEMPO); and (Z10-15-TEMPO) 38. A process for producing a composition comprising a) at least one active ingredient selected from the group consisting of fatty aldehydes, fatty alcohols, and combinations thereof; and b) an N-alkoxyamine; wherein the process comprises the following steps: i) Provide a reaction mixture comprising a fatty alcohol, a catalyst containing a copper source, and a solvent, and ii) The fatty alcohol is oxidized by adding O2 to the reaction mixture in an amount sufficient to convert more than 50% by weight of the fatty alcohol into fatty aldehydes and less than 50% by weight of the fatty alcohol into fatty acids.

39. The process of claim 38, wherein the process is used for the large-scale conversion of fatty alcohols into fatty aldehydes, the method comprising the following steps: a) Provide a reaction mixture comprising at least 1 kg of a fatty alcohol, a catalyst containing a copper source, at least 1 kg of a solvent, and a water-absorbing or adsorbing material for absorbing or adsorbing water, and b) By feeding a gas or liquid containing O2 into the reaction medium, at least 0.01 μmol O2 is dissolved per μmol copper per minute in the reaction mixture or at least 0.001 μmol O2 is dissolved per μmol initial fatty alcohol per minute in the reaction mixture, thereby oxidizing more than 50% by weight of the fatty alcohol to fatty aldehydes and less than 50% by weight of the fatty alcohol to fatty acids.

40. The process according to claims 38-39, wherein the removal of carbon atoms from the fatty alcohol includes covalently attaching hydrogen atoms to the carbon atoms, wherein the carbon atoms are covalently bonded to oxygen atoms of the hydroxyl groups of the fatty alcohol.

41. A composition obtained by the process according to any one of claims 38-40.

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