N-alkoxyamine marker and processes

Abstract

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

Description

/ V-alkoxyamine marker and processesField

[0001] The present disclosure describes compositions comprising in particular fatty alcohols, fatty aldehydes, and an / V-alkoxyamine. The present disclosure further describes the / V-alkoxyamines and their use as markers for determining if a particular process has been used.Background

[0002] Integrated Pest Management (IPM) is playing an increasing role for both increasing the crop yield and for minimizing environmental impact and enabling organic food production. IPM employs alternative pest control methods, such as using pheromones for pest insect mating disruption or mass trapping, or attraction of beneficial insects etc.

[0003] Pheromones constitute a group of diverse chemical compounds that insects (like other organisms) use to communicate between individuals of the same species in various contexts, including mate attraction, alarm, trail marking and aggregation. Insect pheromones associated with long-range mate finding are already used in agriculture and forestry applications for monitoring and control of pests, as a safe and environmentally friendly alternative to pesticides. The biological production of pheromones for use in pest control is advantageous over chemical synthesis in respect to 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 for converting cellular precursor metabolites into the desired pheromones and pheromone precursors, such described in WO2021078452 and WO2021123128.

[0005] Known pheromones include fatty acyl alcohols, aldehydes and acetates having one or more double bonds at specific positions of the carbon backbone having specific Z or / and E orientation.

[0006] W02023 / 012151 describes a convenient method of converting an alcohol composition into an aldehyde composition, in particular for fatty alcohols into fatty aldehydes. The method described therein utilises a relatively small amount of solvent, is scalable, to industrial scale, even to 100 kilogram batch size or more and provides for a product of high purity, in particular with respect to removal of catalyst composition. However, whether the proprietary process in W02023 / 012151 or other methodology have been used for alcohol oxidation remains difficult to investigate when examining the final aldehyde composition.Summary

[0007] The present inventors have discovered a characteristic marker, namely an / V-alkoxyamine resulting from their alcohol oxidation processes of W02023 / 012151 using copper catalysis and OH- TEMPO (4-hydroxy-2,2,6,6-tetramethylpiperidin-l-yl)oxyl. The / V-alkoxyamine marker results from shortening of the carbon chain of the fatty alcohol to be oxidized or the fatty aldehyde including a displacement of the the original oxygen of the fatty alcohol in turn for the OH-TEMPO moiety. The fatty alcohols are oxidized to provide pheromones of high bioindustrial importance, and the resulting / V-alkoxyamine obtained from the process has a highly characteristic analytical profile, such as mass spectrometry profile, and / or retention time which makes it possible to determine if the particular oxidation process has been used.

[0008] Thus, in one aspect, a method is provided for determining if a composition comprising: a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, a fatty alcohol acetate, and a combination thereof; and b) an / V-alkoxyamine; has been prepared by a process for producing the composition; wherein the process comprises the steps of:(I) providing a reaction mixture comprising a fatty alcohol, a catalyst comprising a copper source, and a solvent, and(II) oxidizing the fatty alcohol by adding Oj to the reaction mixture in an amount sufficient for converting more than 50 wt% of the fatty alcohol to fatty aldehyde and less than 50 wt% into fatty acid; wherein the method comprises the steps of:A) providing a composition for analysis;B) subjecting a sample of the composition in A) for analysis by mass spectrometry to obtain a mass spectrum, preferably analytical chromatography coupled to mass spectrometry;C) wherein if the mass spectrum obtained in B) comprises a mass (m / z) corresponding to an N- alkoxyamine, then the composition comprising a) and b) has been obtained by said process.

[0009] In a further aspect, a composition is provided comprising: a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, a fatty alcohol acetate, and a combination thereof; and b) an / V-alkoxyamine.

[0010] In a further aspect, an / V-alkoxyamine of a formula selected from the group consisting of: Z10- 15-A-TEMPO; Z10,Z12-15-A-TEMPO; and Z8,E10-15-A-TEMPO is added:(Z8,E10-15- A-TEMPO);

[0011] wherein A is selected from the group consisting of: hydrogen, hydroxy, carbonyl, an alkyl, such as a Ci-g alkyl, an amine, an amide, such as a Ci-g-amide, an alkoxy, such as a Ci.g alkoxy, and an ester, such as a Ci-g ester; or an ion or salt thereof.

[0012] In a further aspect, a process for producing a composition is provided comprising a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, and a combination thereof; and b) an / V-alkoxyamine; wherein the method comprises the steps of: i) providing a reaction mixture comprising a fatty alcohol, a catalyst comprising a copper source, and a solvent, and ii) oxidizing the fatty alcohol by adding O2 to the reaction mixture in an amount sufficient for converting more than 50 wt% of the fatty alcohol to fatty aldehyde and less than 50 wt% into fatty acid.

[0013] In a further aspect, a composition obtainable by the process of the present disclosure isprovided.

[0014] In a further aspect, a method is provided for determining if a composition has been prepared by the process of the present disclosure, wherein the method comprises the steps of: a) providing a composition for analysis; b) subjecting a sample of the composition in a) for analysis by mass spectrometry to obtain a mass spectrum, preferably analytical chromatography coupled to mass spectrometry; c) wherein if the mass spectrum obtained in b) comprises a mass corresponding to an / V-alkoxyamine as defined herein, then the composition has been obtained by the process herein.Drawings and figures

[0015] Figure 1 shows the gas chromatography mass spectrometry (GCMS) areas in % measured as a function of reaction time for oxidation of the alcohol using conditions set out in Example 1 for the alcohol (filled black circle), aldehyde (empty black circle), and the TEMPO adduct i.e. / V-alkoxyamine (filled black star), respectively.

[0016] Figure 2 shows the GC-FID chromatograms of a representative sample (A) of the N- alkoxyamine obtained from the oxidation process of Example 1 and a synthesized standard of same (B) obtained as described in Example 2.

[0017] Figure 3 shows the GC-MS chromatogram of a representative sample of the / V-alkoxyamine obtained from the oxidation process of Example 1.

[0018] Figure 4 shows the mass spectrum of a representative sample of the / V-alkoxyamine obtained from the oxidation process of Example 1.

[0019] Figure 5 shows the GC-MS chromatogram of a synthesized standard of / V-alkoxyamine obtained as described in Example 2.

[0020] Figure 6 shows the mass spectrum of a synthesized standard of / V-alkoxyamine obtained as described in Example 2.

[0021] Figure 7 shows the GC-FID Chromatogram of a Representative Sample of the / V-alkoxyamine marker 2 obtained from the oxidation process of Example 1.

[0022] Figure 8 shows the GC-FID Chromatogram of a Synthesized Standard of / V-alkoxyamine (Zll- 16-OH-TEMPO-2) obtained as described in Example 3.

[0023] Figure 9 shows the GC-MS Chromatogram (A) and Spectrum (B) of a Synthesized Standard of / V-alkoxyamine marker 2 (Z11-16-OH-TEMPO-2) obtained as described in Example 3.Incorporation by reference

[0024] All publications, patents, and patent applications referred to herein are incorporated byreference to the same extent as if each individual publication, patent, or patent application was specifically and individually indicated to be incorporated by reference. In the event of a conflict between a term herein and a term in an incorporated reference, the term herein prevails and controls.DetailsDefinitions

[0025] Throughout this disclosure where reference is made to a pheromone component or a precursor for example (Z,E)-9,ll-hexandecadienal referring to the fatty aldehyde having a carbon chain of 16, having an aldehyde at Cl, having a Z configured double bond at C9 and an E configured double bond at Cll, alternative terms such as Z9, ll-16:Ald or (Z9, Ell)-hexadecadienal may be used interchangeably. Similar nomenclature may be used about other pathway compounds such as corresponding fatty acids, CoA derivatives, alcohols, acids or acetates.

[0026] The term "saturated" refers to a compound which is devoid of double or triple carbon-carbon bonds.

[0027] The term "desaturated" as used herein interchangeably with the term "unsaturated" about compounds refers to the compound containing one or more double or triple carbon-carbon bonds, preferably a double carbon-carbon bond. The following nomenclature is used herein throughout: a Ai desaturated compound, where / is an integer, refers to a compound having a double or triple carboncarbon bond in position / of the carbon chain. The carbon chain length is thus at least equal to / . For example, a A12 desaturated compound refers to a compound having a double or triple carbon-carbon bond in position 12 and having a carbon chain length of 13 or more. The double or triple bond can be in an E configuration or in a Z configuration. Thus, an E / or a Z / desaturated compound will refer to a compound having a double carbon-carbon bond in an E configuration or in a Z configuration, respectively, in position / of the carbon chain, which has a total length at least equal to / . For example, an Ell fatty alcohol has a desaturation in position 11 in an E configuration and has a carbon chain length of 12 or more.

[0028] The term "biobased" as used herein is used to characterize biobased products wherein:(I) the total carbon content of the product is at least 30%, and(II) the carbon content of a renewable raw material (biobased) is at least 20%.

[0029] Both fossil and renewable raw materials consist mainly of carbon (C). Carbon occurs in several isotopes. Isotope14C is radioactive and occurs naturally in all living organisms (plants, animals, etc) in a fixed relative concentration which is nearly identical to the relative14C concentration in the atmosphere. At this concentration, the radioactivity level of14C is 100%. Once an organism is no longer living, this concentration, and thus the radioactivity rate, decays with a half-life of approximately 5700years. The radioactive14C level of an unknown substance can therefore help determine how old the carbon contained in the substance is.

[0030] "Young" carbon (0 to 10 years) derived from renewable raw materials, such as plants or animals, has a relative isotope14C concentration which is nearly identical to the relative14C concentration in the atmosphere and the radioactive14C level of such young carbon is thus about 100%.

[0031] "Old" carbon (millions of years) derived from synthetic or fossil (petrochemical) sources is greatly depleted from isotope14C as the age of such synthetic and fossil sources far exceeds the halflife of isotope14C which is approximately 5700 years. Hence, carbon derived from synthetic or fossil sources has a relative isotope14C concentration around 0% and the radioactive14C level of such old carbon is thus about 0%.

[0032] In one embodiment the term "radioactive14C level" refer to the total radioactive14C level of a given substance, product, or composition, as defined above.

[0033] The isotope14C method may be used to determine the concentration of young (renewable) materials in comparison with the concentration of old (fossil) resources. The carbon content of a renewable raw material is referred to as the "biobased carbon content". The carbon content of a renewable raw material or the "biobased carbon content" may be determined as described below.

[0034] When measuring the biobased carbon content, the result may be reported as "% biobased carbon". This indicates the percentage carbon from "natural" (plant or animal by-product) sources versus "synthetic" or "fossil" (petrochemical) sources . For reference, 100 % biobased carbon indicates that a material is entirely sourced from plants or animal by-products and 0 % biobased carbon indicates that a material did not contain any carbon from plants or animal by-products. A value in between represents a mixture of natural and fossil sources.

[0035] Example: If a product has a radioactive14C level of 80%, it means that the product consists of 80% renewable and 20% fossil carbon (C). In other words, the product is 80% bio-based.

[0036] The analytical measurement may be cited as "percent modern carbon (pMC)". This is the percentage of14C measured in the sample relative to a modern reference standard (NIST 4990C). The % Biobased Carbon content is calculated from pMC by applying a small adjustment factor for14C in carbon dioxide in air today. It is important to note that all internationally recognized standards using14C assume that the plant or biomass feedstocks were obtained from natural environments. pMC may be analysed by a standard test method, such as "ASTM D6866".

[0037] The term "fatty acyl compounds" as used herein refers to fatty compounds having a long aliphatic chain, i.e. an aliphatic chain typically having 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 fattyacids are unbranched. They can be saturated, or desaturated. Fatty acyl compounds can include various functional end groups.

[0038] The term "Fatty acyl-CoA" as used herein interchangeably with "fatty acyl-CoA ester" refers to and refers to compounds of general formula R-CO-SCoA, where R is a fatty carbon chain having a carbon chain length of 12 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. The fatty carbon chain is joined to the -SH group of CoA by a thioester bond. Fatty acyl-CoAs can be saturated or desaturated, depending on whether the fatty acid which it is derived from is saturated or desaturated.

[0039] The term "fatty alcohol" as used herein 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.

[0040] The term "fatty alcohol acetate" as used herein refers to an acetate having a fatty carbon chain, i.e. an aliphatic chain 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.

[0041] The term "fatty aldehyde" as used herein 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. Fatty aldehydes can be saturated or desaturated.

[0042] The term "functional variant" as used herein refers to functional variants of an enzyme, which retain at least some of the activity of the parent enzyme. Thus, functional variants of desaturases, or other pathway enzymes catalyze similar reactions as their parent enzymes, although the efficiency and specificity of reaction may be different, e.g. the efficiency is decreased or increased compared to the parent enzyme.

[0043] The term "pheromone" as used herein is used about naturally occurring signalling compounds used in nature for chemical communation between indiduals of a species. Lepidopteran pheromones for example are designated by an unbranched aliphatic chain (between 9 and 18 carbons, such as 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms) ending in an alcohol, aldehyde or acetate functional group and containing up to 3 double bonds in the aliphatic backbone. Thus, desaturated fatty alcohols, desaturated fatty aldehydes and desaturated fatty alcohol acetates are typically comprised in pheromones. Pheromone compositions may be produced chemically or biochemically, for example as described herein. Pheromones thus comprise desaturated fatty alcohols, desaturated fatty aldehydes and / or desaturated fatty alcohol acetates, such as can be obtained by the methods and cells described herein.

[0044] The term "comprise" and "include" as used throughout the specification and the accompanying items as well as variations such as "comprises", "comprising", "includes" and"including" are to be interpreted inclusively. These words are intended to convey the possible inclusion of other elements or integers not specifically recited, where the context allows.

[0045] The articles "a" and "an" are used herein refers to one or to more than one (i.e. to one or at least one) of the grammatical object of the article. By way of example, "an element" may mean one element or more than one element.

[0046] Terms like "preferably", "commonly", "particularly", and "typically" are not utilized herein to limit the scope of the itemed invention or to imply that certain features are critical, essential, or even important to the structure or function of the itemed invention. Rather, these terms are merely intended to highlight alternative or additional features that can or cannot be utilized in a particular embodiment of the present invention.

[0047] All methods described herein can be performed in any suitable order of steps unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., "such as") provided herein is intended merely to better illuminate the invention and does not pose a limitation on the scope of the invention otherwise claimed. No language in the specification should be construed as indicating any non-claimed element essential to the practice of the invention.

[0048] All percentages, ratios and proportions herein are by weight, unless otherwise specified. A weight percent (weight %, also as wt. %) of a component, unless specifically stated to the contrary, is based on the total weight of the composition in which the component is included (e.g., on the total amount of the reaction mixture).

[0049] The terms "substantially" or "approximately" or "about", as used herein refers to a reasonable deviation around a value or parameter such that the value or parameter is not significantly changed. These terms of deviation from a value should be construed as including a deviation of the value where the deviation would not negate the meaning of the value deviated from. For example, in relation to a reference numerical value the terms of degree can include a range of values plus or minus 10% from 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% from the specified value.

[0050] The term "and / or" as used herein is intended to represent an inclusive "or". The wording X and / or Y is meant to mean both X or Y and X and Y. Further the wording X, Y and / or Z is intended to mean X, Y and Z alone or any combination of X, Y, and Z.

[0051] The term "isolated" as used herein about a compound, refers to any compound, which by means of human intervention, has been put in a form or environment that differs from the form or environment in which it is found in nature. Isolated compounds include but is no limited to compoundsof the disclosure for which the ratio of the compounds relative to other constituents with which they are associated in nature is increased or decreased. In an important embodiment the amount of compound is increased relative to other constituents with which the compound is associated in nature. In an embodiment the compound of the disclosure may be isolated into a pure or substantially pure form. In this context a substantially pure compound means that the compound is separated from other extraneous or unwanted material present from the onset of producing the compound or generated in the manufacturing process. Such a substantially pure compound preparation contains 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 extraneous or unwanted material usually associated with the compound when expressed natively or recombinantly. In an embodiment the isolated compound is at least 90% pure, 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 by weight.Composition

[0052] In some embodiments, a composition is provided comprising: a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, a fatty alcohol acetate, and a combination thereof; and b) an / V-alkoxyamine. The / V-alkoxyamine of the present disclosure has a highly characteristic analytical profile rendering it suitable for detecting if the process for production of the composition of the present disclosure has been used.

[0053] In sone embodiments, the composition is provided where the at least one active ingredient is a pheromone.Biobased compositions

[0054] In some embodiments, the composition provided is a biobased composition. In some embodiments, the composition is a biopesticide. In some embodiments, the composition comprises at least 20% biobased carbon, such as at least 30% biobased carbon, such as at least 40% biobased carbon, such as at least 50% biobased carbon, such as at least 60% biobased carbon, such as at least 70% biobased carbon, such as at least 75% biobased carbon, such as at least 80% biobased carbon, such as at least 85% biobased carbon, such as at least 90% biobased carbon, such as at least 95% biobased carbon, such as 100% biobased carbon.

[0055] In some embodiments, the composition comprises from 20% to 100% biobased carbon, such as from 30% to 100% biobased carbon, such as from 40% to 100% biobased carbon, such as from 50%to 100% biobased carbon, such as from 60% to 100% biobased carbon, such as from 70% to 100% biobased carbon, such as from 75% to 100% biobased carbon, such as from 80% to 100% biobased carbon, such as from 85% to 100% biobased carbon, such as from 90% to 100% biobased carbon, such as from 95% to 100% biobased carbon, such as 100% biobased carbon.

[0056] In some embodiments, the at least one active ingredient of the composition comprises at least 20% biobased carbon, such as at least 30% biobased carbon, such as at least 40% biobased carbon, such as at least 50% biobased carbon, such as at least 60% biobased carbon, such as at least 70% biobased carbon, such as at least 75% biobased carbon, such as at least 80% biobased carbon, such as at least 85% biobased carbon, such as at least 90% biobased carbon, such as at least 95% biobased carbon, such as 100% biobased carbon.

[0057] In some embodiments, the at least one active ingredient of the composition comprises from 20% to 100% biobased carbon, such as from 30% to 100% biobased carbon, such as from 40% to 100% biobased carbon, such as from 50% to 100% biobased carbon, such as from 60% to 100% biobased carbon, such as from 70% to 100% biobased carbon, such as from 75% to 100% biobased carbon, such as from 80% to 100% biobased carbon, such as from 85% to 100% biobased carbon, such as from 90% to 100% biobased carbon, such as from 95% to 100% biobased carbon, such as 100% biobased carbon.

[0058] In some embodiments, the composition comprises a radioactive14C level (%) corresponding to the % biobased carbon. In this case, a radioactive14C level (%) of for example 50% would correspond to 50% biobased carbon.

[0059] In some embodiments, the composition comprises at least one biologically derived substance, for example at least one substance derived from a yeast cell, such as a metabolite derived from a yeast cell.

[0060] In some embodiments, the composition comprises at least one biologically derived substance selected from the group consisting of: hexadecan-l-ol, (Z)-9-hexadecen-l-ol, (Z)-ll-hexadecen-l-ol, and (Z,E)-9,ll-hexadecadien-l-ol. In some embodiments, the composition comprising these biologically derived substances is biobased according to the definitions herein.

[0061] In some embodiments, the composition further comprises one or more carriers, agents, additives, stabilizers, antioxidants, UV absorbers, light stabilizers, antifreeze agents, diols, polyols, adjuvants and / or excipients.

[0062] In some embodiments, the composition of the present disclosure further comprises a protective agent comprising a sulfur containing compound, optionally wherein the protective agent comprises a conjugated sulfur.

[0063] In some embodiments, the composition defined herein further comprises: a) a protective agent comprising a conjugated sulfur compound selected from the group consisting of:zinc pyrithione, 5-amino-l,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl-l,3,4-thiadiazole-2- thiol, 2-mercapto-benzimidazole, 2-mercapto-l-methylimidazole and sodium pyrithione, which protects the target compound from from being converted into an acid; and / or b) a carrier facilitating slow release of the (Z,E)-9,ll-hexadecadienal, (Z)-9-hexadecenal, (Z)-ll- hexadecenal and / or hexadecanal from the mixture, optionally being (i) a polymeric substrate selected from plastic, wax emulsion, oil emulsion, or microcapsules and / or (ii) a zeolite.Fatty alcohol

[0064] In some embodiments, the composition of the present disclosure is provided, wherein the fatty alcohol is a primary alcohol.

[0065] In some embodiments, the fatty alcohol is a saturated fatty alcohol or a desaturated fatty alcohol.

[0066] In some embodiments, the fatty alcohol is a CIO to C26 fatty alcohol.

[0067] In some embodiments, the fatty alcohol is a CIO to C22 fatty alcohol.

[0068] In some embodiments, the fatty alcohol is a C12 to C20 fatty alcohol.

[0069] In some embodiments, the fatty alcohol is a C12 to C18 fatty alcohol.

[0070] In some embodiments, the fatty alcohol is a C12, C14, C16 or C18 fatty alcohol.

[0071] In some embodiments, the composition is provided wherein the desaturated fatty alcohol has a double bond at position 9, 11 or 13, or wherein the desaturated fatty alcohol has double bonds at positions 9 and 11, or at positions 11 and 13.

[0072] In some embodiments, the composition of the present disclosure is provided wherein the desaturated fatty alcohol has a double bond at position 9 or 12, or wherein the desaturated fatty alcohol has double bonds at positions 9 and 12.

[0073] In some embodiments, the composition of the present disclosure is provided, wherein the desaturated fatty alcohol has a double bond at position 8 or 10, or wherein the desaturated fatty alcohol has double bonds at positions 8 and 10.

[0074] In some embodiments, the composition of the present disclosure is provided, wherein the fatty alcohol has a carbon chain length of 12, 14, or 16. In some embodiments, the composition of the present disclosure is provided, wherein the fatty alcohol has a carbon chain length of from 12 to 16.

[0075] In some embodiments, the composition of the present disclosure is provided, wherein the fatty alcohol is an unbranched fatty alcohol.

[0076] In some embodiments, the composition of the present disclosure is provided, wherein the fatty alcohol is selected from the group consisting of:(Z)-A3 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22;(E)-A3 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A5 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A5 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A6 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A6 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A7 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A7 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22;(Z)-A8 desaturated fatty alcohols having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(E)-A8 desaturated fatty alcohols having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(Z)-A9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19,20, 21 or 22;(E)-A9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A10 desaturated fatty alcohols having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A10 desaturated fatty alcohols having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-All desaturated fatty alcohols having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-All desaturated fatty alcohols having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A12 desaturated fatty alcohols having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A12 desaturated fatty alcohols having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or22;(Z)-A13 desaturated fatty alcohols having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22; and(E)-A13 desaturated fatty alcohols having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0077] In some embodiments, the composition of the present disclosure is provided, wherein the fatty alcohol is selected from the group consisting of:(E)7,(Z)9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21, or 22,(E)3,(Z)8,(Z)11 desaturated fatty alcohols having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19,20, 21, or 22,(Z)9,(E)11,(E)13 desaturated fatty alcohols having a carbon chain length of 14, 15, 16, 17, 18, 19, 20,21, or 22,(Z)11,(Z)13 desaturated fatty alcohols having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or22,(Z)9,(E)12 desaturated fatty alcohols having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22,(E)7,(E)9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22, and(E8,E10) desaturated fatty alcohols having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19,20, 21, or 22.

[0078] In some embodiments, the composition of the present disclosure is provided, wherein the fatty alcohol is selected from the group consisting of:(E)7,(Z)9 desaturated fatty alcohol having a carbon chain length of 14,(E)3,(Z)8,(Z)11 desaturated fatty alcohol having a carbon chain length of 14,(Z)9,(E)11,(E)13 desaturated fatty alcohol having a carbon chain length of 14,(E)7,(Z)9 desaturated fatty alcohol having a carbon chain length of 12,(E)3,(Z)8,(Z)11 desaturated fatty alcohol having a carbon chain length of 12,(Z)9,(E)11,(E)13 desaturated fatty alcohol having a carbon chain length of 12,(E)8,(E)10 desaturated fatty alcohol having a carbon chain length of 12,(E)7,(E)9 desaturated fatty alcohol having a carbon chain length of 11,(Z)11,(Z)13 desaturated fatty alcohol having a carbon chain length of 16, and(Z)9,(E)12 desaturated fatty alcohol having a carbon chain length of 14.

[0079] In some embodiments, the fatty alcohol is selected from the group consisting of tetradecan- l-ol, pentadecan-l-ol, hexadecan-l-ol, pentadecen-l-ol, (Z)-9-hexadecen-l-ol, (Z)-ll-hexadecen-l-ol,(7E,9E)-undeca-7,9-dien-l-ol, (11Z, 13Z)-hexadecadien-l-ol, (9Z, 12E)-tetradecadien-l-ol, and (8E,10E)-dodecadien-l-ol.Fatty aldehyde

[0080] In some embodiments, the composition of the present disclosure is provided, wherein the fatty aldehyde is a saturated fatty aldehyde. In some embodiments, the composition of the present disclosure is provided, wherein the fatty aldehyde is a desaturated fatty aldehyde. In some embodiments, the fatty aldehyde is a CIO to C26 fatty aldehyde. In some embodiments, the fatty aldehyde is a CIO to C22 fatty aldehyde. In some embodiments, the fatty aldehyde is a C12 to C20 fatty aldehyde. In some embodiments, the fatty aldehyde is a C12, C14, or C16 fatty aldehyde. In some embodiments, the fatty aldehyde is an unbranched fatty aldehyde. In some embodiments, the desaturated fatty aldehyde has a double bond at position 9, 11 or 13, or wherein the desaturated fatty aldehyde has double bonds at positions 9 and 11, or at positions 11 and 13.

[0081] In some embodiments, the desaturated fatty aldehyde has a double bond at position 9 or 12, or the desaturated fatty aldehyde has double bonds at positions 9 and 12.

[0082] In some embodiments, the desaturated fatty aldehyde has a double bond at position 8 or 10, or wherein the desaturated fatty aldehyde has double bonds at positions 8 and 10.

[0083] In some embodiments, the fatty aldehyde has a carbon chain length of 12, 14, or 16. In some embodiments, the fatty aldehyde has a carbon chain length of from 12 to 16.

[0084] In some embodiments, the fatty aldehyde is selected from the group consisting of:(Z)-A3 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A3 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A5 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A5 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A6 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A6 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A7 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A7 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22;(Z)-A8 desaturated fatty aldehydes having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(E)-A8 desaturated fatty aldehydes having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(Z)-A10 desaturated fatty aldehydes having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19,20, 21 or 22;(E)-A10 desaturated fatty aldehydes having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19,20, 21 or 22;(Z)-All desaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-All desaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A12 desaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A12 desaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A13 desaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22; and(E)-A13 desaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22.

[0085] In some embodiments, the fatty aldehyde is selected from the group consisting of:(E)7,(Z)9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21, or 22,(E)3,(Z)8,(Z)11 desaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17, 18,19, 20, 21, or 22,(Z)9,(E)11,(E)13 desaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20,21, or 22,(Z)11,(Z)13 desaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21or 22,(Z)9,(E)12 desaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22,(E)7,(E)9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22, and(E)8,(E)10 desaturated fatty aldehydes having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, or 22.

[0086] In some embodiments, the fatty aldehyde is selected from the group consisting of:(E)7,(Z)9 desaturated fatty aldehyde having a carbon chain length of 14,(E)3,(Z)8,(Z)11 desaturated fatty aldehyde having a carbon chain length of 14,(Z)9,(E)11,(E)13 desaturated fatty aldehyde having a carbon chain length of 14,(E)7,(Z)9 desaturated fatty aldehyde having a carbon chain length of 12,(E)3,(Z)8,(Z)11 desaturated fatty aldehyde having a carbon chain length of 12,(Z)9,(E)11,(E)13 desaturated fatty aldehyde having a carbon chain length of 12,(E)8,(E)10 desaturated fatty aldehyde having a carbon chain length of 12(E)7,(E)9 desaturated fatty aldehyde having a carbon chain length of 11,(Z)11,(Z)13 desaturated fatty aldehyde having a carbon chain length of 16, and(Z)9,(E)12 desaturated fatty aldehyde having a carbon chain length of 14.

[0087] In some embodiments, the fatty aldehyde is selected from the group consisting of tetradecan- 1-al, pentadecan-l-al, hexadecan-l-al, pentadecen-l-al, (Z)-9-hexadecen-l-al, (Z)-ll-hexadecen-l-al, (7E,9E)-undeca-7,9-dien-l-al, (11Z, 13Z)-hexadecadien-l-al, (9Z,12E)-tetradecadien-l-al, and (8E,10E)-dodecadien-l-al.

[0088] In some embodiments, the composition of the present disclosure further comprises: a) at least 30 wt% of one or more of the fatty aldehydes, such as at least 40 wt%, 50 wt%, 55 wt%, such as 60 wt% of one or more of the fatty aldehydes, and / or b) at least 30 wt% of one or more fatty alcohols, such as at least 40 wt%, 50 wt%, 55 wt%, such as 60 wt% of one or more fatty alcohols; wherein the sum of fatty aldehydes, fatty alcohols, and the / V-alkoxyamine does not exceed 100 wt%.N-alkoxyamine

[0089] In some embodiments, the composition of the present disclosure is provided wherein the N- alkoxyamine is detectable by mass spectrometry (MS). In some embodiments, the / V-alkoxyamine is ionizable by a mass spectrometry (MS) method. Whether or not a particular compound, such as an N-alkoxyamine is detectable by MS can readily be determined by the skilled person by subjecting a sample of the particular compound to MS.

[0090] In some embodiments, the / V-alkoxyamine is detectable by an MS method selected from the group consisting of: Electron ionization (El), Electrospray ionization (ESI); Matrix-assisted laser desorption / ionization (MALDI); Time-of-flight (TOF); Quadrupole; Ion trap; Orbitrap; Fourier transform ion cyclotron resonance (FT-ICR). In some embodiments, more than one MS methods are combined, for example TOF with ESI, or TOF with MALDI.

[0091] In some embodiments, the / V-alkoxyamine is ionizable by an MS method selected from the group consisting of: Electron ionization (El), Electrospray ionization (ESI); Matrix-assisted laser desorption / ionization (MALDI); Time-of-flight (TOF); Quadrupole; Ion trap; Orbitrap; Fourier transform ion cyclotron resonance (FT-ICR).

[0092] In some embodiments, the / V-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, 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, 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, 415.4, 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, 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, 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.

[0093] The m / z values or peaks provided in

[0092] correspond to one or more / V-alkoxyamines according to the following table 1:Table 1: overview of selected / V-alkoxyamines of the present disclosure.

[0094] In some embodiments, the / V-alkoxyamine exhibits one or more m / z peaks when measured using mass spectrometry (MS), wherein the one or more peaks are selected from the masses of table 2.Table 2: overview of further / V-alkoxyamines of the present disclosure.

[0095] In some embodiments, the / V-alkoxyamine is detectable by analytical chromatography. In the present context, analytical chromatography allows separation of a plurality of compounds in a sample. The compounds can then be investigated for example by visual inspection using chemicals that react with the compounds to provide colored compounds or by means of a detector. Preferably, the compounds are investigated using a detector such as a suitable MS detector.

[0096] In some embodiments, the / V-alkoxyamine is detectable by an analytical chromatography 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), size-exclusion chromatography (SEC-MS).

[0097] In some embodiments, the / V-alkoxyamine is of formula (Z10-15-A-TEMPO):wherein A is selected from the group consisting of: hydrogen, hydroxy, an alkyl, such as a Ci.g alkyl, an amine, an amide, an alkoxy, such as a Ci-g alkoxy, and an ester, such as a Ci.g ester; or an ion or salt thereof.

[0098] In some embodiments, the composition of the present disclosure comprises an / V-alkoxyamine selected from the group consisting of:(Z10-15-TEMPO).

[0099] In some embodiments, the composition comprises at least 0.02 area% of the / V-alkoxyamine as determined by analytical chromatography coupled to 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% as determined by analytical chromatography coupled to mass spectrometry.

[0100] In some embodiments, the composition comprises at least 0.01 area% of the / V-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% as determined by GC MS.

[0101] In some embodiments, the composition further comprises copper, such as copper(l) or copper(ll).

[0102] In some embodiments, the composition comprises copper(ll) in the form of a copper(ll) salt,such as a copper(ll) salt selected from the group consisting of: a copper(ll) carboxylate, copper(ll) triflate, copper(ll) tetrafluoroborate, copper(ll) hexafluorophosphate, copper(ll) bromide, copper(ll) chloride, copper(ll) iodide, and copper(ll) perchlorate.

[0103] In some embodiments, the composition comprises copper(l) in the form of a copper(l) salt, such as a copper(l) salt selected from the group consisting of: copper(l) chloride, copper(l) bromide, copper(l) iodide, copper(l) cyanide, copper(l) oxide, copper(l) trifluoromethanesulfonate, tetrakis(acetonitrile) copper(l) tetrafluoroborate, tetrakis(acetonitrile) copper(l) tetraphenylborate, tetrakis(acetonitrile) copper(l) hexafluorophosphate, tetrakis(acetonitrile) copper(l) trifluoromethanesulfonate, copper(l) sulfide, copper(l) thiocyanate, Cu[l,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidene]CI, Cu[l,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Br, CuBr(l,10-phenanthroline)2, CuCI(l,10-phenanthroline)h, Cul(l,10-phenanthroline)2, copper(l) trifluoroacetate, [Cu(PPh3)3]Br, [Cu(PPh3)3]F, [Cu(PPh3)3]CI, Cu(OCOR2), Cu(SR2), Cu(SR22)Br, Cu(SR22)CI, CU(SR22)I, CU(OSO2R2), CUOR2, wherein R2is selected from alkyl, preferably C1-C20 alkyl, optionally substituted with one or more aryl, alkoxy and aryloxy and from aryl, preferably C5-C7 aryl, optionally substituted with one or more alkyl, aryl, alkoxy and aryloxy and mixtures thereof. / V-alkoxyamines perse

[0104] In some embodiments, an / V-alkoxyamine is provided of a formula selected from the group consisting of: Z10-15-A-TEMPO; Z10,Z12-15-A-TEMPO; and Z8,E10-15-A-TEMPO:(Z10,Z12-15-A-TEMPO);(Z8,E10-15-A-TEMPO); wherein A is selected from the group consisting of: hydrogen, hydroxy, carbonyl, an alkyl, such as aCi-6 alkyl, an amine, an amide, such as a Ci-g-amide, an alkoxy, such as a Ci.g alkoxy, and an ester, such as a Ci-6 ester; or an ion or salt thereof.

[0105] In some embodiments, A is H. In some embodiments, A is OH. In some embodiments, A is an amide such as a Ci.g-amide, for example a Ci-amide. In some embodiments, A is carbonyl.

[0106] In some embodiments, the / V-alkoxyamine is of formula Z10-15-A-TEMPO wherein A is H. In some embodiments, the / V-alkoxyamine is of formula Z10-15-A-TEMPO wherein A is OH. In some embodiments, the / V-alkoxyamine is of formula Z10-15-A-TEMPO wherein A is Ci-amide (-NHCOMe).In some embodiments, the / V-alkoxyamine is of formula Z10-15-A-TEMPO wherein A is carbonyl.

[0107] In some embodiments, the / V-alkoxyamine is of formula Z10,Z12-15-A-TEMPO wherein A is H.In some embodiments, the / V-alkoxyamine is of formula Z10,Z12-15-A-TEMPO wherein A is OH. In some embodiments, the / V-alkoxyamine is of formula Z10,Z12-15-A-TEMPO wherein A is Ci-amide (-NHCOMe). In some embodiments, the / V-alkoxyamine is of formula Z10,Z12-15-A-TEMPO wherein A is carbonyl.

[0108] In some embodiments, the / V-alkoxyamine is of formula Z8,E10-15- A-TEMPO wherein A is H.In some embodiments, the / V-alkoxyamine is of formula Z8,E10-15- A-TEMPO wherein A is OH. In some embodiments, the / V-alkoxyamine is of formula Z8,E10-15-A-TEMPO wherein A is Ci-amide (-NHCOMe). In some embodiments, the / V-alkoxyamine is of formula Z8,E10-15-A-TEMPO wherein A is carbonyl.

[0109] In some embodiments, the / V-alkoxyamine is selected from the group consisting of:

[0110] In some embodiments, an / V-alkoxyamine is provided of a formula selected from the group consisting of: Z11-16-A-TEMPO-2; Zll,Z13-16-A-TEMPO-2; and Z9,Ell-16-A-TEMPO-2:wherein A is selected from the group consisting of: hydrogen, hydroxy, carbonyl, an alkyl, such as a Ci- s alkyl, an amine, an amide, such as a Ci.g-amide, an alkoxy, such as a Ci-g alkoxy, and an ester, such as a Ci-6 ester; or an ion or salt thereof.

[0111] In some embodiments, A is H. In some embodiments, A is OH. In some embodiments, A is an amide such as a Ci.g-amide, for example a Ci-amide. In some embodiments, A is carbonyl.

[0112] In some embodiments, the / V-alkoxyamine is of formula Z11-16-A-TEMPO-2 wherein A is H. Insome embodiments, the / V-alkoxyamine is of formula Z11-16-A-TEMPO-2 wherein A is OH. In some embodiments, the / V-alkoxyamine is of formula Z11-16-A-TEMPO-2 wherein A is Ci-amide (-NHCOMe). In some embodiments, the / V-alkoxyamine is of formula Z11-16-A-TEMPO-2 wherein A is carbonyl.

[0113] In some embodiments, the / V-alkoxyamine is of formula Zll,Z13-16-A-TEMPO-2 wherein A is H. In some embodiments, the / V-alkoxyamine is of formula Zll,Z13-16-A-TEMPO-2 wherein A is OH. In some embodiments, the / V-alkoxyamine is of formula Zll,Z13-16-A-TEMPO-2 wherein A is Ci-amide (-NHCOMe). In some embodiments, the / V-alkoxyamine is of formula Zll,Z13-16-A-TEMPO-2 wherein A is carbonyl.

[0114] In some embodiments, the / V-alkoxyamine is of formula Z9,Ell-16-A-TEMPO-2 wherein A is H. In some embodiments, the / V-alkoxyamine is of formula Z9,Ell-16-A-TEMPO-2 wherein A is OH. In some embodiments, the / V-alkoxyamine is of formula Z9,Ell-16-A-TEMPO-2 wherein A is Ci-amide (- NHCOMe). In some embodiments, the / V-alkoxyamine is of formula Z9,Ell-16-A-TEMPO-2 wherein A is carbonyl.

[0115] In some embodiments, the / V-alkoxyamine is Z11-16-OH-TEMPO-2:(Z11-16-OH-TEMPO-2).Process for production of the composition

[0116] In some embodiments, a process is provided for producing a composition comprising a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, and a combination thereof; and b) an / V-alkoxyamine; wherein the method comprises the steps of: i) providing a reaction mixture comprising a fatty alcohol, a catalyst comprising a copper source, and a solvent, and ii) oxidizing the fatty alcohol by adding O2 to the reaction mixture in an amount sufficient for converting more than 50 wt% of the fatty alcohol to fatty aldehyde and less than 50 wt% into fatty acid.

[0117] In some embodiments, the process is for large scale conversion of a fatty alcohol into a fatty aldehyde, said method comprising the steps of: a) providing a reaction mixture comprising at least 1 kilogram of fatty alcohol, a catalystcomprising a copper source, at least 1 kilogram of solvent, and a water absorbing or adsorbing material absorbing or adsorbing water, and b) dissolving at least 0,01 pmol O2 per minute per pmol copper in the reaction mixture or at least 0.001 pmol O2 per minute per pmol initial fatty alcohol in the reaction mixture to the reaction mixture by feeding a gas or a liquid comprising O2 into the reaction medium and thereby oxidizing more than 50 wt% of the fatty alcohol into fatty aldehyde and less than 50 wt% into fatty acid.

[0118] In some embodiments, the process removes a carbon atom of the fatty alcohol including covalently attached hydrogen atoms to said carbon atom, wherein the carbon atom is covalently bound to the oxygen atom of the fatty alcohol's hydroxy group.

[0119] In some embodiments, the present disclosure provides a composition obtainable by the process as defined herein for production of the composition.Catalyst composition

[0120] The process for production of the composition of the present disclosure regards oxidation of primary alcohols to produce the corresponding aldehydes. The oxidation of primary alcohol to aldehyde is catalysed by a catalyst composition.

[0121] The catalyst composition comprises a copper(l) source, such as for example a copper(l) salt. The copper(l) source is a substance or mixtures of substances containing a copper(l) compound available for the desired catalysis involving copper(l). Examples include, among others, copper(l) chloride, copper(l) bromide, copper(l) iodide, copper(l) cyanide, copper(l) oxide, copper(l) trifluoromethanesulfonate, tetrakis(acetonitrile) copper(l) tetrafluoroborate, tetrakis(acetonitrile) copper(l) tetraphenylborate, tetrakis(acetonitrile) copper(l) hexafluorophosphate, tetrakis(acetonitrile) copper(l) trifluoromethanesulfonate, copper(l) sulfide, copper(l) thiocyanate, Cu[l,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]CI, Cu[l,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidene]Br, CuBr(l,10-phenanthroline)2, CuCI(l,10-phenanthroline)]2, Cul(l,10-phenanthroline)2, copper(l) trifluoroacetate, [CufPPhahJBr, [CufPPhahJF, [CufPPhaJaJCI, Cu(OCOR2), Cu(SR2), Cu(SR22)Br, CU(SR22)CI, CU(SR22)I, CU(OSO2R2), CUOR2, wherein R2is selected from alkyl, preferably C1-C20 alkyl, optionally substituted with one or more aryl, alkoxy and aryloxy and from aryl, preferably C5-C7 aryl, optionally substituted with one or more alkyl, aryl, alkoxy and aryloxy and mixtures thereof. In addition, the copper(l) source can be a substance or mixtures of substances containing copper in any other oxidation state, provided it can be converted to copper in the oxidation state of +1 by means of reduction or oxidation, either chemically or electrochemically.

[0122] In a preferred embodiment of the present disclosure, the copper(l) source comprises copperpresent in oxidation state of +1.

[0123] In one embodiment of the disclosure, the copper(l) source is soluble in an organic solvent. In a preferred embodiment, the organic solvent is acetonitrile. Solubility of reagents generally improves reaction rate. In a preferred embodiment of the disclosure, the copper(l) source is a copper(l) salt comprises a counter ion, i.e. a negatively charged ion, which has good solubility in the organic solvent. Examples of negatively charged ions which are generally considered to have good solubility in organic solvents such as acetonitrile includes triflate, tetrafluoroborate, hexafluorophosphate, and halides.

[0124] The copper(l) source maybe further comprise ligands coordinated to copper. Examples copper one sources having coordinated ligands include tetrakisacetonitrile copper(l) triflate, tetrakisacetonitrile copper(l) tetrafluoroborate, tetrakisacetonitrile copper(l) hexafluorophosphate, tetrakisacetonitrile copper(l) halide, CuBr(l,10-phenanthroline)2, CuCI(l,10-phenanthroline)h, and Cul(l,10-phenanthroline)2.

[0125] In a preferred embodiment of the present disclosure, the copper(l) source is selected from the group consisting of tetrakisacetonitrile copper(l) triflate, tetrakisacetonitrile copper(l) tetrafluoroborate, tetrakisacetonitrile copper(l) hexafluorophosphate, and tetrakisacetonitrile copper(l) halide.

[0126] Copper(l) ions can be generated in situ from a copper (II) compound and a reductant. Thus, in one embodiment, the copper(l) source comprises a copper(ll) compound and a reductant. In one embodiment, the copper(l) source is a copper(ll) compound and a reductant.

[0127] In one embodiment, the copper(ll) compound is a copper(ll) salt. In one embodiment, the copper(ll) salt comprises counter ion that is soluble in organic solvents. Counter ions that are soluble in organic solvents typically comprise larger organic moieties and / or delocalisable (e.g. by resonance or induction) negative charge. In one embodiment, the copper(ll) salt is selected from the group consisting of copper(ll) triflate, copper(ll) tetrafluoroborate, copper(ll) hexafluorophosphate, copper(ll) bromide, copper(ll) chloride, copper(ll) iodide, and copper(ll) perchlorate.

[0128] The reductant as disclosed herein is capable of reducing copper(ll) to copper(l). The reductant can be either of an organic or an inorganic reductant. In one embodiment of the present disclosure, the reductant is selected from the group consisting of copper metal, zinc metal, aluminium metal, sodium hydrogensulfite, formic acid, salts of formic acid, oxalic acid, and salts of oxalic acid. The metalbased reductants may advantageously be on powder, pellet, shavings, or otherwise finely divided form. The reductant may advantageously be chosen as to not produce any side product(s), or to produce side product(s) that are easily removed, for instance by evaporation. In one embodiment of the present disclosure, the copper(l) source comprises a copper(ll) salt and copper metal.

[0129] In one embodiment of the present disclosure, the catalyst composition of the presentdisclosure comprises a ligand. It is contemplated that the role of the ligand is to coordinate to the copper(l) of the catalyst composition, thereby improving the solubility of the copper(l), stabilising the catalyst composition, and / or improving the catalytic activity of the catalyst composition.

[0130] Suitable ligands include ligands coordinating via nitrogen, oxygen, phosphorous, or other atoms having a lone-pair. In one embodiment of the present disclosure, the ligand coordinates via a moiety selected from the group consisting of a pyridine, a triarylphosphine, a diarylphosphine, an amine, an imidazole, a pyrazole, a pyrrole, a triazole, a tetrazole, an imine, an enamine, a phenol, or a moiety comprising any one of the listed moieties. In a preferred embodiment, the ligand coordinates via a pyridine moiety.

[0131] The ligand may be a monodentate or a polydentate ligand. In one embodiment of the present disclosure, the ligand is a monodentate ligand. In another embodiment of the disclosure, the ligand is a bidentate ligand. In another embodiment, the ligand is a polydentate ligand coordinating with 3 or more atoms.

[0132] In one embodiment of the present disclosure, the catalyst composition comprises a single type of ligand as described herein. In another embodiment of the present disclosure, the catalyst composition comprises a mixture of two or more types of ligands as described herein.

[0133] In one embodiment of the disclosure, the ligand is selected from the group consisting of DETA, PMDETA, TETA, HMTETA, MegTREN, cyclam, Megcyclam, DMCBCy, bpy, dNbpy, 1,10-Phen, tpy, tNtpy, BPMPrA, BPMOA, BPMODA, TPMA, and TPEA. In one embodiment of the disclosure, the ligand is a secondary amine, such as a secondary amine having bulky substituents (i.e. to reduce nucleophilicity of the amine). In one embodiment of the present 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, 2,2'-bipyridine-5,5'-dicarboxylic acid or an ester thereof. In a preferred embodiment of the present disclosure, the ligand is 2,2'-bipyridine (bpy).

[0134] The catalyst composition used for the process of the present disclosure the aminoxyl radical compound (2,2,6,6-tetramethylpiperidin-l-yl)oxyl (TEMPO) or a derivative thereof. In one embodiment of the present disclosure, the aminoxyl radical compound is selected from the group consisting of TEMPO, (4-hydroxy-2,2,6,6-tetramethylpiperidin-l-yl)oxyl (4-OH-TEMPO), 4-acetamido- TEMPO, 4-hydroxy-TEMPO benzoate, 4-amino-TEMPO, 2-azaadamantane-N-oxyl, 9- azabicyclo[3.3.1]nonane N-oxyl, 4-carboxy-TEMPO, 4-maleimido-TEMPO, 4-methoxy-TEMPO, 1- methyl-2-azaadamantane-N-oxyl, 4-oxo-TEMPO, and a polymer functionalised with any of said aminoxyl radical compounds. In a preferred embodiment of the present disclosure, the aminoxylradical compound is selected from the group consisting of TEMPO or (4-hydroxy-2,2,6,6- tetramethylpiperidin-l-yl)oxyl (4-OH-TEMPO). It is contemplated that the aminoxyl radical compound is part of the catalytic cycle which effect oxidation of the fatty alcohol composition of the present disclosure. It is acknowledged that TEMPO and its derivatives described herein act as catalysts for the oxidation of alcohol functional groups to aldehyde functional groups while the oxidant is O2. However, as used herein, TEMPO and the derivatives disclosed herein are also termed "oxidants".

[0135] In one embodiment of the present disclosure, the catalyst composition comprises a base. While some specific bases are mentioned herein below, it is contemplated many different bases will be useful in carrying out the present disclosure. In one embodiment of the present disclosure, the base is an organic base. Using an organic base may be advantageous as it may effect solubility of the base in the reaction medium as disclosed herein. In one embodiment of the present 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 the present disclosure, the base is selected from the group consisting of 1-methylimidazole, l,8-diazabicyclo[5.4.0]undec-7-ene, l,5-diazabicyclo[4.3.0]non-5- ene, l,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,1,3,3-tetramethylguanidine, 7-methyl-l,5,7- triazabicyclo[4.4.0]dec-5-ene, and potassium t-butoxide. In one embodiment of the present disclosure, the base is selected from the group consisting of: 1 -methyl imidazole, potassium tert- butoxide, or l,8-diazabicyclo(5.4.0)undec-7-ene (DBU).

[0136] In one embodiment of the 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 separately to the reaction mixture. In another embodiment, a subset of the elements of the catalyst composition may be mixed and added to reaction mixture, whereas the remaining elements of the catalyst composition is added separately and / or pre-mixed and then added to the reaction mixture.Oxidation

[0137] The process for production of the composition of the present disclosure is contemplated to be useful for the oxidation of various different primary alcohol composition, e.g. composition comprising primary alcohols having chain lengths of at least two carbon atoms. The disclosed methods are nevertheless especially suitable for the oxidation of primary alcohols having chain lengths of eight or more carbon atoms (i.e. fatty alcohols), as further defined in the sections "fatty alcohols" and "fatty aldehydes" herein. Other known methods of carrying out oxidation will often only produce fatty aldehydes compositions in low yield and / or in low purity. "Over oxidation", i.e. further oxidation of the aldehyde to the corresponding carboxylic acid is often a major contributor to the low reactionyields and / or purity of the aldehyde composition. Other known methods of carrying out oxidation of short primary alcohol may not be suitable for oxidation of fatty alcohols, because oxidation may be incomplete, "over oxidation" may occur, and / or it may be infeasible to purify the reaction product. In further relation to oxidation of fatty alcohols to fatty aldehydes, other known methods will often use a relatively large amount of solvent and / or the purification of the reaction product, as outlined in the background section. However, the presently disclosed methods make use of a relatively small volume of solvent for the oxidation reaction, as well as a relative small amount of solvent for the purification of the reaction product. The presently disclosed methods are also advantageous, as they are scalable, i.e. they work on both on small scale (e.g. less than 10 g fatty alcohol composition) or on a large scale (e.g. more than 100 g fatty alcohol composition, such as more than 500 g fatty alcohol composition). Other known methods of oxidising fatty alcohols to the corresponding fatty aldehydes might work well on a small scale (e.g. less than 10 g fatty alcohol composition), but they may not be scalable, i.e. they may not provide for good reaction yields or product purity at a larger scale (e.g. more than 100 g fatty alcohol composition, such as more than 500 g fatty alcohol composition). It is advantageous to obtain an aldehyde composition which is relatively free of by-products such as the corresponding fatty carboxylic acids or unreacted fatty alcohol, as this eliminates the need for time-consuming or expensive purification steps such as distillation. Each of the above mentioned features (small solvent volume, scalability, and substrate scope) makes the presently disclosed methods especially suitable for use in industry.

[0138] One embodiment of the present disclosure provides for a method of converting a fatty alcohol to a fatty aldehyde, said method comprising the steps of: a. providing a reaction mixture comprising a fatty alcohol composition comprising the fatty alcohol, a catalyst composition, and a solvent, and b. exposing the reaction mixture to at least 0.25 ml oxygen per minute per gram of fatty alcohol by means of bubbling a gas mixture comprising oxygen through the reaction mixture. thereby obtaining the fatty aldehyde.

[0139] In one embodiment of the present disclosure, a method is provided for large scale conversion of a fatty alcohol into a fatty aldehyde, said method comprising the steps of: a) providing a reaction mixture comprising at least 1 kilogram of fatty alcohol, a catalyst comprising a copper source, at least 1 kilogram of solvent, and a water absorbing or adsorbing material absorbing or adsorbing water, and b) dissolving at least 0,01 pmol O2 per minute per pmol copper in the reaction mixture or at least 0.001 pmol O2 per minute per pmol initial fatty alcohol in the reaction mixture to the reaction mixture by feeding a gas or a liquid comprising O2 into the reaction medium and thereby oxidizingmore than 50 wt% of the fatty alcohol into fatty aldehyde and less than 50 wt% into fatty acid.

[0140] The presently disclosed methods can be carried out without any external cooling and without any external heating. However, the present oxidation reactions are generally exothermic, and accordingly the reaction mixture is expected to rise in temperature over the course of the reaction. In one embodiment of the present disclosure, the reaction is carried out at 5 to 80 °C, such as 10 to 70 °C, such as 15 to 65 °C. In a further embodiment of the reaction, the reaction mixture is exposed to oxygen at 5 to 80 °C, such as 10 to 70 °C, such as 15 to 65 °C.

[0141] The presently disclosed methods can be carried out at ambient pressure or at elevated pressure. In one embodiment, the exposure of the reaction mixture to oxygen is performed at a pressure 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 exposition of the reaction mixture to oxygen is performed at a pressure 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 the present disclosure exposition of the reaction mixture to oxygen is performed at a pressure of 0.8 to 1.2 bar. However, it is contemplated that the presently disclosed methods can be carried out pressures lower than 0.5 bar or 0.8 bar, provided the amount of oxygen provided to the reaction mixture is as disclosed herein. In one embodiment, the pressure disclosed herein is the pressure in the reaction vessel wherein the exposure of the reaction mixture to oxygen is carried out. In one embodiment, the pressure disclosed herein is the partial pressure of oxygen in the reaction vessel.

[0142] In additional or alternative embodiments, the O2 is added to the reaction medium by mixing the reaction mixture with a gas (such as air) or a liquid comprising O2, optionally enriched with O2. The said mixing can be made made by bubbling a gas mixture comprising O2 through the reaction mixture.

[0143] In some embodiments, the copper source of the present disclosure comprises a copper (I) salt or a combination of copper (II) and a reductant.Oxygen transfer rate

[0144] It is an essential element of the present disclosure that the amount of oxygen supplied to the reaction mixture is above a certain threshold.

[0145] In one embodiment of the present disclosure, the reaction mixture is exposed to at least 0.3 ml 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, 1.4 ml, such as at least 1.5 ml oxygen per minute per gram of fatty alcohol composition. In a preferred embodiment of the present disclosure, the reaction mixture is exposed to at least 1.5 ml oxygen per minute per gram of fatty alcohol composition.

[0146] In one embodiment of the present disclosure, the reaction mixture is exposed to at least 0.3ml oxygen per minute per gram of fatty alcohol, 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, 1.4 ml, such as at least 1.5 ml oxygen per minute per gram of fatty alcohol. In a preferred embodiment of the present disclosure, the reaction mixture is exposed to at least 1.5 ml oxygen per minute per gram of fatty alcohol.

[0147] As used herein, whenever a volume of gas is described, it is intended that this corresponds to the volume of the gas at essentially 1 bar of pressure.

[0148] In one embodiment of the present disclosure, the reaction mixture is exposed to at least 60 ml oxygen per minute per mol of fatty alcohol, such as at least 100 ml, 150 ml, 200 ml, 250 ml, 300 ml, 350 ml, 400 ml, such as at least 450 ml oxygen per minute per mol of fatty alcohol. In a preferred embodiment of the present disclosure, the reaction mixture is exposed to at least 450 ml oxygen per minute per mol of fatty alcohol.

[0149] In one embodiment of the present disclosure, the reaction mixture is exposed to at least 10 pmol oxygen per minute per gram of fatty alcohol, such as at least 12 pmol, 16 pmol, 20 pmol, 24 pmol, 28 pmol, 32 pmol, 36 pmol, 40 pmol, 44 pmol, 48 pmol, 52 pmol, 56 pmol, 60 pmol oxygen per minute per gram of fatty alcohol. In a preferred embodiment of the present disclosure, the reaction mixture is exposed to at least 60 pmol oxygen per minute per gram of fatty alcohol.

[0150] In one embodiment of the present disclosure, the reaction mixture is exposed to at least 2,5 mmol oxygen per minute per mol of fatty alcohol, such as at least 4 mmol, 6 mmol, 8 mmol, 10 mmol, 12 mmol, 14 mmol, 16 mmol, such as at least 18 mmol oxygen per minute per mol of fatty alcohol. In a preferred embodiment of the present disclosure, the reaction mixture is exposed to at least 18 mmol oxygen per minute per mol fatty alcohol.

[0151] The oxygen provided to the reaction mixture of the present disclosure may be provided either as pure oxygen or as a gas mixture comprising oxygen. In one embodiment of the present disclosure, the gas mixture comprises 5 to 100 % oxygen. In a further embodiment of the present disclosure, the gas mixture comprises 15 - 25 % oxygen. In one embodiment of the present disclosure, the gas mixture comprises at least 90 % oxygen. In one embodiment of the present disclosure, the gas mixture is substantially pure oxygen. As outlined herein in the section "water removal", it is beneficial if the amount of water present in the reaction mixture is minimized. Accordingly, in a preferred embodiment of the present disclosure, the gas mixture does not comprise H2O.

[0152] It is contemplated that the sufficient exposure of oxygen to the reaction mixture is achieved in part using a sufficient supply of oxygen as outlined herein but 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 a sufficiently high exposure of oxygen to the reaction mixture, such as by ensuring a sufficiently high dissolution of oxygen in the liquid phase of the reaction mixture. This canbe achieved by using equipment for bubbling gas through a liquid, such as for instance sparging equipment. It is contemplated that increasing the sparging of the gas mixture through the solution improves oxygen transfer rate. It is contemplated that increasing the partial pressure of the oxygen supplied to the reaction mixture improves the oxygen transfer rate. It is contemplated that stirring the reaction mixture improves the oxygen transfer rate. Accordingly, it is desirable that the reaction mixture of the present disclosure is stirred. In one embodiment of the present disclosure, the gas mixture comprising oxygen is bubbled through the reaction mixture. In a further embodiment of the disclosure, the bubbling of gas mixture through the reaction is carried out with sparging equipment. In one embodiment of the present disclosure, the reaction mixture is stirred while it is exposed to oxygen.

[0153] In one embodiment of the present 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 contemplated that the exposure to oxygen does not need to be maintained for a continuous time as specified herein, but can be interrupted. Accordingly, in one embodiment of the present 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 the present disclosure, the reaction mixture is exposed to oxygen for two or more periods of time, wherein the combined periods of time add to at least 60 minutes, such as at least 70 minutes, 80 minutes, 90 minutes, such as at least 100 minutes.

[0154] In one embodiment of the present disclosure, the exposure to O2 is carried out in a bubble column reactor or in a trickle bed reactor.

[0155] It is contemplated that longer reaction times can lead to lower conversion and / or lower yields of the disclosed aldehyde composition. It is contemplated this is due to for example over-oxidation of the aldehyde and / or introduction of water to the reaction mixture beyond the drying capacity of the means of drying. In one embodiment of the present disclosure, the reaction mixture is exposed to oxygen for at most 2000 minutes, such as at most 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 at most 250 minutes.

[0156] It is important that the amount of oxygen added to the reaction medium is balanced to the amount of fatty alcohol in the reaction medium and / or to the amount and effectiveness of the catalyst. The feed of oxygen to the reaction medium for optimal formation of aldehyde may also beinfluenced by the amount of fatty acid in the reaction medium, of which formation of higher amounts of acid requiring increased oxygen feed. Accordingly, in additional or alternative embodiments, the process for production of the composition described herein comprises adding at least 0.010, such as at least 0.020, such as at least 0.030, such as at least 0.040, such as at least 0.049, such as at least 0.060, such as at least 0.070, such as at least 0.080, such as at least 0.090, such as at least 0.100 pmol dissolved O2 per minute per pmol copper in the reaction mixture and / or at least 0.0010, such as at least 0.0020, such as at least 0.0025, such as at least 0.0030, such as at least 0.0050, such as at least 0.0075, such as at least 0.0100 pmol dissolved O2 per minute per pmol initial fatty alcohol in the reaction mixture and / or at least 0.010, such as at least 0.015, such as at least 0.020, such as at least 0.025, such as at least 0.030, such as at least 0.050, such as at least 0.075, such as at least 0.100 pmol dissolved O2 per minute per pmol fatty acid in the reaction mixture.

[0157] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving at least 0.049 pmol dissolved O2 per minute per pmol copper in the reaction mixture.

[0158] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving at least 0.02 pmol dissolved O2 per minute per pmol copper in the reaction mixture, such as at least 0.03 pmol, such as at least 0.04 pmol dissolved O2 per minute per pmol copper in the reaction mixture.

[0159] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving from 0.01 to 1.00 pmol dissolved O2 per minute per pmol copper in the reaction mixture, such as from 0.01 to 0.80 pmol, such as from 0.01 to 0.60 pmol, such as from 0.01 to 0.40 pmol, such as from 0.01 to 0.20 pmol, such as from 0.01 to 0.10 pmol dissolved O2 per minute per pmol copper in the reaction mixture.

[0160] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving at least 0.0025 pmol dissolved O2 per minute per pmol initial fatty alcohol in the reaction mixture.

[0161] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving at least 0.002 pmol dissolved O2 per minute per pmol initial fatty alcohol in the reaction mixture, such as at least 0.003 pmol, such as at least 0.004 pmol dissolved O2 per minute per pmol initial fatty alcohol in the reaction mixture.

[0162] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving from 0.001 to 1.00 pmol dissolved O2 per minute per pmol initial fatty alcohol in the reaction mixture, such as from 0.001 to 0.80 pmol, such as from 0.001 to 0.60 pmol, such as from 0.001 to 0.40 pmol, such as from 0.001 to 0.20 pmol, such as from 0.001 to0.10 pmol dissolved O2 per minute per pmol initial fatty alcohol in the reaction mixture.

[0163] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving at least 0.025 pmol dissolved O2 per minute per pmol fatty acid in the reaction mixture.

[0164] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving at least 0.01 pmol dissolved O2 per minute per pmol fatty acid in the reaction mixture, such as at least 0.02 pmol, such as at least 0.03 pmol, such as at least 0.04 pmol dissolved O2 per minute per pmol fatty acid in the reaction mixture.

[0165] In some embodiments, the process for production of the composition of the present disclosure further comprises dissolving at least 10 pmol O2, such as at least 20 pmol O2, at least 40 pmol O2, or at least 60 pmol O2 per minute per gram of fatty alcohol in the reaction mixture, thereby obtaining the fatty aldehyde, optionally wherein the fatty alcohol and the fatty aldehyde are desaturated.

[0166] In some embodiments the process for production of the composition of the present disclosure further comprises dissolving O2 in the reaction medium at a rate sufficient for maintaining at least 80% O2 saturation in the reaction medium during the oxidation reaction, 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.

[0167] In some embodiments, the gas or a liquid comprising O2 is air, optionally enriched with O2.

[0168] In some embodiments, the process for production of the composition of the present disclosure is provided wherein the feeding of gas or a liquid comprising O2 into the reaction medium is made by pumping or bubbling a gas or liquid mixture comprising O2 through the reaction mixture.Reaction conditions

[0169] The present disclosure achieves conversion of a fatty alcohol composition to a fatty aldehyde composition using a relatively small volume of solvent. In particular, the previously reported methods of converting fatty alcohols to fatty aldehydes as outlined herein utilises a relatively large volume of solvent for the reaction mixture. Large solvent volumes are often considered infeasible in large-scale production because of the costs of the solvent, the environmental footprint, and because handling large reaction volumes can be challenging. Accordingly, the presently disclosed methods of oxidation can advantageously be employed for large scale production of fatty aldehyde compositions due to the relatively small solvent volume required. By "relatively small solvent volume" is meant a volume as outlined herein.

[0170] In one embodiment of the present disclosure, the reaction mixture comprises a solvent. Thesolvent forming part of the reaction mixture may be either a substantially pure solvent or it may be a mixture of solvents. Accordingly, a reference to a solvent of the reaction mixture can in one embodiment also mean a solvent mixture comprising two or more solvents.

[0171] In one embodiment of the present disclosure, the solvent is selected from the group consisting of acetonitrile, dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), alkanes such as pentane, hexane, and heptane, cycloalkanes, petroleum ether such as heavy or light petroleum ether, dioxane, diethyl ether, dichloromethane, tetrahydrofuran, ethyl acetate, acetone, nitromethane, propylene carbonate, and a solvent mixture comprising any one of said solvents.

[0172] In one embodiment, the solvent is an aprotic solvent. It is advantageous that the solvent is aprotic, as protons such as those originating from OH-groups or amines may interfere deleteriously with the components such as for example the catalyst composition, such as for example by inactivating the base. In one embodiment of the present disclosure, the solvent is selected from the list consisting of acetonitrile, dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), alkanes such as pentane, hexane, and heptane, cycloalkanes, petroleum ether such as heavy or light petroleum ether, dioxane, diethyl ether, dichloromethane, tetrahydrofuran, ethyl acetate, acetone, nitromethane, propylene carbonate, and a solvent mixture comprising any one of said solvents. In a preferred embodiment, the solvent is selected from the list consisting of acetonitrile, DMSO, DMF, and a solvent mixture comprising any one of said solvents. In a further preferred embodiment, the solvent is or comprises acetonitrile. In another preferred embodiment of the disclosure, the solvent is acetonitrile.

[0173] In one embodiment, the solvent is a polar solvent. It is advantageous that the solvent is polar as this improves the solubility of at least some of the components of the reaction mixture and / or the components of the gas mixture. In one embodiment of the present disclosure, the solvent is selected from dichloromethane, tetrahydrofuran, ethyl acetate, acetone, dimethyl formamide (DMF), acetonitrile, dimethyl sulfoxide (DMSO), nitromethane, propylene carbonate, and a solvent mixture comprising any one of said solvents. In a preferred embodiment, the solvent is selected from the group consisting of acetonitrile, DMSO, DMF, or a solvent mixture comprising any one of said solvents. In an even further preferred embodiment, the solvent is acetonitrile or a solvent mixture comprising acetonitrile. In yet a further preferred embodiment, the solvent is acetonitrile.

[0174] In assessing the relative amount of solvent utilised for a chemical reaction, the amount of the solvent can be compared to the amount of the reagents or one of the reagents being converted in the chemical reaction, or the amount of the product or one of the products obtained in the chemical reaction.

[0175] The amount of solvent in the reaction mixture can be compared to the amount of fatty alcohol composition. In one embodiment of the present disclosure, the weight of solvent in the reactionmixture is 0 to 2000 % 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 comprise other chemical compounds than fatty alcohol. For the assessment of amount of solvent, it is preferred that these other compounds are excluded when calculating the amount of solvent. Furthermore, the fatty alcohol composition may comprise one or more solvent, i.e. "fatty alcohol composition solvent". In a preferred embodiment of the present disclosure, the fatty alcohol composition solvent is disregarded when assessing the amount of fatty alcohol composition. In one embodiment of the present disclosure, the weight of solvent corresponds to 100 to 2000 % the weight of the fatty alcohol or fatty alcohols of the fatty alcohol composition, such as 100 to 1500 %, such as 100 to 1000 %, such as 100 to 500 %.

[0176] The amount of solvent in the reaction mixture can be compared to the amount of fatty aldehyde composition obtained from said reaction mixture. In one embodiment of the present disclosure, the weight of solvent in the reaction mixture is 100 to 2000 % the weight of the fatty aldehyde composition, such as 100 to 1500 %, such as 100 to 1000 %, such as 100 to 500 %. The fatty aldehyde composition may comprise other chemical compounds than fatty aldehyde. For the assessment of amount of solvent, it is preferred that these other compounds are excluded when calculating the amount of solvent. Furthermore, the fatty aldehyde composition may comprise one or more solvent, i.e. "fatty aldehyde composition solvent". In a preferred embodiment of the present disclosure, the fatty aldehyde composition solvent is disregarded when assessing the amount of fatty aldehyde composition. In one embodiment of the present disclosure, the weight of solvent corresponds to 100 to 2000 % the weight of the fatty aldehyde or fatty aldehydes of the fatty aldehyde composition, such as 100 to 1500 %, such as 100 to 1000 %, such as 100 to 500 %.

[0177] In some embodiments, the solvent is a non-halogenated solvent. In some embodiments, the solvent is selected from acetonitrile, dimethyl sulfoxide (DMSO), dimethyl formamide (DMF), pentane, hexane, heptane, cycloalkane, petroleum ether, dioxane, diethyl ether, tetrahydrofuran, ethyl acetate, acetone, nitromethane, propylene carbonate, or a combination thereof.Determining if production method has been used

[0178] In some embodiments, a method is provided for determining if a composition has been prepared by the process of the present disclosure, wherein the method comprises the steps of: a) providing a composition for analysis; b) subjecting a sample of the composition in a) for analysis by mass spectrometry to obtain a mass spectrum, preferably analytical chromatography coupled to mass spectrometry; c) wherein if the mass spectrum obtained in b) comprises a mass corresponding to an / V-alkoxyamineas defined herein, then the composition has been obtained by the process herein.

[0179] In some embodiments, the method of

[0178] is provided wherein the mass spectrum corresponds essentially to the mass spectrum of Figure 4.

[0180] In some embodiments, the method of the present disclosure is provided, wherein analysis of the sample in b) of

[0178] reveals at least 0.01 area% of the / V-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%.

[0181] In some embodiments, the method of the present disclosure is provided, wherein analysis of the sample in b) of

[0178] by GC MS reveals at least 0.01 area% of the / V-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%.ExamplesExample 1: Monitoring Fatty alcohol oxidation and / V-al oxyamine formation

[0182] A 1-liter bottle was equipped with an air sparger connected to a flow controller, a temperature probe and a stirring magnet. The bottle was filled with 100 g of Zll-hexadecenol oil, 3.25 g of 2,2'- Bipyridine, 1.8 g 4-HydroxyTEMPO 1.7 g N-Methyl Imidazole, and 100 g of acetonitrile. To the mixture, a solution of 7.8 g Cu(ACN)OTf in 100 g of acetonitrile was added. The sparger was started with an air flow of 2.5 L / min. Samples were taken regularly over all the reaction progression. 3 pL of reaction mixture was diluted in 1 ml of Ethyl acetate and analyzed by GC to provide the conversion profile of Figure 1.Example 2: Characterization of / V-alkoxyamine markerCharacterization of N-alkoxyamine maker

[0183] The / V-alkoxyamine Z10-15-TEMPO derived from oxidation toward Zll-16:aldehyde was observed by two gas chromatography (GC) techniques. GC coupled to a Flame Ionization Detector (GC- FID) was able to confirm the compound in a representative sample by retention time matching to the N-alkoxyamine Z10-15-TEMPO derived by chemical synthesis according to the procedure of the present example. GC coupled to a mass spectrometer (GC-MS) operating with an election ionization source at the industry standard 70 eV was able to confirm the compound in a representative sample by retention time matching and mass spectral confirmation when compared against the synthesized standard. Due to the additional confirmatory power of mass spectrometry, the / V-alkoxyamines of thepresent disclosure are ideally identified using GC-MS to confirm their presence in samples, with GC- FID being a complementary technique and useful for quantitative purposes.Instrument MethodsGC-FID Conditions:GC System: Agilent 7890BColumn: Agilent (CAT#19091S-433UI), HP-5MS, 30 m X 250 pm X 0.25 pmInlet Temp: 230°CSplit Ratio: 20:1Column Flow: 1.5 mL / minCarrier Gas: H2Injection Volume: 1 pLOven: 80°C hold 1 min, 15°C / min to 150°C hold 6 min, 5°C / min to 200°C, 20°C / min to 300°C hold 8 minDetector: FIDGC-MS Conditions:GC System: Agilent 6890Column: Agilent (CAT#19091S-433UI), HP-5MS, 30 m X 250 pm X 0.25 pmInlet Temp: 230°CSplit Ratio: Variable based on sample / standard concentrationColumn Flow: 1 mL / minCarrier Gas: HeInjection Volume: 1 pLOven: 80°C Hold 1 min, 15°C / min to 150°C hold 7 min, 10°C / min to 210°C, 20°C / min to 300°C hold 5 minMass Spectrometer: Agilent 5975 MSDIon Source: El at 70eVAcquisition Type: ScanExample 3: Characterization of alternative W-alkoxyamine marker 2Characterization of N-alkoxyamine maker

[0184] The TEMPO Adduct of Zll-16:aldehyde was observed by two gas chromatography (GC) techniques. GC coupled to a Flame Ionization Detector (GC-FID) was able to confirm the compound ina representative sample by retention time matching to a synthesized standard. GC coupled to a mass spectrometer (GC-MS) operating with an election ionization source at the industry standard 70 eV was able to confirm the compound in a representative sample by retention time matching and mass spectral confirmation when compared against a synthesized standard. Due to the additional confirmatory power of mass spectrometry, GC-MS would be the preferred technique to confirm presence of the adduct in future samples, with GC-FID being a complementary technique and useful for quantitative purposes. The structure of / V-alkoxyamine marker 2 is found below:MARKER 2 (4-HYDROXY-2,2,6,6-TETRAMETHYL-1 -PIPERIDYL) (Z)-HEXADEC-11 -ENOATEInstrument MethodsGC-FID Conditions:GC System: Agilent 7890BColumn: Agilent (CAT#19091S-433UI), HP-5MS, 30 m X 250 pm X 0.25 pmInlet Temp: 230°CSplit Ratio: 20:1Column Flow: 1.5 mL / minCarrier Gas: H2Injection Volume: 1 pLOven: 80°C hold 1 min, 15°C / min to 150°C hold 6 min, 5°C / min to 200°C, 20°C / min to 300°C hold 8 minDetector: FIDGC-MS Conditions:GC System: Agilent 6890Column: Agilent (CAT#19091S-433UI), HP-5MS, 30 m X 250 pm X 0.25 pmInlet Temp: 230°CSplit Ratio: Variable based on sample / standard concentrationColumn Flow: 1 mL / minCarrier Gas: HeInjection Volume: 1 pLOven: 80°C Hold 1 min, 15°C / min to 150°C hold 7 min, 10°C / min to 210°C, 20°C / min to 300°C hold 5 minMass Spectrometer: Agilent 5975 MSDIon Source: El at 70eVAcquisition Type: Scan

Claims

Claims1. A method for determining if a composition comprising: a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, a fatty alcohol acetate, and a combination thereof; and b) an / V-alkoxyamine; has been prepared by a process for producing the composition; wherein the process comprises the steps of: i) providing a reaction mixture comprising a fatty alcohol, a catalyst comprising a copper source, and a solvent, and ii) oxidizing the fatty alcohol by adding Ojto the reaction mixture in an amount sufficient for converting more than 50 wt% of the fatty alcohol to fatty aldehyde and less than 50 wt% into fatty acid; wherein the method comprises the steps of:A) providing a composition for analysis;B) subjecting a sample of the composition in A) for analysis by mass spectrometry to obtain a mass spectrum, preferably analytical chromatography coupled to mass spectrometry;C) wherein if the mass spectrum obtained in B) comprises a mass (m / z) corresponding to an N- alkoxyamine, then the composition comprising a) and b) has been obtained by said process.

2. The method according to claim 1, wherein the mass spectrum corresponds essentially to the mass spectrum of Figure 4.

3. The method according to any one of claims 1-2, wherein: a. analysis of the sample in b) reveals at least 0.01 area% of the / V-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%; and / or b. analysis of the sample in b) by GC MS reveals 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%.

4. A composition comprising: a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, a fatty alcohol acetate, and a combination 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 biobased 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% biobased carbon, such as at least 30% biobased carbon, such as at least 40% biobased carbon, such as at least 50% biobased carbon, such as at least 60% biobased carbon, such as at least 70% biobased carbon, such as at least 75% biobased carbon, such as at least 80% biobased carbon, such as at least 85% biobased carbon, such as at least 90% biobased carbon, such as at least 95% biobased carbon, such as 100% biobased carbon; and / or b. from 20% to 100% biobased carbon, such as from 30% to 100% biobased carbon, such as from 40% to 100% biobased carbon, such as from 50% to 100% biobased carbon, such as from 60% to 100% biobased carbon, such as from 70% to 100% biobased carbon, such as from 75% to 100% biobased carbon, such as from 80% to 100% biobased carbon, such as from 85% to 100% biobased carbon, such as from 90% to 100% biobased carbon, such as from 95% to 100% biobased carbon, such as 100% biobased 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% biobased carbon, such as at least 30% biobased carbon, such as at least 40% biobased carbon, such as at least 50% biobased carbon, such as at least 60% biobased carbon, such as at least 70% biobased carbon, such as at least 75% biobased carbon, such as at least 80% biobased carbon, such as at least 85% biobased carbon, such as at least 90% biobased carbon, such as at least 95% biobased carbon, such as 100% biobased carbon; and / or b. from 20% to 100% biobased carbon, such as from 30% to 100% biobased carbon, such as from 40% to 100% biobased carbon, such as from 50% to 100% biobased carbon, such as from 60% to 100% biobased carbon, such as from 70% to 100% biobasedcarbon, such as from 75% to 100% biobased carbon, such as from 80% to 100% biobased carbon, such as from 85% to 100% biobased carbon, such as from 90% to 100% biobased carbon, such as from 95% to 100% biobased carbon, such as 100% biobased 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 a radioactive14C level (%) corresponding to the % biobased carbon.

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, for example at least one substance derived from a yeast cell, such as a metabolite derived from a yeast cell, such as at least one biologically derived substance selected from the group consisting of: hexadecan-l-ol, (Z)-9-hexadecen-l-ol, (Z)-ll-hexadecen-l-ol, (Z,Z)-9,ll-hexadecadien-l-ol, and (Z,E)-9,ll-hexadecadien-l-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, agents, additives, stabilizers, antioxidants, UV absorbers, light stabilizers, antifreeze agents, diols, polyols, adjuvants and / or excipients; and / or b. a protective agent comprising a sulfur containing compound, optionally wherein the protective agent comprises a 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-l,3,4-thiadiazole-2-thiol, 2-thiazoline-2-thiol, 5-methyl- l,3,4-thiadiazole-2-thiol, 2-mercapto-benzimidazole, 2-mercapto-l-methylimidazole and sodium pyrithione, which protects the target compound from from being converted into an acid; and / or b) a carrier facilitating slow release of the (Z,E)-9,ll-hexadecadienal, (Z)-9-hexadecenal, (Z)-ll- hexadecenal and / or hexadecanal from the mixture, optionally being (i) a polymeric substrate selected from plastic, wax emulsion, oil emulsion, or microcapsules and / or (ii) a zeolite.

13. The method according to any one of claims 1-3 or the composition according to any one of claims4-12, wherein the fatty alcohol: a. is a primary alcohol; b. is a saturated fatty alcohol or a desaturated fatty alcohol; and / or c. is a CIO to C26 fatty alcohol, such as a CIO to C22 fatty alcohol or such as a C12 to C20 fatty alcohol, such as a C12 to C18 fatty alcohol, for example a C12, C14, C16 or C18 fatty alcohol.

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 has: a. a double bond at position 9, 11 or 13, or wherein the fatty alcohol has double bonds at positions 9 and 11, or at positions 11 and 13; or b. a double bond at position 9 or 12, or wherein the fatty alcohol has double bonds at positions 9 and 12; or c. a double bond at position 8 or 10, or wherein the fatty alcohol has double bonds 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)-A3 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A3 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A5 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A5 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A6 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A6 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A7 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A7 desaturated fatty alcohols having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16,17, 18, 19, 20, 21 or 22;(Z)-A8 desaturated fatty alcohols having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22;(E)-A8 desaturated fatty alcohols having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22;(Z)-A10 desaturated fatty alcohols having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(E)-A10 desaturated fatty alcohols having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(Z)-All desaturated fatty alcohols having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19,20, 21 or 22;(E)-All desaturated fatty alcohols having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A12 desaturated fatty alcohols having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A12 desaturated fatty alcohols having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A13 desaturated fatty alcohols having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22; and(E)-A13 desaturated fatty alcohols having a carbon chain length 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 claims4-16, wherein the fatty alcohol is selected from the group consisting of:(E)7,(Z)9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21, or 22,(E)3,(Z)8,(Z)11 desaturated fatty alcohols having a carbon chain length of 12, 13, 14, 15, 16, 17,18, 19, 20, 21, or 22,(Z)9,(E)11,(E)13 desaturated fatty alcohols having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21, or 22,(Z)11,(Z)13 desaturated fatty alcohols having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22,(Z)9,(E)12 desaturated fatty alcohols having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22,(E)7,(E)9 desaturated fatty alcohols having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22, and(E8,E10) desaturated fatty alcohols having a carbon chain length 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 alcohol having a carbon chain length of 14, (E)3,(Z)8,(Z)11 desaturated fatty alcohol having a carbon chain length of 14, (Z)9,(E)11,(E)13 desaturated fatty alcohol having a carbon chain length of 14, (E)7,(Z)9 desaturated fatty alcohol having a carbon chain length of 12, (E)3,(Z)8,(Z)11 desaturated fatty alcohol having a carbon chain length of 12, (Z)9,(E)11,(E)13 desaturated fatty alcohol having a carbon chain length of 12, (E)8,(E)10 desaturated fatty alcohol having a carbon chain length of 12, (E)7,(E)9 desaturated fatty alcohol having a carbon chain length of 11, (Z)11,(Z)13 desaturated fatty alcohol having a carbon chain length of 16, and (Z)9,(E)12 desaturated fatty alcohol having 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 tetradecan-l-ol, pentadecan-l-ol, hexadecan-l-ol, pentadecen-l-ol, (Z)-9-hexadecen-l-ol, (Z)-ll-hexadecen-l-ol, (7E,9E)-undeca-7,9-dien-l-ol, (11Z, 13Z)-hexadecadien-l-ol, (9Z,llE)-hexadecadien-l-ol, (9Z, 12E)-tetradecadien-l-ol, and (8E,10E)-dodecadien-l-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 fatty aldehyde is: a. a saturated fatty aldehyde or a desaturated fatty aldehyde;b. a CIO to C26 fatty aldehyde, such as a CIO to C22 fatty aldehyde or a C12 to C20 fatty aldehyde, for example a C12, C14, or C16 fatty aldehyde; and / or c. an unbranched fatty aldehyde.

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 wherein the desaturated fatty aldehyde has double bonds at positions 9 and 11, or at positions 11 and 13; b. the desaturated fatty aldehyde has a double bond at position 9 or 12, or wherein the desaturated fatty aldehyde has double bonds at positions 9 and 12; or c. the desaturated fatty aldehyde has a double bond at position 8 or 10, or wherein the desaturated fatty aldehyde has double bonds 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 fatty 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 fatty aldehyde is selected from the group consisting of:(Z)-A3 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A3 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A5 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A5 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A6 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A6 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A7 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A7 desaturated fatty aldehydes having a carbon chain length of 8, 9, 10, 11, 12, 13, 14, 15, 16,17, 18, 19, 20, 21 or 22;(Z)-A8 desaturated fatty aldehydes having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A8 desaturated fatty aldehydes having a carbon chain length of 9, 10, 11, 12, 13, 14, 15, 16,17, 18, 19, 20, 21 or 22;(Z)-A9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22;(E)-A9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16, 17,18, 19, 20, 21 or 22;(Z)-A10 desaturated fatty aldehydes having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(E)-A10 desaturated fatty aldehydes having a carbon chain length of 11, 12, 13, 14, 15, 16, 17, 18,19, 20, 21 or 22;(Z)-All desaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19,20, 21 or 22;(E)-All desaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A12 desaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(E)-A12 desaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22;(Z)-A13 desaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22; and(E)-A13 desaturated fatty aldehydes having a carbon chain length 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 fatty aldehyde is selected from the group consisting of:(E)7,(Z)9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16,17, 18, 19, 20, 21, or 22,(E)3,(Z)8,(Z)11 desaturated fatty aldehydes having a carbon chain length of 12, 13, 14, 15, 16, 17,18, 19, 20, 21, or 22,(Z)9,(E)11,(E)13 desaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18,19, 20, 21, or 22,(Z)11,(Z)13 desaturated fatty aldehydes having a carbon chain length of 14, 15, 16, 17, 18, 19, 20, 21 or 22,(Z)9,(E)12 desaturated fatty aldehydes having a carbon chain length of 13, 14, 15, 16, 17, 18, 19, 20, 21 or 22,(E)7,(E)9 desaturated fatty aldehydes having a carbon chain length of 10, 11, 12, 13, 14, 15, 16,17, 18, 19, 20, 21 or 22, and(E)8,(E)10 desaturated fatty aldehydes having a carbon chain length 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 fatty aldehyde is selected from the group consisting of:(E)7,(Z)9 desaturated fatty aldehyde having a carbon chain length of 14, (E)3,(Z)8,(Z)11 desaturated fatty aldehyde having a carbon chain length of 14, (Z)9,(E)11,(E)13 desaturated fatty aldehyde having a carbon chain length of 14, (E)7,(Z)9 desaturated fatty aldehyde having a carbon chain length of 12, (E)3,(Z)8,(Z)11 desaturated fatty aldehyde having a carbon chain length of 12, (Z)9,(E)11,(E)13 desaturated fatty aldehyde having a carbon chain length of 12, (E)8,(E)10 desaturated fatty aldehyde having a carbon chain length of 12 (E)7,(E)9 desaturated fatty aldehyde having a carbon chain length of 11, (Z)11,(Z)13 desaturated fatty aldehyde having a carbon chain length of 16, and (Z)9,(E)12 desaturated fatty aldehyde having 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 fatty aldehyde is selected from the group consisting of tetradecanal, pentadecanal, hexadecanal, pentadecenal, (Z)-9-hexadecenal, (Z)-ll-hexadecenal, (7E,9E)- undeca-7,9-dienal, (llZ,13Z)-hexadecadienal, (9Z,llE)-hexadecadienal, (9Z,12E)- tetradecadienal, and (8E,10E)-dodecadienal.

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 wt% of one or more of the fatty aldehydes, such as at least 40 wt%, 50 wt%, 55 wt%, such as 60 wt% of one or more of the fatty aldehydes, and / or d) at least 30 wt% of one or more fatty alcohols, such as at least 40 wt%, 50 wt%, 55 wt%, such as 60 wt% of one or more fatty alcohols;wherein the sum of fatty aldehydes, fatty alcohols, and the / V-alkoxyamine does not exceed 100 wt%.

28. The method according to any one of claims 1-3 or the composition according to any one of claims 4-27, wherein the / V-alkoxyamine is: a. detectable by mass spectrometry (MS); b. ionizable by a mass spectrometry (MS) method; c. detectable by an MS method selected from the group consisting of: Electron ionization (El), Electrospray ionization (ESI); Matrix-assisted laser desorption / ionization (MALDI); Time-of-flight (TOF); Quadrupole; Ion trap; Orbitrap; Fourier transform ion cyclotron resonance (FT-ICR); and / or d. ionizable by an MS method selected from the group consisting of: Electron ionization (El), Electrospray ionization (ESI); Matrix-assisted laser desorption / ionization (MALDI); Time-of-flight (TOF); Quadrupole; Ion trap; Orbitrap; 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 / V-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, 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, 361.3,375.4, 389.4, 403.4, 417.4, 431.4, 445.4, 459.4, 317.3, 331.3, 345.3, 359.3, 373.3, 387.4, 401.4,415.4, 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, 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, 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 claims4-29, wherein the / V-alkoxyamine is detectable by analytical chromatography, for example detectable by an analytical chromatography 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), size-exclusion chromatography (SEC-MS).

31. The method according to any one of claims 1-3 or the composition according to any one of claims4-30, wherein the / V-alkoxyamine is of a formula selected from the group consisting of: Z10-15-A-TEMPO; Z10,Z12-15-A-TEMPO; and Z8,E10-15-A-TEMPO:(Z10,Z12-15-A-TEMPO);(Z8,E10-15- A-TEMPO); wherein A is selected from the group consisting of: hydrogen, hydroxy, carbonyl, an alkyl, such as a Ci-6 alkyl, an amine, an amide, such as a Ci.g-amide, an alkoxy, such as a Ci.g alkoxy, and an ester, such as a Ci-g ester; or an ion or salt thereof.The method according to any one of claims 1-3 or the composition according to claim 31, wherein the / V-alkoxyamine is selected from the group consisting of:(Z10-15-TEMPO).

33. The method according to any one of claims 1-3 or the composition according to claim 31, wherein the / V-alkoxyamine is of formula: a. Z10,Z12-15-A-TEMPO and wherein A is H or wherein A is OH; or b. Z8,E10-15-A-TEMPO and wherein A is H or wherein A is OH.

34. The method according to any one of claims 1-3 or the composition according to any one of claims4-33, wherein a. the composition comprises at least 0.02 area% of the / V-alkoxyamine as determined by analytical chromatography coupled to mass spectrometry, such as at least 0.03area%, 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% as determined by analytical chromatography coupled to mass spectrometry; and / or b. the composition comprises at least 0.01 area% of the / V-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% as determined by GC MS.

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(l) or copper(ll), for example in the form of a copper(ll) salt, such as a copper(ll) salt selected from the group consisting of: a copper(ll) carboxylate, copper(ll) triflate, copper(ll) tetrafluoroborate, copper(ll) hexafluorophosphate, copper(ll) bromide, copper(ll) chloride, copper(ll) iodide, and copper(ll) perchlorate; or for example in the form of of a copper(l) salt, such as a copper(l) salt selected from the group consisting of: copper(l) chloride, copper(l) bromide, copper(l) iodide, copper(l) cyanide, copper(l) oxide, copper(l) trifluoromethanesulfonate, tetrakis(acetonitrile) copper(l) tetrafluoroborate, tetrakis(acetonitrile) copper(l) tetraphenylborate, tetrakis(acetonitrile) copper(l) hexafluorophosphate, tetrakis(acetonitrile) copper(l) trifluoromethanesulfonate, copper(l) sulfide, copper(l) thiocyanate, Cu[l,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]CI, Cu[l,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]Br, CuBr(l,10-phenanthroline)2, CuCI(l,10- phenanthroline)h, Cul(l,10-phenanthroline)2, copper(l) trifluoroacetate, [Cu(PPh3)3]Br, [Cu(PPh3)3]F, [Cu(PPh3)3]CI, Cu(OCOR2), Cu(SR2), Cu(SR22)Br, Cu(SR22)CI, Cu(SR22)l, Cu(OSO2R2), CuOR2, wherein R2is selected from alkyl, preferably C1-C20 alkyl, optionally substituted with one or more aryl, alkoxy and aryloxy and from aryl, preferably C5-C7 aryl, optionally substituted with one or more alkyl, aryl, alkoxy and aryloxy and mixtures thereof.

36. An / V-alkoxyamine of a formula selected from the group consisting of: Z10-15-A-TEMPO; Z10,Z12- 15-A-TEMPO; and Z8,E10-15-A-TEMPO:(Z8,E10-15- A-TEMPO); wherein A is selected from the group consisting of: hydrogen, hydroxy, carbonyl, an alkyl, such as a Ci-6 alkyl, an amine, an amide, such as a Ci.g-amide, an alkoxy, such as a Ci.g alkoxy, and an ester, such as a CI-B ester; or an ion or salt thereof.

37. The alkoxyamine according to claim 36, wherein the / V-alkoxyamine is selected from the group consisting of:

38. A process for producing a composition comprising a) at least one active ingredient selected from the group consisting of: a fatty aldehyde, a fatty alcohol, and a combination thereof; and b) an N- alkoxyamine; wherein the method comprises the steps of: i) providing a reaction mixture comprising a fatty alcohol, a catalyst comprising a copper source, and a solvent, and ii) oxidizing the fatty alcohol by adding O2 to the reaction mixture in an amount sufficient for converting more than 50 wt% of the fatty alcohol to fatty aldehyde and less than 50 wt% into fatty acid.

39. The process according to claim 38, wherein the process is for large scale conversion of a fatty alcohol into a fatty aldehyde, said method comprising the steps of: a) providing a reaction mixture comprising at least 1 kilogram of fatty alcohol, a catalyst comprising a copper source, at least 1 kilogram of solvent, and a water absorbing or adsorbing material absorbing or adsorbing water, and b) dissolving at least 0,01 pmol O2 per minute per pmol copper in the reaction mixture or at least 0.001 pmol O2 per minute per pmol initial fatty alcohol in the reaction mixture to the reaction mixture by feeding a gas or a liquid comprising O2 into the reaction medium and thereby oxidizing more than 50 wt% of the fatty alcohol into fatty aldehyde and less than 50 wt% into fatty acid.

40. The process according to claims 38-39, wherein the process removes a carbon atom of the fatty alcohol including covalently attached hydrogen atoms to said carbon atom, wherein the carbon atom is covalently bound to the oxygen atom of the fatty alcohol's hydroxy group.

41. A composition obtainable by the process of any one of claims 38-40.* * *

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