Biologically-produced fluorinated monomers and polymers

Abstract

The present invention related to the field of sustainable chemicals production and particularly the bio-based production of fluorinated building blocks as a sustainable alternative to traditional petroleum-derived chemical synthesis processes. The present invention provides a chemical precursor and monomer comprising 2-fluoroadipic acid (2FAA), a polymer comprising fluorinated polyamide 66 and polyamide 46 and a method for producing said precursor, monomer and polymer.

Description

Biologically-produced fluorinated monomers and polymersField

[0001] The present invention related to the field of sustainable chemicals production and particularly the bio-based production of fluorinated building blocks as a sustainable alternative to traditional petroleum-derived chemical synthesis processes.The present invention provides a chemical precursor and monomer comprising 2-fluoroadipic acid (2FAA), a polymer comprising fluorinated polyamide 66 and polyamide 46 and a method for producing said precursor, monomer and polymer.Background

[0002] Polyamides are engineering plastics and represent the largest and most important class of these materials. The combination of mechanical and thermal properties allows them to be employed in highly specialized end uses. Polyamides encompass a range of materials, depending on the monomers used.

[0003] Nylon 66, also known as polyamide 66 (PA66), is a versatile engineering thermoplastic used in a wide range of applications due to its excellent mechanical and thermal properties. Nylon 66 is composed of two monomers, each containing six carbon atoms: hexamethylenediamine (HMDA) and adipic acid (AA). Its relatively low manufacturing costs make it an essential thermoplastic used in various applications, including automotive, electrical and electronics, aerospace, medical, consumer goods, textiles and carpets and industrial sectors.

[0004] Nylon 46, also known as polyamide 46 (PA46), is an aliphatic polyamide created through the polycondensation of two monomers: 1,4-diaminobutane (DAB) (putrescine), which has 4 carbon atoms, and adipic acid, which has 6 carbon atoms, contributing to the name of nylon 46. Besides having excellent mechanical properties, it has improved thermal properties compared to Nylon 66 and thus its preferred for applications requiring higher thermal and wear resistance, such as automotive engine parts, high-temperature industrial components, gears, and bearings.In addition, both Nylon 66 and Nylon 46 are recyclable through mechanical and chemical processes, offering options for end-of-life management of these polymers to reduce environmental impact.

[0005] However, to fully leverage their versatility, enhancing the material properties of these polyamides is crucial. This enhancement can expand its application range targeting advanced engineering applications by enabling its use in more demanding environments. An illustrative example of this necessity is Nylon 66's increasing role as a polyamide fiber in the textile industry, although itswidespread adoption is hindered by its high water absorption tendencies. This high moisture absorption can lead to dimensional changes, reduced mechanical properties, and potential swelling.

[0006] This can be a significant drawback in applications where dimensional stability is critical. Furthermore, Nylon 66 shows limited high-temperature performance and prolonged exposure to high temperatures can lead to degradation and loss of mechanical properties. While Nylon 46 has better performance at higher temperatures and absorbs less moisture than some other nylons, it can still absorb moisture from the environment, which may affect its mechanical properties and dimensional stability over time. Moreover, both polyamides present sensitivity to strong acids and bases, as they can be susceptible to degradation when exposed to these substances limiting their use in environments where such chemicals are present.

[0007] W02022003144A1 in the name of DANMARKS TEKNISKE UNIVERSITET appears to disclose bacterial cells and methods for production of 2-fluoro-c / s,c / s-muconate.Wirth et al, 2021 appears to disclose biosynthetic access to 2-fluoro-c / s,c / s-muconate in engineered Pseudomonas putida.

[0008] Direct chemical fluorination of polyamides appears to be described in Solomun, Tihomir, Schimanski, Arnd, Sturm, Heinz, Mix, Renate and lllenberger, Eugen. "Surface modification of polyamides by direct fluorination" e-Polymers, vol. 4, no. 1, 2004, pp. 008, and LJ. Hayes, D.D. Dixon, Direct fluorination of polyamide, Journal of Fluorine Chemistry, Volume 10, Issue 1, 1977, Pages 17-26, ISSN 0022-1139.Summary

[0009] Advancements in biotechnology and material science have paved the way for exploring new avenues to enhance the properties of polyamides. Specifically, the incorporation of fluorine into materials lead to enhanced material properties, leading to improvements in water repellency, chemical resistance, thermal stability, electrical properties, and mechanical performance, making fluorine a valuable element for improving material properties across various industries.

[0010] The incorporation of fluorine into the molecular structure of polyamides holds the promise of creating a new material with enhanced properties, potentially overcoming the limitations of its nonfluorinated counterparts. So far, classical chemistry approaches have not been able to provide a method for producing fluorinated polyamides.

[0011] The synthesis of fluorinated polyamides could be enabled by harnessing the power of biotechnology and biofluorination in bacterial cells, making it possible to produce precursors and materials that traditional chemistry has deemed impossible to synthesize.

[0012] As previously mentioned, polyamides 66 and 46 are synthesized using AA, also known ashexanedioic acid, as a monomer. AA is one of the most extensively produced commodity chemicals globally as, besides its primary use is being a monomer for the synthesis of polyamides, it serves as a versatile building block in a multitude of processes across the chemical, pharmaceutical, and food industries. Additionally, AA is widely employed in the production of polyester and polyurethane resins. It acts as a plasticizer in the manufacturing of polyvinyl chloride (PVC) and polyvinyl butyral (PVB), enhancing their flexibility and usability. Beyond these applications, AA is approved as an additive in cosmetics, gelatins, lubricants, fertilizers, adhesives, insecticides, paper, and waxes.

[0013] Despite of this, AA is primarily produced by an industrial process that can form nitrous oxide, a gas that has a 300-fold higher global warming potential than carbon dioxide, as a byproduct. An estimated 10% of nitrous oxide annual global emissions are a result of AA production. There is the need to find alternative ways to produce this valuable chemical precursor.

[0014] The fluorination of AA expands its utility, enabling the synthesis of a wide array of fluorinated compounds, which potentially have significant industrial and pharmaceutical applications. Specifically, the synthesis of 2F-adipic acid (2FAA) as a polyamide monomer is a strategy to enable the synthesis of fluorinated variants of polyamides 66 and 46 with emerging material properties.

[0015] This invention presents a method for producing 2 F-adipic acid from biologically derived 2FMA. This approach circumvents the environmental issues associated with the chemical synthesis of nonfluorinated adipic acid. By reducing the environmental impact of traditional production methods, this process offers a greener alternative for manufacturing this fluorinated precursor.

[0016] Moreover, there is the pressing need to replace fossil-based plastics with more sustainable alternatives. As environmental concerns continue to escalate, there's a growing consensus on the necessity of shifting towards materials that have a lower carbon footprint and are derived from renewable sources. In response to this imperative, there has been increasing interest in polymers produced from biologically sourced precursors. These biologically sourced monomers and polymers have the potential to reduce reliance on finite fossil resources and mitigate the environmental impacts associated with traditional plastic production.

[0017] Additionally, due to their recyclability, biologically-produced fluorinated polyamides have the potential to be used as Per- and polyfluoroalkyl substances (PFAS) replacements. PFAS are widely used in sectors such as MedTech, transportation, electronics, and renewable energy, praised for their unique features like resistance to water and stains, ability to withstand various temperatures, and chemical stability. These substances are considered irreplaceable for enhancing product longevity, safety, and performance under demanding conditions where alternatives do not measure up. Despite of this, PFAS, pose a significant environmental and health hazard. These compounds are non- degradable and thus highly persistent in the environment, leading to lasting environmental andecological impacts. Moreover, the production of PFAS, is highly unsustainable, as it is an energy- intensive process that relies on fossil-derived feedstocks and toxic catalysts, resulting in the noncontrolled creation of harmful by-products and highly fluorinated substances that persist in the environment.

[0018] Classical chemistry approaches are not able to provide an environmentally sustainable route to produce fluorochemicals and fluorinated polymers. Moreover, no other production approach for the synthesis of fluorinated polyamides or bioproduction approach for the synthesis of bio-based monomers for polyamide synthesis is known so far.

[0019] The present invention comprises an embodiment, where the halogen atom fluorine has been introduced into a novel molecule 2-fluoroadipic acid (2FAA) derived from 2-fluoromuconic acid (2FMA) enabling access to novel molecules, building blocks and polymers that could not be obtained otherwise. 2FAA serves as a valuable building block enabling the potential synthesis of numerous value-added fluorinated compounds for various industries, including but not limited to the production of monomers for polymer synthesis.

[0020] Additionally, the presence of fluorine atoms in the molecules enhances their material properties making them more resistant towards harsh conditions.

[0021] 2FAA was used as a monomer for new types of fluorinated polyamides, specifically, polyamide 66 (Nylon 66) and polyamide 46 (Nylon 46). Regular Nylon 66 is polymerized from adipic acid (AA) and hexamethylenediamine (HMDA). Previous attempts to produce fluorinated versions of nylons were unsuccessful, as chemical fluorination of the polymers destroyed the molecules. Achieving synthesis of 2FAA through our 2FMA precursor opens the door to a new strategy for producing fluorinated nylons by introducing fluorine into the monomer rather than the final polymer enhancing material properties. Additionally, direct fluorination of polyamides does not allow for precision fluorination (which is possible when the monomer is fluorinated).

[0022] The invention comprises the conversion of 2-fluoromuconic acid (2FMA) to 2-fluoroadipic acid (2FAA) by reduction, for example via a hydrogenation reaction, or an enzymatic method. 2FAA can serve as a valuable building block leading to the synthesis of multiple value-added fluorinated compounds across various industries including but not limited to the production of monomers for polymer synthesis or pharmaceutical drugs synthesis. The present invention describes a novel method of producing 2FAA from 2FMA.

[0023] Additionally, the invention comprises the production of fluorinated Nylon 66 polymerized from varying ratios of fluorinated and non-fluorinated adipic acid (2FAA and AA) (50%) and hexamethylenediamine (HMDA) (50%). Additionally, it comprises the production of Nylon 46 from varying ratios of fluorinated and non-fluorinated adipic acid. The approach to introduce fluorinedirectly in the monomer compared to the polymer via synthesis of 2FAA through our 2FMA precursor is a breakthrough in fluorinated Nylon production as previous attempts were unsuccessful leading to the destruction of the molecule from the chemical fluorination.

[0024] The present invention provides bio-based and sustainable alternative to PFAS, with a lower fluorine content and controlled degree of fluorination.

[0025] There is a need for monomers and polymers that offer end-of-life management options, unlike traditional PFAS which are persistent "forever chemicals". Additionally, there is a need for monomers and polymers as alternatives to PFAS, that are energy efficient and environmentally safe.

[0026] As a sustainable alternative to PFAS, the present invention is using a bio-based approach to produce fluorinated polyamides derived from 2-fluoromuconic acid (2FMA). Targeted introduction of single fluorine atoms is challenging to achieve through chemical synthesis as traditional methods involve highly reactive and toxic chemicals and are often unable to produce a specific stereoisomer product. P. putida has been previously efficiently engineered to convert fluorinated benzoates into the corresponding halogenated c / s,c / s-muconate. In this patent application, 2FMA is further converted to 2-fluoroadipic acid (2FAA), for example via a hydrogenation reaction.

[0027] Adipic acid (AA) is a top-50 bulk chemical that is used for the production of Nylon 66 and Nylon 46 where it serves as a building block to produce the polymer but is also used to manufacture other polymers or polyamides for the textile fiber, yarn and plastic industry as well as polyurethane for flexible and semi-rigid foams. The value of bio-based adipic acid is increased by introducing halogen atoms into the molecule and its derivatives, generating products that cannot be accessed chemically. The introduction of a fluorine atom into a molecule or polymer structure could generate industrially relevant properties such as water-repellency, inertness to acids, bases and solvents; low dielectric constant; low refractive index; high resistance to aging and oxidation; and low surface tension.

[0028] The present invention provides a method to produce 2FAA from 2FMA, which can be used for a broad spectrum of applications ranging from polyamides such as Nylon 66 and Nylon 46, advanced oils, greases, fluids, lubricants, coatings, plastics, plasticizers, wet strength resins, adhesives, sealants and elastomers, specialty filters, membranes, perfumes and cosmetics, semiconductors and pharmaceuticals.

[0029] In contrast to traditional fluorochemistry methods that generate products with CF? and CF3 bonds, the bioengineered approach described herein specifically yields targeted CF bonds. The presence of C— F bonds in the materials, as opposed to the CF? and CF3 bonds found in traditional PFAS, results in a distinct classification for the products, which are not anticipated to be subject to existing or potential future usage restrictions and can thus be used as PFAS replacements.

[0030] The biofluorination technology is also energy-efficient and can potentially utilize renewablecarbon sources and waste materials as feedstock. It also minimizes the generation of pollutants and greenhouse gas emissions (GHG) compared to traditional chemical fluorination.

[0031] According to an aspect, the invention relates to a monomer comprising 2-fluoro adipic acid (2FAA), having the following structure:

[0032] The presence of fluorine atoms in the molecule enhances the material properties making it more resistant towards harsh conditions. The introduction of a fluorine atom into a molecule or polymer structure could generate industrially relevant properties such as water-repellency, inertness to acids, bases, solvents and oils; low dielectric constant; low refractive index; high resistance to aging and oxidation; and low surface tension.

[0033] According to another aspect, the invention relates to a polymer comprising: a. 1,4-diaminobutane (DAB) or hexamethylenediamine (HMDA), b. at least one monomer according to the invention, and c. optionally, adipic acid (AA).

[0034] According to another aspect, the invention relates to a polymer comprising fluorinated polyamide 66, wherein said fluorinated polyamide 66 comprises at least one monomer, at least two or at least three monomers according to the invention.

[0035] According to another aspect, the invention relates to a polymer comprising fluorinated polyamide 46, wherein said fluorinated polyamide 46 comprises at least one monomer, at least two or at least three monomers according to the invention.

[0036] According to another aspect, the invention relates to a method of producing the monomer and / or the polymer according to the invention.

[0037] In another aspect, the present disclosure provides a method for purifying a crude composition of 2-fluoromuconic acid, comprising: a) obtaining a crude composition comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90%; and b) subjecting the composition to purification by filtration, solvent evaporation, precipitation, and / or recrystallization to provide a solid composition of 2-fluoromuconic acid having at least 90% purity.

[0038] In another aspect of the present disclosure, a method is provided for producing 2-fluoro adipic acid (2FAA), said method comprising: a) Providing a composition comprising 2-fluoromuconic acid (2FMA), such as 2-fluoro-cis,cis-muconic acid, in a solvent; b) Subjecting the composition comprising 2-fluoromuconic acid to reduction, such as by hydrogenation, providing 2FAA; and c) Thereby obtaining 2FAA.

[0039] In another aspect of the present disclosure, a method is provided of forming a 2-fluoroadipic acid (2FAA) salt comprising, a) Mixing 2FAA or a composition comprising 2FAA with a base, such as an amine base, to provide a mixture, optionally in an aqueous solution; b) Adding a polar protic solvent to the mixture, such an alcohol, for example isopropyl alcohol forming a precipitate; and c) Collecting the precipitate, optionally by filtration, as the 2FAA salt.

[0040] In some embodiments, a method is provided for preparing a polymer comprising a fluorinated polyamide by melt polymerization comprising: a) providing a composition comprising a 2-fluoroadipic acid (2FAA) salt; b) subjecting the 2-fluoroadipic acid (2FAA) salt to melt polymerization providing the polymer comprising the fluorinated polyamide.

[0041] According to another aspect, the invention relates to a method of producing the 2FAA monomer according to the invention, wherein said method comprises the following steps: a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, wherein said reduction is performed in the presence of Ethyl Acetate, b. Obtaining the 2FAA monomer.

[0042] According to another aspect, the invention relates to a method of producing a monomer and / or a polymer, wherein said method comprises the steps of a. Introducing fluorine into a monomer, and / or b. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, c. Obtaining the monomer and / or polymer.

[0043] The fluorine atom is introduced directly in the monomer, thus avoiding destruction of the polymer from chemical fluorination.

[0044] In another aspect of the present disclosure, a process is provided for preparing a polymer comprising a fluorinated polyamide from a crude composition of 2-fluoromuconic acid, comprising the consecutive steps of: a) purifying a crude composition of 2-fluoromuconic acid comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90% using a method as defined herein;b) producing 2-fluoroadipic acid (2FAA) using a method as defined herein; c) producing a 2-fluoroadipic acid (2FAA) salt using a method as defined herein, and d) producing the polymer comprising the fluorinated polyamide by polymerization using a method as defined herein.

[0045] In another aspect of the present disclosure, a process is provided for preparing a polymer comprising a fluorinated polyamide from 3-fluorobenzoate, comprising the consecutive steps of: a) Culturing a cell culture comprising a growth medium and a bacterial cell capable of producing 2-fluoromuconic acid (2FMA) in the presence of 3-fluorobenzoate or a salt thereof at conditions allowing the bacterial cell to produce a crude composition of 2-fluoromuconic acid; and b) purifying the crude composition of 2-fluoromuconic acid obtained in "step a" using a method as defined herein to provide a solid composition of 2-fluoromuconic acid having at least 90% purity; c) producing 2-fluoro adipic acid (2FAA) using a method as defined herein; d) producing a 2-fluoroadipic acid (2FAA) salt using a method as defined herein, and e) producing the polymer comprising the fluorinated polyamide by polymerization using a method as defined herein.

[0046] In a further aspect, a method is provided for purifying a crude composition of 2-fluoromuconic acid, comprising: obtaining a crude composition comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90%; and subjecting the composition to purification by filtration, solvent evaporation, precipitation, and / or recrystallization to provide a solid composition of 2-fluoromuconic acid having at least 90% purity.

[0047] In a further aspect, a method is provided for producing 2-fluoro adipic acid (2FAA), said method comprising: providing a composition comprising 2-fluoromuconic acid (2FMA), such as 2-fluoro-cis,cis-muconic acid, in a solvent; subjecting the composition comprising 2-fluoromuconic acid to reduction, such as by hydrogenation, providing 2FAA; and thereby obtaining 2FAA.

[0048] In a further aspect, a method is provided for producing a monomer and / or a polymer, wherein said method comprises the steps of: introducing fluorine into a monomer, and / or reduction of 2FMA to 2FAA, such as via a hydrogenation reaction,obtaining the monomer and / or polymer.

[0049] In a further aspect, a method is provided for forming a 2-fluoroadipic acid (2FAA) salt comprising, mixing 2FAA or a composition comprising 2FAA with a base, such as an amine base, to provide a mixture, optionally in an aqueous solution; adding a polar protic solvent to the mixture, such an alcohol, for example isopropyl alcohol forming a precipitate; and collecting the precipitate, optionally by filtration, as the 2FAA salt.

[0050] In a further aspect, a method is provided for preparing a polymer comprising a fluorinated polyamide by polymerization comprising: a) providing a composition comprising a 2-fluoroadipic acid (2FAA) salt; b) subjecting the 2-fluoroadipic acid (2FAA) salt to polymerization providing the polymer comprising the fluorinated polyamide.

[0051] In a further aspect, a process is provided for preparing a polymer comprising a fluorinated polyamide from a crude composition of 2-fluoromuconic acid, comprising the consecutive steps of: a) purifying a crude composition of 2-fluoromuconic acid comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90% using a method as defined herein; b) producing 2-fluoroadipic acid (2FAA) using a method as defined herein; c) producing a 2-fluoroadipic acid (2FAA) salt using a method as defined herein, and d) producing the polymer comprising the fluorinated polyamide by polymerization using a method as defined herein.

[0052] In a further aspect, a process is provided for preparing a polymer comprising a fluorinated polyamide from 3-fluorobenzoate, comprising the consecutive steps of: a) culturing a cell culture comprising a growth medium and a bacterial cell capable of producing 2-fluoromuconic acid (2FMA) in the presence of 3-fluorobenzoate or a salt thereof at conditions allowing the bacterial cell to produce a crude composition of 2-fluoromuconic acid; and b) purifying the crude composition of 2-fluoromuconic acid obtained in "step a" using a method as defined herein to provide a solid composition of 2-fluoromuconic acid having at least 90% purity; c) producing 2-fluoro adipic acid (2FAA) using a method as defined herein; d) producing a 2-fluoroadipic acid (2FAA) salt using a method as defined herein, and e) producing the polymer comprising the fluorinated polyamide by polymerization using amethod as defined herein.

[0053] In a further aspect, a polymer obtainable by the method as defined herein or the process as defind herein, is provided.Drawings and figures

[0054] The accompanying Figures and Examples are provided to explain rather than limit the present invention.

[0055] When describing the embodiments of the present invention, the combinations of all possible embodiments have not been explicitly described. Nevertheless, the mere fact that certain measures are recited in mutually different dependent claims or described in different embodiments does not indicate that a combination of these measures cannot be used to advantage. The present invention envisages all possible combinations and permutations of the described embodiments.Unless specifically defined herein, all technical and scientific terms used have the same meaning as commonly understood by a skilled artisan in the field.

[0056] All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety. In case of conflict, the present specification, including definitions, will prevail.

[0057] Further, the materials, methods, and examples are illustrative only and are not intended to be limiting, unless otherwise specified.Figure 1 shows an overview of 2FAA, F-fluorinated Nylon 66 and fluorinated nylon 46 production. By incorporating non-fluorinated adipic acid as a third monomer into the polymerization reaction, it is possible to produce a copolymer comprising both fluorinated and non-fluorinated monomers. Furthermore, varying the ratios of 2FAA and AA in the polymerization process allows for the creation of different variants with varying fluorine content.Figure 2 shows an overview of three possible results for the polymerization reaction of 2FAA with HMDA or DAB:1. 2FAA polymerizes with HMDA through the Cl position.2. 2FAA polymerizes with HMDA at the C6 position.3. Polymerization with HMDA could occur at either the Cl or C6 position.4. 2FAA polymerizes with DAB through the Cl position.5. 2FAA polymerizes with DAB at the C6 position.6. Polymerization with DAB could occur at either the Cl or C6 position.Figures 3 shows a FTIR spectrum of a polymer of the present disclosure comprising polyamide 46. Figures 4 shows a FTIR spectrum of a polymer of the present disclosure comprising polyamide 66.Incorporation by reference

[0058] All publications, patents, and patent applications referred to herein are incorporated by reference 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

[0059] Any EC numbers used herein refers to Enzyme Nomenclature 1992 from NC-IUBMB, Academic Press, San Diego, California, including 30 supplements 1-5 published in Eur. J. Bio-chem. 1994, 223, 1- 5; Eur. J. Biochem. 1995, 232, 1-6; Eur. J. Biochem. 1996, 237, 1-5; Eur. J. Biochem. 1997, 250, 1-6; and Eur. J. Biochem. 1999, 264, 610-650; respectively. The nomenclature is regularly supplemented and updated; see e.g. http: / / enzyme.expasy.org / . The term "PEP" as used herein refers to phosphoenol pyruvate.

[0060] The terms "heterologous" or "recombinant" or "genetically modified" and their grammatical equivalents as used herein interchangeably refers to entities "derived from a different species or cell". For example, a heterologous or recombinant polynucleotide gene is a gene in a bacterial cell not naturally containing that gene, i.e. the gene is from a different species or cell type than the bacterial cell.

[0061] The term "metabolic pathway" as used herein is intended to mean two or more enzymes acting sequentially in a live cell to convert chemical substrate(s) into chemical product(s). Enzymes are characterized by having catalytic activity, which can change the chemical structure of the substrate(s). An enzyme may have more than one substrate and produce more than one product. The enzyme may also depend on cofactors, which can be iganic chemical compounds or organic compounds such as proteins for example enzymes (co-enzymes). The term "operative biosynthetic metabolic pathway" refers to a metabolic pathway that occurs in a live recombinant cell, as described herein.

[0062] The term "in vivo", as used herein refers to within a living cell or organism, including, for example animal, a plant or a microorganism.

[0063] The term "in vitro", as used herein refers to outside a living cell or organism, including, without limitation, for example, in a microwell plate, a tube, a flask, a beaker, a tank, a reactor and the like.

[0064] The term "in planta", as used herein refers to within a plant or plant cell.

[0065] The term "substrate" or "precursor", as used herein refers to any compound that can be converted into a different compound. For clarity, substrates and / or precursors include both compounds generated in situ by a enzymatic reaction in a cell or exogenously provided compounds, such as exogenously provided organic molecules which the bacterial cell can metabolize into a desired compound.

[0066] Term "endogenous" or "native" as used herein refers to a gene or a polypepetide in a bacterial cell which originates from the same bacterial cell.

[0067] 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.

[0068] 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.

[0069] 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 are not limited to compounds of 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 atleast 98% pure, such as at least 99% pure, such as at least 99.5% pure, such as 100 % pure by weight.

[0070] The term "non-naturally occurring" as used herein about a substance, refers to any substance that is not mally found in nature or natural biological systems. In this context the term "found in nature or in natural biological systems" does not include the finding of a substance in nature resulting from releasing the substance to nature by deliberate or accidental human intervention. Non-naturally occurring substances may include substances completely or partially synthetized by human intervention and / or substances prepared by human modification of a natural substance.

[0071] The term "% identity" is used herein about the relatedness between two amino acid sequences or between two nucleotide sequences.

[0072] The term "% identity" as used herein about amino acid sequences refers to the degree of identity in percent between two amino acid sequences obtained when using the Needleman-Wunsch algorithm (Needleman and Wunsch, 1970, J. Mol. Biol. 48: 443-453) as implemented in the Needle program of the EMBOSS package (EMBOSS: The European Molecular Biology Open Software Suite, Rice et al., 2000, Trends Genet. 16: 276-277), preferably version 5.0.0 or later. The parameters used are gap open penalty of 10, gap extension penalty of 0.5, and the EBLOSUM62 (EMBOSS version of BLOSUM62) substitution matrix. The output of Needle labeled "longest identity" (obtained using the -nobrief option) is used as the percent identity and is calculated as follows: identical amino acid residues- x 100Length of alignment — total number of gaps in alignment

[0073] The term "% identity" as used herein about nucleotide sequences refers to the degree of identity in percent between two nucleotide sequences obtained when using the Needleman-Wunsch algorithm (Needleman and Wunsch, 1970, supra) as implemented in the Needle program of the EMBOSS package (EMBOSS: The European Molecular Biology Open Software Suite, Rice et al., 2000, supra), preferably version 5.0.0 or later. The parameters used are gap open penalty of 10, gap extension penalty of 0.5, and the EDNAFULL (EMBOSS version of NCBI NUC4.4) substitution matrix.

[0074] The output of Needle labeled "longest identity" (obtained using the -nobrief option) is used as the percent identity and is calculated as follows: identical deoxyribonucleotides- - - x 100Length of alignment — total number of gaps in alignment

[0075] The protein sequences of the present disclosure can further be used as a "query sequence" to perform a search against sequence databases, for example to identify other family members or relatedsequences. Such searches can be performed using the BLAST programs. Software for performing BLAST analyses is publicly available through the National Center for Biotechnology Information (http: / / www.ncbi.nlm.nih.gov). BLASTP is used for amino acid sequences and BLASTN for nucleotide sequences. The BLAST program uses as defaults:Cost to open gap: default= 5 for nucleotides / 11 for proteinsCost to extend gap: default = 2 for nucleotides / 1 for proteinsPenalty for nucleotide mismatch: default = -3Reward for nucleotide match: default= 1Expect value: default = 10Wordsize: default = 11 for nucleotides / 28 for megablast / 3 for proteins.

[0076] Furthermore, the degree of local identity between the amino acid sequence query or nucleic acid sequence query and the retrieved homologous sequences is determined by the BLAST program. However only those sequence segments are compared that give a match above a certain threshold. Accordingly, the program calculates the identity only for these matching segments. Therefore, the identity calculated in this way is referred to as local identity.

[0077] The term "bacterial cell" refers to any bacterial cell type that is susceptible to transformation, transfection, transduction, or the like with a nucleic acid construct or expression vector comprising a polynucleotide of the present disclosure. Bacterial cell encompasses any progeny of a parent cell that is not identical to the parent cell due to mutations that occur during replication.

[0078] The term "polynucleotide construct" refers to a polynucleotide, either single- or double stranded, which is isolated from a naturally occurring gene or is modified to contain segments of nucleic acids in a manner that would not otherwise exist in nature or which is synthetic, and which comprises a polynucleotide encoding a polypeptide and one or more control sequences.

[0079] The term "operably linked" refers to a configuration in which a control sequence is placed at an appropriate position relative to the coding polynucleotide such that the control sequence directs expression of the coding polynucleotide.

[0080] The terms "nucleotide sequence and "polynucleotide" are used herein interchangeably.

[0081] 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.

[0082] The articles "a" and "an" are used herein refers to one or to more than one (i.e. to one or atleast one) of the grammatical object of the article. By way of example, "an element" may mean one element or more than one element.

[0083] Terms like "preferably", "commonly", "particularly", and "typically" are not utilized herein to limit the scope of the itemed disclosure or to imply that certain features are critical, essential, or even important to the structure or function of the itemed disclosure. 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 disclosure.

[0084] The term "cell culture" as used herein refers to a culture medium comprising a plurality of bacterial cells of the disclosure. A cell culture may comprise a single strain of bacterial cells or may comprise two or more distinct bacterial cell strains. The culture medium may be any medium that may comprise a recombinant host, e.g., a liquid medium ( / .e., a culture broth) or a semi-solid medium, and may comprise additional components, e.g., a carbon source such as dextrose, sucrose, glycerol, or acetate; a nitrogen source such as ammonium sulfate, urea, or amino acids; a phosphate source; vitamins; trace elements; salts; amino acids; nucleobases; yeast extract; aminoglycoside antibiotics such as G418 and hygromycin B.

[0085] As used herein, when a polymer is described as comprising at least one monomer, such as wherein the monomer is 2-fluoroadipic acid or a monomer as defined herein, it is to be understood that the monomer refers to its structural unit as it is incorporated in the polymer. In particular, the monomer does not retain its original functional groups (e.g., hydroxy or carboxy groups), but has undergone a chemical transformation, such as esterification or amidation, as a result of its covalent incorporation into the polymer backbone. Accordingly, references to monomers such as 2-fluoroadipic acid in the context of a polymer are to be interpreted as referring to the corresponding units within the polymer structure, which are no longer present in their free or unreacted form.

[0086] The term "crude composition" of 2-fluoromuconic acid as used herein refers to a composition comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90% by weight relative to the total weight of the composition. The impurities may include, for example, by-products, residual nutrients, host cell components, or other fermentation- derived materials. The crude composition may, for instance, be an unpurified or only partially purified fermentation broth comprising 2-fluoromuconic acid, such that 2-fluoromuconic acid has not yet been isolated to high purity through downstream processing steps, such as by the methods of the present disclosure. Unless stated otherwise, purity is chemical purity as determined by HPLC.

[0087] The term "polar protic solvent" as used herein refers to a solvent (or a mixture of solvents) that is polar, meaning it has a dipole moment, and that contains at least one hydrogen atom bound to a highly electronegative atom such as oxygen or nitrogen (e.g., in -OH or -NH groups), allowing thesolvent to act as a proton donor in hydrogen bonding. Polar protic solvents are capable of stabilizing charged species via both dipole interactions and hydrogen bonding. Examples of polar protic solvents include, but are not limited to, water, methanol, ethanol, n-propanol, isopropanol, n-butanol, secbutanol, tert-butanol, acetic acid, formic acid, ethylene glycol, and ammonia. In some embodiments, the polar protic solvent is ethanol.

[0088] The term "polar aprotic solvent" as used herein refers to a solvent (or a mixture of solvents) that is polar, meaning it has a dipole moment, but lacks acidic protons (like those in OH or NH2 groups) and therefore cannot act as a proton donor in hydrogen bonding. Examples of polar aprotic solvents include, but are not limited to, acetone, acetonitrile, chloroform, dichloromethane (methylene chloride or DCM), N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), N- methylpyrrolidone (NMP), dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO), ethyl acetate (EtOAc), hexamethylphosphoramide (HMPA), 1,4-dioxane, pyridine, methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), methyl tert-butyl ether (MTBE), isopropyl acetate (iPrOAc), tetrahydrofuran (THF), and 2-methyltetrahydrofuran (MeTHF). In some embodiments, the polar aprotic solvent is ethyl acetate.

[0089] The term "apolar solvent" (also referred to as a non-polar solvent) as used herein refers to a solvent (or a mixture of solvents) that has a low dielectric constant and little or no dipole moment, and therefore does not readily participate in dipole-dipole or hydrogen bonding interactions. Apolar solvents are generally poor at solvating ionic or highly polar species, but are suitable for dissolving non-polar or weakly polar compounds. Examples of apolar solvents include, but are not limited to, n- hexane, n-heptane, cyclohexane, benzene, toluene, diethyl ether, petroleum ether, and carbon tetrachloride (CCI4).

[0090] The term "catalyst metal loading" as used herein refers to the amount of catalyst metal present in a supported catalyst composition, expressed as a weight percentage of the total weight of the supported catalyst. For example, in the case of palladium on carbon (Pd / C), a catalyst metal loading of 5% means that palladium constitutes 5% by weight of the total weight of the Pd / C catalyst, including both the palladium and the carbon support. The catalyst metal loading may vary depending on the application and is typically reported as a nominal or average value based on the preparation or supplier specification.

[0091] The term "melt polymerization" as used herein refers to a polymerization process carried out in the absence of a solvent or without large amounts of solvent, for example at most 30 volumes of solvent relative to the reactant, wherein the monomers and / or oligomers are heated to a temperature above their melting point(s) to form a molten phase in which the polymerization reaction occurs. In melt polymerization, the reaction components are typically in the liquid (molten) state, allowingpolymer chains to form and grow without the use of a separate liquid reaction medium. The process may be conducted under atmospheric or reduced pressure and may involve the removal of volatile by-products such as water, alcohols, or other condensates. Melt polymerization can be used for the production of polymers, such as the polyamides of the present disclosure, and other condensation polymers.

[0092] The term "Rope polymerization" as used herein refers to a polymerization process, typically conducted as a continuation or subsequent stage of a melt polymerization process, wherein the polymer melt is discharged or extruded in the form of elongated strands, ropes, or filaments. In rope polymerization, the polymerization reaction continues within these elongated molten strands, often under reduced pressure and / or elevated temperature, to allow further polymer chain growth and removal of volatile by-products, such as water, alcohols, or other condensates. The rope-like configuration of the polymer melt provides an increased surface area-to-volume ratio that facilitates efficient devolatilization and promotes the attainment of higher molecular weights. Rope polymerization is particularly applicable to the production of the polyamides of the present disclosure.

[0093] As used herein, the variables m, n, and o represent integers indicating the number of times a given structural unit is repeated in a polymer or oligomer. Unless otherwise specified, m, n, and o are independently any integer greater than or equal to 1, and may vary depending on the length, composition, or architecture of the polymer. These variables are used to indicate the degree of polymerization of one or more repeating units within the polymer backbone or side chains, and do not necessarily imply a uniform or fixed value across all polymer chains in a composition. The terms, "m, n, and o" are in some embodiments, independently from 1 to 10.000, such as from 1 to 10, such as from 10 to 50, such as from 50 to 75, such as from 75 to 100, such as from 100 to 150, such as from 150 to 200, such as from 200 to 250, such as from 250 to 300, such as from 300 to 350, such as from 350 to 400, such as from 400 to 450, such as from 450 to 500, such as from 500 to 1,000, such as from 1,000 to 2,000, such as from 2,000 to 3,000, such as from 3,000 to 4,000, such as from 4,000 to 5,000, such as from 5,000 to 6,000, such as from 6,000 to 7,000, such as from 7,000 to 8,000, such as from 8,000 to 9,000, such as from 9,000 to 10,000.

[0094] The term "NyFon66" used herein refers to fluorinated polyamide 66, and the "NyFon46" refers to fluorinated polyamide 46. NyFon66 comprises or consists of repetitive units (oligomers) of two covalently linked monomers each containing six carbon atoms, i.e. the condensation product of hexamethylenediamine and 2-fluoroadipic acid. NyFon66 may contain a mixture of repetitive units each comprising i) the condensation product of hexamethylenediamine and 2-fluoroadipic acid or ii) the condensation product of hexamethylenediamine and adipic acid. NyFon46 comprises or consists of repetitive units (oligomers) of two covalently linked monomers one containing six carbon atomsand one containing 4 carbon atoms, i.e. the condensation product of 1,4-diaminobutane and 2- fluoroadipic acid. NyFon46 may contain a mixture of repetitive units each comprising i) the condensation product of 1,4-diaminobutane and 2-fluoroadipic acid or ii) the condensation product of 1,4-diaminobutane and adipic acid.

[0095] The terms "Nyfon66", "Nyfon 66" and "F-Nylon 6,6" are used interchangeably.

[0096] The terms "Nyfon46", "Nyfon 46" and "F-Nylon 4,6" are used interchangeably.

[0097] The terms "2-fluoroadipic acid", "2-FAA", "2FAA" and "FAA" are used interchangeably to refer to 2-fluoroadipic acid.

[0098] The terms "2-fluoromuconic acid", "2FMA", "2-FMA" are used interchangeably to refer to 2- fluoromuconic acid."Monomers and polymers

[0099] The polymers of the present disclosure have important properties in materials sciences, and by design of polymers having a predefined fluorine content, properties such as solubility, general resistance and anti-adhesion can be modulated. Generally, a higher fluorine content provides a higher polymer resistance and thus lower solubility, but such polymers with a predefined fluorine content has previously not been accessible.

[0100] According to an embodiment, the invention relates to a monomer comprising 2-fluoro adipic acid (2FAA), having the following structure:

[0101] According to an embodiment, the invention relates to a polymer comprising: a. 1,4-diaminobutane (DAB) or hexamethylenediamine (HMDA), b. at least one monomer according to the invention, and c. optionally, adipic acid (AA).

[0102] According to an embodiment, the invention relates to a polymer comprising fluorinated polyamide 66, wherein said fluorinated polyamide 66 comprises at least one monomer, at least two or at least three monomers according to the invention.

[0103] According to an embodiment, the invention relates to a polymer comprising fluorinated polyamide 46, wherein said fluorinated polyamide 46 comprises at least one monomer, at least two or at least three monomers according to the invention.

[0104] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer consists of fluorinated polyamide 66 or polyamide 46, and preferably wherein said polymer comprises the monomer according to the invention.

[0105] According to an embodiment, the invention relates to the polymer according to the invention, wherein the fluorine content is about 0.1 -10 % F (w / w), 1 - 10 % F (w / w), about 2-8 % F (w / w), about 3 - 7 % F (w / w), or about 4 -6 % F (w / w).

[0106] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer is selected among: i) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; and vi) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n [-OC-(CH2)4-CO- NH-(CH2)6-NH-]O.

[0107] In some embodiments, m, n, and o are independently any integer. The variables m, n, and o represent integers indicating the number of times a given structural unit is repeated in a polymer or oligomer. Unless otherwise specified, m, n, and o are independently any integer greater than or equal to 1, and may vary depending on the length, composition, or architecture of the polymer. These variables are used to indicate the degree of polymerization of one or more repeating units within the polymer backbone or side chains, and do not necessarily imply a uniform or fixed value across all polymer chains in a composition.

[0108] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer is selected among: i) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n[-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m[-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m[-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; and vi) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m[-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n [-OC-(CH2)4-CO- NH-(CH2)4-NH-]O.

[0109] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises any of the following structures:

[0110] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises the any of the following structures:

[0111] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises any of the following structures:

[0112] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises the any of the following structures:

[0113] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises one or more oligomers selected from the group consisting of:

[0114] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises one or more oligomers selected from the group consisting of:

[0115] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises one or more oligomers selected from the group consisting of:

[0116] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises one or more oligomers selected from the group consisting of:

[0117] In some embodiments, a polymer is provided obtainable by the method or process as disclosed herein.

[0118] In some embodiments, a polymer composition is provided obtainable by Rope polymerization as defined herein.

[0119] In some embodiments, a polymer composition is provided obtainable by Melt polymerization as defined herein.

[0120] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises a non-fluorinated monomer.

[0121] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer does not comprise CF? or CF3 bonds.

[0122] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer does not comprise CF? or CF3 groups.

[0123] According to an embodiment, the invention relates to the polymer according to the invention, wherein the fluorine content in % F (w / w) is about 0.1 - 10 % F (w / w), 1 -10 % F (w / w), about 2-8 % F (w / w), about 3 - 7 % F (w / w), or about 4 -6 % F (w / w).

[0124] In some embodiments, the fluorinated polymer comprises from 0.1% w / w fluorine to 10.0% w / w fluorine, such as from 0.1% to 0.5%, such as from 0.5% to 1.0%, such as from 1.0% to 1.5%, such as from 1.5% to 2.0%, such as from 2.0% to 2.5%, such as from 2.5% to 3.0%, such as from 3.0% to 3.5%, such as from 3.5% to 4.0%, such as from 4.0% to 4.5%, such as from 4.5% to 5.0%, such as from 5.0% to 5.5%, such as from 5.5% to 6.0%, such as from 6.0% to 6.5%, such as from 6.5% to 7.0%, such as from 7.0% to 7.5%, such as from 7.5% to 8.0%, such as from 8.0% to 8.5%, such as from 8.5% to 9.0%, such as from 9.0% to 9.5%, such as from 9.5% to 10.0%.

[0125] As used herein, the fluorine content of a polymer according to the present disclosure, expressed as a weight percentage, may be determined using any suitable analytical technique capable of accurately quantifying fluorine atoms in the polymer material. Such techniques include, but are not limited to, elemental analysis (e.g., combustion analysis followed by ion-selective detection or ion chromatography), X-ray fluorescence (XRF) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy, such as19F NMR. The choice of method may depend on the nature of the polymer, the form of the sample, and the required sensitivity or specificity. Unless otherwise indicated, the fluorine content refers to the total fluorine atoms present in the polymer, regardless of their position in the polymer structure.

[0126] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises and / or is made of about 37.5 % (w / w) AA, about 12.5 % (w / w) 2FAAand about 50 % (w / w) HMDA, and preferably wherein said polymer has a fluorine content of about 2 % F (w / w).

[0127] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises and / or is made of about 25 % (w / w) AA, about 25 % (w / w) 2FAA and about 50 % (w / w) HMDA, and preferably wherein said polymer has a fluorine content of about 4 % F (w / w).

[0128] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises and / or is made of about 12.5 % (w / w) AA, about 37.5% (w / w) 2FAA and about 50 % (w / w) HMDA, and preferably wherein said polymer has a fluorine content of about 6 % F (w / w).

[0129] According to an embodiment, the invention relates to the polymer according to the invention, wherein said polymer comprises and / or is made of about 50 % (w / w) 2FAA and about 50 % (w / w) HMDA, and preferably wherein said polymer has a fluorine content of about 8 % F (w / w).

[0130] In some embodiments, the polymer comprises a mixture of fluorinated and non-fluorinated oligomers or monomers. In some embodiments, the polymer comprises the oligomers and / or monomers defined herein.

[0131] In some embodiments, a polymer is provided comprising from 0.1 mol% fluorinated oligomer or monomer to 100 mol% fluorinated oligomer or monomer with the balance being non-fluorinated oligomer or monomer.

[0132] In some embodiments, the polymer comprises from 0.1% w / w fluorine to 10% w / w fluorine, such as from 0.1% to 0.5%, such as from 0.5% to 1.0%, such as from 1.0% to 1.5%, such as from 1.5% to 2.0%, such as from 2.0% to 2.5%, such as from 2.5% to 3.0%, such as from 3.0% to 3.5%, such as from 3.5% to 4.0%, such as from 4.0% to 4.5%, such as from 4.5% to 5.0%, such as from 5.0% to 5.5%, such as from 5.5% to 6.0%, such as from 6.0% to 6.5%, such as from 6.5% to 7.0%, such as from 7.0% to 7.5%, such as from 7.5% to 8.0%, such as from 8.0% to 8.5%, such as from 8.5% to 9.0%, such as from 9.0% to 9.5%, such as from 9.5% to 10.0%.

[0133] In some embodiments, the polymer is provided comprising from 0.1 mol% fluorinated oligomer or monomer to 100 mol% fluorinated oligomer or monomer, such as from 0.1 mol% to 1 mol%, such as from 1 mol% to 5 mol%, such as from 5 mol% to 10 mol%, such as from 10 mol% to 15 mol%, such as from 15 mol% to 20 mol%, such as from 20 mol% to 25 mol%, such as from 25 mol% to 30 mol%, such as from 30 mol% to 35 mol%, such as from 35 mol% to 40 mol%, such as from 40 mol% to 45 mol%, such as from 45 mol% to 50 mol%, such as from 50 mol% to 55 mol%, such as from 55 mol% to 60 mol%, such as from 60 mol% to 65 mol%, such as from 65 mol% to 70 mol%, such as from 70 mol% to 75 mol%, such as from 75 mol% to 80 mol%, such as from 80 mol% to 85 mol%, such asfrom 85 mol% to 90 mol%, such as from 90 mol% to 95 mol%, such as from 95 mol% to 100 mol%.

[0134] In some embodiments, the polymer is provided comprising 25 mol%, 50 mol%, 75 mol%, or 100 mol% fluorinated oligomer or monomer.

[0135] In some embodiments, the polymer is fluorinated polyamide 66 comprising 25 mol%, 50 mol%, 75 mol%, or 100 mol% fluorinated oligomer.

[0136] In some embodiments, the polymer is fluorinated polyamide 46 comprising 25 mol%, 50 mol%, 75 mol%, or 100 mol% fluorinated oligomer.

[0137] In some embodiments, the polymer comprises from about 12.5 % to about 50 % VJ / VJ 2- fluoroadipic acid, about 50% w / w hexamethylenediamine or 1,4-diaminobutane, the balance being adipic acid.

[0138] In some embodiments, the polymer comprises: a) about 37.5 % (w / w) adipic acid, about 12.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 2.1% w / w; b) about 25 % (w / w) adipic acid, about 25 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 4.1% w / w; c) about 12.5 % (w / w) adipic acid, about 37.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 6.0% w / w; and / or d) about 50 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 7.8% w / w.

[0139] In some embodiments, the polymer comprises: a) about 37.5 % (w / w) adipic acid, about 12.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4-diaminobutane and a maximum theoretical fluorine content of 2.3% w / w; b) about 25 % (w / w) adipic acid, about 25 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4- diaminobutane and a maximum theoretical fluorine content of 4.5% w / w; c) about 12.5 % (w / w) adipic acid, about 37.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4-diaminobutane and a maximum theoretical fluorine content of 6.7% w / w; and / or d) about 50 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4-diaminobutane and a maximum theoretical fluorine content of 8.7% w / w.

[0140] In some embodiments, the polymer of the present disclosure is obtainable by the method as disclosed herein, in particular by a polymerization method as disclosed herein. In some embodiments, the polymer of the present disclosure is obtainable by a process as defined herein.

[0141] In some embodiments, the polymer is obtainable by the method comprising polymerization of a mixture of adipic acid, 2-fluoroadipic acid, and hexamethylenediamine.

[0142] In some embodiments, the polymer is obtainable by the method comprising polymerizationof a mixture of 2-fluoroadipic acid, and hexamethylenediamine.

[0143] In some embodiments, the polymer obtainable by the method comprises polymerization of about 50% w / w hexamethylenediamine, and from 0% w / w to 50% w / w 2-fluoroadipic acid, the balance being adipic acid, such as from 12.5% w / w 2-fluoroadipic acid to 50% w / w 2-fluoroadipic acid.

[0144] In some embodiments, the polymer is obtainable by polymerization of a mixture of 2- fluoroadipic acid, and hexamethylenediamine.

[0145] In some embodiments, the polymer is obtainable by polymerization of a mixture of adipic acid, 2-fluoroadipic acid, and 1,4-diaminobutane.

[0146] In some embodiments, the polymer is obtainable by polymerization comprises about 50% w / w 1,4-diaminobutane, and from 0% w / w to 50% w / w 2-fluoroadipic acid, the balance being adipic acid, such as from 12.5% w / w 2-fluoroadipic acid to 50% w / w 2-fluoroadipic acid.

[0147] In some embodiments, the polymer is obtainable by polymerization of a mixture of 2- fluoroadipic acid, and 1,4-diaminobutane.

[0148] In some embodiments, the polymer is obtainable by Rope polymerization or melt polymerization as defined herein.Polymer profiling

[0149] The polymers and polymer compositions of the present disclosure can be characterized according to the methods of Example 5 provided herein. In some embodiments, the polymers and polymer compositions of the present disclosure are PFAS replacement products that are produced in an environmentally friendly way with important properties for the materials industry but with environmentally more benign properties than PFAS counterparts. Unless otherwise stated, the characterization data defining the polymers and polymer compositions are obtained according to the methods of Example 5. The profiles obtained for the polymers are linked to their unique properties. In some embodiments, the polymer is characterized by one, more or all of the below characteristics, for example by having a FTIR spectrum as specified herein, and a melting point as specified herein. In some embodiments, the polymers referred to herein are NyFon64 or NyFon66 with different ratios of fluorinated vs. non-fluorinated oligomers and / or monomers.FTIR

[0150] In some embodiments, a polymer is provided having a FTIR spectrum as defined in Figure 3.

[0151] In some embodiments, a polymer is provided having a FTIR spectrum as defined in Figure 4.Melting point

[0152] In some embodiments, a polymer is provided having a melting point (Tmelt) of from 100 °C to300 °C, such as from 100 °C to 110 °C, such as from 110 °C to 120 °C, such as from 120 °C to 130 °C,such as from 130 °C to 140 °C, such as from 140 °C to 150 °C, such as from 150 °C to 160 °C, such as from 160 °C to 170 °C, such as from 170 °C to 180 °C, such as from 180 °C to 190 °C, such as from 190 °C to 200 °C, such as from 200 °C to 210 °C, such as from 210 °C to 220 °C, such as from 220 °C to 230 °C, such as from 230 °C to 240 °C, such as from 240 °C to 250 °C, such as from 250 °C to 260 °C, such as from 260 °C to 270 °C, such as from 270 °C to 280 °C, such as from 280 °C to 290 °C, such as from 290 °C to 300 °C.

[0153] In some embodiments, the polymer has a melting point of from 100 °C to 250 °C, such as from 140 to 170 °C, 220 °C, 235 °C, 240 °C or 244 °C.

[0154] In some embodiments, the polymer has a melting point of from 100 °C ± 5°C to 250 °C± 5°C, such as from 140 °C ± 5°C to 170 °C ± 5°C, 220 °C ± 5°C, 235 °C ± 5 °C, 240 °C ± 5°C or 244 °C ± 5°C.Maximum temperature

[0155] In some embodiments, a polymer is provided having a maximum temperature (Tmax) of from 250 °C to 400 °C, such as from 250 °C to 260 °C, such as from 260 °C to 270 °C, such as from 270 °C to 280 °C, such as from 280 °C to 290 °C, such as from 290 °C to 300 °C, such as from 300 °C to 310 °C, such as from 310 °C to 320 °C, such as from 320 °C to 330 °C, such as from 330 °C to 340 °C, such as from 340 °C to 350 °C, such as from 350 °C to 360 °C, such as from 360 °C to 370 °C, such as from 370 °C to 380 °C, such as from 380 °C to 390 °C, such as from 390 °C to 400 °C.

[0156] In some embodiments, a polymer is provided having a maximum temperature (Tmax) of 300 °C ± 5°C or 350 °C ± 5°C.Melting enthalpy

[0157] In some embodiments, a polymer is provided having a melting enthalpy of from 50 to 120 J / g, such as from 50 to 51 J / g, such as from 51 to 52 J / g, such as from 52 to 53 J / g, such as from 53 to 54 J / g, such as from 54 to 55 J / g, such as from 55 to 56 J / g, such as from 56 to 57 J / g, such as from 57 to 58 J / g, such as from 58 to 59 J / g, such as from 59 to 60 J / g, such as from 60 to 61 J / g, such as from 61 to 62 J / g, such as from 62 to 63 J / g, such as from 63 to 64 J / g, such as from 64 to 65 J / g, such as from 65 to 66 J / g, such as from 66 to 67 J / g, such as from 67 to 68 J / g, such as from 68 to 69 J / g, such as from 69 to 70 J / g, such as from 70 to 71 J / g, such as from 71 to 72 J / g, such as from 72 to 73 J / g, such as from 73 to 74 J / g, such as from 74 to 75 J / g, such as from 75 to 76 J / g, such as from 76 to 77 J / g, such as from 77 to 78 J / g, such as from 78 to 79 J / g, such as from 79 to 80 J / g, such as from 80 to 81 J / g, such as from 81 to 82 J / g, such as from 82 to 83 J / g, such as from 83 to 84 J / g, such as from 84 to 85 J / g, such as from 85 to 86 J / g, such as from 86 to 87 J / g, such as from 87 to 88 J / g, such as from 88 to 89 J / g, such as from 89 to 90 J / g, such as from 90 to 91 J / g, such as from 91 to 92 J / g, such as from 92 to 93 J / g, such as from 93 to 94 J / g, such as from 94 to 95 J / g, such as from 95 to 96 J / g, such as from 96 to 97 J / g, such as from 97 to 98 J / g, such as from 98 to 99 J / g, such as from 99 to100 J / g, such as from 100 to 101 J / g, such as from 101 to 102 J / g, such as from 102 to 103 J / g, such as from 103 to 104 J / g, such as from 104 to 105 J / g, such as from 105 to 106 J / g, such as from 106 to 107 J / g, such as from 107 to 108 J / g, such as from 108 to 109 J / g, such as from 109 to 110 J / g, such as from 110 to 111 J / g, such as from 111 to 112 J / g, such as from 112 to 113 J / g, such as from 113 to 114 J / g, such as from 114 to 115 J / g, such as from 115 to 116 J / g, such as from 116 to 117 J / g, such as from 117 to 118 J / g, such as from 118 to 119 J / g, such as from 119 to 120 J / g.

[0158] In some embodiments, the polymer has a melting enthalpy of 57.3 ± 5.0 J / g, 61.0 ± 5.0 J / g, 95.8 ± 5.0 J / g, 72.6 ± 5.0 J / g, 73.77 ± 5.0 J / g, 76.67 ± 5.0 J / g.

[0159] In some embodiments, the polymer has a melting enthalpy of 57.3 J / g, 61.0 J / g, 95.8 J / g, 72.6 5.0 J / g, 73.77 J / g, 76.67 J / g.TGA

[0160] In some embodiments, the polymer is characterized by TGA analysis with degradation temperature, estimated temperature for 4% weight loss, and / or estimated ash content%. A 4% weight loss is early enough to capture the beginning of significant thermal degradation but high enough to avoid noise from minor surface moisture or solvent residues. The ash content indicates the remaining mass at 900 °C. Estimated temperature for 4% weight loss was determined from weight at 1009C.

[0161] In some embodiments, the polymer has a degradation temperature determined by TGA of from 250 to 500 °C, such as from 250 °C to 260 °C, such as from 260 °C to 270 °C, such as from 270 °C to 280 °C, such as from 280 °C to 290 °C, such as from 290 °C to 300 °C, such as from 300 °C to 310 °C, such as from 310 °C to 320 °C, such as from 320 °C to 330 °C, such as from 330 °C to 340 °C, such as from 340 °C to 350 °C, such as from 350 °C to 360 °C, such as from 360 °C to 370 °C, such as from 370 °C to 380 °C, such as from 380 °C to 390 °C, such as from 390 °C to 400 °C, such as from 400 °C to 410 °C, such as from 410 °C to 420 °C, such as from 420 °C to 430 °C, such as from 430 °C to 440 °C, such as from 440 °C to 450 °C, such as from 450 °C to 460 °C, such as from 460 °C to 470 °C, such as from 470 °C to 480 °C, such as from 480 °C to 490 °C, such as from 490 °C to 500 °C.

[0162] In some embodiments, the polymer has a degradation temperature determined by TGA of 420 °C ± 3 °C, 402 °C ±3 °C, 290 °C ±3 °C, 378 °C ±3 °C, 356 °C ±3 °C, or 298 °C ±3 °C.

[0163] In some embodiments, the polymer has a degradation temperature determined by TGA of 420 °C, 402 °C, 290 °C, 378 °C, 356 °C, or 298 °C.

[0164] In some embodiments, the polymer is characterized by an estimated temperature for 4% weight loss of from 250 to 400 °C, such as from 250 °C to 255 °C, such as from 255 °C to 260 °C, such as from 260 °C to 265 °C, such as from 265 °C to 270 °C, such as from 270 °C to 275 °C, such as from 275 °C to 280 °C, such as from 280 °C to 285 °C, such as from 285 °C to 290 °C, such as from 290 °C to 295 °C, such as from 295 °C to 300 °C, such as from 300 °C to 305 °C, such as from 305 °C to 310 °C,such as from 310 °C to 315 °C, such as from 315 °C to 320 °C, such as from 320 °C to 325 °C, such as from 325 °C to 330 °C, such as from 330 °C to 335 °C, such as from 335 °C to 340 °C, such as from 340 °C to 345 °C, such as from 345 °C to 350 °C, such as from 350 °C to 355 °C, such as from 355 °C to 360 °C, such as from 360 °C to 365 °C, such as from 365 °C to 370 °C, such as from 370 °C to 375 °C, such as from 375 °C to 380 °C, such as from 380 °C to 385 °C, such as from 385 °C to 390 °C, such as from 390 °C to 395 °C, such as from 395 °C to 400 °C.

[0165] In some embodiments, the polymer is characterized by an estimated temperature for 4% weight loss of 358 °C ± 3 °C, 320 °C ± 3 °C, 303 °C ± 3 °C, 320 °C ± 3 °C, 315 °C ± 3 °C, or 285 °C ± 3 °C.

[0166] In some embodiments, the polymer is characterized by an estimated temperature for 4% weight loss of 358 °C, 320 °C, 303 °C, 320 °C, 315 °C, or 285 °C.

[0167] In some embodiments, the polymer is characterized by an estimated ash content (%) of from 0.5 to 4.5, such as from 0.5 to 0.6, such as from 0.6 to 0.7, such as from 0.7 to 0.8, such as from 0.8 to 0.9, such as from 0.9 to 1.0, such as from 1.0 to 1.1, such as from 1.1 to 1.2, such as from 1.2 to 1.3, such as from 1.3 to 1.4, such as from 1.4 to 1.5, such as from 1.5 to 1.6, such as from 1.6 to 1.7, such as from 1.7 to 1.8, such as from 1.8 to 1.9, such as from 1.9 to 2.0, such as from 2.0 to 2.1, such as from 2.1 to 2.2, such as from 2.2 to 2.3, such as from 2.3 to 2.4, such as from 2.4 to 2.5, such as from 2.5 to 2.6, such as from 2.6 to 2.7, such as from 2.7 to 2.8, such as from 2.8 to 2.9, such as from 2.9 to 3.0, such as from 3.0 to 3.1, such as from 3.1 to 3.2, such as from 3.2 to 3.3, such as from 3.3 to 3.4, such as from 3.4 to 3.5, such as from 3.5 to 3.6, such as from 3.6 to 3.7, such as from 3.7 to 3.8, such as from 3.8 to 3.9, such as from 3.9 to 4.0, such as from 4.0 to 4.1, such as from 4.1 to 4.2, such as from 4.2 to 4.3, such as from 4.3 to 4.4, such as from 4.4 to 4.5.

[0168] In some embodiments, the polymer is characterized by an estimated ash content (%) of 1.9±0.2, 2.8±0.2, 1.5±0.2, 3.5±0.2, or 2.8±0.2.

[0169] In some embodiments, the polymer is characterized by an estimated ash content (%) of 1.9, 2.8, 1.5, 3.5, or 2.8.Methods and processes

[0170] According to an embodiment, the invention relates to a method of producing the monomer and / or the polymer according to the invention. In some embodiments, the method or process disclosed herein provides a monomer as disclosed herein, an oligomer as disclosed herein, or a polymer as disclosed herein.Purifying a crude composition of2FMA

[0171] In some embodiments, a method is provided for purifying a crude composition of 2FMA asdemonstrated in the Examples, e.g. Example 4.

[0172] In some embodiments, a method for purifying a crude composition of 2-fluoromuconic acid is provided, comprising: a) obtaining a crude composition comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90%; and b) subjecting the composition to purification by filtration, solvent evaporation, precipitation, and / or recrystallization to provide a solid composition of 2-fluoromuconic acid having at least 90% purity.

[0173] In some embodiments, the purification is conducted essentially as set out in Example 4, Method A or Method B.

[0174] In some embodiments, the the method comprises: a) Subjecting the crude composition of 2-fluoromuconic acid to concentration in vacuo, b) Centrifuging the crude composition; c) Subjecting the crude composition to filtration after centrifugation to provide a filtrate; d) Adjusting the temperature of the filtrate obtained by filtration to a temperature of -20 °C to 20 °C; e) Adjusting the pH of the filtrate to from 0 to 3, such as from 0 to 1, such as from 1 to 2, such as from 2 to 3, for example 1, and allowing the the composition of 2-fluoromuconic acid to convert into a solid; and f) resuspending the solid in a polar protic solvent, such as ethanol and / or collecting the solid, optionally by filtration, to provide the solid composition of 2-fluoromuconic acid having at least 90% purity.

[0175] The temperature in step d) is optionally achieved using an ice-bath. In some embodiments, the temperature in step d) is from -20 °C to 20 °C, such as from -20 °C to -19 °C, such as from -19 °C to -18 °C, such as from -18 °C to -17 °C, such as from -17 °C to -16 °C, such as from -16 °C to -15 °C, such as from -15 °C to -14 °C, such as from -14 °C to -13 °C, such as from -13 °C to -12 °C, such as from - 12 °C to -11 °C, such as from -11 °C to -10 °C, such as from -10 °C to -9 °C, such as from -9 °C to -8 °C, such as from -8 °C to -7 °C, such as from -7 °C to -6 °C, such as from -6 °C to -5 °C, such as from -5 °C to -4 °C, such as from -4 °C to -3 °C, such as from -3 °C to -2 °C, such as from -2 °C to -1 °C, such as from - 1 °C to 0 °C, such as from 0 °C to 1 °C, such as from 1 °C to 2 °C, such as from 2 °C to 3 °C, such as from 3 °C to 4 °C, such as from 4 °C to 5 °C, such as from 5 °C to 6 °C, such as from 6 °C to 7 °C, such as from 7 °C to 8 °C, such as from 8 °C to 9 °C, such as from 9 °C to 10 °C, such as from 10 °C to 11 °C, such as from 11 °C to 12 °C, such as from 12 °C to 13 °C, such as from 13 °C to 14 °C, such as from 14 °C to 15 °C, such as from 15 °C to 16 °C, such as from 16 °C to 17 °C, such as from 17 °C to 18 °C, such asfrom 18 °C to 19 °C, such as from 19 °C to 20 °C.

[0176] In some embodiments, the polar protic solvent used in step f) is as defined herein, optionally wherein the polar protic solvent used in step f) is selected from the group consisting of: water, methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, acetic acid, formic acid, ethylene glycol, and ammonia.

[0177] In some embodiments, the method for purifying 2FMA further comprises the consecutive steps of: a) Subjecting the crude composition of 2-fluoromuconic acid to an apolar solvent, and optionally stirring the apolar solvent; b) Adjusting the temperature of the apolar solvent to above 30 °C, such as to a temperature from 31 °C to 60 °C; c) Adjusting the temperature of the apolar solvent to 30 °C or less, such as from 15 to 30 °C providing a solid in the apolar solvent; d) Separating the apolar solvent from the solid, optionally on a filter and optionally washing the solid one or more times using an apolar solvent; e) Optionally drying the solid in vacuo; f) Collecting the solid to provide the solid composition of 2-fluoromuconic acid having at least 90% purity.

[0178] In some embodiments, the temperature of the apolar solvent in step b) is adjusted to from 31 °C to 80 °C, such as from 31 °C to 33 °C, such as from 33 °C to 35 °C, such as from 35 °C to 37 °C, such as from 37 °C to 39 °C, such as from 39 °C to 41 °C, such as from 41 °C to 43 °C, such as from 43 °C to 45 °C, such as from 45 °C to 47 °C, such as from 47 °C to 49 °C, such as from 49 °C to 51 °C, such as from 51 °C to 53 °C, such as from 53 °C to 55 °C, such as from 55 °C to 57 °C, such as from 57 °C to 59 °C, such as from 59 °C to 61 °C, such as from 61 °C to 63 °C, such as from 63 °C to 65 °C, such as from 65 °C to 67 °C, such as from 67 °C to 69 °C, such as from 69 °C to 71 °C, such as from 71 °C to 73 °C, such as from 73 °C to 75 °C, such as from 75 °C to 77 °C, such as from 77 °C to 79 °C, such as from 79 °C to 80 °C.

[0179] In some embodiments, the apolar solvent in step b) is as defined herein, optionally wherein the apolar solvent in step b) is selected from the group consisting of: n-hexane, n-heptane, cyclohexane, benzene, toluene, diethyl ether, petroleum ether, and carbon tetrachloride (CCI4).

[0180] In some embodiments, the temperature of the apolar solvent in step c) is adjusted to from - 10 °C to 30 °C, such as from -10 °C to -8 °C, such as from -8 °C to -6 °C, such as from -6 °C to -4 °C, such as from -4 °C to -2 °C, such as from -2 °C to 0 °C, such as from 0 °C to 2 °C, such as from 2 °C to 4 °C, such as from 4 °C to 6 °C, such as from 6 °C to 8 °C, such as from 8 °C to 10 °C, such as from 10 °C to12 °C, such as from 12 °C to 14 °C, such as from 14 °C to 16 °C, such as from 16 °C to 18 °C, such as from 18 °C to 20 °C, such as from 20 °C to 22 °C, such as from 22 °C to 24 °C, such as from 24 °C to 26 °C, such as from 26 °C to 28 °C, such as from 28 °C to 30 °C. The temperature is selected such that the solid precipitates and balances yield with purity.

[0181] In some embodiments, the apolar solvent used in different steps is the same or different. In some embodiments, the apolar solvent used in step a) is the same as the apolar solvent used in step d). In some embodiments, the apolar solvent used in step a) is not the same as the apolar solvent used in step d). In some embodiments, the apolar solvent used in step a) is n-hexane, and the apolar solvent used in step d) is n-hexane.Reduction of 2FM A

[0182] In some embodiments, the present disclosure concerns a reduction of 2-fluoromuconic acid, such as 2-fluoro-cis,cis-muconic acid, to 2-fluoroadipic acid.

[0183] In some embodiments, a method of producing 2-fluoro adipic acid (2FAA) is provided, said method comprising: a) Providing a composition comprising 2-fluoromuconic acid (2FMA), such as 2-fluoro-cis,cis- muconic acid, in a solvent; b) Subjecting the composition comprising 2-fluoromuconic acid to reduction, such as by hydrogenation, providing 2FAA; and c) Thereby obtaining 2FAA.

[0184] According to an embodiment, the invention relates to a method of producing the 2FAA monomer according to the invention, wherein said method comprises the following steps: a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, wherein said reduction is performed in the presence of Ethyl Acetate, b. Obtaining the 2FAA monomer.

[0185] According to an embodiment, the invention relates to a method of producing a monomer and / or a polymer, wherein said method comprises the steps of a. Introducing fluorine into a monomer, and / or b. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, c. Obtaining the monomer and / or polymer.

[0186] The fluorine is introduced directly in the monomer, thus avoiding destruction of the polymer from chemical fluorination.

[0187] According to an embodiment, the invention relates to the method according to the invention, wherein said method comprises the steps:a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, b. Providing a specific amount of said 2FAA, and optionally providing a specific amount of AA, c. Adding a specific amount of HMDA to 2FAA in solvent to form 2FAA.HMDA salt, d. Adding water to said 2-FAA.HMDA salt and increasing the temperature to about 150- 240 °C, about 160 - 230 °C, about 170 - 220 °C, about 170 - 180 °C, about 180 - 210 °C, about 190 - 200 °C, about 195 - 220 °C, or preferably about 205 - 210 °C, e. Obtaining a polymer.

[0188] In some embodiments, the solvent used for the reduction is a polar solvent, such as a polar aprotic solvent or a polar protic solvent.

[0189] In some embodiments, the polar aprotic solvent is selected from the group consisting of: Ethyl acetate (EtOAc), acetone, acetonitrile (MeCN), tetrahydrofuran (THF), dichloromethane (DCM), 1,4- dioxane, dimethylformamide (DMF), and dimethyl sulfoxide (DMSO), for example wherein the polar aprotic solvent is ethyl acetate.

[0190] In some embodiments, a catalyst is added to the solvent to facilitate or increase the speed of the reduction.

[0191] In some embodiments, the catalyst is selected from the group consisting of: Palladium on carbon (Pd / C), platinum on carbon (Pt / C), platinum oxide (PtO2), Raney nickel, rhodium on carbon (Rh / C), ruthenium on carbon (Ru / C), Wilkinson's catalyst (RhCI(PPh3)3), Crabtree's catalyst, an iridium complexe (such as lr(cod)(PPh3)2), a cobalt catalyst (e.g., Co2(CO)8), nickel(ll) acetate with phosphine ligands, copper chromite; for example wherein the catalyst is palladium on carbon (Pd / C).

[0192] In some embodiments, the catalyst metal loading is least 1%, such as at least 2%, such as at least 3%, such as at least 4%, such as at least 5%, such as at least 6%, such as at least 7%, such as at least 8%, such as at least 9%, such as at least 10%, and for example up to 30%.

[0193] In some embodiments, from 2% to 50% catalyst w / w is added relative to 2FMA, such as from 2% to 4%, such as from 4% to 6%, such as from 6% to 8%, such as from 8% to 10%, such as from 10% to 12%, such as from 12% to 14%, such as from 14% to 16%, such as from 16% to 18%, such as from18% to 20%, such as from 20% to 22%, such as from 22% to 24%, such as from 24% to 26%, such as from 26% to 28%, such as from 28% to 30%, such as from 30% to 32%, such as from 32% to 34%, such as from 34% to 36%, such as from 36% to 38%, such as from 38% to 40%, such as from 40% to 42%, such as from 42% to 44%, such as from 44% to 46%, such as from 46% to 48%, such as from 48% to50%, for example 25%.

[0194] In some embodiments, the reduction is performed using hydrogenation and Pd / C, optionally from 10% to 30% Pd / C w / w relative to 2FMA of a 5% metal loading.

[0195] According to an embodiment, the invention relates to the method according to the invention, wherein said method comprises an additional step of melt polymerisation, wherein said step comprises increasing the temperature to about 205 - 210 °C.Formation of2FAA salt

[0196] In some embodiments, a method is provided for forming a 2-fluoroadipic acid (2FAA) salt comprising, a) Mixing 2FAA or a composition comprising 2FAA with a base, such as an amine base, to provide a mixture, optionally in an aqueous solution; b) Adding a polar protic solvent to the mixture, such an alcohol, for example isopropyl alcohol forming a precipitate; and c) Collecting the precipitate, optionally by filtration, as the 2FAA salt.

[0197] In some embodiments, the amine base is selected from the group consisting of: hexamethylenediamine (HMDA), and 1,4-diaminobutane.Producing polymers

[0198] In some embodiments, the present disclosure provides a method of producing a polymer as defined herein.

[0199] In some embodiments, a method is provided for preparing a polymer comprising a fluorinated polyamide by polymerization comprising: a) providing a composition comprising a 2-fluoroadipic acid (2FAA) salt; b) subjecting the 2-fluoroadipic acid (2FAA) salt to polymerization providing the polymer comprising the fluorinated polyamide.

[0200] In some embodiments, the polymerization is melt polymerization or Rope polymerization.

[0201] In some embodiments, melt polymerization comprises adding a solvent to the 2-fluoroadipic acid (2FAA) salt such as water, for example deionized water.

[0202] In some embodiments, the melt polymerization is performed in a dean stark apparatus.

[0203] In some embodiments, the temperature is first adjusted to a temperature from 150 °C to 200 °C, for example from 170 °C to 180 °C, allowing evaporation of water, and secondly to from 180 °C to 230 °C, such as from 205 °C to 210 °C for a period of time.

[0204] In some embodiments, the period of time is from 4 to 10 hours, such as from 4 to 5 hours, such as from 5 to 6 hours, such as from 6 to 7 hours, such as from 7 to 8 hours, such as from 8 to 9 hours, such as from 9 to 10 hours.

[0205] In some embodiments, the composition further comprises an adipic acid salt.

[0206] According to an embodiment, the invention relates to the method according to the invention, wherein said method is a method of producing fluorinated polyamide 66 and polyamide 46.

[0207] According to an embodiment, the invention relates to the method according to the invention, wherein the steps of said method are performed in said order.

[0208] According to an embodiment, the invention relates to the method according to the invention, wherein said conversion of 2FMA to 2FAA comprises a step of adding Ethyl Acetate.

[0209] According to an embodiment, the invention relates to the method according to the invention, wherein said conversion of 2FMA to 2FAA comprises a step of adding methanol and diethyl ether.

[0210] According to an embodiment, the invention relates to the method according to the invention, wherein said specific amount of AA, 2FAA and HMDA is selected among any of the following combinations: a. About 12.5 % (w / w) AA, about 37.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, b. About 25 % (w / w) AA, about 25 % (w / w) 2FAA and about 50 % (w / w) HMDA, c. About 37.5 % (w / w) AA, about 12.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, or d. About 50 % (w / w) 2FAA and about 50 % (w / w) HMDA.

[0211] According to an embodiment, the invention relates to the method according to the invention, wherein said method comprises a step of melt polymerization.Polyamide 66 and polyamide 46 is further described below:Polyamide 66:[-OC-(CH2)4-CO-NH-(CH2)6-NH-]nPolyamide 46:[-OC-(CH2)4-CO-NH-(CH2)4-NH-]n

[0212] In some embodiments, a process for preparing a polymer comprising a fluorinated polyamide from a crude composition of 2-fluoromuconic acid is provided, comprising theconsecutive steps of: a) purifying a crude composition of 2-fluoromuconic acid comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90% using a method as defined herein; b) producing 2-fluoro adipic acid (2FAA) using a method as defined herein; c) producing a 2-fluoroadipic acid (2FAA) salt using a method as defined herein, and d) producing the polymer comprising the fluorinated polyamide by melt polymerization using a method as defined herein.

[0213] In some embodiments, the polymerization is Rope polymerization.

[0214] In some embodiments, the Rope polymerization comprises a) converting 2-fluoroadipic acid into 2-fluorohexanedioyl dichloride, optionally by the addition of SOCl2to 2-fluoroadipic acid, and then b) further converting 2-fluorohexanedioyl dichloride into the fluorinated polymer, such as NyFon-66 or NyFon-46.

[0215] In some embodiments, the Rope polymerization is conducted at a temperature of from 20 °C to 100 °C, such as from 20 °C to 25 °C, such as from 25 °C to 30 °C, such as from 30 °C to 35 °C, such as from 35 °C to 40 °C, such as from 40 °C to 45 °C, such as from 45 °C to 50 °C, such as from 50 °C to 55 °C, such as from 55 °C to 60 °C, such as from 60 °C to 65 °C, such as from 65 °C to 70 °C, such as from 70 °C to 75 °C, such as from 75 °C to 80 °C, such as from 80 °C to 85 °C, such as from 85 °C to 90 °C, such as from 90 °C to 95 °C, such as from 95 °C to 100 °C, for example 75 °C.

[0216] In some embodiments, the Rope polymerization is conducted over the course of from 30 minutes to 24 hours, such as from 30 minutes to 1 hour, such as from 1 hourto 2 hours, such as from 2 hours to 3 hours, such as from 3 hours to 4 hours, such as from 4 hours to 5 hours, such as from 5 hours to 6 hours, such as from 6 hours to 7 hours, such as from 7 hours to 8 hours, such as from 8 hours to 9 hours, such as from 9 hours to 10 hours, such as from 10 hours to 11 hours, such as from 11 hours to 12 hours, such as from 12 hours to 13 hours, such as from 13 hours to 14 hours, such as from 14 hours to 15 hours, such as from 15 hours to 16 hours, such as from 16 hours to 17 hours, such as from 17 hours to 18 hours, such as from 18 hours to 19 hours, such as from 19 hours to 20 hours, such as from 20 hours to 21 hours, such as from 21 hours to 22 hours, such as from 22 hours to 23 hours, such as from 23 hours to 24 hours.

[0217] In some embodiments, the composition further comprises an adipic acid salt.

[0218] In some embodiments, the 2-fluorohexanedioyl dichloride is converted to the fluorinated polymer by mixing with a diamine in a mixture, such as 1 ,4-diaminobutane or hexamethylenediamine.

[0219] In some embodiments, the mixture is kept at from 0 °C to 40 °C during mixing, such as from 0 °C to 5 °C, such as from 5 °C to 10 °C, such as from 10 °C to 15 °C, such as from 15 °C to 20 °C, such as from 20 °C to 25 °C, such as from 25 °C to 30 °C, such as from 30 °C to 35 °C, such as from 35 °C to 40 °C.

[0220] In some embodiments, the fluorinated polymer is isolated by filtration and optionally dried.Combined process with a bacterial cell

[0221] Further embodiments of the present disclosure relates to combined processes where the monomer precursor, such as 2-fluoromuconic acid is derived from a bacterial cell, such as a bacterial cell defined herein, and then further purified using a method as defined herein, and subsequently converted into 2-fluoroadipic acid or the equivalent monomer obtained by reduction of monomer precursor, which in turn can be converted into a corresponding salt as defined herein followed by polymerization into a target polymer, for example melt polymerization or Rope polymerization. The bacterial cell and processes for providing 2-fluoromuconic acid is detailed in WO 2022 / 003144 the contents of which including its sequences are incorporated herein in its entirety for combination with the methods and processes disclosed herein.

[0222] In some embodiments, a process is provided for preparing a polymer comprising a fluorinated polyamide, comprising the consecutive steps of: a) Culturing a cell culture comprising a growth medium and a bacterial cell, such as a bacterial cell as defined herein, capable of producing 2-fluoromuconic acid (2FMA) in the presence of 3-fluorobenzoate or a salt thereof at conditions allowing the bacterial cell to produce a crude composition of 2-fluoromuconic acid; and b) purifying the crude composition of 2-fluoromuconic acid obtained in “step a” using a method as defined herein to provide a solid composition of 2-fluoromuconic acid having at least 90% purity; c) producing 2-fluoro adipic acid (2FAA) using a method as defined herein; d) producing a 2-fluoroadipic acid (2FAA) salt using a method as defined herein; and e) producing the polymer comprising the fluorinated polyamide by polymerization using a method as defined herein.

[0223] In some embodiments, the bacterial cell comprises a native or heterologous benzoate 1,2- dioxygenase (EC: 1.14.12.10), a benzoate-l,2-dihydrodiol dehydrogenase (EC: 1.3.1.25), and a first, and optionally a second, catechol 1,2-dioxygenase (EC: 1.13.11.1).

[0224] In some embodiments, the expression of the benzoate 1 ,2-dioxygenase is under thecontrol of a medium-strong constitutive promoter, whereby the benzoate 1 ,2-dioxygenase is constitutively overexpressed.

[0225] In some embodiments, the expression of the first catechol 1 ,2-dioxygenase is under the control of a first expression module comprising a first promoter and a first strong translational initiation sequence.

[0226] In some embodiments, the expression of the second catechol 1,2-dioxygenase is under the control of a second expression module comprising a second promoter and a second strong translational initiation sequence.

[0227] In some embodiments, the first and / or second promoter is a medium-to-weak constitutive promoter, such as P14b (SEQ ID NO: 49 of WO 2022 / 003144) or a variant thereof having at least 80% sequence identity thereto. In some embodiments, the sequence identity is at least 85%, such as at least 90%, such as at least 95%, such as at least 96%, such as at least 97%, such as at least 98%, such as at least 99%, such as at least 100% to SEQ ID NO: 49 of WO 2022 / 003144.

[0228] In some embodiments, the bacterial cell expresses BenABC as the benzoate 1,2-dioxygenase, BenD as the benzoate-l,2-dihydrodiol dehydrogenase, and CatA-l and / or CatA-ll as the first and second catechol 1,2-dioxygenases, respectively.

[0229] In some embodiments, the bacterial cell is a cell of the Pseudomonas, Burkholderia, Escherichia, Rhodococcus, Bacillus, or Vibrio genus, preferably a Pseudomonas putida cell, such as Pseudomonas putida KT2440.

[0230] In some embodiments, one or more of the genes encoding the benzoate 1,2-dioxygenase, benzoate-l,2-dihydrodiol dehydrogenase, and catechol l,2-dioxygenase(s) are integrated into the genome of the bacterial cell or expressed from a vector such as a plasmid.

[0231] In some embodiments, the bacterial cell is capable of producing at least 1 g / L of 2- fluoromuconic acid in the presence of 3-fluorobenzoate or a salt thereof.

[0232] In some embodiments, the bacterial cell comprises or expresses one or more or all of polynucleotides or polypeptides of SEQ ID NO: 1-84 of the present disclosure. In some embodiments, the bacterial cell comprises or expresses variants of one or more or all of polynucleotides or polypeptides of SEQ ID NO: 1-84 having at least 80% sequence identity to the polypeptides or polynucleotides, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 96%, such as at least 97%, such as at least 98%, such as at least 99%, such as at least 100%.

[0233] In some embodiments, the bacterial cell comprises or expresses the polynucleotides or polypeptides of SEQ ID NO: 1-84 of the present disclosure to produce 2-fluoromuconic acid.

[0234] In some embodiments, the benzoate 1 ,2-dioxygenase is a native or heterologous benzoate 1 ,2-dioxygenase. In some embodiments, the benzoate 1 ,2-dioxygenase is BenABC or afunctional variant thereof having at least 80%, such as at least 81%, such as at least 82%, such as at least 83%, such as at least 84% such as at least 85%, such as at least 86%, such as at least 87%, such as at least 88%, such as at least 89%, such as at least 90%, such as at least 91 %, such as at least 92%, such as at least 93%, such as at least 94%, such as at least 95%, such as at least 96%, such as at least 97%, such as at least 98%, such as at least 99% homology or identity thereto. The benzoate 1 ,2-dioxygenase is capable of converting 3-fluorobenzoate to 3- fluorocyclohexadiene-cis,cis-1 ,2-diol-1 -carboxylate. In some embodiments, the benzoate 1 ,2- dioxygenase comprises: i) BenA (SEQ ID NO: 1 ), ii) BenB (SEQ ID NO: 2), and iii) BenC (SEQ ID NO: 3) or functional variants thereof having at least 80%, such as at least 81 %, such as at least 82%, such as at least 83%, such as at least 84% such as at least 85%, such as at least 86%, such as at least 87%, such as at least 88%, such as at least 89%, such as at least 90%, such as at least 91 %, such as at least 92%, such as at least 93%, such as at least 94%, such as at least 95%, such as at least 96%, such as at least 97%, such as at least 98%, such as at least 99% homology or identity thereto.

[0235] In some embodiments, the benzoate 1 ,2-dioxygenase consists of BenA, BenB and BenC or functional variants thereof having at least 80% homology or identity thereto.

[0236] In some preferred embodiments, the benzoate 1 ,2-dioxygenase originates from the organism Pseudomonas putida.

[0237] In some embodiments, the benzoate 1 ,2-dioxygenase, for example a benzoate 1 ,2- dioxygenase consisting of BenA, BenB and BenC or functional variants thereof having at least 80% homologyoridentitythereto, is expressed underthe controlof a medium-strongconstitutive promoter, whereby the benzoate 1 ,2-dioxygenase is constitutively overexpressed. In some embodiments, the medium-strong constitutive promoter is Ptac (SEQ ID NO: 15) or a variant thereof having at least 80%, such as at least 81 %, such as at least 82%, such as at least 83%, such as at least 84% such as at least 85%, such as at least 86%, such as at least 87%, such as at least 88%, such as at least 89%, such as at least 90%, such as at least 91 %, such as at least 92%, such as at least 93%, such as at least 94%, such as at least 95%, such as at least 96%, such as at least 97%, such as at least 98%, such as at least 99% homology or identity thereto. In some embodiments, the native promoter of the benzoate 1 ,2-dioxygenase, such as the Pben promoter (SEQ ID NO: 13) or a variant thereof having at least 80%, such as at least 81 %, such as at least 82%, such as at least 83%, such as at least 84% such as at least 85%, such as at least 86%, suchas at least 87%, such as at least 88%, such as at least 89%, such as at least 90%, such as at least 91 %, such as at least 92%, such as at least 93%, such as at least 94%, such as at least 95%, such as at least 96%, such as at least 97%, such as at least 98%, such as at least 99% homology or identity thereto, has been replaced with a medium-strong constitutive promoter as described herein above.

[0238] In some embodiments, the medium-strong constitutive promoter is P14g (SEQ ID NO: 50) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is P14f (SEQ ID NO: 53) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is P14e (SEQ ID NO: 54) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is P14d (SEQ ID NO: 55) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is BG19 (SEQ ID NO: 56) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is BG34 (SEQ ID NO: 57) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is P14c (SEQ ID NO: 58) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is PEM7 (SEQ ID NO: 59) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is J23119 (SEQ ID NO: 60) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is J23101 (SEQ ID NO: 61 ) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is J23107 (SEQ ID NO: 62) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments,the medium-strong constitutive promoter is JEc3 (SEQ ID NO: 63) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is JEa3 (SEQ ID NO: 64) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is JE1611 (SEQ ID NO: 65) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto. In some embodiments, the medium-strong constitutive promoter is JEa2 (SEQ ID NO: 66) or a variant thereof having at least 80%, such as at least 85%, such as at least 90%, such as at least 95%, such as at least 99% homology or identity thereto.

[0239] In some embodiments, the translation initiation region of the gene encodingthe benzoate 1 ,2-dioxygenase, for example the benzoate 1 ,2-dioxygenase consisting of BenA, BenB and BenC or functional variants thereof having at least 80% homology or identity thereto, is unmodified. In some embodiments, the translation initiation region of the gene encoding the benzoate 1 ,2- dioxygenase subunit BenA described herein above is unmodified. In some embodiments, the translation initiation region consisting of the 34 base pairs upstream from the start codon of said gene comprises or consists of SEQ ID NO: 24 or a variant thereof having at least 80%, such as at least 81 %, such as at least 82%, such as at least 83%, such as at least 84% such as at least 85%, such as at least 86%, such as at least 87%, such as at least 88%, such as at least 89%, such as at least 90%, such as at least 91%, such as at least 92%, such as at least 93%, such as at least 94%, such as at least 95%, such as at least 96%, such as at least 97%, such as at least 98%, such as at least 99% homology or identity thereto.

[0240] In some embodiments, the bacterial cell expresses the benzoate 1 ,2-dioxygenase BenABC consisting of BenA (SEQ ID NO: 1), BenB (SEQ ID NO: 2) and BenC (SEQ ID NO: 2), the benzoate-1 ,2-dihydrodiol dehydrogenase BenD (SEQ ID NO: 7), and the catechol 1 ,2- dioxygenase CatA-l (SEQ ID NO: 9), or functional variants thereof as described herein.

[0241] In some embodiments, the bacterial cell expresses the benzoate 1 ,2-dioxygenase BenABC consisting of BenA (SEQ ID NO: 1), BenB (SEQ ID NO: 2) and BenC (SEQ ID NO: 2), the benzoate-1 ,2-dihydrodiol dehydrogenase BenD (SEQ ID NO: 7), and the catechol 1 ,2- dioxygenases CatA-l (SEQ ID NO: 9) and CatA-l I (SEQ ID NO: 11 ), or functional variants thereof as described herein.

[0242] In some embodiments, the bacterial cell expresses the benzoate 1 ,2-dioxygenase BenABC consisting of BenA (SEQ ID NO: 1), BenB (SEQ ID NO: 2) and BenC (SEQ ID NO: 2), thebenzoate-1 ,2-dihydrodiol dehydrogenase BenD (SEQ ID NO: 7), and the catechol 1 ,2- dioxygenase CatA-l (SEQ ID NO: 9), wherein BenABC is expressed under the control of the medium-strong constitutive promoter Ptac (SEQ ID NO: 15) and CatA-l is expressed under the control of the first expression module comprising or consisting of the medium-to-weak constitutive promoter P14b (SEQ ID NO: 49), and the first strong translational coupler BCD2 (SEQ ID NO: 22) or BCD10 (SEQ ID NO: 16), orfunctional variants thereof as described herein.

[0243] In some embodiments, the bacterial cell expresses the benzoate 1 ,2-dioxygenase BenABC consisting of BenA (SEQ ID NO: 1), BenB (SEQ ID NO: 2) and BenC (SEQ ID NO: 2), the benzoate-1 ,2-dihydrodiol dehydrogenase BenD (SEQ ID NO: 7), and the catechol 1 ,2- dioxygenase CatA-l (SEQ ID NO: 9), wherein BenABC is expressed under the control of the medium-strong constitutive promoter Ptac (SEQ ID NO: 15) and CatA-l is expressed under the control of the first expression module comprising or consisting of the first inducible promoter Pm variant ML1-17 (SEQ ID NO: 18), the associated activator protein is XylS (SEQ ID NO: 21), and the first strong translational coupler BCD2 (SEQ ID NO: 22) or BCD10 (SEQ ID NO: 16), or functional variants thereof as described herein.

[0244] In some embodiments, the bacterial cell expresses the benzoate 1 ,2-dioxygenase BenABC consisting of BenA (SEQ ID NO: 1), BenB (SEQ ID NO: 2) and BenC (SEQ ID NO: 2), the benzoate-1 ,2-dihydrodiol dehydrogenase BenD (SEQ ID NO: 7), and the catechol 1 ,2- dioxygenases CatA-l (SEQ ID NO: 9) and CatA-ll (SEQ ID NO: 11 ), wherein BenABC is expressed under the control of the medium-strong constitutive promoter Ptac (SEQ ID NO: 15) and CatA-l is expressed under the control of the first expression module comprising or consisting of the medium-to-weak constitutive promoter P14b (SEQ ID NO: 49), and the first strong translational coupler BCD2 (SEQ ID NO: 22) or BCD10 (SEQ ID NO: 16), and wherein CatA-ll is expressed under the control of the second expression module comprising or consisting of the medium-to-weak constitutive promoter P14b (SEQ ID NO: 49) and the second strong translational coupler BCD10 (SEQ ID NO: 16), or functional variants thereof as described herein.

[0245] In some embodiments, the bacterial cell expresses the benzoate 1 ,2-dioxygenase BenABC consisting of BenA (SEQ ID NO: 1), BenB (SEQ ID NO: 2) and BenC (SEQ ID NO: 2), the benzoate-1 ,2-dihydrodiol dehydrogenase BenD (SEQ ID NO: 7), and the catechol 1 ,2- dioxygenases CatA-l (SEQ ID NO: 9) and CatA-ll (SEQ ID NO: 11 ), wherein BenABC is expressed under the control of the medium-strong constitutive promoter Ptac (SEQ ID NO: 15) and CatA-l is expressed under the control of the first expression module comprising or consisting of the first inducible promoter Pm variant ML1-17 (SEQ ID NO: 18), the associated activator protein XylS (SEQ ID NO: 21), and the first strong translational coupler BCD2 (SEQ ID NO: 22) or BCD10 (SEQID NO: 16), and wherein CatA-ll is expressed under the control of the second expression module comprising or consisting of the inducible promoter Pm (SEQ ID NO: 15) and the second strong translational coupler BCD10 (SEQ ID NO: 16), or functional variants thereof as described herein.ExamplesMaterials and methods

[0246] Chemicals used in the examples herein, e.g. for buffers and substrates, are commercial products of at least reagent grade. All examples presented herein are working examples that have been performed, irrespective of whether they are described in the past or present tense.Example 1 - Method to produce 2FAA and fluorinated Nylon 66

[0247] Step 1 involves the reduction of 2FMA using Pd / C under hydrogen atmosphere to obtain 2FAA. In Step 2, 2FAA reacts with HMDA to form 2FAA.HMDA salt, which upon further reaction at high temperature (Step 3) in presence of water, yields fluorinated Nylon 66. Various fluorinated Nylon 66 variants can be produced as illustrated in figures 1, 2 and 3. a) Purification of 2-fluoromuconic acid (2-FMA) isolated from the biosynthesis

[0248] Production of 2FMA may be performed as described in W02022003144A1, which is incorporated by reference in its entirety.Step 1: Reduction of 2-fluoromuconic acid (2FMA) to 2-fluoroadipic acid (2FAA)Description:

[0249] The reduction of 2FMA using Pd / C under Hz atmosphere gives 2FAA.Procedure:

[0250] The reduction of 2FMA to 2FAA in ethyl acetate (EtOAc) led to the lowest amount of AA compared to other solvents such as methanol and diethyl ether. Reduction reaction in EtOAc solvent is performed on 100 mg scale using 25% (w / w) of 5% Pd / C using hydrogen gas balloon pressure. The reaction continued at 25-30 °C for 6 h. The mixture is then filtered through celite bed and washed with EtOAc. The combined organic layers are concentrated under vacuum to obtain a solid.Step 2: Salt formationDescription:

[0251] 1.00 equiv. of hexamethylenediamine (HMDA) reacts with 1.00 equiv. of AA (or 1.00 equiv. of2FAA) in solvent to form salt. The precipitated salt is filtered and washed with organic solvents.Procedure:

[0252] A multineck round bottom flask containing 50% aq. solution of 2FAA or a mixture of 2FAA / AA is charged with 80% aq. solution of HMDA at 5-10 °C. The temperature of the mixture is then slowly raised to 25-30 °C and stirred for 1 h. IPA (30 vol) is added to the reaction mixture to precipitate the salt. The precipitated salt is stirred for another 1 h and then filtered through a sintered funnel. The wet cake is then washed with IPA (2 vol) and MTBE (2 vol) and dried under vacuum at ambient temperature till a constant weight of compound is observed.Combinations of AA, 2FAA and HMDA salts:- 12.5 % (w / w) AA, 37.5 % (w / w) 2FAA and 50 % (w / w) HMDA- 25 % (w / w) AA, 25 % (w / w) 2FAA and 50 % (w / w) HMDA- 37.5 % (w / w) AA, 12.5 % (w / w) 2FAA and 50 % (w / w) HMDA- 50 % (w / w) 2 FAA + 50 % (w / w) HMDA

[0253] The maximum theoretical fluorine content is as follows:Example 1, Table 1Step 3 A: Melt PolymerizationDescription:

[0254] The salts previously obtained are then subjected to melt polymerization.Procedure:

[0255] A multineck round bottom flask equipped with nitrogen inlet, Dean Stark tube and reflux condenser is charged with salt and 5 vol of DI water under inert atmosphere. The temperature of the reaction mixture is then increased to 170-180 °C while collecting the water in the Dean Stark tube. The temperature of the reaction is then increased to 205-210 °C and maintained for 6-8 h. During thistime period the solid compound turns into liquid and forms solid again. After 6-8 h, the reaction mixture is cooled to 25-30 °C and the solid is taken out of the flask. The obtained solid is then crushed into powder using Mortar Pestle.5.8 gram scale:

[0256] To a multineck round bottom flask equipped with nitrogen inlet, Dean Stark tube and reflux condenser was charged with 5.80 g of the salt of Fluoroadipic acid [FAA] and Hexamethylene diamine [HMDA]) and 5 vol of DI water under inert atmosphere. The temperature of the reaction mixture was then increased to 170 - 180 °C while collecting the water in the Dean Stark tube. The temperature of the reaction was then increased to 205 - 210 °C and maintained for 6 - 8 h. During this time period the solid compound turns into liquid and formed solid again. After 6 - 8 h, the reaction mixture is cooled to 25 - 30 °C and solid was taken out of the flask. The obtained solid was then crushed into powder using Mortar Pestle. Isolated yield of the polymer was 5.20 g (91% yield).Step 3B: Rope polymerization

[0257] The salt obtained in prior steps was then subjected to Rope polymerization.-fluorohexanedioyl dichloride F-Nyfon-66

[0258] 1.00 g of 2-FAA (1.00 equivalent) was charged into a dry round-bottom flask. 3.00 equivalents of SOCI2was added to the flask. The reflux condenser was set up and the mixture heated to 75 °C. The reaction mixture was heated at 75 °C for 3 h and the reaction progress monitored using TLC and1H NMR.IPC analysis

[0259] A small aliquot of the reaction mixture in MeOH was quenched to convert to its methyl ester. Methanol was removed under reduced pressure. The sample was analyzed using1H NMR and TLC to confirm completion.Work-up

[0260] The reaction mixture was destilled under vacuum at 50-55 °C to remove excess SOCI2and volatile by-products. Azeotropic drying was performed on the crude product by co-distilling with toluene 3-4 times to remove residual moisture and SOCL. After final toluene removal a colourless liquid was obtained providing 1.10 g of 2-Fluorohexanedioyl dichloride. Product formation was confirmed by1H NMR analysis of derivatized samplePreparation of Aq. HMDA Solution

[0261] 1.00 equivalent of HMDA was weighted and dissolved in 40 mL of distilled water in a clean beaker.Preparation of Acid Chloride Solution

[0262] In a separate container, 1.00 equivalent of the acid chloride in 30 mL of DCM was dissolved.Complete dissolution by gentle stirring was ensured.Addition and Reaction

[0263] While maintaining the HMDA aqueous solution at 25 °C, the acid chloride solution was added dropwise into the HMDA solutionObservation of Product Formation

[0264] A white solid began to form at the interface of the two immiscible layers.Product Isolation

[0265] Once the addition is complete, collect the white solid from the interface of two layers by filtration under vacuum and wash with water. The filtered solid was dried thoroughly in a vacuum oven or at room temperature until completely free from solvents.Example 2 - Production of polyamide 46Method A

[0266] Polyamide 46 is to be produced by the method described in example 1. To produce polyamide 46, 2FAA is to be combined with 1,4-diaminobutane.Method B

[0267] In Step 1, 2FAA was reacted with 1,4-diaminobutane (DAB) to form 2FAA.DAB salt, which upon further reaction at high temperature (Step 3) in presence of water, yielded fluorinated Nylon 46.

[0268] Various fluorinated Nylon 46 variants can be produced as illustrated in figures 1, 2 and 3.Purification of 2-fluoromuconic acid (2-FMA) isolated from the biosynthesis

[0269] Production of 2FMA may be performed as described in W02022003144A1, which is incorporated by reference in its entirety.Reduction of 2-fluoromuconic acid (2FMA) to 2-fluoroadipic acid (2FAA)

[0270] Production of 2FAA may be performed as described in Example 1 Stepl.Step 1: Salt formationDescription:

[0271] 1.00 equiv. of 1,4-diaminobutane (DAB) reacts with 1.00 equiv. of AA (or 1.00 equiv. of 2FAA)in solvent to form salt. The precipitated salt is filtered and washed with organic solvents.Procedure:

[0272] A multineck round bottom flask containing 50% aq. solution of 2FAA or a mixture of 2FAA / AA was charged with 80% aq. solution of DAB at 5-10 °C. The temperature of the mixture was then slowly raised to 25-30 °C and stirred for 1 h. IPA (30 vol) was added to the reaction mixture to precipitate the salt. The precipitated salt was stirred for another 1 h and then filtered through a sintered funnel. The wet cake was then washed with IPA (2 vol) and MTBE (2 vol) and dried under vacuum at ambient temperature till a constant weight of compound was observed.

[0273] Combinations of AA, 2FAA and DAB salts:12.5 % (w / w) AA, 37.5 % (w / w) 2FAA and 50 % (w / w) DAB25 % (w / w) AA, 25 % (w / w) 2FAA and 50 % (w / w) DAB37.5 % (w / w) AA, 12.5 % (w / w) 2FAA and 50 % (w / w) DAB50 % (w / w) 2FAA + 50 % (w / w) DAB

[0274] The maximum theoretical fluorine content was as follows:Example 2, Table 1Step 2: Melt PolymerizationDescription:

[0275] The salts previously obtained were then subjected to melt polymerization.Procedure:

[0276] A multineck round bottom flask equipped with nitrogen inlet, Dean Stark tube and reflux condenser was charged with salt and 5 vol of DI water under inert atmosphere. The temperature of the reaction mixture was then increased to 170-180 °C while collecting the water in the Dean Stark tube. The temperature of the reaction was then increased to 205-210 °C and maintained for 6-8 h.During this time-period, the solid compound turned into liquid and formed solid again. After 6-8 h, the reaction mixture was cooled to 25-30 °C and the solid was taken out of the flask. The obtained solid was then crushed into powder using Mortar Pestle.Example 3 - Production of polyamide 66

[0277] To a multineck round bottom flask, was charged with 5 g of 2-FMA followed by Hexane (10 vol). The mixture was stirred at 25 - 30 °C for 1 h. The temperature of the reaction mixture was increased to 40 °C and stirred for additional 1 h. After 1 h, the mixture was cooled to 25- 30 °C and filtered. The wet cake was washed with n-Hexane (2 vol x 2) and dried under vacuum at ambient temperature till a constant weight of the compound was achieved. 4.20 g (84% recovery) of 2-FMA was recovered.

[0278] 2-FMA on reduction using Pd / C under H2 atmosphere gives 2-FAA as shown below:

[0279] The reaction was carried out in MeOH, diethyl ether, and in ethyl acetate using otherwise essentially similar conditions.

[0280] Reduction reaction in EtOAc solvent was performed on 100 mg scale using 25% w / w of 5% Pd / C using hydrogen gas balloon pressure. The reaction continued at 25 - 30 °C for 6 h. TLC analysis showed complete conversion of 2-FMA. The mixture was then filtered through celite bed, washed with EtOAc. The combined organic layers were concentrated under vacuum to obtained a solid.

[0281] Salt formation was relatively simple reaction, in which, 1.00 equiv. of Hexamethylene diamine (HMDA) reacts with 1.00 equiv. of AA (or 1.00 equiv. of FAA) in solvent to form salt. The precipitated salt was filtered and washed with organic solvents.

[0282] Various combination of AA, 2-FAA and HMDA salts were prepared as captured in Example 3, table 1 below.Example 3, Table 1. The different combination of 2-FAA, AA and HMDA were then taken forward to prepare the salt.General Procedure for the Salt preparation

[0283] To a multineck round bottom flask containing 50% aq. solution of 2-FAA or AA or a mixture of 2-FAA / AA was charged with 80% aq. Solution of HMDA at 5 - 10 °C. The temperature of the mixture was then slowly raised to 25 - 30 °C and stirred for 1 h. IPA (30 vol) was added to the reaction mixture to precipitate the salt. The precipitated salt was stirred for another 1 h and then filtered through sintered funnel. The wet cake was then washed with IPA (2 vol) and MTBE (2 vol) and dried under vacuum at ambient temperature till a constant weigh of compound was observed.

[0284] The salt obtained from Example 3, Table 1 were then subjected to melt polymerization using the below general procedure.

[0285] To a multineck round bottom flask equipped with nitrogen inlet, Dean Stark tube and reflux condenser was charged with 5.80 g of salt (Entry 1 in Example 3, Table 1) and 5 vol of DI water under inert atmosphere. The temperature of the reaction mixture was then increased to 170 - 180 °C while collecting the water in the Dean Stark tube. The temperature of the reaction was then increased to 205 - 210 °C and maintained for 6 - 8 h. During this time period the solid compound turns into liquid and formed solid again. After 6 - 8 h, the reaction mixture is cooled to 25 - 30 °C and solid was taken out of the flask. The obtained solid was then crushed into powder using Mortar Pestle. Isolated yield of the polymer was 5.20 g (91% yield)

[0286] The details of each polymer synthesized are captured in Example 3, Table 2.Example 3, Table 2Conclusions

[0287] n-Hexane was identified as a good solvent for purifying 2-FMA, yielding a high recovery of the compound.

[0288] In Step 1, reduction reaction conducted in MeOH resulted in higher levels of AA formation, while the reaction in Diethyl ether was notably sluggish.

[0289] The reduction of 2-FMA to 2-FAA demonstrated successful outcomes when conducted in Ethyl Acetate, although a minor amount (4 - 5%) of AA was observed in synthesized 2-FAA

[0290] Different combinations of 2-FAA, AA and HMDA salt were prepared using various proportions of 2-FAA and AA

[0291] A Melt polymerization approach was employed to successfully prepare the target polymer.Example 4 - Recovery of 2-fluoromuconic acid (2FMA) and conversion into polyamidesMethod ARecovery

[0292] 2FMA was recovered using filtration, water evaporation, acid pH precipitation and washing with ethanol to provide 2FMA in >99% purity.

[0293] The final broth comprising 2FMA obtained as described in W02022003144 was concentrated around 10 times through rotary evaporation. After concentration, the broth was centrifuged and filtered through a Buchner funnel with Whatman® filter paper, grade 1 (11 pm pore size). Subsequently, the permeate was filtered through a 0.2 pm Fisherbrand™ disposable filter unit and immediately after, filtered twice through a sintered funnel with activated charcoal (5g / L). The flowthrough was chilled on ice and the pH brought down to 1.0 with concentrated H2SO4. The permeate was stored at 4 °C to promote crystallization and filtered through a Buchner funnel with Whatman® filter paper, grade 1 (11 pm pore size). Solids were subsequently dried in a vacuum oven until dryness. The dry solids were resuspended in ethanol, filtered through a Fisherbrand™ disposablefilter unit (0.2 pm pore size). Ethanol was then evaporated on a rotary evaporator and the wet solids further dried in a vacuum oven. The final product presented as an off-white color after the first stage of drying. The purity was >99% purity as determined by HPLC and confirmed by NMR.Salt formation

[0294] 2-FMA was subsequently converted to 2-fluoroadipic acid (2-FAA), then to a salt, and subsequently polymerized to two polyamides depending on the salt's cation.

[0295] 2-FMA was reduced to 2-FAA using Pd / C under a hydrogen atmosphere in Ethyl acetate (EtOAc). This reaction was performed on a 9.00 g scale at 25-30°C for 6 hours, the product was isolated and analyzed by 1H NMR. The challenge was to minimize the formation of Adipic acid (AA) due to potential fluorine displacement.

[0296] Salt formation was subsequently achieved by reacting Tetramethylene diamine (DAB) with AA or FAA. The reaction mixture was stirred at 5-10°C and then slowly raised to 25-30°C. Subsequently, isopropyl alcohol (IPA) is added to precipitate the salt. The precipitated salt was collected by filtration, washed with organic solvents, and dried under vacuum.Polymerization

[0297] Finally, the obtained salt was subjected to melt polymerization. The salt was combined with deionized (DI) water in a multineck round bottom flask under an inert atmosphere. The temperature was first increased to 170-180°C, then to 205-210°C, and maintained for 6-8 hours. The solid compound turns liquid and then solidifies again. The mixture was then cooled to approximately 25-30 °C and the solid was crushed into powder, yielding the polymer with an 80% yield.Method B

[0298] The scheme for the synthesis of F-Nylon 4,6 is captured below.F-Nylon-4,6Example 4, Scheme 1. Synthesis of F-Nylon 4,6.

[0299] Step 1 involves the reduction of 2-FMA using Pd / C under hydrogen atmosphere to obtain 2-FAA. In Step 2, 2-FAA is reacted with DAB to form the 2-fluoro adipic acid (2-FAA)-DAB salt, which upon further reaction at high temperature (Step 3) in presence of water yields F-Nylon 4,6.Purification

[0300] The starting material for the purification was a composition of 2-FMA produced by biosynthesis as specified in W02022003144.

[0301] A multineck round bottom flask was charged with 44 g of 2-FMA obtained by biosynthesis followed by n-Hexane (10 vol). The mixture was stirred at 25 - 30 °C for 1 h. The temperature of the reaction mixture was subsequently increased to 40 °C and stirred for additional 1 h. After 1 h, the mixture was cooled to 25- 30 °C and filtered. The wet cake was washed with n-Hexane (2 vol x 2) and dried under vacuum at ambient temperature till a constant weight of the compound was achieved.1H NMR analysis data of the resulting compound showed the disappearance of prior impurity peaks at both aliphatic and aromatic regions indicating pure 2-FMA.Reduction

[0302] 2-FMA on reduction using Pd / C under H2 atmosphere gives 2-FAA as shown in Example 4,Scheme 2.2-FMA 2-FAAExample 4, Scheme 2. Reduction of 2-FMA to 2-FAA.Example 4, Table 1. Step 1 Reaction Conditions

[0303] Reduction in EtOAc solvent was performed on 9.00 g scale using ~50% wet 5% Pd / C using hydrogen gas balloon pressure. The reaction continued at 25 - 30 °C for 6 h. TLC analysis showed complete conversion of 2-FMA. The mixture was then filtered through a Celite bed and washed with EtOAc. The combined organic layers were concentrated under vacuum to provide a 2-FAA (8.50 g) as a solid.Salt formation

[0304] l.OO equiv. of Tetramethylene diamine (DAB) was reacted with 1.00 equiv. of AAor l.OO equiv. of FAA in solvent to form the respective salt. The precipitated salt was collected by filteration and washed with isopropyl alcohol. Various combinations of AA, 2-FAA and DAB salts were prepared as captured in Example 4, Table 2 below.Example 4, Table 2. Preparation of salts.

[0305] A multineck round bottom flask containing 50% aq. solution of 2-FAA or AA or a mixture of 2-FAA / AA was charged with a 80% aq. solution of DAB at 5 - 10 °C. The temperature of the mixture was then slowly raised to 25 - 30 °C and stirred for 1 h. Isopropyl alcohol (IPA) (30 vol.) was added to the reaction mixture precipitating the salt. The suspension of precipitated salt was stirred for another 1 h and then subjected to a sintered funnel. The wet cake was then washed with IPA (2 vol.) and methyl tert-butyl ether (MTBE) (2 vol.) and subsequently dried under vacuum at ambient temperature till a constant weigh of compound was observed.Polymerisation

[0306] The salts obtained from Table 2 were then subjected to melt polymerization using below general procedure.

[0307] A multineck round bottom flask equipped with nitrogen inlet, Dean Stark tube and reflux condenser was charged with 2.57 g of salt (Entry 1 in Table 2) and 5 vol. of deionized (DI) water under inert atmosphere. The temperature of the reaction mixture was then increased to 170 - 180 °C while collecting the water in the Dean Stark tube. The temperature of the reaction mixture was then increased to 205 - 210 °C and maintained for 6 - 8 h. During this time period the solid compound turned liquid and then solidified again. After 6 - 8 h, the reaction mixture was cooled to 25 - 30 °C after which the solid was collected and crushed into powder using a Mortar Pestle to provide the polymer with an isolated yield of 80% (2.10 g). The results of the polymerization reactions can be found in Example 4, Table 3.Example 4, Table 3. Po ymer synthesis.Conclusions

[0308] Apolar solvents, such as n-hexane were highly efficient for purification of 2-FMA. Reduction of 2-FMA to 2-FAA proceeded successfully in polar aprotic solvents, such as ethyl acetate with low amounts of byproduct formation. Lastly, a melt polymerization approach yielded the desired polymers from the adipic acid compounds in high yields.Example 5 - Analysis of polymer compositions

[0309] The present example outlines representative methods for characterizing the polymers and / or polymer compositions of the present disclosure.Thermal characterization and profiling

[0310] The present example demonstrates a representive method for thermal characterization and FTIR spectroscopy to obtain a profile specific to a particular polymer and / or polymer composition.

[0311] Thermal characterization and FTIR spectroscopy were performed for NyFon66 and NyFon46 at three different fluorine content. The samples were named as follows:Example 5, Table 1Infrared spectroscopyFTIR using ATR iZIO-method.

[0312] To perform the ATR iZIO method for obtaining an infrared spectrum, a FTIR spectrometer with the iZIO ATR accessory was first calibrated, and the crystal surface was cleaned. A small amount of the polymer containing sample was then placed directly onto the diamond crystal plate of the iZIO module, ensuring full contact with the surface. The built-in pressure arm was used to apply uniform pressure, securing optimal contact between the sample and the crystal. The sample compartment was closed, and a background scan was performed to record a reference spectrum. Subsequently, the sample scan was initiated. The resulting spectrum was analyzed to identify characteristic absorptionpeaks as shown in Figures 3 and 4. Finally, the sample was removed, and the crystal was cleaned with an appropriate solvent or wipe to prepare for the next measurement.Differential Scanning Calorimetry (DSC) was performed according to DS / EN ISO 11357-2:2020 and DS / EN ISO 11357-3:2018, under the following conditions: o Heating from -50°C to 300°C in N2 and scanning at 10 K / min. o Purity gas of nitrogen: 99.5% o Half-step-height method

[0313] The thermal behaviors of the polymers during DSC analysis are summarized in Table 1. All values are rounded, and the unit is °C.• Tg = Glass transition temperature• Tmelt = Melting point• Tmax = Maximum temperature• J / g = melting enthalpy (how much energy it takes to melt the polymer)Example 5, Table 2Thermogravimetric Analysis (TGA) according to DS / EN ISO 11358-1:2022, was performed under the following conditions: o Heating from 50°C to 60°C in N2 scanning at 1 K / min. o Heating from 60°C to 600°C in N2 scanning at 20 K / min. o Cooling from 600°C to 200°C in N2 scanning at -100 K / min. o Heating from 200°C to 900°C in 02 scanning at 30 K / min o Purity gas of nitrogen: 99.5%

[0314] The thermogravimetric analyses of the different polymers and estimation of 4% weight loss and the ash content (remaining mass at 900 °C) are shown in the below Table. Estimated temperature for 4% weight loss was determined from weight at 100 °C.Example 5, Table 3Solubility characterizationFormic acid

[0315] Studying the solubility of polymers, such as Nyfon 66, in formic acid under sonication at 45-50 °C.Procedure:Sample charging:

[0316] 50 mg of Nyfon 66 was weighted in a clean and dry test tube.

[0317] The test tube was placed in a sonicator water bath, and the temperature maintained between 47-50 °C throughout the experiment.

[0318] Formic acid was added dropwise to the Nyfon 66 sample under continued sonication.

[0319] The Nyfon 66 gradually dissolved in formic acid during sonication. A clear solution was formed, indicating complete dissolution.

[0320] To remaining volume of formic acid left in the funnel after the complete dissolution of the compound was measured.Result:1) 50 mg of Nyfon 66 (from Rope polymerization technique) dissolved in 0.6 mL of formic acid.2) 50 mg of Nyfon 66 (from Melt polymerization technique) did not dissolved completely (~80% dissolution observed) in 2.0 mL of formic acid m-Cresol

[0321] 50 mg of Nyfon 66 (prepared using the rope technique) was transferred into a clean, dry test tube suitable for sonication.

[0322] The test tube was placed in a sonicator water bath and the temperature maintaind between 47-50 °C throughout the experiment.

[0323] 1.0 mL of m-Cresol was added into an addition funnel. Further, m-Cresol was added dropwise to the test tube under continuous sonication. The dissolution was monitored visually during the addition. A clear solution was observed, indicating complete dissolution, and the addition of m-Cresol was stopped.

[0324] 1 mL of m-Cresol was consumed to dissolve 50 mg of Nyfon 66.Embodiments i. A monomer comprising 2-fluoro adipic acid (2FAA), having the following structure:ii. A polymer comprising: a. 1,4-diaminobutane (DAB) or hexamethylenediamine (HMDA), b. at least one monomer according to embodiment 1, and c. optionally, adipic acid (AA). ill. A polymer comprising fluorinated polyamide 66, wherein said fluorinated polyamide 66 comprises at least one monomer, at least two or at least three monomers according to embodiment 1. iv. A polymer comprising fluorinated polyamide 46, wherein said fluorinated polyamide 46 comprises at least one monomer, at least two or at least three monomers according to embodiment 1. v. The polymer according to embodiment 2-3, wherein said polymer consists of fluorinated polyamide 66 or polyamide 46, and preferably wherein said polymer comprises the monomer according to embodiment 1. vi. The polymer according to any of the previous embodiments, wherein said polymer has a fluorine content of about 0.1 - 10 % F (w / w), 1 -10 % F (w / w), about 2-8 % F (w / w), about 3- 7 % F (w / w), or about 4 -6 % F (w / w). vii. The polymer according to any of the previous embodiments, wherein said polymer is selected among : i) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; and vi) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n [-OC-(CH2)4-CO- NH-(CH2)6-NH-]O.viii. The polymer according to any of the previous embodiments, wherein said polymer is selected among: i) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n[-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m [-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m [-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; and vi) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n [-OC-(CH2)4-CO-NH-(CH2)4-NH-]O. ix. The polymer according to any of the previous embodiments, wherein said polymer comprises any of the following structures:x. The polymer according to any of the previous embodiments, wherein said polymer comprises the any of the following structures:xi. The polymer according to any of the previous embodiments, wherein said polymer comprises any of the following structures:xii. The polymer according to any of the previous embodiments, wherein said polymer comprises the any of the following structures:xiii. The polymer according to any of the previous embodiments, wherein said polymer comprises a non-fluorinated monomer. xiv. The polymer according to any of the previous embodiments, wherein said polymer does not comprise CF? or CF3 bonds. xv. A method of producing the monomer and / or the polymer according to any of the previous embodiments. xvi. A method of producing the 2FAA monomer according to any of the proceeding embodiments, wherein said method comprises the following steps: a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, wherein said reduction is performed in the presence of Ethyl Acetate, b. Obtaining the 2FAA monomer. xvii. A method of producing a monomer and / or a polymer, wherein said method comprises the steps of a. Introducing fluorine into a monomer, and / or b. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, c. Obtaining the monomer and / or polymer. xviii. The method according to any of the previous embodiments, wherein said method comprises the steps: a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, b. Providing a specific amount of said 2FAA, and optionally providing a specific amount of AA, c. Adding a specific amount of HMDA to 2FAA in solvent to form 2FAA.HMDA salt,d. Adding water to said 2FAA.HMDA salt and increasing the temperature to about 150- 240 °C, about 160 - 230 °C, about 170 - 220 °C, about 170 - 180 °C, about 180 - 210 °C, about 190 - 200 °C, about 195 - 220 °C, or preferably about 205 - 210 °C, e. Obtaining a polymer. xix. The method according to any of the previous embodiments, wherein said method is a method of producing fluorinated polyamide 66. xx. The method according to any of the previous embodiments, wherein the steps of said method are performed in said order. xxi. The method according to any of the previous embodiments, wherein said conversion of 2FMA to 2FAA comprises a step of adding Ethyl Acetate. xxii. The method according to any of the previous embodiments, wherein said specific amount of AA, 2FAA and HMDA is selected among any of the following combinations: a. About 12.5 % (w / w) AA, about 37.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, b. About 25 % (w / w) AA, about 25 % (w / w) 2FAA and about 50 % (w / w) HMDA, c. About 37.5 % (w / w) AA, about 12.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, or d. About 50 % (w / w) 2FAA and about 50 % (w / w) HMDA. xxiii. The method according to any of the previous embodiments, wherein said method comprises a step of melt polymerization.ItemsThe present disclosure further provides the following embodiments and items: a) A monomer comprising 2-fluoro adipic acid (2FAA), having the following structure:b) A polymer comprising: a. 1,4-diaminobutane (DAB) or hexamethylenediamine (HMDA), b. at least one monomer according to item 1, and c. optionally, adipic acid (AA). c) A polymer comprising fluorinated polyamide 66, wherein said fluorinated polyamide 66 comprises at least one monomer according to item 1.d) A polymer comprising fluorinated polyamide 46, wherein said fluorinated polyamide 46 comprises at least one monomer according to item 1. e) The polymer according to any of the previous items, wherein said polymer has a fluorine content of about 0.1 - 10 % F (w / w), 1 -10 % F (w / w), about 2-8 % F (w / w), about 3 - 7 % F (w / w), or about 4 -6 % F (w / w). f) The polymer according to any of the previous items, wherein said polymer is selected among : i) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; and vi) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n [-OC-(CH2)4-CO- NH-(CH2)6-NH-]O. g) The polymer according to any of the previous items, wherein said polymer is selected among: i) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n[-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m[-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m[-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; and vi) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m[-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n [-OC-(CH2)4-CO- NH-(CH2)4-NH-]O. h) The polymer according to any of the previous items, wherein said polymer comprises any of the following structures:i) The polymer according to any of the previous items, wherein said polymer comprises the any of the following structures:j) The polymer according to any of the previous items, wherein said polymer comprises any of the following structures:k) The polymer according to any of the previous items, wherein said polymer comprises the any of the following structures:I) A method of producing a monomer and / or a polymer according to any of the previous items, wherein said method comprises the steps of a. Introducing fluorine into a monomer, and / or b. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, c. Obtaining the monomer and / or polymer. m) The method according to any of the previous items, wherein said method comprises the steps: a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, b. Providing a specific amount of said 2FAA, and optionally providing a specific amount of AA, c. Adding a specific amount of HMDA to 2FAA in solvent to form 2-FAA.HMDA salt,d. Adding water to said 2-FAA.HMDA salt and increasing the temperature to about 150- 240 °C, about 160 - 230 °C, about 170 - 220 °C, about 170 - 180 °C, about 180 - 210 °C, about 190 - 200 °C, about 195 - 220 °C, or preferably about 205 - 210 °C, e. Obtaining a polymer. n) The method according to any of the previous items, wherein said specific amount of AA, 2FAA and HMDA is selected among any of the following combinations: a. About 12.5 % (w / w) AA, about 37.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, b. About 25 % (w / w) AA, about 25 % (w / w) 2FAA and about 50 % (w / w) HMDA, c. About 37.5 % (w / w) AA, about 12.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, or d. About 50 % (w / w) 2FAA and about 50 % (w / w) HMDA.ReferencesWirth et al, Combinatorial pathway balancing provides biosynthetic access to 2-fluoro-cis,cismuconate in engineered Pseudomonas putida, Chem Catalysis 1, 1234-1259, November 18, 2021Solomun, Tihomir, et al. "Surface modification of polyamides by direct fluorination." e-Polymers 4.1 (2004): 008.Mahmud, M. B., et al. "Hydrophilic-to-hydrophobic conversion of polyamide 6-based mat via polyvinylidene fluoride nanofiber integration with enhanced oil-water separation." Materials Today Sustainability 24 (2023): 100559.Hayes, L. J., and D. D. Dixon. "Direct fluorination of polyamide." Journal of Fluorine Chemistry 10.1 (1977): 17-26.Lee, Muncheul, et al. "Chemical modification of nylon 6 and polyester fabrics by ozone-gas treatment." Journal of Applied Polymer Science 100.2 (2006): 1344-1348.Jordanov, Igor, et al. "Enzymatic modification of polyamide for improving the conductivity of waterbased multilayer nanocoatings." ACS omega 4.7 (2019): 12028-12035.Mark, James E (ed.), Polymer Data Handbook: Second Edition (New York, NY, 2009; online edn, Oxford Academic, 31 Oct. 2023), https: / / doi.org / 10.1093 / oso / 9780195181012.001.0001, accessed 27 May 2024.Shakiba, Mohamadreza, et al. "Nylon— A material introduction and overview for biomedical applications." Polymers for advanced technologies 32.9 (2021): 3368-3383.Rios, Jeovanna, et al. "A critical review on the progress and challenges to a more sustainable, cost competitive synthesis of adipic acid." Green Chemistry 23.9 (2021): 3172-3190.Van de Vyver, Stijn, and Yuriy Roman-Leshkov. "Emerging catalytic processes for the production of adipic acid." Catalysis Science & Technology 3.6 (2013): 1465-1479.

Claims

1. Claims1. A monomer comprising 2-fluoro adipic acid (2FAA), having the following structure:

2. A polymer comprising: a. 1,4-diaminobutane (DAB) or hexamethylenediamine (HMDA), b. at least one monomer according to claim 1, and c. optionally, adipic acid (AA).

3. A polymer comprising fluorinated polyamide 66, wherein said fluorinated polyamide 66 comprises at least one monomer, at least two or at least three monomers according to claim 1.

4. A polymer comprising fluorinated polyamide 46, wherein said fluorinated polyamide 46 comprises at least one monomer, at least two or at least three monomers according to claim 1.

5. The polymer according to claim 2-4, wherein said polymer consists of fluorinated polyamide 66 or polyamide 46, and preferably wherein said polymer comprises the monomer according to claim 1.

6. The polymer according to any of the previous claims, wherein said polymer has a fluorine content of about 0.1 - 10 % F (w / w), 1 -10 % F (w / w), about 2-8 % F (w / w), about 3 - 7 % F (w / w), or about 4 -6 % F (w / w).

7. The polymer according to any of the previous claims, wherein said polymer is selected among : i) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]n [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]m[-OC-(CH2)4-CO-NH-(CH2)6-NH-]n; andvi) [-OC-(CH2)3-CFH-CO-NH-(CH2)6-NH-]m[-OC-CFH-(CH2)3-CO-NH-(CH2)6-NH-]n [-OC-(CH2)4-CO- NH-(CH2)6-NH-]O; wherein m, n, and o are independently any integer.

8. The polymer according to any of the previous claims, wherein said polymer is selected among: i) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n; ii) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n; iii) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]n[-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m; iv) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m [-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; v) [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]m [-OC-(CH2)4-CO-NH-(CH2)4-NH-]n; and vi) [-OC-(CH2)3-CFH-CO-NH-(CH2)4-NH-]m [-OC-CFH-(CH2)3-CO-NH-(CH2)4-NH-]n [-OC-(CH2)4-CO- NH-(CH2)4-NH-]O; wherein m, n, and o are independently any integer.

9. The polymer according to any of the previous claims, wherein said polymer comprises any of the following structures:wherein m, n, and o are independently any integer10. The polymer according to any of the previous claims, wherein said polymer comprises the any of the following structures:wherein m, n, and o are independently any integer.

11. The polymer according to any of the previous claims, wherein said polymer comprises any ofwherein m, n, and o are independently any integer.

12. The polymer according to any of the previous claims, wherein said polymer comprises the any of the following structures:wherein m, n, and o are independently any integer.

13. The polymer according to any of the previous claims, wherein said polymer comprises a nonfluorinated monomer.

14. The polymer according to any of the previous claims, wherein said polymer does not comprise CF? or CF3 groups.

15. The polymer according to any of the preceding claims, wherein the polymer comprises a mixture of at least one fluorinated monomer and at least one non-fluorinated monomer.

16. The polymer of claim 15, wherein the at least one non-fluorinated monomer is adipic acid.

17. The polymer of any of claims 15-16, wherein the at least one fluorinated monomer is 2- fluoroadipic acid.

18. The polymer according to any of the preceding claims, wherein the polymer comprises fluorinated polyamide 46 or fluorinated polyamide 66.

19. The polymer according to any of the preceding claims, wherein the polymer comprises from 0.1% w / w fluorine to 10% w / w fluorine, such as from 0.1% to 0.5%, such as from 0.5% to 1.0%, such as from 1.0% to 1.5%, such as from 1.5% to 2.0%, such as from 2.0% to 2.5%, such as from 2.5% to 3.0%, such as from 3.0% to 3.5%, such as from 3.5% to 4.0%, such as from4.0% to 4.5%, such as from 4.5% to 5.0%, such as from 5.0% to 5.5%, such as from 5.5% to6.0%, such as from 6.0% to 6.5%, such as from 6.5% to 7.0%, such as from 7.0% to 7.5%, such as from 7.5% to 8.0%, such as from 8.0% to 8.5%, such as from 8.5% to 9.0%, such as from9.0% to 9.5%, such as from 9.5% to 10.0%.

20. The polymer according to any of the preceding claims, wherein the polymer comprises from about 12.5 % to about 50 % w / w 2-fluoroadipic acid, about 50% w / w hexamethylenediamine or 1,4-diaminobutane, the balance being adipic acid.

21. The polymer according to any of the preceding claims, wherein the polymer comprises: a. about 37.5 % (w / w) adipic acid, about 12.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 2.1% w / w; b. about 25 % (w / w) adipic acid, about 25 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 4.1% w / w; c. about 12.5 % (w / w) adipic acid, about 37.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 6.0% w / w; and / or d. about 50 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) hexamethylenediamine and a maximum theoretical fluorine content of 7.8% w / w.

22. The polymer according to any of claims 1-19, wherein the polymer comprises: a. about 37.5 % (w / w) adipic acid, about 12.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4-diaminobutane and a maximum theoretical fluorine content of 2.3% w / w; b. about 25 % (w / w) adipic acid, about 25 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4-diaminobutane and a maximum theoretical fluorine content of 4.5% w / w; c. about 12.5 % (w / w) adipic acid, about 37.5 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4-diaminobutane and a maximum theoretical fluorine content of 6.7% w / w; and / or d. about 50 % (w / w) 2-fluoroadipic acid and about 50 % (w / w) 1,4-diaminobutane and a maximum theoretical fluorine content of 8.7% w / w.

23. The polymer according to any of the preceding claims, wherein the polymer is characterized by having a melting point (Tmelt) of from 100 °C to 300 °C.

24. The polymer according to any of the preceding claims, wherein the polymer is characterized by having a maximum temperature (Tmax) of from 250 °C to 400 °C.

25. The polymer according to any of the preceding claims, wherein the polymer is characterized by a degradation temperature determined by thermogravimetric analysis (TGA) of from 250 to 500 °C.

26. A method for purifying a crude composition of 2-fluoromuconic acid, comprising: obtaining a crude composition comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90%; and subjecting the composition to purification by filtration, solvent evaporation, precipitation, and / or recrystallization to provide a solid composition of 2- fluoromuconic acid having at least 90% purity.

27. The method of claim 26, wherein the method comprises: a. Subjecting the crude composition of 2-fluoromuconic acid to concentration in vacuo, b. Centrifuging the crude composition; c. Subjecting the crude composition to filtration after centrifugation to provide a filtrate; d. Adjusting the temperature of the filtrate obtained by filtration to a temperature of - 20 °C to 20 °C; e. Adjusting the pH of the filtrate to from 0 to 3, such as from 0 to 1, such as from 1 to 2, such as from 2 to 3, for example 1, and allowing the the composition of 2- fluoromuconic acid to convert into a solid; and f. resuspending the solid in a polar protic solvent, such as ethanol and / or collecting the solid, optionally by filtration, to provide the solid composition of 2-fluoromuconic acid having at least 90% purity.

28. The method of claim 27, wherein the method further comprises the consecutive steps of: a. Subjecting the crude composition of 2-fluoromuconic acid to an apolar solvent, and optionally stirring the apolar solvent;b. Adjusting the temperature of the apolar solvent to above 30 °C, such as to a temperature from 31 °C to 60 °C; c. Adjusting the temperature of the apolar solvent to 30 °C or less, such as from 15 to 30 °C providing a solid in the apolar solvent; d. Separating the apolar solvent from the solid, optionally on a filter and optionally washing the solid one or more times using an apolar solvent; e. Optionally drying the solid in vacuo; f. Collecting the solid to provide the solid composition of 2-fluoromuconic acid having at least 90% purity.

29. A method of producing the monomer and / or the polymer according to any of the previous claims.

30. A method of producing 2-fluoro adipic acid (2FAA), said method comprising: a. Providing a composition comprising 2-fluoromuconic acid (2FMA), such as 2-fluoro- cis,cis-muconic acid, in a solvent; b. Subjecting the composition comprising 2-fluoromuconic acid to reduction, such as by hydrogenation, providing 2FAA; and c. Thereby obtaining 2FAA.

31. A method of producing the 2FAA monomer according to any of the proceeding claims, wherein said method comprises the following steps: a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, wherein said reduction is performed in the presence of Ethyl Acetate, b. Obtaining the 2FAA monomer.

32. A method of producing a monomer and / or a polymer, wherein said method comprises the steps of a. Introducing fluorine into a monomer, and / or b. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, c. Obtaining the monomer and / or polymer.

33. The method according to any of the previous claims, wherein said method comprises the steps:a. Reduction of 2FMA to 2FAA, such as via a hydrogenation reaction, b. Providing a specific amount of said 2FAA, and optionally providing a specific amount of AA, c. Adding a specific amount of HMDA to 2FAA in solvent to form 2FAA.HMDA salt, d. Adding water to said 2FAA.HMDA salt and increasing the temperature to about 150- 240 °C, about 160 - 230 °C, about 170 - 220 °C, about 170 - 180 °C, about 180 - 210 °C, about 190 - 200 °C, about 195 - 220 °C, or preferably about 205 - 210 °C, e. Obtaining a polymer.

34. The method according to any of claims 30-33, wherein the solvent is a polar solvent.

35. The method according to claim 34, wherein the polar solvent is a polar aprotic solvent or a polar protic solvent.

36. The method according to claim 35, wherein the polar aprotic solvent is selected from the group consisting of: Ethyl acetate (EtOAc), acetone, acetonitrile (MeCN), tetrahydrofuran (THF), dichloromethane (DCM), 1,4-dioxane, dimethylformamide (DMF), and dimethyl sulfoxide (DMSO), for example wherein the polar aprotic solvent is ethyl acetate.

37. The method according to any of claims 30-36, wherein a catalyst is added to the solvent.

38. The method according to claim 37, wherein the catalyst is selected from the group consisting of: Palladium on carbon (Pd / C), platinum on carbon (Pt / C), platinum oxide (PtO2), Raney nickel, rhodium on carbon (Rh / C), ruthenium on carbon (Ru / C), Wilkinson's catalyst (RhCI(PPh3)3), Crabtree's catalyst, an iridium complexe (such as lr(cod)(PPh3)2), a cobalt catalyst (e.g., Co2(CO)8), nickel(ll) acetate with phosphine ligands, copper chromite; for example wherein the catalyst is palladium on carbon (Pd / C).

39. The method according to any of claims 37-38, wherein the catalyst metal loading is least 1%, such as at least 2%, such as at least 3%, such as at least 4%, such as at least 5%, such as at least 6%, such as at least 7%, such as at least 8%, such as at least 9%, such as at least 10%, and for example up to 30%.

40. The method according to any of claims 37-39, wherein from 2% to 50% catalyst w / w is added relative to 2FMA, such as from 2% to 4%, such as from 4% to 6%, such as from 6% to 8%, such as from 8% to 10%, such as from 10% to 12%, such as from 12% to 14%, such as from 14% to 16%, such as from 16% to 18%, such as from 18% to 20%, such as from 20% to 22%, such as from 22% to 24%, such as from 24% to 26%, such as from 26% to 28%, such as from 28% to 30%, such as from 30% to 32%, such as from 32% to 34%, such as from 34% to 36%, such as from 36% to 38%, such as from 38% to 40%, such as from 40% to 42%, such as from 42% to 44%, such as from 44% to 46%, such as from 46% to 48%, such as from 48% to 50%, for example 25%.

41. The method according to any of claims 30-40, wherein the reduction is performed using hydrogenation and Pd / C, optionally from 10% to 30% Pd / C w / w relative to 2FMA of a 5% metal loading.

42. A method of forming a 2-fluoroadipic acid (2FAA) salt comprising, a. Mixing 2FAA or a composition comprising 2FAA with a base, such as an amine base, to provide a mixture, optionally in an aqueous solution; b. Adding a polar protic solvent to the mixture, such an alcohol, for example isopropyl alcohol forming a precipitate; and c. Collecting the precipitate, optionally by filtration, as the 2FAA salt.

43. The method of claim 42, wherein the amine base is selected from the group consisting of: hexamethylenediamine (HMDA), and 1,4-diaminobutane.

44. The method according to any of the previous claims, wherein said method is a method of producing fluorinated polyamide 66 or fluorinated polyamide 46.

45. The method according to any of the previous claims, wherein the steps of said method are performed in said order.

46. The method according to any of the previous claims, wherein said conversion of 2FM A to 2FAA comprises a step of adding Ethyl Acetate.

47. The method according to any of the previous claims, wherein said specific amount of AA, 2FAA and HMDA is selected among any of the following combinations: a. About 12.5 % (w / w) AA, about 37.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, b. About 25 % (w / w) AA, about 25 % (w / w) 2FAA and about 50 % (w / w) HMDA, about 37.5 % (w / w) AA, about 12.5 % (w / w) 2FAA and about 50 % (w / w) HMDA, orAbout 50 % (w / w) 2FAA and about 50 % (w / w) HMDA.

48. The method according to any of the previous claims, wherein said method comprises a step of polymerization, such as melt polymerization or Rope polymerization.

49. A method for preparing a polymer comprising a fluorinated polyamide by polymerization comprising: a. providing a composition comprising a 2-fluoroadipic acid (2FAA) salt; and b. subjecting the 2-fluoroadipic acid (2FAA) salt to polymerization providing the polymer comprising the fluorinated polyamide.

50. The method of claim 49, wherein the polymerization is melt polymerization or Rope polymerization.

51. The method of claim 50, wherein melt polymerization comprises adding a solvent to the 2- fluoroadipic acid (2FAA) salt such as water, for example deionized water.

52. The method of any of claims 49-51, wherein the melt polymerization is performed in a dean stark apparatus.

53. The method of claim 52, wherein the temperature is first adjusted to a temperature from 150 °C to 200 °C, for example from 170 °C to 180 °C, allowing evaporation of water, and secondly to from 180 °C to 230 °C, such as from 205 °C to 210 °C for a period of time.

54. The method of claim 52, wherein the period of time is from 4 to 10 hours, such as from 4 to 5 hours, such as from 5 to 6 hours, such as from 6 to 7 hours, such as from 7 to 8 hours, such as from 8 to 9 hours, such as from 9 to 10 hours.

55. The method method of any of claims 49-54, wherein the polymerization is Ropepolymerization.

56. The method of claim 55, wherein the Rope polymerization comprises a) converting 2- fluoroadipic acid into 2-fluorohexanedioyl dichloride, optionally by the addition of SOCL to 2- fluoroadipic acid, and then b) further converting 2-fluorohexanedioyl dichloride into the fluorinated polymer, such as NyFon-66 or NyFon-46.

57. The method of claim 56, wherein the Rope polymerization is conducted at a temperature of from 20 °C to 100 °C, such as from 20 °C to 25 °C, such as from 25 °C to 30 °C, such as from 30 °C to 35 °C, such as from 35 °C to 40 °C, such as from 40 °C to 45 °C, such as from 45 °C to 50 °C, such as from 50 °C to 55 °C, such as from 55 °C to 60 °C, such as from 60 °C to 65 °C, such as from 65 °C to 70 °C, such as from 70 °C to 75 °C, such as from 75 °C to 80 °C, such as from 80 °C to 85 °C, such as from 85 °C to 90 °C, such as from 90 °C to 95 °C, such as from 95 °C to 100 °C, for example 75 °C.

58. The method of any of claims 56-57, wherein the Rope polymerization is conducted over the course of from 30 minutes to 24 hours, such as from 30 minutes to 1 hour, such as from 1 hour to 2 hours, such as from 2 hours to 3 hours, such as from 3 hours to 4 hours, such as from 4 hours to 5 hours, such as from 5 hours to 6 hours, such as from 6 hours to 7 hours, such as from 7 hours to 8 hours, such as from 8 hours to 9 hours, such as from 9 hours to 10 hours, such as from 10 hours to 11 hours, such as from 11 hours to 12 hours, such as from 12 hours to 13 hours, such as from 13 hours to 14 hours, such as from 14 hours to 15 hours, such as from 15 hours to 16 hours, such as from 16 hours to 17 hours, such as from 17 hours to 18 hours, such as from 18 hours to 19 hours, such as from 19 hours to 20 hours, such as from 20 hours to 21 hours, such as from 21 hours to 22 hours, such as from 22 hours to 23 hours, such as from 23 hours to 24 hours.

59. The method of any of claims 49-58, wherein the composition further comprises an adipic acid salt.

60. The method of any of claims 49-59, wherein the 2-fluorohexanedioyl dichloride is converted to the fluorinated polymer by mixing with a diamine in a mixture, such as 1,4-diaminobutane or hexamethylenediamine.

61. The method of claim 60, wherein the mixture is kept at from 0 °C to 40 °C during mixing, such as from 0 °C to 5 °C, such as from 5 °C to 10 °C, such as from 10 °C to 15 °C, such as from 15 °C to 20 °C, such as from 20 °C to 25 °C, such as from 25 °C to 30 °C, such as from 30 °C to 35 °C, such as from 35 °C to 40 °C.

62. The method of any of claims 56-61, wherein the fluorinated polymer is isolated by filtration and optionally dried.

63. A process for preparing a polymer comprising a fluorinated polyamide from a crude composition of 2-fluoromuconic acid, comprising the consecutive steps of: a. purifying a crude composition of 2-fluoromuconic acid comprising 2-fluoromuconic acid and one or more impurities, wherein the purity of 2-fluoromuconic acid is less than 90% using a method as defined in any one of claims 26-28; b. producing 2-fluoroadipic acid (2FAA) using a method as defined in any one of claims 30-41; c. producing a 2-fluoroadipic acid (2FAA) salt using a method as defined in any one of claims 42-43, and d. producing the polymer comprising the fluorinated polyamide by polymerization using a method as defined in any one of claims 49-62.

64. A process for preparing a polymer comprising a fluorinated polyamide from 3- fluorobenzoate, comprising the consecutive steps of: a. Culturing a cell culture comprising a growth medium and a bacterial cell capable of producing 2-fluoromuconic acid (2FMA) in the presence of 3-fluorobenzoate or a salt thereof at conditions allowing the bacterial cell to produce a crude composition of 2- fluoromuconic acid; and b. purifying the crude composition of 2-fluoromuconic acid obtained in "step a" using a method as defined in any one of claims 26-28 to provide a solid composition of 2- fluoromuconic acid having at least 90% purity; c. producing 2-fluoro adipic acid (2FAA) using a method as defined in any one of claims 30-41; d. producing a 2-fluoroadipic acid (2FAA) salt using a method as defined in any one of claims 42-43, ande. producing the polymer comprising the fluorinated polyamide by polymerization using a method as defined in any one of claims 49-62.

65. The process of claim 64, wherein the bacterial cell comprises a native or heterologous benzoate 1,2-dioxygenase (EC: 1.14.12.10), a benzoate-l,2-dihydrodiol dehydrogenase (EC: 1.3.1.25), and a first, and optionally a second, catechol 1,2-dioxygenase (EC: 1.13.11.1).

66. The process of any of claims 64-65, wherein the expression of the benzoate 1,2-dioxygenase is under the control of a medium-strong constitutive promoter, whereby the benzoate 1,2- dioxygenase is constitutively overexpressed.

67. The process of any of claims 64-66, wherein the expression of the first catechol 1,2- dioxygenase is under the control of a first expression module comprising a first promoter and a first strong translational initiation sequence.

68. The process of any of claims 64-67, wherein the expression of the second catechol 1,2- dioxygenase is under the control of a second expression module comprising a second promoter and a second strong translational initiation sequence.

69. The process of any of claims 64-68, wherein the first and / or second promoter is a medium- to-weak constitutive promoter, such as P14b or a variant thereof having at least 80% sequence identity thereto.

70. The process of any of claims 64-69, wherein the first and / or second promoter is an inducible promoter, optionally coupled with a sequence encoding an associated activator protein.

71. The process of any of claims 64-70, wherein the bacterial cell expresses BenABC as the benzoate 1,2-dioxygenase, BenD as the benzoate-l,2-dihydrodiol dehydrogenase, and CatA-l and / or CatA-l I as the first and second catechol 1,2-dioxygenases, respectively.

72. The process of any of claims 64-71, wherein the bacterial cell is a cell of the Pseudomonas, Burkholderia, Escherichia, Rhodococcus, Bacillus, or Vibrio genus, preferably a Pseudomonas putida cell, such as Pseudomonas putida KT2440.

73. The process of any of claims 64-72, wherein one or more of the genes encoding the benzoate 1,2-dioxygenase, benzoate-l,2-dihydrodiol dehydrogenase, and catechol 1,2- dioxygenase(s) are integrated into the genome of the bacterial cell or expressed from a vector such as a plasmid.

74. The process of any of claims 64-73, wherein the bacterial cell is capable of producing at least 1 g / L of 2-fluoromuconic acid in the presence of 3-fluorobenzoate or a salt thereof.

75. The process of any of claims 64-74, further comprising one or more elements selected from: a. culturing the cell culture in a nutrient medium; b. culturing the cell culture under aerobic or anaerobic conditions c. culturing the cell culture under agitation; d. culturing the cell culture at a temperature of between 25 to 50 °C; e. culturing the cell culture at a pH of between 3-9; and f. culturing the cell culture for between 10 hours to 30 days.

76. A polymer obtainable by the method of any of claims 26-62, or by the process of any of claims 63-75.

77. The polymer of claim 76, wherein the method comprises polymerization of a mixture of adipic acid, 2-fluoroadipic acid, and hexamethylenediamine.

78. The polymer of claim 77, wherein the polymerization comprises about 50% w / w hexamethylenediamine, and from 0% w / w to 50% w / w 2-fluoroadipic acid, the balance being adipic acid, such as from 12.5% w / w 2-fluoroadipic acid to 50% w / w 2-fluoroadipic acid.

79. The polymer of claim 76, wherein the method comprises polymerization of a mixture of 2- fluoroadipic acid, and hexamethylenediamine.

80. The polymer of claim 76, wherein the method comprises polymerization of a mixture of adipic acid, 2-fluoroadipic acid, and 1,4-diaminobutane.

81. The polymer of claim 80, the polymerization comprises about 50% w / w 1,4-diaminobutane, and from 0% w / w to 50% w / w 2-fluoroadipic acid, the balance being adipic acid, such as from 12.5% w / w 2-fluoroadipic acid to 50% w / w 2-fluoroadipic acid.

82. The polymer of claim 76, wherein the method comprises polymerization of a mixture of 2- fluoroadipic acid, and 1,4-diaminobutane.

83. The polymer of any of claims 76-82, wherein the polymerization is Rope polymerization or melt polymerization.

Images