Solvolysis and oxidation of mixed plastic streams

Abstract

Disclosed herein are methods of recycling mixed plastics streams without the need to sort or pre-treat the mixed plastic streams prior to treatment. The methods generally comprise solvolysis of a first fraction of the mixed plastics, and oxidation of a second fraction of the mixed plastics in the presence of oxygen, where the solvolysis deconstructs the first fraction to a first compound, and the oxidation deconstructs the second fraction to a second compound. Methods of separating both the first and second compounds are also provided.

Description

SOLVOLYSIS AND OXIDATION OF MIXED PLASTIC STREAMSCROSS-REFERENCE TO RELATED APPLICATIONSThis application claims priority from U.S. Provisional Patent Application No. 63 / 642,959 filed on May 6, 2024, the contents of which are incorporated herein by reference in their entirety.CONTRACTUAL ORIGINThis invention was made with government support under Contract No. DE-AC36-08GO28308 awarded by the Department of Energy. The government has certain rights in the invention.FIELD OF THE INVENTIONThe present invention relates generally to the deconstruction of end-of-life mixed plastic streams for the recovery and reuse of the deconstruction products in a single process, without the need for pre-sorting and separating the different plastics.BACKGROUNDAs of 2018, the EPA reports that 35.7 million tons of plastic waste is generated annually accounting for 12.2 percent of municipal solid waste generation. Only between 4 and 5% of this material is recycled, with the majority going to either landfill or incineration. Thus, there is an urgent need for practical and potentially industrially viable methods for the deconstruction of mixed polymer streams with minimal need for pre-sorting steps allowing for the recovery of high value chemicals of utility to the chemical industry.SUMMARYThe present disclosure provides methods of deconstructing plastics into one or more components of the plastics. In various aspects, the process comprises solvolysis of a first fraction of plastics, and oxidizing a second fraction of the plastics in the presence of oxygen, wherein the solvolysis deconstructs the first fraction to a first compound, and the oxidizing deconstructs the second fraction to a second compound. The present disclosure therefore describes a chemical recycling process that uses solvolysis and oxidation to deconstruct and upcycle plastic polymer streams with minimal pre-sorting steps, using, in some embodiments, acetic acid as the solvent for solvolysis. In one aspect, the disclosed process is capable of effectively deconstructing a single type of plastic. In other aspects, the disclosed process is capable of effectively deconstructing two or more chemically distinct forms of plastics at the same time, using the same solvolysis and oxidation process. In such aspects, the plastics may comprise one, two, three, four, five, six, seven, or more chemically distinct forms of plastic that can all be deconstructed at the same time.An advantage provided by the disclosed methods is that two or more chemically distinct forms of plastic may be deconstructed at the same time, without the need for any sorting or pretreatment of the plastics. In that regard, commercial plastic recycling centers may utilize the disclosed methods in order to efficiently, and in some embodiments completely, deconstruct a plurality of plastics all at the same time, efficiently completing recycling tasks without the need to sort or pretreat the plastics at all. While in some embodiments it may be desirable to pretreat the plastics, for example to remove non-plastic components such as labels, food products, and / or the like, this is not required by the disclosed methods. It is anticipated that the disclosed methods will dramatically increase the efficiency of commercial recycling facilities.In various aspects, the present disclosure provides methods of deconstructing mixed plastic streams, without the need for any pre-treatment and / or sorting of the mixed plastic streams. In embodiments, the method includes solvolysis of a first fraction of the mixed plastics, and oxidation of a second fraction of the mixed plastics in the presence of oxygen, where the solvolysis deconstructs the first fraction to a first compound, and the oxidation deconstructs the second fraction to a second compound.In some embodiments, the solvolysis is performed before the oxidation, whereas in other embodiments the oxidation is performed before the solvolysis. In yet other embodiments, the solvolysis and the oxidation are performed simultaneously. In some embodiments, the solvolysis and / or the oxidation are performed in a reactor. In other embodiments, the solvolysis and the oxidation are performed in the same reactor. Consistent with the foregoing, in some embodiments the mixed plastics comprise at least two different types of plastic. The at least two different types of plastics are selected from two or more of a polyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, or polyethylene terephthalate.In one aspect, the solvolysis occurs by contacting the first fraction with a first liquid. In embodiments, the first liquid is selected from acetic acid, water, or both acetic acid and water. In further embodiments, the first liquid further comprises hydrochloric acid, sulfuric acid, or both hydrochloric and sulfuric acid. In some embodiments, the solvolysis is performed at a temperature selected from 22 °C - 300 °C or 120 °C - 280 °C. In further embodiments, the solvolysis is performed for 0.5 hours - 4 hours. In some embodiments, the first fraction comprises chemical bonds capable of being broken by the first liquid.In some embodiments, the polyamide is selected from the group consisting of polycaprolactam (Nylon 6), poly[imino(l,6-dioxohexamethylene)iminohexamethylene] (Nylon 6,6), and bothNylon 6 and Nylon 6,6. In other embodiments, the polyamide is selected from Nylon 11, Nylon 12, or both Nylon 11 and Nylon 12. In some embodiments, the polycarbonate is 1,2-diacyl-sn- glycero-3 -phosphocholine. In some embodiments, the first fraction comprises a polyolefin selected from the group consisting of polyethylene, polypropylene, and both polyethylene and polypropylene.In some embodiments, the first compound is soluble in the first liquid. In further embodiments, the disclosed methods further include separating the first compound from the first liquid. The first compound may be separated from the first liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof. In another aspect, the second fraction is present as a solid. In embodiments, the oxidation occurs by contacting the second fraction with a second liquid. In further embodiments, the second liquid comprises water, acetic acid, para-xylene, or any combination thereof. In some embodiments, the second liquid further comprises benzoic acid. In some embodiments, the first liquid can also comprise benzoic acid. In further embodiments, the second liquid further comprises an initiator. The initiator may be N-hydroxypthalimide (NHPI), NaBr, or both NHPI and NaBr. In still further embodiments, the second liquid further comprises a catalyst. The catalyst may be a transition metal, for example cobalt, manganese, or both cobalt and manganese.In some embodiments, the oxidation is performed at a temperature selected from 22 °C - 300 °C or 140 °C - 180 °C. In further embodiments, the oxidation is performed for 1 hour - 6 hours. In still further embodiments, the oxidation is performed at pressure of 1 - 200 bar or 10 - 80 bar of oxygen and inert gas. In still further embodiments, the oxidation is performed at an oxygen concentration of 0.1 mol% - 50 mol% or 5 mol% - 20 mol%.In some embodiments, the disclosed methods further include separating the second compound from the second liquid. The second compound may be separated from the second liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof. In some embodiments, a plastic may be deconstructed by solvolysis. In some embodiments, deconstruction of a plastic or mixed plastic may be achieved by contacting the plastic or mixed plastic with a liquid such as water and / or acetic acid. In some embodiments, plastics may be deconstructed by exposing them to an oxidizing agent, e.g. O2. In some embodiments, the second liquid further comprises benzoic acid and the oxidation is performed at a pressure between 1 bar and 10 bar. In some embodiments, the oxidation is performed at a nressure between 1 bar and 10 bar.An additional aspect of the present disclosure provides a method of deconstructing plastics, the method comprising providing a feedstock that comprises polyesters (PET), polyurethanes (PU), nylons, polypropylene (PP), and polyethylene (PE). The method also comprises initiating a first acidolysis process at a first temperature without oxygen present during the reaction, thereby selectively deconstructing PU. Additionally, the method comprises initiating a second acidolysis process at a second temperature without oxygen present during the reaction, thereby selectively deconstructing nylon. The method further comprises initiating a third acidolysis process at a third temperature without oxygen present during the reaction, thereby selectively depolymerize PET to obtain TPA, unreacted PP, and unreacted PE.In some embodiments, the first temperature is between 140 °C and 160 °C. In some embodiments, the first temperature is about 140 °C. In some embodiments, the first temperature is about 150 °C. In some embodiments, the first temperature is about 160 °C. In some embodiments, the second temperature is between 200 °C and 240 °C. In some embodiments, the first temperature is about 200 °C. In some embodiments, the first temperature is about 220 °C. In some embodiments, the first temperature is about 240 °C. In some embodiments, the third temperature is about 280 °C. In some embodiments, at least some of the deconstructed PU is removed while at least a portion of the first reaction is occurring. In some embodiments, at least some of the deconstructed nylon is removed while at least a portion of the second reaction is occurring.Another aspect of the present disclosure provides a method of deconstructing mixed plastics. The method comprises contacting a first fraction of the mixed plastics with a first liquid. The method also comprises oxidizing a second fraction of the mixed plastics, wherein the contacting deconstructs the first fraction to a first compound, and the oxidizing deconstructs the second fraction to a second compound. In some embodiments, the contacting is performed before the oxidizing. In some embodiments, the oxidizing is performed before the solvolysis. In some embodiments, the contacting and the oxidizing are performed simultaneously. In some embodiments, the contacting and / or the oxidizing are performed in a reactor. In some embodiments, the contacting and the oxidizing are performed in the same reactor.In some embodiments, the mixed plastics comprise at least two different types of plastic. In some embodiments, the mixed plastics are selected from two or more of a polyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, or polyethylene terephthalate. In some embodiments, the mixed plastics are selected from three or more of apolyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, or polyethylene terephthalate.In some embodiments, the first liquid is selected from acetic acid, water, or both acetic acid and water. In some embodiments, the first liquid further comprises hydrochloric acid, sulfuric acid, or both hydrochloric and sulfuric acid. In some embodiments, the contacting is performed at a temperature selected from 22 °C - 300 °C or 120 °C - 280 °C. In some embodiments, the contacting is performed for 0.5 hours - 4 hours.In some embodiments, the first fraction comprises chemical bonds capable of being broken by the first liquid. In some embodiments, the polyamide is selected from the group consisting of polycaprolactam (Nylon 6), poly[imino(l,6-dioxohexamethylene)iminohexamethylene] (Nylon 6,6), and both Nylon 6 and Nylon 6,6. In some embodiments, the polyamide is selected from Nylon 11, Nylon 12, or both Nylon 11 and Nylon 12. In some embodiments, the polycarbonate is l,2-diacyl-sn-glycero-3-phosphocholine.In some embodiments, the first compound is soluble in the first liquid. In some embodiments, the method further comprises separating the first compound from the first liquid. In some embodiments, the first compound is separated from the first liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof. In some embodiments, the second fraction is present as a solid. In some embodiments, the oxidizing occurs by contacting the second fraction with a second liquid. In some embodiments, the second liquid comprises water, acetic acid, para-xylene, or any combination of thereof. In some embodiments, the second liquid further comprises benzoic acid. In some embodiments, the second liquid further comprises an initiator. In some embodiments, the initiator is N-hydroxypthalimide (NHPI), NaBr, or both NHPI and NaBr.In some embodiments, the second liquid further comprises a catalyst. In some embodiments, the catalyst comprises a transition metal. In some embodiments, the transition metal comprises cobalt, manganese, or both cobalt and manganese. In some embodiments, the oxidizing is performed at a temperature selected from 22 °C - 300 °C or 140 °C - 180 °C. In some embodiments, the oxidizing is performed for 1 hour - 6 hours. In some embodiments, the oxidizing is performed at pressure of 1 - 200 bar or 10 - 80 bar of oxygen and inert gas. In some embodiments, the oxidizing is performed at an oxygen concentration of 0.1 mol% - 50 mol% or 5 mol% - 20 mol%.In some embodiments, the first fraction comprises the polyolefin. In some embodiments, the polyolefin is selected from the group consisting of polyethylene, polypropylene, and both polyethylene and polypropylene. In some embodiments, the method further comprises separating the second compound from the second liquid. In some embodiments, the second compound is separated from the second liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof.Without being bound by any particular theory, there may be discussion herein of beliefs or understandings of underlying principles relating to the devices and methods disclosed herein. It is recognized that regardless of the ultimate correctness of any mechanistic explanation or hypothesis, an embodiment of the invention can nonetheless be operative and useful.BRIEF DESCRIPTION OF DRAWINGSSome embodiments are illustrated in referenced figures of the drawings. It is intended that the embodiments and figures disclosed herein are to be considered illustrative rather than limiting.Figure 1 illustrates a process for the solvolysis and / or oxidizing of mixed plastic streams, according to some embodiments of the present disclosure.Figure 2A illustrates deconstruction results of Nylon 6 by acetolysis, according to some embodiments of the present disclosure.Figure 2B illustrates deconstruction results of Nylon 6,6 by acetolysis, according to some embodiments of the present disclosure.Figures 3A, 3B, and 3C illustrate deconstruction results of polyethylene terephthalate (PET) by acetolysis, according to some embodiments of the present disclosure.Figure 4 illustrates deconstruction results of a polycarbonate by acetolysis, according to some embodiments of the present disclosure.Figures 5A, 5B, 5C, and 5D illustrate deconstruction results of polyethylene (PE) by oxidizing, according to some embodiments of the present disclosure.Figure 6 lists examples of deconstruction products resulting from the oxidizing of PE, according to some embodiments of the present disclosure.Figure 7A and 7B illustrate comparisons of acetolysis results to autoxidation of PE, according to some embodiments of the present disclosure.Figure 8 illustrates a series of processes for deconstructing mixed plastics, according to embodiments of the present disclosure.Figure 9 illustrates an annotated schematic of acidolysis according to Process 1 of Figure 8, according to embodiments of the present disclosure.Figure 10 illustrates examples of deconstructed Patagonia recircled materials consistent with Process 1 of Figure 8, according to embodiments of the present disclosure.Figure 11 illustrates process steps 3A and 3B of Figure 8, according to embodiments of the present disclosure.Figure 12 illustrates examples of deconstructed Patagonia recircled materials consistent with Process 3 of Figure 8, according to embodiments of the present disclosure.Figure 13 illustrates the solubility of PU at lower temperatures, according to embodiments of the present disclosure.Figure 14 illustrates the depolymerization of nylon 6,6 into soluble products, according to embodiments of the present disclosure.Figure 15 illustrates the generation of TPA after increasing the temperature to 280 C in a reaction that had initially contained both nylon and PET, according to embodiments of the present disclosure.Figure 16 illustrates conversion of plastics to soluble products, gaseous products, or TPA, according to embodiments of the present disclosure.Figure 17 illustrates the production of MEET and TPA in accordance with embodiments of the present disclosure.DETAILED DESCRIPTIONReferences in the specification to “one embodiment”, “an embodiment”, “an example embodiment”, “some embodiments”, etc., indicate that the embodiment described may include a particular feature, structure, or characteristic, but every embodiment may not necessarily include the particular feature, structure, or characteristic. Moreover, such phrases are not necessarily referring to the same embodiment. Further, when a particular feature, structure, or characteristic is described in connection with an embodiment, it is within the knowledge of one skilled in the art to affect such feature, structure, or characteristic in connection with other embodiments whether or not explicitly described.The present disclosure relates to, among other things, a plastics recovery and recycling process, which utilizes sequential solvolysis and oxidation to deconstruct plastic and / or mixed plastics into deconstruction products that are useful for the production of new materials including polymers, resins, and / or monomers used to construct polymers and / or resins. In some embodiments, methods provided herein may be used to deconstruct mixed plastic streams and recover recyclable deconstruction products. Advantages of the disclosed process include the minimization and / or elimination of presorting the plastics into their various polymer classes (e.g., polyolefins, polyamides, polycarbonates, polyurethanes, etc.) prior to processing. In some embodiments, both the solvolysis and the oxidation may utilize the same treating liquid (e.g., acetic acid for the example of acetolysis). Soluble materials generated by the disclosed process may be subsequently separated from insoluble solid plastic materials and / or deconstruction products (e.g., terephthalic acid) to form a stream containing soluble components, substantially free of solids, and a stream containing any remaining insoluble solid compounds. The insoluble solid compounds may then be deconstructed via oxidation to produce additional soluble deconstruction products.The deconstruction products produced by the disclosed solvolysis may produce insoluble plastics, oligomers, monomers, residues, etc., as not all forms of plastic are capable of being broken down via solvolysis. This insoluble fraction may be oxidized, however, resulting in the further deconstruction of those insoluble components and the converting of at least a portion of the insoluble materials into soluble compounds. In some embodiments all, or substantially all, of the insoluble materials may be converted into soluble compounds. These newly formed soluble materials may be subsequently separated from any remaining insoluble solid plastic materials and / or deconstruction products to form a first stream containing soluble components substantially free of solids and a second stream containing any remaining solid compounds.As used herein, the term "about" is used to indicate that exact values are not necessarily attainable. Therefore, the term "about" is used to indicate this uncertainty limit. In some embodiments of the present invention, the term "about" is used to indicate an uncertainty limit of less than or equal to ±20%, ±15%, ±10%, ±5%, or ±1% of a specific numeric value or target. In some embodiments of the present invention, the term "about" is used to indicate an uncertainty limit of less than or equal to ±1%, ±0.9%, ±0.8%, ±0.7%, ±0.6%, ±0.5%, ±0.4%, ±0.3%, ±0.2%, or ±0.1% of a specific numeric value or target.As used herein, “deconstruct” and related terms (e.g., “deconstruction”) refers to chemically breaking one or more carbon-carbon bonds and / or one or more non-carbon-carbon bonds (e.g.,C-N and / or C-0 bonds) present in a plastic (of any type). In various aspects, this can result in the generation of processable intermediates from the plastic, sometimes resulting in the complete breakdown of a plastic into its original monomers. In various aspects, the deconstruction of a polymeric plastic results in the depolymerization of that polymer.As used herein, “mixed plastic,” “mixed plastics,” “mixed plastic streams” and the like refer to a combination of at least two chemically distinct forms of plastic. In various aspects, the mixed plastics can comprise two or more of a polyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, a polyethylene, a polyethylene terephthalate, a polypropylene, a polyvinyl chloride, a polymethyl methacrylate, an acrylonitrile-butadiene- styrene, or combinations thereof. In the context of the present disclosure, deconstruction of “mixed plastics” refers to the deconstruction of two or more chemically distinct forms of plastic via the same sequential solvolysis and oxidation process, as described herein. In some embodiments, for example in the embodiment shown in Figure 1, mixed plastics may include two or more of polyethylene terephthalate (PET), polyethylene (PE), polypropylene (PP), polystyrene (PS), a polycarbonate, a polyurethane, cellulose, polyoxymethylene, and / or other commonly used commercial plastics. Examples of polyamides that may be deconstructed via the disclosed methods to yield useful downstream products include polycaprolactam (Nylon 6), poly[imino(l,6-dioxohexamethylene)iminohexamethylene] (Nylon 6,6), Nylon 11 (also known as PA11), and / or Nylon 12 (also known as PA12). An example of a polycarbonate that may be treated and deconstructed to yield useful downstream products includes 1,2-diacyl-sn- glycero-3 -phosphocholine (also known as PC-1).As used herein, “plastic” means a synthetic material made from one or more of a wide range of organic polymers (e.g., polyethylene, PVC, nylon, etc.) that can be molded into shape while soft and then set into a rigid or slightly elastic form, and generally includes both polymers and resins.As used herein, “solvolysis” means a nucleophilic substitution or elimination reaction where the nucleophile is a solvent molecule. In various aspects, “solvolysis” refers to a liquid phase reaction utilizing a nucleophile solubilized in a liquid that reacts with the plastic and / or the mixed plastics by breaking non-carbon-carbon bonds within the mixed plastics, forming soluble monomers and / or oligomers (e.g., via the breaking of C-N and / or C-0 bonds). Examples of suitable liquids to perform solvolysis in the disclosed methods include water, resulting in hydrolysis, and / or acetic acid, resulting in acetolysis. In some embodiments, solvolysis can include the use of a catalvst selected from cobalt, manganese, zirconium, andcombinations thereof. Such a catalyst may be used with acetic acid to oxidize and / or autoxidize insoluble deconstruction products resulting from acetolysis.As used herein the term "substantially" is used to indicate that exact values are not necessarily attainable or necessary in order to properly implement a disclosed embodiment. By way of example, one of ordinary skill in the art will understand that in some chemical reactions 100% conversion of a reactant is possible, yet unlikely. Most of a reactant may be converted to a product and conversion of the reactant may asymptotically approach 100% conversion. So, although from a practical perspective 100% of the reactant is converted, from a technical perspective, a small and sometimes difficult to define amount remains. For this example of a chemical reactant, that amount may be relatively easily defined by the detection limits of the instrument used to test for it. However, in many cases, this amount may not be easily defined, hence the use of the term "substantially". In some embodiments of the present invention, the term "substantially" is defined as approaching a specific numeric value or target to within 20%, 15%, 10%, 5%, or within 1% of the value or target. In further embodiments of the present invention, the term "substantially" is defined as approaching a specific numeric value or target to within 1%, 0.9%, 0.8%, 0.7%, 0.6%, 0.5%, 0.4%, 0.3%, 0.2%, or 0.1% of the value or target.Deconstruction via Solvolysis, OxidationFigure 1 illustrates a method 100 for deconstructing mixed plastics 105, resulting in the formation of one or more products (165A, 165B, and / or 165C), according to some embodiments of the present disclosure. Deconstruction products (165 A, 165B, and / or 165C) resulting from the method 100 illustrated in Figure 1 can include, for example, a dicarboxylic acid and / or a lactone acid. Specific examples of deconstruction products (165A, 165B, and / or 165C) include acetaminocaproic acid, diacetyl hexamethylene diamine, adipic acid, ethylene glycol diacetate, and / or benzoic acid.Referring again to Figure 1, a method 100 for deconstructing mixed plastics 105 may include pre-treating 110 one or more mixed plastics stream(s). Mixed plastics streams may originate from plastics recycling centers or other sources of multiple plastic waste products, such as community trash collection, commercial waste streams, textiles companies disposing of plastic-based textile materials, companies disposing of plastic-based manufacturing materials containing multiple types of plastics, etc. Pre-treating 110 may include a variety of different procedures, for example, washing, removal of non-plastic material(s), size-reduction of themixed plastics, and the like, or combinations of any of the foregoing. Washing may occur conventionally, such as by using a water rinse or spray. Metal materials may be removed magnetically and / or by density differences. Size-reduction may be achieved using a variety of mechanical procedures, including a knife-mill. The result of pretreating 110 is pre-treated, mixed plastics 115, which are then subjected to solvolysis 120. Pre-treating 110 mixed plastics 105 is optional and not required for the disclosed processes. Whether or not pre-treating 110 of the mixed plastics 105 occurs is discretionary and may depend, for example, on the source and composition of the original mixed plastics, the amount and type of non-plastic materials present, the discretion of the operator, and the like.The mixed plastics 105 and / or the pre-treated mixed plastics 115 are then subjected to solvolysis 120 where the mixed plastics 105 and / or the pre-treated mixed plastics 115 are contacted with a liquid 122A that reacts with the mixed plastics (105 and / or 115) by breaking non-carbon-carbon bonds within the mixed plastics. In the depicted embodiment, the liquid 122A may be water and / or acetic acid. Solvolysis 120 includes combining the mixed plastics (105 and / or 115) with the liquid 122A under process conditions that facilitate and support the reactions (e.g., hydrolysis and / or acetolysis) resulting in fast degradation of the mixed plastics (105, 115) and yielding high degrees of completion. In some embodiments, solvolysis 120 occurs at a temperature of 22 °C - 300 °C or 120 °C - 280 °C for 0.5 hours - 4 hours. In some embodiments, solvolysis 120 occurs at a pressure of 1 bar - 100 bar or 1 bar - 30 bar. In some embodiments, solvolysis 120 occurs in an inert atmosphere, for example under nitrogen gas (N2). In some embodiments, solvolysis 120 occurs via the addition of at least one more acid and / or a base (in addition to the water and / or acetic acid) to facilitate faster reaction rates and / or increased deconstruction rates of the plastics to deconstruction products. Suitable acids that may be included into the solvolysis 120 reaction include hydrochloric acid, sulfuric acid, nitric acid, boric acid, carbonic acid, perchloric acid, phosphoric acid, hydrofluoric acid, or any other suitable inorganic acid.In embodiments, mixed plastics (such as 105) and / or the pre-treated mixed plastics (such as mixed plastics 115) may be subjected to a contacting step where the mixed plastics and / or the pre-treated mixed plastics are contacted with a liquid (such as liquid 122 A), resulting in the deconstruction of the mixed plastics and / or the pre-treated mixed plastics. In some embodiments, the contacting may result in the solvolysis of the mixed plastics and / or the pretreated mixed plastics, consistent with a solvolysis process described herein. A liquid may be water and / or acetic acid. Contacting may include combining the mixed plastics and / or the pre-treated mixed plastics with the liquid under process conditions that facilitate fast deconstruction (e.g., via hydrolysis and / or acetolysis) of the mixed plastics and / or the pre-treated mixed plastics and yielding high degrees of completion. In some embodiments, contacting may be performed at a temperature of 22 °C - 300 °C for 0.5 hours - 4 hours. In some embodiments, contacting may be performed at a temperature of 120 °C - 280 °C for 0.5 hours - 4 hours. In some embodiments, contacting may be performed at a pressure of 1 bar - 100 bar. In some embodiments, contacting may be performed at a pressure of 1 bar - 30 bar. In some embodiments, contacting may be performed in an inert atmosphere, for example under nitrogen gas (N2). In some embodiments, contacting may be performed via the addition of at least one more acid and / or a base (in addition to the water and / or acetic acid) to facilitate faster reaction rates and / or increased deconstruction rates of the plastics to deconstruction products. Suitable acids that may be included in the contacting of a plastic or mixed plastic with a liquid include hydrochloric acid, sulfuric acid, nitric acid, boric acid, carbonic acid, perchloric acid, phosphoric acid, hydrofluoric acid, and / or any other suitable inorganic acid.Depending upon the composition of the mixed plastics (105 / 115), solvolysis 120 may result in a mixture that includes soluble deconstruction compounds and insoluble plastic materials that are resistant to the solvolysis and / or deconstruction products that remain insoluble in the liquid 122. This stream, resulting from the solvolysis 120, is a first solid / liquid mixture 125. For example, polyolefins such as PE and PP may remain unaffected by solvolysis, remaining essentially in their same original composition and form, and present as an insoluble phase in the first solid / liquid mixture 125. PET may partially deconstruct during solvolysis 120, resulting in soluble deconstruction products such as ethylene glycol, ethylene glycol monoacetate, and / or ethylene glycol diacetate as well as solid, insoluble deconstruction products such as terephthalic acid. The insoluble, solid compounds resulting from solvolysis (and / or that remain unreacted after solvolysis), such as polyolefins and / or terephthalic acid, are then deconstructed into useful soluble compounds in a downstream oxidizing 140 step.Similarly, with respect to contacting processes, depending upon the composition of the mixed plastics, contacting may result in a mixture that includes soluble deconstruction compounds and insoluble plastic materials that are resistant to deconstruction and / or deconstruction products that remain insoluble in the liquid. This stream, resulting from the contacting, is a first solid / liquid mixture. For example, polyolefins such as PE and PP may remain unaffected by contact with a liquid, remaining essentially in their same original composition and form, and present as an insoluble phase in the first solid / liquid mixture. PET, however, may partiallydeconstruct during contacting with a liquid, resulting in soluble deconstruction products such as ethylene glycol, ethylene glycol monoacetate, and / or ethylene glycol diacetate as well as solid, insoluble deconstruction products such as terephthalic acid. The insoluble, solid compounds resulting from the contacting (and / or that remain unreacted after contacting), such as polyolefins, may then be deconstructed into useful soluble compounds in a downstream oxidizing step.As shown in Figure 1, in some embodiments the first solid / liquid mixture 125 is directed to a first separating 130 step, which separates the first solid / liquid mixture 125 into a first liquid fraction 136 and a first solid fraction 138. The first liquid fraction 136 may be essentially solids- free and include soluble deconstruction products such as ethylene glycol, ethylene glycol monoacetate, and / or ethylene glycol diacetate (e.g., derived from the deconstruction of PET) in a mixture with the liquid 122 A, whereas the first solid stream 138 may be essentially liquid- free and include only the non-soluble, solid components (such as terephthalic acid and / or unreacted polyolefins such as PP and / or PE). The first separating 130 may be achieved using at least one of filtration, centrifugation, and / or a gravimetric method (e.g., a settling tank). The first liquid fraction 136 may then be directed to a post-treating 160 A step, for example a separating step to purify the deconstruction products it contains and / or an upgrading step to react the deconstruction products to form other products 165 A from the deconstruction products. In those embodiments where the post-treating 160A step is a separating step, the separation and production of pure deconstruction products may be achieved using at least one of distillation, extraction, crystallization, or similar separation techniques.

[0001] Referring again to Figure 1, the first solid fraction 138 resulting from solvolysis 120 and / or the first separating 130 step is thereafter directed to an oxidizing 140 step. During the oxidizing 140, oxygen (O2) 142 is introduced into the process such that the first solid fraction 138 is placed into contact with the oxygen 142. Oxidation 140 therefore proceeds in the presence of oxygen 142. In contacting processes as discussed herein, a first solid fraction resulting from a contacting step and / or a first separating step may be thereafter directed to an oxidizing step. During the oxidizing step, oxygen (O2) may be introduced into the process such that the first solid fraction is placed into contact with the oxygen, resulting in the deconstruction of at least a portion of the first solid fraction. Oxidizing, therefore, may proceed in the presence of diatomic oxygen, or some other suitable oxidizing agent. In some embodiments, a suitable oxidizing agent is ozone. In some embodiments, a suitable oxidizing agent is hydrogen peroxide. In some embodiments, a suitable oxidizing agent is calcium oxide.

[0002] Some examples of oxidizing agents include ABNO, Acetone, Acrylonitrile, Allyl diethyl phosphate, Ammonium cerium (IV) nitrate, Ammonium peroxy di sulfate, 2- Azaadamantane A-oxyl, 9-Azabicyclo[3.3.1]nonane A-oxyl, AZADO, 9- Azanoradamantane A-oxyl, 1,4-Benzoquinone, Benzaldehyde, Benzophenone, Benzoyl peroxide, Bi s(m ethanesulfonyl) peroxide, Bis(trimethylsilyl) peroxide, Bleach, A- Bromosaccharin, A-Bromosuccinimide, BTSP, Burgess reagent, (E)-But-2-enenitrile, A- Fluoro-2,4,6-trimethylpyridinium tritiate, A-Zc / V-Butylbenzenesulfinimidoyl chloride, tert- Butyl hydroperoxide, Zc / V-Butyl hypochlorite, / c / V-Butyl nitrite, / c / V-Butyl peroxybenzoate, CAN, Carbon tetrabromide, Cerium ammonium nitrate, Choline peroxy di sulfate, Chloramine- B, Chloramine-T, Chloranil, Chloromethyl-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate), 3 -Chloroperoxybenzoic acid, ChPS, Chromium compounds, Chromium trioxide, Collins Reagent, Corey-Suggs Reagent, CMHP, Copper compounds, Crotononitrile, Cumene hydroperoxide, 1,1 -Cyclohexanediyl dihydroperoxide, Davis Reagent, DBDMH, DCP, DDQ, DEAD, DEAP, Dess-Martin periodinane, DIAD, l,3-Dibromo-5,5- dimethylhydantoin, 2,3-Dichloro-5,6-dicyanobenzoquinone, Dicumyl peroxide, Diethyl azodicarboxylate, Diethyl allyl phosphate, DIH, 1,1 -Dihydroperoxy cyclohexane, 1,3-Diiodo- 5, 5 -dimethylhydantoin, Diisopropyl azodicarboxylate, Dimethyl sulfoxide, Di-tert-butyl peroxide, DMP, DMSO, DPQ, DQ, DTBP, Duroquinone, (E)-But-2-enenitrile, Ferric chloride, Ferric nitrate, A-Fluorobenzenesulfonimide, A-Fluoropyridinium tritiate, A-Fluoro-2,4,6- trimethylpyridinium tritiate, Formic acid, 1-HCPK, Hydrogen peroxide, Hydrogen peroxide urea adduct, 2-Hydroperoxy-4,6-diphenyl-l,3,5-triazine,l-Hydroxycyclohexyl phenyl ketone,Hydroxy(tosyloxy)iodobenzene, Hypervalent bromine compounds, Hypervalent iodine compounds, HTIB, IBX, Iodine, Iodine pentoxide, lodobenzene dichloride, lodosobenzene bis(trifluoroacetate), lodosobenzene diacetate, A-Iodosuccinimide, lodosylbenzene, 2- lodoxybenzoicacid, Iron(III), (V) and (IV), Jones Reagent, Koser's Reagent, Magnesium monoperoxyphthalate hexahydrate, Manganese compounds, Manganese(IV) oxide, MCPBA, meto-Chloroperbenzoic acid, (Methoxycarbonylsulfamoyl)tri ethylammonium hydroxide,A-Methylmorpholine-A-oxide, Methyltrioxorhenium, MMPP • 6 H2O, Molybdenum compounds, MTO, A-Bromosaccharin, A-Bromosuccinimide, A-Chlorobenzenesulfonamide sodium salt, A-Chloro tosylamide sodium salt, A-Chlorosuccinimide, A- Fluorobenzenesulfonimide, A-Fluoropyridinium tritiate, A-Fluoro-2,4,6-trimethylpyridinium tritiate, A-Iodosuccinimide, AAA'A-Tetrachlorobenzene-l,3-disulfonamide, Nitric Acid, Nitrobenzene, Nitrosobenzene, Nitrous Oxide, A-Methylmorpholine-A-oxide, NMO, Nor-AZADO, V-tert-Butylbenzenesulfinimidoyl chloride, Osmium tetroxide, Oxalyl chloride, Oxone, Oxygen, Ozone, PCC, PDC, , Periodic acid, Peroxides, Peroxy acids, Phenyliodonium diacetate, 2-(Phenylsulfonyl)-3-phenyloxaziridine, Phthaloyl peroxide, PIFA, Pivaldehyde, Potassium ferricyanide , Potassium periodate, Potassium permanganate, Potassium peroxy di sulfate, Potassium peroxomonosulfate, PPO, 2 -Propanone, Pyridine A-oxide, Pyridinium hydrobromide perbromide, Pyridinium chlorochromate, Pyridinium dichromate, Pyridinium tribromide, Ruthenium (III - VII) compounds, Sarett Reagent, Selectfluor, Selenium dioxide, Sodium bromate, Sodium chlorate, Sodium chlorite, Sodium di chloroiodate, Sodium hypochlorite, Sodium nitrite, Sodium perborate, Sodium percarbonate, Sodium periodate, Sodium peroxy di sulfate, Sulfur, Styrene, TBCA, TBHP, TBN, TBPB, TCBDA, TCCA, TEMPO, Tetrabromomethane, Tetrachloro- 1,4-benzoquinone, N-tert- Butylbenzenesulfmimidoyl chloride, tert-butyl hydroperoxide, tert-Butyl hypochlorite, tert- Butyl nitrite, tert-Butyl peroxybenzoate, Tetrabutylammonium peroxy di sulfate, N,N,N',N'~ Tetrachlorobenzene-l,3-disulfonamide, 2, 3, 5, 6-tetramethyl- 1,4-benzoquinone, 2, 2,6,6- T etram ethylpiperidinyloxy, Tetrapropylammonium Perruthenate, 3,3',5,5'-Tetra-tert- butyldiphenoquinone, TPAP, Triacetoxyperiodinane, Triazox, Tribromoisocyanuric acid, Trichloroisocyanuric acid, 1,1,1-Trifluoroacetone, Trifluoroacetic peracid, Trimethylacetaldehyde, UHP, Urea hydrogen peroxide adduct, Vanadium compounds, Vinyl cyanide, and Water.As set forth above, the first separating 130, which separates the first solid fraction 138 from the first liquid fraction 136, can result in the first solid fraction 138 being essentially liquid- free. Therefore, in some embodiments, a liquid 122B is mixed with the first solid fraction 138, either prior to the oxidizing and / or during the oxidizing 140. In some embodiments, the liquid 122B is the same as liquid 122A used in solvolysis 120. In other embodiments, liquid 122B is different from liquid 122A. Liquid 122B may include water and / or acetic acid, among other things. In some embodiments, sufficient liquid 122A may remain in the first solid fraction 138 that additional liquid 122B does not need to be added to the oxidizing 140 step.In some embodiments, the liquid present during oxidizing 140, which may be liquid 122 A and / or 122B, may include additional components apart from the liquids used to achieve solvolysis 120. For example, in some embodiments the liquid used during oxidizing 140 may further include para-xylene and / or benzoic acid. In some embodiments, liquid 122A and / or 122B may include an initiator and / or a catalyst to help promote faster oxidation rates and / or higher deconstruction percentages. Examples of suitable initiators for oxidizing 140 includeN-hydroxypthalimide (NHPI) and NaBr, though other suitable initiators may also be used. Examples of suitable catalysts for oxidizing 140 include transition metals such as cobalt, manganese, and / or zirconium. In some embodiments, oxidizing 140 of the first solid fraction 138 may be performed at a temperature of 22 °C - 300 °C or 140 °C - 180 °C for period of time of one hour to six hours. In embodiments, oxidizing 140 may be performed at pressure of 1 - 200 bar or 10 - 80 bar of oxygen and inert gas. The oxygen 142 introduced in the oxidizing 140 step may be oxygen gas (O2) diluted with an inert gas and / or air diluted with an inert gas and, in some embodiments, contains oxygen at a concentration of 0.1 mol% - 50 mol% or 5 mol% - 20 mol%. Examples of suitable inert gases that may be utilized for the foregoing dilution include nitrogen, helium, neon, argon, krypton, xenon, and / or combinations thereof.

[0003] Depending upon the composition of the first solid fraction 138, oxidation 140 may result in a mixture that includes additional soluble deconstruction compounds and additional insoluble plastic materials that that remain insoluble in the liquid 122A and / or 122B. This stream, resulting from the oxidation 140, is a second solid / liquid mixture 145. For example, plastics such as PE, PS, and PP, as well as the monomer TPA from PET deconstruction, may remain unaffected by solvolysis, remaining essentially in their same original composition and form, and present as an insoluble phase in the first solid / liquid mixture 125. Upon oxidation 140 however, PE, PS and PP may break down into deconstructions products including dicarboxylic acids, lactone acids, and benzoic acid, among other things, leaving TPA in its solid, insoluble form. The insoluble, solid compounds resulting from oxidation 140 (and / or that remain unreacted after oxidation 140) are then capable of further separation.As shown in Figure 1, in some embodiments the second solid / liquid mixture 145 is directed to a second separating 150 step, which separates the second solid / liquid mixture 145 into a second liquid fraction 156 and a second solid fraction 158. The second liquid fraction 156 may be essentially solids-free and include soluble deconstruction products such as dicarboxylic acids, lactone acids, benzoic acid, and the like e.g., derived from the deconstruction of PE, PS and / or PP) in a mixture with the liquid 122B, whereas the second solid stream 158 may be essentially liquid-free and include only the non-soluble, solid components (such as TPA). The second separating 150 may be achieved using at least one of filtration, centrifugation, and / or a gravimetric method (e.g., a settling tank). The second liquid fraction 156 may then be directed to a post-treating 160B step, for example a separating step to purify the deconstruction products it contains and / or an upgrading step to react the deconstruction products to form other products 165B from the deconstruction products. In those embodiments where the post-treating 160Bstep is a separating step, the separation and production of pure deconstruction products may be achieved using at least one of distillation, extraction, crystallization, or similar separation techniques.Finally, the second solid fraction 158, once separated from the second liquid fraction 156, may be subjected to a post-treating step 160C in order to yield a product 165C. This post-treating step 160C may be as simple as a purification step, where any remaining liquid 122B is removed and the final product 165C dried. The resulting product 165C, for example TPA remaining unreacted after both solvolysis and oxidation, may then be recycled, reused and / or upcycled for new purposes. In some embodiments, TPA remaining unreacted may result from deconstruction by contacting and / or oxidizing.ReactorsThe disclosed methods can be performed in any number of reactor configurations. In some embodiments, contacting processes may be performed in order to deconstruct plastic materials. In some embodiments, solvolysis 120 and oxidizing 140 may be performed in series, for example in two separate unit operations and thus two separate reactors. In such embodiments, solvolysis 120 may be performed in a first reactor and oxidizing 140 may be performed in a second reactor, with the first reactor and second reactor configured in series. In other embodiments, solvolysis 120 and oxidizing 140 may occur simultaneously in a single reactor. There are advantages to both configurations. For example, a tandem, two-reactor configuration may allow for constant, or near constant, feeding of mixed plastic reactants into a linear system. Known reactions (solvolysis 120 and oxidation 140) occur in tandem, in some embodiments in different liquids (122A and 122B, respectively). This allows for known deconstruction products to be removed at discrete portions of the process. For instance, deconstruction product 165A can be removed from the same point after solvolysis, from the first liquid fraction 136. Similarly, deconstruction product 165B can also be removed from the same point after oxidation 140, from the second liquid fraction 156. Lastly, products 165C can be removed from the second solid fraction 158 after oxidation 140.Single reactor configurations also provide several advantages. For example, a single reactor configuration reduces the capital costs of the manufacturing plant and simplifies the plant’s operation, resulting in more reliable operation and increased on-line time. Examples of single reactor configurations and methods of operating single reactor configurations will now be provided.In some embodiments of the present disclosure, a single reactor configuration may be very effective at deconstructing a mixed plastics 105 stream that includes, for example, polyamides, Nylon 6, Nylon 6,6, polyolefins, PE, PP, at least one polycarbonate, polyurethanes, and PET (or any subset of mixed plastics 15 streams derived therefrom). After any optional pre-treating 110 step(s) are performed, this mixed plastics 105 stream is directed to a single reactor where it is combined with a liquid 122A that comprises acetic acid, water and / or both, resulting in the solvolysis of at least a portion of the mixed plastics 105 and the creation of a first solid / liquid mixture 125. In these embodiments, solvolysis 120 may occur at a temperature of 22 °C - 300 °C or 120 °C - 280 °C, for a period of time of 0.5 hours - 4 hours, and at a pressure of 1 bar - 100 bar or 1 bar - 30 bar. These solvolysis conditions may result in the deconstruction (which may be complete or partial deconstruction) of the Nylon 6, Nylon 6,6, the polycarbonate, polyurethanes, and / or the PET, whereas the PE and PP may remain essentially unreacted by the solvolysis, remaining as a solid phase (a first solid fraction 138) in the reacting liquid 122A. Nylon 6 may deconstruct, such as through solvolysis, to acetyl amino caproic acid, Nylon 6,6, may deconstruct to at least one of diacetyl hexamethylene diamine and / or adipic acid, the polycarbonate may deconstruct to at least one of bisphenol A, monoacetylated bisphenol A, diacetylated bisphenol A, phenol, phenol acetate, and / or 4-isopropylphenylacetate, with each or most of these deconstruction products (individually and collectively, 165 A) present as soluble components within the first solid / liquid mixture 125. In addition, the PET may deconstruct, such as through solvolysis, to form the soluble components of at least one of ethylene glycol, ethylene glycol monoacetate, and / or ethylene glycol diacetate and insoluble terephthalic acid (again, individually and collectively, 165 A) present as soluble components within the first solid / liquid mixture 125. Additionally, polyurethane may deconstruct into polyols or acetylated polyols including propanediol, propanediol diacetate, ethylene glycol, ethylene glycol diacetate, glycerol, and glycerol triacetate, in addition to 4,4'- diacetamidodiphenylmethane or 2,4-diacetylaminotoluene.The first solid fraction 138, resulting either from the solvolysis 120 and / or present as unreacted components from the solvolysis 120, may be deconstructed in the same reactor via oxidizing 140. In that regard, oxidizing 140 may occur either at the same time as the solvolysis 120 (e.g., substantially in parallel with the solvolysis 120) or may occur at a different time than the solvolysis 120 (e.g., substantially in series with the solvolysis 120). These single reactor embodiments, therefore, include methods where solvolysis 120 and oxidation 140 occur simultaneously; where solvolysis 120 occurs before oxidation 140; or where solvolysis 120occurs after oxidation 140. Thus, in some embodiments of the present disclosure, a reacting mixture, such as the first solid / liquid mixture 125 and / or the second solid / liquid mixture 145, may include both the components needed for solvolysis 120 as well as the components needed for oxidizing 140. The reacting mixture (the first solid / liquid mixture 125 and / or the second solid / liquid mixture 145) may then be subjected to reaction conditions that enable both reactions, solvolysis 120 and oxidizing 140, to occur substantially simultaneously, or for one reaction to occur substantially prior to the other. Thus, in some embodiments of the present disclosure, the solvolysis and oxidizing may be performed in parallel, in the same unit operation (z.e., reactor).A single reactor can also facilitate the occurrence of multiple solvolysis reactions across a range of temperatures, deconstructing multiple plastics by varying a single reaction parameter. For example, in some embodiments a mixed plastics 105 stream introduced into a single reaction vessel may include nylon, PU, PET, PE and PP plastics. In these embodiments, solvolysis 120 reaction temperatures may begin at a relatively low starting temperature, for example about 160 °C, in order to preferentially deconstruct PU into one or more deconstruction products 165A, substantially eliminating it from the mixed plastics 105 by solvolysis 120. In some embodiments, a relatively low starting temperature may be between about 100 °C and 160 °C.In some embodiments, a relatively low starting temperature may be about 100 °C. In some embodiments, a relatively low starting temperature may be about 110 °C. In some embodiments, a relatively low starting temperature may be about 120 °C. In some embodiments, a relatively low starting temperature may be about 130 °C. In some embodiments, a relatively low starting temperature may be about 140 °C. In some embodiments, a relatively low starting temperature may be about 150 °C. In some embodiments, a relatively low starting temperature may be about 160 °C.Thereafter, the temperature in the reaction vessel may be increased to between about 160 °C and 220 °C in order to preferentially deconstruct the nylon into one or more deconstruction products 165A, also substantially eliminating it from the mixed plastics 105 by solvolysis 120. In some embodiments, the temperature in the reaction vessel may be raised to about 160 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 170 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 180 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 190 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 200 °C. Insome embodiments, the temperature in the reaction vessel may be raised to about 210 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 220 °C.Finally, the temperature in the reaction vessel may be increased again to between about 220 °C and 280 °C in order to deconstruct PET into one or more deconstruction products 165 A as well as an insoluble solid (TP A). In some embodiments, the temperature in the reaction vessel may be raised to about 220 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 230 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 240 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 250 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 260 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 270 °C. In some embodiments, the temperature in the reaction vessel may be raised to about 280 °C. In this embodiment, the staged solvolysis 120 reactions, each occurring at a different temperature, will yield a plurality of deconstruction products 165 A that are soluble in the resulting first solid / liquid mixture 125 (each derived from the deconstruction of PU, nylon and PET), as well as an insoluble first solid fraction 138 that includes PE and PP. As will be appreciated, in other embodiments this type of varied solvolysis 120 reactions can occur across a plurality of reaction vessels, for example each reaction temperature can occur in a single reaction vessel, as shown in Figure 12.In the singe reactor embodiments, at the completion of these three temperature range, the solvolysis steps may result in each of the nylon, PU and PET at least partially, and in some embodiments fully, deconstructing into soluble deconstruction compounds, and the PET deconstructing into both soluble and insoluble compounds. In these embodiments, the single reactor, now containing the first solid / liquid mixture 125 generated by the three sequential solvolysis 120 reactions, is subjected to oxidizing 140 conditions. The oxidation 140 is then performed in the same vessel, without the need to separate the first solid / liquid mixture 125 into its corresponding liquid (136) and solid (138) fractions. Additionally, during the solvolysis 120 reactions, oxygen 142 may also be directed into the single reactor to allow oxidation 140 to occur, such that the oxidizing 140 step proceeds substantially in parallel with the solvolysis 120. Both reactions therefore occur at the same time, in the same reaction vessel, resulting in the deconstruction of the solid polyolefins (PP and PE) and / or the solid terephthalic acid into additional soluble components that will be present in the resulting second liquid fraction 156. In the above embodiment, both the first (136) and second (156) solid / liquid mixtures are present in the reactor at the end of the solvolysis 120 / oxidation 140 processes, as are bothproducts 165A (derived from each of the three solvolysis 120 reactions) and products 165B (derived from oxidation 140). Products 165C, representing the insoluble solids that still remain after solvolysis 120 and oxidation 140, may also be present in the single reactor. Therefore, in such embodiments, the solvolysis and oxidizing may occur substantially simultaneously at the same temperatures and / or pressures, or at least over temperature ranges and pressure ranges that overlap.However, in other embodiments of the present disclosure, solvolysis and oxidation may be performed substantially in series, yet still in a single reactor. For example, the temperature ramping described above for solvolysis 120 may be performed in the absence of any oxygen 142, oxidizing catalyst, and / or oxidizing initiator. Once the deconstruction of the plastic components capable of deconstruction by solvolysis 120 has gone to completion and / or to a desirable level of completion, the materials needed to begin oxidizing 140 may be added, resulting in the preferential oxidizing 140 deconstruction of those deconstruction products derived from solvolysis 120 (such as, for example, polyolefins PE and PP) to produce additional soluble compounds. Both methods, operating the reactions in series and operating the reactions in parallel, can therefore occur in a single reaction vessel. Additionally, both methods can occur in separate reactions vessels, as may be desired and / or appropriate for a given mixed plastics 105 stream.Another advantage imparted by the use of a single reaction vessel is that multiple rounds of solvolysis 120 / oxidation 140 can be performed on the same mixed plastics 105 stream, to ensure complete, or nearly complete, deconstruction of the mixed plastics 105 into their deconstructions products. For example, a method may include a first step of only solvolysis 120, including different operating temperatures to preferentially deconstruct specific targeted plastics as described above. This method may then follow with the addition of the components needed for oxidizing 140, at the temperature determined to be optimum for oxidizing 140 the polyolefins present in the exemplary plastics mixture. Once the oxidizing 140 reaction is sufficiently complete, the method may then continue by changing the reaction conditions to those needed to deconstruct any particularly recalcitrant plastics by either solvolysis 120 and / or oxidizing 140 again. This can occur for two, three, four, five, six, or more rounds of solvolysis 120 / oxidation 140, until the mixed plastics 105 have been sufficiently deconstructed which, in some embodiments, can be fully deconstructed into their monomeric subunits.Referring again to Figure 1, in some embodiments of the present disclosure, the first separating 130 and the second separating 150 may be achieved using either two separate unit operationse.g., filters), or a single unit operation may be used for both separating steps (130 and 150). For example, in those embodiments described herein where a method is employed that utilizes a single reactor for both solvolysis 120 and oxidizing 140, a single filter may be employed at one or more points during the reaction cycle(s) in order to separate deconstruction products from the first (125) and second (145) solid / liquid mixtures as may be needed for a particular mixture of plastics. For example, to prevent unwanted side reactions and / or the decomposition of deconstruction products to unwanted compounds, for example due to high temperatures needed to complete sufficient solvolysis 120 and / or oxidizing 140, in some embodiments the disclosed methods may periodically and / or continuously include the removal of some of the first (125) and second (145) solid / liquid mixtures from the reactor to preferentially remove at least one of insoluble materials and / or soluble degradation products (165A, 165B, as appropriate), with the remainder recycled back to the reactor. In so doing, the removed components may avoid exposure to unfavorable process conditions that may result in unwanted side reactions, etc. In some embodiments of the present disclosure, soluble deconstruction products, present in either the first (136) or second (156) liquid fractions, may be removed from the reaction vessel using a separating (130, 150, as appropriate) technique selected from at least one of a membrane separation, distillation, extraction, and / or crystallization. Such removal can occur in a number of ways, for example as a continuous filtration of the liquid as the reaction processes occur, at one or more discrete points during the solvolysis 120 process, during one or more discrete points during the oxidation 140 process, and so on. The removed soluble products may then be directed to a post-treating 160 step, as described above and the result liquid 122, e.g., acetic acid, recycled back to the reactor for reuse in the disclosed processes.In some embodiments of the present disclosure, an oxidizing step may be completed before a solvolysis step. In some embodiments of the present disclosure, an oxidizing step may be completed after a solvolysis step. In some embodiments of the present disclosure, an oxidizing step may be completed simultaneously with a solvolysis step.EXPERIMENTAL RESULTSWhat follows are specific examples of solvolysis and oxidation reactions performed by the instant inventors. Unless otherwise stated, experiments were performed on an individual type of plastic by itself, not in a mixed plastics setting. Additionally, unless otherwise stated, solvolysis occurred via acetolysis, as a carboxylic acidolysis, the exchange reaction occurring between a carboxylic acid present in acetic acid and an ester bond present in the plastic.Figures 2A and 2B illustrate the deconstruction of Nylon 6 and Nylon 6,6, respectively, by acetolysis (solvolysis via the use of acetic acid) according to some embodiments of the present disclosure. Reaction conditions were 1 gram of plastic (either Nylon 6 or Nylon 6,6) immersed in acetic acid at about 5 wt% of the plastic relative to the total weight. The reactions were performed under a nitrogen (N2) atmosphere at 25 bar. The acetolysis was completed at temperatures of 180 °C - 280 °C for the time periods shown, which range from 30 minutes - four hours. Gas chromatography-mass spectroscopy was utilized to measure the final concentrations of degradation products, acetyl amino caproic acid for Nylon 6 and each of acetyl amino caproic acid, diacetyl hexamethylene diamine, and adipic acid for Nylon 6,6.In particular, as seen in Figure 2A, Nylon 6 can be deconstructed into acetyl amino caproic acid by the solvolysis methods disclosed herein. Data sets compiled for decreasing temperatures are presented. Generally, higher yields of deconstruction products are seen at higher temperatures in a shorter amount of time, with the total amount of deconstruction products obtained after 30 minutes at 280 °C far exceeding those seen at 180 °C, although similar results can be seen for each of the data sets represented by 240 °C, 260 °C, and 280 °C.Similar trends can be seen in Figure 2B, confirming that Nylon 6,6 can be deconstructed into acetyl amino caproic acid, diacetyl hexamethylene diamine, and adipic acid via the solvolysis methods disclosed herein. As with Figure 2A, higher yields of deconstruction products are seen at higher temperatures in a shorter amount of time, with the total amount of deconstruction products obtained after 30 minutes at 280 °C far exceeding those seen at 180 °C, although similar results can be seen for each of the data sets represented by 260 °C and 280 °C.In these Figure 2 examples, C-N bonds of the Nylon 6 and Nylon 6,6 were efficiently cleaved in about 30 minutes by acetic acid during solvolysis at temperatures of about 240 °C - 280 °C (Nylon 6) and about 260 °C - 280 °C (Nylon 6,6).Figures 3A, 3B, and 3C illustrate deconstruction results of polyethylene terephthalate (PET) by acetolysis, according to some embodiments of the present disclosure. Reaction conditions were 1 gram of PET immersed in only acetic acid at about 5 wt% of the PET relative to the total weight. The reactions were performed under a nitrogen (N2) atmosphere at 25 bar. The acetolysis was completed at temperatures of 220 °C - 280 °C for the time periods shown, which range from 30 minutes - four hours. Gas chromatography-mass spectroscopy was utilized to measure the final concentrations of degradation products, including terephthalic acid, ethylene glycol, ethylene glycol monoacetate, and ethylene glycol diacetate.In particular, PET is shown as deconstructed into terephthalic acid (TP A), ethylene glycol monoacetate (EGMA), and ethylene glycol diacetate (EGDA). Figure 3A depicts the production of TPA via acetolysis at varying hours and temperatures. Generally, higher yields of TPA are seen at higher temperatures in a shorter amount of time, with the total amount of deconstruction products obtained after 30 minutes at 280 °C far exceeding those seen at 220 °C. Additionally, higher yields of TPA were shown at longer solvolysis times, with 2 hours depicting the highest TPA yield seen.Similar results are shown for TPA production in Figure 3A, which depicts the production of TPA via acetolysis at varying hours and temperatures. Again, higher yields of TPA are seen at higher temperatures in a shorter amount of time, with the total amount of deconstruction products obtained after 30 minutes at 280 °C far exceeding those seen at 220 °C. Additionally, while higher yields of TPA were shown at longer solvolysis times, with 2 hours again depicting the highest TPA yield seen, even longer solvolysis times did not appear to produce higher yields. These data show that TPA production via acetolysis appears to peak at solvolysis conditions of 280 °C for 2 hours.Figure 3B shows the production of EGMA and EGDA at varying hours and temperatures. Generally, higher yields of both EGMA and EGDA are seen at higher temperatures in a shorter amount of time, with the total amount of deconstruction products obtained after 30 minutes at 280 °C far exceeding those seen at 220 °C. Additionally, while higher yields of EGDA were obtained at longer solvolysis times, with 2 hours depicting the highest diacetate (EGDA) yield seen, longer solvolysis times did appear to result in a decrease of production of the monoacetate (EGMA).In these Figure 3 examples, efficient TPA production was achieved in about 2 hours by acetolysis at a temperature of about 280 °C. Similar results were seen with the production of EGDA, while EGMA production appears to have peaked, according to these data, after 30 minutes at about 280 °C.An assessment of acetolysis of polycarbonates in provided in Figure 4. A polycarbonate may be deconstructed into products such as bisphenol A (BP A), monoacetylated bisphenol A (MABPA), diacetylated bisphenol A (DABPA), phenol (Ph), phenyl acetate (PA), or 4- isopropylphenyl acetate (IPPA).Figure 4 illustrates photographs of a starting polycarbonate (PC-1) film, as well as solid / liquid mixtures resulting from acetolysis of the starting polycarbonate, according to some embodiments of the present disclosure. Two separate acetolysis reactions were performed.First, the polycarbonate starting material was subjected to acetolysis for a period of 2 hours at five separate temperatures, 200 °C, 220 °C, 240 °C, 260 °C, and 280 °C. The reactions were set up such that the only difference between each reaction was the temperature. As shown in Figure 4, deconstruction products were generated at each temperature; evaluation of the presence of deconstruction products occurred visually, with the acetolysis solutions either changing color and / or becoming cloudy. The photographs of samples provided on the left side of this figure clearly indicate, by color change, that the polycarbonate was at least partially deconstructed as a result of acetolysis. Generally speaking, more deconstruction products can be seen in the samples taken at higher temperatures, as evidenced by darker coloration.Second, the polycarbonate starting material was subjected to acetolysis at a single temperature, 280 °C, for 6 different time points, 30 minutes, 1 hour, 2 hours, 3 hours, 4 hours, and 6 hours. The reactions were set up such that the only difference between each reaction was the duration of time acetolysis was performed. As shown in Figure 4, deconstruction products were generated at each time point; evaluation of the presence of deconstruction products occurred visually, with the acetolysis solutions either changing color and / or becoming cloudy. The photographs of samples provided on the right side of this figure clearly indicate, by color change, that the polycarbonate was at least partially deconstructed as a result of acetolysis. Generally speaking, more deconstruction products can be seen in the samples taken at longer periods of time, as evidenced by darker coloration.In this Figure 4 example, polycarbonate is shown to break down by acetolysis in a time and / or temperature-dependent manner, with more deconstructions products seen at higher temperatures and longer periods of time.Each of the foregoing examples, which are summarized in Figures 2-4, provides data showing that each of Nylon 6 / Nylon 6,6 (Figure 2), polyethylene terephthalate (PET, Figure 3), and polycarbonate (Figure 4) can be successfully deconstructed using acetolysis. These data also show that all three of these plastics can be successfully deconstructed via acetolysis performed under similar conditions, for example similar temperatures and times. It is therefore reasonable to conclude that these varied plastics can be deconstructed together via solvolysis, using similar solvents, times and temperatures, without the need to sort the plastics individually.Figures 5A, 5B, 5C, and 5D illustrate deconstruction results of polyethylene (PE) by oxidation, according to some embodiments of the present disclosure.The data shown in Figure 5A are from experiments conducted with 350 grams of PE immersed in acetic acid, using both Co(OAc)2 at 9.7 wt% and Mn(0Ac)2 at 9.5 wt% as catalysts and either NHPI or NaBr as an initiator, in the weight percentages shown. The two initiators were tested separately, in triplicate. These oxidizing reactions were performed at 160 °C, under an atmosphere of 8 bar O2 and 72 barN2, for a total of 2.5 hours. The amount of PET deconstructed to oligomers of different lengths, between C11 and C22 (z.e., having between 11 and 22 carbon atoms, inclusively), C7 and C10, and C4 and Ce was determined.Figure 5B summarizes the results of oxidizing PE using 0.5 wt% NaBr as the initiator for different reaction times. 350 mg of PE were combined and reacted with 20 ml of acetic acid. Both CO(OAC)2 at 9.7 wt% and Mn(0Ac)2 at 9.5 wt% were used as catalysts and oxidation proceeded at 160 °C, under an atmosphere of 8 bar O2 and 72 bar N2, for a total of 2.5 hours. The amount of PET deconstructed to oligomers of different lengths, between C10 and C22, C7 and C10, and C4 and Ce, was determined.The amount of oligomers generated via oxidation increased from time points 0.5 hours - 3.0 hours. The results between the time points 3.0 and 3.5 hours appeared to be similar, with slight loss in the total amount of C7 - C10 oligomers shown at time point 3.5 hours.Figure 5C summarizes experimental results evaluating the effect of cobalt catalyst loading on the oxidizing of PET, using a constant 0.5 wt% of NaBr initiator and a constant 9.5wt% of cocatalyst Mn(0Ac)2. A total of 6 experiments were conducted, with the cobalt concentration varying between each at 0 wt%, 1 wt%, 2 wt%, 4 wt%, 8 wt%, and 9.7 wt% of cobalt. 350 mg of PE were combined and reacted with 20 ml of acetic acid; oxidation proceeded at 160 °C, under an atmosphere of 8 bar O2 and 72 bar N2, for a total of 2.5 hours. The amount of PET deconstructed to oligomers of different lengths, between C10 and C22, C7 and C10, and C4 and Ce, was determined.These data show that the efficiency of deconstruction of PET via oxidation can be increased with increasing cobalt concentration.Figure 5D summarizes experimental results evaluating the effect of both cobalt and manganese catalyst loadings on the oxidizing of PET, using a constant 0.5 wt% of NaBr initiator. A total of 6 experiments were run, with the Co / Mn concentrations changing across each as follows (all percentages shown are wt%): 0% / 0%, l% / 0.97%, 2% / 1.96%, 4% / 3.88%, 8% / 7.79%, and9.7% / 9.5%. 350 mg of PE were combined and reacted with 20 ml of acetic acid; oxidation proceeded at 160 °C, under an atmosphere of 8 bar O2 and 72 bar N2, for a total of 2.5 hours. The amount of PET deconstructed to oligomers of different lengths, between C11 and C22, C7 and C10, and C4 and Ce, was determined.These data show that the efficiency of deconstruction of PET via oxidation can be increased with increasing concentration of cobalt / manganese catalysts.Figure 6 lists examples of deconstruction products resulting from the oxidation of PE, according to some embodiments of the present disclosure. The chemical formulas and molecular weights are provided for each.Figure 7A and 7B illustrate comparisons of the results of acetolysis and oxidation of common, plastic-containing materials, according to some embodiments of the present disclosure. In these experiments, acetolysis and oxidation were performed separately. Regarding Figure 7A, yields are of TPA concentration after depolymerization of several postconsumer materials including (from left to right) - a 50% cotton / 50% polyester fabric from a sweater, a 7% polyurethane / 93% polyester fabric from exercise shorts, 100% polyester fabric from a fleece sweater, PET grade A flake, and PET from a Dr. Pepper soda bottle. Blue is yields after oxidation of these materials, yellow is yields after acetolysis of these materials. Regarding Figure 7B, yields of ethylene glycol, ethylene glycol monoacetate, and ethylene glycol diacetate under the same conditions as for Figure 7A.Figure 8 illustrates a series of processes for deconstructing mixed plastics, according to embodiments of the present disclosure. Each of the processes shown in Figure 8 begin with a starting feedstock of polyesters (PET), polyurethanes (PU), nylons, polypropylene (PP), and polyethylene (PE).Process 1, as illustrated in Figure 8, provides that when a feedstock containing PET, PU, nylons, PP, and PE undergoes a process of acidolysis at high temperatures without oxygen present during the reaction, these plastics can be successfully deconstructed yielding PU, nylons, and ethylene glycol diacetate (EGDA) as soluble deconstruction products and terephthalic acid (TPA), PP, and PE as insoluble, solid products. EGDA is a co-monomer generated from depolymerization of PET, and TPA is a co-monomer generated from depolymerization of PET. The process of acidolysis may be completed using one or more appropriate solvents. Non-limiting examples of solvents that may be used for Process 1 mayinclude levulinic acid, benzoic acid, 2-methoxyacetic acid, succinic acid, monomethyl ester, octanoic acid, caproic acid, valeric acid, 2-methoxybenzoic acid, and 4-methoxybenzoic acid.Process 2, as illustrated in Figure 8, provides that when a feedstock containing PET, PU, nylons, PP, and PE undergoes a process of acidolysis at high temperatures coupled with the addition of oxygen, these plastics can be successfully deconstructed yielding PU, nylons, EGDA, PP, and PE as soluble deconstruction products and TPA s insoluble, solid products. The process of acidolysis may be completed using one or more appropriate solvents. Nonlimiting examples of solvents that may be used for Process 2 may include levulinic acid, benzoic acid, 2-methoxyacetic acid, succinic acid, monomethyl ester, octanoic acid, caproic acid, valeric acid, 2-methoxybenzoic acid, and 4-methoxybenzoic acid.Process 3, as illustrated in Figure 8, provides that when a feedstock containing PET, PU, nylons, PP, and PE undergoes a process of acidolysis at sequential temperatures (e.g., where the temperature is changed during the course of acidolysis) coupled with an inert environment and / or addition of oxygen, these plastics can be successfully deconstructed yielding PU and nylons as sequentially soluble deconstruction products and TPA and EGDA as insoluble, solid products. The process of acidolysis may be completed using one or more appropriate solvents. Non-limiting examples of solvents that may be used for Process 3 may include levulinic acid, benzoic acid, 2-methoxyacetic acid, succinic acid, monomethyl ester, octanoic acid, caproic acid, valeric acid, 2-methoxybenzoic acid, and 4-methoxybenzoic acid. The temperature at which acidolysis occurs can vary. In some embodiments, the temperature is increased during acidolysis. In other embodiments, the temperature is decreased during acidolysis.Process 4, as illustrated in Figure 8, provides that when a feedstock containing PET, PU, nylons, PP, and PE undergoes a process of oxidation in the presence of Co / Mn / Br, these plastics can be successfully deconstructed yielding TPA as an insoluble, solid product.Figure 9 illustrates an annotated schematic of acidolysis according to Process 1 of Figure 8, in accordance with embodiments of the present disclosure. In particular, Figure 9 clarifies that while TPA, PP, and PE are generated as solid deconstruction products, PU, Nylons, and EGDA are generated as soluble products.Figure 10 illustrates examples of deconstructed Patagonia recircled materials consistent with Process 1 of Figure 8, in accordance with embodiments of the present disclosure. As seen in Figure 10, deconstructed components are illustrated as a percentage of liquid components and as a percentage of recovered solid components, respectively. Each of the green, blue, red,brown, and black recircled materials was tested in its own experiment. For each experiment, 5 wt% solid in solution was used, e.g. one gram of solid per 20g of an acetic acid solution. Acetic acid was heated in an inert atmosphere to 280 °C with the substrates, resulting in deconstruction of the recircles materials and the generation of various condensation polymers (PET, PU, and nylons), leaving the additional polymers (PP and PE) intact. The products from nylon and PU depolymerization are soluble under these conditions, whereas the TPA generated from PET, as well as the unreacted PP and PE, will remain solids at the end of the reaction.Figure 11 illustrates process steps 3A and 3B of Figure 8, according to embodiments of the present disclosure. In step 3 A, the temperature is sequentially increased in order to deconstruct first PU, then nylons, then PET, and collect deconstruction products as they are evolved. The process illustrated in this step occurs in the absence of added oxygen. First, acidolysis is performed at 140 °C - 160 °C in order to selectively deconstruct PU. While this first acidolysis step is happening, the soluble PU deconstruction products are filtered out of the acidolysis solution, to separate them from the rest of the materials and to help drive the acidolysis of PU to completion. Second, the temperature of the acidolysis reaction is increased to 200 °C - 240 °C in order to selectively deconstruct the nylons. Again, as acidolysis is occurring, the acidolysis solution is filtered in order to separate the unreacted, solid materials from the soluble nylon deconstruction products as they are evolved, and to help drive the reaction to completion. Third, the temperature of the acidolysis is increased to 280 °C, in order to selectively depolymerize PET to obtain TPA and unreacted PP and PE.In step 3B, the process is essentially the same as 3 A, except with the introduction of oxygen as described herein. Oxidation is therefore allowed to occur at the same time as acidolysis, as described herein. In this case, the soluble PP and PE deconstructions products from oxidation of these substrates will be removed at the first separation, along with the soluble PU deconstruction products.Figure 12 illustrates examples of deconstructed Patagonia recircled polymer materials consistent with Process 3 of Figure 8, according to embodiments of the present disclosure. As seen in this process, the temperature is increased in stages in order to separate out the products of the various inputs over the course of the reaction. This can be done using either set of conditions from scenario (1) or (2) above, as 3A or 3B, respectively, with or without oxygen in the headspace.Figure 13 illustrates the solubility of PU at lower temperatures, according to embodiments of the present disclosure. This is outlined in Process 3 of Figure 8 to separate the material from solid products. Additionally, this illustration also identifies some of the various monomers that are able to be obtained using Process 3 of Figure 8.Figure 14 illustrates the deconstruction of nylon into soluble products, according to embodiments of the present disclosure. This is also outlined in Process 3 of Figure 8. On the right hand side of this figure, deconstruction products of nylon obtained after acetolysis at 220 °C performed for 30 minutes, 1 hour, and 2 hours have been identified and quantified. In this example, the quantity of deconstruction generally increases the longer acetolysis is allowed to occur.Figure 15 illustrates the generation of TPA after increasing the temperature to 280 °C in an acidolysis reaction that had initially contained both nylon and PET, according to embodiments of the present disclosure. This also illustrates the ability to separate materials sequentially as described in Process 3 of Figure 8. As seen in Figure 15, the separation of TPA into a solid phase is not 100% completed.Figure 16 illustrates conversion of polyester-containing fabrics to soluble products, gaseous products, or TPA, according to embodiments of the present disclosure. As seen in Figure 16, #6 is a polyester / polyurethane blend; in #4, both purple and green are both 100% polyester sweater fabric; and #7 is 100% polyester jacket fabric. In particular, as shown in Figure 16, the starting materials are reacted in acetic acid under an oxidative environment (typically 10% O2 in N2) in the presence of cobalt acetate, manganese acetate, and sodium bromide. These oxidation conditions result in the complete deconstruction of all plastics (PP, PE, Nylons, PU) to soluble or gaseous products, with the exception of PET, which is converted to TPA. Figure 16 further illustrates a variety of substrates that include PET as well as PU. This reaction has been conducted on all of the listed polymers, with the only solid product obtained being TPA.Figure 17 illustrates the production of MEET and TPA in accordance with embodiments of the present disclosure. Figure 17 also illustrates components that contain TPA. In particular, Figure 17 illustrates TPA and MEET yields from the various materials shown in Figure 16 after oxidation.Low-Pressure Acidolysis of condensation polymersIn addition to the discussion provided hereinabove, there are further approaches towards implementing low-pressure acylolysis (acidolysis) systems for the depolymerization of PET(and other condensation polymers). For example, additional methods and systems are provided for providing a scalable system for PET depolymerization with readily available carboxylic acids under low-pressure conditions. In some embodiments, non-limiting examples of one or more carboxylic acids may include levulinic acid, benzoic acid, 2-methoxyacetic acid, succinic acid monomethyl ester, octanoic acid, caproic acid, valeric acid, 4-methoxybenzoic acid, and 2-methoxybenzoic acid.Levulinic AcidLevulinic acid benefits from being a bio-derived solvent that is currently undergoing further R&D to optimize production yields and separations.To a 500 mL round bottom flask equipped with a stir bar was added levulinic acid (100 g, 0.86 mol - can be lower or higher wt% of levulinic acid) and waste polyester fabric swatches (10 g, 8.6 g w / r / t TPA wt% in polymer, 0.052 mol). The flask was capped and placed in a heating oil bath (a heating block may also be used) on a magnetic stir plate which was set to heat to 220 °C (or between 180-250 °C, depending on solvent identity) for 18 hours (can be lower or higher time depending on temperature and solvent). Upon elapsed reaction time, a conversion of fabric to fine powder was observed, and reaction was set to cool to room temperature. The mixture was then vacuum filtered using a Buchner funnel and impure terephthalic acid was washed with acetone to obtain crude TPA (7.3 g, 85% yield w / r / t TPA).Benzoic AcidBenzoic acid benefits from potential sourcing from waste polystyrene. It is easy to purify by sublimation.To a 500 mL round bottom flask equipped with a stir bar was added benzoic acid (100 g, 0.82 mol - can be lower or higher wt% of benzoic acid) and waste polyester fabric swatches (10 g, 8.6 g w / r / t TPA wt% in polymer, 0.052 mol). The flask was capped and placed in a heating oil bath (a heating block may also be used) on a magnetic stir plate which was set to heat to 220 °C (or between 180-250 °C, depending on solvent identity) for 18 hours (can be lower or higher time depending on temperature and solvent). Upon elapsed reaction time, a conversion of fabric to fine powder was observed, and reaction was set to cool to room temperature. The mixture solidified and excess benzoic acid was dissolved in ethanol (2x50 mL). The mixture was then vacuum filtered using a Buchner funnel and impure terephthalic acid was washed with acetone to obtain crude TPA (6.2 g, 72% molar yield w / r / t TPA).ExamplesExample 1. A method of deconstructing mixed plastics, comprising: solvolysis of a first fraction of the mixed plastics, and oxidation of a second fraction of the mixed plastics in the presence of oxygen, wherein: the solvolysis deconstructs the first fraction to a first compound, and the oxidation deconstructs the second fraction to a second compound.Example 2. The method of Example 1, wherein the solvolysis is performed before the oxidation.Example 3. The method of either Example 1 or Example 2, wherein the oxidation is performed before the solvolysis.Example 4. The method of any one of Examples 1-3, wherein the solvolysis and the oxidation are performed simultaneously.Example 5. The method of any one of Examples 1-4, wherein the solvolysis and / or the oxidation are performed in a reactor.Example 6. The method of any one of Examples 1-5, wherein the solvolysis and the oxidation are performed in the same reactor.Example 7. The method of any one of any one of Examples 1-6, wherein the mixed plastics comprise at least two different types of plastic.Example 8. The method of any one of Examples 1-7, wherein the mixed plastics are selected from two or more of a polyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, or polyethylene terephthalate.Example 9. The method of any one of Examples 1-8, wherein the solvolysis occurs by contacting the first fraction with a first liquid.Example 10. The method of any one of Examples 1-9, wherein the first liquid is selected from acetic acid, water, or both acetic acid and water.Example 11. The method of any one of Examples 1-10 or Example 10, wherein the first liquid further comprises hydrochloric acid, sulfuric acid, or both hydrochloric and sulfuric acid.Example 12. The method of any one of Examples 1-11, wherein the solvolysis is performed at a temperature selected from 22 °C - 300 °C or 120 °C - 280 °C.Example 13. The method of any one of Examples 1-12, wherein the solvolysis is performed for 0.5 hours - 4 hours.Example 14. The method of any one of Examples 1-13, wherein the first fraction comprises chemical bonds capable of being broken by the first liquid.Example 15. The method of any one of Examples 1-14, wherein the polyamide is selected from the group consisting of polycaprolactam (Nylon 6), poly[imino(l,6- dioxohexamethylene)iminohexamethylene] (Nylon 6,6), and both Nylon 6 and Nylon 6,6.Example 16. The method of any one of Examples 1-15, wherein the polyamide is selected from Nylon 11, Nylon 12, or both Nylon 11 and Nylon 12.Example 17. The method of any one of Examples 1-16, wherein the polycarbonate is 1,2- diacyl-sn-glycero-3-phosphocholine.Example 18. The method of any one of Examples 1-17, wherein the first compound is soluble in the first liquid.Example 19. The method of any one of Examples 1-18, further comprising separating the first compound from the first liquid.Example 20. The method of any one of Examples 1-19, wherein the first compound is separated from the first liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof.Example 21. The method of any one of Examples 1-20, wherein the second fraction is present as a solid.Example 22. The method of any one of Examples 1-21, wherein the oxidation occurs by contacting the second fraction with a second liquid.Example 23. The method of any one of Examples 1-22, wherein the second liquid comprises water, acetic acid, para-xylene, or any combination of thereof.Example 24. The method of any one of Examples 1-23, wherein the second liquid further comprises benzoic acid.Example 25. The method of any one of Examples 1-24, wherein the second liquid further comprises an initiator.Example 26. The method of any one of Examples 1-25, wherein the initiator is N-hydroxypthalimide (NHPI), NaBr, or both NHPI and NaBr.Example 27. The method of any one of Examples 1-26, wherein the second liquid further comprises a catalyst.Example 28. The method of any one of Examples 1-27, wherein the catalyst comprises a transition metal.Example 29. The method of any one of Examples 1-28, wherein the transition metal comprises cobalt, manganese, or both cobalt and manganese.Example 30. The method of any one of Examples 1-29, wherein the oxidation is performed at a temperature selected from 22 °C - 300 °C or 140 °C - 180 °C.Example 31. The method of any one of Examples 1-30, wherein the oxidation is performed for 1 hour - 6 hours.Example 32. The method of any one of Examples 1-31, wherein the oxidation is performed at pressure of 1 - 200 bar or 10 - 80 bar of oxygen and inert gas.Example 33. The method of any one of Examples 1-32, wherein the oxidation is performed at an oxygen concentration of 0.1 mol% - 50 mol% or 5 mol% - 20 mol%.Example 34. The method of any one of Examples 8-33, wherein the first fraction comprises the polyolefin.Example 35. The method of any one of Examples 1-34, wherein the polyolefin is selected from the group consisting of polyethylene, polypropylene, and both polyethylene and polypropylene.Example 36. The method of any one of Examples 1-35, further comprising separating the second compound from the second liquid.Example 37. The method of any one of Examples 1-36, wherein the second compound is separated from the second liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof.Example 38. The method of any one of Examples 1-37, wherein the second liquid further comprises benzoic acid and wherein the oxidation is performed at a pressure between 1 bar and 10 bar.Example 39. The method of any of Examples 1-18, wherein the oxidation is performed at a pressure between 1 bar and 10 bar.Example 40. A method of deconstructing mixed plastics, the method comprising: providing a feedstock that comprises polyesters (PET), polyurethanes (PU), nylons, polypropylene (PP), and polyethylene (PE); and initiating a first acidolysis process at a first temperature withoutoxygen present during the reaction, thereby selectively deconstructing PU; initiating a second acidolysis process at a second temperature without oxygen present during the reaction, thereby selectively deconstructing nylon; initiating a third acidolysis process at a third temperature without oxygen present during the reaction, thereby selectively depolymerize PET to obtain TPA, unreacted PP, and unreacted PE.Example 41. The method of Example 40, wherein the first temperature is between 140 °C and 160 °C.Example 42. The method of either Example 40 or Example 41, wherein the first temperature is about 140 °C.Example 43. The method of any one of Examples 40-42, wherein the first temperature is about 150 °C.Example 44. The method of any one of Examples 40-43, wherein the first temperature is about 160 °C.Example 45. The method of any one of Examples 40-44, wherein the second temperature is between 200 °C and 240 °C.Example 46. The method of any one of Examples 40-45, wherein the first temperature is about 200 °C.Example 47. The method of any one of Examples 40-46, wherein the first temperature is about 220 °C.Example 48. The method of any one of Examples 40-47, wherein the first temperature is about 240 °C.Example 49. The method of any one of Examples 40-48, wherein the third temperature is about 280 °C.Example 50. The method of any one of Examples 40-49, wherein at least some of the deconstructed PU is removed while at least a portion of the first reaction is occurring.Example 51. The method of any one of Examples 40-50, wherein at least some of the deconstructed nylon is removed while at least a portion of the second reaction is occurring.Example 52. A method of deconstructing mixed plastics, comprising: contacting a first fraction of the mixed plastics with a first liquid, and oxidizing a second fraction of the mixed plastics,wherein: the contacting deconstructs the first fraction to a first compound, and the oxidizing deconstructs the second fraction to a second compound.Example 53. The method of Example 52, wherein the contacting is performed before the oxidizing.Example 54. The method of either Example 52 or Example 53, wherein the oxidizing is performed before the solvolysis.Example 55. The method of any one of Examples 52-54, wherein the contacting and the oxidizing are performed simultaneously.Example 56. The method of any one of Examples 52-55, wherein the contacting and / or the oxidizing are performed in a reactor.Example 57. The method of any one of Examples 52-56, wherein the contacting and the oxidizing are performed in the same reactor.Example 58. The method of any one of Examples 52-57, wherein the mixed plastics comprise at least two different types of plastic.Example 59. The method of any one of Examples 52-58, wherein the mixed plastics are selected from two or more of a polyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, or polyethylene terephthalate.Example 60. The method of any one of Examples 52-59, wherein the mixed plastics are selected from three or more of a polyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, or polyethylene terephthalate.Example 61. The method of any one of Examples 52-60, wherein the first liquid is selected from acetic acid, water, or both acetic acid and water.Example 62. The method of any one of Examples 52-61, wherein the first liquid further comprises hydrochloric acid, sulfuric acid, or both hydrochloric and sulfuric acid.Example 63. The method of any one of Examples 52-62, wherein the contacting is performed at a temperature selected from 22 °C - 300 °C or 120 °C - 280 °C.Example 64. The method of any one of Example s52-63, wherein the contacting is performed for 0.5 hours - 4 hours.Example 65. The method of any one of Examples 60-64, wherein the first fraction comprises chemical bonds capable of being broken by the first liquid.Example 66. The method of any one of Examples 59-65, wherein the polyamide is selected from the group consisting of polycaprolactam (Nylon 6), poly[imino(l,6- dioxohexamethylene)iminohexamethylene] (Nylon 6,6), and both Nylon 6 and Nylon 6,6.Example 67. The method of any one of Examples 59-66, wherein the polyamide is selected from Nylon 11, Nylon 12, or both Nylon 11 and Nylon 12.Example 68. The method of any one of Examples 59-67, wherein the polycarbonate is 1,2- diacyl-sn-glycero-3-phosphocholine.Example 69. The method of any one of Examples 52-68, wherein the first compound is soluble in the first liquid.Example 70. The method of any one of Examples 52-69, further comprising separating the first compound from the first liquid.Example 71. The method of any one of Examples 52-70, wherein the first compound is separated from the first liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof.Example 72. The method of any one of Examples 52-71, wherein the second fraction is present as a solid.Example 73. The method of any one of Examples 52-72, wherein the oxidizing occurs by contacting the second fraction with a second liquid.Example 74. The method of any one of Examples 52-73, wherein the second liquid comprises water, acetic acid, para-xylene, or any combination of thereof.Example 75. The method of any one of Examples 52-74, wherein the second liquid further comprises benzoic acid.Example 76. The method of any one of Examples 52-75, wherein the second liquid further comprises an initiator.Example 77. The method of any one of Examples 52-76, wherein the initiator is N-hydroxypthalimide (NHPI), NaBr, or both NHPI and NaBr.Example 78. The method of any one of Examples 52-77, wherein the second liquid further comprises a catalyst.Example 79. The method of any one of Examples 52-78, wherein the catalyst comprises a transition metal.Example 80. The method of any one of Examples 52-79, wherein the transition metal comprises cobalt, manganese, or both cobalt and manganese.Example 81. The method of any one of Examples 52-80, wherein the oxidizing is performed at a temperature selected from 22 °C - 300 °C or 140 °C - 180 °C.Example 82. The method of any one of Examples 52-81, wherein the oxidizing is performed for 1 hour - 6 hours.Example 83. The method of any one of Examples 52-82, wherein the oxidizing is performed at pressure of 1 - 200 bar or 10 - 80 bar of oxygen and inert gas.Example 84. The method of any one of Examples 52-83, wherein the oxidizing is performed at an oxygen concentration of 0.1 mol% - 50 mol% or 5 mol% - 20 mol%.Example 85. The method of any one of Examples 59-84, wherein the first fraction comprises the polyolefin.Example 86. The method of any one of Examples 52-85, wherein the polyolefin is selected from the group consisting of polyethylene, polypropylene, and both polyethylene and polypropylene.Example 87. The method of any one of Examples 72-86, further comprising separating the second compound from the second liquid.Example 88. The method of any one of Examples 52-87, wherein the second compound is separated from the second liquid by mechanical filtration, size exclusion, density differences, near infrared sortation, centrifugation, or any combination thereof.The foregoing discussion and examples have been presented for purposes of illustration and description. The foregoing is not intended to limit the aspects, embodiments, or configurations to the form or forms disclosed herein. In the foregoing Detailed Description for example, various features of the aspects, embodiments, or configurations are grouped together in one or more embodiments, configurations, or aspects for the purpose of streamlining the disclosure. The features of the aspects, embodiments, or configurations, may be combined in alternate aspects, embodiments, or configurations other than those discussed above. This method of disclosure is not to be interpreted as reflecting an intention that the aspects, embodiments, or configurations require more features than are expressly recited in each claim. Rather, as the following claims reflect, inventive aspects lie in less than all features of a single foregoing disclosed embodiment, configuration, or aspect. While certain aspects of conventionaltechnology have been discussed to facilitate disclosure of some embodiments of the present invention, the Applicant in no way disclaims these technical aspects, and it is contemplated that the claimed invention may encompass one or more of the conventional technical aspects discussed herein. Thus, the following claims are hereby incorporated into this Detailed Description, with each claim standing on its own as a separate aspect, embodiment, or configuration.

Claims

CLAIMSWhat is claimed is:

1. A method of deconstructing mixed plastics, comprising: solvolysis of a first fraction of the mixed plastics, and oxidation of a second fraction of the mixed plastics in the presence of oxygen, wherein: the solvolysis deconstructs the first fraction to a first compound, and the oxidation deconstructs the second fraction to a second compound.

2. The method of claim 1, wherein the solvolysis is performed before the oxidation.

3. The method of claim 1, wherein the oxidation is performed before the solvolysis.

4. The method of claim 1, wherein the solvolysis and the oxidation are performed simultaneously.

5. The method of claim 1, wherein the mixed plastics are selected from two or more of a polyamide, a polycarbonate, a polyolefin, a polyurethane, a cellulose, a polyoxymethylene, or polyethylene terephthalate.

6. The method of claim 1, wherein the solvolysis occurs by contacting the first fraction with a first liquid.

7. The method of claim 6, wherein the first liquid is selected from acetic acid, water, or both acetic acid and water.

8. The method of 7, wherein the first liquid further comprises hydrochloric acid, sulfuric acid, or both hydrochloric and sulfuric acid.

9. The method of claim 5, wherein the polyamide is selected from the group consisting of polycaprolactam (Nylon 6), poly[imino(l,6-dioxohexamethylene)iminohexamethylene] (Nylon 6,6), and both Nylon 6 and Nylon 6,6.

10. The method of claim 5, wherein the polycarbonate is l,2-diacyl-sn-glycero-3- phosphocholine.

11. The method of claim 1, further comprising separating the first compound from the first liquid.

12. The method of any one of claims 1, wherein the oxidation occurs by contacting the second fraction with a second liquid.

13. The method of claim 12, wherein the second liquid comprises water, acetic acid, paraxylene, or any combination of thereof.

14. A method of deconstructing mixed plastics, the method comprising: providing a feedstock that comprises polyesters (PET), polyurethanes (PU), nylons, polypropylene (PP), and polyethylene (PE); initiating a first acidolysis process at a first temperature without oxygen present during the reaction, thereby selectively deconstructing PU; initiating a second acidolysis process at a second temperature without oxygen present during the reaction, thereby selectively deconstructing nylon; and initiating a third acidolysis process at a third temperature without oxygen present during the reaction, thereby selectively depolymerize PET to obtain TPA, unreacted PP, and unreacted PE.

15. A method of deconstructing mixed plastics, comprising: contacting a first fraction of the mixed plastics with a first liquid, and oxidizing a second fraction of the mixed plastics, wherein: the contacting deconstructs the first fraction to a first compound, and the oxidizing deconstructs the second fraction to a second compound.

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