Pitch produced from aromatic feeds

Abstract

Methods, systems, and compositions involving forming isotropic pitch by reacting an aromatic hydrocarbon feed and a linker in the presence of a catalyst, and forming mesophase pitch by heating the isotropic pitch.

Description

PITCH PRODUCED FROM AROMATIC FEEDSFIELD

[0001] Systems and methods are provided for producing mesophase pitch or amorphous carbon from isotropic pitch formed from aromatic hydrocarbons.BACKGROUND

[0002] Conversion of hydrocarbons to structured carbon materials for composites or battery applications can be a driver for carbon materials. Petroleum byproducts with abundant aromatic fractions have been used to produce high-quality mesophase pitches due to their lower cost and melt processability options in comparison with polyacrylonitrile (PAN) precursors. Thus, one of the primary’ focus areas in this field is to synthesize mesophase pitch precursors from aromatic petroleum feedstocks in economically viable scalable routes. Further, softening point (Ts) and rheological properties (e.g., viscosity and spinnability) are generally correlated to the pitch chemistry, mesophase content, homogeneity7, and purity’ of the precursor materials. However, controlling all parameters utilizing conventional economically feasible synthetic techniques for various feedstocks remains challenging. Previously, synthetic pitches prepared by oligomerization of naphthalene using hydrogen fluoride / boron trifluoride (HF / BF3) catalyst addressed some of the aforementioned concerns (e.g., homogeneity, spinnability, purity, etc.), though the super acid catalyst used in this chemistry raised concerns about the process and operational efficacy .SUMMARY

[0003] Disclosed herein is an example method of producing mesophase pitch for further processing, the method comprising: forming isotropic pitch by reacting components comprising an aromatic hydrocarbon feed and a linker in presence of a catalyst at a first temperature, yvherein the isotropic pitch compnses a weight average molecular weight (Mw) of about 150 grams per mole (g / mol) to about 1,500 g / mol, a softening point (Tsp) of 50 °C or greater, and a micro carbon residue (MCR) of about 5 w eight percent (wt%) or greater based on total weight of the isotropic pitch; and forming the mesophase pitch by heating the isotropic pitch at a second temperature.

[0004] Further disclosed herein is an example mesophase pitch comprising: a first softening point in a first range of 200 °C to 450 °C; a mesophase content in a range of 0.01 volume percent (vol%) to 100 vol%; wherein the mesophase pitch is produced from an isotropic pitch at a temperature in a temperature range of 300 °C to 500 °C, and wherein the isotropic pitch comprises a second softening point in a second range of 200 °C to 400 °C; and wherein the isotropic pitch is derived, without acetic acid, from an aromatic hydrocarbon feed and a linker comprising trioxane.

[0005] These and other features and attributes of the disclosed methods and systems of the present disclosure and their advantageous applications and / or uses will be apparent from the detailed description which follows.BRIEF DESCRIPTION OF THE DRAWINGS

[0006] To assist those of ordinary skill in the relevant art in making and using the subject matter hereof, reference is made to the appended drawings, wherein:

[0007] FIG. 1 is a diagram of examples of the catalyst in the synthesis of isotropic pitch.

[0008] FIG. 1A is a flow diagram of techniques to produce graphite or amorphous carbon from an aromatic hy drocarbon feed

[0009] FIG. 2 is 'H nuclear magnetic resonance (NMR) spectra of isotropic pitches in the Examples.

[0010] FIG. 3, FIG. 4, FIG. 5, FIG. 6, and FIG. 7 are mass spectra of pitch materials in the Examples.

[0011] FIG. 8 is optical micrographs of mesophase pitches in the Examples.

[0012] Like reference numbers and designations in the various drawings indicate like elements.DETAILED DESCRIPTION

[0013] In various embodiments, systems and methods are provided for producing mesophase pitch or amorphous carbon, including first forming (synthesizing) isotropic pitch by reacting an aromatic hydrocarbon feed and a linker (e.g., trioxane, paraformaldehyde, etc.) in presence of a catalyst at a specified temperature. An aspect can be utilizing trioxane as the linker. Another aspect can be not including acetic acid in the reaction mixture for the synthesis of the isotropic pitch. The mesophase pitch (a mesophase pitch composition) is then formed by heating the isotropic pitch (an isotropic pitch composition) at another specified temperature. On the other hand, the amorphous carbon can be formed stabilizing by the isotropic pitch and then carbonizing the stabilized isotropic pitch.

[0014] To address issues with super acid catalyst and other issues, advances have been made in the chemistry’ of conversion of single aromatics to heavy hydrocarbon isotropic pitches utilizing acid catalyst (H2SO4). See, for instance, US Patent Application Publication No. 2024 / 0209208A1, which is incorporated by reference herein in its entirety. Acetic acid has been used as solvent for the synthesis of isotropic pitches. Advances have been made in the thermal conversion of isotropic pitch to mesophase pitches. See, for example, US Patent Application Publication No.2024 / 0182788A1, which is incorporated by reference herein in its entirety.

[0015] Unfortunately, acetic acid as a solvent can react with benzyl alcohol to form benz l ester. The acetic acid as solvent can also be an issue large scale production of isotropic pitches. Therefore, embodiments of the present techniques include production of isotropic pitches either (1) without acetic acid as solvent or (2) without solvent. Other embodiments can include solvent generally or acetic acid in particular.

[0016] Embodiments provide a scalable methodology and systems for synthesizing homogenous isotropic and mesophase pitches derived from single-ring aromatic feedstocks (e.g., xylene isomers). In the laboratory Examples presented below, isotropic pitches were prepared from xylene using trioxane as a linker and p-toluene sulfonic acid as a catalyst in bulk. This example technique facilitates to produce isotropic pitches without any solvent so the reaction can scale-up without any restriction of solvent. In the Examples, softening point and composition of the isotropic pitches were controlled by the concentration of trioxane and p-toluene sulfonic acid. Subsequently, in the Examples, the synthesized isotropic pitches were heat treated under nitrogen flow to achieve mesophase pitches with various softening points and mesophase content.

[0017] In the Examples, aromatic hydrocarbons were successfully converted to isotropic pitches using trioxane and p-toluene sulfonic acid. The softening point of the synthetic isotropic pitches ranged from 50 °C to 400 °C, which was controlled by the concentration of the linker and the catalyst. Mesophase pitches were achieved by heat treatment of the isotropic pitches under various conditions varying the temperature and time, which advanced control of the softening point and mesophase content of the mesophase pitch. These techniques give avenues to prepare synthetic pitches (e.g., high quality synthetic pitches) for battery anode applications and also as an outlet for hydrocarbon feedstocks.

[0018] Although mesophase pitch has been recognized as an excellent precursor for advanced carbon materials, better mesophase properties are continuously demanded for higher performance in production of mesophase and mesophase derived products. Pitches consisting of a series of components with unique structures have been prepared from definite starting substances through controlled reactions.. Two-step preparations of mesophase pitch have included: [1] a first step where single-ring aromatics such as xylenes are coupled by methylene (CPU) linkage through the condensation with paraformaldehyde in the presence of sulfuric acid as a catalyst and acetic acid as a solvent to produce isotropic pitch; and [2] a second step in which subsequently, the synthesized isotropic pitches are heat treated into the mesophase pitch. Such structures (e.g., unique structures) of mesophase pitches lead to controllable softening points, low melt-viscosity, and mesophase contents. In the present Examples, the chemical structures of the isotropic and mesophase pitchesderived from mix-xylenes were characterized to clarify the origins of their unique properties and structural requirements for development of the nature of the liquid cry stal.

[0019] Embodiments of the present techniques provide for producing mesophase pitch. Isotropic pitch can be formed by reacting an aromatic hydrocarbon feed and a linker (linking agent) in the presence of a catalyst at a temperature, for example, in a range of 50°C to 300 °C. Other applicable temperature ranges for the reaction temperature in the synthesis of the isotropic pitch include, for example. 90 °C to 140 °C. 40 °C to 400 °C, 60 °C to 300 °C, 70 °C to 250 °C, and 70 °C to 200 °C. The isotropic pitch is then subjected to heat as a thermal treatment (heat treatment) at a temperature, for example, in the range of 300 °C to 500 °C to give the mesophase pitch. Other applicable temperature ranges for this thermal treatment can include include, for example, 325 °C to 500 °C, 350 °C to 500 °C, 375 °C to 500 °C, 400 °C to 500 °C, 325 °C to 475 °C, 350 °C to 475 °C, 375 °C to 475 °C, and 350 °C to 450 °C, The synthesis of the isotropic pitch from aromatic hydrocarbon feed and the subsequent thermal treatment (heating) of the isotropic pitch to give the mesophase pitch can be performed in the same vessel or in different vessels.

[0020] In implementations, the forming the isotropic pitch is not performed in the presence of acetic acid. In implentations. the forming of the isotropic pitch is not performed in the presence of a solvent. The isotropic pitch formed (synthesized) can have a softening point, for example, in a range of 50 °C to 400 °C. Other softening point ranges of the formed isotropic pitch include, for example, 90 °C to 400 °C, 90 °C to 375 °C, 125 °C to 375 °C, 100 °C to 400 °C, and 125 °C to 400 °C. Other ranges for the softening point of the isotropic pitch can be applicable. The controlling of the softening point of the isotropic pitch can include adjusting the temperature of the reaction (temperature of the synthesis of the isotropic pitch). The controlling of the mesophase content of the mesophase pitch can include adjusting the heating time of the heating (the amount of time of the thermal treatment) of the isotropic pitch that gives the mesophase pitch. The mesophase content of the mesophase can be, for example, in the ranges of 0.01 volume percent (vol%) to 100 vol%, 1 vol% to 100 vol%, 1 vol% to 90 vol%, 1 vol% to 80 vol%, 3 vol% to 99 vol%, 3 vol% to 95 vol%, 3 vol% to 90 vol%, 3 vol% to 80 vol%, 5 vol% to 70 vol%, and 5 vol% to 60 vol%.

[0021] The aromatic hydrocarbon feed can include a single-ring aromatic compound(s) or a multi-ring aromatic compound(s). or both. Single-ring aromatic compounds (single-ring aromatics) are compounds having one aromatic ring. Single-ring aromatic compounds include, for example, benzene, toluene, xylene, tetralin, ethyl benzene, indene, etc., and can be labeled as a 1-ring aromatic or as having an aromatic class that is 1-ring aromatics. Multi-ring aromatic compounds (multi-ring aromatics) are compounds having multiple aromatic rings (more than one aromatic ring). For instance, a two-ring aromatic compound (e.g., naphthalenes, methylnaphthalenes, etc.) has two aromatic rings and can be labeled as a 2-ring aromatic or as having an aromatic class that is 2-ring aromatics. A three-ring aromatic compound has three aromatic rings (e.g., phenanthrenes, etc.) and can be labeled as a 3-ring aromatic or as having an aromatic class that is 3-ring aromatics.

[0022] The one or more aromatic classes of the aromatic hydrocarbon feed can be unsubstituted aromatics and / or substituted aromatics selected from the group consisting of l-ring aromatics (referring to aromatic compounds having a single aromatic ring), 2-ring aromatics (referring to aromatic compounds having two aromatic rings), 3-ring aromatics (referring to aromatic compounds having three aromatic rings), 4-ring aromatics, 5-ring aromatics, 6-ring aromatics, 7-ring aromatics, 8-ring aromatics, 9-ring aromatics, 10 or more-ring aromatics, and any combinations thereof. The general phrase "X-ring aromatics” is for aromatic classes in referring to aromatic compounds having “X” number of aromatic rings.

[0023] The aromatic hydrocarbon feed can include toluene, xylene, indene, naphthalene, anthracene, phenanthrene, or pyrene, crysene or any combinations thereof. For instance, the xylene can be mixed xylenes (xylene isomers). The xylene isomers can include o-xylene, m-xylene, and / or p-xylene. The aromatic hydrocarbon feed can include an aromatic mixed feed from a refinery. The aromatic hydrocarbon feed can include refinery bottoms, slurry oil, vacuum resid, cracker bottoms, main column bottoms (MCB), or heavy residue oil, or any combinations thereof.

[0024] The aromatic hydrocarbon feed can include benzene, toluene, xylene, indene, naphthalene, 1 -methyl naphthalene, 2-methyl naphthalene, anthracene, phenanthrene, pyrene, chrysene, benzopyrene, picenecoronene, chrysene, tetracene, pentacene, triphenylene, corannulene, benzo [j] fluoranthene, benzo[c]fluorene, perylene, benzo-perylene, ovalene, Aromatic-200™, or an aromatic mixed feed from a refinery, or any combinations thereof. As indicated, the xylene can include ortho-xylene, meta-xylene, or para-xylene, or any combinations thereof. Aromatic-200™ is an aromatic fluid manufactured by ExxonMobil Chemical Company having headquarters in Spring, Texas USA. Aromatic-200™ is a mixture of eleven carbon (Cll) aromatic hydrocarbons that is napthalene-depleted.

[0025] The linker can be a linker that is not aromatic, which can be labeled as a non-aromatic linker. The linker can be an aromatic linker, such as aromatic benzyl alcohols (e.g.. benzene dimethanol) and other aromatic linkers. The linker (linker molecule) may be involved in the connecting of components or molecules of the aromatic hydrocarbon feed to give the isotropic pitch. The reaction mixture (including the aromatic hydrocarbon feed, the linker, the catalyst, and any other compoments) to form (synthesize) the isotropic pitch can include the linker, for example in a range of 10% to 500% by weight of (based on) the aromatic hydrocarbon feed.

[0026] Examples of non-aromatic linkers include formaldehyde (e.g., as gas), formaldehyde in water (e.g., known as formalin that is formaldehyde solutions in water), paraformaldehyde, trioxane, and so forth. Both paraformaldehyde and trioxane are each a molecule that when heated can generate formaldehyde. The heating can occur, for example, when the reaction mixture having the aromatic hydrocarbon feed and the linker are heated in the forming (synthesis) of the isotropic pitch. Paraformaldehyde (a polymerized chain of formaldehyde molecules) is generally a solid version of formaldehyde that can be converted back into formaldehyde gas when heated.

[0027] Trioxane is a heterocyclic organic compound with a six-membered ring made up of three carbon atoms and three oxygen atoms. Trioxane (CsHeCh). also know n as 1,3,5-trioxane or trioxin, can be characterized as a cyclic trimer of formaldehyde. Trioxane (a cyclic molecule composed of three formaldehyde units linked together) breaks down when heated into three formaldehyde molecules and thus can be a source of formaldehyde (e.g., formaldehyde gas) when heated.

[0028] FIG. 1 gives examples of the catalyst. As depicted, the examples include aromatic rings (6 carbons). The example structures include the elements carbon (C), sulfur (S), oxygen (O), and hydrogen (H). In implementations, the catalyst is a sulfonated aromatic compound. The catalyst can be. for example, para-toluene sulfonic acid (p-toluene sulfonic acid) and / or derivatives of p-toluene sulfonic acid, as depicted in FIG. 1. The organic compound p-toluene sulfonic has the formula CH3C6H4SO3H.

[0029] The catalyst advances or promotes the reaction of the of the aromatic hydrocarbon feed, and the reaction of the hydrocarbon feed with the linker, to give (synthesize) the isotropic pitch. The reaction mixture can include the catalyst, for example, in the ranges of 0.1% to 20% by weight of the reaction mixture, 0.1 % to 15% by weight of the reaction mixture, and 0.2% to 12% by weight of the reaction mixture.

[0030] Embodiments include a mesophase pitch derived (e.g., at a temperature in a temperature range of 300 °C to 500 °C) from an isotropic pitch derived (e.g., without acetic acid) from an aromatic hydrocarbon and a linker (e.g., trioxane). The mesophase pitch can include a softening point, for example, in a range of 300 °C to 450 °C. As indicated, the isotropic pitch can have a softening point, for example in a range of 50 °C to 400 °C. Again, the aromatic hydrocarbon feed can include, for example, toluene, xylene, naphthalene, anthracene, phenanthrene, pyrene, or an aromatic mixed feed from a refinery, or any combinations thereof.

[0031] In embodiments, isotropic pitches are prepared using aromatic feedstocks, which can be toluene, xylenes, naphthalenes, anthracenes, phenanthrenes, pyrene, as well as various aromatic mix feeds from refinery. The linking agent in the synthesis of the isotropic pitch can be, for example, trioxane at various concentrations ranging from 10% to 500% by weight of the aromatichydrocarbon feed. Sulfonated aromatic compounds, such as para-toluene sulfonic acid, can be used as the catalyst, for example, with the concentration of 0.1% and 20% by weight of the reaction mixture in the synthesis of the isotropic pitch. Other concentration ranges for the catalyst are applicable. As mentioned, the synthesis (reaction) can be performed at a temperature, for example, in a range of 50 °C to 300 °C. The softening point of the isotropic pitch can be generally controlled by the reaction conditions. The reaction pressure (e.g., in the vessel having the reaction mixture or the reactor vessel) can be, for example, ambient pressure or in the ranges of 0 pounds per square inch gauge (psig) to 50 psig, 0 psig to 30 psig, or 0 psig to 20 psig. Benzyl ester formation is generally not observed in the absence of acetic acid in the synthesis of the isotropic pitch. In implementations, the formation of benzy l alcohols in the synthesis can be managed by the concentration of the linker(s), such as by adjusting the concentration of trioxane in the reaction mixture. The formation of benzyl alcohols including amount (if any) can be confirmed by!H NMR and FT-ICR mass spectroscopy.

[0032] Mesophase pitches are prepared by heating isotropic pitches at elevated temperatures, for example, in the range of 300 °C to 500 °C. Heat treatment of the isotropic pitch can performed under inert gas flow such as nitrogen. In other implementations, an inert gas is not utilized. In implementations, mesophase content of the mesophase pitches is controlled at least in part by heating time, such as in the range of 0.5 hour to 24 hours, as well as via the composition of the isotropic pitch. The heating time can also be, for example, in the range of 0.5 hour to 48 hours, 1 hour to 36 hours, 1.5 hour to 24 hours, and 0.5 hour to 18 hours. In implementations, mesophase content of the mesophase pitch can be confirmed by polarized microscopy. Softening point of mesophase pitch generally does not only depend on heat treatment conditions but also on the composition of the isotropic pitch. As mentioned, the mesophase content of the mesophase pitch composition can be, for example, in the ranges of 0.01 vol% to 100 vol% or 1 vol% to 100 vol%, or other ranges.

[0033] The MCRT to give the a micro carbon residue (MCR) property is the micro carbon residue test (MCRT) per American Society for Testing and Materials (ASTM) standard D4530-15 (2020) “Standard Test Method for Determination of Carbon Residue (Micro Method)” (last updated June 9, 2020) of ASTM International. The softening point (Ts) is the temperature at which a given material softens. Here, for pitch materials, the softening point (Ts) is per ASTM standard D3104-14a (2018) “Standard Test Method for Softening Point of Pitches (Mettler Softening Point Method)” (last updated December 12, 2018) of ASTM International.

[0034] The mesophase pitch can be utilized as a precursor to make graphite. Before forming the graphite, the mesophase mesophase pitch can be stabilized (e.g., via oxidative stabilization). Forinstance, the mesophase pitch can be heated, such as below the softening point of the mesophase pitch, to stabilize the mesophase pitch.. The stabilized mesophase pitch can be heated under inert atmosphere to form graphitic carbon from the mesophase pitch. The graphitic carbon can be used, for example, as battery anode material. In embodiments, battery anodes are formed from the graphitic carbon composition.

[0035] Carbon products can be prepared from mesophase pitch via series of steps including stabilization, carbonization, and graphitization. The carbonization refers to the removal of all (or substantially all) non-carbon material from a substance under an inert atmosphere such as nitrogen or argon. For the carbonization, the stabilized mesophase pitch may be heated (e.g., between 700-1500 °C) in a carbonization furnace in an inert atmosphere. The graphitization refers to the high temperature treatment of the carbonized product at temperatures, for example, between 2000-3100 °C to achieve structured (stacked) graphene layer leading to hexagonally ordered carbon products such as graphite. Graphitic carbon materials (e.g., graphite particles and fibers, etc.) may be formed for negative electrodes for secondary7batteries, fiber reinforced composites, electrodes for steel making, graphite plates useful for nuclear and fuel cells, wherein electrical conductivity, higher stiffness, and thermal conductivity, are needed or beneficial. Mesophase pitch materials undergo a thermoplastic deformation (or flow) at temperatures near and above its softening point. These materials thus benefit from an air (or oxidative) stabilization to make them generally infusible during carbonization and graphitization processes.

[0036] FIG. 1A is a flow diagram 100 of techniques to produce graphite 102 (a graphitic composition) or amorphous carbon 104 from an aromatic hydrocarbon feed 106. In the illustrated implementation, the aromatic hydrocarbon feed 106 includes xylene that may be mixed xylenes which are the three xylene isomers. The aromatic hydrocarbon feed 106 can instead be other aromatic hydrocarbon compounds or include additional aromatic hydrocarbon compounds. The feed 106 can include other single-ring aromatic compounds. The feed 106 can include multi-ring aromatic compounds. The aromatic hydrocarbon feed 106 can include a process feed (e.g., a mixed feed) from a refinery7.

[0037] Isotropic pitch 108 is formed (e.g., synthesized) from the aromatic hydrocarbon feed 108, for example, at a reaction temperature in the range of 50 °C to 300 °C. Other reaction temperature ranges are applicable. In implementations, the isotropic pitch can be formed by reacting the aromatic hydrocarbon feed 108 with a linker (e.g., anon-aromatic linker, such as trioxane or others) in the presence of a catalyst (e.g., a sulfonated aromatic compound, such as para-toluene sulfonic acid and / or its derivative). In implementations, the linker is in the range of 10% to 500% by weight of the aromatic hydrocarbon feed 106. The reaction mixture having the aromatic hydrocarbon feed106 and the linker can have the catalyst, for example, in the range of 0.1% to 20% by weight of the reaction mixture. The softening point of the isotropic pitch 108 may be controlled, for example, by adjusting at least one of the reaction temperature, the concentration of the linker in the reaction mixture, or the concentration of the catalyst in the reaction mixture. In implementations, the forming of the isotropic pitch 108 is not performed in presence of acetic acid. In implementations, the forming of the isotropic pitch 108 is not performed in presence of a solvent.

[0038] The softening point of the isotropic pitch 108 may be, for example, 50 °C or greater, such as in the range of 50 °C to 400 °C or the range of 200 °C to 400 °C, and the like. Other softening point ranges for the istropic pitch are applicable. The isotropic pitch 108 can include dimers, trimers, tetramers, or pentamers, or any combination thereof, wherein the isotropic pitch comprises a weight average molecular weight (Mw) of about 150 grams per mole (g / mol) to about 1,500 g / mol, a softening point (Tsp) of 50 °C or greater, and a MCR of about 5 weight percent (wt%) or greater based on total weight of the isotropic pitch. The MCR may be, for example, in the ranges of 5 wt% to 95 wt%, 5 wt% to 90 wt%, 5 wt% to 80 wt%, or 5 wt% to 70 wt%.

[0039] To produce amorphous carbon 104, the isotropic pitch 108 may first be stabilized (subjected to stabilization, such as oxidative stabilization, etc.) to give the isotropic pitch as stabilized isotropic pitch 110. For example, the isotropic pitch 108 may be heated at a temperature below the softening point of the isotropic pitch 108 in an atmosphere comprising oxygen (e.g., in a vessel, etc.) to form the stabilized isotropic pitch 110. The stabilization may involve increasing the softening point of the pitch 108. wherein increasing the softening point stabilizes the pitch or at least renders the isotropic pitch infusible, or both. The stabilization may make pitch generally infusible during the subsequent carbonization process. A complete stabilization (or near complete) can refer to increasing the softening point to a level in which the pitch material stops flowing. One of the salient features of stabilization may be the kinetics of the process at different temperatures. As time proceeds, softening point increases due to changes in molecular structure or crosslinking. When the pitch material is fully stabilized, the material generally stops flowing or does not soften.

[0040] Stabilization or stabilizing of the pitch increases softening point of the pitch. Thus, stabilization can be determined by an increase in softening point of the pitch. The softening point increases in the stabilization due to changes in molecular structure or crosslinking. Complete stabilization generally increases the softening point to the point at which the pitch material stops flowing. When the pitch material is fully stabilized, the pitch stops flowing or does not soften, and is generally rendered infusible. Therefore, pitch can be determined as fully or completely stabilized when the pitch will not flow or soften and / or is infusible, e.g., not able to be melted or fused.

[0041] The technique may include heating the stabilized isotropic pitch 110 at a carbonization temperature in an inert atmosphere to form a carbonaceous composition including the amorphous carbon 104. The carbonization temperature can be, for example, in the ranges of about 700 °C to about 1800 °C, 700 °C to 1500 °C, 700 °C to 1300 °C, 700 °C to 1200 °C, 700 °C to 1100 °C, and / or 700 °C to 900 °C. The carbonization refers to the removal of all (or substantially all) noncarbon material from a substance under an inert atmosphere such as nitrogen or argon. The heating for the carbonization of the isotropic pitch 110 (into the amorphous carbon 104) can be performed, for instance, in a furnace (e.g. carbonization furnace) in an inert atmosphere in the furnace. Embodiments provide for conversion of the synthetic isotropic pitch 108, 110 materials into the amorphous carbon 104. Generally, there are two types of carbon structures: crystalline carbon (graphitizing) and amorphous carbon (non-graphitizing). Soft carbon can be transformed into graphite-like materials after high temperature graphitization, while amorphous carbon generally cannot form ordered but turbostratic structure with heat treatment.

[0042] To form graphite 102, the isotropic pitch 108 (e.g., without being subjected to a stabilization process) can be otherwise processed to give graphite 102. As depicted, the isotropic pitch 108 can be thermally treated (heat treated) to give mesophase pitch 112. For instance, the isotropic pitch 108 can be heated, for example, at a temperature in a temperature range of about 300 °C to about 500 °C. In particular implementations, the isotropic pitch 108 can be heated at a specified temperature, such as in that temperature range, in an inert atmosphere for a time period, for example, in a range of about 5 minutes to about 24 hours. The technique can include controlling the mesophase content of the mesophase pitch. Such control of the mesophase content may include, for example, adjusting the the temperature at which the isotropic pitch 108 is synthesized upstream, and / or adjusting the heating time of heating of the isotropic pitch 108 to form the mesophase pitch 112. The mesophase content of the mesophase pitch 112 may be in the range of 0.01 vol% to 100 vol%, or more narrow ranges therein. The softening point of the mesophase pitch 112 may be, for example, in the range of 200 °C to 450 °C. Other softening point ranges are applicable for the mesophase pitch 112.

[0043] Carbon products including graphite can be prepared from mesophase pitch via series of steps including carbonization and graphitization. The technique may include heating the mesophase pitch at a temperature below the softening point of the mesophase pitch in an atmosphere including oxygen to form a stabilized mesophase pitch 114. The stabilized mesophase pitch 114 may be heated at a carbonization temperature (e.g., in a range of from about 700 °C to about 1800 °C) to form a carbonaceous composition, and that carbonaceous composition heated at a graphitization temperature (e.g., in a range of from about 2000 °C to about 3400 °C) in an inertatmosphere to form a graphitic composition or graphite 102. In implementations, the graphitization refers to the high temperature treatment of the carbonized product to achieve structured (stacked) graphene layer leading to hexagonally ordered carbon products such as graphite. Lastly, the technique can include forming a battery anode (or other product) having the graphitic composition or graphite 102.Additional Embodiments

[0044] Accordingly, the present disclosure may provide for .... The methods and systems may include any of the various features disclosed herein, including one or more of the following statements.

[0045] Embodiment 1. A method of producing mesophase pitch for further processing, the method comprising: forming isotropic pitch by reacting components comprising an aromatic hydrocarbon feed and a linker in presence of a catalyst at a first temperature, wherein the isotropic pitch comprises a weight average molecular weight (Mw) of about 150 grams per mole (g / mol) to about 1,500 g / mol, a softening point (Tsp) of 50 °C or greater, and a micro carbon residue (MCR) of about 5 weight percent (wt%) or greater based on total w eight of the isotropic pitch; and forming the mesophase pitch by heating the isotropic pitch at a second temperature.

[0046] Embodiment 2. The method of Embodiment 1, wherein the linker comprises a nonaromatic linker, wherein one or more aromatic classes of the aromatic hydrocarbon feed comprises 1-ring aromatics, 2-ring aromatics, 3-ring aromatics, 4-ring aromatics, 5-ring aromatics, 6-ring aromatics, 7-ring aromatics, 8-ring aromatics. 9-ring aromatics, or 10 or more-ring aromatics, or any combinations thereof, and w herein forming the isotropic pitch is not performed in presence of acetic acid.

[0047] Embodiment 3. The method of Embodiment 1 or Embodiment 2, wherein the linker comprises trioxane, and wherein the softening point of the isotropic pitch is in a range of 50 °C to 400 °C.

[0048] Embodiment 4. The method of any preceding Embodiment, wherein the aromatic hydrocarbon feed comprises a single-ring aromatic compound or a multi-ring aromatic compound, or both, wherein the first temperature is in a first temperature range of 50 °C to 300 °C, wherein the second temperature is in a second temperature range of 300 °C to 500 °C, and wherein the catalyst comprises a sulfonated aromatic compound.

[0049] Embodiment 5. The method of any preceding Embodiment, wherein the aromatic hydrocarbon feed comprises benzene, toluene, xylene, indene, naphthalene, 1 -methyl naphthalene, 2-methyl naphthalene, anthracene, phenanthrene, pyrene, chrysene, benzopyrene, picenecoronene, tetracene, pentacene, triphenylene, corannulene, benzo [j J fluoranthene, benzo[c]fluorene, perylene.benzo-perylene, ovalene, eleven carbon (Cl 1) aromatic hydrocarbons, or an aromatic mixed feed from a refinery, or any combinations thereof, wherein the xylene comprises at least one of orthoxylene, meta-xylene, or para-xylene, and wherein the catalyst comprises para-toluene sulfonic acid or a derivative thereof, or both.

[0050] Embodiment 6. The method of any preceding Embodiment, wherein the aromatic hydrocarbon feed comprises xylene isomers.

[0051] Embodiment 7. The method of any preceding Embodiment, wherein the aromatic hydrocarbon feed comprises refinery bottoms, slurry oil, vacuum resid, cracker bottoms, main column bottoms (MCB), or heavy residue oil, or any combinations thereof.

[0052] Embodiment 8. The method of any preceding Embodiment, wherein forming the isotropic pitch is not performed in presence of a solvent.

[0053] Embodiment 9. The method of any preceding Embodiment, wherein the linker is in a first range of 10% to 500% by weight of the aromatic hydrocarbon feed, wherein forming the isotropic pitch by the reacting is with a reaction mixture comprising the components and the catalyst, and wherein the reaction mixture comprises the catalyst in a second range of 0.1% to 20% by weight of the reaction mixture.

[0054] Embodiment 10. The method of any preceding Embodiment, comprising controlling the softening point of the isotropic pitch, wherein controlling the softening point of the isotropic pitch comprises adjusting at least one of the first temperature, a first concentration of the linker in a reaction mixture, and a second concentration of the catalyst in the reaction mixture, wherein the reaction mixture comprises the components and the catalyst, and wherein the isotropic pitch comprises dimers, trimers, tetramers, or pentamers, or any combination thereof.

[0055] Embodiment 11. The method of any preceding Embodiment, comprising controlling mesophase content of the mesophase pitch, wherein controlling the mesophase content of the mesophase pitch comprises adjusting the second temperature or heating time of the heating of the isotropic pitch, or both.

[0056] Embodiment 12. The method of any preceding Embodiment, comprising heating the isotropic pitch at a temperature below the softening point of the isotropic pitch in an atmosphere comprising oxygen to form a stabilized isotropic pitch.

[0057] Embodiment 13. The method of Embodiment 12, comprising heating the stabilized isotropic pitch at a carbonization temperature in an inert atmosphere to form a carbonaceous composition comprising amorphous carbon.

[0058] Embodiment 14. The method of Embodiment 1, wherein forming the mesophase pitch comprises heating the isotropic pitch at the second temperature in an inert atmosphere for a timeperiod in a range of about 5 minutes to about 24 hours, and wherein the second temperature is in a temperature range of about 300 °C to about 500 °C.

[0059] Embodiment 15. The method of Embodiment 1 or Embodiment 14, comprising heating the mesophase pitch at a temperature below the softening point of the mesophase pitch in an atmosphere comprising oxygen to form a stabilized mesophase pitch.

[0060] Embodiment 16. The method of Embodiment 15, comprising heating the stabilized mesophase pitch at a carbonization temperature in a carbonization temperature range of from about 700 °C to about 1800 °C to form a carbonaceous composition.

[0061] Embodiment 17. The method of Embodiment 16, comprising heating the carbonaceous composition at a graphitization temperature in a graphitization temperature range of from about 2000 °C to about 3400 °C in an inert atmosphere to form a graphitic composition.

[0062] Embodiment 18. The method of Embodiment 17, comprising forming a batten- anode comprising the graphitic composition.

[0063] Embodiment 19. A mesophase pitch comprising: a first softening point in a first range of 200 °C to 450 °C; a mesophase content in a range of 0.01 volume percent (vol%) to 100 vol%; wherein the mesophase pitch is produced from an isotropic pitch at a temperature in a temperature range of 300 °C to 500 °C, and wherein the isotropic pitch comprises a second softening point in a second range of 200 °C to 400 °C; and wherein the isotropic pitch is derived, without acetic acid, from an aromatic hydrocarbon feed and a linker comprising trioxane.

[0064] Embodiment 20. The mesophase pitch of Embodiment 19, wherein the aromatic hydrocarbon feed comprises benzene, toluene, xylene, naphthalene, anthracene, phenanthrene, pyrene, or an aromatic mixed feed from a refinery, or any combinations thereof.

[0065] To facilitate a better understanding of the present invention, the following examples of certain aspects of some embodiments are given. In no way should the following examples be read to limit, or define, the entire scope of the disclosure.

[0066] While the disclosure has been described with respect to a number of embodiments and examples, those skilled in the art, having benefit of this disclosure, will appreciate that other embodiments can be devised which do not depart from the scope and spirit of the disclosure as disclosed herein. Although individual embodiments are discussed, the present disclosure covers all combinations of all those embodiments.

[0067] While compositions, methods, and processes are described herein in terms of “comprising,” “containing,” “having,” or “including” various components or steps, the compositions and methods can also “consist essentially of’ or “consist of’ the various components and steps. The phrases, unless otherwise specified, “consists essentially of’ and "consistingessentially of’ do not exclude the presence of other steps, elements, or materials, whether or not, specifically mentioned in this specification, so long as such steps, elements, or materials, do not affect the basic and novel characteristics of the disclosure, additionally, they do not exclude impurities and variances normally associated with the elements and materials used.

[0068] All numerical values within the detailed description are modified by “about” the indicated value, and take into account experimental error and variations that would be expected by a person having ordinary skill in the art.

[0069] Many alterations, modifications, and variations will be apparent to those skilled in the art in light of the foregoing description without departing from the spirit or scope of the present disclosure and that when numerical lower limits and numerical upper limits are listed herein, ranges from any lower limit to any upper limit are contemplated.

[0070] Examples

[0071] Synthesis Examples giving isotropic pitch (IP) and thermal treatments Examples giving mesophase pitch (MP) are presented. The Examples are not meant to limit the present techniques.

[0072] Synthesis of Isotropic Pitches

[0073] For IP-1, trioxane (1 equiv.) was dissolved in xylene (1.0 equiv.) and diluted with acetic acid (0.15M as molar concentration of xylene, mole of xylene / liter of acetic acid) in an a round bottom flask. Sulfuric acid (0.75 equiv.) was added dropwise to the flask. The resulting mixture was stirred at 100 °C for 16 hours (h), and then cooled to ambient temperature and poured into water. The precipitates were filtered and washed with water and dried under vacuum at 50 °C. This Example for IP-1 is represented by Scheme 1 below;Scheme 1. Synthesis of isotropic pitches in acetic acid.

[0074] For IP -2, trioxane (1.0 equiv.) was dissolved in xylene (1.0 equiv.) in an around bottom flask, and p-toluene sulfonic acid (p-TSA) (0.1 equiv.) added to the flask. The resulting mixture was stirred at 100 °C for 16 h and then cooled to ambient temperature, and then diluted with the addition of dichloromethane, subsequently precipitated into water. The precipitates were filteredand washed with water and dried under vacuum at 50 °C. This Example for IP-2 is represented by Scheme 2 below.Scheme 2. Synthesis of isotropic pitches in the presence of p-TSA.

[0075] For IP-3, trioxane (0.66 equiv.) was dissolved in xylene (1.0 equiv.) in an a round bottom flask, and p-toluene sulfonic acid (0.1 equiv.) added to the flask. The resulting mixture was stirred at 100 °C for 16 h and then cooled to ambient temperature, then diluted with the addition of dichloromethane, subsequently precipitated into water. The precipitates were filtered and washed with water and dried under vacuum at 50 °C. This Example for IP-3 is represented by Scheme 3 below;Scheme 3. Synthesis of isotropic pitches in the presence of p-TSA.

[0076] For IP-4, trioxane (0.33 equiv.) was dissolved in xylene (1.0 equiv.) in an a round bottom flask, and p-toluene sulfonic acid (0.1 equiv.) was added to the flask. The resulting mixture was stirred at 100 °C for 16 h, then cooled to ambient temperature, and then diluted with the addition of dichloromethane, subsequently precipitated into water. The precipitates were filtered, washed with water, and dried under vacuum at 50 °C. This Example for IP-4 is represented by Scheme 4 below.Scheme 4. Synthesis of the isotropic pitches in the presence of p-TSA.

[0077] If a solvent is employed commercially for dilution, as in the laboratory Examples, the solvent can be dicholoromethane. The solvent can generally any halogenated solvent, such as chloroform. The solvent could be other solvents, such as ethyl acetate, acetone, etc.

[0078] The Examples for IP-5, IP-6, IP-7, and IP-8 were performed similar as the Examples for IP-2, IP-3, and IP -4, except for some differences in temperature (in which the mixture was stirred for 16 h) and some weight percent (wt.%) differences with components, as indicated in Table 1 below. Table 1 gives xylene at 100 wt.% as a basis and with the respective wt.% of trioxane and catalyst (p-toluene sulfonic acid) as relative to xylene. The softening point of the synthesized IP is given.Table 1. IP Synthesis Conditions and Softening Point Results

[0079] Table 2 below gives complementary information for the IP synthesis Examples. The percent of oxy gen-containing molecules in synthesized IP is given, which was estimated by Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS) data. See FIG. 4.Table 2. IP Synthesis Components and Results*Estimated by FT-ICR-MS data (FIG. 4)

[0080] FIG. 2 is1H nuclear magnetic resonance (NMR) spectra of the isotropic pitches (IP-1 , IP-2, IP-3, and IP-4) in deuterated chloroform (CDCh) at ambient temperature. All protons are observed in theNMR spectra of the isotropic pitches in CDCh with the expected chemical shifts. Again, theNMR spectra of the isotropic pitches (IP-1, IP-2, IP-3, and IP-4) are shown in FIG. 2, which the resonances at 5.5-7.5 part per million (ppm) assigned to the aromatic protons and the resonances at 5.1-5.5 ppm assigned to the benzylic protons of the esters. Resonances at 4.2-5.1 ppm reflect the benzylic protons of alcohols, which gradually decreased its intensity in the order of IP-2, IP-3, IP-4 due to decreasing the concentration of trioxane. Meanwhile, the benzylic protons of the esters completely disappeared in the spectra of IP-2, IP-3 and IP-4 in the absence of acetic acid. Resonances assigned to the methyl protons next to the aromatic rings are seen at 1 -3 ppm. These results fromNMR confirmed that composition of the isotropic pitches can be controlled by the reaction conditions.

[0081] FIG. 3 and FIG. 4 are mass spectra of pitch materials. FIG. 3 is FTI-CR-MS mass spectra of IP-1, IP-2, IP-3, and IP-4. The base axis is molecular weight (MW). The curve 302 is the molecular weight distribution. The vertical axis is the Z Class or hydrogen deficiency and is a measure of aromaticity with lower negative numbers meaning higher aromaticity (higher C / H ratio). The curve 302 is a distribution made via projection of the data along the axis. The curve 306 is the solubility line.

[0082] FIG. 4 is FTI-CR-MS mass spectra of IP-1, IP-2, IP-3, and IP-4 including oxygen containing species. The base axis is molecular weight (MW). As with FIG. 3, the curve 402 in FIG.4 is the molecular weight distribution, and the vertical axis is the Z Class or hydrogen deficiency. The curve 402 is a distribution made via projection of the data along the axis. The curve 406 is the solubility7line.

[0083] The FT-ICR-MS spectra of the isotropic pitches (IP-1. IP-2, IP-3, and IP -4), as shown in FIG. 3 and FIG. 4, indicate the occurrence of major peaks suggested the presence of trimers to octamers of xylenes. The concentration of trioxane as well as acetic acid used in the reaction was found to play a key role in determining the composition of the isotropic pitches. The FT-ICR-MS mass spectra of the oxygen containing isotropic pitches are compared in FIG. 4 indicate that the oxygen containing species significantly decreased by decreasing the trioxane concentration as well as in the absence of acetic acid. This is consistent with the resultsNMR spectra of the isotropic pitches, which show very similar distribution of oxygenated molecules in the isotropic pitches.

[0084] Thermal Treatment to give Mesophase Pitch

[0085] The thermal treatment (heat treatment) applies heat to the synthetic isotropic pitch material (composition), thereby increasing temperature of the isotropic pitch material. The thermal treatment can be considered a synthesis of the mesophase pitch by applying heat to the isotropic pitch. The molecules may be cracked and reacted at elevated temperature to form mesophase pitches, such as under inert atmosphere.

[0086] The second step of the process is thermal treatment of the synthesized isotropic pitches. The isotropic pitches were treated at 425 °C for 75 minutes under a nitrogen flow, as indicated in Scheme 5 depicted below.Scheme 5. Thermal treatment of IP giving synthesis of MP

[0087] Table 3 below gives the MP synthesis (thermal treatment) conditions and results. The Examples MP-1. MP-2, MP-3, and MP-4 correspond to the thermal treatment of IP-1. IP-2, IP-3, amd IP-4, respectively. The time of the thermal treatment is given in minutes (min). The softening point in °C is for mesophase pitch. The yield in percent (%) is the (final mass) / (mass of feed + 0.46 times trioxane mass). Trioxane also releases water during reaction. Thus, 46% of trioxane can incorporate into the final molecule by weight.Table 3. MP Synthesis Conditions and Results*Estimated by FT-ICR-MS data (FIG. 7)

[0088] FIG. 5 is mass spectra of IP -4 and MP-4. In particular, the FT-ICR-MS spectra of IP-4 and MP-4 (IP -4 as further pyrolyzed) are shown in FIG. 5. Thus, FIG. 5 gives a comparison of themass spectra of IP-4 and MP-4. Molecular weight (MW) is given along the base axis. The mass / charge (M / Z) peaks of the isotropic pitch IP-4 range from 300 to 1000, which corresponds to trimer to octamers of the xylene unit. The mass / charge (M / Z) peaks of the MP-4 (pyrolyzed sample) appear from 300 to 1250 and condensation of isotropic pitch IP-4 are observed implying the formation of mesogenic species.

[0089] FIG. 6 is FTI-CR-MS mass spectra of IP-2 and MP -2. The base axis is MW. The curve 602 is the molecular weight distribution. The Z-class versus carbon number of the IP-2 and MP-2 as plotted in FIG. 6 indicates that MP-2 (the pyrolyzed sample) has an increased average molar mass. Further, it evident that the sample after heat treatment indicate much broader Z-class. More interestingly, the slope of the solubility line 606 changed indicating decrease in the alkyl group and functional groups (esters / alcohols). Mass spectroscopy analysis revealed that the thermally treated material underwent dehydrogenative cyclization reactions to result in the formation of new aromatic molecules. The resulting species are thought to be highly conjugated aromatic species, which we postulate, are desirable molecules for high quality mesophase pitches.

[0090] FIG. 7 is FTI-CR-MS mass spectra of mesophase pitches (MP-1, MP-2, MP-3, and MP-4) including oxygen containing species. The base axis is MW. The curve 702 is the molecular weight distribution. Oxygenated species as plotted in FIG. 7 are approximately 2-3% of the mesophase pitch oxygen-containing molecules. The oxygenated species may help to stabilize the mesophase pitches.FIG. 8 is optical micrographs of pitches (MP-2 and MP-3) under cross-polarized light via -plate. white balanced for clarity. The scale bar 802 is 100 microns (pm). Cross-polarized light microscopy was utilized to determine the concentration of mesophase pitch of the samples. After pyrolysis (thermal treatment), the samples were cooled down to room temperature and embedded in epoxy before being polished smooth for optical imaging, producing cross-sections of the sample. The data (image features) as shown in FIG. 8 indicate mesophase ordering in the samples. The cross-polarized images of MP-1 and MP-2 pyrolyzed at 425 °C for 75 min indicate about 50% of mesophase content indicating a broader distribution of mesophase droplets and droplet aggregates. MP-3 showed only 25 % mesophase and more homogenous droplets, while MP-4 carried trace amount mesogen species. It likely that the mesophase content is not only controlled by pyrolysis time and temperature but also the composition of the isotropic pitches. The samples (MP-1 and MP-2) with the more oxygenated species showed more mesophase content in comparison to the samples (MP-3 and MP-4) with the less oxygenated species under identical pyrolysis (thermal treatment) conditions demonstrating the more oxygenated species led to the more mesogen formation.

Claims

CLAIMS:

1. A method of producing mesophase pitch for further processing, the method comprising:forming isotropic pitch by reacting components comprising an aromatic hydrocarbon feed and a linker in presence of a catalyst at a first temperature, wherein the isotropic pitch comprises a weight average molecular weight (Mw) of about 150 grams per mole (g / mol) to about 1,500 g / mol, a softening point (Tsp) of 50 °C or greater, and a micro carbon residue (MCR) of about 5 weight percent (wt%) or greater based on total weight of the isotropic pitch; andforming the mesophase pitch by heating the isotropic pitch at a second temperature.

2. The method of claim 1, wherein the linker comprises a non-aromatic linker, wherein one or more aromatic classes of the aromatic hydrocarbon feed comprises 1-ring aromatics, 2-ring aromatics, 3-ring aromatics, 4-ring aromatics, 5-ring aromatics, 6-ring aromatics, 7-ring aromatics, 8-ring aromatics, 9-ring aromatics, or 10 or more-ring aromatics, or any combinations thereof, and wherein forming the isotropic pitch is not performed in presence of acetic acid.

3. The method of claim 1 or claim 2, wherein the linker comprises trioxane, and wherein the softening point of the isotropic pitch is in a range of 50 °C to 400 °C.

4. The method of any preceding claim, wherein the aromatic hydrocarbon feed comprises a single-ring aromatic compound or a multi-ring aromatic compound, or both, wherein the first temperature is in a first temperature range of 50 °C to 300 °C, wherein the second temperature is in a second temperature range of 300 °C to 500 °C. and wherein the catalyst comprises a sulfonated aromatic compound.

5. The method of any preceding claim, wherein the aromatic hydrocarbon feed comprises benzene, toluene, xylene, indene, naphthalene, 1 -methyl naphthalene, 2-methyl naphthalene, anthracene, phenanthrene, pyrene, chrysene, benzopyrene, picenecoronene, tetracene, pentacene, triphenylene, corannulene, benzo[j]fluoranthene, benzo [c] fluorene, perylene, benzo-perylene, ovalene, eleven carbon (Cl 1) aromatic hydrocarbons, or an aromatic mixed feed from a refinery, or any combinations thereof, wherein the xylene comprises at least one of ortho-xylene, metaxylene. or para-xylene, and wherein the catalyst comprises para-toluene sulfonic acid or a derivative thereof, or both.

6. The method of any preceding claim, wherein the aromatic hydrocarbon feed comprises xylene isomers.

7. The method of any preceding claim, wherein the aromatic hydrocarbon feed comprises refinery bottoms, slurry oil, vacuum resid, cracker bottoms, main column bottoms (MCB), or heavy residue oil, or any combinations thereof.

8. The method of any preceding claim, wherein forming the isotropic pitch is not performed in presence of a solvent.

9. The method of any preceding claim, wherein the linker is in a first range of 10% to 500% by weight of the aromatic hydrocarbon feed, wherein forming the isotropic pitch by the reacting is with a reaction mixture comprising the components and the catalyst, and wherein the reaction mixture comprises the catalyst in a second range of 0.1% to 20% by weight of the reaction mixture.

10. The method of any preceding claim, comprising controlling the softening point of the isotropic pitch, wherein controlling the softening point of the isotropic pitch comprises adjusting at least one of the first temperature, a first concentration of the linker in a reaction mixture, and a second concentration of the catalyst in the reaction mixture, wherein the reaction mixture comprises the components and the catalyst, and wherein the isotropic pitch comprises dimers, trimers, tetramers, or pentamers, or any combination thereof.

11. The method of any preceding claim, comprising controlling mesophase content of the mesophase pitch, wherein controlling the mesophase content of the mesophase pitch comprises adjusting the second temperature or heating time of the heating of the isotropic pitch, or both.

12. The method of any preceding claim, comprising heating the isotropic pitch at a temperature below the softening point of the isotropic pitch in an atmosphere comprising oxygen to form a stabilized isotropic pitch.

13. The method of claim 12, comprising heating the stabilized isotropic pitch at a carbonization temperature in an inert atmosphere to form a carbonaceous composition comprising amorphous carbon.

14. The method of claim 1, wherein forming the mesophase pitch comprises heating the isotropic pitch at the second temperature in an inert atmosphere for a time period in a range of about 5 minutes to about 24 hours, and wherein the second temperature is in a temperature range of about 300 °C to about 500 °C.

15. The method of claim 1 or claim 14, comprising heating the mesophase pitch at a temperature below the softening point of the mesophase pitch in an atmosphere comprising oxygen to form a stabilized mesophase pitch.

16. The method of claim 15, comprising heating the stabilized mesophase pitch at a carbonization temperature in a carbonization temperature range of from about 700 °C to about 1800 °C to form a carbonaceous composition.

17. The method of claim 16, comprising heating the carbonaceous composition at a graphitization temperature in a graphitization temperature range of from about 2000 °C to about 3400 °C in an inert atmosphere to form a graphitic composition.

18. The method of claim 17, comprising forming a battery anode comprising the graphitic composition.

19. A mesophase pitch comprising:a first softening point in a first range of 200 °C to 450 °C;a mesophase content in a range of 0.01 volume percent (vol%) to 100 vol%; wherein the mesophase pitch is produced from an isotropic pitch at a temperature in a temperature range of 300 °C to 500 °C, and wherein the isotropic pitch comprises a second softening point in a second range of 200 °C to 400 °C; andwherein the isotropic pitch is derived, without acetic acid, from an aromatic hydrocarbon feed and a linker comprising trioxane.

20. The mesophase pitch of claim 19, wherein the aromatic hydrocarbon feed comprises benzene, toluene, xylene, naphthalene, anthracene, phenanthrene, pyrene, or an aromatic mixed feed from a refinery7, or any combinations thereof.

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