Pitches from aromatic feedstocks

Abstract

A composition may include: a pitch composition having an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

Description

CROSS REFERENCE TO RELATED APPLICATIONS

[0001] This application is a national stage application, filed under 35 U.S.C. 371, of International Patent Application No. PCT / US2024 / 025195, filed Apr. 18, 2024, which claims the priority of U.S. Provisional Patent Application No. 63 / 467,821, filed May 19, 2023, which is incorporated by reference in its entirety.FIELD

[0002] The present disclosure relates to pitch compositions, and more particularly to hydrocarbon solvent soluble pitch compositions produced from aromatic feedstocks.BACKGROUND

[0003] Pitch is a carbon-containing feedstock which can be classified as an isotropic pitch, or a mesophase pitch. Both isotropic and mesophase pitch can be complex mixtures of aromatic molecules; however, the aromatic molecules in an isotropic pitch are randomly oriented, whereas in a mesophase pitch, at least a portion of these aromatic molecules are ordered. A mesophase pitch may have a heterogeneous two-phase structure comprising the said ordered aromatic molecules (e.g., anisotropic region), and an isotropic region. In general, an isotropic pitch formation precedes a mesophase pitch formation. Both types of pitches will be collectively referred to herein as “pitch,” unless otherwise indicated.

[0004] Conventional methods for pitch production include conversion processes such as thermal and / or catalytic conversion of aromatic hydrocarbon feedstocks at elevated temperatures under vigorous stirring and long residence times to produce a crude pitch product. High temperatures and vacuum are often required to effectively separate components of the crude pitch product to produce a finished pitch product. The application of vacuum adds cost to the process, limits throughput, and can only be used to remove the lowest molecular weight compounds. Furthermore, as the temperature of the separation processes increases, undesirable chemical side reactions occur, leading to the formation of a mixture comprising coke and a pitch of poor qualities, which is unfit for the production of carbon materials. Additionally, non-volatile impurities such as ashes, metal contaminants, and other undesirable particulate present in the hydrocarbon feedstock and formed during the reaction, may remain in the pitch, thus making the pitch unsuitable for carbon product manufacturing. Conventional distillation processes are not sufficient to mitigate / eliminate such impurities.

[0005] Isotropic pitches are useful materials to produce carbon products. Liquid isotropic pitches can be easily coated onto solids or formed into arbitrary shapes. Isotropic pitch is readily thermoset by high temperature calcination in the absence of air to form solid carbon. High quality isotropic pitches can be calcined such that a majority of the composition (e.g., >50 wt. %) is converted to solid carbon. The high carbon yield upon calcination enables the production of strong, high density carbon parts. Isotropic pitch is useful in production of electric arc furnace electrodes, aluminum-carbon electrodes, battery electrodes, as well as in carbon part manufacturing where isotropic pitch is used as a glue to bond carbon fiber strands and sheets, among other uses. Pitch is also used in a number of product applications, such as carbon fiber, binder pitch, impregnation pitch, high-performance and general-purpose carbon fiber, refractories, carbon / carbon composites, synthetic graphite, graphite parts, mesocarbon microbeads for anodes for lithium ion batteries, carbon foam for heat transfer applications, sound absorbers, roofing products, lubricants, and consumer products such as cosmetics, among other uses.

[0006] Pitches are fouling and tend to stick to machinery and components which contact the pitch during production of the pitch and production of carbon products from the pitch. Pitches are generally insoluble to minimally soluble in hydrocarbon solvents making cleaning of machinery and components which the pitch contacts difficult. Over time, surfaces contacted by pitch tend to become covered by solid carbon.SUMMARY

[0007] Disclosed herein is an example method including a composition comprising: a pitch composition having an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0008] Further disclosed herein is a method comprising: introducing an aromatic feedstock into a deasphalting unit; and deasphalting at least a portion of the aromatic feedstock to produce a deasphalted oil and a deasphalted rock, wherein the deasphalted rock has an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the deasphalted rock is 100 wt. % soluble in toluene.

[0009] Further disclosed herein is a method comprising: introducing an aromatic feedstock produced from a SATC process into a deasphalting unit; deasphalting at least a portion of the aromatic feedstock with a C4-C7 solvent to produce a deasphalted oil and a deasphalted rock; and blending the deasphalted rock with an aromatic feedstock to produce a pitch composition with an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0010] These and other features and attributes of the disclosed methods and compositions 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

[0011] 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:

[0012] FIG. 1 illustrates process for producing a pitch composition from an aromatic feedstock, in accordance with some embodiments of the present disclosure.

[0013] FIG. 2 illustrates process for producing a pitch composition from an aromatic feedstock, in accordance with some embodiments of the present disclosure.

[0014] FIG. 3 is a graph of softening point versus wt. % MCRT coking for pitches, in accordance with some embodiments of the present disclosure.

[0015] FIG. 4 is a graph of softening point versus MCRT coking value for commercially produced pitches as well as pitches produced from Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid, in accordance with some embodiments of the present disclosure.DETAILED DESCRIPTION

[0016] The present disclosure relates to pitch compositions and more particularly to hydrocarbon solvent soluble pitch compositions produced from aromatic feedstocks. The disclosed pitch compositions may be soluble in toluene and other hydrocarbon solvents and have relatively low softening points. In some embodiments, the pitch compositions, including mesophase pitch compositions, are produced from petroleum tars such as from the vacuum resid fraction of hydrotreated steam cracker tar, FCC main column bottoms, a composition from a SATC process, sweet vacuum resid, and / or coal tar.

[0017] The present disclosure further relates to a process for upgrading sweet vacuum resid fractions from atmospheric distillation of crude oil to form pitch compositions. Sweet vacuum resid fractions are the residues from distillation of crude oil which contain less than 1 wt. % sulfur and are typically used in a low sulfur fuel oil (LSFO) and as part of a feed to an FCC unit to produce gasoline. The demand for sweet vacuum resid fractions is expected to decline as the demand for these types of fuel also declines. Further conversion of the sweet vacuum resid fractions are limited as sweet vacuum resid typically can't be driven to high 1050° F.+ (565° C.) conversion in a visbreaker unit due to incompatibility. The present disclosure allows for the sweet vacuum resid fractions to be converted to useful materials such as deasphalted oil (DAO), fuels, lubricant base stock, and pitch compositions.

[0018] Pitch compositions have been previously made from naphthalene using acid catalysis. The naphthalene derived pitch may be fluxed with methyl-naphthalene which results in a solvated mesophase pitch having a softening point in a range of 200-300° C. and an MCRT wt. % of 65-78.

[0019] The presently disclosed methods of producing pitch compositions from petroleum tar have a similar MCRT but a much lower softening point in a range of 30° C.-150° C. for the approximately same MCRT value of pitch derived from naphthalene.Definitions and Test Methods

[0020] All numerical values within the detailed description and the claims herein are modified by “about” or “approximately” with respect to the indicated value, and take into account experimental error and variations that would be expected by a person having ordinary skill in the art. Unless otherwise indicated, ambient temperature (room temperature or “RT”) is about 25° C.

[0021] As used in the present disclosure and claims, the singular forms “a,”“an,” and “the” include plural forms unless the context clearly dictates otherwise.

[0022] The term “and / or” as used in a phrase such as “A and / or B” herein is intended to include “A and B,”“A or B,”“A,” and “B.”

[0023] For the purposes of the present disclosure and the claims thereto, the following definitions shall be used.

[0024] As used herein, the term “pitch” refers to hydrocarbons with softening points above 30° C., consisting of mainly aromatic and alkyl-substituted aromatic compounds. These aromatic compounds are primarily hydrocarbons, but heteroatoms and traces of metals can be present within these materials. When cooled from a melt, a pitch can solidify into an amorphous solid. Pitches may include petroleum pitches, coal tar pitches, natural asphalts, pitches contained as by products in the naphtha cracking industry, pitches of high carbon content obtained from petroleum asphalt and other substances having properties of pitches produced as products in various industrial production processes. Pitches exhibit a broad softening temperature range and are typically derived from petroleum, coal tar, plants, or catalytic oligomerization of small molecules (e.g., acid-catalyzed oligomerization). A pitch can also be referred to as tar, bitumen, or asphalt. When a pitch is produced from plants, it is also referred to as resin. Various pitches may be obtained as products in the gas oil or naphtha cracking industry as a carbonaceous residue consisting of a complex mixture of primarily aromatic organic compounds, which are solids at room temperature, and exhibit a relatively broad softening temperature range. Hence, a pitch can be obtained from heat treatment and distillation of petroleum fractions. A “petroleum pitch” refers to the residuum carbonaceous material obtained from distillation of crude oils and from the catalytic cracking of petroleum distillates. A “coal tar pitch” refers to the material obtained by distillation of coal.

[0025] As used herein, the term “mesophase” refers to a discotic liquid crystalline material consisting of planar aromatic molecules with a broader molecular weight distribution. A “mesophase pitch” consists of “mesophase” and optionally an isotropic phase. The mesophase exhibits optical anisotropy (birefringence) when examined using a polarized light microscope. For example, a mesophase pitch can be a pitch containing more than about 10 vol % mesophase, based on the total volume of the pitch. A mesophase content of a pitch can be measured, according to ASTM D4616 (Standard Test Method for Microscopical Analysis by Reflected Light and Determination of Mesophase in a Pitch), from reflected polarized light microscopy images by imbedding various samples of the pitch in epoxy, followed by polishing the samples until they become highly reflective. A series of images can be recorded in order to quantify the anisotropic content.

[0026] The term “softening point” or “SP,” and grammatical variants, as used herein, refers to a temperature or a range of temperatures at which a substance softens. Herein, the softening point is measured using a METTLER TOLEDO dropping point instrument, such as METTLER TOLEDO DP70, according to a procedure analogous to the American Society for Testing and Materials (ASTM) ASTM D3104-14a.

[0027] As used herein, the term “microcarbon residue” or “MCR,” and grammatical variants thereof, refers to an amount of carbonaceous residue formed after evaporation and pyrolysis of petroleum materials under particular conditions. The term “microcarbon residue test” or “MCRT,” and grammatical variants thereof, as used herein, refers to a standard method for the determination of MCR and is measured according to ASTM D4530 (2020).

[0028] As used herein, the term “mesocarbon microbead,” refers to a porous graphite carbon material wherein an inner core is composed of amorphous carbon while an outer shell is composed of graphitic carbon. Both the inner core and the outer shell are porous. The mesocarbon microbeads have an diameter ranging from 10 microns to 100 microns.

[0029] As used herein, the term “hydrogen to carbon ratio” or “H / C Ratio,” and grammatical variants thereof, refers to an amount of elemental hydrogen to elemental carbon within a pitch composition. The H / C Ratio is measured according to ASTM D5291-21.

[0030] “SCT” means (a) a mixture of hydrocarbons having one or more aromatic components and optionally (b) non-aromatic and / or non-hydrocarbon molecules, the mixture being derived from hydrocarbon pyrolysis and having a 90% Total Boiling Point >550° F. (290° C.) (e.g., >90.0 wt % of the SCT molecules have an atmospheric boiling point >550° F. (290° C.)). SCT can contain >50.0 wt % (e.g., >75.0 wt %, such as >90.0 wt %), based on the weight of the SCT, of hydrocarbon molecules (including mixtures and aggregates thereof) having (i) one or more aromatic components and (ii) a number of carbon atoms >15. SCT generally has a metals content, <1.0×103 ppmw, based on the weight of the SCT (e.g., an amount of metals that is far less than that found in crude oil (or crude oil components) of the same average viscosity). SCT typically has a mass density >1.0 Kg / L, e.g., >1.05 Kg / L, such as >1.1 Kg / L, or >1.15 Kg / L.

[0031] “Solvent assisted tar conversion” or (“SATC”) is a process for producing an upgraded tar, such as SCT. The process includes hydroprocessing a tar stream in the presence of a utility fluid, and is generally described in P.C.T. Patent Application Publication No. WO 2018 / 111577, which is incorporated by reference in its entirety. For example, SATC can include hydroprocessing one or more SCT streams, including those that have been subjected to prior pretreatments, in the presence of a utility fluid, to produce a hydroprocessed tar having a lesser viscosity, improved blending characteristics, fewer heteroatom impurities, and a lesser content of solids and semi-solids (e.g., fewer particles) as compared to the SCT feed. The SATC process produces several intermediate streams including a SATC stage 1 product, sometimes referred to as SATC stage 1 vacuum resid, which is the bottoms fraction I which is fed to a 2nd Stage hydroprocessing reactor L for an additional hydroprocessing step that provides desulfurization.Methods of Making Pitch Compositions

[0032] FIG. 1 illustrates process 100 for producing a pitch composition from an aromatic feedstock. In FIG. 1, an aromatic feed 102 is introduced into a deasphalter 104. The deasphalter 104 generates a deasphalted oil 106 and deasphalted rock 108 which is the pitch composition. The deasphalted oil 106 is then processed in a sour processing stage 110. Optionally, a portion 144 of recycled light neutral base product 142 can be combined with deasphalted oil 106. Sour processing stage 110 can include one or more of a demetallation catalyst, a hydrotreating catalyst, a hydrocracking catalyst, and / or an aromatic saturation catalyst. The conditions in sour processing stage 110 can be selected to at least reduce the sulfur content of the hydroprocessed effluent 112 to 20 wppm or less. This can correspond to 15 wt. % to 40 wt. % conversion of the feed relative to 370° C. Optionally, the amount of conversion in the sour processing stage 110 can be any convenient higher amount so long as the combined conversion in sour processing stage 110 and sweet processing stage 132 is 90 wt. % or less.

[0033] The hydroprocessed effluent 112 can then be passed into fractionation stage 114 for separation into a plurality of fractions. In the example shown in FIG. 1, the hydroprocessed effluent is separated into a light neutral portion 118, a heavy neutral portion 124, and a brightstock portion 128. To allow for blocked operation, the light neutral portion 118 can be sent to corresponding light neutral storage 120, the heavy neutral portion 124 can be sent to corresponding heavy neutral storage 122, and the brightstock portion 128 can be sent to corresponding brightstock storage 126. A lower boiling range fraction 116 corresponding to fuels and / or light ends can also be generated by fractionation stage 114. Optionally, fractionation stage can generate a plurality of lower boiling range fractions 116.

[0034] FIG. 1 shows an example of the processing system during a light neutral processing block. In FIG. 1, the feed 130 to sweet processing stage 132 corresponds to a feed derived from light neutral storage 120. The sweet processing stage 132 can include at least dewaxing catalyst, and optionally can further include one or more of hydrocracking catalyst and aromatics saturation catalyst. The dewaxed effluent 136 from sweet processing stage 132 can then be passed into a fractionator 138 to form light neutral base stock product 142. A lower boiling fraction 140 corresponding to fuels and / or light ends can also be separated out by fractionator 138. Optionally, a portion of light neutral base stock 142 can be recycled. The recycled portion of light neutral base stock 142 can be used as a recycled feed portion 144 and / or as a recycled portion 134 that is added to light neutral storage 120. Recycling a portion 144 for use as part of the feed can be beneficial for increasing the lifetime of the catalysts in sour processing stage 110. Recycling a portion 134 to light neutral storage 120 can be beneficial for increasing conversion and / or viscosity index (VI).

[0035] FIG. 2 illustrates a process 200 for producing a pitch composition from an aromatic feedstock. Process 200 begins with introducing an aromatic feed 202 and solvent feed 206 into deasphalter 204. In deasphalter 204, the solvent feed and aromatic feed are contacted to generate a deasphalted oil 208 and deasphalted rock 216 which is the pitch composition. The deasphalted oil 206 is then processed in a hydrocracker 210 with hydrogen from hydrogen stream 212 to produce a hydrocracked stream 214. Hydrocracked stream 214 may be further separated into fuels and lubricant base stock such as a Group II or a Group III base stock. The deasphalted rock 216 is introduced into visbreaker unit 220 where the deasphalted rock is subjected to visbreaking conditions to produce pitch composition 218. In embodiments, visbreaker unit 220 includes a furnace containing tubes which the deasphalted rock flows through and optionally a soaker drum. Visbreaker unit 220 is operated at conditions suitable to thermally crack at least a portion of the deasphalted rock such as a temperature at a point in a range of 900° F. to 1400° F.

[0036] Suitable aromatic feeds include SATC products, main-column-bottom (MCB), hydrotreated main column bottom, steam cracker tar, hydrotreated steam cracker tar (HDT-SCT), crude oils, hydrotreated crude oils, coal tar pitch, petroleum pitch, vacuum residue (VR), atmospheric residue, asphalt, asphaltenes, bitumen, reformate, coker gas oil, heavy coker gas oil, thermal tar, thermal distillation cuts, tar, naphtha tar, pyrolysis tar, decant oil, or pitch-like substances produced by distillation, thermal treatment of such heavy oils, and combinations thereof. Suitable solvents for deasphalting include alkanes or other hydrocarbons (such as alkenes) containing 4 to 7 carbons (C4-C7) per molecule. Examples of suitable solvents include n-butane, isobutane, n-pentane, C4+ alkanes, C5+ alkanes, C4+ hydrocarbons, and C5+ hydrocarbons. In other aspects, suitable solvents can include C3 hydrocarbons, such as propane. In such other aspects, examples of suitable solvents include propane, n-butane, isobutane, n-pentane, C3+ alkanes, C4+ alkanes, C5+ alkanes, C3+ hydrocarbons, C4+ hydrocarbons, and C5+ hydrocarbons. Typical solvent deasphalting conditions include mixing a feedstock fraction with a solvent in a weight ratio of from about 1:2 to about 1:10, such as about 1:8 or less. Typical solvent deasphalting temperatures range from 40° C. to 200° C., or 40° C. to 150° C., depending on the nature of the feed and the solvent. The pressure during solvent deasphalting can be from about 50 psig (345 kPag) to about 500 psig (3447 kPag).Pitch Compositions

[0037] The pitch composition of the present disclosure may have a softening point at a point in a range of 30° C. to 240° C. Alternatively, the pitch composition of the present disclosure may have a softening point at a point in a range of 30° C. to 50° C., 50° C. to 100° C., 100° C. to 150° C., 150° C. to 200° C., 200° C. to 240, or any ranges therebetween. The pitch composition of the present disclosure may have an MCR at a point in a range of 5 wt. % to 100 wt. %. Alternatively, the pitch composition may have an MCR at a point in a range of 5 wt. % to 15 wt. %, 15 wt. % to 25 wt. %, 25 wt. % to 50 wt. %, 50 wt. % to 75 wt. %, 75 wt. % to 100 wt. %, or any ranges therebetween. In some embodiments, the pitch composition has a softening point between 40° C. and 100° C. and an MCRT of >30 wt. %. In some embodiments, the pitch composition has a softening point between 100° C. and 160° C. and an MCRT of >40 wt. %. In some embodiments, the pitch composition has a softening point between 160° C. and 220° C. and an MCRT of >50 wt. %. In some embodiments, the pitch composition has a softening point greater than >220° C. and an MCRT of >60 wt. %.

[0038] The pitch composition of the present disclosure may have a boiling point range of 480° C. to 760° C. Alternatively, the pitch composition of the present disclosure may have a boiling point range of 480° C. to 550° C., from 550° C. to 600° C., from 600° C. to 650° C., from 650° C. to 700° C., from 700° C. to 760° C., or any ranges therebetween.

[0039] The pitch composition of the present disclosure may have a T10, i.e. temperature where 10% of the volume is distilled, in a range of 480° C. to 550° C. Alternatively, a T10 in a range of 480° C. to 500° C., 500° C. to 520° C., 520° C. to 550° C. or any ranges therebetween. The pitch composition of the present disclosure may have a T50, i.e. temperature where 50% of the volume is distilled, in a range of 680° C. to 800° C. Alternatively, a T50 in a range of 680° C. to 720° C., 720° C. to 750° C., 750° C. to 775° C., 775° C. to 800° C., or any ranges therebetween.

[0040] The pitch composition of the present disclosure may have aromaticity in the range of 0.3 to 0.9. Alternatively, an aromaticity in the range of 0.3 to 0.8, 0.3 to 0.7, 0.3 to 0.6, 0.3 to 0.5, 0.4 to 0.8, 0.5 to 0.8, 0.6 to 0.8, 0.7 to 0.8, 0.8 to 0.9, or any ranges therebetween.

[0041] The pitch composition of the present disclosure may have a hydrogen content in a range of 5 wt. % to 15 wt. %. Alternatively, in a range of 5 wt. % to 7 wt. %, 7 wt. % to 9 wt. %, 9 wt. % to 11 wt. %, 11 wt. % to 15 wt. %, or any ranges therebetween.

[0042] The pitch composition of the present disclosure may have an H / C Ratio in the range of 0.5 to 1.0, encompassing any value and subset therebetween, such as 0.5 to 0.9, or 0.5 to 0.8, or 0.5 to 0.7, or 0.5 to 0.6, or 0.6 to 0.7, or 0.7 to 0.8, or 0.8 to 0.9, or 0.9 to 1.0.

[0043] The pitch compositions of the present composition may be toluene soluble. For example, the pitch compositions may be 95 wt. % or more soluble in toluene such as from 95 wt. % soluble to 100 wt. % soluble in toluene. Alternatively, from 95 wt. % to 97 wt. %, 97 wt. % to 99 wt. %, from 99 wt. % to 100 wt. %, or any ranges therebetween.

[0044] The pitch compositions may have a mesophase content of about 5 vol % or less (or about 4.5 vol % or less, or about 4 vol % or less, or about 3.5 vol % or less, or about 3 vol % or less, or about 2.5 vol % or less, or about 2 vol % or less, or about 1.5 vol % or less, or about 1 vol % or less, or about 0.5 vol % or less), based on the total volume of the pitch composition.

[0045] Alternately, the pitch compositions may have a mesophase content greater than about 5 vol % (or about 10 vol % or greater, or about 15 vol % or greater, or about 20 vol % or greater, or about 25 vol % or greater, or about 30 vol % or greater, or about 35 vol % or greater, or about 40 vol % or greater, or about 45 vol % or greater, or about 50 vol % or greater, or about 55 vol % or greater, or about 60 vol % or greater, or about 65 vol % or greater, or about 70 vol % or greater, or about 75 vol % or greater, or about 80 vol %, or about 85 vol % or greater, or about 90 vol % or greater, or about 95 vol % or greater, or about 98 vol % or greater), based on the total volume of the pitch composition.

[0046] The pitch composition may be fluxed with one or more aromatic solvents to produce a pitch composition with desired properties such as softening point and MCR. Aromatic solvents may include C6-C20 aromatic compounds. Some specific aromatic solvents include naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof. In embodiments, the pitch composition may be fluxed with 1 wt. % to 75 wt. % of the aromatic solvent. Alternatively, the pitch composition may be fluxed with 1 wt. % to 15 wt. % of the aromatic solvent, with 15 wt. % to 30 wt. % of the aromatic solvent, with 45 wt. % to 60 wt. % of the aromatic solvent, with 60 wt. % to 75 wt. % of the aromatic solvent, or any ranges therebetween.Carbon Fiber Application

[0047] The present disclosure also relates to methods for making carbon fiber comprising combining one or more carbon fibers derived from the pitch compositions or blended pitch compositions prepared according to the present disclosure. In some instances, the carbon fiber derived from the pitch may be combined with a thermoset polymer (e.g., cyclopentadiene, dicyclopentadiene, epoxy, pitch, phenolic resins, vinylester, polyimide and polyesters), a thermoplastic polymer (e.g., a thermoplastic polymer including one or more of: polyethylene, polypropylene, high-density polyethylene, linear low-density polyethylene, low-density polyethylene, polyamides, polyvinylchloride, polyetheretherketone, polyetherketoneketone, polyaryletherketone, polyetherimide and polyphenylene sulfide), cement, concrete, ceramic, metal, metal alloy, or any combination thereof. In other instances, the pitch composition itself can be used as a matrix and / or binder for producing a carbon fiber, thus enabling production of carbon-carbon composites.

[0048] In addition to carbon fibers, other suitable products can also be prepared from the pitch composition or blended pitch compositions in accordance with the present disclosure. For example, mesocarbon microbeads, graphite, and / or needle coke, among others, may be produced from the pitch composition or blended pitch compositions. Any suitable technique may be used for production of mesocarbon microbeads includes a condensation process that may include thermal polycondensation of the pitch or blended pitch composition. Additional techniques for production of mesocarbon microbeads may include emulsion or suspension processes.End Uses

[0049] Non-limiting examples of carbon articles may include automotive body parts (e.g., deck lids, hoods, front end, bumpers, doors, chassis, suspension systems such as leaf springs, drive shafts), off-shore tethers and drilling risers, wind turbine blades, insulating and sealing materials used in construction and road building (e.g., concrete), aircraft and space systems, high-performance aquatic vessels, airplanes, sports equipment, flying drones, armor, armored vehicles, military aircraft, energy storage systems, fireproof materials, lightweight cylinders and pressure vessels, and medical devices. Furthermore, fibers of the present disclosure (e.g., fiber filaments or webs) may be used as insulation materials (e.g., thermal or acoustic), or as shielding materials (e.g., electromagnetic or radio frequency), or in friction control surfaces (e.g., brake pads, such as aircraft brake pads). Further example, of carbon product applications may include graphitic foams for heat dissipation, protection against explosions and the like. Additional uses may include binder pitch, graphitizable carbon microbeads, solid lubricants, activated carbon fiber, and battery anodes.ADDITIONAL EMBODIMENTS

[0050] Accordingly, the present disclosure relates to pitch compositions, and more particularly to hydrocarbon soluble pitch compositions produced from aromatic feedstocks. The methods and systems may include any of the various features disclosed herein, including one or more of the following embodiments.

[0051] Embodiment 1. A composition comprising: a pitch composition having an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0052] Embodiment 2. The composition of embodiment 1 wherein the softening point is between about 40° C. to about 100° C.

[0053] Embodiment 3. The composition of embodiment 1 wherein the softening point is between about 100° C. to about 160° C. and wherein the pitch composition has an MCR of greater than 40 wt. %.

[0054] Embodiment 4. The composition of embodiment 1 wherein the softening point is between about 160° C. to about 220° C. and wherein the pitch composition has an MCR of greater than 50 wt. %.

[0055] Embodiment 5. The composition of embodiment 1 wherein the softening point is between about 220° C. to about 240° C. and wherein the pitch composition has an MCR of greater than 60 wt. %.

[0056] Embodiment 6. The composition of any of embodiments 1-5 wherein the pitch composition further comprises an aromatic solvent comprising a C6-C20 aromatic compound.

[0057] Embodiment 7. The composition of any of embodiments 1-5 wherein the pitch composition further comprises an aromatic solvent selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof.

[0058] Embodiment 8. The composition of embodiment 7 wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt. % to 75 wt. % of the aromatic solvent.

[0059] Embodiment 9. The composition of any of embodiments 1-8 wherein the pitch composition is produced from an aromatic feedstock produced from a SATC process.

[0060] Embodiment 10. A method comprising: introducing an aromatic feedstock into a deasphalting unit; and deasphalting at least a portion of the aromatic feedstock to produce a deasphalted oil and a deasphalted rock, wherein the deasphalted rock has an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the deasphalted rock is 100 wt. % soluble in toluene.

[0061] Embodiment 11. The method of embodiment 10 further comprising deasphalting at least a portion of the deasphalted oil to produce a deasphalted oil product and a soft rock product.

[0062] Embodiment 12. The method of any of embodiments 10-11 further comprising fluxing the deasphalted rock with an aromatic solvent comprising a C6-C20 aromatic compound.

[0063] Embodiment 13. The method of any of embodiments 10-12 wherein the pitch composition further comprises an aromatic solvent selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof.

[0064] Embodiment 14. The method of any of embodiments 10-13 wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt. % to 75 wt. % of the aromatic solvent.

[0065] Embodiment 15. The method of any of embodiments 10-14 wherein the aromatic feedstock comprises an aromatic feedstock produced from a SATC process or a sweet vacuum resid.

[0066] Embodiment 16. The method of any of embodiments 10-15 further comprising hydrocracking at least a portion of the deasphalted oil to produce a group II or a group III base stock.

[0067] Embodiment 17. The method of any of embodiments 10-16 further comprising introducing the deasphalted rock into a visbreaking unit and exposing the deasphalted rock to visbreaking conditions to produce a pitch composition.

[0068] Embodiment 18. The method of any of embodiments 10-17 wherein the softening point is between about 100° C. to about 160° C. and wherein the deasphalted rock has an MCR of greater than 40 wt. %.

[0069] Embodiment 19. The method of any of embodiments 10-18 wherein the softening point is between about 160° C. to about 220° C. and wherein the deasphalted rock has an MCR of greater than 50 wt. %.

[0070] Embodiment 20. The method of any of embodiments 10-19 wherein the softening point is between about 220° C. to about 240° C. and wherein the deasphalted rock has an MCR of greater than 60 wt. %.

[0071] Embodiment 21. A method comprising: introducing an aromatic feedstock produced from a SATC process into a deasphalting unit; deasphalting at least a portion of the aromatic feedstock with a C4-C7 solvent to produce a deasphalted oil and a deasphalted rock; and blending the deasphalted rock with an aromatic feedstock to produce a pitch composition with an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0072] Embodiment 22. The method of embodiment 21 wherein the aromatic solvent is selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof.

[0073] Embodiment 23. The method of any of embodiments 21-22 wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt. % to 75 wt. % of the aromatic solvent.

[0074] Embodiment 24. The method of any of embodiments 21-23 wherein the softening point is between about 100° C. to about 160° C. and wherein the pitch composition has an MCR of greater than 40 wt. %.

[0075] Embodiment 25. The method of any of embodiments 21-24 wherein the softening point is between about 220° C. to about 240° C. and wherein the pitch composition has an MCR of greater than 60 wt. %.EXAMPLES

[0076] To facilitate a better understanding of the embodiments of the present invention, the following examples of preferred or representative embodiments are given. In no way should the following examples be read to limit, or to define, the scope of the invention.Example 1

[0077] In this example, Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid was separated into deasphalted oil (DAO) and rock and further processed to form a low softening point, high MCRT isotropic pitch.

[0078] The SATC stage 1 vacuum resid was analyzed by simulated distillation and found to have a T10 distillation temperature of 950° F. (510° C.), a T50 distillation temperature of 1123° F. (606° C.), and a T90 distillation temperature of 1330° C. (721° C.). Further analysis found 0.4 wt. % sulfur, 40 wt. % MCRT, 7.2 wt. % hydrogen, 0.13 wt. % nitrogen, a density of 0.992 g / cc at 40° C., and a softening point of 165° C. The SATC stage 1 vacuum resid was 100% toluene soluble.

[0079] First, 1250 grams of SATC stage 1 vacuum resid and 750 grams of toluene were blended in a 3-liter pitcher. The pitcher was separated into DAO and rock in 12 1-liter batch separations. The separation began by pouring 64 grams of mixture from the pitcher into a 1 liter round bottomed flask. Next 250 grams of toluene was added to the flask, stoppered, and shaken to mix well. Next 250 grams of heptane were added to the flask and shaken. The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula was used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. Next 150 grams heptane mixed with 150 grams toluene was used to rinse the rock filter cake in the Buchner funnel. The filtration was carried out under vacuum for between 10 to 25 minutes. It was observed that the filter cake cracked into pieces as it dried and vacuum was applied for a further 3 to 10 minutes until the filter cake was dry. The filter cake was transferred to a vacuum oven equipped with a vacuum pump and the toluene and heptane solvents were removed at 75° C. overnight to form a rock of isotropic pitch.

[0080] After separation of the SATC stage 1 vacuum resid, the yield of DAO was 71 wt. % and the yield of isotropic pitch was 29 wt. %. The isotropic pitch was analyzed by simulated distillation and found to have a T10 distillation temperature of 965° F. (518° C.) and a T50 distillation temperature of 1350° F. (732° C.). The softening point of the isotropic pitch was measured as greater than 350° C. and the MCRT of the isotropic pitch was measured at 65 wt. %. The isotropic pitch was 100% toluene soluble.

[0081] A 4.0 gram sample of the isotropic pitch was ground into a powder and mixed with 0.73 grams of ExxonMobil™ Aromatic 200 which is a C11 high aromatic fluid with a minimum initial boiling point of 200° C. and a maximum final boiling point of 290° C. to form an isotropic pitch mixture. The isotropic pitch mixture was measured to have a softening point of 157° C. and an MCRT of 53 wt. %.

[0082] A 4.0 gram sample of the isotropic pitch was ground into a powder and mixed with 1.48 grams of ExxonMobil™ Aromatic 200 to form an isotropic pitch mixture. The isotropic pitch mixture was measured to have a softening point of 102° C. and an MCRT of 48 wt. %.Example 2

[0083] In this example, the isotropic pitch from example 1 was further transformed into mesophase pitch. An 80 gram sample of the isotropic pitch from example 1 was loaded into a 500 cc autoclave heated by a molten tin bath pre-heated to 810° F. (432° C.). A hydrogen flow of 50 standard cubic centimeters (sccm) is established. The autoclave was brought to 800° F. (426° C.) over a period of 10 minutes. The autoclave was held in the tin bath for another 110 minutes. The autoclave was pulled from the tin bath and cooled to 650° F. (343° C.) in less than 10 minutes. The autoclave was stripped with a flow of 200 sccm of hydrogen for 10 minutes at 650° F. (343° C.), and then cooled to room temperature. The yield of mesophase containing pitch was 78 wt. %. It was observed that the mesophase containing pitch had a softening point of greater than 350° C. and an MCRT of 83 wt. %.

[0084] The mesophase containing pitch was fluxed with 17.5 wt. % naphthalene. The resulting fluxed mesophase pitch had an MCRT of 68.5 wt. % and a softening point of 136° C. The fluxed mesophase pitch was analyzed using a polarized light microscope to produce the image in FIG. 3. In FIG. 3, the dots are roughly 5-micron spheres. It was observed that the mesophase pitch in the sample was contained in spheres with diameters of less than 1 micron. FIG. 4 is a graph of softening point versus MCRT coking value for commercially produced pitches as well as pitches produced from Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid. In FIG. 4 the cluster of “HDT SCT VR” pitches with softening point of less than 120° C. were produced by treating the SATC stage 1 vacuum resid from example 1 in an autoclave at 425° C. for 2 to 12 hours. The pitch at 170° C. softening point and 74 wt. % MCRT was produced by removing some of the material in the sample via vacuum distillation. The yield of the 170° C. softening point 74 wt. % MCRT sample on SATC Stage 1 Vacuum Resid was 60 wt. %. The process using deasphalting to tailor the feedstock composition, achieves a 72 wt. % yield and does not require a final vacuum distillation step. It was observed that the fluxed mesophase pitch has a higher coking value at lower softening point than the commercially produced pitches.Example 3

[0085] In this example, 50 grams of the DAO from example 1 was separated into two fractions. The 50 grams of DAO was added to a 1 liter round bottomed flask and 25 grams of toluene was added to the flask, stoppered, and shaken to mix well. Next, 50 grams of heptane was added to the flask and shaken. Thereafter, an additional 100 grams of heptane was added to the flask and shaken. The heptane step was repeated 3 more times. A total of 450 grams of heptane was added to the flask. The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula was used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. 270 grams heptane is used to rinse the rock filter cake. The filtration took between 10 and 25 minutes and the filter cake cracked into pieces as it dried and the filter cake was dried under vacuum for an additional 3 to 10 minutes. The filter cake was transferred to a vacuum oven equipped with a vacuum pump and the toluene and heptane solvents are removed at 75° C. overnight. The soft rock produced from the filtration is isotropic pitch. The deasphalted oil produced from the second deasphalting step is also a useful product.Example 4

[0086] In this example, the isotropic pitch from example 3 was further transformed into mesophase pitch. An 80 grams sample of isotropic pitch from example 3 was loaded into a 500 cc autoclave heated by a molten tin bath pre-heated to 810° F. (432° C.). A hydrogen flow of 50 standard cubic centimeters (sccm) is established. The autoclave was brought to 800° F. (426° C.) over a period of 10 minutes. The autoclave was held in the tin bath for another 110 minutes. The autoclave was pulled from the tin bath and cooled to 650° F. (343° C.) in less than 10 minutes. The autoclave was stripped with a flow of 200 sccm of hydrogen for 10 minutes at 650° F. (343° C.), and then cooled to room temperature. The yield of mesophase containing pitch was 71 wt. % pitch (<5 wt % mesophase). It was observed that the mesophase containing pitch had a softening point of 176° C. and an MCRT of 72 wt. %.Example 5

[0087] In this example, a crude oil vacuum resid was used to make an isotropic pitch. The vacuum resid has a 25 wt. % yield on crude. A sample of the crude oil vacuum resid was analyzed and found to have a T20 boiling point of 1078 F, a T50 boiling point of 1187 F, and a T80 boiling point of 1330 F. The crude oil was found to have 0.12 wt. % sulfur, 12.6 wt. % MCRT, 5.4 wt. % n-heptane insolubles (NHI), 0.4 wt. % N, and 18 API gravity.

[0088] A 1500-gram sample of the crude oil vacuum resid and 500 grams of toluene were blended in a 3 liter pitcher. The pitcher was separated into deasphalted oil (DAO) and rock in 28 1-liter batch separations. The separation starts by pouring 70 grams of the oil / toluene mixture from the pitcher into a 1 liter round bottomed flask. Then 50 grams of pentane chilled in dry ice was added to the flask, stoppered, and shaken to mix well. Next 130 grams of cold pentane was added to the flask and shaken. That step was repeated two more times resulting in a total addition of 440 g cold pentane in 4 increments (50 grams, then 130 grams, 130 grams, and 130 grams). The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula is used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. 270 grams pentane (pre chilled in dry ice) was used to rinse the rock filter cake. If the filtration slowed, some of the 270 g of rinse pentane is added to the Buchner funnel to facilitate the filtration. At least 50 g of the 270 g of rinse pentane was reserved for the end of the filtration. A successful filtration took between 10 and 25 minutes and the filter cake cracked into pieces as it dried. The vacuum was maintained for 3 to 10 minutes. The filter cake was transferred to a vacuum oven equipped with a vacuum pump and the toluene and pentane solvents were removed at 50° C. overnight. The DAO yield was 49 wt. %, contained 11.7 wt. % hydrogen, and had an MCRT of 5.7 wt. %. The rock was the isotropic pitch and had a yield of 51 wt. %, contained 11.9 wt. % hydrogen, had an MCRT of 19.2 wt. %, a sulfur content of 0.16 wt. %, and a softening point of 96° C. The results show that the MCRT of the isotropic pitch is higher than the DAO and therefore the aromatic compounds concentrate in the isotropic pitch. The high aromatic content of the isotropic pitch is compatible with visbreaking processes.

[0089] A visbreaking model was used to predict high severity visbreaking yield for the isotropic pitch. Visbreakers operate within a temperature window of 440 to 500 C, a pressure window of 3 to 10 bar (45 to 150 psig), and a residence time window of 1 to 10 minutes. The feed travels through a natural gas fired tubular heat exchanger to quickly heat the feed to the reaction temperature. The hot, visbroken products are depressured into a distillation tower operating at 5 to 30 psig which ends the thermal cracking reactions by rapid cooling (quenching) to temperatures below the distillation tower bottoms temperature (300-380 C). The visbreaking model converted 51 tons of visbreaker feedstock into the listed ton quantities of products. The model yielded a predicted effluent as follows:

[0090] A lube hydrocracking model was used to predict processing the deasphalted oil (DAO) to a group III base stock with a viscosity index (VI) of 124 and a pour point of −15° C. The lube hydrocracking model converted 49 tons of visbreaker feedstock into the listed ton quantities of products. The lube hydrocracking model yielded a predicted effluent as follows:

[0091] The models indicate that the crude oil vacuum resid of the example was upgraded to 49 wt. % lube hydrocracker feedstock, 7.5 wt. % carbon black feedstock, and 7.5 wt. % isotropic pitch. Once processed through a lube hydrocracker, the expected base stock yield on the starting crude oil vacuum resid is 34 wt. %.

[0092] All documents described herein are incorporated by reference herein for purposes of all jurisdictions where such practice is allowed, including any priority documents and / or testing procedures to the extent they are not inconsistent with this text. As is apparent from the foregoing general description and the specific embodiments, while forms of the disclosure have been illustrated and described, various modifications can be made without departing from the spirit and scope of the disclosure. Accordingly, it is not intended that the disclosure be limited thereby. For example, the compositions described herein may be free of any component, or composition not expressly recited or disclosed herein. Any method may lack any step not recited or disclosed herein. Likewise, the term “comprising” is considered synonymous with the term “including.” Whenever a method, composition, element or group of elements is preceded with the transitional phrase “comprising,” it is understood that we also contemplate the same composition or group of elements with transitional phrases “consisting essentially of,”“consisting of,”“selected from the group of consisting of,” or “is” preceding the recitation of the composition, element, or elements and vice versa.

[0093] Unless otherwise indicated, all numbers expressing quantities of ingredients, properties such as molecular weight, reaction conditions, and so forth used in the present specification and associated claims are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the embodiments of the present invention. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claim, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0094] Whenever a numerical range with a lower limit and an upper limit is disclosed, any number and any included range falling within the range is specifically disclosed, including the lower limit and upper limit. In particular, every range of values (of the form, “from about a to about b,” or, equivalently, “from approximately a to b,” or, equivalently, “from approximately a-b”) disclosed herein is to be understood to set forth every number and range encompassed within the broader range of values. Also, the terms in the claims have their plain, ordinary meaning unless otherwise explicitly and clearly defined by the patentee. Moreover, the indefinite articles “a” or “an,” as used in the claims, are defined herein to mean one or more than one of the element that it introduces.

[0095] One or more illustrative embodiments are presented herein. Not all features of a physical implementation are described or shown in this application for the sake of clarity. It is understood that in the development of a physical embodiment of the present disclosure, numerous implementation-specific decisions must be made to achieve the developer's goals, such as compliance with system-related, business-related, government-related and other constraints, which vary by implementation and from time to time. While a developer's efforts might be time-consuming, such efforts would be, nevertheless, a routine undertaking for one of ordinary skill in the art and having benefit of this disclosure.

[0096] Therefore, the present disclosure is well adapted to attain the ends and advantages mentioned as well as those that are inherent therein. The particular embodiments disclosed above are illustrative only, as the present disclosure may be modified and practiced in different but equivalent manners apparent to one having ordinary skill in the art and having the benefit of the teachings herein. Furthermore, no limitations are intended to the details of construction or design herein shown, other than as described in the claims below. It is therefore evident that the particular illustrative embodiments disclosed above may be altered, combined, or modified and all such variations are considered within the scope and spirit of the present disclosure. The embodiments illustratively disclosed herein suitably may be practiced in the absence of any element that is not specifically disclosed herein and / or any optional element disclosed herein.

Examples

example 1

[0077]In this example, Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid was separated into deasphalted oil (DAO) and rock and further processed to form a low softening point, high MCRT isotropic pitch.

[0078]The SATC stage 1 vacuum resid was analyzed by simulated distillation and found to have a T10 distillation temperature of 950° F. (510° C.), a T50 distillation temperature of 1123° F. (606° C.), and a T90 distillation temperature of 1330° C. (721° C.). Further analysis found 0.4 wt. % sulfur, 40 wt. % MCRT, 7.2 wt. % hydrogen, 0.13 wt. % nitrogen, a density of 0.992 g / cc at 40° C., and a softening point of 165° C. The SATC stage 1 vacuum resid was 100% toluene soluble.

[0079]First, 1250 grams of SATC stage 1 vacuum resid and 750 grams of toluene were blended in a 3-liter pitcher. The pitcher was separated into DAO and rock in 12 1-liter batch separations. The separation began by pouring 64 grams of mixture from the pitcher into a 1 liter round bottomed flask. Next 250 gr...

example 2

[0083]In this example, the isotropic pitch from example 1 was further transformed into mesophase pitch. An 80 gram sample of the isotropic pitch from example 1 was loaded into a 500 cc autoclave heated by a molten tin bath pre-heated to 810° F. (432° C.). A hydrogen flow of 50 standard cubic centimeters (sccm) is established. The autoclave was brought to 800° F. (426° C.) over a period of 10 minutes. The autoclave was held in the tin bath for another 110 minutes. The autoclave was pulled from the tin bath and cooled to 650° F. (343° C.) in less than 10 minutes. The autoclave was stripped with a flow of 200 sccm of hydrogen for 10 minutes at 650° F. (343° C.), and then cooled to room temperature. The yield of mesophase containing pitch was 78 wt. %. It was observed that the mesophase containing pitch had a softening point of greater than 350° C. and an MCRT of 83 wt. %.

[0084]The mesophase containing pitch was fluxed with 17.5 wt. % naphthalene. The resulting fluxed mesophase pitch ha...

example 3

[0085]In this example, 50 grams of the DAO from example 1 was separated into two fractions. The 50 grams of DAO was added to a 1 liter round bottomed flask and 25 grams of toluene was added to the flask, stoppered, and shaken to mix well. Next, 50 grams of heptane was added to the flask and shaken. Thereafter, an additional 100 grams of heptane was added to the flask and shaken. The heptane step was repeated 3 more times. A total of 450 grams of heptane was added to the flask. The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula was used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. 270 grams heptane is used to rinse the rock filter cake. The filtration took...

CROSS REFERENCE TO RELATED APPLICATIONS

[0001] This application is a national stage application, filed under 35 U.S.C. 371, of International Patent Application No. PCT / US2024 / 025195, filed Apr. 18, 2024, which claims the priority of U.S. Provisional Patent Application No. 63 / 467,821, filed May 19, 2023, which is incorporated by reference in its entirety.FIELD

[0002] The present disclosure relates to pitch compositions, and more particularly to hydrocarbon solvent soluble pitch compositions produced from aromatic feedstocks.BACKGROUND

[0003] Pitch is a carbon-containing feedstock which can be classified as an isotropic pitch, or a mesophase pitch. Both isotropic and mesophase pitch can be complex mixtures of aromatic molecules; however, the aromatic molecules in an isotropic pitch are randomly oriented, whereas in a mesophase pitch, at least a portion of these aromatic molecules are ordered. A mesophase pitch may have a heterogeneous two-phase structure comprising the said ordered aromatic molecules (e.g., anisotropic region), and an isotropic region. In general, an isotropic pitch formation precedes a mesophase pitch formation. Both types of pitches will be collectively referred to herein as “pitch,” unless otherwise indicated.

[0004] Conventional methods for pitch production include conversion processes such as thermal and / or catalytic conversion of aromatic hydrocarbon feedstocks at elevated temperatures under vigorous stirring and long residence times to produce a crude pitch product. High temperatures and vacuum are often required to effectively separate components of the crude pitch product to produce a finished pitch product. The application of vacuum adds cost to the process, limits throughput, and can only be used to remove the lowest molecular weight compounds. Furthermore, as the temperature of the separation processes increases, undesirable chemical side reactions occur, leading to the formation of a mixture comprising coke and a pitch of poor qualities, which is unfit for the production of carbon materials. Additionally, non-volatile impurities such as ashes, metal contaminants, and other undesirable particulate present in the hydrocarbon feedstock and formed during the reaction, may remain in the pitch, thus making the pitch unsuitable for carbon product manufacturing. Conventional distillation processes are not sufficient to mitigate / eliminate such impurities.

[0005] Isotropic pitches are useful materials to produce carbon products. Liquid isotropic pitches can be easily coated onto solids or formed into arbitrary shapes. Isotropic pitch is readily thermoset by high temperature calcination in the absence of air to form solid carbon. High quality isotropic pitches can be calcined such that a majority of the composition (e.g., >50 wt. %) is converted to solid carbon. The high carbon yield upon calcination enables the production of strong, high density carbon parts. Isotropic pitch is useful in production of electric arc furnace electrodes, aluminum-carbon electrodes, battery electrodes, as well as in carbon part manufacturing where isotropic pitch is used as a glue to bond carbon fiber strands and sheets, among other uses. Pitch is also used in a number of product applications, such as carbon fiber, binder pitch, impregnation pitch, high-performance and general-purpose carbon fiber, refractories, carbon / carbon composites, synthetic graphite, graphite parts, mesocarbon microbeads for anodes for lithium ion batteries, carbon foam for heat transfer applications, sound absorbers, roofing products, lubricants, and consumer products such as cosmetics, among other uses.

[0006] Pitches are fouling and tend to stick to machinery and components which contact the pitch during production of the pitch and production of carbon products from the pitch. Pitches are generally insoluble to minimally soluble in hydrocarbon solvents making cleaning of machinery and components which the pitch contacts difficult. Over time, surfaces contacted by pitch tend to become covered by solid carbon.SUMMARY

[0007] Disclosed herein is an example method including a composition comprising: a pitch composition having an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0008] Further disclosed herein is a method comprising: introducing an aromatic feedstock into a deasphalting unit; and deasphalting at least a portion of the aromatic feedstock to produce a deasphalted oil and a deasphalted rock, wherein the deasphalted rock has an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the deasphalted rock is 100 wt. % soluble in toluene.

[0009] Further disclosed herein is a method comprising: introducing an aromatic feedstock produced from a SATC process into a deasphalting unit; deasphalting at least a portion of the aromatic feedstock with a C4-C7 solvent to produce a deasphalted oil and a deasphalted rock; and blending the deasphalted rock with an aromatic feedstock to produce a pitch composition with an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0010] These and other features and attributes of the disclosed methods and compositions 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

[0011] 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:

[0012] FIG. 1 illustrates process for producing a pitch composition from an aromatic feedstock, in accordance with some embodiments of the present disclosure.

[0013] FIG. 2 illustrates process for producing a pitch composition from an aromatic feedstock, in accordance with some embodiments of the present disclosure.

[0014] FIG. 3 is a graph of softening point versus wt. % MCRT coking for pitches, in accordance with some embodiments of the present disclosure.

[0015] FIG. 4 is a graph of softening point versus MCRT coking value for commercially produced pitches as well as pitches produced from Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid, in accordance with some embodiments of the present disclosure.DETAILED DESCRIPTION

[0016] The present disclosure relates to pitch compositions and more particularly to hydrocarbon solvent soluble pitch compositions produced from aromatic feedstocks. The disclosed pitch compositions may be soluble in toluene and other hydrocarbon solvents and have relatively low softening points. In some embodiments, the pitch compositions, including mesophase pitch compositions, are produced from petroleum tars such as from the vacuum resid fraction of hydrotreated steam cracker tar, FCC main column bottoms, a composition from a SATC process, sweet vacuum resid, and / or coal tar.

[0017] The present disclosure further relates to a process for upgrading sweet vacuum resid fractions from atmospheric distillation of crude oil to form pitch compositions. Sweet vacuum resid fractions are the residues from distillation of crude oil which contain less than 1 wt. % sulfur and are typically used in a low sulfur fuel oil (LSFO) and as part of a feed to an FCC unit to produce gasoline. The demand for sweet vacuum resid fractions is expected to decline as the demand for these types of fuel also declines. Further conversion of the sweet vacuum resid fractions are limited as sweet vacuum resid typically can't be driven to high 1050° F.+ (565° C.) conversion in a visbreaker unit due to incompatibility. The present disclosure allows for the sweet vacuum resid fractions to be converted to useful materials such as deasphalted oil (DAO), fuels, lubricant base stock, and pitch compositions.

[0018] Pitch compositions have been previously made from naphthalene using acid catalysis. The naphthalene derived pitch may be fluxed with methyl-naphthalene which results in a solvated mesophase pitch having a softening point in a range of 200-300° C. and an MCRT wt. % of 65-78.

[0019] The presently disclosed methods of producing pitch compositions from petroleum tar have a similar MCRT but a much lower softening point in a range of 30° C.-150° C. for the approximately same MCRT value of pitch derived from naphthalene.Definitions and Test Methods

[0020] All numerical values within the detailed description and the claims herein are modified by “about” or “approximately” with respect to the indicated value, and take into account experimental error and variations that would be expected by a person having ordinary skill in the art. Unless otherwise indicated, ambient temperature (room temperature or “RT”) is about 25° C.

[0021] As used in the present disclosure and claims, the singular forms “a,”“an,” and “the” include plural forms unless the context clearly dictates otherwise.

[0022] The term “and / or” as used in a phrase such as “A and / or B” herein is intended to include “A and B,”“A or B,”“A,” and “B.”

[0023] For the purposes of the present disclosure and the claims thereto, the following definitions shall be used.

[0024] As used herein, the term “pitch” refers to hydrocarbons with softening points above 30° C., consisting of mainly aromatic and alkyl-substituted aromatic compounds. These aromatic compounds are primarily hydrocarbons, but heteroatoms and traces of metals can be present within these materials. When cooled from a melt, a pitch can solidify into an amorphous solid. Pitches may include petroleum pitches, coal tar pitches, natural asphalts, pitches contained as by products in the naphtha cracking industry, pitches of high carbon content obtained from petroleum asphalt and other substances having properties of pitches produced as products in various industrial production processes. Pitches exhibit a broad softening temperature range and are typically derived from petroleum, coal tar, plants, or catalytic oligomerization of small molecules (e.g., acid-catalyzed oligomerization). A pitch can also be referred to as tar, bitumen, or asphalt. When a pitch is produced from plants, it is also referred to as resin. Various pitches may be obtained as products in the gas oil or naphtha cracking industry as a carbonaceous residue consisting of a complex mixture of primarily aromatic organic compounds, which are solids at room temperature, and exhibit a relatively broad softening temperature range. Hence, a pitch can be obtained from heat treatment and distillation of petroleum fractions. A “petroleum pitch” refers to the residuum carbonaceous material obtained from distillation of crude oils and from the catalytic cracking of petroleum distillates. A “coal tar pitch” refers to the material obtained by distillation of coal.

[0025] As used herein, the term “mesophase” refers to a discotic liquid crystalline material consisting of planar aromatic molecules with a broader molecular weight distribution. A “mesophase pitch” consists of “mesophase” and optionally an isotropic phase. The mesophase exhibits optical anisotropy (birefringence) when examined using a polarized light microscope. For example, a mesophase pitch can be a pitch containing more than about 10 vol % mesophase, based on the total volume of the pitch. A mesophase content of a pitch can be measured, according to ASTM D4616 (Standard Test Method for Microscopical Analysis by Reflected Light and Determination of Mesophase in a Pitch), from reflected polarized light microscopy images by imbedding various samples of the pitch in epoxy, followed by polishing the samples until they become highly reflective. A series of images can be recorded in order to quantify the anisotropic content.

[0026] The term “softening point” or “SP,” and grammatical variants, as used herein, refers to a temperature or a range of temperatures at which a substance softens. Herein, the softening point is measured using a METTLER TOLEDO dropping point instrument, such as METTLER TOLEDO DP70, according to a procedure analogous to the American Society for Testing and Materials (ASTM) ASTM D3104-14a.

[0027] As used herein, the term “microcarbon residue” or “MCR,” and grammatical variants thereof, refers to an amount of carbonaceous residue formed after evaporation and pyrolysis of petroleum materials under particular conditions. The term “microcarbon residue test” or “MCRT,” and grammatical variants thereof, as used herein, refers to a standard method for the determination of MCR and is measured according to ASTM D4530 (2020).

[0028] As used herein, the term “mesocarbon microbead,” refers to a porous graphite carbon material wherein an inner core is composed of amorphous carbon while an outer shell is composed of graphitic carbon. Both the inner core and the outer shell are porous. The mesocarbon microbeads have an diameter ranging from 10 microns to 100 microns.

[0029] As used herein, the term “hydrogen to carbon ratio” or “H / C Ratio,” and grammatical variants thereof, refers to an amount of elemental hydrogen to elemental carbon within a pitch composition. The H / C Ratio is measured according to ASTM D5291-21.

[0030] “SCT” means (a) a mixture of hydrocarbons having one or more aromatic components and optionally (b) non-aromatic and / or non-hydrocarbon molecules, the mixture being derived from hydrocarbon pyrolysis and having a 90% Total Boiling Point >550° F. (290° C.) (e.g., >90.0 wt % of the SCT molecules have an atmospheric boiling point >550° F. (290° C.)). SCT can contain >50.0 wt % (e.g., >75.0 wt %, such as >90.0 wt %), based on the weight of the SCT, of hydrocarbon molecules (including mixtures and aggregates thereof) having (i) one or more aromatic components and (ii) a number of carbon atoms >15. SCT generally has a metals content, <1.0×103 ppmw, based on the weight of the SCT (e.g., an amount of metals that is far less than that found in crude oil (or crude oil components) of the same average viscosity). SCT typically has a mass density >1.0 Kg / L, e.g., >1.05 Kg / L, such as >1.1 Kg / L, or >1.15 Kg / L.

[0031] “Solvent assisted tar conversion” or (“SATC”) is a process for producing an upgraded tar, such as SCT. The process includes hydroprocessing a tar stream in the presence of a utility fluid, and is generally described in P.C.T. Patent Application Publication No. WO 2018 / 111577, which is incorporated by reference in its entirety. For example, SATC can include hydroprocessing one or more SCT streams, including those that have been subjected to prior pretreatments, in the presence of a utility fluid, to produce a hydroprocessed tar having a lesser viscosity, improved blending characteristics, fewer heteroatom impurities, and a lesser content of solids and semi-solids (e.g., fewer particles) as compared to the SCT feed. The SATC process produces several intermediate streams including a SATC stage 1 product, sometimes referred to as SATC stage 1 vacuum resid, which is the bottoms fraction I which is fed to a 2nd Stage hydroprocessing reactor L for an additional hydroprocessing step that provides desulfurization.Methods of Making Pitch Compositions

[0032] FIG. 1 illustrates process 100 for producing a pitch composition from an aromatic feedstock. In FIG. 1, an aromatic feed 102 is introduced into a deasphalter 104. The deasphalter 104 generates a deasphalted oil 106 and deasphalted rock 108 which is the pitch composition. The deasphalted oil 106 is then processed in a sour processing stage 110. Optionally, a portion 144 of recycled light neutral base product 142 can be combined with deasphalted oil 106. Sour processing stage 110 can include one or more of a demetallation catalyst, a hydrotreating catalyst, a hydrocracking catalyst, and / or an aromatic saturation catalyst. The conditions in sour processing stage 110 can be selected to at least reduce the sulfur content of the hydroprocessed effluent 112 to 20 wppm or less. This can correspond to 15 wt. % to 40 wt. % conversion of the feed relative to 370° C. Optionally, the amount of conversion in the sour processing stage 110 can be any convenient higher amount so long as the combined conversion in sour processing stage 110 and sweet processing stage 132 is 90 wt. % or less.

[0033] The hydroprocessed effluent 112 can then be passed into fractionation stage 114 for separation into a plurality of fractions. In the example shown in FIG. 1, the hydroprocessed effluent is separated into a light neutral portion 118, a heavy neutral portion 124, and a brightstock portion 128. To allow for blocked operation, the light neutral portion 118 can be sent to corresponding light neutral storage 120, the heavy neutral portion 124 can be sent to corresponding heavy neutral storage 122, and the brightstock portion 128 can be sent to corresponding brightstock storage 126. A lower boiling range fraction 116 corresponding to fuels and / or light ends can also be generated by fractionation stage 114. Optionally, fractionation stage can generate a plurality of lower boiling range fractions 116.

[0034] FIG. 1 shows an example of the processing system during a light neutral processing block. In FIG. 1, the feed 130 to sweet processing stage 132 corresponds to a feed derived from light neutral storage 120. The sweet processing stage 132 can include at least dewaxing catalyst, and optionally can further include one or more of hydrocracking catalyst and aromatics saturation catalyst. The dewaxed effluent 136 from sweet processing stage 132 can then be passed into a fractionator 138 to form light neutral base stock product 142. A lower boiling fraction 140 corresponding to fuels and / or light ends can also be separated out by fractionator 138. Optionally, a portion of light neutral base stock 142 can be recycled. The recycled portion of light neutral base stock 142 can be used as a recycled feed portion 144 and / or as a recycled portion 134 that is added to light neutral storage 120. Recycling a portion 144 for use as part of the feed can be beneficial for increasing the lifetime of the catalysts in sour processing stage 110. Recycling a portion 134 to light neutral storage 120 can be beneficial for increasing conversion and / or viscosity index (VI).

[0035] FIG. 2 illustrates a process 200 for producing a pitch composition from an aromatic feedstock. Process 200 begins with introducing an aromatic feed 202 and solvent feed 206 into deasphalter 204. In deasphalter 204, the solvent feed and aromatic feed are contacted to generate a deasphalted oil 208 and deasphalted rock 216 which is the pitch composition. The deasphalted oil 206 is then processed in a hydrocracker 210 with hydrogen from hydrogen stream 212 to produce a hydrocracked stream 214. Hydrocracked stream 214 may be further separated into fuels and lubricant base stock such as a Group II or a Group III base stock. The deasphalted rock 216 is introduced into visbreaker unit 220 where the deasphalted rock is subjected to visbreaking conditions to produce pitch composition 218. In embodiments, visbreaker unit 220 includes a furnace containing tubes which the deasphalted rock flows through and optionally a soaker drum. Visbreaker unit 220 is operated at conditions suitable to thermally crack at least a portion of the deasphalted rock such as a temperature at a point in a range of 900° F. to 1400° F.

[0036] Suitable aromatic feeds include SATC products, main-column-bottom (MCB), hydrotreated main column bottom, steam cracker tar, hydrotreated steam cracker tar (HDT-SCT), crude oils, hydrotreated crude oils, coal tar pitch, petroleum pitch, vacuum residue (VR), atmospheric residue, asphalt, asphaltenes, bitumen, reformate, coker gas oil, heavy coker gas oil, thermal tar, thermal distillation cuts, tar, naphtha tar, pyrolysis tar, decant oil, or pitch-like substances produced by distillation, thermal treatment of such heavy oils, and combinations thereof. Suitable solvents for deasphalting include alkanes or other hydrocarbons (such as alkenes) containing 4 to 7 carbons (C4-C7) per molecule. Examples of suitable solvents include n-butane, isobutane, n-pentane, C4+ alkanes, C5+ alkanes, C4+ hydrocarbons, and C5+ hydrocarbons. In other aspects, suitable solvents can include C3 hydrocarbons, such as propane. In such other aspects, examples of suitable solvents include propane, n-butane, isobutane, n-pentane, C3+ alkanes, C4+ alkanes, C5+ alkanes, C3+ hydrocarbons, C4+ hydrocarbons, and C5+ hydrocarbons. Typical solvent deasphalting conditions include mixing a feedstock fraction with a solvent in a weight ratio of from about 1:2 to about 1:10, such as about 1:8 or less. Typical solvent deasphalting temperatures range from 40° C. to 200° C., or 40° C. to 150° C., depending on the nature of the feed and the solvent. The pressure during solvent deasphalting can be from about 50 psig (345 kPag) to about 500 psig (3447 kPag).Pitch Compositions

[0037] The pitch composition of the present disclosure may have a softening point at a point in a range of 30° C. to 240° C. Alternatively, the pitch composition of the present disclosure may have a softening point at a point in a range of 30° C. to 50° C., 50° C. to 100° C., 100° C. to 150° C., 150° C. to 200° C., 200° C. to 240, or any ranges therebetween. The pitch composition of the present disclosure may have an MCR at a point in a range of 5 wt. % to 100 wt. %. Alternatively, the pitch composition may have an MCR at a point in a range of 5 wt. % to 15 wt. %, 15 wt. % to 25 wt. %, 25 wt. % to 50 wt. %, 50 wt. % to 75 wt. %, 75 wt. % to 100 wt. %, or any ranges therebetween. In some embodiments, the pitch composition has a softening point between 40° C. and 100° C. and an MCRT of >30 wt. %. In some embodiments, the pitch composition has a softening point between 100° C. and 160° C. and an MCRT of >40 wt. %. In some embodiments, the pitch composition has a softening point between 160° C. and 220° C. and an MCRT of >50 wt. %. In some embodiments, the pitch composition has a softening point greater than >220° C. and an MCRT of >60 wt. %.

[0038] The pitch composition of the present disclosure may have a boiling point range of 480° C. to 760° C. Alternatively, the pitch composition of the present disclosure may have a boiling point range of 480° C. to 550° C., from 550° C. to 600° C., from 600° C. to 650° C., from 650° C. to 700° C., from 700° C. to 760° C., or any ranges therebetween.

[0039] The pitch composition of the present disclosure may have a T10, i.e. temperature where 10% of the volume is distilled, in a range of 480° C. to 550° C. Alternatively, a T10 in a range of 480° C. to 500° C., 500° C. to 520° C., 520° C. to 550° C. or any ranges therebetween. The pitch composition of the present disclosure may have a T50, i.e. temperature where 50% of the volume is distilled, in a range of 680° C. to 800° C. Alternatively, a T50 in a range of 680° C. to 720° C., 720° C. to 750° C., 750° C. to 775° C., 775° C. to 800° C., or any ranges therebetween.

[0040] The pitch composition of the present disclosure may have aromaticity in the range of 0.3 to 0.9. Alternatively, an aromaticity in the range of 0.3 to 0.8, 0.3 to 0.7, 0.3 to 0.6, 0.3 to 0.5, 0.4 to 0.8, 0.5 to 0.8, 0.6 to 0.8, 0.7 to 0.8, 0.8 to 0.9, or any ranges therebetween.

[0041] The pitch composition of the present disclosure may have a hydrogen content in a range of 5 wt. % to 15 wt. %. Alternatively, in a range of 5 wt. % to 7 wt. %, 7 wt. % to 9 wt. %, 9 wt. % to 11 wt. %, 11 wt. % to 15 wt. %, or any ranges therebetween.

[0042] The pitch composition of the present disclosure may have an H / C Ratio in the range of 0.5 to 1.0, encompassing any value and subset therebetween, such as 0.5 to 0.9, or 0.5 to 0.8, or 0.5 to 0.7, or 0.5 to 0.6, or 0.6 to 0.7, or 0.7 to 0.8, or 0.8 to 0.9, or 0.9 to 1.0.

[0043] The pitch compositions of the present composition may be toluene soluble. For example, the pitch compositions may be 95 wt. % or more soluble in toluene such as from 95 wt. % soluble to 100 wt. % soluble in toluene. Alternatively, from 95 wt. % to 97 wt. %, 97 wt. % to 99 wt. %, from 99 wt. % to 100 wt. %, or any ranges therebetween.

[0044] The pitch compositions may have a mesophase content of about 5 vol % or less (or about 4.5 vol % or less, or about 4 vol % or less, or about 3.5 vol % or less, or about 3 vol % or less, or about 2.5 vol % or less, or about 2 vol % or less, or about 1.5 vol % or less, or about 1 vol % or less, or about 0.5 vol % or less), based on the total volume of the pitch composition.

[0045] Alternately, the pitch compositions may have a mesophase content greater than about 5 vol % (or about 10 vol % or greater, or about 15 vol % or greater, or about 20 vol % or greater, or about 25 vol % or greater, or about 30 vol % or greater, or about 35 vol % or greater, or about 40 vol % or greater, or about 45 vol % or greater, or about 50 vol % or greater, or about 55 vol % or greater, or about 60 vol % or greater, or about 65 vol % or greater, or about 70 vol % or greater, or about 75 vol % or greater, or about 80 vol %, or about 85 vol % or greater, or about 90 vol % or greater, or about 95 vol % or greater, or about 98 vol % or greater), based on the total volume of the pitch composition.

[0046] The pitch composition may be fluxed with one or more aromatic solvents to produce a pitch composition with desired properties such as softening point and MCR. Aromatic solvents may include C6-C20 aromatic compounds. Some specific aromatic solvents include naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof. In embodiments, the pitch composition may be fluxed with 1 wt. % to 75 wt. % of the aromatic solvent. Alternatively, the pitch composition may be fluxed with 1 wt. % to 15 wt. % of the aromatic solvent, with 15 wt. % to 30 wt. % of the aromatic solvent, with 45 wt. % to 60 wt. % of the aromatic solvent, with 60 wt. % to 75 wt. % of the aromatic solvent, or any ranges therebetween.Carbon Fiber Application

[0047] The present disclosure also relates to methods for making carbon fiber comprising combining one or more carbon fibers derived from the pitch compositions or blended pitch compositions prepared according to the present disclosure. In some instances, the carbon fiber derived from the pitch may be combined with a thermoset polymer (e.g., cyclopentadiene, dicyclopentadiene, epoxy, pitch, phenolic resins, vinylester, polyimide and polyesters), a thermoplastic polymer (e.g., a thermoplastic polymer including one or more of: polyethylene, polypropylene, high-density polyethylene, linear low-density polyethylene, low-density polyethylene, polyamides, polyvinylchloride, polyetheretherketone, polyetherketoneketone, polyaryletherketone, polyetherimide and polyphenylene sulfide), cement, concrete, ceramic, metal, metal alloy, or any combination thereof. In other instances, the pitch composition itself can be used as a matrix and / or binder for producing a carbon fiber, thus enabling production of carbon-carbon composites.

[0048] In addition to carbon fibers, other suitable products can also be prepared from the pitch composition or blended pitch compositions in accordance with the present disclosure. For example, mesocarbon microbeads, graphite, and / or needle coke, among others, may be produced from the pitch composition or blended pitch compositions. Any suitable technique may be used for production of mesocarbon microbeads includes a condensation process that may include thermal polycondensation of the pitch or blended pitch composition. Additional techniques for production of mesocarbon microbeads may include emulsion or suspension processes.End Uses

[0049] Non-limiting examples of carbon articles may include automotive body parts (e.g., deck lids, hoods, front end, bumpers, doors, chassis, suspension systems such as leaf springs, drive shafts), off-shore tethers and drilling risers, wind turbine blades, insulating and sealing materials used in construction and road building (e.g., concrete), aircraft and space systems, high-performance aquatic vessels, airplanes, sports equipment, flying drones, armor, armored vehicles, military aircraft, energy storage systems, fireproof materials, lightweight cylinders and pressure vessels, and medical devices. Furthermore, fibers of the present disclosure (e.g., fiber filaments or webs) may be used as insulation materials (e.g., thermal or acoustic), or as shielding materials (e.g., electromagnetic or radio frequency), or in friction control surfaces (e.g., brake pads, such as aircraft brake pads). Further example, of carbon product applications may include graphitic foams for heat dissipation, protection against explosions and the like. Additional uses may include binder pitch, graphitizable carbon microbeads, solid lubricants, activated carbon fiber, and battery anodes.ADDITIONAL EMBODIMENTS

[0050] Accordingly, the present disclosure relates to pitch compositions, and more particularly to hydrocarbon soluble pitch compositions produced from aromatic feedstocks. The methods and systems may include any of the various features disclosed herein, including one or more of the following embodiments.

[0051] Embodiment 1. A composition comprising: a pitch composition having an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0052] Embodiment 2. The composition of embodiment 1 wherein the softening point is between about 40° C. to about 100° C.

[0053] Embodiment 3. The composition of embodiment 1 wherein the softening point is between about 100° C. to about 160° C. and wherein the pitch composition has an MCR of greater than 40 wt. %.

[0054] Embodiment 4. The composition of embodiment 1 wherein the softening point is between about 160° C. to about 220° C. and wherein the pitch composition has an MCR of greater than 50 wt. %.

[0055] Embodiment 5. The composition of embodiment 1 wherein the softening point is between about 220° C. to about 240° C. and wherein the pitch composition has an MCR of greater than 60 wt. %.

[0056] Embodiment 6. The composition of any of embodiments 1-5 wherein the pitch composition further comprises an aromatic solvent comprising a C6-C20 aromatic compound.

[0057] Embodiment 7. The composition of any of embodiments 1-5 wherein the pitch composition further comprises an aromatic solvent selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof.

[0058] Embodiment 8. The composition of embodiment 7 wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt. % to 75 wt. % of the aromatic solvent.

[0059] Embodiment 9. The composition of any of embodiments 1-8 wherein the pitch composition is produced from an aromatic feedstock produced from a SATC process.

[0060] Embodiment 10. A method comprising: introducing an aromatic feedstock into a deasphalting unit; and deasphalting at least a portion of the aromatic feedstock to produce a deasphalted oil and a deasphalted rock, wherein the deasphalted rock has an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the deasphalted rock is 100 wt. % soluble in toluene.

[0061] Embodiment 11. The method of embodiment 10 further comprising deasphalting at least a portion of the deasphalted oil to produce a deasphalted oil product and a soft rock product.

[0062] Embodiment 12. The method of any of embodiments 10-11 further comprising fluxing the deasphalted rock with an aromatic solvent comprising a C6-C20 aromatic compound.

[0063] Embodiment 13. The method of any of embodiments 10-12 wherein the pitch composition further comprises an aromatic solvent selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof.

[0064] Embodiment 14. The method of any of embodiments 10-13 wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt. % to 75 wt. % of the aromatic solvent.

[0065] Embodiment 15. The method of any of embodiments 10-14 wherein the aromatic feedstock comprises an aromatic feedstock produced from a SATC process or a sweet vacuum resid.

[0066] Embodiment 16. The method of any of embodiments 10-15 further comprising hydrocracking at least a portion of the deasphalted oil to produce a group II or a group III base stock.

[0067] Embodiment 17. The method of any of embodiments 10-16 further comprising introducing the deasphalted rock into a visbreaking unit and exposing the deasphalted rock to visbreaking conditions to produce a pitch composition.

[0068] Embodiment 18. The method of any of embodiments 10-17 wherein the softening point is between about 100° C. to about 160° C. and wherein the deasphalted rock has an MCR of greater than 40 wt. %.

[0069] Embodiment 19. The method of any of embodiments 10-18 wherein the softening point is between about 160° C. to about 220° C. and wherein the deasphalted rock has an MCR of greater than 50 wt. %.

[0070] Embodiment 20. The method of any of embodiments 10-19 wherein the softening point is between about 220° C. to about 240° C. and wherein the deasphalted rock has an MCR of greater than 60 wt. %.

[0071] Embodiment 21. A method comprising: introducing an aromatic feedstock produced from a SATC process into a deasphalting unit; deasphalting at least a portion of the aromatic feedstock with a C4-C7 solvent to produce a deasphalted oil and a deasphalted rock; and blending the deasphalted rock with an aromatic feedstock to produce a pitch composition with an MCR of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

[0072] Embodiment 22. The method of embodiment 21 wherein the aromatic solvent is selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof.

[0073] Embodiment 23. The method of any of embodiments 21-22 wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt. % to 75 wt. % of the aromatic solvent.

[0074] Embodiment 24. The method of any of embodiments 21-23 wherein the softening point is between about 100° C. to about 160° C. and wherein the pitch composition has an MCR of greater than 40 wt. %.

[0075] Embodiment 25. The method of any of embodiments 21-24 wherein the softening point is between about 220° C. to about 240° C. and wherein the pitch composition has an MCR of greater than 60 wt. %.EXAMPLES

[0076] To facilitate a better understanding of the embodiments of the present invention, the following examples of preferred or representative embodiments are given. In no way should the following examples be read to limit, or to define, the scope of the invention.Example 1

[0077] In this example, Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid was separated into deasphalted oil (DAO) and rock and further processed to form a low softening point, high MCRT isotropic pitch.

[0078] The SATC stage 1 vacuum resid was analyzed by simulated distillation and found to have a T10 distillation temperature of 950° F. (510° C.), a T50 distillation temperature of 1123° F. (606° C.), and a T90 distillation temperature of 1330° C. (721° C.). Further analysis found 0.4 wt. % sulfur, 40 wt. % MCRT, 7.2 wt. % hydrogen, 0.13 wt. % nitrogen, a density of 0.992 g / cc at 40° C., and a softening point of 165° C. The SATC stage 1 vacuum resid was 100% toluene soluble.

[0079] First, 1250 grams of SATC stage 1 vacuum resid and 750 grams of toluene were blended in a 3-liter pitcher. The pitcher was separated into DAO and rock in 12 1-liter batch separations. The separation began by pouring 64 grams of mixture from the pitcher into a 1 liter round bottomed flask. Next 250 grams of toluene was added to the flask, stoppered, and shaken to mix well. Next 250 grams of heptane were added to the flask and shaken. The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula was used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. Next 150 grams heptane mixed with 150 grams toluene was used to rinse the rock filter cake in the Buchner funnel. The filtration was carried out under vacuum for between 10 to 25 minutes. It was observed that the filter cake cracked into pieces as it dried and vacuum was applied for a further 3 to 10 minutes until the filter cake was dry. The filter cake was transferred to a vacuum oven equipped with a vacuum pump and the toluene and heptane solvents were removed at 75° C. overnight to form a rock of isotropic pitch.

[0080] After separation of the SATC stage 1 vacuum resid, the yield of DAO was 71 wt. % and the yield of isotropic pitch was 29 wt. %. The isotropic pitch was analyzed by simulated distillation and found to have a T10 distillation temperature of 965° F. (518° C.) and a T50 distillation temperature of 1350° F. (732° C.). The softening point of the isotropic pitch was measured as greater than 350° C. and the MCRT of the isotropic pitch was measured at 65 wt. %. The isotropic pitch was 100% toluene soluble.

[0081] A 4.0 gram sample of the isotropic pitch was ground into a powder and mixed with 0.73 grams of ExxonMobil™ Aromatic 200 which is a C11 high aromatic fluid with a minimum initial boiling point of 200° C. and a maximum final boiling point of 290° C. to form an isotropic pitch mixture. The isotropic pitch mixture was measured to have a softening point of 157° C. and an MCRT of 53 wt. %.

[0082] A 4.0 gram sample of the isotropic pitch was ground into a powder and mixed with 1.48 grams of ExxonMobil™ Aromatic 200 to form an isotropic pitch mixture. The isotropic pitch mixture was measured to have a softening point of 102° C. and an MCRT of 48 wt. %.Example 2

[0083] In this example, the isotropic pitch from example 1 was further transformed into mesophase pitch. An 80 gram sample of the isotropic pitch from example 1 was loaded into a 500 cc autoclave heated by a molten tin bath pre-heated to 810° F. (432° C.). A hydrogen flow of 50 standard cubic centimeters (sccm) is established. The autoclave was brought to 800° F. (426° C.) over a period of 10 minutes. The autoclave was held in the tin bath for another 110 minutes. The autoclave was pulled from the tin bath and cooled to 650° F. (343° C.) in less than 10 minutes. The autoclave was stripped with a flow of 200 sccm of hydrogen for 10 minutes at 650° F. (343° C.), and then cooled to room temperature. The yield of mesophase containing pitch was 78 wt. %. It was observed that the mesophase containing pitch had a softening point of greater than 350° C. and an MCRT of 83 wt. %.

[0084] The mesophase containing pitch was fluxed with 17.5 wt. % naphthalene. The resulting fluxed mesophase pitch had an MCRT of 68.5 wt. % and a softening point of 136° C. The fluxed mesophase pitch was analyzed using a polarized light microscope to produce the image in FIG. 3. In FIG. 3, the dots are roughly 5-micron spheres. It was observed that the mesophase pitch in the sample was contained in spheres with diameters of less than 1 micron. FIG. 4 is a graph of softening point versus MCRT coking value for commercially produced pitches as well as pitches produced from Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid. In FIG. 4 the cluster of “HDT SCT VR” pitches with softening point of less than 120° C. were produced by treating the SATC stage 1 vacuum resid from example 1 in an autoclave at 425° C. for 2 to 12 hours. The pitch at 170° C. softening point and 74 wt. % MCRT was produced by removing some of the material in the sample via vacuum distillation. The yield of the 170° C. softening point 74 wt. % MCRT sample on SATC Stage 1 Vacuum Resid was 60 wt. %. The process using deasphalting to tailor the feedstock composition, achieves a 72 wt. % yield and does not require a final vacuum distillation step. It was observed that the fluxed mesophase pitch has a higher coking value at lower softening point than the commercially produced pitches.Example 3

[0085] In this example, 50 grams of the DAO from example 1 was separated into two fractions. The 50 grams of DAO was added to a 1 liter round bottomed flask and 25 grams of toluene was added to the flask, stoppered, and shaken to mix well. Next, 50 grams of heptane was added to the flask and shaken. Thereafter, an additional 100 grams of heptane was added to the flask and shaken. The heptane step was repeated 3 more times. A total of 450 grams of heptane was added to the flask. The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula was used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. 270 grams heptane is used to rinse the rock filter cake. The filtration took between 10 and 25 minutes and the filter cake cracked into pieces as it dried and the filter cake was dried under vacuum for an additional 3 to 10 minutes. The filter cake was transferred to a vacuum oven equipped with a vacuum pump and the toluene and heptane solvents are removed at 75° C. overnight. The soft rock produced from the filtration is isotropic pitch. The deasphalted oil produced from the second deasphalting step is also a useful product.Example 4

[0086] In this example, the isotropic pitch from example 3 was further transformed into mesophase pitch. An 80 grams sample of isotropic pitch from example 3 was loaded into a 500 cc autoclave heated by a molten tin bath pre-heated to 810° F. (432° C.). A hydrogen flow of 50 standard cubic centimeters (sccm) is established. The autoclave was brought to 800° F. (426° C.) over a period of 10 minutes. The autoclave was held in the tin bath for another 110 minutes. The autoclave was pulled from the tin bath and cooled to 650° F. (343° C.) in less than 10 minutes. The autoclave was stripped with a flow of 200 sccm of hydrogen for 10 minutes at 650° F. (343° C.), and then cooled to room temperature. The yield of mesophase containing pitch was 71 wt. % pitch (<5 wt % mesophase). It was observed that the mesophase containing pitch had a softening point of 176° C. and an MCRT of 72 wt. %.Example 5

[0087] In this example, a crude oil vacuum resid was used to make an isotropic pitch. The vacuum resid has a 25 wt. % yield on crude. A sample of the crude oil vacuum resid was analyzed and found to have a T20 boiling point of 1078 F, a T50 boiling point of 1187 F, and a T80 boiling point of 1330 F. The crude oil was found to have 0.12 wt. % sulfur, 12.6 wt. % MCRT, 5.4 wt. % n-heptane insolubles (NHI), 0.4 wt. % N, and 18 API gravity.

[0088] A 1500-gram sample of the crude oil vacuum resid and 500 grams of toluene were blended in a 3 liter pitcher. The pitcher was separated into deasphalted oil (DAO) and rock in 28 1-liter batch separations. The separation starts by pouring 70 grams of the oil / toluene mixture from the pitcher into a 1 liter round bottomed flask. Then 50 grams of pentane chilled in dry ice was added to the flask, stoppered, and shaken to mix well. Next 130 grams of cold pentane was added to the flask and shaken. That step was repeated two more times resulting in a total addition of 440 g cold pentane in 4 increments (50 grams, then 130 grams, 130 grams, and 130 grams). The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula is used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. 270 grams pentane (pre chilled in dry ice) was used to rinse the rock filter cake. If the filtration slowed, some of the 270 g of rinse pentane is added to the Buchner funnel to facilitate the filtration. At least 50 g of the 270 g of rinse pentane was reserved for the end of the filtration. A successful filtration took between 10 and 25 minutes and the filter cake cracked into pieces as it dried. The vacuum was maintained for 3 to 10 minutes. The filter cake was transferred to a vacuum oven equipped with a vacuum pump and the toluene and pentane solvents were removed at 50° C. overnight. The DAO yield was 49 wt. %, contained 11.7 wt. % hydrogen, and had an MCRT of 5.7 wt. %. The rock was the isotropic pitch and had a yield of 51 wt. %, contained 11.9 wt. % hydrogen, had an MCRT of 19.2 wt. %, a sulfur content of 0.16 wt. %, and a softening point of 96° C. The results show that the MCRT of the isotropic pitch is higher than the DAO and therefore the aromatic compounds concentrate in the isotropic pitch. The high aromatic content of the isotropic pitch is compatible with visbreaking processes.

[0089] A visbreaking model was used to predict high severity visbreaking yield for the isotropic pitch. Visbreakers operate within a temperature window of 440 to 500 C, a pressure window of 3 to 10 bar (45 to 150 psig), and a residence time window of 1 to 10 minutes. The feed travels through a natural gas fired tubular heat exchanger to quickly heat the feed to the reaction temperature. The hot, visbroken products are depressured into a distillation tower operating at 5 to 30 psig which ends the thermal cracking reactions by rapid cooling (quenching) to temperatures below the distillation tower bottoms temperature (300-380 C). The visbreaking model converted 51 tons of visbreaker feedstock into the listed ton quantities of products. The model yielded a predicted effluent as follows:

[0090] A lube hydrocracking model was used to predict processing the deasphalted oil (DAO) to a group III base stock with a viscosity index (VI) of 124 and a pour point of −15° C. The lube hydrocracking model converted 49 tons of visbreaker feedstock into the listed ton quantities of products. The lube hydrocracking model yielded a predicted effluent as follows:

[0091] The models indicate that the crude oil vacuum resid of the example was upgraded to 49 wt. % lube hydrocracker feedstock, 7.5 wt. % carbon black feedstock, and 7.5 wt. % isotropic pitch. Once processed through a lube hydrocracker, the expected base stock yield on the starting crude oil vacuum resid is 34 wt. %.

[0092] All documents described herein are incorporated by reference herein for purposes of all jurisdictions where such practice is allowed, including any priority documents and / or testing procedures to the extent they are not inconsistent with this text. As is apparent from the foregoing general description and the specific embodiments, while forms of the disclosure have been illustrated and described, various modifications can be made without departing from the spirit and scope of the disclosure. Accordingly, it is not intended that the disclosure be limited thereby. For example, the compositions described herein may be free of any component, or composition not expressly recited or disclosed herein. Any method may lack any step not recited or disclosed herein. Likewise, the term “comprising” is considered synonymous with the term “including.” Whenever a method, composition, element or group of elements is preceded with the transitional phrase “comprising,” it is understood that we also contemplate the same composition or group of elements with transitional phrases “consisting essentially of,”“consisting of,”“selected from the group of consisting of,” or “is” preceding the recitation of the composition, element, or elements and vice versa.

[0093] Unless otherwise indicated, all numbers expressing quantities of ingredients, properties such as molecular weight, reaction conditions, and so forth used in the present specification and associated claims are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that may vary depending upon the desired properties sought to be obtained by the embodiments of the present invention. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claim, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0094] Whenever a numerical range with a lower limit and an upper limit is disclosed, any number and any included range falling within the range is specifically disclosed, including the lower limit and upper limit. In particular, every range of values (of the form, “from about a to about b,” or, equivalently, “from approximately a to b,” or, equivalently, “from approximately a-b”) disclosed herein is to be understood to set forth every number and range encompassed within the broader range of values. Also, the terms in the claims have their plain, ordinary meaning unless otherwise explicitly and clearly defined by the patentee. Moreover, the indefinite articles “a” or “an,” as used in the claims, are defined herein to mean one or more than one of the element that it introduces.

[0095] One or more illustrative embodiments are presented herein. Not all features of a physical implementation are described or shown in this application for the sake of clarity. It is understood that in the development of a physical embodiment of the present disclosure, numerous implementation-specific decisions must be made to achieve the developer's goals, such as compliance with system-related, business-related, government-related and other constraints, which vary by implementation and from time to time. While a developer's efforts might be time-consuming, such efforts would be, nevertheless, a routine undertaking for one of ordinary skill in the art and having benefit of this disclosure.

[0096] Therefore, the present disclosure is well adapted to attain the ends and advantages mentioned as well as those that are inherent therein. The particular embodiments disclosed above are illustrative only, as the present disclosure may be modified and practiced in different but equivalent manners apparent to one having ordinary skill in the art and having the benefit of the teachings herein. Furthermore, no limitations are intended to the details of construction or design herein shown, other than as described in the claims below. It is therefore evident that the particular illustrative embodiments disclosed above may be altered, combined, or modified and all such variations are considered within the scope and spirit of the present disclosure. The embodiments illustratively disclosed herein suitably may be practiced in the absence of any element that is not specifically disclosed herein and / or any optional element disclosed herein.

Examples

example 1

[0077]In this example, Solvent Assisted Tar Conversion (SATC) Stage 1 Vacuum Resid was separated into deasphalted oil (DAO) and rock and further processed to form a low softening point, high MCRT isotropic pitch.

[0078]The SATC stage 1 vacuum resid was analyzed by simulated distillation and found to have a T10 distillation temperature of 950° F. (510° C.), a T50 distillation temperature of 1123° F. (606° C.), and a T90 distillation temperature of 1330° C. (721° C.). Further analysis found 0.4 wt. % sulfur, 40 wt. % MCRT, 7.2 wt. % hydrogen, 0.13 wt. % nitrogen, a density of 0.992 g / cc at 40° C., and a softening point of 165° C. The SATC stage 1 vacuum resid was 100% toluene soluble.

[0079]First, 1250 grams of SATC stage 1 vacuum resid and 750 grams of toluene were blended in a 3-liter pitcher. The pitcher was separated into DAO and rock in 12 1-liter batch separations. The separation began by pouring 64 grams of mixture from the pitcher into a 1 liter round bottomed flask. Next 250 gr...

example 2

[0083]In this example, the isotropic pitch from example 1 was further transformed into mesophase pitch. An 80 gram sample of the isotropic pitch from example 1 was loaded into a 500 cc autoclave heated by a molten tin bath pre-heated to 810° F. (432° C.). A hydrogen flow of 50 standard cubic centimeters (sccm) is established. The autoclave was brought to 800° F. (426° C.) over a period of 10 minutes. The autoclave was held in the tin bath for another 110 minutes. The autoclave was pulled from the tin bath and cooled to 650° F. (343° C.) in less than 10 minutes. The autoclave was stripped with a flow of 200 sccm of hydrogen for 10 minutes at 650° F. (343° C.), and then cooled to room temperature. The yield of mesophase containing pitch was 78 wt. %. It was observed that the mesophase containing pitch had a softening point of greater than 350° C. and an MCRT of 83 wt. %.

[0084]The mesophase containing pitch was fluxed with 17.5 wt. % naphthalene. The resulting fluxed mesophase pitch ha...

example 3

[0085]In this example, 50 grams of the DAO from example 1 was separated into two fractions. The 50 grams of DAO was added to a 1 liter round bottomed flask and 25 grams of toluene was added to the flask, stoppered, and shaken to mix well. Next, 50 grams of heptane was added to the flask and shaken. Thereafter, an additional 100 grams of heptane was added to the flask and shaken. The heptane step was repeated 3 more times. A total of 450 grams of heptane was added to the flask. The shaken mixture in the stoppered 1-liter flask was placed in a 3-gallon bucket and covered top and bottom with dry ice. A Teflon sleeve was used to prevent the stopper from binding tightly as the flask chills. After 2 hours in the dry ice, the flask was removed. A metal spatula was used to scrape the walls of the flask, which was then shaken vigorously and poured through a Buchner funnel loaded with a 125 mm Whatman 2 paper filter. 270 grams heptane is used to rinse the rock filter cake. The filtration took...

Claims

1. A composition comprising:a pitch composition having a microcarbon residue “MCR” of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene, wherein MCR is measured according to ASTM D4530 (2020).

2. The composition of claim 1 wherein the softening point is between about 40° C. to about 100° C.

3. The composition of claim 1 wherein the softening point is between about 100° C. to about 160° C. and wherein the pitch composition has an MCR of greater than 40 wt. %.

4. The composition of claim 1 wherein the softening point is between about 160° C. to about 220° C. and wherein the pitch composition has an MCR of greater than 50 wt. %.

5. The composition of claim 1 wherein the softening point is between about 220° C. to about 240° C. and wherein the pitch composition has an MCR of greater than 60 wt. %.

6. (canceled)7. The composition of claim 1 further comprising an aromatic solvent selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof, or aromatic solvent comprising a C6-C20 aromatic compound, wherein the aromatic solvent is present in an amount of 1 wt % to 75 wt. % of the composition.

8. (canceled)9. The composition of claim 1 wherein the pitch composition is produced from an aromatic feedstock produced from a solvent assisted tar conversion (SATC) process.

10. A method comprising:introducing an aromatic feedstock into a deasphalting unit; anddeasphalting at least a portion of the aromatic feedstock to produce a deasphalted oil and a pitch composition,wherein the pitch composition has a microcarbon residue “MCR” of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

11. The method of claim 10 further comprising deasphalting at least a portion of the deasphalted oil to produce a deasphalted oil product and a soft rock product.

12. The method of claim 10 further comprising fluxing the deasphalted rock with an aromatic solvent comprising a C6-C20 aromatic compound.

13. The method of claim 10 wherein the pitch composition further comprises an aromatic solvent selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt % to 75 wt % of the aromatic solvent.

14. (canceled)15. The method of claim 10 wherein the aromatic feedstock comprises an aromatic feedstock produced from a solvent assisted tar conversion (SATC) process or a sweet vacuum resid.

16. The method of any of claim 10 further comprising hydrocracking at least a portion of the deasphalted oil to produce a group II or a group III base stock.

17. The method of claim 10 further comprising introducing the deasphalted rock into a visbreaking unit and exposing the deasphalted rock to visbreaking conditions to produce a pitch composition.

18. The method of claim 10 wherein the softening point is between about 100° C. to about 160° C. and wherein the deasphalted rock has an MCR of greater than 40 wt. %.

19. The method of claim 10 wherein the softening point is between about 160° C. to about 220° C. and wherein the deasphalted rock has an MCR of greater than 50 wt. %.

20. The method of claim 10 wherein the softening point is between about 220° C. to about 240° C. and wherein the deasphalted rock has an MCR of greater than 60 wt. %.

21. A method comprising:introducing an aromatic feedstock produced from a solvent assisted tar conversion (SATC) process into a deasphalting unit;deasphalting at least a portion of the aromatic feedstock with a C4-C7 solvent to produce a deasphalted oil and a deasphalted rock; andblending the deasphalted rock with an aromatic feedstock to produce a pitch composition with an microcarbon residue “MCR” of greater than 30 wt. %, a softening point between about 30° C. to about 240° C., and wherein the pitch composition is 100 wt. % soluble in toluene.

22. The method of claim 21 wherein the aromatic solvent is selected from the group consisting of naphthalene, methylnaphthalene, steam cracker naphtha, steam cracker gasoil, FCC light cycle oil, main column bottoms, and combinations thereof wherein the pitch composition comprises the aromatic solvent in an amount of 1 wt % to 75 wt. % of the aromatic solvent.

23. (canceled)24. The method of claim 21 wherein the softening point is between about 100° C. to about 160° C. and wherein the pitch composition has an MCR of greater than 40 wt. % or wherein the softening point is be ween about 220° C. to about 240° C. and wherein the pitch composition has an MCR of greater than 60 wt %.

25. (canceled)

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