Solvent extraction apparatus and methods

Abstract

A solvent extraction plant includes a solvent tank. A coal slurry tank is configured to receive a solvent from the solvent tank receive coal from a coal source and form a feed slurry from the solvent and the coal. A solvent extraction reactor is configured to receive the solvent from the solvent tank, receive the feed slurry from the coal slurry tank, and form a solution from the feed slurry. The solution includes a solvent and a dissolved coal species. A solvent extraction distillation column is configured to receive the coal extract from the evaporator, provide a coal extract to an extract collection tank. The solvent extraction reactor may include a co-current extraction reactor, a countercurrent extraction reactor, or a combination of co-current and countercurrent extraction reactors.

Description

Attorney Docket No.: UWYO / 0134PCSOLVENT EXTRACTION APPARATUS AND METHODSBACKGROUNDField

[0001] Embodiments of the present disclosure generally relate to extracts of coal, compositions thereof, and uses thereof. Embodiments of the present disclosure also generally relate to processes for extracting coal.Description of the Related Art

[0002] Coal is utilized in industry as both a fuel and as a source of chemicals. Such fuels and chemicals are produced from coal using coal liquefaction or solvent extraction. Conventional technologies for coal liquefaction and solvent extraction rely on tetralin or aromatic oils to react with the coal macrostructure to break it down into smaller molecules. These solvents are produced from petroleum, are carcinogenic, and in the case of tetralin, are very expensive. Other technologies for coal liquefaction and solvent extraction are inefficient and costly, as they utilize catalysts and hydrogen at high temperatures and / or high pressures, well within the pyrolysis regime, to improve the conversion.

[0003] In addition, coal is becoming increasingly attractive as an alternative to petroleum for use in the manufacture of intermediate, derivative, and finished high value products such as asphalt, among others. Because carbon dioxide is generated by both crude oil production, and from the fact that asphalt is a byproduct after removing very large amounts of fuel fractions which are combusted and turned into carbon dioxide during the asphalt production process itself, asphalt production is currently a leading source of current carbon dioxide emissions for asphalt pavements. As climate change becomes an increasing problem and the desire to reduce carbon dioxide gas emissions (a principal cause of climate change) continues, the asphalt production industry and other industries must become more efficient and less environmentally hazardous. Overall, improved coal extraction processes to achieve new high- value, non-hazardous and low-carbon intensity asphalt products are needed.8788859 1Attorney Docket No.: UWYO / 0134PC

[0004] Thus, there is a need for new and improved extracts of coal and for methods of extracting coal. There is also a need to utilize higher amounts of coal for higher value products.SUMMARY

[0005] In one embodiment, a co-current solvent extraction reactor includes a reactor and a first inlet proximate to a bottom of the reactor. The co-current solvent extraction reactor also includes a motor and a shaft. A set of agitators are coupled to the shaft and more of more chambers are defined by a plurality of baffles and a first outlet proximate to the top of the reactor.

[0006] In another embodiment, a countercurrent solvent extraction reactor includes a reactor, a first inlet proximate to a bottom of the reactor and a second inlet proximate to a top of the reactor. The countercurrent solvent extraction reactor also includes a motor and a shaft. A set of agitators are coupled to the shaft and more of more chambers are defined by a plurality of baffles and a first outlet proximate to the top of the reactor.

[0007] In yet another embodiment, a solvent extraction plant includes a solvent tank. A coal slurry tank is configured to receive a solvent from the solvent tank and coal from a coal source. The coal slurry tank forms a feed slurry from the solvent and the coal. A solvent extraction reactor receives the solvent from the solvent tank and the feed slurry from the coal slurry tank to form a solution. The solution includes the solvent and a dissolved coal species. An evaporator is configured to receive the solution from the solvent extraction reactor and form a first recycled solvent and a coal extract. The first recycled solvent is provided to the solvent tank. The coal extract is provided to a solvent extraction distillation column. The solvent extraction distillation column is configured to receive the coal extract from the evaporator and form a second recycled solvent from the coal extract. The coal extract is provided to an extract collection tank and the second recycled solvent is provided to the evaporator.8788859 2Attorney Docket No.: UWYO / 0134PCBRIEF DESCRIPTION OF THE DRAWINGS

[0008] So that the manner in which the above recited features of the present disclosure can be understood in detail, a more particular description of the disclosure, briefly summarized above, may be had by reference to embodiments, some of which are illustrated in the appended drawings. It is to be noted, however, that the appended drawings illustrate only exemplary embodiments and are therefore not to be considered limiting of its scope, may admit to other equally effective embodiments.

[0009] FIG. 1 A is a process flow diagram for coal slurry tanks of a pilot plant, according to at least one embodiment of the present disclosure.

[0010] FIG. 1 B is a process flow diagram for solvent feed tanks of a pilot plant, according to at least one embodiment of the present disclosure.

[0011] FIG. 1 C is a process flow diagram for solvent extraction reactors of a pilot plant, according to at least one embodiment of the present disclosure.

[0012] FIG. 1 D is a process flow diagram for an evaporator of a pilot plant, according to at least one embodiment of the present disclosure.

[0013] FIG. 1 E is a process flow diagram for a solvent extraction distillation column of a pilot plant, according to at least one embodiment of the present disclosure.

[0014] FIG. 2 is a co-current coal-solvent extraction reactor, according to at least one embodiment of the present disclosure.

[0015] FIG. 3 is a counter current coal-solvent extraction reactor, according to at least one embodiment of the present disclosure.

[0016] FIG. 4 is a separator used to recover an extracted product from a solution, according to at least one embodiment of the present disclosure.

[0017] FIG. 5 is an alternative process flow diagram for an alternative solvent extraction reactor of a pilot plant, according to at least one embodiment of the present disclosure.8788859 3Attorney Docket No.: UWYO / 0134PC

[0018] To facilitate understanding, identical reference numerals have been used, where possible, to designate identical elements that are common to the figures. It is contemplated that elements and features of one embodiment may be beneficially incorporated in other embodiments without further recitation.DETAILED DESCRIPTION

[0019] Embodiments of the present disclosure generally relate to extracts of coal, compositions thereof, and uses thereof. Embodiments of the present disclosure also generally relate to processes for extracting coal. The inventors have found more sustainable, and higher conversion, processes for converting subbitum inous and lignite lower-rank coals, and bio-based oxygen containing feedstocks, into desirable products or precursors thereof. Such desirable conversion products (or precursors thereof) include materials for asphalt products, hybrid biofuels, polymers, chemicals, coatings, adhesives, building materials, carbon fiber, or graphene products, among other materials. Embodiments described herein can enable improved coal extraction processes to achieve new high-value, non-hazardous and low-carbon intensity asphalt products. Furthermore, utilizing domestic feedstocks, such as coal and vegetable oil derived solvents, can help US contractors be compliant with “Buy American” policies without applying for waivers, which often happens with many petroleum asphalts.

[0020] As described above, traditional technologies for direct coal liquefaction or solvent extraction utilize tetralin or aromatic oils to react with the coal macrostructure to break it down into smaller molecules. Such solvents are produced from petroleum, are carcinogenic, and, in the case of tetralin, are expensive. Other technologies for coal liquefaction and solvent extraction are inefficient and costly, as they utilize catalysts and hydrogen at high temperatures and / or high pressures to improve the conversion. In contrast, embodiments described herein are free of catalysts. For example, a composition that includes a fatty alcohol extract of coal can be derived from coal without the use of a catalyst.8788859 4Attorney Docket No.: UWYO / 0134PC

[0021] Unlike conventional technologies, embodiments described herein enable thermochemical treatment of coal with alcohols, such as fatty alcohols, to convert coal into an alcohol soluble liquid with high extraction yields. In some examples, the extraction yields can be 85% by mass (or more) of the dried coalbased feedstock. Depending on, for example, the extraction conditions, the conversion can remove from about 50% to about 98% of the coal organic phase. During operation of processes described herein, the alcohol can react with coal oxygen functional groups, and possibly other reactive carbonhydrogen and carbon-carbon bonds, to produce hydrophobic coal extracts that are soluble in common organic solvents, such as dichloromethane or toluene, and exhibit partial solubility in other organic solvents, such as cyclohexane and especially heptane.

[0022] The inventors also found that adjustments in retention time, reactor pressure, temperature, and / or changes in alcohol type or alcohol length can further convert the coal extract molecules into more soluble molecules that are fully soluble in aliphatic solvents like heptane. In addition, the selection of alcohol type (for example, fully saturated versus partially unsaturated, or monohydric alcohol versus polyhydric alcohol) and / or the alcohol length (for example, C12 versus C18) for extracting coal can be utilized to tune the conversion processes. As a non-limiting example, conversion products having improved fluidity can be produced using alcohols having unsaturation (such as oleyl alcohol).

[0023] Fatty alcohols are a renewable carbon solvent that can be derived from fatty acids or triglyceride oils from biological sources (for example, algae, fungi, animal, plant, and lichen oil sources). Unlike tetralin and aromatic oils conventionally utilized for coal extraction, fatty alcohols are non-toxic, and for longer chain solvents they are not classified as flammable. Resultant fatty alcohol coal extracts can be further reacted to tune, for example, chemical and physical properties. As an example, different asphalt grades are utilized for different climates and traffic conditions, and embodiments described herein can enable tuning of the alcohol coal extracts so as to provide for various asphalt grades. As another example, alcohol coal extracts described herein can be8788859 5Attorney Docket No.: UWYO / 0134PC utilized to produce soft oils for recycling agents. For example, alcohol coal extracts can be further reacted with additional alcohols, ethers, aldehydes, ketones, carboxylic acids, amines, among other reactive functional groups to produce recycling agents.

[0024] In the case of polyfunctional (or polyhydric) alcohols, such as ethylene glycol and glycerin, functionalized coal extracts can be produced with pendant hydroxyl groups due to reaction of one alcohol group with the coal while the other alcohol group remains unreacted. This unreacted hydroxyl group provides a functional group for follow-on chemistry, such as the production of, for example, surfactants, polymers, or thermoset resins. The coal alcohol extracts can be further reacted with other fatty alcohols, fatty amines, or fatty acids to produce materials suitable for coatings, emulsions, sealants, asphalt, asphalt products, and recycling agents.

[0025] As an additional application, the hybrid bio-coal extracts are soluble in biodiesel (fatty acid methyl esters (FAME)) and, in some cases, renewable diesel. These blends can be used to reduce the cost of biodiesel and renewable diesel to make more cost competitive, low carbon emission fuels relative to other renewable and petroleum fuels. The blends can be very low sulfur fuels such as marine fuel oils. Various other non-limiting applications are described herein.

[0026] As used herein, the term “coal-based feedstock” refers to a feedstock at least partially derived from coal. A coal-based feedstock includes a solid, powder, slurry, liquid, residual, extract, fluid, mixture or other material that has been generated at least in part from a coal source, such as run of mine coal source and / or conversion products. For example, coal can be crushed into a powder prior to processing, sieved, and / or formed into a slurry. A coal-based feedstock can also include environmental reclamation by using waste fines from coal production that were backfilled into coal mines, buried, or deposited in tailings ponds.

[0027] A coal-based feedstock can be subject to various physical, thermal, and / or chemical treatments to further facilitate processing of the feedstock, for8788859 6Attorney Docket No.: UWYO / 0134PC example, by thermal treatment, mechanical treatment, and / or chemical treatment to produce an intermediate. A coal-based feedstock (or intermediate / derivative product thereof) can be subjected to pyrolysis and / or solvent extraction treatments. The feedstock can also act as a recycled stream from one or more of the downstream processes or intermediates (for example, solid material remaining after solvent extraction) for augmentation, so that additional products, such as liquid products, can be promoted and / or enhanced by reprocessing with less valuable or unwanted intermediate products.

[0028] As used herein, the term “coal” refers to predominately solid hydrocarbons that can contain some amount of fluid material. Coal is generally composed of hydrogen, carbon, sulfur, oxygen, and nitrogen, and optionally some other elements such as metals. Coal, as described herein, can refer to bituminous coal, subbituminous coal, and lignite. Coal can also refer to ash or peat. In some embodiments, coal can be sourced from Powder River Basin (Wyoming, USA) or other suitable sources. The Powder River Basin coal can be very low in sulfur, such as about 0.5 wt% or less. Other coal sources from other formations may also be utilized in accordance with the embodiments of the present disclosure.

[0029] As used herein, the term “solvent extraction” refers to the process of contacting a feedstock (or intermediate / derivative product thereof) with a solvent to facilitate the extraction and / or transformation of components of the material via chemical reaction(s) and / or mass transfer processes via solubility in the solvent. In some embodiments, solvent extraction is carried out by flowing a liquid solvent or mixture of solvents through, across, or over, a feedstock (or intermediate / derivative product thereof). In some embodiments, solvent extraction can be carried out as a batch process by bringing a feedstock (or intermediate / derivative product thereof) in physical contact with one or more solvents.

[0030] As described herein, solvent extraction can utilize one or more solids in one or more solvent extraction operatioms, including in multistage solvent extractions in which the same or similar solvents are repeatedly used on a8788859 7Attorney Docket No.: UWYO / 0134PC material. Solvents, as described herein, can be pure solvents or mixtures including mixtures of solvents generated by the processes described herein. Solvents can be derived from petrochemicals or from processes that build up higher alcohols from synthesis gas. Synthesis gas can originate from coal, or from the residues after solvent extraction processes described herein. Accordingly, solvents originating from synthesis gas can further maximize utilization of coal.

[0031] Solvents, as described herein, can be mixtures of a number of solvents. Solvents can be recycled and reused. Solvent extraction may be at subcritical temperatures. Solvent extraction can be performed at reduced pressures, atmospheric pressures or increased pressures. Solvent extraction can be carried out at supercritical pressures and temperatures.

[0032] As used herein, the term “solvent” refers to a liquid or a mixture of liquids having solubility and / or reactivity with regard to hydrocarbons or other species and molecules present in coal (or intermediate / derivative product thereof). Solvent can refer to a liquid organic solvent or hydrocarbon or a mixture of liquids, including organic solvents (such as solvents containing at least one hydroxyl group, such as alcohols), or mixtures of solvents. The solvents can be defined by boiling point ranges or other properties. In embodiments utilizing two or more solvents, solvents can be distinguished by composition, additives, molecular design, boiling point ranges, or combinations thereof. In some embodiments, the solvent can include a monohydric alcohol and / or a polyhydric alcohol, such as a C2 to C28 alcohol, such as ethanol, butanol, lauryl alcohol, oleyl alcohol, stearyl alcohol, 2-ethyl-1 -hexanol, cardanol, ethylene glycol, glycerin, partially hydrogenated oils from oils that contain 2 or more olefins, or combinations thereof, among others. Solvents may be sourced from biomass. Here, carbon capture storage and utilization can be utilized when using biomass derived solvents.

[0033] Some embodiments described herein relate to compositions comprising an alcohol extract of coal, blends of such compositions, and / or formulations comprising compositions. The alcohol extract of coal can be, or8788859 8Attorney Docket No.: UWYO / 0134PC include, a “high value coal product.” As used herein, the term “high value coal product(s)” can describe chemicals and materials (both solid and liquid) that are more valuable than the coal or feedstock at least partially derived from coal. High value coal products include non-fuel products, such as a product having value provided by properties, compositions and / or uses more valuable than its ability to generate energy on combustion. High value coal products can refer to liquid products generated from predominately solid coal. High value coal products can refer to products that are not fuel (for example, created for the purpose of burning to generate energy).

[0034] Examples of high value coal products include polymers (for example, polyurethane, polyesters, polyamides), high value chemicals (for example, BTX, paraffins, olefins), composite materials, carbon fiber, graphene, graphitic products, porous carbons, building materials, road, paving and roofing materials, and agricultural materials such as soil amendments, among others. High value coal products can represent a fraction of the total material converted from the feedstock, for example, 50% of the total products on a dry basis, 70% of the total products on a dry basis, 80% of the total products on a dry basis, or optionally, 90% of the total products on a dry basis.

[0035] Pressure values described herein are provided as absolute pressure values, unless otherwise indicated.

[0036] As used herein, a “composition” can include component(s) of the composition, reaction product(s) of two or more components of the composition, a remainder balance of remaining starting component(s), or combinations thereof. Compositions of the present disclosure can be prepared by any suitable mixing process.

[0037] The use of headings is for purposes of convenience only and does not limit the scope of the present disclosure. Embodiments described herein can be combined with other embodiments.Compositions8788859 9Attorney Docket No.: UWYO / 0134PC

[0038] Embodiments described herein generally relate to compositions comprising, consisting essentially of, or consisting of an alcohol extract of coal. As described below, such compositions that include the alcohol extract of coal can be utilized as-is, as a component in a blend, mixture, or formulation, or as a reactant for a chemical reaction to form a reaction product, among other uses.

[0039] Unlike conventional asphalt, recycling agents, anti-stripping agents, sealants, coatings, and adhesives, among other products which are typically formed from petroleum feedstocks, embodiments described herein are derived from coal-based feedstocks. Moreover, conventional technologies for converting petroleum to useful products may require catalysts or other upgrading processes. Here, for example, catalytic and upgraded oil streams do not typically produce good asphalts and need to be blended with normal distilled asphalts to be useful. In contrast, compositions described herein can be formed from coal without the use of a catalyst. Further, the solvents comprising alcohol utilized for coal extraction can be sourced from biomass, such as vegetable fats, vegetable oils, animal fats, animal oils, lipids, or combinations thereof, rather than petroleum sources. In addition, conventional technologies pursue fuel applications. In contrast, embodiments described herein can include compositions comprising intermediates, derivatives, and / or finished high value products for non-fuel applications. It is contemplated that compositions described herein can be used for fuel applications.

[0040] The alcohol extract of coal can be formed by processes described herein such as solvent extraction. During solvent extraction, the alcohol can serve to depolymerize, deoligomerize, and / or deconstruct the coal macromolecular structure and react with, for example, oxygen-containing functional groups in coal molecules, coal C-H groups, and / or coal C-C bonds (alkylation) to generate an alcohol extract with modified properties. The term “alcohol extract” refers to an extract obtained with a solvent that includes at least one alcohol.

[0041] Suitable alcohols can include monohydric alcohols (alcohols having a single hydroxyl (-OH) group), polyhydric alcohols (alcohols having more than8788859 10Attorney Docket No.: UWYO / 0134PC one hydroxyl (-OH) group), or combinations thereof. Suitable alcohols include those represented by formula (I):R— OH(|)

[0042] R of formula (I) is an unsubstituted hydrocarbyl, a substituted hydrocarbyl, or a functional group comprising at least one element from Group 13-17 of the periodic table of the elements. The alcohols of formula (I) can be referred to as “fatty alcohols”.

[0043] R of formula (I) can have any suitable number of carbon atoms such as from 1 to 40 carbon atoms, such as from 2 to 32 carbon atoms, such as from 4 to 28 carbon atoms, such as from 6 to 24 carbon atoms, such as from 8 to 18 carbon atoms or from 8 to 24 carbon atoms, such as from 10 to 16 carbon atoms, such as from 12 to 14 carbon atoms, or from 8 to 40 carbon atoms, such as from 10 to 30 carbon atoms, such as from 12 to 24 carbon atoms, such as from 14 to 22 carbon atoms. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. In some embodiments, the number of carbon atoms in R of formula (I) can be 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29, 30, 31 , 32, 33, 34, 35, 36, 37, 38, 39, 40. Each of the foregoing numbers can be preceded by the word “about,” “at least about,” “less than about,” or “more than about,” and any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0044] R of formula (I) can be linear or branched, saturated or unsaturated (for example, at least one C=C double bond), cyclic or acyclic, aromatic or not aromatic. Regarding saturation, R of formula (I) can be fully saturated, partially unsaturated, or fully unsaturated. Alcohols can have a double bond present at the alpha-carbon (for example, an alpha-olefin), present on an internal carbon (for example, an internal olefin), or combinations thereof. A non-limiting example of an alcohol having an internal olefin can be oleyl alcohol. Phenols8788859 11Attorney Docket No.: UWYO / 0134PC or alcohols containing aromatic groups, such as cardanol, resorcinol, cresol, phenol, bisphenol, or combinations thereof, among others can be utilized.

[0045] R of formula (I) can be an unsubstituted hydrocarbyl. An “unsubstituted hydrocarbyl” refers to a group that consists of hydrogen and carbon atoms only. Non-limiting examples of unsubstituted hydrocarbyl include an alkyl group having from 1 to 40 carbon atoms such as n-butyl, iso-butyl, secbutyl, and tert-butyl, pentyl, hexyl, heptyl, octyl, ethyl-2-hexyl, isooctyl, nonyl, n- decyl, isodecyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, or isomers thereof.

[0046] In some embodiments, R of formula (I) can be a substituted hydrocarbyl. A “substituted hydrocarbyl” refers to an unsubstituted hydrocarbyl in which at least one hydrogen of the unsubstituted hydrocarbyl has been substituted with at least one heteroatom or heteroatom-containing group, such as one or more elements from Group 13-17 of the periodic table of the elements, such as halogen (F, Cl, Br, or I), O, N, Se, Te, P, As, Sb, S, B, Si, Ge, Sn, Pb, and the like, such as C(O)R*, C(C)NR*2, C(O)OR*, NR*2, OR*, SeR*, TeR*, PR*2, AsR*2, SbR*2, SR*, SOx (where x = 2 or 3), BR*2, SiR*3, GeR*3, SnR*3, PbR*3, and the like, where R* is, independently, hydrogen or unsubstituted hydrocarbyl, or where at least one heteroatom has been inserted within the unsubstituted hydrocarbyl.

[0047] As used herein, reference to an R group, alkyl, substituted alkyl, hydrocarbyl, substituted hydrocarbyl, aromatic, or compound name without specifying a particular isomer (such as butyl) expressly discloses all isomers (such as n-butyl, iso-butyl, sec-butyl, and tert-butyl). For example, reference to an R group having 3 or more carbon atoms expressly discloses all isomers thereof. When a compound is described herein such that a particular isomer, enantiomer or diastereomer of the compound is not specified, for example, in a formula or in a chemical name, that description is intended to include each8788859 12Attorney Docket No.: UWYO / 0134PC isomer and enantiomer of the compound described individual or in any combination.

[0048] Polyhydric alcohols (compounds having more than one -OH) group can be utilized. The polyhydric alcohols can include R groups that are the same as or similar to those described above. Non-limiting examples of polyhydric alcohols can include diols and / or triols such as ethylene glycol, propylene glycol, glycerol (also called glycerin), among others.

[0049] In some embodiments, the R group is an alkoxy group (OR*) where R* is, independently, hydrogen or unsubstituted hydrocarbyl, or where at least one heteroatom has been inserted within the unsubstituted hydrocarbyl. Solvents having such R groups can include polyethers, such as fatty alcohol alkoxylates, polyethylene glycols, polysorbates, or combinations thereof. Such solvents can be utilized alone or with other solvents described herein. Combinations of alcohols having different R groups are contemplated. In some embodiments, the alcohol includes lauryl alcohol (1 -dodecanol), undecyl alcohol, myristyl alcohol (1 -tetradecanol), cetearyl alcohol (C16-C18 alcohol), cetyl alcohol (1 -hexadecanol), stearyl alcohol (1 -octadecanol), arachidyl alcohol (1 -eicosanol), behenyl alcohol (1 -docosanol), lignoceryl alcohol (1- tetracosanol), ceryl alcohol (1 -hexacosanol), montanyl alcohol (1 -octacosanol), linalool (a C10 alcohol), oleyl alcohol (a C18 alcohol), myricylic alcohol (1 - triacontanol), linoleic alcohol (a C18 alcohol), isocetyl alcohol, isostearyl alcohol (a C18 alcohol), 2-octyl-1 -dodecanol, 2-butyloctanol, 2-hexyl-1 -decanol, 2- decyl-1 -tetradecanol, 2-tetradecyl-1 -cetanol, partially hydrogenated oils from oils that contain 2 or more olefins, partially hydrogenated oils poly-unsaturated fatty alcohols, or combinations thereof.

[0050] Compositions that include an alcohol extract of coal can be partially vacuum distilled or fully vacuum distilled to provide a partially vacuum distilled alcohol extract of coal or a fully vacuum distilled alcohol extract of coal, respectively. A partially vacuum distilled alcohol extract of coal can be made by subjecting the alcohol extract of coal to vacuum distillation at an absolute pressure of about 5 Pa to about 6 Pa, such as about 5.3 Pa, while heating at a8788859 13Attorney Docket No.: UWYO / 0134PC temperature of about 225°C to about 275°C, such as about 250°C. A fully vacuum distilled alcohol extract of coal can be made by subjecting the alcohol extract of coal to vacuum distillation at an absolute pressure of about 5 Pa to about 6 Pa, such as about 5.3 Pa, while heating at a temperature of about 275°C or more, such as from about 275°C to about 325°C, such as about 300°C.

[0051] In some embodiments, compositions that include an alcohol extract of coal can further include decomposed products such as, for example, polymerized solvent such as a dimerized solvent. For example, the alcohol solvent can polymerize (for example, dimerize) during coal extraction and / or distillation to provide a polymer comprising an ether. The polymerized solvent can include a polymer derived from an alcohol monomer, such as a C4 to C28 alcohol monomer.

[0052] After distillation, the ether as well as other decomposed products may be present in the composition. Such vacuum distilled compositions can be characterized as being very stiff, for example, having a softening point of 300°C using a Mettler Toledo Dropping / Softening Point Apparatus (DP70).

[0053] Compositions that include an alcohol extract of coal can be adjusted by, for example, residence time, during solvent extraction of the coal and / or distillation of the alcohol extract of coal. For example, the amount of polymerized solvent formation (e.g., dimer formation) can be increased with longer residence time during extraction and / or distillation. Higher amounts of solvent polymer (e.g., dimer) can affect the viscosity of the compositions that include an alcohol extract of coal.

[0054] Illustrative, but non-limiting, examples of apparatus and processes for extracting coal and forming compositions of the present disclosure are described below.Uses of Compositions

[0055] Embodiments of the present disclosure also generally relate to uses of compositions described herein (for example, composition that comprise,8788859 14Attorney Docket No.: UWYO / 0134PC consist essentially of, or consist of an alcohol extract of coal). The compositions can be used as-is or further processed. Illustrative, but non-limiting, uses include: use as an asphalt binder; use as a partial replacement of asphalt; use as a recycling agent (also referred to as a rejuvenator or a softener); use as an anti-stripping agent; use as a crack sealant; use as a sealant for construction / roofing / automotive industry; use as a shingle / roofing coating; use as an adhesive for roofing industry; and use as a fuel. Other uses and applications are contemplated.Asphalt Binder

[0056] Compositions that include an alcohol extract of coal as described herein can be utilized as at least a portion of an asphalt binder. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above.

[0057] In some embodiments, an asphalt binder includes a composition that includes an alcohol extract of coal (such as a C4 to C28 alcohol extract of coal) and optionally one or more additives. The one or more additives can include a polymer, an oil, a fluxing agent, and / or a surfactant or combinations thereof, among others. Illustrative, but non-limiting, examples of polymers can include natural rubber, a styrene-butadiene-rubber copolymer, a styrene-butadiene- styrene (SBS) copolymer, styrene-isoprene-styrene (SIS) copolymer, polyethylene, polypropylene, nylon, polyvinyl chloride, ethylene methacrylate copolymer, ethylene propylene rubber, an ethylene vinylacetate copolymer, polybutadiene, polyisoprene, butyl rubber, styrene-butadiene rubber, polychloroprene rubber, waste tire rubber, reactive isocyanates, polymethylene diphenyl diisocyanate (poly-MDI), polyester, polyamide, or combinations thereof, among others. In at least one example, the polymer includes styrene-butadiene-styrene (SBS) tri-block copolymer.

[0058] The polymer can be derived from any suitable monomer such as styrene, butadiene, isoprene, ethylene, propylene, vinyl chloride, methyl acrylate, vinylacetate, chloroprene, isocyanate, amide, ester, or combinations8788859 15Attorney Docket No.: UWYO / 0134PC thereof, among others. In some embodiments, the polymer can have a weight average molecular weight of about 10,000 g / mol to 600,000 g / mol, such as from about 50,000 g / mol to about 200,000 g / mol. The polymers may be physical blends or also chemically cross-linked using sulfur or other cross-linking agents.

[0059] Illustrative, but non-limiting, examples of oils can include vegetable oils, animal oils, aromatic oils, paraffin oils, or combinations thereof. Here, the vacuum distilled compositions can be characterized as being very stiff and the oils can serve to soften the composition that includes the alcohol extract of coal. Soybean oil, including high oleic alcohol soybean oil, is an example of a vegetable oil that can be used. High oleic alcohol soybean oil can be utilized for oxidative stability.

[0060] Any suitable aromatic oil can be utilized such as Hydrolene products available from Holly Frontier Specialty Products (for example, C50T, N 90T, H100T, C180 TN, H225T, H600T, and LPH, among others) and those available from HF Sinclair (such as Sundex 53). Any suitable paraffinic oil can be used such as those available from Holly Frontier Specialty Products (for example, SP 125, SP 250, RF10, RF18 and RF20, among others). These oils can help improve compatibility and performance when utilizing polymer additives with the alcohol extract of coal.

[0061] An amount of optional polymer additive in the asphalt binder, based on the total wt% of the asphalt binder, can be about 10 wt% or less, such as about 8 wt% or less, such as from about 0.3 wt% to about 8 wt%, such as from about 1 .5 wt% to about 6 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. A total weight percent (wt%) of the asphalt binder is based on a total wt% of the composition that includes the alcohol extract of coal and the one or more optional additives. The total wt% does not exceed 100 wt%.

[0062] An amount of the composition that includes the alcohol extract of coal used in the asphalt binder, based on the total wt% of the asphalt binder, can be about 90 wt% or more, such as about 92 wt% or more, such as from about 928788859 16Attorney Docket No.: UWYO / 0134PC wt% to about 99.5 wt%, such as from about 94 wt% to about 98 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close- ended range.

[0063] If used, an amount of oil (such as vegetable oil, animal oil, aromatic oil, paraffin oils, or combinations thereof) in the asphalt binder, based on the total wt% of the asphalt binder, can be about 5 wt% or more, about 40 wt% or less, or combinations thereof, such as from about 5 wt% to about 40 wt%, such as from about 10 wt% to about 35 wt%, such as form about 15 wt% to about 30 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0064] In some embodiments, the one or more additives of the asphalt binder can optionally include a re-refined engine oil bottoms (REOB), a vacuum tower asphalt extender (VTAE), a component thereof, or combination thereof. REOB, VTAE, or components thereof can be utilized to soften the alcohol extract of coal, to meet low-temperature properties, or combinations thereof.

[0065] If used, an amount of REOB, VTAE, component thereof, or combination thereof in the asphalt binder, based on the total wt% of the asphalt binder, can be about 0.1 wt% or more, 20 wt% or less, or combinations thereof, such as from about 0.1 wt% to about 20 wt%, such as from about 0.5 wt% to about 15 wt%, such as form about 1 wt% to about 10 wt%, such as from about 2 wt% to about 8 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. In at least one embodiment, an amount of REOB, VTAE, component thereof, or combination thereof in the asphalt binder, based on the total wt% of the asphalt binder, can be about 10 wt% or less.

[0066] In some embodiments, the one or more additives can further include soft base asphalts. In other embodiments, the one or more additives can include non-cross-linking polymers to improve crack resistance. The non-8788859 17Attorney Docket No.: UWYO / 0134PC cross-linking polymers may include deblock triblock polymers, such as styrene isoprene styrene (SIS; e.g., Kraton 1119 series) or cross-linking deblock or triblock polymers (e.g., Kraton 1118 or G1118) which may cross-link with itself. The non-cross-linking polymers exhibit high shear elongation.

[0067] In some embodiments, the one or more additives of the asphalt binder can optionally include a cross-linking agent. Illustrative, but non-limiting, examples of cross-linking agents can include sulfur in various forms, peroxide, a transition metal, other radical generating chemical, or combinations thereof. When a cross-linking agent is utilized in an asphalt binder, the cross-linking agent can serve to cross-link the polymer which can reduce the amount of polymer and can enable use of lower or higher molecular weight polymers for the same end point. Cross-linking can improve the compatibility and storage stability of the polymer with the asphalt binder.

[0068] Asphalt binders can be produced by physically blending the one or more optional additives, and the composition that includes the alcohol extract of coal according to any suitable method. When a cross-linking agent is utilized, addition of the cross-linking agent can result in new chemical bonds between portions of the polymer, portions of the composition described herein (for example, the composition comprising the alcohol extract of coal), and portions of the polymer with portions of the composition described herein. Any suitable method for cross-linking can be used such as by utilizing elevated temperatures, an optional accelerator, and an optional activator.Solid or Highly Viscous Asphalt or Bitumen Composition Material at Selected Temperatures

[0069] Generally, asphalt (or bitumen) is stored and transported under hot conditions, in bulk, in tank trucks or by boats at elevated temperatures of the order of 120°C to 180°C. The storage and the transportation of bitumen under hot conditions can be problematic in terms of hazardous conditions, high energy costs to keep asphalt or bitumen at elevated temperatures in vessels or in tank trucks, and decreased final performance of the asphalt or bitumen, among other disadvantages.8788859 18Attorney Docket No.: UWYO / 0134PC

[0070] Compositions that include an alcohol extract of coal as described herein can be utilized as at least a solid or viscous asphalt or bitumen material. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above.

[0071] In some embodiments, an asphalt or bitumen composition includes a composition that includes an alcohol extract of coal (such as a C4 to C28 alcohol extract of coal) and optionally one or more additives. The composition that includes the alcohol extract of coal can resist flow at certain temperatures such as a temperature that is from about ambient temperature (20°C) to about 50°C. The asphalt or bitumen composition can exist as a solid or highly viscous product at ambient temperature or elevated temperatures (such as about 50°C or less).

[0072] In some embodiments, the asphalt or bitumen composition is solid at ambient temperature (about 20°C). In some embodiments, the asphalt or bitumen composition that is solid at ambient temperature, that is highly viscous at ambient temperature, and / or that resists flow at ambient temperature can be utilized for the purpose of shipping at ambient temperature so that the composition does not need to be shipped, transported, or otherwise handled in the molten state.

[0073] Because the asphalt or bitumen composition resists flow at such temperatures, the asphalt or bitumen composition can be transported, stored, and / or handled at ambient temperature, thereby making it possible to overcome the disadvantages of conventional technologies. That is, the asphalt or bitumen composition can be more environmentally friendly as a result of, for example, reduced energy for transportation and storage.

[0074] The optional one or more additives can include polymers (such as those described above), an oil (such as those described above, such as a vegetable oil, aromatic oil, a REOB, a VTAE, or combinations thereof).8788859 19Attorney Docket No.: UWYO / 0134PC

[0075] An amount of the composition that includes the alcohol extract of coal used in the asphalt or bitumen composition, based on the total wt% of the asphalt or bitumen composition, can be about 60 wt% or more, such as from about 60 wt% to about 99.5 wt%, such as from about 65 wt% to about 95 wt%, such as from about 70 wt% to about 90 wt%, such as from about 75 wt% to about 85 wt%, or about 90 wt% or more, such as about 92 wt% or more, such as from about 92 wt% to about 99.5 wt%, such as from about 94 wt% to about 98 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0076] A total weight percent (wt%) of the asphalt or bitumen composition is based on a total wt% of the composition that includes the alcohol extract of coal and the one or more optional additives. The total wt% does not exceed 100 wt%.

[0077] If used, an amount of oil (such as vegetable oil, animal oil, aromatic oil, paraffin oils, or combinations thereof) in the asphalt or bitumen composition, based on the total wt% of the asphalt or bitumen composition, can be about 5 wt% or more, about 40 wt% or less, or combinations thereof, such as from about 5 wt% to about 40 wt%, such as from about 10 wt% to about 35 wt%, such as form about 15 wt% to about 30 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0078] In some embodiments, the one or more additives of the asphalt or bitumen composition can optionally include a REOB, a VTAE, a component thereof, or combinations thereof. REOB, VTAE, or components thereof can be utilized to soften the alcohol extract of coal, to meet low-temperature properties, or combinations thereof.

[0079] If used, an amount of REOB, VTAE, component thereof, or combination thereof in the asphalt or bitumen composition, based on the total wt% of the asphalt or bitumen composition, can be about 0.1 wt% or more, 20 wt% or less, or combinations thereof, such as from about 0.1 wt% to about 208788859 20Attorney Docket No.: UWYO / 0134PC wt%, such as from about 0.5 wt% to about 15 wt%, such as form about 1 wt% to about 10 wt%, such as from about 2 wt% to about 8 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. In at least one embodiment, an amount of REOB, VTAE, component thereof, or combination thereof in the asphalt or bitumen composition, based on the total wt% of the asphalt or bitumen composition, can be about 10 wt% or less.

[0080] Asphalt or bitumen compositions can be produced by physically blending the one or more optional additives, and the composition that includes the alcohol extract of coal according to any suitable method.Partial Replacement of Asphalt

[0081] Compositions that include an alcohol extract of coal as described herein can be utilized as a partial replacement of asphalt. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above

[0082] The partial replacement of asphalt is also an asphalt binder (with various additive modifications, as described above) that further includes an asphalt that is not derived from coal. That is, an asphalt that is not derived from coal can be added to an asphalt binder described above in suitable proportions. Illustrative, but non-limiting, examples of asphalts not derived from coal include petroleum-based asphalt, petroleum-based pitch, oxidized asphalt, soft bases, hard grade asphalt, multi-grade asphalt, flux, viscous oils, reclaimed asphalt, or combinations thereof, among others. The reclaimed asphalt means asphalt extracted from or remaining in reclaimed asphalt pavement.

[0083] A total weight percent of the asphalt binder is based on a total wt% of the composition that includes the alcohol extract of coal, the one or more optional additives, and the asphalt not derived from coal. The total wt% of the asphalt binder does not exceed 100 wt%.8788859 21Attorney Docket No.: UWYO / 0134PC

[0084] Amounts of the composition that includes the alcohol extract of coal in the asphalt binder are described above. Amounts of the optional additives that can be utilized are described above.

[0085] An amount of asphalt not derived from coal used in the asphalt binder, based on a total wt% of the asphalt binder, can be from about 1 wt% to about 99 wt%, such as from about 10 wt% to about 90 wt%, such as from about 20 wt% to about 80 wt%, such as from about 30 wt% to about 70 wt%, such as from about 40 wt% to about 60 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0086] Asphalt binders that include an asphalt not derived from coal can be produced by physically blending the composition that includes the alcohol extract of coal, the asphalt not derived from coal, and the one or more optional additives according to any suitable method.Recycling Agent (Rejuvenator)

[0087] Compositions that include an alcohol extract of coal as described herein can be utilized as a recycling agent. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above.

[0088] In certain applications, recycling agents are also referred to as rejuvenators or softeners. The recycling agent (or rejuvenator) can be utilized to produce a pavement. In these and other embodiments, the recycling agent can serve to ease or facilitate the mixing and incorporation of components in a pavement formulation (for example, eases the mixing of a recuperated or reclaimed asphalt pavement (RAP) or reclaimed bituminous product into fresh bitumen or into an asphalt mix, during an asphalt mix production process). The pavement formulation can be a recycled pavement formulation.

[0089] In some embodiments, a recycling agent includes a composition described herein (for example, a composition comprising an alcohol extract of coal). Additionally, or alternatively, a recycling agent includes a composition8788859 22Attorney Docket No.: UWYO / 0134PC comprising a reaction product of a composition described herein (for example, a composition comprising an alcohol extract of coal) with an amine of formula (II), a carboxylic acid of formula (III), an acid chloride of formula (IV), or combinations thereof:R— NH3 (N)

[0090] Each R of formula (II), formula (III), or formula (IV) can be, independently, those R groups described herein for formula (I). In some embodiments, the amine of formula (II) is a primary amine. In some embodiments, the carboxylic acid of formula (III) is a primary carboxylic acid. In some embodiments, the acid chloride of formula (IV) is a primary acid chloride.

[0091] Each R of formula (II), formula (III), or formula (IV) can be, independently, linear or branched, saturated or unsaturated (for example, at least one C=C double bond), cyclic or acyclic, aromatic or not aromatic. Each R of formula (II), formula (III), or formula (IV) can have, independently, any suitable number of carbon atoms such as from 4 to 28 carbon atoms. The amine of formula (II), the carboxylic acid of formula (III), and the acid chloride of formula (IV) can be referred to as “fatty amines”, “fatty acids”, and “fatty acid chlorides”, respectively.

[0092] The reaction product can be formed from reacting one or more oxygen groups (for example, hydroxyl groups) present in the alcohol extract of coal with an amine, carboxylic acid, an acid chloride, or combinations thereof. Additionally, or alternatively, the reaction product can be an alkylation reaction product formed from reacting a coal -OH group, a coal -CH group, or coal - CC group present in the alcohol extract of coal with an amine, carboxylic acid,8788859 23Attorney Docket No.: UWYO / 0134PC acid chloride, or combinations thereof. With amines, an alkyl chain transfer type reaction can occur. Additionally, or alternatively, the reaction product can be an ester product formed from reacting a hydroxyl group present in the alcohol extract of coal with a carboxylic acid. Such esterification reactions can occur at temperatures of about 200°C or more. In some cases, a condensation reaction product can be formed by reaction of the alcohol extract of coal (e.g., a hydroxyl group) with the production of water. In some embodiments, the reaction product can be an ester, an ether, an alkyl chain transfer product, or combinations thereof.

[0093] In some embodiments, the recycling agent can further include an oil such as a vegetable oil, animal oil, aromatic oil, paraffin oil, or combinations thereof, such as those vegetable oils, animal oils, aromatic oils, and paraffin oils described above. Addition of oil can make the alcohol extract of coal softer, more recyclable, more soluble in heptane, lower in viscosity, or combinations thereof. Similarly, reaction products of a composition described herein with an amine of formula (II), a carboxylic acid of formula (III), an acid chloride of formula (IV), or combinations thereof can also make the alcohol extract of coal softer, more recyclable, more soluble in heptane, lower in viscosity, or combinations thereof. The recycling agent can be viscous or an oil at room temperature.

[0094] The recycling agent, with or without an oil, can be utilized in a pavement formulation such as a recycled pavement formulation. Accordingly, a pavement formulation can include a recycling agent and one or more optional additives.

[0095] The one or more optional additives can include bitumen (or asphalt), reclaimed asphalt pavement (RAP), bituminous products, reclaimed bituminous products, fresh (or virgin) bitumen, or combinations thereof. RAPs also include recycled asphalt mixes wherein the mineral aggregates are replaced in whole or in part with other common components, such as, organic and inorganic fibers (for example, glass fibers, metal fibers, carbon fibers, cellulose, cotton, aramid, or combinations thereof, among others), polymers (for example,8788859 24Attorney Docket No.: UWYO / 0134PC polypropylenes, polyesters, poly(vinyl alcohol)s, polyamides, polyurethanes, polyureas, ethyl vinyl acetate (EVA), SIS, SBS polymers, or combinations thereof, among others).

[0096] Recuperated or reclaimed aggregates, commonly known as RAP, are the result of milling (or other grinding method) of previously constructed pavements, which are generally damaged and need to be replaced. These recuperated or reclaimed aggregates contain bitumen (the one used as binder during their previous fabrication). RAP can also include asphalt binder and fines. Other sources of bituminous products that may also be recycled into pavement fabrication are, for example, roofing products (such as shingles or waterproofing membranes, as well as waste materials coming from their production), isolation or sound damping materials, or combinations thereof, among others.

[0097] The term “reclaimed bituminous product” and “reclaimed asphalt products” refers to any suitable manufactured product that includes bitumen or asphalt as one of its components, and the manufactured product that includes bitumen or asphalt has been previously used or discarded after production. Illustrative, but non-limiting, examples of such reclaimed bituminous products and reclaimed asphalt products can include are the reclaimed asphalt pavement (also known as RAP) obtained from the milling of roads and other rolling surfaces, waterproof membranes, bituminous shingles used in roofing (reclaimed asphalt shingle, RAS), sound-proof panels, wastes coming from their production, or combinations thereof, among others. The term “fresh bitumen” and “fresh asphalt” refers to bitumen and asphalt which has not already been contacted with aggregates for the preparation of pavement or asphalt mixes.

[0098] A total weight percent of the pavement formulation is based on a total wt% of the recycling agent and the one or more optional additives. The total wt% of the pavement formulation does not exceed 100 wt%.

[0099] An amount of recycling agent in the pavement formulation, based on a total wt% of the pavement formulation, can be about 0.5 wt% or more, such8788859 25Attorney Docket No.: UWYO / 0134PC as from about 3 wt% to about 10 wt%, such as from about 5 wt% to about 9 wt%, such as from about 6 wt% to about 8 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0100] An amount of the one or more optional additives in the pavement formulation, based on a total wt% of the pavement formulation, can be about 99.5 wt% or less, such as from about 90 wt% to about 97 wt%, such as from about 91 wt% to about 95 wt%, such as from about 92 wt% to about 94 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0101] Pavement formulations can be produced by physically blending the aforementioned materials according to any suitable method.Anti-Stripping Agent

[0102] Anti-stripping agents are used for bituminous (or asphalt) mixes and materials to increase the strength of adhesion between bitumen (or asphalt) and aggregates, even when submerged in water.

[0103] Compositions that include an alcohol extract of coal as described herein can be utilized as at least a portion of an anti-stripping agent. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above. In some embodiments, an anti-stripping agent includes a composition comprising a reaction product of a composition described herein (for example, a composition comprising an alcohol extract of coal) with an amine of formula (II). The reaction product can be formed from reacting one or more oxygen groups (for example, hydroxyl groups) present in the alcohol extract of coal with the amine of formula (II). Additionally, or alternatively, the reaction product can be an alkylation reaction product formed from reacting a coal -OH group, a coal -CH group, or coal -CC group present in the alcohol extract of coal with an amine. With amines, an alkyl chain transfer type reaction8788859 26Attorney Docket No.: UWYO / 0134PC can occur. In some cases, a condensation reaction product can be formed by reaction of the alcohol extract of coal (e.g., a hydroxyl group) with the production of water. In some embodiments, the reaction product can be an alkyl chain transfer product.

[0104] The composition comprising the reaction product can be used as an anti-stripping agent. The anti-stripping agent can be applied to bitumen (or asphalt), recuperated or reclaimed asphalt pavement (RAP), asphalt products, reclaimed asphalt products, bituminous products, reclaimed bituminous products, fresh bitumen, fresh asphalt, or combinations thereof. The antistripping agent described herein can be utilized to increase the stripping resistance of the bitumen-coated (or asphalt-coated) aggregates.Crack Sealant

[0105] Cracks in roadways made of, for example, cement concrete pavement or asphaltic concrete pavement, can develop over time. As a treatment, cracks can be filled with a crack sealant.

[0106] Compositions that include an alcohol extract of coal as described herein can be utilized as at least a portion of a crack sealant. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above.

[0107] In some embodiments, a crack sealant includes a composition that includes an alcohol extract of coal (such as a C4 to C28 alcohol extract of coal) and optionally one or more additives. The one or more additives can include a polymer. Illustrative, but non-limiting, examples of polymers can include natural rubber, a styrene-butadiene-rubber copolymer, a styrene-butadiene-styrene (SBS) copolymer, styrene-isoprene-styrene (SIS) copolymer, polyethylene, polypropylene, nylon, polyvinyl chloride, ethylene methacrylate copolymer, ethylene propylene rubber, an ethylene vinylacetate copolymer, polybutadiene, polyisoprene, butyl rubber, styrene-butadiene rubber, polychloroprene rubber, waste tire rubber, reactive isocyanates, poly-methylene diphenyl diisocyanate8788859 27Attorney Docket No.: UWYO / 0134PC(poly-MDI), polyester, polyamide, or combinations thereof, among others. In at least one example, the polymer includes styrene-butadiene-styrene (SBS) triblock copolymer.

[0108] The polymer can be derived from any suitable monomer such as styrene, butadiene, isoprene, ethylene, propylene, vinyl chloride, methyl acrylate, vinylacetate, chloroprene, isocyanate, amide, ester, or combinations thereof, among others. In some embodiments, the polymer can have a weight average molecular weight of about 10,000 g / mol to 600,000 g / mol, such as from about 50,000 g / mol to about 200,000 g / mol. The polymers may be physical blends or also chemically cross-linked using sulfur or other cross-linking agents.

[0109] An amount of optional polymer additive in the crack sealant, based on the total wt% of the crack sealant, can be about 40 wt% or less, such as from about 0.5 wt% to about 40 wt%, such as from about 1 wt% to about 35 wt%, such as from about 5 wt% to about 30 wt%, such as from about 10 wt% to about 25 wt%, such as from about 15 wt% to about 20 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. A total wt% of the crack sealant is based on a total wt% of the composition comprising (or consisting of) the alcohol extract of coal and the one or more optional additives. The total wt% of the crack sealant does not exceed 100 wt%.

[0110] An amount of the composition that includes the alcohol extract of coal used in the crack sealant, based on the total wt% of the crack sealant, can be about 60 wt% or more, such as from about 60 wt% to about 99.5 wt%, such as from about 65 wt% to about 99 wt%, such as from about 70 wt% to about 95 wt%, such as from about 75 wt% to about 90 wt%, such as from about 80 wt% to about 85 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0111] In some embodiments, the one or more additives of the crack sealant can optionally include a cross-linking agent. Illustrative, but non-limiting,8788859 28Attorney Docket No.: UWYO / 0134PC examples of cross-linking agents can include sulfur in various forms, peroxide, a transition metal, other radical generating chemical or combinations thereof. When a cross-linking agent is utilized in a crack sealant, the cross-linking agent can serve to cross-link the polymer which can reduce the amount of polymer and can permit use of lower or higher molecular weight polymers for the same end point. Cross-linking can improve the compatibility and storage stability of the polymer with the crack sealant.

[0112] Crack sealants can be produced by physically blending the one or more optional additives, and the composition that includes the alcohol extract of coal according to any suitable method. When a cross-linking agent is utilized, addition of the cross-linking agent can result in new chemical bonds between portions of the polymer, portions of the composition described herein (for example, the composition comprising the alcohol extract of coal), and portions of the polymer with portions of the composition described herein. Any suitable method for cross-linking can be used such as by utilizing elevated temperatures, an optional accelerator, and an optional activator.

[0113] The crack sealant can be applied to roadways, sidewalks, parking lots and structures, bridge decks, concrete pavements, and other matter that includes cement concrete pavement and / or asphaltic concrete pavement.Sealant for Construction or Roofing industry

[0114] Compositions that include an alcohol extract of coal as described herein can be utilized as at least a portion of a sealant used in, for example, in the construction or roofing industry. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above.

[0115] In some embodiments, a sealant includes a composition that includes an alcohol extract of coal and optionally one or more additives. The one or more additives can include a polymer. Illustrative, but non-limiting, examples of polymers can include natural rubber, a styrene-butadiene-rubber copolymer, a styrene-butadiene-styrene (SBS) copolymer, styrene-isoprene-8788859 29Attorney Docket No.: UWYO / 0134PC styrene (SIS) copolymer, polyethylene, polypropylene, nylon, polyvinyl chloride, ethylene methacrylate copolymer, ethylene propylene rubber, an ethylene vinylacetate copolymer, polybutadiene, polyisoprene, butyl rubber, styrenebutadiene rubber, polychloroprene rubber, waste tire rubber, reactive isocyanates, poly-methylene diphenyl diisocyanate (poly-MDI), polyester, polyamide, or combinations thereof, among others. In at least one example, the polymer includes styrene-butadiene-styrene (SBS) tri-block copolymer.

[0116] The polymer can be derived from any suitable monomer such as styrene, butadiene, isoprene, ethylene, propylene, vinyl chloride, methyl acrylate, vinylacetate, chloroprene, isocyanate, amide, ester, or combinations thereof, among others. In some embodiments, the polymer can have a weight average molecular weight of about 10,000 g / mol to 600,000 g / mol, such as from about 50,000 g / mol to about 200,000 g / mol. The polymers may be physical blends or also chemically cross-linked using sulfur or other cross-linking agents.

[0117] The choice of polymer(s) can impact properties of the sealant. For example, use of a styrene-butadiene-rubber copolymer, a styrene-butadiene- styrene (SBS) copolymer, or combinations thereof, among others, can impart softness to the sealant. As another example, polypropylene, polyethylene, or combinations thereof, among others, can impart stiffness to the sealant.

[0118] An amount of optional polymer additive in the sealant, based on the total wt% of the sealant, can be about 40 wt% or less, such as from about 0.5 wt% to about 40 wt%, such as from about 1 wt% to about 35 wt%, such as from about 5 wt% to about 30 wt%, such as from about 10 wt% to about 25 wt%, such as from about 15 wt% to about 20 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. A total wt% of the sealant is based on a total wt% of the composition that includes the alcohol extract of coal and the one or more optional additives. The total wt% of the sealant does not exceed 100 wt%.

[0119] An amount of the composition that includes the alcohol extract of coal used in the sealant, based on the total wt% of the sealant, can be about 60 wt%8788859 30Attorney Docket No.: UWYO / 0134PC or more, such as from about 60 wt% to about 99.5 wt%, such as from about 65 wt% to about 99 wt%, such as from about 70 wt% to about 95 wt%, such as from about 75 wt% to about 90 wt%, such as from about 80 wt% to about 85 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0120] In at least one embodiment, a sealant includes from about 80 wt% to about 90 wt% (such as about 85 wt%) of a composition that includes the alcohol extract of coal based on the total wt% of the sealant; and from about 10 wt% to about 20 wt% (such as about 15 wt%) of a polymer based on the total wt% of the sealant.

[0121] Sealants can be produced by physically blending the composition that includes the alcohol extract of coal and the one or more optional additives according to any suitable method. The sealant can be applied to, for example, roofs, commercial structures, residential structures, among other structures.Coatings and Adhesives

[0122] Compositions that include an alcohol extract of coal as described herein can be utilized as at least a portion of a coating or an adhesive used in, for example, in the roofing industry. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above.

[0123] In some embodiments, a coating or an adhesive can include a composition comprising a heavily or fully vacuum distilled alcohol extract of coal. Such heavily or fully distilled alcohol extracts of coal can be stiff and useful to replace, for example, air blown coatings.

[0124] In some embodiments, a coating or an adhesive includes a composition that includes an at least partially distilled alcohol extract of coal and optionally one or more additives. The one or more additives can include a polymer. Illustrative, but non-limiting, examples of polymers can include natural rubber, a styrene-butadiene-rubber copolymer, a styrene-butadiene-styrene8788859 31Attorney Docket No.: UWYO / 0134PC(SBS) copolymer, styrene-isoprene-styrene (SIS) copolymer, polyethylene, polypropylene, nylon, polyvinyl chloride, ethylene methacrylate copolymer, ethylene propylene rubber, an ethylene vinylacetate copolymer, polybutadiene, polyisoprene, butyl rubber, styrene-butadiene rubber, polychloroprene rubber, waste tire rubber, reactive isocyanates, poly-methylene diphenyl diisocyanate (poly-MDI), polyester, polyamide, or combinations thereof, among others. In at least one example, the polymer includes styrene-butadiene-styrene (SBS) triblock copolymer.

[0125] The polymer can be derived from any suitable monomer such as styrene, butadiene, isoprene, ethylene, propylene, vinyl chloride, methyl acrylate, vinylacetate, chloroprene, isocyanate, isocyanate, amide, ester, or combinations thereof, among others. In some embodiments, the polymer can have a weight average molecular weight of about 10,000 g / mol to 600,000 g / mol, such as from about 50,000 g / mol to about 200,000 g / mol. The polymers may be physical blends or also chemically cross-linked using sulfur or other cross-linking agents.

[0126] An amount of optional polymer additive in the coating (or adhesive), based on the total wt% of the coating (or adhesive), can be about 40 wt% or less, such as from about 0.5 wt% to about 40 wt%, such as from about 1 wt% to about 35 wt%, such as from about 5 wt% to about 30 wt%, such as from about 10 wt% to about 25 wt%, such as from about 15 wt% to about 20 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. A total wt% of the coating (or adhesive) is based on a total wt% of the composition that includes the alcohol extract of coal and the one or more optional additives. The total wt% of the coating (or adhesive) does not exceed 100 wt%.

[0127] An amount of the composition that includes the alcohol extract of coal used in the coating (or adhesive), based on the total wt% of the coating (or adhesive), can be about 60 wt% or more, such as from about 60 wt% to about 99.5 wt%, such as from about 65 wt% to about 99 wt%, such as from about 708788859 32Attorney Docket No.: UWYO / 0134PC wt% to about 95 wt%, such as from about 75 wt% to about 90 wt%, such as from about 80 wt% to about 85 wt%, though other amounts are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0128] Coatings and adhesives can be produced by physically blending the composition that includes the alcohol extract of coal and the one or more optional additives according to any suitable method. The coating (or adhesive) can be applied to, for example, a shingle utilized for roofs such as sloped roofs.Fuel

[0129] Compositions that include an alcohol extract of coal as described herein can be utilized as at least a portion of a fuel. Such compositions can include a partially vacuum distilled alcohol extract of coal, a fully vacuum distilled alcohol extract of coal, or combinations thereof, as described above.

[0130] In some embodiments, a fuel includes a composition that includes an alcohol extract of coal and one or more of a biodiesel (FAME), renewable diesel, bio-oils, pyrolysis oils from biomass, oils from depolymerization of waste, pyrolysis oils from wastes, bunker fuels, bunker crudes, heavy fuel oil, marine fuel oil, upgraded petroleum fuels, catalytically upgrade petroleum fuels, heavy oils, petroleum residues, or combinations thereof, among others.

[0131] The fuel blend can include any suitable ratio of alcohol extract of coal to the one or more of biodiesel, renewable diesel, bio-oils, pyrolysis oils from biomass, oils from depolymerization of waste, pyrolysis oils from wastes, bunker fuels, bunker crudes, heavy fuel oil, marine fuel oil, upgraded petroleum fuels, catalytically upgrade petroleum fuels, heavy oils, petroleum residues, or combinations thereof, among others. Such ratios (volume ratios) include from about 1 :10 to about 10:1 , such as from about 1 :5 to about 5:1 , such as from about 1 :3 to about 3: 1 , such as from about 1 :2 to about 2: 1 , such as about 1 :1 , though other values are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.8788859 33Attorney Docket No.: UWYO / 0134PC

[0132] Use of the alcohol extract of coal can reduce the cost of fuels such as biodiesel and renewable diesel to make more cost competitive, low carbon emission fuels relative to conventional renewable and petroleum fuels. The fuel blends can be very low sulfur fuels such as those utilized as marine fuel oils.

[0133] Fuel blends can be produced by physically blending the composition that includes the alcohol extract of coal and the one or more optional additives according to any suitable method.Apparatus and Processes

[0134] Embodiments described herein also relate to processes for extracting coal. The processes rely, at least in part, on utilizing a solvent that includes an alcohol. Compositions described herein (for example, compositions comprising an alcohol extract of coal) can be formed using suitable processes and apparatus as described in, for example, US Patent Application Publication Nos. 2022 / 0177312, 2022 / 0154075, 2020 / 0332197, and, each of which are incorporated herein by reference in their entireties to the extent it is not inconsistent with the description herein. One suitable apparatus and process is described herein.

[0135] The apparatus generally includes an extraction reactor and, in some embodiments, a staged product precipitation scheme and distillation column, further described below. An extractor provides an example of an apparatus for reducing the volume of solvent (for example, solvent / coal ratio) needed to effectively extract effective / target yields of solid and liquid intermediate products from coal. The extractor enables greater coal throughput. The extractor is one example of a large number of systems and techniques for solvent extraction including batch and flow processes for a wide range of feedstock compositions and scales. The systems and methods can use a solvent / coal weight ratio selected from 1 :1 to 50:1 , such as from about 5:1 to about 50:1 . In an embodiment, for example, a batch extraction system can use a 20:1 (±10%) solvent / coal weight ratio and optionally a 10:1 (±10%) solvent / coal weight ratio.8788859 34Attorney Docket No.: UWYO / 0134PC

[0136] Processes for forming an alcohol extract of coal can include solvent extraction, fractionation, pyrolysis, or combinations thereof. The process conditions can be adjusted to control yields, composition, and product properties, for example, to provide tunable control of the identity, properties, and branching to products. In some embodiments, a coal-based feedstock is split into at least 2 fractions including: (1 ) Residue: a component that doesn't dissolve in the solvent(s) under the solvent extraction conditions; (2) Alcohol soluble (Al): a component that dissolves in the solvent(s) under the solvent extraction conditions and is generally soluble in the liquid solvent(s).

[0137] The coal-based feedstock and / or intermediate can be extracted with a solvent comprising an alcohol, and the resultant extract can be optionally fractionated. The coal-based feed can be prepared via one or more preextraction treatments and / or processes prior to solvent extraction and / or fractionation. Pre-extraction treatments can include mechanical treatment (for example, pulverizing, grinding, sieving, mixing, and / or formation of a slurry, among others), thermal treatment (for example, drying, heating, and / or pyrolysis, among others) and / or chemical treatment (for example, solvent extraction, and / or chemical reaction, among others).

[0138] Prior to extraction, the coal can be ground and sieved, for example, to a particle size range of about 10 mesh to about 300 mesh (about 50 microns to about 2,000 microns in size). The coal or a derivative thereof can be dried in an oven, for example, by heating to a temperature greater than about 60°C for a time period greater than about 10 hours, such as heating to a temperature of about 60°C to about 120°C for a time period of about 10 hours to about 70 hours. In some examples, the coal can be dried at about 90°C for about 48 hours to remove moisture. In some examples, the drying can be performed under a reduced pressure using a vacuum. In some embodiments, depending on the solvent utilized, the coal or a derivative therefore may not be dried, as the water may be advantageous.

[0139] After the optional pre-extraction treatment, the coal-based feedstock is contacted with a solvent to enable solvent extraction and / or chemical8788859 35Attorney Docket No.: UWYO / 0134PC modification. For example, after drying, the coal-based feedstock is loaded into the reactor(s) and into the oven. The system is then pressurized with N2 or argon to a pressure of about 120 psi (0.83 MPa) to about 1 ,000 psi (6.89 MPa), such as from about 250 psi (1.7 MPa) to about 500 psi (3.45 MPa). The reactors are then heated to about 250°C to about 400°C, such as from about 275°C to about 370°C, at a rate of about 5°C / minute. Solvent is flowed through the system until the reactors are full of solvent. The solvent flow continues at a calculated flow rate throughout the duration of the extraction.

[0140] Any suitable flow rate can be utilized. For example, the solvent flow rate can be from about 1 mL / h to about 100 mL / h, such as from about 20 mL / h to about 80 mL / h, such as from about 30 mL / h to about 50 mL / h, or from about 5 mL / h to about 40 mL / h, such as from about 10 mL / h to about 30 mL / h, such as from about 15 mL / h to about 25 mL / h. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. The solvent flow rate can be calculated at about 0.1 ml per min per gram of dry coal in the reactor(s). The duration of the extraction can be any suitable period such as about 2 hours starting when the reactor temperature, as measured by a thermocouple in the solvent line in the oven, reaches about 350° C. This results in a solvent use to coal ratio of about 20:1 by volume.

[0141] If desired, the product(s) of solvent extraction or a derivative thereof can be subjected to fractionation. The remainder insoluble phase can be physically separated from the soluble phase. The soluble phase can be fractionated to generate two or more fractionation products, for example via partial precipitation fractional crystallization, fractional freezing, which may be carried out by a range of techniques well known in the art including but not limited to via flash precipitation. Collection of precipitated fractions may be carried out by a range of techniques well known in the art include but not limited to filtration, washing, purification and / or drying.

[0142] In some embodiments, staged cooling can be used to fractionate products. In some embodiments, for example for commercial production, the8788859 36Attorney Docket No.: UWYO / 0134PC mixture pressure may be sequentially lowered thereby vaporizing a portion of the solvent, causing precipitation to occur primarily due to concentration of the dissolved species and secondarily by the temperature reduction that occurs when the solvent vaporizes.

[0143] If desired, at least a portion of the solvent comprising alcohol can be distilled off by, for example, using a rotary evaporator or other suitable apparatus such as distillation tower. The distilled residue (DR) material can remain liquid at distillation temperatures but may solidify at room temperature. The DR material can be further dried in a vacuum oven to remove remaining solvent.

[0144] In some embodiments, the solvent can include a single alcohol or a mixture of alcohols. In some embodiments, and when the solvent includes two or more alcohols, the proportions of at least two of the alcohols in the solvent mixture can be from about 9:1 to about 1 :9, such as form about 8:2 to about 2:8, such as form about 7:3 to about 3:7, such as form about 6:4 to about 4:6, such as about 1 :1 , though other values are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0145] In some embodiments, the solvent may further include a nonalcoholic solvent such as a hydrocarbon solvent, such as a hydrocarbon that includes from 2 to 28 carbon atoms, such as from 6 to 24 carbon atoms, such as from 8 to 18 carbon atoms, such as from 10 to 16 carbon atoms, such as from 12 to 14 carbon atoms, or from 8 to 40 carbon atoms, such as from 10 to 30 carbon atoms, such as from 12 to 24 carbon atoms, such as from 14 to 22 carbon atoms. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. In some embodiments, the number of carbon atoms in the optional hydrocarbon solvent can be 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 , 12, 13, 14, 15, 16, 17, 18, 19, 20, 21 , 22, 23, 24, 25, 26, 27, 28, 29, 30, 31 , 32, 33, 34, 35, 36, 37, 38, 39, 40. Each of the foregoing numbers can be preceded by the word “about,” “at least about,” “less than about,” or “more than about,” and any of the foregoing8788859 37Attorney Docket No.: UWYO / 0134PC numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range.

[0146] The optional hydrocarbon solvent (which can form part of the solvent for extraction) can be linear or branched, saturated or unsaturated (for example, at least one C=C double bond), cyclic or acyclic, aromatic or not aromatic. When an optional hydrocarbon solvent is utilized, the mixture of solvents can include the same or similar proportions described above with respect to a solvent that include two or more alcohols.

[0147] In operation, compositions described herein can be formed or produced utilizing any suitable reactor. An illustrative, but non-limiting, example of a reactor includes a Swagelok tube reactor. Coal, which may be milled, is positioned in the reactor. The reactor can be pressurized and heated at a temperature of about 250°C to about 400°C, such as from about 275°C to about 370°C. A solvent or solvent mixture is then flowed into the reactor at a selected flow rate where it contacts the coal. The solvent containing the extract of coal is collected.

[0148] Compositions described herein can be formed or produced utilizing an example continuous plant that uses solvent extraction of coal. As will be generally understood by one having skill in the art, the processes, systems and conditions of this example may be scaled up via known techniques and systems to provide for commercial implementation.

[0149] As described above, coal solvent extraction can be a useful step in processing converting coal-based feedstocks into compositions comprising high value products. Products from coal solvent extraction can result in end products and / or intermediates useful to produce salable end products.

[0150] The plant throughput can be initially set at 4 Ibs / hour coal feed. This small size can address material handling issues with feedstocks and products. A typical plant run can be expected to last at least 2 hours. As will be readily understood, the scale, dimensions, components and process conditions8788859 38Attorney Docket No.: UWYO / 0134PC described herein can be adapted to large scale commercial implementation via well-known systems and techniques in the art.

[0151] FIG. 1A is a process flow diagram for coal slurry tanks 100A of a pilot plant 100. The process flow diagram for a pilot plant 100 that can be utilized to form or produce compositions described herein. Coal sufficient for a 2 hour run is batch loaded into a first feed slurry tank 101 and a second feed slurry tank 102, along with sufficient solvent to produce a pumpable feed slurry. The coal is provided to the first feed slurry tank 101 from a first coal source 105A and to the second feed slurry tank 102 from a second coal source 105B. The first coal source 105A is a ground coal source, while the second coal source 105B is a crushed coal source. The solvent is provided from the solvent feed tanks 100B and the solvent extraction reactor 100C of the pilot plant 100, as will be described in further detail below. In an embodiment, the first feed slurry tank 101 and second feed slurry tank 102 are at ambient pressure (for example, 1 bar) and at a temperature of about 65°C to about 75°C. Optionally, an agitator mixes the feed slurry to keep it at a relatively uniform composition. The first feed slurry tank 101 and the second feed slurry tank 102 may be covered or may be opened to reload the first feed slurry tank 101 and the second feed slurry tank 102.

[0152] A vent line, which can include a safety-check valve, is attached to the first feed slurry tank 101 and second feed slurry tank 102 to enable vent gas to exit the first feed slurry tank 101 and second feed slurry tank 102 in order to minimize vapor exposure to operators and other building occupants. In an embodiment, a feed pump 104 is coupled to the first feed slurry tank 101 and second feed slurry tank 102. The feed pump 104 can be a Moyno-style progressive cavity pump, which is capable of pumping high solids slurries. The feed pump 104 can have a variable speed drive to control the feed rate. An inert gas purge cylinder is coupled to the first feed slurry tank 101 and second feed slurry tank 102. The feed pump 104 feeds the feed slurry to the solvent extraction reactor 100C. The feed slurry passes through a pre-heater 103 as the feed slurry is fed to the solvent extraction reactor 100C. In some embodiments, a solvent from an evaporator 100D of a pilot plant 100, described8788859 39Attorney Docket No.: UWYO / 0134PC in further detail below, is fed to the solvent feed tanks 100B through the preheater 103 of the coal slurry tanks 100A. Additional solvent produced from the feed slurry as the feed slurry passes through the pre-heater 103 is fed to the solvent feed tanks 100B. In some embodiments, the pre-heater 103 is a heat exchanger.

[0153] FIG. 1 B is a process flow diagram for solvent feed tanks 100B of a pilot plant 100. The plant 100 includes a first solvent tank 107 and a second solvent tank 109. A first solvent drum 106 feeds the solvent to the first solvent tank 107 and a second solvent drum 108 feed the solvent to the second solvent tank 109. In some embodiments, the first solvent drum 106 is a fresh solvent drum and the first solvent tank 107 is a fresh solvent tank, while the second solvent drum 108 is a recycled solvent drum and the second solvent tank 109 is a recycled solvent tank. The first solvent drum 106 contains fresh solvent, i.e., solvent that has not yet been passed through the pilot plant 100. The second solvent drum 108, in contrast, contains solvent that has already been passed through the pilot plant 100. The second solvent drum 108 receives solvent from the coal slurry tanks 100A and the evaporator 100D via the preheater 103 of the coal slurry tanks 100A.

[0154] A first solvent pump 130A is coupled to the first solvent tank 107. Solvent is fed to the solvent extraction reactor 100C via the first solvent pump 130A. A second solvent pump 130B is coupled to the first solvent tank 107 and the second solvent tank 109. A mixture of recycled solvent and fresh solvent is fed to the coal slurry tanks 100A via the second solvent pump 130B.

[0155] FIG. 1 C is a process flow diagram for solvent extraction reactors 100C of a pilot plant 100. The pilot plant 100 includes an extraction reactor 110 coupled to the coal slurry tanks 100A and to the solvent feed tanks 100B. In some embodiments, the extraction reactor 110 is a coal-solvent extraction reactor. In some embodiments, the extraction reactor 110 may be more than one extraction reactors, i.e., a first extraction reactor 110A and a second extraction reactor 110B. Feed slurry is fed to the extraction reactor 110 via feed pump 104 and solvent is fed to the extraction reactor 110 via first solvent pump8788859 40Attorney Docket No.: UWYO / 0134PC130A. In some embodiments, a slurry pre-heater (e.g., pre-heater 103) is positioned between the feed pump 104 and the extraction reactor 110. In some embodiments, a solvent pre-heater is positioned between the second solvent pump 130B and the extraction reactor 110. In one embodiment, the extraction reactor 110 is a co-current extraction reactor. In another embodiment, the extraction reactor 110 is a countercurrent extraction reactor. In the illustrated embodiment, the first extraction reactor 110A and the second extraction reactor 110B are co-current extraction reactors. The feed slurry is fed into the first extraction reactor 110A and the second extraction reactor 110B proximate to the bottom of the first extraction reactor 110A and the second extraction reactor 110B. The extraction reactor 110 extracts and / or transforms the feed slurry into the solution and coal residue.

[0156] The solution and coal residue exit the first extraction reactor 110A and the second extraction reactor 110B proximate to the top of the first extraction reactor 110A and the second extraction reactor 110B. In some embodiments, the solution and coal residue may exit the first extraction reactor 110A and the second extraction reactor 110B proximate the bottom of the first extraction reactor 110A and the second extraction reactor 110B. The solution includes a solvent and a dissolved coal species (e.g., coal extract). In cocurrent extraction reactors, the solvent extraction results in a particle size reduction of the dissolved coal species, which maintains extraction rates within the co-current extraction reactor, as diffusion flux is inversely proportional to the length. In addition, the co-current extraction reactors are less likely to plug.

[0157] In countercurrent coal extraction reactors, fresh solvent is utilized to keep the driving force of extraction high, while the driving force in co-current coal extraction reactors is highest at the inlet of the co-current coal extraction reactor and diminishes as the feed slurry and solvent pass through the cocurrent coal extraction reactor. The increased driving forces increase the amount of dissolved coal species extracted from feed slurry while in the extraction reactor. Furthermore, countercurrent extraction reactors minimize the extract product on the residue solids that exit the solvent extraction reactor.8788859 41Attorney Docket No.: UWYO / 0134PC

[0158] The solution from the extractor contains a wide range of dissolved coal components with varying degrees of solubility, boiling points, and molecular weights. The solution may also include a quantity of undissolved coal species and residue (e.g., a suspended coal species and residue). This can be used to fractionate the extracted product into multiple product streams. In some embodiments, a staged reduction in temperature (resulting in pressure reductions) or partial evaporation of solvent can be used to fractionate the dissolved coal into any number of product streams to improve the properties of the solvent extraction products so that high quality final products can be made and isolated.

[0159] The feed slurry and solvent that are pumped into the first extraction reactor 110A via the feed pump 104 and the second solvent pump 130B are processed within the first extraction reactor 110A by contacting the feed slurry with the solvent. A motor (e.g. , a first motor 113A) facilitates flowing the solvent through, across, or over the feed slurry within the first extraction reactor 110A. A set of agitators, such as agitator paddles on a common shaft, are connected to the first motor 113A to improve feed slurry / solvent contacting. Baffles (e.g., horizontal baffles) between sets of agitators separator the extraction reactor 110 into a sequence of individual chambers and further improve feed slurry / solvent contacting. In some embodiments, the extraction reactors 110 include vertical baffles to improve mixing (e.g., liquid / solid contacting). The interaction of the solvent with the feed slurry facilitates the extraction and / or transformation of the feed slurry into the solution and coal residue. The agitators may be driven by a variety of methods such as a variable speed drive, and the rotational speed is adjusted to find a workable speed. Higher rotational speeds may improve feed slurry / solvent contacting, but in some instances (e.g., with countercurrent reactors) may interfere with coal settling, which is desirable to direct the solids down through the extractor. In some embodiments, the coal residue can be removed from the bottom of the first extraction reactor 110A and collected in a first residue collection tank 133 or a second residue collection tank 134. The coal residue can be filtered by a filter. A wash solvent can be fed from the solvent feed tanks 100B to the filter where it can be utilized to wash8788859 42Attorney Docket No.: UWYO / 0134PC the coal residue. Chilled or cooled solvent can enter the bottom of the first extraction reactor 110A to cool the components within the first extraction reactor 110A and to provide fluidized bearing (e.g., uplift) within the first extraction reactor 110A.

[0160] The solution is pumped from the first extraction reactor 110A to the second extraction reactor 110B to continue the extraction process. A second motor 113B facilitates the flowing the solvent through, across, or over the feed slurry within the second extraction reactor 11 OB. A set of agitators, such as agitator paddles on a common shaft, are connected to the second motor 113B to improve feed slurry / solvent contacting. Static baffles between sets of agitators further improve feed slurry / solvent contacting. The agitators may be driven by a variety of methods such as a variable speed drive, and the rotational speed is adjusted to find a workable speed. In some embodiments, the coal residue can be removed from the bottom of the second extraction reactor 110B and collected in the first residue collection tank 133 or the second residue collection tank 134. The coal residue can be filtered by a filter. A wash solvent can be fed from the solvent feed tanks 100B to the filter where it can be utilized to wash the coal residue. Chilled or cooled solvent can enter the bottom of the second extraction reactor 11 OB to cool the components within the second extraction reactor 110B and to provide fluidized bearing (e.g., uplift) within the second extraction reactor 110B.

[0161] The solution is pumped from the second extraction reactor to a first filter 111 and the second filter 112. The first filter 111 includes a first agitator 131 and the second filter 112 includes a second agitator 132. The first agitator 131 and the second agitator 132 facilitate the filtering of the solution. The first filter 111 and the second filter 112 may be any suitable solid / liquid separator, such as a centrifuge (or series of centrifuges), a hydroclone (or a series of hydroclones), filters, or settlers. The solution is filtered to separate any remaining coal residue from the solution. In some embodiments, once the solution passes through the first filter 111 , the coal residue is pumped to the second filter 112 separate any remaining solution from the coal residue. The coal residue is collected in the first residue collection tank 133 or the second8788859 43Attorney Docket No.: UWYO / 0134PC residue collection tank 134. Additional solvent from the solvent feed tanks 100B facilitates the transfer of the coal residue to the first residue collection tank 133 or the second residue collection tank 134. The solution that is separated from the coal residue is pumped to the evaporator 100D. Additional solvent from the solvent feed tanks 100B facilitates the transfer of the solution to the evaporator 100D. Any remaining feed slurry is recycled to the coal slurry tanks 100A.

[0162] FIG. 5 is an alternative process flow diagram for an alternative solvent extraction reactors 500C of a pilot plant 100. The alternative solvent extraction reactors 500C may be used in place of the solvent extraction reactors 100C. The first extraction reactor 110A is a co-current extraction reactor and the second extraction reactor 110B is a countercurrent extraction reactor. By passing the feed slurry through the co-current extraction reactor, the pilot plant receives the operational benefits and reduces particle sizes from the co-current reactor, while being able increase the amount of dissolved coal species extracted from the feed slurry. Furthermore, the decrease in the particle size from the co-current increases (in some embodiments, exponentially increases) the amount of dissolved coals species extracted from the feed slurry while the feed slurry passes through the countercurrent extraction reactor. The second extraction reactor 11 OB (countercurrent extraction reactor) receives solution and coal residue from the first extraction reactor 110A proximate to the top of the second extraction reactor 11 OB. Additionally, solvent is provided to the second extraction reactor 110B via the bottom of the second solvent reactor 110B for flushing of mechanicals, while preheated solvent is fed into the second extraction reactor 110B via a preheater 136 to an inlet proximate to the bottom of the second extraction reactor 11 OB. The solution can exit the second extraction reactor 11 OB proximate to the top of the second extraction reactor 110B, while coal residue exits proximate to the bottom of the second extraction reactor 11 OB. The solution exits the solvent extraction reactor 11 OB at a position closer to the top of the second solvent extraction reactor 110B than the inlet for the solution and coal residue.

[0163] FIG. 1 D is a process flow diagram for an evaporator 100D of a pilot plant 100. At the evaporator 100D includes an evaporator tank 114. The8788859 44Attorney Docket No.: UWYO / 0134PC solution can be heated to a selected temperature and pressurized at a certain pressure to separate components (e.g., vapors, liquids, and solids) within the evaporator tank 114. Vapor comprising dissolved coal species can be separated into a volatile phase and a differently volatile phase within the evaporator tank 114. The differently volatile phase containing coal extract (e.g. , alcohol extract of coal, dissolved coal species, etc.) can exit evaporator tank 114 proximate to the bottom of the evaporator tank 114 and collected in a first accumulation tank 127 and a second accumulation tank 128. Excess solvent and coal extract are pumped to the solvent extraction distillation column 100E from the first accumulation tank 127 and the second accumulation tank 128.

[0164] The volatile phase exiting via the top of the evaporator tank 114 can travel through a water-cooled condenser 115 and chilled condenser 116. Water is fed from a water source 135 to the water-cooled condenser 115 and the chilled condenser 116. The resulting condensed component is collected in a first condensate tank 117 and a second condensate tank 118. The condensed component can be fed back to the solvent feed tanks 100B. A vent line, which can include a safety-check valve, enables a vent gas to exit the water-cooled condenser 115 and the chilled condenser 116 via a vacuum pump 123 of the solvent extraction distillation column 100E, further described below.

[0165] In some embodiments, the solution is heated in a flash evaporator prior to being fed into the evaporator tank 114. At the flash evaporator, the solvent and the dissolved coal species (e.g., the coal extract) can be heated to a selected temperature and pressurized at a certain pressure to separate components. Vapor comprising dissolved coal species can travel to an evaporator tank 114. Components not vaporized at the flash evaporator can travel through an optional filter where it can contact the solvent. The resulting mixture can be fed to a second flash evaporator. Insolubles at the optional filter can exit the optional filter and be collected in an insoluble collector tank.

[0166] FIG. 1 E is a process flow diagram for a solvent extraction distillation column 100E of a pilot plant 100. Coal extract is pumped from the evaporator 100D into a coal extract drum 120 of the solvent extraction distillation column8788859 45Attorney Docket No.: UWYO / 0134PC100E. The coal extract is fed from the coal extract drum 120 to the distillation column 119. The distillation column 119 distills the coal extract to recover solvent from the coal extract. The solvent is evaporated into a solvent vapor and is removed from the top of the distillation column 119. The solvent vapor exits the distillation and passes through an exchanger 126 before entering a condensate drum 129, where the vapor condenses. The exchanger 126 condenses the solvent vapor. The condensed solvent is pumped from the condensate drum 129 and either recirculated into the distillation column 119 or to a first recycle solvent tank 124 and a second recycle solvent tank 125. The condensate drum 129 separates the condensed solvent and the solvent vapor. Some of the solvent may be fed back into the distillation column 119 as reflux. Any excess vent gas is pumped out of the pilot plant 100 by the vacuum pump 123.

[0167] Any remaining coal extract is removed from the bottom of the distillation column 119 and pumped to an extract tank 122. A portion of the coal extract is diverted to a reboiler 121. The reboiler 121 provides heat to the distillation column 119 and recycles the coal extract to the distillation column 119 to remove excess solvent.

[0168] FIG. 2 is a co-current coal-solvent extraction reactor 200. In a cocurrent extraction reactor, the feed slurry is pumped to into the extraction reactor 110 via or proximate to the bottom of the extraction reactor 110. The extraction reactor 110 can include a reactor 201 . Feed slurry and solvent can enter the reactor 201 via inlet 203. Chilled or cooled solvent can enter the reactor 201 via inlet 208 at the bottom of the reactor 201 and exit the reactor 201 via outlet 205 where it can contact a filter 206 (such as a Fines filter). Mixing inside the reactor 201 can be accomplished by use of a motor 213. The motor 213 may include a variable speed magnet drive motor assembly or other suitable drive assembly. In some embodiments, coal residue can be removed from the reactor 201 as a slurry via the bottom of the reactor 201 using a coal residue pump. The coal residue pump can be a Moyno-style progressive cavity pump or a Moyno dosing pump. Chilled or cooled solvent can enter the reactor 201 via inlet proximate the bottom of the reactor 201 to cool the components8788859 46Attorney Docket No.: UWYO / 0134PC within the reactor 201 and to provide fluidized bearing (e.g., uplift) within the reactor 201 .

[0169] A set of agitators, such as angled agitator paddles 210A and flat agitator paddles 21 OB, are coupled to a common shaft 211 . The common shaft 211 is connected to the motor 213 to improve feed slurry / solvent contacting. Baffles 212 between sets of agitators define chamber 214 and further improve feed slurry / solvent contacting. The baffles 212 may include horizontal baffles, as shown, or vertical baffles. In some embodiments, each chamber 214 has at least one angled agitator paddle 210A and at least one flat agitator paddle 21 OB disposed within the chamber 214. The interaction of the solvent with the feed slurry is facilitated by the at least one angled agitator paddle 210A and at least one flat agitator paddle 21 OB by creating a vortex within each chamber 214. As the solvent and feed slurry are pulled through the vortex, coal residue is separated from the solution. The coal residue settles at the bottom of the reactor 201 while the solution is propelled from the chamber 214 into an adjacent chamber 214 positioned directly above the chamber 214. After being propelled upward to the top of the reactor 201 through a series of chambers 214, the solution exits the reactor 201 via outlet 205 proximate to the top of the reactor 201 .

[0170] FIG. 3 is a counter current coal-solvent extraction reactor 300. In a counter current extraction reactor, the feed slurry is pumped to into the extraction reactor 110 via or proximate to the top of the extraction reactor 110. Feed slurry can enter the reactor 301 via inlet 302. Solvent can enter the reactor 301 via inlet 303. The solution can exit the reactor 301 via outlet 305 where it can contact a filter 306 (such as a Fines filter). Mixing inside the reactor 301 can be accomplished by use of a motor 313. The motor 313 can be a variable speed magnet drive motor assembly. In some embodiments, coal residue can be removed from the reactor 301 as a slurry via the bottom of the reactor 301 using a coal residue pump. The coal residue slurry pump may be a Moyno- style progressive cavity pump, a Moyno dosing pump or a cascading centrifugal pump. Chilled or cooled solvent can enter via inlet 308 where it can mix with the coal residue, cool components within the reactor 301 and to provide8788859 47Attorney Docket No.: UWYO / 0134PC fluidized bearing (e.g., uplift) within the reactor 301. Coal residue exits the counter current coal-solvent extraction reactor 300 via outlet 310.

[0171] A set of agitators, such as angled agitator paddles 310A, are coupled to a common shaft 311 . The common shaft 311 is connected to the motor 313 to improve feed slurry / solvent contacting. Baffles 312 between sets of agitators define chamber 314 and further improve feed slurry / solvent contacting. The baffles 212 may include horizontal baffles, as shown, or vertical baffles. In some embodiments, each chamber 314 has at least one angled agitator paddle 310A disposed within the chamber 314. The reactor 301 has solids (e.g., feed slurry) entering the reactor 301 near the top of the reactor 301 and falling down through the reactor 301 . Most of the solvent (aside from the solvent used to slurry the feed coal) enters the reactor 301 near the bottom of the vessel, so liquid flows up the reactor 301 , contacting the solids falling down the reactor 301. The interaction of the solvent with the feed slurry is facilitated by the at least one angled agitator paddle 310A. As the solvent and feed slurry are pulled through the vortex, coal residue is separated from the solution. The coal residue settles at the bottom of the reactor 301 while the solution is propelled from the chamber 314 into an adjacent chamber 314 positioned directly above the chamber 314. After being propelled upward to the top of the reactor 301 through a series of chambers 314, the solution exits the reactor 301 via outlet 305 proximate to the top of the reactor 301 .

[0172] In example batch experiments, solvent flows at a rate, for example, a constant rate, through a cylinder packed with coal until the produced liquid starts to clear, indicative that no more coal components are being extracted. This results in a high solvent / coal ratio, about 20:1 , and a 2 hour extraction time. Other solvent / coal ratios and extraction times are potentially useful in the present reactor, such as a solvent ratio (volume solvent to volume coal) selected from the range of 5:1 to 100: 1 and extraction selected over 0.5 hours to 100 hrs. A reduction in the solvent / coal ratio may be desirable in some embodiments to reduce the cost of coal extraction and may reduce the extraction time.8788859 48Attorney Docket No.: UWYO / 0134PC

[0173] The extraction reactor 110 may have a 10: 1 solvent / coal ratio and an extraction time of about one hour. The extractor operates at about 250°C to about 400°C, which is the same temperature used for at least some of the batch experiments. The extractor temperature is maintained by a thermal control system, such as an electric clamshell heater. In some embodiments, the extractor pressure may be set to a certain pressure to keep the solvent in the liquid state. A variety of temperature, pressure, and flow rate conditions are compatible with the present systems and methods.

[0174] FIG. 4 is a separator 400 used to recover an extracted product from the solution. The separator 400 may be used in place of the evaporation tank 114 in FIG. 1 D. In some embodiments, the solution leaving the extraction reactor 110 is separated into the extracted product and a recycle solvent. The solution enters the separator 400 via line 401 and is flashed in the separator 400 to produce solvent vapor and a relatively low vapor pressure product. The solvent vapor exits the separator 400 via a first line 402. This approach is compatible, for example, with a plant wherein the heated, pressurized solution is sprayed into an atmospheric pressure chamber to produce solvent vapor and solid product, which includes small, solid particles. The solid product exits the separator 400 via a second line 403.

[0175] Depending on the desired composition, the pilot plant 100 can be designed to produce two or more extraction products from the solution exiting the extraction reactor 110, such as two extraction products, three extraction products, and so forth. The three extraction products can be separated based on, for example, boiling points and use of apparatus such as partial flash evaporators and flash evaporators. Use of multiple flash evaporators can allow for careful control over properties, such as chemical compositions, solubilities, and molecular weights, among others.

[0176] In small scale plants, hot materials rapidly cool to ambient temperature unless the material is heated. At large scale, active cooling may be employed to achieve a significant cooling rate, such as by use of indirect heat transfer (heat exchangers) to cool liquids that are simultaneously8788859 49Attorney Docket No.: UWYO / 0134PC precipitating solids. Additionally, or alternatively, the pressure of the solution can be dropped, causing a portion of the solvent to flash. This results in concentrating the remaining solution and lowering the temperature of the solution due to the heat of vaporization. Using this method, the pilot plant 100 can be operated to drop the pressure of the solution from the extraction reactor 110 from about 500 psi (3.45 MPa) to about 200 psi (1 .38 MPa). Additionally, or alternatively, flash precipitators, flash evaporators, and filtering schemes can be utilized for separation of product streams.

[0177] Apparatus described above can be utilized to extract coal using a solvent comprising alcohol. Processes for treating (or processing) a coal-based feedstock to produce a high value product (a composition described herein) can include contacting a coal-based feedstock with a solvent comprising an alcohol under solvent treatment conditions for generating a soluble phase product and a remainder insoluble phase product and fractionating the soluble phase product generating at least two fractions under conditions such that at least one of said fractionated products includes a composition described herein (for example, a high value product).

[0178] Implementations can include one or more of the following. The coalbased feedstock can be at least partially derived from coal. The coal-based feedstock can be at least partially derived from subbituminous coal or a derivative thereof. The coal-based feedstock can be generated by thermal treatment of coal or a derivative thereof, such as drying, pyrolysis, heating, or combinations thereof, among others. The coal-based feedstock can be generated by mechanical processing of coal or a derivative thereof such as grinding, pulverizing, sieving, changing particle size, formation of a slurry, or combinations thereof, among others.

[0179] As described herein, solvent treatment is useful for separating one or more components of a coal-based feedstock and / or chemically converting components of coal-based feedstock to generate useful intermediate, derivative, or finished products. In some examples, the solvent can comprise, consist essentially of, or consist of a C2 to C28 monohydric alcohol, a C2 to8788859 50Attorney Docket No.: UWYO / 0134PCC28 polyhydric alcohol, or combinations thereof. The solvent can be a pure solvent. The solvent can be a mixed solvent. The solvent can at least partially comprise one or more recycle streams derived from a coal treatment process, a biomass treatment process, a petrochemical process, or combinations thereof.

[0180] Selection of the volume of solvent to volume of coal can be beneficial to achieve target yields and to address efficiency. The solvent treatment conditions can include a ratio of a volume of the solvent to a volume of the coal of about 1 : 1 to about 100: 1 , such as from about 1 :1 to 50: 1 , such as from about 1 :1 to about 20:1 , such as from about 1 :1 to 10:1 , though other ratios are contemplated.

[0181] The contacting can comprise extracting the coal-based feedstock with the solvent, chemically reacting the coal-based feedstock with the solvent, or combinations thereof. The contacting can be performed for a duration of about 5 minutes to about 60 hours, such as from about 10 minutes to about 20 hours, such as from about 20 minutes to about 10 hours, such as from about 30 minutes to about 5 hours, though other durations are contemplated. The contacting can be performed at a temperature of about 100°C or more, such as about 200°C or more, such as about 300°C or more, such as from about 300°C to about 500°C, such as from about 325°C to about 425°C, such as from about 350°C to about 400°C, though other temperatures are contemplated. The contacting can be performed at or near (for example, ±10%) a temperature at which the solvent boils.

[0182] The contacting can be performed at a pressure high enough such that the solvent is at least partially a liquid during the contacting. The contacting can be performed at a pressure high enough such that the solvent is at least partially a dense supercritical fluid during the contacting. The contacting can be performed at supercritical fluid conditions. The contacting can be performed using a countercurrent flow. The contacting can be performed using a countercurrent extraction.8788859 51Attorney Docket No.: UWYO / 0134PC

[0183] The contacting can convert at least 3% by mass of the coal-based feedstock to the soluble phase product, such as about 10% by mass or more, such as about 25% by mass or more, such as about 50% by mass or more, such as about 70% by mass or more, such as about 80% mass or more, such as about 85% by mass or more. The contacting can convert from about 3% to about 95% by mass of the coal-based feedstock to the soluble phase product. The contacting can be performed as a flow through process, a batch process, a co-current process, a countercurrent process, or combinations thereof.

[0184] The alcohol extract of coal can have any suitable weight average molecular weight. In some embodiments, the alcohol extract of coal can be characterized as having a weight average molecular weight that is from about 50 Daltons (Da) to about 2,000 Da, such as from about 100 Da to about 1 ,500 Da, such as from about 150 Da to about 1 ,300 Da, such as from about 250 Da to about 1 ,100 Da, such as from about 300 Da to about 1 ,000 Da, such as from about 400 Da to about 900 Da, such as from about 500 Da to about 800 Da, such as from about 600 Da to about 700 Da, though other average molecular weights are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. In at least one example, the alcohol extract of coal can have a weight average molecular weight of about 300 Da to about 2,000 Da. The weight average molecular weight is determined by matrix-assisted laser desorption / ionization (MALDI) mass spectrometry.

[0185] The C2 to C28 alcohol extract of coal can have a weight average molecular weight that is from about 300 Da to about 2,000 Da as determined by matrix-assisted laser desorption / ionization (MALDI) mass spectrometry. The alcohol extract of coal can have an apparent weight average molecular weight that is from about 300 to about 25,000 Da, such as from about 300 Da to about 13,000 Da, such as from about 350 Da to about 10,000 Da, such as from about 400 Da to about 2,500 Da, though other average molecular weights are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. The8788859 52Attorney Docket No.: UWYO / 0134PC apparent weight average molecular weight is determined by size exclusion chromatography.

[0186] The alcohol extract of coal can be subject to fractionation. The fractionating of the alcohol extract of coal (if performed) can be achieved by vacuum distillation. Conditions for distillation can be selected such that a vacuum distilled product can be characterized as having a weight average molecular weight that is from about 50 Daltons (Da) to about 2,000 Da, such as from about 100 Da to about 1 ,500 Da, such as from about 150 Da to about 1 ,300 Da, such as from about 250 Da to about 1 ,100 Da, such as from about 300 Da to about 1 ,000 Da, such as from about 400 Da to about 900 Da, such as from about 500 Da to about 800 Da, such as from about 600 Da to about 700 Da, though other average molecular weights are contemplated. Any of the foregoing numbers can be used singly to describe an open-ended range or in combination to describe a close-ended range. In at least one example, the vacuum distilled product can have a weight average molecular weight of about 300 Da to about 2,000 Da.

[0187] The high value product can comprise a non-fuel product. The high value product can comprise a product or precursor thereof, the product or precursor thereof comprising: polymers or polymer precursors; asphaltenic intermediates and / or finished products; asphalt binder; partial replacement of asphalt; recycling agent; anti-stripping agent; crack sealant; sealant for construction; sealant for roofing; coating; adhesive; coal tar; distillates; pitch; bulk asphalt; paving asphalt; graphitic materials; carbon fibers; graphene; building materials; or combinations thereof.

[0188] The high value product can comprise polyols, polyurethanes, polyamides, polyesters, epoxy polymers precursors thereof, derivatives thereof, or combinations thereof. The high value product can comprise a nonfuel product, a polymer or polymer precursor, a high value chemical, a composite material, a carbon fiber or a graphene product, a building material, a road material, a paving material, a roofing material, or combinations thereof.8788859 53Attorney Docket No.: UWYO / 0134PC

[0189] The following examples are put forth to provide those of ordinary skill in the art with a complete disclosure and description of how to make and use embodiments of the present disclosure, and are not intended to limit the scope of embodiments of the present disclosure. Efforts have been made to ensure accuracy with respect to numbers used (for example, amounts, dimensions, et cetera) but some experimental errors and deviations should be accounted for.Embodiments Listing

[0190] The present disclosure provides, among others, the following embodiments, each of which can be considered as optionally including any alternate embodiments:

[0191] Clause 1 . A co-current solvent extraction reactor, comprising: a reactor; a first inlet proximate to a bottom of the reactor; a motor; a shaft; a set of agitators coupled to the shaft; one or more chambers defined by a plurality of baffles; and a first outlet proximate to a top of the reactor.

[0192] Clause 2. The co-current solvent extraction reactor of claim 1 , wherein the set of agitators comprises: one or more angled agitator paddles; and one or more flat agitator paddles.

[0193] Clause 3. The co-current solvent extraction reactor of claims 2 or 3, wherein at least one angled agitator paddle and at least one flat agitator paddle are disposed within a chamber of the one or more chambers.8788859 54Attorney Docket No.: UWYO / 0134PC

[0194] Clause 4. The co-current solvent extraction reactor of claims 1-3, further comprising a filter coupled to the first outlet.

[0195] Clause 5. The co-current solvent extraction reactor of claims 1-4, further comprising a second outlet proximate to the bottom of the reactor and a pump coupled to the second outlet.

[0196] Clause 6. The co-current solvent extraction reactor of claims 1-5, wherein the pump a Moyno-style progressive cavity pump or a Moyno dosing pump.

[0197] Clause 7. The co-current solvent extraction reactor of claims 1-6, further comprising a second inlet at the bottom of reactor.

[0198] Clause 8. A countercurrent solvent extraction reactor, comprising: a reactor; a first inlet proximate to a bottom of the reactor; a second inlet proximate to a top of the reactor; a motor; a shaft; a set of agitators coupled to the shaft; one or more chambers defined by a plurality of baffles; and a first outlet proximate to the top of the reactor; and a second outlet proximate the bottom of the reactor.

[0199] Clause 9. The countercurrent solvent extraction reactor of claim 8, wherein the set of agitators comprises: one or more angled agitator paddles; and one or more flat agitator paddles.8788859 55Attorney Docket No.: UWYO / 0134PC

[0200] Clause 10. The countercurrent solvent extraction reactor of claims 9 or 10, wherein at least one angled agitator paddle are disposed within a chamber of the one or more chambers.

[0201] Clause 11 . The countercurrent solvent extraction reactor of claims 8-10, further comprising a filter coupled to the first outlet.

[0202] Clause 12. The countercurrent solvent extraction reactor of claims 8-11 , further comprising a second outlet proximate to the bottom of the reactor and a pump coupled to the second outlet.

[0203] Clause 13. The countercurrent solvent extraction reactor of claims 8-12, wherein the pump a Moyno-style progressive cavity pump or a Moyno dosing pump.

[0204] Clause 14. The countercurrent solvent extraction reactor of claims 8-13, further comprising a third inlet at the bottom of reactor.

[0205] Clause 15.A solvent extraction plant, comprising: a solvent tank; a coal slurry tank configured to: receive a solvent from the solvent tank; receive coal from a coal source; and form a feed slurry from the solvent and the coal; a solvent extraction reactor configured to: receive the solvent from the solvent tank; receive the feed slurry from the coal slurry tank; and8788859 56Attorney Docket No.: UWYO / 0134PC form a solution from the feed slurry, the solution comprising solvent, a dissolved coal species, and a coal extract.

[0206] Clause 16. The solvent extraction plant of claims 15, wherein the solvent extraction plant comprises an evaporator configured to: receive the solution from the solvent extraction reactor; form a first recycled solvent and a coal extract; provide the first recycled solvent to the solvent tank; and provide the coal extract to a solvent extraction distillation column.

[0207] Clause 17. The solvent extraction plant of claims 15 or 16, wherein the coal extract comprises a solvent extraction distillation column configured to: to receive the coal extract from the evaporator; form a second recycled solvent from the coal extract; provide a coal extract to an extract collection tank; and provide the second recycled solvent to the evaporator.

[0208] Clause 18. The solvent extraction plant of claim 15, wherein the solvent extraction reactor comprises a reactor to form the solution, wherein the reactor is one or a co-current reactor or a countercurrent reactor.

[0209] Clause 19. The solvent extraction plant of claims 15 or 16, wherein the coal extract comprises: a C2 to C28 alcohol extract of coal.

[0210] Clause 20. The solvent extraction plant of claims 15-17, wherein the C2 to C28 alcohol extract of coal is a linear or branched C2 to C28 alcohol, saturated or unsaturated C2 to C28 alcohol, cyclic or acyclic C2 to C28 alcohol, aromatic or nonaromatic C2 to C28 alcohol, lauryl alcohol, myristyl alcohol,8788859 57Attorney Docket No.: UWYO / 0134PC stearyl alcohol, cetyl alcohol, oleyl alcohol, linoleic alcohol, isostearyl alcohol, vardonal, ether, internal olefin, or combination thereof.

[0211] Clause 21 . The solvent extraction plant of claims 15-18, wherein the C2 to C28 alcohol extract of coal comprises an apparent weight average molecular weight that is from about 300 Da to about 25,000 Da as determined by size exclusion chromatography.

[0212] Clause 22. The solvent extraction plant of claims 15-19, wherein the C2 to C28 alcohol extract of coal comprises a weight average molecular weight that is from about 300 Da to about 2,000 Da.

[0213] Clause 23. The solvent extraction plant of claims 15-21 , wherein the coal extract is a coal residue.

[0214] Clause 24. The solvent extraction plant of claim 15-23, wherein the coal extract includes a coal fly ash.

[0215] Clause 25. The solvent extraction plant of claims 15-24, further comprising a first solvent extraction reactor and a second solvent extraction reactor, wherein the first solvent extraction reactor and the second solvent extraction reactor are co-current solvent extraction reactors.

[0216] Clause 26. The solvent extraction plant of claims 15-24, further comprising a first solvent extraction reactor and a second solvent extraction reactor, wherein the first solvent extraction reactor is a co-current solvent extraction reactor and the second solvent extraction reactor is a countercurrent solvent extraction reactor.

[0217] As is apparent from the foregoing general description and the specific aspects, while forms of the aspects have been illustrated and described, various modifications can be made without departing from the spirit and scope of the present disclosure. Accordingly, it is not intended that the present disclosure be limited thereby. Likewise, the term “comprising” is considered synonymous with the term “including.” Likewise whenever a composition, process operation, process operations, an element or a group of elements is8788859 58Attorney Docket No.: UWYO / 0134PC 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, process operation, process operations, element, or elements and vice versa, such as the terms “comprising,” “consisting essentially of,” “consisting of” also include the product of the combinations of elements listed after the term.

[0218] For purposes of this present disclosure, and unless otherwise specified, all numerical values within the detailed description and the claims herein are modified by “about” or “approximately” the indicated value, and consider experimental error and variations that would be expected by a person having ordinary skill in the art. For the sake of brevity, only certain ranges are explicitly disclosed herein. However, ranges from any lower limit may be combined with any upper limit to recite a range not explicitly recited, as well as, ranges from any lower limit may be combined with any other lower limit to recite a range not explicitly recited, in the same way, ranges from any upper limit may be combined with any other upper limit to recite a range not explicitly recited. For example, the recitation of the numerical range 1 to 5 includes the subranges 1 to 4, 1.5 to 4.5, 1 to 2, among other subranges. As another example, the recitation of the numerical ranges 1 to 5, such as 2 to 4, includes the subranges 1 to 4 and 2 to 5, among other subranges. Additionally, within a range includes every point or individual value between its end points even though not explicitly recited. For example, the recitation of the numerical range 1 to 5 includes the numbers 1 , 1.5, 2, 2.75, 3, 3.80, 4, 5, among other numbers. Thus, every point or individual value may serve as its own lower or upper limit combined with any other point or individual value or any other lower or upper limit, to recite a range not explicitly recited.

[0219] References cited herein are incorporated by reference herein in their entirety to indicate the state of the art as of their publication or filing date and it is intended that this information can be employed herein, if needed, to exclude specific embodiments that are in the prior art.8788859 59Attorney Docket No.: UWYO / 0134PC

[0220] As used herein, the indefinite article “a” or “an” shall mean “at least one” unless specified to the contrary or the context clearly indicates otherwise. For example, embodiments comprising “a solvent” include embodiments comprising one, two, or more solvents, unless specified to the contrary or the context clearly indicates only one solvent is included.

[0221] While the foregoing is directed to embodiments of the present disclosure, other and further embodiments of the disclosure may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow.8788859 60

Claims

Attorney Docket No.: UWYO / 0134PCWhat is claimed is:1 . A co-current solvent extraction reactor, comprising: a reactor; a first inlet proximate to a bottom of the reactor; a motor; a shaft; a set of agitators coupled to the shaft; one or more chambers defined by a plurality of baffles; and a first outlet proximate to a top of the reactor.

2. The co-current solvent extraction reactor of claim 1 , wherein the set of agitators comprises: one or more angled agitator paddles; and one or more flat agitator paddles.

3. The co-current solvent extraction reactor of claim 2, wherein at least one angled agitator paddle and at least one flat agitator paddle are disposed within a chamber of the one or more chambers.

4. The co-current solvent extraction reactor of claim 1 , further comprising: a second outlet proximate to the bottom of the reactor and a pump coupled to the second outlet.

5. The co-current solvent extraction reactor of claim 1 , further comprising: a second inlet at the bottom of reactor.

6. A countercurrent solvent extraction reactor, comprising: a reactor; a first inlet proximate to a bottom of the reactor; a second inlet proximate to a top of the reactor; a motor; a shaft;8788859 61Attorney Docket No.: UWYO / 0134PC a set of agitators coupled to the shaft; one or more chambers defined by a plurality of baffles; and a first outlet proximate to the top of the reactor; a second outlet proximate the bottom of the reactor.

7. The countercurrent solvent extraction reactor of claim 6, wherein the set of agitators comprises: one or more angled agitator paddles.

8. The countercurrent solvent extraction reactor of claim 7, wherein at least one angled agitator paddle are disposed within a chamber of the one or more chambers.

9. The countercurrent solvent extraction reactor of claim 6, further comprising: a second outlet proximate to the bottom of the reactor and a pump coupled to the second outlet.

10. The countercurrent solvent extraction reactor of claim 6, further comprising a third inlet at the bottom of reactor.

11. A solvent extraction plant, comprising: a solvent tank; a coal slurry tank configured to: receive a solvent from the solvent tank; receive coal from a coal source; and form a feed slurry from the solvent and the coal; a solvent extraction reactor configured to: receive the solvent from the solvent tank; receive the feed slurry from the coal slurry tank; and form a solution from the feed slurry, the solution comprising solvent and a dissolved coal species; an evaporator configured to:8788859 62Attorney Docket No.: UWYO / 0134PC receive the solution from the solvent extraction reactor; form a first recycled solvent and a coal extract; provide the first recycled solvent to the solvent tank; and provide the coal extract to a solvent extraction distillation column; and the solvent extraction distillation column configured: to receive the coal extract from the evaporator; form a second recycled solvent from the coal extract; provide a coal extract to an extract collection tank; and provide the second recycled solvent to the evaporator.

12. The solvent extraction plant of claim 11 , wherein the solvent extraction reactor comprises a reactor to form the solution, wherein the reactor is a cocurrent reactor, a countercurrent reactor, or a combination of a co-current reactor and a countercurrent reactor.

13. The solvent extraction plant of claim 11 , wherein the coal extract comprises a C2 to C28 alcohol extract of coal, wherein the C2 to C28 alcohol extract of coal is a linear or branched C2 to C28 alcohol, saturated or unsaturated C2 to C28 alcohol, cyclic or acyclic C2 to C28 alcohol, aromatic or nonaromatic C2 to C28 alcohol, lauryl alcohol, myristyl alcohol, stearyl alcohol, cetyl alcohol, oleyl alcohol, linoleic alcohol, isostearyl alcohol, vardonal, ether, internal olefin, or combination thereof.

14. The solvent extraction plant of claim 13, wherein the C2 to C28 alcohol extract of coal comprises an apparent weight average molecular weight that is from about 300 Da to about 25,000 Da as determined by size exclusion chromatography.

15. The solvent extraction plant of claim 13, wherein the C2 to C28 alcohol extract of coal comprises a weight average molecular weight that is from about 300 Da to about 2,000 Da.8788859 63

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