GB2105741A - Two stage coal liquefaction process - Google Patents

Two stage coal liquefaction process Download PDF

Info

Publication number
GB2105741A
GB2105741A GB08127714A GB8127714A GB2105741A GB 2105741 A GB2105741 A GB 2105741A GB 08127714 A GB08127714 A GB 08127714A GB 8127714 A GB8127714 A GB 8127714A GB 2105741 A GB2105741 A GB 2105741A
Authority
GB
United Kingdom
Prior art keywords
coal
solvent
process according
hydrocracking
dissolved
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
GB08127714A
Other versions
GB2105741B (en
Inventor
Arthur J Dahlberg
Joel W Rosenthal
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron USA Inc
Original Assignee
Chevron Research and Technology Co
Chevron Research Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chevron Research and Technology Co, Chevron Research Co filed Critical Chevron Research and Technology Co
Priority to GB08127714A priority Critical patent/GB2105741B/en
Priority to NL8104248A priority patent/NL8104248A/en
Priority to FR8118225A priority patent/FR2513652B1/en
Priority to BE0/206089A priority patent/BE890526A/en
Publication of GB2105741A publication Critical patent/GB2105741A/en
Application granted granted Critical
Publication of GB2105741B publication Critical patent/GB2105741B/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10GCRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G1/00Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/002Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal in combination with oil conversion- or refining processes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

Subdivided coal is dissolved at 20 in a metal contaminants-containing crude petroleum solvent or petroleum- derived solvent at an elevated temperature, for example from 400 to 480 DEG C in the presence of added hydrogen 25 to form a mixture of dissolved coal, solvent and insoluble solids. This mixture is then contacted at 45 a hydrocracking catalyst and hydrogen under hydrocracking conditions at a reduced temperature below 425 DEG C, resulting in a product 50 having a normally liquid portion which may be used directly as a low- sulfur, low-nitrogen fuel oil. <IMAGE>

Description

SPECIFICATION Two-stage coal liquefaction process This invention relates to an improved process for the liquefaction of raw subdivided coal. More particularly, the invention relates to an improved liquefaction process wherein coal is dissolved in a crude petroleum or petroleum-derived solvent at an elevated temperature and hydrocracked at a lower temperature to produce acceptable fuel oils accompanied by minimum gas production.
Coal is our most abundant indigenous fossil fuel resource, and as a result of dwindling petroleum reserves, concerted research efforts are being directed towards recovery of liquid hydrocarbons from coal on a commercial scale. A promising approach in this field relates to the direct liquefaction of coal accompanied with minimum gas production. The approach has principally evolved from the early work of F.
Bergius, who discovered that transportation fuels could be produced by the high-pressure hydrogenation of a paste of coal, solvent and catalyst. Later discoveries revealed the advantageous use of specific hydrogenation solvents at lower temperatures and pressures.
With these solvents, such as partially saturated polycyclic aromatics, hydrogen is transferred from the solvent to the coal molecules, thus causing depolymerization and dissolution of the coal. The resulting coal liquid, however, has a high molecular weight and an accordingly high viscosity, which presents considerable obstacles to removing the fine coal residue remaining in the liquid, since these particles typically range in size from 1 to 25 microns in diameter. The complete nature of the coal residue, or undissolved solids, is not wholly understood; however, the residue appears to be a composite of organic and inorganic species. The residue organic matter is similar to coke, and the residue inorganic matter is representative of the well-known ash constituents.Removal of the residue from the coal liquid has been considered a critical step in the prior art in the preparation of clean fuels, particularly in those processes in which the coal liquids are subjected to catalytic upgrading, such as hydrocracking.
In our Specification No. 1,551,177, there is described a coal liquefaction process which comprises.
(a) forming a slurry from particulate coal and a hydrogen donor solvent; (b) substantially dissolving the coal in the solvent by heating the slurry to a temperature in the range from 750 to 9000F (399--482 OC) and thereby forming a mixture comprising solvent, dissolved coal and insoluble solids; (c) contacting said mixture in a reaction zone with hydrogen and a hydrocracking catalyst under hydrocracking conditions including a temperature below 8000F (4270C); and (d) withdrawing from the reaction zone an effluent stream, the normally liquid portion of which has an API gravity of at least -3, a sulfur content of less than 0.1 0 weight percent and a nitrogen content of less than 0.50 weight percent.
Nearly all crude petroleum stocks and especially crude residua contain metal compounds, but the amounts and types of metals may vary considerably depending upon the geographic and geological origin of the coal.
Certain South American crudes, for example, contain large amounts of vanadium but only small amounts of other metals. Other crudes, for example, Middle Eastern, contain a broad spectrum of metals in only moderate concentrations, mostly metals such as nickel and vanadium, and smaller amounts of such metals as iron and sodium. Still other crudes, for example, California crudes, contain large amounts of many metals, including large amounts of iron and sodium. In the processing of petroleum feedstocks over fixed-bed hydrocracking catalysts to convert the higher-boiling fractions to lowerboiling fractions, it is generally recognized that a high metals content in the feed tends to rapidly foul the catalyst bed. The metal compounds present in the residua will form metalliferous deposits on and between catalysts in the bed and with the pores of the catalyst.The deposits on and between the catalyst particles may clog the catalyst bed, thereby restricting the oil throughout. Deposits within the catalyst pores result in an overall deactivation of the catalyst.
We have now surprisingly found that the presence of coal particles when a metal-containing crude petroleum feedstock is contacted with a hydrocracking catalyst significantly inhibits coking of the catalyst, and that accordingly metal containing petroleum or petroleum-derived solvents can advantageously be used in a coal liquefaction process such as that described in our earlier specification.
Thus, in accordance with the present invention, there is provided a process for the liquefaction of coal wherein subdivided coal is substantially dissolved in crude petroleum solvent or a petroleum-derived solvent containing metal contaminants at a temperature of, for example, between 400 and 4800 C, in the presence of added hydrogen to form a mixture comprising solvent, dissolved coal and insoluble solids, which is then contacted in a reaction zone with hydrogen in the presence of an externally supplied hydrocracking catalyst under hydrocracking conditions. Preferably, the mixture is cooled before hydrocracking to a temperature below 4250C and lower than the temperature at which the coal is dissolved.The normally liquid portion of the hydrocracked effluent stream generally has a specific gravity of less than 1, a low sulfur and nitrogen content and a low metals content.
The coal is advantageously dissolved in the presence of added hydrogen at a pressure above 35 atmospheres. The weight ratio of petroleum solvent to coal is generally maintained in the range 5:1 to 0.5:1 and said petroleum solvent can comprise a crude fraction boiling above 2000C.
The hydrocracking reaction zone may comprise a fixed bed, moving bed, or ebullating bed of catalyst. The hydrocracking catalyst will preferably comprise a group VIII and/or Group VIB metal on a cracking support.
A preferred embodiment of the invention will now be described, by way of example, with reference to the accompanying drawing which shows a block flow diagram of suitable flow paths for use in practising this embodiment of the invention.
Referring to the drawing, comminuted coal is slurried with a metal-containing petroelumderived solvent boiling above 2000C in a mixing zone 10. The effluent slurry from zone 10 passes to a dissolver 20, wherein the slurry is heated to dissolve at least 50 weight percent of the coal in the presence of added hydrogen, thereby forming a mixture of solvent, dissolved coal and coal residue. The mixture from dissolver 20 is cooled if desired in zone 35 to a temperature lower than the temperature of the dissolver and preferably, at least below 425 OC. The cooled mixture is then hydrocracked in zone 40 to produce a relatively low-viscosity liquid product which may be readiiy separated from any remaining coal residue.
Referring to the drawing in detail, subdivided coal is mixed with a petroleum solvent in mixing zone 10. The basic feedstock for the present invention is a solid subdivided coal such as anthracite, bituminous coal, sub-butuminous coal, lignite, or mixtures thereof. The bituminous and sub-bituminous coals are particularly preferred, and it is also preferred that said coals be ground to a particle size smaller than 100 mesh, Tyler Standard Sieve Size, although larger coal sizes may be processed. The solvent will typically comprise partially hydrogenated polycyclic aromatic hydrocarbons, generally one or more rings at least partially saturated. Examples of such materials are tetrahydronaphthalene, dihydronaphthalene, dihydroanthracene, and similar materials.Such solvents may be obtained from numerous materials, but it is particularly preferred to use a 2000C or higher-boiling petroleum fraction, such as a topped naphthenic crude or a vacuum residua. Asphaltic or naphthenic crudes are generally higher in aromatics and naphthenes in comparison to paraffinic base crudes. As a result, such crudes are preferable over the paraffinic crudes for use as solvents in the present invention, although since such crudes are also usually higher in sulfur, nitrogen and metals than paraffinic crudes, they give rise to greater problems in refining processes than said paraffinic crudes. The process of the present invention, however, is capable of tolerating the higher metals content in the hydrocracking zone without prior demetallation or pretreatment precautions.It is believed that a substantial portion of the metals of the crude are bound to or deposit upon the coal residue suspended in the liquid and thus do not tend to deposit on the cracking catalyst.
The subdivided coal is generally mixed with the solvent in a solvent-to-coai weight ratio from about 0.5:1 to 5:1, and preferably from about 1:1 to 2:1. From mixing zone 10, the slurry is fed or pumped through line 1 5 to a dissolving zone 20, wherein the slurry is heated, in the presence of added hydrogen, for example, to a temperature in the range of 4000C to 4800C, preferably 4250C to 4550C, for a length of time sufficient to substantially dissolve the coal. At least 50 weight percent, and preferably greater than 90 percent of the coal, on a moisture- and ash-free basis, is dissolved in zone 20, thereby forming a mixture of solvent, dissolved coal and insoluble solids, or coal residue. It is usually necessary that the slurry be heated to at least 400or to obtain a 50% dissolution of the coal.Further, it is usually required that the coal slurry not be heated to temperatures above 480 OC to prevent thermal cracking, which substantially reduces the overall yield of normally liquid products.
Hydrogen is also introduced into the dissolving zone through line 25 and normally comprises fresh hydrogen and recycle gas. Other reaction conditions in the dissolving zone include, for example, a residence time of 0.01 to 3 hours, preferably 0.1 to 1 hour; a pressure in the range of 35 to 680 atmospheres, preferably 100 to 340 atmospheres; and a hydrogen gas rate of 355 to 3550 liters per liter of slurry and preferably 380 to 1 780 liters per liter of slurry. The physical structuring of the dissolving zone is such that the slurry may flow upwardly or downwardly in said zone. Preferabiy, the zone is sufficiently elongated to attain plug flow conditions, which permits the process of the present invention to be practiced on a continuous basis.
The dissolving zone preferably contains no catalyst from any external source, although the mineral matter contained in the coal may have some catalytic effect. If cooling is desired, the mixture of solvent, dissolved coal and insoluble solids from dissolver 20 passes via line 30 to cooling zone 35. Cooling zone 35 will typically contain a heat exchanger or similar means whereby the effluent from dissolver 20 is cooled to a temperature below the temperature of the dissolving stage and preferably at least below 4250C. Some cooling in zone 35 may also be effected by the addition of fresh cold hydrogen, if desired. The cooled mixture of solvent, dissolved coal, insoluble solids and hydrogen is fed through line 40 into reaction zone 45 containing a hydrocracking catalyst. In the hydrocracking reaction zone, hydrogenation and cracking occur simultaneously and the higher-molecular-weight compounds are converted to lower-molecularweight compounds; the sulfur compounds are converted to hydrogen sulfide; the nitrogen compounds are converted to ammonia; and the oxygen compounds are converted to water.
Preferably, the catalytic reaction zone is a fixedbed type, but an ebullating or moving bed may also be used. The mixture of gases, liquids and insoluble solids preferably passes upwardly through the catalytic reaction zone, but may also pass downwardly.
The catalyst used in the hydrocracking zone may be any of the well-known commercially available hydrocracking catalysts. A suitable catalyst for use in the hydrocracking reaction stage comprises a hydrogenation component and a cracking component. Preferably, the hydrogenation component is supported on a refractory cracking base. Suitable bases include, for example, silica, alumina, or composites of two or more refractory oxides such as silica-alumina, silica-magnesia, silica-zirconia, silica-boria, silicatitania, silica-zirconia-titania, acid-treated clays, and the like. Acidic metal phosphates such as alumina phosphate may also be used. Preferred cracking bases comprise alumina and composites of silica and alumina. Suitable hydrogenation components are selected from Group Vl-B metals, Group VIII metals, and their oxides, or mixtures thereof.Particularly useful are cobaltmolybdenum, nickel-molybdenum, or nickeltungsten on silica-alumina supports.
It is preferred to maintain the temperature in the hydrocracking zone below 4250C, preferably in the range 3400C to 425 OC, and more preferably 3400C to 4000C, to prevent catalyst fouling. The temperature in the hydrocracking zone should be preferably maintained below the temperature in the dissolving zone by 550 to 850 C. Other hydrocracking conditions include, for example, a pressure from 35 to 680 atmospheres, preferably 70 to 200 atmospheres; a hydrogen rate of 355 to 3550 liters per liter of slurry, preferably 380 to 1 780 liters per liter of slurry; and a slurry-liquid hourly space velocity in the range 0.1 to 2, preferably 0.2 to 0.5.
Preferably, the pressures in the noncatalytic dissolving stage and the catalytic hydrocracking stage are maintained substantially equal.
Preferably, the entire effluent from the dissolver is passed to the hydrocracking zone.
However, since small quantities of water and light gases (C1-C4) are produced in the dissolver, the catalyst in the second stage is subjected to a lower hydrogen partial pressure than if these materials were absent. Since higher hydrogen partial pressures tend to increase catalyst life, it may be desired in a commercial operation to remove a portion of the water and light gases before the stream enters the hydrocracking stage.
Furthermore, interstage removal of the carbon monoxide and other oxygen-containing gases may reduce the hydrogen consumption in the hydrocracking stage due to reduction of the carbon oxides. The product effluent 50 from reaction zone 45 may be separated into a gaseous fraction 60 and a solids-liquid fraction 65 in zone 55. The gaseous fraction comprises light oils boiling below about 650C to 1 300C and normally gaseous components such as hydrogen, carbon monoxide, carbon dioxide, water and the C1-C4 hydrocarbons. Preferably, the hydrogen is separated from the other gaseous components and recycled to the hydrocracking or dissolving stages.The liquid-solids fraction 65 may be fed to solids separation zone 70 wherein the insoluble solids are separated from the liquid by conventional means, for example, hydroclones, filters, centrifugal separators, cokers and gravity settlers, or any combination of said means in zone 70.
The process of the present invention produces extremely clean, normally liquid products. The normally liquid products, that is, all of the product fractions boiling above C4, have an unusually low specific gravity; a low sulfur content of less than 0.2 weight percent; and a low nitrogen content, less than 0.5 weight percent. The advantages of the present invention will be readily apparent from consideration of the following illustrative Example.
Example A slurry consisting of 33 weight percent River King coal and 67 weight percent topped Kern River crude was passed sequentially through a first stage dissolving zone and a second stage hydrocracking zone in the presence of added hydrogen. The coal was ground to a particle size of 100 mesh (Tyler standard sieve) and had the following analysis on a weight percent dry basis: carbon 59%; hydrogen, 4.14%; nitrogen, 1.14%; oxygen, 11.03%; sulfur, 4.36%; ash, 20.33%. The crude solvent comprised a 2000C+ fraction having the following characteristics: specific gravity, 0.977; saturates, 37.3 weight percent; aromatics, 59.2 weight percent; sulfur compounds, 3.5 weight percent; metals: nickel, 67 ppm; vanadium, 33 ppm; iron, 27 ppm; a thermal gravimetric analysis (TGA) is given below for comparison with the C4+ product effluent.
Hydrogen was introduced into the dissolver at a rate of 1 780 m3 of slurry. The slurry had a residence time of approximately one hour in the dissolver which was maintained at a pressure of 1 63 atmospheres and a temperature of 4550C.
The effluent mixture of gases, liquids and solids was passed to the second stage which was maintained at 1 63 atmospheres and 400"C. The second stage contained a fixed bed of hydrocracking catalyst comprising 10 weight percent nickel and 24 weight percent tungsten on an alumina base. A space velocity in the hydrocracking stage was maintained at 0.38/hour based upon the feed slurry and a hydrogen consumption rate of 349 cubic meters per cubic meter of C4+ product was observed. The hydrocracker effluent had the following properties: Product Distribution Weight Percent C1-C3 5.4 C4+ liquid 86.8 Unreacted coal 2.8 H2S, NH3, H2O, COx 7.7 The C4+ liquid product had a specific gravity of 0.898, a sulfur content of 0.02 weight percent, and a nitrogen content of 0.23 weight percent.
Thermal gravimetric analyses of C4+ liquid are shown immediately following in comparison to the thermal gravimetric analysis of the Kern River crude.
Liquid Kern Product River Fraction Effluent Crude C4-2000C 18.7 - 2000--3450C 46.2 1 6.4 3450-5400C 30.5 45.0 5400C+ 4.5 38.0

Claims (1)

  1. Claims A process for liquefying coal, which comprises: (a) substantially dissolving subdivided coal in a crude petroleum solvent or petroleum-derived solvent at an elevated temperature in the presence of added hydrogen, said solvent containing metal contaminants, thereby forming a mixture comprising solvent, dissolved coal and insoluble solids; and (b) contacting at least a portion of said mixture in a reaction zone with hydrogen and an externally supplied hydrocracking catalyst under hydrocracking conditions to produce an effluent comprising a normally liquid portion having a reduced metal content and comprising undissolved solids containing metal from said metal contaminants.
    2. A process according to Claim 1, wherein the subdivided coal is dissolved in the presence of added hydrogen at a pressure above 35 atmospheres.
    3. A process according to Claim 1 or 2, wherein the normally liquid portion of said effluent has a specific gravity less than 1.0, a sulfur content less than 0.2 weight percent and a nitrogen content of less than 0.5 weight percent.
    4. A process according to Claim 1, 2 or 3, wherein the weight ratio of solvent to coal is in the range from 5:1 to 0.5:1 and said solvent comprises a petroleum fraction boiling above 2000C.
    4. A process according to Claim 1, 2, 3 or 4, wherein said petroleum solvent comprises an asphaltic crude fraction boiling above 2000C.
    6. A process according to any preceding claim, wherein the entire mixture comprising solvent, dissolved coal and insoluble solids is passed to said reaction zone containing hydrocracking catalyst.
    7. A process according to any one of Claims 1 to 5, wherein water and light gases are removed prior to passage of the mixture to the reaction zone containing hydrocracking catalyst.
    8. A process according to any preceding claim, wherein the subdivided coal is dissolved in the solvent at a temperature between 400or and 4800C and the hydrocracking is conducted at a temperature below 4250C and 55 to 850C lower than the dissolving temperature.
    9. A process according to Claim 8, wherein the coal is dissolved at a temperature between 4250C and 4550C and said hydrocracking is conducted at a temperature in the range from 345 to 4000C and a pressure in the range of 70 to 680 atmospheres.
    1 0. A process according to any preceding claim, wherein the hydrocracking catalyst is maintained as a fixed bed.
    11. A process according to any preceding claim, wherein said hydrocracking catalyst comprises at least one hydrogenation component selected from Group VIB and Group VIII metals and their oxides supported on an alumina support.
    1 2. A process for liquefying coal, substantially as hereinbefore described with reference to the accompanying drawing.
    1 3. A process for liquefying coal, substantially as described in the foregoing Example.
GB08127714A 1981-09-14 1981-09-14 Two stage coal liquefaction process Expired GB2105741B (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB08127714A GB2105741B (en) 1981-09-14 1981-09-14 Two stage coal liquefaction process
NL8104248A NL8104248A (en) 1981-09-14 1981-09-15 TWO STAGE PROCESS FOR LIQUIDIFYING CARBON WITH PETROLEUM DERIVED CARBON SOLVENTS.
FR8118225A FR2513652B1 (en) 1981-09-14 1981-09-28 COAL LIQUEFACTION PROCESS
BE0/206089A BE890526A (en) 1981-09-14 1981-09-28 TWO-STAGE PROCESS FOR LIQUEFACTION OF COAL USING SOLVENTS OF OIL ORIGIN

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB08127714A GB2105741B (en) 1981-09-14 1981-09-14 Two stage coal liquefaction process
NL8104248A NL8104248A (en) 1981-09-14 1981-09-15 TWO STAGE PROCESS FOR LIQUIDIFYING CARBON WITH PETROLEUM DERIVED CARBON SOLVENTS.
FR8118225A FR2513652B1 (en) 1981-09-14 1981-09-28 COAL LIQUEFACTION PROCESS
BE0/206089A BE890526A (en) 1981-09-14 1981-09-28 TWO-STAGE PROCESS FOR LIQUEFACTION OF COAL USING SOLVENTS OF OIL ORIGIN

Publications (2)

Publication Number Publication Date
GB2105741A true GB2105741A (en) 1983-03-30
GB2105741B GB2105741B (en) 1985-01-30

Family

ID=27424704

Family Applications (1)

Application Number Title Priority Date Filing Date
GB08127714A Expired GB2105741B (en) 1981-09-14 1981-09-14 Two stage coal liquefaction process

Country Status (4)

Country Link
BE (1) BE890526A (en)
FR (1) FR2513652B1 (en)
GB (1) GB2105741B (en)
NL (1) NL8104248A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3705092A (en) * 1970-12-18 1972-12-05 Universal Oil Prod Co Solvent extraction of coal by a heavy oil
US4283268A (en) * 1978-09-18 1981-08-11 Chevron Research Company Two-stage coal liquefaction process with interstage guard bed

Also Published As

Publication number Publication date
GB2105741B (en) 1985-01-30
FR2513652A1 (en) 1983-04-01
FR2513652B1 (en) 1985-07-19
NL8104248A (en) 1983-04-05
BE890526A (en) 1982-01-18

Similar Documents

Publication Publication Date Title
US4082643A (en) Process for the liquefaction of coal and separation of solids from the product stream
US4354922A (en) Processing of heavy hydrocarbon oils
US4334976A (en) Upgrading of residual oil
US4411767A (en) Integrated process for the solvent refining of coal
US4389303A (en) Process of converting high-boiling crude oils to equivalent petroleum products
US4325801A (en) Three-stage coal liquefaction process
US3143489A (en) Process for making liquid fuels from coal
US4422922A (en) Coal liquefaction and hydroprocessing of petroleum oils
US4081360A (en) Method for suppressing asphaltene formation during coal liquefaction and separation of solids from the liquid product
US4330389A (en) Coal liquefaction process
JPS5853983A (en) Coal liquification
US4317711A (en) Coprocessing of residual oil and coal
US4391699A (en) Coal liquefaction process
US4264429A (en) Two-stage coal liquefaction process with process-derived solvent
US4325800A (en) Two-stage coal liquefaction process with interstage guard bed
US4330393A (en) Two-stage coal liquefaction process with petroleum-derived coal solvents
US4331531A (en) Three-stage coal liquefaction process
US4330390A (en) Two-stage coal liquefaction process with petroleum-derived coal solvents
US4347116A (en) Two-stage coal liquefaction
US4350582A (en) Two-stage coal liquefaction process with process-derived solvent
US4255248A (en) Two-stage coal liquefaction process with process-derived solvent having a low heptane-insolubiles content
US4264430A (en) Three-stage coal liquefaction process
US4354920A (en) Coal liquefaction process
US4510038A (en) Coal liquefaction using vacuum distillation and an external residuum feed
US4358359A (en) Two-stage coal liquefaction process with process-derived solvent having a low heptane-insolubles content

Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee