CA1171013A - Process for hydrogenation of coal, heavy oil, bitumen and the like - Google Patents
Process for hydrogenation of coal, heavy oil, bitumen and the likeInfo
- Publication number
- CA1171013A CA1171013A CA000405046A CA405046A CA1171013A CA 1171013 A CA1171013 A CA 1171013A CA 000405046 A CA000405046 A CA 000405046A CA 405046 A CA405046 A CA 405046A CA 1171013 A CA1171013 A CA 1171013A
- Authority
- CA
- Canada
- Prior art keywords
- temperature
- pressure
- sludge
- hydrogenation
- process gas
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/002—Production 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/06—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation
- C10G1/065—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation in the presence of a solvent
Abstract
ABSTRACT
A process for hydrogenation of carbonaceous materials such as coal, heavy oil, bitumen, and the like comprising a) contacting said carbonaceous materials with hydrogen and a hydrogenation catalyst at a temperature of 250°C to 550°C and a pressure of 50 to 700 bar, whereby gaseous products, liquid products and a solid sludge are formed, b) separating said sludge from said products at a temperature up to 100 K lower than the hydrogenation temperature of step a), c) stripping said sludge of any liquid products contained therein by contacting said sludge with a process gas comprising at least a portion of said gaseous products at a temperature of 20°C to 300°C and a pressure of 10 to 300 bar, whereby a process gas stream containing said liquid product is formed, and d) separating said liquid products from said process gas stream.
A process for hydrogenation of carbonaceous materials such as coal, heavy oil, bitumen, and the like comprising a) contacting said carbonaceous materials with hydrogen and a hydrogenation catalyst at a temperature of 250°C to 550°C and a pressure of 50 to 700 bar, whereby gaseous products, liquid products and a solid sludge are formed, b) separating said sludge from said products at a temperature up to 100 K lower than the hydrogenation temperature of step a), c) stripping said sludge of any liquid products contained therein by contacting said sludge with a process gas comprising at least a portion of said gaseous products at a temperature of 20°C to 300°C and a pressure of 10 to 300 bar, whereby a process gas stream containing said liquid product is formed, and d) separating said liquid products from said process gas stream.
Description
~ 17~0~3 TITLE: PROCESS OF HYDROGENATION OF COAL, HEAVY OIL, BITUMEN AND THE LIKE
~rhis invention relates to the liquid-phase or combined liquid- and gas-phase hydrogenation o~ coal, heavy oil, bitumen and similar materials such as the residues from the pot distillation or vacuum distillation of crude oil. More particularly, the invention relates to the separation and recovery of liquid products ~rom the residues remaining after primary separation of products immediately after the hydrogenation step in such processes.
..
It is known, for example from ~. Kronig, " m e : Catalytic Pressure Hydrogenation of Coal, Tars and Mineral Oils", Berlin~Gottingen/Heidelberg (1950), that coal, heavy oils and bitumen as well as other re~idual carbonaceous materials can be converted into low boiling hydrocarbon mixtures by a process wherein they are mixed with hydrogen and a catalyst, and optionally also with a filurrying oil derived ~rom the product, and this mixture is heated under a pressure of 500-700 bar, pre~erably 100-325 bar, in a heater to a temperature of 200-500C, : ' :
, preferably 350-450C. AEter passing through a preheater the mixture is fed from below through a reactor system in which the hydrocracking reaction takes place at temperatures between 250 and 550C, preferably 38~-400C, which produces cleaving of larger molecules as well as partial desulfurization, denitrification and deoxygenation.
The preferred catalysts are single-pass catalysts.
In the hydroyenation of coal these are for example molybdic acid, tin oxalate/ammonium chloride, sayer-process aluminas and red mud. For the hydrogenation of heavy oil and bitumen, catalysts are used which contain catalytically active metal compounds, for example, of tungsten, molybdenum, lead, tin, chromium, cobalt and nickel, and especially of iron, on a carrier such as activated carbon or especially coke. The catalysts are used in proportions up to 10 %, by weight, preferably 1 to 6 %~ by weight, calculated on the startin~ material.
Especially ef~ec~ive catalysts are iron compounds which are converted into iron sulfide under the reaction conditions, e.g., iron sulfate, in amounts of 2 to 7 ~ by weight on activated carbon or coke.
From the top of the reactor the reaction mixture is taken to a hot separator, from the top of which gaseous and vapor-phase reaction products are withdrawn. From the bottom of the separator the unreacted starting 3 ~ 3 material, asphaltenes, and catalyst, as well as a certain heavy and middle oil fraction are witlldrawn as a hot sludge. The hot separator, which may also comprise a system of several separators connected in series, i~
operated at temperatures up to 100 K, preferably 20 to 40 K, below the reactor temperature.
me gaseous and vapor-phase products withdrawn from the top of the hot separator are either taken to a cold depressurization system and then to further operations, or are immediately fed under the prevailing reaction pressure into the top of a system of reactors in which the gaseous or vapor-phase products are further desulfurized, denitrified, deoxygenated as well as cleaved on a fixed-bed catalyst (cf. W. Urban, "Petroleum Processing in the Scholvener 300 Atmosphere Combination Hydrogenation Reactor", Erdol und Kohle, 8 ~1955), pages 780-782). me products of this "combination hydrogenation" are also taken to a co:Ld separator system and thence to further processing.
It is known to subject the material withdrawn from the bottom of the hot separator to a vacuum distillation or a destructive distillation to increase the yield of liquid product. It can also be recycled in part to the liquid phase reactor. This recycling has the disadvantage that the asphaltene level in the reactor increases, which increases the coking tendency of the ,.
reaction material. Distillation and destructive distillation are difficult to control because of the particular type of sludges produced in this process, and, for the most part only a limited yield of liquid products is possible even from the principal method, destructive distillation.
Therefore, a need has continued to exist for a process for recovering liquid products from the residues from hydrogenation oE coal, heavy oil and the like, which does not sufer from the drawbacks of the known processes.
Accordingly, it is an object of the disclosure to provide a method or recovering liquid products from the residues from hydrogenation of coal, heavy oil, bitumen, and the like.
A further object is to increase the yield of useful products from hydrogenation of coal, heavy oil, and the like.
A further object is to use process gases in a method of recovering additional liquid products in the hydrogenation of coal, heavy oil, and the like.
Further ohjects will be apparent from the description which ~olLows.
The objects have been achieved by a process for hydrogena~ion of carbonaceous materials such as coal, heavy oil, bitumen, and the like comprising a~
contacting said carbonaceous materials with hydrogen and a hydrogenation catalyst at a temperature oE 250C to 550C and a pressure of 50 to 700 bar, whereby gaseous products, liquid products and a solid sludge are formed, b) separating said sludge from said prod~cts at a temperature up to 100 K lower than the hydrogenation temperature of step a), c) stripping the sludge of any liquid products contained therein by contacting it with a process gas comprising at least a portion of the gaseous products at a temperature of 20C to 300C and a pressure of 10 to 300 bar, whereby a process gas stream containing said liquid product is formed, and d) separating said liquid products from said process gas stream.
' : Accordiny to the disclosure, the yield of liquid product of the liquid~phase or combined liquid-phase and gas-phase hydrogenation is increased by stripping a portion of the liquid constituents from the bottom product o~ the hot separator with the help of process gases. For this purpose the process gas is passed through the product at temperatures between 20 and 300C, ., preferably 50 to 200C and a pressure between lO and 300 bar, preferably 50 to 200 bar. Any gas prod~ced in the process can be used as the stripping gas. Preferably an enriched fraction, obtained by scrubbing the process gas, which contains methane, ethane, propane, butanes and pentanes, especially a gas containing a high proportion of propane, butane and/or pentane, is used.
The treatment of the hot sludge with the process gases is conveniently carried out continuously by feeding a pressure vessel connected to the hot separakor system from the top with the hot sludge and from below with the process gases. The weight ratio hot sludge : process gases is l : 10 r pre~erably l : 3; the throughput is 0.2 to 2,0 m3r preferably 0.3 to 0.6 m3 of sludge per m3 of the pressure vessel volume.
The stripping gas can be freed from the components removed from the hydrogenation residue by decreasing the pressure from lO0 to l bar, pre~erably 70 to 30 bar or by -increasing the temperature by 20 to 150 K, preferably 50 to 100 K, or a combination of both procedures, for example, an increa~se in temperature of 20 to 70 K with a decrease in the pressure from 100 to 50 bar. The liquid products are refined or cracked after reheating in the gas phase reactor; in the case of coal hydrogenation they ; can be used as a slurrying oil free of asphaltenes. lhe strippiny gas can be used again for the separation after ' ~ ,.., i 17~.0~3 increasing the pressure by means of a compressor or a blower or after cooling.
The residue from the treatment of the hot sludge with the process gases, which contains solid materials and is enriched in rnetals and asphaltenes, is removed from the process via a purging system under gas pressure and can be taken to a gasification process in order to supply'the hydrogen requirernents of the hydrogenation process.
Having generally described the inventive subject matter, a more complete understanding can be obtained by reference to certain specific examples, which are provided herein for purposes of illustration only and are not intended to be limiting unless otherwise 'specified.
'Example In a vertically oriented tubular reactor of 4.5 1 capacity, 4.0 kg/h of a residue'from the vacuum distillation of Arabian light crude oil was hydrogenated with 3 Nm3/h of hydrogen at 450C and 280 bar. To the vacuum residue was added 5 % by weight oE a finely divided coke, on which 50 g FeSO4/kg ~f coke were supported. From the hydrogenation product leavlng the top of the reactor 1.6 kg/h of hot sludge were removed in a hot separator operated at 420C.
..
~ is hot sludge was treated in a downstream vessel of 5 1 capacity, provided with integral means for separation of gas and liquid, with 4.8 kg/h of a propane-butane mixture ~propane : butane weight ratio 3 : 2) at 200 bar and 150C. The gaseous product was depre.ssurized to 40 bar, whereby 0.9 kg/h of a liquid product with a boiling point end of 520C separated. me product was free of asphaltenes and metals, its H/C ratio was 1.3;
the sulfur content was about 1.5 ~ by weight.
The æolids in the residue were increased to 28 %, by weight. The residue contained all metals which were introduced with the oil as well as the single-pass catalyst used ln the process.
Having now ully described the invention, it will be apparent to one of ordinary skill in the art that many changes and modifications can be made therto without departing from the spirit or scope of the invention as set forth herein.
:
,,,
~rhis invention relates to the liquid-phase or combined liquid- and gas-phase hydrogenation o~ coal, heavy oil, bitumen and similar materials such as the residues from the pot distillation or vacuum distillation of crude oil. More particularly, the invention relates to the separation and recovery of liquid products ~rom the residues remaining after primary separation of products immediately after the hydrogenation step in such processes.
..
It is known, for example from ~. Kronig, " m e : Catalytic Pressure Hydrogenation of Coal, Tars and Mineral Oils", Berlin~Gottingen/Heidelberg (1950), that coal, heavy oils and bitumen as well as other re~idual carbonaceous materials can be converted into low boiling hydrocarbon mixtures by a process wherein they are mixed with hydrogen and a catalyst, and optionally also with a filurrying oil derived ~rom the product, and this mixture is heated under a pressure of 500-700 bar, pre~erably 100-325 bar, in a heater to a temperature of 200-500C, : ' :
, preferably 350-450C. AEter passing through a preheater the mixture is fed from below through a reactor system in which the hydrocracking reaction takes place at temperatures between 250 and 550C, preferably 38~-400C, which produces cleaving of larger molecules as well as partial desulfurization, denitrification and deoxygenation.
The preferred catalysts are single-pass catalysts.
In the hydroyenation of coal these are for example molybdic acid, tin oxalate/ammonium chloride, sayer-process aluminas and red mud. For the hydrogenation of heavy oil and bitumen, catalysts are used which contain catalytically active metal compounds, for example, of tungsten, molybdenum, lead, tin, chromium, cobalt and nickel, and especially of iron, on a carrier such as activated carbon or especially coke. The catalysts are used in proportions up to 10 %, by weight, preferably 1 to 6 %~ by weight, calculated on the startin~ material.
Especially ef~ec~ive catalysts are iron compounds which are converted into iron sulfide under the reaction conditions, e.g., iron sulfate, in amounts of 2 to 7 ~ by weight on activated carbon or coke.
From the top of the reactor the reaction mixture is taken to a hot separator, from the top of which gaseous and vapor-phase reaction products are withdrawn. From the bottom of the separator the unreacted starting 3 ~ 3 material, asphaltenes, and catalyst, as well as a certain heavy and middle oil fraction are witlldrawn as a hot sludge. The hot separator, which may also comprise a system of several separators connected in series, i~
operated at temperatures up to 100 K, preferably 20 to 40 K, below the reactor temperature.
me gaseous and vapor-phase products withdrawn from the top of the hot separator are either taken to a cold depressurization system and then to further operations, or are immediately fed under the prevailing reaction pressure into the top of a system of reactors in which the gaseous or vapor-phase products are further desulfurized, denitrified, deoxygenated as well as cleaved on a fixed-bed catalyst (cf. W. Urban, "Petroleum Processing in the Scholvener 300 Atmosphere Combination Hydrogenation Reactor", Erdol und Kohle, 8 ~1955), pages 780-782). me products of this "combination hydrogenation" are also taken to a co:Ld separator system and thence to further processing.
It is known to subject the material withdrawn from the bottom of the hot separator to a vacuum distillation or a destructive distillation to increase the yield of liquid product. It can also be recycled in part to the liquid phase reactor. This recycling has the disadvantage that the asphaltene level in the reactor increases, which increases the coking tendency of the ,.
reaction material. Distillation and destructive distillation are difficult to control because of the particular type of sludges produced in this process, and, for the most part only a limited yield of liquid products is possible even from the principal method, destructive distillation.
Therefore, a need has continued to exist for a process for recovering liquid products from the residues from hydrogenation oE coal, heavy oil and the like, which does not sufer from the drawbacks of the known processes.
Accordingly, it is an object of the disclosure to provide a method or recovering liquid products from the residues from hydrogenation of coal, heavy oil, bitumen, and the like.
A further object is to increase the yield of useful products from hydrogenation of coal, heavy oil, and the like.
A further object is to use process gases in a method of recovering additional liquid products in the hydrogenation of coal, heavy oil, and the like.
Further ohjects will be apparent from the description which ~olLows.
The objects have been achieved by a process for hydrogena~ion of carbonaceous materials such as coal, heavy oil, bitumen, and the like comprising a~
contacting said carbonaceous materials with hydrogen and a hydrogenation catalyst at a temperature oE 250C to 550C and a pressure of 50 to 700 bar, whereby gaseous products, liquid products and a solid sludge are formed, b) separating said sludge from said prod~cts at a temperature up to 100 K lower than the hydrogenation temperature of step a), c) stripping the sludge of any liquid products contained therein by contacting it with a process gas comprising at least a portion of the gaseous products at a temperature of 20C to 300C and a pressure of 10 to 300 bar, whereby a process gas stream containing said liquid product is formed, and d) separating said liquid products from said process gas stream.
' : Accordiny to the disclosure, the yield of liquid product of the liquid~phase or combined liquid-phase and gas-phase hydrogenation is increased by stripping a portion of the liquid constituents from the bottom product o~ the hot separator with the help of process gases. For this purpose the process gas is passed through the product at temperatures between 20 and 300C, ., preferably 50 to 200C and a pressure between lO and 300 bar, preferably 50 to 200 bar. Any gas prod~ced in the process can be used as the stripping gas. Preferably an enriched fraction, obtained by scrubbing the process gas, which contains methane, ethane, propane, butanes and pentanes, especially a gas containing a high proportion of propane, butane and/or pentane, is used.
The treatment of the hot sludge with the process gases is conveniently carried out continuously by feeding a pressure vessel connected to the hot separakor system from the top with the hot sludge and from below with the process gases. The weight ratio hot sludge : process gases is l : 10 r pre~erably l : 3; the throughput is 0.2 to 2,0 m3r preferably 0.3 to 0.6 m3 of sludge per m3 of the pressure vessel volume.
The stripping gas can be freed from the components removed from the hydrogenation residue by decreasing the pressure from lO0 to l bar, pre~erably 70 to 30 bar or by -increasing the temperature by 20 to 150 K, preferably 50 to 100 K, or a combination of both procedures, for example, an increa~se in temperature of 20 to 70 K with a decrease in the pressure from 100 to 50 bar. The liquid products are refined or cracked after reheating in the gas phase reactor; in the case of coal hydrogenation they ; can be used as a slurrying oil free of asphaltenes. lhe strippiny gas can be used again for the separation after ' ~ ,.., i 17~.0~3 increasing the pressure by means of a compressor or a blower or after cooling.
The residue from the treatment of the hot sludge with the process gases, which contains solid materials and is enriched in rnetals and asphaltenes, is removed from the process via a purging system under gas pressure and can be taken to a gasification process in order to supply'the hydrogen requirernents of the hydrogenation process.
Having generally described the inventive subject matter, a more complete understanding can be obtained by reference to certain specific examples, which are provided herein for purposes of illustration only and are not intended to be limiting unless otherwise 'specified.
'Example In a vertically oriented tubular reactor of 4.5 1 capacity, 4.0 kg/h of a residue'from the vacuum distillation of Arabian light crude oil was hydrogenated with 3 Nm3/h of hydrogen at 450C and 280 bar. To the vacuum residue was added 5 % by weight oE a finely divided coke, on which 50 g FeSO4/kg ~f coke were supported. From the hydrogenation product leavlng the top of the reactor 1.6 kg/h of hot sludge were removed in a hot separator operated at 420C.
..
~ is hot sludge was treated in a downstream vessel of 5 1 capacity, provided with integral means for separation of gas and liquid, with 4.8 kg/h of a propane-butane mixture ~propane : butane weight ratio 3 : 2) at 200 bar and 150C. The gaseous product was depre.ssurized to 40 bar, whereby 0.9 kg/h of a liquid product with a boiling point end of 520C separated. me product was free of asphaltenes and metals, its H/C ratio was 1.3;
the sulfur content was about 1.5 ~ by weight.
The æolids in the residue were increased to 28 %, by weight. The residue contained all metals which were introduced with the oil as well as the single-pass catalyst used ln the process.
Having now ully described the invention, it will be apparent to one of ordinary skill in the art that many changes and modifications can be made therto without departing from the spirit or scope of the invention as set forth herein.
:
,,,
Claims (21)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for hydrogenation of carbonaceous materials such as coal, heavy oil, bitumen, and the like comprising a) contacting said carbonaceous materials with hydrogen and a hydrogenation catalyst at a temperature of 250°C to 550°C and a pressure of 50 to 700 bar, whereby gaseous products, liquid products and a solid sludge are formed, b) separating said sludge from said products at a temperature up to 100 K lower than the hydrogenation temperature of step a), c) stripping said sludge of any liquid products contained therein by contacting said sludge with a process gas comprising at least a portion of said gaseous products at a temperature of 20°C to 300°C and a pressure of 10 to 300 bar, whereby a process gas stream containing said liquid products is formed, and d) separating said liquid products from said process gas stream.
2. The process of Claim 1 wherein said hydrogenation in step a) is conducted at a temperature of 380°C to 480°C.
3. The process of Claim 1 wherein said hydrogenation in step a) is conducted at a pressure of 100 to 325 bar.
4. The process of Claim 1 wherein said sludge is separated from said products in step b) at a temperature 20 to 40 K below the hydrogenation temperature of step a).
5. The process of Claim 1 wherein said process gas contains a hydrocarbon gas selected from the group consisting of methane, ethane, propane, butanes and pentanes.
6. The process of Claim 1 wherein said process gas contains a major proportion of hydrocarbon gases selected from the group consisting of propane, butanes, and pentanes.
7. The process of Claim 1 wherein step c) is conducted at a temperature of 50°C to 200°C.
8. The process of Claim 1, wherein step c) is conducted at a pressure of 200 to 500 bar.
9. The process of Claim 1 wherein said separation in step d) is carried out by decreasing the pressure of said process gas stream containing liquid products formed in step c) to a pressure of 1 to 100 bar.
10. The process of Claim 9 wherein said pressure is decreased to a pressure of 30 to 270 bar.
11. The process of Claim 1 wherein said separation in step d) is carried out by increasing the temperature of said process gas stream containing liquid products formed in step c) by 20 to 50 K.
12. The process of Claim 11 wherein said temperature is increased by 50 to 100 K.
13. The process of Claim 1 wherein said separation in step d) is carried out by increasing the temperature of said process gas stream containing liquid products formed in step c) by 20 to 70 K and decreasing the pressure to 50 to 100 bar.
14. The process of Claim 1 wherein e) after the separation of said liquid products, said process gas stream is recycled to step c).
15. The process of Claim 14 wherein the pressure of said process gas stream is increased before it is recycled.
16. The process of Claim 14 wherein the temperature of said process gas stream is decreased before it is recycled.
17. The process of Claim 14 wherein the pressure of said process gas stream is increased and its temperature is decreased before it is recycled.
18. The process of Claim 1 wherein in step c) the weight ratio of sludge to process gas is from about 1:1 to about 10:1.
19. The process of Claim l wherein in step c) the weight ratio of sludge to process gas is about 3:1!
20. The process of Claim 1 wherein in step c) said contacting is conducted in a pressure vessel and the throughtput of said sludge is 0.2 to 2.0 m3 of sludge per m3 of volume of said pressure vessel.
21. The process of Claim 20 wherein the throughput of said sludge is 0.3 to 0.6 m3 of sludge per m3 of volume of said pressure vessel.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813123535 DE3123535A1 (en) | 1981-06-13 | 1981-06-13 | METHOD FOR HYDROGENATING COAL, HEAVY OIL, BITUMEN AND THE LIKE. |
| DEP3123535.2 | 1981-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1171013A true CA1171013A (en) | 1984-07-17 |
Family
ID=6134663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000405046A Expired CA1171013A (en) | 1981-06-13 | 1982-06-11 | Process for hydrogenation of coal, heavy oil, bitumen and the like |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0068231B1 (en) |
| CA (1) | CA1171013A (en) |
| DE (2) | DE3123535A1 (en) |
| NO (1) | NO162864C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3914057A1 (en) * | 1989-04-28 | 1990-10-31 | Ruhrkohle Ag | STRIPING OF RESIDUES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB892113A (en) * | 1957-05-08 | 1962-03-21 | Apv Co Ltd | Separation of low boiling point impurities from hydrocarbons |
| GB1527570A (en) * | 1976-12-15 | 1978-10-04 | Texaco Development Corp | Coal liquefaction |
-
1981
- 1981-06-13 DE DE19813123535 patent/DE3123535A1/en not_active Withdrawn
-
1982
- 1982-06-03 NO NO821844A patent/NO162864C/en unknown
- 1982-06-11 CA CA000405046A patent/CA1171013A/en not_active Expired
- 1982-06-11 DE DE8282105119T patent/DE3276003D1/en not_active Expired
- 1982-06-11 EP EP82105119A patent/EP0068231B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3123535A1 (en) | 1982-12-30 |
| EP0068231B1 (en) | 1987-04-08 |
| NO162864C (en) | 1990-02-28 |
| EP0068231A2 (en) | 1983-01-05 |
| DE3276003D1 (en) | 1987-05-14 |
| EP0068231A3 (en) | 1984-09-12 |
| NO821844L (en) | 1982-12-14 |
| NO162864B (en) | 1989-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |