US2213272A - Treatment of liquid hydrocarbon products - Google Patents
Treatment of liquid hydrocarbon products Download PDFInfo
- Publication number
- US2213272A US2213272A US187661A US18766138A US2213272A US 2213272 A US2213272 A US 2213272A US 187661 A US187661 A US 187661A US 18766138 A US18766138 A US 18766138A US 2213272 A US2213272 A US 2213272A
- Authority
- US
- United States
- Prior art keywords
- treatment
- liquid
- products
- coal
- liquid hydrocarbon
- 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 - Lifetime
Links
- 239000007788 liquid Substances 0.000 title description 20
- 229930195733 hydrocarbon Natural products 0.000 title description 13
- 150000002430 hydrocarbons Chemical class 0.000 title description 13
- 239000004215 Carbon black (E152) Substances 0.000 title description 3
- 239000003245 coal Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- 239000002641 tar oil Substances 0.000 description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000001131 transforming effect Effects 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 244000007645 Citrus mitis Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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
- C10G19/00—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C1/00—Working-up tar
- C10C1/20—Refining by chemical means inorganic or organic compounds
-
- 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
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/02—Non-metals
-
- 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
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/04—Metals, or metals deposited on a carrier
Definitions
- This invention relates to the treatment of liquid hydrocarbon products and in particular to the treatment of tar oils and other liquid products obtained from coal.
- the tar oils obtained contain quantities of oxygen-containing compounds mainly of phenolic character.
- the present invention is concerned broadly with the treatment of these tar oils and otherliquid products obtained from coal, for instance the products obtained by extraction of coal with organic solvents, with the object of forming products consisting substantially of hydrocarbons.
- liquid coal products are subjected to treatment with metals or metal compounds, and in particular with oxides or hydroxides of alkaline earth metals or alkali metals.
- the treatment of such liquid coal products with an oxide or hydroxide of an alkaline earth metal or of an alkali metal results in the production of salts by reaction between the oxide or hydroxide and phenolic compounds contained in the material treated, and decomposition of these salts produces hydrocarbons, the alkali metal or alkaline earth metal being recovered usually in the form of a carbonate.
- oxygencontaining compounds contained in the liquid coal product treated are transformed into hydrocarbons without the utilisation of hydrogen or any other reducing gas.
- sulphur contained in the liquid coal product combines with the alkali metal or alkaline earth metal and may be removed from the liquid coal product by separation of the salts formed.
- Formation of the salt can be efiected at room temperatures but, if desired, higher temperatures may be employed to accelerate the reaction, e. g. temperatures of 50-100 C. or more.
- Decomposition of the salt formed is preferably effected at as low a temperature as is possible in order to avoid decomposition or polymerisation of the hydrocarbons formed. In practice it is convenient to efiect the decomposition during a distillation operation, for instance when fractionating the liquid coal product.
- the salt produced by treating the liquid coal product with the alkali metal or alkaline earth metal oxide or hydroxide may, if desired, be separated from the liquid coal product before being decomposed.
- the decomposition may be effected in the liquid coal product itself and thus the process of the invention may consist of mixing the liquid coal product with the oxide or hydroxide chosen, e. g. lime or caustic soda, and subjecting the resulting mixture to a sufficiently high temperature to produce hydrocarbons from oxygen-containing compounds present.
- the oxide or hydroxide chosen, e. g. lime or caustic soda
- metals such as zinc and copper which when heated with the liquid coal products cause decomposition of oxygen containing organic compounds present with the formation of hydrocarbons.
- Metal oxides formed as a result of such an operation may be regenerated by reduction, particularly with a reducing gas which is cheaper than hydrogen; this may be, for instance, carbon monoxide, water gas or methane according to the processes being operated. Alternatively, the metal oxide may be reduced by heating with carbon. 1
- Example 1 Tar oil produced by the low temperature distillation of coal is mixed with lime in the proportion of 5 to 6 parts by weight of lime per 100 parts of tar oil. The mixture is heated to a temperature of 70-75 C. and maintained at this temperature for an hour, during which the mixture is maintained in agitation.
- the tar oil is then subjected to fractional distillation to separate it into high and low boiling fractions and during the later stages of distillation the calcium salts present in the tar oil are decomposed to produce hydrocarbons which distil over.
- the semi-solid residue from the fractional distillation is burnt to remove carbonaceous matter and the zinc oxide thus obtained is reduced by treatment with water-gas.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
Patented Sept. 3, 1940 UNITED STATES TREATBIENT OF LIQUID HYDROCARBON PRODUCTS Henry Dreyfus, London, England No Drawing. Application January 29, 1938, Se-
rial No. 187,661. 1937 2 Claims.
This invention relates to the treatment of liquid hydrocarbon products and in particular to the treatment of tar oils and other liquid products obtained from coal.
In the distillation of coal both by low temperature and high temperature processes the tar oils obtained contain quantities of oxygen-containing compounds mainly of phenolic character. The present invention is concerned broadly with the treatment of these tar oils and otherliquid products obtained from coal, for instance the products obtained by extraction of coal with organic solvents, with the object of forming products consisting substantially of hydrocarbons.
According to the invention liquid coal products are subjected to treatment with metals or metal compounds, and in particular with oxides or hydroxides of alkaline earth metals or alkali metals. The treatment of such liquid coal products with an oxide or hydroxide of an alkaline earth metal or of an alkali metal results in the production of salts by reaction between the oxide or hydroxide and phenolic compounds contained in the material treated, and decomposition of these salts produces hydrocarbons, the alkali metal or alkaline earth metal being recovered usually in the form of a carbonate. In this manner oxygencontaining compounds contained in the liquid coal product treated are transformed into hydrocarbons without the utilisation of hydrogen or any other reducing gas. Furthermore, sulphur contained in the liquid coal product combines with the alkali metal or alkaline earth metal and may be removed from the liquid coal product by separation of the salts formed.
Formation of the salt can be efiected at room temperatures but, if desired, higher temperatures may be employed to accelerate the reaction, e. g. temperatures of 50-100 C. or more. Decomposition of the salt formed is preferably effected at as low a temperature as is possible in order to avoid decomposition or polymerisation of the hydrocarbons formed. In practice it is convenient to efiect the decomposition during a distillation operation, for instance when fractionating the liquid coal product.
The salt produced by treating the liquid coal product with the alkali metal or alkaline earth metal oxide or hydroxide may, if desired, be separated from the liquid coal product before being decomposed. On the other hand the decomposition may be effected in the liquid coal product itself and thus the process of the invention may consist of mixing the liquid coal product with the oxide or hydroxide chosen, e. g. lime or caustic soda, and subjecting the resulting mixture to a sufficiently high temperature to produce hydrocarbons from oxygen-containing compounds present. There may also be used instead of alkali metal or alkaline earth metal oxides or In Great Britain February 3,
hydroxides, metals such as zinc and copper which when heated with the liquid coal products cause decomposition of oxygen containing organic compounds present with the formation of hydrocarbons. Metal oxides formed as a result of such an operation may be regenerated by reduction, particularly with a reducing gas which is cheaper than hydrogen; this may be, for instance, carbon monoxide, water gas or methane according to the processes being operated. Alternatively, the metal oxide may be reduced by heating with carbon. 1
The following examples illustrate the process of the invention:
Example 1 Tar oil produced by the low temperature distillation of coal is mixed with lime in the proportion of 5 to 6 parts by weight of lime per 100 parts of tar oil. The mixture is heated to a temperature of 70-75 C. and maintained at this temperature for an hour, during which the mixture is maintained in agitation.
The tar oil is then subjected to fractional distillation to separate it into high and low boiling fractions and during the later stages of distillation the calcium salts present in the tar oil are decomposed to produce hydrocarbons which distil over.
Erwmple 2 Tar oil produced by the low temperature distillation of coal is mixed with finely powdered metallic zinc in the proportion of 3 to 4 parts by Weight of zinc per 100 parts of tar oil and the mixture is immediately subjected to fractional distillation. During the distillation process the metallic zinc reacts with oxygen-containing compounds contained in the tar oil forming metal compounds which decompose subsequently to produce hydrocarbons.
The semi-solid residue from the fractional distillation is burnt to remove carbonaceous matter and the zinc oxide thus obtained is reduced by treatment with water-gas.
Having described my invention, what I desire to secure by Letters Patent is:
1. Process for the treatment of crude liquid coal products, which comprises transforming phenolic compounds contained therein into liquid hydrocarbons Without utilization of hydrogen by heating the crude liquid coal products with a finely divided metallic zinc.
2. Process for the treatment of crude liquid coal products, which comprises transforming phenolic compounds contained therein into liquid hydrocarbons without utilization of hydrogen by subjecting the crude liquid coal products to distillation in the presence of finely divided metallic zinc.
HENRY DREYFUS.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2213272X | 1937-02-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2213272A true US2213272A (en) | 1940-09-03 |
Family
ID=10901351
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US187661A Expired - Lifetime US2213272A (en) | 1937-02-03 | 1938-01-29 | Treatment of liquid hydrocarbon products |
Country Status (1)
Country | Link |
---|---|
US (1) | US2213272A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5236576A (en) * | 1990-10-31 | 1993-08-17 | Gilman Michael G | Carbonaceous mineral refining process |
-
1938
- 1938-01-29 US US187661A patent/US2213272A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5236576A (en) * | 1990-10-31 | 1993-08-17 | Gilman Michael G | Carbonaceous mineral refining process |
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