US2814586A - Process for refining hydrocarbons with boron trifluoride and oxygen - Google Patents
Process for refining hydrocarbons with boron trifluoride and oxygen Download PDFInfo
- Publication number
- US2814586A US2814586A US517365A US51736555A US2814586A US 2814586 A US2814586 A US 2814586A US 517365 A US517365 A US 517365A US 51736555 A US51736555 A US 51736555A US 2814586 A US2814586 A US 2814586A
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- US
- United States
- Prior art keywords
- oxygen
- hydrocarbon
- oil
- sludge
- hydrocarbons
- 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
- 229930195733 hydrocarbon Natural products 0.000 title claims description 56
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 56
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 29
- 229910052760 oxygen Inorganic materials 0.000 title claims description 29
- 239000001301 oxygen Substances 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 26
- 238000007670 refining Methods 0.000 title claims description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 title description 4
- 229910015900 BF3 Inorganic materials 0.000 title description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 37
- 150000003464 sulfur compounds Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 5
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 5
- 150000002927 oxygen compounds Chemical class 0.000 claims description 5
- 239000010802 sludge Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 17
- 239000003209 petroleum derivative Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- -1 sulfur compounds Chemical class 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
- C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
- C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
Definitions
- This invention relates to a process for refining hydrocarbon materials containing one or more undesirable rimpurities. More particularly, the invention relates to a process for removing non-hydrocarbons, such as sulfur compounds, from admixtures thereof with hydrocarbons, such as petroleum oil fractions containing sulfur compounds.
- a refined, stable hydrocarbon product can be obtained from a mixture of a hydrocarbon material and one or more non-hydrocarbon materials by treating the mixture with BF, and simultaneously, or subsequently, contacting the BF treated hydrocarbon material with oxygen.
- a hydrocarbon material mixed with one or more non-hydrocarbon materials is treated with BB, and is subsequently contacted with oxygen.
- the B1 treatment converts a large proportion of the non-hydrocarbons to materials insoluble in the hydrocarbon material.
- the insoluble material separates from the body of the hydrocarbon material as a sludge.
- the BF treated hydrocarbon material is then contacted with oxygen such as by bubbling an oxygen-containing gas, preferably air, through the hydrocarbon material.
- oxygen-containing gas preferably air
- BF and oxygen are simultaneously contacted with the hydrocarbon material being treated.
- the BE, and oxygen may be admixed prior to their introduction into the hydrocarbon material, or they may be introduced simultaneously but separately therein.
- a hydrocarbon material containing non-hydrocarbons is treated with BF to form a sludge.
- the so-formed sludge is separated such as by decanting or centrifuging.
- the separated rhydrocarbon material containing the soluble portion of the reaction products of BF and the non-hydrocarbons is then contacted with oxygen such as by bubbling air therethrough.
- oxygen such as by bubbling air therethrough.
- additional sludge is formed due to the conversion of the soluble-reaction products of BF, and non-hydrocarbons to insoluble materials. 'This sludge is thereafter separated from the hydrocarbon material by any convenient means, such as by decanting or centrifuging.
- the washing step is conveniently accomplished by intimately contacting water with the hydrocarbon materials continuously in an extraction tower, or batchwise by mechanical mixing, allowing the Water to form a separate phase, and decanting.
- the drying step is conveniently accomplished by passing an inert gas such as flue gas or nitrogen through the washed hydrocarbon materials, preferably at an elevated temperature, but other drying means known to .the art can be employed if desired.
- the quantity of non-hydrocarbons present in such fractions will generally be from about .05 to 8% and usually from .1 to 2%.
- Such petroleum hydrocarbon oils may have been subjected to various treatments prior to their use in the process of the invention. For example, oils which have been subjected to solvent extraction, acid treatment, clay contacting, and the like, can advantageously be employed.
- the quantity of BF to employ is advantageously varied in accordance with the quantity of non-hydrocarbons present in the hydrocarbon material being treated.
- the quantity of BF should be maintained within the range of from 0.01 to 10% by Weight of the oil, and usually will be within the range of from 0.05 to 5% by weight of the oil.
- the quantity of oxygen to employ does not appear critical, but an excessive quantity should be avoided to prevent oxidation of the hydrocarbons. From about 2 to 8 volumes of oxygen (measured at standard temperature and pressure) per volume of oil, or from about 10 to 40 volumes of air (measured at standard temperature and pressure) per volume of oil, gives good results. In general, a suflicient quantity of oxygen should be used so that further addition thereof does not precipitate any significant quantity of sludge.
- the oxygen is conveniently introduced by bubbling air through the material being treated, However, other sources of'oxygen such as substantially pure oxygen or oxygen admixed with an inert gas such as nitrogen or carbon dioxide can be used.
- the time, temperature and pressure to employ during the BE, and/ or oxygen contacting do not appear critical, except that oxygen should not be contacted with the oil for an excessive time.
- the pressure can be sub-atmos pheric, atmospheric or super-atmospheric, but is advantageously maintained in the range of from atmospheric to 200 p. s. i. g.
- ambient temperature is used, but a relatively low temperature, say about 30 F.,
- An ele vated temperature is advantageously used, for example, to lower the viscosity of a heavy oil for the BF and/or oxygen contacting.
- a lubricating oil containing about 0.4% by weight sulfur compounds (calculated as sulfur) is contacted with about 1% by weight BF for about 10 minutes at ambient temperature.
- a quantity of sludge is formed by this treatment. Air is then bubbled, for about 30 minutes, through the hydrocarbon material containing the sludge, about 25 volumes of air per volume of oil being used.
- An additional quantity of sludge is formed by contacting with air. Sludge is separated by centrifuging. The separated hydrocarbon material is then washed with water and dried.
- the resulting product is a refined hydrocarbon oil, stable to oxidation, having a substantially reduced quantity of sulfur compounds.
- Process for refining ahydrocarbon material con-- taining non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof which comprises contacting said hydrocarbon material with BF and oxygen and separating refined hydrocarbon material from the reaction mixture.
- Process for refining a petroleum hydrocarbon fraction containing non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof which comprises contacting said fraction with BF to form a sludge and subsequently contacting the BF treated fraction with oxygen, and separating a refined petroleum hydrocarbon fraction from the reaction mixture.
- Process for refining a petroleum hydrocarbon fraction containing non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof which comprises contacting said fraction with BF to form a sludge, separating said sludge from the reaction mixture, contacting the resulting petroleum hydrocarbon fraction with oxygen to form an additional quantity of sludge, and separating a refined petroleum hydrocarbon fraction from the reaction mixture.
- Process for refining a petroleum hydrocarbon fraction containing non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof which comprises simultaneously contacting said fraction with BF; and oxygen to form a sludge and separating a refined petroleum hydrocarbon fraction from the reaction mixture.
- Process for removing sulfur compounds from a petroleum oil which comprises contacting a petroleum oil containing sulfur compounds with from 0.01 to 10% by weight BE, and thereafter contacting the BF treated petroleum oil with from 10 to 40 volumes of air per volume of oil, and separating a petroleum oil having the reduced content of sulfur compounds from the reaction mixture.
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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
United States Patent PROCESS FOR REFINING HYDROCARBONSWITH .BORON TRIFLUORIDE AND OXYGEN Archibald P. Stuart, Media, Pa., assignor to Sun Oil Cornpany, Philadelphia, Pa., a corporation of New Jersey No Drawing. Application June 22, 1955, Serial No. 517,365
7 Claims. (Cl. 196--29) This invention relates to a process for refining hydrocarbon materials containing one or more undesirable rimpurities. More particularly, the invention relates to a process for removing non-hydrocarbons, such as sulfur compounds, from admixtures thereof with hydrocarbons, such as petroleum oil fractions containing sulfur compounds.
Various processes for removing non-hydrocarbons from hydrocarbon materials have heretofore been described. It is known, for example, to treat hydrocarbon oils with BF either alone or as a complex with another material 'such as an oxygenated organic compound. After the BF treatment such processes generally require a neutralization step, which is accomplished by washing the treated hydrocarbon material with an aqueous caustic solution :or by treating with ammonia gas. Such processes, however, while effective for removing a portion of the non-hydrocarbons have generally been unsatisfactory in that a refined product that is stable to oxidation is .not obtained.
It has now been found that a refined, stable hydrocarbon product can be obtained from a mixture of a hydrocarbon material and one or more non-hydrocarbon materials by treating the mixture with BF, and simultaneously, or subsequently, contacting the BF treated hydrocarbon material with oxygen.
In an embodiment of the process of the invention, a hydrocarbon material mixed with one or more non-hydrocarbon materials is treated with BB, and is subsequently contacted with oxygen. The B1 treatment converts a large proportion of the non-hydrocarbons to materials insoluble in the hydrocarbon material. The insoluble material separates from the body of the hydrocarbon material as a sludge. The BF treated hydrocarbon material is then contacted with oxygen such as by bubbling an oxygen-containing gas, preferably air, through the hydrocarbon material. As has been found, the quantity of sludge is increased by the oxygen contacting. The soformed sludge is then separated from the body of hydrocarbon material, and the resulting hydrocarbon material is the refined, stable hydrocarbon product of the process of the invention.
While it is not known with certainty why the process of the invention is remarkably effective when producing a highly refined stable hydrocarbon product, it is believed that while a large proportion of the reaction products of BF with non-hydrocarbons is insoluble in the hydrocarbon material, at least a portion of such reaction product is soluble in the hydrocarbon material. Such soluble reaction products are not separated in heretofore used processes and appear as impurities in the final product. In the process of the present invention, such soluble reaction products of BF are converted to insoluble materials by contacting with oxygen, and are hence con verted to sludge which is separated with the sludge formed by the initial BF treatment.
In another embodiment of the process of the inven tion, BF and oxygen are simultaneously contacted with the hydrocarbon material being treated. In this embodiment, the BE, and oxygen may be admixed prior to their introduction into the hydrocarbon material, or they may be introduced simultaneously but separately therein.
In a further embodiment of the process, a hydrocarbon material containing non-hydrocarbons is treated with BF to form a sludge. The so-formed sludge is separated such as by decanting or centrifuging. The separated rhydrocarbon material containing the soluble portion of the reaction products of BF and the non-hydrocarbons is then contacted with oxygen such as by bubbling air therethrough. On contacting with oxygen, additional sludge is formed due to the conversion of the soluble-reaction products of BF, and non-hydrocarbons to insoluble materials. 'This sludge is thereafter separated from the hydrocarbon material by any convenient means, such as by decanting or centrifuging.
After the final separation of sludge, regardless of the embodiment of the process employed, it is generally advantageous to wash the treated hydrocarbon material with water and to dry the Washed hydrocarbon material. The washing step is conveniently accomplished by intimately contacting water with the hydrocarbon materials continuously in an extraction tower, or batchwise by mechanical mixing, allowing the Water to form a separate phase, and decanting. The drying step is conveniently accomplished by passing an inert gas such as flue gas or nitrogen through the washed hydrocarbon materials, preferably at an elevated temperature, but other drying means known to .the art can be employed if desired.
Hydrocarbon materialscontaining non-hydrocarbon impurities which can be employed in the process of the invention are the petroleum hydrocarbon fractions such as gasoline, :naphtha, :kerosene, fuel :oil, gas oil and lubricating=oil fractions which contain minor quantities of nonhydrocarbons such as sulfur, oxygen or nitrogen 'compounds, or mixtures thereof. The quantity of non-hydrocarbons present in such fractions will generally be from about .05 to 8% and usually from .1 to 2%. Such petroleum hydrocarbon oils may have been subjected to various treatments prior to their use in the process of the invention. For example, oils which have been subjected to solvent extraction, acid treatment, clay contacting, and the like, can advantageously be employed.
The quantity of BF to employ is advantageously varied in accordance with the quantity of non-hydrocarbons present in the hydrocarbon material being treated. The quantity of BF should be maintained Within the range of from 0.01 to 10% by Weight of the oil, and usually will be within the range of from 0.05 to 5% by weight of the oil.
The quantity of oxygen to employ does not appear critical, but an excessive quantity should be avoided to prevent oxidation of the hydrocarbons. From about 2 to 8 volumes of oxygen (measured at standard temperature and pressure) per volume of oil, or from about 10 to 40 volumes of air (measured at standard temperature and pressure) per volume of oil, gives good results. In general, a suflicient quantity of oxygen should be used so that further addition thereof does not precipitate any significant quantity of sludge. The oxygen is conveniently introduced by bubbling air through the material being treated, However, other sources of'oxygen such as substantially pure oxygen or oxygen admixed with an inert gas such as nitrogen or carbon dioxide can be used.
The time, temperature and pressure to employ during the BE, and/ or oxygen contacting do not appear critical, except that oxygen should not be contacted with the oil for an excessive time. When the BF, and oxygen are simultaneously contacted with the oil, a time of from 5 to 60 minutes will be employed because of practical considerations. The pressure can be sub-atmos pheric, atmospheric or super-atmospheric, but is advantageously maintained in the range of from atmospheric to 200 p. s. i. g. Preferably ambient temperature is used, but a relatively low temperature, say about 30 F.,
or a relatively high temperature, say about 300 F., can
be advantageously used in some instances. An ele vated temperature is advantageously used, for example, to lower the viscosity of a heavy oil for the BF and/or oxygen contacting. When BF, is first contacted with the oil, followed by contacting with oxygen, reaction conditions substantially equivalent to those above described give good results.
To illustrate an embodiment in the process of the invention, 500 parts by weight of a lubricating oil containing about 0.4% by weight sulfur compounds (calculated as sulfur) is contacted with about 1% by weight BF for about 10 minutes at ambient temperature. A quantity of sludge is formed by this treatment. Air is then bubbled, for about 30 minutes, through the hydrocarbon material containing the sludge, about 25 volumes of air per volume of oil being used. An additional quantity of sludge is formed by contacting with air. Sludge is separated by centrifuging. The separated hydrocarbon material is then washed with water and dried. The resulting product is a refined hydrocarbon oil, stable to oxidation, having a substantially reduced quantity of sulfur compounds.
Theinvention claimed is:
1. Process for refining ahydrocarbon material con-- taining non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof, which comprises contacting said hydrocarbon material with BF and oxygen and separating refined hydrocarbon material from the reaction mixture.
2. Process for refining a petroleum hydrocarbon fraction containing non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof, which comprises contacting said fraction with BF to form a sludge and subsequently contacting the BF treated fraction with oxygen, and separating a refined petroleum hydrocarbon fraction from the reaction mixture.
3. Process for refining a petroleum hydrocarbon fraction containing non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof, which comprises contacting said fraction with BF to form a sludge, separating said sludge from the reaction mixture, contacting the resulting petroleum hydrocarbon fraction with oxygen to form an additional quantity of sludge, and separating a refined petroleum hydrocarbon fraction from the reaction mixture.
4. Process for refining a petroleum hydrocarbon fraction containing non-hydrocarbons selected from the group consisting of sulfur compounds, oxygen compounds, nitrogen compounds, and mixtures thereof, which comprises simultaneously contacting said fraction with BF; and oxygen to form a sludge and separating a refined petroleum hydrocarbon fraction from the reaction mixture.
5. Process for removing sulfur compounds from a petroleum oil which comprises contacting a petroleum oil containing sulfur compounds with from 0.01 to 10% by weight BE, and thereafter contacting the BF treated petroleum oil with from 10 to 40 volumes of air per volume of oil, and separating a petroleum oil having the reduced content of sulfur compounds from the reaction mixture.
6. Process according to claim 5 wherein said petroleum oil containing sulfur compounds is a lubricating oil.
7. Process according to claim 5 wherein said petroleum oil containing sulfur compounds is gasoline.
References Cited in the file of this patent UNITED STATES PATENTS Burk Mar. 7, 1944 Axe Feb. 25, 1947 OTHER REFERENCES
Claims (1)
1. PROCESS FOR REFINING A HYDROCARBON MATERIAL CONTAINING NON-HYDROCARBONS SELECTED FROM THE GROUP CONSISTING OF SULFUR COMPOUNDS, OXYGEN COMPOUNDS, NITROGEN COMPOUNDS, AND MIXTURE THEREOF, WHICH COMPRISES CONTACTING SAID HYDROCARBON MATERIAL WITH BF3 AND OXYGEN AND SEPARATING REFINED HYDROCARBON MATERIAL FROM THE REACTION MIXTURE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US517365A US2814586A (en) | 1955-06-22 | 1955-06-22 | Process for refining hydrocarbons with boron trifluoride and oxygen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US517365A US2814586A (en) | 1955-06-22 | 1955-06-22 | Process for refining hydrocarbons with boron trifluoride and oxygen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2814586A true US2814586A (en) | 1957-11-26 |
Family
ID=24059512
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US517365A Expired - Lifetime US2814586A (en) | 1955-06-22 | 1955-06-22 | Process for refining hydrocarbons with boron trifluoride and oxygen |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2814586A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2343841A (en) * | 1943-06-08 | 1944-03-07 | Standard Oil Co | Removal of aromatics, sulphur, or unsaturates from hydrocarbons |
| US2416465A (en) * | 1943-11-16 | 1947-02-25 | Phillips Petroleum Co | Treatment of hydrocarbons with boron fluoride hydrate |
-
1955
- 1955-06-22 US US517365A patent/US2814586A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2343841A (en) * | 1943-06-08 | 1944-03-07 | Standard Oil Co | Removal of aromatics, sulphur, or unsaturates from hydrocarbons |
| US2416465A (en) * | 1943-11-16 | 1947-02-25 | Phillips Petroleum Co | Treatment of hydrocarbons with boron fluoride hydrate |
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