US2594044A - Solvent extraction of oils with dimethylammonium dimethylcarbamate - Google Patents
Solvent extraction of oils with dimethylammonium dimethylcarbamate Download PDFInfo
- Publication number
- US2594044A US2594044A US144193A US14419350A US2594044A US 2594044 A US2594044 A US 2594044A US 144193 A US144193 A US 144193A US 14419350 A US14419350 A US 14419350A US 2594044 A US2594044 A US 2594044A
- Authority
- US
- United States
- Prior art keywords
- dimethylammonium
- solvent
- extraction
- oils
- dimethylcarbamate
- 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
- JIYXHCMRGZVYMA-UHFFFAOYSA-N dimethylcarbamic acid;n-methylmethanamine Chemical compound C[NH2+]C.CN(C)C([O-])=O JIYXHCMRGZVYMA-UHFFFAOYSA-N 0.000 title claims description 14
- 239000003921 oil Substances 0.000 title claims description 8
- 238000000638 solvent extraction Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims description 18
- 238000000605 extraction Methods 0.000 claims description 11
- 238000007670 refining Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 8
- 239000002480 mineral oil Substances 0.000 claims description 6
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 239000003209 petroleum derivative Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000000295 fuel oil Substances 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 230000005484 gravity Effects 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000003464 sulfur compounds Chemical class 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- KMNQFZQGWMMCIO-UHFFFAOYSA-N azanium;n,n-dimethylcarbamate Chemical compound [NH4+].CN(C)C([O-])=O KMNQFZQGWMMCIO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/20—Nitrogen-containing compounds
Definitions
- This invention relates to the treatment of mineral oils and more particularly to refining petroleum distillates by solvent extraction processes employing dimethylammonium dimethylcarbamate as an extractive solvent.
- the processes of the invention are applicable to mineral oils and to all petroleum distillates, including gasoline, kerosene, fuel oil, and lubricating oil.
- the processes are particularly useful for the treatment of distillates obtained as a result of catalytic cracking and especially catalytically cracked fuel oil containing unsaturated compounds and sulfur compounds.
- the extraction is suitably carried out according to methods well known in the petroleum in dustry for effecting liquid-liquid contact in $01 vent extraction processes.
- the oil may be treated with one or more successive portions of the solvent, which portions may vary in size ac: cording to the degree of refining required' Al ternatively, the operation may be continuous by causing the oil and the solvent to flow countercurrent, as for example, thru a vertical extraction tower.
- the temperature at which the extraction step is carried out may be varied depending on the physical and chemical characteristics of the material treated. The use of ordinary or ambient temperatures gives good results in most cases. In some cases, better results will be obtained using lower temperatures, say down to 32 F. or below, while in others, as when the distillate is viscous or solid at normal temperatures, the extraction may suitably be carried out at temperatures up to the atmospheric boiling point of dimethylammonium dimethylcarbamate (140.3" E), or even higher by use of pressure.
- the mixture is separated into extract and rafflnate phases.
- the extract phase contains impurities dissolved in the main body of the solvent; the rafiinate phase contains the treated improved distillate and generally a small portion of the solvent.
- the solvent is removed from the separated phases according to conventional methods.
- the solvent may be suitably separated and recovered by distillation or alternatively by washing the phases with water in which dimethylammonium dimethylcarbamate is extremely soluble.
- a catalytically cracked 'fuel oil was extracted with dimethylammonium Charge Raliinate Extract Gravity at 60(60" F., "API 30.7 i 33.3 13.2 Spec fic Gravity at 60/60 F 0872 5 0.859 0.978 Aniline Point, F 128.5 140.9 -4 Diesel Index No 39.5 46.9 -O.5 Total Su1fur,.we1ght per cent. 0.66 i 0.46 1.8
- the above data show marked refining of the fuel oil by the single treatment.
- the sulfur content was reduced and important increase in the parafiinic character of the oil is indicated by the increase in API gravity and aniline point and the decrease in specific gravity.
- the non-- parafiinic character of the extract is shown by avery low aniline number and high specific gravity.
- the Diesel index number (the aniline point multiplied by the API gravity at 60 F. and divided by 100) which is Widely used as a measure of ignition quality is much improved by the refining operation.
- a process for refining a mineral oil which comprises subjecting the oil in liquid state to extraction by means of dimethylammonium dimethylcarbamate whereby an extract phase and a raffinate phase are obtained, and separating the two phases.
- a process for refining a petroleum distillate which comprises bringing the distillate into intimate contact in the liquid state with dimethylammonium dimethylcarbamate, forming an extract phase containing extracted impurities dissolved in the dimethyl'ammonium dimethylcarbamate and a raffinate phase containing refined petroleum distillate, and separating the two phases.
- a process for refining a catalytically cracked fuel oil which comprises bringing the fuel oil into intimate contact in a liquid state with dimethylammonium dimethylcarbamate, forming an extract phase containing extracted impurities dissolved in the dimethylammonium dimethylcarbamate and a rafiinate phase containing refined fuel oil, and separating the two phases.
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
Patented Apr. 22, 1952 SOLVENT EXTRACTION F OILS WITH DIMETHYLAM'MONIUM DIMETHYLCAR- BAMATE Donald J. Loder, Wilmington, Del., assignor to E. I. du Pont de Nemours and Company, Wilmington, Del., a corporation of Delaware No Drawing.
This invention relates to the treatment of mineral oils and more particularly to refining petroleum distillates by solvent extraction processes employing dimethylammonium dimethylcarbamate as an extractive solvent.
It is known that petroleum fractions contain undesired components such as sulfur compounds and unsaturated hydrocarbons. Selective solvents have heretofore been suggested for extracting such components. Furfural and liquid sulfur dioxide are perhaps the most favorably received of such solvents. The use of these materials, however, entails process complicating factors. For example, sulfur dioxide. must be used under pressure and furfural is rather difiicult to remove from the refined materials particularly if the refined material is a light distillate.
It is an object of this invention to provide solvent extraction processes for refining mineral oils which overcome the aforementioned disadvantages of the methods used heretofore. Another obiect is to provide methods for removing undesired components from petroleum distillates. A further object is to provide processes for removing unsaturated compounds, aromatic compounds and especially sulfur compounds from petroleum distillates. A still further object is to provide methods for improving the diesel index of fuel oils. Another object is to provide solvent extraction processes in which the solvent is readily separated from the refined petroleum distillate by extraction with water. Other objects will become apparent hereinafter.
The foregoing and other objects of the invention are attained by subjecting mineral oils to extraction by means of dimethylammonium dimethylcarbamate. vention are carried out by bringing a petroleum distillate into intimate contact in the liquid state with dimethylammonium dimethylcarbamate, forming an extract phase containing impurities dissolved in dimethylammonium climethylcarbamate and a raflinate phase containing refined petroleum distillate, and separating the two phases.
The processes of the invention are applicable to mineral oils and to all petroleum distillates, including gasoline, kerosene, fuel oil, and lubricating oil. The processes are particularly useful for the treatment of distillates obtained as a result of catalytic cracking and especially catalytically cracked fuel oil containing unsaturated compounds and sulfur compounds.
Dimethylammonium dimethylcarbamate, the extractant employed in the processes of the in- Thus processes of the in Application February 14, 1950, Serial No. 144,193
3 Claims. (01. 196-4435) vention, is a water-white liquid having an amine odor and the following physical properties:
The extraction is suitably carried out according to methods well known in the petroleum in dustry for effecting liquid-liquid contact in $01 vent extraction processes. Thus, the oil may be treated with one or more successive portions of the solvent, which portions may vary in size ac: cording to the degree of refining required' Al ternatively, the operation may be continuous by causing the oil and the solvent to flow countercurrent, as for example, thru a vertical extraction tower.
The ratio of dimethylammonium diniethylcar bamate to petroleum distillate employed in the processes of the invention will be varied widely depending upon the particular distillate used,
the efiiciency of the extraction method employed and the degree of refining desired. In general, good results will be obtained with solvent:distillate volume ratios from about 0.1:1 to 41:1.
The temperature at which the extraction step is carried out may be varied depending on the physical and chemical characteristics of the material treated. The use of ordinary or ambient temperatures gives good results in most cases. In some cases, better results will be obtained using lower temperatures, say down to 32 F. or below, while in others, as when the distillate is viscous or solid at normal temperatures, the extraction may suitably be carried out at temperatures up to the atmospheric boiling point of dimethylammonium dimethylcarbamate (140.3" E), or even higher by use of pressure.
Changes in the relative solvent action of dimethylammonium dimethylcarbamate on components of petroleum distillates are realized by varying the temperature.
Following the intimate mixing of the solvent and the distillate oil in the extraction step, the mixture is separated into extract and rafflnate phases. The extract phase contains impurities dissolved in the main body of the solvent; the rafiinate phase contains the treated improved distillate and generally a small portion of the solvent.
The solvent is removed from the separated phases according to conventional methods. For example, the solvent may be suitably separated and recovered by distillation or alternatively by washing the phases with water in which dimethylammonium dimethylcarbamate is extremely soluble.
As a specific example, a catalytically cracked 'fuel oil was extracted with dimethylammonium Charge Raliinate Extract Gravity at 60(60" F., "API 30.7 i 33.3 13.2 Spec fic Gravity at 60/60 F 0872 5 0.859 0.978 Aniline Point, F 128.5 140.9 -4 Diesel Index No 39.5 46.9 -O.5 Total Su1fur,.we1ght per cent. 0.66 i 0.46 1.8
The above data show marked refining of the fuel oil by the single treatment. The sulfur content was reduced and important increase in the parafiinic character of the oil is indicated by the increase in API gravity and aniline point and the decrease in specific gravity. The non-- parafiinic character of the extract is shown by avery low aniline number and high specific gravity. The Diesel index number (the aniline point multiplied by the API gravity at 60 F. and divided by 100) which is Widely used as a measure of ignition quality is much improved by the refining operation.
In a similar test in which a West Coast gasoline: was used as the petroleum distillate, the raflinate comprised about 83.5% by volume of the recovered petroleum distillate, and the following data were obtained on the original distillate, the raffinate and the extract:
The results show especially the value of dimethylammonium dimethylcarbamate in removing sulfur compounds from the fuel.
I claim:
1. A process for refining a mineral oil which comprises subjecting the oil in liquid state to extraction by means of dimethylammonium dimethylcarbamate whereby an extract phase and a raffinate phase are obtained, and separating the two phases.
2. A process for refining a petroleum distillate which comprises bringing the distillate into intimate contact in the liquid state with dimethylammonium dimethylcarbamate, forming an extract phase containing extracted impurities dissolved in the dimethyl'ammonium dimethylcarbamate and a raffinate phase containing refined petroleum distillate, and separating the two phases.
3. A process for refining a catalytically cracked fuel oil which comprises bringing the fuel oil into intimate contact in a liquid state with dimethylammonium dimethylcarbamate, forming an extract phase containing extracted impurities dissolved in the dimethylammonium dimethylcarbamate and a rafiinate phase containing refined fuel oil, and separating the two phases.
DONALD J. LODER.
REFERENCES CITED UNITED STATES PATENTS Name Date Taveau July 2, 1918 Number
Claims (1)
1. A PROCESS FOR REFINING A MINERAL OIL WHICH COMPRISES SUBJECTING THE OIL IN LIQUID STATE TO EXTRACTION BY MEANS OF DIMETHYLAMMONIUM DIMETHYLCARBAMATE WHEREBY AN EXTRACT PHASE AND A RAFFINATE PHASE ARE OBTAINED, AND SEPARATING THE TWO PHASES.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US144193A US2594044A (en) | 1950-02-14 | 1950-02-14 | Solvent extraction of oils with dimethylammonium dimethylcarbamate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US144193A US2594044A (en) | 1950-02-14 | 1950-02-14 | Solvent extraction of oils with dimethylammonium dimethylcarbamate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2594044A true US2594044A (en) | 1952-04-22 |
Family
ID=22507498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US144193A Expired - Lifetime US2594044A (en) | 1950-02-14 | 1950-02-14 | Solvent extraction of oils with dimethylammonium dimethylcarbamate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2594044A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801151A (en) * | 1953-11-04 | 1957-07-30 | Phillips Petroleum Co | Dialkylammonium dialkylcarbamates as selective solvents for carbon dioxide and hydrogen sulfide |
| US2915569A (en) * | 1957-12-23 | 1959-12-01 | Pure Oil Co | Extraction process for recovery of aromatics utilizing carbamate solvents |
| US2936283A (en) * | 1957-11-08 | 1960-05-10 | Pure Oil Co | Extraction process wherein the desired material is recovered by azeotropic distillation of the extract |
| US2954397A (en) * | 1958-09-25 | 1960-09-27 | Pure Oil Co | Stabilization of carbamate esters and extraction of aromatic hydrocarbons therewith |
| US2954396A (en) * | 1958-05-16 | 1960-09-27 | Pure Oil Co | Stabilization of carbamate esters |
| US2956088A (en) * | 1957-12-27 | 1960-10-11 | Pure Oil Co | Extraction process |
| US2963428A (en) * | 1957-11-27 | 1960-12-06 | Pure Oil Co | Extraction process |
| US2966532A (en) * | 1959-06-03 | 1960-12-27 | Monsanto Chemicals | Aliphatic hydrocarbon separation with cyanoethylated polysaccharides |
| US2978520A (en) * | 1958-06-16 | 1961-04-04 | Pure Oil Co | Process for recovery of aromatic hydrocarbons |
| US2983766A (en) * | 1957-12-03 | 1961-05-09 | Pure Oil Co | Extraction process |
| US3003005A (en) * | 1957-12-27 | 1961-10-03 | Pure Oil Co | Extraction process |
| US4379928A (en) * | 1981-03-04 | 1983-04-12 | Union Carbide Corporation | Synthesis of amides |
| US10093862B2 (en) | 2014-06-17 | 2018-10-09 | Kemira Oyj | Method for separating hydrocarbons and use of molten salt |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1271387A (en) * | 1914-07-06 | 1918-07-02 | Atlantic Refining Co | Petroleum product and process of making the same. |
-
1950
- 1950-02-14 US US144193A patent/US2594044A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1271387A (en) * | 1914-07-06 | 1918-07-02 | Atlantic Refining Co | Petroleum product and process of making the same. |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801151A (en) * | 1953-11-04 | 1957-07-30 | Phillips Petroleum Co | Dialkylammonium dialkylcarbamates as selective solvents for carbon dioxide and hydrogen sulfide |
| US2936283A (en) * | 1957-11-08 | 1960-05-10 | Pure Oil Co | Extraction process wherein the desired material is recovered by azeotropic distillation of the extract |
| US2963428A (en) * | 1957-11-27 | 1960-12-06 | Pure Oil Co | Extraction process |
| US2983766A (en) * | 1957-12-03 | 1961-05-09 | Pure Oil Co | Extraction process |
| US2915569A (en) * | 1957-12-23 | 1959-12-01 | Pure Oil Co | Extraction process for recovery of aromatics utilizing carbamate solvents |
| US2956088A (en) * | 1957-12-27 | 1960-10-11 | Pure Oil Co | Extraction process |
| US3003005A (en) * | 1957-12-27 | 1961-10-03 | Pure Oil Co | Extraction process |
| US2954396A (en) * | 1958-05-16 | 1960-09-27 | Pure Oil Co | Stabilization of carbamate esters |
| US2978520A (en) * | 1958-06-16 | 1961-04-04 | Pure Oil Co | Process for recovery of aromatic hydrocarbons |
| US2954397A (en) * | 1958-09-25 | 1960-09-27 | Pure Oil Co | Stabilization of carbamate esters and extraction of aromatic hydrocarbons therewith |
| US2966532A (en) * | 1959-06-03 | 1960-12-27 | Monsanto Chemicals | Aliphatic hydrocarbon separation with cyanoethylated polysaccharides |
| US4379928A (en) * | 1981-03-04 | 1983-04-12 | Union Carbide Corporation | Synthesis of amides |
| US10093862B2 (en) | 2014-06-17 | 2018-10-09 | Kemira Oyj | Method for separating hydrocarbons and use of molten salt |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2594044A (en) | Solvent extraction of oils with dimethylammonium dimethylcarbamate | |
| US2343841A (en) | Removal of aromatics, sulphur, or unsaturates from hydrocarbons | |
| US2276526A (en) | Process for refining hydrocarbon oils | |
| US2769768A (en) | Method of removing high molecular weight naphthenic acids from hydrocarbon oils | |
| US2450588A (en) | Desulfurization of oils | |
| US1844362A (en) | Process of producing an antiknock compound | |
| US2451025A (en) | Method of refining lubricating oils | |
| US2906693A (en) | Pretreatment of catalytic cracking feed to remove metals | |
| US2745792A (en) | Hydrocarbon treating process | |
| US3309309A (en) | Denitrification of hydrocarbons | |
| US3052627A (en) | Removing metals with a 2-pyrrolidone-alcohol mixture | |
| US2414252A (en) | Solvent separation of hydrocarbons | |
| US2161567A (en) | Solvent refining of oil | |
| US3228870A (en) | Treatment of asphaltic crude oils | |
| US2288853A (en) | Hydrocarbon oil treatment | |
| US2115960A (en) | Method of treating mineral oils | |
| US2953523A (en) | Chemical process | |
| US2401852A (en) | Solvent extraction | |
| US3284347A (en) | Solvent extraction of hydrocarbons with hexafluoroisopropyl and trifluoroethyl alcohols | |
| US2092199A (en) | Solvent fractionation of hydrocarbon oils | |
| US3567627A (en) | Lube extraction with an ethyl glycolate solvent | |
| US3565795A (en) | Lube extraction with hydroxy ketones | |
| US3349028A (en) | Continuous solvent extraction of decant, cycle and gas oils | |
| US2226092A (en) | Solvent refining of hydrocarbon oil | |
| US2726989A (en) | Heater oil purification using sulfur dioxide and a halogen |