US1686136A - And one-half to associated oil - Google Patents
And one-half to associated oil Download PDFInfo
- Publication number
- US1686136A US1686136A US1686136DA US1686136A US 1686136 A US1686136 A US 1686136A US 1686136D A US1686136D A US 1686136DA US 1686136 A US1686136 A US 1686136A
- Authority
- US
- United States
- Prior art keywords
- nitrogenous bases
- gasoline
- bases
- acid
- crude
- 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
- 239000002585 base Substances 0.000 description 58
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 50
- 239000002253 acid Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000463 material Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000004821 distillation Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003079 shale oil Substances 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- SNICXCGAKADSCV-JTQLQIEISA-N Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 4
- 229960002715 Nicotine Drugs 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000001721 combination Effects 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229930015196 nicotine Natural products 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- 229940003969 Adrenergic and dopaminergic agents combinations Drugs 0.000 description 2
- 229940001019 Aluminium antacid compound combinations Drugs 0.000 description 2
- 229940010996 Amide local anesthetic combinations Drugs 0.000 description 2
- 229940084438 Antiinfective irrigating solution combinations Drugs 0.000 description 2
- 229940095835 Beta-lactamase sensitive penicillin combinations Drugs 0.000 description 2
- 229940001469 Calcium antacid compound combinations Drugs 0.000 description 2
- 229940073688 Caries prophylactic agent combinations Drugs 0.000 description 2
- 229940060167 Enema combinations Drugs 0.000 description 2
- 229960003366 Hepatitis vaccine combinations Drugs 0.000 description 2
- 229940031471 Imidazole and triazole derivative topical antifungal combinations Drugs 0.000 description 2
- 229940000248 Intermediate-acting sulfonamide combinations Drugs 0.000 description 2
- 229940107315 Local hemostatic combinations Drugs 0.000 description 2
- 229940007270 Long-acting sulfonamide combinations Drugs 0.000 description 2
- 229940000523 Magnesium antacid compound combinations Drugs 0.000 description 2
- 229940111336 Other anti-dementia drug combinations in ATC Drugs 0.000 description 2
- 229940032419 Other antifungal combinations for topical use in ATC Drugs 0.000 description 2
- 229940106059 Other intestinal adsorbent combinations in ATC Drugs 0.000 description 2
- 229940076421 Other irrigating solution combinations in ATC Drugs 0.000 description 2
- 229940097635 Penicillins with extended spectrum combinations Drugs 0.000 description 2
- 229940001079 Platelet aggregation inhibitor combinations excl. heparin Drugs 0.000 description 2
- 229940086052 Potassium supplement combinations Drugs 0.000 description 2
- 229940084925 Salt solution combinations Drugs 0.000 description 2
- 229940000628 Short-acting sulfonamide combinations Drugs 0.000 description 2
- 229940036145 Specific immunoglobulin combinations Drugs 0.000 description 2
- 239000012445 acidic reagent Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940086715 combination drugs used in erectile dysfunction Drugs 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 229940050438 excl. combinations with cough suppressants expectorant combinations Drugs 0.000 description 2
- 229940048784 expectorant combinations excluding combinations with cough suppressants Drugs 0.000 description 2
- 229940050564 fast-acting combinations Insulins and analogs for injection Drugs 0.000 description 2
- -1 for example Substances 0.000 description 2
- 229940090613 gonadotropin combinations Drugs 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000000749 insecticidal Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 229940052038 intermediate-acting combinations Insulins and analogs for injection Drugs 0.000 description 2
- 229940052297 intermediate-acting combined with fast-acting- combinations Insulins and analogs for injection Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229940074591 local opthalmologic anesthetic combinations Drugs 0.000 description 2
- 229940051883 long-acting insulins and analogs for injection combinations Drugs 0.000 description 2
- 229940042835 lung surfactant combinations Drugs 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000003472 neutralizing Effects 0.000 description 2
- 229940064925 opium alkaloids and derivative combination cough suppressants Drugs 0.000 description 2
- 229940064347 other cough suppressant combinations in ATC Drugs 0.000 description 2
- 229940021273 other nasal preparation combinations in ATC Drugs 0.000 description 2
- 229940067531 otologic analgesic and anesthetic combinations Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940030476 topical antibiotic combinations Drugs 0.000 description 2
- 229940022453 vitamin D and analog combinations Drugs 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
Definitions
- My invention relates, ingeneral, to the treatment of hydrocarbon materials, such for example as petroleum or shale oil, for the purpose of obtaining nitrogenous bases.
- hydrocarbon materials such for example as petroleum or shale oil
- a crude gasoline which may be defined and identified as all the material boiling up to and including 450 F. approximately, and which has had no treatment except distillation. Any method commonly known in the art may be employed to secure this crude gasoline.
- gasoline is a term which is quite broadly used and may include products the properties of WlllCll vary considerably, I may state that the mate- .rial which, in carrying out my method I wish initially to secure, and which I call crude gasoline, is the first distillation from crude oil having a maximum boiling point of 450 F. approximately.
- the next step in my method is to bring it into intimate contact with a suitable reagent, preferably an acidic substance as, for example, sulphuric acid containing 25% H SO and then separate the reaction product or acidic material which contains substantially all of the nitrogenous bases in the form of sulphates.
- a suitable reagent preferably an acidic substance as, for example, sulphuric acid containing 25% H SO and then separate the reaction product or acidic material which contains substantially all of the nitrogenous bases in the form of sulphates.
- any reagent whether acidic or not may be employed, for example, other acids or combinations thereof or clays or com binations of acids and clays which also have the property of combining with nitrogenous bases, may be used. 7
- the treatment with dilute acid may be conducted in a suitable counter-flow apparatus so that the gasoline after passing through is subbases freed by the addition of an excess of caustic alkali, as, for example, caustic soda.
- This alkaline liquor is then distilled, pref: erably accompanied with injection of steam into the liquor.
- the distillate from such distillation consists, in general, of two parts, viz :nitrogenous bases insoluble in water, which being lighter than water float on it in oily form, and the water solution consisting of steam condensate and soluble nitrogenous bases.
- the nitrogenous bases herein referred to may be definedas a mixture of basic compounds ofcarbon, hydrogen and nitrogen, of which the larger proportion is composed of nitrogen bases with nitrogen in the ring; as for example, pyridine, quinoline, and pipcridine, and homologues thereof. Relatively small amounts of pyrrol and amino derivatives are also present in some cases in the crude material. Generally speaking, the product is an oily liquid, soluble in acid and insoluble in alkali. It precipitates with silieo-tungstic acid from acid solution. Analysis of the recovered nitrogenous bases by the standard silico-tuugstic method for nicotine shows from 30% to calculated as nicotine. These nitrogenous bases may be used, among other things, as an insecticide.
- the method of obtaining nitrogenous bases which comprises obtaining a crude gasoline from a hydrocarbon material; treating said crude gasoline with a reagent to form compounds with the nitrogenous bases; separating'the reaction compound; making said reaction compound alkaline; distilling the alkaline liquor containing said compounds to separate the nitrogenous bases in two types, soluble and insoluble, respectively, in water; separating said types, one from the other, in accordance with their differential solubility.
Description
Patented Oct. 2, 1928.
UNITED STATES PATENT OFFICE.
HARRY K. IHRIG, OF MARTINEZ, CALIFORNIA, ASSIGNOR OF ONE-HALF TO SUMNER E. CAMPBELL, OF ASSOCIATED, CALIFORNIA, AND ONE-HALF TO ASSOCIATED OIL COMPANY, OF SAN FRANCISCO, CALIFORNIA, A CORPORATION OF CALIFORNIA.
METHOD OF OBTAINING NITBOGENOUS BASES FROM HYDROCARBON MATERIALS.
No Drawing.
My invention relates, ingeneral, to the treatment of hydrocarbon materials, such for example as petroleum or shale oil, for the purpose of obtaining nitrogenous bases.
I have found that nitrogenous bases are present in appreciable quantity in crude gasoline ,obtained from hydrocarbon materials containing nitrogenous compounds.
By my method I first secure from the hydrocarbon material a crude gasoline, which may be defined and identified as all the material boiling up to and including 450 F. approximately, and which has had no treatment except distillation. Any method commonly known in the art may be employed to secure this crude gasoline. Although gasoline is a term which is quite broadly used and may include products the properties of WlllCll vary considerably, I may state that the mate- .rial which, in carrying out my method I wish initially to secure, and which I call crude gasoline, is the first distillation from crude oil having a maximum boiling point of 450 F. approximately.
I do not, however, confine myself to crude gasoline obtained by a simple distillation from crude oil, for it may be done by other methods, as by cracking, or distillation under pressure; and also crude gasoline may be secured from shale oil, or cracked shale oil. But in any case the crude gasoline on which I work maybe considered, as defined above, as all of the material boiling up to and including 450 F. approximately, and which has had no treatment other than distillation.
Having secured the crude gasoline, the next step in my method is to bring it into intimate contact with a suitable reagent, preferably an acidic substance as, for example, sulphuric acid containing 25% H SO and then separate the reaction product or acidic material which contains substantially all of the nitrogenous bases in the form of sulphates.
In cases where sulphur compounds are present in considerable quantities, I have found it desirable to first treat the crude or raw gasoline with a suitable solution, for example, caustic soda, to remove the majority of these sulphur compounds, prior to treatment with the reagent or dilute acid.
While I choose to employ dilute sulphuric acid as a convenient material for removing Application filed December 21, 1926. Serial No. 156,249.
nitrogenous bases, any reagent whether acidic or not may be employed, for example, other acids or combinations thereof or clays or com binations of acids and clays which also have the property of combining with nitrogenous bases, may be used. 7
The treatment with dilute acid may be conducted in a suitable counter-flow apparatus so that the gasoline after passing through is subbases freed by the addition of an excess of caustic alkali, as, for example, caustic soda.
This alkaline liquor is then distilled, pref: erably accompanied with injection of steam into the liquor. The distillate from such distillation consists, in general, of two parts, viz :nitrogenous bases insoluble in water, which being lighter than water float on it in oily form, and the water solution consisting of steam condensate and soluble nitrogenous bases.
I have found that there are two types of nitrogenous bases recoverable from gasoline,
viz :-those soluble in water and those insoluble in water. The bases insoluble in water are separated from the distillate and are dried for use. The water portion distillate, which contains an appreciable quantity of nitrogenous bases soluble in this medium, is made acid and concentrated to small volume by evaporation. To this evaporated liquor is then added an excess of alkali. When the nitrogenous bases separate and come to the top they are removed and thoroughly dried, after which theymay be subjected to distillation for purification.
The nitrogenous bases herein referred to may be definedas a mixture of basic compounds ofcarbon, hydrogen and nitrogen, of which the larger proportion is composed of nitrogen bases with nitrogen in the ring; as for example, pyridine, quinoline, and pipcridine, and homologues thereof. Relatively small amounts of pyrrol and amino derivatives are also present in some cases in the crude material. Generally speaking, the product is an oily liquid, soluble in acid and insoluble in alkali. It precipitates with silieo-tungstic acid from acid solution. Analysis of the recovered nitrogenous bases by the standard silico-tuugstic method for nicotine shows from 30% to calculated as nicotine. These nitrogenous bases may be used, among other things, as an insecticide.
I cite an example of one Way in which nitrogenous bases may be obtained by this process: 5000 gallons of crude gasoline were first passed through 15 gallons of a 20 Baum solution of caustic soda for the removal of objectionable compounds. The gasoline was next passed through 2 gallons of a solution of sulphuric acid containing 25.46% of H 80 The acid liquor which had absorbed substantiallyiall of the nitrogenous bases from the gasoline was then. removed. Examination of the acid liquor disclosed that its acidity had been reduced from 25.46% ILSO to-11.50% 11 80,. The acid liquor was then made strongly alkaline by the addition of an excess of caustic soda and distilled with steam. From this distillation there was obtained 150 c. c. of nitrogenous bases insoluble in water. An analysis of these bases showed them to contain 8.41% nitrogen and a boiling point range of 260 F. to 520 F. The water portion of the distillate was made acid and this acid liquor concentrated by evaporation to approximately 5000 c. c. This concentrated portion of the distillate. containing the sulphates of the bases soluble in water, was then made strongly alkaline, causing the free nitrogenous bases to separate and come tothe bases which comprises obtaining from a hydrocarbon material a crude gasoline; treating said crude gasoline with an acidic reagent to form compounds with the nitrogenous bases; separating the acid liquor resulting from said treatment; neutralizing the excess acid to free the nitrogenous bases, by the addition of an excess of an alkali; distilling said alkaline liquor in the presence of water to separate the nitrogenous bases in two types, soluble and insoluble, respectively, in water; removing the insoluble type; concentrating the liquor containing the soluble type; adding to said concentrated liquor an excess of alkali; and separating the nitrogenous bases therefrom.
2. The method of obtaining nitrogenous bases which comprises obtaining a crude gasoline from a hydrocarbon material; treating said crude gasoline with a reagent to form compounds with the nitrogenous bases; separating'the reaction compound; making said reaction compound alkaline; distilling the alkaline liquor containing said compounds to separate the nitrogenous bases in two types, soluble and insoluble, respectively, in water; separating said types, one from the other, in accordance with their differential solubility.
In testimony whereof I have signed my name to this specification.
HARRY K. IHRIG.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1686136A true US1686136A (en) | 1928-10-02 |
Family
ID=3416318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1686136D Expired - Lifetime US1686136A (en) | And one-half to associated oil |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1686136A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2454019A (en) * | 1948-11-16 | Purification of hetekocyclic | ||
| US2518353A (en) * | 1947-03-18 | 1950-08-08 | Union Oil Co | Purification of oils |
| US2519412A (en) * | 1950-08-22 | Swietoslawski | ||
| US2566353A (en) * | 1948-08-04 | 1951-09-04 | Houdry Process Corp | Purification of oils |
| US4671865A (en) * | 1985-09-27 | 1987-06-09 | Shell Oil Company | Two step heterocyclic nitrogen extraction from petroleum oils |
| US4749472A (en) * | 1985-09-27 | 1988-06-07 | Shell Oil Company | Two step heterocyclic nitrogen extraction from petroleum oils |
| US4790930A (en) * | 1987-05-29 | 1988-12-13 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils |
| US4960508A (en) * | 1989-01-30 | 1990-10-02 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils |
| US4960507A (en) * | 1989-03-20 | 1990-10-02 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils |
| US4985139A (en) * | 1988-07-14 | 1991-01-15 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils with reduced refinery equipment |
-
0
- US US1686136D patent/US1686136A/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2454019A (en) * | 1948-11-16 | Purification of hetekocyclic | ||
| US2519412A (en) * | 1950-08-22 | Swietoslawski | ||
| US2518353A (en) * | 1947-03-18 | 1950-08-08 | Union Oil Co | Purification of oils |
| US2566353A (en) * | 1948-08-04 | 1951-09-04 | Houdry Process Corp | Purification of oils |
| US4671865A (en) * | 1985-09-27 | 1987-06-09 | Shell Oil Company | Two step heterocyclic nitrogen extraction from petroleum oils |
| US4749472A (en) * | 1985-09-27 | 1988-06-07 | Shell Oil Company | Two step heterocyclic nitrogen extraction from petroleum oils |
| US4790930A (en) * | 1987-05-29 | 1988-12-13 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils |
| US4985139A (en) * | 1988-07-14 | 1991-01-15 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils with reduced refinery equipment |
| US4960508A (en) * | 1989-01-30 | 1990-10-02 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils |
| US4960507A (en) * | 1989-03-20 | 1990-10-02 | Shell Oil Company | Two-step heterocyclic nitrogen extraction from petroleum oils |
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