US2315182A - Process for recovering neutral substances containing oxygen from oils containing such substances - Google Patents
Process for recovering neutral substances containing oxygen from oils containing such substances Download PDFInfo
- Publication number
- US2315182A US2315182A US387610A US38761041A US2315182A US 2315182 A US2315182 A US 2315182A US 387610 A US387610 A US 387610A US 38761041 A US38761041 A US 38761041A US 2315182 A US2315182 A US 2315182A
- Authority
- US
- United States
- Prior art keywords
- substances
- neutral
- oxygen
- oils
- solution
- 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
- 239000000126 substance Substances 0.000 title description 23
- 230000007935 neutral effect Effects 0.000 title description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title description 16
- 229910052760 oxygen Inorganic materials 0.000 title description 16
- 239000001301 oxygen Substances 0.000 title description 16
- 239000003921 oil Substances 0.000 title description 14
- 238000000034 method Methods 0.000 title description 7
- 229940031826 phenolate Drugs 0.000 description 12
- 238000009835 boiling Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- -1 alkali metal phenolate Chemical class 0.000 description 3
- 238000003763 carbonization Methods 0.000 description 3
- 230000001066 destructive effect Effects 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000011269 tar Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000003077 lignite Substances 0.000 description 2
- 239000003415 peat Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- LMWMTSCFTPQVCJ-UHFFFAOYSA-N 2-methylphenol;phenol Chemical compound OC1=CC=CC=C1.CC1=CC=CC=C1O LMWMTSCFTPQVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
- 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
- C10G21/16—Oxygen-containing compounds
Definitions
- the present invention relates to a process for recovering neutral substances containing oxygen from oils containing such substances.
- the tars and oils obtained by the thermal treatment for example the low temperature carbonization or destructive hydrogenation of mineral coal, brown coal, peat, Wood, bituminous shale or similar materials, are known to contain in the lower fractions in addition to hydrocarbons smaller percentages of neutral substances containing oxygen, in particular ketones, alcohols, ethers and esters, hereinafter briefly referred to as the neutral oxygen substances.
- the neutral oxygen substances can be extracted with the aid of suitable solvents, for example chlorinated hydrocarbons, the boiling point of which is preferably widely different from that of the neutral oxygen substances so as to make their separation easier. Since as a rule the neutral oxygen substances boiling between about 50 and 150 C. are desirable, solvents are used which boil below 50 C., as for example methylene chloride, or such as boil above 150 C., as for example a phenol fraction.
- suitable solvents for example chlorinated hydrocarbons
- the neutral oxygen substances can be separated from the phenolate solution also by distillation, preferably with the introduction of inert gases or water vapor.
- the distillate containing water and the neutral oxygen substances usually separates into two liquid layers, of which the lower one contains the greater portion of the water along with acetone and methylethylketone, whereas the upper one contains little water and, in addition to acetone and methylethylketone,
- alcohols containing more than 3 carbon atoms ketones containing more than 4 carbon atoms, and a small amount of light-boiling hydrocarbons.
- a distilling column can be used which is fitted with a reflux condenser and allows to remove first the lighter boiling neutral oxygen substances from the solution and then the higher boiling hydrocarbons.
- the oil is divided into a light oil boiling below about 180 and a middle oil containing phenols.
- a middle oil containing phenols By treating this middle oil with caustic soda a phenolate solution is obtained which serves for the extraction of the neutral oxygen substances from the low boiling frac-. tion of the initial oil.
- the phenolat solution after the removal of the neutral substances by distillation or extraction, is acidified and freed from the phenols in known manner.
- Example 100 parts (by volume) of a gasoline boiling between 30 and 150 C. and obtained by the destructive hydrogenation of brown coal in the liquid phase are extracted with 100 parts (by volume) of a solution of an alkali metal phenolate obtained by mixing 25 parts (by volume) of a phenol-cresol mixture with 75 parts (by volume) of caustic soda solution of 10 per cent strength.
- the phenolate solution is then distilled in a still provided with a column.
- 3 parts (by volume) of a distillate pass over between 55.5 and 58 C., having a spec. gravity of 0.787 and mainly consisting of acetone, while another 3 parts (by volume) of a distillate havin a spec. gravity of 0.814 and mainly containing methylethylketone in addition to some acetone and water are obtained between 58 and 87 C.
- a process for recovering organic neutral substances containing oxygen selected from the class consisting of ketones, alcohols, ethers and esters from a hydrocarbon oil boiling between about 30 and 150 C. which comprises extracting the oil with a solution of an alkali metal phenolate and then separating the neutral oxygen substances from the extract.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
Patented Mar. 30, 1943 PROCESS FOR RECOVERING NEUTRAL SUB- STANCES CONTAINING OXYGEN FROM OILS CONTAINING SUCH SUBSTANCES Rudolf Bemmann, Leuna, Germany; vested in the Alien Property Custodian No Drawing. Application April 9, 1941, Serial No. 387,610. In Germany April 26, 1940 4 Claims.
The present invention relates to a process for recovering neutral substances containing oxygen from oils containing such substances.
The tars and oils obtained by the thermal treatment, for example the low temperature carbonization or destructive hydrogenation of mineral coal, brown coal, peat, Wood, bituminous shale or similar materials, are known to contain in the lower fractions in addition to hydrocarbons smaller percentages of neutral substances containing oxygen, in particular ketones, alcohols, ethers and esters, hereinafter briefly referred to as the neutral oxygen substances.
While in the carbonization of wood these neutral oxygen substances are formed in a quantity which allows them to be easily separated from the tars and oils and divided into their components by fractional distillation, in products obtained by the low temperature carbonization or destructive hydrogenation of coal, peat or bituminous shale they are contained in so small a percentage that their recovery was not possible from an economical point of View.
I have now found that the neutral oxygen substances contained in the fractions, boiling below about 180 C. and preferably between about 30 and 150 C., of the said oils can be recovered in a simple manner by extracting them with a solution of an alkali metal phenolate and afterwards separating them from the phenolate solution. I have made the discovery that phenolate solutions have a high selective dissolving power towards the said neutral substances, especially to ketones and alcohols.
From the phenolate solutions the neutral oxygen substances can be extracted with the aid of suitable solvents, for example chlorinated hydrocarbons, the boiling point of which is preferably widely different from that of the neutral oxygen substances so as to make their separation easier. Since as a rule the neutral oxygen substances boiling between about 50 and 150 C. are desirable, solvents are used which boil below 50 C., as for example methylene chloride, or such as boil above 150 C., as for example a phenol fraction.
The neutral oxygen substances can be separated from the phenolate solution also by distillation, preferably with the introduction of inert gases or water vapor. The distillate containing water and the neutral oxygen substances usually separates into two liquid layers, of which the lower one contains the greater portion of the water along with acetone and methylethylketone, whereas the upper one contains little water and, in addition to acetone and methylethylketone,
alcohols containing more than 3 carbon atoms, ketones containing more than 4 carbon atoms, and a small amount of light-boiling hydrocarbons.
In case the phenolate solution used for extraction also contains dissolved hydrocarbons, a distilling column can be used which is fitted with a reflux condenser and allows to remove first the lighter boiling neutral oxygen substances from the solution and then the higher boiling hydrocarbons.
It is advantageous to combine the process according to the present invention with the usual working up of tars or other oils containing phenols. For this purpose the oil is divided into a light oil boiling below about 180 and a middle oil containing phenols. By treating this middle oil with caustic soda a phenolate solution is obtained which serves for the extraction of the neutral oxygen substances from the low boiling frac-. tion of the initial oil. The phenolat solution, after the removal of the neutral substances by distillation or extraction, is acidified and freed from the phenols in known manner.
The following example serves to illustrate how the present invention may be carried out in practice but the invention is not restricted to the example. 7
Example 100 parts (by volume) of a gasoline boiling between 30 and 150 C. and obtained by the destructive hydrogenation of brown coal in the liquid phase are extracted with 100 parts (by volume) of a solution of an alkali metal phenolate obtained by mixing 25 parts (by volume) of a phenol-cresol mixture with 75 parts (by volume) of caustic soda solution of 10 per cent strength. The phenolate solution is then distilled in a still provided with a column. During this distillation 3 parts (by volume) of a distillate pass over between 55.5 and 58 C., having a spec. gravity of 0.787 and mainly consisting of acetone, while another 3 parts (by volume) of a distillate havin a spec. gravity of 0.814 and mainly containing methylethylketone in addition to some acetone and water are obtained between 58 and 87 C.
2. The process as claimed in claim 1 which comprises separating the said neutral substances from the phenolate solution by distillation.
3. The process as claimed in claim 1 which comprises separating the said neutral substances from the phenolate solution by extraction with an organic solvent.
4. A process for recovering organic neutral substances containing oxygen selected from the class consisting of ketones, alcohols, ethers and esters from a hydrocarbon oil boiling between about 30 and 150 C. which comprises extracting the oil with a solution of an alkali metal phenolate and then separating the neutral oxygen substances from the extract. 1
' RUDOLF BEMMANN.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2315182X | 1940-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2315182A true US2315182A (en) | 1943-03-30 |
Family
ID=7994548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US387610A Expired - Lifetime US2315182A (en) | 1940-04-26 | 1941-04-09 | Process for recovering neutral substances containing oxygen from oils containing such substances |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2315182A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2535069A (en) * | 1948-08-12 | 1950-12-26 | Standard Oil Co | Separation of organic oxygenated compounds from hydrocarbons |
| US2641616A (en) * | 1953-06-09 | Purification of chemical | ||
| US2683750A (en) * | 1954-07-13 | Purification of vinyl ethers | ||
| US2892348A (en) * | 1955-08-03 | 1959-06-30 | Jr Regner A Ekstrom | Flowmeter for fluids |
-
1941
- 1941-04-09 US US387610A patent/US2315182A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2641616A (en) * | 1953-06-09 | Purification of chemical | ||
| US2683750A (en) * | 1954-07-13 | Purification of vinyl ethers | ||
| US2535069A (en) * | 1948-08-12 | 1950-12-26 | Standard Oil Co | Separation of organic oxygenated compounds from hydrocarbons |
| US2892348A (en) * | 1955-08-03 | 1959-06-30 | Jr Regner A Ekstrom | Flowmeter for fluids |
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