US1945376A - Extraction of phenols - Google Patents
Extraction of phenols Download PDFInfo
- Publication number
- US1945376A US1945376A US520479A US52047931A US1945376A US 1945376 A US1945376 A US 1945376A US 520479 A US520479 A US 520479A US 52047931 A US52047931 A US 52047931A US 1945376 A US1945376 A US 1945376A
- Authority
- US
- United States
- Prior art keywords
- phenols
- impurities
- tar
- solution
- oils
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
- C07C37/007—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up from the tar industry
Definitions
- the impurities are frequently found to amount to as much as in a crude acid prepared as above.
- the crude phenate or cresylate or like compound is heated with steam and simultaneously blown with air, which process removes naphthalene and neutral oil, but must be continued for a considerable period in the most favourable circumstances to obtain the desired result, and in some cases is carried on for as long as forty-eight hours, and is attended by a considerable loss of tar acids as hydrolysis is considerable at the temperature at which blowing is conducted.
- Phenates, cresylates, and like compounds derived from horizontal retort and coke oven tars contain impurities which have a relatively high vapor pressure.
- the known process is more or less effective for the treatment of those products; but the phenates, cresylates, and like compounds obtained from low temperature tar oils, cracked mineral oils, or shale oil contain impurities which have a relatively low vapor pressure, and for the treatment of these oils it has been found necessary to prolong the process of purification by steam or air blowing, with the consequence that loss of tar acid product is substantially increased; the degree of refinement attained is also unsatisfactory.
- the present invention consists in distilling the phenates, cresylates, or like compounds in aqueous solution containing the impurities, un-
- the neutral oils and other impurities which will distil at subsequent stages of refining are thus taken ofi.
- the tar acids are held in combination with the alkali, and as they are not volatile when in such combination, they remain in the still with a proportion of heavy and gummy impurities which do not pass over; these heavy and gummy impurities, however, cause no difliculty in the later steps in the process.
- the known process is then again followed, and the still liquor from which the impurities have been removed in the distillation step are treated with sulphuric acid or carbon dioxide, following known practice, to liberate the tar acids.
- the mixed acid product thus obtained is fractionated under appropriate temperature and pressure conditions to obtain the particular phenols or other tar acids required.
- the distillate acids may be treated by air blowing or with a metallic oxide and subjected to final redistillation to obtain them in a condition of great purity.
- the removal of the impurities by distillation prior to the decomposing of the alkali phenolic or similar compounds is efiected under high vacuum. It is desirable that the vacuum should be as high as practicable; the results are less satisfactory as the vacuum falls.
- cresylate solution is then pumped to a vacuum pan; a single effect pan such as used for concentration of weak caustic soda liquor is suitable for this operation.
- the charge is boiled vigorously under a vacuum of 27-28" vacuum; the bulk of the oil and bases come away in the first five minutes.
- acid which gives a completely miscible solution in caustic soda it is necessary to prolong the process; when so prolonged the process is generally completed in forty-five minutes.
- the completeness of the operation can be determined by decomposing a small sample of the cresylate with sulphuric acid, distilling the separated cresylic acid, and re-dissolving in 10% caustic soda solution.
- the refined sodium cresylate can then be decomposed by known process and distilled.
- the step of removing neutral oils and other alkali insoluble bodies from the solution which step comprises distilling the solution of phenols in the hydroxide of an alkali metal at a pressure substantially below atmospheric pressure.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 30, 1934 STATES PATENT OFFICE EXTRACTION OF PHENOLS Wales No Drawing. Application March 5, 1931, Serial No. 520,479, and in Australia April 4, 1930 3 Claims.
In the known process of extracting phenols, phenol homologues, and other hydroxy aromatic compounds from oils, crude phenates, cresylates, and like compounds obtained by washing the oil with caustic soda or other alkali hydroxide, are decomposed with acid and settled out and the crude tar acids thus liberated are separated by distillation. In the distillation step, neutral oils, pyridine, naphthalene, and certain other substances come overwith the acids, and the products are thus rendered impure. The impurities unfit the acids for many uses, as for instance in the manufacture of synthetic resins and fine antiseptic s.
The impurities are frequently found to amount to as much as in a crude acid prepared as above. In the known method of purification, the crude phenate or cresylate or like compound is heated with steam and simultaneously blown with air, which process removes naphthalene and neutral oil, but must be continued for a considerable period in the most favourable circumstances to obtain the desired result, and in some cases is carried on for as long as forty-eight hours, and is attended by a considerable loss of tar acids as hydrolysis is considerable at the temperature at which blowing is conducted.
Phenates, cresylates, and like compounds derived from horizontal retort and coke oven tars contain impurities which have a relatively high vapor pressure. The known process is more or less effective for the treatment of those products; but the phenates, cresylates, and like compounds obtained from low temperature tar oils, cracked mineral oils, or shale oil contain impurities which have a relatively low vapor pressure, and for the treatment of these oils it has been found necessary to prolong the process of purification by steam or air blowing, with the consequence that loss of tar acid product is substantially increased; the degree of refinement attained is also unsatisfactory.
The present invention consists in distilling the phenates, cresylates, or like compounds in aqueous solution containing the impurities, un-
der high vacuum, before the tar acids are liberated from it by treatment with mineral acid, carbonic acid, or other reagent. The neutral oils and other impurities which will distil at subsequent stages of refining are thus taken ofi. The tar acids are held in combination with the alkali, and as they are not volatile when in such combination, they remain in the still with a proportion of heavy and gummy impurities which do not pass over; these heavy and gummy impurities, however, cause no difliculty in the later steps in the process.
The known process is then again followed, and the still liquor from which the impurities have been removed in the distillation step are treated with sulphuric acid or carbon dioxide, following known practice, to liberate the tar acids. The mixed acid product thus obtained is fractionated under appropriate temperature and pressure conditions to obtain the particular phenols or other tar acids required. The distillate acids may be treated by air blowing or with a metallic oxide and subjected to final redistillation to obtain them in a condition of great purity.
The removal of the impurities by distillation prior to the decomposing of the alkali phenolic or similar compounds is efiected under high vacuum. It is desirable that the vacuum should be as high as practicable; the results are less satisfactory as the vacuum falls.
In practice the process is operated as follows:
Sodium cresylate solution of specific gravity about 1.075 obtained from washing tar oil is run to settling tanks where any oil that settles out on standing for twelve hours is skimmed off.
The cresylate solution is then pumped to a vacuum pan; a single effect pan such as used for concentration of weak caustic soda liquor is suitable for this operation. The charge is boiled vigorously under a vacuum of 27-28" vacuum; the bulk of the oil and bases come away in the first five minutes. However, to obtain acid which gives a completely miscible solution in caustic soda it is necessary to prolong the process; when so prolonged the process is generally completed in forty-five minutes.
The completeness of the operation can be determined by decomposing a small sample of the cresylate with sulphuric acid, distilling the separated cresylic acid, and re-dissolving in 10% caustic soda solution.
The refined sodium cresylate can then be decomposed by known process and distilled.
What I claim as my invention and desire to secure by Letters Patent is:-
1. In the recovery of phenols from tar oils by extraction with a solution of a hydroxide of an alkali metal, the step of removing neutral oils and other alkali insoluble bodies from the solution which step comprises distilling the solution of phenols in the hydroxide of an alkali metal at a pressure substantially below atmospheric pressure.
2. In the recovery of phenols from tar oils by 3. The herein described method of removing neutral oils from a caustic soda phenolate solution, comprising distilling the solution at a pressure substantially below atmospheric pressure.
JVOHN GRIFFITH PEAKE.
Howl]
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU1945376X | 1930-04-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
US1945376A true US1945376A (en) | 1934-01-30 |
Family
ID=3837813
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US520479A Expired - Lifetime US1945376A (en) | 1930-04-04 | 1931-03-05 | Extraction of phenols |
Country Status (1)
Country | Link |
---|---|
US (1) | US1945376A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3036135A (en) * | 1957-03-20 | 1962-05-22 | Kermit M Bleese | Treatment of primary tar acid compounds |
-
1931
- 1931-03-05 US US520479A patent/US1945376A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3036135A (en) * | 1957-03-20 | 1962-05-22 | Kermit M Bleese | Treatment of primary tar acid compounds |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2199208A (en) | Purification of petroleum phenols | |
EP0029695B1 (en) | Removal of phenols from phenol-containing streams | |
US3176041A (en) | Separation of naphthenic acids from a petroleum oil | |
US1945376A (en) | Extraction of phenols | |
US2410906A (en) | Methods of recovering pykibine | |
US2150656A (en) | Process for desulphurizing alkyl phenols | |
US2043102A (en) | Process of producing phenols | |
US2163227A (en) | Process for desulphurizing alkyl phenols | |
NO823368L (en) | PROCEDURE FOR RECOVERY OF ORGANOPHOSPHATE-BASED FLUIDS | |
US2247523A (en) | Process for refining phenols | |
US1873900A (en) | Removal of phenols from waste and other liquors | |
US2218139A (en) | Process of separating thiophenols from alkyl phenols | |
US2773806A (en) | Refining hydrocarbon oil vapors with alkali and high boiling naphthenic acids | |
US2203217A (en) | Process for recovering alkyl phenols from petroleum oils | |
US1954959A (en) | Method of freeing oils from sulphur dioxide | |
US1528313A (en) | Process for disintegrating or decomposing coal tar or its distillat?s into phenols and neutral oils | |
US1830725A (en) | Extraction of phenols from aqueous condensate from coal distillation | |
US2560178A (en) | Regenerating mercaptan solvent | |
US2369022A (en) | Treatment of crude tar acids for the selective removal of acidic contaminants | |
DE686700C (en) | Process for the recovery of purified phenols from crude phenols | |
US2039106A (en) | Method for purifying naphthenic acids | |
US2593851A (en) | Method of removing mercaptans from hydrocarbons | |
US2236928A (en) | Process of separating thiophenols from alkyl phenols | |
US2358229A (en) | Treatment of pyroligneous acid | |
US2997477A (en) | Extraction and recovery of phenols and pyridines from phenol containing oils |