US2724001A - Method for the recovery of tar acids by extraction in the presence of an alkali soluble hydrosulfite - Google Patents
Method for the recovery of tar acids by extraction in the presence of an alkali soluble hydrosulfite Download PDFInfo
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- US2724001A US2724001A US283236A US28323652A US2724001A US 2724001 A US2724001 A US 2724001A US 283236 A US283236 A US 283236A US 28323652 A US28323652 A US 28323652A US 2724001 A US2724001 A US 2724001A
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- United States
- Prior art keywords
- extraction
- hydrosulfite
- products
- tar acids
- tar
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- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims description 26
- 150000007513 acids Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 12
- 238000000605 extraction Methods 0.000 title description 23
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 title description 9
- 239000003513 alkali Substances 0.000 title description 8
- 238000011084 recovery Methods 0.000 title description 7
- 239000003518 caustics Substances 0.000 claims description 19
- 239000003245 coal Substances 0.000 claims description 13
- 238000003763 carbonization Methods 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000011269 tar Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 17
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003077 lignite Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 229910004878 Na2S2O4 Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- -1 alkali metal hydrosulfite Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 229940051043 cresylate Drugs 0.000 description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical class OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000011289 tar acid Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- ZETCGWYACBNPIH-UHFFFAOYSA-N azane;sulfurous acid Chemical compound N.OS(O)=O ZETCGWYACBNPIH-UHFFFAOYSA-N 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- HEZHYQDYRPUXNJ-UHFFFAOYSA-L potassium dithionite Chemical compound [K+].[K+].[O-]S(=O)S([O-])=O HEZHYQDYRPUXNJ-UHFFFAOYSA-L 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C1/00—Working-up tar
- C10C1/18—Working-up tar by extraction with selective solvents
Definitions
- This invention is concerned with an improved method for the recovery of tar acids.
- the basic step in the recovery procedure is the extraction of the tar acid-containing material with an aqueous caustic solution.
- the tar acids are sprung by acidification of the extract and then subjected to the usual purification procedures.
- tar acids obtained by this procedure are highly colored and possess an undesirably high viscosity.
- darkening and high viscosity are the result of side reactions occurring during the caustic extraction.
- an alkali soluble hydrosulfite preferably an alkali metal hydrosulfite such as sodium hydrosulfite, Na2S2O4.
- the alkali soluble hydrosulfite is addedto the aqueous caustic solution employed as the extractant which contains usually from 5% to 20% of a strong alkali such as NaOH or KOH.
- the amount of hydrosulfite required will depend upon the material being extracted, more or less being necessary depending upon the tendency of the material to undergo reactions which lead to darkening and other undesirable side effects.
- the minimum amount necessary in any particular case can be determined by simple experiment. In most cases, a relatively small amount of the order of .2% to 3% based upon the weight of the caustic solution employed as the extractant will be found satisfactory.
- Alkali soluble hydrosulfites suitable for use in accord ance with the invention include, for example, alkali metal hydrosulfites such as sodium hydrosulfite Na2S2O4, potassium hydrosulfite K2S2O4, as well as ammonium hydrosulfite (NH4)2S2O4.
- Sodium hydrosulfite is to be preferred for its cheapness and availability. While the action of the hydrosulfites in preventing the undesirable effects discussed above is not completely understood, it is believed that these materials prevent the oxidation and subsequent polymerization of such compounds as dihydric phenols which are present in the mixture being extracted.
- Example 1 A tar obtained by the low temperature carbonization of lignite was distilled into the following fractions:
- Example 2 A distillation fraction boiling between 150 and 300 C. of a tar obtained from the low temperature carbonization of lignite was extracted with an aqueous solution of 5% KOH containing 1% Na2S2O4. A similar fraction was extracted with a 5% aqueous solution of KOH Without any added hydrosulfite. In each case, the alkaline extract was back washed with benzene, acidified with dilute sulfuric acid, and the tar acids recovered by extraction with ether. a v
- the tar acids extracted by the caustic solution containing added Na2S2O4 were light yellow in color, and did not darken upon standing.
- the acids extracted in the absence of NazSzOr were reddish brown in color, and became progressively darker upon storage.
- Example 3 A distillation fraction boiling between 300 and 400 C. of a tar obtained from the low temperature carbonization of lignite was'refluxed in a benzene solution over The mix- KOH and 1% NazSzOt, and the :other The containing with 5% KOH withoutthe addition of Na2S204.
- Example 4 The tar acids produced in Examples 2 and 3 by extraction in the presence of sodium hydrosulfite were combined and distilled to a vapor end point of 210 at mm.
- the tar acid'distillate which had been extracted without the use of the "hydrosulfite was initially darker in color and became progressively darker upon storage.
- Example 5 Several fractions from a coal hydrogenation oil produced by the hydrogenation of a bituminous coal under a pressure of 7500 pounds per square inch and .at a tem- F. were extracted with an aque- .perature of about 850 ous solution containing 10% sodium hydroxide and 2% by Weight of sodium hydrosulfite. Similar fractions were extractedwith a 10% sodium hydroxide solution without added sodium hydrosulfite. After phase separation, the cresylatelayer was inspected for coloration. The following results were obtained:
- aim-645 c ams fite during the extraction step the high or low temperature caris particularly useful in connection with the recovery of tar acids from the products of the low temperature carbonization of coal, especially from the low temperature carbonization products of the lower rank coals such as lignite.
- These low temperature tars apparently contain a greater amount of material which undergoes undesirable side reactions during caustic extraction than do high temperature tars.
- the final tar acid products are usually recovered in greater yields and are often substantially improved in marketability. They are generally colorless or only slightly colored, and of low viscosity, whereas those produced in accordance with conventional procedures are often opaque .or highly colored, and of relatively high viscosity. These improvements :are obtained without introducing an additional stage in .present tar refinery practice, and with the use of only small amounts of a relatively inexpensive reagent.
- .l. .A method for recovering ta-r acids from materials selected from the group consisting of coal carbonization products and coal hydrogenation products which comprises extracting said products with an aqueous caustic solution containing from 2% to 3% of sodium hydro- .sulfite.
- a method for recovering tar acids from the products of the low temperature carbonization of coal which comprises extracting said products with an aqueous caustic solution containing from .2% to 3% ,of sodium hydrosulfite.
- a method'for recovering tar acids from aproductso'f the low temperature icarbonization of lignite which comprises extracting said products -with an aqueous caustic :solution' containing from .2% to 3% sodium .hydro- .sulfite.
- a method for recovering tar acids from materials selected from the group consisting of coal carbonization products .and coal hydrogenation products whichcomprises extracting said products with an aqueous caustic solution containing trom 0.2% to 3% of sodium hydrosulfite, acidifying the causticsolution with a weak mineral .acid, and extracting the resulting tar phase with ether. 5.
- a method for recovering tar acids from the .materials selected from the group consisting of .coal carbonization products and coal hydrogenation products which comprises extracting said products with an aqueous caustic solution containing from 0.2% to 3% of a compound selected from the group consisting of the hydrosulfites-of sodium, potassium, and ammonium, acidifying the caustic solution with .a weak mineral acid, and extracting .the resulting solution with ether. 7
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Working-Up Tar And Pitch (AREA)
Description
2,724,001 Patented Nov. 15, 1955 ice METHOD FOR THE RECOVERY OF ACIDS BY EXTRACTION IN THE PRESENCE OF AN ALKALI SOLUBLE HYDROSULFITE Calvin Golumbic, Pittsburgh, Pa., assignor to the United States of America as represented by the Secretary of the Interior No Drawing. Application April 19, 1952, Serial No. 283,236
Claims. of. 260-627) (Granted under Title 35, U. S. Code (1952), sec. 266) The invention herein described and claimed maybe manufactured and used by or for the Government of the United States of America for governmental purposes without the payment of royalties thereon or therefor.
This invention is concerned with an improved method for the recovery of tar acids.
In the recovery of tar acids from the products of the carbonization or the hydrogenation of coal or from petroleum and similar materials, the basic step in the recovery procedure is the extraction of the tar acid-containing material with an aqueous caustic solution. After extraction, the tar acids are sprung by acidification of the extract and then subjected to the usual purification procedures. Oftentimes, tar acids obtained by this procedure are highly colored and possess an undesirably high viscosity. Apparently, darkening and high viscosity are the result of side reactions occurring during the caustic extraction. These undesirable effects are particularly apparent in the recovery of tar acids from low temperature tars produced by the low temperature carbonization of coal, lignite, and the like. With this type of material, furthermore, serious loss of potentially recoverable tar acids often occurs owing to the precipitation of resinous, and insoluble material during the caustic extraction.
In accordance with the present invention, it has been found that undesirable side effects occurring during caustic extraction which often lead to darkening, increased viscosity, and diminished yields, can be substantially mitigated or entirely prevented by conducting the extrac tion in the presence of a relatively small amount of an alkali soluble hydrosulfite, preferably an alkali metal hydrosulfite such as sodium hydrosulfite, Na2S2O4. Most desirably, the alkali soluble hydrosulfite is addedto the aqueous caustic solution employed as the extractant which contains usually from 5% to 20% of a strong alkali such as NaOH or KOH. The amount of hydrosulfite required will depend upon the material being extracted, more or less being necessary depending upon the tendency of the material to undergo reactions which lead to darkening and other undesirable side effects. The minimum amount necessary in any particular case can be determined by simple experiment. In most cases, a relatively small amount of the order of .2% to 3% based upon the weight of the caustic solution employed as the extractant will be found satisfactory.
Alkali soluble hydrosulfites suitable for use in accord ance with the invention include, for example, alkali metal hydrosulfites such as sodium hydrosulfite Na2S2O4, potassium hydrosulfite K2S2O4, as well as ammonium hydrosulfite (NH4)2S2O4. Sodium hydrosulfite is to be preferred for its cheapness and availability. While the action of the hydrosulfites in preventing the undesirable effects discussed above is not completely understood, it is believed that these materials prevent the oxidation and subsequent polymerization of such compounds as dihydric phenols which are present in the mixture being extracted. It is to be understood however, that the invention does not depend upon this, or any other particular theory as to the ultimate explanation of the beneficial effects pro- While the efiicacy of the hydrosulfites is probably due at least in part to their reducing properties, it has been found that other similar reducing agents such as sodium sulfite, NazSO3, and sodium bisulfite, NaHSO3, are ineffectual in preventing the undesirable side effects of alkali extraction. These other relatively strong reducing agents such as sodium sulfoxylate HzCOHSO3Na, sometimes produce transient beneficial effects but after short storage periods the extracted products rapidly deteriorate, increasing in color and viscosity, and often the end result of the addition of these other compounds is actually deleterious rather than beneficial.
Example 1 A tar obtained by the low temperature carbonization of lignite was distilled into the following fractions:
Fraction, boiling range, C.
pitch Appearance of cresylate layer Fraction, boiling range, 0. i p Extraction with- Of N32520: out NaaSzOl 150200 colorless..." reddish brown. 200-250 do deep red-brown. ZEN-300. .do Do. 300350- yellow dark brown. 350-400 -do Do.
Similar extraction tests using sodium sulfite NazSOz, sodium bisulfite NaHSOz, and sodium sulfoxylate HzCOHSOsNa were conducted. Although the cresylates initially obtained were somewhat lighter in color than those obtained with a straight caustic solution, darkened rapidly on standing and dark precipitates indicating reaction of the reducing agent with substances present in the cresylate.
Example 2 A distillation fraction boiling between 150 and 300 C. of a tar obtained from the low temperature carbonization of lignite was extracted with an aqueous solution of 5% KOH containing 1% Na2S2O4. A similar fraction was extracted with a 5% aqueous solution of KOH Without any added hydrosulfite. In each case, the alkaline extract was back washed with benzene, acidified with dilute sulfuric acid, and the tar acids recovered by extraction with ether. a v
The tar acids extracted by the caustic solution containing added Na2S2O4 were light yellow in color, and did not darken upon standing. The acids extracted in the absence of NazSzOr were reddish brown in color, and became progressively darker upon storage.
7 solid .sodium bicarbonate .for several hours. ture was filtered, and the filtrate divided into two portions. One portion was treated with an aqueous solution Y readily,
Example 3 A distillation fraction boiling between 300 and 400 C. of a tar obtained from the low temperature carbonization of lignite was'refluxed in a benzene solution over The mix- KOH and 1% NazSzOt, and the :other The containing with 5% KOH withoutthe addition of Na2S204.
V, tar acids were recovered from the alkaline extracts by acidifiation of .the extracts With dilute sulfuric acid and extraction ether.
During the caustic extraction, the portion extracted in the presence of NazSzOrz underwent phase separation both phases during the extraction were light in color, and there was no perceptible precipitation. During the extraction in the absence of added NazSzO4, both phases were dark and'noticeab'le precipitation of insoluble material occurred. The tar acids extracted in the presence of added NazSzOr were recovered as a mobile liquid of relatively low viscosity, while those extracted without the addition of NazSzOr had an undesirably high viscosity.
Example 4 The tar acids produced in Examples 2 and 3 by extraction in the presence of sodium hydrosulfite were combined and distilled to a vapor end point of 210 at mm. The ta-r acids produced in Examples 2 and 3 by extraction'without the use of sodium hydrosulfite were combined and distilled in a similar manner. The distilled tar acids which had been extracted in the presence ofisodium hydrosulfite were light in color and did not darken after several weeks storage. The tar acid'distillate which had been extracted without the use of the "hydrosulfite was initially darker in color and became progressively darker upon storage. Example 5 Several fractions from a coal hydrogenation oil produced by the hydrogenation of a bituminous coal under a pressure of 7500 pounds per square inch and .at a tem- F. were extracted with an aque- .perature of about 850 ous solution containing 10% sodium hydroxide and 2% by Weight of sodium hydrosulfite. Similar fractions were extractedwith a 10% sodium hydroxide solution without added sodium hydrosulfite. After phase separation, the cresylatelayer was inspected for coloration. The following results were obtained:
: Appearanceof cresylate layer 'Fractlon,boiling;range,F. V, Extraction Egtmcmn with gg gyg out NerSzO:
s1-3so j ellow".-- brown. 210452 amber darkbrown.
o black opaque.
aim-645 c ams fite during the extraction step the high or low temperature caris particularly useful in connection with the recovery of tar acids from the products of the low temperature carbonization of coal, especially from the low temperature carbonization products of the lower rank coals such as lignite. These low temperature tars apparently contain a greater amount of material which undergoes undesirable side reactions during caustic extraction than do high temperature tars.
If desired, other precautions may be taken in addition to the use of the alkali soluble hydrosulfite to prevent undesirable side effects during the caustic extraction. For example, by conducting the extraction in an oxygenfree atmosphere, further improved results can be obtained.
By operation in accordance with the invention, the final tar acid products are usually recovered in greater yields and are often substantially improved in marketability. They are generally colorless or only slightly colored, and of low viscosity, whereas those produced in accordance with conventional procedures are often opaque .or highly colored, and of relatively high viscosity. These improvements :are obtained without introducing an additional stage in .present tar refinery practice, and with the use of only small amounts of a relatively inexpensive reagent.
It is to be understood that the above description, together with the specific examples and embodiments described, is intendedmerely to illustrate the invention, and that the invention is not to be limited thereto, nor in any way except by the scope of the appended claims.
I claim: I
.l. .A method for recovering ta-r acids from materials selected from the group consisting of coal carbonization products and coal hydrogenation products which comprises extracting said products with an aqueous caustic solution containing from 2% to 3% of sodium hydro- .sulfite.
2. A method for recovering tar acids from the products of the low temperature carbonization of coal which comprises extracting said products with an aqueous caustic solution containing from .2% to 3% ,of sodium hydrosulfite.
3. A method'for recovering tar acids from aproductso'f the low temperature icarbonization of lignite which comprises extracting said products -with an aqueous caustic :solution' containing from .2% to 3% sodium .hydro- .sulfite.
-4. A method for recovering tar acids from materials selected from the group consisting of coal carbonization products .and coal hydrogenation products whichcomprises extracting said products with an aqueous caustic solution containing trom 0.2% to 3% of sodium hydrosulfite, acidifying the causticsolution with a weak mineral .acid, and extracting the resulting tar phase with ether. 5. A method for recovering tar acids from the .materials selected from the group consisting of .coal carbonization products and coal hydrogenation products which comprises extracting said products with an aqueous caustic solution containing from 0.2% to 3% of a compound selected from the group consisting of the hydrosulfites-of sodium, potassium, and ammonium, acidifying the caustic solution with .a weak mineral acid, and extracting .the resulting solution with ether. 7
References Cited in the tile of this patent UNITED STATESPATENTS
Claims (1)
- 5. A METHOD FOR RECOVERING TAR ACIDS FROM THE MATERIALS SELECTED FROM THE GROUP CONSISTING OF COAL CARBONIZATION PRODUCTS AND COAL HYDROGENATION PRODUCTS WHICH COMPRISES EXTRACTING SAID PRODUCTS WITH AN AQUEOUS CAUSTIC SOLUTION CONTAINING FROM 0.2% TO 3% OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE HYDROXULFITES OF SODIUM, POTASSIUM, AND AMMONIUM, ACIDIFYING THE CAUSTIC SOLUTION WITH A WEAK MINERAL ACID, AND EXTRACTING THE RESULTING SOLUTION WITH ETHER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US283236A US2724001A (en) | 1952-04-19 | 1952-04-19 | Method for the recovery of tar acids by extraction in the presence of an alkali soluble hydrosulfite |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US283236A US2724001A (en) | 1952-04-19 | 1952-04-19 | Method for the recovery of tar acids by extraction in the presence of an alkali soluble hydrosulfite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2724001A true US2724001A (en) | 1955-11-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US283236A Expired - Lifetime US2724001A (en) | 1952-04-19 | 1952-04-19 | Method for the recovery of tar acids by extraction in the presence of an alkali soluble hydrosulfite |
Country Status (1)
| Country | Link |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191227890A (en) * | 1912-12-03 | 1914-01-05 | Jacoub Aktschourin | Improved Manufacture of Resin-soap and Resin. |
| US1736464A (en) * | 1923-07-20 | 1929-11-19 | Westinghouse Electric & Mfg Co | Deoxidizer |
| US2006589A (en) * | 1934-03-05 | 1935-07-02 | Barrett Co | Method of purifying phenols |
| US2597497A (en) * | 1949-07-19 | 1952-05-20 | Allied Chem & Dye Corp | Purification of crude phenolacetone mixtures |
-
1952
- 1952-04-19 US US283236A patent/US2724001A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB191227890A (en) * | 1912-12-03 | 1914-01-05 | Jacoub Aktschourin | Improved Manufacture of Resin-soap and Resin. |
| US1736464A (en) * | 1923-07-20 | 1929-11-19 | Westinghouse Electric & Mfg Co | Deoxidizer |
| US2006589A (en) * | 1934-03-05 | 1935-07-02 | Barrett Co | Method of purifying phenols |
| US2597497A (en) * | 1949-07-19 | 1952-05-20 | Allied Chem & Dye Corp | Purification of crude phenolacetone mixtures |
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