US1758802A - Process of resolving oil emulsions and reagents therefor - Google Patents
Process of resolving oil emulsions and reagents therefor Download PDFInfo
- Publication number
- US1758802A US1758802A US77981A US7798125A US1758802A US 1758802 A US1758802 A US 1758802A US 77981 A US77981 A US 77981A US 7798125 A US7798125 A US 7798125A US 1758802 A US1758802 A US 1758802A
- Authority
- US
- United States
- Prior art keywords
- oil
- mineral oil
- emulsion
- sulfonated
- emulsions
- 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
- 239000000839 emulsion Substances 0.000 title description 68
- 239000003153 chemical reaction reagent Substances 0.000 title description 25
- 238000000034 method Methods 0.000 title description 21
- 239000002480 mineral oil Substances 0.000 description 57
- 235000010446 mineral oil Nutrition 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000002253 acid Substances 0.000 description 17
- 235000014113 dietary fatty acids Nutrition 0.000 description 16
- 239000000194 fatty acid Substances 0.000 description 16
- 229930195729 fatty acid Natural products 0.000 description 16
- 150000004665 fatty acids Chemical class 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 239000010685 fatty oil Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 235000012343 cottonseed oil Nutrition 0.000 description 5
- 239000002385 cottonseed oil Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229940097789 heavy mineral oil Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 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
- C10G33/00—Dewatering or demulsification of hydrocarbon oils
- C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
Definitions
- This invention relates to processesof treating oil emulsions and reagents therefor, and more particularly to the treatment of petroleum oil and water emulsions for breakin or resolving such emulsions.
- An important object of the present invention is to provide an inexpensive, practical, effective and quick method ,of breaking the emulsion to separate the oil from the water and foreign matter therein.
- Another object of the invention is the provision of a deemulsifying reagent which is sufliciently soluble in or miscible with the dispersing phase or both the dispersing and dispersed phases of the oil and water emulsion to quickly act upon one or both of them to effect the rapid brealn'ng of the emulsion.
- a further object of the invention is to provide a de-emulsifying reagent of such potency and effectiveness that emulsions can be completely broken by the use of a much smaller quantity of reagent than is required in the case of prior de-emulsifying reagents.
- a further object of the invention is to provide a de-emulsifying reagent which may be effectively used in breaking oil and water emulsions from different wells and of different characters which are incapable of being effectively broken by any single prior deemulsifying reagent.
- Such products may be obtained by treatment of the mineral oils or ingredients thereof by known methods with mineral acids as for example, phosphoric acid, or-organic acids, as for example, acetic acid, capable of forming acid addition or substitution products therewith.
- acid derivatives of a mineral oil as herein employed contemplates any acid addition or substitution product of a mineral oil or ingredient or ingredients thereof capable of forming acid addition or substitution products and the term fatty acid glycerid aslherein used contemplates any fat or fatt o1
- a sulfonated mineral oil preferably sulfonated parafiin petroleum oil or ingredients thereof capable of being sulfonated
- a fat or fatty oil preferably a vegetable oil such as cottonseed oil, olive oil, castor oil or the like.
- the mixture preferably contains the sulfonated mineral oil and the fat or fatty oil in the proportions of about two parts by Weight of the former to one part by weight of the latter.
- a 7 mixture of the ingredients in such proportions constitutes a deemulsifying reagent adapted for effectively breaking emulsions from quite a large number of different wells requiring different, treatments by prior processes.
- the proportions of these materials may in some cases be varied, satisfactory deemulsification' being possible in the case of emulsions from certain different individual wells by the use of the ingredients in difierent proportions varying from 1 to 4 parts by weight of the sulfonated mineral oil to 2 to 10 parts by weight of the fatty oils.
- sulfonated mineral oil is prepared by any known method of sulfonation from'natural or cracked petroleum oil, preferably paraflin petroleum oil or ingredients thereof capable of being sulfonated, any excess of the acid employed being preferably removed and the product freed from byproducts of the sulfonating process so that the product is preferably substantially free from uncombined acid and other impurities.
- a fatty oil in preparing my deemulsifying reagent, some measure of success ordinarily is obtainable by the use of a fat, even one of high stearine content such as tallow, but fatty bodies of low stearine and high olein content, such as vegetable oils, are preferred.
- I may with some degree of success employ any of the well known fatty acids, such for example, as oleic acid, but I prefer to employ the glycerids.
- the fatty acid glycerids may, if desired, be dissolved in a suitable solvent such as naphtha before being added to thesulfonated mineral acid and in the use of a fat of high stearine content, the reagentmay be more readily prepared by first dissolving the fat.
- a small amount preferably from .02 to .1 per cent. by weight of the reagent is placed in a quantity of the oil and-water emulsion to be treated and the emulsion allowed to stand until the oil separates and rises to the top.
- the oil and water may then be separated and the impurities or foreign matter removed with the water.
- the emulsion may advantageously be heated preferably to the oil when mixed in the preferred proportions I of about 2 parts by weight of the former to 1 part by weight of the latter and employed in the proportion of about .025 per cent. by weight with respectto the emulsion, is generally operative in effecting rapid and satisfactory deemulsification of most mineral oil and water emulsions.
- I prepare the reagent by first sulfonating ingredients of paraflin petroleum oil ca.-
- the process is performed in substantially the same manner and substantially the same percentage of the reagent is preferably used, regardless of changes in the specific composition of thereagentexcept that in using organic acid addition or substitution products of mineral oil I preferably employ about twice as much of the reagent as I employ in using sulfonated mineral oil.
- I claim: p 1. The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto an acid derivative of a mineral oil and a fatty acid glycerid and causing such added materials to a'ctupon the emulsion until such emulsion'is broken or resolved.
- I 17 A reagent for breaking or resolving emulsions of mineral oil and water containing a sulfonated mineral oil, a fatty acid glycerid, and phenol.
- a rea ent for breaking or resolving emulsions o mineral oil and water containing an acid derivative of a mineral oil and a fatty acid glycerid.
- a reagent for breaking or resolving emulsions of mineral oil and water contain-
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)
- Colloid Chemistry (AREA)
Description
Patented May 13, 1930 PATENT OFFICE FREDERICK H. PENN, OF DALLAS, TEXAS PROCESS OF RESOLV'ING OIL EMULSIONS AND REAGENTS THEREFOR Ho Drawing. Application filed December 28, 1925, Serial No.77,981. Renewed April 20, 1928'.
This invention relates to processesof treating oil emulsions and reagents therefor, and more particularly to the treatment of petroleum oil and water emulsions for breakin or resolving such emulsions.
- ariousmineral oils as they are. obtained from the wells containsubstances which have caused them to emulsify with the water pres-- cut, and in such condition, they are not ad- 'vantageously marketable. The emulsions from different wells and sometimes even from the same well at different periods, differ in character and ordinarily require the use of different reagents for their satisfactory treatment.
An important object of the present invention is to provide an inexpensive, practical, effective and quick method ,of breaking the emulsion to separate the oil from the water and foreign matter therein.
Another object of the invention is the provision of a deemulsifying reagent which is sufliciently soluble in or miscible with the dispersing phase or both the dispersing and dispersed phases of the oil and water emulsion to quickly act upon one or both of them to effect the rapid brealn'ng of the emulsion.
. A further object of the invention is to provide a de-emulsifying reagent of such potency and effectiveness that emulsions can be completely broken by the use of a much smaller quantity of reagent than is required in the case of prior de-emulsifying reagents.
A further object of the invention is to provide a de-emulsifying reagent which may be effectively used in breaking oil and water emulsions from different wells and of different characters which are incapable of being effectively broken by any single prior deemulsifying reagent.
I have discovered that numerous naturally occurring mineral oil and water emulsions can bebroken or resolved by treating them with an acid addition or substitution product of a mineral oil soluble in the dispersing phase of such emulsions and preferably such addition or substitution product soluble in both phases of the emulsion. I also have discovered that better results are obtained and that all naturally occurring mineral oil and water emulsions with which I am acquainted can be resolved by treating such emulsions with such addition or substitution product and a fat or fatty oil preferably a vegetable oil such as cottonseed oil.
I prefer to employ a sulfonated mineral .Oil preferabl sulfonated paraflinpetroleum oil or ingredients thereof but may use any acid addition or substitution product of a mineral oil soluble in the dispersing phase of a mineral oil and water emulsion. Such products may be obtained by treatment of the mineral oils or ingredients thereof by known methods with mineral acids as for example, phosphoric acid, or-organic acids, as for example, acetic acid, capable of forming acid addition or substitution products therewith. It is preferable to employ mineral acid addition or substitution products of the mineral oil owing totheir greater effectiveness and owing to the difiiculty of forming addition or substitution products of mineral oil with organic acids and I have obtained the most satisfactory results with sulfonated-mineral oil particularly when employed with a fat or fatty oil.
'The term acid derivatives of a mineral oil as herein employed contemplates any acid addition or substitution product of a mineral oil or ingredient or ingredients thereof capable of forming acid addition or substitution products and the term fatty acid glycerid aslherein used contemplates any fat or fatt o1 In the preferred practice of my invention, I employ a sulfonated mineral oil preferably sulfonated parafiin petroleum oil or ingredients thereof capable of being sulfonated and a fat or fatty oil preferably a vegetable oil such as cottonseed oil, olive oil, castor oil or the like. The mixture preferably contains the sulfonated mineral oil and the fat or fatty oil in the proportions of about two parts by Weight of the former to one part by weight of the latter. I have found that a 7 mixture of the ingredients in such proportions constitutes a deemulsifying reagent adapted for effectively breaking emulsions from quite a large number of different wells requiring different, treatments by prior processes. However, the proportions of these materials may in some cases be varied, satisfactory deemulsification' being possible in the case of emulsions from certain different individual wells by the use of the ingredients in difierent proportions varying from 1 to 4 parts by weight of the sulfonated mineral oil to 2 to 10 parts by weight of the fatty oils. To obtain the most economical and in some cases the best results, I preferably apply a test treatment of my reagent mixed in different proportions to the particular emulsion to be broken and thus readily ascertain the proportions of sulfonated mineral oil and fat or fatty oil which can most advantageously be used. The sulfonated mineral oil is prepared by any known method of sulfonation from'natural or cracked petroleum oil, preferably paraflin petroleum oil or ingredients thereof capable of being sulfonated, any excess of the acid employed being preferably removed and the product freed from byproducts of the sulfonating process so that the product is preferably substantially free from uncombined acid and other impurities.
While I prefer to employ a fatty oil in preparing my deemulsifying reagent, some measure of success ordinarily is obtainable by the use of a fat, even one of high stearine content such as tallow, but fatty bodies of low stearine and high olein content, such as vegetable oils, are preferred. In place of the fat or fatty oil I may with some degree of success employ any of the well known fatty acids, such for example, as oleic acid, but I prefer to employ the glycerids.
The fatty acid glycerids may, if desired, be dissolved in a suitable solvent such as naphtha before being added to thesulfonated mineral acid and in the use of a fat of high stearine content, the reagentmay be more readily prepared by first dissolving the fat.
I have found that numerous mineral oil and water emulsions can be broken by the use of a sulfonated mineral oil preferably sulfonated paraflin petroleum oil or ingredients thereof capable of being sulfonated without the use therewith of a fat or fatty oil but in my experiments I have obtained better results by employing fat' or fatty oilwith the sulfonated mineral oil. i
In practicing my process, a small amount preferably from .02 to .1 per cent. by weight of the reagent is placed in a quantity of the oil and-water emulsion to be treated and the emulsion allowed to stand until the oil separates and rises to the top. The oil and water may then be separated and the impurities or foreign matter removed with the water. In some instanpes, as for example, where a fat is employed in the deemulsifying reagent or where an emulsion of a heavy mineral oil and water is under treatment the emulsion may advantageously be heated preferably to the oil when mixed in the preferred proportions I of about 2 parts by weight of the former to 1 part by weight of the latter and employed in the proportion of about .025 per cent. by weight with respectto the emulsion, is generally operative in effecting rapid and satisfactory deemulsification of most mineral oil and water emulsions.
In some particular emulsions I have found 1 that the addition of a'small quantity of phenol to the reagent is advantageous and in such cases, I employ phenol of about 25 to 35 per cent. strength in the proportion of about from 3 to 10 per cent. by weight of the mixture of sulfonated mineral oil and fatty acid glycerids. I
In the preferred embodiment of the invention, I prepare the reagent by first sulfonating ingredients of paraflin petroleum oil ca.-
pable of being sulfonated. Any excess acid is removed and the product purified and the sulfonated product is then mixed with cottonseed oil in the proper proportion as hereinbefore indicated. This material is then added to the emulsion to be treated in the proportion of about from .02to .1 per cent. and ordinarily preferably about 02 per cent. by Weight of the emulsion and the emulsion is allowed'to stand until it breaks and the oil rises to the top. The oil may then be readily separated from the water and foreign matter. The process is performed in substantially the same manner and substantially the same percentage of the reagent is preferably used, regardless of changes in the specific composition of thereagentexcept that in using organic acid addition or substitution products of mineral oil I preferably employ about twice as much of the reagent as I employ in using sulfonated mineral oil. a While I have described in detail the preferred practice of my process, it is to-be understood that the details of procedure may be widely varied without departing from the spirit of the invention or the scope of the subjoined claims.
I claim: p 1. The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto an acid derivative of a mineral oil and a fatty acid glycerid and causing such added materials to a'ctupon the emulsion until such emulsion'is broken or resolved.
2. The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto a mineral acid derivative of a mineral oil and a fatty acid glycerid and causing such added materials to act upon the emulsion until such emulsion is broken or resolved.
3. The process of breaking or resolving emulsions of mineral oil and Water comprising adding thereto an acid derivative of a mineral oil and a fatty acid glycerid, heating the mixture, and causing such added mate rials to act upon the emulsion until such emulsion is broken or resolved.
4., The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto an acid derivative of a mineral oil, a fatty acid glycerid and phenol,
. and causing such added materials to act upon the emulsion until such emulsion is broken or resolved.
5. The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto a sulfonated mineral oil and a fatty acid glycerid and causing such added materials to act upon the emulsion until such emulsion is broken or resolved.
6. The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto a sulfonated mineral oil and a fatty oil and causing such added materials to act upon the emulsion until such emulsion is broken or resolved.
7. The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto a sulfonated mineral oil and cotton seed oil and causing such added materials to act upon the emulsion until such emulsion is broken or resolved.
8. The process of breaking or resolving emulsions of mineral oil and water comprising adding thereto a sulfonated mineral oil, a fatty acid glycerid and phenol, and causing such added materials to act upon the emulsion until such emulsion is broken or resolved.
9. The process of breaking or resolving emulsions of mineral oil and Water comprising adding thereto a sulfonated mineral oil, a fatty 011 and phenol, and causing such added materials to act u on the emulsion until such emulsion is bro en or resolved.
10. The process of breaking or resolving emulsions of mineral oil and-water compris- 16. A reagent for breaking or resolving emulsions of mineral oil and water containing a sulfonated-mineral oil and cottonseed oil.
I 17. A reagent for breaking or resolving emulsions of mineral oil and water containing a sulfonated mineral oil, a fatty acid glycerid, and phenol.
18. A reagent for breaking or resolving emulsions of mineral oil and Water containing a sulfonated mineral oil and a fatty acid glycerid in the proportions of about 1 to 4 parts by weight of the former to 2 to 10 parts by Weight of the latter.
19. A reagent for breaking or resolving emulsions of mineral oil and water containing a sulfonated mineral oil and a fatty oil in the proportions of about two parts by weight of the former to one part by weight of the latter.
20. A reagent for breaking or resolving emulsions of mineral oil and water containing a sulfonated mineral oil, a fatty acid glycerid and phenol in the proportions of about 2 parts by Weight of the sulfonated mineral oil, 1 part by weight of the fatty acid glycerid and .09 to .3 parts by weight of the phenol. In testimony whereof I aflix my signature.
' FREDERICK H. PENN.
ing adding thereto a sulfonated mineral oil and a fatty acid glycerid,-heating themixture, and causing such added materials to act up the emulsion until such emulsion is broken or resolved.
11. A rea ent for breaking or resolving emulsions o mineral oil and water containing an acid derivative of a mineral oil and a fatty acid glycerid.
'12. A reagent for breaking or resolving emulsions of mineral oil and water contain-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77981A US1758802A (en) | 1925-12-28 | 1925-12-28 | Process of resolving oil emulsions and reagents therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77981A US1758802A (en) | 1925-12-28 | 1925-12-28 | Process of resolving oil emulsions and reagents therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1758802A true US1758802A (en) | 1930-05-13 |
Family
ID=22141144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US77981A Expired - Lifetime US1758802A (en) | 1925-12-28 | 1925-12-28 | Process of resolving oil emulsions and reagents therefor |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1758802A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486493A (en) * | 1947-01-09 | 1949-11-01 | Tidewater Associated Oil Compa | Oil compositions |
| US2793193A (en) * | 1955-11-25 | 1957-05-21 | Union Oil Co | Sludge treatment |
-
1925
- 1925-12-28 US US77981A patent/US1758802A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486493A (en) * | 1947-01-09 | 1949-11-01 | Tidewater Associated Oil Compa | Oil compositions |
| US2793193A (en) * | 1955-11-25 | 1957-05-21 | Union Oil Co | Sludge treatment |
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