US2411160A - Beneficiating mineral oils - Google Patents
Beneficiating mineral oils Download PDFInfo
- Publication number
- US2411160A US2411160A US374203A US37420341A US2411160A US 2411160 A US2411160 A US 2411160A US 374203 A US374203 A US 374203A US 37420341 A US37420341 A US 37420341A US 2411160 A US2411160 A US 2411160A
- Authority
- US
- United States
- Prior art keywords
- oil
- phosphorus
- nut shell
- cashew nut
- reaction product
- 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
- 239000002480 mineral oil Substances 0.000 title description 21
- 239000003921 oil Substances 0.000 description 21
- 235000019198 oils Nutrition 0.000 description 21
- 235000010446 mineral oil Nutrition 0.000 description 17
- 244000226021 Anacardium occidentale Species 0.000 description 16
- 235000020226 cashew nut Nutrition 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 14
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 3
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 3
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 3
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 description 3
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 3
- 235000014571 nuts Nutrition 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000010466 nut oil Substances 0.000 description 2
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- -1 alkyl sulphates Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CYGDSXFTXXFMNI-OTYYAQKOSA-N hydrofuramide Chemical compound C=1C=COC=1/C=N/C(C=1OC=CC=1)\N=C\C1=CC=CO1 CYGDSXFTXXFMNI-OTYYAQKOSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/067—Polyaryl amine alkanes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/28—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/12—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy
- C10M2223/121—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions obtained by phosphorisation of organic compounds, e.g. with PxSy, PxSyHal or PxOy of alcohols or phenols
Definitions
- the cashew nut shell oil is particularly advantageou as starting material. Chemically it is a phenol containing an unsaturated aliphatic side chain, which is known as cardanol, Other phenols having unsaturated aliphatic side chains may be employed in some cases. Temperatures of reaction may be 200-450 F., preferably around 350 F., and the time of reaction may be up to six hours, preferably about one hour. As aboveindicated, the amount of phosphorus sulphide or the like may vary. such as up to 40 per cent, depending upon the extent of properties desired in the product. The nut shell oil or the like may be diluted with mineral oil or other solvent before reacting with the phosphorus sulphide or the like. The product is ultimately desirably settled or centrifuged, and where preferred a final acid or clay treatment or both may be applied.
- the mineral oil treated with the addition prod uct may be of character desired, for instance a mineral oil of 45 to 200 sec. Saybolt Universal at 210" F. And, the amount of the addition agent employed may be for instance 0.1-10 per cent.
- the present products are not only compatible with organic inhibitors, such as hydrof-uramide.
- reaction product of cashew nut oil, and polymerization and chlorinated derivatives thereof with a phosphorus sulfide is to be distinguished from a sulfurization reaction with elemental sulfur or a sulfurlzing agent capable of yielding elemental sulfur under the conditions of the reaction, and the latter reaction is not included within the invention.
- a mineral oil beneficiating component comprising the reaction product of phosphorus sulphlde and cashew nut shell oil.
- a lubricant comprising a mineral oil and a small amount of the reaction product of a phosphorus sulfide and a chlorinated phenol containing an unsaturated aliphatic side chain.
- a lubricant comprising a hydrocarbon oil and a small quantity of, an oil-soluble reaction product of cardanol and a phosphorus sulfide,
- a mineral oil beneficiating component comprising the reaction product of phosphorus sulphlde and cashew nut shell oil.
- a lubricant comprising a mineral oil and a small amount of the reaction product of a phosphorus sulfide and a chlorinated phenol containing an unsaturated aliphatic side chain.
- a lubricant comprising a hydrocarbon oil and a small quantity of, an oil-soluble reaction product of cardanol and a phosphorus sulfide,
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)
- Lubricants (AREA)
Description
Patented Nov. 19, 1946 BENEFIOIATING MINERAL OILS Everett 0. Hughes, Cleveland Heights, Ohio, assignor to The Standard Oil Company, Cleveland, Ohio, a corporation of Ohio No Drawing.
Application January 13, 194i,
Serial No. 374,203 11 Claims. (01. 2:52-40:15
Mineral oils while having certain fundamental properties fitting them for important industrial usages, have also certain limitations which prevent desirably extended utility in various directions. In an effort to help out some of the deficiencies, addition agents of different character have been suggested and used to some extent. VlThile some of these have utility, a particular difflculty has been that an agent which aifords some improvement in one property of the oil is unable to give away assistance in other respects, and in practice it has been necessary to employ several addition agents for respectively different effects desired. In accordance with the present invention, however, an agent may be had to perform several heneflciating functions simultaneously in combination with mineral oils.
To the accomplishment of the foregoing and related ends, the invention, then, comprises the features hereinafter fully described. and particularly pointed out in the claims, the following description setting forth in detail certain illustrative embodiments of the invention, these being indicative however, of but a few of the various ways in which the principle of the invention may be employed.
The invention will be readily understood by reference to an example of its practice: Oil from the shells of cashew nuts, preferably the distillate grade, although the crude oil may be employed if desired, is heated with about 20 per cent by weight of phosphorus pentasulphide for an hour at 350 F. The product is settled or centrifuged, and is incorporated in amount of 0.5 per cent in a mineral oil such as a S. A. E. 20 petroleum lubricating oil of Mid-Continent stock. This oil, tested y the accelerated test method involving exposure a temperature of 310 F. and metal surfaces, air
ing blown through the oil at the rate of 30 ll rs per hour for 65 hours, showed a viscosity increase of 102',sec. Saybolt Universal at 100 F., naphtha insolubles 0.4 per cent, lacquer formation 15.5, and appearance rating H. In contrast, the oil without the addition agent, subjected to the same test, showed viscosity increase 362 sec. Saybolt Universal at 100 F naphtha insolubles 4.1 per cent, lacquer formation 87.4 mg., and appearance rating minus.
This composition also has pour-point depressing action and v.1. improving action The higher the state of polymerization which takes place in the forming of the product, the more pronounced are these properties, and the total properties of the product may thus be gauged as closely as desired, the degree of polymerization being controlled by the temperature of reaction, the per cent of phosphorus sulphide employed, etc. Polymerization may be effected also by alkyl sulphates or aldehydes, or both, if desired.
The cashew nut shell oil is particularly advantageou as starting material. Chemically it is a phenol containing an unsaturated aliphatic side chain, which is known as cardanol, Other phenols having unsaturated aliphatic side chains may be employed in some cases. Temperatures of reaction may be 200-450 F., preferably around 350 F., and the time of reaction may be up to six hours, preferably about one hour. As aboveindicated, the amount of phosphorus sulphide or the like may vary. such as up to 40 per cent, depending upon the extent of properties desired in the product. The nut shell oil or the like may be diluted with mineral oil or other solvent before reacting with the phosphorus sulphide or the like. The product is ultimately desirably settled or centrifuged, and where preferred a final acid or clay treatment or both may be applied.
As a further refinement of the invention, the cashew nut oil or the like is chlorinated more or less extensively as desired, before being subjected to the polymerizing action or the treatment with a phosphorus sulphide, as described heretofore.
The mineral oil treated with the addition prod uct may be of character desired, for instance a mineral oil of 45 to 200 sec. Saybolt Universal at 210" F. And, the amount of the addition agent employed may be for instance 0.1-10 per cent. The present products are not only compatible with organic inhibitors, such as hydrof-uramide.
tetramethyl diamino diphenyl methane. etc. but
with particular advantage may be associated therewith.
The reaction product of cashew nut oil, and polymerization and chlorinated derivatives thereof with a phosphorus sulfide is to be distinguished from a sulfurization reaction with elemental sulfur or a sulfurlzing agent capable of yielding elemental sulfur under the conditions of the reaction, and the latter reaction is not included within the invention.
Other modes of applying the principle of the invention may be employed, change being made as regards the details described, provided the features stated in any of the following claims, or the equivalent of such, be employed.
I therefore particularly point out and distinctly claim as my invention:
\l. A mineral oil beneflciated with a small amount of the reaction product of c'ashew'nut shell oil and phosphorus pentasulphide.
2. A mineral oil beneficiated with a small amount of the reaction product of phosphorus pentasulphide and a, phenol'.containing an unsaturated aliphatic side chainiof the kind occurring in cashew nut shell oil.. I
3. A mineral oil beneficiating component comprising the reaction product of phosphorus sulphlde and cashew nut shell oil.
4. A mineral oil beneflgiated with a small amount of a phosphorus pjentasulphide reacted phenol containing an unsaturated aliphatic side 4 cashew nut shell oil and phosphorus pentasulphide.
8. A mineral oil beneficiated with a small amount of the reaction product of a phosphorus sulphide and chlorinated cashew nut shell oil.
9. A mineral oil beneficiated with a small amount of the reaction product of phosphorus pe'ntasulphide and a chlorinated phenol containing an unsaturated aliphatic side chain of the kind occurring in cashew nut shell oil.
10. A lubricant comprising a mineral oil and a small amount of the reaction product of a phosphorus sulfide and a chlorinated phenol containing an unsaturated aliphatic side chain.
11. A lubricant comprising a hydrocarbon oil and a small quantity of, an oil-soluble reaction product of cardanol and a phosphorus sulfide,
Certificate of Correction Patent No. 2,411,1e0Q
EVERETT c. HUGHES Novemberlil, 1946.
It is hereby certified that error appears in the rinted specification oi the above numbered patent requiring correction as follows:
olumn 4, line 14, claim 10, after the word chain" and before the period insert of the kind occurring in cashew nut shell ml; and that the said Letters Patent should be read with this correction therein that. the same may conform to the record of the case in the Patent Oflice.
Signed and sealed this 4th day of February, A. D. 1947.
LESLIE FRAZER,
First Ambient flommiefimfi of PM.
2. A mineral oil beneficiated with a small amount of the reaction product of phosphorus pentasulphide and a, phenol'.containing an unsaturated aliphatic side chainiof the kind occurring in cashew nut shell oil.. I
3. A mineral oil beneficiating component comprising the reaction product of phosphorus sulphlde and cashew nut shell oil.
4. A mineral oil beneflgiated with a small amount of a phosphorus pjentasulphide reacted phenol containing an unsaturated aliphatic side 4 cashew nut shell oil and phosphorus pentasulphide.
8. A mineral oil beneficiated with a small amount of the reaction product of a phosphorus sulphide and chlorinated cashew nut shell oil.
9. A mineral oil beneficiated with a small amount of the reaction product of phosphorus pe'ntasulphide and a chlorinated phenol containing an unsaturated aliphatic side chain of the kind occurring in cashew nut shell oil.
10. A lubricant comprising a mineral oil and a small amount of the reaction product of a phosphorus sulfide and a chlorinated phenol containing an unsaturated aliphatic side chain.
11. A lubricant comprising a hydrocarbon oil and a small quantity of, an oil-soluble reaction product of cardanol and a phosphorus sulfide,
Certificate of Correction Patent No. 2,411,1e0Q
EVERETT c. HUGHES Novemberlil, 1946.
It is hereby certified that error appears in the rinted specification oi the above numbered patent requiring correction as follows:
olumn 4, line 14, claim 10, after the word chain" and before the period insert of the kind occurring in cashew nut shell ml; and that the said Letters Patent should be read with this correction therein that. the same may conform to the record of the case in the Patent Oflice.
Signed and sealed this 4th day of February, A. D. 1947.
LESLIE FRAZER,
First Ambient flommiefimfi of PM.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US374203A US2411160A (en) | 1941-01-13 | 1941-01-13 | Beneficiating mineral oils |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US374203A US2411160A (en) | 1941-01-13 | 1941-01-13 | Beneficiating mineral oils |
Publications (1)
Publication Number | Publication Date |
---|---|
US2411160A true US2411160A (en) | 1946-11-19 |
Family
ID=23475766
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US374203A Expired - Lifetime US2411160A (en) | 1941-01-13 | 1941-01-13 | Beneficiating mineral oils |
Country Status (1)
Country | Link |
---|---|
US (1) | US2411160A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2520331A (en) * | 1950-08-29 | Anacardic-chloroanacardic | ||
US2954720A (en) * | 1954-12-09 | 1960-10-04 | Domeshek Sol | Rangefinder with adjustable reticle |
US5916850A (en) * | 1997-11-06 | 1999-06-29 | Indian Oil Corporaton Limited | Multifunctional additives from cashew nut shell liquid |
-
1941
- 1941-01-13 US US374203A patent/US2411160A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2520331A (en) * | 1950-08-29 | Anacardic-chloroanacardic | ||
US2954720A (en) * | 1954-12-09 | 1960-10-04 | Domeshek Sol | Rangefinder with adjustable reticle |
US5916850A (en) * | 1997-11-06 | 1999-06-29 | Indian Oil Corporaton Limited | Multifunctional additives from cashew nut shell liquid |
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