US2125961A - Color stable viscous hydrocarbon oil - Google Patents
Color stable viscous hydrocarbon oil Download PDFInfo
- Publication number
- US2125961A US2125961A US159370A US15937037A US2125961A US 2125961 A US2125961 A US 2125961A US 159370 A US159370 A US 159370A US 15937037 A US15937037 A US 15937037A US 2125961 A US2125961 A US 2125961A
- Authority
- US
- United States
- Prior art keywords
- aluminum
- group
- zinc
- color
- radical
- 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
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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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/027—Neutral salts thereof
-
- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/06—Groups 3 or 13
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/135—Steam engines or turbines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/17—Electric or magnetic purposes for electric contacts
Definitions
- This invention relates to a method of protecting viscous hydrocarbon oils against discoloration and. in particular, to the color stabilization of hydrocarbon oils, such as lubricating oils, turbine oils, electrical insulating oils and the like.
- Hydrocarbon oils of the type defined deteriorate in colorand appearance during use and when kept in storage over long periods. Since the deterioration in color and appearance is accompanied by more or less impairment of the oils in other respects, it is desirable that such oils be inhibited against discoloration.
- These metallic alcoholates or thio alcoholates have the general formula M(XR) 3 0r M(XR) z in which M is a metal selected from the group consisting of aluminum and zinc, X is an element selected from the group consisting of oxygen and sulfur, and R is a radical selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and a hydro aryl radical.
- the alkyl radical is preferably one containing at least three carbon atoms in the radical.
- the alcoholates or thio alcoholates may be prepared by treating themetal with an alcohol or the following specific example.
- laurylmercaptan using iodine or tin tetra chloride as a carrier.
- aluminum butylate may be prepared by treating aluminum with butyl alcohol in the presence of iodine. The reaction which takes place may be illustrated by the following equation:
- the corresponding thio alcoholates may be prepared by substituting the corresponding mercaptan for the alcohol in the above equation.
- a color stable viscous hydrocarbon oil containing from about 0.01% to about 5% of a metal alcoholate selected from the group consisting of compounds having the general formulas M(XR) a and M(XR.) 2 in which M is a metal selected from the group consisting of aluminum and zinc, X is an element selected from the group consisting of oxygen and sulfur, and R is a radical selected from the group consisting of an alkyl radical, an
- aryl radical an aralkyl radical and a hydro aryl radical.
- a color stable viscous hydrocarbon oil containing a small proportion of a metal alcoholate selected from the group consisting of compounds having the general formulas M(OR) a and M(OR) a in which M is a metal selected from the group consisting of aluminum and zinc and R is a radical selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical, and a hydro aryl radical.
- the method of color stabilizing viscous hydrocarbon oils of the class consisting of lubricating oils, turbine oils and electrical insulating oils which comprises adding thereto a small proportion of a metal alcoholateselected from the group consisting of compounds having the general and M(OR): in which M is a metal selected from the group consisting of aluminum and zinc, and R is an alkyl radical containing at least three carbon atoms.
- a color stable viscous hydrocarbon oil which comprises addingthereto from about 0.01% to about 0.5% of a metal alcoholate selected from the group consisting of aluminum butylate and zinc butylate.
- the method of stabilizing viscous hydrocarbon oils which comprises adding thereto a small proportion of a metal alc'oholate selected from the group consisting of compounds having the general formulas M(OR): and M is a metal selected from the group consisting of aluminum and zinc, and R is an alkyl radical having at least 3 carbon atoms.
- a color stable viscous hydrocarbon oil containing about from 0.001% to about 0.5% aluminum laurylate.
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 Aug. 9, 1938 PATENT OFFICE COLOR STABLE VIECIZSUS HYDROCARBON Bernard H. Shoemaker and Clarence M. Loane,
Hammond, Ind.,
assignors to Standard Oil Company, Chicago,.Ill., a corporation of Indiana No Drawing. Application August 16, 1937-,
. Serial No.159,370
10 Claims.
This invention relates to a method of protecting viscous hydrocarbon oils against discoloration and. in particular, to the color stabilization of hydrocarbon oils, such as lubricating oils, turbine oils, electrical insulating oils and the like.
Hydrocarbon oils of the type defined deteriorate in colorand appearance during use and when kept in storage over long periods. Since the deterioration in color and appearance is accompanied by more or less impairment of the oils in other respects, it is desirable that such oils be inhibited against discoloration.
We have found that by adding to such oils from about 0.001% to about 5%, and'preferably from about 0.01% to about 0.5% of certain metallic alcoholates and thio alcoholates, the deterioration of color is reduced to a large extent. These metallic alcoholates or thio alcoholates have the general formula M(XR) 3 0r M(XR) z in which M is a metal selected from the group consisting of aluminum and zinc, X is an element selected from the group consisting of oxygen and sulfur, and R is a radical selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical and a hydro aryl radical. The alkyl radical is preferably one containing at least three carbon atoms in the radical.
As specific examples of the alcoholates or thio alcoholates which may be effectively used are:
Aluminum propylate, Al(OCaH1) 3 Aluminum butylate, AI(OC4H9) 3 Aluminum amylate, Al (0052111) 3 Aluminum laurylate, Al(OC12I-l2t) 3 Aluminum phenylate, Al(OCtH5)a Aluminum cyclo hexylate, Al(O(cyclo)CtH1i)a Aluminum thio butylate, Al(SC4H9) a Zinc propylate, Zn (OCaH'D 21 Zinc butylate, Zn(OC4I-I9) 2 Zinc amylate, Zn(OC.-.H11)z Zinc laurylate, Zn(OC12I-Iza) a Zinc phenylate, Zn(OCaH5) a Zinc cyclo hexylate, Zn(0(cyclo) Cal-I11) 2 Zinc thio butylate, Zn(SC4H9) 2 Our invention contemplates the use of the cor responding isomers of any of the above compounds and mixtures of the alcoholates and/or thio alcoholates, such as ates which are a mixture of alkyl alcoholates having 12 to 18 carbon atoms in the alkyl chain but predominately dodecyl and tetra decyl derivatives.
The alcoholates or thio alcoholates may be prepared by treating themetal with an alcohol or the following specific example. An S.
for example the laurylmercaptan using iodine or tin tetra chloride as a carrier. For example, aluminum butylate may be prepared by treating aluminum with butyl alcohol in the presence of iodine. The reaction which takes place may be illustrated by the following equation:
The corresponding thio alcoholates may be prepared by substituting the corresponding mercaptan for the alcohol in the above equation.
The efficacy of our invention is illustrated by A. E. 20 motor oil prepared from Mid-Continent crude oil, and the same oil containing (1) 0.25% of aluminum butylate and (2) 0.25% of zinc butylate were heated at 220 F. for a period of several days and the color periodically determined with the following results:
, 220 F. color stability,
N. P. A. color Oil initial 2 days 4 days Control l 3.0 4.8 3+ Control-+0.25% zinc butylate 3.0 3. 7 Control+0.25% aluminum butylate 3. 0 3. 4 3. 7
The effectiveness of aluminum and zinc alcoholates in inhibiting color formation is well demonstrated by the above results, in which the color of the control after {1 days was too dark to transmit light, while the sample with 0.25% aluminum butylate had substantially the same color after 4 days that it had at the start of the test.
While we have described our invention by reference to a preferred embodiment thereof we do not wish to be limited to the specific examples which are merely set forth to illustrate our invention and not intended to be a limitation thereof, except insofar as defined in the appended claims, which should be given the broadest interpretation permitted by the prior art.
We claim:
1. A color stable viscous hydrocarbon oil containing from about 0.01% to about 5% of a metal alcoholate selected from the group consisting of compounds having the general formulas M(XR) a and M(XR.) 2 in which M is a metal selected from the group consisting of aluminum and zinc, X is an element selected from the group consisting of oxygen and sulfur, and R is a radical selected from the group consisting of an alkyl radical, an
aryl radical. an aralkyl radical and a hydro aryl radical.
2. A color stable viscous hydrocarbon oil containing a small proportion of a metal alcoholate selected from the group consisting of compounds having the general formulas M(OR) a and M(OR) a in which M is a metal selected from the group consisting of aluminum and zinc and R is a radical selected from the group consisting of an alkyl radical, an aryl radical, an aralkyl radical, and a hydro aryl radical. g
3. A color stable viscous hydrocarbon oil containing a small proportion of a.meta1 alcoholate selected from the group consisting of compounds having the general formulas M(OR): and M(ORM in which M is a metal selected from the group consisting of aluminum and zinc, and R is an alkyl radical containing at least three carbon atoms.
viscous hydrocarbon oil con- 0.01% to about 0.5% of aluviscous hydrocarbon oil con- 0.01% to about 0.5% of zinc portion of a metallic alcoholate selected from the group consisting of compounds having the general formulas"M(XR)a and M(XR): in which M is a metal selected from the group consisting of aluformulas M OR) 3 minum and zinc, X is an element selected from the group consisting of oxygen and sulfur, and R e is a radical selected from the group consisting of an alkyl radical. an aryl radical, an aralkyl radical and a hydro airy] radical.
7. The method of color stabilizing viscous hydrocarbon oils of the class consisting of lubricating oils, turbine oils and electrical insulating oils which comprises adding thereto a small proportion of a metal alcoholateselected from the group consisting of compounds having the general and M(OR): in which M is a metal selected from the group consisting of aluminum and zinc, and R is an alkyl radical containing at least three carbon atoms.
8. A color stable viscous hydrocarbon oil which comprises addingthereto from about 0.01% to about 0.5% of a metal alcoholate selected from the group consisting of aluminum butylate and zinc butylate.
9. The method of stabilizing viscous hydrocarbon oils which comprises adding thereto a small proportion of a metal alc'oholate selected from the group consisting of compounds having the general formulas M(OR): and M is a metal selected from the group consisting of aluminum and zinc, and R is an alkyl radical having at least 3 carbon atoms.
10. A color stable viscous hydrocarbon oil containing about from 0.001% to about 0.5% aluminum laurylate.
BERNARD H. SHOEMAKER. CLARENCE M. LOANE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US159370A US2125961A (en) | 1937-08-16 | 1937-08-16 | Color stable viscous hydrocarbon oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US159370A US2125961A (en) | 1937-08-16 | 1937-08-16 | Color stable viscous hydrocarbon oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2125961A true US2125961A (en) | 1938-08-09 |
Family
ID=22572320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US159370A Expired - Lifetime US2125961A (en) | 1937-08-16 | 1937-08-16 | Color stable viscous hydrocarbon oil |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2125961A (en) |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2461335A (en) * | 1938-12-16 | 1949-02-08 | Standard Oil Dev Co | Organometallic compound |
| US2472504A (en) * | 1939-12-30 | 1949-06-07 | Standard Oil Dev Co | Organometallic compound |
| US2480743A (en) * | 1946-05-03 | 1949-08-30 | Krantz | Basic aluminum salt of an aliphatic amino acid and method of preparing the same |
| US2491116A (en) * | 1943-11-16 | 1949-12-13 | Standard Oil Dev Co | Friedel-crafts type catalyst complexes and their preparation |
| US2493987A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Aluminum salts of alkylated phenol sulfides |
| US2493986A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Heavy metal salts of alkyl phenol sulfides and method of making same |
| US2543734A (en) * | 1948-11-08 | 1951-02-27 | California Research Corp | Mineral lubricating oil containing a combination of metal salts |
| US2566195A (en) * | 1948-10-09 | 1951-08-28 | Monsanto Chemicals | Dielectric composition of halogenated aromatic compound and aluminum isopropylate asa corrosion inhibitor |
| US2656311A (en) * | 1949-10-31 | 1953-10-20 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2673162A (en) * | 1950-08-01 | 1954-03-23 | Eastman Kodak Co | Stabilized lower fatty acid ester of cellulose |
| US2713546A (en) * | 1952-01-25 | 1955-07-19 | Eastman Kodak Co | Stabilized lower fatty acid ester of cellulose |
| US2714087A (en) * | 1949-10-31 | 1955-07-26 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2735857A (en) * | 1956-02-21 | Uranium alkoxy compoundsand method | ||
| US2768140A (en) * | 1953-03-05 | 1956-10-23 | Shell Dev | Oil-soluble sodium hydrocarbyl phenates as color stabilizers for mineral lubricatingoils |
| US2988498A (en) * | 1956-01-04 | 1961-06-13 | Exxon Research Engineering Co | Processes for producing alumina containing materials |
| US3256188A (en) * | 1963-06-21 | 1966-06-14 | Socony Mobil Oil Co Inc | Oil-soluble metal halide complexes and improved lubricating oil compositions containing same |
| US3277002A (en) * | 1961-07-17 | 1966-10-04 | Continental Oil Co | Process for stably dispersing metal compounds |
| US3490737A (en) * | 1966-08-26 | 1970-01-20 | Monsanto Co | Functional fluid compositions |
| US3856841A (en) * | 1973-03-28 | 1974-12-24 | Merkl George | Aluminum organoiodides |
| US3996346A (en) * | 1975-03-18 | 1976-12-07 | Dominic Thomas Staffier | Composition for reducing bodily odor and perspiration |
| USRE29389E (en) * | 1973-03-28 | 1977-09-06 | Method of preparing aluminum organoiodides | |
| US4052429A (en) * | 1975-01-13 | 1977-10-04 | Merkl George C | Method of forming a compound containing aluminum and glycerol |
-
1937
- 1937-08-16 US US159370A patent/US2125961A/en not_active Expired - Lifetime
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2735857A (en) * | 1956-02-21 | Uranium alkoxy compoundsand method | ||
| US2461335A (en) * | 1938-12-16 | 1949-02-08 | Standard Oil Dev Co | Organometallic compound |
| US2493987A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Aluminum salts of alkylated phenol sulfides |
| US2493986A (en) * | 1939-12-27 | 1950-01-10 | Standard Oil Dev Co | Heavy metal salts of alkyl phenol sulfides and method of making same |
| US2472504A (en) * | 1939-12-30 | 1949-06-07 | Standard Oil Dev Co | Organometallic compound |
| US2491116A (en) * | 1943-11-16 | 1949-12-13 | Standard Oil Dev Co | Friedel-crafts type catalyst complexes and their preparation |
| US2480743A (en) * | 1946-05-03 | 1949-08-30 | Krantz | Basic aluminum salt of an aliphatic amino acid and method of preparing the same |
| US2566195A (en) * | 1948-10-09 | 1951-08-28 | Monsanto Chemicals | Dielectric composition of halogenated aromatic compound and aluminum isopropylate asa corrosion inhibitor |
| US2543734A (en) * | 1948-11-08 | 1951-02-27 | California Research Corp | Mineral lubricating oil containing a combination of metal salts |
| US2656311A (en) * | 1949-10-31 | 1953-10-20 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2714087A (en) * | 1949-10-31 | 1955-07-26 | Gulf Research Development Co | Stabilization of phenol alkylates |
| US2673162A (en) * | 1950-08-01 | 1954-03-23 | Eastman Kodak Co | Stabilized lower fatty acid ester of cellulose |
| US2713546A (en) * | 1952-01-25 | 1955-07-19 | Eastman Kodak Co | Stabilized lower fatty acid ester of cellulose |
| US2768140A (en) * | 1953-03-05 | 1956-10-23 | Shell Dev | Oil-soluble sodium hydrocarbyl phenates as color stabilizers for mineral lubricatingoils |
| US2988498A (en) * | 1956-01-04 | 1961-06-13 | Exxon Research Engineering Co | Processes for producing alumina containing materials |
| US3277002A (en) * | 1961-07-17 | 1966-10-04 | Continental Oil Co | Process for stably dispersing metal compounds |
| US3256188A (en) * | 1963-06-21 | 1966-06-14 | Socony Mobil Oil Co Inc | Oil-soluble metal halide complexes and improved lubricating oil compositions containing same |
| US3490737A (en) * | 1966-08-26 | 1970-01-20 | Monsanto Co | Functional fluid compositions |
| US3856841A (en) * | 1973-03-28 | 1974-12-24 | Merkl George | Aluminum organoiodides |
| USRE29389E (en) * | 1973-03-28 | 1977-09-06 | Method of preparing aluminum organoiodides | |
| US4052429A (en) * | 1975-01-13 | 1977-10-04 | Merkl George C | Method of forming a compound containing aluminum and glycerol |
| US3996346A (en) * | 1975-03-18 | 1976-12-07 | Dominic Thomas Staffier | Composition for reducing bodily odor and perspiration |
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