US2792346A - Stabilized diester lubricant - Google Patents
Stabilized diester lubricant Download PDFInfo
- Publication number
- US2792346A US2792346A US463806A US46380654A US2792346A US 2792346 A US2792346 A US 2792346A US 463806 A US463806 A US 463806A US 46380654 A US46380654 A US 46380654A US 2792346 A US2792346 A US 2792346A
- Authority
- US
- United States
- Prior art keywords
- percent
- lubricant
- diester
- carbon atoms
- dilauryl
- 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
- 239000000314 lubricant Substances 0.000 title claims description 24
- 150000005690 diesters Chemical class 0.000 title description 13
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 claims description 8
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 7
- 229950000688 phenothiazine Drugs 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical group 0.000 claims 1
- KUUNNVBBPBDFJZ-UHFFFAOYSA-N 1-dodecylselanyldodecane Chemical compound CCCCCCCCCCCC[Se]CCCCCCCCCCCC KUUNNVBBPBDFJZ-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- XWVQUJDBOICHGH-UHFFFAOYSA-N dioctyl nonanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCC(=O)OCCCCCCCC XWVQUJDBOICHGH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- CJFLBOQMPJCWLR-UHFFFAOYSA-N bis(6-methylheptyl) hexanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCC(=O)OCCCCCC(C)C CJFLBOQMPJCWLR-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000000571 coke Substances 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 150000003346 selenoethers Chemical class 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 229940067597 azelate Drugs 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 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
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- 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
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- 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
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
-
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
-
- 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
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2040/12—Gas-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
- C10N2040/12—Gas-turbines
- C10N2040/13—Aircraft turbines
Definitions
- This invention relates to a diester synthetic lubricant of improved thermal and oxidation stability.
- Specification MiL-L-7808A sets forth properties that must be met by lubricants for jet engines, gas turbines, aircraft, etc. including rigid viscosity requirements at 210 F. and -65 F., low temperature storage stability, oxidation-corrosion resistance, evaporation loss at 400 F., a 10,000 R. P. M. gear test and a panel-coking test conducted at 600 F. These requirements are met by certain diester synthetic lubricants such, for example, as dioctyl sebacate, azelate and/or adipate containing about percent tricresyl phosphate, about .5 percent phenothiazine with or without a viscosity index improver.
- An object of this invention is to provide an improved diester synthetic lubricant which not only meets the MIL-L-7808A specification (except for possible corrosion requirements on certain metals under certain conditions) but which is of improved stability with respect to oxidation and thermal degradation. Another object is to provide such a lubricant which gives less coke deposit in the 600 F. panel-coking test. A further object is to provide a lubricant of a higher load carrying capacity, particularly as a gear lubricant operating at high temperature. Other objects will be apparent as the detailed description of the invention proceeds.
- a lubricant which meets most of the MIL-L-7808A requirements and, at the same time, possesses outstanding stability against oxidation and thermal degradation can be obtained by adding to a suitable base fluid dilauryl selenide in amounts of about .5 to 5 percent, preferably about 2 percent.
- a suitable base fluid dilauryl selenide in amounts of about .5 to 5 percent, preferably about 2 percent.
- An example of the new lubricant composition is as follows:
- dioctyl azelate may use diisooctyl adipate, or a mixture of the adipate with azelate in any desired proportions.
- the diester component is preferably employed in amounts in the range of 90 to 95 percent and, while the octyl esters are preferred, other diesters may be employed, said diesters preferably being of dicarboxylic acids containing about 4 to 8 carbon atoms, the added ester groups each having a chain length of about 5 to 15 carbon atoms.
- the tricresyl phosphate may be employed in amounts of about 4 to 6 percent and this component may be replaced by other organic phosphates of similar properties.
- the phenotiazine may be employed in amounts ranging from about .3 to .7 percent.
- the dilauryl 7 selenide is preferably employed in amounts of about 2. percent or in the range of about .5 to 5 percent and other 2,792,346 Patented May 14, 1957 organic selenides of approximately the same carbon chain length as the dilauryl selenide may be used.
- the lubricant may be prepared by simply mixing the components at a temperature in the range of about 100 to 150 F. Alternately, the dilauryl selenide may be warmed to its melting point and admixed in the described amount with a previously formed diester lubricant.
- the lubricant composition described in the foregoing example was tested for lubricating the plungers and bushings of a high temperature pump on a jet engine and found to increase by about three times the length of running obtainable with the base lubricant in the absence of the dilauryl selenide.
- the high temperature in this case was a 200 to 300 F. oil sump temperature but, with close clearances and high speed operation, the actual temperature of the oil between movmg parts was probably much higher.
- the dilauryl selenide-containing lubricant is slightly corrosive to silver and copper under high temperature test conditions, no corrosion problem was apparent in the test on the jet pump.
- dilauryl selenide is substantially nontoxic as opposed to the organic selenides which are quite poisonous; however, it is recommended that adequate safety precautions be employed in handling this material, particularly when it is subjected to high temperatures.
- a lubricant consisting essentially of about to percent of a diester of a dicarboxylic acid containing about 4 to 8 carbon atoms per molecule, the added ester groups having a carbon chain length of about 5 to 15 carbon atoms, about 4 to 6 percent tricresyl phosphate, about .3 to .7 percent phenothiazine and about .5 to 5 weight percent dilauryl selenide.
- the lubricant of claim 1 wherein the diester is a mixture of diisooctyl adipate and dioctyl azelate.
- a lubricant consisting essentially of a diester of a dicarboxylic acid containing about 4 to 8 carbon atoms, the added ester groups having a chain length of about 5 to 15 carbon atoms, about 5 weight percent of tricresyl phosphate, about .5 weight percent phenothiazine and about 2 percent dilauryl selenide.
- a lubricant having approximately the following composition: 92.5 percent dioctyl azelate, 5 percent tricresyl phosphate, .5 percent phenothiazine, and 2 percent dilauryl selenide.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
STABILIZED DESTER LUBRICANT Albert W. Lindert, Homewood, llL, assignor to Standard Oil Company, Chicago, 1111., a corporation of iridiana No Drawing. Application October 21, 1954, Serial No. 463,806
6 Claims. (Cl. 25246.7)
This invention relates to a diester synthetic lubricant of improved thermal and oxidation stability.
Specification MiL-L-7808A sets forth properties that must be met by lubricants for jet engines, gas turbines, aircraft, etc. including rigid viscosity requirements at 210 F. and -65 F., low temperature storage stability, oxidation-corrosion resistance, evaporation loss at 400 F., a 10,000 R. P. M. gear test and a panel-coking test conducted at 600 F. These requirements are met by certain diester synthetic lubricants such, for example, as dioctyl sebacate, azelate and/or adipate containing about percent tricresyl phosphate, about .5 percent phenothiazine with or without a viscosity index improver. However, when such compositions are employed as lubricants for moving parts operating at close clearances and/or carrying heavy loads at high temperatures, they are subject to undesirable oxidation and/or thermal degradation which may result in seizure of moving parts. An object of this invention is to provide an improved diester synthetic lubricant which not only meets the MIL-L-7808A specification (except for possible corrosion requirements on certain metals under certain conditions) but which is of improved stability with respect to oxidation and thermal degradation. Another object is to provide such a lubricant which gives less coke deposit in the 600 F. panel-coking test. A further object is to provide a lubricant of a higher load carrying capacity, particularly as a gear lubricant operating at high temperature. Other objects will be apparent as the detailed description of the invention proceeds.
It has been found that a lubricant which meets most of the MIL-L-7808A requirements and, at the same time, possesses outstanding stability against oxidation and thermal degradation can be obtained by adding to a suitable base fluid dilauryl selenide in amounts of about .5 to 5 percent, preferably about 2 percent. An example of the new lubricant composition is as follows:
92.5% dioctyl azelate 5 tricresyl phosphate .5 phenothiazine 2% dilauryl selenide Instead of dioctyl azelate I may use diisooctyl adipate, or a mixture of the adipate with azelate in any desired proportions. The diester component is preferably employed in amounts in the range of 90 to 95 percent and, while the octyl esters are preferred, other diesters may be employed, said diesters preferably being of dicarboxylic acids containing about 4 to 8 carbon atoms, the added ester groups each having a chain length of about 5 to 15 carbon atoms. The tricresyl phosphate may be employed in amounts of about 4 to 6 percent and this component may be replaced by other organic phosphates of similar properties. The phenotiazine may be employed in amounts ranging from about .3 to .7 percent. As above stated, the dilauryl 7 selenide is preferably employed in amounts of about 2. percent or in the range of about .5 to 5 percent and other 2,792,346 Patented May 14, 1957 organic selenides of approximately the same carbon chain length as the dilauryl selenide may be used.
The lubricant may be prepared by simply mixing the components at a temperature in the range of about 100 to 150 F. Alternately, the dilauryl selenide may be warmed to its melting point and admixed in the described amount with a previously formed diester lubricant.
The remarkable stabilizing eflect of the added dilauryl selenide is shown by the results of 600 F. panel-coking tests made on a base fluid containing 94.5 percent dioctyl azelate, 5 percent tricresyl phosphate and .5 percent phenothiazine with the following results:
From the above test data it will be seen that the dilauryl selenide reduced the coke deposit to about one-fourth the level obtained in the absence of stabilizer. Tributyl tin, which might be expected to have a similar result, actually gives about five times as much coke deposit as the base fluid.
The lubricant composition described in the foregoing example was tested for lubricating the plungers and bushings of a high temperature pump on a jet engine and found to increase by about three times the length of running obtainable with the base lubricant in the absence of the dilauryl selenide. The high temperature in this case was a 200 to 300 F. oil sump temperature but, with close clearances and high speed operation, the actual temperature of the oil between movmg parts was probably much higher. Although the dilauryl selenide-containing lubricant is slightly corrosive to silver and copper under high temperature test conditions, no corrosion problem was apparent in the test on the jet pump.
lt is believed that dilauryl selenide is substantially nontoxic as opposed to the organic selenides which are quite poisonous; however, it is recommended that adequate safety precautions be employed in handling this material, particularly when it is subjected to high temperatures.
I claim:
1. A lubricant consisting essentially of about to percent of a diester of a dicarboxylic acid containing about 4 to 8 carbon atoms per molecule, the added ester groups having a carbon chain length of about 5 to 15 carbon atoms, about 4 to 6 percent tricresyl phosphate, about .3 to .7 percent phenothiazine and about .5 to 5 weight percent dilauryl selenide.
2. The lubricant of claim 1 wherein at least a part of the diester is diisooctyl adipate.
3. The lubricant of claim 1 wherein at least a part of the diester is dioctyl azelate.
4. The lubricant of claim 1 wherein the diester is a mixture of diisooctyl adipate and dioctyl azelate.
5. A lubricant consisting essentially of a diester of a dicarboxylic acid containing about 4 to 8 carbon atoms, the added ester groups having a chain length of about 5 to 15 carbon atoms, about 5 weight percent of tricresyl phosphate, about .5 weight percent phenothiazine and about 2 percent dilauryl selenide.
6. A lubricant having approximately the following composition: 92.5 percent dioctyl azelate, 5 percent tricresyl phosphate, .5 percent phenothiazine, and 2 percent dilauryl selenide.
References Cited in the file of this patent UNITED STATES PATENTS 2,167,867 Benning Aug. 1, 1939 2,190,648 Cantrell Feb. 20, 1940 2,398,415 Denison Apr. 16, 1946
Claims (1)
1. A LUBRICANT CONSISTING ESSENTIALLY OF ABOUT 90 TO 95 PERCENT OF A DIESTER OF A DICARBOXYLIC ACID CONTAINING ABOUT 4 TO 8 CARBON ATOMS PER MOLECULE, THE ADDED ESTER GROUPS HAVING A CARBON CHAIN LENGTH OF ABOUT 5 TO 15 CARBON ATOMS, ABOUT 4 TO 6 PERCENT TRICRESYL PHOSPHATE, ABOUT 3 TO 7 PERCENT PHENOTHIAZINE AND ABOUT 5 TO 5 WEIGHT PERCENT DILAURYL SELEMIDE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US463806A US2792346A (en) | 1954-10-21 | 1954-10-21 | Stabilized diester lubricant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US463806A US2792346A (en) | 1954-10-21 | 1954-10-21 | Stabilized diester lubricant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2792346A true US2792346A (en) | 1957-05-14 |
Family
ID=23841433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US463806A Expired - Lifetime US2792346A (en) | 1954-10-21 | 1954-10-21 | Stabilized diester lubricant |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2792346A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2167867A (en) * | 1936-05-07 | 1939-08-01 | Du Pont | Lubricant |
| US2190648A (en) * | 1936-06-09 | 1940-02-20 | Gulf Oil Corp | Lubrication of alloy bearings |
| US2398415A (en) * | 1943-02-22 | 1946-04-16 | California Research Corp | Mineral oil composition and the like |
-
1954
- 1954-10-21 US US463806A patent/US2792346A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2167867A (en) * | 1936-05-07 | 1939-08-01 | Du Pont | Lubricant |
| US2190648A (en) * | 1936-06-09 | 1940-02-20 | Gulf Oil Corp | Lubrication of alloy bearings |
| US2398415A (en) * | 1943-02-22 | 1946-04-16 | California Research Corp | Mineral oil composition and the like |
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