US3105820A - Mineral oil compositions containing azulene compounds - Google Patents
Mineral oil compositions containing azulene compounds Download PDFInfo
- Publication number
- US3105820A US3105820A US34891A US3489160A US3105820A US 3105820 A US3105820 A US 3105820A US 34891 A US34891 A US 34891A US 3489160 A US3489160 A US 3489160A US 3105820 A US3105820 A US 3105820A
- Authority
- US
- United States
- Prior art keywords
- oil
- azulene
- compounds
- compositions containing
- mineral oil
- 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
- 150000001545 azulenes Chemical class 0.000 title description 11
- 239000000203 mixture Substances 0.000 title description 5
- 239000002480 mineral oil Substances 0.000 title description 2
- 235000010446 mineral oil Nutrition 0.000 title description 2
- 239000003921 oil Substances 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- 239000010688 mineral lubricating oil Substances 0.000 claims description 13
- CUFNKYGDVFVPHO-UHFFFAOYSA-N Azulene Natural products C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims description 12
- -1 AZULENE COMPOUND Chemical class 0.000 claims description 8
- 238000012360 testing method Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- DIRVKNYGBKMFEJ-UHFFFAOYSA-N 5-propan-2-ylazulene Chemical compound CC(C)C1=CC=CC2=CC=CC2=C1 DIRVKNYGBKMFEJ-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229960002350 guaiazulen Drugs 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/022—Well-defined aliphatic compounds saturated
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/02—Well-defined aliphatic compounds
- C10M2203/024—Well-defined aliphatic compounds unsaturated
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/04—Well-defined cycloaliphatic compounds
-
- 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
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
Definitions
- This invention relates to the art of lubrication. More particularly, it is concerned with lubricating oil compositions having improved resistance to oxidation.
- mineral lubricating oils tend to oxidize in use, especially under heat and oxidizing conditions, such as those encountered in internal combustion engines.
- the oxidation products formed in the oil are acidic in nature and exert a corrosive action on the metal surfaces being lubricated.
- the present invention is concerned with a class of chemical compounds which are highly effective in counteracting this tndency of an oil to oxidize in use and thus harm the metal surfaces.
- Azulene compound-s in general are contemplated in the invention.
- a preferred class, however, are those represented by the formula:
- R may be hydrogen in all instances (azulene) or in one or more instances a substituent group selected from alkly, aryl, alkaryl, aralkyl and alkoxy groups.
- R may be hydrogen in all instances (azulene) or in one or more instances a substituent group selected from alkly, aryl, alkaryl, aralkyl and alkoxy groups.
- the number and variety of the said substituent groups, or the molecular weight thereof, is not critical from the stand point of the suitability of the compounds for use in the invention, the choice of a particular compound being chiefly a matter of its availability and/ or cost of manufacture.
- Non-limiting examples of azulene compounds suitable for the invention are the following:
- Cyclopentacycloheptene (azulene) 2-isopropyl-4,8-dimethylazulene (vetivazulene) 3,8-dimethyl-5-isopropylazulene (guaiazulene) 2-isopropyl-S-methylazulene 1,3,5-trimethy1azulene 1,3,5-trimethoxyazulene 2-ethyl-8-methoxy-4-methylazulene 2-ethy1-4-methylazulene Z-phenylazulene 2-(octylphenyl)-azulene S-benzylazulene 5-isopropylazulene Z-ethylazulene 2-laurylazulene S-octadecylazulene 6-naphthylazulene Patented Oct.
- the tests were conducted in an oxidations-tability apparatus, essentially the same as that described by Larsen et al., Industrial and Engineering Chemistry, vol. 34, pp. 183-193 (1942), as follows.
- the test oil is maintained at 300 F. while pure oxygen is recycled therethrough in a closed system. Gaseous oxidation products which are formed are removed by suitable adsorbents in the system in order to maintain the purity of the oxygen during the test.
- the corresponding pressure drop activates a solenoid valve which admits make-up oxygen in fixed increments which are recorded on a time chart.
- a record of the quantity of oxygen with which the oil has been reacted is thus available at any given'time.
- the results are expressed in terms of the time required for the oil sample to absorb a given amount of oxygen.
- the base oil used in the tests was a solvent-refined mineral lubricating oil having a Saybolt Universal viscosity of 54 seconds at 210 F. and 368 seconds at F.
- the test results are given in Table I.
- the azulene compounds of the invention may be used in lubricating oil in amounts ranging from about 0.01 to about 10 weight percent, depending upon the particular oil to be improved and the application for which it is designed. For most purposes, however, the use of from about 0.5 to about 3.0 percent of the additive is sufiicient to provide the desired improvement.
- the azulene compounds may be used in lubricating oils along with other addition agents designed to impart different improving properties to the oil, such as deter gents, V.I. improvers, pour point depressants, anti-foam agents, anti-rust agents, extreme pressure agents, etc.
- R represents a radical selected from the group consisting of hydrogen, alkyl, aryl, alkaryl, aralkyl and alkoxy radicals.
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
United States Patent 3,105,820 MINERAL OIL COMPOSITIONS CONTAINING AZULENE COMPOUNDS Samuel J. Leonardi, Pitman, and Edward A. Oberright,
Woodbury, N.J., assignors to Socony Mobil Oil Compauy, Inc., a corporation of New York No Drawing. Filed June 9, 1960, Ser. No. 34,891 6 Claims. (Cl. 252-- -52) This invention relates to the art of lubrication. More particularly, it is concerned with lubricating oil compositions having improved resistance to oxidation.
As is well known, mineral lubricating oils tend to oxidize in use, especially under heat and oxidizing conditions, such as those encountered in internal combustion engines. The oxidation products formed in the oil are acidic in nature and exert a corrosive action on the metal surfaces being lubricated. The present invention is concerned with a class of chemical compounds which are highly effective in counteracting this tndency of an oil to oxidize in use and thus harm the metal surfaces.
It has now been discovered, in accordance with the present invention, that compounds containing an azulene nucleus when added in minor amounts to a mineral lubricating oil will effectively stabilize the oil against the deleterious effects of oxidation. It is, therefore, the primary object of this invention to provide mineral lubricating oil compositions of improved oxidation stability, said compositions containing minor amounts of azulene compounds. Other and further objects will be apparent from the following description of the invention.
Azulene compound-s in general are contemplated in the invention. A preferred class, however, are those represented by the formula:
wherein R may be hydrogen in all instances (azulene) or in one or more instances a substituent group selected from alkly, aryl, alkaryl, aralkyl and alkoxy groups. The number and variety of the said substituent groups, or the molecular weight thereof, is not critical from the stand point of the suitability of the compounds for use in the invention, the choice of a particular compound being chiefly a matter of its availability and/ or cost of manufacture.
Non-limiting examples of azulene compounds suitable for the invention are the following:
Cyclopentacycloheptene (azulene) 2-isopropyl-4,8-dimethylazulene (vetivazulene) 3,8-dimethyl-5-isopropylazulene (guaiazulene) 2-isopropyl-S-methylazulene 1,3,5-trimethy1azulene 1,3,5-trimethoxyazulene 2-ethyl-8-methoxy-4-methylazulene 2-ethy1-4-methylazulene Z-phenylazulene 2-(octylphenyl)-azulene S-benzylazulene 5-isopropylazulene Z-ethylazulene 2-laurylazulene S-octadecylazulene 6-naphthylazulene Patented Oct. 1, 1963 ICC Further information relative to the various azulene compounds and their preparation may be obtained by reference to the article entitled The Azulenes, by Maxwell Gordon, Chemical Reviews, vol. 50, pp. 127-200 (1952) V ANTIOXIDANT ACTION The effectiveness of the azulene compounds contemplated herein as oxidation inhibitors for mineral lubricating oil has been demonstrated by oxidation-stability tests conducted on mineral lubricating oil alone and on the same oil blended with small amounts of representative azulene compounds. For purpose of comparison, naphthalene, the common benzenoid isomer of azulene, was also tested. The tests were conducted in an oxidations-tability apparatus, essentially the same as that described by Larsen et al., Industrial and Engineering Chemistry, vol. 34, pp. 183-193 (1942), as follows. The test oil is maintained at 300 F. while pure oxygen is recycled therethrough in a closed system. Gaseous oxidation products which are formed are removed by suitable adsorbents in the system in order to maintain the purity of the oxygen during the test. As oxygen is taken up by the oil, the corresponding pressure drop activates a solenoid valve which admits make-up oxygen in fixed increments which are recorded on a time chart. A record of the quantity of oxygen with which the oil has been reacted is thus available at any given'time. The results are expressed in terms of the time required for the oil sample to absorb a given amount of oxygen.
The base oil used in the tests was a solvent-refined mineral lubricating oil having a Saybolt Universal viscosity of 54 seconds at 210 F. and 368 seconds at F. The test results are given in Table I.
It will be observed from the test results that both of the azulene compounds were highly efiective in reducing the oxidation of the oil. On the other hand, the naphthalene was not significantly effective.
The azulene compounds of the invention may be used in lubricating oil in amounts ranging from about 0.01 to about 10 weight percent, depending upon the particular oil to be improved and the application for which it is designed. For most purposes, however, the use of from about 0.5 to about 3.0 percent of the additive is sufiicient to provide the desired improvement.
The azulene compounds may be used in lubricating oils along with other addition agents designed to impart different improving properties to the oil, such as deter gents, V.I. improvers, pour point depressants, anti-foam agents, anti-rust agents, extreme pressure agents, etc.
Although the invention has been illustrated herein by means of certain specific examples and tests, it is not intended that the scope of the invention be limited thereby, but only as indicated by the following claims.
We claim:
1. A mineral lubricating oil containing a minor amount,
suflicient to inhibit said oil against oxidation, of an azulene compound of the formula:
wherein R represents a radical selected from the group consisting of hydrogen, alkyl, aryl, alkaryl, aralkyl and alkoxy radicals.
2. A mineral lubricating oil containing a minor amount, sufiicient to inhibit said oil against oxidation, of azulene.
3. A mineral lubricating oil containing a minor amount, sufiicient to inhibit said oil against oxidation, of 3,8-dimethyl-5-isopropylazulene.
4. A mineral lubricating oil containing a minor amount, sufficient to inhibit said oil against oxidation, of 1,3,5 trimethoxyazulene.
5. A mineral lubricating oil containing a minor amount,
5 sufiicient to inhibit said oil against oxidation, of 2-pheny1- azulene.
6. A mineral lubricating oil containing a minor amount, sufficient to inhibit said oil against oxidation, of 2-is0- propyl-4,8-dimethylazulene.
References Cited in the file of this patent UNITED STATES PATENTS 2,217,173 Lincoln et al. Oct. 8, 1940 15 2,629,750 Rath Feb. 24, 1953 2,766,304 Ziegler et a1. Oct. 9, 1956
Claims (1)
1. A MINERAL LUBRICATING OIL CONTAINING A MINOR AMOUNT, SUFFICIENT TO INHIBIT SAID OIL AGAINST OXIDATION, OF AN AZULENE COMPOUND OF THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34891A US3105820A (en) | 1960-06-09 | 1960-06-09 | Mineral oil compositions containing azulene compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34891A US3105820A (en) | 1960-06-09 | 1960-06-09 | Mineral oil compositions containing azulene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3105820A true US3105820A (en) | 1963-10-01 |
Family
ID=21879258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US34891A Expired - Lifetime US3105820A (en) | 1960-06-09 | 1960-06-09 | Mineral oil compositions containing azulene compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3105820A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108865174A (en) * | 2018-05-25 | 2018-11-23 | 山西义诺电子材料有限公司 | A kind of liquid-crystal compounds and its preparation method and application containing Azulene ring |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2217173A (en) * | 1936-02-19 | 1940-10-08 | Continental Oil Co | Stabilized high film strength lubricating oil |
| US2629750A (en) * | 1948-09-25 | 1953-02-24 | Science Associates Inc | Stabilized azulene oil |
| US2766304A (en) * | 1953-08-07 | 1956-10-09 | Ziegler Karl | Process for preparing azulenes |
-
1960
- 1960-06-09 US US34891A patent/US3105820A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2217173A (en) * | 1936-02-19 | 1940-10-08 | Continental Oil Co | Stabilized high film strength lubricating oil |
| US2629750A (en) * | 1948-09-25 | 1953-02-24 | Science Associates Inc | Stabilized azulene oil |
| US2766304A (en) * | 1953-08-07 | 1956-10-09 | Ziegler Karl | Process for preparing azulenes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108865174A (en) * | 2018-05-25 | 2018-11-23 | 山西义诺电子材料有限公司 | A kind of liquid-crystal compounds and its preparation method and application containing Azulene ring |
| CN108865174B (en) * | 2018-05-25 | 2020-04-24 | 山西义诺电子材料有限公司 | Liquid crystal compound containing azulene ring and preparation method and application thereof |
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