US3832304A - Hydrocracked lubes stabilized with aromatic azo compounds - Google Patents
Hydrocracked lubes stabilized with aromatic azo compounds Download PDFInfo
- Publication number
- US3832304A US3832304A US00231749A US23174972A US3832304A US 3832304 A US3832304 A US 3832304A US 00231749 A US00231749 A US 00231749A US 23174972 A US23174972 A US 23174972A US 3832304 A US3832304 A US 3832304A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- hydrocracked
- alkyl group
- formula
- lubes
- 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
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000010687 lubricating oil Substances 0.000 abstract description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000004611 light stabiliser Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 9
- 238000004517 catalytic hydrocracking Methods 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- LYMAPPPYTSLWDN-UHFFFAOYSA-N [4-[(4-ethoxyphenyl)diazenyl]phenyl] pentanoate Chemical compound C1=CC(OC(=O)CCCC)=CC=C1N=NC1=CC=C(OCC)C=C1 LYMAPPPYTSLWDN-UHFFFAOYSA-N 0.000 description 3
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QXTOLYZIJUDOIT-UHFFFAOYSA-N n,n,3-trimethyl-4-phenyldiazenylaniline Chemical compound CC1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 QXTOLYZIJUDOIT-UHFFFAOYSA-N 0.000 description 3
- QUICZVHSJNKDBL-UHFFFAOYSA-N (4-ethoxyphenyl)-(4-ethoxyphenyl)imino-oxidoazanium Chemical compound C1=CC(OCC)=CC=C1N=[N+]([O-])C1=CC=C(OCC)C=C1 QUICZVHSJNKDBL-UHFFFAOYSA-N 0.000 description 2
- KQIKKETXZQDHGE-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(N)C=C1 KQIKKETXZQDHGE-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- -1 V.I. improver Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- KJMATSUHPOPLMT-UHFFFAOYSA-N oxido-(4-pentoxyphenyl)-(4-pentoxyphenyl)iminoazanium Chemical compound C1=CC(OCCCCC)=CC=C1N=[N+]([O-])C1=CC=C(OCCCCC)C=C1 KJMATSUHPOPLMT-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- ITRNXVSDJBHYNJ-UHFFFAOYSA-N tungsten disulfide Chemical compound S=[W]=S ITRNXVSDJBHYNJ-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 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
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
-
- 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
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
-
- 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
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/108—Residual fractions, e.g. bright stocks
-
- 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
- C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
-
- 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
- C10M2215/18—Containing nitrogen-to-nitrogen bonds, e.g. hydrazine
- C10M2215/182—Azo compounds
Definitions
- the azoxy compounds have the formula:
- R, R n and m have the meanings defined above, or the formula:
- hydrocracking petroleum stocks for the production of lubes has been recognized as a superior technique for the production of lubricating oil.
- Hydrocracking has a number of distinct advantages over the conventional solvent refining technique in that it generally produces base stocks which have a higher viscosity index and that many crude stocks which do not produce a satisfactory solvent refined lube can be used.
- hydrocracked lubes suffer from poor stability to light and when exposed to sunlight for an extended period of time of say 30 days discolor and form considerable quantities of sludge. This instability to light can be improved by further refining but this is expensive.
- hydrocracked lubricating oils are prepared by treating a deasphalted residuum having a viscosity index in the range of about to 100 and a viscosity at 210 F. in the range of about to 200 SUS with hydrogen at a temperature of from 650 F. to 825 F.
- the catalysts used are generally mixtures of nickel sulfide with either molybdenum sulfide or tungsten sulfide supported on alumina or silica alumina.
- the specifics of hydrocracking are well known in the art. Patents disclosing the technique of hydrocracking include US. Pat. No. 2,960,548, issued Nov. 15, 1960, to George W. Ayers et al.
- the present invention involves incorporating in the hydrocracked oil a minor amount which usually is less than 0.5 wt. percent and preferably is from 0.01 to 0.2 wt. percent of the oil of a light stabilizer. Below the 0.01 wt. percent level insufiicient stabilization is obtained while above 0.2 wt. percent and especially above 0.5 wt. percent the orange-red color of the azo dye stabilizer becomes undesirably noticeable.
- the stabilizer compounds have one of the following formulae:
- R 1) 1: (Rl)m 1) n (R1) n T /N- -N N- or R wherein R is an alkyl group of from 1 to 10 carbon atoms, R is an alkyl group of from 1 to 5 carbon atoms, R is an alkyl group of from 1 to 10 carbon atoms, R is either an alkyl group of from 1 to 10 carbon atoms or a group of the formula wherein R is an alkyl group of from 1 to 10 carbon atoms, R has the meaning defined above, n is a number from 0 to 4 and m is a number from 0 to 5.
- the oil would normally also contain the usual additives such as V.I. improver, antifoam agent, pour depressant, etc.
- a composition comprising a major portion of a hydrocracked petroleum lubricating oil and as a light stabilizer from 0.05 to 0.2 wt. percent as based on said oil of a compound having a formula selected from the class consisting of:
- R is an alkyl group of from 1 to 10 carbon atoms
- R is an alkyl group of from 1 to 5 carbon atoms
- R is an alkyl group of from 1 to 10 carbon atoms
- R is an alkyl group of from 1 to 10 carbon atoms or a group of the formula where R, is an alkyl group of from 1 to 10 carbon atoms and n is a number from 0 to 4 and m is a number from 0 to 5.
- composition of Claim 1 wherein the light stabilizer has the formula 3.
- composition of Claim 2 wherein the light stabilizer is 4-N,N-dimethylaminoazobenzene.
- composition of Claim 1 wherein the light stabilizer has the formula 8.
- the composition of Claim 7 wherein the light stabilizer is 4,4-azodiphenetole.
- composition of Claim 1 wherein the light stabilizer has the formula US. Cl. X.R.
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00231749A US3832304A (en) | 1972-03-03 | 1972-03-03 | Hydrocracked lubes stabilized with aromatic azo compounds |
| CA158,520A CA972698A (en) | 1972-03-03 | 1972-12-08 | Hydrocracked lubes stabilized with aromatic azo compounds |
| JP48020313A JPS48101402A (cg-RX-API-DMAC7.html) | 1972-03-03 | 1973-02-21 | |
| NL7302631A NL7302631A (cg-RX-API-DMAC7.html) | 1972-03-03 | 1973-02-26 | |
| GB1016173A GB1368727A (en) | 1972-03-03 | 1973-03-02 | Lubricating oils |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00231749A US3832304A (en) | 1972-03-03 | 1972-03-03 | Hydrocracked lubes stabilized with aromatic azo compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3832304A true US3832304A (en) | 1974-08-27 |
Family
ID=22870508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00231749A Expired - Lifetime US3832304A (en) | 1972-03-03 | 1972-03-03 | Hydrocracked lubes stabilized with aromatic azo compounds |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3832304A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS48101402A (cg-RX-API-DMAC7.html) |
| CA (1) | CA972698A (cg-RX-API-DMAC7.html) |
| GB (1) | GB1368727A (cg-RX-API-DMAC7.html) |
| NL (1) | NL7302631A (cg-RX-API-DMAC7.html) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2525626B1 (fr) * | 1982-04-22 | 1985-07-05 | Asulab Sa | Lubrifiant a base de cristaux liquides |
| US5156653A (en) * | 1991-04-18 | 1992-10-20 | Morton International, Inc. | Silent markers for petroleum, method of tagging, and method of detection |
-
1972
- 1972-03-03 US US00231749A patent/US3832304A/en not_active Expired - Lifetime
- 1972-12-08 CA CA158,520A patent/CA972698A/en not_active Expired
-
1973
- 1973-02-21 JP JP48020313A patent/JPS48101402A/ja active Pending
- 1973-02-26 NL NL7302631A patent/NL7302631A/xx unknown
- 1973-03-02 GB GB1016173A patent/GB1368727A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7302631A (cg-RX-API-DMAC7.html) | 1973-09-06 |
| JPS48101402A (cg-RX-API-DMAC7.html) | 1973-12-20 |
| GB1368727A (en) | 1974-10-02 |
| CA972698A (en) | 1975-08-12 |
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