US2249564A - Addition agent for lubricating oils - Google Patents
Addition agent for lubricating oils Download PDFInfo
- Publication number
- US2249564A US2249564A US219354A US21935438A US2249564A US 2249564 A US2249564 A US 2249564A US 219354 A US219354 A US 219354A US 21935438 A US21935438 A US 21935438A US 2249564 A US2249564 A US 2249564A
- Authority
- US
- United States
- Prior art keywords
- naphthenic
- aromatic
- radical
- ketones
- oils
- 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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- 239000010687 lubricating oil Substances 0.000 title description 8
- 239000003795 chemical substances by application Substances 0.000 title description 6
- 150000002576 ketones Chemical class 0.000 description 23
- -1 compound radical Chemical class 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 15
- 239000003921 oil Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000003350 kerosene Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- UMNSMBWAESLVOC-UHFFFAOYSA-N n-pentylaniline Chemical compound CCCCCNC1=CC=CC=C1 UMNSMBWAESLVOC-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000010688 mineral lubricating oil Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 125000005608 naphthenic acid group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical class CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- 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
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
-
- 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
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- 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
- C10M2207/08—Aldehydes; Ketones
-
- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
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- 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
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/142—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings polycarboxylic
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- 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
- C10M2207/284—Esters of aromatic monocarboxylic acids
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- 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
- C10M2207/285—Esters of aromatic polycarboxylic acids
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- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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- 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
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/06—Perfluorinated compounds
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- 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
- C10M2215/064—Di- and triaryl amines
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- 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
- C10M2215/30—Heterocyclic compounds
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- 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
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- 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
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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- 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
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- 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
- C10M2219/106—Thiadiazoles
Definitions
- the present invention relates to improved addition agents for lubricating oils and more specifically to agents for reducing the pour point of waxy oils and for improving other properties as well.
- ketones had the power of increasing oiliness and in some instances reducing the pour point of waxy oils.
- the said ketones are of the general formula:
- R is a ring compound radical, either carbocyclic or heterocyclic, and R is an alky radical of at least 11 carbon atoms.
- ketones are very weak pour inhibitors except in a few instances, particularly where complex polycyclic or condensed ring aromatic radicals are employed, such as anthracyl or phenanthryl radicals, and it would appear that compounds of this type would find whatever use they may have as oiliness agents.
- R. is an aromatic, hydroaromatic radical, or heterocyclic radical and R" is a naphthenic radical.
- R. is an aromatic, hydroaromatic radical, or heterocyclic radical
- R" is a naphthenic radical.
- the ketones referred to above, which constitute the present invention, are made by reaction of approximately equimolal quantities of naphthenic acidhalides, preferably naphthenic acid chloride, with aromatic hydroaromatic or heterocyclic compounds.
- the naphthenic acid chloride is obtained from naphthenic acids which occur naturally in certain crude oils, notably the so-called naphthenic crudes of the Texas Coastal region, from certain California crudes, as well as the crudes of Roumania, Aruba and Venezuela.
- the acids occur in almost all fractions from the kerosene range upward into the heavy lubricating oils.
- the acids are separated from the oil fractions by known methods and can be converted to the acid chloride by treatment with phosphorous tri or pentachlorides, or sulfuryl chloride or the like, at slightly elevated temperatures.
- the acid halide may be also made from alkali metal salts of the acids as well as from the acids themselves. The products are then purified by distillation or otherwise.
- the naphthenic acid chloride or other halide is caused to react with a suitable aromatic, hydroaromatic, or heterocyclic compound in order to produce ketones.
- suitable aromatics may be mentioned the hydrocarbons such as benzol, naphthalene, anthracene, diphenyl, xylene, or higher aromatics such as Propy1-, buty1-, amyl-benzenes, naphthalenes and the like.
- Hydrogenated aromatic hydrocarbons may also be employed such as cyclo-hexane, cyclo-hexene, tetra and decachlor naphthalene.
- oxygen-containing aromatics such as phenols and naphthol's. Cresols and the higher alkylated phenolic compounds are also useful, such as amylor butyl phenols and naphthols.
- Aromatic ethers can be used for the present purpose such as diphenyl oxide, phenyl ether and complex aromatic-aliphatic ethers. Aromatic atives.
- the reaction is brought about between thenaphthenic acid halide and the suitable aromatic or heterocyclic compound through the agency of the Friedel-Crafts type catalysts among which aluminum chloride, zinc chloride and the like may be mentioned. These are preferably employed in relatively large quantities, for example in substantially molecular proportions, preferably at room temperature or thereabout.
- the reaction is extremely vigorous and takes place quite rapidly although it is desirable to reflux the mixturefor an hour or more after the action.
- the product is then hydrolyzed, for example by adding water, aqueous alcohol or acid, and the ketone is then extracted with kerosene, naphtha or other suitable solvent from the inorganic products of hydrolysis. It may be recovered by distilling oi the acid.
- the products obtained are of an oily character, in some cases heavy viscous oils, and in others are solid at room temperature. The color varies from a brilliant green to a dark brown. They are all soluble in mineral oils and some have excellent fluorescent properties, so that they may be used for this purpose in lubricating oil. Particularly desirable materials of this type are the hydroaromatic naphthenic ketones such as tetralin naphthenic ketone. Further, some of these products have the additional valuable property of imparting oiliness to natural mineral oils into which they are blended. For example, when added in even small amounts to mineral lubricating oils, say of the order 01 1 to 3%, there results a very marked improvement in the oiliness of the oil.
- the alkylated aniline naphthenic ketones are especially desirable for this specific use.
- the compounds When the compounds are to be usedas depressants for waxy oils, it is preferred that they be made from monocyclic aromatic materials, preferably the hydrocarbons or the hydroxy aromatics.
- the proportion in which they are added varies from about .1% to about 5%, but depends oi the particular product and on the oil to which it is-added. Some compounds are considerably more active than others and, as is well known, certain oils are much more susceptible to treatment than others. With reasonably small amounts, it i possible to obtain depressions of 20 to 50 F. .As an example of the method of making the present compounds, and their effectiveness in'oilpthe following data are ofi'ered. In each case the same procedure for manui'actm'ing the ketones 'was used and the products were tested in the 'same oil.
- Example I 80 grams of naphthenic acids having an acid- A. S. T. M. ours of- R&R' p
- R naphthenic radical
- AmyMXy-phenyI +10 l5 Anyl-phenyl-amyl-ether +20 5 Aniline +20 -15 Tetmii n +20 1O Xylen 5 AlphaFnaphthoL. +10 -15 Beta-naphtha] +15 20 Beta naphthylamine +20 15 2O PolY-amyl-naphthyl- +25 +10 Amyl-aniline 5 15 Phenyl other -- +20 0 Dimethyl aniline. +20
- Diphenylamine +15 15 number of 212.5 and a saponification number of 214.8 were heated with 20 gram of phosphorus; trichloride on the water bath.
- the resultingnaphthenic acid chloride was decanted from the phosphorus acid and mixed with one molar proportion of the particular aromatic compound used contained in 100-150 cc. of tetrachlorethane as solvent.
- 40 grams of anhydrous AlCla were then slowly added to the reaction mixture while agitating at room temperature. Vigorous reaction took place with all of the aromatic compounds studied when adding the A1013 at room temperature. After the reaction of the AlCls, the reaction mixture was refluxed under areturn condenser for 3 hours.
- Example I The following example will illustrate the oiliness imparting properties of a number of the ketones whose preparation is described in Example I.
- test blends comprised 3% of the respective aromatic naphthenic ketone in a light lubricating oil. These were tested for oiliness imparting property by means of the "Almen lubricant testing machine.” A description of the use of this machine for testing oiliness can be found in a monograph issued by the Virginia Polytechnic Institute by James I. Clower (see Bulletin #33, V. P. 1., vol. 27, No. 11, part 2, September, 1934).
- R is a naphthenic radical having a molecular weight at least as high as that of the naphthenic radicals obtainable from kerosene and R is a closed ring radical selected from the group consisting of poly-nuclear aromatic hydrocarbons and alkyl, hydrogenated, oxyand nitrogen derivatives of aromatic hydrocarbons.
- Product comprising a lubricating oil and a minor amount of an alkylated aromatic amine naphthenic ketone.
- Product comprising a lubricating oil and a v 11.
- An improved lubricating oil-blending agent comprising a mixed ketone condensation product from a Friedel-Crafts reaction of petroleum naphthenic acid chlorides with a cyclic organic compound, said ketone condensation. product beingconstituted by poly-nuclear naphthenic hydrocarbon radicals from the naphthenic acid chlorides joined to closed ring radicals of said cyclic organic compound through a ketone linkage.
- closed ring radical is an oxy-aromatic radical having a single oxygen group substituent in the aromatic ring.
- said cyclic organic compound is amyl-aniline.
- An improved lubricant comprising mineral lubricating oil and a ketone otthe following formula: R-fiI-R where R is a naphthenic radical and R is a heterocyclic radical.
- R-c-w 0 where R is a poly-nuclear naphthenic radical derived from a petroleum fraction at least as heavy as kerosene, and R'is a closed ring radical.
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Description
Patented July 15, 1941 ADDITION AGENT FOR LUBRICATING OILS Eugene Lieber, Linden, N.
ard Oil Development Company,
of Delaware J., assignor to Standa corporation No Drawing. Application July 15, 1938,
Serial No. 219,354
15 Claims.
The present invention relates to improved addition agents for lubricating oils and more specifically to agents for reducing the pour point of waxy oils and for improving other properties as well.
It had been previously found that certain complex ketones had the power of increasing oiliness and in some instances reducing the pour point of waxy oils. The said ketones are of the general formula:
where R is a ring compound radical, either carbocyclic or heterocyclic, and R is an alky radical of at least 11 carbon atoms. These ketones are very weak pour inhibitors except in a few instances, particularly where complex polycyclic or condensed ring aromatic radicals are employed, such as anthracyl or phenanthryl radicals, and it would appear that compounds of this type would find whatever use they may have as oiliness agents.
It has now been found that better pour depressants can be made from naphthenic ketones which are of the following general formula:
where R. is an aromatic, hydroaromatic radical, or heterocyclic radical and R" is a naphthenic radical. These compounds differ very widely from the complex ketones heretofore described in that it appears that the preferable compounds of the present type contain monocyclicaromatic or heretocyclic radicals combined with the naphthenic group whereas the monocyclicalkyl ketones hitherto known have very little value as pour depressants. While there are other differences, these seem to suffice to show that the naphthenic-aromatlc or heterocyclic ketones do not follow the course that would be supposed from the known properties of the aromaticalkyl or heterocyclic-alkyl ketones.
The ketones referred to above, which constitute the present invention, are made by reaction of approximately equimolal quantities of naphthenic acidhalides, preferably naphthenic acid chloride, with aromatic hydroaromatic or heterocyclic compounds. The naphthenic acid chloride is obtained from naphthenic acids which occur naturally in certain crude oils, notably the so-called naphthenic crudes of the Texas Coastal region, from certain California crudes, as well as the crudes of Roumania, Aruba and Venezuela. The acids occur in almost all fractions from the kerosene range upward into the heavy lubricating oils. The acids are separated from the oil fractions by known methods and can be converted to the acid chloride by treatment with phosphorous tri or pentachlorides, or sulfuryl chloride or the like, at slightly elevated temperatures. As is well known, the acid halide may be also made from alkali metal salts of the acids as well as from the acids themselves. The products are then purified by distillation or otherwise.
As stated before, the naphthenic acid chloride or other halide is caused to react with a suitable aromatic, hydroaromatic, or heterocyclic compound in order to produce ketones. Among the suitable aromatics may be mentioned the hydrocarbons such as benzol, naphthalene, anthracene, diphenyl, xylene, or higher aromatics such as Propy1-, buty1-, amyl-benzenes, naphthalenes and the like. Hydrogenated aromatic hydrocarbons may also be employed such as cyclo-hexane, cyclo-hexene, tetra and decachlor naphthalene. Another group of compounds that are suitable are the oxygen-containing aromatics such as phenols and naphthol's. Cresols and the higher alkylated phenolic compounds are also useful, such as amylor butyl phenols and naphthols.
Aromatic ethers can be used for the present purpose such as diphenyl oxide, phenyl ether and complex aromatic-aliphatic ethers. Aromatic atives.
The reaction is brought about between thenaphthenic acid halide and the suitable aromatic or heterocyclic compound through the agency of the Friedel-Crafts type catalysts among which aluminum chloride, zinc chloride and the like may be mentioned. These are preferably employed in relatively large quantities, for example in substantially molecular proportions, preferably at room temperature or thereabout. The reaction is extremely vigorous and takes place quite rapidly although it is desirable to reflux the mixturefor an hour or more after the action. The product is then hydrolyzed, for example by adding water, aqueous alcohol or acid, and the ketone is then extracted with kerosene, naphtha or other suitable solvent from the inorganic products of hydrolysis. It may be recovered by distilling oi the acid.
The products obtained are of an oily character, in some cases heavy viscous oils, and in others are solid at room temperature. The color varies from a brilliant green to a dark brown. They are all soluble in mineral oils and some have excellent fluorescent properties, so that they may be used for this purpose in lubricating oil. Particularly desirable materials of this type are the hydroaromatic naphthenic ketones such as tetralin naphthenic ketone. Further, some of these products have the additional valuable property of imparting oiliness to natural mineral oils into which they are blended. For example, when added in even small amounts to mineral lubricating oils, say of the order 01 1 to 3%, there results a very marked improvement in the oiliness of the oil. The alkylated aniline naphthenic ketones are especially desirable for this specific use. When the compounds are to be usedas depressants for waxy oils, it is preferred that they be made from monocyclic aromatic materials, preferably the hydrocarbons or the hydroxy aromatics. The proportion in which they are added varies from about .1% to about 5%, but depends oi the particular product and on the oil to which it is-added. Some compounds are considerably more active than others and, as is well known, certain oils are much more susceptible to treatment than others. With reasonably small amounts, it i possible to obtain depressions of 20 to 50 F. .As an example of the method of making the present compounds, and their effectiveness in'oilpthe following data are ofi'ered. In each case the same procedure for manui'actm'ing the ketones 'was used and the products were tested in the 'same oil.
Example I 80 grams of naphthenic acids having an acid- A. S. T. M. ours of- R&R' p
- R=naphthenic radical R: 1% blend 5% blend Blank (Original Oil) +30 +30 Phenyl +30 +15 Phenanthryl +25 +10 0 Diphenyi.-. +20 0 Fiuoryl +25 +25 Oxy-phenyl- 0 20 Oxy-cresyl 0 -25 Diamyl-oxy-phenyl- +25 0 O-hydroxy-diphen +20 Amyl-beta-oxy-naphthyl. l5
15 AmyMXy-phenyI +10 l5 Anyl-phenyl-amyl-ether +20 5 Aniline +20 -15 Tetmii n +20 1O Xylen 5 AlphaFnaphthoL. +10 -15 Beta-naphtha] +15 20 Beta naphthylamine +20 15 2O PolY-amyl-naphthyl- +25 +10 Amyl-aniline 5 15 Phenyl other..." +20 0 Dimethyl aniline. +20
Diphenylamine +15 15 number of 212.5 and a saponification number of 214.8 were heated with 20 gram of phosphorus; trichloride on the water bath. The resultingnaphthenic acid chloride was decanted from the phosphorus acid and mixed with one molar proportion of the particular aromatic compound used contained in 100-150 cc. of tetrachlorethane as solvent. 40 grams of anhydrous AlCla were then slowly added to the reaction mixture while agitating at room temperature. Vigorous reaction took place with all of the aromatic compounds studied when adding the A1013 at room temperature. After the reaction of the AlCls, the reaction mixture was refluxed under areturn condenser for 3 hours. It was then poured into a mixture of alcohol and water and extracted, after cooling, with kerosene. The kerosene extract was then washedseveral times with the'water-alcohol mixture and then distilled with fire and steam had an original pour point of 30 F. and the pour depression was noted. The data are given in the table below:
Example I! The following example will illustrate the oiliness imparting properties of a number of the ketones whose preparation is described in Example I.
The test blends comprised 3% of the respective aromatic naphthenic ketone in a light lubricating oil. These were tested for oiliness imparting property by means of the "Almen lubricant testing machine." A description of the use of this machine for testing oiliness can be found in a monograph issued by the Virginia Polytechnic Institute by James I. Clower (see Bulletin #33, V. P. 1., vol. 27, No. 11, part 2, September, 1934).
The data obtained can be tabulated as follows:
Weights Ketone ed Unblended nn 2 Phenol naph 5 Oresoi hanhfhanin 7 C-amyl aniline flnnhfhnnin 12 where R is a naphthenic radical having a molecular weight at least as high as that of the naphthenic radicals obtainable from kerosene and R is a closed ring radical selected from the group consisting of poly-nuclear aromatic hydrocarbons and alkyl, hydrogenated, oxyand nitrogen derivatives of aromatic hydrocarbons.
2. Product according to claim 1 in which R is an aromatic radical.
3. Product according to claim 1 in which R is an oxy-aromatic radical.
4. Product comprising a lubricating oil and a minor amount of an alkylated aromatic amine naphthenic ketone.
5. Product comprising a lubricating oil and a v 11. A product according to claim 15 in which minor amount of amyl aniline naphthenic ketone.
6. An improved lubricating oil-blending agent comprising a mixed ketone condensation product from a Friedel-Crafts reaction of petroleum naphthenic acid chlorides with a cyclic organic compound, said ketone condensation. product beingconstituted by poly-nuclear naphthenic hydrocarbon radicals from the naphthenic acid chlorides joined to closed ring radicals of said cyclic organic compound through a ketone linkage.
7. A product according to claim 15 in which the closed ring radicalin an aromatic radical.
8. A product according to claim 15 in which said closed ring radical is an oxy-aromatic radical having a single oxygen group substituent in the aromatic ring.
9. A product according to claim 15 in which said closed ring radical is an aromatic amine radical.
10. A product according to claim 15 in which said closed ring radical is an alkylated aromatic amine radical.
said cyclic organic compound is amyl-aniline.
12. An improved lubricant comprising mineral lubricating oil and a ketone otthe following formula: R-fiI-R where R is a naphthenic radical and R is a heterocyclic radical.
' 13. Product according to claim 12 where R is an' oxygen-containing aromatic radicaL.
14. Product according-to claim 12 where R is a nitrogen-containing aromatic radical.
15. An improved product comprising a ketone of the following formula:
R-c-w 0 where R is a poly-nuclear naphthenic radical derived from a petroleum fraction at least as heavy as kerosene, and R'is a closed ring radical.
- EUGENE LIEBER.
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US6750183B2 (en) * | 2000-12-22 | 2004-06-15 | Infineum International Ltd. | Lubricating oil composition |
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US6750183B2 (en) * | 2000-12-22 | 2004-06-15 | Infineum International Ltd. | Lubricating oil composition |
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