JPH0144276B2 - - Google Patents

Info

Publication number: JPH0144276B2
Authority: JP; Japan
Prior art keywords: methylbenzyl; aniline; metal; alpha; methyl
Prior art date: 1979-05-31
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

Application number

JP7364580A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55161894A (en

Inventor

Kumaa Bandoritsushu Barudebu

Shii Raburesu Furederitsuku

Nuudenbaagu Uorutaa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Uniroyal Inc

Original Assignee

Uniroyal Inc

Priority date (The priority date 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 date listed.)

1979-05-31

Filing date

1980-05-31

Publication date

1989-09-26

1980-05-31 Application filed by Uniroyal Inc filed Critical Uniroyal Inc

1980-12-16 Publication of JPS55161894A publication Critical patent/JPS55161894A/ja

1989-09-26 Publication of JPH0144276B2 publication Critical patent/JPH0144276B2/ja

Status Granted legal-status Critical Current

Links

239000010687 lubricating oil Substances 0.000 claims description 35
239000003963 antioxidant agent Substances 0.000 claims description 18
229920000728 polyester Polymers 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
230000003078 antioxidant effect Effects 0.000 claims description 10
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
239000003921 oil Substances 0.000 claims description 8
239000004215 Carbon black (E152) Substances 0.000 claims description 5
229930195733 hydrocarbon Natural products 0.000 claims description 5
150000002430 hydrocarbons Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
GDPWWAKUQIHZIT-UHFFFAOYSA-N n-[1-(4-octylphenyl)ethyl]aniline Chemical compound C1=CC(CCCCCCCC)=CC=C1C(C)NC1=CC=CC=C1 GDPWWAKUQIHZIT-UHFFFAOYSA-N 0.000 claims description 5
FUWVSQBMDYXSMK-UHFFFAOYSA-N 2-chloro-n-(1-phenylethyl)aniline Chemical compound C=1C=CC=CC=1C(C)NC1=CC=CC=C1Cl FUWVSQBMDYXSMK-UHFFFAOYSA-N 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
MSRXKOAPHWUNNM-UHFFFAOYSA-N 2-methoxy-n-(1-phenylethyl)aniline Chemical compound COC1=CC=CC=C1NC(C)C1=CC=CC=C1 MSRXKOAPHWUNNM-UHFFFAOYSA-N 0.000 claims description 3
GAORUNDHDPHKLT-UHFFFAOYSA-N 3-chloro-n-(1-phenylethyl)aniline Chemical compound C=1C=CC=CC=1C(C)NC1=CC=CC(Cl)=C1 GAORUNDHDPHKLT-UHFFFAOYSA-N 0.000 claims description 3
LURKEPOVOHKECE-UHFFFAOYSA-N 4-chloro-n-(1-phenylethyl)aniline Chemical compound C=1C=CC=CC=1C(C)NC1=CC=C(Cl)C=C1 LURKEPOVOHKECE-UHFFFAOYSA-N 0.000 claims description 3
UQLHDYGJWYHXET-UHFFFAOYSA-N 4-dodecyl-n-(1-phenylethyl)aniline Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1NC(C)C1=CC=CC=C1 UQLHDYGJWYHXET-UHFFFAOYSA-N 0.000 claims description 3
QKBUMGWVDNFABU-UHFFFAOYSA-N 4-methoxy-n-(1-phenylethyl)aniline Chemical compound C1=CC(OC)=CC=C1NC(C)C1=CC=CC=C1 QKBUMGWVDNFABU-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000002480 mineral oil Substances 0.000 claims description 2
230000001050 lubricating effect Effects 0.000 claims 3
FATHMPJPUNLQAC-UHFFFAOYSA-N 3-methoxy-n-(1-phenylethyl)aniline Chemical compound COC1=CC=CC(NC(C)C=2C=CC=CC=2)=C1 FATHMPJPUNLQAC-UHFFFAOYSA-N 0.000 claims 2
125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
235000010446 mineral oil Nutrition 0.000 claims 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
229910052751 metal Inorganic materials 0.000 description 23
239000002184 metal Substances 0.000 description 23
229910052802 copper Inorganic materials 0.000 description 18
239000010949 copper Substances 0.000 description 18
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 17
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
239000003381 stabilizer Substances 0.000 description 13
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 12
238000009835 boiling Methods 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
150000001412 amines Chemical class 0.000 description 10
239000000314 lubricant Substances 0.000 description 10
IUERBKSXAYWVGE-UHFFFAOYSA-N n-(1-phenylethyl)aniline Chemical compound C=1C=CC=CC=1C(C)NC1=CC=CC=C1 IUERBKSXAYWVGE-UHFFFAOYSA-N 0.000 description 10
239000006078 metal deactivator Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 8
239000002808 molecular sieve Substances 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
238000006386 neutralization reaction Methods 0.000 description 7
238000010525 oxidative degradation reaction Methods 0.000 description 7
239000010802 sludge Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
230000032683 aging Effects 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000004508 fractional distillation Methods 0.000 description 6
238000005259 measurement Methods 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002262 Schiff base Substances 0.000 description 3
150000004753 Schiff bases Chemical class 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000000034 method Methods 0.000 description 3
RMYXIOOSZJVXLA-UHFFFAOYSA-N n-(2-chlorophenyl)-1-phenylethanimine Chemical compound C=1C=CC=CC=1C(C)=NC1=CC=CC=C1Cl RMYXIOOSZJVXLA-UHFFFAOYSA-N 0.000 description 3
GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical class C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000006641 stabilisation Effects 0.000 description 3
238000011105 stabilization Methods 0.000 description 3
230000000087 stabilizing effect Effects 0.000 description 3
CTYZQDUUGUUTKB-UHFFFAOYSA-N 1-(4-octylphenyl)-n-phenylethanimine Chemical compound C1=CC(CCCCCCCC)=CC=C1C(C)=NC1=CC=CC=C1 CTYZQDUUGUUTKB-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
-1 N-(alpha-methyl-p-octylbenzyl)aniline N-(alpha-methylbenzyl)-p-dodecylaniline N-(alpha-methylbenzyl)-p-methoxyaniline N-(alpha-methylbenzyl)-m- Methoxyaniline N-(alpha-methylbenzyl)-o-methoxyaniline Chemical compound 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
KICQGFIBESUFTC-UHFFFAOYSA-N n-(3-chlorophenyl)-1-phenylethanimine Chemical compound C=1C=CC=CC=1C(C)=NC1=CC=CC(Cl)=C1 KICQGFIBESUFTC-UHFFFAOYSA-N 0.000 description 2
IOOMCIKHTFGETB-UHFFFAOYSA-N n-(4-dodecylphenyl)-1-phenylethanimine Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1N=C(C)C1=CC=CC=C1 IOOMCIKHTFGETB-UHFFFAOYSA-N 0.000 description 2
WATIYJMFKFSKGZ-UHFFFAOYSA-N n-(4-methoxyphenyl)-1-phenylethanimine Chemical compound C1=CC(OC)=CC=C1N=C(C)C1=CC=CC=C1 WATIYJMFKFSKGZ-UHFFFAOYSA-N 0.000 description 2
125000005609 naphthenate group Chemical group 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
GARQDIVXKVBJFP-UHFFFAOYSA-N p-Octylacetophenone Chemical compound CCCCCCCCC1=CC=C(C(C)=O)C=C1 GARQDIVXKVBJFP-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003335 secondary amines Chemical group 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
239000004711 α-olefin Substances 0.000 description 2
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
HFWHTGSLDKKCMD-UHFFFAOYSA-N 2,2-bis(octanoyloxymethyl)butyl octanoate Chemical compound CCCCCCCC(=O)OCC(CC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC HFWHTGSLDKKCMD-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
FKHKSWSHWLYDOI-UHFFFAOYSA-N 2-phenylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C=2C=CC=CC=2)=C1 FKHKSWSHWLYDOI-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 description 1
OPSCELGIEGNCMF-UHFFFAOYSA-N 4-methyl-n-(1-phenylethyl)aniline Chemical compound C=1C=CC=CC=1C(C)NC1=CC=C(C)C=C1 OPSCELGIEGNCMF-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical class CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000005643 Pelargonic acid Substances 0.000 description 1
CFRNDJFRRKMHTL-UHFFFAOYSA-N [3-octanoyloxy-2,2-bis(octanoyloxymethyl)propyl] octanoate Chemical compound CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)COC(=O)CCCCCCC CFRNDJFRRKMHTL-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000003939 benzylamines Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
239000008380 degradant Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
WIYAGHSNPUBKDT-UHFFFAOYSA-N dinonyl hexanedioate Chemical compound CCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCC WIYAGHSNPUBKDT-UHFFFAOYSA-N 0.000 description 1
MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000010696 ester oil Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000002431 foraging effect Effects 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
CBXWICRJSHEQJT-UHFFFAOYSA-N n,1-diphenylethanimine Chemical compound C=1C=CC=CC=1C(C)=NC1=CC=CC=C1 CBXWICRJSHEQJT-UHFFFAOYSA-N 0.000 description 1
YXIIXSXZNDIDFR-UHFFFAOYSA-N n-(2-methoxyphenyl)-1-phenylethanimine Chemical compound COC1=CC=CC=C1N=C(C)C1=CC=CC=C1 YXIIXSXZNDIDFR-UHFFFAOYSA-N 0.000 description 1
ZHVXOUDFYNBYJK-UHFFFAOYSA-N n-(4-chlorophenyl)-1-phenylethanimine Chemical compound C=1C=CC=CC=1C(C)=NC1=CC=C(Cl)C=C1 ZHVXOUDFYNBYJK-UHFFFAOYSA-N 0.000 description 1
150000005002 naphthylamines Chemical class 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
238000006864 oxidative decomposition reaction Methods 0.000 description 1
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
150000004989 p-phenylenediamines Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920013636 polyphenyl ether polymer Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000010689 synthetic lubricating oil Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000004580 weight loss 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
- C10M133/14—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- 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
- C10M2207/16—Naphthenic 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- 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
- C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Lubricants (AREA)
Anti-Oxidant Or Stabilizer Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP7364580A 1979-05-31 1980-05-31 Antioxidant for lubricant oil Granted JPS55161894A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4399679A	1979-05-31	1979-05-31

Publications (2)

Publication Number	Publication Date
JPS55161894A JPS55161894A (en)	1980-12-16
JPH0144276B2 true JPH0144276B2 (2)	1989-09-26

Family

ID=21929979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7364580A Granted JPS55161894A (en)	1979-05-31	1980-05-31	Antioxidant for lubricant oil

Country Status (5)

Country	Link
EP (1)	EP0022281B1 (2)
JP (1)	JPS55161894A (2)
BR (1)	BR8003141A (2)
CA (1)	CA1138472A (2)
DE (1)	DE3064808D1 (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9920285D0 (en)	1999-08-27	1999-10-27	Johnson Matthey Plc	Improved catalytic process
US7501386B2 (en)	2005-12-21	2009-03-10	Chevron Oronite Company, Llc	Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH312721A (de) *	1952-02-07	1956-02-29	Yair Dr Sprinzak	Verfahren zur Herstellung sekundärer cyclischer Benzylamine
US3366683A (en) *	1963-10-23	1968-01-30	Gen Aniline & Film Corp	Method for the production of benzyl anilines
US3579582A (en) *	1967-02-16	1971-05-18	Universal Oil Prod Co	Hydroxy and/or hydrocarbyloxy and amino substituted tetrahydronaphthalenes
US3822284A (en) *	1970-07-16	1974-07-02	Shell Oil Co	1-and 3-substituted (3,5-di-t-butyl-4-hydroxybenzyl)carbazole

1979
- 1979-08-22 CA CA000334239A patent/CA1138472A/en not_active Expired
1980
- 1980-05-20 BR BR8003141A patent/BR8003141A/pt unknown
- 1980-05-30 EP EP19800200511 patent/EP0022281B1/en not_active Expired
- 1980-05-30 DE DE8080200511T patent/DE3064808D1/de not_active Expired
- 1980-05-31 JP JP7364580A patent/JPS55161894A/ja active Granted

Also Published As

Publication number	Publication date
EP0022281A1 (en)	1981-01-14
EP0022281B1 (en)	1983-09-14
JPS55161894A (en)	1980-12-16
BR8003141A (pt)	1980-12-23
DE3064808D1 (en)	1983-10-20
CA1138472A (en)	1982-12-28

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AU755427C (en)	2003-07-03	Poly(neopentyl polyol) ester based coolants and improved additive package
DE2233542C3 (de)	1981-11-05	Schmiermittelgemisch
ITMI981274A1 (it)	1999-12-05	Defenilammine nonilate
US3290307A (en)	1966-12-06	Nu-substituted melamines
JPS6289796A (ja)	1987-04-24	新規な組合せの安定化剤を含む潤滑油組成物
DE69527652T2 (de)	2003-04-03	Antioxydant aus monosubstituierten diphenyl-aminen für syntetische schmiermittel
CN101925668A (zh)	2010-12-22	抗氧化剂和/或抗腐蚀剂、含有所述试剂的润滑组合物以及制备它们的方法
JP2923341B2 (ja)	1999-07-26	潤滑油添加剤及びそれを含有する潤滑油組成物
DE1695400A1 (de)	1971-03-18	Verfahren zur Oxydation aromatischer sekundaerer Naphthylamine
BR9915862B1 (pt)	2010-11-30	composição lubrificante e método de aumentar a estabilidade à axidação de óleo lubrificante.
US7307049B1 (en)	2007-12-11	Antioxidants for synthetic lubricants and methods and manufacture
US4090970A (en)	1978-05-23	Antioxidant compositions
US4122021A (en)	1978-10-24	Antioxidant stabilized lubricating oils
US4335006A (en)	1982-06-15	Method of stabilizing lubricating fluids
EP0019985B1 (en)	1983-11-23	A method for stabilizing a lubricating oil
US4225448A (en)	1980-09-30	Copper thiobis(alkylphenols) and antioxidant compositions thereof
US4260501A (en)	1981-04-07	Lubricant compositions containing antioxidant mixtures comprising substituted thiazoles and substituted thiadiazole compounds
US3919269A (en)	1975-11-11	Acylated phenylene diamines
EP0089023B1 (en)	1987-10-07	Stabilizer systems useful in lubricating oils and method for stabilizing lubricating oils
EP0164471B1 (en)	1989-11-08	Composition containing benzothiazolines as antioxidants
EP0022281B1 (en)	1983-09-14	Amino compounds and use of amino compounds as antioxydant in lubricating oils
US4151100A (en)	1979-04-24	Novel cobalt thiobis(alkylphenolates) and antioxidant compositions thereof
US3260672A (en)	1966-07-12	Synthetic ester lubricating oil containing certain haloalkyl carboxylic acid esters
US20080317964A1 (en)	2008-12-25	High Temperature Lubricant Compositions and Methods of Making the Same
US4962234A (en)	1990-10-09	Antioxidant for polyester fluids - alpha - methyl - n phenylbenzenemethanamine