CA2382802A1 - Method of manufacturing alkylated phenylnaphthylamine compositions; and products - Google Patents

Method of manufacturing alkylated phenylnaphthylamine compositions; and products Download PDF

Info

Publication number: CA2382802A1
Authority: CA; Canada
Prior art keywords: phenylnaphthylamine; nonalkylated; composition; olefin; alkylating
Prior art date: 1999-09-30
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.): Abandoned

Application number

CA002382802A

Other languages

English (en)

French (fr)

Inventor

John Ta-Yuan Lai

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.)

Noveon IP Holdings Corp

Original Assignee

Individual

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.)

1999-09-30

Filing date

2000-09-07

Publication date

2001-04-05

2000-09-07 Application filed by Individual filed Critical Individual

2001-04-05 Publication of CA2382802A1 publication Critical patent/CA2382802A1/en

Status Abandoned legal-status Critical Current

Links

XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 title claims abstract description 349
239000000203 mixture Substances 0.000 title claims abstract description 133
238000004519 manufacturing process Methods 0.000 title claims abstract description 11
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 72
239000004927 clay Substances 0.000 claims abstract description 70
239000003054 catalyst Substances 0.000 claims abstract description 64
150000001336 alkenes Chemical class 0.000 claims abstract description 61
230000002152 alkylating effect Effects 0.000 claims abstract description 38
238000000034 method Methods 0.000 claims abstract description 33
239000003963 antioxidant agent Substances 0.000 claims abstract description 32
239000000314 lubricant Substances 0.000 claims abstract description 27
230000003078 antioxidant effect Effects 0.000 claims abstract description 23
239000000376 reactant Substances 0.000 claims description 73
238000006243 chemical reaction Methods 0.000 claims description 44
125000004432 carbon atom Chemical group C* 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 5
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
239000013638 trimer Substances 0.000 claims 4
238000005804 alkylation reaction Methods 0.000 description 32
230000029936 alkylation Effects 0.000 description 24
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 22
239000000047 product Substances 0.000 description 21
239000007795 chemical reaction product Substances 0.000 description 14
230000035484 reaction time Effects 0.000 description 12
239000002253 acid Substances 0.000 description 11
-1 Olefins Olefins Chemical class 0.000 description 8
230000001050 lubricating effect Effects 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000012530 fluid Substances 0.000 description 7
125000000524 functional group Chemical group 0.000 description 7
150000001875 compounds Chemical class 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000003381 stabilizer Substances 0.000 description 5
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
238000005336 cracking Methods 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
125000005266 diarylamine group Chemical group 0.000 description 3
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000547 substituted alkyl group Chemical group 0.000 description 3
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
ZQICGTYUOSVFMN-UHFFFAOYSA-N Iselin Natural products CC1=C(COc2c3ccoc3cc3oc(=O)ccc23)CC(C)(C)CC1 ZQICGTYUOSVFMN-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
235000012216 bentonite Nutrition 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000003599 detergent Substances 0.000 description 2
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
229910052901 montmorillonite Inorganic materials 0.000 description 2
SNWVRVDHQRBBFG-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)naphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 SNWVRVDHQRBBFG-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000010525 oxidative degradation reaction Methods 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
LAAVYEUJEMRIGF-UHFFFAOYSA-N 2,4,4-trimethylpent-2-ene Chemical compound CC(C)=CC(C)(C)C LAAVYEUJEMRIGF-UHFFFAOYSA-N 0.000 description 1
PFCCSTRBUBCYSK-UHFFFAOYSA-N 2-methylprop-1-ene Chemical group CC(C)=C.CC(C)=C.CC(C)=C.CC(C)=C PFCCSTRBUBCYSK-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
229940123457 Free radical scavenger Drugs 0.000 description 1
238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Chemical group 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical group [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000032683 aging Effects 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
150000001565 benzotriazoles Chemical class 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
238000001354 calcination Methods 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000002734 clay mineral Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000029087 digestion Effects 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052909 inorganic silicate Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000002386 leaching Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000010687 lubricating oil Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
NDVVCLKNUSBRJS-UHFFFAOYSA-N n-decyl-n-phenylnaphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1N(CCCCCCCCCC)C1=CC=CC=C1 NDVVCLKNUSBRJS-UHFFFAOYSA-N 0.000 description 1
UMKFCWWZAONEEQ-UHFFFAOYSA-N n-nonyl-n-phenylnaphthalen-1-amine Chemical class C=1C=CC2=CC=CC=C2C=1N(CCCCCCCCC)C1=CC=CC=C1 UMKFCWWZAONEEQ-UHFFFAOYSA-N 0.000 description 1
CQOJLEZMTZNHBO-UHFFFAOYSA-N n-phenyl-n-tetradecylnaphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1N(CCCCCCCCCCCCCC)C1=CC=CC=C1 CQOJLEZMTZNHBO-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229910052756 noble gas Inorganic materials 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
- 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
- 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
- C10M2215/065—Phenyl-Naphthyl amines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Lubricants (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA002382802A 1999-09-30 2000-09-07 Method of manufacturing alkylated phenylnaphthylamine compositions; and products Abandoned CA2382802A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US40932799A	1999-09-30	1999-09-30
US09/409,327		1999-09-30
PCT/US2000/024500 WO2001023343A2 (en)	1999-09-30	2000-09-07	Method of manufacturing alkylated phenylnaphthylamine compositions; and products

Publications (1)

Publication Number	Publication Date
CA2382802A1 true CA2382802A1 (en)	2001-04-05

Family

ID=23620009

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002382802A Abandoned CA2382802A1 (en)	1999-09-30	2000-09-07	Method of manufacturing alkylated phenylnaphthylamine compositions; and products

Country Status (7)

Country	Link
EP (1)	EP1216224A2 (cs)
AU (1)	AU7119300A (cs)
BR (1)	BR0014367A (cs)
CA (1)	CA2382802A1 (cs)
CZ (1)	CZ20021049A3 (cs)
MX (1)	MXPA02003261A (cs)
WO (1)	WO2001023343A2 (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8828916B2 (en)	2006-12-28	2014-09-09	Chevron Oronite Company Llc	Method to prepare nonylated diphenylamine using recycle sequential temperatures
CN117529539A (zh)	2021-04-21	2024-02-06	朗盛公司	液体单烷基化N-苯基-α-萘胺组合物及其制造方法
WO2024194115A1 (en) *	2023-03-20	2024-09-26	Basf Se	Liquid alkylated phenyl-alpha-naphthylamine with reduced aquatic toxicity

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4770802A (en) *	1986-02-04	1988-09-13	Nippon Oil Co., Ltd.	Lubricating oil compositions
DE69405410T2 (de) *	1993-12-15	1998-03-19	Goodrich Co B F	Stabilisatormischung für synthetisches estergleitmittel

2000
- 2000-09-07 CZ CZ20021049A patent/CZ20021049A3/cs unknown
- 2000-09-07 MX MXPA02003261A patent/MXPA02003261A/es unknown
- 2000-09-07 BR BR0014367-7A patent/BR0014367A/pt not_active Application Discontinuation
- 2000-09-07 CA CA002382802A patent/CA2382802A1/en not_active Abandoned
- 2000-09-07 WO PCT/US2000/024500 patent/WO2001023343A2/en not_active Ceased
- 2000-09-07 AU AU71193/00A patent/AU7119300A/en not_active Abandoned
- 2000-09-07 EP EP00959963A patent/EP1216224A2/en not_active Withdrawn

Also Published As

Publication number	Publication date
CZ20021049A3 (cs)	2002-07-17
AU7119300A (en)	2001-04-30
WO2001023343A3 (en)	2001-11-29
BR0014367A (pt)	2002-06-11
EP1216224A2 (en)	2002-06-26
MXPA02003261A (es)	2002-09-30
WO2001023343A2 (en)	2001-04-05

Legal Events

Date	Code	Title	Description
2004-09-07	FZDE	Discontinued

Publication	Publication Date	Title
EP1171415B1 (en)	2003-12-03	Method of manufacturing alkylated diphenylamine compositions
CA2399479C (en)	2010-10-19	Alkylation of diphenylamine with polyisobutylene oligomers
CA2649975C (en)	2013-07-16	Lubricating compositions containing ashless catalytic antioxidant additives
EP3322690B1 (en)	2021-08-11	Diaryl amine antioxidants prepared from branched olefins
EP3172296B1 (en)	2021-05-19	Selective alkylation method for producing p,p'-di-alkylated diphenylamine antioxidants
EP1020425B1 (en)	2004-01-21	Liquid alkylated diphenylamine antioxidant
US5672752A (en)	1997-09-30	Liquid alkylated diphenylamine antioxidant
CA2616569C (en)	2015-02-17	Method to prepare nonylated diphenylamine using recycle and sequential temperatures
CA2382802A1 (en)	2001-04-05	Method of manufacturing alkylated phenylnaphthylamine compositions; and products
EP4326842B1 (en)	2025-01-15	Liquid mono-alkylated n-phenyl-alpha-napthylamine compositions and methods of manufacturing the same
EP2139977B1 (en)	2012-09-05	Lubricating compositions containing ashless catalytic antioxidant additives
EP4689027A1 (en)	2026-02-11	Efficient, low-energy, low waste alkylation and arylation method for producing safe, enviromentally-friendly disubstituted diphenylamine antioxidants
HK1029579B (en)	2004-06-11	Liquid alkylated diphenylamine antioxidant
CA2526180A1 (en)	1997-11-30	Liquid alkylated diphenylamine antioxidant
HK1065529B (en)	2008-04-25	Oxidation stabilized lubricating oils and polyol solutions