CN1135221C - 壬基化二苯胺 - Google Patents
壬基化二苯胺 Download PDFInfo
- Publication number
- CN1135221C CN1135221C CNB981096557A CN98109655A CN1135221C CN 1135221 C CN1135221 C CN 1135221C CN B981096557 A CNB981096557 A CN B981096557A CN 98109655 A CN98109655 A CN 98109655A CN 1135221 C CN1135221 C CN 1135221C
- Authority
- CN
- China
- Prior art keywords
- area
- mixture
- pentanoic
- acid
- diphenylamine
- 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 - Fee Related
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- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 34
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- -1 diphenylamine compound Chemical class 0.000 claims description 63
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 46
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 claims description 42
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 27
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 claims description 24
- 239000004927 clay Substances 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 11
- 230000000996 additive effect Effects 0.000 abstract description 11
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 27
- 238000012360 testing method Methods 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- 230000001939 inductive effect Effects 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229960003742 phenol Drugs 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 150000003863 ammonium salts Chemical class 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- 239000000314 lubricant Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 230000002152 alkylating effect Effects 0.000 description 6
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- 150000001412 amines Chemical class 0.000 description 5
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- 238000010438 heat treatment Methods 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
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- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 229950006389 thiodiglycol Drugs 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000009434 installation Methods 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 3
- 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 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical class CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- BVALZCVRLDMXOQ-UHFFFAOYSA-N 1-nitropentane Chemical compound CCCCC[N+]([O-])=O BVALZCVRLDMXOQ-UHFFFAOYSA-N 0.000 description 2
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
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- 229910000831 Steel Inorganic materials 0.000 description 2
- 241000534944 Thia Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
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- ZIJHTQPOUJBOHK-UHFFFAOYSA-N (3-tert-butyl-4-hydroxy-5-methylphenyl)methylphosphonic acid Chemical class CC1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZIJHTQPOUJBOHK-UHFFFAOYSA-N 0.000 description 1
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- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical class S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
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- UDAKRDQBQXLJHF-UHFFFAOYSA-N 1-(3-amino-4-hydroxyphenyl)nonan-1-one Chemical compound CCCCCCCCC(=O)C1=CC=C(O)C(N)=C1 UDAKRDQBQXLJHF-UHFFFAOYSA-N 0.000 description 1
- LNZBQIBHNKDRIL-UHFFFAOYSA-N 1-(3-amino-4-hydroxyphenyl)octadecan-1-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)C1=CC=C(O)C(N)=C1 LNZBQIBHNKDRIL-UHFFFAOYSA-N 0.000 description 1
- SQZCAOHYQSOZCE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N=C(N)N SQZCAOHYQSOZCE-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- DVQDEYTXFHYBNP-UHFFFAOYSA-N 2,5-di(pentan-2-yl)phenol Chemical compound CCCC(C)C1=CC=C(C(C)CCC)C(O)=C1 DVQDEYTXFHYBNP-UHFFFAOYSA-N 0.000 description 1
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- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical class CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/55—Diphenylamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paper (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1377/1997 | 1997-06-06 | ||
| CH1377/97 | 1997-06-06 | ||
| CH137797 | 1997-06-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1201781A CN1201781A (zh) | 1998-12-16 |
| CN1135221C true CN1135221C (zh) | 2004-01-21 |
Family
ID=4209007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB981096557A Expired - Fee Related CN1135221C (zh) | 1997-06-06 | 1998-06-05 | 壬基化二苯胺 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6315925B1 (enExample) |
| JP (3) | JP4833387B2 (enExample) |
| KR (1) | KR100624206B1 (enExample) |
| CN (1) | CN1135221C (enExample) |
| BE (1) | BE1013124A3 (enExample) |
| BR (1) | BR9802365A (enExample) |
| CA (1) | CA2240971C (enExample) |
| CZ (1) | CZ294662B6 (enExample) |
| DE (1) | DE19824790B4 (enExample) |
| ES (1) | ES2151819B1 (enExample) |
| FR (1) | FR2764887B1 (enExample) |
| GB (1) | GB2325929B (enExample) |
| IT (1) | ITMI981274A1 (enExample) |
| NL (1) | NL1009331C2 (enExample) |
| RU (1) | RU2198870C2 (enExample) |
| SG (1) | SG65759A1 (enExample) |
| SK (1) | SK285027B6 (enExample) |
| TW (1) | TW555733B (enExample) |
| ZA (1) | ZA984871B (enExample) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2513669B2 (ja) | 1987-03-26 | 1996-07-03 | 東レ株式会社 | 引裂直線性のある二軸延伸ポリエステルフイルム |
| SG65759A1 (en) * | 1997-06-06 | 1999-06-22 | Ciba Sc Holding Ag | Nonylated diphenylamines |
| US6684759B1 (en) | 1999-11-19 | 2004-02-03 | Vladimir Gorokhovsky | Temperature regulator for a substrate in vapor deposition processes |
| US6871700B2 (en) | 2000-11-17 | 2005-03-29 | G & H Technologies Llc | Thermal flux regulator |
| US7189875B2 (en) * | 2003-04-04 | 2007-03-13 | Crompton Corporation | Diphenylamine alkylated with olefin mixtures containing fractions with varying degrees of activity |
| US6930183B2 (en) * | 2003-04-17 | 2005-08-16 | Crompton Corporation | Alkylated iminodibenzyls as antioxidants |
| SK14562003A3 (sk) * | 2003-11-25 | 2005-06-02 | Duslo,A.S. | Antioxidačné kompozície oktylovaných difenylamínov a spôsob ich výroby |
| PL1730101T3 (pl) * | 2004-04-01 | 2016-05-31 | Basf Se | Kompozycje alkilowanej PANA i DPA |
| US7816308B2 (en) * | 2004-04-14 | 2010-10-19 | Crompton Corporation | Ketone diarylamine condensates |
| US8202829B2 (en) * | 2004-11-04 | 2012-06-19 | Afton Chemical Corporation | Lubricating composition |
| EA200702666A1 (ru) * | 2005-06-02 | 2008-06-30 | Альбемарл Корпорейшн | Усовершенствованный процесс синтеза алкилированных ариламинов |
| US7145038B1 (en) | 2005-12-14 | 2006-12-05 | Chemtura Corporation | Alkylation of a diphenylamine compound in ionic liquid |
| US7390928B2 (en) | 2005-12-14 | 2008-06-24 | Chemtura Corporation | Alkylation of N′-phenyl-N-alkylphenylenediamines in ionic liquid, N′-phenyl-N-alkyl (alkylphenylene) diamines produced thereby, and lubricant compositions containing same |
| 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 |
| US8003583B2 (en) * | 2005-12-21 | 2011-08-23 | Chevron Oronite Company Llc | Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions |
| US7285518B2 (en) * | 2005-12-21 | 2007-10-23 | Chevron Oronite Company Llc | Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions |
| US8828916B2 (en) * | 2006-12-28 | 2014-09-09 | Chevron Oronite Company Llc | Method to prepare nonylated diphenylamine using recycle sequential temperatures |
| RU2346029C2 (ru) * | 2007-03-27 | 2009-02-10 | Открытое акционерное общество "Всероссийский научно-исследовательский институт по переработке нефти" | Способ получения антиокислительной присадки к смазочным маслам |
| JP5509484B2 (ja) | 2007-06-08 | 2014-06-04 | インフィニューム インターナショナル リミテッド | 添加剤及びそれを含む潤滑油組成物 |
| US7683017B2 (en) * | 2007-06-20 | 2010-03-23 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine |
| US8110532B2 (en) * | 2008-11-24 | 2012-02-07 | Chemtura Corporation | Antioxidant compositions |
| RU2476587C2 (ru) * | 2010-11-12 | 2013-02-27 | Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации | Смазочная композиция высокотемпературного масла для теплонапряженных газотурбинных двигателей сверхзвуковой авиации |
| CN102659606B (zh) * | 2012-05-07 | 2014-04-09 | 常州大学 | 一种色泽稳定的烷基化二苯胺抗氧剂的制备方法 |
| US9617201B2 (en) | 2013-10-14 | 2017-04-11 | Chemtura Corporation | Fixed bed process for clay catalyzed alkylation of aromatic amines |
| GB2523756B (en) | 2014-03-03 | 2017-01-11 | Addivant Switzerland Gmbh | Antioxidant compositions |
| US9890346B2 (en) | 2014-07-21 | 2018-02-13 | Lanxess Solutions Us Inc. | Selective alkylation method for producing p, p′-di-alkylated diphenylamine antioxidants |
| US9744531B2 (en) | 2015-03-03 | 2017-08-29 | Lanxess Solutions Us Inc. | Regeneration of clay catalysts for alkylation of aromatic rings |
| KR20180030831A (ko) | 2015-07-15 | 2018-03-26 | 란세스 솔루션즈 유에스 인코퍼레이티드 | 분지형 올레핀으로부터 제조된 디아릴 아민 항산화제 |
| US20190367833A1 (en) | 2016-12-27 | 2019-12-05 | The Lubrizol Corporation | Lubricating composition including n-alkylated dianiline |
| WO2018125567A1 (en) | 2016-12-27 | 2018-07-05 | The Lubrizol Corporation | Lubricating composition with alkylated naphthylamine |
| CN106699677B (zh) * | 2016-12-28 | 2019-07-09 | 利安隆（中卫）新材料有限公司 | 紫外线吸收剂uv-571的制备方法 |
| MX2023005680A (es) * | 2020-11-17 | 2023-06-29 | Songwon Ind Co Ltd | Composiciones que comprenden difenilaminas alquiladas con propiedades mejoradas. |
| TW202311225A (zh) | 2021-06-25 | 2023-03-16 | 韓商松原產業股份有限公司 | O-烷基化位阻抗氧化劑 |
| CN115254088B (zh) * | 2022-08-30 | 2023-11-21 | 华东理工大学 | 一种生产烷基二苯胺的催化剂及其制备方法和应用 |
| WO2024158648A1 (en) | 2023-01-24 | 2024-08-02 | The Lubrizol Corporation | Lubricating composition with phenolic antioxidant and low active sulfur |
| CN121219388A (zh) | 2023-03-31 | 2025-12-26 | 朗盛公司 | 用于生产安全、环保的二取代二苯胺抗氧化剂的高效、低能耗、低废弃物的烷基化和芳基化方法 |
| CN121548626A (zh) | 2023-07-27 | 2026-02-17 | 路博润公司 | 含有酚类抗氧化剂、水杨酸钙洗涤剂和低活性硫的润滑组合物 |
| US20250136889A1 (en) * | 2023-10-27 | 2025-05-01 | Infineum International Limited | Lubricant Compositions Containing High C9 Disubstituted Diphenylamine Antioxidant Content |
| WO2026087620A1 (en) | 2024-10-23 | 2026-04-30 | Infineum International Limited | Lubricant compositions containing high c9 disubstituted diphenylamine antioxidant content |
| CN120818190B (zh) * | 2025-09-17 | 2026-02-03 | 天津利安隆新材料股份有限公司 | 一种生橡胶组合物以及抗老化剂组合物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776994A (en) | 1954-03-03 | 1957-01-08 | Goodrich Co B F | Preparation of a solid diphenylamine antioxidant |
| US2943112A (en) * | 1957-11-06 | 1960-06-28 | Pennsalt Chemicals Corp | Alkylation of diphenylamine |
| US3496230A (en) | 1966-02-17 | 1970-02-17 | American Cyanamid Co | Process for mixture of mono- and dialkyl-diphenylamines |
| CA1083606A (en) * | 1975-04-18 | 1980-08-12 | Vipin M. Kothari | Process of preparing para styrenated diphenylamine. |
| JPS58108296A (ja) * | 1981-12-21 | 1983-06-28 | Sumitomo Chem Co Ltd | 燃料油用液状酸化防止剤 |
| GB8332797D0 (en) * | 1983-12-08 | 1984-01-18 | Ciba Geigy Ag | Antioxidant production |
| JPS60202845A (ja) * | 1984-03-28 | 1985-10-14 | Seikou Kagaku Kk | 白度または透明度の高いｐ−置換ジフエニルアミン類の製造法 |
| US4739121A (en) | 1984-05-24 | 1988-04-19 | The B. F. Goodrich Company | Process for otho- and para-alkylating diphenylamines |
| JPS6197378A (ja) * | 1984-10-18 | 1986-05-15 | Toyoda Gosei Co Ltd | エアダクト用シ−ラント |
| US4769164A (en) * | 1987-05-22 | 1988-09-06 | The Lubrizol Corporation | Anti-oxidant products |
| US4798684A (en) * | 1987-06-09 | 1989-01-17 | The Lubrizol Corporation | Nitrogen containing anti-oxidant compositions |
| JP2539677B2 (ja) * | 1989-01-13 | 1996-10-02 | 日本石油株式会社 | 潤滑油組成物 |
| RU2015959C1 (ru) * | 1992-07-06 | 1994-07-15 | Александр Константинович Аветисов | Способ получения дифениламина |
| JPH0959227A (ja) * | 1995-08-11 | 1997-03-04 | Seiko Kagaku Kk | スチレン化ジフェニルアミンの製造方法 |
| US5750787A (en) * | 1995-09-13 | 1998-05-12 | B. F. Goodrich Company | Liquid alkylated diphenylamine antioxidant |
| US5672752A (en) * | 1995-09-13 | 1997-09-30 | The Bfgoodrich Company | Liquid alkylated diphenylamine antioxidant |
| SG65759A1 (en) * | 1997-06-06 | 1999-06-22 | Ciba Sc Holding Ag | Nonylated diphenylamines |
-
1998
- 1998-05-21 SG SG1998001100A patent/SG65759A1/en unknown
- 1998-06-01 GB GB9811583A patent/GB2325929B/en not_active Expired - Fee Related
- 1998-06-02 RU RU98110273/04A patent/RU2198870C2/ru not_active IP Right Cessation
- 1998-06-03 DE DE19824790A patent/DE19824790B4/de not_active Expired - Fee Related
- 1998-06-03 CZ CZ19981716A patent/CZ294662B6/cs not_active IP Right Cessation
- 1998-06-04 CA CA002240971A patent/CA2240971C/en not_active Expired - Fee Related
- 1998-06-04 TW TW087108805A patent/TW555733B/zh not_active IP Right Cessation
- 1998-06-04 SK SK743-98A patent/SK285027B6/sk not_active IP Right Cessation
- 1998-06-04 JP JP17230998A patent/JP4833387B2/ja not_active Expired - Fee Related
- 1998-06-04 ES ES009801159A patent/ES2151819B1/es not_active Expired - Lifetime
- 1998-06-04 FR FR9806996A patent/FR2764887B1/fr not_active Expired - Fee Related
- 1998-06-05 BE BE9800425A patent/BE1013124A3/fr active
- 1998-06-05 NL NL1009331A patent/NL1009331C2/nl not_active IP Right Cessation
- 1998-06-05 ZA ZA984871A patent/ZA984871B/xx unknown
- 1998-06-05 KR KR1019980020780A patent/KR100624206B1/ko not_active Expired - Fee Related
- 1998-06-05 IT IT98MI001274A patent/ITMI981274A1/it unknown
- 1998-06-05 BR BR9802365-9A patent/BR9802365A/pt not_active Application Discontinuation
- 1998-06-05 CN CNB981096557A patent/CN1135221C/zh not_active Expired - Fee Related
-
2000
- 2000-02-14 US US09/503,264 patent/US6315925B1/en not_active Expired - Lifetime
-
2009
- 2009-06-08 JP JP2009137187A patent/JP2009197026A/ja active Pending
-
2012
- 2012-07-27 JP JP2012167148A patent/JP5650692B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CZ294662B6 (cs) | 2005-02-16 |
| JP5650692B2 (ja) | 2015-01-07 |
| JP2012197462A (ja) | 2012-10-18 |
| DE19824790B4 (de) | 2013-06-20 |
| JP2009197026A (ja) | 2009-09-03 |
| ZA984871B (en) | 1998-12-07 |
| JP4833387B2 (ja) | 2011-12-07 |
| SG65759A1 (en) | 1999-06-22 |
| FR2764887A1 (fr) | 1998-12-24 |
| FR2764887B1 (fr) | 2004-04-02 |
| US6315925B1 (en) | 2001-11-13 |
| GB2325929B (en) | 2001-08-29 |
| CZ171698A3 (cs) | 1998-12-16 |
| ITMI981274A1 (it) | 1999-12-05 |
| SK74398A3 (en) | 1999-04-13 |
| TW555733B (en) | 2003-10-01 |
| NL1009331C2 (nl) | 2001-05-08 |
| CN1201781A (zh) | 1998-12-16 |
| JPH1112234A (ja) | 1999-01-19 |
| ES2151819A1 (es) | 2001-01-01 |
| RU2198870C2 (ru) | 2003-02-20 |
| BR9802365A (pt) | 2000-03-28 |
| SK285027B6 (sk) | 2006-04-06 |
| ES2151819B1 (es) | 2001-08-16 |
| CA2240971C (en) | 2008-02-12 |
| NL1009331A1 (nl) | 1998-12-08 |
| KR100624206B1 (ko) | 2006-12-05 |
| BE1013124A3 (fr) | 2001-10-02 |
| GB9811583D0 (en) | 1998-07-29 |
| GB2325929A (en) | 1998-12-09 |
| DE19824790A1 (de) | 1999-04-15 |
| KR19990006677A (ko) | 1999-01-25 |
| CA2240971A1 (en) | 1998-12-06 |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
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Granted publication date: 20040121 Termination date: 20170605 |