ES2573690T3 - Productos de reacción heterocíclicos alquilados útiles como antioxidantes - Google Patents
Productos de reacción heterocíclicos alquilados útiles como antioxidantes Download PDFInfo
- Publication number
- ES2573690T3 ES2573690T3 ES07854115.8T ES07854115T ES2573690T3 ES 2573690 T3 ES2573690 T3 ES 2573690T3 ES 07854115 T ES07854115 T ES 07854115T ES 2573690 T3 ES2573690 T3 ES 2573690T3
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- ES
- Spain
- Prior art keywords
- isomer
- heterocyclic compounds
- dihydrocarbyl
- minutes
- compounds substituted
- 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.)
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- 239000007795 chemical reaction product Substances 0.000 title abstract 2
- 239000003963 antioxidant agent Substances 0.000 title 1
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 27
- 229930192474 thiophene Natural products 0.000 abstract description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 8
- 150000002391 heterocyclic compounds Chemical group 0.000 abstract 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- DPHVWRMZSWGLLA-UHFFFAOYSA-N 1,2-benzodithiine Chemical compound C1=CC=C2C=CSSC2=C1 DPHVWRMZSWGLLA-UHFFFAOYSA-N 0.000 abstract 1
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 abstract 1
- HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 abstract 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 abstract 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- AXLOCHLTNQDFFS-BESJYZOMSA-N azastene Chemical compound C([C@H]1[C@@H]2CC[C@@]([C@]2(CC[C@@H]1[C@@]1(C)C2)C)(O)C)C=C1C(C)(C)C1=C2C=NO1 AXLOCHLTNQDFFS-BESJYZOMSA-N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- RIYVKHUVXPAOPS-UHFFFAOYSA-N dithiine Chemical compound S1SC=CC=C1 RIYVKHUVXPAOPS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 abstract 1
- -1 monoalkylamino Chemical group 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- SCXYLTWTWUGEAA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methoxymethyl)phenol Chemical compound COCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SCXYLTWTWUGEAA-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 238000006388 chemical passivation reaction Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/82—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of another six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
-
- 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
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
-
- 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
-
- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino 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
- 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
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
- 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
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyethers (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82983806P | 2006-10-17 | 2006-10-17 | |
| US829838P | 2006-10-17 | ||
| PCT/US2007/081603 WO2008048988A2 (en) | 2006-10-17 | 2007-10-17 | Alkylated heterocyclic reaction products useful as antioxidants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2573690T3 true ES2573690T3 (es) | 2016-06-09 |
Family
ID=37907571
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07854115.8T Active ES2573690T3 (es) | 2006-10-17 | 2007-10-17 | Productos de reacción heterocíclicos alquilados útiles como antioxidantes |
| ES13171810.8T Active ES2575779T3 (es) | 2006-10-17 | 2007-10-17 | Productos de reacción heterocíclicos alquilados útiles como antioxidantes |
| ES07854116.6T Active ES2513822T3 (es) | 2006-10-17 | 2007-10-17 | Composiciones antioxidantes amino-fenólicas macromoleculares, tecnología de fabricación de las mismas, y sus usos |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13171810.8T Active ES2575779T3 (es) | 2006-10-17 | 2007-10-17 | Productos de reacción heterocíclicos alquilados útiles como antioxidantes |
| ES07854116.6T Active ES2513822T3 (es) | 2006-10-17 | 2007-10-17 | Composiciones antioxidantes amino-fenólicas macromoleculares, tecnología de fabricación de las mismas, y sus usos |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8410084B2 (enExample) |
| EP (3) | EP2079677B1 (enExample) |
| JP (2) | JP2010522136A (enExample) |
| KR (2) | KR101520880B1 (enExample) |
| CN (2) | CN101610992B (enExample) |
| AU (4) | AU2007311083A1 (enExample) |
| BR (2) | BRPI0717811A2 (enExample) |
| CA (2) | CA2665012C (enExample) |
| EA (2) | EA015929B1 (enExample) |
| ES (3) | ES2573690T3 (enExample) |
| PL (3) | PL2084142T3 (enExample) |
| PT (2) | PT2662351T (enExample) |
| SG (1) | SG175624A1 (enExample) |
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| WO (4) | WO2008048988A2 (enExample) |
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| WO2009073378A1 (en) * | 2007-11-29 | 2009-06-11 | Albemarle Corporation | Industrial oil formulations containing macromolecular antioxidants |
| EP2331493A1 (en) * | 2008-08-08 | 2011-06-15 | Albemarle Corporation | Octylated phenyl-alpha-naphthylamine product mixtures and production of such mixtures having a high content of octylated phenyl-alpha-naphthylamine |
| TW201031621A (en) | 2009-01-14 | 2010-09-01 | Albemarle Corp | Processes for production of macromolecular amine-phenolic antioxidant compositions containing low amounts of non-macromolecular byproducts |
| IT1393117B1 (it) * | 2009-03-04 | 2012-04-11 | Eni Spa | Lubrificanti di elevate caratteristiche prestazionali formulati con basi di gruppo ii per applicazioni motoristiche |
| KR101121922B1 (ko) * | 2011-10-20 | 2012-03-20 | 남성환 | 차체의 부식을 방지하기 위한 처리방법 |
| WO2015026577A1 (en) * | 2013-08-23 | 2015-02-26 | Chevron U.S.A. Inc. | Diesel fuel composition |
| CN103450379B (zh) * | 2013-09-06 | 2016-01-20 | 中国科学院化学研究所 | 一类高效、抗迁移受阻酚抗氧剂及其制备方法 |
| CN105585536B (zh) * | 2014-10-23 | 2018-05-18 | 中国石油化工股份有限公司 | 一种抗氧剂及其制备方法和应用 |
| CN106318536B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种液压润滑油组合物及其制备方法 |
| CN106318558B (zh) * | 2015-06-16 | 2019-04-16 | 中国石油化工股份有限公司 | 一种摩托车发动机润滑油组合物及其制备方法 |
| CN106318518B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种自动传动液润滑油组合物及其制备方法 |
| CN106318545B (zh) * | 2015-06-16 | 2019-04-16 | 中国石油化工股份有限公司 | 一种柴油发动机润滑油组合物及其制备方法 |
| CN106318521B (zh) * | 2015-06-16 | 2019-04-16 | 中国石油化工股份有限公司 | 一种曲轴箱系统润滑油组合物及其制备方法 |
| CN106318522B (zh) * | 2015-06-16 | 2019-05-17 | 中国石油化工股份有限公司 | 一种燃气发动机润滑油组合物及其制备方法 |
| CN106318534B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种金属加工润滑油组合物及其制备方法 |
| CN106318519B (zh) * | 2015-06-16 | 2019-05-21 | 中国石油化工股份有限公司 | 一种汽油机油润滑油组合物及其制备方法 |
| CN106318520B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种润滑油组合物及其制备方法 |
| CN106318557B (zh) * | 2015-06-16 | 2019-05-21 | 中国石油化工股份有限公司 | 一种甲醇燃料发动机润滑油组合物及其制备方法 |
| CN106318556B (zh) * | 2015-06-16 | 2019-05-21 | 中国石油化工股份有限公司 | 一种车辆齿轮润滑油组合物及其制备方法 |
| KR20170018718A (ko) | 2015-08-10 | 2017-02-20 | 삼성전자주식회사 | 비정질 합금을 이용한 투명 전극 및 그 제조 방법 |
| JP6856629B2 (ja) * | 2015-09-02 | 2021-04-07 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | 潤滑剤組成物 |
| CN106753700B (zh) * | 2015-11-23 | 2019-07-23 | 中国石油化工股份有限公司 | 汽油发动机润滑油组合物及其制备方法、用途 |
| CN105505532B (zh) * | 2015-11-30 | 2018-05-25 | 江阴市苏达塑业有限公司 | 一种高温模具润滑颗粒及其制备方法 |
| CN122256066A (zh) * | 2016-04-13 | 2026-06-23 | 卡斯特罗尔有限公司 | 从烃流体中除去芳族化合物 |
| CN107304379B (zh) * | 2016-04-18 | 2019-08-16 | 中国石油化工股份有限公司 | 一种燃气汽轮机油组合物及其制备方法 |
| CN107304377B (zh) * | 2016-04-18 | 2019-08-16 | 中国石油化工股份有限公司 | 一种高温链条油组合物及其制备方法 |
| CN107304382B (zh) * | 2016-04-18 | 2019-08-16 | 中国石油化工股份有限公司 | 一种空气压缩机油组合物及其制备方法 |
| US10577307B2 (en) | 2016-06-03 | 2020-03-03 | Dic Corporation | Methods for producing polycyclic aromatic aminophenol compound and resin composition, and polycyclic aromatic aminophenol compound, resin composition, and cured product |
| US11084909B2 (en) * | 2016-08-30 | 2021-08-10 | Basf Se | Liquid antioxidant composition for raw rubbers |
| CN113293046B (zh) * | 2021-05-26 | 2021-11-30 | 安徽博洋润滑科技有限公司 | 一种低发尘润滑脂及其制备方法 |
| CN113831592B (zh) * | 2021-08-26 | 2023-02-28 | 贵州省材料产业技术研究院 | 一种酚胺类抗氧剂及其制备方法和应用 |
| CN117626102B (zh) * | 2024-01-26 | 2024-05-10 | 钢铁研究总院有限公司 | 一种高强韧超高强度钢及其制备方法 |
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| US2528769A (en) * | 1947-05-28 | 1950-11-07 | Socony Vacuum Oil Co Inc | Reaction product of haloalkylthiophenes and hydroxyaryl compounds |
| CH533097A (de) * | 1970-03-13 | 1973-01-31 | Sandoz Ag | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen |
| US3673091A (en) * | 1970-07-16 | 1972-06-27 | Shell Oil Co | Lubricants containing oxidation inhibitors |
| US3822284A (en) | 1970-07-16 | 1974-07-02 | Shell Oil Co | 1-and 3-substituted (3,5-di-t-butyl-4-hydroxybenzyl)carbazole |
| US3989738A (en) | 1975-07-21 | 1976-11-02 | The Goodyear Tire & Rubber Company | Method of preparing phenolic antioxidants by condensing active methylene compounds with 3,5-di-tert alkyl-4-hydroxybenzylpyridinium salts |
| SU572457A1 (ru) | 1976-03-09 | 1977-09-15 | Предприятие П/Я А-7253 | 1-3,5-Дитрет бутил-4-оксибензил-3метилпиразолон-5 в качестве противостарител светлых резин |
| US4833155A (en) | 1986-11-25 | 1989-05-23 | Syntex (U.S.A.) Inc. | 3-(ω-(3,5,-di-t-butyl-4-hydroxyphenyl)-alkanoyl)pyrroles, and anti-inflammatory uses thereof |
| ES2028130T3 (es) * | 1986-12-31 | 1992-07-01 | Ciba-Geigy Ag | Fenotiacinas substituidas como estabilizadores de lubricantes. |
| GB8804457D0 (en) * | 1988-02-25 | 1988-03-23 | Ciba Geigy Ag | Compositions |
| US4994628A (en) | 1989-09-25 | 1991-02-19 | Ethyl Corporation | Phenolic antioxidant process |
| JP3269658B2 (ja) | 1992-06-02 | 2002-03-25 | エーザイ株式会社 | フェノール誘導体 |
| JP2002062673A (ja) * | 2000-08-14 | 2002-02-28 | Fuji Denki Gazo Device Kk | 電子写真用感光体 |
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