US2011230680A1PendingUtilityA1
Lubricating compositions containing ashless catalytic antioxidant additives
Est. expiryMay 9, 2026(expired)· nominal 20-yr term from priority
C10M 133/12C10N 2030/10C10M 2215/066C07C 211/50C10N 2040/08C10M 169/04
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Claims
Abstract
The invention comprises lubricating compositions and hydraulic to fluids containing N,N′-diaryl-o-phenylenediamine compounds that impart good levels of oxidation inhibition in the lubricants and hydraulic fluids. The invention further comprises a method of making N,N′-diaryl-o-phenylenediamine compounds.
Claims
exact text as granted — not AI-modified1 . (canceled)
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11 . A method of making a N,N′-diaryl-o-phenylenediamine antioxidant comprising reacting a compound having Formula II
where X is a halogen and R 2 and R 3 have the same meaning as in Formula I, with aniline derivatives having Formula III
where R 1 and R 4 have the same meaning as in Formula I, in the presence of a palladium catalyst, and wherein said halogen is chlorine.
12 . The method of claim 11 , wherein R 2 and R 3 are hydrogen.
13 . The method of claim 11 , wherein the palladium catalyst is a palladium/phosphine catalyst or palladium/carbine catalyst.
14 . The method of claim 11 , wherein the palladium catalyst is a preformed palladium complex coupling catalyst.
15 . The method of claim 14 , wherein the preformed palladium complex coupling catalyst is dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) or dichlorobis(di-tert-butylphenylphosphine)palladium (II).
16 . A method of making a N,N′-diaryl-o-phenylenediamine antioxidant comprising reacting a compound having Formula II
where X is a halogen and R 2 and R 3 have the same meaning as in Formula I, with aniline derivatives having Formula III
where R 1 and R 4 have the same meaning as in Formula I, in the presence of a preformed palladium complex coupling catalyst, and wherein said halogen is bromine.
17 . The method of claims 16 , wherein the preformed palladium complex coupling catalyst is dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) or dichlorobis(di-tert-butylphenylphosphine)palladium (II).
18 . A method of making a N,N′-diaryl-o-phenylenediamine antioxidant comprising reacting a compound having Formula IV
where X is a halogen and R 1 and R 4 have the same meaning as in Formula I, preferably chlorine or bromine, with aniline derivatives having Formula V
where R 2 and R 3 have the same meaning as in Formula I, in the presence of a palladium catalyst.
19 . The method of claim 18 , wherein the compound of Formula IV is 2-choro-m-xylene.
20 . The method of claim 18 , wherein the palladium catalyst is a palladium/phosphine catalyst or palladium/carbine catalyst.
21 . The method of claim 18 , wherein the palladium catalyst is a preformed palladium complex coupling catalyst.
22 . The method of claim 21 , wherein the preformed palladium complex coupling catalyst is dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) or dichlorobis(di-tert-butylphenylphosphine)palladium (II).
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