CN103601748A - Hydroxyalkylated heterocycle boric acid ester and preparation method and purpose thereof - Google Patents
Hydroxyalkylated heterocycle boric acid ester and preparation method and purpose thereof Download PDFInfo
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Abstract
The present invention relates to a kind of hydroxyalkylation heterocyclic boronic acids ester and preparation method thereof,Purposes; The structural formula of the additive such as formula (I) or (II) are shown; The invention further relates to the preparation method of hydroxyalkylation heterocyclic boronic acids ester lubricating additive above-mentioned,Described method includes following steps: step 1,Under conditions of organic solvent and catalyst,Heterocyclic compound and alkyl epoxide reaction,Generate compound A; Step 2,Under conditions of organic solvent and catalyst,Compound B and compound A,Or reacted containing heterocyclic alcohol, ; The invention further relates to the purposes of aforementioned hydroxyalkylation heterocyclic boronic acids ester.
Description
Technical field
The present invention relates to a kind of organic compound and preparation method thereof, especially a kind of hydroxyalkylation heterocyclic boronic acids ester and preparation method thereof, purposes.
Background technology
Along with the continuous enhancing of people's environmental protection consciousness, existing slip additive (as ZDDP) is because himself limitation more and more can not meet the harsh requirement of environmental regulation, so the slip additive of developing green environmental protection becomes current common recognition gradually.
Organic boric acid ester is a class multi-functional environment-protection lubricating oil additive, has good antiwear and friction reduction property.There are some researches show, organic boric acid ester slip additive is corrosion-free to metal, in lubricating oil, mainly play a part anti-oxidant, reduce friction, reduce wearing and tearing, be that the promising environmental friendliness of a class is lubricated multifunction additive.
In addition, Hete rocyclic derivatives, as slip additive, has good antiwear and friction reduction property.Patent No. US7598211 has announced a kind of heterogeneous ring compound containing dimercaptothiodiazole and has had good tribological property; Chen Huan etc. are at J Engineering Tribology, and 2012,226(8), in 668-677, introduced a kind of imidazoline type dimercaptothiodiazole derivative and in lithium saponify, there is good antiwear and friction reduction property.
Therefore, heterogeneous ring compound and organic boronic ester cpds are combined, develop the multifunctional lubricating additive with good antiwear and friction reduction property, the focus that the person that become current research pays close attention to.
Summary of the invention
The object of this invention is to provide a kind of hydroxyalkylation heterocyclic boronic acids ester and preparation method thereof, purposes.
The object of the invention is to realize by following technical scheme:
First aspect, the present invention relates to a kind of hydroxyalkylation heterocyclic boronic acids ester, and the structural formula of described hydroxyalkylation heterocyclic boronic acids ester is suc as formula (I) or (II):
Wherein, R
1for OH, R
5-O,
R
2for OH, R
5-O,
R
3for
or R
7;
R
4for
R
5straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
6for
R
7for
R
8for H or R
9;
R
9straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
10for H or R
11;
R
11straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
12for H or R
13;
R
13straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
14, R
15, R
16, R
17, R
18straight chain, side chain, aryl or cycloalkyl for C1～C30.
Preferably, described hydroxyalkylation heterocyclic boronic acids ester is boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, boric acid three [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters,
Boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, boric acid three [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters,
Boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, boric acid three [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-butylbenzene boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-butylbenzene boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-octyl group phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-octyl group phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-dodecyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-eicosyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, boric acid ethylene glycol [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters or boric acid (1, 2-dihydroxy ethyl 20 amine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters.
Second aspect, the present invention relates to a kind of preparation method of hydroxyalkylation heterocyclic boronic acids ester,, comprise the steps:
Step 1, under the condition of organic solvent and catalyzer, heterogeneous ring compound and alkyl epoxide reaction, generate compd A, and its reactive mode is as follows:
Step 2, under the condition of organic solvent and catalyzer, compd B reacts with compd A or containing heterocyclic alcohol, obtains hydroxyalkylation heterocyclic boronic acids ester, and its reactive mode is as follows:
Described heterogeneous ring compound is dihydroxy ethyl alkylamine or alkyl diol,
The structural formula of described compd A is as shown in the formula (III):
Described is dihydroxy ethyl alkylamine or alkyl diol containing heterocyclic alcohol;
Described compd B is boric acid or alkylbenzene boric acid;
Described heterogeneous ring compound is 2-mercaptobenzothiazole, 2-mercaptobenzimidazole, benzotriazole, 2-mercaptobenzoxazole, tri-thiol central Shanxi plain derivative, melamine derivative, dimercaptothiodiazole derivative.
Preferably, the mol ratio of described heterogeneous ring compound and alkyl epoxide is 1:(1～3), the mol ratio of described compd B and compd A is 1:(1～3), described boric acid is (1～3) with containing heterocyclic alcohol mol ratio: (1～6); Described alkylbenzene boric acid is 1:1 with containing heterocyclic alcohol mol ratio.
Preferably, described organic solvent is acetone, benzene, toluene, chloroform, ethyl acetate, DMF, N,N-dimethylacetamide, tetrahydrofuran (THF) or dimethyl sulfoxide (DMSO).
Preferably, described catalyzer is the vitriol oil, potassium hydroxide, sodium hydroxide, triethylamine, acidic resins, DMAP.
The third aspect, the invention still further relates to a kind of aforesaid hydroxyalkylation heterocyclic boronic acids ester as the purposes of lubricating oil additive.
Compared with prior art, the present invention has following beneficial effect:
(1) the present invention is owing to having introduced various dissimilar heterogeneous ring compounds, form boric acid ester with different types of boric acid, the hydroxyalkylation heterocyclic boronic acids ester that the present invention makes forms the antifriction antiwear materials such as boron oxide, boron nitride in friction process, thereby improves the extreme pressure and antiwear behavior of lubricating oil;
(2) the hydroxyalkylation heterocyclic boronic acids ester that the present invention makes can add in lubricating oil and use separately, can obtain the lubricating system of good wear-resistant and anti-extreme pressure energy, makes lubricating oil PB value improve 30～110%, and wear scar diameter reduces 30～50%.Can also with other lubricating oil additive compound use, can reach synergistic function.
Accompanying drawing explanation
By reading the detailed description of non-limiting example being done with reference to the following drawings, it is more obvious that other features, objects and advantages of the present invention will become:
Fig. 1 is the infrared spectrogram of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 1;
Fig. 2 is the infrared spectrogram of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 2;
Fig. 3 is the infrared spectrogram of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 3;
Fig. 4 is the infrared spectrogram of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 4;
Fig. 5 is the thermogravimetric analysis figure of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 1;
Fig. 6 is the thermogravimetric analysis figure of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 2;
Fig. 7 is the thermogravimetric analysis figure of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 3;
Fig. 8 is the thermogravimetric analysis figure of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the embodiment of the present invention 4.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in detail.Following examples will contribute to those skilled in the art further to understand the present invention, but not limit in any form the present invention.It should be pointed out that to those skilled in the art, without departing from the inventive concept of the premise, can also make some distortion and improvement.These all belong to protection scope of the present invention.
embodiment 1
The present embodiment relates to the hydroxyalkylation heterocyclic boronic acids ester (BPTT) shown in a kind of following structural formula,
The present embodiment also relates to the preparation method of aforesaid hydroxyalkylation heterocyclic boronic acids ester (BPTT), and its method comprises the steps:
Step 1, will be equipped with 2 of 15.0g, in the there-necked flask of 5-dimercaptothiodiazole, add catalyzer, stirring at room, after half an hour, drips propylene oxide 11.6g, continue room temperature reaction and spend the night, after reaction finishes, pickling, washing, anhydrous magnesium sulfate drying, filters, and removes organic solvent under reduced pressure, obtain intermediate product red-brown oily liquids DMTO23.1g, productive rate 86.8%;
Step 2,35.8g N will be housed, in the there-necked flask of N-dihydroxy ethyl stearylamine, 13.3g DMTO and 6.2g boric acid, add catalyzer, reflux, minute water reaction 8 hours, after reaction finishes, organic solvent is removed in decompression, obtains the reddish-brown viscous liquid of take the hydroxyalkylation heterocyclic boronic acids ester slip additive that BPTT is primary product of 38.6g, yield 100%.Overall yield 74.35%.
Implementation result: in Table 1, its results of elemental analyses that is BPTT, from table 1, results of elemental analyses is known, and the measured value of the C of all target compounds, H, N, S, B element meets substantially with the theoretical value of calculating by molecular formula, and absolute error is in allowed band.
Table 1
Fig. 1 is the Infrared spectroscopy of embodiment 1 product, and analytical results is as follows: IR(cm
-1): 2919.85,2922.21,2851.21(-CH
2-,-CH
3), 1638.33(-S-C=N), 1312.34 (B-O).
Fig. 5 is the thermogravimetric analysis figure of embodiment 1 product, and as can be seen from the figure decomposition temperature, more than 200 ℃, has higher thermostability, is suitable as lubricating oil additive.
embodiment 2
The present embodiment relates to the hydroxyalkylation heterocyclic boronic acids ester (DBMT) shown in a kind of following structural formula,
The present embodiment relates to the preparation method of aforesaid hydroxyalkylation heterocyclic boronic acids ester (DBMT), and its method comprises the steps:
Step 1, by being equipped with in the there-necked flask of 2-mercaptobenzothiazole of 16.7g, adds catalyzer, stirring at room, after half an hour, drips propylene oxide 6.0g, continues room temperature reaction and spends the night, after reaction finishes, pickling, washing, anhydrous magnesium sulfate drying, filter, remove organic solvent under reduced pressure, obtain intermediate product red-brown oily liquids 2-[4-morpholinodithio-2-base sulfo--1-methyl-ethanol (PBT) 19.35g, productive rate 86.1%;
Step 2,11.61g is added in the there-necked flask that has toluene solvant dodecyl phenylo boric acid and 18.03gPBT, add catalyzer, reflux, divide water reaction 8 hours, after reaction finishes, organic solvent is removed in decompression, the light yellow viscous liquid 26.8g of hydroxyalkylation heterocyclic boronic acids ester slip additive that to obtain take DBMT be primary product, productive rate 95.05%.Overall yield 81.84%.
Implementation result: in Table 2, it is the results of elemental analyses of DBMT in the present embodiment, and results of elemental analyses is known from table 2, Elements C, H, N, S, B measured value meet substantially with the theoretical value of calculating by molecular formula, and absolute error is in allowed band.
Table 2
Fig. 2 is the Infrared spectroscopy schematic diagram of embodiment 2 products, and analytical results is as follows: 2955.73 (CH3); 2925.72 (CH2), 2854.24 (CH2); (1608.39 C=C, C=N); 1457.48 (CH3), 1371.17 (CH3); 1428.24 (phenyl ring); 1316.72 (B-O); 1241.00 (C-N); 1101.56 (C-N-C); 1005.72 (C-O); (754.46 phenyl ring); 725.46 (C-B); 653.59 (C-S). infrared spectrogram can determine that gained compound is target compound.
Fig. 6 is the thermogravimetric analysis figure of embodiment 2 products, and as can be seen from the figure decomposition temperature, more than 250 ℃, has higher thermostability, is suitable as lubricating oil additive.
embodiment 3
The present embodiment relates to the hydroxyalkylation heterocyclic boronic acids ester (DSSB) shown in a kind of following structural formula,
The present embodiment relates to the preparation method of aforesaid hydroxyalkylation heterocyclic boronic acids ester (DSSB), and its method comprises the steps:
Step 1, in the there-necked flask of 17.73g tri-thiol triazine is housed, slowly drips 50.0g bromododecane, add 9g sodium hydroxide as acid binding agent, spend the night, add 6g propylene oxide, continue reaction until react completely, obtain yellow oily intermediate DSEP45.76g, productive rate 80.5%;
Step 2,11.61g is added in the there-necked flask that has toluene solvant dodecyl phenylo boric acid and 45.76g DSEP, add catalyzer, reflux, divide water reaction 8 hours, after reaction finishes, organic solvent is removed in decompression, the yellow viscous liquid 53.13g of hydroxyalkylation heterocyclic boronic acids ester slip additive that to obtain take DSSB be primary product, productive rate 95.05%.Overall yield 76.52%.
Implementation result: in Table 3, it is the results of elemental analyses of DSSB in the present embodiment, and results of elemental analyses is known from table 3, Elements C, H, N, S, B measured value meet substantially with the theoretical value of calculating by molecular formula, and absolute error is in allowed band.
Table 3
Fig. 3 is the Infrared spectroscopy schematic diagram of embodiment 3 products, and analytical results is as follows: IR(cm
-1): 2955.23 (CH
3); 2925.22 (CH
2), 2853.74 (CH
2); 1607.99 (C=C; C=N); 1520.02(C-S); 1457.00 (CH
3), 1370.17 (CH3); 1427.74 (phenyl ring); 1316.22 (B-O); 1005.22 (C-O); (754.01 phenyl ring); 725.00 (C-B); 653.09 (C-S).
Fig. 7 is the thermogravimetric analysis figure of embodiment 3 products, and as can be seen from the figure decomposition temperature, more than 250 ℃, has higher thermostability, is suitable as lubricating oil additive.
embodiment 4
The present embodiment relates to the hydroxyalkylation heterocyclic boronic acids ester (DSB) shown in a kind of following structural formula,
The present embodiment relates to the preparation method of aforesaid hydroxyalkylation heterocyclic boronic acids ester (DSB), and its method comprises the steps:
Step 1, in the there-necked flask of 17.73g tri-thiol triazine is housed, slowly drips 50.0g bromododecane, add 9g sodium hydroxide as acid binding agent, spend the night, add 6g propylene oxide, continue reaction until react completely, obtain yellow oily intermediate DSEP45.76g, productive rate 80.5%;
Step 2,2.47g boric acid and 45.76g DSEP are added in the there-necked flask that has toluene solvant, add catalyzer, reflux, divide water reaction 8 hours, after reaction finishes, organic solvent is removed in decompression, the yellow viscous liquid 43.93g of hydroxyalkylation heterocyclic boronic acids ester slip additive that to obtain take DSB be primary product, productive rate 94.1%.Overall yield 75.75%.
Fig. 4 is the infrared spectrogram of the hydroxyalkylation heterocyclic boronic acids ester that obtains of the present embodiment.
Implementation result: in Table 4, it is the results of elemental analyses of DSB in the present embodiment, and results of elemental analyses is known from table 4, Elements C, H, N, S, B measured value meet substantially with the theoretical value of calculating by molecular formula, and absolute error is in allowed band.
Table 4
embodiment 5 contrast tests
(1) it is as follows that four kinds of hydroxyalkylation heterocyclic boronic acids esters that above embodiment 1,2,3,4 obtained carry out extreme pressure and antiwear behavior test, and its testing method is as follows:
According to GB3142-82 standard, the hydroxyalkylation heterocyclic boronic acids ester that base oil, example example 1, embodiment 2, embodiment 3 and embodiment 4 are made is added on respectively in base oil, carries out last non seizure load (P
bvalue) mensuration (addition is 1.0wt%).Testing method is as follows: the MS-10JB type four-ball tester that uses Xiamen trier factory to produce, and steel ball used is secondary GCr15 standard steel ball (AISI-52100), and its diameter is 12.7mm, and hardness is 59～61HRC.At room temperature carry out, rotating speed is 1760rpm.Test result is shown in Table 4:
Table 4
| ? | Concentration (wt%) | P BValue (N) |
| |
100 | 372 |
| Embodiment 1 | 1.0 | 784 |
| Embodiment 2 | 1.0 | 725 |
| Embodiment 3 | 1.0 | 666 |
| Embodiment 4 | 1.0 | 627 |
(2) the vertical omnipotent friction-wear test of MMW-1 of producing with Jinan trier factory, under 294N load, four kinds of hydroxyalkylation heterocyclic boronic acids ester slip additives of test commodity ZDDP, embodiment 1, embodiment 2, embodiment 3 and embodiment 4 preparations, experimental period is 30 minutes, additive level is 1.0wt%, the wear scar diameter that rotating speed is 1450rpm (WSD).Steel ball used is secondary GCr15 standard steel ball (AISI-52100), and its diameter is 12.7mm, and hardness is 59～61HRC.Experiment is at room temperature carried out, and it the results are shown in Table shown in 5:
Table 5
| Additive | Concentration (%) | Wear scar diameter (mm) |
| |
100 | 0.634 |
| ZDDP | 1.0 | 0.432 |
| Embodiment 1 | 1.0 | 0.356 |
| Embodiment 2 | 1.0 | 0.405 |
| Embodiment 3 | 1.0 | 0.401 |
| Embodiment 4 | 1.0 | 0.421 |
Result demonstration, compound synthetic in embodiment can effectively reduce WSD value, and embodiment 1,2,3 effects are better than ZDDP, and embodiment 4 effects and ZDDP approach.
Above specific embodiments of the invention are described.It will be appreciated that, the present invention is not limited to above-mentioned specific implementations, and those skilled in the art can make various distortion or modification within the scope of the claims, and this does not affect flesh and blood of the present invention.
Claims (7)
1. a hydroxyalkylation heterocyclic boronic acids ester, is characterized in that, the structural formula of described hydroxyalkylation heterocyclic boronic acids ester is suc as formula (I) or (II):
Wherein, R
1for OH, R
5-O,
R
2for OH, R
5-O,
R
3for
or R
7;
R
4for
R
5straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
6for
R
7for
R
8for H or R
9;
R
9straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
10for H or R
11;
R
11straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
12for H or R
13;
R
13straight chain, side chain, aryl or cycloalkyl for C1～C30;
R
14, R
15, R
16, R
17, R
18straight chain, side chain, aryl or cycloalkyl for C1～C30.
2. hydroxyalkylation heterocyclic boronic acids ester as claimed in claim 1, it is characterized in that, described hydroxyalkylation heterocyclic boronic acids ester is boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzothiazole-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzothiazole-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, boric acid three [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzotriazole-1-yl)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzotriazole-1-yl)-1-methyl] ethanol three esters,
Boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, boric acid three [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzimidazolyl-2 radicals-Ji sulfo-)-1-methyl] ethanol three esters,
Boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [2-(benzoxazoles-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [(4, 6-dioctyl sulfo-triazine-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid three [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-butylbenzene boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-octyl group phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl phenylo boric acid [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethyl ester, boric acid ethylene glycol [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl 20 amine) [(4, 6-bis-(dodecyl base sulfo-) triazine-2-base sulfo-)-1-methyl] ethanol three esters,
Boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, boric acid three [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-butylbenzene boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-butylbenzene boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-diisobutyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-diisobutyl phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-octyl group phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-octyl group phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-dodecyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-dodecyl base phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-hexadecyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-hexadecyl base phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-eicosyl phenylo boric acid [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, 4-eicosyl base phenylo boric acid two [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethyl ester, boric acid ethylene glycol [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-propylene glycol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-butyleneglycol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-pentanediol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-hexylene glycol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-heptanediol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-ethohexadiol) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl dodecane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl n-Hexadecane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxyl eicosane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-diethanolamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl methylamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl ethamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl butylamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl octylame) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl amino dodecane) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters, boric acid (1, 2-dihydroxy ethyl stearylamine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters or boric acid (1, 2-dihydroxy ethyl 20 amine) [(4, the different pungent aminotriazine of 6-bis--2-is amino)-1-methyl isophthalic acid-methyl] ethanol three esters.
3. a preparation method for hydroxyalkylation heterocyclic boronic acids ester as claimed in claim 1, is characterized in that, comprises the steps:
Step 1, under the condition of organic solvent and catalyzer, heterogeneous ring compound and alkyl epoxide reaction, generate compd A;
Step 2, under the condition of organic solvent and catalyzer, compd B reacts with compd A or containing heterocyclic alcohol, obtains hydroxyalkylation heterocyclic boronic acids ester;
Described heterogeneous ring compound is dihydroxy ethyl alkylamine or alkyl diol,
The structural formula of described compd A is as shown in the formula (III):
Described is dihydroxy ethyl alkylamine or alkyl diol containing heterocyclic alcohol;
Described compd B is boric acid or alkylbenzene boric acid;
Described heterogeneous ring compound is 2-mercaptobenzothiazole, 2-mercaptobenzimidazole, benzotriazole, 2-mercaptobenzoxazole, tri-thiol central Shanxi plain derivative, melamine derivative, dimercaptothiodiazole derivative.
4. the preparation method of hydroxyalkylation heterocyclic boronic acids ester as claimed in claim 3, it is characterized in that, the mol ratio of described heterogeneous ring compound and alkyl epoxide is 1:(1～3), the mol ratio of described compd B and compd A is 1:(1～3), described boric acid is (1～3) with containing heterocyclic alcohol mol ratio: (1～6); Described alkylbenzene boric acid is 1:1 with containing heterocyclic alcohol mol ratio.
5. the preparation method of hydroxyalkylation heterocyclic boronic acids ester as claimed in claim 3, it is characterized in that, described organic solvent is acetone, benzene, toluene, chloroform, ethyl acetate, DMF, N,N-dimethylacetamide, tetrahydrofuran (THF) or dimethyl sulfoxide (DMSO).
6. the preparation method of hydroxyalkylation heterocyclic boronic acids ester as claimed in claim 3, is characterized in that, described catalyzer is the vitriol oil, potassium hydroxide, sodium hydroxide, triethylamine, acidic resins or DMAP.
7. a hydroxyalkylation heterocyclic boronic acids ester as claimed in claim 1 is as the purposes of lubricating oil additive.
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| US4335005A (en) * | 1980-09-11 | 1982-06-15 | Mobil Oil Corporation | Lubricant compositions containing metal antifatigue additives |
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| US4335005A (en) * | 1980-09-11 | 1982-06-15 | Mobil Oil Corporation | Lubricant compositions containing metal antifatigue additives |
| US4701274A (en) * | 1985-04-26 | 1987-10-20 | Union Oil Company Of California | Trisubstituted-borate compounds |
| CN1791664A (en) * | 2003-05-21 | 2006-06-21 | 西巴特殊化学品控股有限公司 | Borate ester lubricant additives |
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