Hydroxyalkylated heterocyclic boronic acid ester, its preparation method and use

A technology of heterocyclic boronate and hydroxyalkylation, which is applied in the field of organic compounds and their preparation, and can solve the problems of harsh requirements of lubricating additives

Active Publication Date: 2016-11-02
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] With the increasing awareness of environmental protection, existing lubricating additives (such as ZDDP) are increasingly unable to meet the stringent requirements of environmental protection regulations due to their own limitations, so the development of green and environmentally friendly lubricating additives has gradually become the current consensus

Method used

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  • Hydroxyalkylated heterocyclic boronic acid ester, its preparation method and use
  • Hydroxyalkylated heterocyclic boronic acid ester, its preparation method and use
  • Hydroxyalkylated heterocyclic boronic acid ester, its preparation method and use

Examples

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Embodiment 1

[0059] This embodiment relates to a hydroxyalkylated heterocyclic boronic acid ester (BPTT) shown in the following structural formula,

[0060]

[0061] This embodiment also relates to the preparation method of the aforementioned hydroxyalkylated heterocyclic boronic acid ester (BPTT), the method comprising the following steps:

[0062] Step 1: Add catalyst to a three-necked flask containing 15.0 g of 2,5-dimercaptothiadiazole, and after stirring at room temperature for half an hour, add 11.6 g of propylene oxide dropwise, and continue the reaction at room temperature overnight. After the reaction, the acid washing, washing with water, drying over anhydrous magnesium sulfate, filtering, and evaporating the organic solvent under reduced pressure to obtain 23.1 g of the intermediate product brownish-red oily liquid DMTO, with a yield of 86.8%;

[0063] Step 2: In a three-necked flask containing 35.8g N,N-dihydroxyethyl octadecylamine, 13.3g DMTO and 6.2g boric acid, add a cat...

Embodiment 2

[0070] This embodiment relates to a hydroxyalkylated heterocyclic boronic acid ester (DBMT) shown in the following structural formula,

[0071]

[0072] This embodiment relates to the preparation method of the aforementioned hydroxyalkylated heterocyclic boronic acid ester (DBMT), and the method includes the following steps:

[0073] Step 1: Add a catalyst to a three-necked flask containing 16.7 g of 2-mercaptobenzothiazole, stir at room temperature for half an hour, add 6.0 g of propylene oxide dropwise, and continue to react overnight at room temperature. After the reaction is complete, wash with acid and water , dried over anhydrous magnesium sulfate, filtered, and the organic solvent was evaporated under reduced pressure to obtain 19.35 g of the intermediate product brownish-red oily liquid 2-benzothiazol-2-ylthio-1-methyl-ethanol (PBT), with a yield of 86.1 %;

[0074] Step 2: Add 11.61g p-dodecylbenzeneboronic acid and 18.03g PBT into a three-necked flask with toluen...

Embodiment 3

[0082] This example relates to a hydroxyalkylated heterocyclic boronic acid ester (DSSB) shown in the following structural formula,

[0083]

[0084] This embodiment relates to the preparation method of the aforementioned hydroxyalkylated heterocyclic boronic acid ester (DSSB), and the method includes the following steps:

[0085] Step 1, in a three-necked flask equipped with 17.73g of trimercaptotriazine, slowly add 50.0g of dodecane bromide dropwise, add 9g of sodium hydroxide as an acid-binding agent, overnight, add 6g of propylene oxide, and continue the reaction until the reaction Completely, the yellow oily intermediate DSEP45.76g was obtained, and the yield was 80.5%;

[0086] Step 2: Add 11.61g p-dodecylbenzeneboronic acid and 45.76g DSEP into a three-necked flask with toluene solvent, add catalyst, heat to reflux, and divide water for 8 hours. After the reaction, remove the organic solvent under reduced pressure to obtain DSSB is 53.13 g of hydroxyalkylated hetero...

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Abstract

The present invention relates to a hydroxyalkylated heterocyclic boronic acid ester and its preparation method and use; the structural formula of the additive is shown in formula (I) or (II); the present invention also relates to the aforementioned hydroxyalkylated heterocyclic borate The preparation method of borate lubricating additive comprises the following steps: Step 1, under the condition of organic solvent and catalyst, heterocyclic compound and alkyl epoxide react to generate compound A; Step 2, in organic solvent and Under the conditions of the catalyst, compound B can be reacted with compound A or the heterocyclic alcohol; the present invention also relates to the use of the aforementioned hydroxyalkylated heterocyclic boronic acid ester.

Description

technical field [0001] The invention relates to an organic compound and a preparation method thereof, in particular to a hydroxyalkylated heterocyclic boronic acid ester, a preparation method and an application thereof. Background technique [0002] As people's awareness of environmental protection continues to increase, existing lubricant additives (such as ZDDP) are increasingly unable to meet the stringent requirements of environmental protection regulations due to their own limitations. Therefore, the development of green and environmentally friendly lubricant additives has gradually become the current consensus. [0003] Organic borate is a kind of multifunctional environmental protection lubricating oil additive, which has excellent anti-wear and anti-friction performance. Existing studies have shown that organic borate lubricating additives are non-corrosive to metals and mainly play the role of anti-oxidation, reducing friction and reducing wear in lubricating oils. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/04C10M139/00C10N30/06
Inventor 李志鹏张雅文李建昌任天辉
Owner SHANGHAI JIAOTONG UNIV
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