Organic phosphorus compound, preparation method therefor, and uses thereof

Patent metadata

Field	Value
Publication number	US-2025034476-A1
Application number	US-202418825555-A
Country	US
Kind code	A1
Filing date	Sep 5, 2024
Priority date	Oct 16, 2018
Publication date	Jan 30, 2025
Grant date	—

Abstract

An organophosphorus compound has a structure represented by the general formula (I):

The functional groups are defined in the description. The organophosphorus compound has prominent bearing capacity and excellent antiwear and antifriction performances, and can be used as an extreme pressure antiwear additive and used in lubricating oil and lubricating grease.

First claim

1 . A process for preparing an organophosphorus compound, which comprises the following steps:
step A of subjecting a phenol compound represented by the general formula (X) to an epoxidation reaction or a sulfurization reaction or an optional hydrogenation reaction, the molar ratio of the phenol compound represented by the general formula (X) to the epoxidizing agent is 1:1-10 (preferably 1:2-5); the epoxidation reaction temperature is 0° C.-100° C. (preferably 10° C.-80° C.), or the molar ratio of the phenol compound represented by the general formula (X) or the product of step B to the sulfurizing agent is 1:1-6 (preferably 1:2-4); the sulfurization reaction temperature is 100° C.-240° C. (preferably 140° C.-190° C.), the conditions of the optional hydrogenation reaction comprise: hydrogen pressure: 1.0-6.0 MPa (preferably 3.0-4.0 MPa), temperature: 60° C.-260° C. (preferably 180° C.-220° C.), time: 0.5-10 h (preferably 3-5 h); and step B of reacting the product obtained in step A with a phosphorous compound represented by the general formula (X′);

wherein, in the general formula (X), groups R 1 ″, R 2 ″, R 3 ″, R 4 ″ and R 5 ″ are, identical to or different from each other, each independently selected from H, and a group represented by the general formula (Y), wherein at least one group is a group represented by the general formula (Y);

wherein group R 1 ″ is selected from single bond and C 1 -C 20 linear or branched alkylene (preferably selected from single bond and C 1 -C 4 linear or branched alkylene); groups R 2 ″ in m repeating units are, identical to or different from each other, each independently selected from single bond and C 1 -C 20 linear or branched alkylene (preferably each independently selected from single bond and C 1 -C 4 linear or branched alkylene); group R 3 ″ is selected from hydrogen and C 1 -C 20 linear or branched alkyl (preferably selected from hydrogen and C 1 -C 4 linear or branched alkyl); groups R 4 ″ in m repeating units are, identical to or different from each other, each independently selected from hydrogen and C 1 -C 20 linear or branched alkyl (preferably each independently selected from hydrogen and C 1 -C 4 linear or branched alkyl); groups R 5 ′″ in m repeating units are, identical to or different from each other, each independently selected from hydrogen and C 1 -C 20 linear or branched alkyl (preferably each independently selected from hydrogen and C 1 -C 4 linear or branched alkyl); m is a positive integral number (preferably a positive integral number of 1-10, more preferably a positive integral number of 1-3), and the total carbon number in formula (Y) is 10-20;

groups G′ present in the general formula (X′) are, identical to or different from each other, each independently selected from O, S and NR 0 ′ or absence (the absence of group G′ means that P is a tervalent P atom), wherein R 0 ′ is selected from H, C 6 -C 20 aryl, C 1 -C 20 linear or branched alkyl C 6 -C 20 aryl and C 1 -C 30 linear or branched alkyl (preferably selected from phenyl, C 1 -C 14 alkyl phenyl and C 1 -C 20 linear or branched alkyl);
groups G′ present in the general formula (X′) are, identical to or different from each other, each independently selected from single bond, O, S and NR 0 ′, wherein R 0 ′ is selected from H, C 6 -C 20 aryl, C 1 -C 20 linear or branched alkyl C 6 -C 20 aryl and C 1 -C 30 linear or branched alkyl (preferably selected from phenyl, C 1 -C 14 alkyl phenyl and C 1 -C 20 linear or branched alkyl);
groups R in the general formula (X′) are independently selected from single bond, C 1 -C 20 linear or branched alkylene and C 6 -C 20 arylene (preferably selected from single bond, C 1 -C 10 linear or branched alkylene, C 6 -C 10 arylene);
groups G′″ present in the general formula (X′) are, identical to or different from each other, each independently selected from A, —N(R 0 ′) 2 and R Z ; wherein group R Z is each independently selected from H, C 1 -C 30 linear or branched alkyl, C 1 -C 30 linear or branched alkoxyl, C 6 -C 20 aryl, C 1 -C 20 linear or branched alkyl C 6 -C 20 aryl (preferably each independently selected from H, C 1 -C 10 linear or branched alkyl, C 1 -C 10 linear or branched alkoxyl, C 6 -C 10 aryl, C 1 -C 14 alkyl phenyl), groups R 0 ′ are each independently selected from H, C 6 -C 20 aryl, C 1 -C 20 linear or branched alkyl C 6 -C 20 aryl and C 1 -C 30 linear or branched alkyl (preferably each independently selected from phenyl, C 1 -C 14 alkyl phenyl and C 1 -C 20 linear or branched alkyl), wherein groups A are each independently selected from F, Cl, Br, I and OH (preferably each independently selected from Cl and Br), wherein at least one group G″ is A;
in the general formula (X′), n 0 is an integral number of 0-10, preferably an integral number of 0-5, more preferably 0, 1, 2, 3 or 4, the conditions for reacting the phenol compound represented by the general formula (X) or the product of step A obtained from subjecting the phenol compound represented by the general formula (X) to the epoxidation reaction or the sulfurization reaction or the optional hydrogenation reaction with the phosphorous compound represented by the general formula (X′) comprise: the molar ratio of the phosphorous compound represented by the general formula (X′) to the phenol compound represented by the general formula (X) or the product of step A is 1:1-10 (preferably 1:1-5); the reaction temperature is 50° C.-150° C. (preferably 60° C.-100° C.).

2 . The preparation process according to claim 1 , wherein in the general formula (X), groups R 1 ″, R 3 ″ and R 5 ″ are, identical to or different from each other, each independently selected from hydrogen and C 1 -C 4 linear or branched alkyl; preferably, groups R 1 ″, R 3 ″ and R 5 ″ are, identical to or different from each other, each independently selected from H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl.

3 . The preparation process according to claim 1 , wherein in the general formula (X), groups R 2 ″ and R 4 ″ are, identical to or different from each other, each independently selected from hydrogen, C 1 -C 20 linear or branched alkyl and a group represented by the general formula (Y), wherein at least one group is a group represented by the general formula (Y); preferably, one group of groups R 2 ″ and R 4 ″ is selected from a group represented by the general formula (Y), the other group is selected from hydrogen.

4 . The preparation process according to claim 1 , wherein the phosphorous compound represented by the general formula (X′) is selected from a epoxidation agent and/or a phosphorus-nitridizing agent.

5 . The preparation process according to claim 4 , wherein the epoxidation agent has a structure as represented by the formula (Z):

wherein R Z is selected from H, C 1 -C 30 linear or branched alkyl, C 1 -C 30 linear or branched alkoxyl, C 6 -C 20 aryl, C 1 -C 20 linear or branched alkyl C 6 -C 20 aryl (preferably each independently selected from H, C 1 -C 10 linear or branched alkyl, C 1 -C 10 linear or branched alkoxyl, C 6 -C 10 aryl, C 1 -C 14 alkyl phenyl); groups A are each independently selected from F, Cl, Br, I and OH (preferably each independently selected from Cl and Br);
the phosphorus-nitridizing agent has a structure as represented by the formula (Z′):

Assignees

• China Petroleum & Chem Corp
• Sinopec Res Inst Petroleum

Inventors

• Chen Xiaowei
• Wei Kecheng

Classifications

• C10N2050/10

  semi-solid; greasy · CPC title

• C10N2030/06

  Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure · CPC title

• C10M2223/08

  having phosphorus-to-nitrogen bonds · CPC title

• C10M2223/065

  containing sulfur · CPC title

• C10M2203/003

  used as base material · CPC title