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US 2025/0011341 A1Published application
Organoboron compound, preparation method thereof, and use thereof
AssigneesChina Petroleum & Chemical Corporation, Sinopec Research Institute of Petroleum Processing Co., Ltd.
InventorsXiaowei CHEN, Hongjin TANG, Jingjian HE
Life of this patent
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Abstract
The present invention provides a sulfur-free and phosphorus-free organoboron compound, and preparation method thereof and use thereof. The organoboron compound of the present invention has a structure as shown in formula (I): The definition of each group can be found in the specification. The organoboron compound of the present invention has excellent antioxidant properties and anti-wear and friction-reducing properties.
Claims17
An organoboron compound, which has a structure as shown in formula (I):
- in formula (I), there are a L group(s) and b boron-containing group(s), a is an integer of 1-10 (preferably an integer of 1-5, more preferably 1, 2 or 3), b is an integer of 1-10 (preferably an integer of 1-7, more preferably 1, 2, 3, 4 or 5), each of said a L groups is identical or different from each other and each L group is independently selected from a group represented by formula (II);
- in formula (II), RO is bonded to the benzene ring (RO is preferably located at the meta position of the R1 group on the benzene ring);
- y R group(s) is/are bonded to the benzene ring;
- y is selected from an integer of 0-4 (preferably an integer of 1-3, more preferably 1 or 2);
- the R group is each independently selected from H and C1-20 linear or branched alkyl (preferably each independently selected from H and C1-6 linear or branched alkyl, preferably each independently selected from H and C1-4 linear or branched alkyl, more preferably selected from H and tert-butyl);
- n is an integer of 1-10 (preferably an integer of 1-5, more preferably 1, 2 or 3);
- R1 is each independently selected from a single bond and C˜˜1-30 linear or branched alkylene (preferably selected from a single bond and C1-20 linear or branched alkylene, preferably C1-10 linear or branched alkylene);
- each of R2s in n structure units is identical or different from each other and each R2 is independently selected from a single bond and C1-20 linear or branched alkylene (preferably each independently selected from a single bond and C1-6 linear or branched alkylene, preferably each independently selected from a single bond and C1-4 linear or branched alkylene);
- R3 is selected from H and C1-30 linear or branched alkyl (preferably selected from H and C1-20 linear or branched alkyl, more preferably H and C1-10 linear or branched alkyl, further preferably H and C1-6 linear or branched alkyl);
- each of A groups in n structure units is identical or different from each other and each A group is independently selected from
- a group represented by formula (III) and a group represented by formula (IV),
- the R4 group is each independently selected from H and C1-20 linear or branched alkyl (preferably each independently selected from H and C1-6 linear or branched alkyl, more preferably selected from H and C1-4 linear or branched alkyl);
- m is independently an integer of 0-10 (preferably an integer of 0-5, more preferably 0, 1 or 2);
- the R5 group is each independently selected from 3-valent C1-20 linear or branched alkyl (preferably each independently selected from 3-valent C1-6 linear or branched alkyl, more preferably each independently selected from 3-valent C1-4 linear or branched alkyl);
- each G2 group is independently selected from a bonding end bonded to G4 groups present in other L group(s) than the L group in which it is located, C1-10 linear or branched alkyl, —R6G3, H (preferably each independently selected from a bonding end bonded to G4 groups present in other L group(s) than the L group in which it is located, C1-6 linear or branched alkyl, —R6G3, H, more preferably each independently selected from a bonding end bonded to G4 groups present in other L group(s) than the L group in which it is located, C1-4 linear or branched alkyl, —R6G3, H);
- each G3 group is independently selected from —OG1, C1-10 linear or branched alkyl, OH, H (preferably each independently selected from —OG1, C1-6 linear or branched alkyl, OH, H, more preferably each independently selected from —OG1, C1-4 linear or branched alkyl, OH, H);
- the R6 group is selected from a single bond, C1-20 linear or branched alkylene (preferably each independently selected from a single bond, C1-6 linear or branched alkylene, more preferably each independently selected from a single bond, C1-4 linear or branched alkylene);
- G1 group is selected from a bonding end bonded to the boron atom in the boron-containing group, C1-6 linear or branched alkyl, H (preferably selected from a bonding end bonded to the boron atom in the boron-containing group, C1-4 linear or branched alkyl, H);
- G4 group is selected from a bonding end bonded to G2 groups present in other L group(s) than the L group in which it is located, H;
- in a L group(s), there is at least one A group that is a group represented by formula (III), there is at least one G1 group that is a bonding end bonded to the boron atom in the boron-containing group;
- each A′ group in the b boron-containing group(s) is independently selected from a bonding end bonded to the G1 group present in the L group, a group represented by formula (V), —OR′, the R′ group is H or C1-20 linear or branched alkyl (preferably H or C1-6 linear or branched alkyl, preferably H or C1-4 linear or branched alkyl);
- in formula (V), m is independently an integer of 0-10 (preferably an integer of 0-5, more preferably 0, 1 or 2);
- the R0 group is each independently selected from C1-10 linear or branched alkyl, —R6G5, H (preferably each independently selected from C1-6 linear or branched alkyl, —R6G5, H, preferably each independently selected from C1-4 linear or branched alkyl, —R6G5, H);
- in formula (V), the R5 group is each independently selected from 3-valent C1-20 linear or branched alkyl (preferably each independently selected from 3-valent C1-6 linear or branched alkyl, preferably each independently selected from 3-valent C1-4 linear or branched alkyl);
- in formula (V), the G6 group is selected from —R6G5, C1-10 linear or branched alkyl, H (preferably selected from —R6G5, C1-6 linear or branched alkyl, H, preferably selected from —R6G5, C1-4 linear or branched alkyl, H);
- the G6 group is independently selected from a single bond, C1-20 linear or branched alkylene (preferably each independently selected from a single bond, C1-6 linear or branched alkylene, more preferably each independently selected from a single bond, C1-4 linear or branched alkylene);
- each G5 group is independently selected from —OG1, C1-10 linear or branched alkyl, OH, H (preferably each independently selected from —OG1, C1-6 linear or branched alkyl, OH, H, more preferably each independently selected from —OG1, C1-4 linear or branched alkyl, OH, H), wherein the G1 group is selected from a bonding end bonded to the boron atom in the boron-containing group, C1-6 linear or branched alkyl, H (preferably selected from a bonding end bonded to the boron atom in the boron-containing group, C1-4 linear or branched alkyl, H);
- in the case that the group represented by formula (V) is present, in the group represented by formula (V), there is at least one G1 group that is a bonding end bonded to the boron atom in the boron-containing group;
- in the b boron-containing group(s), there is at least one A′ group that is a bonding end bonded to the G1 group present in the L group;
- each group in the organoboron compound complies with the bonding rules.
27 more elements
A process for preparing an organoboron compound, which comprises the following steps:
- (1) reacting a compound represented by formula (X) with a peroxide;
- in formula (X), RO is bonded to the benzene ring (RO is preferably located at the meta position of the R1 group on the benzene ring);
- y R group(s) is/are bonded to the benzene ring;
- y is selected from an integer of 0-4 (preferably an integer of 1-3, more preferably 1 or 2);
- the R group is each independently selected from H and C1-20 linear or branched alkyl (preferably each independently selected from H and C1-6 linear or branched alkyl, preferably each independently selected from H and C1-4 linear or branched alkyl, more preferably selected from H and tert-butyl);
- n is an integer of 1-10 (preferably an integer of 1-5, more preferably 1, 2 or 3);
- R1 is each independently selected from a single bond and C1-30 linear or branched alkylene (preferably selected from a single bond and C1-20 linear or branched alkylene, preferably C1-10 linear or branched alkylene);
- each of R2s in n structure units is identical or different from each other and each R2 is independently selected from a single bond and C1-20 linear or branched alkylene (preferably each independently selected from a single bond and C1-6 linear or branched alkylene, preferably each independently selected from a single bond and C1-4 linear or branched alkylene);
- R3 is selected from H and C1-30 linear or branched alkyl (preferably selected from H and C1-20 linear or branched alkyl, preferably H and C1-10 linear or branched alkyl, further preferably H and C1-6 linear or branched alkyl);
- A″s in n structural units are identical or different from each other and each independently selected from
- wherein the R4 group is each independently selected from H and C1-20 linear or branched alkyl (preferably each independently selected from H and C1-6 linear or branched alkyl, preferably selected from H and C1-4 linear or branched alkyl);
- in formula (X) there is at least one A″ that is
- (2) reacting the reaction product of step (1) with a compound represented by formula (Y);
- in formula (Y), m is an integer of 0-10 (preferably an integer of 0-5, more preferably 0, 1 or 2);
- the R0′ group is each independently selected from C1-10 linear or branched alkyl, —R6OH, H (preferably each independently selected from C1-6 linear or branched alkyl, —R6OH, H, preferably each independently selected from C1-4 linear or branched alkyl, —R6OH, H);
- the R5 group is each independently selected from 3-valent C1-20 linear or branched alkyl (preferably each independently selected from 3-valent C1-6 linear or branched alkyl, preferably each independently selected from 3-valent C1-4 linear or branched alkyl);
- each G5′ group is independently selected from C1-10 linear or branched alkyl, OH, H (preferably each independently selected from C1-6 linear or branched alkyl, OH, H, more preferably independently selected from C1-4 linear or branched alkyl, OH, H);
- G6′ group is selected from C1-10 linear or branched alkyl, —R6OH, H (preferably selected from —R6OH, C1-6 linear or branched alkyl, H, preferably selected from —R6OH, C1-4 linear or branched alkyl, H);
- the R6 group is each independently selected from a single bond, C1-20 linear or branched alkylene (preferably each independently selected from a single bond, C1-6 linear or branched alkylene, preferably each independently selected from a single bond, C1-4 linear or branched alkylene);
- in formula (Y), at least one of R0′ group and G6′ group is H, and optionally at least one G5′ group is OH and/or at least one G6′ group and/or at least one R0′ group is —R6OH;
- (3) reacting the reaction product of step (2) with an inorganic boron compound to obtain an organoboron compound.
18 more elements
Dependencies are inferred from the claim text.