CN109517640A - 6-(2- pyridyl group) the application of -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant - Google Patents
6-(2- pyridyl group) the application of -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant Download PDFInfo
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- CN109517640A CN109517640A CN201811389218.5A CN201811389218A CN109517640A CN 109517640 A CN109517640 A CN 109517640A CN 201811389218 A CN201811389218 A CN 201811389218A CN 109517640 A CN109517640 A CN 109517640A
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- Prior art keywords
- fluorophenyl
- pyridyl group
- aminopyrimidine
- oil
- antioxidant
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
Abstract
The present invention relates to a kind of additives for lubricating oil, and in particular to application of 6- (2- the pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant.There are multiple heterocycles, thermal stability and antioxygen antiseptic property are stronger, are able to satisfy the particular/special requirement in terms of mechanical equipment and environment on the pyrimidine compound molecule.Pyrimidine compound belongs to Ashless type antioxidant, can reduce the abrasion of parts to avoid the generation of greasy filth；The oxidation induction period of the pyrimidine compound is more than 2000min, and has better effects to a variety of base oils, on other properties of lube base oil without influence.
Description
Technical field
The present invention relates to a kind of additives for lubricating oil, and in particular to 6- (2- pyridyl group) -4- p-fluorophenyl -2- ammonia
Application of the yl pyrimidines as lubrication oil antioxidant.
Background technique
Lubricating oil is easy that oxidation, organic polymer and condensation, decomposition occurs with the chemical substance in environment in use
It Deng reaction, while being also easy to generate the organic components such as alcohol, ketone, carboxylic acid, is further oxidized to colloid, or formation oil film is adsorbed on and sets
Electrochemical corrosion occurs for standby surface, reduces the greasy property of lubricating oil, influences the normal use of mechanical equipment.Therefore, lubricating oil
In must be added to antioxidant additive extend Working Life of Lubricating Oil and guarantee engine efficiency.Currently, whole world antioxidant produces
Amount occupies third, is only second to detergent-dispersant additive and Viscosity Index agent, and remain strong growth.With the hair of technology
Exhibition, the lubricating condition of machinery lubrication system is more and more harsher, and to oil ageing stability, higher requirements are also raised.
Oil ageing stability is the important performance indexes of lube product, how to improve lubricating oil oxidation stability
It is an important topic.The undesirable component in lubricating oil is removed by furfural treatment, clay-filtered mode, hydrocracking,
The modes such as hydroisomerizing improve oil property, and antioxidant is added in treated lubricating oil, and can significantly improve oil product uses the longevity
Life.Related research has shown that service life extends nearly 10a when antioxidant is added in certain transformer oil.It is therefore seen that antioxidant is lubricating
Irreplaceable role is played in oil.
In Rong Liangce doctoral thesis " study on the synthesis of multi-component reaction building heterocyclic compound " (2013) article, preparation
A kind of pyrimidine compound of the tridentate ligand with larger steric hindrance --- 6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
Pyridine, and product yield is very high.Pass through the analysis to structure, it is believed that above-mentioned 6- (2- pyridyl group) -4- p-fluorophenyl -2-
Aminopyrimidine may be used as lubrication oil antioxidant, for this purpose, researcher passes through lot of experiments, and achieve satisfied effect
Fruit, but above-mentioned 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied to lubrication oil antioxidant and does not see any document
Or patent report.
Summary of the invention
The present invention is directed to the deficiency of currently available technology and provides a kind of 6- (2- pyridyl group) -4- p-fluorophenyl -2- amino
Application of the pyrimidine as lubrication oil antioxidant, the anti-oxidant energy of the 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine
Power and the strong feature of heat resistance.
Specifically, in the application, the 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, molecule
Formula is as follows:
Specifically, in application, the preparation method of described 6- (2- the pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, referring to
Rong Liangce doctoral thesis " study on the synthesis of multi-component reaction building heterocyclic compound " (2013).
Specifically, in application, being the 6- (2- pyridyl group) -4- p-fluorophenyl-in terms of 100% by lubricating oil total weight
Additional amount when 2- aminopyrimidine is as lubrication oil antioxidant is 0.5-1.0%, remaining is basic lubricating oil.
The present invention is provided to lubricate 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine of oil antioxidant, this is phonetic
There are multiple heterocycles, thermal stability and antioxygen antiseptic property are stronger, are able to satisfy mechanical equipment and environment on acridine compound molecule
The particular/special requirement of aspect.There are two the mechanisms of action for its tool: (1) heterocyclic compound of the pyrimidine compound is easy to attached in metal surface
, metal or metal ion can be prevented to enter in oil, and then from preventing the rotten of metal ion catalysis lube base oil, oxygen
Change；(2) there is amino, the group is more active, and a dissociable H ion out is supplied to base on the molecule of the pyrimidine compound
Alkoxy free group, carbon radicals and the peroxylradicals that the oxidation of plinth oil generates, make its chain terminate.
The present invention is had the following advantages and beneficial effects: compared with prior art
(1) it prepares and comes as the raw material of 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine of lubrication oil antioxidant
Source is extensive, and synthesis technology is simple, adaptable, and dosage is few；
(2) it is anti-to belong to Ashless type for 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant
Oxidant can reduce the abrasion of parts to avoid the generation of greasy filth；
(3) 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant when, lubricating oil it is resistance to
Mild antioxygenic property is strong, and highest heatproof reaches 300~320 DEG C, and oxidation induction period is more than 2000min, and to a variety of base oils
There are better effects, on other properties of lube base oil without influence.
Specific embodiment
The present invention is described in further detail below with reference to specific embodiment, and referring to data.It should be understood that these embodiments
It is of the invention solely for the purpose of illustration, rather than limit the scope of the invention in any way.
Embodiment 1:
6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant, the 6-
(2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, molecular formula are as follows:
The preparation method of described 6- (2- the pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, referring to Rong Liangce doctoral thesis
" study on the synthesis of multi-component reaction building heterocyclic compound " (2013).
A1: when the 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant,
It is the lubrication oil antioxidant 0.5% in terms of 100%, Yanshan Mountain 150SN (lubricating base oils) by lubricating oil total weight
99.5%.
A2: it is T541 0.5% in terms of 100% by lubricating oil total weight when using commercially available T541 as oil antioxidant is lubricated,
Yanshan Mountain 150SN (lubricating base oils) 99.5%.
A3: it is T5440.5% in terms of 100% by lubricating oil total weight when using commercially available T544 as oil antioxidant is lubricated,
Yanshan Mountain 150SN (lubricating base oils) 99.5%.
The lubricating oil A of above-mentioned three kinds different antioxidants after tested1、A2、A3The resistance to temperature value of highest be respectively 305 DEG C, 215
DEG C, 210 DEG C, the resistance to temperature value of Yanshan Mountain 150SN lubricating base oils is 180 DEG C, and the resistance to temperature value of highest extends 125 DEG C, 35 DEG C, 30 respectively
℃。
The lubricating oil A of above-mentioned three kinds different antioxidants after tested1、A2、A3Oxidation induction period be respectively 2560min,
The oxidation induction period of 356min, 423min, Yanshan Mountain 150SN lubricating base oils are 64min, and oxidation induction period extends respectively
2496min、292min、359min。
Test result shows: compared with commercially available T541 and T544,6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
The resistance to temperature value of highest and oxidation induction of Yanshan Mountain 150SN lubricating base oils can be improved when pyridine is as lubrication oil antioxidant significantly
Phase, the resistance to temperature value of highest reach 305 DEG C, and oxidation induction period is more than 2500min, and 6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
With outstanding resistance to mild oxidation resistance when pyridine is as lubrication oil antioxidant, Yanshan Mountain 150SN oil product can be significantly extended
Service life.
Embodiment 2:
6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant, the 6-
(2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, molecular formula are as follows:
The preparation method of described 6- (2- the pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, referring to Rong Liangce doctoral thesis
" study on the synthesis of multi-component reaction building heterocyclic compound " (2013).
B1: when the 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant,
It is the lubrication oil antioxidant 0.6% in terms of 100%, Yanshan Mountain 350SN (lubricating base oils) by lubricating oil total weight
99.4%.
B2: it is T541 0.6% in terms of 100% by lubricating oil total weight when using commercially available T541 as oil antioxidant is lubricated,
Yanshan Mountain 350SN (lubricating base oils) 99.4%.
B3: it is T5440.6% in terms of 100% by lubricating oil total weight when using commercially available T544 as oil antioxidant is lubricated,
Yanshan Mountain 350SN (lubricating base oils) 99.4%.
The lubricating oil B of above-mentioned three kinds different antioxidants after tested1、B2、B3The resistance to temperature value of highest be respectively 310 DEG C, 240
DEG C, 265 DEG C, the resistance to temperature value of Yanshan Mountain 350SN lubricating base oils is 156 DEG C, and the resistance to temperature value of highest extends 154 DEG C, 84 DEG C, 100 respectively
℃。
The lubricating oil B of above-mentioned three kinds different antioxidants after tested1、B2、B3Oxidation induction period be respectively 2452min,
The oxidation induction period of 378min, 340min, Yanshan Mountain 350SN lubricating base oils are 75min, and oxidation induction period extends respectively
2377min、303min、265min。
Test result shows: compared with commercially available T541 and T544,6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
The resistance to temperature value of highest and oxidation induction of Yanshan Mountain 350SN lubricating base oils can be improved when pyridine is as lubrication oil antioxidant significantly
Phase, the resistance to temperature value of highest reach 310 DEG C, and oxidation induction period is more than 2400min, and 6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
With outstanding resistance to mild oxidation resistance when pyridine is as lubrication oil antioxidant, Yanshan Mountain 350SN oil product can be significantly extended
Service life.
Embodiment 3:
6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant, the 6-
(2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, molecular formula are as follows:
The preparation method of described 6- (2- the pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, referring to Rong Liangce doctoral thesis
" study on the synthesis of multi-component reaction building heterocyclic compound " (2013).
C1: when the 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant,
It is the lubrication oil antioxidant 0.8% in terms of 100%, high bridge 400SN (lubricating base oils) by lubricating oil total weight
99.2%.
C2: it is T541 0.8% in terms of 100% by lubricating oil total weight when using commercially available T541 as oil antioxidant is lubricated,
High bridge 400SN (lubricating base oils) 99.2%.
C3: it is T5440.8% in terms of 100% by lubricating oil total weight when using commercially available T544 as oil antioxidant is lubricated,
High bridge 400SN (lubricating base oils) 99.2%.
The lubricating oil C of above-mentioned three kinds different antioxidants after tested1、C2、C3The resistance to temperature value of highest be respectively 308 DEG C, 237
DEG C, 253 DEG C, the resistance to temperature value of high bridge 400SN lubricating base oils is 164 DEG C, and the resistance to temperature value of highest extends 144 DEG C, 73 DEG C, 89 respectively
℃。
The lubricating oil C of above-mentioned three kinds different antioxidants after tested1、C2、C3Oxidation induction period be respectively 2862min,
The oxidation induction period of 453min, 438min, high bridge 400SN lubricating base oils are 94min, and oxidation induction period extends respectively
2768min、359min、344min。
Test result shows: compared with commercially available T541 and T544,6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
The resistance to temperature value of highest and oxidation induction of high bridge 400SN lubricating base oils can be improved when pyridine is as lubrication oil antioxidant significantly
Phase, the resistance to temperature value of highest reach 308 DEG C, and oxidation induction period is more than 2800min, and 6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
With outstanding resistance to mild oxidation resistance when pyridine is as lubrication oil antioxidant, high bridge 400SN oil product can be significantly extended
Service life.
Embodiment 4:
6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant, the 6-
(2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, molecular formula are as follows:
The preparation method of described 6- (2- the pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine, referring to Rong Liangce doctoral thesis
" study on the synthesis of multi-component reaction building heterocyclic compound " (2013).
D1: when the 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is applied as lubrication oil antioxidant,
It is the lubrication oil antioxidant 1.0% in terms of 100%, high bridge 500SN (lubricating base oils) by lubricating oil total weight
99.0%.
D2: it is T5411.0% in terms of 100% by lubricating oil total weight when using commercially available T541 as oil antioxidant is lubricated,
High bridge 500SN (lubricating base oils) 99.0%.
D3: it is T5441.0% in terms of 100% by lubricating oil total weight when using commercially available T544 as oil antioxidant is lubricated,
High bridge 500SN (lubricating base oils) 99.0%.
The lubricating oil D of above-mentioned three kinds different antioxidants after tested1、D2、D3The resistance to temperature value of highest be respectively 320 DEG C, 205
DEG C, 278 DEG C, the resistance to temperature value of high bridge 500SN lubricating base oils is 169 DEG C, and the resistance to temperature value of highest extends 151 DEG C, 36 DEG C, 109 respectively
℃。
The lubricating oil D of above-mentioned three kinds different antioxidants after tested1、D2、D3Oxidation induction period be respectively 2732min,
The oxidation induction period of 386min, 353min, high bridge 500SN lubricating base oils are 105min, and oxidation induction period extends respectively
2627min、281min、248min。
Test result shows: compared with commercially available T541 and T544,6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
The resistance to temperature value of highest and oxidation induction of high bridge 500SN lubricating base oils can be improved when pyridine is as lubrication oil antioxidant significantly
Phase, the resistance to temperature value of highest reach 320 DEG C, and oxidation induction period is more than 2600min, and 6- (2- pyridyl group) -4- p-fluorophenyl -2- amino is phonetic
With outstanding resistance to mild oxidation resistance when pyridine is as lubrication oil antioxidant, high bridge 500SN oil product can be significantly extended
Service life.
The test result of embodiment 1-4 shows: 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is as different bases
Plinth lubricates lubricating oil when oil antioxidant, and the resistance to temperature value of highest is more than 320 DEG C, and oxidation induction period is more than 2400min.Cause
This, not only resistance to mild oxidation resistance when 6- (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is as lubrication oil antioxidant
By force, and the oil product range of adaptation lubricating oil is wide.
Claims (3)
- Application of 1.6- (2- the pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant.
- 2. application according to claim 1, which is characterized in that described 6- (2- the pyridyl group) -4- p-fluorophenyl -2- amino Pyrimidine, molecular formula are as follows:
- 3. application according to claim 1 or 2, which is characterized in that by lubricating oil total weight be 100% in terms of, the 6- Additional amount when (2- pyridyl group) -4- p-fluorophenyl -2- aminopyrimidine is as lubrication oil antioxidant is 0.5-1.0%, remaining For basic lubricating oil.
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| CN201811389218.5A CN109517640A (en) | 2018-11-21 | 2018-11-21 | 6-(2- pyridyl group) the application of -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111909760A (en) * | 2020-07-08 | 2020-11-10 | 上海佳士特润滑科技有限公司 | Lubricating oil applied to motor vehicle and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111909760A (en) * | 2020-07-08 | 2020-11-10 | 上海佳士特润滑科技有限公司 | Lubricating oil applied to motor vehicle and preparation method thereof |
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