CN105294904B - The synthetic method of polyalphaolefin lubricating oil with antioxygenic property - Google Patents
The synthetic method of polyalphaolefin lubricating oil with antioxygenic property Download PDFInfo
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- CN105294904B CN105294904B CN201510882728.6A CN201510882728A CN105294904B CN 105294904 B CN105294904 B CN 105294904B CN 201510882728 A CN201510882728 A CN 201510882728A CN 105294904 B CN105294904 B CN 105294904B
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- antioxygenic property
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Abstract
The present invention relates to a kind of preparation method of the polyalphaolefin lubricating oil with antioxygenic property, this method is by β 3, the hydroxy-phenylpropionic acid of 5 di-t-butyl 4 is esterified with the part of hydroxyl in hexylene glycol or trimethylolpropane or pentaerythrite or bipentaerythrite, obtains the hydroxy compounds containing antioxidant groups；The hydroxy compounds is fully esterified with acrylic acid again, you can obtain the response type antioxidant with end group double bond；In the polymerization process that alhpa olefin is octene, decene, 1 laurylene, this response type antioxidant with end group double bond is added, the polyalphaolefin lube base oil with antioxygenic property can be obtained after polymerisation.Polyalphaolefin lubricating oil prepared by the present invention itself has good antioxygenic property, substantial amounts of antioxidant groups is contained in structure, while the content of antioxidant groups can also be adjusted according to different requirements.In use without adding phenol antioxidant again.
Description
Technical field
The present invention relates to a kind of synthetic method of the polyalphaolefin lubricating oil with antioxygenic property.
Background technology
Polyalphaolefin (PAO) be synthesize aeroengine oil main constituents, be influence oil product combination property it is crucial because
Element, at home and abroad aviation engine lubricating oil field is using quite varied.PAO not only has the same hydro carbons of petroleum base base oil
Structure, but also the long side chain for the unique marshalling not possessed with petroleum base hydro carbons.Therefore, PAO has compared with petroleum base
Base oil more comprehensively performance, it is a kind of aviation engine lubricating oil base oil of function admirable.
High-temperature thermal oxidation stability is one of important performance of aviation engine lubricating oil, and determines that it uses temperature
The important parameter of degree.Aero-engine high temperature, high-revolving work characteristics, easily make the quality acute variation of engine lubricating oil,
When especially lubricating oil operating temperature is more than 200 DEG C, oil oxidation speed can be multiplied, lubricating oil thermal oxide decay adds
It is acute.Therefore, aero-engine has the requirement of harshness to the oxidation stability of lube base oil.
Antioxidant can eliminate caused free radical and free radical during lubricating oil use, effectively delay lubricating oil
Oxidation deterioration, extend machinery equipment service life.DBPC 2,6 ditertiary butyl p cresol (antioxidant T501) is most popular
Phenolic antioxidant kind, dosage 0.1%-1.0%.Its manufacturing process is simple, cost is low, but volatile, and antioxidant effect can not
Persistently, thermal weight loss temperature is low, should not use at high temperature.In addition, phenol antioxidant has larger polarity, and polyalphaolefin
Polarity is smaller, add antioxidants in polyalphaolefin it is possible that due to different polarities are big and antioxidant is from polyalphaolefin
The problem of being separated out in lubricating oil.This be also at present mostly lube oil additive in mineral oil and polyalphaolefin lubricating oil using depositing
The problem of.Antioxidant is embedded in polyalphaolefin in the present invention so that itself contain antioxidant in the polyalphaolefin of preparation,
Solve the problems, such as that antioxidant separates out from base oil.
The content of the invention
It is an object of the present invention to provide a kind of preparation method of the polyalphaolefin lubricating oil with antioxygenic property, the party
Method is by β -3,5- di-tert-butyl-hydroxy phenyls propionic acid and hexylene glycol or trimethylolpropane or pentaerythrite or bipentaerythrite
In part of hydroxyl esterification, obtain the hydroxy compounds containing antioxidant groups；The hydroxy compounds is abundant with acrylic acid again
Esterification, you can obtain the response type antioxidant with end group double bond；In the polymerization that alhpa olefin is octene, decene, 1- laurylenes
Cheng Zhong, this response type antioxidant with end group double bond is added, can be obtained with antioxygenic property after polymerisation
Polyalphaolefin lube base oil.Polyalphaolefin lubricating oil prepared by the present invention itself has good antioxygenic property, structure
In contain substantial amounts of antioxidant groups, while the content of antioxidant groups can also be adjusted according to different requirements.Using
During without adding phenol antioxidant again.
The synthetic method of polyalphaolefin lubricating oil of the present invention with antioxygenic property, follows these steps to carry out：
A. by β -3,5- di-tert-butyl-hydroxy phenyls propionic acid and acrylic acid and hexylene glycol, trimethylolpropane, Ji Wusi
Alcohol or bipentaerythrite are inserted in reaction unit, and it is stannous chloride or p-methyl benzenesulfonic acid to add catalyst, adds solvent toluene
Or dimethylbenzene, reaction temperature are 110 DEG C -190 DEG C, reaction time 4h-12h, are cooled to room temperature, obtain mixture；
B, the mixture for obtaining step a adds acrylic acid, and control temperature reacts 6-7h, be cooled to room at 130-140 DEG C
Temperature；Neutrality is washed with distilled water to, then boils off water and dimethylbenzene, obtains the response type antioxygen with end group double bond
Agent；
C, it is octene, decene or 1- ten that the response type antioxidant with end group double bond for obtaining step b, which is added to alhpa olefin,
In the polymerisation of diene, in AlCl3、BF3Or under the conditions of Ziegler-Natta catalyst, polymerisation occurs, finally obtains
Polyalphaolefin lubricating oil with antioxygenic property.
The dosage of catalyst is mass fraction 0.3%-1.0% in step a.
The synthetic method of polyalphaolefin lubricating oil of the present invention with antioxygenic property, this method is by β -3,5- bis-
One or more of tert-butyl-hydroxy phenyl propionic acid and hexylene glycol, trimethylolpropane, pentaerythrite and bipentaerythrite
Hydroxy esterification, obtain the polyol with antioxidant groups.The polyol with acroleic acid esterification, is had again
There is the response type antioxidant of antioxidant groups.Then the response type antioxidant carries out polymerisation with alhpa olefin, and synthesis has
The polyalphaolefin lube base oil of antioxygenic property.The polyalphaolefin lubricating oil that the present invention obtains, containing substantial amounts of anti-in structure
Oxide group, therefore itself there is good antioxygenic property.
The present invention is compared with prior art：The common practice of the antioxidant of lube base oil addition at present is will be anti-oxidant
Agent is added in the base oil under certain temperature, is dispersed with stirring uniformly.Such a method can be as required antioxidant matter
Amount condition, but there is also the drawbacks of antioxidant and base oil poor compatibility.Antioxidant is addition at slightly higher temperature
In base oil, at this moment antioxidant and basic oil compatibility are good.After base oil cools down, due to the pole of antioxidant and base oil
Property difference it is larger, antioxidant may separate out from base oil, can not play the effect of antioxidation in use.Cause
This, antioxidant is embedded in base oil by the method for the invention, fundamentally solves antioxidant and basic oil compatibility
Difference and the problem of cause antioxidant to be separated out from base oil.
Brief description of the drawings
Fig. 1 is infrared spectrogram of the present invention.
Embodiment
Following example is the further explanation to the present invention, rather than is limited the invention.
Embodiment 1
Weigh 11.8g hexylene glycols and 27.8g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid inserts band electric stirring, temperature
In the 250mL there-necked flask reaction units of degree meter, water knockout drum and condenser, the stannous chloride of catalyst quality fraction 0.3% is added, then
Solvent 70mL dimethylbenzene is added, reaction temperature reaction time 5h, is cooled to room temperature at 110 DEG C, obtains the change containing antioxidant group
The mixture of compound and toluene；
It will obtain adding 7.2g acrylic acid in the mixture of the compound containing antioxidant group and toluene, control temperature exists
140 DEG C, 6.5h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, obtain
Response type antioxidant with end group double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of octene,
AlCl3Polymerisation is carried out under catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 2
Weigh 11.8g hexylene glycols and 27.8g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid inserts band electric stirring, temperature
In the 250mL there-necked flask reaction units of degree meter, water knockout drum and condenser, the stannous chloride of catalyst quality fraction 0.5% is added, then
Solvent 70mL dimethylbenzene is added, control temperature reacts 4h, be cooled to room temperature, obtain the compound containing antioxidant group at 140 DEG C
And the mixture of toluene；
The mixture for obtaining the compound containing antioxidant group and toluene is added into 7.2g acrylic acid, control temperature is 130
DEG C, 7h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, is obtained with end
The response type antioxidant of base double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of decene,
AlCl3Polymerisation is carried out under catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 3
Weigh 11.8g hexylene glycols and 27.8g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid inserts band electric stirring, temperature
In the 250mL there-necked flask reaction units of degree meter, water knockout drum and condenser, the p-methyl benzenesulfonic acid of catalyst quality fraction 0.5% is added,
Solvent 70mL dimethylbenzene is added, 150 DEG C of reaction temperature, reaction time 6h, room temperature is cooled to, obtains the change containing antioxidant group
The mixture of compound and toluene；
The mixture for obtaining the compound containing antioxidant group and toluene is added into 7.2g acrylic acid, control temperature is 130
DEG C, 7h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, is obtained with end
The response type antioxidant of base double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of 1- laurylenes,
BF3Polymerisation is carried out under catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 4
Weigh 13.4g trimethylolpropanes and 55.6g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid inserts band electric mixing
Mix, in the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, add the protochloride of catalyst quality fraction 0.5%
Tin, solvent 70mL toluene is added, reaction temperature reacts 8h, be cooled to room temperature, obtain the change containing antioxidant group at 150 DEG C
The mixture of compound and toluene；
The mixture for obtaining the compound containing antioxidant group and toluene is added into 7.2g acrylic acid, control temperature is 130
DEG C, 7h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and toluene, obtain carrying end group
The response type antioxidant of double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of octene, in BF3
Polymerisation is carried out under catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 5
Weigh 13.4g trimethylolpropanes and 55.6g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid inserts band electric mixing
Mix, in the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, add the protochloride of catalyst quality fraction 1%
Tin, adds solvent 70mL toluene, and reaction temperature reaction time 4h, is cooled to room temperature, obtained containing antioxidant group at 160 DEG C
Compound and toluene mixture；
The mixture for obtaining the compound containing antioxidant group and toluene is added into 7.2g acrylic acid, control temperature is 130
DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and toluene, obtain carrying end group
The response type antioxidant of double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of decene,
Polymerisation is carried out under Ziegler-Natta catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 6
Weigh 13.4g trimethylolpropanes and 55.6g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid inserts band electric mixing
Mix, in the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, add the protochloride of catalyst quality fraction 1%
Tin, solvent 60mL dimethylbenzene is added, 170 DEG C of reaction temperature, reaction time 8h, room temperature is cooled to, obtains containing antioxidant group
Compound and dimethylbenzene mixture；
The mixture for obtaining the compound containing antioxidant group and dimethylbenzene is added into 7.2g acrylic acid, control temperature exists
130 DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, obtain band
There is the response type antioxidant of end group double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of 1- laurylenes,
Polymerisation is carried out under Ziegler-Natta catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 7
Weigh 13.6g pentaerythrites and 83.4g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid insert band electric stirring,
In the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, the stannous chloride of catalyst quality fraction 1% is added, then
Solvent 70mL toluene is added, reaction temperature reacts 10h, be cooled to room temperature, obtain the compound containing antioxidant group at 180 DEG C
And the mixture of toluene；
The mixture for obtaining the compound containing antioxidant group and toluene is added into 7.2g acrylic acid, control temperature is 130
DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and toluene, obtain carrying end group
The response type antioxidant of double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of octene,
AlCl3Polymerisation is carried out under catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 8
Weigh 13.6g pentaerythrites and 83.4g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid insert band electric stirring,
In the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, catalyst quality fraction 0.7% is added to toluene sulphur
Acid, solvent 70mL dimethylbenzene is added, 190 DEG C of reaction temperature, reaction time 4h, room temperature is cooled to, obtains containing antioxidant group
Compound and dimethylbenzene mixture；
The mixture for obtaining the compound containing antioxidant group and dimethylbenzene is added into 7.2g acrylic acid, control temperature exists
140 DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, obtain band
There is the response type antioxidant of end group double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of decene, in BF3
Polymerisation is carried out under catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 9
Weigh 13.6g pentaerythrites and 83.4g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid insert band electric stirring,
In the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, catalyst quality fraction 0.7% is added to toluene sulphur
Acid, adds solvent 70mL dimethylbenzene, and reaction temperature reaction time 12h, is cooled to room temperature at 110 DEG C, obtained containing antioxygen base
The compound of group and the mixture of dimethylbenzene；
The mixture for obtaining the compound containing antioxidant group and dimethylbenzene is added into 7.2g acrylic acid, control temperature exists
140 DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, obtain band
There is the response type antioxidant of end group double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of 1- laurylenes,
BF3Polymerisation is carried out under catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 10
Weigh 25.4g bipentaerythrites and 139g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid insert band electric stirring,
In the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, catalyst quality fraction 0.1% is added to toluene sulphur
Acid, solvent 70mL dimethylbenzene is added, reaction temperature reacts 5h, be cooled to room temperature, obtain containing antioxidant group at 190 DEG C
The mixture of compound and dimethylbenzene；
The mixture for obtaining the compound containing antioxidant group and dimethylbenzene is added into 7.2g acrylic acid, control temperature exists
140 DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, obtain band
There is the response type antioxidant of end group double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of 1- octenes,
Polymerisation is carried out under Ziegler-Natta catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 11
Weigh 25.4g bipentaerythrites and 139g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid insert band electric stirring,
In the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, catalyst quality fraction 0.5% is added to toluene sulphur
Acid, solvent 70mL dimethylbenzene is added, reaction temperature reacts 10h, be cooled to room temperature, obtain containing antioxidant group at 180 DEG C
The mixture of compound and dimethylbenzene；
The mixture for obtaining the compound containing antioxidant group and dimethylbenzene is added into 7.2g acrylic acid, control temperature exists
140 DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, obtain band
There is the response type antioxidant of end group double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of 1- decene,
Polymerisation is carried out under Ziegler-Natta catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
Embodiment 12
Weigh 25.4g bipentaerythrites and 139g β -3,5- di-tert-butyl-hydroxy phenyl propionic acid insert band electric stirring,
In the 250mL there-necked flask reaction units of thermometer, water knockout drum and condenser, catalyst quality fraction 0.5% is added to toluene sulphur
Acid, adds solvent 70mL dimethylbenzene, and reaction temperature reaction time 5h, is cooled to room temperature at 170 DEG C, obtained containing antioxygen base
The compound of group and the mixture of dimethylbenzene；
The mixture for obtaining the compound containing antioxidant group and dimethylbenzene is added into 7.2g acrylic acid, control temperature exists
135 DEG C, 6h is reacted, room temperature is cooled to, is washed with distilled water to neutrality, then boil off water and dimethylbenzene, obtain band
There is the response type antioxidant of end group double bond；
The obtained response type antioxidant with end group double bond is added in the polymerization reaction system of 1- laurylenes,
Polymerisation is carried out under BF3 catalytic action, finally obtains the polyalphaolefin lubricating oil with antioxygenic property.
The synthetic method of polyalphaolefin lubricating oil of the present invention with antioxygenic property, this method can be with from figure
Find out occur the characteristic absorption peak of phenolic hydroxyl group at 3648cm-1, occur C=O bond in ester group at 1746cm-1
Stretching vibration absworption peak.Do not occur any absworption peak at 1640cm-1, this explanation passes through polymerisation, and carbon-carbon double bond is complete
Polymerization.Due to antioxidant groups in polyalphaolefin ratio very little, the peak intensity that the two absworption peaks are shown in infrared spectrogram
Degree is little, but can also absolutely prove that antioxidant groups are embedded into the structure of polyalphaolefin.
Infrared absorpting light spectra can prove the inventive method prepare with antioxygenic property polyalphaolefin lubricating oil be can
Capable.
Claims (1)
1. a kind of synthetic method of the polyalphaolefin lubricating oil with antioxygenic property, it is characterised in that follow these steps to carry out：
A. by β -3,5- di-tert-butyl-hydroxy phenyls propionic acid and hexylene glycol, trimethylolpropane, pentaerythrite or double Ji Wusi
Alcohol is inserted in reaction unit, and it is stannous chloride or p-methyl benzenesulfonic acid to add catalyst, adds solvent xylene, reaction temperature is
110 DEG C -190 DEG C, reaction time 4h-12h, room temperature is cooled to, obtains mixture, the wherein dosage of catalyst is mass fraction
0.3%-1.0%；
B, the mixture for obtaining step a adds acrylic acid, and control temperature reacts 6-7h, be cooled to room temperature at 130-140 DEG C；
Neutrality is washed with distilled water to, then boils off water and dimethylbenzene, it is anti-oxidant to obtain the response type with end group double bond
Agent；
C, it is octene, decene or 1- laurylenes that the response type antioxidant with end group double bond for obtaining step b, which is added to alhpa olefin,
Polymerisation in, in AlCl3、BF3Or under the conditions of Ziegler-Natta catalyst, polymerisation occurs, finally obtaining has
The polyalphaolefin lubricating oil of antioxygenic property.
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| CN106635328A (en) * | 2016-12-01 | 2017-05-10 | 新沂市中诺新材料科技有限公司 | Preparation method of lubricating oil containing nano-modified material |
| CN110330430B (en) * | 2019-06-06 | 2022-04-19 | 深圳市优宝新材料科技有限公司 | Poly-alpha-olefin compound with polar ester group branched chain and preparation method thereof |
| CN110951522A (en) * | 2019-11-15 | 2020-04-03 | 山西潞安矿业(集团)有限责任公司 | Coal-based fully-synthetic long-life gas turbine lubricating oil and preparation method thereof |
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| CN101892112A (en) * | 2010-07-15 | 2010-11-24 | 中国科学院新疆理化技术研究所 | Method for preparing phenolic ester type basic lubricating grease with oxygen resistance |
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