CN107522670A - A kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive and preparation method thereof - Google Patents

A kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive and preparation method thereof Download PDF

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CN107522670A
CN107522670A CN201710411992.0A CN201710411992A CN107522670A CN 107522670 A CN107522670 A CN 107522670A CN 201710411992 A CN201710411992 A CN 201710411992A CN 107522670 A CN107522670 A CN 107522670A
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amido
lube oil
oil additive
benzotriazole derivative
alkyl acetoacetates
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韩利芬
戴康徐
赵鸿斌
曹华
鲁浩
廖俊旭
官彩霞
胡嘉漫
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Dongguan University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • 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
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings 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
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • 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
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/41—Chlorine free or low chlorine content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/42—Phosphor free or low phosphor content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/43—Sulfur free or low sulfur content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/45—Ash-less or low ash content
    • 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
    • C10N2030/64—Environmental friendly compositions

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Lubricants (AREA)

Abstract

The invention discloses a kind of not sulfur-bearing, phosphorus, halogen, metallic element biodegradable alkyl acetoacetates amido Benzotriazole Derivative lube oil additive and preparation method and application.The present invention is first in the presence of alkali, and alkylamine obtains alkyl chloroacetamide with chloracetyl chloride through amidatioon, then obtains the target compound of formula I with BTA nucleo philic substitution reaction.The preparation method of the present invention is simple, and process conditions are gentle, and raw material is easy to get, and preparation cost is low, and synthetic yield is high.This new alkyl acetoacetates amido Benzotriazole Derivative can be used alone as the extreme-pressure anti-wear anticorrosive additive of lubricating oil, also can be used in combination with other lube oil additives, available for general operating mode and worst hot case environment, the bearing capacity of base oil can be significantly improved, improve its abrasion resistance, be a kind of environment-friendly multi-functional lube oil additive.

Description

A kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive and its preparation Method
Technical field：
, should the present invention relates to a kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive and preparation method thereof Analog derivative can be widely applied to the fields such as the energy, environment, material science, be particularly suitable as lube oil additive.
Background technology：
Traditional lube oil additive in MOLECULE DESIGN primarily to meet the performance of additive, less consideration It is mostly harmful to environment and health containing sulphur, phosphorus, halogen, metallic element etc. in its molecular structure to factors such as environment, health Element, and these traditional lube oil additives are faced with to environment, ecology and human health stern challenge now.It is modern Lubrication technology from be concerned only with effective utilization to and meanwhile development in terms of paying close attention to effective utilization and ecological Efficiency duality, develop new Environment-friendly biodegradable lube oil additive has become an important subject of lubricating oil industry.
Numerous studies show that BTA not only has good bearing capacity and greasy property, and its molecule knot The N element enriched in structure can grow the nutritional ingredient for providing abundance for microorganism, therefore can improve the biology drop of additive Solve performance；Lube oil additive containing amide group not only has the performance such as good extreme pressure, anticorrosive, anti-oxidant, and Also there is certain biodegradable.Angle of the invention from MOLECULE DESIGN, with reference to the advantages of above-mentioned all kinds of groups, if Meter synthesizes the environment-friendly biodegradable alkyl acetoacetates amido Benzotriazole Derivative of a series of new, applied to lubrication In oil base oil, the lube oil additive of a kind of function admirable has been obtained.
The content of the invention：
The purpose of the present invention is to provide a kind of alkyl acetoacetates amido Benzotriazole Derivative in view of the shortcomings of the prior art Lube oil additive, the alkyl acetoacetates amido Benzotriazole Derivative lube oil additive is not phosphorous, sulphur, chlorine and metal etc. pair The harmful element of environment, has excellent extreme-pressure anti-wear corrosion resistance.
It is a further object to provide the alkyl acetoacetates amido Benzotriazole Derivative lube oil additive Preparation method.
To achieve the above object, the present invention uses following technical scheme：
A kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive, there is formula I structure：
Wherein, R1For C4H9, C6H13, C8H17Straight or branched alkyl；
R2For H or C4H9, C6H13, C8H17Straight or branched alkyl.
A kind of preparation method of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive, comprises the following steps：
(1) in the presence of alkali, with chloracetyl chloride, through amidatioon, intermediate 1 is made, its structure is in alkylamine：
(2) in the presence of alkali, intermediate 1 and BTA nucleo philic substitution reaction, the alkyl second such as formula I is made Amide groups Benzotriazole Derivative.
As the preferred of above-mentioned technical proposal, the reaction medium of reaction is acetonitrile, methanol, ethanol, four in step (1), (2) One or more of mixing in hydrogen furans, chloroform, triethylamine, acetone.
As the preferred of above-mentioned technical proposal, in step (2), the molar ratio of BTA and intermediate 1 is 1.0: (1.0~3.0).
As the preferred of above-mentioned technical proposal, the amount ratio of reaction substrate and reaction medium is 1mol in step (1), (2): (500~2000) mL.
As the preferred of above-mentioned technical proposal, the reaction temperature of reaction is -5~80 DEG C in step (1), (2).
As the preferred of above-mentioned technical proposal, the reaction time of reaction is 2~12h in step (1), (2).
As the preferred of above-mentioned technical proposal, lube oil additive disclosed in this invention can be used alone, and be added to In mineral oil, artificial oil, lubricating oil (fat), good extreme pressure, wear-resistant and corrosion resistance are made it have.Can also be with other profits Oil additive is used in combination, and reaches synergistic function.
As the preferred of above-mentioned technical proposal, the addition when lube oil additive uses is the 0.1wt% of lubricating oil ~15wt%.
Compared with prior art, the invention has the advantages that：
The alkyl acetoacetates amido Benzotriazole Derivative of the present invention is used as lube oil additive, with excellent heat-resisting Property, good extreme pressure anti-wear, excellent corrosion resistance, be a kind of excellent combination property lube oil additive；It prepares work Skill is simple, and reaction condition is gentle, raw materials used cheap and easy to get, and synthetic yield is high；Such additive " no sulphur ", " without phosphorus ", " nothing Halogen ", " ashless ", it is a kind of biodegradable environmentally friendly lube oil additive.
Brief description of the drawings：
Fig. 1 is the hydrogen nuclear magnetic resonance spectrogram of embodiment 1；
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of embodiment 2；
Fig. 3 is the hydrogen nuclear magnetic resonance spectrogram of embodiment 3；
Fig. 4 is the hydrogen nuclear magnetic resonance spectrogram of embodiment 4；
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram of embodiment 5；
Fig. 6 is the mass spectrogram of embodiment 1.
Fig. 7 is the mass spectrogram of embodiment 2.
Fig. 8 is the mass spectrogram of embodiment 3.
Fig. 9 is the mass spectrogram of embodiment 4.
Figure 10 is the mass spectrogram of embodiment 5.
Embodiment：
For a better understanding of the present invention, below by embodiment, the present invention is further described, and embodiment is served only for solving The present invention is released, any restriction will not be formed to the present invention.
Embodiment 1
0.1mol (12.9g) di-n-butylamine, 0.1mol (12.2g) 4- dimethylamino pyrroles are added into 250mL there-necked flask Pyridine (DMAP) and 75mL chloroforms, under ice bath (0 DEG C~5 DEG C), chloracetyl chloride 0.1mol (11.3g), stirring reaction 3h is added dropwise.Reaction After end, reaction solution with saturated common salt water washing three times, dry by anhydrous magnesium sulfate, and filtering, filtrate rotary evaporation removes solvent, obtains To N, N- dibutyl -2- chloroacetamides.
0.1mol (11.9g) BTA, 0.1mol (4.0g) NaOH, 100mL second are added into 250mL there-necked flasks Alcohol, at room temperature, the N for being dissolved in 20mL tetrahydrofurans is added dropwise, N- dibutyl -2- chloroacetamides, after stirring 1.5h, temperature rising reflux reacts 3.5h.After reaction terminates, it is cooled to room temperature, is filtered to remove insoluble matter, filtrate removes solvent, with silica gel column chromatography separating-purifying, obtained To white flock powder 7.2g, yield 91.1%.M.p.79.6~80.0 DEG C.1H NMR(400MHz,CDCl3,TMS,ppm)δ: 8.06 (d, J=8.3Hz, 1H), 7.65-7.35 (m, 3H), 5.49 (s, 2H), 3.46-3.28 (m, 4H), 1.65-1.17 (m, 8H), 0.94 (dt, J=44.0,7.3Hz, 6H) .MALDI-TOF-MS, m/z:calcd for C16H24N4O[M+1]+: 289.195,found:289.195。
Embodiment 2
0.1mol (18.5g) two n-hexylamine, 0.1mol (12.2g) 4- dimethylamino pyrroles are added into 250mL there-necked flask Pyridine (DMAP), 75mL chloroforms, under ice bath (0 DEG C~5 DEG C), chloracetyl chloride 0.1mol (11.3g), stirring reaction 3h is added dropwise.Reaction After end, reaction solution with saturated common salt water washing three times, dry by anhydrous magnesium sulfate, and filtering, filtrate rotary evaporation removes solvent, obtains To N, N- dihexyl -2- chloroacetamides.
0.1mol (11.9g) BTA, 0.1mol (4.0g) NaOH, 100mL second are added into 250mL there-necked flasks Alcohol, at room temperature, the N for being dissolved in 20mL tetrahydrofurans is added dropwise, N- dihexyl -2- chloroacetamides, after stirring 1.5h, temperature rising reflux reacts 3.5h.After reaction terminates, it is cooled to room temperature, is filtered to remove insoluble matter, filtrate removes solvent, with silica gel column chromatography separating-purifying, obtained To colourless liquid 6.8g, yield 89.1%.1H NMR(400MHz,CDCl3,TMS,ppm)δ:8.06 (d, J=7.9Hz, 1H), 7.59 (d, J=7.7Hz, 1H), 7.50 (t, J=7.6Hz, 1H), 7.37 (dd, J=8.1,7.1Hz, 1H), 5.49 (s, 2H), 3.47-3.25 (m, 4H), 1.29 (dd, J=36.5,5.3Hz, 16H), 0.96-0.80 (m, 6H) .MALDI-TOF-MS, m/z: calcd for C20H32N4O[M+1]+:345.258,found:345.264。
Embodiment 3
The n-octyl amines of 0.1mol (24.1g) two, 0.1mol (12.2g) 4- diformazan ammonia are separately added into 250mL there-necked flask Yl pyridines (DMAP), 75mL chloroforms, under ice bath (0 DEG C~5 DEG C), chloracetyl chloride 0.1mol (11.3g), stirring reaction 3h is added dropwise. After reaction terminates, reaction solution with saturated common salt water washing three times, dry by anhydrous magnesium sulfate, and filtering, filtrate rotary evaporation removes molten Agent, obtain N, N- dioctyl -2- chloroacetamides.
0.1mol (11.9g) BTA, 0.1mol (4.0g) NaOH, 100mL second are added into 250mL there-necked flasks Alcohol, at room temperature, the N for being dissolved in 20mL tetrahydrofurans is added dropwise, N- dioctyl -2- chloroacetamides, after stirring 1.5h, temperature rising reflux reacts 3.5h.After reaction terminates, it is cooled to room temperature, is filtered to remove insoluble matter, filtrate removes solvent, with silica gel column chromatography separating-purifying, obtained To colourless liquid 7.7g, yield 91.3%.1H NMR(400MHz,CDCl3,TMS,ppm)δ:8.04 (d, J=8.4Hz, 1H), 7.57 (d, J=8.3Hz, 1H), 7.48 (t, J=7.3Hz, 1H), 7.36 (t, J=7.3Hz, 1H), 5.46 (s, 2H), 3.45- 3.25 (m, 4H), 1.53 (dd, J=20.5,12.3Hz, 4H), 1.26 (dd, J=31.0,15.2Hz, 20H), 0.90-0.80 (m,6H).MALDI-TOF-MS,m/z:calcd for C24H40N4O[M+1]+:401.320,found:401.319。
Embodiment 4
0.1mol (10.1g) n-hexylamine, 0.1mol (12.2g) DMAP are added into 250mL there-necked flask (DMAP), 75mL chloroforms, under ice bath (0 DEG C~5 DEG C), chloracetyl chloride 0.1mol (11.3g), stirring reaction 3h is added dropwise.Reaction knot Shu Hou, reaction solution with saturated common salt water washing three times, dry by anhydrous magnesium sulfate, and filtering, filtrate rotary evaporation removes solvent, obtains N- n-hexyl -2- chloroacetamides.
0.1mol (11.9g) BTA, 0.1mol (4.0g) NaOH, 100mL second are added into 250mL there-necked flasks Alcohol, at room temperature, the N- n-hexyl -2- chloroacetamides for being dissolved in 20mL tetrahydrofurans are added dropwise, after 1.5h is stirred at room temperature, temperature rising reflux is anti- Answer 3.5h.After reaction terminates, it is cooled to room temperature, is filtered to remove insoluble matter, filtrate removes solvent, with silica gel column chromatography separating-purifying, Obtain faint yellow solid 8.4g, yield 90.2%.M.p.89.4~90.5 DEG C,1H NMR(400MHz,CDCl3,TMS,ppm)δ 7.98-7.85 (m, 2H), 7.46 (dd, J=6.6,3.1Hz, 2H), 6.24 (s, 1H), 5.44 (s, 2H), 3.25 (dd, J= 13.4,6.9Hz, 2H), 1.23 (t, J=7.1Hz, 8H), 0.84 (t, J=6.7Hz, 3H) .MALDI-TOF-MS, m/z:calcd for C14H20N4O[M+1]+:261.164,found:261.185。
Embodiment 5
0.1mol (12.9g) octodrine, 0.1mol (12.2g) DMAP are added into 250mL there-necked flask (DMAP), 75mL chloroforms, under ice bath (0 DEG C~5 DEG C), chloracetyl chloride 0.1mol (11.3g), stirring reaction 3h is added dropwise.Reaction knot Shu Hou, reaction solution with saturated common salt water washing three times, dry by anhydrous magnesium sulfate, and filtering, filtrate rotary evaporation removes solvent, obtains N- iso-octyl -2- chloroacetamides.
0.1mol (11.9g) BTA, 0.1mol (4.0g) NaOH, 100mL second are added into 250mL there-necked flasks Alcohol, at room temperature, the N- iso-octyl -2- chloroacetamides for being dissolved in 20mL tetrahydrofurans are added dropwise, after 1.5h is stirred at room temperature, temperature rising reflux is anti- Answer 3.5h.After reaction terminates, it is cooled to room temperature, is filtered to remove insoluble matter, filtrate removes solvent, with silica gel column chromatography separating-purifying, Obtain white solid 7.2g, yield 90.0%.M.p.66.1~67.6 DEG C,1H NMR(400MHz,CDCl3,TMS,ppm)δ7.90 (m,2H),7.45(m,2H),6.29(s,1H),5.45(s,2H),3.63–3.52(m,1H),1.30–1.05(m,10H),0.81 (dd, J=8.8,5.4Hz, 6H) .MALDI-TOF-MS, m/z:calcd for C16H24N4O[M+1]+:289.195,found: 289.237。
Performance test is carried out to lube oil additive made from above-described embodiment 1-5 below.
1st, tribological property is tested
With reference to GB-3142-82, the alkyl acetoacetates amido Benzotriazole Derivative prepared in embodiment 1~5 is dispersed in In atoleine, lubricating oil is evaluated most using the MS-10A types four-ball friction and wear test machine of Xiamen nature's mystery testing machine factory production Greatly without seizing load (PBValue).II grade of GCr15 steel ball of standard that steel ball used in experiment produces for Shanghai Steel Ball Plant, diameter 12.7mm, hardness 59-61RC.Experimental condition is room temperature (25 DEG C), rotating speed 1450r/min, time 10s.PBValue is listed in table 1.
Maximum nonseizure load (the P of table 1BValue)
As a result show, such alkyl acetoacetates amido Benzotriazole Derivative additive is added in atoleine, liquid The P of paraffinBValue is significantly improved.Film strength when lubricating oil works can be improved by showing the additive of embodiment 1~5.
With reference to GB-3142-82, using the sintering load (P of MS-10A types four-ball friction and wear test machine evaluation lubricating oilD Value).Experimental condition is room temperature (25 DEG C), rotating speed 1450r/min, time 10s.PDValue is listed in table 2.
Sintering load (the P of table 2DValue)
As a result show, such alkyl acetoacetates amido Benzotriazole Derivative additive is added in atoleine, liquid The PD values of paraffin are significantly improved.The maximal work ability of lubricating oil can be improved by showing the additive of embodiment 1~5.
Use Xiamen nature's mystery testing machine factory produce MS-10A types four-ball friction and wear test machine measure addition for 1.0wt%, load are that rotating speed 1450r/min, the wear scar diameter (WSD) of steel ball, is as a result arranged when the time is 30min under 392N In table 3, corresponding average friction coefficient is listed in table 4.
The wear scar diameter of table 3 (WSD)
As a result show, such alkyl acetoacetates amido Benzotriazole Derivative additive is added in atoleine, liquid The WSD values of paraffin are obvious to be reduced.The abrasion resistance of lubricating oil can be obviously improved by showing the additive of embodiment 1~5.
The average friction coefficient of table 4
As a result show, such alkyl acetoacetates amido Benzotriazole Derivative additive is added in atoleine, liquid The average friction coefficient of paraffin substantially reduces.The antifriction performance of lubricating oil can be improved by showing the additive of embodiment 1~5.
2nd, heat stability testing
The heat endurance of synthesized additive is investigated using 209 type thermogravimetric analyzers (TGA).Test condition is：Ar Atmosphere, 10 DEG C/min of programming rate.As a result it is listed in table 5.
The TGA decomposition temperatures of table 5
As a result show, the starting of synthesized alkyl acetoacetates amido Benzotriazole Derivative additive in embodiment 1~5 Heat decomposition temperature is 281 DEG C~326 DEG C, and final heat decomposition temperature is 326 DEG C~378 DEG C, has excellent thermal stability, excellent In conventional additive ZDDP, it is suitable for general operating mode and worst hot case.
3rd, corrosion resistance is tested
With reference to GB/T 5096-1985, additive synthesized in embodiment 1~5 is added with 1.0wt% addition Into atoleine, oil sample is made, carries out corrosion test.Experiment copper sheet used is put into oil sample after polishing, is placed in 100 DEG C baking oven, constant temperature places 3.0h, after off-test, takes out copper sheet, is cleaned up with petroleum ether, contrasts Corrosion standards colour table, obtain Go out the corrosion level of synthesized additive.Result of the test is listed in table 6.
The copper strip test result of table 6
As a result show, the corrosion level of the oil sample containing additive 1~5 is 1a, and it is excellent to illustrate that additive 1~5 has Corrosion resistance.
The present invention illustrates the detailed synthetic method of the present invention by above-described embodiment, but the invention is not limited in above-mentioned Method, that is, do not mean that the present invention has to rely on above-mentioned reaction condition and could implemented.Person of ordinary skill in the field should Understand, any improvement in the present invention, the change of equivalence replacement and reaction actual conditions to reaction dissolvent catalyst of the present invention Deng within the scope of all falling within protection scope of the present invention and disclosing.

Claims (9)

1. a kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive, it is characterised in that there is formula I knot Structure：
Wherein, R1For C4H9, C6H13, C8H17Straight or branched alkyl；
R2For H or C4H9, C6H13, C8H17Straight or branched alkyl.
A kind of 2. preparation side of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 1 Method, it is characterised in that comprise the following steps：
(1) in the presence of alkali, with chloracetyl chloride, through amidatioon, intermediate 1 is made, its structure is in alkylamine：
(2) in the presence of alkali, intermediate 1 and BTA nucleo philic substitution reaction, the alkyl acetoacetates amine such as formula I is made Base Benzotriazole Derivative.
A kind of 3. preparation side of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 2 Method, it is characterised in that the reaction medium of reaction is acetonitrile, methanol, ethanol, tetrahydrofuran, chloroform, three second in step (1), (2) One or more of mixing in amine, acetone.
A kind of 4. preparation side of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 2 Method, it is characterised in that in step (2), the molar ratio of BTA and intermediate 1 is 1.0:(1.0~3.0).
A kind of 5. preparation side of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 2 Method, it is characterised in that the amount ratio of reaction substrate and reaction medium is 1mol in step (1), (2):(500~2000) mL.
A kind of 6. preparation side of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 2 Method, it is characterised in that the reaction temperature of reaction is -5~80 DEG C in step (1), (2).
A kind of 7. preparation side of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 2 Method, it is characterised in that the reaction time of reaction is 2~12h in step (1), (2).
8. a kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 1, its feature exist In the lube oil additive can be used as lubricating oil extreme-pressure anti-wear anticorrosive additive to be used alone, can also be with other lubricating oil Additive is used in combination.
9. a kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive as claimed in claim 1, its feature exist In the addition when lube oil additive uses is 0.1wt%~15wt% of lubricating oil.
CN201710411992.0A 2017-06-05 2017-06-05 A kind of alkyl acetoacetates amido Benzotriazole Derivative lube oil additive and preparation method thereof Pending CN107522670A (en)

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Application publication date: 20171229