CN110205181A - One kind lube oil additive of benzothiazole derivant containing ester group and its preparation and application - Google Patents
One kind lube oil additive of benzothiazole derivant containing ester group and its preparation and application Download PDFInfo
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- CN110205181A CN110205181A CN201910490041.6A CN201910490041A CN110205181A CN 110205181 A CN110205181 A CN 110205181A CN 201910490041 A CN201910490041 A CN 201910490041A CN 110205181 A CN110205181 A CN 110205181A
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- ester group
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- containing ester
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
-
- 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
- C10N2030/45—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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
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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 present invention provides one kind lube oil additive of benzothiazole derivant containing ester group and its preparation and application react dialkylamine with carbon disulfide to obtain waste propylhomoserin salt first under alkaline condition；2-mercaptobenzothiazole reacts to obtain 3- (benzothiazole -2- base is thio) propyl -1- alcohol with chloropropyl alcohol, and 3- (benzothiazole 2- base is thio) propyl -1- alcohol is reacted to obtain 3- (benzothiazole -2- base is thio) propyl -2- chloracetate with chloracetyl chloride；3- (benzothiazole -2- base is thio) propyl -2- chloracetate and waste propylhomoserin reactant salt are obtained having such as general formula I againThe lube oil additive of benzothiazole derivant containing ester group.Preparation method of the present invention is simple, and process conditions are mild, and raw material is easy to get, and synthesis cost is low, and synthetic yield is high, and product is used as the extreme pressure of lubricating oil, wear-resistant, antifriction and anticorrosive additive, hence it is evident that the bearing capacity for improving base oil improves its wear-resistant and antifriction performance.
Description
Technical field
The present invention relates to a kind of lube oil additive of benzothiazole derivant containing ester group and its preparation and application, such derivatives
Object can be widely applied to the fields such as machinery, the energy, environment, material, chemical industry, be particularly suitable as lubricating oil (rouge) additive.
Background technique
Lubricating oil is most important and ubiquitous in industrial processes, with the reinforcement of people's environmental consciousness, also wants
Seek lubricating oil and additive environmental-friendlyization as far as possible in production, use and treatment process.Zinc dialkyl dithiophosphate
(ZDDP) it is used as additive for wear resistance of lubricating oil, the wear-resistant and corrosion resistance of oil product can be improved, in addition its low production cost,
Receive approval in the industry.However, ZDDP is in use, there are unavoidable limitations, add so exploitation is novel
Agent is added to be of great significance.
Benzothiazole has good bearing capacity and greasy property, while having both anti-oxidant, erosion-resisting feature.It is existing
Studies have shown that its derivative can be improved the biological degradability of mineral base oil, it is latency environment close friend's additive；In addition, waste
Ortho esters is the functional group that can be obviously improved additive tribological property, while element sulphur and aromatic ring have synergistic function,
Be conducive to improve the extreme pressure property of oil product.Therefore, this above-mentioned functional group design is combined, is expected to synthesizing property of design
The efficient and environmental-friendly lube oil additive of energy.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of lube oil additive of benzothiazole derivant containing ester group and its
Preparation and application, the derivative is phosphorous, halogen, metallic element etc. are to environment and the harmful element of health, have function admirable,
Environmental-friendly feature.
In order to solve the above technical problems, the technical scheme is that
A kind of lube oil additive of benzothiazole derivant containing ester group, which is characterized in that the benzothiazole containing ester group spreads out
Biolubrication oil additive has the chemical structure such as general formula I:
Wherein, R is the linear or branched alkyl group that C atomicity is 1~30.
The present invention also provides a kind of preparation methods of lube oil additive of benzothiazole derivant containing ester group, special
Sign is, comprising the following steps:
(1) in the presence of alkali, dialkylamine is reacted with carbon disulfide, and intermediate 1, general structure is made are as follows:
Wherein, R is the linear or branched alkyl group that C atomicity is 1~30, and M is Na or K
(2) in the presence of alkali, 2-mercaptobenzothiazole is reacted with trimethylene chlorohydrin, and intermediate 2, structure is made are as follows:
(3) in the presence of alkali, intermediate 2 is reacted with chloracetyl chloride, and intermediate 3, structure is made are as follows:
(4) intermediate 1 prepared by step (1) is reacted with intermediate 3 prepared by step (2), the thiophene of benzo containing ester group is made
Zole derivatives lube oil additive.
As a preferred embodiment of the above technical solution, in the step (1), dialkylamine be di-n-butylamine, two n-octyl amines or
Two octodrines.
As a preferred embodiment of the above technical solution, in step (1)-(4), the reaction medium of reaction is chloroform, dichloromethane
The mixing of one or more of alkane, water, ethyl alcohol, tetrahydrofuran, acetone.
As a preferred embodiment of the above technical solution, in the step (4), the molar ratio of intermediate 1 and intermediate 3 is 0.8:
1~1.2.
As a preferred embodiment of the above technical solution, in step (1)-(4), the reaction temperature of reaction is -5~80 DEG C.
As a preferred embodiment of the above technical solution, in step (1)-(4), the reaction time of reaction is 0.5-12.0h.
The present invention also provides a kind of application of lube oil additive of benzothiazole derivant containing ester group, feature exists
In addition is used alone as lubricating oil or grease additive in the lube oil additive of benzothiazole derivant containing ester group
Enter in base oil or is added into base oil with other lubricating oil or grease additive compound use.
As a preferred embodiment of the above technical solution, the additive amount of the lube oil additive of benzothiazole derivant containing ester group accounts for
The 0.1-10wt% of lubricating oil or lubricating grease gross mass.
Compared with prior art, the invention has the following advantages:
The lube oil additive of benzothiazole derivant containing ester group of the present invention has excellent thermal stability and anti-corruption
Corrosion, excellent extreme pressure, wear-resistant and antifriction performance are the lube oil additives of a kind of excellent combination property；Its preparation process letter
Single, reaction condition is mild, raw materials used cheap and easy to get, and synthetic yield is high；Derivative " without phosphorus ", " Halogen ", " ashless ", are one
The environmentally friendly lube oil additive of class.
Detailed description of the invention:
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 mass spectrogram of embodiment 1.
Fig. 5 is the mass spectrogram of embodiment 2.
Fig. 6 is the mass spectrogram of embodiment 3.
Fig. 7 is the mill spot surface topography scanning electron microscope diagram of plant oil base oil.
Fig. 8 is the mill spot surface topography scanning electron microscope for adding the base oil of 1.0wt%ZDDP lube oil additive
Figure.
Fig. 9 is the mill spot surface topography scanning electron microscope for adding the oil sample of additive prepared by 1.0wt% embodiment 1
Figure.
Figure 10 is the mill spot surface topography scanning electron microscopy for adding the oil sample of additive prepared by 1.0wt% embodiment 2
Mirror figure.
Figure 11 is the mill spot surface topography scanning electron microscopy for adding the oil sample of additive prepared by 1.0wt% embodiment 3
Mirror figure.
Specific embodiment
Below in conjunction with specific embodiment, the present invention will be described in detail, herein illustrative examples and explanation of the invention
For explaining the present invention, but it is not as a limitation of the invention.
Embodiment 1
Sequentially add 0.05mol (6.45g) di-n-butylamine in 250mL there-necked flask, 0.06mol (2.40g) sodium hydroxide and
0.05mol (3.80g) carbon disulfide is added dropwise under ice bath, is stirred to react 3.0h by 50mLTHF.After reaction, it filters, filtrate rotation
Turn evaporative removal solvent, obtains waste propylhomoserin sodium salt.
0.05mol (8.35g) 2-mercaptobenzothiazole is sequentially added in 250mL there-necked flask, 60mL mass fraction is 10%
NaOH aqueous solution, heat up 65 DEG C, stir 0.5h, be added dropwise 0.05mol (4.70g) trimethylene chlorohydrin, heating 80 DEG C be stirred to react
10h.After reaction, it filters, ethyl acetate extraction, for several times, anhydrous magnesium sulfate dries, filters saturated common salt water washing, removes
Solvent obtains 3- (benzothiazole -2- base is thio) propyl -1- alcohol.
0.05mol (11.25g) 3- (benzothiazole -2- base is thio) propyl -1- alcohol is sequentially added in 250mL there-necked flask,
0.06mol (6.72g) chloracetyl chloride is added dropwise under ice bath, is stirred to react 3.0h for 0.06mol (6.06g) triethylamine, 60mL chloroform.
After reaction, reaction solution saturated common salt water washing, anhydrous magnesium sulfate dry, filter, and filtrate removes solvent and obtains 3- (benzo
Thiazol-2-yl is thio) propyl -2- chloracetate.
Above-mentioned waste propylhomoserin sodium salt is sequentially added in 250mL there-necked flask, 3- (benzothiazole -2- is added dropwise in 50mLTHF at room temperature
Base is thio) propyl -2- chloracetate, after being stirred to react 0.5h, temperature rising reflux is stirred to react 5.0h.After reaction, decompression is steamed
Solvent is removed in distillation, and residue is dissolved with ethyl acetate, and saturated common salt water washing, anhydrous magnesium sulfate dries, filters, and filtrate removes molten
Agent obtains yellow oily compound 20.64g, yield 87.6%.1H NMR(400MHz,CDCl3) δ 7.85 (d, J=8.0Hz,
1H), 7.73 (d, J=7.9Hz, 1H), 7.38 (d, J=7.3Hz, 1H), 7.28 (d, J=7.9Hz, 1H), 4.34-4.31 (m,
2H), 4.14 (s, 2H), 3.90 (s, 2H), 3.65 (s, 2H), 3.45-3.41 (m, 2H), 2.21 (dd, J=8.3,4.8Hz,
2H), 1.73-1.64 (m, 4H), 1.34 (dd, J=15.4,7.7Hz, 4H), 0.97-0.90 (m, 6H) .MALDI-TOF-MS, m/
z:calcd for C21H30N2O2S4[M+1]+:470.12,found:471.002。
Embodiment 2
Sequentially add two octodrine of 0.05mol (12.07g) in 250mL there-necked flask, 0.06mol (2.40g) sodium hydroxide and
0.05mol (3.80g) carbon disulfide is added dropwise under ice bath, is stirred to react 3.0h by 50mLTHF.After reaction, it filters, filtrate rotation
Turn evaporative removal solvent, obtains waste propylhomoserin sodium salt.
0.05mol (8.35g) 2-mercaptobenzothiazole is sequentially added in 250mL there-necked flask, 60mL mass fraction is 10%
NaOH aqueous solution, heat up 65 DEG C, stir 0.5h, be added dropwise 0.05mol (4.70g) trimethylene chlorohydrin, heating 80 DEG C be stirred to react
10h.After reaction, it filters, ethyl acetate extraction, for several times, anhydrous magnesium sulfate dries, filters saturated common salt water washing, removes
Solvent obtains 3- (benzothiazole -2- base is thio) propyl -1- alcohol.
0.05mol (11.25g) 3- (benzothiazole -2- base is thio) propyl -1- alcohol is sequentially added in 250mL there-necked flask,
0.06mol (6.72g) chloracetyl chloride is added dropwise under ice bath, is stirred to react 3.0h for 0.06mol (6.06g) triethylamine, 60mL chloroform.
After reaction, reaction solution saturated common salt water washing, anhydrous magnesium sulfate dry, filter, and filtrate removes solvent and obtains 3- (benzo
Thiazol-2-yl is thio) propyl -2- chloracetate.
Above-mentioned waste propylhomoserin sodium salt is sequentially added in 250mL there-necked flask, 3- (benzothiazole -2- is added dropwise in 50mLTHF at room temperature
Base is thio) propyl -2- chloracetate, after being stirred to react 0.5h, temperature rising reflux is stirred to react 5.0h.After reaction, decompression is steamed
Solvent is removed in distillation, and residue is dissolved with ethyl acetate, and saturated common salt water washing, anhydrous magnesium sulfate dries, filters, and filtrate removes molten
Agent obtains yellow oily compound 25.61g, yield 87.8%.1H NMR(400MHz,CDCl3) δ 7.86 (d, J=8.1Hz,
1H), 7.74 (d, J=7.9Hz, 1H), 7.40 (t, J=7.6Hz, 1H), 7.32-7.25 (m, 1H), 4.32 (t, J=5.4Hz,
2H), 4.16 (s, 2H), 3.94 (d, J=6.8Hz, 2H), 3.65 (d, J=7.0Hz, 2H), 3.44 (t, J=6.7Hz, 2H),
2.29-1.96 (m, 4H), 1.27 (s, 16H), 0.89 (d, J=6.2Hz, 12H) .MALDI-TOF-MS, m/z:calcd for
C29H46N2O2S4[M+1]+:582.24,found:583.321。
Embodiment 3
Sequentially add two n-octyl amine of 0.05mol (12.07g) in 250mL there-necked flask, 0.06mol (2.40g) sodium hydroxide and
0.05mol (3.80g) carbon disulfide is added dropwise under ice bath, is stirred to react 3.0h by 50mLTHF.After reaction, it filters, filtrate rotation
Turn evaporative removal solvent, obtains waste propylhomoserin sodium salt.
0.05mol (8.35g) 2-mercaptobenzothiazole is sequentially added in 250mL there-necked flask, 60mL mass fraction is 10%
NaOH aqueous solution, heat up 65 DEG C, stir 0.5h, be added dropwise 0.05mol (4.70g) trimethylene chlorohydrin, heating 80 DEG C be stirred to react
10h.After reaction, it filters, ethyl acetate extraction, for several times, anhydrous magnesium sulfate dries, filters saturated common salt water washing, removes
Solvent obtains 3- (benzothiazole -2- base is thio) propyl -1- alcohol.
0.05mol (11.25g) 3- (benzothiazole -2- base is thio) propyl -1- alcohol is sequentially added in 250mL there-necked flask,
0.06mol (6.72g) chloracetyl chloride is added dropwise under ice bath, is stirred to react 3.0h for 0.06mol (6.06g) triethylamine, 60mL chloroform.
After reaction, reaction solution saturated common salt water washing, anhydrous magnesium sulfate dry, filter, and filtrate removes solvent and obtains 3- (benzo
Thiazol-2-yl is thio) propyl -2- chloracetate.
Above-mentioned waste propylhomoserin sodium salt is sequentially added in 250mL there-necked flask, 3- (benzothiazole -2- is added dropwise in 50mLTHF at room temperature
Base is thio) propyl -2- chloracetate, after being stirred to react 0.5h, temperature rising reflux is stirred to react 5.0h.After reaction, decompression is steamed
Solvent is removed in distillation, and residue is dissolved with ethyl acetate, and saturated common salt water washing, anhydrous magnesium sulfate dries, filters, and filtrate removes molten
Agent obtains yellow oily compound 26.19g, yield 89.8%.1H NMR(400MHz,CDCl3) δ 7.88 (d, J=8.1Hz,
1H), 7.76 (d, J=8.0Hz, 1H), 7.46-7.38 (m, 1H), 7.33-7.29 (m, 1H), 4.34 (t, J=6.0Hz, 2H),
4.17 (s, 2H), 3.95-3.87 (m, 2H), 3.71-3.63 (m, 2H), 3.46 (t, J=7.1Hz, 2H), 2.30-2.17 (m,
2H), 1.77-1.69 (m, 4H), 1.30 (d, J=5.4Hz, 20H), 0.89 (d, J=4.6Hz, 6H) .MALDI-TOF-MS, m/
z:calcd for C29H46N2O2S4[M+1]+:582.24,found:583.205。
The extreme pressure of additive, wear-resistant and antifriction performance and steel ball mill spot surface topography:
By the benzothiazole derivant containing ester group prepared in Examples 1 to 3 lube oil additive and commercially available ZDDP with matter
The additive amount that amount score is 1.0% is added in vegetable oil, and test oil sample is made.Referring to GB-3142-82, using Xiamen nature's mystery
Maximum nonseizure load (the P of four ball frictional testing machine of the MS-10A type evaluation lubricating oil of testing machine factory productionBValue) and be sintered negative
Lotus (PDValue).Experimental condition is room temperature (25 DEG C), revolving speed 1450r/min, time 10s.Testing steel ball used is Shanghai Steel Ball Plant
II grade of GCr15 steel ball of standard of production, diameter 12.7mm, hardness 59-61RC.PBValue and PDThe test result of value is listed in table 1.
1 maximum nonseizure load (P of tableBValue) and sintering load (PDValue)
| Oil sample | PB/N | PD/N |
| Vegetable oil | 470 | 784 |
| ZDDP | 647 | 980 |
| Embodiment 1 | 862 | 1235 |
| Embodiment 2 | 862 | 1235 |
| Embodiment 3 | 862 | 1235 |
The results show that such benzothiazole derivant containing ester group is added in vegetable oil, the P of vegetable oilBAnd PDIt is worth big
Amplitude improves, and shows that the additive of Examples 1 to 3 can significantly improve the extreme pressure property of lubricating oil, extreme pressure property is better than
Conventional additive ZDDP.
By the benzothiazole derivant containing ester group prepared in Examples 1 to 3 lube oil additive and commercially available ZDDP with matter
The additive amount that amount score is 1.0% is added in vegetable oil, and test oil sample is made.Measuring load is on four ball frictional testing machines
392N, revolving speed 1450r/min, steel ball mill spot diameter (WSD), is as a result listed in table 2, averagely rubs accordingly when the time is 30min
It wipes coefficient and is listed in table 3.
2 steel ball mill spot diameter (WSD) of table
| Oil sample | WSD/mm |
| Vegetable oil | 1.405 |
| ZDDP | 0.782 |
| Embodiment 1 | 0.792 |
| Embodiment 2 | 0.774 |
| Embodiment 3 | 0.760 |
The result shows that such benzothiazole derivant containing ester group is added in vegetable oil, the WSD value of vegetable oil is obvious
It reduces.Show that the additive of Examples 1 to 3 can be obviously improved the abrasion resistance of lubricating oil, abrasion resistance and tradition are added
Agent ZDDP is close.
3 average friction coefficient of table
| Oil sample | Coefficient of friction |
| Vegetable oil | 0.122 |
| ZDDP | 0.097 |
| Embodiment 1 | 0.070 |
| Embodiment 2 | 0.064 |
| Embodiment 3 | 0.060 |
The result shows that such benzothiazole derivant containing ester group is added in vegetable oil, the average friction system of vegetable oil
Number is substantially reduced.Show that the additive of Examples 1 to 3 can be improved the antifriction performance of lubricating oil, antifriction performance is better than biography
Unite additive ZDDP.
Fig. 7-11 is that the mill spot surface topography of the oil sample of 3 kinds of additives synthesized by vegetable oil and addition 1.0% scans electricity
Sub- microscope figure.The results show that compared with the steel ball mill spot surface under plant oil lubrication, under the plant oil lubrication containing additive
Steel ball mill spot is shallower, wear scar diameter is smaller, and polishing scratch is more regular, quantity is reduced, and illustrates that additive is added in vegetable oil and plays
Wear-resistant effect.
The thermal stability of additive:
Institute in Examples 1 to 3 is investigated using the TG209 type thermogravimetric analyzer of German Nai Chi instrument manufacturing Co., Ltd production
The thermal stability of the additive of preparation.Test condition are as follows: nitrogen atmosphere, 20 DEG C/min of heating rate, test result are listed in table 4.
The thermal decomposition temperature of 4 additive of table
The results show that the starting thermal decomposition temperature of the benzothiazole derivant containing ester group synthesized in embodiment is 206 DEG C
~235 DEG C, final thermal decomposition temperature is 327 DEG C~350 DEG C, has good thermal stability, is better than conventional additive ZDDP,
It can satisfy the requirement of general operating condition.
The corrosion resistance of additive:
The benzothiazole derivant containing ester group prepared in Examples 1 to 3 is added with the additive amount that mass fraction is 1.0%
Into vegetable oil, test oil sample is made.Corrosion test is carried out referring to the method for GB/T 5096-2017.Test result is listed in table 5.
5 copper strip test result of table
The results show that the corrosion level of the oil sample containing 3 kinds of additives is 1a, it is excellent to illustrate that 3 kinds of additives all have
Corrosion resistance.
Detailed synthetic method of the invention that the present invention is explained by the above embodiments, but the invention is not limited to above-mentioned
Method does not mean that the present invention must rely on above-mentioned reaction condition and could implement.Person of ordinary skill in the field should
It is illustrated, any improvement in the present invention, the change of equivalence replacement and reaction actual conditions to reaction dissolvent catalyst of the present invention
Deng all of which fall within the scope of protection and disclosure of the present invention.
The above-described embodiments merely illustrate the principles and effects of the present invention, and is not intended to limit the present invention.It is any ripe
The personage for knowing this technology all without departing from the spirit and scope of the present invention, carries out modifications and changes to above-described embodiment.Cause
This, institute is complete without departing from the spirit and technical ideas disclosed in the present invention by those of ordinary skill in the art such as
At all equivalent modifications or change, should be covered by the claims of the present invention.
Claims (9)
1. a kind of lube oil additive of benzothiazole derivant containing ester group, which is characterized in that the benzothiazole containing ester group is derivative
Object lube oil additive has the chemical structure such as general formula I:
Wherein, R is the linear or branched alkyl group that C atomicity is 1~30.
2. a kind of preparation method of lube oil additive of benzothiazole derivant containing ester group described in claim 1, feature exist
In, comprising the following steps:
(1) in the presence of alkali, dialkylamine is reacted with carbon disulfide, and intermediate 1, general structure is made are as follows:
Wherein, R is the linear or branched alkyl group that C atomicity is 1~30, and M is Na or K
(2) 2-mercaptobenzothiazole is reacted with trimethylene chlorohydrin, intermediate 2, structure is made are as follows:
(3) intermediate 2 prepared by step (2) is reacted with chloracetyl chloride, intermediate 3, structure is made are as follows:
(4) intermediate 1 prepared by step (1) is reacted with intermediate 3 prepared by step (3), the benzene containing ester group such as general formula I is made
And thiazole.
3. a kind of system containing waste propylhomoserin base Benzotriazole Derivative multifunctional additive for lubricating oil according to claim 2
Preparation Method, which is characterized in that in the step (1), dialkylamine is di-n-butylamine, two n-octyl amines or two octodrines.
4. a kind of preparation method of lube oil additive of benzothiazole derivant containing ester group according to claim 2, special
Sign is, in step (1)-(4), the reaction medium of reaction is chloroform, methylene chloride, water, ethyl alcohol, tetrahydrofuran, acetone
One or more of mixing.
5. a kind of preparation method of the lube oil additive of benzothiazole derivant containing ester group as claimed in claim 2, feature
It is, in the step (4), the molar ratio of intermediate 1 and intermediate 3 is 0.8:1~1.2.
6. a kind of preparation method of lube oil additive of benzothiazole derivant containing ester group according to claim 2, special
Sign is, in step (1)-(4), the reaction temperature of reaction is -5~80 DEG C.
7. a kind of preparation method of lube oil additive of benzothiazole derivant containing ester group according to claim 2, special
Sign is, in step (1)-(4), the reaction time of reaction is 0.5-12.0h.
8. a kind of application of lube oil additive of benzothiazole derivant containing ester group described in claim 1, which is characterized in that institute
The lube oil additive of benzothiazole derivant containing ester group is stated as lubricating oil or grease additive exclusive use and is added into base
It is added into base oil in plinth oil or with other lubricating oil or grease additive compound use.
9. a kind of application of the lube oil additive of benzothiazole derivant containing ester group as claimed in claim 8, which is characterized in that
The additive amount of the lube oil additive of benzothiazole derivant containing ester group accounts for the 0.1- of lubricating oil or lubricating grease gross mass
10wt%.
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Citations (3)
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|---|---|---|---|---|
| CN107935963A (en) * | 2017-11-09 | 2018-04-20 | 东莞理工学院 | A kind of benzothiazole derivant multifunctional additive for lubricating oil and preparation method and application |
| CN108034476A (en) * | 2017-12-15 | 2018-05-15 | 东莞理工学院 | A kind of benzothiazole xanthate derivative multifunctional additive for lubricating oil and preparation method and application |
| CN108048163A (en) * | 2018-01-19 | 2018-05-18 | 东莞理工学院 | A kind of famine propylhomoserin base Striazine derivative multifunctional additive for lubricating oil and preparation method and application |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107935963A (en) * | 2017-11-09 | 2018-04-20 | 东莞理工学院 | A kind of benzothiazole derivant multifunctional additive for lubricating oil and preparation method and application |
| CN108034476A (en) * | 2017-12-15 | 2018-05-15 | 东莞理工学院 | A kind of benzothiazole xanthate derivative multifunctional additive for lubricating oil and preparation method and application |
| CN108048163A (en) * | 2018-01-19 | 2018-05-18 | 东莞理工学院 | A kind of famine propylhomoserin base Striazine derivative multifunctional additive for lubricating oil and preparation method and application |
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| 王清华等: "2-巯基苯并噻唑衍生物摩擦学性能的研究", 《石油炼制与化工》 * |
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