CN110256366A - A kind of preparation method of benzotriazole derivative - Google Patents
A kind of preparation method of benzotriazole derivative Download PDFInfo
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- CN110256366A CN110256366A CN201910584904.6A CN201910584904A CN110256366A CN 110256366 A CN110256366 A CN 110256366A CN 201910584904 A CN201910584904 A CN 201910584904A CN 110256366 A CN110256366 A CN 110256366A
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- benzotriazole
- octadecylamine
- mannich
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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
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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)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Lubricants (AREA)
Abstract
The invention discloses a kind of preparation methods of benzotriazole derivative, comprising: under certain condition, benzotriazole, formaldehyde and octadecylamine is carried out Mannich and electrophilic addition reaction in organic solvent, generate benzotriazole derivative.The present invention uses Mannich reaction, it is determined that reaction optimum charging ratio and feeding sequence do not use catalyst, also do not react in water phase；Technique simplification, stable reaction, side reaction is few, yield is high (having reached 96% or more), and it is a kind of green synthesis process that post-processing is simple, the content that generates octadecylamine in gained oil product simultaneously without the three wastes is lower.
Description
Technical field
The invention belongs to lube oil additive technical fields, are related to a kind of synthetic method of lubricating oil oiliness improver, specifically relate to
And a kind of preparation method of benzotriazole derivative.
Background technique
The application of oiliness improver is for the purpose of reducing friction, it is dissolved in lubricating oil, can be formed in friction surface firm
Oriented attachment film can improve the frictional behaviour of lubricating oil, reduce the friction and wear between moving component.
Common oiliness improver domestic at present has the types such as vulcanization cotton seed oil, aliphatic ester, benzotriazole fatty amine salt.Benzotriazole
Fatty amine salt oiliness improver (benzotriazole derivative) is to collect antirust agent, antioxidant, matal deactivator, antiwear additive, preservative in one
The multipurpose additive of body is chiefly used in gear oil, hypoid gear oil, antiwear hydraulic oil, Oil Film of Bearing Oil and lubricating grease, may be used also
As antirust agent and vapour phase inhibitor in anti-corrosive grease.The preparation method operation of traditional benzotriazole fatty amine salt derivative is multiple
Miscellaneous, reaction condition control is stringent.Such as solid-state benzotriazole fatty amine salt T406 additive used at present, preferably resist although having
Mill, anti-oxidant, antiseptic property, but its production method and production technology could be improved.
CN1107470A discloses a kind of preparation method of benzotriazole aliphatic amine derivative, which has following step
Rapid composition: is reacted with acid catalyst, is divided after reaction using benzotriazole sodium, fatty amine or formaldehyde, fatty amine as raw material
Layer, washing, drying and other steps.The preparation of raw material benzotriazole sodium is complicated in above-mentioned preparation method, increases cost, also multistep is needed to close
At；It it is introduced into acid in reaction makees catalyst and be easy to remain in product, be not easy to remove；Last repeated multiple times washing can be brought largely
Industrial wastewater, it is not environmentally economical.
Summary of the invention
Aiming at the shortcomings existing in the above problems, the present invention provides a kind of preparation method of benzotriazole derivative.
The invention discloses a kind of preparation methods of benzotriazole derivative, comprising:
Under certain condition, benzotriazole, formaldehyde and octadecylamine are subjected to Mannich in organic solvent and electrophilic addition is anti-
It answers, generates benzotriazole derivative.
As a further improvement of the present invention, comprising:
Benzotriazole and octadecylamine and a certain amount of organic solvent are mixed, heating, dissolution, heat preservation；Again in certain temperature
Under, it is slowly added into formaldehyde and carries out aminomethylation reaction；Mannich and electrophilic addition reaction are finally carried out under conditions of reflux, it is raw
At benzotriazole derivative.
As a further improvement of the present invention, the reaction process of the benzotriazole, formaldehyde and octadecylamine are as follows:
S1、
S2、
S3、
S4、
As a further improvement of the present invention, catalyst is not used in preparation method.
As a further improvement of the present invention, the organic solvent includes one of ethyl alcohol and 120# gasoline or a variety of.
As a further improvement of the present invention, when the organic solvent is ethyl alcohol and 120# gasoline, the ethyl alcohol and 120#
Quality of gasoline ratio is 1:(0.9~1.2).
As a further improvement of the present invention, the molar ratio of the benzotriazole, formaldehyde and octadecylamine are as follows: (2.0~2.5):
(2.0~2.5): (0.9~1.2).
As a further improvement of the present invention, the temperature of the Mannich reaction is 70~85 DEG C, time of reaction is 3~
8 hours.
As a further improvement of the present invention, further includes:
By product gasoline extracting, the extraction liquid separation, vacuum distillation after Mannich reaction, benzotriazole derivative is obtained.
As a further improvement of the present invention, the vacuum degree of the vacuum distillation is 0.08MPa~0.095MPa.
Compared with prior art, the invention has the benefit that
The present invention uses Mannich reaction, it is determined that and reaction optimum charging ratio and feeding sequence do not use catalyst,
It is not reacted in water phase；Technique simplification, stable reaction, side reaction is few, yield is high (having reached 96% or more), post-processing is simple,
The content for not having the three wastes to generate octadecylamine in gained oil product simultaneously is lower, is a kind of green synthesis process.
Detailed description of the invention
Fig. 1 is the infrared spectrum of benzotriazole derivative disclosed in an embodiment of the present invention.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention
In attached drawing, technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is
A part of the embodiments of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, ordinary skill people
Member's every other embodiment obtained without making creative work, shall fall within the protection scope of the present invention.
The present invention is described in further detail with reference to the accompanying drawing:
The present invention provides a kind of preparation method of benzotriazole derivative, comprising: under certain condition, by benzotriazole (benzo
Triazole), formaldehyde and octadecylamine carry out Mannich and electrophilic addition reaction in organic solvent, generate benzotriazole derivative.
Specifically:
Benzotriazole and octadecylamine and a certain amount of organic solvent are mixed, heating, dissolution, heat preservation；Again in certain temperature
Under, it is slowly added into formaldehyde and carries out aminomethylation reaction；Mannich and electrophilic addition reaction are finally carried out under conditions of reflux, it is raw
At benzotriazole derivative.
Wherein, the reaction of benzotriazole of the present invention, formaldehyde and octadecylamine according to certain feed ratio under reflux conditions
Process are as follows:
S1、
S2、
S3、
S4、
Further, catalyst, the molar ratio of benzotriazole, formaldehyde and octadecylamine are not used in preparation method of the invention are as follows:
(2.0~2.5): (2.0~2.5): (0.9~1.2)；Benzotriazole itself has acidity, itself can do the catalysis of Mannich reaction
Agent does not need to introduce additional acidic catalyst, finally the experimental results showed that reaction simple is feasible.Simultaneous reactions do not introduce water
Phase, post-processing is uncomplicated, generates without the three wastes, enormously simplifies production technology.
Further, the temperature of Mannich reaction of the present invention is 70~85 DEG C, and the time of reaction is 3~8 hours.
Further, the quality and ratio of the additional amount of solvent and solid material benzotriazole and octadecylamine be 1:(0.9~
1.2)。
Further, organic solvent used in reaction of the invention can be single solvent ethyl alcohol, be also possible to mixed solvent
Ethyl alcohol and 120# gasoline are used in mixed way in proportion, and ethyl alcohol and 120# quality of gasoline ratio are 1:(0.9~1.2).
It is extracted after reaction of the invention with 120# gasoline, if it is single solvent ethyl alcohol, then the 120# gasoline matter extracted
Amount is 1.1~2.0 times of ethyl alcohol quality；If it is mixed solvent ethyl alcohol and 120# gasoline, then the 120# quality of gasoline extracted
Take 0.3~0.6 times of mixed solvent.
In a specific embodiment of the present invention:
Benzotriazole, octadecylamine and solvent are added in four-hole boiling flask with the air in nitrogen displacement bottle, beginning by the present invention
Heating, is then turned on stirring.The rate of the stirring is preferably 280~350rpm.Continue to be heated to 45 DEG C, heat preservation 25~
35min.After heat preservation, formaldehyde is slowly added dropwise at this temperature, is added dropwise, stirs 1~2h at this temperature.Temperature continues
Reflux temperature is raised to be reacted.The molar ratio of the benzotriazole, formaldehyde and octadecylamine is preferably 2.0~2.5:2.0~2.5:
0.9~1.2.In the present invention, the temperature of the Mannich reaction is preferably 70~85 DEG C；The time of the Mannich reaction is excellent
It is selected as 3~8 hours.
In the present invention, after the Mannich reaction it is also preferable to include:
By the extracting of Mannich reaction products gasoline, extraction liquid separation, vacuum distillation, benzotriazole disubstituted derivatives are obtained.Its
In:
The present invention is preferably removed solvent by way of vacuum distillation, and the solvent recycled can be used as recycling design
It continues to use.The vacuum degree of vacuum distillation is preferably 0.08MPa~0.095MPa.
The preparation method of benzotriazole derivative provided by the invention, simple process post-process uncomplicated and do not generate waste water.
The present invention mainly optimizes synthetic route, it is determined that reaction optimum charging ratio and feeding sequence, the benzene made
Triazole derivative product appearance is light yellow solid, and octadecylamine residual quantity is 0.01wt% in product, is had very to the performance of product
It is big to improve.The results showed that product appearance is light yellow solid；Octadecylamine 0.01wt%；Fusing point is 52~63 DEG C；Copper sheet is rotten
Lose (150 DEG C, 1h)≤1b；Moisture content % (m/m)≤0.35；Oil-soluble is good.
In order to further illustrate the present invention, the benzotriazole derivative new to one kind provided by the invention below with reference to embodiment
Preparation method be described in detail, but they cannot be interpreted as limiting the scope of the present invention.
Embodiment 1
119g benzotriazole, 134.5g 18 are added in the 1000ml four-hole boiling flask for being equipped with thermometer, condenser
Amine, 120g ethyl alcohol and 125g120# gasoline.It is passed through nitrogen into reaction flask, is sufficiently displaced from bottle after air, begins to warm up.Work as temperature
Degree starts to open stirring when reaching 30 DEG C or so, and stirring rate is 350 revs/min.45 DEG C are gradually heated to, half an hour is kept the temperature,
98.5g formalin is added in Dropping feeder, formalin is slowly added dropwise at 45 DEG C and starts to react, is added dropwise, herein
At a temperature of react 1.5h, then proceed to heating at 70~72 DEG C, react 4h at reflux, stop reaction；Reaction is cooled to
Room temperature is added 125 grams of 120# gasoline and is stripped, then carries out layered filtration, obtain organic phase and water phase.Organic phase is poured into separately
In an outer there-necked flask, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 150 DEG C and obtain yellow liquid, pour out
It is solid-state benzotriazole derivative product that three-necked flask, which is cooled to light yellow solid, and the distillate of collection is that 120# gasoline continues to follow
Ring uses；Water phase is poured into another there-necked flask, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 120 DEG C
Distillate is obtained, recycling design is can be used as and continues cycling through use.
The present invention carries out Appearance Visual, infrared analysis, liquid chromatogram point to benzotriazole derivative product prepared by embodiment 1
Analysis, oil-soluble, copper corrosion and wear resistence measuring；Infrared spectrum such as Fig. 1 of solid-state benzotriazole derivative prepared by embodiment 1
Shown, octadecylamine content is 0.01%wt% in benzotriazole derivative product made from embodiment 1, and product appearance is light yellow solid
Body；Fusing point is 58~60 DEG C；(150 DEG C, 1h) of copper corrosion are 1b；Moisture content % (m/m) is 0.18；Oil-soluble is good；It is wear-resistant
Wear scar diameter D is 0.245cm, yield 96.3% in experiment.
Embodiment 2
121.8g benzotriazole, 121.1g ten are added in the 1000ml four-hole boiling flask for being equipped with thermometer, condenser
Eight amine and 240g ethyl alcohol.It is passed through nitrogen into reaction flask, is sufficiently displaced from bottle after air, begins to warm up.When temperature reaches 30 DEG C
Start to open stirring when left and right, stirring rate is 350 revs/min.45 DEG C are gradually heated to, half an hour is kept the temperature, in Dropping feeder
Middle addition 101.3g formalin, is slowly added dropwise formalin at 45 DEG C and starts to react, be added dropwise, and then proceedes to heating and exists
82~84 DEG C, 4h is reacted at reflux, stops reaction；Reaction is cooled to room temperature, and 350 grams of 120# gasoline are added and are taken out
It mentions, then carries out layered filtration, obtain organic phase and water phase.Organic phase is poured into another there-necked flask, is in vacuum degree
Subtract steaming under the conditions of 0.08MPa~0.095Mpa and obtain yellow liquid to 150 DEG C, pours out three-necked flask and be cooled to light yellow solid i.e.
For solid-state benzotriazole derivative product, the distillate of collection is that 120# gasoline continues cycling through use；Water phase pour into another three
In mouth bottle, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 120 DEG C and obtain distillate, can be used as recycling design
Continue cycling through use.
The present invention carries out Appearance Visual, infrared analysis, liquid chromatogram point to benzotriazole derivative product prepared by embodiment 2
Analysis, oil-soluble, copper corrosion and wear resistence measuring, octadecylamine content is in benzotriazole derivative product made from embodiment 2
0.01%wt%, product appearance are light yellow solid；Fusing point is 54~58 DEG C；(150 DEG C, 1h) of copper corrosion are 1a；Moisture contains
Measuring % (m/m) is 0.22；Oil-soluble is good；Wear scar diameter D is 0.350cm, yield 96.1% in wear-resistant experiment.
Embodiment 3
119g benzotriazole, 161.4g 18 are added in the 1000ml four-hole boiling flask for being equipped with thermometer, condenser
Amine and 140g ethyl alcohol and 140g120# gasoline.It is passed through nitrogen into reaction flask, is sufficiently displaced from bottle after air, begins to warm up.When
Temperature starts to open stirring when reaching 30 DEG C or so, and stirring rate is 350 revs/min.45 DEG C are gradually heated to, is kept the temperature half small
When, 93.2g formalin is added in Dropping feeder, formalin is slowly added dropwise at 45 DEG C and starts to react, is added dropwise,
1.5h is reacted at a temperature of this, is then proceeded to heating at 70~72 DEG C, is reacted 4h at reflux, stops reaction；Reaction cooling
To room temperature, 140 grams of 120# gasoline are added and are stripped, then carries out layered filtration, obtains organic phase and water phase.Organic phase is poured into
In another there-necked flask, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 150 DEG C and obtain yellow liquid,
It is solid-state benzotriazole derivative product that three-necked flask, which is cooled to light yellow solid, out, and the distillate of collection is the continuation of 120# gasoline
It is recycled；Water phase is poured into another there-necked flask, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 120
DEG C distillate is obtained, can be used as recycling design and continue cycling through use.
The present invention carries out Appearance Visual, infrared analysis, oil-soluble, liquid to benzotriazole derivative product prepared by embodiment 3
Analysis of hplc, copper corrosion and wear resistence measuring, octadecylamine content is in benzotriazole derivative product made from embodiment 3
0.01wt%, product appearance are light yellow solid；Fusing point is 54~57 DEG C；(150 DEG C, 1h) of copper corrosion are 1b；Moisture contains
Measuring % (m/m) is 0.24；Oil-soluble is good；Wear scar diameter D is 0.376cm, yield 96.8% in wear-resistant experiment.
Embodiment 4
130.9g benzotriazole, 147.1g ten are added in the 1000ml four-hole boiling flask for being equipped with thermometer, condenser
Eight amine and 140g ethyl alcohol and 130g120# gasoline.It is passed through nitrogen into reaction flask, is sufficiently displaced from bottle after air, begins to warm up.
Start to open stirring when temperature reaches 30 DEG C or so, stirring rate is 350 revs/min.45 DEG C are gradually heated to, is kept the temperature half small
When, 92.30g formalin is added in Dropping feeder, formalin is slowly added dropwise at 45 DEG C and starts to react, is added dropwise,
1.5h is reacted at this temperature, is then proceeded to heating at 70~72 DEG C, is reacted 4h at reflux, stops reaction；React cold
But room temperature is arrived, 150 grams of 120# gasoline are added and are stripped, then carries out layered filtration, obtains organic phase and water phase.Organic phase is fallen
Enter in another there-necked flask, subtract steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 150 DEG C and obtain yellow liquid,
Pouring out three-necked flask and being cooled to light yellow solid is solid-state benzotriazole derivative product, the distillate of collection be 120# gasoline after
It is continuous to be recycled；Water phase is poured into another there-necked flask, is subtracted steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa and is arrived
120 DEG C obtain distillate, can be used as recycling design and continue cycling through use.
The present invention carries out Appearance Visual, infrared analysis, oil-soluble, liquid to benzotriazole derivative product prepared by embodiment 4
Analysis of hplc, copper corrosion and wear resistence measuring, octadecylamine content is in benzotriazole derivative product made from embodiment 4
0.01wt%, product appearance are light yellow solid；Fusing point is 58~60 DEG C；(150 DEG C, 1h) of copper corrosion are 1b；Moisture contains
Measuring % (m/m) is 0.23；Oil-soluble is good；Wear scar diameter D is 0.33cm, yield 96.5% in wear-resistant experiment.
Embodiment 5
119g benzotriazole, 147.5g 18 are added in the 1000ml four-hole boiling flask for being equipped with thermometer, condenser
Amine and 270g ethyl alcohol.It is passed through nitrogen into reaction flask, is sufficiently displaced from bottle after air, begins to warm up.When temperature reaches 30 DEG C of left sides
Start to open stirring when right, stirring rate is 350 revs/min.45 DEG C are gradually heated to, half an hour is kept the temperature, in Dropping feeder
85.1g formalin is added, formalin is slowly added dropwise at 45 DEG C and starts to react, is added dropwise, reacts at this temperature
1.5h then proceedes to heating at 82~84 DEG C, reacts 4h at reflux, stops reaction；Reaction is cooled to room temperature, is added
300 grams of 120# gasoline are stripped, and are then carried out layered filtration, are obtained organic phase and water phase.Organic phase pour into another three
In mouth bottle, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 150 DEG C and obtain yellow liquid, pour out three-necked flask
Being cooled to light yellow solid is solid-state benzotriazole derivative product, and the distillate of collection is that 120# gasoline continues cycling through use；
Water phase is poured into another there-necked flask, is subtracted steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa and is distillated to 120 DEG C
Liquid can be used as recycling design and continue cycling through use.
The present invention carries out Appearance Visual, infrared analysis, oil-soluble, liquid to benzotriazole derivative product prepared by embodiment 5
Analysis of hplc, copper corrosion and wear resistence measuring, octadecylamine content is in benzotriazole derivative product made from embodiment 5
0.01wt%, product appearance are light yellow solid；Fusing point is 54~56 DEG C；(150 DEG C, 1h) of copper corrosion are 1b；Moisture contains
Measuring % (m/m) is 0.25；Oil-soluble is good；Wear scar diameter D is 0.256cm, yield 96.7% in wear-resistant experiment.
Embodiment 6
125g benzotriazole, 147.2g 18 are added in the 1000ml four-hole boiling flask for being equipped with thermometer, condenser
Amine and 140g ethyl alcohol and 135g120# gasoline.It is passed through nitrogen into reaction flask, is sufficiently displaced from bottle after air, begins to warm up.When
Temperature starts to open stirring when reaching 30 DEG C or so, and stirring rate is 350 revs/min.45 DEG C are gradually heated to, is kept the temperature half small
When, 89.3g formalin is added in Dropping feeder, formalin is slowly added dropwise at 45 DEG C and starts to react, is added dropwise,
1.5h is reacted at a temperature of this, is then proceeded to heating at 70~72 DEG C, is reacted 4h at reflux, stops reaction；Reaction cooling
To room temperature, 135 grams of 120# gasoline are added and are stripped, then carries out layered filtration, obtains organic phase and water phase.Organic phase is poured into
In another there-necked flask, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 150 DEG C and obtain yellow liquid,
It is solid-state benzotriazole derivative product that three-necked flask, which is cooled to light yellow solid, out, and the distillate of collection is the continuation of 120# gasoline
It is recycled；Water phase is poured into another there-necked flask, subtracts steaming under the conditions of vacuum degree is 0.08MPa~0.095Mpa to 120
DEG C distillate is obtained, can be used as recycling design and continue cycling through use.
The present invention carries out Appearance Visual, infrared analysis, oil-soluble, liquid to benzotriazole derivative product prepared by embodiment 6
Analysis of hplc, copper corrosion and wear resistence measuring, octadecylamine content is in benzotriazole derivative product made from embodiment 6
0.01wt%, product appearance are light yellow solid；Fusing point is 54~56 DEG C；(150 DEG C, 1h) of copper corrosion are 1b；Moisture contains
Measuring % (m/m) is 0.23；Oil-soluble is good；Wear scar diameter D is 0.302cm, yield 97.1% in wear-resistant experiment.
Test
Wear resistence is done using four ball tester for friction between and oil-soluble is tested, and base oil selects the refining limited public affairs of lubricating oil on Longyan
The 500SN and 150BS of department, being made into 40 DEG C of kinematic viscosity is 220mm2Product of the invention is added according to 0.3% ratio by/s,
Wear resistence and oil-soluble experiment are done, and is compared with reference substance, the two performance is better, illustrates that the performance of oiliness improver is better.It is real
Test that the results are shown in Table 1.
Table 1
| Additive | Additive amount (Wt%) | Wear resistence length rubs D (cm) | Oil-soluble |
| Embodiment 1 | 0.3 | 0.245 | It is bright |
| Reference substance 1 | 0.3 | 0.335 | Unclarity |
| Reference substance 2 | 0.3 | 0.375 | It is transparent |
| Base oil (500SN+150BS) | 0 | 0.576 |
Reference substance is the commodity of available oiliness improver benzotriazole derivative in the market, as it can be seen from table 1 according to this
The benzotriazole derivative oil-soluble for the technical solution preparation that invention provides is good, and wear resistence is good.The residual content of octadecylamine in product
It is lower, it is greatly improved to properties of product.
From above embodiment as can be seen that any acidic catalyst is not added in the invention, it is convenient for using organic solvent
Subtract steaming, and does not introduce a large amount of waste water.Two substitution products are obtained simultaneously, optimize synthetic route, it is determined that reaction optimum charging ratio
And feeding sequence.The benzotriazole product appearance color made is light yellow, and octadecylamine residual quantity is 0.01wt% in product, right
The oil-soluble and wear resistence performance of product are greatly improved.The results showed that product appearance is light yellow solid；Octadecylamine
Residual content is 0.01wt%；Fusing point is 58~60 DEG C；(150 DEG C, 1h) of copper corrosion are 1b；Moisture content % (m/m) is
0.18；Oil-soluble is good；Wear scar diameter D is 0.245cm, yield 96.3% in wear-resistant experiment.
These are only the preferred embodiment of the present invention, is not intended to restrict the invention, for those skilled in the art
For member, the invention may be variously modified and varied.All within the spirits and principles of the present invention, it is made it is any modification,
Equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of benzotriazole derivative characterized by comprising
Under certain condition, benzotriazole, formaldehyde and octadecylamine are subjected to Mannich and electrophilic addition reaction in organic solvent, it is raw
At benzotriazole derivative.
2. preparation method as described in claim 1 characterized by comprising
Benzotriazole and octadecylamine and a certain amount of organic solvent are mixed, heating, dissolution, heat preservation；Again at a certain temperature, slowly
The slow formaldehyde that is added carries out aminomethylation reaction；Mannich and electrophilic addition reaction are finally carried out under conditions of reflux, generate benzene
Triazole derivative.
3. preparation method as described in claim 1, which is characterized in that the reaction process of the benzotriazole, formaldehyde and octadecylamine
Are as follows:
S1、
S2、
S3、
S4、
4. the preparation method as described in claims 1 or 2 or 3, which is characterized in that do not use catalyst in preparation method.
5. the preparation method as described in claims 1 or 2 or 3, which is characterized in that the organic solvent includes ethyl alcohol and 120# vapour
One of oil is a variety of.
6. preparation method as claimed in claim 5, which is characterized in that when the organic solvent is ethyl alcohol and 120# gasoline, institute
It states ethyl alcohol and 120# quality of gasoline ratio is 1:(0.9~1.2).
7. the preparation method as described in claims 1 or 2 or 3, which is characterized in that the benzotriazole, formaldehyde and octadecylamine rub
That ratio are as follows: (2.0~2.5): (2.0~2.5): (0.9~1.2).
8. the preparation method as described in claims 1 or 2 or 3, which is characterized in that the temperature of the Mannich reaction is 70~85
DEG C, the time of reaction is 3~8 hours.
9. the preparation method as described in claims 1 or 2 or 3, which is characterized in that further include:
By product gasoline extracting, the extraction liquid separation, vacuum distillation after Mannich reaction, benzotriazole derivative is obtained.
10. preparation method as claimed in claim 9, which is characterized in that the vacuum degree of the vacuum distillation be 0.08MPa~
0.095MPa。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910584904.6A CN110256366A (en) | 2019-07-01 | 2019-07-01 | A kind of preparation method of benzotriazole derivative |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111454225A (en) * | 2020-05-06 | 2020-07-28 | 新乡市瑞丰新材料股份有限公司 | Preparation method of liquid oiliness agent |
| CN111471029A (en) * | 2020-05-06 | 2020-07-31 | 滨州市坤厚工贸有限责任公司 | Liquid multi-effect lubricating oil oiliness agent and preparation method thereof |
| CN112111316A (en) * | 2020-09-07 | 2020-12-22 | 珠海格力节能环保制冷技术研究中心有限公司 | Refrigerating machine oil, working fluid composition and compressor |
| CN114292244A (en) * | 2022-01-06 | 2022-04-08 | 新乡市瑞丰新材料股份有限公司 | Preparation method of oleic acid modified liquid oiliness agent |
| CN115678643A (en) * | 2021-07-28 | 2023-02-03 | 雅富顿化学公司 | Hydraulic fluid |
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| CN1107470A (en) * | 1994-08-19 | 1995-08-30 | 辽宁省化工研究院 | Method for preparing benzotriazole aliphatic amine derivative |
| CN107973757A (en) * | 2016-10-25 | 2018-05-01 | 中国石油化工股份有限公司 | Double Benzotriazole Derivatives and preparation method thereof, transformer insulation oil complexing agent and transformer insulation oil |
| CN109748879A (en) * | 2019-02-28 | 2019-05-14 | 盘锦辽河油田大力集团有限公司 | A kind of modified benzotriazole and preparation method thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111454225A (en) * | 2020-05-06 | 2020-07-28 | 新乡市瑞丰新材料股份有限公司 | Preparation method of liquid oiliness agent |
| CN111471029A (en) * | 2020-05-06 | 2020-07-31 | 滨州市坤厚工贸有限责任公司 | Liquid multi-effect lubricating oil oiliness agent and preparation method thereof |
| CN111471029B (en) * | 2020-05-06 | 2023-03-10 | 滨州市坤厚工贸有限责任公司 | Liquid multi-effect lubricating oil oiliness agent and preparation method thereof |
| CN112111316A (en) * | 2020-09-07 | 2020-12-22 | 珠海格力节能环保制冷技术研究中心有限公司 | Refrigerating machine oil, working fluid composition and compressor |
| CN115678643A (en) * | 2021-07-28 | 2023-02-03 | 雅富顿化学公司 | Hydraulic fluid |
| CN115678643B (en) * | 2021-07-28 | 2023-12-29 | 雅富顿化学公司 | Hydraulic fluid |
| CN114292244A (en) * | 2022-01-06 | 2022-04-08 | 新乡市瑞丰新材料股份有限公司 | Preparation method of oleic acid modified liquid oiliness agent |
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Application publication date: 20190920 |