CN104327054A - Water-soluble benzotriazole imidazoline extreme-pressure anti-wear reagent and preparation method thereof - Google Patents
Water-soluble benzotriazole imidazoline extreme-pressure anti-wear reagent and preparation method thereof Download PDFInfo
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- CN104327054A CN104327054A CN201410640382.4A CN201410640382A CN104327054A CN 104327054 A CN104327054 A CN 104327054A CN 201410640382 A CN201410640382 A CN 201410640382A CN 104327054 A CN104327054 A CN 104327054A
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- benzotriazole
- water
- acetic acid
- imidazole group
- containing imidazole
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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- 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
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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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 relates to a synthetic process of a benzotriazole derivative containing an imidazole group. By taking benzotriazole as a raw material, the synthetic process comprises the steps of reacting benzotriazole with chloroacetic acid to obtain benzotriazole acetic acid; and sequentially reacting benzotriazole acetic acid with diethylenetriamine, N-hydroxy ethanediamine, ethanediamine, triethylene tetramine and tetraethylenepentamine, wherein dimethylbenzene or toluene is used as a water carrying agent, the molar ratio of benzotriazole acetic acid to the amine including diethylenetriamine and N-hydroxy ethanediamine is 1 to 1.1, the reaction temperatures are 130-160 DEG C and 180-220 DEG C, and the reaction time is about 4 hours and about 2 hours. The synthetic process is simple to operate and high in yield, and reaction conditions are easy to control. The product, namely the benzotriazole imidazoline derivative, can be applied to water-based lubricating liquid, a copper corrosion inhibitor, an anti-rust agent and the like.
Description
The present invention relates to the benzotriazole imidazolidine derivatives and preparation method thereof containing imidazole group, it can be used as water-soluble wear preventive additive, also can be used as copper inhibitor, belongs to field of chemical technology.
Background technology
Benzotriazole and methyl benzotriazazole are well-known copper corrosion inhibitors.Benzotriazole has good tribological property in mineral oil, is often used in the extreme pressure in lubricating oil, anti-wear agent, but its oil soluble and water-soluble all poor.As the inhibiter in the aqueous solution benzotriazole in use should with other solubility promoter with the use of, increase its solubleness, make benzotriazole convenient in use.When general intramolecular polar group is for power supply subtype, the cloud density on central atom is larger, and corrosion mitigating effect is better.Tetrahydroglyoxaline has water-soluble preferably, and can form complex compound with metallic element, forms good adsorption layer, in Benzotriazole Derivative, introduce water soluble functional group on surface, as amino and hydroxyl, can increase that it is water-soluble.This patent considers the properties that benzotriazole and tetrahydroglyoxaline have, and in order to make additive play antiwear and reducing friction, antioxygen or performance, has synthesized the imidazolidine derivatives containing benzotriazole functional group.
Patent CN1837338 has synthesized two 1-(benzotriazole base-1-alkyl) polysulfide, can be used as the extreme pressure of lubricating grease, rut preventives be used alone or and other lubricating oil and grease additive compound uses, there is excellent extreme pressure anti-corrosion performance.
Patent CN101205216 has synthesized benzotriazole ammonium salts, as oil solubility lubricant additive.
Patent CN102746279A discloses a kind of containing benzotriazole group ionic liquid and its preparation method and application.The positively charged ion of ionic liquid is glyoxaline cation, and negatively charged ion is hexafluoro-phosphate radical, tetrafluoroborate or two (trimethyl fluoride sulfonyl) amine negative ion, and the cyclosubstituted end group of its imidazoles is containing benzotriazole group.Ionic liquid uses as lubricating oil additive or grease additive.
Summary of the invention
The object of the invention is, the problem poor according to the solubleness of benzotriazole in lubricating oil and water, a kind of synthesis technique of the Benzotriazole Derivative containing imidazole group is provided, this compound has good extreme pressure, abrasion resistance and corrosion resistance, simultaneously in water base lubricant, there is good solubleness, and the method for synthesis above-claimed cpd is provided.
Technical scheme of the present invention is, take benzotriazole as raw material, benzotriazole acetic acid is formed with chloroacetate reaction, and then carry out dehydration cyclization with diethylenetriamine, N-hydroxyethyl-ethylenediamine, quadrol, triethylene tetramine and tetraethylene pentamine etc., generate benzotriazole tetrahydroglyoxaline, reaction conditions is easy to control, and productive rate is high.
The synthesis of the Benzotriazole Derivative containing imidazole group involved in the present invention can represent by chemical equation below:
Wherein, Y is diethylenetriamine, N-hydroxyethyl-ethylenediamine, quadrol, triethylene tetramine and tetraethylene pentamine; X is corresponding terminated radical.
Benzotriazole Derivative containing imidazole group of the present invention can as a kind of multifunctional water-base lubricating oil additive, also can as inhibiter.
The present invention's beneficial effect is compared with the prior art that compound of the present invention can be used alone, and also can add in water base basal liquid using to, has good water-soluble and good extreme pressure, abrasion resistance, also has erosion-resisting ability simultaneously.When using as additive, its addition is 0.1wt% ~ 5.0wt%.
The present invention containing imidazole group Benzotriazole Derivative also can with other lubricating oil and grease additive compound use, can reach synergy synergy.
The present invention is a class very effective multifunctional lubricant (fat) additive and inhibiter containing the Benzotriazole Derivative of imidazole group, having of concrete synthesis:
synthesis;
synthesis;
synthesis.
Product of the present invention is applicable to do additive in the water-based lubricating liquids such as water, water-ethylene glycol, water-glycerine, polyoxyethylene glycol, polyethers, improves the extreme pressure of water-based lubricating liquid, abrasion resistance and erosion-resisting ability.
Embodiment
In order to understand the present invention better, be described by three examples:
Example 1: the benzotriazole adding 20g in the there-necked flask of 1 250ml, the water adding 100ml makees solvent, add the NaOH of 8.0g, stirring reaction 3h at 90 DEG C, the Mono Chloro Acetic Acid aqueous solution of 18g is dripped continuously in half hour, 90 DEG C of reaction 3h, product room temperature cools and adds HCl until there is a large amount of white precipitate, filter washing chlorion, 11.24g is obtained after the benzotriazole acetic acid drying obtained, and then in the there-necked flask of 250ml, add dimethylbenzene respectively make solvent and azeotropic agent, the diethylenetriamine of 8ml, the water produced in 140-160 DEG C of reaction 4h is except dereaction, the water produced in 190-210 DEG C of reaction 2h is except dereaction, underpressure distillation, namely light yellowish brown viscous liquid benzotriazole acetic acid imidazolyl ethamine is obtained.
Example 2: the benzotriazole adding 20g in the there-necked flask of 1 250ml, the water adding 100ml makees solvent, add the NaOH of 8.0g, stirring reaction 3h at 90 DEG C, the Mono Chloro Acetic Acid aqueous solution of 18.0g is dripped continuously in half hour, 90 DEG C of reaction 3h, product room temperature cools and adds HCl until there is a large amount of white precipitate, filter washing chlorion, 11.09g is obtained after the benzotriazole acetic acid drying obtained, and then in the there-necked flask of 250ml, add dimethylbenzene respectively make solvent and azeotropic agent, the N-hydroxyethyl-ethylenediamine of 8ml, the water produced in 140-160 DEG C of reaction 4h is except dereaction, the water produced in 190-210 DEG C of reaction 2 ~ 3h is except dereaction, underpressure distillation, namely light yellowish brown viscous liquid benzotriazole acetic acid imidazolyl ethanol is obtained.
Example 3: the benzotriazole adding 20g in the there-necked flask of 1 250ml, the water adding 100ml makees solvent, add the NaOH of 8.0g, stirring reaction 3h at 90 DEG C, the Mono Chloro Acetic Acid aqueous solution of 18.0g is dripped continuously in half hour, 90 DEG C of reaction 3h, product room temperature cools and adds HCl until there is a large amount of white precipitate, filter washing chlorion, 11.19g is obtained after the benzotriazole acetic acid drying obtained, and then in the there-necked flask of 250ml, add dimethylbenzene respectively make solvent and azeotropic agent, the triethylene tetramine of 8.2ml, the water produced in 140-160 DEG C of reaction 4 ~ 6h is except dereaction, the water produced in 190-210 DEG C of reaction 2 ~ 3h is except dereaction, underpressure distillation, namely light yellowish brown viscous liquid benzotriazole acetic acid imidazolyl ethylamino-ethamine is obtained.
All target compounds have the generation of imidazole ring through Spectrum One type infrared spectrometer determination synthetic, and C, H, the N element analytical results of additive are as shown in table 1.From table 1, results of elemental analyses is known, and C, the H of all target compounds, the measured value of N element conform to substantially with the theoretical value calculated by molecular formula, and absolute error is in allowed band.Can determine that gained compound is target compound.
The results of elemental analyses (being calculated value in bracket) of the various example of table 1
| Example | C％ | H％ | N％ |
| Example 1 | 58.37(59.01) | 6.68(6.55) | 34.11(34.42) |
| Example 2 | 58.15(58.77) | 6.16(6.12) | 27.80(28.57) |
| Example 3 | 58.17(58.53) | 6.99(7.32) | 34.78(34.15) |
The performance evaluation of target compound:
Due to the density of water and viscosity low, freezing point is higher, in order to expand its use range, usually adds the polyvalent alcohols such as ethylene glycol, glycerol, polyoxyethylene glycol to reduce its freezing point and to improve its viscosity in water.Use deionized water and ethylene glycol to be used as basal liquid with mass ratio 1: 1 herein, additive is configured to the solution of 0.5wt%, 1.0wt%, 1.5wt%, 2.0wt%.
Adopt the MRS-10A type friction wear testing machine that Jinan trier factory produces, measure the last non seizure load (PB value) of the Benzotriazole Derivative containing imidazole group prepared by example 1, example 2, test period is 10s.Long mill is carried out according to SH/T0189-92 (392N) standard, test conditions is: rotating speed 1450r/min, room temperature (about 20 DEG C), test period 30min, the wear scar diameter (WSD) of trying under adopting reading microscope (precision 0.01) to measure 3, gets its mean value as wear scar diameter measured value.Steel ball is secondary GCr15 standard steel ball (AISI-52100) that Shanghai Bearing Factory produces, and diameter 12.7mm, hardness HRC are 59-61.
P
bunder value and 392N, wear scar diameter (WSD) the results are shown in table 2.
Table 2 result shows such imidazolyl Benzotriazole Derivative and adds in water based lubrication basal liquid and have excellent solubility property, extreme pressure property and abrasion resistance.
Last non seizure load (the P of table 2 base oil and various additive
bvalue)
In addition, the corrosion resistance of the product of preparation in example 2, example 4 is determined by GB5096-85 standard method.Known after measured, two kinds of production concentrations are that polyoxyethylene glycol constant temperature 3h corrosion to copper sheet at 100 DEG C of 1.0wt% is 1A level.
Claims (7)
1. containing imidazole group the preparation method of Benzotriazole Derivative and it is as an application for water-soluble extreme-pressure anti-friction additive, it is characterized in that, the described Benzotriazole Derivative containing imidazole group, this material has following structural formula:
X is-H,
2. a kind of Benzotriazole Derivative containing imidazole group according to claim 1, is characterized in that radicals X is-H,
3. a kind of its group feature of Benzotriazole Derivative containing imidazole group according to claim 1, it is characterized in that, the described Benzotriazole Derivative containing imidazole group is for reacting containing N heterocycle benzotriazole carboxylic acid and polyamines, parent is benzotriazole, obtaining group after reaction is corresponding imidazoline group, and OH and NH in imidazoline group structural formula
2can as and the reactive group of boric acid ester and phosphoric acid ester.
4. a kind of Benzotriazole Derivative containing imidazole group according to claim 1 and its preparation method and application, it is characterized in that, described Benzotriazole Derivative benzotriazole acetic acid imidazolyl ethanol (ethamine) containing imidazole group as additive application in water, water-ethylene glycol, water-glycerine and other water base basal liquid, and can and other Water-based Lubricating Additives compound use.
5. a kind of Benzotriazole Derivative containing imidazole group according to claim 1 and its preparation method and application, it is characterized in that, the preparation method of described Benzotriazole Derivative benzotriazole acetic acid imidazolyl ethanol (ethamine) containing imidazole group is:
(1) use benzotriazole and aqueous sodium hydroxide solution to react 3 hours at 90 DEG C, then slowly drip Mono Chloro Acetic Acid, react three hours, take out reaction solution, cooling, adds hydrochloric acid until there is a large amount of white precipitate, washing removing chlorion, obtains benzotriazole acetic acid;
(2) the benzotriazole acetic acid that the first step obtains reacts with diethylenetriamine, N-hydroxyethyl-ethylenediamine, quadrol, triethylene tetramine and tetraethylene pentamine respectively;
(3) second step is under reaction medium exists, and reaction medium is: the non-polar organic solvent one of in toluene, benzene, dimethylbenzene and hexanaphthene, and dimethylbenzene is the 20%-25% that azeotropic agent accounts for cumulative volume;
(4) temperature of reaction is reacted at 130-160 DEG C, and except the moisture produced in dereaction, the time is 3-5 hour, and react at 180-220 DEG C, except the moisture produced in dereaction, the time is 2-3 hour;
(5) mol ratio of benzotriazole acetic acid and diethylenetriamine, N-hydroxyethyl-ethylenediamine, triethylene tetramine is 1: 1.0 ~ 1.2.
6. a kind of Benzotriazole Derivative containing imidazole group according to claim 1 and its preparation method and application, is characterized in that, the described Benzotriazole Derivative containing imidazole group mainly contains: benzotriazole acetic acid imidazolyl ethamine; Benzotriazole acetic acid imidazolyl ethanol, benzotriazole acetic acid imidazolinyl ethylamino-ethamine etc.
7. according to claim 3 as water based lubrication oil additive, it is characterized in that water miscible addition mass percent is 0.1%-3.0%.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632277A (en) * | 2016-11-11 | 2017-05-10 | 西安交通大学 | Metal deactivator used for preventing corrosive sulfur corrosion, and preparation method and applications thereof |
| CN107253945A (en) * | 2017-07-04 | 2017-10-17 | 华东交通大学 | BTA imidazolidine derivatives and its preparation method and application |
| CN107311931A (en) * | 2017-07-04 | 2017-11-03 | 华东交通大学 | Water-soluble fatty acid imidazoline quinoline and its preparation method and application |
| CN108138069A (en) * | 2015-10-30 | 2018-06-08 | 雪佛龙奥伦耐有限责任公司 | Lubricant oil composite containing amidine antioxidant |
| CN109679717A (en) * | 2017-10-18 | 2019-04-26 | 中国石油化工股份有限公司 | Compressor lubrication fluid composition and preparation method thereof |
| CN110845419A (en) * | 2019-11-14 | 2020-02-28 | 安徽金德润滑科技有限公司 | Extreme pressure antiwear agent and road vehicle gear oil containing same |
| CN111423913A (en) * | 2020-04-21 | 2020-07-17 | 中国科学院兰州化学物理研究所 | Plant-based base oil with copper corrosion inhibition function |
| CN114656588A (en) * | 2022-05-06 | 2022-06-24 | 中国科学院兰州化学物理研究所 | Polyion liquid, preparation method and application thereof, lubricating and tackifying additive and supramolecular gel lubricant |
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| CN102746279A (en) * | 2011-04-19 | 2012-10-24 | 中国科学院兰州化学物理研究所 | Benzotriazole group-containing ionic liquid and its preparation method and use |
| CN103539786A (en) * | 2013-10-25 | 2014-01-29 | 武汉工程大学 | Benzotriazole imidazoline and derivative and synthesis process and application thereof |
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2014
- 2014-11-05 CN CN201410640382.4A patent/CN104327054B/en active Active
Patent Citations (2)
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| CN102746279A (en) * | 2011-04-19 | 2012-10-24 | 中国科学院兰州化学物理研究所 | Benzotriazole group-containing ionic liquid and its preparation method and use |
| CN103539786A (en) * | 2013-10-25 | 2014-01-29 | 武汉工程大学 | Benzotriazole imidazoline and derivative and synthesis process and application thereof |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108138069A (en) * | 2015-10-30 | 2018-06-08 | 雪佛龙奥伦耐有限责任公司 | Lubricant oil composite containing amidine antioxidant |
| CN108138069B (en) * | 2015-10-30 | 2021-09-24 | 雪佛龙奥伦耐有限责任公司 | Lubricating oil compositions containing amidine antioxidants |
| CN106632277A (en) * | 2016-11-11 | 2017-05-10 | 西安交通大学 | Metal deactivator used for preventing corrosive sulfur corrosion, and preparation method and applications thereof |
| CN106632277B (en) * | 2016-11-11 | 2019-04-16 | 西安交通大学 | A kind of matal deactivator and the preparation method and application thereof for preventing active sulfur from corroding |
| CN107253945A (en) * | 2017-07-04 | 2017-10-17 | 华东交通大学 | BTA imidazolidine derivatives and its preparation method and application |
| CN107311931A (en) * | 2017-07-04 | 2017-11-03 | 华东交通大学 | Water-soluble fatty acid imidazoline quinoline and its preparation method and application |
| CN109679717A (en) * | 2017-10-18 | 2019-04-26 | 中国石油化工股份有限公司 | Compressor lubrication fluid composition and preparation method thereof |
| CN109679717B (en) * | 2017-10-18 | 2022-06-24 | 中国石油化工股份有限公司 | Compressor lubricating oil composition and preparation method thereof |
| CN110845419A (en) * | 2019-11-14 | 2020-02-28 | 安徽金德润滑科技有限公司 | Extreme pressure antiwear agent and road vehicle gear oil containing same |
| CN111423913A (en) * | 2020-04-21 | 2020-07-17 | 中国科学院兰州化学物理研究所 | Plant-based base oil with copper corrosion inhibition function |
| CN114656588A (en) * | 2022-05-06 | 2022-06-24 | 中国科学院兰州化学物理研究所 | Polyion liquid, preparation method and application thereof, lubricating and tackifying additive and supramolecular gel lubricant |
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