CN105061223A - High-temperature benzenetriamine antioxidants for lubricating oil and preparation method of high-temperature benzenetriamine antioxidants - Google Patents
High-temperature benzenetriamine antioxidants for lubricating oil and preparation method of high-temperature benzenetriamine antioxidants Download PDFInfo
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- CN105061223A CN105061223A CN201510426390.3A CN201510426390A CN105061223A CN 105061223 A CN105061223 A CN 105061223A CN 201510426390 A CN201510426390 A CN 201510426390A CN 105061223 A CN105061223 A CN 105061223A
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Abstract
The invention provides high-temperature benzenetriamine antioxidants for lubricating oil and a preparation method of the high-temperature benzenetriamine antioxidants. 1, 3, 5-benzenetriol and substituted aniline are taken as raw materials, methylbenzene is taken as a high boiling point solvent, the mixture reacts for 1-3 hours at the temperature ranging from 110 DEG C to 130 DEG C in the atmosphere of inert gas under the action of a catalyst and preferably reacts for 2 hours at the temperature of 120 DEG C, a product is treated, and a target product is obtained. With the adoption of the method, the prepared product has high heat stability, good solubility in various lubricating oil and good antioxidation effect at the high temperature, the service life of the lubricating oil can be greatly prolonged, and the high-temperature benzenetriamine antioxidants have an excellent antioxidation effect in a high-temperature lubricating oil oxidation experiment and has a broad application prospect.
Description
Technical field
The invention belongs to lubricating oil additive technical field, be specifically related to a kind of lubricating oil benzene triamine type high temp antioxidant and preparation method thereof.
Background technology
As everyone knows, the effect of lubricating oil is mainly: 1) reduce friction: add lubricant at attrition surface, coefficient of friction can be made to reduce, thus decrease frictional resistance, save energy consumption.2) reduce wear: lubricant can reduce the abrasion that abrasive wear, surface fatigue, adhesive wear etc. cause between attrition surface.3) cooling effect: lubricant can absorb heat, conducts heat and dispel the heat, thus can reduce the temperature rising that frictional heat causes.4) rust inhibition, 5) transmit power, 6) peace and quiet effect etc.Be subject to, under the effects such as air, water, metal, oxidizing reaction to occur in lubricating oil use procedure, particularly in high-temperature work environment, very fast deterioration by oxidation, loses self function.So antioxidant must be added stop lubricating oil Quick Oxidation, extend the working life of lubricating oil.Antioxidant is the important additives that effectively can extend lubricating oil life cycle and ensure lubricating oil oxidation stability at high temperature.
At present, the high-temperature anti-oxidant of domestic and international various document and patent report is mainly aniline, naphthylamines, phenols, sulfur-bearing compounds etc.Amine is widely studied with its outstanding high-temperature behavior and applies.As United States Patent (USP) 2,891,094 reports and uses alkyl-substituted diphenylamine as antioxidant for lubricant oil, has higher thermally-stabilised, decrease the generation of greasy filth simultaneously compared to pentanoic, therefore by a large amount of in engine oil and industrial lubricant.United States Patent (USP) 5,489,711 report mono-substituted pentanoic and be polymerized to linear oligopolymer under oxide compound exist situation, and polymkeric substance and monomer mix wherein, and this product shows particularly preferred high-temperature oxidation resistance in lubricating oil in esters.European patent Appl.072575A1 reports by N, N ' replacement of-diphenyl-para-phenylene diamine modifies, and substituting group is mainly alkyl or the alkoxy grps such as methyl, ethyl, methoxyl group.This kind antioxidant shows high thermostability and stronger control greasy filth ability in lubricating oil.But all there is defect in various degree in above-mentioned antioxidant, as: there is dispersion problem in amine type polymkeric substance, and greasy filth is serious in lubricating oil.Alkylated diphenylamine and substituted p-phenylenediamine height temp effect still treat further raising.
Summary of the invention
The object of the invention is to overcome prior art defect, provides a kind of lubricating oil benzene triamine type high temp antioxidant and preparation method thereof, such high-temperature anti-oxidant excellent performance, is particularly suitable for adding in various lubricating oil under the high temperature conditions using.
For achieving the above object, the present invention adopts following technical scheme:
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, its with Phloroglucinol monomethyl ether and substituted aniline for raw material, use toluene as high boiling solvent, 120 DEG C of reaction 2h are wherein preferable in 110-130 DEG C of reaction 1-3h(under catalyst action and atmosphere of inert gases), product obtains target product through aftertreatment.
Reaction equation is as follows:
R is alkyl or the alkoxy substituent of hydrogen atom or carbonatoms 1-10, comprises straight chain and branched alkyl substituent;
Or R position is monosubstituted polysubstituted during ortho position, contraposition or position replace.
Concrete, described substituted aniline is ortho position, contraposition or a position replace in monosubstituted or polysubstituted; The substituting group of substituted aniline is alkyl or the alkoxy substituent of hydrogen atom or carbonatoms 1-10, comprises straight chain substituent and branched alkyl substituent.
Described rare gas element is preferably argon gas or nitrogen.
Described catalyzer is the concentrated hydrochloric acid of mass concentration 37.5%, and the mass ratio of concentrated hydrochloric acid and Phloroglucinol monomethyl ether is 1:1.5-3.Optimum proportion is 1:2.
Described Phloroglucinol monomethyl ether and the mol ratio of substituted aniline are 1:3.5-5.Optimum proportion is 1:4.
Described Phloroglucinol monomethyl ether and the mass ratio of toluene are 1:3-8.Optimum proportion is 1:5.
Above-mentioned either method is adopted to prepare the lubricating oil benzene triamine type high temp antioxidant of gained.
Preparation method of the present invention is with substituted aniline; Phloroglucinol monomethyl ether is raw material; under atmosphere of inert gases protection; concentrated hydrochloric acid catalysis; one-step synthesis obtains benzene triamine series product; its oxidation inhibitor being that a kind of thermostability is high, control greasy filth ability is strong, effectively can extending lubricating oil working life, is applicable to various lubricating oil.Synthetic method of the present invention is simple, and aftertreatment is simple and easy to do.Product has very high thermostability, and in various lubricating oil, solvability is good, and at high temperature antioxidant effect is good, greatly can extend the work-ing life of lubricating oil, has outstanding antioxygen performance, have broad application prospects in high temperature grease oxidation test.
Accompanying drawing explanation
Fig. 1 is structure and the nucleus magnetic hydrogen spectrum of embodiment 1 product;
Fig. 2 is that embodiment 1 product compares spectrogram with the thermogravimetric of commercial oxidation inhibitor pentanoic;
Fig. 3 is the rotary oxygen bomb test data spectrogram of embodiment 1 product adding different mass concentration at 150 DEG C in lubricating oil diisooctyl sebacate (DIOS);
Fig. 4 is the rotary oxygen bomb data spectrogram at embodiment 1 product 150 DEG C in lubricating oil tricarboxymethyl propane oleate (Priolube1427), whiteruss (LP), poly-alpha olefins (PAO6), diisooctyl sebacate (DIOS), petrochemical industry diester (Priolube3959) and trimellitate (Priolube1938);
Fig. 5 is high pressure means of differential scanning calorimetry (PDSC) the data spectrogram at embodiment 1 product 210 DEG C in lubricating oil diisooctyl sebacate (DIOS), trimellitate (Priolube1938), petrochemical industry diester (Priolube3959) and tricarboxymethyl propane oleate (Priolube1427);
The rotary oxygen bomb data spectrogram of Fig. 6 embodiment 1 to embodiment 7 product in lubricating oil diisooctyl sebacate.
Embodiment
Do to introduce in detail further to technical scheme of the present invention below in conjunction with embodiment, but protection scope of the present invention is not limited thereto.
embodiment 1
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 1.44ml aniline (15.86mmol) adds in 10ml sealed reaction bottle, nitrogen replacement 3 times, add the dense HCl(mass concentration 37.5% of 0.2ml, lower same) and 3ml toluene, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.17 grams of oyster white needle-like crystals.Products therefrom is carried out a series of characterization test, and result is as follows.
The nucleus magnetic hydrogen spectrum display of Fig. 1:
1hNMR (400MHz, DMSO): δ=798 (s, 3H, 3 secondary amine hydrogen), 6.33-7.23 (m, 18H, Ar-H), 3.36 water peaks, 2.50 deuterium band methyl-sulphoxide base peaks.The structure of the data fit embodiment product 1 of nucleus magnetic hydrogen spectrum is seen from collection of illustrative plates.
Thermogravimetric Data from Fig. 2: the thermosteresis starting temperature of commercial oxidation inhibitor pentanoic (DPA) is 80 DEG C, and embodiment product 1 is about 270 DEG C, and thermosteresis speed maximum temperature is respectively 189 DEG C, 370 DEG C.Compared with conventional commercial high-temperature antioxidant pentanoic (DPA), embodiment 1 product has higher thermostability.
Fig. 3 is the rotary oxygen bomb test data spectrogram of embodiment 1 product adding different mass concentration at 150 DEG C in lubricating oil diisooctyl sebacate (DIOS).When can find to add concentration more than 0.5% diisooctyl sebacate from these data, the oxidation induction period of diisooctyl sebacate does not significantly increase, and cost can be made on the contrary to improve.Consider effect and cost, embodiment 1 product optimum concn in diisooctyl sebacate is 0.5%, and at this moment it is better than the commercial oxidation inhibitor pentanoic (DPA) of homogenous quantities concentration to the effect of oil oxidation prolongation inductive phase.
As can be seen from Figure 4: when adding 0.5% embodiment 1 product for 150 DEG C, several lubricating oil Priolube1427, LP, PAO6, DIOS, Priolube3959, the oxidation induction of Priolube1938 is from 20min, 25min, 43min, 48min, 50min, 391min extend to 73min respectively, 1280min, 1960min, 2230min, 1890min, 2194min.Embodiment 1 product is added on the work-ing life all extending oil product in this several lubricating oil, has outstanding resistance of oxidation, is applicable to being added in various lubricating oil using.
As can be seen from Figure 5: after the commercial oxidation inhibitor DPA that with the addition of homogenous quantities concentration (0.5%) 210 DEG C time in several lubricating oil diisooctyl sebacate (DIOS), trimellitate (Priolube1938), petrochemical industry diester (Priolube3959) and tricarboxymethyl propane oleate (Priolube1427) or embodiment 1 product, oxidation of lubricating oil inductive phase is respectively from 1min, 10.9min, 3.3min, 2.6min extends to 5.3min, 28.5min, 39.5min, 45.6min.Under 210 DEG C of high temperature are described, embodiment 1 product is added on the work-ing life that still effectively can extend oil product in this several lubricating oil, has outstanding high-temperature oxidation resistance.
embodiment 2
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 1.7 grams of open-chain crown ether (15.86mmol) add in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.27 grams of white needle-like crystals.
embodiment 3
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 1.92 grams 2,4-xylidine (15.86mmol) adds in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.46 grams of white needle-like crystals.
embodiment 4
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 2.14 grams 2,4,6-xylidine (15.86mmol) adds in 10ml sealed reaction bottle, nitrogen replacement 3 times, adds dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.4 grams of white solids.
embodiment 5
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 1.95 grams of P-nethoxyaniline (15.86mmol) add in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.28 grams of gray crystals look needle-like crystals.
embodiment 6
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 2.43 grams 3,4-dimethoxyaniline (15.86mmol) adds in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.54 grams of black solids.
embodiment 7
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 2.12 grams of p-ethoxyanilines (15.86mmol) add in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.68 grams of grey black needle-like crystals.
Embodiment 1 product to the rotary oxygen bomb data of embodiment 7 product in diisooctyl sebacate as shown in Figure 6.As seen from Figure 6: when interpolation mass concentration is 0.5%, oxidation of lubricating oil extends to 2230min, 1850min, 1710min, 1620min, 1415min, 720min, 1220min respectively from 48min inductive phase.Illustrate that this series product has outstanding resistance of oxidation in lubricating oil diisooctyl sebacate.
embodiment 8
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 2.87 grams 2,5-diethoxy aniline (15.86mmol) adds in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.83 black solids.
embodiment 9
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 2.5ml adds in 10ml sealed reaction bottle to n-butyl aniline (15.86mmol), nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, freezing 30min, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.28 grams of white needle-like crystals.
embodiment 10
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 2.47ml p-tert-butyl-aniline (15.86mmol) adds in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.6 grams of white solids.
embodiment 11
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 2.81 grams add in 10ml sealed reaction bottle to hexyl aniline (15.86mmol), nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, freezing 30min, products therefrom suction filtration, 10ml methanol wash 3 times, dry, obtain 1.73 grams of white needle-like crystals.
embodiment 12
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 3.5 grams add in 10ml sealed reaction bottle to nonyl aniline (15.86mmol), nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom underpressure distillation, column chromatography for separation (sherwood oil: methylene dichloride=2:1), dry, obtain 2.25 grams of incarnadine oily liquids.
embodiment 13
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 3.69 grams add in 10ml sealed reaction bottle to decyl aniline (15.86mmol), nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom underpressure distillation, column chromatography for separation (sherwood oil: methylene dichloride=2:1), dry, obtain 2.1 grams of incarnadine oily liquids.
embodiment 14
A kind of preparation method of lubricating oil benzene triamine type high temp antioxidant, be specially: get 0.5 gram of Phloroglucinol monomethyl ether (3.96mmol), 3.95 grams to adding alkoxyl aniline in the last of the ten Heavenly stems (15.86mmol) in 10ml sealed reaction bottle, nitrogen replacement 3 times, add dense HCl and the 3ml toluene of 0.2ml, tube sealing, 120 DEG C of reaction 2h.After reaction terminates, be cooled to room temperature, products therefrom underpressure distillation, column chromatography for separation (sherwood oil: methylene dichloride=2:1), dry, obtain 2.3 grams of red oil.
Claims (7)
1. the lubricating oil preparation method of benzene triamine type high temp antioxidant, it is characterized in that, with Phloroglucinol monomethyl ether and substituted aniline for raw material, use toluene as high boiling solvent, in 110-130 DEG C of reaction 1-3h under catalyst action and atmosphere of inert gases, product obtains target product through aftertreatment.
2. the lubricating oil preparation method of benzene triamine type high temp antioxidant as claimed in claim 1, is characterized in that, described substituted aniline is ortho position, contraposition or a position replace in monosubstituted or polysubstituted; The substituting group of substituted aniline is hydrogen atom or carbonatoms at the alkyl of 1-10 or alkoxy substituent, comprises straight chain substituent and branched alkyl substituent.
3. the lubricating oil preparation method of benzene triamine type high temp antioxidant as claimed in claim 1, it is characterized in that, described rare gas element is argon gas or nitrogen.
4. the lubricating oil preparation method of benzene triamine type high temp antioxidant as claimed in claim 1, it is characterized in that, described catalyzer is the concentrated hydrochloric acid of mass concentration 37.5%, and the mass ratio of concentrated hydrochloric acid and Phloroglucinol monomethyl ether is 1:1.5-3.
5. the lubricating oil preparation method of benzene triamine type high temp antioxidant as claimed in claim 1, it is characterized in that, the mol ratio of Phloroglucinol monomethyl ether and substituted aniline is 1:3.5-5.
6. the lubricating oil preparation method of benzene triamine type high temp antioxidant as claimed in claim 1, it is characterized in that, the mass ratio of Phloroglucinol monomethyl ether and toluene is 1:3-8.
7. adopt claim 1 to 6 either method to prepare the lubricating oil benzene triamine type high temp antioxidant of gained.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109517640A (en) * | 2018-11-21 | 2019-03-26 | 烟台索山机械有限公司 | 6-(2- pyridyl group) the application of -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant |
| CN114105783A (en) * | 2020-08-25 | 2022-03-01 | 王兴路 | Anti-aging agent and preparation method thereof |
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| US2882136A (en) * | 1954-08-23 | 1959-04-14 | Eastman Kodak Co | 1, 3, 5-tri(arylamino)benzene and derivatives thereof as stabilizers for petroleum products |
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2015
- 2015-07-20 CN CN201510426390.3A patent/CN105061223A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882136A (en) * | 1954-08-23 | 1959-04-14 | Eastman Kodak Co | 1, 3, 5-tri(arylamino)benzene and derivatives thereof as stabilizers for petroleum products |
Non-Patent Citations (2)
| Title |
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| AGNIESZKA PRON ET AL.: "Phenylene Bridged Boron-Nitrogen Containing Dendrimers", 《ORGANIC LETTERS》 * |
| AMERICAN CHEMICAL SOCIETY: "FIL REG", 《STN ON THE WEB》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109517640A (en) * | 2018-11-21 | 2019-03-26 | 烟台索山机械有限公司 | 6-(2- pyridyl group) the application of -4- p-fluorophenyl -2- aminopyrimidine as lubrication oil antioxidant |
| CN114105783A (en) * | 2020-08-25 | 2022-03-01 | 王兴路 | Anti-aging agent and preparation method thereof |
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Application publication date: 20151118 |