CN1078241C - Antioxidizing disperser of butanediimide for lubricating oil and its preparing process - Google Patents
Antioxidizing disperser of butanediimide for lubricating oil and its preparing process Download PDFInfo
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- CN1078241C CN1078241C CN98117281A CN98117281A CN1078241C CN 1078241 C CN1078241 C CN 1078241C CN 98117281 A CN98117281 A CN 98117281A CN 98117281 A CN98117281 A CN 98117281A CN 1078241 C CN1078241 C CN 1078241C
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- polyisobutene
- succimide
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Abstract
The present invention relates to an oxygen resistance succinimide lubricating oil dispersing agent and preparation thereof, and the chemical formula of the oxygen resistance succinimide lubricating oil dispersing agent is disclosed in detail in the attached figure. The dispersing agent has the characteristics that the oxygen resistance succinimide lubricating oil dispersing agent is prepared by a method that low-carbon acid ester containing screen phenol reacts with polyisobutylene succinimide when an acid catalyst or a base catalyst exists at the temperature of 80 to 200DEG C. The dispersing agent has good decentrality to lubricating oil, and also has good high temperature anti-oxidation performance.
Description
The present invention relates to nitrogen containing polymer compound lubricating oil additive and preparation thereof, specifically a kind of succimide dispersion agent and preparation thereof that is used for lubricating oil with antioxidant property.
China is a country that the territory is vast, and the engine operating temperature scope is very wide.Under the condition of stopping in the winter time to stop out, the temperature in the gasoline crankcase is very low, and fuel hydrocarbon and wet steam are difficult for discharging from lubricating oil, cause engine to produce a large amount of greasy filth, influence normal working of engine.Under the situation of driving continuously summer, engine temperature is very high, the easy oxidation of I. C. engine oil, and viscosity increases, and causes carbon deposit and paint film increase on the piston.For this reason, require I. C. engine oil that good low temperature greasy filth dispersing property should be arranged, excellent high temperature oxidation resistance is arranged again.
Polyisobutene succinimide is a kind of very effective sludge dispersant, accounts for 40～50% of whole additive total amounts usually in I. C. engine oil.But the oxidation stability of this dispersion agent and heat-resistant quality are all relatively poor.In order to satisfy the service requirements of I. C. engine oil, exploitation have concurrently other function particularly the succimide dispersion agent of antioxidant property have very important significance.US 4; 973,412 disclose a kind of multifunctional additive for lubricating oil, and its preparation method is: earlier with the partially acylated succimide of organic dibasic acid coupling; use the unsaturated fatty acids acid treatment again, react promptly with nitroso-group Ursol D more at last with antioxidant property.This additive improved the antioxidant property of succimide, but its preparation technology's more complicated.In order to improve dispersed and to reduce nitrogen content; US 5; 182; 038 has reported that a kind of succimide dispersion agent that utilizes nonyl phenol coupling amide group to generate is to pass through mannich reaction coupling succimide by phenol, dihydroxyphenyl propane, Resorcinol, single nonyl phenol and 2-Naphthol, is prepared from oxyacetic acid acidylate part polyethylene polyamine again.This additive has improved dispersed and to the adaptability of rubber seal, has not improved the oxidation stability problem but mention.
The object of the present invention is to provide a kind of succimide dispersion agent different with the prior art structure, that have antioxidant property.
Another object of the present invention is to provide a kind of preparation technology preparation method of the fairly simple succimide dispersion agent with antioxidant property.
Antioxidative succinimide dispersion agent provided by the invention is the compound with following structure:
R wherein
1For number-average molecular weight is 500～5000 polyisobutene, m is 0～6 integer; The structure of A is:
R wherein
2Be C
1～C
7Alkylidene group, t-Bu is the tertiary butyl; The structure of Y is:
R wherein
1' for number-average molecular weight 500～5000 polyisobutene.
Constitute by three groups on the dispersion agent structure provided by the invention:
(a) allyl butyrate diacyl group can be a mono alkenyl succinyl group, also can be diene base succinyl group.Thiazolinyl wherein, i.e. R in the said structure formula
1And R
1' be polyisobutene, number-average molecular weight can be 500～5000, and is better 500～3500, preferably 800～2300.R
1And R
1' molecular weight can be the same or different.
(b) contain the low carbonic acyl radical group of shielding phenol, i.e. A in the said structure formula.R wherein
2Can be C
1～C
7Alkylidene group, preferred C
2～C
5Alkylidene group, as ethylidene, propylidene, isobutylidene, pentylidene etc." A " group continuous with different secondary amino groups can be identical, also can be different.
(c) polyamines group.Polyamines shown in the said structure formula has two kinds of situations, first kind is that m is 0 situation in the structural formula, at this moment said polyamines is a quadrol, two primary aminos are arranged in its structure, there is not secondary amino group, have only a kind ofly with group (a) and combination (b), promptly a primary amino links to each other with group (a), and another primary amino links to each other with group (b).Second kind of situation be except that m be situation 0, promptly said polyamines can be diethylenetriamine, triethylene tetramine, tetraethylene pentamine, five ethene hexamines, six ethene, seven amine etc.Contain two primary aminos and several secondary amino groups in this class polyamines structure, then at least one primary amino will link to each other with group (a), another primary amino and/or at least one secondary amino group link to each other with group (b), when having only a primary amino and group (a) when linking to each other, products obtained therefrom is to contain the mono alkenyl succimide that shields phenol; When linking to each other, products obtained therefrom is to contain the diene base succimide that shields phenol as two primary aminos and group (a).M is 0～6 integer in the structural formula, preferably 2～5 integer.
Dispersion agent provided by the invention prepares as follows: low-carbon ester is mixed with succimide, in the presence of the acid of catalytic amount or alkaline catalysts, in 80～200 ℃ of reactions 1～10 hour, separated product, low-carbon ester has structure shown in the formula (I), succimide have formula (II) or one of (III) shown in structure:
R wherein
1And R
1' be the polyisobutene of identical or different number-average molecular weight 500～5000, R
2Be C
1～C
7Alkylidene group, R
3Be C
1～C
3Alkyl, m is 0～6 integer, n is 1～6 integer.
Exactly, dispersion agent provided by the invention can prepare as follows: will contain the low-carbon ester that shields phenol and mix with the allyl butyrate imide, at consumption is reactant gross weight 0.3～10%, under preferred 1～6% the acid or the existence of alkaline catalysts, in 80～200 ℃, better be 100～160 ℃, preferably reacted under 120～150 ℃ the temperature 1～10 hour, preferred 2～8 hours, get final product by underpressure distillation and/or filtering mode separated product.When temperature of reaction is low, together can be slightly long during reaction, when temperature of reaction was higher, the reaction times can be shorter, but when temperature of reaction surpassed 200 ℃, product darkened.The ratio of mixture of said low-carbon ester and succimide can be decided on the number of the N atom that links to each other with H in the succimide, suppose that it is P, then ratio of mixture can be 1～P: 1, be that the H that links to each other with nitrogen-atoms in the succimide can partly be replaced by low-carbon ester, also can be all replaced by low-carbon ester.In order to make reaction more even, can in reactant, add thinning oil, under nitrogen protection, carry out simultaneously, to avoid side reaction.Also can in reactant, add aromatic hydrocarbon solvent in addition,, under reflux temperature, react and get final product as toluene, dimethylbenzene, ethylbenzene etc.Have low-carbon alcohol such as methyl alcohol or ethanol in the reaction and produce, can discharge at any time by exhaust duct.
The said low-carbon ester that shields phenol that contains can be C
2～C
8Low-carbon ester, preferred C
3～C
6Low-carbon ester as propionic ester, isobutyrate or valerate, that is to say the R shown in the structural formula (I)
2Be C
1～C
7Alkylidene group, preferred C
2～C
5Alkylidene group.Said ester group can be methyl esters, ethyl ester, propyl ester etc., preferred methyl esters and ethyl ester, i.e. R
3Be C
1～C
3Alkyl, preferred C
1～C
2Alkyl.
Said allyl butyrate imide can be the polyisobutene mono butonediimide, shown in structural formula (II), also can be the two succimides of polyisobutene, shown in structural formula (III), they are traditional ashless dispersants, its preparation method has been as well known to those skilled in the art, generally is earlier polyisobutene and maleic anhydride to be reacted, and products therefrom can make with the polyamines reaction again.If obtain mono butonediimide, then the mol ratio of thiazolinyl maleic anhydride and polyamines is 1: 1; If obtain two mono butonediimides, then the mol ratio of thiazolinyl maleic anhydride and polyamines is 2: 1.Wherein, polyisobutene is R
1And R
1' number-average molecular weight can be 500～5000, better be 500～3500, preferably 800～2300.R
1And R
1' molecular weight can be the same or different.The polyamines that can be used to prepare compound shown in the structural formula (II) is H
2N (CH
2CH
2NH)
M+1H, m is 0～6 integer, is preferably 2～5 integer.The polyamines that can be used to prepare compound shown in the structural formula (III) is H
2N (CH
2CH
2NH)
nCH
2CH
2NH
2, n is 1～6 integer, is preferably 2～5 integer.
Said acid or alkaline catalysts can be organic acids, as phosphonic acids, Phenylsulfonic acid etc., also can be mineral acids, and example hydrochloric acid, acidic resins etc. can also be mineral alkalis, as sodium hydroxide, basic resin etc.Wherein the consumption of resin can determine that for example, acidity is more weak then can to increase consumption according to its acidity or alkaline power, otherwise then consumption is less.
Antioxidative succinimide lubricating oil dispersant provided by the invention is owing to introduce new antioxidant group in the succimide structure, compare with diene base succimide dispersion agent T154 with mono alkenyl succimide dispersion agent T151, its antioxygen property and detergent-dispersant performance can all have clear improvement.For example, the T151 oxide thin layer test-induced phase is 50 minutes, and sample of the present invention can reach 65 minutes; Thermogravimetric analysis test (TGA) temperature of initial decomposition of T154 is 179.5 ℃, differential thermal analysis test (DSC) temperature of initial decomposition is 185.8 ℃, and sample of the present invention reaches as high as 198.5 ℃ and 198.1 ℃ respectively, illustrates that the heat-resistant quality of sample of the present invention and thermal oxidation stability all have improvement.And for example, T154 coking plate test board face is rated 13.5, and sample of the present invention can reach 14.5; T154 spot value in spot test is 60, and sample of the present invention can reach 66, illustrates that the detergent-dispersant performance of additive provided by the invention can also have clear improvement.
The preparation method of antioxidative succinimide lubricating oil dispersant provided by the invention is more simpler than the preparation of the succimide that has antioxidant property in the prior art, US4 for example, 973,412 needed for three steps just can finish, and preparation method provided by the invention only needs a step to finish.
The invention will be further described below by embodiment.
Example 1～3 is the preparation of allyl butyrate imide.Example 1
Be equipped with in the there-necked flask of agitator and thermometer at 1L, add 250g (0.19mole) polyisobutenyl succinic anhydride (Lanzhou oil-refining chemical company product, soap valency 80mg KOH/g, polyisobutene Mn=1300) and 250g 150SN neutral oil (Dalian Petrochemical Industry Company's product), behind the nitrogen purging air, be warming up to 130 ℃, drip (the Japanese import packing of 41.8g (0.18mole) five ethene hexamines, Shanghai reagent company supply station) kept 1.5 hours, be cooled to 110 ℃, add 5.4g diatomite (Changbai mountain, Jilin chemical plant product), stir the back filtered while hot, obtain mono alkenyl succimide enriched material, concentration is 54m%.Example 2
Be equipped with in the there-necked flask of agitator and thermometer at 1L, add 250g (0.227mole, soap valency 99.2mgKOH/g, polyisobutene Mn=1000) polyisobutenyl succinic anhydride and 250g 150SN neutral oil, behind the nitrogen purging air, be warming up to 130 ℃, drip 16.6g (0.114mole) triethylene tetramine, be warming up to 150 ℃ again, kept 2.5 hours, the water of generation is removed in nitrogen flushing simultaneously, is cooled to 110 ℃, add 5g diatomite, stir the back filtered while hot, obtain diene base succimide enriched material, concentration is 51m%.Example 3
Be equipped with in the there-necked flask of agitator and thermometer at 1L, add 250g (0.10mole) polyisobutenyl succinic anhydride (soap valency 40mg KOH/g, polyisobutene Mn=2300) and 250g 150SN neutral oil, behind the nitrogen purging air, be warming up to 140 ℃, drip (the Japanese import packing of 18.5g (0.10mole) tetraethylene pentamine, Shanghai reagent company supply station) kept 5 hours, be cooled to 110 ℃, add 5g diatomite, stir the back filtered while hot, obtain mono alkenyl succimide enriched material, concentration is 51m%.
Example 4～7 is the preparation of antioxidative succinimide.Example 4
The mono alkenyl succimide enriched material 329g (0.11mole) that gets example 1 preparation joins in the there-necked flask that agitator and thermometer are housed; add 96g (0.33mol) (3 again; 5-di-t-butyl-4 hydroxy phenyl) methyl propionate (Beijing Chemical Factory No. 3's product) and 4g acidic resins (Rohm.Haas company product; Aberlyst 36) under nitrogen protection; be warming up to 140 ℃; kept 4 hours, the methyl alcohol of generation is removed in nitrogen flushing simultaneously.Be cooled to 110 ℃, add the 2.5g super-cell, stir the back filtered while hot, obtain containing the succimide sample of shield phenol type, nitrogen content 2.0m%.Example 5
The diene base succimide enriched material 498g (0.11mole) that gets example 2 preparations joins in the there-necked flask that agitator and thermometer are housed, add 33.2g (0.11mol) (3 again, 5-di-t-butyl-4 hydroxy phenyl) ethyl propionate (Beijing Chemical Factory No. 3's product) and 5g caustic soda and 500g toluene, reaction is 4 hours under reflux temperature, tell 1.7ml ethanol, reclaim toluene, residual toluene is removed in underpressure distillation, add the 5g super-cell, stir the back filtered while hot, obtain containing the succimide sample of shield phenol type, nitrogen content 1.0m%.Example 6
The diene base succimide enriched material 498g (0.11mole) that gets example 2 preparations joins in the there-necked flask that agitator and thermometer are housed; add 69g (0.22mol) (3 again; 5-di-t-butyl-4 hydroxy phenyl) methyl valerate (Beijing Chemical Factory No. 3's product) and 10g acidic resins (Rohm.Haas company product; Aberlyst 15); under nitrogen protection, be warming up to 150 ℃, kept 3 hours; the methyl alcohol of generation is removed in nitrogen flushing simultaneously.Be cooled to 110 ℃, add the 2.5g super-cell, stir the back filtered while hot, obtain containing the succimide sample of shield phenol type, nitrogen content 1.0m%.Example 7
The mono alkenyl succimide enriched material 554g (0.11mole) that gets example 3 preparations joins in the there-necked flask that agitator and thermometer are housed; add 33.2g (0.11mol) (3 again; 5-di-t-butyl-4 hydroxy phenyl) methyl isobutyrate (Beijing Chemical Factory No. 3's product) and 6g tosic acid; under nitrogen protection; be warming up to 130 ℃; kept 5 hours, the methyl alcohol of generation is removed in nitrogen flushing simultaneously.Be cooled to 110 ℃, add the 2.5g super-cell, stir the back filtered while hot, obtain containing the succimide sample of shield phenol type, nitrogen content 1.1m%.Example 8
This example be oxide thin layer test (TFOUT, ASTMD4742)
The chemical environment in oxide thin layer test simulation petrol engine when running, in the presence of 160 ℃ and special catalyst, the pure oxygen catalytic oxidation I. C. engine oil of usefulness certain pressure, to estimate its antioxidant property inductive phase, inductive phase is long more, illustrates that oxidation susceptibility is good more, the results are shown in Table 1.In contrast, the test-results one with commercially available mono butonediimide additive T151A is listed in the table 1.
Table 1
Example 9
| Sequence number | Sample | Inductive phase, minute |
| 1 | Example 4 | 60 |
| 2 | Example 5 | 65 |
| 3 | T151A | 50 |
This example is thermogravimetric analysis (TGA) and differential thermal analysis (DSC) test.
Thermogravimetric analysis condition: nitrogen flow rate 140ml/min, 10 ℃/min of heat-up rate, the heavy 10mg of sample;
The differential thermal analysis condition: oxygen gas flow rate 50ml/min, 5 ℃/min of heat-up rate, 5 ℃/min of heat-up rate, sample weighs 2～5mg.
Analytical results sees Table 2, in contrast, the test-results one of commercially available couple of succimide additive T154 is listed in the table 2.As can be seen from Table 2, sample of the present invention has heat-resistant quality preferably and thermal oxidation stability, and its TGA temperature of initial decomposition and DSC temperature of initial decomposition are all than T154 height.
Table 2
Example 10
| Sequence number | Sample | The TGA temperature of initial decomposition | The DSC temperature of initial decomposition |
| 1 | Example 6 | 198.5 | 198.1 |
| 2 | Example 7 | 195.1 | 194.5 |
| 3 | T154 | 179.5 | 185.8 |
This example is coking plate test (SH/T 0300-92).
The test of coking plate is the analogy method of evaluation I. C. engine oil thermal oxidation stability and detergent-dispersant performance.The settling proterties is estimated detergency on the heavy and plate face with Jiao of generating on the aluminium sheet.Jiao Chongyue is big, and the grading of plate face is low more, and its high temperature detergent-dispersant performance is poor more.
Coking plate test conditions: formation testing amount 260g, motor rotary speed 1000rpm, 300 ℃ of aluminium sheet temperature, 100 ℃ of formation testing temperature are spattered the 15 seconds time of oil, storing time 45 seconds, test period 1 hour, test-results sees Table 3.
As can be seen from Table 3, sample comparison provided by the invention is better than the high temperature detergent-dispersant performance of sample T154.
Table 3
| Sequence number | Sample | Burnt heavy, mg | The grading of plate face |
| 1 | Example 5 | 18.7 | 14.0 |
| 2 | Example 7 | 26.8 | 14.5 |
| 3 | T154 | 30.7 | 13.5 |
Annotate: totally 15 grades of plate face gradings, 0 grade is the poorest, and 15 grades are best.Example 11
This example is spot test
The spot genealogy of law is with after carbon black ointment (or engine sludge) and the dispersant, disperse through high-speed stirring and sonic oscillation, in 50 ℃ of baking ovens, left standstill 18 hours then, drop in after the taking-up on the filter paper, the oil droplet amount is controlled at 0.02～0.025g, filter paper is placed in 50 ℃ of baking ovens left standstill 2 hours, take out and measure diffusion circle diameter (d) and scraper ring diameter (D), its ratio r=d/D * 100 are as the index of weighing dispersive ability, and the r value is big more, and dispersiveness is good more.
Table 4 has been listed the spot test result of sample provided by the invention and T154.
Table 4
| Numbering | Sample | Spot (r) |
| 1 | Example 5 | 64 |
| 2 | Example 6 | 65 |
| 3 | Example 7 | 64 |
| 4 | Example 8 | 65 |
| 5 | T154 | 60 |
Claims (13)
1. an antioxidative succinimide lubricating oil dispersant is characterized in that, it is the compound with following structure:
R wherein
1For number-average molecular weight is 500～5000 polyisobutene, m is 0～6 integer; The structure of A is:
R wherein
2Be C
1～C
7Alkylidene group, t-Bu is the tertiary butyl; The structure of Y is:
R wherein
1' for number-average molecular weight 500～5000 polyisobutene.
2. according to the described dispersion agent of claim 1, it is characterized in that R
1And R
1' for number-average molecular weight 500～3500 polyisobutene.
3. according to claim 1 or 2 described dispersion agents, it is characterized in that R
1And R
1' for number-average molecular weight 800～2300 polyisobutene.
4. according to the described dispersion agent of claim 1, it is characterized in that m is 2～5 integer.
5. according to the described dispersion agent of claim 1, it is characterized in that R
2Be C
2～C
5Alkylidene group.
6. the preparation method of the described antioxidative succinimide lubricating oil dispersant of claim 1, it is characterized in that be with low-carbon ester and succimide according to 1～P: 1 mixed in molar ratio, in the presence of the acid of catalytic amount or alkaline catalysts, in 80～200 ℃ of reactions 1～10 hour, separated product, wherein P is the number of the N atom that links to each other with H in the succimide, and low-carbon ester has structure shown in the formula (I), succimide have formula (II) or one of (III) shown in structure:
R wherein
1And R
1' be the polyisobutene of identical or different number-average molecular weight 500～5000, R
2Be C
1～C
7Alkylidene group, R
3Be C
1～C
3Alkyl, m is 0～6 integer, n is 1～6 integer.
7. according to the described preparation method of claim 6, it is characterized in that R
1And R
1' be 500～3500 polyisobutene.
8. according to claim 6 or 7 described preparation methods, it is characterized in that R
1And R
1' be 800～2300 polyisobutene.
9. according to the described preparation method of claim 6, it is characterized in that R
2Be C
2～C
5Alkylidene group.
10. according to the described preparation method of claim 6, it is characterized in that m and n are 2～5 integer.
11., it is characterized in that said catalyzer is selected from one of phosphonic acids, Phenylsulfonic acid, hydrochloric acid, acidic resins, sodium hydroxide, basic resin according to the described preparation method of claim 6.
12., it is characterized in that said catalyst levels is 0.3～10% of a reactant gross weight according to claim 6 or 11 described preparation methods.
13. according to the described preparation method of claim 6, it is characterized in that temperature of reaction is 100～160 ℃, the reaction times is 2～8 hours.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98117281A CN1078241C (en) | 1998-08-14 | 1998-08-14 | Antioxidizing disperser of butanediimide for lubricating oil and its preparing process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98117281A CN1078241C (en) | 1998-08-14 | 1998-08-14 | Antioxidizing disperser of butanediimide for lubricating oil and its preparing process |
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|---|---|
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| CN1078241C true CN1078241C (en) | 2002-01-23 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100344739C (en) * | 2004-11-30 | 2007-10-24 | 中国石油化工股份有限公司 | Lubricating oil additive composition |
| CN101709242B (en) * | 2009-11-11 | 2012-07-04 | 济南开发区星火科学技术研究院 | Lubricant dispersant |
| CN105272892B (en) * | 2014-06-05 | 2019-01-29 | 中国石油化工股份有限公司 | A kind of shielding phenolic compounds, its manufacturing method and its application as antioxidant |
| CN106635255A (en) * | 2016-12-13 | 2017-05-10 | 中国科学院宁波材料技术与工程研究所 | Bio-based oil product dispersant as well as preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4973412A (en) * | 1990-05-07 | 1990-11-27 | Texaco Inc. | Multifunctional lubricant additive with Viton seal capability |
| US5182038A (en) * | 1991-04-24 | 1993-01-26 | Texaco, Inc. | Mannich base phenol coupled mono and/or bis-succinimide lubricating oil additives |
-
1998
- 1998-08-14 CN CN98117281A patent/CN1078241C/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4973412A (en) * | 1990-05-07 | 1990-11-27 | Texaco Inc. | Multifunctional lubricant additive with Viton seal capability |
| US5182038A (en) * | 1991-04-24 | 1993-01-26 | Texaco, Inc. | Mannich base phenol coupled mono and/or bis-succinimide lubricating oil additives |
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