CN111676080A - Preparation method of novel efficient soot dispersant - Google Patents
Preparation method of novel efficient soot dispersant Download PDFInfo
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- CN111676080A CN111676080A CN202010582879.0A CN202010582879A CN111676080A CN 111676080 A CN111676080 A CN 111676080A CN 202010582879 A CN202010582879 A CN 202010582879A CN 111676080 A CN111676080 A CN 111676080A
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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
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/46—Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
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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
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/58—Heterocyclic compounds
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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
- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
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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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- 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
- C10M2215/30—Heterocyclic compounds
Abstract
The invention discloses a preparation method of a novel high-efficiency soot dispersing agent, which comprises the following steps: selecting a linear or branched polyacid compound containing two or more carboxyl groups in one molecule; carrying out polymerization reaction on a polybasic acid compound and an amine substance to obtain an oligomer terminated by amine; and (3) carrying out dehydration reaction on the oligomer and polyisobutylene succinic anhydride to obtain a high molecular weight product containing polyimide, amide and/or amino. One molecule of the dispersant prepared by the invention contains a plurality of amide or imide groups with stronger polarity, and each molecule at least contains two PIB non-polar long chains, so that the adsorption capacity of the novel high molecular weight ashless dispersant, the capacity of combining soot and suspended soot are obviously improved; because the existence of mono-substituted polyisobutylene succinimide (a dispersant with only one non-polar long chain PIB in a molecule) is avoided, the corrosion of an oil product prepared by the dispersant on copper is also improved.
Description
Technical Field
The invention relates to the technical field of dispersants, and particularly relates to a preparation method of a novel efficient soot dispersant.
Background
In internal combustion engine oils, the base number of the dispersant is an important factor affecting its soot dispersing properties. Generally, to achieve better soot dispersing properties, the base number of succinimide dispersants tends to be higher, and structures tend to be monosubstituted. This type of dispersant, because it contains more basic nitrogen, has a very good effect of partitioning soot particles and preventing them from aggregating into large particles, and relieves to some extent the thickening of the internal combustion engine oil caused by the increase in soot content.
From the beginning of this century to the present, as emission standards become more stringent, the design of diesel engines has been improved, for example, in order to reduce the emission of nitrogen oxides, many engine manufacturers have adopted the delayed injection technique, so that the insufficient combustion of diesel can reduce the generation of nitrogen oxides to a certain extent, but more soot is generated at the same time, and the soot finally entering a crankcase is also increased obviously; this requires a continuous increase in the soot dispersion capacity of the oil to extend the oil change period.
Therefore, the base number of the dispersant is increased, and the monosubstituted structure is added, so that the dispersion effect of the oil product on soot can be improved to a certain extent. But at the same time, the increase of basic nitrogen and monosubstituted structure in the oil product also leads the corrosion of the oil product to the rubber sealing element to be aggravated, the interaction between the dispersant and the ZDDP is also strengthened, the development of the oxidation resistance and the corrosion resistance of the ZDDP is limited, and one intuitive result is that the corrosion of the oil product to copper is strengthened in an HTCBT test.
Disclosure of Invention
In view of the above problems in the prior art, the present invention provides a method for preparing a novel high efficiency soot dispersant; the prepared dispersant can obtain more excellent dispersing performance through structural recombination, can still realize effective dispersion of soot under the condition of lower addition amount, and simultaneously obviously reduces the corrosion of oil products to copper.
The invention discloses a preparation method of a novel high-efficiency soot dispersing agent, which comprises the following steps:
selecting a linear or branched polyacid compound containing two or more carboxyl groups in one molecule;
carrying out polymerization reaction on the polybasic acid compound and an amine substance to obtain an oligomer terminated by amine;
and (3) carrying out dehydration reaction on the oligomer and polyisobutylene succinic anhydride to obtain a high molecular weight product containing polyimide, amide and/or amino.
As a further improvement of the invention, the reaction formula of the preparation method is as follows:
wherein n is an integer of 1, 2 or 3 …, and R is1Is a linear or branched alkyl or aryl radical, R2Is a straight chain or branched chain alkyl or aromatic group containing amine or no amine.
As a further improvement of the invention, n is 1-5.
As a further refinement of the present invention, the polyacid compound includes, but is not limited to, one or more of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, dodecanedioic acid, hexadecanedioic acid, octadecanedioic acid, docosanedioic acid, phthalic acid, dimer acid, and trimer acid.
As a further improvement of the present invention, the amine-based substance includes, but is not limited to, one or more of aliphatic diamine or polyamine including ethylenediamine, propylenediamine, butylenediamine, pentylenediamine, hexylenediamine, decyldiamine, diethylenetriamine, triethylenetetramine and tetraethylenepentamine, and aromatic diamine or polyamine including phenylenediamine, xylylenediamine, diaminodiphenylmethane and the like.
As a further improvement of the invention, the molar ratio of the polybasic acid compound to the amine substance is 1:1-1:10, the reaction temperature of the polymerization reaction is 100-250 ℃, and the reaction time is 0.5-12 h.
As a further improvement of the invention, the molar ratio of the polybasic acid compound to the amine substance is 1:1-1:3, the reaction temperature of the polymerization reaction is 140-240 ℃, and the reaction time is 1-6 h.
As a further improvement of the invention, the dehydration reaction temperature is 70-250 ℃.
As a further improvement of the invention, the dehydration reaction temperature is 120-230 ℃.
As a further improvement of the invention, the oligomer is a macromolecular intermediate diamine or polyamine with a molecular weight larger than that of diamine or polyamine, and the molecular configuration of the oligomer is linear or reticular.
Compared with the prior art, the invention has the beneficial effects that:
one molecule of the dispersant prepared by the invention contains a plurality of amide or imide groups with stronger polarity, and each molecule at least contains two PIB non-polar long chains, so that the adsorption capacity of the novel high molecular weight ashless dispersant, the capacity of combining soot and suspended soot are obviously improved; because the existence of mono-substituted polyisobutylene succinimide (a dispersant with only one non-polar long chain PIB in a molecule) is avoided, the corrosion of an oil product prepared by the dispersant on copper is also improved.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The invention is described in further detail below:
the invention provides a preparation method of a novel high-efficiency soot dispersant, and the types of raw materials and synthesis conditions required by synthesizing the ashless dispersant are determined. Compared with the traditional high molecular weight ashless dispersant, the dispersant has more excellent soot dispersing capacity, and the unique molecular structure of the dispersant effectively reduces the corrosion of oil products to copper. The dispersion performance of the ashless dispersant is better than that of the traditional high molecular weight polyisobutylene succinimide ashless dispersant even when the addition amount is the same or even lower.
Specifically, the method comprises the following steps:
the invention provides a preparation method of a novel high-efficiency soot dispersing agent, which comprises the following steps:
step 1, selecting a linear or branched polyacid compound containing two or more carboxyl groups in one molecule; wherein the content of the first and second substances,
the polyacid compound has the structural formula:
in the formula, R1Is a linear or branched alkyl or aryl group; including but not limited to oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, dodecanedioic acid, hexadecanedioic acid, octadecanedioic acid, docosanedioic acid, phthalic acid, dimer acid, trimer acid, and the like.
Step 2, carrying out polymerization reaction on a polybasic acid compound and an amine substance to obtain an oligomer terminated by amine; wherein the content of the first and second substances,
the polybasic acid compound (diacid or polybasic acid) and the amine substance (diamine or polyamine) react for a certain time at a certain molar ratio and under a certain temperature condition to obtain oligomers, the oligomers are all terminated by amine by improving the molar weight of the diamine or polyamine, the oligomers are macromolecular intermediate diamine or polyamine with molecular weight obviously larger than that of the diamine or polyamine, and the molecular configuration can be linear or reticular;
the structural formula of the amine substance is as follows:
H2N-R2-NH2
in the formula, R2Amine or polyamine compounds include but are not limited to aliphatic diamines or polyamines such as ethylenediamine, propylenediamine, butylenediamine, pentylenediamine, hexylenediamine, decylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, polyethylenepolyamines, and the like, and also include but are not limited to aromatic diamines or polyamines such as phenylenediamine, xylylenediamine, diaminodiphenylmethane, and the like;
the reaction molar ratio of the dibasic acid or polybasic acid to the diamine or polyamine is 1:1-1:10, preferably 1:1-1: 3; the reaction temperature ranges from 100 ℃ to 250 ℃, preferably from 140 ℃ to 240 ℃. The reaction time is in the range of 0.5-12h, preferably 1-6 h;
the reaction formula of the polybasic acid compound (dibasic acid or polybasic acid) and the amine substance (diamine or polyamine) is as follows:
in the formula, n is an integer of 1, 2, 3 …, preferably n is 1 to 5.
Step 3, carrying out dehydration reaction on the oligomer and polyisobutylene succinic anhydride to obtain a high molecular weight product containing polyimide, amide and/or amino; wherein the content of the first and second substances,
the temperature of the dehydration reaction is 70-250 ℃, preferably 120-230 ℃;
the structural formula of the polyisobutylene succinic anhydride is as follows:
the reaction formula of the dehydration reaction is:
in the formula, n is an integer of 1, 2 and 3 …, preferably n is 1-5; r1Is a linear or branched alkyl or aryl radical, R2Is a straight chain or branched chain alkyl or aromatic group containing amine or no amine.
The above reaction formula shows that:
one molecule of the dispersant prepared by the invention contains a plurality of amide or imide groups with stronger polarity, and each molecule at least contains two PIB non-polar long chains, so that the adsorption capacity of the novel high molecular weight ashless dispersant, the capacity of combining soot and suspended soot are obviously improved; because the existence of mono-substituted polyisobutylene succinimide (a dispersant with only one non-polar long chain PIB in a molecule) is avoided, the corrosion of an oil product prepared by the dispersant on copper is also improved.
The principle of the invention is as follows:
the invention selects a polybasic acid compound to pre-react with amine substances to prepare linear or reticular intermediate diamine or polyamine oligomers of some macromolecules, and then the linear or reticular intermediate diamine or polyamine oligomers react with polyisobutylene succinic anhydride with different molecular weights (molecular weight 300-. Compared with the traditional mono-substituted polyisobutylene succinimide ashless dispersant, the ashless dispersant has obviously improved dispersion performance and simultaneously obviously improves the corrosion to copper.
The comparative experiment shows that the dispersant of the invention still has more excellent dispersing performance than the traditional polyisobutylene succinimide even if the dosage is reduced, can obviously improve the corrosion of oil products to copper, and can be used as a novel dispersant to replace the polyisobutylene succinimide type ashless dispersant in the internal combustion engine oil.
Examples
Example 1:
in a 500ml four-necked glass bottle, 154.8g (1.5mol) of diethylenetriamine and 174.2g (1.0mol) of suberic acid were charged, stirred and heated to 185 ℃ to continue the reaction for 4 hours. During the reaction, a small stream of nitrogen is continuously introduced to carry out the water generated by the amidation reaction. The reaction product contains trace amount of diethylenetriamine and no longer contains suberic acid through gas chromatography detection. The acid value of the product was 0mgKOH/g, and the base value was 480 mgKOH/g.
Example 2:
189.3g (1.0mol) of tetraethylenepentamine and 115.2g (0.5mol) of dodecanedioic acid are added to a 500ml four-neck glass bottle, stirred and heated to 185 ℃ for continuous reaction for 4 h. During the reaction, a small stream of nitrogen is continuously introduced to carry out the water generated by the amidation reaction. The reaction product contained trace amount of tetraethylenepentamine and no dodecanedioic acid. The acid value of the product is 0mgKOH/g, and the base value is 780 mgKOH/g.
Example 3:
adding 2300g (1.0mol) of high-activity polyisobutylene (with the number average molecular weight of 2300 and the alpha olefin content of not less than 85 wt%) into a 5000ml stainless steel high-pressure reaction kettle, introducing nitrogen for protection, stirring and heating to 200 ℃; 176.5g (1.8mol) of molten maleic anhydride are slowly added dropwise via a dropping device over a period of 30 min. After the dropwise addition, slowly raising the temperature in the reaction kettle to 230 ℃, continuously reacting for 4 hours at the temperature, blowing nitrogen into the reaction kettle after the reaction is finished, and blowing unreacted maleic anhydride out of the reaction kettle. The saponification value of the reaction product was found to be 60 mgKOH/g.
Example 4:
243g (0.13mol) of polyisobutylene succinic anhydride obtained in example 3 and 38.1g (0.065mol) of amidated product obtained in example 1 are added into a 1000ml four-mouth glass bottle, 200g of 150N hydrogenated base oil is added, the temperature is raised to 180 ℃ by stirring, the reaction is carried out for 4h, and a small amount of nitrogen is continuously introduced during the reaction to remove oxygen. The product obtained by the reaction is the novel ashless dispersant, the base number of the product is 22mgKOH/g, and the nitrogen content is 1.7 wt%.
Example 5:
243g (0.13mol) of polyisobutylene succinic anhydride obtained in example 3 and 37.2g (0.065mol) of amidated product obtained in example 2 are added into a 1000ml four-mouth glass bottle, 200g of 150N hydrogenated base oil is added, the temperature is raised to 180 ℃ by stirring, the reaction is carried out for 4h, and a small amount of nitrogen is continuously introduced during the reaction to remove oxygen. The product obtained by the reaction is the novel ashless dispersant, the base number of the product is 45mgKOH/g, and the nitrogen content is 1.9 wt%.
Comparative example 1:
243g (0.13mol) of polyisobutylene succinic anhydride obtained in example 2 and 200g of 150N hydrogenated base oil are added into a 1000ml four-mouth glass bottle, the temperature is raised to 100 ℃ by stirring, 24.6g (0.13mol) of tetraethylenepentamine is slowly dropped into the bottle, the temperature is slowly raised to 180 ℃ for reaction for 4 hours, and a small amount of nitrogen is continuously introduced into the bottle during the reaction to remove oxygen. The product obtained by the reaction is the mono-substituted high molecular weight polyisobutylene succinimide dispersant, the base number of the product is 60mgKOH/g, and the nitrogen content is 1.9 wt%.
The final products obtained in example 4, example 5 and comparative example 1 were added to the old oil for engine bench test at a dosage of 0.5 wt% and 1.0 wt%, respectively, and the oil had a soot content of 6.2 wt% by TGA analysis and a kinematic viscosity of 57.65mm at 100 deg.C2And s. And (3) stirring the old oil added with the dispersant for 2 hours at 100 ℃, detecting the kinematic viscosity at 100 ℃ and calculating the viscosity reduction rate, wherein the lower the kinematic viscosity and the higher the reduction rate, the stronger the capability of the added dispersant for preventing the oil product from thickening.
From the above dispersibility evaluation data, it can be seen that the novel ashless dispersants prepared in the examples of the present invention have better inhibitory effects on old oil thickening than the monosubstituted high molecular weight polyisobutylene succinimide at the same dosages as the comparative examples.
The dispersants from example 4, example 5 and comparative example 1 were blended in the same amount (5.0 wt%) in the same fuel starvation to produce diesel oil of 15W/40 viscosity grade and tested according to the HTCBT test (high temperature corrosion bench test) according to ASTM D6594. As shown by the results in the table above, the dispersants prepared in examples 4 and 5 can significantly improve the corrosion of the oil to copper parts under the test conditions, compared to the mono-substituted polyisobutylene succinimide dispersant.
The reason for this was analyzed as follows:
in the invention, the low polymer intermediate polyamine obtained by reacting polyamine with a special structure with polybasic acid is prepared in advance and then reacts with polyisobutylene succinic anhydride, so that the dispersant with a structure obviously different from that of the traditional polyisobutylene succinimide can be obtained. The intermediate polyamine is further aminated to obtain the dispersant, and the polar groups in the molecules are linear or latticed and occupy relatively large space, so that the coating capability of the soot particles is enhanced, and the aggregation of the soot can be more effectively prevented. Meanwhile, due to the double-substituted structure, the corrosion inhibitor can play a role in preventing the corrosion of a polar head on copper in space as same as other double-substituted polyisobutylene succinimide, thereby improving the corrosion of the copper.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method for preparing a novel highly efficient soot dispersant, comprising:
selecting a linear or branched polyacid compound containing two or more carboxyl groups in one molecule;
carrying out polymerization reaction on the polybasic acid compound and an amine substance to obtain an oligomer terminated by amine;
and (3) carrying out dehydration reaction on the oligomer and polyisobutylene succinic anhydride to obtain a high molecular weight product containing polyimide, amide and/or amino.
2. The method of claim 1, wherein the method is according to the formula:
wherein n is an integer of 1, 2 or 3 …, and R is1Is straightChain or branched alkyl or aryl radicals, R2Is a straight chain or branched chain alkyl or aromatic group containing amine or no amine.
3. The method according to claim 2, wherein n is 1 to 5.
4. The method of claim 1, wherein the polyacid compounds include, but are not limited to, one or more of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, dodecanedioic acid, hexadecanedioic acid, octadecanedioic acid, docosanedioic acid, phthalic acid, dimer acid, and trimer acid.
5. The method of claim 1, wherein the amine includes, but is not limited to, one or more of aliphatic diamine or polyamine including ethylenediamine, propylenediamine, butylenediamine, pentylenediamine, hexylenediamine, decyldiamine, diethylenetriamine, triethylenetetramine, and tetraethylenepentamine, and aromatic diamine or polyamine including phenylenediamine, xylylenediamine, diaminodiphenylmethane.
6. The method according to any one of claims 1 to 5, wherein the molar ratio of the polybasic acid compound to the amine is 1:1-1:10, the reaction temperature of the polymerization reaction is 100 ℃ and the reaction time is 0.5-12 h.
7. The method according to claim 6, wherein the molar ratio of the polybasic acid compound to the amine is 1:1-1:3, the polymerization temperature is 140-240 ℃ and the reaction time is 1-6 h.
8. The method according to any one of claims 1 to 4, wherein the dehydration reaction temperature is 70 to 250 ℃.
9. The method according to claim 8, wherein the dehydration reaction temperature is 120-230 ℃.
10. The method according to any one of claims 1 to 4, wherein the oligomer is a macromolecular intermediate diamine or polyamine having a molecular weight greater than that of the diamine or polyamine, and the molecular configuration thereof is linear or network.
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