CN102517132A - Method for synthesizing lubricating oil additive from low-molecular weight polyisobutene - Google Patents
Method for synthesizing lubricating oil additive from low-molecular weight polyisobutene Download PDFInfo
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- CN102517132A CN102517132A CN2011104085965A CN201110408596A CN102517132A CN 102517132 A CN102517132 A CN 102517132A CN 2011104085965 A CN2011104085965 A CN 2011104085965A CN 201110408596 A CN201110408596 A CN 201110408596A CN 102517132 A CN102517132 A CN 102517132A
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Abstract
The invention relates to a method for synthesizing a lubricating oil additive from low-molecular weight polyisobutene. The method provided by the invention comprises the following steps of uniformly mixing polyisobutylene, formic acid and a solvent at a room temperature, dropwisely adding a mixture of hydrogen peroxide and a catalyst into the mixture of polyisobutylene, formic acid and the solvent, standing for layering, removing a water layer, washing an oil layer by soft water until the oil layer has a pH value of 7, carrying out reduced pressure distillation to remove the solvents and to obtain epoxy polyisobutylene, wherein an epoxy value is greater than a value of 0.6 to 1; an acid value is less than 1; and a yield is in a range of 90 to 96%, adding calcium carbonate or calcium oxide into a formic acid aqueous solution obtained by the reaction to obtain calcium formate, wherein the calcium formate can be recovered, and carrying out an epoxy polyisobutylene esterification reaction process to obtain an epoxy polyisobutylene-mixed fatty acid ester, wherein an acid value is less than a value of 0.5 to 2; the viscosity at a temperature of 40 DEG C is in a range of 8000 to 12000; the viscosity at a temperature of 100 DEG C is in a range of 350 to 520 DEG C; a viscosity index is in a range of 140 to 180; a flash point is in a range of 230 to 240; and a pour point is in a range of -2 to -10. The method provided by the invention has clean processes, is safe in implementation, is convenient for operation, can realize effective utilization of low concentration hydrogen peroxide and is convenient for large-scale production.
Description
Technical field
The present invention relates to a kind of method from low-molecular-weight high-activity polyisobutene ucon oil additive.
Background technology
Domestic nearest petroleum industry and automotive industry all are in Rapid development stage; The increase of production of lubricating oil is rapid, and when the river rises the boat goes up to the demand of oil dope nature, because the difference of lubricated operating mode; Different requirement has been proposed lubricant: the carbon deposit of two stroke engine oil and smoke evacuation; The carbon deposit of chain oils and wearing and tearing, the shear resistant of multiviscosisty gear oil are stopped up in the carbon deposit and the filtration of rotary compressor oil.For these problems, general base oil and additive can not solve fully.
In recent years, through the Application Research of low-molecular-weight high-activity polyisobutene (HRPIB) is found that HRPIB can improve the lubricity of lubricating oil, reduces formation of carbonly, the reduction equipment energy consumption increases the service life.Low-molecular-weight high-activity polyisobutene is a transparent thick high molecular polymer colourless, nontoxic, no special odor, and wherein the end group double bond content is about 80%, and HRPIB has been widely used.But contain unsaturated link(age) in the polyisobutene molecule, oxidation stability is poor, thereby has limited the use of polyisobutene as lubricant base oil.After low-molecular-weight high-activity polyisobutene carried out modification and functional changing, can make polyisobutene have advantages such as good oxidation-resistance, extreme pressure and antiwear behavior, improve the performance that polyisobutene uses as lubricant base or additive.
Owing to high-activity polyisobutene is the product of newly releasing in recent years, how the process that the user has a understanding and promotes the use of changes into effective consumption with the market potential demand, and this is the problem that high-activity polyisobutene supplier pendulum solves in present urgent need.If this type low-molecular-weight high-activity polyisobutene is converted into the polyisobutene type lubricating oil additive; Not only help the utilization again of resource; Increased added value of product, reduced environmental pollution, this type lubricating oil additive also has good consistency with lubricant base oil simultaneously; Can reduce the influence of the consistency difference that lubricating oil brings in using the additive process, have additive to open up new approach for producing novel lubricating.
Alkene and other unsaturated hydrocarbons contain active intermediate, and these species can generate the useful organic chemicals of difference in functionality after by epoxidation, and very deep meaning is arranged in Synthetic Organic Chemistry.Epoxidizing method is because of the difference of its raw material and catalyzer difference to some extent.More common method has: (1) uses peroxy acid to be oxygenant, is catalyzer with acid or enzyme; (2) use the organic or inorganic peroxy acid to adopt transition metal-catalyzed method as oxygenant; (3) through halohydrin (halohydrines); (4) come (James.Kener Functionlization of oleyl carbonate by epoxidation such as epoxidation with molecular oxygen; Idation of cottonseed oil by aqueous hydrogen peroxide catalysed by liquid inorganic acids such as JAOCS (2007) 84:457-461 and Srikanta Dinda; Bioresourse echnology, 99 (2008): 3737-3744.
The modification of polyisobutene is to introduce some functional group through chemical reaction; Common modification has chlorination, esterification, carboxylation etc.; Generate polyisobutylene butanedioic anhydride like polyisobutene and maleic anhydride reaction; And then carry out amination reaction with TEPA and obtain polyisobutene succinimide, it be a kind of purposes extensively, lubricating oil and gasoline and diesel oil ashless dispersant that usage quantity is maximum.Epoxy compounds is one type of important organic oxygen-containing compound; Has important industrial application value; The epoxidation research of superpolymer has a lot of reports like epoxidized polybutadiene; And reported that for the epoxidised research US 6 448 418 of polyisobutene employing peroxy acid in-situ method carries out epoxidation to polyisobutene, but wherein do not provide the performance and the index of product, and domesticly do not see relevant report as yet.
Summary of the invention
The object of the invention is, a kind of method from low-molecular-weight polyisobutylene ucon oil additive is provided, and this method is with polyisobutene; Formic acid and solvent, mix the back and stir down and heat up, drip hydrogen peroxide and mixture of catalysts in proportion, dropwise and temperature steadily after; System temperature is transferred to temperature of reaction, after reaction finishes with reactant standing demix, branch vibration layer; Oil reservoir is washed till neutrality with soft water, and the pressure reducing and steaming solvent can obtain water white transparency oily thing epoxy polyisobutene; With epoxy polyisobutene and mixing-in fat acid-respons, obtain light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester then.This method catalyst levels is little, clean process, and implementation condition is simple, is convenient to carry out large-scale production.Overcome deficiency of the prior art.
A kind of method from low-molecular-weight polyisobutylene ucon oil additive of the present invention follows these steps to carry out:
A, with polyisobutene, formic acid and solvent are even, under agitation are warming up to 20-50 ℃, dripping concentration is the mixture of 20-30% hydrogen peroxide and phosphoric acid;
B, dropwise and temperature steadily after, system temperature is transferred to temperature of reaction 30-65 ℃, reaction times 3-7 hour;
After c, reaction finish with the reaction mixture sat layering, branch vibration layer, oil reservoir is washed till neutrality with soft water, the pressure reducing and steaming solvent obtains the epoxy polyisobutene of water white transparency oily thing;
D, will react that to add raw materials quality per-cent in the remaining aqueous formic acid in back be quicklime or lime carbonate 5-15%, can obtain calcium formiate, reclaim;
E, mixed fatty acid is heated to temperature 100-130 ℃, again step c epoxy polyisobutene is slowly joined in the lipid acid, reacted 5-8 hour;
F, the decompression of reaction back steam unreacted mixed fatty acid, and can obtain oil dope is light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester.
Step a concentration of hydrogen peroxide is 30%.
The mass ratio of step a polyisobutene, formic acid, solvent is 1:0.25:0.5.
The mass ratio of step a hydrogen peroxide and catalyzer is 1.3:0.005.
The mass ratio of step e epoxy polyisobutene and mixed fatty acid is 1:0.3-1.3.
A kind of method of the present invention from low-molecular-weight polyisobutylene ucon oil additive, the oxirane value 0.6-1 of the epoxy polyisobutene that this method steps c obtains, acid number＜1, yield is 90-96%.
Working concentration is preferably 30% hydrogen peroxide in the reaction process, can realize effective utilization of lower concentration hydrogen peroxide.
Prepare in the method for epoxy polyisobutene at hydrogen peroxide method, select formic acid to cook epoxidizing agent, obviously be superior to acetate and dichloro acetic acid.
Acid number＜0.5～2 of the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester that step f obtains, 8000～12000,100 ℃ of viscosity 350～520 of 40 ℃ of viscosity, viscosity index 140～180, flash-point 230～240, pour point-2～-10.
Method of the present invention, its characteristics are: adopting peroxyformic acid and ydrogen peroxide 50 under the relatively mild condition under catalyst action, making the two keys in the polyisobutene molecule generate the epoxy product; Epoxide and mixed fatty acid carry out the partial esterification reaction under suitable reaction conditions then, with this structure that changes polyisobutene, reach the requirement that improves the lubricating oil use properties.Simultaneously, the remaining aqueous formic acid of reaction just can obtain a kind of new product---calcium formiate through the alkaline purification of routine, thus Atom economy that fully can realization response, and used reaction mass is industry raw material commonly used, makes things convenient for, is easy to get, inexpensive.
Not only can obtain the epoxy polyisobutene and the mixed aliphatic ester of high yield and higher degree through this method; And can get rid of and use the operation unsafe factor of high-strength hydrogen peroxide in suitability for industrialized production, realize the greenization of synthesis technique and the Atom economy of entire reaction.So clean process of the present invention, environmental friendliness need not high-pressure and high-temperature device, and implementation condition is simple, is convenient to carry out the mass-producing continuous production.
Compare with existing processes, the method for preparing epoxy polyisobutene mixed aliphatic ester among the present invention has tangible difference:
1. in reaction process, use 20～30 % hydrogen peroxide, realized effective utilization of lower concentration hydrogen peroxide; Significantly reduce industrial production cost, practiced thrift resource;
2. no matter the epoxy polyisobutene that obtains of this method has reached higher level on product yield and purity;
3. adopt esterification techniques that epoxidised polyisobutene is gone on foot esterification and obtain extreme-pressure anti-wear and oxidation resistant oil dope;
4. the used raw material of this method is the industrial goods commonly used that are easy to get, and all can effectively transform in the reaction, has realized making full use of of reaction raw materials.
Embodiment
Through specific embodiment the present invention is described further below:
Embodiment 1
A, the mixture that will make with extra care 50g polyisobutene, 12.5g formic acid and 25g sherwood oil place three mouthfuls of reaction flasks that have electronic stirring, tap funnel, prolong and are placed on water bath with thermostatic control; Mix under the stirring of back and be warming up to 45 ℃, dripping mass ratio is the hydrogen peroxide of 1.3:0.005 and the mixture of phosphoric acid;
The mixture of b, hydrogen peroxide and phosphoric acid dropwise and temperature steadily after, system temperature is transferred to 55 ℃ of temperature of reaction, reaction times 3;
C, reaction are transferred to standing demix in the separating funnel with reaction mixture after finishing, branch vibration layer, and oil reservoir is washed till neutrality with soft water, and the pressure reducing and steaming solvent obtains the epoxy polyisobutene, and wherein oxirane value 0.85, iodine number 1.3, acid number 0.3, yield can reach 90 %;
Add mass percent 5% quicklime of raw material in d, the remaining aqueous formic acid in reaction back, can obtain calcium formiate, reclaim;
E, mixed fatty acid is heated to 100 ℃ of temperature, step c epoxy polyisobutene is slowly joined in the lipid acid again, reacted 5 hours, the mass ratio of epoxy polyisobutene and mixed fatty acid is 1:0.3;
F, the decompression of reaction back steam unreacted mixed fatty acid, can obtain the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester of oil dope, and yield is 86.8%.
Embodiment 2
A, with the 50g polyisobutene; 12.5g the mixture of formic acid and 25g sherwood oil places three mouthfuls of reaction flasks that have electronic stirring, tap funnel, prolong and is placed on water bath with thermostatic control; Mix under the stirring of back and be warming up to 20 ℃, the dropping mass ratio is that the concentration of 1.3:0.005 is the mixture of 22% hydrogen peroxide and phosphoric acid;
The mixture of b, hydrogen peroxide and phosphoric acid dropwise and temperature steadily after, system temperature is transferred to temperature of reaction, 30 ℃, 4 hours reaction times;
C, reaction are transferred to standing demix in the separating funnel with reaction mixture after finishing, branch vibration layer, and oil reservoir is washed till neutrality with soft water, and the pressure reducing and steaming solvent obtains the epoxy polyisobutene, and wherein oxirane value 0.86, and acid number 0.5, yield are 91.3%;
Add mass percent 6% lime carbonate of raw material in d, the remaining aqueous formic acid in reaction back, can obtain calcium formiate, reclaim;
E, mixed fatty acid is heated to 110 ℃ of temperature, the epoxy polyisobutene is slowly joined in the lipid acid again, reacted 6 hours, the mass ratio of epoxy polyisobutene and mixed fatty acid is 1:0.5;
F, the decompression of reaction back steam unreacted mixed fatty acid, can obtain the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester of oil dope, and yield is 87.2%.。
Embodiment 3
A, with the 50g polyisobutene; 12.5g the mixture of formic acid and 25g sherwood oil places three mouthfuls of reaction flasks that have electronic stirring, tap funnel, prolong and is placed on water bath with thermostatic control; Mix under the stirring of back and be warming up to 45 ℃, the dropping mass ratio is that the concentration of 1.3:0.005 is the mixture of 30% hydrogen peroxide and phosphoric acid;
The mixture of b, hydrogen peroxide and phosphoric acid dropwise and temperature steadily after, system temperature is transferred to 65 ℃ of temperature of reaction, 7 hours reaction times;
C, reaction are transferred to standing demix in the separating funnel with reaction mixture after finishing, branch vibration layer, and oil reservoir is washed till neutrality with soft water, and the pressure reducing and steaming solvent obtains the epoxy polyisobutene, and wherein oxirane value 0.87, and acid number 0.7, yield are 92%;
Add mass percent 15% quicklime of raw material in d, the remaining aqueous formic acid in reaction back, can obtain calcium formiate, reclaim;
E, mixed fatty acid is heated to 120 ℃, epoxidation polyisobutene thing is slowly joined in the lipid acid again, reacted 7 hours, the mass ratio of epoxy polyisobutene and mixed fatty acid is 1:0.8;
F, the decompression of reaction back steam unreacted mixed fatty acid, can obtain the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester of oil dope, and yield is 91%.
Embodiment 4
A, with the 50g polyisobutene, the mixture of 12.5g formic acid and 25g sherwood oil places three mouthfuls of reaction flasks that have electronic stirring, tap funnel, prolong and is placed on water bath with thermostatic control, mixes the back and is warming up to 35 ℃ under stirring; The dropping mass ratio is that the concentration of 1.3:0.005 is the mixture of 25% hydrogen peroxide and phosphoric acid;
The mixture of b, hydrogen peroxide and phosphoric acid dropwise and temperature steadily after, system temperature is transferred to 50 ℃ of temperature of reaction, 3 hours reaction times;
C, reaction are transferred to standing demix in the separating funnel with reaction mixture after finishing, branch vibration layer, and oil reservoir is washed till neutrality with soft water, and the pressure reducing and steaming solvent obtains the epoxy polyisobutene, and wherein oxirane value 0.872, and acid number 0.6, yield are 92.5%;
Add mass percent 8% lime carbonate of raw material in d, the remaining aqueous formic acid in reaction back, can obtain calcium formiate, reclaim;
E, with mixed fatty acid be heated to 130 the degree, again epoxidation polyisobutene thing is slowly joined in the lipid acid, reacted 8 hours, the mass ratio of epoxy polyisobutene and mixed fatty acid is 1:1.0;
F, the decompression of reaction back steam unreacted mixed fatty acid, can obtain the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester of oil dope, and yield is 92.6%.。
Embodiment 5
A, with the 50g polyisobutene; 12.5g the mixture of formic acid and 25g sherwood oil places three mouthfuls of reaction flasks that have electronic stirring, tap funnel, prolong and is placed on water bath with thermostatic control; Mix under the stirring of back and be warming up to 25 ℃, the dropping mass ratio is that the concentration of 1.3:0.005 is the mixture of 28% hydrogen peroxide and phosphoric acid;
The mixture of b, hydrogen peroxide and phosphoric acid dropwise and temperature steadily after, system temperature is transferred to temperature of reaction, 40 ℃, 5 hours reaction times;
C, reaction are transferred to standing demix in the separating funnel with reaction mixture after finishing, branch vibration layer, and oil reservoir is washed till neutrality with soft water, and the pressure reducing and steaming solvent obtains the epoxy polyisobutene, its oxirane value 0.875, acid number 0.6, yield are 93.2%;
Add mass percent 10% quicklime of raw material in d, the remaining aqueous formic acid in reaction back, can obtain calcium formiate, reclaim;
E, mixed fatty acid is heated to 115 ℃, epoxidation polyisobutene thing is slowly joined in the lipid acid again, reacted 5.5 hours, the mass ratio of epoxy polyisobutene and mixed fatty acid is 1:1.2;
F, the decompression of reaction back steam unreacted mixed fatty acid, can obtain the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester of oil dope, and yield is 93%.
Embodiment 6
A, with the 50g polyisobutene; 12.5g the mixture of formic acid and 25g sherwood oil places three mouthfuls of reaction flasks that have electronic stirring, tap funnel, prolong and is placed on water bath with thermostatic control; Mix under the stirring of back and be warming up to 50 ℃, the dropping mass ratio is that the concentration of 1.3:0.005 is the mixture of 30% hydrogen peroxide and phosphoric acid;
The mixture of b, hydrogen peroxide and phosphoric acid dropwise and temperature steadily after, system temperature is transferred to temperature of reaction, 60 ℃, 6 hours reaction times;
C, reaction are transferred to standing demix in the separating funnel with reaction mixture after finishing, branch vibration layer, and oil reservoir is washed till neutrality with soft water, and the pressure reducing and steaming solvent obtains the epoxy polyisobutene, and wherein oxirane value 0.89, and acid number 0.5, yield are 96%;
Add mass percent 13% lime carbonate of raw material in d, the remaining aqueous formic acid in reaction back, can obtain calcium formiate, reclaim;
E, mixed fatty acid is heated to 130 ℃, epoxidation polyisobutene thing is slowly joined in the lipid acid again, reacted 6.5 hours, the mass ratio of epoxy polyisobutene and mixed fatty acid is 1:1.3;
F, the decompression of reaction back steam unreacted mixed fatty acid, can obtain the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester of oil dope, and yield is 95.1%.Key in summary of the invention herein and describe paragraph.
Claims (5)
1. method from low-molecular-weight polyisobutylene ucon oil additive is characterized in that following these steps to carry out:
A, with polyisobutene, formic acid and sherwood oil mix, and under agitation are warming up to 20-50 ℃, dripping concentration is the mixture of 20-30% hydrogen peroxide and phosphoric acid;
B, dropwise and temperature steadily after, system temperature is transferred to temperature of reaction 30-65 ℃, reaction times 3-7 hour;
After c, reaction finish with the reaction mixture sat layering, branch vibration layer, oil reservoir is washed till neutrality with soft water, the pressure reducing and steaming solvent obtains the epoxy polyisobutene of water white transparency oily thing;
D, will react that to add raw materials quality per-cent in the remaining aqueous formic acid in back be quicklime or lime carbonate 5-15%, can obtain calcium formiate, reclaim;
E, mixed fatty acid is heated to temperature 100-130 ℃, again step c epoxy polyisobutene is slowly joined in the lipid acid, reacted 5-8 hour;
F, the decompression of reaction back steam unreacted mixed fatty acid, can obtain the light yellow transparent oily matter epoxy polyisobutene mixed aliphatic ester of oil dope.
2. method according to claim 1, its characterization step a concentration of hydrogen peroxide is 30%.
3. method according to claim 2, the mass ratio that it is characterized in that step a polyisobutene, formic acid, solvent is 1:0.25:0.5.
4. method according to claim 3, the mass ratio that it is characterized in that step a hydrogen peroxide and catalyzer is 1.3:0.005.
5. method according to claim 1, the mass ratio that it is characterized in that step e epoxy polyisobutene and mixed fatty acid is 1:0.3-1.3.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102978011A (en) * | 2012-12-13 | 2013-03-20 | 中国科学院新疆理化技术研究所 | Method for preparing low-pour-point lubricant additive from low-priced cotton seed oil |
| CN103695080A (en) * | 2013-12-13 | 2014-04-02 | 中国科学院新疆理化技术研究所 | Method for modifying lubricating oil additive by using thioacetic acid |
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| JPH0326284B2 (en) * | 1984-05-16 | 1991-04-10 | Hitachi Ltd | |
| US6262310B1 (en) * | 1991-02-26 | 2001-07-17 | Ferro Corporation | Halogen-free, deposit-control fuel additives comprising a hydroxypolyalkene amine, and a process for its production |
| CN101200423A (en) * | 2007-11-13 | 2008-06-18 | 浙江大学 | Epoxy ester wastewater recycling treatment method |
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| US4069242A (en) * | 1969-02-06 | 1978-01-17 | The Dow Chemical Company | Process for preparation of β-hydroxy esters by reaction of organic carboxylic acids and vicinal epoxides |
| JPH0326284B2 (en) * | 1984-05-16 | 1991-04-10 | Hitachi Ltd | |
| US6262310B1 (en) * | 1991-02-26 | 2001-07-17 | Ferro Corporation | Halogen-free, deposit-control fuel additives comprising a hydroxypolyalkene amine, and a process for its production |
| CN101200423A (en) * | 2007-11-13 | 2008-06-18 | 浙江大学 | Epoxy ester wastewater recycling treatment method |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102978011A (en) * | 2012-12-13 | 2013-03-20 | 中国科学院新疆理化技术研究所 | Method for preparing low-pour-point lubricant additive from low-priced cotton seed oil |
| CN103695080A (en) * | 2013-12-13 | 2014-04-02 | 中国科学院新疆理化技术研究所 | Method for modifying lubricating oil additive by using thioacetic acid |
| CN103695080B (en) * | 2013-12-13 | 2015-02-04 | 中国科学院新疆理化技术研究所 | Method for modifying lubricating oil additive by using thioacetic acid |
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Application publication date: 20120627 |