CN109810744B - Method for preparing biological lubricating oil by catalysis of acidic polymeric ionic liquid - Google Patents
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Abstract
The application discloses a method for preparing biological lubricating oil by catalyzing acidic polymeric ionic liquid, and belongs to the field of preparation of biological lubricating oil. The invention takes acidic polymerization ionic liquid as a catalyst for reaction, catalyzes epoxy methyl ester to react with short-chain alcohol for 10 to 20 hours at the temperature of between 60 and 80 ℃ to obtain reaction liquid, the reaction liquid is cooled to room temperature, gravity sedimentation is carried out, and the product is layered with the acidic polymerization ionic liquid. The method has the advantages of wide reaction raw materials, relatively mild reaction conditions, simple and convenient operation, recyclable acidity and high catalyst activity; the synthesis is convenient.
Description
Technical Field
The invention relates to a method for catalyzing an epoxy ring opening isomerization reaction by acidic polymeric ionic liquid, in particular to a method for preparing biological lubricating oil by acidic polymeric ionic liquid catalysis.
Background
Biodiesel is mainly composed of a mixture of Fatty Acid Methyl Esters (FAMEs), the molecular structure of the fatty acid methyl ester has epoxy bonds with unstable chemical properties through epoxidation reaction, and the epoxy bonds can react with various substances due to the strong tension of the epoxy groups, for example, hydrolysis reaction can occur under acidic conditions, and the epoxy bonds can polymerize with metal oxides to cause explosion, so that the epoxy biodiesel needs to be chemically modified. The addition reaction of the ring opening of the epoxy bond is a reasonable route for preparing the biological lubricating oil by the biological diesel oil. The lubricating oil base oil is synthesized by chemically modifying the biodiesel, so that the additional value of the biodiesel can be improved, and the market competitiveness of the biodiesel can be improved. The most studied is the use of organic alcohols to bond epoxy groups.
In the reaction of generating the biological lubricating oil by ring opening of the epoxy fatty acid methyl ester, the catalyst plays an important role, and has influence on the conversion rate of the epoxy fatty acid methyl ester and the yield of the biological lubricating oil. In addition, the problem of catalyst recovery is also a problem in industrial production that the disposal of the catalyst at will causes great damage to the ecological environment. Green catalysts are of increasing interest in the form of current catalyst development, including: nanoparticle catalysts, ionic liquid catalysts, sandwich catalysts, enzyme or biomimetic catalysts, phase transfer catalysts, and the like. The ionic liquid catalyst is more and more paid attention by researchers because of the advantages of easy chemical stability, good thermal stability and the like, but the ionic liquid is difficult to recover, and the wide application of the ionic liquid catalyst is hindered due to the difficulty in separation. Research on the ionic liquid polymerization which can maintain the high catalytic activity and is convenient to recover is an important direction in the future catalyst research.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for preparing biological lubricating oil by catalyzing acidic polymeric ionic liquid so as to overcome the defects in the known technology.
In order to achieve the purpose, the method for preparing the biological lubricating oil by the catalysis of the acidic polymeric ionic liquid provided by the invention comprises the following steps:
A) taking acidic polymerization ionic liquid as a catalyst for reaction, catalyzing epoxy methyl ester to react with organic alcohol for 10-20 hours at the temperature of 60-80 ℃;
the polymerized monomer of the acidic polymerized ionic liquid can be one of vinyl, allyl or alkene butyl imidazole ionic liquids.
The structural formula of the acidic ionic liquid monomer is shown as
Wherein R is-CH ═ CH2、-CH2-CH＝CH2or-CH2-CH2-CH＝CH2
The reactants are epoxy methyl ester and organic alcohol, wherein the molar ratio of the epoxy methyl ester to the organic alcohol is 1:1 to 1: 6;
the mass ratio of the acidic polymeric ionic liquid to the epoxy methyl ester is 1:4 to 1: 60.
B) And D, cooling the reaction liquid prepared in the step A to room temperature, performing gravity settling, layering the product and the acidic polymeric ionic liquid, and decompressing the upper layer liquid to remove unreacted organic alcohol to obtain the product.
Wherein the acidic polymeric ionic liquid separated in the step B is repeatedly used for reaction.
Wherein, the raw material in the step A is the epoxy methyl ester prepared by the ester exchange epoxidation of vegetable oil; the alcohol is one or more of methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, pentanol and octanol.
Compared with the background technology, the invention achieves the technical progress that:
the invention innovatively provides that B acid ionic liquid polymers with different carbon chain lengths are used for catalyzing the ring opening of epoxy methyl ester to prepare the biological lubricating oil. The ionic liquid is formed by polymerizing acid groups with adjustable carbon chain length, the polymerization degree is controllable and adjustable, and the catalytic reaction in a multiphase system is efficiently realized in a reactor; thus, the acidity and surface activity thereof can be utilized to promote the ring-opening reaction to proceed continuously. The catalyst can be used as a catalyst for synthesizing biological lubricating oil to perform an epoxy ring-opening isomerization etherification reaction process, and the acidic ionic liquid polymer has great application potential in the field of biological lubricating oil production, thereby laying a foundation for promoting the domestic popularization of degradable lubricating oil. The method has the following specific advantages:
1. the reaction raw materials are wide and are derived products of vegetable oil, waste cooking oil and the like, namely epoxidized fatty acid methyl ester.
2. The reaction condition is relatively mild, and the operation is simple and convenient.
3. The reaction product phase and the catalyst phase are immiscible and can be automatically layered and easily separated.
4. The catalyst is acidic polymerization ionic liquid, has controllable and adjustable structure, stable performance, no loss of acidity, recycling and high catalyst activity; the synthesis is convenient, and the atom is economic and good.
5. The problems of difficult liquid separation and weak catalytic activity of the common catalyst in the background art are solved.
6. The preparation process has no wastewater discharge, and redundant reactants can be recycled for multiple times, thus belonging to an environment-friendly process route.
Detailed Description
The method for preparing the biological lubricating oil by the catalysis of the acidic polymeric ionic liquid, provided by the invention, is used for catalyzing the cycloisomerization reaction of epoxy methyl ester, and provides an environment-friendly process route for the preparation of the biological lubricating oil.
The acidic polymeric ionic liquid used in the invention is sulfonic group functionalized alkyl polyvinyl imidazole sulfonic acid, and the synthesis process is shown as follows, wherein the polymeric monomer can be vinyl, allyl or alkene butyl imidazole ionic liquid. The polymerization degree is controllable and adjustable.
The acid polymerization vinyl ionic liquid catalyst comprises the following specific synthesis steps:
the acidic polymerized vinyl ionic liquid used in the invention can be prepared by the following method:
at 0 ℃, 1-vinylimidazole and butane sultone are slowly added into the flask and stirred at room temperature for 24h, and finally the product is washed with diethyl ether and dried in vacuum (25 ℃,6h) to obtain 1-vinylimidazole butane sulfonic acid. Slowly adding equimolar trifluoromethanesulfonic acid and 1-vinyl imidazole butane sulfonic acid into a round-bottom flask at 0 ℃, and reacting for 12h at 60 ℃ to obtain [ VIm (CH)2)4SO3H][CF3SO3]. The reaction product was washed with diethyl ether and dried in vacuo (50 ℃ C., 2 h).Taking a certain amount of [ VIm (CH)2)4SO3H][CF3SO3]Adding N, N-dimethyl formamide (DMF), stirring to dissolve completely, adding Azodiisobutyronitrile (AIBN) as initiator, heating to 60 deg.C under nitrogen protection, and stirring for 24 hr. After the reaction is finished, adding ethyl acetate into the reaction liquid to promote the product to be separated out, thereby obtaining the acidic polymerization vinyl ionic liquid catalyst.
The preparation method and conditions of the acidic polymeric allyl ionic liquid or acidic polymeric alkenyl butyl ionic liquid catalyst are the same as those of the above catalyst, and the difference is that 1-vinyl imidazole in the acidic polymeric allyl ionic liquid or acidic polymeric alkenyl butyl ionic liquid catalyst is replaced by 1-allyl imidazole or 1-butenyl imidazole group, and the acidic polymeric allyl ionic liquid or acidic polymeric alkenyl butyl ionic liquid catalyst is obtained after reaction.
The structural formula of the acidic polymeric allyl ionic liquid catalyst is shown as follows:
the structural formula of the acidic polymerization alkene butyl ionic liquid catalyst is shown as follows:
the invention is that after the ring-opening reaction of the epoxy fatty acid methyl ester and the organic alcohol is catalyzed by the prepared catalyst, gravity sedimentation is carried out, the product and the catalyst are layered, the liquid of the reaction product is decompressed and steamed to remove volatile matters, thus preparing the biological lubricating oil, and the acidic polymerization ionic liquid catalyst can be reused after being recovered.
The steps of catalyzing the ring opening of epoxy bonds in epoxy fatty acid methyl ester by adopting the prepared catalyst to carry out addition reaction to synthesize the biological lubricating oil are as follows:
preparation of biological lubricating oil: adding epoxy methyl ester, organic alcohol and the acidic polymeric ionic liquid catalyst in a certain ratio into a three-necked flask provided with a magnetic stirrer or a mechanical stirring and refluxing condenser pipe and a thermometer, wherein the molar ratio of the epoxy methyl ester to the organic alcohol is 1:1 to 1:6, and the mass ratio of the acidic polymeric ionic liquid to the epoxy methyl ester is 1:4 to 1: 60. Heating to the reaction temperature, starting reaction timing, stopping reaction after a preset reaction time, cooling and standing the reaction liquid, layering the product and the acidic polymeric ionic liquid, simply treating the polymer ionic liquid separated from the lower layer for reuse, and distilling the upper layer reaction product liquid to remove organic alcohol to obtain the biological lubricating oil product.
The mechanism for preparing the biological lubricating oil is as follows:
the method of the present invention is further illustrated by the following examples, which are not intended to be limiting.
Example 1:
68g of ethanol and 4g of acidic vinyl ionic liquid monomer catalyst were weighed into a four-necked flask with a condenser and a thermometer, heated to 80 ℃ with stirring, and then 200g of epoxidized methyl soyate was added to obtain a reaction system having an initial epoxy value of 5.46, and a ring-opening reaction was carried out at that temperature. Sampling every 30min during the reaction, measuring the epoxy value, and stopping the reaction when the reaction time t is 12 h. And cooling the solution to room temperature, standing and settling, centrifugally separating the acidic vinyl ionic liquid monomer, finding that the ionic liquid monomer catalyst is difficult to separate and recycle, and distilling the reaction solution under reduced pressure to finally obtain the clear and transparent ethanol modified biological lubricating oil. The biological lubricating oil has an epoxy value of 1.076, a conversion rate of 80.3%, an acid value of 1.73(mgKOH/g), and a kinematic viscosity of 38.49 (mm) at 40 DEG C2/s)。
Example 2:
68g of ethanol and 4g of acidic polymerization vinyl ionic liquid catalyst are weighed and placed in a four-neck flask with a condenser pipe and a thermometer, the mixture is heated to 80 ℃ under the stirring state, then 200g of epoxidized soyate methyl ester is added, the initial epoxy value of a reaction system is measured to be 5.46, and ring opening reaction is carried out at the temperatureShould be used. Samples were taken every 30min during the reaction, the epoxy value was determined, and the reaction was stopped when the epoxy value was less than 0.08 (t 10 h). And cooling the solution to room temperature, standing and settling, layering the product and the acidic polymeric ionic liquid, performing centrifugal separation on the lower layer to obtain an acidic polymeric ionic liquid catalyst, and performing reduced pressure distillation on the upper layer reaction solution to finally obtain the clear and transparent ethanol modified biological lubricating oil. The bio-lubricating oil had an epoxy value of 0.172, a conversion of 96.8%, an acid value of 0.95(mgKOH/g), and a kinematic viscosity at 40 ℃ of 38.51 (mm)2/s)。
Example 3:
68g of ethanol and 4g of acidic polymerization vinyl ionic liquid catalyst were weighed into a four-necked flask equipped with a condenser tube and a thermometer, heated to 80 ℃ with stirring, and then 200g of epoxidized methyl soyate was added to measure the initial epoxy value of the reaction system to be 5.46, and ring-opening reaction was carried out at that temperature. Samples were taken every 30min during the reaction, the epoxy value was determined, and the reaction was stopped when the epoxy value was less than 0.08 (t-12 h). And cooling the solution to room temperature, standing and settling, layering the product and the acidic polymeric ionic liquid, performing centrifugal separation on the lower layer to obtain an acidic polymeric ionic liquid catalyst, and performing reduced pressure distillation on the upper layer reaction solution to finally obtain the clear and transparent ethanol modified biological lubricating oil. The biological lubricating oil had an epoxy value of 0.069, a conversion of 98.7%, an acid value of 0.78(mgKOH/g), and a kinematic viscosity at 40 ℃ of 38.53 (mm)2/s)。
Example 4:
84.4g of isopropanol and 4g of acidic polymerization vinyl ionic liquid catalyst were weighed into a four-necked flask with a condenser tube and a thermometer, heated to 70 ℃ with stirring, and then 200g of epoxy rapeseed oil fatty acid methyl ester was added to measure the initial epoxy value of the reaction system to be 5.46, and a ring-opening reaction was performed at that temperature. Sampling is carried out every 30min during the reaction process, the epoxy value is measured, and when the epoxy value is less than 0.08 (t is 14h), the reaction is stopped. Cooling the solution to room temperature, standing for settling, separating the product from the acidic polymeric ionic liquid to obtain a lower layer, performing centrifugal separation to obtain an acidic polymeric ionic liquid catalyst, and distilling the upper layer reaction solution under reduced pressure to obtain a clear and transparent isopropanol modified crude productThe product is lubricating oil. The biological lubricating oil had an epoxy value of 0.068, a conversion of 98.8%, an acid value of 0.79(mgKOH/g), and a kinematic viscosity at 40 ℃ of 37.54 (mm)2/s)。
Example 5:
114.4g of n-butanol and 4g of an acidic polymerization vinyl ionic liquid catalyst were weighed out in a four-necked flask equipped with a condenser tube and a thermometer, heated to 70 ℃ with stirring, and then 200g of methyl ricinoleic acid ester was added to measure the initial epoxy value of the reaction system to be 5.46, and a ring-opening reaction was carried out at that temperature. Sampling is carried out every 30min during the reaction process, the epoxy value is measured, and when the epoxy value is less than 0.08 (t is 10h), the reaction is stopped. And cooling the solution to room temperature, standing and settling, layering the product and the acidic polymeric ionic liquid, performing centrifugal separation on the lower layer to obtain an acidic polymeric ionic liquid catalyst, and performing reduced pressure distillation on the upper layer reaction solution to finally obtain the clear and transparent n-butyl alcohol modified biological lubricating oil. The bio-lubricating oil had an epoxy value of 0.075, a conversion of 98.6%, an acid value of 0.72(mgKOH/g) and a kinematic viscosity at 40 ℃ of 34.48 (mm)2/s)。
Example 6:
114.4g of isobutanol and 4g of an acidic polymeric vinyl ionic liquid catalyst were weighed into a four-necked flask with a condenser tube and a thermometer, heated to 70 ℃ with stirring, and then 200g of methyl ricinoleate was added to obtain a reaction system, the initial epoxy value of which was 5.46, and a ring-opening reaction was carried out at that temperature. Samples were taken every 30min during the reaction, the epoxy value was determined, and the reaction was stopped when the epoxy value was less than 0.08 (t 10 h). And cooling the solution to room temperature, standing and settling, layering the product and the acidic polymeric ionic liquid, performing centrifugal separation on the lower layer to obtain an acidic polymeric ionic liquid catalyst, and performing reduced pressure distillation on the upper layer reaction solution to finally obtain the clear and transparent isobutanol modified biological lubricating oil. The biological lubricating oil had an epoxy value of 0.066, a conversion of 98.8%, an acid value of 0.79(mgKOH/g), and a kinematic viscosity at 40 ℃ of 35.50(mm KOH/g)2/s)。
Example 7:
68g of ethanol and 4g of acidic polymeric allyl ionic liquid catalyst were weighed into a four-neck flask equipped with a condenser tube and a thermometer, heated to 80 ℃ with stirring, and then 200g of epoxidized methyl soyate was added to measure the initial epoxy value of the reaction system to be 5.46, and ring-opening reaction was carried out at that temperature. Samples were taken every 30min during the reaction, the epoxy value was determined, and the reaction was stopped when the epoxy value was less than 0.08 (t 10 h). And cooling the solution to room temperature, standing and settling, layering the product and the acidic polymeric ionic liquid, performing centrifugal separation on the lower layer to obtain an acidic polymeric ionic liquid catalyst, and performing reduced pressure distillation on the upper layer reaction solution to finally obtain the clear and transparent ethanol modified biological lubricating oil. The biological lubricating oil had an epoxy value of 0.07, a conversion of 98.7%, an acid value of 0.76(mgKOH/g), and a kinematic viscosity at 40 ℃ of 38.32 (mm)2/s)。
Example 8:
68g of ethanol and 4g of acidic polymerized alkenyl butyl ionic liquid catalyst were weighed into a four-neck flask with a condenser and a thermometer, heated to 80 ℃ with stirring, and then 200g of epoxidized methyl soyate was added to measure the initial epoxy value of the reaction system to be 5.46, and ring-opening reaction was performed at that temperature. Samples were taken every 30min during the reaction, the epoxy value was determined, and the reaction was stopped when the epoxy value was less than 0.08 (t 10 h). And cooling the solution to room temperature, standing and settling, layering the product and the acidic polymeric ionic liquid, centrifuging the lower layer to separate the acidic polymeric ionic liquid catalyst, and distilling the upper layer reaction solution under reduced pressure to finally obtain the clear and transparent ethanol modified biological lubricating oil. The biological lubricating oil had an epoxy value of 0.069, a conversion of 98.7%, an acid value of 0.77(mgKOH/g), and a kinematic viscosity at 40 ℃ of 38.23(mm KOH/g)2/s)。
Claims (3)
1. A method for preparing biological lubricating oil by acidic polymerization ionic liquid catalysis is characterized in that: the acidic polymeric ionic liquid is one of the following structural formulas:
the method for preparing the biological lubricating oil by the catalysis of the acidic polymeric ionic liquid comprises the following steps:
A. taking the acidic polymerized ionic liquid as a catalyst for reaction, catalyzing epoxy fatty acid methyl ester to react with short-chain alcohol at the temperature of 60-80 ℃ for 10-20 hours, and stopping the reaction when the epoxy value is less than 0.08 to obtain reaction liquid;
B. cooling the reaction liquid prepared in the step A to room temperature, standing and settling to enable the product to be layered with the acidic polymeric ionic liquid, separating the lower layer to obtain an acidic polymeric ionic liquid catalyst, and decompressing the upper layer liquid product to remove short-chain alcohol to obtain biological lubricating oil;
the epoxidized fatty acid methyl ester is epoxidized castor oil fatty acid methyl ester, epoxidized soybean oil fatty acid methyl ester or epoxidized rapeseed oil fatty acid methyl ester, and the short-chain alcohol is ethanol, propanol, isopropanol, n-butanol or isobutanol;
the preparation method of the acidic polymeric ionic liquid comprises the following steps: slowly adding 1-vinylimidazole and butane sultone into a flask at 0 ℃, stirring for 24 hours at room temperature, washing a product with diethyl ether, and performing vacuum drying for 6 hours at 25 ℃ to obtain 1-vinylimidazole butane sulfonic acid; slowly adding equimolar trifluoromethanesulfonic acid and 1-vinyl imidazole butane sulfonic acid into a round-bottom flask at 0 ℃, and reacting for 12h at 60 ℃ to obtain [ VIm (CH)2)4SO3H] [CF3SO3]Washing the reaction product with ether, vacuum drying at 50 deg.C for 2 hr, and collecting certain amount of [ VIm (CH)2)4SO3H] [CF3SO3]Adding N, N-dimethyl formamide (DMF), stirring to dissolve completely, adding a certain amount of initiator Azobisisobutyronitrile (AIBN), heating to 60 deg.C under nitrogen protection, stirring for 24 hr, and adding into the reaction solution after reactionAdding ethyl acetate to promote the product to be separated out, and obtaining the acidic polymerization vinyl ionic liquid catalyst;
and (2) replacing the 1-vinyl imidazole with 1-allyl imidazole or 1-butenyl imidazole, and reacting to obtain the acidic polymeric allyl ionic liquid or acidic polymeric alkenyl butyl ionic liquid catalyst respectively.
2. The method for preparing biological lubricating oil catalyzed by acidic polymeric ionic liquid according to claim 1, wherein: the molar ratio of the epoxy methyl ester to the short-chain alcohol is 1: 1-1: 4; the mass ratio of the acidic polymeric ionic liquid to the epoxy methyl ester is 1: 4-1: 60.
3. The method for preparing biological lubricating oil catalyzed by acidic polymeric ionic liquid according to claim 1, wherein: and the acidic polymeric ionic liquid separated in the step B is repeatedly used for reaction.
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