CN111533657A - Method for purifying trimethylolpropane oleate and preparation method thereof - Google Patents
Method for purifying trimethylolpropane oleate and preparation method thereof Download PDFInfo
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- CN111533657A CN111533657A CN202010309557.9A CN202010309557A CN111533657A CN 111533657 A CN111533657 A CN 111533657A CN 202010309557 A CN202010309557 A CN 202010309557A CN 111533657 A CN111533657 A CN 111533657A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
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Abstract
The invention provides a method for purifying trimethylolpropane oleate and a preparation method thereof, wherein the method for purifying trimethylolpropane oleate comprises the following steps: and sequentially adding normal salt of weak polybasic acid and porous silicate into the crude trimethylolpropane oleate, and filtering to obtain the purified trimethylolpropane oleate. According to the purification method, normal salt and porous silicate of the polybasic weak acid are sequentially added into a trimethylolpropane oleate crude product, so that the normal salt of the polybasic weak acid and redundant oleic acid in the crude product form acid salt, the formed acid salt is adsorbed by the porous silicate, other tiny impurities in a system can be removed by the porous silicate, and then the purified trimethylolpropane oleate is obtained by filtering; is suitable for purifying the trimethylolpropane oleate crude product prepared by the invention and various methods disclosed in the prior art.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a method for purifying trimethylolpropane oleate and a preparation method thereof.
Background
The trimethylolpropane oleate is green lubricating oil and is ideal base oil of flame-retardant hydraulic oil; the lubricating oil has the advantages of excellent lubricity, high temperature resistance, low toxicity, viscosity-temperature characteristics, high biodegradation rate and the like, so the lubricating oil has wide application in the fields of chemical fiber oil agents, aircraft engine lubricating oil, metal processing oil and the like.
The synthesis method of the trimethylolpropane oleate mainly comprises an ester exchange method, an acyl chloride method and a direct esterification method, wherein the ester exchange method is carried out along with the reaction, the steric hindrance of the trimethylolpropane can influence the reaction, and the yield is low; the acyl chloride method can generate a large amount of hydrogen chloride in the preparation process, causes serious pollution to the environment and cannot realize industrial production; the direct esterification method has smooth reaction, high yield and no pollution to the environment, and is suitable for industrial production, so the method is most widely applied at present.
For example, chinese patent document CN103159625A discloses a method for producing trimethylolpropane oleate in a single reactor, which comprises adding oleic acid, trimethylolpropane and a solid acid catalyst into a reaction kettle, heating to 160-. Although the method reduces the quality of by-products and residual acid in the product, the process for removing the residual acid by steam stripping is complex and has high energy consumption, and the product obtained by purification has poor chroma, so that the emulsification and lubrication performance is reduced.
Therefore, chinese patent document CN104387271A discloses a purification process of a trimethylolpropane oleate crude product, which is to flow the crude product through an adsorption tower at a certain flow rate to adsorb fine particles and colloid to improve the purity of trimethylolpropane oleate, but although the purification process simplifies the process and reduces energy consumption, the product obtained by purification still has poor chromaticity to reduce the emulsification and lubrication performance.
Disclosure of Invention
Therefore, the invention aims to overcome the defects of poor chromaticity and reduced emulsification and lubricating properties of a product purified by a trimethylolpropane oleate purification method in the prior art, and provides a trimethylolpropane oleate purification method and a preparation method.
Therefore, the invention provides the following technical scheme:
a method for purifying trimethylolpropane oleate comprises the following steps: and sequentially adding normal salt of weak polybasic acid and porous silicate into the crude trimethylolpropane oleate, and filtering to obtain the purified trimethylolpropane oleate.
Further, the mass ratio of the normal salt of the weak polybasic acid to the crude trimethylolpropane oleate is 0.01-0.05: 1.
Furthermore, the mass ratio of the normal salt of the weak polybasic acid to the crude trimethylolpropane oleate is 0.02-0.03: 1.
Further, the addition temperature of the normal salt of the weak polybasic acid is 60-90 ℃.
Further, the addition temperature of the normal salt of the weak polybasic acid is 70-85 ℃.
Further, the time interval between the addition of the normal salt of the weak polybasic acid and the porous silicate is 0.5-3 h.
Further, the addition time interval of the normal salt of the polybasic weak acid and the porous silicate is 1-1.5 h.
Furthermore, the mass ratio of the porous silicate to the crude trimethylolpropane oleate is 0.002-0.01: 1.
Furthermore, the mass ratio of the porous silicate to the crude trimethylolpropane oleate is 0.005-0.008: 1.
Furthermore, the adding temperature of the porous silicate is 50-110 ℃, and the reaction time after the porous silicate is added is 3-7 h.
Furthermore, the adding temperature of the porous silicate is 80-90 ℃;
and/or the reaction time after the porous silicate is added is 4-6 h.
Further, the normal salt of the weak polybasic acid is at least one of sodium oxalate, potassium oxalate, sodium carbonate, potassium sodium carbonate, sodium phosphate and potassium phosphate;
the porous silicate is porous magnesium silicate.
Further, the specific surface area of the porous magnesium silicate is 400m or more2/g；
The apparent volume is more than or equal to 20ml/10 g;
the bulk density is 400-500 g/L.
The apparent volume refers to the sum of the solid volume of the porous magnesium silicate and the volume of the closed pores.
Furthermore, the content of MgO in the porous magnesium silicate is 10-20 wt%, and SiO is2The content is 50-70 wt%.
The invention also provides a preparation method of the trimethylolpropane oleate, which comprises the purification method of the trimethylolpropane oleate crude product.
Further, the preparation method of the trimethylolpropane oleate also comprises the steps of uniformly mixing trimethylolpropane and oleic acid, adding a catalyst, and performing vacuum dehydration to obtain a crude product of the trimethylolpropane oleate.
Further, the molar ratio of the trimethylolpropane to the oleic acid is 1: 3.0-3.4;
the ratio of the mass of the catalyst to the sum of the masses of trimethylolpropane and oleic acid is 0.05-3: 100.
Further, the molar ratio of trimethylolpropane to oleic acid is 1: 3.05-3.15.
Further, the ratio of the mass of the catalyst to the sum of the masses of trimethylolpropane and oleic acid is 0.1-0.2: 100.
Further, the temperature of vacuum dehydration is 80-120 ℃, and the time is 4-9 h.
Further, the temperature of vacuum dehydration is 90-110 ℃;
and/or the vacuum dehydration time is 4-9 h.
Further, the catalyst is at least one of solid super acid, p-toluenesulfonic acid and benzenesulfonic acid.
The technical scheme of the invention has the following advantages:
1. the trimethylolpropane oleate crude product is a mixture of trimethylolpropane oleate and impurities (except the trimethylolpropane oleate), and is prepared by esterifying trimethylolpropane and oleic acid under the catalysis of an acid catalyst, or a strong-acid ion exchange resin, or heteropoly acid and the like; or prepared by ester exchange of trimethylolpropane and oleate compounds under the catalysis of an alkaline catalyst, or other existing methods for synthesizing trimethylolpropane oleate. The impurities can not meet the requirement of direct application, so the crude product needs to be purified, and the method for purifying the trimethylolpropane oleate provided by the invention comprises the following steps: and sequentially adding the polybasic weak acid normal salt and the porous silicate into the trimethylolpropane oleate crude product, and filtering to obtain the purified trimethylolpropane oleate. The inventor finds that the combination of the polybasic weak acid normal salt and the porous silicate has unexpected technical effect on treating the crude trimethylolpropane oleate: according to the purification method, normal salt and porous silicate of the polybasic weak acid are sequentially added into a trimethylolpropane oleate crude product, so that the normal salt of the polybasic weak acid and redundant oleic acid in the crude product form acid salt, the formed acid salt is adsorbed by the porous silicate, meanwhile, other tiny impurities, colloid and the like in a system can be removed by the porous silicate, and then the purified trimethylolpropane oleate is obtained by filtering; and the method has the advantages of small filter residue yield, high yield, simplicity, convenience, short period and low energy consumption, and is suitable for purifying the trimethylolpropane oleate crude product prepared by the invention and various methods disclosed in the prior art.
2. According to the method for purifying the trimethylolpropane oleate, provided by the invention, the product chromaticity, period and energy consumption can be further reduced by limiting the mass ratio of the normal salt of the weak polybasic acid to the crude trimethylolpropane oleate.
3. According to the method for purifying trimethylolpropane oleate provided by the invention, the adding temperature of the normal salt of the weak polybasic acid is limited, so that the rate and the effect of forming the acid salt by the normal salt of the weak polybasic acid and redundant oleic acid in the crude product can be further improved, the product chromaticity is further reduced, the emulsification and lubrication performance of the product is improved, and the yield of the purified product is improved.
4. According to the method for purifying trimethylolpropane oleate provided by the invention, the time interval for adding the normal salt of the weak polybasic acid and the porous silicate is limited, so that the adsorption effect of the acidic salt formed by the normal salt of the weak polybasic acid and redundant oleic acid in the crude product and the porous silicate can be improved, the product chromaticity is further reduced, and the emulsification and lubrication performance of the product is improved.
5. According to the method for purifying the trimethylolpropane oleate, provided by the invention, the product chromaticity and the filter residue yield can be further reduced by limiting the mass ratio of the porous silicate to the crude trimethylolpropane oleate.
6. The method for purifying the trimethylolpropane oleate provided by the invention can further improve the adsorption effect of the porous silicate, reduce the product chromaticity and improve the emulsification and lubrication performance of the product by limiting the adding temperature of the porous silicate and the reaction time after the porous silicate is added.
7. The method for purifying the trimethylolpropane oleate limits the normal salt of the weak polybasic acid to be at least one of sodium oxalate, potassium oxalate, sodium carbonate, sodium potassium carbonate, sodium phosphate and potassium phosphate; the porous silicate is limited to be porous magnesium silicate, so that the removal rate of redundant oleic acid and impurities can be further improved, and the chroma is reduced.
8. The method for purifying the trimethylolpropane oleate provided by the invention can further improve the removal rate of redundant oleic acid and impurities and reduce the chroma by limiting the specific surface area, the apparent volume and the bulk density of the porous magnesium silicate.
9. According to the method for purifying trimethylolpropane oleate provided by the invention, the content of magnesium oxide and silicon dioxide in the porous magnesium silicate is limited, so that the adsorption effect of the porous silicate can be further improved, the product chromaticity is reduced, and the emulsification and lubrication performance of the product is improved.
10. The preparation method of the trimethylolpropane oleate provided by the invention comprises a purification method of a trimethylolpropane oleate crude product, and the product obtained by the method has low chroma, improves the emulsification and lubrication performance, and is simple and convenient, short in period and low in energy consumption; in addition, the product obtained by purification has high purity and small filter residue yield.
11. According to the preparation method of the trimethylolpropane oleate provided by the invention, the molar ratio of the trimethylolpropane to the oleic acid and the ratio of the mass of the catalyst to the sum of the masses of the trimethylolpropane and the oleic acid are limited, so that the esterification rate of the product can be improved.
12. The preparation method of the trimethylolpropane oleate provided by the invention can further improve the esterification reaction rate and the esterification rate and reduce the product chromaticity by limiting the temperature and time of vacuum dehydration.
Detailed Description
The following examples are provided to further understand the present invention, not to limit the scope of the present invention, but to provide the best mode, not to limit the content and the protection scope of the present invention, and any product similar or similar to the present invention, which is obtained by combining the present invention with other prior art features, falls within the protection scope of the present invention.
The examples do not show the specific experimental steps or conditions, and can be performed according to the conventional experimental steps described in the literature in the field. The reagents or instruments used are not indicated by manufacturers, and are all conventional reagent products which can be obtained commercially.
Example 1
The embodiment provides a preparation method of trimethylolpropane oleate, which specifically comprises the following steps:
234kg of trimethylolpropane and 1500kg of oleic acid were mixed and added to a reaction vessel, and 1.7kg of SO was added4 2-/TiO2Solid super acid, controlling the reaction temperature at 110 ℃, and vacuumizing and dehydrating for 5 h; then cooling to 70 ℃, adding 45kg of sodium oxalate, and stirring for 1.5 h; the temperature was raised to 90 ℃ and 8.7kg of porous magnesium silicate was added, stirred for 4 hours and then filtered to obtain 1599kg of trimethylolpropane oleate.
Wherein the specific surface area of the porous magnesium silicate is 500m2(ii)/g; the apparent volume is 30ml/10 g; the bulk density is 450 g/L; MgO content 10 wt%, SiO2The content was 60 wt%.
Example 2
The embodiment provides a preparation method of trimethylolpropane oleate, which specifically comprises the following steps:
347kg of trimethylolpropane and 2300kg of oleic acid are mixed and added into a reaction kettle, 5.3kg of benzenesulfonic acid is added, the reaction temperature is controlled at 90 ℃, and vacuumizing dehydration is carried out for 7 hours; then cooling to 85 ℃, adding 52.9kg of potassium phosphate, and stirring for 1 h; the temperature is reduced to 80 ℃, 21.2kg of porous magnesium silicate is added, stirred for 6h and then filtered, thus obtaining 2374kg of trimethylolpropane oleate.
Wherein the specific surface area of the porous magnesium silicate is 400m2(ii)/g; the apparent volume is 27ml/10 g; the bulk density is 400-500 g/L; MgO content 18 wt%, SiO2The content was 50 wt%.
Example 3
The embodiment provides a preparation method of trimethylolpropane oleate, which specifically comprises the following steps:
mixing 123kg of trimethylolpropane and 800kg of oleic acid, adding the mixture into a reaction kettle, adding 1.4kg of p-toluenesulfonic acid, controlling the reaction temperature to be 100 ℃, and vacuumizing and dehydrating for 6 hours; then, the temperature is reduced to 75 ℃, 27.7kg of sodium carbonate is added, and the mixture is stirred for 1.2 hours; the temperature is raised to 85 ℃, 5.5kg of porous magnesium silicate is added, stirred for 5h and then filtered, and 842kg of trimethylolpropane oleate is obtained.
Wherein the specific surface area of the porous magnesium silicate is 450m2(ii)/g; apparent appearanceThe volume is 23ml/10 g; the bulk density is 400 g/L; MgO content 15 wt%, SiO2The content was 70 wt%.
Example 4
The embodiment provides a preparation method of trimethylolpropane oleate, which specifically comprises the following steps:
mixing 200kg of trimethylolpropane and 1271kg of oleic acid, adding the mixture into a reaction kettle, adding 0.74kg of p-toluenesulfonic acid, controlling the reaction temperature to be 80 ℃, and vacuumizing and dehydrating for 4 hours; then cooling to 85 ℃, adding 4.0kg of sodium oxalate and 10.71kg of potassium oxalate, and stirring for 0.5 h; the temperature was raised to 110 ℃, 2.9kg of porous magnesium silicate was added, stirred for 3 hours, and then filtered to obtain 1376kg of trimethylolpropane oleate.
Wherein the specific surface area of the porous magnesium silicate is 420m2(ii)/g; the apparent volume is 25ml/10 g; the bulk density is 500 g/L; MgO content of 12 wt%, SiO2The content was 55 wt%.
Example 5
The embodiment provides a preparation method of trimethylolpropane oleate, which specifically comprises the following steps:
mixing 280kg of trimethylolpropane and 2004kg of oleic acid, adding the mixture into a reaction kettle, adding 30.5kg of p-toluenesulfonic acid and 38.02kg of benzenesulfonic acid, controlling the reaction temperature to be 120 ℃, and vacuumizing and dehydrating for 9 hours; then cooling to 60 ℃, adding 34.7kg of sodium oxalate, 30kg of potassium oxalate and 39.3kg of sodium carbonate, and stirring for 3 hours; the temperature was reduced to 50 ℃ and 22.84kg of porous magnesium silicate was added, stirred for 7 hours and then filtered to obtain 1918kg of trimethylolpropane oleate.
Wherein the specific surface area of the porous magnesium silicate is 430m2(ii)/g; the apparent volume is 20ml/10 g; the bulk density is 430 g/L; MgO content of 20 wt%, SiO2The content was 65 wt%.
Comparative example 1
The comparative example provides a preparation method of trimethylolpropane oleate, which specifically comprises the following steps:
234kg of trimethylolpropane and 1500kg of oleic acid were mixed and added to a reaction vessel, and 1.7kg of SO was added4 2-/TiO2Controlling the reaction temperature to be 110 ℃ by using a solid super acidic catalyst, and vacuumizing and dehydrating for 5 hours; then cooling to 70 ℃, and stirring for 1.5 h; the temperature was raised to 90 ℃ and 8.7kg of porous magnesium silicate was added, stirred for 4 hours and then filtered to obtain 1596kg of trimethylolpropane oleate.
Wherein the specific surface area of the porous magnesium silicate is 500m2(ii)/g; the apparent volume is 30ml/10 g; the bulk density is 450 g/L; MgO content 10 wt%, SiO2The content was 60 wt%.
Examples of the experiments
The trimethylolpropane oleate obtained in each example and each comparative example was measured for color, acid value, hydroxyl value, viscosity, flash point, pour point, saponification value and iodine value, and the specific measurement results are shown in table 1.
Wherein, the chromaticity is detected according to GB/T22295-;
detecting the acid value according to a method for measuring the acid value of the fifth part in GB/T12008.5-2010;
the hydroxyl value was measured according to the phthalic anhydride method in GB/T7383-2007;
the viscosity was measured according to GB/T265-1988;
the flash point is detected according to GB/T1671-;
the pour point is detected according to GB/T3535-;
the saponification value is detected according to HG/T3505-2000;
iodine number was determined according to DIN 53241;
the calculation formula of the esterification rate is as follows:
the esterification rate [% ], [% ] is (1254.38-hydroxyl value)/(6.32 × hydroxyl value +1254.38) × 100, and the unit of hydroxyl value is mgKOH/g.
TABLE 1 test results
Note: the viscosity was measured at 40 ℃.
The data in the table show that the method for purifying trimethylolpropane oleate provided by the invention adds normal salt of polybasic weak acid and porous magnesium silicate into the crude trimethylolpropane oleate in turn, so that the obtained product has low chroma, low hydroxyl value and low acid value, and the chroma, the hydroxyl value, the acid value, the viscosity, the iodine value, the flash point, the pour point and the saponification value all meet the quality index requirements of the trimethylolpropane oleate; the preparation method of the trimethylolpropane oleate provided by the invention has high esterification rate.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the spirit or scope of the invention.
Claims (22)
1. A method for purifying trimethylolpropane oleate is characterized by comprising the following steps: and sequentially adding normal salt of weak polybasic acid and porous silicate into the crude trimethylolpropane oleate, and filtering to obtain the purified trimethylolpropane oleate.
2. The purification method according to claim 1, wherein the mass ratio of the normal salt of the weak polybasic acid to the crude trimethylolpropane oleate is 0.01-0.05: 1.
3. The purification method according to claim 2, wherein the mass ratio of the normal salt of the weak polybasic acid to the crude trimethylolpropane oleate is 0.02-0.03: 1.
4. A purification process according to any one of claims 1 to 3, wherein the addition temperature of the normal salt of a weak polybasic acid is from 60 to 90 ℃.
5. Purification process according to claim 4, characterized in that the addition temperature of the normal salt of a weak polybasic acid is between 70 and 85 ℃.
6. The purification process according to any one of claims 1 to 5, wherein the addition time interval between the normal salt of the weak polybasic acid and the porous silicate is 0.5 to 3 hours.
7. The purification process according to claim 6, wherein the addition time interval between the normal salt of the weak polybasic acid and the porous silicate is 1 to 1.5 hours.
8. The purification method according to any one of claims 1 to 7, wherein the mass ratio of the porous silicate to the crude trimethylolpropane oleate is 0.002 to 0.01: 1.
9. The purification method according to claim 8, wherein the mass ratio of the porous silicate to the crude trimethylolpropane oleate is 0.005-0.008: 1.
10. The purification process according to any one of claims 1 to 9, wherein the porous silicate is added at a temperature of 50 to 110 ℃ and the reaction time after the addition of the porous silicate is 3 to 7 hours.
11. The purification process according to claim 10, wherein the porous silicate is added at a temperature of 80 to 90 ℃;
and/or the reaction time after the porous silicate is added is 4-6 h.
12. The purification method according to claim 11, wherein the normal salt of a weak polybasic acid is at least one of sodium oxalate, potassium oxalate, sodium carbonate, potassium sodium carbonate, sodium phosphate, and potassium phosphate;
the porous silicate is porous magnesium silicate.
13. The purification method according to claim 12, wherein the porous magnesium silicate has a specific surface area of 400m or more2/g；
The apparent volume is more than or equal to 20ml/10 g;
the bulk density is 400-500 g/L.
14. The purification method according to claim 12 or 13, wherein the porous magnesium silicate has an MgO content of 10 to 20 wt% and SiO2The content is 50-70 wt%.
15. A method for producing trimethylolpropane oleate, which comprises the method for purifying a crude trimethylolpropane oleate as described in any one of claims 1 to 14.
16. The method according to claim 15, further comprising a step of mixing trimethylolpropane and oleic acid uniformly, adding a catalyst, and performing vacuum dehydration to obtain a crude trimethylolpropane oleate.
17. The method of claim 16, wherein the molar ratio of trimethylolpropane to oleic acid is 1: 3.0-3.4;
the ratio of the mass of the catalyst to the sum of the masses of trimethylolpropane and oleic acid is 0.05-3: 100.
18. The method of claim 17, wherein the molar ratio of trimethylolpropane to oleic acid is 1: 3.05-3.15.
19. The production method according to any one of claims 16 to 18, wherein the ratio of the mass of the catalyst to the sum of the masses of trimethylolpropane and oleic acid is 0.1 to 0.2: 100.
20. The process according to any one of claims 16 to 19, wherein the temperature of the vacuum dehydration is 80 to 120 ℃ and the time is 4 to 9 hours.
21. The method of claim 20, wherein the temperature of the vacuum dehydration is 90-110 ℃;
and/or the vacuum dehydration time is 4-9 h.
22. The method according to any one of claims 16 to 21, wherein the catalyst is at least one of a solid super acid, p-toluenesulfonic acid and benzenesulfonic acid.
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| CN102643197A (en) * | 2012-03-31 | 2012-08-22 | 江苏利田科技股份有限公司 | Cleaning production method for di-trimethylolpropane tetra-acrylic ester or pentaerythritol tetra-acrylic ester |
| CN102887825A (en) * | 2012-09-04 | 2013-01-23 | 陕西省石油化工研究设计院 | Method for preparing polyol ester lubricating oil by using composite solid acid catalyst |
| CN105330543A (en) * | 2015-10-19 | 2016-02-17 | 中国石油化工股份有限公司 | Refining processing method of polyol esters |
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