CN112898235A - Epoxy neopentyl glycol oleate and synthesis method and application thereof - Google Patents
Epoxy neopentyl glycol oleate and synthesis method and application thereof Download PDFInfo
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Abstract
The invention discloses epoxy neopentyl glycol oleate with a structure shown as a formula (I), which can be used as a plasticizer to be applied to plastics, and the synthesis steps comprise: 1) carrying out esterification reaction on oleic acid and neopentyl glycol to synthesize neopentyl glycol oleate; 2) and carrying out epoxidation reaction on neopentyl glycol oleate and hydrogen peroxide to synthesize the epoxy neopentyl glycol oleate. The preparation process is simple, the product has excellent processing performance, higher ultraviolet blocking rate and good solvent precipitation resistance when the plasticizer is used in plastics; the product has good aging resistance and low-temperature impact embrittlement performance, is a nontoxic plastic plasticizer with excellent properties, and has wide market prospect.
Description
Technical Field
The invention relates to a plasticizer, in particular to neopentyl glycol epoxidized oleate, and further relates to a synthesis method and application of the neopentyl glycol epoxidized oleate.
Background
In recent years, with the increasing awareness of environmental protection, plastics such as medicines, food packages, daily necessities, toys, etc. have been more demanding for hygiene than plasticizers. For a long time, plasticizers are mainly based on o-benzene products, but it has been found that such plasticizers have some toxic and side effects on human bodies, and for this reason, the european union food safety agency (EFSA) stipulates the limits of concentration of dioctyl phthalate (DOP), dioctyl adipate (DOA) and the like, so that non-toxic and environment-friendly plasticizers become the focus of the current global plasticizer research.
Because the epoxy vegetable oil has the characteristics of good heat resistance, light resistance, mutual permeability, low-temperature flexibility, low volatility and the like, the epoxy vegetable oil is widely applied in the plastic industry in recent years, is the only plasticizer which is approved by the Food and Drug Administration (FDA) and can be used for instrument packaging materials, and is particularly suitable for the fields with strict environmental protection requirements such as food/drug plastic packaging materials, children toys, household decorative materials and the like. However, the epoxy vegetable oil has a large molecular weight and viscosity and poor fluidity, which limits its further application.
Neopentyl glycol oleate is an ester compound with excellent performance, has excellent viscosity-temperature property, good low temperature resistance, good high-temperature stability, low volatility, lower kinematic viscosity, stable rheological property, and better biodegradation performance and friction performance than mineral oil, thereby meeting higher lubricating requirements. And because the biodegradation rate is high and can reach 97 percent, the lubricating oil can be directly vaporized at higher temperature, almost no coking and residue exist, the lubricating oil is an environment-friendly green lubricating oil with great development potential, and becomes an important basic raw material for preparing high-grade lubricating oil and chemical fiber oil agent. The neopentyl glycol oleate crude product shows acidity, and the traditional deacidification method (CN 102826999A) is to add NaHCO accounting for 10-40% of the total weight of oleic acid and neopentyl glycol3The saturated solution is subjected to alkali washing, then the saturated solution is subjected to water washing, vacuum drying and other steps, the method has very high alkali consumption and water consumption, a large amount of alkali can not only corrode production equipment, but also cause partial saponification of a neopentyl glycol oleate crude product, so that the product yield is reduced, and the product quality is influenced, for example, the resistivity of the product is obviousA significant decrease, etc. There is therefore a need to find a more efficient deacidification process.
In addition, neopentyl glycol oleate is mainly used as lubricating oil, and further extended application thereof is rarely reported. The applicant hopes to develop a novel plasticizer with excellent properties by combining the characteristics of epoxy plasticizers and neopentyl glycol oleate.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a novel plasticizer epoxy neopentyl glycol oleate with excellent processability, good solvent precipitation resistance and good aging resistance.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention takes oleic acid and neopentyl glycol as raw materials, and the esterification reaction is carried out by 1): carrying out esterification reaction on oleic acid and neopentyl glycol under the action of a catalyst to synthesize neopentyl glycol oleate: 2) epoxidation reaction: carrying out epoxidation reaction on neopentyl glycol oleate generated in the step 1) and hydrogen peroxide under the action of weak acid and a catalyst to synthesize epoxy neopentyl glycol oleate, and the like, so as to synthesize a novel plasticizer epoxy neopentyl glycol oleate with excellent processing performance, good solvent precipitation resistance and good aging resistance, and the novel plasticizer epoxy neopentyl glycol oleate has a structure shown in the following formula (I):
it is preferable that: in the esterification reaction in the step 1), the weight ratio of oleic acid to neopentyl glycol is 4.9-6.0: 1.
it is preferable that: in the esterification reaction in the step 1), the reaction temperature is 160-250 ℃, and the reaction time is 8-16 hours. Further preferred are: the reaction temperature is respectively kept at 170 ℃, 190 ℃ and 210 ℃ for 2 hours, and kept at 230 ℃ for 8 hours.
It is preferable that: and (2) introducing nitrogen for protection in the esterification reaction in the step 1), and removing acidic substances in the neopentyl glycol oleate crude product by adopting a high-temperature nitrogen deodorization method.
It is preferable that: in the esterification reaction in the step 1), the catalyst is at least one of tetrabutyl titanate, phosphoric acid and sodium phosphate, and the dosage of the catalyst is 0.1-0.4% of the total weight of oleic acid and neopentyl glycol.
It is preferable that: in the epoxidation reaction in the step 2), the reaction temperature is 60-80 ℃, and the reaction time is 4-10 hours.
It is preferable that: in the epoxidation reaction in the step 2), the catalyst is sulfuric acid or phosphoric acid.
It is preferable that: in the epoxidation reaction in the step 2), the weak acid is formic acid and/or acetic acid.
It is preferable that: in the epoxidation reaction in the step 2), the weight ratio of neopentyl glycol oleate, hydrogen peroxide, weak acid and a catalyst is 1: 0.4-0.7: 0.04-0.08: 0.001-0.003.
The epoxy neopentyl glycol oleate prepared by the method can be used as a plasticizer, is commonly used in plastics, especially wires and cables, and has the characteristics of small viscosity, good stability, high fluidity and good plasticizing effect with plastics.
Compared with the prior art, the invention has the beneficial effects that:
1. the epoxy neopentyl glycol oleate serving as a novel compound is applied to plastics as a plasticizer, so that the product has excellent processing performance, high ultraviolet blocking rate and good solvent precipitation resistance; the product has good aging resistance and low-temperature impact embrittlement performance, and is a nontoxic plastic plasticizer with excellent properties, and is particularly applied to electric wire and cable materials;
2. the novel method for synthesizing the epoxy neopentyl glycol oleate serving as the plasticizer is provided, wherein nitrogen is introduced while the esterification reaction is carried out in the step 1), and an acidic substance in a crude neopentyl glycol oleate product is removed by adopting a high-temperature nitrogen deodorization method, so that deacidification methods such as alkali washing, water washing and the like are avoided, the corrosion to equipment is greatly reduced, and the yield and the quality of the neopentyl glycol oleate are improved.
Drawings
FIG. 1 shows a NMR spectrum of oleic acid as a starting material in example 1 of the present invention;
FIG. 2 shows the NMR spectrum of neopentyl glycol as the starting material in example 1 of the present invention;
FIG. 3 shows a NMR spectrum of neopentyl glycol oleate obtained in example 1 of the present invention;
FIG. 4 shows a NMR spectrum of neopentyl glycol epoxy oleate prepared in example 1 of the present invention.
FIG. 5 shows an infrared spectrum of neopentyl glycol oleate prepared in example 1 according to the present invention;
FIG. 6 shows an infrared spectrum of neopentyl glycol epoxy oleate prepared in example 1 according to the present invention;
FIG. 7 shows a graph of the rheological properties of a PVC compound plasticized with epoxy neopentyl glycol oleate obtained in example 1 according to the invention and other plasticizers of the prior art.
Detailed Description
The following further describes embodiments of the present invention with reference to specific examples. The raw materials used in the examples of the present invention are commercially available unless otherwise specified.
The synthesis process of the epoxy neopentyl glycol oleate provided by the invention comprises the following steps:
1) esterification reaction: oleic acid and neopentyl glycol are subjected to esterification reaction to synthesize neopentyl glycol oleate, in the reaction step, the reaction temperature is 160-250 ℃, the reaction time is 8-16 hours, and the reaction principle is as follows;
2) epoxidation reaction: carrying out epoxidation reaction on neopentyl glycol oleate generated in the step 1) and hydrogen peroxide under the action of weak acid and a catalyst to synthesize epoxy neopentyl glycol oleate, wherein in the reaction step, the reaction temperature is 60-80 ℃, the reaction time is 4-10 hours, and the reaction principle is as follows:
introducing nitrogen for protection in the esterification reaction in the step 1), wherein the weight ratio of oleic acid to neopentyl glycol is 4.9-6.0: 1, the catalyst can be at least one of tetrabutyl titanate, phosphoric acid and sodium phosphate, and the dosage of the catalyst is 0.1-0.4 percent of the total weight of oleic acid and neopentyl glycol;
in the epoxidation reaction in the step 2), the catalyst is sulfuric acid or phosphoric acid, the weak acid is formic acid and/or acetic acid, and the weight ratio of the neopentyl glycol oleate, the hydrogen peroxide, the weak acid and the catalyst is 1: 0.4-0.7: 0.04-0.08: 0.001-0.003.
The epoxy value (%) of the epoxy neopentyl glycol oleate product synthesized by the steps is more than or equal to 4.5, and the iodine value (I) is2100g) is not more than 3.0, the acid value (mgKOH/g) is not more than 3.0, the flash point (opening, DEG C) is not less than 260, the moisture content (percent) is not more than 0.2, the freezing point (DEG C) is not more than-10, and the volume resistivity/(omega cm) is not less than 1.2 x 1011。
Example 1
Oleic acid and neopentyl glycol are used as raw materials to synthesize epoxy neopentyl glycol oleate, and the synthesis steps comprise:
1) esterification reaction: 513.24g of oleic acid, 104g of neopentyl glycol and 0.93g of catalyst phosphoric acid are sequentially added into a three-neck round-bottom flask provided with a stirring device, a thermometer and a reflux condenser, nitrogen is introduced, the temperature is raised to 220 ℃ by stirring, the reaction is kept for 4 hours, and the reaction is kept for 4 hours at 250 ℃. And (3) intermittently taking the material, and finishing the reaction when the acid value of the sample is less than 2.0 to obtain the neopentyl glycol oleate which is a light yellow oily substance, wherein the acid value is detected to be 1.93 mgKOH/g.
2) Epoxidation reaction: 509g of neopentyl glycol oleate, 22g of formic acid and 0.5g of concentrated sulfuric acid as a catalyst, which are prepared in the step 1), are added into a four-neck round-bottom flask with a stirring device, a thermometer, a separating funnel and a reflux condenser, the mixture is stirred and heated to 60 ℃, 219g of 50% hydrogen peroxide is slowly dropped while stirring, after the addition is completed, the reaction is carried out for 4 hours at 80 ℃, the lower acid water layer is separated, the upper oil ester is washed to be neutral, the neopentyl glycol oleate epoxy light yellow oily substance is obtained by reduced pressure distillation to remove water and filtration, and the detection results of the physical and chemical indexes are shown in table 1.
Structural analysis:
a. nuclear magnetic resonance hydrogen spectrum
As shown in fig. 1, in the nmr hydrogen spectrum of oleic acid, the peak at δ of 0.86 to 0.90ppm represents a methyl group, the peaks at δ of 1.25 ppm and 1.38ppm represent methylene groups on the backbone chain, the peak at δ of 1.6ppm represents a methylene group bonded to a methyl group, the peak at δ of 2.0ppm represents a methylene group bonded to an ethylenic bond, the peak at δ of 2.3ppm represents a methylene group bonded to a carboxyl group, and the peak at δ of 5.30 to 5.41ppm represents a carbon-carbon double bond-CH*＝CH*-. In addition, the peak at δ ═ 2.7ppm represents a methylene group between two olefinic bonds, and is an impurity peak; the hydrogen on the carboxyl group of oleic acid was 9.75ppm at δ, which is not shown due to too small peak intensity.
As shown in fig. 2, in the nmr hydrogen spectrum of neopentyl glycol, the peak at δ ═ 0.9ppm represents a methyl group, and the peak at δ ═ 2.8ppm represents a hydroxyhydro-OH group*And the peak at δ ═ 3.5ppm represents methylene-CH attached to the hydroxyl group* 2-OH。
Referring to FIG. 2, it can be seen that in the NMR spectrum of the intermediate neopentyl glycol oleate synthesized in step 1) in FIG. 3, the methylene group-CH bonded to the hydroxyl group is represented at a concentration of 3.5ppm* 2The peak of-OH disappears, and a strong peak appears at the position of delta-3.8 ppm, which represents a methylene group connected with a carbonyl group in neopentyl glycol group, so that the hydroxyl group in neopentyl glycol and the carboxyl group in oleic acid are subjected to esterification reaction to synthesize neopentyl glycol oleate.
Referring to fig. 1 and 3, in the nmr hydrogen spectrogram of the neopentyl glycol epoxy oleate synthesized in step 2) in fig. 4, the part where δ is 5.30 to 5.41ppm represents a carbon-carbon double bond — CH*＝CH*Disappearance of the peak at δ of 3.1ppm and new appearance of a peak indicating a hydrogen proton peak of the epoxy bond, indicating that the carbon-carbon double bond in neopentyl glycol oleate as an intermediate synthesized in step 1) was epoxidized to synthesize neopentyl glycol oleate.
b. Infrared spectrogram
In addition to the detailed analysis of the nuclear magnetic resonance hydrogen spectrograms of the raw materials and products of the invention to prove that the target product is synthesized by the method of the invention, the applicant also analyzes the structures of intermediate products and final products by infrared spectroscopy to further prove the feasibility of the invention.
As shown in FIG. 5, 3008cm in the infrared spectrum of the neopentyl glycol oleate as an intermediate product synthesized in the step 1)-1C-H stretching shock absorption for unsaturated hydrocarbon CH ═ CH; 2926cm-1Is a saturated hydrocarbon CH2C-H asymmetric telescopic vibration absorption; 2855cm-1Is a saturated hydrocarbon CH2C-H symmetric telescopic vibration absorption; 1741cm-1C ═ O stretching shock absorption for the ester, indicating that more carbonyl groups are present in the intermediate product; 1464cm-1C-H asymmetric bending vibration of methyl; 1378cm-1C-H symmetric bending vibration of methyl; 1166cm-1C-O-C asymmetric stretching vibration; 1097cm-1C-O-C symmetric stretching vibration; 724cm-1Plane rocking vibration of methylene. Thus, the intermediate product is a long fatty acid chain compound containing a large number of carbonyl groups.
As can be seen from a comparison of FIG. 5, 3008cm is shown in the infrared spectrum of the neopentyl glycol oleate epoxy final product synthesized in step 2) in FIG. 6-1The C-H stretching vibration absorption peak of the unsaturated hydrocarbon CH ═ CH does not disappear, and the peak is 843 cm-1A new peak appears, and the peak represents the asymmetric stretching vibration of the ternary cyclic ether (epoxy bond) C-O-C. Thus, it was found that the carbon-carbon double bond in neopentyl glycol oleate, which is an intermediate product synthesized in step 1), was epoxidized to synthesize neopentyl glycol oleate.
Detailed analysis of FIGS. 1-6 fully illustrates that the method of the present invention can be used to synthesize a novel compound, epoxy neopentyl glycol oleate.
Example 2
Oleic acid and neopentyl glycol are used as raw materials to synthesize epoxy neopentyl glycol oleate, and the synthesis steps comprise:
1) esterification reaction: 549.9g of oleic acid, 104g of neopentyl glycol and 1.63g of tetrabutyl titanate serving as a catalyst are sequentially added into a three-neck round-bottom flask provided with a stirring device, a thermometer and a reflux condenser, nitrogen is introduced, the mixture is stirred and heated to 160 ℃, 180 ℃ and 200 ℃ for heat preservation reaction for 2 hours respectively, the mixture is subjected to heat preservation reaction for 2 hours at 230 ℃ and is subjected to heat preservation reaction for 3 hours at 250 ℃. And (3) intermittently taking the material, and finishing the reaction when the acid value of the sample is less than 2.0 to obtain the neopentyl glycol oleate which is a light yellow oily substance, wherein the acid value is detected to be 1.85 mgKOH/g.
2) Epoxidation reaction: 470g of neopentyl glycol oleate, 28g of formic acid and 1.40g of catalyst phosphoric acid which are prepared in the step 1) are added into a four-mouth round-bottom flask with a stirring device, a thermometer, a separating funnel and a reflux condenser, the temperature is raised to 60 ℃ by stirring, 320g of 50% hydrogen peroxide is slowly dropped while stirring, after the addition is finished, the reaction is carried out for 6 hours at 70 ℃, the lower layer of acid water is separated, the upper layer of oil ester is washed to be neutral by water, and the neopentyl glycol oleate epoxy light yellow oily substance is obtained by reduced pressure distillation to remove water and filtration, wherein the detection results of the physical and chemical indexes are shown in table 1.
Example 3
Oleic acid and neopentyl glycol are used as raw materials to synthesize epoxy neopentyl glycol oleate, and the synthesis steps comprise:
1) esterification reaction: 624g of oleic acid, 104g of neopentyl glycol and 2.76g of catalyst sodium phosphate are sequentially added into a three-neck round-bottom flask provided with a stirring device, a thermometer and a reflux condenser, nitrogen is introduced, the mixture is stirred and heated to 170 ℃, 190 ℃ and 210 ℃ for heat preservation reaction for 2 hours respectively, and the mixture is subjected to heat preservation reaction for 8 hours at 230 ℃. And (3) intermittently taking the material, and finishing the reaction when the acid value of the sample is less than 2.0 to obtain the neopentyl glycol oleate which is a light yellow oily substance, wherein the acid value is detected to be 1.90 mgKOH/g.
2) Epoxidation reaction: adding 500g of neopentyl glycol oleate prepared in the step 1), 39g of formic acid and 1.05g of catalyst phosphoric acid into a four-neck round-bottom flask with a stirring device, a thermometer, a separating funnel and a reflux condenser, stirring and heating to 60 ℃, slowly dropping 250g of 50% hydrogen peroxide while stirring, reacting at 65 ℃ for 10 hours after the addition is finished, separating out lower acid water, washing upper oil ester to be neutral, removing water by reduced pressure distillation and filtering to obtain light yellow oily epoxy neopentyl glycol oleate, wherein the detection results of the physical and chemical indexes are shown in table 1.
TABLE 1 physical and chemical indexes of neopentyl glycol epoxy oleate obtained in examples 1 to 3
Examples of the use of neopentyl glycol epoxy oleate
The neopentyl glycol epoxy oleate prepared in example 1 of the present invention and the commonly used commercial plasticizers DOP, DOA and TOTM in the prior art were subjected to comparative experiments on application properties. The experimental formula is as follows: 100 parts of PVC, 46 parts of plasticizer and 1.5 parts of heat stabilizer. The detection items and results are as follows:
1) processing time of different plasticized PVC mixed materials on an open mill, wherein the temperature of the open mill is 190 ℃;
during the plasticizing and forming process of a plurality of different plasticized PVC mixed materials on an open mill, the applicant finds that DOP, DOA and TOTM begin to stick wheels and can not be pulled out after 20 min; the plasticizing time of the PVC mixed material plasticized by epoxy neopentyl glycol oleate is prolonged to 40min, and the phenomenon of wheel sticking does not occur. It can be seen that the processing time of the epoxidized neopentyl glycol oleate plasticized PVC compound is much longer than that of the DOP, DOA and TOTM plasticized PVC compound.
2) The rheological properties of different plasticized PVC mixed materials in a rheometer are mainly considered, wherein the torque, the energy consumption and the decomposition time in the balance process are mainly considered, the temperature of the rheometer is 180 ℃, and the rotating speed of a rotor is 40 r/min;
as shown in fig. 7, the torques (Nm) of the different plasticized PVC mixes at equilibrium: DOP 3.8, DOA 3.7, epoxy neopentyl glycol oleate 4.8, TOTM 5.5, i.e. the torque of the PVC mixture plasticized by epoxy neopentyl glycol oleate at equilibrium is greater than DOP and DOA but less than TOTM; energy consumption (kJ) of different plasticized PVC mixtures in equilibrium: TOTM > epoxy neopentyl glycol oleate > DOA > DOP; final decomposition time of different plasticized PVC mixes: DOP 15min, DOA 13.8min, TOTM 15.5min and epoxy neopentyl glycol oleate 40min are still not decomposed, so that the processability of the PVC mixed material plasticized by epoxy neopentyl glycol oleate is better than that of the PVC mixed material plasticized by DOP, DOA and TOTM, and the result corresponds to the detection result of the item 1).
3) Low temperature embrittlement of different plasticized PVC articles;
as shown in Table 2, the epoxy neopentyl glycol oleate plasticized PVC products have a low temperature embrittlement performance of-30 ℃ and are inferior to DOP, DOA and TOTM plasticized PVC products, but still applicable to climatic conditions in most regions of China.
TABLE 2 Low temperature embrittlement of different plasticized PVC articles
Note: 8/30 represents 30 sample bars, breaking 8 upon impact.
4) Light transmittance and hardness of different plasticized PVC products;
as shown in Table 3, the visible light transmittance and the infrared ray blocking rate of different plasticized PVC products are not greatly different, but the ultraviolet ray blocking rate of the PVC product plasticized by the neopentyl glycol epoxy oleate is obviously superior to that of DOP, DOA and TOTM. Shore hardness A/15: TOTM plasticized PVC products are larger, DOP and epoxy neopentyl glycol oleate are inferior, and DOA is smaller.
TABLE 3 light transmittance and hardness of different plasticized PVC articles
5) Selecting common representative non-polar solvent n-hexane and polar solvent absolute ethyl alcohol for testing the solvent extraction resistance of different plasticized PVC products, wherein the soaking temperature is 25 ℃, the soaking time is 72 hours, and drying for 2 hours at 90 ℃ after taking out;
as shown in Table 4, in the n-hexane extraction resistance test, the residual rates of elongation at break of the PVC products plasticized by DOP and neopentyl glycol epoxy oleate are 88.24% and 87.99% respectively; while DOA and TOTM have almost no residue, 1.69% and 0.71%, respectively; the mass loss of different plasticized PVC products in normal hexane is sequentially DOA > TOTM > DOP > neopentyl glycol epoxy oleate. In the ethanol extraction resistance test, the DOP plasticized PVC article had an elongation at break residual of 79%, slightly lower for DOA and TOTM, 72.76% and 74.52%, respectively; the elongation at break residual rate of the epoxy neopentyl glycol oleate plasticized PVC product is up to 96.22%; the mass loss of different plasticized PVC products in ethanol is sequentially DOA > DOP > neopentyl glycol epoxy oleate > TOTM. It is thus seen that neopentyl glycol epoxy oleate has very good resistance to extraction in both of these representative solvents.
TABLE 4 resistance to extraction of different plasticized PVC articles in n-hexane, ethanol
6) Aging resistance tests are carried out on epoxy neopentyl glycol oleate and TOTM plasticized PVC products, and the thermal aging quality loss test conditions are 115 ℃ and 240 hours; the tensile property thermal aging test conditions are 136 ℃, 168h and 240 h;
as shown in Table 5, the elongation at break change rate and tensile strength change rate of the PVC product plasticized by epoxy neopentyl glycol oleate after aging are both smaller than those of the PVC product plasticized by TOTM, and the heat aging mass loss is only 1.88g/m2Also less than 8.48g/m of TOTM2It can be seen that the aging resistance of the epoxy neopentyl glycol oleate plasticized PVC product is superior to TOTM.
TABLE 5 ageing resistance of epoxy neopentyl glycol oleate and TOTM plasticized PVC articles
In conclusion, the epoxy neopentyl glycol oleate prepared by the invention can be used as a plasticizer, and has the characteristics of small viscosity, good stability, high fluidity and good plasticizing effect with plastics. When the ultraviolet-resistant coating is applied to plastics, the product has excellent processing performance, high ultraviolet blocking rate and good solvent precipitation resistance; the product has good aging resistance and low-temperature impact embrittlement performance, is a nontoxic plastic plasticizer with excellent properties, and has wide market application prospect.
The present invention has been described in detail with reference to the preferred embodiments. However, variations and additions to the embodiments will become apparent to those of ordinary skill in the art upon a reading of the foregoing description. It is the intention of the applicants that all such variations and additions fall within the scope of the claims. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Any modification and improvement of this product, and the substitution and use of the same or similar substances within the scope or range of patents, shall fall within the scope of protection of this invention.
Claims (13)
1. An epoxy neopentyl glycol oleate is characterized in that: has the following structural formula shown in the specification,
2. a method for synthesizing neopentyl glycol epoxidized oleate is characterized by comprising the following steps: comprises the following steps of (a) carrying out,
1) esterification reaction: oleic acid and neopentyl glycol are subjected to esterification reaction under the action of a catalyst to synthesize neopentyl glycol oleate,
2) epoxidation reaction: carrying out epoxidation reaction on neopentyl glycol oleate generated in the step 1) and hydrogen peroxide under the action of weak acid and a catalyst to synthesize epoxy neopentyl glycol oleate,
3. the method for synthesizing neopentyl glycol epoxy oleate according to claim 2, wherein: in the esterification reaction in the step 1), the weight ratio of oleic acid to neopentyl glycol is 4.9-6.0: 1.
4. the method for synthesizing neopentyl glycol epoxy oleate according to claim 2 or 3, characterized in that: in the esterification reaction in the step 1), the reaction temperature is 160-250 ℃, and the reaction time is 8-16 hours.
5. The method for synthesizing neopentyl glycol epoxy oleate according to claim 4, wherein: in the esterification reaction of the step 1), the reaction temperature is respectively kept at 170 ℃, 190 ℃ and 210 ℃ for 2 hours, and the temperature is kept at 230 ℃ for 8 hours.
6. The method for synthesizing neopentyl glycol epoxy oleate according to claim 4, wherein: and (2) introducing nitrogen for protection in the esterification reaction in the step 1).
7. The method for synthesizing neopentyl glycol epoxy oleate according to claim 2 or 3, characterized in that: in the esterification reaction in the step 1), the catalyst is at least one of tetrabutyl titanate, phosphoric acid and sodium phosphate.
8. The method for synthesizing neopentyl glycol epoxy oleate according to claim 7, wherein: in the esterification reaction in the step 1), the dosage of the catalyst is 0.1-0.4% of the total weight of oleic acid and neopentyl glycol.
9. The method for synthesizing neopentyl glycol epoxy oleate according to claim 2, wherein: in the epoxidation reaction in the step 2), the reaction temperature is 60-80 ℃, and the reaction time is 4-10 hours.
10. The method for synthesizing neopentyl glycol epoxy oleate according to claim 2 or 9, characterized in that: in the epoxidation reaction in the step 2), the catalyst is sulfuric acid or phosphoric acid.
11. The method for synthesizing neopentyl glycol epoxy oleate according to claim 2 or 9, characterized in that: in the epoxidation reaction in the step 2), the weak acid is formic acid and/or acetic acid.
12. A synthesis method according to claim 2 or 9, characterized in that: in the epoxidation reaction in the step 2), the weight ratio of neopentyl glycol oleate, hydrogen peroxide, weak acid and a catalyst is 1: 0.4-0.7: 0.04-0.08: 0.001-0.003.
13. Use of neopentyl glycol epoxy oleate according to claim 1 as plasticizer.
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