CN111423328B - Preparation method of decyl oleate - Google Patents
Preparation method of decyl oleate Download PDFInfo
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- CN111423328B CN111423328B CN202010254158.7A CN202010254158A CN111423328B CN 111423328 B CN111423328 B CN 111423328B CN 202010254158 A CN202010254158 A CN 202010254158A CN 111423328 B CN111423328 B CN 111423328B
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- SASYSVUEVMOWPL-NXVVXOECSA-N decyl oleate Chemical compound CCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC SASYSVUEVMOWPL-NXVVXOECSA-N 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 80
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 19
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims abstract description 16
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 15
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 15
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000005642 Oleic acid Substances 0.000 claims abstract description 15
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 15
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 239000005489 Bromoxynil Substances 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 17
- 239000003930 superacid Substances 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 9
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 9
- 235000011150 stannous chloride Nutrition 0.000 claims description 9
- 239000001119 stannous chloride Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 7
- -1 n-decyl ester Chemical class 0.000 claims description 7
- 229910016287 MxOy Inorganic materials 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000009286 beneficial effect Effects 0.000 description 9
- 238000007086 side reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 229960005486 vaccine Drugs 0.000 description 8
- 238000001514 detection method Methods 0.000 description 7
- 230000002349 favourable effect Effects 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000001737 promoting effect Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FAKFSJNVVCGEEI-UHFFFAOYSA-J tin(4+);disulfate Chemical compound [Sn+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O FAKFSJNVVCGEEI-UHFFFAOYSA-J 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
- C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/135—Compounds comprising a halogen and titanum, zirconium, hafnium, germanium, tin or lead
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of compound synthesis, and provides a preparation method of decyl oleate aiming at the problem that the prior art does not have a preparation method of decyl oleate, which comprises the following steps: mixing oleic acid and decanol to form a premix; step (2), adding a catalyst into the premix to form a mixture; and (3) heating the mixture to 160-280 ℃, reacting for 2-12h, and taking the reacted mixture to obtain decyl oleate. The method has the effects of accelerating the reaction rate and improving the yield and the purity of the product.
Description
Technical Field
The invention relates to the technical field of compound synthesis, in particular to a preparation method of decyl oleate.
Background
Currently, from a biological point of view, decyl oleate is a skin fat-like substance, is non-irritating, is a yellowish transparent liquid at room temperature, and is miscible with most commonly used fat-like raw materials.
Decyl oleate has good fluidity, strong diffusivity, strong osmosis and high temperature resistance, and is proved to be suitable for the physiological condition of a human body by a large number of toxicity tests and skin tests.
According to the latest research, the decyl oleate is expected to be used for preparing a stabilizer of a new corona vaccine to improve the stability of the new corona vaccine in the storage process, so that the new corona vaccine is less prone to losing activity in the storage process, and the efficacy of the new corona vaccine is less prone to being influenced, therefore, the decyl oleate has great significance for further research of the new corona vaccine.
However, a preparation method of decyl oleate is not found at present, the purity of decyl oleate purchased from the market is difficult to guarantee, and if the purity of decyl oleate cannot reach more than 98%, the effect of improving the stability of the new crown vaccine cannot be achieved, and even the effect of the new crown vaccine may be influenced, so that the preparation method of decyl oleate is of great significance for further research of the new crown vaccine.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a preparation method of decyl oleate.
The above object of the present invention is achieved by the following technical solutions:
a method of making decyl oleate, comprising the steps of:
mixing oleic acid and decanol to form a premix;
step (2), adding a catalyst into the premix to form a mixture;
and (3) heating the mixture to 160-280 ℃, reacting for 2-12h, and taking the reacted mixture to obtain decyl oleate.
By adopting the technical scheme, the reaction temperature and the reaction time are controlled, so that the reaction is favorably promoted to be carried out better, the reaction conversion rate is higher, and meanwhile, the side reaction and the reverse reaction are favorably inhibited better, so that the reaction yield is favorably improved, and the product purity is favorably improved.
In addition, the reaction temperature is controlled, so that the reaction rate is favorably improved, the reaction time is shorter, the production efficiency is favorably improved, and the production cost is favorably saved.
The present invention in a preferred example may be further configured to: in the step (2), the catalyst is one or two of solid super acid or stannous chloride.
By adopting the technical scheme, the solid super acid or stannous chloride is used as the catalyst, so that the reaction rate is favorably improved, reactants are easily and completely converted into target products, the reaction time is favorably shortened, the production efficiency is favorably improved, and the production cost is favorably saved.
In the present invention, the solid super acid may be SO4 2-/Fe2O3Solid super acid, SO4 2-/TiO2Solid super acid, SO4 2-/ZnO2Solid super acid, WO3/ZnO2Solid super acid, MoO3/ZnO2One or more of solid super acids.
The present invention in a preferred example may be further configured to: the solid super acid is SO4 2-/MxOyThe type solid super acid, wherein M is Zr or Ti or Fe.
By adopting the technical scheme, SO is adopted4 2-/MxOyThe solid super acid is used as the solid super acid, which is beneficial to better promoting the reaction and improving the reaction rate, thereby being beneficial to better shortening the reaction time, being beneficial to better improving the production efficiency and ensuring that the production cost is lower.
The present invention in a preferred example may be further configured to: in the step (2), the adding mass of the catalyst is 3-10% of the mass of the premix.
By adopting the technical scheme, the catalyst can better play a catalytic role by controlling the adding quality of the catalyst, so that the reaction rate can be better improved, and the reaction time is shorter; meanwhile, the dosage of the catalyst is not easy to be excessive, which is beneficial to better saving resources; in addition, the method is favorable for inhibiting side reactions and reverse reactions better, so that the yield and the purity of the product are higher.
The present invention in a preferred example may be further configured to: in the step (2), 4-bromoxynil is also added into the premix.
By adopting the technical scheme, the 4-bromoxynil is added, so that the catalytic action of the catalyst is promoted better, the forward reaction rate of the reaction is higher, the reaction time is shortened better, the production efficiency is improved better, and the production cost is lower.
The present invention in a preferred example may be further configured to: in the step (2), the adding mass of the 4-bromoxynil is 0.1-0.5% of the mass of the catalyst.
By adopting the technical scheme, the catalytic action of the catalyst can be better promoted by controlling the addition amount of the 4-bromoxynil, so that the forward reaction rate of the reaction is higher, the reaction time can be better shortened, the production efficiency is higher, and the production cost can be better reduced; meanwhile, the dosage of the 4-bromoxynil is not easy to be excessive, which is beneficial to better saving resources; in addition, the method is favorable for better reducing side reactions and reverse reactions, so that the yield and the purity of the product are improved.
The present invention in a preferred example may be further configured to: in the step (1), the mass part ratio of the oleic acid to the n-decyl ester is 1.1-2.1: 1.
by adopting the technical scheme, the method is favorable for better complete reaction of reactants and better improvement of the conversion rate of the reaction by controlling the mass part ratio of the oleic acid and the n-decyl ester, so that the yield of the reaction and the purity of the product are higher.
The present invention in a preferred example may be further configured to: in the step (3), the mixture is heated to 220-260 ℃ and reacts for 2-4 h.
By adopting the technical scheme, the reaction speed is favorably accelerated better by controlling the reaction temperature, so that the reaction time is shorter, the production efficiency is favorably improved better, and the production cost is reduced.
The present invention in a preferred example may be further configured to: and (3) filling inert gas or vacuumizing in the reaction process.
By adopting the technical scheme, the reaction system is less prone to oxygen by filling inert gas or vacuumizing in the reaction process, so that the side reaction is favorably reduced, the reaction yield is favorably improved, and the product purity is favorably improved; meanwhile, the water vapor in the reaction system is easier to be discharged out of the reaction system along with the inert gas and the vacuumized airflow, so that the water vapor content in the reaction system is favorably reduced, the reverse reaction is favorably inhibited better, and the yield and the product purity of the reaction are higher.
The present invention in a preferred example may be further configured to: and (3) placing the reacted mixture in a sealed environment and cooling to room temperature to obtain decyl oleate.
By adopting the technical scheme, the target product is cooled to room temperature in a closed environment, so that the target product is not easily oxidized in the cooling process, the oxidation reaction and the side reaction are favorably reduced, and the purity of the target product is favorably improved.
In summary, the invention includes at least one of the following beneficial technical effects:
1. by controlling the reaction temperature and the reaction time, the method is favorable for better promoting the reaction, so that the conversion rate of the reaction is higher, and simultaneously, the method is favorable for better inhibiting side reaction and reverse reaction, and is favorable for better improving the yield of the reaction and the purity of the product;
2. by controlling the reaction temperature, the reaction rate is favorably improved, the reaction time is shortened, the production efficiency is favorably improved, and the production cost is favorably saved;
3. by adopting solid super acid or stannous chloride as a catalyst, the reaction rate is favorably improved, and reactants are easily and completely converted into target products, so that the reaction time is favorably shortened, the production efficiency is favorably improved, and the production cost is favorably saved;
4. by adding 4-bromoxynil, the catalytic action of the catalyst is promoted better, the forward reaction rate of the reaction is higher, the reaction time is shortened better, the production efficiency is improved better, and the production cost is lower.
Drawings
FIG. 1 is a schematic representation of decyl oleate prepared in the present invention1A HNMR map;
FIG. 2 is an IR spectrum of decyl oleate prepared in the present invention.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings.
Example 1
A method of making decyl oleate, comprising the steps of:
step (1), adding 1kg of oleic acid and 1kg of n-decanol into a four-neck flask, and uniformly mixing to form a premix.
Step (2), 0.22kg of SO was further added into the four-necked flask4 2-/Fe2O3Solid super acid, and mixing to form the mixture.
And (3) putting the four-neck flask filled with the mixture into an oil bath pot, installing a condensing tube at one opening of the four-neck flask to discharge water vapor in the reaction system, meanwhile, placing a conical flask at one end of the condensing tube far away from the four-neck flask to collect water formed by condensing the water vapor, plugging other openings of the four-neck flask by using rubber stoppers, heating the oil bath to 160 ℃, reacting for 12 hours, and cooling to room temperature to obtain decyl oleate.
Referring to FIG. 1, there is shown decyl oleate prepared in this example1The HNMR spectrum, see fig. 2, is an infrared spectrum of decyl oleate prepared in this example, which is obtained by combining fig. 1 and fig. 2, and the decyl oleate is obtained in the reaction.
Example 2
The difference from example 1 is that: the reaction temperature in the step (3) is 280 ℃, and the reaction time is 5 hours.
Example 3
The difference from example 1 is that: the reaction temperature in the step (3) is 220 ℃, and the reaction time is 4h
Example 4
The difference from example 1 is that: the reaction temperature in the step (3) is 240 ℃, and the reaction time is 3 h.
Example 5
The difference from example 1 is that: the reaction temperature in the step (3) is 260 ℃, and the reaction time is 2 h.
Example 6
The difference from example 1 is that: the reaction temperature in the step (3) is 250 ℃, and the reaction time is 2 h.
Example 7
The difference from example 6 is that: the catalyst in the step (2) is stannous chloride.
Example 8
The difference from example 7 is that: the addition amount of stannous chloride in step (2) is 2% of the mass of the premix, i.e. 0.04 kg.
Example 9
The difference from example 7 is that: the addition amount of stannous chloride in step (2) is 3% of the mass of the premix, i.e. 0.06 kg.
Example 10
The difference from example 7 is that: the addition amount of stannous chloride in step (2) is 10% of the mass of the premix, i.e. 0.2 kg.
Example 11
The difference from example 7 is that: 4-bromoxynil was also added in step (2), the amount of 4-bromoxynil added was 0.6% by mass of the catalyst, i.e. 1.32 g.
Example 12
The difference from example 7 is that: 4-bromoxynil was also added in step (2), the amount of 4-bromoxynil added was 0.1% by mass of the catalyst, i.e. 0.22 g.
Example 13
The difference from example 7 is that: 4-bromoxynil was also added in step (2), the amount of 4-bromoxynil added being 0.5% by mass of the catalyst, i.e. 1.1 g.
Example 14
The difference from example 6 is that: the mass ratio of the oleic acid to the n-decyl ester in the step (1) is 2.3: 1, 2.3kg of oleic acid and 1kg of n-decanol are added into a four-neck flask. Accordingly, the amount of catalyst added corresponds to 0.363 kg.
Example 15
The difference from example 6 is that: the mass ratio of the oleic acid to the n-decyl ester in the step (1) is 1.1: 1, namely, 1.1kg of oleic acid and 1kg of n-decanol are added into a four-neck flask. Accordingly, the amount of the catalyst added corresponds to 0.231 kg.
Example 16
The difference from example 6 is that: the mass ratio of the oleic acid to the n-decyl ester in the step (1) is 2.1: 1, 2.1kg of oleic acid and 1kg of n-decanol are added into a four-neck flask. Accordingly, the amount of catalyst added corresponds to 0.341 kg.
Example 17
The difference from example 6 is that:
step (3), placing the four-neck flask filled with the mixture into an oil bath kettle, continuously introducing nitrogen into one opening of the four-neck flask, and controlling the flow rate of the nitrogen to be 10m3And h, simultaneously leading out nitrogen from the other opening of the four-neck flask, installing a condensation pipe at the opening for discharging the nitrogen to condense the water vapor in the reaction system, placing a conical flask at one end of the condensation pipe far away from the four-neck flask to collect water formed by condensing the water vapor, plugging the other openings of the four-neck flask by using rubber plugs, keeping the pressure in the four-neck flask at normal pressure, heating the oil bath to 250 ℃, reacting for 2h, stopping introducing the nitrogen, and cooling to room temperature to obtain decyl oleate.
Example 18
The difference from example 6 is that:
and (3) putting the four-neck flask filled with the mixture into an oil bath pot, installing a vacuum pump at one opening of the four-neck flask to vacuumize, installing a condensing tube at an exhaust port of the vacuum pump to condense water vapor in the reaction system, placing a conical flask at one end of the condensing tube far away from the vacuum pump to collect water formed by condensation of the water vapor, plugging other openings of the four-neck flask by using rubber plugs, controlling the vacuum pressure in the reaction system to be 0.1MPa, heating the oil bath to 250 ℃, reacting for 2h, stopping vacuumizing, and cooling to room temperature to obtain decyl oleate.
Example 19
A method of making decyl oleate, comprising the steps of:
step (1), 1.5kg of oleic acid and 1kg of n-decanol were added to a four-necked flask and mixed uniformly to form a premix.
Step (2), 0.1kg of stannous chloride and 0.2g of 4-bromoxynil were added to the four-neck flask and mixed well to form a mixture.
Step (3), placing the four-neck flask filled with the mixture into an oil bath kettle, continuously introducing nitrogen into one opening of the four-neck flask, and controlling the flow rate of the nitrogen to be 10m3And h, simultaneously leading out nitrogen from the other opening of the four-neck flask, installing a condensing tube at the opening discharged by the nitrogen to condense the water vapor in the reaction system, placing a conical flask at one end of the condensing tube far away from the four-neck flask to collect water formed by condensing the water vapor, plugging the other openings of the four-neck flask by rubber plugs, keeping the pressure in the four-neck flask at normal pressure, heating the oil bath to 250 ℃, reacting for 2h, stopping introducing the nitrogen, plugging the openings of the four-neck flask by rubber plugs, placing the reacted mixture in a sealed environment, and cooling to room temperature to obtain decyl oleate.
Comparative example 1
The difference from example 6 is that: the reaction temperature in the step (3) is 150 ℃, and the reaction time is 13 h.
Comparative example 2
The difference from example 6 is that: the reaction temperature in the step (3) is 300 ℃, and the reaction time is 1.5 h.
Comparative example 3
The difference from example 6 is that: the catalyst added in the step (2) is concentrated sulfuric acid.
Comparative example 4
The difference from example 6 is that: the catalyst added in the step (2) is tin sulfate.
The substances prepared in examples 2 to 19 and comparative examples 1 to 4 were analyzed by the same detection method as in example 1, and the spectra obtained by the detection analysis were almost the same as in example 1, and only the differences in yield and purity were observed, and thus, the details thereof are not repeated.
Performance detection
Detecting and recording the quality index of the decyl oleate prepared in the above embodiment, wherein the acid value obtained by detection is in the range of 0.3-0.5; the hydroxyl value obtained by detection is in the range of 0.5-1; the iodine values obtained by detection are all in the range of 57-60; the ester values obtained by detection are all in the range of 138-143, and accord with the quality index of decyl oleate.
The reaction yield (%) and the product purity (%) of the above examples and comparative examples were measured and recorded.
The reaction time (min) was recorded when the reaction products all meet the following criteria: the acid value is less than or equal to 0.6; hydroxyl value is less than or equal to 1.5; iodine number in the range of 55-60; the ester number is in the range of 135-145.
The data from the above experiments are shown in Table 1.
TABLE 1
Wherein, "-" in the table indicates that the target product cannot reach the quality index in the preparation process.
As can be seen from the comparison of the data in Table 1 of examples 1-6 with comparative examples 1-2, the reaction temperature and reaction time in step (3) are controlled to facilitate the better improvement of the conversion rate of the reaction, and simultaneously, to facilitate the better inhibition of the side reactions and the reverse reactions, thereby facilitating the better improvement of the yield and product purity of the reaction; in addition, the method is favorable for better improving the reaction rate, so that the time for the reaction product to reach the quality index is shorter, the production efficiency is favorably improved, and the production cost is reduced.
As can be seen from the comparison of the data of examples 6 to 7 with comparative examples 3 to 4 in Table 1, the progress of the reaction can be promoted better by controlling the kind of the catalyst, so that the time for the reaction product to reach the quality index can be shortened, the production efficiency can be improved better, and the production cost can be reduced.
According to the comparison of the data of the examples 7-10 in the table 1, the catalyst can be better promoted by controlling the adding amount of the catalyst, so that the reaction rate can be better improved, the time for the reaction product to reach the quality index is shorter, the production efficiency can be better improved, and the production cost is reduced; in addition, the method is beneficial to reducing side reactions and reverse reactions, so that the yield of the reaction and the purity of the product are improved.
According to the comparison of the data of the example 7 and the examples 11-13 in the table 1, the addition of the 4-bromoxynil is beneficial to better promoting the catalytic action of the catalyst, so that the reaction rate is faster, and the time for the reaction product to reach the quality index is favorably shortened; by controlling the addition amount of the 4-bromoxynil, the method is also beneficial to better promoting the catalytic action of the catalyst by the 4-bromoxynil, so that the reaction rate is faster, the time for the reaction product to reach the quality index is shorter, the side reaction and the reverse reaction are better reduced, and the yield of the reaction and the purity of the product are improved.
As can be seen from the comparison of the data of example 6 and examples 14-16 in Table 1, the mass ratio of oleic acid to n-decyl ester is controlled to facilitate the improvement of the conversion rate of the reaction, and to facilitate the better complete conversion of the reactant to the target product, thereby facilitating the better improvement of the yield and purity of the reaction.
According to the comparison of the data of example 6 and examples 17-18 in table 1, the nitrogen is filled in the reaction process or the vacuum is pumped in the reaction process, so that the water vapor content in the reaction system is favorably reduced, the reverse reaction is favorably inhibited, and the yield of the reaction and the purity of the product are improved.
The embodiments of the present invention are preferred embodiments of the present invention, and the scope of the present invention is not limited by these embodiments, so: all equivalent changes made according to the structure, shape and principle of the invention are covered by the protection scope of the invention.
Claims (2)
1. A preparation method of decyl oleate is characterized in that: the method comprises the following steps:
mixing oleic acid and decanol to form a premix;
adding a catalyst and 4-bromoxynil into the premix, wherein the mass of the added 4-bromoxynil is 0.2-0.5% of the mass of the catalyst, and forming a mixture;
step (3), heating the mixture to 220-260 ℃, reacting for 2-4h, taking the reacted mixture, and filling nitrogen or vacuumizing simultaneously in the reaction process to obtain decyl oleate;
the catalyst is one or two of solid super acid or stannous chloride, and the addition amount of the catalyst is 3-10% of the premix;
the mass part ratio of the oleic acid to the n-decyl ester is 1.1-2.1: 1;
the solid super acid is SO4 2-/MxOyThe type solid super acid, wherein M is Zr or Ti or Fe.
2. The method of making decyl oleate according to claim 1, characterized in that: and (3) placing the reacted mixture in a sealed environment and cooling to room temperature to obtain decyl oleate.
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Denomination of invention: Preparation method of decane oleate Granted publication date: 20220415 Pledgee: Industrial and Commercial Bank of China Limited Guangzhou Tianhe Sub-branch Pledgor: GUANGZHOU DREAM BIO-TECH Co.,Ltd. Registration number: Y2024980009170 |