CN108586183B - Supercritical technology-based method for separating and purifying high-purity alpha-methylnaphthalene - Google Patents
Supercritical technology-based method for separating and purifying high-purity alpha-methylnaphthalene Download PDFInfo
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Abstract
The invention provides a method for separating and purifying high-purity alpha-methylnaphthalene based on a supercritical technology, which comprises the following steps: adding ethanolamine into the methylnaphthalene fraction, uniformly mixing by a premixer, transferring the methylnaphthalene fraction into a supercritical reactor, heating to 180 ℃, starting condensed water, cooling and stirring, cooling to 166-168 ℃, stopping heating after constant-temperature reaction, and separating and collecting gas-liquid products to obtain the denitrified methylnaphthalene composition; preheating the denitrified methylnaphthalene composition, slowly dropwise adding an acetic anhydride catalyst and a peroxide hydroxide, heating and ultrasonically stirring at a high speed, and extracting and rectifying to obtain the desulfurized methylnaphthalene composition; adding ethylene glycol into the desulfurized methylnaphthalene composition, performing azeotropic distillation, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition, performing azeotropic distillation, and separating to obtain high-purity alpha-methylnaphthalene with the purity of 99.8%.
Description
Technical Field
The invention belongs to the technical field of separation and purification of alpha-methylnaphthalene, and particularly relates to a separation and purification method of high-purity alpha-methylnaphthalene based on a supercritical technology.
Background
Alpha-methylnaphthalene, also called 1-methylnaphthalene, is a colorless or light yellow liquid with blue fluorescence at normal temperature, has the smell of naphthalene, is insoluble in water and alkali, is easily soluble in diethyl ether, acetone and aromatic hydrocarbon, has a melting point of-22 ℃, a boiling point of 244.6 ℃ and a density of 1.02, and can be used for synthesizing 1, 4-naphthalenedicarboxylic acid, used as a raw material for producing fluorescent brightener dyes and engineering plastics, synthesizing 1-naphthalenedicarboxylic acid as a plant growth hormone and synthesizing 1-naphthoic acid as a raw material for color photographic dyes and also used as a medical intermediate.
At present, the alpha-methylnaphthalene is mainly extracted from coal tar or heavy aromatics, but the separation is difficult by adopting a conventional rectification method because the boiling points of the alpha-methylnaphthalene and the beta-methylnaphthalene are similar. The method for preparing alpha-methylnaphthalene disclosed in Chinese patent CN 101250082A comprises using petroleum-grade mixed methylnaphthalene containing 5-15% of alpha-methylnaphthalene as raw material, adopting batch type rectifying tower, under the vacuum degree of 0.08-0.09MPa, when the temperature at the bottom of the tower is 190-. The purification process of alpha-methylnaphthalene disclosed in chinese patent CN 101270028B is to add metal aluminum/zinc halide to alpha-methylnaphthalene after removing indole as raw material, react, filter to remove solid matter, add methanol/ethanol/propanol/ether/benzene washing solvent to the filtrate, fully oscillate at 30-50 ℃, take the upper solution, remove the solvent, and obtain purified alpha-methylnaphthalene. Fully suspending metal halide in alpha-methylnaphthalene raw material liquid to remove solid small particles and partial flocculate, fully oscillating and standing with a solvent to dissolve most of alpha-methylnaphthalene in the solvent, and removing a small amount of alpha-methylnaphthalene and most of impurities and flocculate again to obtain alpha-methylnaphthalene with the purity of more than 99%. As known from the prior art, the alpha-methylnaphthalene can be separated and purified by adding a solvent and performing batch rectification, wherein the main impurities of the alpha-methylnaphthalene are methylbenzothiophene, biphenyl, quinoline and indole, but the quinoline and the indole are removed in a separation method, so that acid or alkali residue is inevitably present, and the purity of the alpha-methylnaphthalene is influenced.
Disclosure of Invention
The invention aims to solve the technical problem of providing a separation and purification method of high-purity alpha-methylnaphthalene based on a supercritical technology, which is characterized in that methylnaphthalene fractions containing sulfides such as methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene, thianaphthene and methyl thianaphthene and having the total methylnaphthalene content of not less than 60 percent are used as raw materials and are respectively subjected to supercritical treatment, oxidation and azeotropic treatment to prepare the high-purity alpha-methylnaphthalene.
In order to solve the technical problems, the technical scheme of the invention is as follows:
a separation and purification method of high-purity alpha-methylnaphthalene based on supercritical technology is characterized by comprising the following steps: the method comprises the following steps:
(1) adding ethanolamine into the methylnaphthalene fraction, uniformly mixing by a premixer, transferring the methylnaphthalene fraction into a supercritical reactor, reacting at constant temperature, stopping heating, and separating and collecting gas-liquid products to obtain a nitrogen-removed methylnaphthalene composition;
(2) preheating the denitrified methylnaphthalene composition prepared in the step (1), slowly dropwise adding an acetic anhydride catalyst and a peroxide hydroxide, and extracting and rectifying under ultrasonic waves to obtain a desulfurized methylnaphthalene composition;
(3) adding ethylene glycol into the sulphur-removed methylnaphthalene composition prepared in the step (2), heating to 190-195 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropy, and separating to obtain high-purity alpha-methylnaphthalene.
Preferably, in the step (1), the methylnaphthalene fraction contains methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide, and the total methylnaphthalene content is not less than 60%.
Preferably, in the step (1), the volume ratio of the ethanolamine to the total methylnaphthalene is 3: 5-10.
Preferably, in the step (1), ethanolamine is added into the methylnaphthalene fraction, the mixture is uniformly mixed by a premixer, the mixture is transferred to a supercritical reactor, the temperature is raised to 185 ℃ at the speed of 15-20 ℃/min, condensed water is started to cool and stir for 1-2h, the temperature is lowered to 160 ℃ at the speed of 5-10 ℃/min, the heating is stopped after the constant temperature reaction is carried out for 2-4h, and the gas-liquid product is separated and collected to obtain the nitrogen-removed methylnaphthalene composition.
Preferably, in the step (1), the cooling and stirring speed is 150-.
Preferably, in the step (2), the preheating temperature is 70-80 ℃.
Preferably, in the step (2), the molar ratio of the acetic anhydride catalyst, the peroxide hydroxide and the sulfide is 5.1-5.3:6.5-7.5: 1.
Preferably, in the step (2), the mixture is stirred at a high speed for 60-90min at 70-80 ℃ and under ultrasonic waves, the intensity of the ultrasonic waves is 250-400W, and the rotating speed of the high-speed stirring is 2000-5000 r/min.
Preferably, in the step (2), the solvent for extraction is furfural, methanol, ethylenediamine or N-methylpyrrolidone.
Preferably, in the step (3), the mass ratio of the high-purity alpha + beta methylnaphthalene composition to the 2-amino-3-methylpyridine is 1: 0.3-0.8.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention relates to a separation and purification method of high-purity alpha-methylnaphthalene based on supercritical technology, which takes methylnaphthalene fraction containing methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide and not less than 60 percent of the total methylnaphthalene as raw material, firstly adds ethanolamine to remove nitrogen-containing impurities such as indole and quinoline through supercritical treatment, then adopts oxidation reaction, takes acetic anhydride micro-catalyst and hydrogen peroxide as oxide to oxidize the methylbenzothiophene into sulfoxide or sulfone, then takes furfural, methanol, ethylenediamine or N-methylpyrrolidone as extractant to extract and remove the methylbenzothiophene, the oxidation method is mild, avoids using strong acid, has little acid consumption, and further improves the desulfurization effect by combining ultrasonic technology and high-speed stirring technology in the oxidation reaction, has high desulfurization efficiency, removing sulfides such as thianaphthene and methyl thianaphthene, and finally adding ethylene glycol and 2-amino-3-methylpyridine for azeotropy in the desulfurized methylnaphthalene composition, removing biphenyl and dimethylnaphthalene, and separating high-purity alpha-methylnaphthalene by utilizing the characteristic that 2-amino-3-methylpyridine and beta-methylnaphthalene form an azeotrope and do not form an azeotrope with alpha-methylnaphthalene.
(2) The method for separating and purifying the high-purity alpha-methylnaphthalene based on the supercritical technology combines the supercritical technology with the oxidation technology and the azeotropic technology, has strong controllability, prepares the high-purity alpha-methylnaphthalene through the optimized cooperation among all reactions, has the purity of 99.8 percent, fully meets the requirements of all fields on the alpha-methylnaphthalene, can separate the high-purity beta-methylnaphthalene from the prepared by-product beta-methylnaphthalene composition, and has high economic value.
Detailed Description
The present invention will be described in detail with reference to specific embodiments, which are illustrative of the invention and are not to be construed as limiting the invention.
Example 1:
(1) adding ethanolamine into methylnaphthalene fraction containing methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide and having total methylnaphthalene content not lower than 60% according to the volume ratio of ethanolamine to total methylnaphthalene being 3:5, uniformly mixing by a premixer, transferring into a supercritical reactor, heating to 180 ℃ at the rate of 20 ℃/min, cooling condensate water to 166 ℃ at the rate of 150r/min, reacting at constant temperature for 1h, stopping heating, and separating and collecting gas-liquid products to obtain the nitrogen-removed methylnaphthalene composition.
(2) Preheating the methyl naphthalene composition subjected to nitrogen removal to 70 ℃ according to the molar ratio of an acetic anhydride catalyst to peroxide hydroxide to sulfide of 5.1:6.5:1, slowly dropwise adding the acetic anhydride catalyst and the peroxide hydroxide at a rate of 1mL/5min, stirring at a high speed of 2000r/min for 60min at 70 ℃ under 250W of ultrasonic waves, extracting and rectifying by furfural to obtain the methyl naphthalene composition subjected to sulfur removal.
(3) Adding ethylene glycol into the desulfurized methylnaphthalene composition, heating to 190 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropic distillation according to the mass ratio of the high-purity alpha + beta methylnaphthalene composition to 2-amino-3-methylpyridine of 1:0.3, and separating to obtain high-purity alpha-methylnaphthalene.
Example 2:
(1) adding ethanolamine into methylnaphthalene fraction containing methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide and having total methylnaphthalene content not lower than 60% according to the volume ratio of ethanolamine to total methylnaphthalene being 3:10, uniformly mixing by a premixer, transferring to a supercritical reactor, heating to 180 ℃ at the rate of 25 ℃/min, cooling condensate water to 168 ℃ at the rate of 200r/min, reacting at constant temperature for 6h, stopping heating, and separating and collecting gas-liquid products to obtain the nitrogen-removed methylnaphthalene composition.
(2) Preheating the methyl naphthalene composition subjected to nitrogen removal to 80 ℃ according to the molar ratio of an acetic anhydride catalyst to peroxide hydroxide to sulfide of 5.3:7.5:1, slowly dropwise adding the acetic anhydride catalyst and the peroxide hydroxide at a rate of 5mL/5min, stirring at a high speed of 5000r/min for 90min at 80 ℃ under 400W of ultrasonic waves, extracting with methanol, and rectifying to obtain the methyl naphthalene composition subjected to sulfur removal.
(3) Adding ethylene glycol into the desulfurized methylnaphthalene composition, heating to 195 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropic distillation according to the mass ratio of the high-purity alpha + beta methylnaphthalene composition to 2-amino-3-methylpyridine of 1:0.8, and separating to obtain high-purity alpha-methylnaphthalene.
Example 3:
(1) adding ethanolamine into methylnaphthalene fraction containing methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide and having total methylnaphthalene content not lower than 60% according to the volume ratio of ethanolamine to total methylnaphthalene being 3:6, uniformly mixing by a premixer, transferring into a supercritical reactor, heating to 180 ℃ at the rate of 23 ℃/min, cooling condensate water to 167 ℃ at the rate of 180r/min, reacting at constant temperature for 4h, stopping heating, and separating and collecting gas-liquid products to obtain the nitrogen-removed methylnaphthalene composition.
(2) Preheating the methyl naphthalene composition subjected to nitrogen removal to 75 ℃ according to the molar ratio of an acetic anhydride catalyst to peroxide hydroxide to sulfide of 5.2:6.8:1, slowly dropwise adding the acetic anhydride catalyst and the peroxide hydroxide at a rate of 3mL/5min, stirring at a high speed of 3000r/min for 75min at 75 ℃ under 300W of ultrasonic waves, extracting with ethylenediamine, and rectifying to obtain the methyl naphthalene composition subjected to sulfur removal.
(3) Adding ethylene glycol into the desulfurized methylnaphthalene composition, heating to 193 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropic distillation according to the mass ratio of the high-purity alpha + beta methylnaphthalene composition to 2-amino-3-methylpyridine of 1:0.5, and separating to obtain high-purity alpha-methylnaphthalene.
Example 4:
(1) adding ethanolamine into methylnaphthalene fraction containing methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide and having total methylnaphthalene content not lower than 60% according to the volume ratio of ethanolamine to total methylnaphthalene being 3:8, uniformly mixing by a premixer, transferring into a supercritical reactor, heating to 180 ℃ at the rate of 23 ℃/min, cooling condensate water to 167 ℃ at the rate of 190r/min, reacting at constant temperature for 5h, stopping heating, and separating and collecting gas-liquid products to obtain the nitrogen-removed methylnaphthalene composition.
(2) Preheating the denitrified methylnaphthalene composition to 73 ℃ according to the molar ratio of the acetic anhydride catalyst to the peroxide hydroxide to the sulfide of 5.2:7.2:1, slowly dripping the acetic anhydride catalyst and the peroxide hydroxide at the speed of 2mL/5min, stirring at the high speed of 2500r/min for 80min at the temperature of 78 ℃ and under the ultrasonic wave of 350W, extracting and rectifying by using N-methyl pyrrolidone to obtain the desulfurized methylnaphthalene composition.
(3) Adding ethylene glycol into the desulfurized methylnaphthalene composition, heating to 193 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropic distillation according to the mass ratio of the high-purity alpha + beta methylnaphthalene composition to 2-amino-3-methylpyridine of 1:0.7, and separating to obtain high-purity alpha-methylnaphthalene.
Example 5:
(1) adding ethanolamine into methylnaphthalene fraction containing methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide and having total methylnaphthalene content not lower than 60% according to the volume ratio of ethanolamine to total methylnaphthalene being 3:5, uniformly mixing by a premixer, transferring to a supercritical reactor, heating to 180 ℃ at the rate of 20-25 ℃/min, cooling condensate water to 167.5 ℃ at the rate of 9 ℃/min, reacting at constant temperature for 2h, stopping heating, and separating and collecting gas-liquid products to obtain the nitrogen-removed methylnaphthalene composition.
(2) According to the mol ratio of the acetic anhydride catalyst to the peroxide hydroxide to the sulfide of 5.1:7:1, preheating the methyl naphthalene composition without nitrogen to 73 ℃, slowly dripping the acetic anhydride catalyst and the peroxide hydroxide at a speed of 4mL/5min, stirring at a high speed of 2000r/min for 90min at 70 ℃ and under 400W of ultrasonic waves, extracting and rectifying by using N-methyl pyrrolidone to obtain the methyl naphthalene composition without sulfur.
(3) Adding ethylene glycol into the desulfurized methylnaphthalene composition, heating to 190 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropic distillation according to the mass ratio of the high-purity alpha + beta methylnaphthalene composition to 2-amino-3-methylpyridine of 1:0.8, and separating to obtain high-purity alpha-methylnaphthalene.
Example 6:
(1) adding ethanolamine into methylnaphthalene fraction containing methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide and having total methylnaphthalene content not lower than 60% according to the volume ratio of ethanolamine to total methylnaphthalene being 3:9, uniformly mixing by a premixer, transferring into a supercritical reactor, heating to 180 ℃ at the rate of 25 ℃/min, cooling condensate water to 166 ℃ at the rate of 150r/min, reacting at constant temperature for 6h, stopping heating, and separating and collecting gas-liquid products to obtain the nitrogen-removed methylnaphthalene composition.
(2) Preheating the methyl naphthalene composition subjected to nitrogen removal to 80 ℃ according to the molar ratio of an acetic anhydride catalyst to peroxide hydroxide to sulfide of 5.3:6.5:1, slowly dropwise adding the acetic anhydride catalyst and the peroxide hydroxide at a rate of 1mL/5min, stirring at a high speed of 5000r/min for 60min at 80 ℃ under 250W of ultrasonic waves, extracting and rectifying by furfural to obtain the methyl naphthalene composition subjected to sulfur removal.
(3) Adding ethylene glycol into the desulfurized methylnaphthalene composition, heating to 195 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropic distillation according to the mass ratio of the high-purity alpha + beta methylnaphthalene composition to 2-amino-3-methylpyridine of 1:0.3, and separating to obtain high-purity alpha-methylnaphthalene.
The high purity alpha-methylnaphthalene prepared in examples 1-6 was determined to have a purity of 99.81%, 99.79%, 99.82%, 99.73%, 99.78%, 99.80%, respectively.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.
Claims (10)
1. A separation and purification method of high-purity alpha-methylnaphthalene based on supercritical technology is characterized by comprising the following steps: the method comprises the following steps:
(1) adding ethanolamine into the methylnaphthalene fraction, uniformly mixing by a premixer, transferring the methylnaphthalene fraction into a supercritical reactor, reacting at constant temperature, stopping heating, and separating and collecting gas-liquid products to obtain a nitrogen-removed methylnaphthalene composition;
(2) preheating the denitrified methylnaphthalene composition prepared in the step (1), slowly dropwise adding an acetic anhydride catalyst and a peroxide hydroxide, and extracting and rectifying under ultrasonic waves to obtain a desulfurized methylnaphthalene composition;
(3) adding ethylene glycol into the sulphur-removed methylnaphthalene composition prepared in the step (2), heating to 190-195 ℃, collecting gas, condensing to obtain a high-purity alpha + beta methylnaphthalene composition, adding 2-amino-3-methylpyridine into the high-purity alpha + beta methylnaphthalene composition for azeotropy, and separating to obtain high-purity alpha-methylnaphthalene.
2. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 1, which is based on supercritical technology, and is characterized in that: in the step (1), the methylnaphthalene fraction contains methylnaphthalene, quinoline, indole, biphenyl, methylbenzothiophene and thianaphthene sulfide, and the total methylnaphthalene content is not less than 60%.
3. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 1, which is based on supercritical technology, and is characterized in that: in the step (1), the volume ratio of the ethanolamine to the total methylnaphthalene is 3: 5-10.
4. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 1, which is based on supercritical technology, and is characterized in that: in the step (1), ethanolamine is added into the methylnaphthalene fraction, the methylnaphthalene fraction is uniformly mixed by a premixer, then the mixture is transferred to a supercritical reactor, the temperature is raised to 185 ℃ with the speed of 15-20 ℃/min, condensed water is started to cool and stir for 1-2h, the temperature is lowered to 160 ℃ with the speed of 5-10 ℃/min, the heating is stopped after the constant temperature reaction is carried out for 2-4h, and the gas-liquid product is separated and collected to obtain the nitrogen-removed methylnaphthalene composition.
5. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 4, which is based on supercritical technology, and is characterized in that: in the step (1), the cooling and stirring speed is 150-.
6. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 1, which is based on supercritical technology, and is characterized in that: in the step (2), the preheating temperature is 70-80 ℃.
7. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 2, which is based on supercritical technology, and is characterized in that: in the step (2), the molar ratio of the acetic anhydride catalyst, the peroxide hydroxide and the sulfide is 5.1-5.3:6.5-7.5: 1.
8. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 1, which is based on supercritical technology, and is characterized in that: in the step (2), stirring at high speed for 60-90min at 70-80 ℃ and under ultrasonic wave, wherein the intensity of the ultrasonic wave is 250-.
9. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 1, which is based on supercritical technology, and is characterized in that: in the step (2), the solvent for extraction is furfural, methanol, ethylenediamine or N-methylpyrrolidone.
10. The method for separating and purifying high-purity alpha-methylnaphthalene according to claim 1, which is based on supercritical technology, and is characterized in that: in the step (3), the mass ratio of the high-purity alpha + beta methylnaphthalene composition to the 2-amino-3-methylpyridine is 1: 0.3-0.8.
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