CN108395367B - Method for separating phenolic compounds from coal tar - Google Patents
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Abstract
The invention provides a method for separating phenol in coal tar by using piperazine compounds as an extracting agent, which takes piperazine substances as the extracting agent, water and n-butyl ether as a back-extracting agent to recover the piperazine substances, and piperazine and the phenol substances interact to form eutectic substances or complexes insoluble in an oil phase. The method has high extraction rate, avoids the pollution problem of phenol-containing wastewater caused by the traditional acid-base separation method, can recycle the extracting agent and the back-extracting agent for multiple times, has the removal rate of phenolic compounds of over 95 percent, and belongs to a green separation method of high value-added product phenol.
Description
Technical Field
The invention relates to the field of separation of products in coal chemical industry and petrochemical industry, in particular to a method for separating phenolic compounds from coal tar, low-temperature coal pyrolysis oil and other mixtures of oil and phenol.
Background
The coal pyrolysis oil chemical industry in China still stays at the rough processing stage, and only more than 40 products can be extracted at present. The processing technology of the coal pyrolysis oil at home and abroad is developed aiming at the high-temperature coal pyrolysis oil, and the research and the utilization of the medium-low temperature coal pyrolysis oil are less. Due to the characteristics of the low-temperature coal pyrolysis oil in composition and property, the processing route and the product structure of the low-temperature coal pyrolysis oil have larger difference than those of the high-temperature coal pyrolysis oil, and a targeted mild, high-efficiency and low-energy-consumption high-efficiency step separation technology needs to be developed.
The phenolic compound is one of chemical basic raw materials, and is widely applied to the fields of fiber, plastic, pesticide, medicine, preservative, explosive synthesis and the like. They are mainly derived from direct coal liquefaction products, coal tar and petroleum products. In recent years, researches on extracting phenolic compounds from direct coal liquefaction products, coal tar and petroleum products have attracted extensive attention of researchers at home and abroad. The traditional method adopts sodium hydroxide solution for elution, and the principle of the elution method is that phenolic compounds have weak acidity and react with strong base to form sodium phenolate solution which is easy to dissolve in water, so that the phenolic compounds are transferred from an oil phase to a water phase, and the purpose of separation is achieved. The process is as follows: and (3) contacting a sodium hydroxide aqueous solution with the phenol oil mixture, reacting phenol with the sodium hydroxide to generate sodium phenolate, dissolving the sodium phenolate in water, and separating the sodium phenolate aqueous solution from dephenolized oil. The regeneration process of the sodium phenolate is as follows: the net sodium phenolate and the sulfuric acid solution with a certain concentration are simultaneously fed into a reactor, and the reaction product is cooled and then fed into a primary separator. The crude phenol obtained from the reaction was discharged from the upper part of the separator, and the sodium sulfate solution was discharged from the bottom.
The alcohol aqueous solution extraction method has the advantages that the extraction agent is low in cost and easy to recover, but the extraction rate is low. The salt aqueous solution extraction method is to extract phenolic substances by utilizing the solubility of certain salt aqueous solution to the phenolic substances, but like other extraction methods, the process inevitably generates a large amount of phenol-containing wastewater to be treated, thereby undoubtedly increasing the difficulty of subsequent treatment and the production cost.
In the existing coal pyrolysis oil separation method, strong acid and alkali are used or the extraction rate and selectivity are low, and a novel extracting agent suitable for the substance needs to be developed according to the characteristics of the substance to be separated. In the case of phenolics, their Bronsted acidity makes their separation possible by hydrogen bonding with Lewis bases. On the basis, the extraction agent screening principle is established, and the development of a green separation method of phenolic substances is very necessary.
Disclosure of Invention
The invention provides a method for separating phenol from a mixture of coal tar, low-temperature coal pyrolysis oil, other straight-chain alkane oil and phenol by taking a piperazine compound as an extractant, and the method takes the piperazine substance as the extractant, water and n-butyl ether as a back extractant to recover the piperazine substance, and forms a eutectic substance or a complex compound which is insoluble in an oil phase through the interaction of the piperazine substance and the phenol substance. The method has higher extraction rate, avoids the problems of generation and pollution of phenol-containing wastewater caused by the traditional acid-base separation method, can realize the repeated use of the extracting agent, and hardly reduces the separation efficiency; the production cost is effectively reduced; has high separation efficiency.
The method has the characteristics of high extraction efficiency, no use of strong acid and strong base, no generation of a large amount of wastewater and environment-friendly process. The method can repeatedly utilize the extractant, reduce the separation cost, simplify the separation process and have certain practical and environmental protection significance.
The invention discloses a method for separating phenolic compounds from coal tar, which innovatively adopts piperazine compounds as an extracting agent, forms eutectic substances or complexes insoluble in an oil phase through the interaction of piperazine and the phenolic compounds, and recovers the piperazine compounds by taking water and n-butyl ether as a back-extracting agent, thereby realizing the separation of an oil-phenol mixture and the recovery of the piperazine compounds.
The invention discusses the conditions of the separation process in detail, and lists the extraction effect of the extractant and the phenol under different molar ratios of (0.1-1: 1), the extraction effect under different stirring times of 5-60min, the comparison of the extraction effect at the reaction temperature of 0-90 ℃, and the comparison of the extraction effect when the piperazine compound is used as the extractant. Through a large amount of experimental demonstration, the data is reliable, full and full. Under the process conditions, the mol ratio of the extracting agent to the phenol is preferably 0.5:1, the stirring time is preferably 10min, the reaction temperature is preferably 30-60 ℃, and when the piperazine compound is used as the extracting agent, one or two of 2-methylpiperazine and 1-phenylpiperazine are preferably used.
Piperazine compounds also include piperazine, hexahydrate, homopiperazine, 1-methylpiperazine, 2-methylpiperazine, N-ethylpiperazine, 1-phenylpiperazine.
The method comprises the following specific steps:
(1) preparing an oil phenol mixture, wherein the phenol concentration is 10-400 g/L;
(2) extracting and separating real coal tar, low-temperature coal pyrolysis oil or the phenol compound in the oil-phenol mixture prepared in the step (1) by taking a piperazine compound as an extracting agent, wherein the molar ratio of the extracting agent to phenol is 0.1: 1-1.2: 1, so as to obtain a mixture phase of an oil phase, the extracting agent and phenol;
(3) placing the mixture in water bath, controlling reaction temperature at 0-100 deg.C, stirring for 5min-1h, standing, and separating upper oil phase and lower complex or DES phase;
(4) after the separation of the upper layer and the lower layer is finished, the lower layer is subjected to reverse extraction by using water and n-butyl ether, and the volume ratio of the water to the n-butyl ether is 1: 1-1: the volume ratio of water to n-butyl ether is preferably 1:1, stirring for 30min, standing for 20min, carrying out reduced pressure distillation on a lower-layer water phase to recover piperazine compounds, and distilling and extracting phenols from an upper layer by using n-butyl ether to realize recycling of an extracting agent;
in the oil-phenol mixture, the oil is mostly straight-chain alkane, the straight-chain alkane is one or more of n-hexane, n-heptane, n-octane and n-dodecane, the phenolic compound is one or more of phenol, m-cresol, p-cresol, o-cresol, alkylphenol, naphthol, resorcinol and the like, and the oil-phenol mixture contains 1-40% of phenol by mass.
The molar ratio of the added piperazine compound to the phenolic compound in the oil is 0.5:1, the separation temperature is 30-60 ℃, and the separation time is 0.1-2 h. In the step (4), when the mixture of n-butyl ether and water is used for back extraction of the piperazine compound, the operation temperature is 0-50 ℃, the time is 2-30min, the ratio of the back extraction phase to the piperazine compound is 10:1, and the back extraction frequency is 1-3 times.
Detailed Description
Example 1: preparing phenol-n-hexane monophenol simulation oil, wherein the concentration is as follows: 40.1g/L, piperazine was used as extractant to isolate phenol. The reaction temperature is 30 ℃, the molar ratio of the extracting agent to the phenol is 0.5:1, and the reaction time is 30 min. Adding 0.75g of piperazine into 40mL of phenol simulation oil, stirring in a water bath at 30 ℃, standing for 15min, separating an upper oil phase and a lower complex by vacuum filtration, measuring the volume of the upper oil phase and measuring the phenol concentration by GC, wherein the extraction rate of the piperazine to the phenol is 98.9%, adding 5mL of water and 5mL of n-butyl ether into the lower complex, stirring for 30min, standing for 20min, distilling the lower aqueous phase under reduced pressure to recover the extraction agent piperazine, and distilling the upper n-butyl ether to extract the phenol. The recovery rate of piperazine is about 85%, and the extraction rate is about 95% after the piperazine is circulated for three times.
Example 2: preparing o-cresol-n-hexane monophenol simulation oil, wherein the concentration is as follows: 147.58g/L homopiperazine is used as an extractant to separate o-cresol. The reaction temperature is 30 ℃, the molar ratio of the extracting agent to the o-cresol is 0.5:1, and the reaction time is 30 min. Adding 3.41g of piperazine into 50mL of o-cresol simulated oil, stirring in a water bath at 30 ℃, standing for 15min after 30min, separating an upper oil phase and a lower DES phase, measuring the volume of the upper oil phase, measuring the o-cresol concentration by using GC, and controlling the extraction rate of piperazine on o-cresol to be 97.9%.
Example 3: preparing m-cresol-n-hexane monophenol simulation oil, wherein the concentration is as follows: 200.56g/L, piperazine was used as an extractant to separate m-cresol. The reaction temperature is 30 ℃, the mol ratio of the extracting agent to the m-cresol is 0.5:1, and the reaction time is 30 min. Adding 1.60g of piperazine into 20mL of m-cresol simulated oil, stirring in a water bath at 30 ℃, standing for 30min, separating an upper oil phase from a lower DES phase, measuring the volume of the upper oil phase, measuring the concentration of the intermediate cresol by GC, wherein the extraction rate of the piperazine on the m-cresol is 95.2%, adding 10mL of water and 15mL of n-butyl ether into a lower eutectic phase, stirring for 30min, standing for 20min, distilling the lower water phase under reduced pressure to recover the extraction agent piperazine, and distilling the upper n-butyl ether to extract the m-cresol. The recovery rate of piperazine is about 80%, and the extraction rate is about 90% after the piperazine is circulated for three times.
Example 4: preparing paracresol-n-hexane monophenol simulation oil, wherein the concentration is as follows: 147.58g/L, piperazine hexahydrate is used as an extracting agent to separate the p-cresol. The reaction temperature is 30 ℃, the molar ratio of the extracting agent to the p-cresol is 0.5:1, and the reaction time is 30 min. Adding 6.63g of piperazine hexahydrate into 50mL of p-cresol simulated oil, stirring in a water bath at 30 ℃, standing for 15min, performing vacuum filtration to separate an upper oil phase and a lower complex, measuring the volume of the upper oil phase, and measuring the concentration of p-cresol by using GC, wherein the extraction rate of the p-cresol is 95.1%.
Example 5: preparing phenol-m-cresol-o-cresol-p-cresol simulated oil with the mass ratio of 2:1:1:1 and the total phenol concentration of 202.98g/L, and preparing the phenol-m-cresol-o-cresol-p-cresol simulated oil with n-hexane as a solvent and the mass ratio of 2:1:1:1, the phenol concentration of 90.38g/L, the p-cresol concentration of 41.2412g/L, the m-cresol concentration of 40.9803g/L and the o-cresol concentration of 40.3824 g/L. Piperazine as an extractant was stirred at room temperature for 30min, and then left to stand for 30min, and the effect of adding different molar ratios of the extractant on the extraction effect was examined, as shown in table 1. Table 1 shows that the molar ratio of the extractant to phenol (0.1-1: 1) is high, and the phenol extraction rate is mostly more than 95%. The molar ratio is preferably 0.5: 1.
Table 1 effect of different molar ratios of extractant on extraction efficiency.
| Molar ratio of | m (piperazine) | Phenol and its preparation | M-cresol | Para-cresol | Ortho-cresol |
| 0.1：1 | 0.3377 | 87.40% | 78.51% | 84.76% | 85.48% |
| 0.3：1 | 1.012 | 98.63% | 93.09% | 96.39% | 96.47% |
| 0.5：1 | 1.6884 | 99.84% | 98.02% | 99.07% | 99.08% |
| 0.7：1 | 2.3637 | 99.77% | 97.88% | 98.88% | 98.91% |
| 0.9:1 | 3.0397 | 99.76% | 98.02% | 98.94% | 98.98% |
| 1:1 | 3.7144 | 99.76% | 97.96% | 98.90% | 98.93% |
| 1.1：1 | 4.052 | 99.71% | 97.84% | 98.83% | 98.87% |
Example 6: the phenol-m-cresol-o-cresol-p-cresol simulated oil is prepared by using normal hexane as a solvent in a mass ratio of 2:1:1:1, wherein the phenol concentration is 90.38g/L, the p-cresol concentration is 41.2412g/L, the m-cresol concentration is 40.9803g/L, and the o-cresol concentration is 40.3824 g/L. 1.69g of piperazine and 20mL of a simulated oil were added, the mixture was stirred at room temperature and then allowed to stand for 30min, and the influence of the stirring time on the extraction rate was examined, as shown in Table 2. Table 2 shows that in the stirring time of 5 to 60 minutes, 10 minutes is preferable from the viewpoint of the process.
Table 2 influence of stirring time on extraction rate.
| Time (min) | Phenol and its preparation | M-cresol | Para-cresol | Ortho-cresol |
| 5 | 99.94% | 95.09% | 97.38% | 97.29% |
| 10 | 99.98% | 97.64% | 98.68% | 98.63% |
| 15 | 99.98% | 97.45% | 98.62% | 98.56% |
| 30 | 99.98% | 97.58% | 98.72% | 98.67% |
| 45 | 99.98% | 97.76% | 98.70% | 98.65% |
| 60 | 99.98% | 97.81% | 98.74% | 98.70% |
Example 7: the phenol-m-cresol-o-cresol-p-cresol simulated oil is prepared according to the mass ratio of 2:1:1:1, the total phenol concentration is 202.98g/L, n-hexane is used as a solvent, the phenol concentration is 90.38g/L, the p-cresol concentration is 41.2412g/L, the m-cresol concentration is 40.9803g/L, and the o-cresol concentration is 40.3824 g/L. The molar ratio of the piperazine to the total phenols in the n-hexane is 0.5:1, 20mL of simulated oil is taken, about 1.69g of piperazine is added, the mixture is stirred for 30min under the water bath condition and then is kept stand for 30min, and the influence of the reaction temperature on the extraction effect is examined, which is shown in Table 3. Table 3 shows that the reaction temperature is preferably 30 to 60 ℃.
Table 3 effect of reaction temperature on extraction efficiency.
| Reaction temperature (. degree.C.) | Phenol and its preparation | M-cresol | Para-cresol | Ortho-cresol |
| 0 | 97.54% | 94.67% | 96.31% | 96.41% |
| 10 | 99.03% | 95.54% | 97.30% | 97.32% |
| 20 | 99.93% | 98.57% | 99.41% | 99.40% |
| 30 | 99.78% | 97.85% | 98.97% | 98.96% |
| 45 | 99.95% | 99.13% | 99.67% | 99.66% |
| 50 | 99.95% | 99.29% | 99.71% | 99.70% |
| 60 | 99.94% | 99.26% | 99.72% | 99.72% |
| 70 | 99.94% | 99.22% | 99.71% | 99.71% |
| 80 | 99.91% | 98.81% | 99.45% | 99.43% |
| 90 | 99.93% | 99.04% | 99.66% | 99.59% |
Example 7: preparing phenol-m-cresol-o-cresol-p-cresol simulated oil with a mass ratio of 2:1:1:1, a total phenol concentration of 202.98g/L, a phenol concentration of 90.38g/L, a p-cresol concentration of 41.2412g/L, a m-cresol concentration of 40.9803g/L and an o-cresol concentration of 40.3824g/L, and taking piperazine as an extracting agent. Adding 1.69g of piperazine into 20mL of simulated oil, stirring for 30min under the condition of water bath at 30 ℃, standing for 30min, measuring the volume of an upper layer and measuring the phenol content in the upper layer phase by GC, wherein the extraction rate of each phenol is as follows: 98.43 percent of phenol; 97.50 percent of o-cresol; 98.15 percent of p-cresol; and m-cresol 97.94%. Removing the upper phase, adding 10mL of water and 15mL of n-butyl ether into the lower solid, stirring at 10 ℃ until the solid is completely dissolved, and distilling the lower aqueous phase under reduced pressure to recover the extractant, wherein the recovery rate is about 85%, and the extraction rate after four times of recycling is as follows: 96.81% of phenol, 95.50% of m-cresol, 97.01% of p-cresol and 95.16% of m-cresol.
Example 8: preparing phenol-m-cresol-o-cresol-p-cresol simulated oil with a mass ratio of 2:1:1:1, a total phenol concentration of 202.98g/L, a phenol concentration of 90.38g/L, a p-cresol concentration of 41.2412g/L, a m-cresol concentration of 40.9803g/L, an o-cresol concentration of 40.3824g/L, and homopiperazine as an extracting agent, wherein a reaction temperature is 30 ℃, and stirring and standing. Adding 2.1248g homopiperazine into 20mL of simulated oil, stirring for 40min under the condition of 30 ℃ water bath, standing for 20min, measuring the volume of an upper layer and measuring the phenol content in the upper layer phase by GC, wherein the extraction rate of each phenol is as follows: 98.43 percent of phenol; 97.50 percent of o-cresol; 98.15 percent of p-cresol; and m-cresol 97.94%.
Example 9: preparing phenol-m-cresol-o-cresol-p-cresol simulated oil with a mass ratio of 2:1:1:1, a total phenol concentration of 202.98g/L, a phenol concentration of 90.38g/L, a p-cresol concentration of 41.2412g/L, a m-cresol concentration of 40.9803g/L, an o-cresol concentration of 40.3824g/L, and homopiperazine as an extracting agent, wherein a reaction temperature is 30 ℃, and stirring and standing. This example examines the effect of different substituents of piperazine on the extraction effect, among the following piperazine compounds: 1-methylpiperazine, 2-methylpiperazine, 1-ethylpiperazine, 1-phenylpiperazine; the above-mentioned extractants were added to 20mL of simulated oil, stirred for 40min under 30 ℃ water bath, left to stand for 15min, and the volume of the upper phase was measured and the phenol content in the upper phase was measured by GC, the phenol extraction rates are shown in Table 4. Table 4 shows that 2-methylpiperazine and 1-phenylpiperazine exhibit high extraction rates, and when piperazine compounds are used as the extractant, one or both of 2-methylpiperazine and 1-phenylpiperazine are preferable.
Table 4 effect of different substituents of piperazine on extraction effect.
| 1-methylpiperazines | 2-methylpiperazines | 1-ethylpiperazine | 1-phenylpiperazines | |
| Phenol and its preparation | 87.24% | 98.06% | 79.05% | 96.68% |
| Ortho-cresol | 78.92% | 96.14% | 73.70% | 94.18% |
| Para-cresol | 84.38% | 97.27% | 76.10% | 95.57% |
| M-cresol | 84.34% | 97.19% | 76.03% | 95.43% |
Example 10: cutting fractions before 230 ℃ in medium-low temperature coal tar, taking an upper oil phase as an experimental object after standing and layering, taking a small amount of the oil phase as an experimental object, analyzing the phenol content of the oil phase by using GC-MS (gas chromatography-mass spectrometry) to be 38%, taking piperazine as an extracting agent, and stirring and standing the oil phase under the water bath condition, wherein the molar ratio of the piperazine to the phenol is about 0.5: 1. Adding 2.76g of piperazine to 80.1g of medium-low temperature coal tar under the condition of water bath at 30 ℃, stirring for 50min, standing for 30min, separating upper and lower liquid layers, measuring the volume of an upper layer, measuring the phenol content in an upper oil phase by using GC-MS, removing the upper layer, adding 10mL of water and 25mL of n-butyl ether, and distilling the water layer under reduced pressure to recover the piperazine with the recovery rate of about 65%.
Claims (2)
1. A method for separating phenolic compounds from coal tar is characterized in that piperazine compounds are used as an extracting agent, the piperazine compounds are one or more, and the piperazine compounds comprise homopiperazine, 1-methylpiperazine, 2-methylpiperazine, N-ethylpiperazine and 1-phenylpiperazine; the method comprises the following steps of forming an oil-insoluble eutectic substance or a complex through the interaction of piperazine substances and phenolic substances, and recovering the piperazine substances by using water and n-butyl ether as stripping agents, thereby realizing the separation of oil-phenol mixtures and the recovery of piperazine compounds, and comprises the following specific steps:
(1) preparing an oil phenol mixture, wherein the phenol concentration is 10-400 g/L;
(2) extracting and separating real coal tar, low-temperature coal pyrolysis oil or the phenolic compound in the oil-phenol mixture prepared in the step (1) by taking a piperazine compound as an extracting agent, wherein the molar ratio of the extracting agent to phenol is 0.5:1, so as to obtain a mixture phase of an oil phase, the extracting agent and phenol;
(3) placing the mixture in water bath, controlling reaction temperature at 30-60 deg.C, stirring for 5-60min, standing for 0.1-0.5h, and separating upper oil phase and lower complex or DES phase;
(4) after the upper layer and the lower layer are separated, the lower layer is subjected to reverse extraction by using water and n-butyl ether, the volume ratio of the water to the n-butyl ether is 1:1, the mixture is stirred for 30min and then is kept stand for 20min, the upper layer is subjected to distillation by using the n-butyl ether to extract phenols, and the lower aqueous phase is subjected to reduced pressure distillation to recover piperazine compounds, so that the extraction agent is recycled;
the oil in the oil-phenol mixture is composed of straight-chain alkane, the straight-chain alkane is specifically one or more of n-hexane, n-heptane, n-octane and n-dodecane, the phenolic compound is one or more of phenol, m-cresol, p-cresol, o-cresol, alkylphenol, naphthol and resorcinol, and the mass of the phenol in the oil-phenol mixture is 1% -40%.
2. The method for separating phenolic compounds from coal tar according to claim 1, wherein in the step (4), n-butyl ether and water are used for back extraction of the piperazine compounds, the operation temperature is 0-50 ℃, the time is 2-30min, the back extraction time is 10-1 compared with the piperazine compounds, and the back extraction times are 1-3 times.
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| US4418221A (en) * | 1981-03-19 | 1983-11-29 | Koei Chemical Co., Ltd. | Process for treating aqueous solutions containing phenols |
| CN1127241A (en) * | 1995-07-14 | 1996-07-24 | 清华大学 | Separating epuration p-cresol technology by complexing extraction crystallization method |
| CN106986750A (en) * | 2017-04-13 | 2017-07-28 | 榆林市榆神工业区衡溢盐业有限公司 | A kind of method that aldehydes matter is extracted from coal tar or coal direct liquefaction oil |
| CN107937009A (en) * | 2017-11-10 | 2018-04-20 | 中国五环工程有限公司 | The separation method of phenolic compound in coal tar and DCL/Direct coal liquefaction product |
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| US4418221A (en) * | 1981-03-19 | 1983-11-29 | Koei Chemical Co., Ltd. | Process for treating aqueous solutions containing phenols |
| CN1127241A (en) * | 1995-07-14 | 1996-07-24 | 清华大学 | Separating epuration p-cresol technology by complexing extraction crystallization method |
| CN106986750A (en) * | 2017-04-13 | 2017-07-28 | 榆林市榆神工业区衡溢盐业有限公司 | A kind of method that aldehydes matter is extracted from coal tar or coal direct liquefaction oil |
| CN107937009A (en) * | 2017-11-10 | 2018-04-20 | 中国五环工程有限公司 | The separation method of phenolic compound in coal tar and DCL/Direct coal liquefaction product |
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