CN103360201A - Method for extracting, distilling and recovering styrene from hydrocarbon mixture - Google Patents
Method for extracting, distilling and recovering styrene from hydrocarbon mixture Download PDFInfo
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- CN103360201A CN103360201A CN2012100889420A CN201210088942A CN103360201A CN 103360201 A CN103360201 A CN 103360201A CN 2012100889420 A CN2012100889420 A CN 2012100889420A CN 201210088942 A CN201210088942 A CN 201210088942A CN 103360201 A CN103360201 A CN 103360201A
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Abstract
The invention relates to a method for extracting, distilling and recovering styrene from a hydrocarbon mixture. The method comprises the following steps of: extracting, distilling and recovering the styrene from the hydrocarbon mixture by using a composite solvent in the presence of a polymerization inhibitor. The composite solvent comprises 80-99% by mass of a main solvent, 0.01-19% by mass of an auxiliary solvent and 0.1-2.0% by mass of water, wherein the main solvent is a sulfone compound, and the auxiliary solvent is metoxyphenol or the mixture of the metoxyphenol and the glycol monomethyl ether. The polymerization inhibitor comprises 40-80% by mass of free radicals of nitrogen and oxygen, 15-50% by mass of nitro-phenol and derivatives thereof and 5-30% by mass of N, N-diethyl hydroxylamine. The use amount of the polymerization inhibitor is 10-500mug/g of the amount of the hydrocarbon raw material. Because the composite solvent is used together with the polymerization inhibitor, the use amount of the polymerization inhibitor can be decreased, and the rate of polymerization of the styrene can be reduced significantly.
Description
Technical field
The present invention be a kind of from hydrocarbon mixture the method for recycling vinyl benzene with abstraction distillation, specifically, be the method for using double solvents recycling vinyl benzene with abstraction distillation from hydrocarbon mixture.
Background technology
Styrene monomer is important basic organic chemical industry raw material, at aspects such as coating, agricultural chemicals, medicine extensive use is arranged also.According to statistics, contain 3～5% vinylbenzene in the steam cracking gasoline of ethylene cracker by-product, 1,000,000 ton/years of ethylene units of a cover are because of the difference of raw material, and containing vinylbenzene in the pyrolysis gasoline is 2～30,000 ton/years.In the technological process of existing processing pyrolysis gasoline, this part vinylbenzene is hydrogenated into ethylbenzene, is stored in C
8In the cut, this C that is rich in ethylbenzene
8Cut, it is very undesirable as raw material to supply with downstream p-Xylol device.Dehydrogenation becomes vinylbenzene if adopt superfractionation to separate after the ethylbenzene again, and long flow path, energy consumption are high, also unreasonable.
By contrast, direct separating phenylethylene is a very attractive technology from pyrolysis gasoline.Yet pyrolysis gasoline C
8Fractions consisting is very complicated, and boiling point is very approaching between the component, is o-Xylol and phenylacetylene with the most difficult component of separating of vinylbenzene wherein.O-Xylol and cinnamic boiling-point difference only are 0.8 ℃, and the relative volatility of the two only has 1.04, need thousands of theoretical stages with conventional distillation, therefore are actually to realize.
From without separating phenylethylene the pyrolysis gasoline of hydrogenation, feasible method is to adopt extracting rectifying.The extracting rectifying process has two key problem in technology, and the one, solvent, the performance of solvent comprises that selectivity, boiling point, thermo-chemical stability and solvent to cinnamic polymerization inhibition performance etc., have vital impact to the process technology economic target.Next is establishment styrene polymerization how, and this is concerning that can device long-period stable operation.In order to suppress styrene polymerization, key is the screening high-efficiency polymerization inhibitor.In addition, also to solve the solvent reclamation process that removes high boiling substance.
GB1,038,606 proposed a kind of from hydrocarbon mixture the method for separating phenylethylene, this method is processed hydrocarbon raw material with Fuller's earth first, uses the aqueous solution of silver salt as the solvent of extracting rectifying again, and described silver salt is Silver Nitrate, but the cost of this solvent is higher, and industrial utility value is lower.
USP3,763,015 discloses a kind of method of using polymerization retarder and extracting, rectifying and separating phenylethylene from pyrolysis gasoline, this method is carried out extracting rectifying to pyrolysis gasoline in the presence of polar solvent and nitrogenous polymerization retarder, then from solvent, reclaim vinylbenzene, the vinylbenzene that again recovery is obtained and the nitric acid reaction of capacity are removed the impurity in the vinylbenzene, and the vinylbenzene cut of removing behind the impurity from new distillation again obtains substantially colourless and pure vinylbenzene.Described polar solvent is selected from N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone and methyl-sulphoxide etc., and the polymerization retarder that uses is sulphur, Resorcinol, p-ten.-butylcatechol.But the preferred dimethylacetamide solvent of institute is because boiling point (165 ℃) is on the low side, and toluene and vinylbenzene boiling-point difference are too little with the neighbour, so the process energy consumption is high.
USP4,596,655 disclose a kind of from hydrocarbon mixture the method for separating phenylethylene class unsaturated hydrocarbon, adopt aminoethylpiperazine as the solvent of the extracting rectifying stopper of holding concurrently, be also to need 115～125 theoretical stages under 8 the condition in solvent ratio.
CN1077560C disclosed from pyrolysis gasoline the method for extracting, rectifying and separating phenylethylene propose the solvent of extracting rectifying is divided into two portions, solvent is mainly by being selected from propylene carbonate, tetramethylene sulfone, methyl carbitol, 1-Methyl-2-Pyrrolidone, 2-Pyrrolidone or their mixture but do not comprise the first part of water and be comprised of the second section that water consists of, first part's solvent enters from extractive distillation column top, and the second section solvent adds at the bottom of extractive distillation column.
CN1962013A discloses from steam cracking C
8The solvent of recycling vinyl benzene with abstraction distillation in the cut; comprise 15～60% sulfone compound and 40～45% nitrogenous compound; described sulfone compound is selected from dimethyl sulfoxide (DMSO) or tetramethylene sulfone; nitrogenous compound is selected from least a in succinonitrile, N,N-dimethylacetamide, METHYLPYRROLIDONE, 2-Pyrrolidone, aminoethyl piperazine or the N-formyl morpholine.This solvent can make the pH value of solvent be about 7, and improves o-Xylol to cinnamic relative volatility.
CN1962582A discloses a kind of method for prohibiting polymerization of styrene, be that the stopper greater than 50ppm that adds the water-containing solvent dissolving in 5～99% the vinylbenzene Aquo System prevents cinnamic polymerization to weight percent concentration, wherein the stopper weight percent consists of: a) 20%～80% nitrite; B) 10%～50% quinones; C) 1%～35% nitrophenol, many nitrophenol or derivatives thereof.
CN101468938A discloses the double solvents of extracting, rectifying and separating phenylethylene, comprise the main solvent of 62～90 quality % and the solubility promoter of 10～38 quality %, described main solvent is selected from sulfone compound, pyrrolidones, glycols compound or any two or three mixture among them, and solubility promoter is selected from C
9～C
12Aromatic hydrocarbons, the acid amides that contains 2～6 carbon atoms or their mixture.
CN101955409A discloses a kind of method of ethene suppressing base aromatics polymerization in the extractive distillation process, described inhibitor is 2-sec-butyl-4,6-dinitrophenol (DNBP), addition is at least 10 of vinyl aromatic compounds amount, 000wtppm.
Cheng Wenwu is at " the composition and performance research of vinylbenzene Compositional type stopper " (Zhejiang University's master thesis, in May, 2007) discloses by 4-hydroxyl-2 in the literary composition, 2,6, the composite polymerzation inhibitor that 6-tetramethyl piperidine nitrogen oxygen free radical (OH-TEMPO), azanol and DNBP form, this stopper prolongs inductive phase, and the slow poly-effect after finishing inductive phase also increases.
In the prior art, solvent can not take into account selectivity that key ingredient o-Xylol/vinylbenzene is separated well, to structure adaptability and the threes' such as polymerization inhibition performance of itself contradiction, although the tetramethylene sulfone selectivity is good, but on the low side to polymer dissolution, in a single day produce polymkeric substance in the process, separate out easily and occluding device.Existing stopper boiling point is all very high, or solvability is too low to be separated out easily, or consumption is large, polymerization inhibition effect is not good, affects the long-period stable operation of whole device.
Summary of the invention
The purpose of this invention is to provide a kind of from hydrocarbon mixture the method for recycling vinyl benzene with abstraction distillation, the double solvents that this method is selected cooperates with the polycomponent stopper, can reduce the stopper consumption, significantly reduce cinnamic percent polymerization.
Provided by the invention from hydrocarbon mixture the method for recycling vinyl benzene with abstraction distillation, comprise hydrocarbon mixture is carried out extracting rectifying recovery vinylbenzene wherein with double solvents in the presence of stopper, described double solvents comprises the main solvent of 80～99 quality %, 0.01 the water of the solubility promoter of～19 quality % and 0.1～2.0 quality %, wherein main solvent is selected from sulfone compound, solubility promoter is the mixture of methoxyphenol or methoxyphenol and glycol monomethyl ether, described stopper comprises the nitroxyl free radical of 30～80 quality %, the N of the nitrophenol of 15～50 quality % and derivative and 5～35 quality %, the N-diethyl hydroxylamine.
The present invention adds moderate boiling point, has good inhibition, polymkeric substance is had larger dissolving power in the cinnamic main solvent of extracting rectifying solubility promoter itself, be used with the polycomponent stopper, can effectively reduce the temperature at the bottom of the extractive distillation column and at the bottom of the solvent recovery tower, significantly reduce the stopper consumption, greatly reduce cinnamic polymerization, avoid polymkeric substance to separate out, effectively prolong the steady running cycle of recycling vinyl benzene with abstraction distillation device.
Description of drawings
Fig. 1 is from pyrolysis gasoline C with the inventive method
8The schematic flow sheet of recycling vinyl benzene with abstraction distillation in the fraction.
Embodiment
The present invention adds in the cinnamic main solvent of extracting rectifying has larger dissolving power and the methoxyphenol of polymerization inhibition performance is arranged self is solubility promoter to polymkeric substance, and in addition, solubility promoter can also be the mixture of methoxyphenol and glycol monomethyl ether.Double solvents and polycomponent stopper that the inventive method will comprise described solubility promoter are used, and can reduce the stopper consumption, reduce at the bottom of the extractive distillation column and the temperature at the bottom of the solvent recovery tower, prolong the steady running time of extracting rectifying device.
Double solvents of the present invention preferably includes the main solvent of 86～99 quality %, the solubility promoter of 0.1～13.0 quality % and the water of 0.1～1.0 quality %.
Main solvent in the described double solvents is selected from sulfone compound, one or more in preferred tetramethylene sulfone, dimethyl sulfone and the 3-methyl sulfolane, more preferably tetramethylene sulfone.
Solubility promoter in the described double solvents is methoxyphenol, for further increasing the solvability to styrene polymer, also can be the mixture of methoxyphenol and glycol monomethyl ether.Described methoxyphenol is 4-methoxyphenol, 3-methoxyphenol or 2-methoxyphenol, and described glycol monomethyl ether is diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, Tetraglycol 99 monomethyl ether or their mixture.If solubility promoter is the mixture of methoxyphenol and glycol monomethyl ether, the mass ratio of glycol monomethyl ether and methoxyphenol is 5～1: 1, preferred 3～1: 1.
The used stopper of the inventive method contains various ingredients, and described stopper preferably includes the nitroxyl free radical of 30～65 quality %, the nitrophenol of 15～40 quality % and the N of derivative and 15～35 quality %, N-diethyl hydroxylamine.
Nitroxyl free radical in the used stopper of the inventive method also comprises the compound that contains the oxygen nitrogen free radical, is selected from 4-hydroxyl-TEMPO, tricresyl phosphite (TEMPO) ester or its mixture.
Described nitrophenol and derivative thereof are preferred 2,6-dinitro-p-cresol, 2-sec-butyl-4,6-dinitrophenol or 2,4-DNP.
The total amount of described stopper and hydrocarbon mixture, be that the mass ratio of extracting rectifying raw material is 10～500 μ g/g, preferred 30～300 μ g/g.
During with the inventive method recycling vinyl benzene with abstraction distillation, hydrocarbon mixture is introduced from the middle part of extractive distillation column, double solvents is introduced from the extracting rectifying cat head, stopper at the bottom of extractive distillation column charging, the extractive distillation column or the solvent recuperation cat head introduce, through behind the extracting rectifying, raffinate is discharged from the top of extractive distillation column, the rich solvent of rich in styrene is discharged at the bottom of extractive distillation column, enter solvent recovery tower, vinylbenzene is discharged from the solvent recuperation cat head, double solvents is discharged at the bottom of solvent recovery tower, preferably returns the extractive distillation column recycle.
The theoretical plate number of described extractive distillation column is preferred 60～90, and the mass ratio of double solvents and hydrocarbon mixture is 3～6, and the trim the top of column ratio is 1～3, and column bottom temperature is 120～135 ℃, and tower top pressure is 8～20kPa.
The theoretical plate number of described solvent recovery tower is preferred 20～40, and the reflux ratio of cat head is 0.5～2.5, and column bottom temperature is 130～145 ℃, and tower top pressure is 8～20kPa.
The C of the preferred pyrolysis gasoline of hydrocarbon mixture of the present invention
8Fraction, wherein styrene content is 25～70 quality %, C
8Aromatic hydrocarbons and non-aromatics content are 28～70 quality %, and other carbon number aromaticity content is 0.01～5.0 quality %.
Describe the present invention in detail below in conjunction with accompanying drawing.
Among Fig. 1, contain cinnamic hydrocarbon mixture and entered by pipeline 1, enter extractive distillation column 102 from the middle part by pipeline 2 after interchanger 101 heat exchange, double solvents enters extractive distillation column 102 by pipeline 15 from top, and stopper injects pipeline 1 by volume pump.Through extracting rectifying, do not contain cinnamic component and discharged by the overhead line 3 of extractive distillation column, enter return tank 103, raffinate by the return tank outflow, a part passes back into the top of extractive distillation column 102 by pipeline 4, and another part is discharged by pipeline 5, and moisture is discharged from pipeline 6.The rich solvent of rich in styrene is discharged by the extracting rectifying tower bottom, enter solvent recovery tower 104 from the middle part through pipeline 7, vinylbenzene and water are discharged by overhead line 8, enter return tank 105, a vinylbenzene part of discharging from return tank 105 passes back into solvent recovery tower by pipeline 9, and another part is discharged from pipeline 10 as product, does not contain cinnamic poor double solvents and is discharged by solvent recovery tower bottom tube line 13, after interchanger 106 heat exchange, enter pipeline 14, enter pipeline 15 through interchanger 101 again.The hydration that the water of discharging from pipeline 11 and pipeline 6 are discharged and after interchanger 106 and after the double solvents heat exchange from 104 ends of solvent recovery tower, water is vaporized through pipeline 12 and enters solvent recovery tower 104 bottoms as the stripping medium.
Following instance further describes the present invention, but the present invention is not limited to this.
Example 1
With pyrolysis gasoline C
8Cut is raw material, and its composition is listed in table 1.By flow process shown in Figure 1 described raw material is carried out extracting rectifying, reclaim vinylbenzene wherein, used double solvents contains the main solvent tetramethylene sulfone of 99 quality %, the solubility promoter 4-methoxyphenol of 0.5 quality % and the water of 0.5 quality %.Stopper is 4-hydroxyl-TEMPO (OH-TEMPO) of 55 quality %, 4 of 25 quality %, the N of 6-dinitrobenzene-2-sec-butyl phenol (DNBP) and 20 quality %, N-diethyl hydroxylamine.The stopper total amount with for the mass ratio of extraction feed be 100 μ g/g.
The extractive distillation column number of theoretical plate is 70, and the mass ratio of tower top pressure 15kPa, double solvents/raw material is 3.8, reflux ratio 2.0.
The solvent recovery tower number of theoretical plate is 28, tower top pressure 15kPa, and reflux ratio is 1.0.
Be that 99.7 quality %, the rate of recovery are that extracting rectifying the results are shown in Table 2 under the condition of 95 quality % in vinylbenzene purity.
Example 2
Press the method for example 1 from pyrolysis gasoline C
8Reclaim vinylbenzene in the cut, different is that the solubility promoter that uses is the 3-methoxyphenol, is that 99.7 quality %, the rate of recovery are that extracting rectifying the results are shown in Table 2 under the condition of 95 quality % in vinylbenzene purity.
Example 3
Press the method for example 1 from pyrolysis gasoline C
8Reclaim vinylbenzene in the cut, different is that the solubility promoter that uses is the 2-methoxyphenol, is that 99.7 quality %, the rate of recovery are that extracting rectifying the results are shown in Table 2 under the condition of 95 quality % in vinylbenzene purity.
Example 4
Press the method for example 1 from pyrolysis gasoline C
8Reclaim vinylbenzene in the cut, different is main solvent tetramethylene sulfone, the 2-methoxyphenol of 5 quality %, the triethylene glycol monomethyl ether of 6.5 quality % and the water of 0.5 quality % that used double solvents contains 88 quality %, the stopper total amount with for the mass ratio of extraction feed be 150 μ g/g.Be that 99.7 quality %, the rate of recovery are that extracting rectifying the results are shown in Table 2 under the condition of 95 quality % in vinylbenzene purity.
Example 5
Press the method for example 1 from pyrolysis gasoline C
8Reclaim vinylbenzene in the cut, different is that used stopper is the tricresyl phosphite (2 of 40 quality %, 2,6,6-tetramethyl piperidine nitrogen oxygen free radical) 2 of ester, 30 quality %, the N of 6-dinitro-p-cresol (DNPC) and 30 quality %, the N-diethyl hydroxylamine, the mass ratio of stopper total amount and extraction feed is 150 μ g/g, is that 99.7 quality %, the rate of recovery are that extracting rectifying the results are shown in Table 2 under the condition of 95 quality % in vinylbenzene purity.
Comparative Examples 1
Press the method for example 1 from pyrolysis gasoline C
8Reclaim vinylbenzene in the cut, different is that the double solvents that uses is the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality %, stopper is pressed the method preparation of CN1962582A, stopper contains the Sodium Nitrite of 65 quality %, the DNBP of the benzoquinones of 20 quality % and 15 quality %, the mass ratio of stopper total amount and extraction feed is 600 μ g/g, is that 99.7 quality %, the rate of recovery are that extracting rectifying the results are shown in Table 2 under the condition of 95 quality % in vinylbenzene purity.
Comparative Examples 2
Press the method for example 1 from pyrolysis gasoline C
8Reclaim vinylbenzene in the cut, different is that the double solvents that uses is the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality %, and the stopper consumption is 200 μ g/g.Be that 99.7 quality %, the rate of recovery are that extracting rectifying the results are shown in Table 2 under the condition of 95 quality % in vinylbenzene purity.
Table 1
Table 2
As shown in Table 2, under the condition of identical vinylbenzene purity (99.7 quality %) and the rate of recovery (95 quality %), adopt double solvents of the present invention, because its solvability to stopper is good, the stopper consumption reduces than Comparative Examples, the styrene polymerization rate significantly reduces, and without the polymerization suspended substance, more outstanding is to reach the continuous operating time of regulation purity and the rate of recovery than the Comparative Examples significant prolongation in the lean solvent.
Claims (12)
1. the method for a recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, comprise hydrocarbon mixture is carried out extracting rectifying recovery vinylbenzene wherein with double solvents in the presence of stopper, described double solvents comprises the main solvent of 80～99 quality %, 0.01 the water of the solubility promoter of～19 quality % and 0.1～2.0 quality %, wherein main solvent is selected from sulfone compound, solubility promoter is the mixture of methoxyphenol or methoxyphenol and glycol monomethyl ether, described stopper comprises the nitroxyl free radical of 30～80 quality %, the N of the nitrophenol of 15～50 quality % and derivative and 5～35 quality %, the N-diethyl hydroxylamine.
2. in accordance with the method for claim 1, it is characterized in that described double solvents comprises the main solvent of 86～99 quality %, the solubility promoter of 0.1～13.0 quality % and the water of 0.1～1.0 quality %.
3. in accordance with the method for claim 1, it is characterized in that described sulfone compound is selected from one or more in tetramethylene sulfone, dimethyl sulfone and the 3-methyl sulfolane.
4. in accordance with the method for claim 1, it is characterized in that described methoxyphenol is 4-methoxyphenol, 3-methoxyphenol or 2-methoxyphenol, described glycol monomethyl ether is diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, Tetraglycol 99 monomethyl ether or their mixture.
5. in accordance with the method for claim 1, when it is characterized in that solubility promoter is the mixture of methoxyphenol and glycol monomethyl ether, the mass ratio of glycol monomethyl ether and methoxyphenol is 5～1: 1.
6. in accordance with the method for claim 1, it is characterized in that described stopper comprises the nitroxyl free radical of 30～65 quality %, the nitrophenol of 15～40 quality % and the N of derivative and 15～35 quality %, N-diethyl hydroxylamine.
7. in accordance with the method for claim 1, it is characterized in that described nitroxyl free radical is 4-hydroxyl-TEMPO, tricresyl phosphite (TEMPO) ester or its mixture.
8. in accordance with the method for claim 1, it is characterized in that described nitrophenol and derivative thereof are selected from 2,6-dinitro-p-cresol, 2-sec-butyl-4,6-dinitrophenol or 2,4-DNP.
9. in accordance with the method for claim 1, it is characterized in that the total amount of described stopper and the mass ratio of hydrocarbon mixture are 10～500 μ g/g.
10. in accordance with the method for claim 1, when it is characterized in that recycling vinyl benzene with abstraction distillation, hydrocarbon mixture is introduced from the middle part of extractive distillation column, double solvents is introduced from the extracting rectifying cat head, stopper at the bottom of extractive distillation column charging, the extractive distillation column or the solvent recuperation cat head introduce, through behind the extracting rectifying, raffinate is discharged from the top of extractive distillation column, the rich solvent of rich in styrene is discharged at the bottom of extractive distillation column, enter solvent recovery tower, vinylbenzene is discharged from the solvent recuperation cat head, and double solvents is discharged at the bottom of solvent recovery tower.
11. in accordance with the method for claim 10, the theoretical plate number that it is characterized in that described extractive distillation column is 60～90, and the mass ratio of double solvents and hydrocarbon mixture is 3～6, and the trim the top of column ratio is 1～3, column bottom temperature is 120～135 ℃, and tower top pressure is 8～20kPa.
12. in accordance with the method for claim 10, the theoretical plate number that it is characterized in that described solvent recovery tower is 20～40, and the reflux ratio of cat head is 0.5～2.5, and column bottom temperature is 130～145 ℃, and tower top pressure is 8～20kPa.
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| CN111978143B (en) * | 2019-05-23 | 2023-05-05 | 中国石油化工股份有限公司 | Composite solvent for separating aromatic hydrocarbon by extractive distillation and application thereof |
| RU2722271C1 (en) * | 2019-10-02 | 2020-05-28 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Уфимский государственный нефтяной технический университет" | Method of extracting styrene from pyro-condensate fraction c8 |
| WO2024060399A1 (en) * | 2022-09-23 | 2024-03-28 | 上海兖矿能源科技研发有限公司 | Separation method for high-temperature fischer-tropsch synthesized light oil |
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