CN103360201B - The method of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture - Google Patents
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Abstract
A kind of method of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, comprise and hydrocarbon mixture is carried out extracting rectifying recovery vinylbenzene wherein with double solvents under stopper exists, described double solvents comprises the main solvent of 80 ~ 99 quality %, the solubility promoter of 0.01 ~ 19 quality % and the water of 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 40 ~ 80 quality %, the N of the nitrophenol of 15 ~ 50 quality % and derivative and 5 ~ 30 quality %, N-diethyl hydroxylamine, stopper consumption is 10 ~ 500 μ g/g of hydrocarbon raw material amount.The double solvents that the present invention selects coordinates with high-efficiency polymerization inhibitor, can reduce stopper consumption, significantly reduce cinnamic percent polymerization.
Description
Technical field
The present invention is a kind of method of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, specifically, is the method using double solvents recycling vinyl benzene with abstraction distillation from hydrocarbon mixture.
Background technology
Styrene monomer is important basic organic chemical industry raw material, in coating, agricultural chemicals, medicine etc., also have extensive use.According to statistics, containing the vinylbenzene of 3 ~ 5% in the steam cracking gasoline of ethylene cracker by-product, a set of 1,000,000 tons/year of ethylene units are because of the difference of raw material, and containing vinylbenzene in pyrolysis gasoline is 2 ~ 30,000 tons/year.In the technological process of existing process pyrolysis gasoline, this part vinylbenzene is hydrogenated into ethylbenzene, is stored in C
8in cut, this C being rich in ethylbenzene
8cut, supply downstream p-Xylene unit is very undesirable as raw material.If dehydrogenation becomes vinylbenzene again after adopting superfractionation separation ethylbenzene, long flow path, energy consumption are high, also unreasonable.
By contrast, from pyrolysis gasoline, direct separating phenylethylene is a very attractive technology.But pyrolysis gasoline C
8fractions consisting is very complicated, and between component, boiling point closely, and wherein the component that be separated the most difficult with vinylbenzene is o-Xylol and phenylacetylene.O-Xylol and cinnamic boiling-point difference are only 0.8 DEG C, and the relative volatility of the two only has 1.04, need thousands of pieces of theoretical stages with conventional distillation, are therefore actually to realize.
From without separating phenylethylene the pyrolysis gasoline of hydrogenation, feasible method adopts extracting rectifying.Extracting rectifying process has two key problem in technology, and one is solvent, and the performance of solvent comprises selectivity, boiling point, thermo-chemical stability and solvent to cinnamic polymerization inhibition performance etc., has vital impact to process technology economic target.Next how effectively to suppress styrene polymerization, and this is related to that can device long-period stable operation.In order to suppress styrene polymerization, key is screening high-efficiency polymerization inhibitor.In addition, the solvent reclamation process removing high boiling substance will also be solved.
GB1,038, the 606 a kind of methods proposing separating phenylethylene from hydrocarbon mixture, this method first processes hydrocarbon raw material with Fuller's earth, then uses the solvent of the aqueous solution as extracting rectifying of silver salt, 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 using polymerization retarder and extracting, rectifying and separating phenylethylene from pyrolysis gasoline, this method carries out extracting rectifying to pyrolysis gasoline under polar solvent and nitrogenous polymerization retarder exist, then from solvent, vinylbenzene is reclaimed, vinylbenzene recovery obtained again and enough nitric acid reactions remove the impurity in vinylbenzene, then obtain substantially colourless and pure vinylbenzene from the vinylbenzene cut after new distillation removing impurity.Described polar solvent is selected from N,N-DIMETHYLACETAMIDE, dimethyl formamide, N-Methyl pyrrolidone and methyl-sulphoxide etc., and the polymerization retarder of use is sulphur, Resorcinol, p-ten.-butylcatechol.But the preferred dimethylacetamide solvent of institute due to boiling point (165 DEG C) on the low side, with adjacent and toluene and vinylbenzene boiling-point difference too little, therefore process energy consumption is high.
USP4,596, the 655 a kind of methods disclosing separating phenylethylene class unsaturated hydrocarbon from hydrocarbon mixture, adopting aminoethylpiperazine to hold concurrently stopper as the solvent of extracting rectifying, is also need 115 ~ 125 pieces of theoretical stages under the condition of 8 in solvent ratio.
The method of the disclosed extracting, rectifying and separating phenylethylene from pyrolysis gasoline of CN1077560C proposes the solvent of extracting rectifying to be divided into two portions, solvent is primarily of being selected from propylene carbonate, tetramethylene sulfone, methyl carbitol, 1-Methyl-2-Pyrrolidone, 2-Pyrrolidone or their mixture but the first part not comprising water and the second section that is made up of water form, first part's solvent enters from extractive distillation column top, and 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 cut; comprise the sulfone compound of 15 ~ 60% and the nitrogenous compound of 40 ~ 45%; described sulfone compound is selected from dimethyl sulfoxide (DMSO) or tetramethylene sulfone; nitrogenous compound is selected from least one in succinonitrile, N,N-dimethylacetamide, METHYLPYRROLIDONE, 2-Pyrrolidone, aminoethyl piperazine or 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 being greater than 50ppm adding water-containing solvent dissolving in the vinylbenzene Aquo System of 5 ~ 99% prevents cinnamic polymerization to weight percent concentration, wherein stopper weight percent consists of: a) nitrite of 20% ~ 80%; B) quinones of 10% ~ 50%; C) nitrophenol, many nitrophenol or derivatives thereof of 1% ~ 35%.
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 be selected from sulfone compound, pyrrolidones, glycols compound or among them any two or three mixture, solubility promoter is selected from C
9~ C
12aromatic hydrocarbons, containing the acid amides of 2 ~ 6 carbon atoms or their mixture.
CN101955409A discloses a kind of method of ethene suppressing base aromatics polymerization in extractive distillation process, described inhibitor is 2-sec-butyl-4,6-dinitrophenol (DNBP), addition is at least 10,000wtppm of vinyl aromatic compounds amount.
Cheng Wenwu is at " the composition and performance research of vinylbenzene Compositional type stopper " (Zhejiang University's master thesis, in May, 2007) disclose by 4-hydroxyl-2 in a literary composition, 2,6, the composite polymerzation inhibitor of 6-tetramethyl piperidine nitrogen oxygen free radical (OH-TEMPO), azanol and DNBP composition, this stopper extends inductive phase, and the slow poly-effect after terminating inductive phase also increases.
In the prior art, solvent can not be taken into account the key ingredient o-Xylol/selectivity of vinylbenzene separation, the contradiction to threes such as structure adaptability and the polymerization inhibition performances of itself well, although tetramethylene sulfone selectivity is good, but it is on the low side to polymer solubility, once produce polymkeric substance in process, easily separate out and occluding device.Existing stopper boiling point is all very high, or the too low easy precipitation of solvability, or consumption is large, polymerization inhibition effect is not good, affects the long-period stable operation of whole device.
Summary of the invention
The object of this invention is to provide a kind of method of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, the double solvents that this method is selected coordinates with polycomponent stopper, can reduce stopper consumption, significantly reduce cinnamic percent polymerization.
The method of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture provided by the invention, comprise and hydrocarbon mixture is carried out extracting rectifying recovery vinylbenzene wherein with double solvents under stopper exists, described double solvents comprises the main solvent of 80 ~ 99 quality %, the solubility promoter of 0.01 ~ 19 quality % and the water of 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 %, N-diethyl hydroxylamine.
The solubility promoter that the present invention adds moderate boiling point, itself has good inhibition, polymkeric substance is had to larger dissolving power in the cinnamic main solvent of extracting rectifying, with polycomponent stopper with the use of, effectively can reduce the temperature at the bottom of extractive distillation column and at the bottom of solvent recovery tower, significantly reduce stopper consumption, greatly reduce cinnamic polymerization, avoid polymkeric substance to separate out, effectively extend the steady running cycle of recycling vinyl benzene with abstraction distillation device.
Accompanying drawing explanation
Fig. 1 is for using the inventive method from pyrolysis gasoline C
8the schematic flow sheet of recycling vinyl benzene with abstraction distillation in fraction.
Embodiment
The present invention adds in the cinnamic main solvent of extracting rectifying to be had larger dissolving power to polymkeric substance and self has the methoxyphenol of polymerization inhibition performance to be solubility promoter, and in addition, solubility promoter can also be the mixture of methoxyphenol and glycol monomethyl ether.The inventive method by comprise the double solvents of described solubility promoter and polycomponent stopper with the use of, stopper consumption can be reduced, reduce the temperature at the bottom of extractive distillation column and at the bottom of solvent recovery tower, extend the steady running time of extracting rectifying device.
Double solvents of the present invention preferably includes the water of the main solvent of 86 ~ 99 quality %, the solubility promoter of 0.1 ~ 13.0 quality % and 0.1 ~ 1.0 quality %.
Main solvent in described double solvents is selected from sulfone compound, one or more in preferred tetramethylene sulfone, dimethyl sulfone and 3-methyl sulfolane, more preferably tetramethylene sulfone.
Solubility promoter in described double solvents is methoxyphenol, for increasing the solvability to styrene polymer further, 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, preferably 3 ~ 1: 1.
The inventive method stopper used contains various ingredients, and described stopper preferably includes the N of the nitroxyl free radical of 30 ~ 65 quality %, the nitrophenol of 15 ~ 40 quality % and derivative and 15 ~ 35 quality %, N-diethyl hydroxylamine.
Nitroxyl free radical in the inventive method stopper used also comprises the compound containing oxygen nitrogen free radical, is selected from 4-hydroxyl-2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical, tricresyl phosphite (2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical) ester or its mixture.
Described nitrophenol and derivative thereof be 2,6-dinitro-p-cresols, 2-sec-butyl-4,6-dinitrophenol or 2,4-DNP preferably.
The mass ratio of the total amount of described stopper and hydrocarbon mixture, i.e. extracting rectifying raw material is 10 ~ 500 μ g/g, preferably 30 ~ 300 μ g/g.
During with the inventive method recycling vinyl benzene with abstraction distillation, the middle part of hydrocarbon mixture from extractive distillation column is introduced, double solvents is introduced from extracting rectifying tower top, stopper at the bottom of extractive distillation column charging, extractive distillation column or solvent recuperation tower top introduce, after 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 solvent recuperation tower top, double solvents is discharged at the bottom of solvent recovery tower, preferably returns extractive distillation column recycle.
The theoretical plate number of described extractive distillation column preferably 60 ~ 90, the mass ratio of double solvents and hydrocarbon mixture is 3 ~ 6, and trim the top of column ratio is 1 ~ 3, and column bottom temperature is 120 ~ 135 DEG C, and tower top pressure is 8 ~ 20kPa.
The theoretical plate number of described solvent recovery tower preferably 20 ~ 40, the reflux ratio of tower top is 0.5 ~ 2.5, and column bottom temperature is 130 ~ 145 DEG C, 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 %.
The present invention is described in detail below in conjunction with accompanying drawing.
In Fig. 1, entered by pipeline 1 containing cinnamic hydrocarbon mixture, after interchanger 101 heat exchange, enter extractive distillation column 102 by pipeline 2 from middle part, 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 discharged by the overhead line 3 of extractive distillation column containing cinnamic component, enter return tank 103, the raffinate flowed out by return tank, a part is passed back into the top of extractive distillation column 102 by pipeline 4, another part is discharged by pipeline 5, and moisture is discharged from pipeline 6.The rich solvent of rich in styrene is discharged by extracting rectifying tower bottom, solvent recovery tower 104 is entered from 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, is not discharged containing cinnamic poor double solvents by solvent recovery tower bottom tube line 13, after interchanger 106 heat exchange, enter pipeline 14, then enter pipeline 15 through interchanger 101.After the hydration also that the water of discharging from pipeline 11 and pipeline 6 are discharged interchanger 106 and from after the double solvents heat exchange at solvent recovery tower 104 end, water is vaporized and enters bottom solvent recovery tower 104 as stripping fluid through pipeline 12.
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 lists in table 1.Carry out extracting rectifying by the flow process shown in Fig. 1 to described raw material, reclaim vinylbenzene wherein, double solvents used is containing the water of the main solvent tetramethylene sulfone of 99 quality %, the solubility promoter 4-methoxyphenol of 0.5 quality % and 0.5 quality %.Stopper is the 4-hydroxyl-TEMPO (OH-TEMPO) of 55 quality %, 4, the 6-dinitrobenzene-2-sec-butyl phenols (DNBP) of 25 quality % and the N of 20 quality %, N-diethyl hydroxylamine.Stopper total amount is 100 μ g/g with the mass ratio for extraction feed.
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.
Solvent recovery tower number of theoretical plate is 28, tower top pressure 15kPa, and reflux ratio is 1.0.
Vinylbenzene purity be 99.7 quality %, under the rate of recovery is the condition of 95 quality %, extracting rectifying the results are shown in Table 2.
Example 2
By the method for example 1 from pyrolysis gasoline C
8reclaim vinylbenzene in cut, unlike the use of solubility promoter be 3-methoxyphenol, vinylbenzene purity be 99.7 quality %, under the rate of recovery is the condition of 95 quality %, extracting rectifying the results are shown in Table 2.
Example 3
By the method for example 1 from pyrolysis gasoline C
8reclaim vinylbenzene in cut, unlike the use of solubility promoter be 2-methoxyphenol, vinylbenzene purity be 99.7 quality %, under the rate of recovery is the condition of 95 quality %, extracting rectifying the results are shown in Table 2.
Example 4
By the method for example 1 from pyrolysis gasoline C
8vinylbenzene is reclaimed in cut, unlike the double solvents used water containing the main solvent tetramethylene sulfone of 88 quality %, the 2-methoxyphenol of 5 quality %, the triethylene glycol monomethyl ether of 6.5 quality % and 0.5 quality %, stopper total amount is 150 μ g/g with the mass ratio for extraction feed.Vinylbenzene purity be 99.7 quality %, under the rate of recovery is the condition of 95 quality %, extracting rectifying the results are shown in Table 2.
Example 5
By the method for example 1 from pyrolysis gasoline C
8vinylbenzene is reclaimed in cut, unlike the tricresyl phosphite (2 that stopper used is 40 quality %, 2,6,6-tetramethyl piperidine nitrogen oxygen free radical) ester, 2, the 6-dinitro-p-cresols (DNPC) of 30 quality % and the N of 30 quality %, N-diethyl hydroxylamine, the mass ratio of stopper total amount and extraction feed is 150 μ g/g, vinylbenzene purity be 99.7 quality %, under the rate of recovery is the condition of 95 quality %, extracting rectifying the results are shown in Table 2.
Comparative example 1
By the method for example 1 from pyrolysis gasoline C
8vinylbenzene is reclaimed in cut, unlike the use of double solvents be the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality %, the method preparation of CN1962582A pressed by stopper, stopper is containing the Sodium Nitrite of 65 quality %, the benzoquinones of 20 quality % and the DNBP of 15 quality %, the mass ratio of stopper total amount and extraction feed is 600 μ g/g, vinylbenzene purity be 99.7 quality %, under the rate of recovery is the condition of 95 quality %, extracting rectifying the results are shown in Table 2.
Comparative example 2
By the method for example 1 from pyrolysis gasoline C
8reclaim vinylbenzene in cut, unlike the use of double solvents be the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality %, stopper consumption is 200 μ g/g.Vinylbenzene purity be 99.7 quality %, under the rate of recovery is the condition of 95 quality %, extracting rectifying the results are shown in Table 2.
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 it is good to the solvability of stopper, stopper consumption reduces than comparative example, styrene polymerization rate significantly reduces, and without polymerization suspended substance in lean solvent, the continuous operating time that more outstanding is reaches regulation purity and the rate of recovery is than comparative example significant prolongation.
Claims (8)
1. the method for a recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, comprise and hydrocarbon mixture is carried out extracting rectifying recovery vinylbenzene wherein with double solvents under stopper exists, described double solvents comprises the main solvent of 80 ~ 99 quality %, the solubility promoter of 0.01 ~ 19 quality % and the water of 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 %, N--diethyl hydroxylamine,
Described sulfone compound be selected from tetramethylene sulfone, dimethyl sulfone and 3-methyl sulfolane one or more;
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;
Described nitroxyl free radical is 4-hydroxyl-TEMPO, tricresyl phosphite (TEMPO) ester or its mixture;
Described nitrophenol and derivative thereof are selected from 2,6-dinitro-p-cresol, 2-sec-butyl-4,6-dinitrophenol or 2,4-DNP.
2. in accordance with the method for claim 1, it is characterized in that described double solvents comprises the water of the main solvent of 86 ~ 99 quality %, the solubility promoter of 0.1 ~ 13.0 quality % and 0.1 ~ 1.0 quality %.
3., 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.
4. in accordance with the method for claim 1, it is characterized in that described stopper comprises the N of the nitroxyl free radical of 30 ~ 65 quality %, the nitrophenol of 15 ~ 40 quality % and derivative and 15 ~ 35 quality %, N-diethyl hydroxylamine.
5. 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.
6. in accordance with the method for claim 1, when it is characterized in that recycling vinyl benzene with abstraction distillation, the middle part of hydrocarbon mixture from extractive distillation column is introduced, double solvents is introduced from extracting rectifying tower top, stopper at the bottom of extractive distillation column charging, extractive distillation column or solvent recuperation tower top introduce, after 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 solvent recuperation tower top, and double solvents is discharged at the bottom of solvent recovery tower.
7. in accordance with the method for claim 6, it is characterized in that the theoretical plate number of described extractive distillation column is 60 ~ 90, the mass ratio of double solvents and hydrocarbon mixture is 3 ~ 6, and trim the top of column ratio is 1 ~ 3, column bottom temperature is 120 ~ 135 DEG C, and tower top pressure is 8 ~ 20kPa.
8. in accordance with the method for claim 6, it is characterized in that the theoretical plate number of described solvent recovery tower is 20 ~ 40, the reflux ratio of tower top is 0.5 ~ 2.5, and column bottom temperature is 130 ~ 145 DEG C, and tower top pressure is 8 ~ 20kPa.
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| CN107779224B (en) * | 2016-08-25 | 2020-04-17 | 北京安耐吉能源工程技术有限公司 | Gasoline processing method |
| CN108728155B (en) * | 2017-04-13 | 2020-04-17 | 北京安耐吉能源工程技术有限公司 | Composite solvent and application thereof |
| CN109517625B (en) * | 2017-09-20 | 2020-11-20 | 北京安耐吉能源工程技术有限公司 | FCC gasoline processing method |
| 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 |
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