CN103360200B - A kind of double solvents of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture and method - Google Patents
A kind of double solvents of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture and method Download PDFInfo
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Abstract
A kind of double solvents of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, comprise the main solvent of 80 ~ 99 quality %, the solubility promoter of 0.01 ~ 19 quality % and the water of 0.1 ~ 2.0 quality %, described main solvent is sulfone compound, and solubility promoter is methoxyphenol.Described double solvents and stopper with the use of, stopper consumption can be reduced, and 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.
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 from hydrocarbon mixture the cinnamic double solvents of extracting rectifying and method, described double solvents and stopper with the use of, stopper consumption can be reduced, and reduce cinnamic percent polymerization.
Provided by the invention from hydrocarbon mixture the cinnamic double solvents of extracting rectifying, comprise the main solvent of 80 ~ 99 quality %, the solubility promoter of 0.01 ~ 19 quality % and the water of 0.1 ~ 2.0 quality %, described main solvent is sulfone compound, and solubility promoter is methoxyphenol.
The solubility promoter that the present invention adds moderate boiling point, self has good inhibition, styrene polymer is had to larger dissolving power in the cinnamic main solvent of extracting rectifying, effectively can reduce the temperature at the bottom of extractive distillation column and at the bottom of solvent recovery tower, reduce stopper consumption, greatly reduce cinnamic polymerization, avoid polymkeric substance to separate out.With double solvents provided by the invention extracting rectifying vinylbenzene from hydrocarbon mixture, process cost is low, effectively can safeguard the high-quality of main solvent, ensures the device long period steady running of extracting, rectifying and separating phenylethylene, and technique effect is given prominence to.
Accompanying drawing explanation
Fig. 1 is from pyrolysis gasoline C with double solvents of the present invention
8the schematic flow sheet of recycling vinyl benzene with abstraction distillation in fraction.
Embodiment
The present invention adds and self has in right amount good anti-polymerization and make double solvents to the solubility promoter that styrene polymer has a good solubility in moisture main solvent, reclaims vinylbenzene for separation of extractive distillation.Double solvents provided by the invention coordinates with conventional stopper, can effectively reduce recovery column bottom temperature, recovery column bottom temperature reduces, be conducive to reducing cinnamic polymerization, double solvents provided by the invention can under lower recovery column bottom temperature, significantly reduce the consumption of stopper, and reduce styrene polymerization rate.
Described double solvents is preferably containing 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 %.
Described main solvent is sulfone compound, is selected from one or more in tetramethylene sulfone, dimethyl sulfone and 3-methyl sulfolane, preferred tetramethylene sulfone.
Described solubility promoter is methoxyphenol, can be 4-methoxyphenol, 3-methoxyphenol or 2-methoxyphenol, also can be the mixture of in them any two or three.
The C of the preferred pyrolysis gasoline of described hydrocarbon mixture
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 method of recycling vinyl benzene with abstraction distillation from hydrocarbon mixture provided by the invention, comprise and the middle part of hydrocarbon mixture from extractive distillation column is introduced, double solvents of the present invention is introduced from tower top, stopper is introduced abstraction distillation system, and 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 tower, enter solvent recovery tower, vinylbenzene is discharged from solvent recuperation tower top, and double solvents is discharged Posterior circle and utilized at the bottom of solvent recovery tower.
Above-mentioned abstraction distillation system refers to the whole device carrying out extracting rectifying operation, comprises the parts such as extractive distillation column, solvent recovery tower and return tank and is communicated with the pipeline of each parts.The present invention carries out recycling vinyl benzene with abstraction distillation stopper used and any feasible method can be adopted to inject abstraction distillation system.Preferred method stopper being introduced abstraction distillation system is: stopper is injected hydrocarbon mixture, namely in extracting rectifying raw material, or injects double solvents, or enters stopper from extractive distillation column rising pouring, or enter stopper from solvent recovery tower teeming.
Stopper preferred nitrogen oxyradical described in the inventive method or nitrophenol and derivative thereof.Described nitroxyl free radical also comprises the compound containing oxygen nitrogen free radical, preferred 4-hydroxyl-2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical (OH-TEMPO), 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 stopper total amount introduced in abstraction distillation system and the mass ratio of hydrocarbon mixture are 10 ~ 500 μ g/g, preferably 30 ~ 300 μ g/g.The present invention's stopper used can be the one in above-mentioned stopper, also can be wherein two or more, as used nitroxyl free radical and nitrophenol and derivative thereof for stopper simultaneously, the mass ratio of nitroxyl free radical and nitrophenol and derivative thereof is 5 ~ 1: 1.
The theoretical plate number of described extractive distillation column preferably 60 ~ 90, 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 mass ratio of double solvents and hydrocarbon mixture is 3 ~ 6, and trim the top of column ratio is 1 ~ 3.
The theoretical plate number of described solvent recovery tower preferably 20 ~ 40, trim the top of column ratio is 0.5 ~ 2.5, and column bottom temperature is 130 ~ 145 DEG C, and tower top pressure is 8 ~ 20kPa.
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.
Further illustrate the present invention below by example, 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.By the flow process shown in Fig. 1, extracting rectifying is carried out to described raw material, reclaim vinylbenzene wherein.Double solvents used is containing the water of the main solvent tetramethylene sulfone of 98 quality %, the solubility promoter 4-methoxyphenol of 1.5 quality % and 0.5 quality %, stopper is 4-hydroxyl-2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical (OH-TEMPO), stopper injects raw material, and the mass ratio of stopper and raw material is 115 μ g/g.
Extractive distillation column theoretical plate number is 70, the mass ratio of tower top pressure 15kPa, double solvents/raw material is 3.8, reflux ratio 2.0.Solvent recovery tower theoretical plate number 28, tower top pressure 15kPa, reflux ratio is 1.0.Vinylbenzene purity be 99.7 quality %, recycling phenylethylene rate is 95 quality %, and the extracting rectifying do not carried out under the condition of solvent reclamation the results are shown in Table 2.
Example 2
By the method for example 1 from pyrolysis gasoline C
8recycling vinyl benzene with abstraction distillation in cut, unlike the use of solubility promoter be 3-methoxyphenol, vinylbenzene purity be 99.7 quality %, recycling phenylethylene rate is 95 quality %, and the extracting rectifying do not carried out under the condition of solvent reclamation the results are shown in Table 2.
Example 3
By the method for example 1 from pyrolysis gasoline C
8recycling vinyl benzene with abstraction distillation in cut, unlike the use of stopper be 2-sec-butyl-4,6-dinitrophenol (DNBP), vinylbenzene purity be 99.7 quality %, recycling phenylethylene rate is 95 quality %, and the extracting rectifying do not carried out under the condition of solvent reclamation the results are shown in Table 2.
Example 4
By the method for example 1 from pyrolysis gasoline C
8recycling vinyl benzene with abstraction distillation in cut, unlike the double solvents used water containing the main solvent tetramethylene sulfone of 88 quality %, the solubility promoter 2-methoxyphenol of 11.5 quality % and 0.5 quality %, stopper is 2,2,6, the mixture of 6-tetramethyl piperidine nitrogen oxygen free radical (OH-TEMPO) and DNBP, its mass ratio is 1: 1, the mass ratio of stopper total amount and raw material is 50 μ g/g, vinylbenzene purity be 99.7 quality %, recycling phenylethylene rate is 95 quality %, and the extracting rectifying do not carried out under the condition of solvent reclamation the results are shown in Table 2.
Comparative example 1
By the flow process of example 1 from pyrolysis gasoline C
8recycling vinyl benzene with abstraction distillation in cut, be the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality % unlike double solvents, the method preparation of CN1962582A pressed by stopper, stopper is containing the DNBP of the Sodium Nitrite of 65 quality %, the benzoquinones of 20 quality % and 15 quality %, and the mass ratio of stopper total amount and raw material is 600 μ g/g.Vinylbenzene purity be 99.7 quality %, recycling phenylethylene rate is 95 quality %, and the extracting rectifying do not carried out under the condition of solvent reclamation the results are shown in Table 2.
Comparative example 2
By the flow process of example 1 from pyrolysis gasoline C
8recycling vinyl benzene with abstraction distillation in cut, be the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality % unlike the double solvents adopted, stopper is DNBP, and the mass ratio of itself and raw material is 300 μ g/g.Vinylbenzene purity be 99.7 quality %, recycling phenylethylene rate is 95 quality %, and the extracting rectifying do not carried out under the condition of solvent reclamation the results are shown in Table 2.
Comparative example 3
By the flow process of example 1 from pyrolysis gasoline C
8recycling vinyl benzene with abstraction distillation in cut, be the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality % unlike employing double solvents, stopper is OH-TEMPO, and the mass ratio of itself and raw material is 115 μ g/g.Vinylbenzene purity be 99.7 quality %, recycling phenylethylene rate is 95 quality %, and the extracting rectifying do not carried out under the condition of solvent reclamation the results are shown in Table 2.
Table 1
Table 2
As shown in Table 2, under the condition of identical vinylbenzene purity and recycling phenylethylene rate, the double solvents that the present invention adopts has good solvability to stopper, stopper consumption is reduced, styrene polymerization rate reduces, without polymerization suspended substance in lean solvent, more significant effect is the continuous operating time prolongation that vinylbenzene reaches regulation purity (99.7 quality %) and the rate of recovery (95 quality %), illustrate double solvents provided by the invention and stopper with the use of, can effectively reduce stopper consumption, and reduce cinnamic percent polymerization.
Claims (8)
1. the double solvents of a recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, comprise 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 %, described main solvent is sulfone compound, solubility promoter is methoxyphenol, described sulfone compound be selected from tetramethylene sulfone, dimethyl sulfone and 3-methyl sulfolane one or more.
2., according to double solvents according to claim 1, it is characterized in that described methoxyphenol is 4-methoxyphenol, 3-methoxyphenol or 2-methoxyphenol.
3., according to double solvents according to claim 1, it is characterized in that described hydrocarbon mixture is the C of pyrolysis gasoline
8fraction.
4. the method for a recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, comprise and the middle part of hydrocarbon mixture from extractive distillation column is introduced, double solvents according to claim 1 is introduced from tower top, stopper is introduced abstraction distillation system, through 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 tower, enter solvent recovery tower, vinylbenzene is discharged from solvent recuperation tower top, double solvents is discharged Posterior circle and is utilized at the bottom of solvent recovery tower, described stopper is nitroxyl free radical or nitrophenol and derivative thereof, described nitroxyl free radical is 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 are 2, 6-dinitro-p-cresol, 2-sec-butyl-4, 6-dinitrophenol or 2, 2, 4-dinitrophenol.
5. in accordance with the method for claim 4, it is characterized in that method stopper being introduced abstraction distillation system is: stopper is injected hydrocarbon mixture, or injection double solvents, or enter stopper from extractive distillation column rising pouring, or enter stopper from solvent recovery tower teeming.
6. in accordance with the method for claim 4, it is characterized in that the mass ratio of stopper total amount and the hydrocarbon mixture introduced in abstraction distillation system is 10 ~ 500 μ g/g.
7. in accordance with the method for claim 4, it is characterized in that the theoretical plate number of described extractive distillation column is 60 ~ 90, trim the top of column ratio is 1 ~ 3, and column bottom temperature is 120 ~ 135 DEG C, tower top pressure is 8 ~ 20kPa, and the mass ratio of double solvents and hydrocarbon mixture is 3 ~ 6.
8. in accordance with the method for claim 4, it is characterized in that the theoretical plate number of described solvent recovery tower is 20 ~ 40, trim the top of column ratio 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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| CN106316769A (en) * | 2015-06-19 | 2017-01-11 | 中国石油化工股份有限公司 | Apparatus and method for separating styrene from hydrocarbons mixture |
| CN106554245A (en) * | 2015-09-30 | 2017-04-05 | 中国石油化工股份有限公司 | A kind of polymerization inhibitors for styrene rectification and its configuration, application process |
| 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 |
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