CN103360200A - Composite solvent and method for extracting, rectifying and recovering styrene from hydrocarbon mixture - Google Patents
Composite solvent and method for extracting, rectifying and recovering styrene from hydrocarbon mixture Download PDFInfo
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- CN103360200A CN103360200A CN2012100889280A CN201210088928A CN103360200A CN 103360200 A CN103360200 A CN 103360200A CN 2012100889280 A CN2012100889280 A CN 2012100889280A CN 201210088928 A CN201210088928 A CN 201210088928A CN 103360200 A CN103360200 A CN 103360200A
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Abstract
The invention relates to a composite solvent for extracting, rectifying and recovering styrene from a hydrocarbon mixture. The composite solvent comprises the following components in percentage by weight: 80 to 90 percent of main solvent, 0.01 to 19 percent of cosolvent and 0.1 to 2.0 percent of water, wherein the main solvent is a sulfone compound; the cosolvent is metoxyphenol. The composite solvent is used in combination with a polymerization inhibitor, so the using amount of the polymerization inhibitor can be reduced and the polymerization ratio of the styrene can be reduced.
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.
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 cinnamic double solvents of extracting rectifying and method, described double solvents and stopper are used, and can reduce the stopper consumption, 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 present invention adds moderate boiling point, self has good inhibition, styrene polymer is had larger dissolving power in the cinnamic main solvent of extracting rectifying solubility promoter, can effectively reduce the temperature at the bottom of the extractive distillation column and at the bottom of the solvent recovery tower, reduce the 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, can effectively safeguard the high-quality of main solvent, guarantees the device long period steady running of extracting, rectifying and separating phenylethylene, and technique effect is outstanding.
Description of drawings
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 the fraction.
Embodiment
The present invention adds in moisture main solvent and self has in right amount good anti-polymerization and the solubility promoter that styrene polymer has a good solubility is made double solvents, is used for separation of extractive distillation and reclaims vinylbenzene.Double solvents provided by the invention cooperates with the stopper of commonly using, can effectively reduce the recovery column bottom temperature, the recovery column bottom temperature reduces, be conducive to reduce cinnamic polymerization, double solvents provided by the invention can be under lower recovery column bottom temperature, significantly reduce the consumption of stopper, and reduce the styrene polymerization rate.
Described double solvents preferably contains 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, is selected from tetramethylene sulfone, dimethyl sulfone and the 3-methyl sulfolane one or more, preferred tetramethylene sulfone.
Described solubility promoter is methoxyphenol, can be 4-methoxyphenol, 3-methoxyphenol or 2-methoxyphenol, also can be any two or three mixture in them.
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 %.
Provided by the invention from hydrocarbon mixture the method for recycling vinyl benzene with abstraction distillation, comprise hydrocarbon mixture is introduced from the middle part of extractive distillation column, double solvents of the present invention is introduced from cat head, stopper is introduced abstraction distillation system, and 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 tower, enter solvent recovery tower, vinylbenzene is discharged from the solvent recuperation cat head, and double solvents is discharged rear recycle at the bottom of solvent recovery tower.
Above-mentioned abstraction distillation system refers to carry out the whole device of 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 the used stopper of recycling vinyl benzene with abstraction distillation and can adopt any feasible method to inject abstraction distillation system.The method of preferably stopper being introduced abstraction distillation system is: stopper is injected hydrocarbon mixture, namely in the extracting rectifying raw material, or inject double solvents, or enter stopper from the extractive distillation column rising pouring, or enter stopper from the solvent recovery tower teeming.
The inventive method described stopper preferred nitrogen oxyradical or nitrophenol and derivative thereof.Described nitroxyl free radical also comprises the compound that contains the oxygen nitrogen free radical, preferred 4-hydroxyl-TEMPO (OH-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 stopper total amount of introducing in the abstraction distillation system and the mass ratio of hydrocarbon mixture are 10～500 μ g/g, preferred 30～300 μ g/g.The used stopper of the present invention can be a kind of in the above-mentioned stopper, also can be wherein two or more, as using simultaneously nitroxyl free radical and nitrophenol and derivative thereof to be stopper, 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 is preferred 60～90, 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 mass ratio of double solvents and hydrocarbon mixture is 3～6, and the trim the top of column ratio is 1～3.
The theoretical plate number of described solvent recovery tower is preferred 20～40, and the trim the top of column ratio is 0.5～2.5, and column bottom temperature is 130～145 ℃, and tower top pressure is 8～20kPa.
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.
Further specify 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 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 98 quality %, the solubility promoter 4-methoxyphenol of 1.5 quality % and the water of 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.
The 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.Be that 99.7 quality %, recycling phenylethylene rate are 95 quality % in vinylbenzene purity, and the extracting rectifying that does not carry out under the condition of solvent reclamation the results are shown in Table 2.
Example 2
Press the method for example 1 from pyrolysis gasoline C
8Recycling vinyl benzene with abstraction distillation in the cut, different is that the solubility promoter that uses is the 3-methoxyphenol, is that 99.7 quality %, recycling phenylethylene rate are 95 quality % in vinylbenzene purity, and the extracting rectifying that does not carry out under the condition of solvent reclamation the results are shown in Table 2.
Example 3
Press the method for example 1 from pyrolysis gasoline C
8Recycling vinyl benzene with abstraction distillation in the cut, different is that the stopper that uses is 2-sec-butyl-4,6-dinitrophenol (DNBP) is that 99.7 quality %, recycling phenylethylene rate are 95 quality % in vinylbenzene purity, and the extracting rectifying that does not carry out under the condition of solvent reclamation the results are shown in Table 2.
Example 4
Press the method for example 1 from pyrolysis gasoline C
8Recycling vinyl benzene with abstraction distillation in the cut, different is main solvent tetramethylene sulfone, the solubility promoter 2-methoxyphenol of 11.5 quality % and the water of 0.5 quality % that used double solvents contains 88 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, be that 99.7 quality %, recycling phenylethylene rate are 95 quality % in vinylbenzene purity, and the extracting rectifying that does not carry out under the condition of solvent reclamation the results are shown in Table 2.
Comparative Examples 1
Press the flow process of example 1 from pyrolysis gasoline C
8Recycling vinyl benzene with abstraction distillation in the cut, different is that double solvents 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 benzoquinones of 20 quality % and the DNBP of 15 quality %, and the mass ratio of stopper total amount and raw material is 600 μ g/g.Be that 99.7 quality %, recycling phenylethylene rate are 95 quality % in vinylbenzene purity, and the extracting rectifying that does not carry out under the condition of solvent reclamation the results are shown in Table 2.
Comparative Examples 2
Press the flow process of example 1 from pyrolysis gasoline C
8Recycling vinyl benzene with abstraction distillation in the cut, the double solvents that different is adopts is the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality %, and stopper is DNBP, and the mass ratio of itself and raw material is 300 μ g/g.Be that 99.7 quality %, recycling phenylethylene rate are 95 quality % in vinylbenzene purity, and the extracting rectifying that does not carry out under the condition of solvent reclamation the results are shown in Table 2.
Comparative Examples 3
Press the flow process of example 1 from pyrolysis gasoline C
8Recycling vinyl benzene with abstraction distillation in the cut, different is, and to adopt double solvents be the tetramethylene sulfone of 99.5 quality % and the water of 0.5 quality %, and stopper is OH-TEMPO, and the mass ratio of itself and raw material is 115 μ g/g.Be that 99.7 quality %, recycling phenylethylene rate are 95 quality % in vinylbenzene purity, and the extracting rectifying that does not carry 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 preferably solvability to stopper, the stopper consumption is reduced, the styrene polymerization rate reduces, in the lean solvent without the polymerization suspended substance, 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 that double solvents provided by the invention and stopper are used, can effectively reduce the stopper consumption, and reduce cinnamic percent polymerization.
Claims (13)
1. the double solvents of a 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.
2. according to double solvents claimed in 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. according to double solvents claimed in 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. according to double solvents claimed in claim 1, it is characterized in that described methoxyphenol is 4-methoxyphenol, 3-methoxyphenol or 2-methoxyphenol.
5. according to double solvents claimed in claim 1, it is characterized in that described hydrocarbon mixture is the C of pyrolysis gasoline
8Fraction.
6. the method for a recycling vinyl benzene with abstraction distillation from hydrocarbon mixture, comprise hydrocarbon mixture is introduced from the middle part of extractive distillation column, double solvents claimed in claim 1 is introduced from cat head, stopper is introduced abstraction distillation system, and 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 the solvent recuperation cat head, and double solvents is discharged rear recycle at the bottom of solvent recovery tower.
7. in accordance with the method for claim 6, it is characterized in that the method for stopper being introduced abstraction distillation system is: stopper is injected hydrocarbon mixture, or the injection double solvents, or enter stopper from the extractive distillation column rising pouring, or enter stopper from the solvent recovery tower teeming.
8. in accordance with the method for claim 6, it is characterized in that described stopper is nitroxyl free radical or nitrophenol and derivative thereof.
9. in accordance with the method for claim 6, it is characterized in that described nitroxyl free radical is 4-hydroxyl-TEMPO, tricresyl phosphite (TEMPO) ester or its mixture.
10. in accordance with the method for claim 6, it is characterized in that described nitrophenol and derivative thereof are 2,6-dinitro-p-cresol, 2-sec-butyl-4,6-dinitrophenol or 2,4-DNP.
11. in accordance with the method for claim 6, it is characterized in that the stopper total amount introduced and the mass ratio of hydrocarbon mixture are 10～500 μ g/g in abstraction distillation system.
12. in accordance with the method for claim 6, the theoretical plate number that it is characterized in that described extractive distillation column is 60～90, and the trim the top of column ratio is 1～3, and column bottom temperature is 120～135 ℃, tower top pressure is 8～20kPa, and the mass ratio of double solvents and hydrocarbon mixture is 3～6.
13. in accordance with the method for claim 6, the theoretical plate number that it is characterized in that described solvent recovery tower is 20～40, and the trim the top of column ratio is 0.5～2.5, and column bottom temperature is 130～145 ℃, and tower top pressure is 8～20kPa.
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| CN104900882A (en) * | 2015-06-09 | 2015-09-09 | 天津巴莫科技股份有限公司 | Dispersing agent recovering device, dispersing agent recovering method and method for preparing lithium manganese phosphate by using method |
| 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 |
| CN108728155A (en) * | 2017-04-13 | 2018-11-02 | 北京安耐吉能源工程技术有限公司 | A kind of double solvents and its application |
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