CN102295513A - Method for refining isoprene by extractive rectification - Google Patents
Method for refining isoprene by extractive rectification Download PDFInfo
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Abstract
The invention discloses a method for refining isoprene by extractive rectification. Isoprene is subjected to extractive rectification in the presence of dimethyl formamide solvent, and a polymerization inhibitor for inhibiting isoprene polymerization is added into the system, wherein the polymerization inhibitor comprises a component A and a component B. The component A is piperidine oxygen free radical and/or nitrophenol; the component B is diethylene glycol monomethyl ether and/or diethylene glycol monobutyl ether; and based on weight part, the ratio of the component A to the component B is 1: (0.5-2.0). The polymerization inhibitor is prepared into solution by using the dimethyl formamide solvent and then added into the extractive rectification system; based on weight part, the ratio of the sum of the component A and the component B to the dimethyl formamide is (2-8): 10; and the adding amount of the polymerization inhibitor is 3 to 30 weight percent of the quantity of the component A based on the isoprene. By adding an auxiliary component into the polymerization inhibitor, the dissolution dispersibility of the polymerization inhibitor in the extractive rectification system is greatly improved, so that the polymerization inhibitor has better polymerization inhibiting performance.
Description
Technical field
The present invention relates to a kind of method of refining isoprene, particularly adopting dimethyl formamide is the method for the refining isoprene of extraction fractional distillation of solvent.
Background technology
Isoprene is the fine chemical material of having many uses, but many fine chemical products such as synthetic perfume, agricultural chemicals, medicine, as pyrethroid pesticide, phantol, different vegetable alcohol, vitamin-E etc.Simultaneously, isoprene also is the monomer of multiple synthetic rubber, plastics and other synthetic materialss.The basic source of isoprene is the extracting and separating of oil C5 fraction, at present, directly the isoprene that is obtained by oil C5 fraction extracting and separating can reach the purity of chemical grade, can satisfy the requirement of synthetic most of fine chemical products, but, then should further make with extra care the impurity such as carbon four, carbon pentaene hydrocarbon and alkynes that wherein contain to remove as monomer as synthetic rubber, plastics and other synthetic materialss.Cyclopentadiene in the impurity and 2-methyl-2-butene etc. are very approaching with the boiling point of isoprene, and treating process need adopt extraction fractional distillation usually.And isoprene is a kind of typical vinyl compound; be characterized in containing the very active vinyl group of chemical property; in treating process, be subjected to multiple factor affecting such as high temperature; chain radical polymerization very easily takes place and generate polymkeric substance; this not only causes material loss; also can make equipment or line clogging, cause potential safety hazard or reduce the equipment cycle of operation and production efficiency in device interior deposition or fouling.Therefore in treating process, must add stopper in the system to suppress the formation of polymeric generation and foulant.
In the prior art, ethene suppressing based compound polymeric stopper is of a great variety, and wherein piperidines oxyradical and/or nitrophenol are employed with highly versatile more because of polymerization inhibition effect is good.As Chinese patent application 95115274.2 disclose a kind of under high temperature and no air conditions ethene suppressing base aromatics and alicyclic vinyl compounds of group polymeric method.Wherein, with 4-hydroxyl-2,2,6,6-tetramethyl piperidine-N-oxide compound or 4-acetylaminohydroxyphenylarsonic acid 2,2,6,6-tetramethyl piperidine-N-oxide compound separately or with the mixture of p-Nitrosophenol or 2-methyl-4-nitrosophenol as inhibitor.U.S. Pat 5,888,356 disclose a kind of prevention vinyl aromatic (as vinylbenzene, Vinylstyrene), vinyl fat family's (as vinylformic acid, methacrylic ester) polymeric method, it adopts 4-hydroxyl-2,2,6, the mixture of 6-tetramethyl piperidine oxyradical and p-Nitrosophenol or 2-methyl-4-nitrosophenol is a stopper.
Its main mechanism of action of ethene suppressing based compound polymeric stopper is by the living chain free radical reaction in stopper molecule and the system, generates non-free radical or low activity free radical that can not initiated polymerization, thereby polymerization is stopped.Stopper molecule and chain free radical are fully reacted, necessarily require stopper that very good dissolving dispersion state is arranged in system.The stopper that existing employing piperidines oxyradical and/or nitrophenol are mixed with in selectable solvent (as dimethyl formamide) and dissolution dispersity in vinyl compound system (as the mixture of isoprene and dimethyl formamide) can be not very good, this has caused weakening of its poly-effect of resistance.
Summary of the invention
The invention provides the method for the refining isoprene of a kind of extraction fractional distillation, it adds the stopper that component comprises piperidines oxyradical and/or nitrophenol in system in the extracting rectifying process, the present invention is by adding a kind of auxiliary component in stopper, dissolution dispersity can not ideal enough this technical problem in system to solve stopper.
Below be that the present invention solves the problems of the technologies described above concrete technical scheme:
The method of the refining isoprene of a kind of extraction fractional distillation comprises that isoprene carries out extracting rectifying in the presence of the solvent dimethyl formamide, adds inhibition of isoprenyl polymeric stopper in the extracting rectifying system.This stopper is a composition, and its component comprises component A and B component, wherein:
Component A is piperidines oxyradical and/or nitrophenol, and B component is diethylene glycol monomethyl ether and/or diethylene glycol monobutyl ether;
In weight part, component A: B component=1: (0.5～2.0).
Stopper adds the extracting rectifying system after being mixed with solution with the solvent dimethyl formamide earlier again, in weight part, (component A+ B component) generally speaking: dimethyl formamide=(2～8): 10;
The add-on of stopper is benchmark with the isoprene, in the amount of component A, is 0.3～3.0wt. ‰.
Above-mentioned piperidines oxyradical is generally takes from 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical, 2,2,6,6-tetramethyl piperidine oxyradical or 4-oxygen-2,2,6, a kind of in the 6-tetramethyl piperidine oxyradical; Nitrophenol is generally takes from 2,2, 4-dinitrophenol, 2,6-dinitro-p-cresol, o-nitrophenol or 2-sec-butyl-4, a kind of in the 6-dinitrophenol(DNP).
Said components A: B component=1: (1.0～1.5) are best; (component A+ B component): dimethyl formamide=(4～6): 10 is best.
The add-on of stopper is benchmark with the isoprene, in the amount of component A, is preferably 0.6～1.8wt. ‰.
The weight ratio that feeds intake of isoprene and solvent dimethyl formamide is generally isoprene: dimethyl formamide=(1.5～3.0): 10.
Above-mentioned extracting rectifying process is generally carried out in extractive distillation column, and the solvent dimethyl formamide that contains impurity is discharged by the tower still, and cat head must be made with extra care isoprene.
The tower still temperature of extractive distillation column generally is controlled to be 110～140 ℃, preferably is controlled to be 120～135 ℃; Tower still pressure generally is controlled to be 0.08～0.15MPa, preferably is controlled to be 0.10～0.15MPa; Tower top temperature generally is controlled to be 30～48 ℃, preferably is controlled to be 35～43 ℃; Tower top pressure generally is controlled to be 0.02～0.08MPa, preferably is controlled to be 0.02～0.05MP; Reflux ratio generally is controlled to be 2～10, preferably is controlled to be 3～6.
Essence of the present invention is to have added auxiliary component in the stopper that uses of extracting rectifying process, i.e. B component.This is a kind of pure ether compound, the contriver finds in experiment, this type of pure ether compound is at dimethyl formamide and in the extracting rectifying system of dimethyl formamide and isoprene formation, piperidines oxyradical and/or nitrophenol there is good solublization, make their dissolution dispersities in the extracting rectifying system be greatly improved, stopper contacts more fully with the chain free radical and even reaction more fully, more effectively stops chain radical polymerization, and inhibition obviously strengthens.On the other hand, this type of pure ether compound also has certain solvency action for the isoprene copolymer that has generated, can prevent that polymer molecule knot combinate form from becoming the viscosity decorating film, reduces the generation of polymkeric substance in the fouling of equipment inwall deposition.
In the present invention, the proportioning when selection of the compound of stopper component A or two or more compound are used etc. are all basic identical with prior art, do not cause new or special requirement because of the adding of B component; And B component determine that also be not limited by the selection of component A compound or two or more compound uses the time proportioning.The proterties of B component diethylene glycol monomethyl ether or diethylene glycol monobutyl ether is essentially identical, so both can be used alone or as a mixture.When mixing use, owing to do not have synergy, dependence or restricting relation between the two, any proportioning that can infer between them all is feasible.
Compared with prior art, the invention has the advantages that by adding a kind of auxiliary component in the stopper that uses to the extracting rectifying process, improved the dissolution dispersity of stopper in the extracting rectifying system greatly, make stopper have better polymerization inhibition performance, add less stopper in the system and just can obtain the ideal polymerization inhibition effect.
Below will the invention will be further described by specific embodiment.As previously mentioned, proportioning and prior art when the selection of stopper component A or two or more compound are used are basic identical, and the variation of its proportioning does not influence the embodiment of invention effect when B component is the mixture of two kinds of compounds, so embodiment or comparative example will be paid attention to enumerating of proportioning between B component and it and the component A.
In addition, except the prescription of stopper, the technology of whole extracting rectifying process is also basic identical with prior art, for well known to those of ordinary skill in the art, thereby and can infer the extracting rectifying system can be and obviously change physical properties and cause the extraction rectification technique condition changing because of the adding of the stopper B component of trace, so embodiment does not do too much enumerating to the extraction rectification technique condition.
Embodiment
One, the preparation of stopper:
[embodiment 1～10]
Component A and B respectively get suitable compound, drop in the desired amount in the solvent dimethyl formamide (DMF), impose to be stirred to fully dissolving to be mixed with inhibitor solution standby.The concrete component A that adopts of each embodiment and B component, component A and B component and the mutual proportioning of solvent see Table 1.
[comparative example 1～4]
Component A gets suitable compound, drops in the desired amount in the solvent dimethyl formamide (DMF), imposes to be stirred to fully dissolving to be mixed with inhibitor solution standby.Concrete component A that adopts of each comparative example and component A and the mutual proportioning of solvent see Table 1.
Table 1.
| Component A | B component | A: B (weight ratio) | (A+B): DMF (weight ratio) | |
| Embodiment 1 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical 2,2, 4-dinitrophenol | Diethylene glycol monobutyl ether | 1∶0.5 | 2.0∶10 |
| Embodiment 2 | 2,2,6,6-tetramethyl piperidine oxyradical o-nitrophenol | Diethylene glycol monomethyl ether | 1∶1.0 | 4.0∶10 |
| Embodiment 3 | 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical | Diethylene glycol monobutyl ether | 1∶2.0 | 8.0∶10 |
| Embodiment 4 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | The diethylene glycol monomethyl ether diethylene glycol monobutyl ether | 1∶1.5 | 7.0∶10 |
| Embodiment 5 | 2, the 6-dinitro-p-cresol | Diethylene glycol monobutyl ether | 1∶1.0 | 5.0∶10 |
| Embodiment 6 | 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | The diethylene glycol monomethyl ether diethylene glycol monobutyl ether | 1∶1.2 | 4.5∶10 |
| Embodiment 7 | 2-sec-butyl-4, the 6-dinitrophenol(DNP) | The diethylene glycol monomethyl ether diethylene glycol monobutyl ether | 1∶1.4 | 6.0∶10 |
| Embodiment 8 | 2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | Diethylene glycol monomethyl ether | 1∶1.2 | 5.5∶10 |
| Embodiment 9 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical | Diethylene glycol monomethyl ether | 1∶1.3 | 6.0∶10 |
| Embodiment 10 | 2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | Diethylene glycol monobutyl ether | 1∶1.3 | 5.0∶10 |
| Comparative example 1 | 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | - | - | 2.8∶10 |
| Comparative example 2 | 4-oxygen-2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | - | - | 2.1∶10 |
| Comparative example 3 | 2,2,6,6-tetramethyl piperidine oxyradical 2-sec-butyl-4,6-dinitrophenol(DNP) | - | - | 2.5∶10 |
| Comparative example 4 | 2,2,6,6-tetramethyl piperidine oxyradical 2,6-dinitro-p-cresol | - | - | 2.2∶10 |
Annotate: in the foregoing description or the comparative example, when component A or B component were the mixture of two kinds of compounds, the proportioning of two kinds of compounds was 1: 1.
Two, the refining isoprene of extraction fractional distillation
The inhibitor solution of each embodiment and comparative example preparation is applied to the refining isoprene of extraction fractional distillation respectively.Isoprene separates five fractions of petroleum cracked carbon by the DMF extraction process and obtains, and it is composed as follows:
Isoprene 99.16wt.%
Cyclopentadiene 0.23wt.%
2-methyl-2-butene 0.19wt.%
Valylene 0.13wt.%
Crotonylene 0.03wt.%
Other impurity surplus
In being 200 rectifying tower, theoretical stage number carries out the refining isoprene of extracting rectifying.Isoprene is preheated to 60～70 ℃ of middle part chargings by tower, solvent dimethyl formamide and inhibitor solution are by the top charging of tower, the solvent dimethyl formamide that contains impurity (comprising the polymkeric substance of isoprene) is discharged by the tower still that (when the industrial applications, solvent retrieval system after removing impurity recycles.), cat head must be made with extra care the isoprene product.
The weight ratio that feeds intake of isoprene and solvent dimethyl formamide is controlled to be isoprene: dimethyl formamide=(1.5～3.0): 10; Tower still temperature is controlled to be 120～135 ℃; Tower still pressure-controlling is 0.10～0.15MPa; Tower top temperature is controlled to be 35～43 ℃; Tower top pressure is controlled to be 0.02～0.05MP; Control of reflux ratio is 3～6.
The add-on of stopper is a benchmark with the isoprene that feeds intake, and in the amount of component A, the stopper add-on of each embodiment and comparative example sees Table 2.
Adopt the HP-6890 gas chromatograph to analyze refining isoprene product purity that each embodiment and comparative example obtain and the isoprene copolymer mass content in the discharging of extracting rectifying Tata still thereof, and calculate extracting rectifying process isoprene copolymer growing amount G, the results are shown in Table 2.
G is defined as:
Table 2.
| Component A add-on (wt. ‰) | Refining isoprene product purity (wt.%) | G (wt.％) | |
| Embodiment 1 | 0.3 | 99.60 | 0.58 |
| Embodiment 2 | 0.6 | 99.72 | 0.35 |
| Embodiment 3 | 0.8 | 99.66 | 0.25 |
| Embodiment 4 | 1.8 | 99.75 | 0.09 |
| Embodiment 5 | 3.0 | 99.73 | 0.11 |
| Embodiment 6 | 1.5 | 99.64 | 0.12 |
| Embodiment 7 | 1.2 | 99.78 | 0.21 |
| Embodiment 8 | 1.2 | 99.66 | 0.15 |
| Embodiment 9 | 1.0 | 99.70 | 0.28 |
| Embodiment 10 | 1.8 | 99.71 | 0.10 |
| Comparative example 1 | 1.8 | 99.75 | 3.2 |
| Comparative example 2 | 1.5 | 99.66 | 4.3 |
| Comparative example 3 | 1.2 | 99.68 | 5.6 |
| Comparative example 4 | 3.0 | 99.72 | 2.7 |
Claims (10)
1. the method for the refining isoprene of an extraction fractional distillation, comprise that isoprene carries out extracting rectifying in the presence of the solvent dimethyl formamide, it is characterized in that adding in the extracting rectifying system inhibition of isoprenyl polymeric stopper, this stopper is a composition, its component comprises component A and B component, wherein:
Component A is piperidines oxyradical and/or nitrophenol, and B component is diethylene glycol monomethyl ether and/or diethylene glycol monobutyl ether;
In weight part, component A: B component=1: (0.5～2.0);
Stopper adds the extracting rectifying system after being mixed with solution with the solvent dimethyl formamide earlier again, in weight part, (component A+ B component): dimethyl formamide=(2～8): 10;
The add-on of stopper is benchmark with the isoprene, in the amount of component A, is 0.3～3.0wt. ‰.
2. the method for refining isoprene according to claim 1 is characterized in that described piperidines oxyradical takes from 4-hydroxyl-2,2,6,6-tetramethyl piperidine oxyradical, 2,2,6,6-tetramethyl piperidine oxyradical or 4-oxygen-2,2,6, a kind of in the 6-tetramethyl piperidine oxyradical.
3. the method for refining isoprene according to claim 1 is characterized in that described nitrophenol takes from 2,2, 4-dinitrophenol, 2,6-dinitro-p-cresol, o-nitrophenol or 2-sec-butyl-4, a kind of in the 6-dinitrophenol(DNP).
4. the method for refining isoprene according to claim 1 is characterized in that described component A: B component=1: (1.0～1.5).
5. the method for refining isoprene according to claim 1 is characterized in that described (component A+ B component): dimethyl formamide=(4～6): 10.
6. the method for refining isoprene according to claim 1 is characterized in that the add-on of described stopper is benchmark with the isoprene, in the amount of component A, is 0.6～1.8wt. ‰.
7. the method for refining isoprene according to claim 1 is characterized in that the weight ratio that feeds intake of described isoprene and solvent dimethyl formamide is an isoprene: dimethyl formamide=(1.5～3.0): 10.
8. the method for refining isoprene according to claim 1 is characterized in that described extracting rectifying carries out in extractive distillation column, and the solvent dimethyl formamide that contains impurity is discharged by the tower still, and cat head must be made with extra care isoprene.
9. the method for refining isoprene according to claim 8, the tower still temperature that it is characterized in that described extractive distillation column is controlled to be 110～140 ℃, tower still pressure-controlling is 0.08～0.15MPa, tower top temperature is controlled to be 30～48 ℃, tower top pressure is controlled to be 0.02～0.08MPa, and control of reflux ratio is 2～10.
10. the method for refining isoprene according to claim 9, the tower still temperature that it is characterized in that described extractive distillation column is controlled to be 120～135 ℃, tower still pressure-controlling is 0.10～0.15MPa, tower top temperature is controlled to be 35～43 ℃, tower top pressure is controlled to be 0.02～0.05MPa, and control of reflux ratio is 3～6.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232159A (en) * | 2018-09-19 | 2019-01-18 | 山东玉皇化工有限公司 | A kind of polymerization inhibitor preparing isoprene for extracting rectifying |
| CN111233612A (en) * | 2020-03-13 | 2020-06-05 | 淄博鲁华同方化工有限公司 | Efficient polymerization inhibitor for extracting and separating carbon five by DMF (dimethyl formamide) method and application method thereof |
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| CN1119636A (en) * | 1994-08-19 | 1996-04-03 | 希尔斯股份公司 | Inhibition of the polymerization of vinylaromatic or vinyliphatic compounds |
| US5508366A (en) * | 1994-10-18 | 1996-04-16 | S. C. Johnson & Son, Inc. | Continuous production of reduced gel content hydroxylated addition polymers |
| CN1417177A (en) * | 2001-11-08 | 2003-05-14 | 中国石化上海石油化工股份有限公司 | Prepn process of high-purity m-pentadiene from C5 fraction as side product of petroleum cracking to produce ethylene |
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Patent Citations (4)
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| CN1068141A (en) * | 1991-06-24 | 1993-01-20 | 南京大学 | Oil gasification liquid fuel and production technique thereof |
| CN1119636A (en) * | 1994-08-19 | 1996-04-03 | 希尔斯股份公司 | Inhibition of the polymerization of vinylaromatic or vinyliphatic compounds |
| US5508366A (en) * | 1994-10-18 | 1996-04-16 | S. C. Johnson & Son, Inc. | Continuous production of reduced gel content hydroxylated addition polymers |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232159A (en) * | 2018-09-19 | 2019-01-18 | 山东玉皇化工有限公司 | A kind of polymerization inhibitor preparing isoprene for extracting rectifying |
| CN111233612A (en) * | 2020-03-13 | 2020-06-05 | 淄博鲁华同方化工有限公司 | Efficient polymerization inhibitor for extracting and separating carbon five by DMF (dimethyl formamide) method and application method thereof |
| CN111233612B (en) * | 2020-03-13 | 2021-03-12 | 淄博鲁华同方化工有限公司 | Efficient polymerization inhibitor for extracting and separating carbon five by DMF (dimethyl formamide) method and application method thereof |
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Application publication date: 20111228 |