CN102060649A - Method for preparing high-purity cyclopentadiene - Google Patents
Method for preparing high-purity cyclopentadiene Download PDFInfo
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- CN102060649A CN102060649A CN2009102382086A CN200910238208A CN102060649A CN 102060649 A CN102060649 A CN 102060649A CN 2009102382086 A CN2009102382086 A CN 2009102382086A CN 200910238208 A CN200910238208 A CN 200910238208A CN 102060649 A CN102060649 A CN 102060649A
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Abstract
The invention relates to a method for preparing high-purity cyclopentadiene, which comprises the following steps of: heating a thermal decomposer containing purified conduction oil and a composite inhibitor and a rectifying reboiler to a specified temperature; adding dicyclopentadiene serving as a crude product into the thermal decomposer continuously and stably; allowing the depolymerized cyclopentadiene to enter a rectifying column; extracting high-purity cyclopentadiene from a tower top, heating a small amount of dicyclopentadiene and by-products by the reboiler at the tower bottom to rectify the small amount of dicyclopentadiene and by-products again, and recycling kettle liquid. The method has the advantages of simple equipment, high production capacity, little coking and long service life of the conduction oil serving as a raw material and the equipment.
Description
Technical field:
The present invention relates to a kind of method for preparing high-purity cyclopentadiene, it is raw material that invention more specifically relates to the polyester grade dicyclopentadiene, adopts the indirectly continuous depolymerization legal system of liquid phase to be equipped with the method for high-purity cyclopentadiene.
Background technology:
Cyclopentadiene (being called for short CPD) is the important chemical intermediate, and is of many uses, is synthetic pesticide, the raw material of plastics, rubber etc.Adopt recent years cyclopentadiene hydrogenating to prepare cyclopentenes, again so that fine chemical product such as production glutaraldehyde, cyclopentanone obtain the extensive attention of various countries especially.
Just present technology, dicyclopentadiene thermal depolymerization method is mainly adopted in the production of cyclopentadiene, is divided into the direct or indirect depolymerization of liquid phase, gas phase high temperature depolymerization, these methods respectively have its relative merits.The at present direct depolymerization process of liquid phase that adopt of China producer more, promptly simple reaction distillation.This processing unit is huge, the energy consumption height, and yield is low.
Gas phase high temperature depolymerization requires the depolymerization temperature higher, so higher depolymerization rate is arranged, is fit to serialization scale operation.As European patent EP 509445; Chinese patent CN1150942A, CN1093527C have all introduced gas phase high temperature depolymerization.This thermal depolymerization temperature is generally more than 300 ℃, and the depolymerization rate is separated and will be used a large amount of nitrogen or water vapor to be used as thinner to reduce coking phenomenon in the collecting process more than 95%.This method is to the equipment requirements height, and technology is comparatively complicated, requires system's oxygen level few as far as possible, adopts water vapor or high temperature nitrogen to have the energy consumption height as thinner simultaneously, the phenomenon of long obstruction duration of service reactor.This method mainly is that Shanghai research institute of petro-chemical corporation, Qilu Petrochemical research institute are studied at home at present.
Foreign patent (WO0236529A1) report, SAMAUNG company adopts the indirect depolymerization of liquid phase, produces cyclopentadiene, 180～210 ℃ of depolymerization temperature, depolymerization rate 90% adopts single stopper, but inert diluent (carrier thermal oil) reclaims comparatively difficulty.Liquid phase indirect thermal depolymerization method mainly exists coking or olefinic polymerization generation superpolymer to be brought in the carrier thermal oil at present, and the long-time running of equipment is obstructed.
Summary of the invention:
The purpose of this invention is to provide a kind of employing composite polymerzation inhibitor to improve liquid phase depolymerization reaction temperature and depolymerization rate, the technology that the coking of energy good restraining, carbon deposit and superpolymer produce is simple, the method easy to operate, that can the long playing liquid phase indirect depolymerization of equipment is produced high-purity cyclopentadiene.Make continuous liquid phase separate that the yield of cyclopentadiene reaches more than 95% in the collecting process, purity 98%.
The objective of the invention is to be achieved by the following technical programs:
At first composite polymerzation inhibitor and pure thermal oil are joined in thermal decomposer and the rectifying reboiler, feed the nitrogen replacement system air, the heating thermal oil is to the depolymerization temperature, by volume pump the crude product dicyclopentadiene is joined the thermal decomposer from the thermal decomposer bottom then, contact with high temperature heat conductive oil, in thermal decomposer, stop 1.5～2.0S, the dicyclopentadiene gasification, the cyclopentadiene of depolymerization enters in the rectifying column, cat head distillates the cyclopentadiene of higher degree, a small amount of dicyclopentadiene that does not have enough time to gasify and by product be the heating of rectifying reboiler at the bottom of tower, rectifying once more, the cyclopentadiene of depolymerization is purified through rectifying column, process condensation in condenser, to gathering jar, still liquid thermal oil can recycle.
Described thermal depolymerization temperature is 270～300 ℃, thermal depolymerization reaction times 1.5～2S.
Described thermal oil and composite polymerzation inhibitor weight ratio are 1: 0.005～0.01.
Described composite polymerization inhibitor is the compound ligand of the mantoquita of active fixed stopper, thermo-sensitivity stopper and trace, and three's weight ratio is 1: 1: 0.5～1.
Described composite polymerization inhibitor, active fixed stopper is a Resorcinol, 2, at least a in 6-dinitrobenzene p-cresol, the 4-tert-butyl catechol; The thermo-sensitivity stopper is a phenothiazine; Mantoquita is at least a in cuprous chloride, cuprous bromide, three kinds of cuprous halides of cuprous iodide.
The present invention has following significant effect:
(1) the present invention adopt liquid phase indirectly continuously depolymerization produce highly purified cyclopentadiene, to have equipment simple for technology more before, reaction conditions gentleness, operation are easy to control, constant product quality, low cost and other advantages, are easy to realize industrial production.
(2) the present invention adopts composite polymerization inhibitor can improve the generation of liquid phase depolymerization reaction temperature and depolymerization rate and good restraining coking, carbon deposit and superpolymer.
(3) the present invention adopts composite polymerization inhibitor, and equipment moves 600 hours continuously, and running is normal, and heat-carrying solvent thermal oil quality, viscosity do not have to change substantially, and cyclopentadiene is produced in the continous-stable operation, and yield reaches more than 95%, purity 98%.
Description of drawings
Fig. 1 prepares the high-purity cyclopentadiene process flow sheet.
Wherein: 1, head tank; 2, thermal decomposer; 3, rectifying column; 4, condenser; 5, gather jar; 6, rectifying reboiler; 7, water cooler; 8, still liquid holding tank; 9; The nitrogen steel cylinder; 10, volume pump; 11, tower still recycle pump
Embodiment:
Embodiment 1
The pure thermal oil and the composite polymerization inhibitor that with weight ratio are 1: 0.005 earlier join thermal decomposer 2, in the rectifying reboiler 6, feed the nitrogen replacement system air, heating thermal oil to 270 ℃, by volume pump crude product dicyclopentadiene (mass fraction 83.5%) is joined the thermal decomposer from the thermal decomposer bottom then, contact with high temperature heat conductive oil, the control input speed, make it in thermal decomposer, to stop 2.0S, the dicyclopentadiene gasification, the cyclopentadiene of depolymerization enters rectifying column 3 and carries out rectifying, cat head is isolated highly purified cyclopentadiene and is entered (cryopreservation) in the collector 5 through condenser 4, the rectifying once more after tower bottom reboiler 6 heating of a small amount of uncracked dicyclopentadiene and by product.Composite polymerization inhibitor is the compound ligand of Resorcinol, phenothiazine and cuprous chloride, and three's weight ratio is 1: 1: 0.5.
Continous-stable moved more than 48 hours, gas chromatographic analysis cyclopentadiene purity 98.12%, yield 95.7%.
The pure thermal oil and the composite polymerization inhibitor that with weight ratio are 1: 0.008 earlier join thermal decomposer 2, in the rectifying reboiler 6, feed the nitrogen replacement system air, heating thermal oil to 280 ℃, by volume pump crude product dicyclopentadiene (mass fraction 83.5%) is joined the thermal decomposer from the thermal decomposer bottom then, contact with high temperature heat conductive oil, the control input speed, make it in thermal decomposer, to stop 2.0S, the dicyclopentadiene gasification, the cyclopentadiene of depolymerization enters rectifying column 3 and carries out rectifying, cat head is isolated highly purified cyclopentadiene and is entered (cryopreservation) in the collector 5 through condenser 4, the rectifying once more after tower bottom reboiler 6 heating of a small amount of uncracked dicyclopentadiene and by product.Composite polymerization inhibitor is 2, the compound ligand of 6-dinitrobenzene p-cresol, phenothiazine and cuprous bromide, and three's weight ratio is 1: 1: 0.8.
Continous-stable moved more than 48 hours, gas chromatographic analysis cyclopentadiene purity 98.37%, yield 96.1%.
The pure thermal oil and the composite polymerization inhibitor that with weight ratio are 1: 0.01 earlier join thermal decomposer 2, in the rectifying reboiler 6, feed the nitrogen replacement system air, heating thermal oil to 280 ℃, by volume pump crude product dicyclopentadiene (mass fraction 92.7%) is joined the thermal decomposer from the thermal decomposer bottom then, contact with high temperature heat conductive oil, the control input speed, make it in thermal decomposer, to stop 1.5S, the dicyclopentadiene gasification, the cyclopentadiene of depolymerization enters rectifying column 3 and carries out rectifying, cat head is isolated highly purified cyclopentadiene and is entered (cryopreservation) in the collector 5 through condenser 4, the rectifying once more after tower bottom reboiler 6 heating of a small amount of uncracked dicyclopentadiene and by product.Composite polymerization inhibitor is the compound ligand of 4-tert-butyl catechol, phenothiazine and cuprous iodide, and three's weight ratio is 1: 1: 0.5.
Continous-stable moved more than 48 hours, gas chromatographic analysis cyclopentadiene purity 98.17%, yield 96.4%.
The pure thermal oil and the composite polymerization inhibitor that with weight ratio are 1: 0.005 earlier join thermal decomposer 2, in the rectifying reboiler 6, feed the nitrogen replacement system air, heating thermal oil to 300 ℃, by volume pump crude product dicyclopentadiene (mass fraction 92.7%) is joined the thermal decomposer from the thermal decomposer bottom then, contact with high temperature heat conductive oil, the control input speed, make it in thermal decomposer, to stop 1.5S, the dicyclopentadiene gasification, the cyclopentadiene of depolymerization enters rectifying column 3 and carries out rectifying, cat head is isolated highly purified cyclopentadiene and is entered (cryopreservation) in the collector 5 through condenser 4, the rectifying once more after tower bottom reboiler 6 heating of a small amount of uncracked dicyclopentadiene and by product.Composite polymerization inhibitor is the compound ligand of Resorcinol, phenothiazine and cuprous chloride, and three's weight ratio is 1: 1: 1.
Continous-stable moved more than 72 hours, gas chromatographic analysis cyclopentadiene purity 98.44%, yield 95.5%.
The thermal oil and the composite polymerization inhibitor that recycle more than 600 hours were joined thermal decomposer 2 by weight 1: 0.01, in the rectifying reboiler 6, feed the nitrogen replacement system air, heating thermal oil to 300 ℃, by volume pump crude product dicyclopentadiene (mass fraction 92.7%) is joined the thermal decomposer from the thermal decomposer bottom then, contact with high temperature heat conductive oil, the control input speed, make it in thermal decomposer, to stop 2.0S, the dicyclopentadiene gasification, the cyclopentadiene of depolymerization enters rectifying column 3 and carries out rectifying, cat head is isolated highly purified cyclopentadiene and is entered (cryopreservation) in the collector 5 through condenser 4, the rectifying once more after tower bottom reboiler 6 heating of a small amount of uncracked dicyclopentadiene and by product.Composite polymerization inhibitor is 2, the compound ligand of 6-dinitrobenzene p-cresol, phenothiazine and cuprous chloride, and three's weight ratio is 1: 1: 0.5.
Continous-stable moved more than 48 hours, gas chromatographic analysis cyclopentadiene purity 98.67%, yield 95.8%.
Embodiment 6
The thermal oil and the composite polymerization inhibitor that recycle more than 600 hours were joined thermal decomposer 2 by weight 1: 0.008, in the rectifying reboiler 6, feed the nitrogen replacement system air, heating thermal oil to 300 ℃, by volume pump crude product dicyclopentadiene (mass fraction 83.5%) is joined the thermal decomposer from the thermal decomposer bottom then, contact with high temperature heat conductive oil, the control input speed, make it in thermal decomposer, to stop 1.5S, the dicyclopentadiene gasification, the cyclopentadiene of depolymerization enters rectifying column 3 and carries out rectifying, cat head is isolated highly purified cyclopentadiene and is entered (cryopreservation) in the collector 5 through condenser 4, the rectifying once more after tower bottom reboiler 6 heating of a small amount of uncracked dicyclopentadiene and by product.Composite polymerization inhibitor is the compound ligand of 4-tert-butyl catechol, phenothiazine and cuprous chloride, and three's weight ratio is 1: 1: 1.
Continous-stable moved more than 72 hours, gas chromatographic analysis cyclopentadiene purity 98.51%, yield 95.7%.
Claims (2)
1. method for preparing high-purity cyclopentadiene is characterized in that: comprise step:
(a) under nitrogen protection, composite polymerzation inhibitor and pure thermal oil are joined in thermal decomposer (2), the rectifying reboiler (6), be heated to the depolymerization temperature, the crude product dicyclopentadiene be added to continuously and stably in the thermal decomposer (2) then, the cyclopentadiene of depolymerization enters rectifying column (3);
(b) cat head is isolated purity and is entered in the collector (5) through condenser (4) greater than 98% cyclopentadiene, the rectifying once more after tower bottom reboiler (6) heating of a small amount of uncracked dicyclopentadiene and by product, still liquid thermal oil can recycle for a long time;
Described thermal depolymerization temperature is 270～300 ℃, thermal depolymerization reaction times 1.5～2S;
Described thermal oil and composite polymerzation inhibitor weight ratio are 1: 0.005～0.01;
Described composite polymerzation inhibitor is the compound ligand of active fixed stopper, thermo-sensitivity stopper and mantoquita, and three's weight ratio is 1: 1: 0.5～1.
2. the method for preparing high-purity cyclopentadiene as claimed in claim 1 is characterized in that: the active fixed stopper of composite polymerization inhibitor is a Resorcinol, 2, at least a in 6-dinitrobenzene p-cresol, the 4-tert-butyl catechol; The thermo-sensitivity stopper is a phenothiazine; Mantoquita is at least a in cuprous chloride, cuprous bromide, three kinds of cuprous halides of cuprous iodide.
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| CN102336628A (en) * | 2010-07-22 | 2012-02-01 | 中国石油天然气股份有限公司 | Method for preparing cyclopentadiene through continuous depolymerization and rectification |
| CN102992939A (en) * | 2012-12-07 | 2013-03-27 | 四川大学 | High-yield preparation method for high-purity cyclopentadiene |
| EP2781496A1 (en) | 2013-03-20 | 2014-09-24 | Evonik Industries AG | Method and composition for inhibiting the polymerisation of cyclopentadiene compounds |
| RU2540329C1 (en) * | 2014-01-29 | 2015-02-10 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Method of producing cyclopentadiene |
| RU2540322C1 (en) * | 2014-01-29 | 2015-02-10 | Открытое акционерное общество "Нефтяная компания "Роснефть" | Method of producing dicyclopentadiene |
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| EP2781496A1 (en) | 2013-03-20 | 2014-09-24 | Evonik Industries AG | Method and composition for inhibiting the polymerisation of cyclopentadiene compounds |
| DE102013204950A1 (en) | 2013-03-20 | 2014-09-25 | Evonik Industries Ag | Process and composition for inhibiting the polymerization of cyclopentadiene compounds |
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