CN101314596B - Method for continuous preparation of epoxypropane - Google Patents
Method for continuous preparation of epoxypropane Download PDFInfo
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- CN101314596B CN101314596B CN2007100998535A CN200710099853A CN101314596B CN 101314596 B CN101314596 B CN 101314596B CN 2007100998535 A CN2007100998535 A CN 2007100998535A CN 200710099853 A CN200710099853 A CN 200710099853A CN 101314596 B CN101314596 B CN 101314596B
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention discloses a method for continuously preparing epoxy-propane, which is characterized in that a reactant containing propylene and hydrogen peroxide is continuously injected into a reaction system from a feed inlet, the raw powder form titanium silicate molecular sieve as a catalyst and the reactant are mixed uniformly to form slurry for reacting, the molecular sieve and the liquid reactant perform solid-liquid separation in a separation system, the molecular sieve is continuously circulated in a circulation pipeline composed of the reactor and the separation system, and part of liquid product flows out of the reaction system to obtain the objective product. By coupling the reaction and the separation in the method, the liquid product can be effectively discharged from the reaction region in time, the side reaction is reduced, the conversion rate of hydrogen peroxide is higher than 95% and the selectivity of the epoxypropane is higher than 90%.
Description
Technical field
The present invention relates to a kind of method of producing propylene oxide, the method for propylene and hydrogen peroxide epoxidation continuous production propylene oxide under existing more specifically to a kind of HTS.
Background technology
Propylene oxide is a kind of important Organic Chemicals, is only second to polypropylene and vinyl cyanide in acryloyl derivative, and main application is to produce urethane, propylene glycol, polyether glycol, and oil field emulsion splitter, tensio-active agent etc.At present, industrial production propylene oxide mainly adopts chlorohydrination and is total to the oxygen method, and the chlorohydrination weak point is the generation of a large amount of waste water, and environmental pollution is serious; And the oxygen method exists investment greatly altogether, and the problem of other low value-added products of coproduction.
The epoxidation of propylene that is found to be of HTS is produced the road that propylene oxide has been opened up a green.
Titanium molecular sieve catalysis propylene and hydrogen peroxide epoxidation are produced the reaction of propylene oxide, currently used conversion unit mainly contains two types, a kind of is that another kind is the slurry bed reactor that is applicable to former powdery HTS by the fixed-bed reactor that are applicable to moulding macrobead shape catalyzer of U.S. ARCO company (EP0659473) exploitation.
Necessary moulding when HTS is applied to fixed-bed reactor, the binding agents that moulding process adds etc. have certain negative impact to the catalytic performance of HTS, and the heat effect of propylene ring oxidation reaction is bigger, titanium-silicon molecular sieve catalyst after the moulding is unfavorable for conducting heat, mass transfer, is the major cause that causes catalyst deactivation.For the temperature of control catalyst bed, general normal employing strengthens the method for air speed in the actual production, but this method energy consumption is higher, and economy is relatively poor.
Slurry bed reactor is applied to propylene ring oxidation reaction, and HTS does not need moulding, can overcome the defective that fixed-bed reactor exist.
CN1256273A has disclosed a kind of shell and tube cycling stream conversion unit that is applicable to the fine particle HTS.This equipment is to be chief series tubular type cooling section based on the tubular reaction section of carrying out reaction process and one with the heat exchange by one, and formation such as gas-liquid separation section, it is characterized in that tubular reaction section and shell and tube cooling section put side by side, upper and lower ends is connected to form a loop with U type linkage section.When carrying out propylene and hydrogen peroxide epoxidation reaction, catalyzer adds by adding inlet continuously, mix with the raw material of continuous input, being slurry attitude shape circulates in loop by the order of conversion zone, gas-liquid separation section, cooling section, the partial reaction thing is with the bottom extraction of the solvent that contains catalyzer by the gas-liquid separation section, and tail gas flows out from the top simultaneously.
CN1631538A has disclosed a kind of membrane separation plant that is applied to HTS regeneration washing, in HTS regeneration washing process, the material that constantly will contain granules of catalyst, regenerated liquid or washings with pump adds in the membrane separation apparatus of certain pore size, per-meate side at membrane separation apparatus obtains regenerated liquid or washings, the outlet of membrane separation apparatus obtains trapped fluid and catalyzer, and under the effect of pressure reduction, return regeneration or carrying out washing treatment device, thereby can realize the regeneration washing of HTS.
Summary of the invention
The purpose of this invention is to provide a kind of method that is applicable to the propylene and the hydrogen peroxide epoxidation continuous production propylene oxide of former powdery HTS.
The method of continuous production propylene oxide provided by the invention, it is characterized in that with former powdered HTS be catalyzer, the reaction raw materials that contains propylene and hydrogen peroxide continuously injects reaction system by opening for feed, HTS and reaction mass uniform mixing are the reaction of slurry attitude shape, under the effect of inside and outside differential pressure, molecular sieve and liquid reactions material are realized solid-liquid separation in separation system, molecular sieve continues to be circulated in the circulation line of reactor and separation system composition, and the partially liq product flows out reaction system, obtain the purpose product, wherein, the pressure of reaction system is 0.1-3.0MPa, temperature is 30-60 ℃, when empty is 0.5-3h
-1, the mol ratio of propylene and hydrogen peroxide is (0.5-4.0): 1, and the mol ratio of solvent and hydrogen peroxide is (10-60): 1, the concentration of titanium-silicon molecular sieve catalyst is 1.0-30g/L in the reaction system.
In the method provided by the invention, said HTS preferably has the HTS of MFI structure.
In the method provided by the invention, epoxidation of propylene slurry attitude conversion unit mainly is made up of reactor, separation system and back-purge system three parts, wherein reactor and separation system are formed circulation line, it also is the main body of conversion unit, pump in the circulation line drives material and circulates in total system, not only playing the effect of mixture, also is to react the thermal source that normally carries out simultaneously.Reactor and circulation line all can be equipped with cooling outward and add cover, and the size of water coolant is subjected to the control of temperature of reaction system, make the temperature of reactive system be easy to control more.
In the method provided by the invention, said separation system is the solid-liquid separator that is made of the separatory membrane pipe, and film pore footpath is less than the particle diameter of HTS, and solid-liquid separator is one or more parallel connections, can be selected by the substantial sepn treatment capacity.Flow through the slurry attitude material of separatory membrane pipe under the effect of film pipe inside and outside differential pressure, realize the solid-liquid separation of catalyzer and liquid.Isolated a part of clear liquid carries out back flushing through back-purge system to the film pipe.
In the method provided by the invention, preferably the mixed solution with methyl alcohol or methyl alcohol and water is a solvent, a certain amount of HTS is dissolved in the methanol solvate of hydrogen peroxide, forms the paste-like feed liquid, injects reaction system by the catalyzer charging opening, until being full of the full cycle pipeline.The ON cycle pump, reach preset value to system temperature after, open propylene and liquid phase feed fresh feed pump respectively.Regulate the back pressure valve aperture, reach set value to system pressure.After total system was stable, product was flowed out by the stable can products export.
In the method provided by the invention, stop up film pore road, regularly carry out back flushing solid-liquid separator in order to prevent catalyzer, will be attached to the molecular sieve refunds reaction system on the film pipe, the recoil time is 1～3s, recoil is spaced apart 0.5～3h.
Method provided by the invention has the following advantages:
(1) coupling of reactor and solid-liquid separator is integrated, can realize epoxidation of propylene serialization production propylene oxide, HTS and the solvent ON-LINE SEPARATION that contains product, thereby make purpose product propylene oxide in time shift out reaction system, reduce the generation of side reaction, the selectivity height of purpose product propylene oxide.
(2) flow process is simple, and facility investment is little, easy handling.
Description of drawings
Fig. 1 is the schematic flow sheet that the invention provides method.
Wherein, 01 catalyzer charging opening, 02 magnetic flow meter, 03 vent valve, 04 temperature sensor, 05 tensimeter, 06 check valve, 07 tensimeter, 08 spinner-type flowmeter, 09 back pressure valve, 10 condensers, 11 sampling valves, 12 vent valves, 13 products exports, 14 container for storing liquids, 15 liquidometers, 16 tensimeters, 17 cooling water inlets, 18 catalyzer discharge openings, 19 cooling water outlets, 20 variable valve, 21 check valves, 22 hydrogen peroxide opening for feeds, 23 propylene feed mouths, 24 drains, 25 safety valve, 26 fluid level transmitters, 27 pressure transmitters, R-1 reactor, P01 recycle pump, the P02 backwashing pump, F-1 separator, F-2 separator.
Fig. 2 is the solid-liquid separator synoptic diagram.
Embodiment
Below in conjunction with schematic flow sheet 1, method provided by the invention is elaborated.
Reactor (R-1), recycle pump (P01) and separator (F-1, F-2) form a circulation line, wherein separator F-1 and F-2 are parallel in the circulation line, catalytic oxidation takes place in the slurry attitude fluid of reaction mixture that contains molecular sieve in the full cycle pipeline under the driving of recycle pump (P01).The heat effect of reaction is by recycle pump (P01) acting and cooling-water flowing adjustable valve (20) control, wherein flow rate of fluid can be regulated by the frequency-variable controller of Control Circulation pump (P01) rotating speed, and the aperture of cooling-water flowing adjustable valve (20) is controlled by temperature sensor (04).The slurry attitude fluid of separator of flowing through is realized molecular sieve and the solvent solid-liquid separation that contains the epoxidation product of alkene under the effect of separator inside and outside differential pressure, wherein molecular sieve is stayed in the circulation line, and part reaction back clear liquid flows out reaction system.
Separator as shown in Figure 2, its main working parts is a ceramic-film tube, during the equipment normal operation, needs to carry out regular back flushing to membrane separation apparatus, prevents that former powdered catalyst from stopping up fenestra, the specific implementation process is elaborated as follows in conjunction with Fig. 1:
Magnetic valve (09) is in closing condition (pump P02 closes when opening backwashing pump P02, magnetic valve (09) is in normally open), the scavenging solution that is used in the storage tank recoil is squeezed into separator (F-1 by pump P02, F-2), separator membrane pipe inside and outside differential pressure increases sharply, under the effect of pressure, scavenging solution sees through membrane tube wall with catalyzer refunds reaction system attached thereto, finishes backwash process.The best recoil time is 1-3s, and recoil is spaced apart 0.5-3h.
Below in conjunction with embodiment method provided by the invention is described further, but content not thereby limiting the invention.
The HTS that adopts among the embodiment (the method preparation that CN1132699C discloses) catalyzer is built long company by the Hunan and is produced, and trade names are HTS.The quantity of separator is decided by the actual treatment amount, adopts the separator form of two parallel connections in following examples, and the volume of full cycle pipeline is 2.5L.
The HTS molecular sieve that takes by weighing 50g is positioned in the methanol solution of hydrogen peroxide, stirs to be paste-like, injects reactive system by the catalyzer charging opening then.Open liquid phase feed (methanol solution of hydrogen peroxide) feed valve, when back pressure is 2.0MPa to system pressure, open the propylene feed valve then, control reaction temperature is 40 ℃.Wherein in the reaction system, the mol ratio of methyl alcohol and hydrogen peroxide is 40: 1 in the liquid phase feed, and the mol ratio of propylene and hydrogen peroxide is 2: 1, is 1.5h when empty.
The time sampling analytical results is: the transformation efficiency of hydrogen peroxide is greater than 98%, and the selectivity of propylene oxide is 93%, and the selectivity of 1-methoxyl group-2-propyl alcohol is 2.3%, and the selectivity of 2-methoxyl group-1-propyl alcohol is 3.2%, and the selectivity of propylene glycol is 1.5%.
The HTS HTS that takes by weighing 40g is positioned in the methanol solution of hydrogen peroxide, stirs to be paste-like, injects reactive system by the catalyzer charging opening then.Open the liquid phase feed feed valve, when back pressure is 2.0MPa to system pressure, open the propylene feed valve after system pressure is stable, temperature of reaction is controlled at 35 ℃.The mol ratio of methyl alcohol and hydrogen peroxide is 40: 1 in the liquid phase feed, and the mol ratio of propylene and hydrogen peroxide is 2: 1, and reaction is 2.0h when empty.
The time sampling analytical results is: the transformation efficiency of hydrogen peroxide is greater than 98%, and the selectivity of propylene oxide is 95%, and the selectivity of 1-methoxyl group-2-propyl alcohol is 1.7%, and the selectivity of 2-methoxyl group-1-propyl alcohol is 2.3%, and the selectivity of propylene glycol is 1.0%.
Embodiment 3
The HTS HTS that takes by weighing 50g is positioned in the methanol solution of hydrogen peroxide, stirs to be paste-like, injects reactive system by the catalyzer charging opening then.Open the liquid phase feed feed valve, when back pressure is 2.0MPa to system pressure, open the propylene feed valve after system pressure is stable, temperature of reaction is controlled at 35 ℃.The mol ratio of methyl alcohol and hydrogen peroxide is 40: 1 in the liquid phase feed, and the mol ratio of propylene and hydrogen peroxide is 2: 1, and reaction is 3.0h when empty.
The time sampling analytical results is: the transformation efficiency of hydrogen peroxide is greater than 98%, and the selectivity of propylene oxide is 91%, and the selectivity of 1-methoxyl group-2-propyl alcohol is 2.0%, and the selectivity of 2-methoxyl group-1-propyl alcohol is 5.5%, and the selectivity of propylene glycol is 1.5%.
Embodiment 4
The HTS HTS that takes by weighing 50g is positioned in the methanol solution of hydrogen peroxide, stirs to be paste-like, injects reactive system by the catalyzer charging opening then.Open the liquid phase feed feed valve, back pressure to system pressure is 1.5MPa, opens the propylene feed valve after the pressure-stabilisation.Temperature of reaction is controlled at 30 ℃.The mol ratio of methyl alcohol and hydrogen peroxide is 20: 1 in the liquid phase feed, and the mol ratio of propylene and hydrogen peroxide is 3: 1, and reaction is 1.0h when empty.
The time sampling analytical results is: the transformation efficiency of hydrogen peroxide is greater than 98%, and the selectivity of propylene oxide is 98%, and the selectivity of 1-methoxyl group-2-propyl alcohol is 0.5%, and the selectivity of 2-methoxyl group-1-propyl alcohol is 0.8%, and the selectivity of propylene glycol is 0.7%.
Embodiment 5
The HTS HTS that takes by weighing 50g is positioned in the methanol solution of hydrogen peroxide, stirs to be paste-like, injects reactive system by the catalyzer charging opening then.Open the liquid phase feed feed valve, when back pressure is 3.0MPa to system pressure, open the propylene feed valve after the pressure-stabilisation.Temperature of reaction is controlled at 35 ℃.The mol ratio of methyl alcohol and hydrogen peroxide is 60: 1 in the liquid phase feed, and the mol ratio of propylene and hydrogen peroxide is 1: 1, and reaction is 2.5h when empty.
The time sampling analytical results is: the transformation efficiency of hydrogen peroxide is greater than 95%, and the selectivity of propylene oxide is 95%, and the selectivity of 1-methoxyl group-2-propyl alcohol is 2.0%, and the selectivity of 2-methoxyl group-1-propyl alcohol is 1.7%, the selectivity 1.3% of propylene glycol.
Claims (3)
1. the method for a continuous production propylene oxide, it is characterized in that with former powdered HTS be catalyzer, the reaction raw materials that contains propylene and hydrogen peroxide continuously injects reaction system by opening for feed, HTS and reaction mass uniform mixing are the reaction of slurry attitude shape, under the effect of inside and outside differential pressure, molecular sieve and liquid reactions material are realized solid-liquid separation in separation system, molecular sieve continues to be circulated in the circulation line of reactor and separation system composition, and the partially liq product flows out reaction system, obtain the purpose product, wherein, the pressure of reaction system is 0.1-3.0MPa, temperature is 30-60 ℃, when empty is 0.5-3h, the mol ratio of propylene and hydrogen peroxide is (0.5-4.0): 1, the mol ratio of solvent and hydrogen peroxide is (10-60): 1, the concentration of titanium-silicon molecular sieve catalyst is 1.0-30g/L in the reaction system, said separation system is the solid-liquid separator that is made of the separatory membrane pipe, film pore footpath is less than the particle diameter of HTS, solid-liquid separator is one or more parallel connections, solid-liquid separator is regularly recoiled, will be attached to the molecular sieve refunds reaction system on the film pipe, the recoil time is 1～3s, and recoil is spaced apart 0.5～3h.
2. according to the method for claim 1, it is characterized in that described HTS is the HTS with MFI structure.
3. according to the method for claim 1, it is characterized in that said solvent is the mixture of methyl alcohol or methyl alcohol and water.
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| CN2007100998535A CN101314596B (en) | 2007-05-31 | 2007-05-31 | Method for continuous preparation of epoxypropane |
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| CN2007100998535A CN101314596B (en) | 2007-05-31 | 2007-05-31 | Method for continuous preparation of epoxypropane |
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| CN101314596B true CN101314596B (en) | 2011-04-20 |
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Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101747297B (en) * | 2008-12-22 | 2011-11-02 | 中国石油化工股份有限公司 | Method for continuously producing epoxy chloropropane |
| CN101817804B (en) * | 2010-03-16 | 2011-10-05 | 华东理工大学 | Method for preparing propylene oxide by propylene epoxidation under pressure oscillations |
| US8859791B2 (en) | 2010-10-11 | 2014-10-14 | China Petroleum & Chemical Corporation | Process for producing an alkylene oxide by olefin epoxidation |
| CN102442976B (en) * | 2010-10-11 | 2014-01-15 | 中国石油化工股份有限公司 | Method for epoxidizing olefinic hydrocarbon |
| CN103012064B (en) * | 2011-09-28 | 2015-03-18 | 中国石油化工股份有限公司 | Method for preparing propylene glycol from propylene |
| CN103130748B (en) * | 2011-11-29 | 2015-04-29 | 岳阳昌德化工实业有限公司 | Cyclohexene oxidizing method |
| CN104003916B (en) * | 2013-02-26 | 2016-08-24 | 中国石油化工股份有限公司 | A kind of method producing dimethyl sulfoxide (DMSO) |
| CN104557634B (en) * | 2013-10-29 | 2017-01-25 | 中国石油化工股份有限公司 | Method for producing dimethyl sulfone |
| RU2694060C2 (en) | 2014-09-29 | 2019-07-09 | Чайна Петролеум Энд Кемикал Корпорейшн | Olefin oxidation method, reaction device and system |
| CN104311513B (en) * | 2014-10-16 | 2016-04-27 | 河北美邦工程科技有限公司 | A kind of method preparing propylene oxide |
| CN104327016B (en) * | 2014-11-05 | 2016-01-20 | 河北美邦工程科技有限公司 | A kind of method preparing propylene oxide |
| CN104841348B (en) * | 2015-05-07 | 2016-08-24 | 大连交通大学 | A kind of liquid-solid reaction unit of filtering type high pressure continuously |
| CN109748887A (en) * | 2017-11-08 | 2019-05-14 | 中国石油化工股份有限公司 | The method of controlling security of HPPO technique hydrogen peroxide charging |
| CN111718313A (en) * | 2019-03-22 | 2020-09-29 | 中国石油化工股份有限公司 | Method for preparing propylene oxide by TS-1 method |
| CN111978273A (en) * | 2020-09-21 | 2020-11-24 | 江苏扬农化工集团有限公司 | Continuous synthesis process of epoxy chloropropane by hydrogen peroxide method |
| CN115197171A (en) * | 2021-04-13 | 2022-10-18 | 中国石油化工股份有限公司 | Method and system for producing propylene oxide |
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| CN1301599A (en) * | 1999-12-24 | 2001-07-04 | 中国石油化工集团公司 | Titanium-silicon molecular sieve and its preparing method |
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| CN1301599A (en) * | 1999-12-24 | 2001-07-04 | 中国石油化工集团公司 | Titanium-silicon molecular sieve and its preparing method |
| CN1631538A (en) * | 2003-12-22 | 2005-06-29 | 中国石油化工股份有限公司 | Regenerating, cleaning and separating method of titanium silicon molecular sieve catalyst |
Non-Patent Citations (1)
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