CN104098532A - Method for preparing epoxybutane through butene epoxidation - Google Patents
Method for preparing epoxybutane through butene epoxidation Download PDFInfo
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- CN104098532A CN104098532A CN201410345616.2A CN201410345616A CN104098532A CN 104098532 A CN104098532 A CN 104098532A CN 201410345616 A CN201410345616 A CN 201410345616A CN 104098532 A CN104098532 A CN 104098532A
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- butene
- butylene
- hydrogen phosphide
- phosphide cumene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for preparing epoxybutane through butene epoxidation. The method comprises steps as follows: a titanium silicalite molecular sieve is taken as a catalyst, and selected butene is butane-1 or butane-2; an epoxidation reaction is performed on a fixed bed reactor; and a weight ratio of butene to cumyl hydroperoxide as raw reaction materials is (1-15): 1, the feeding weight airspeed of cumyl hydroperoxide is 1.0-10.0 h<-1>, the reaction pressure is 1.0-6.0 MPa according to gage pressure, and the reaction is performed under the condition of the reaction temperature of 50.0-130.0 DEG C for 0.5-48 hours to prepare epoxybutane. The method has the characteristics of high atom economy, environment protection, no pollution, good catalyst activity and stability and high epoxybutane selectivity, the problems that a chlorohydrin method has serious pollution, a peracetic acid method has high operation requirement and high technical promotion difficulty, a vinyl-oxirane hydrogenation catalyst is expensive and the like are solved, further, raw materials are easy to obtain, the technology is simple, and the method can be popularized in industrial production.
Description
Technical field
The present invention relates to a kind of butylene epoxidation and prepare the method for butylene oxide ring, specifically taking a kind of HTS of the one-dimensional linear pore passage structure with hexagonal prism structure as catalyzer, the method for butylene oxide ring is prepared in catalyzing butene and hydrogen phosphide cumene oxidation.
Background technology
Butylene oxide ring be a kind of basic chemical industry raw material for the manufacture of intermediate and polymkeric substance, be for example used for producing 1,2-butyleneglycol.Also be used for replacing the thinner of acetone as pyroxylin(e)finish, can also be used for porous plastics processed, synthetic rubber, nonionic surface active agent etc.Butylene oxide ring also can production high added value propyl carbinol, butyleneglycol or polycarbonate.Be in butylene oxide ring except Isosorbide-5-Nitrae-butylene oxide ring, other two kinds of butylene oxide rings can be directly synthetic as raw material with butene-1 and butene-2, wherein butene feedstock is easy to get, mainly separating obtained by C 4 fraction.
Industrial, the byproduct that butylene oxide ring derives from production of propylene oxide reclaims, and producing in oxyethane, propylene oxide process through hypochlorous acid with cracking tail gas, can obtain butylene oxide ring bottom product.Traditional method for making of 1,2-butylene oxide ring mainly contains two kinds.The one, chlorohydrination, this method is to prepare the traditional technology of low-carbon (LC) epoxide, butylene reacts with chlorine, water and generates butylene-chlorohydrin, then makes butylene oxide ring with liquid caustic soda or milk of lime saponification.Chlorohydrination is due to seriously polluted, trend on the verge of being replaced.The 2nd, peracetic acid method, peracetic acid method synthesizing butyl oxide linkage technique in two steps, the one, oxidation of acetaldehyde generate peracetic acid, the 2nd, peracetic acid and butylene carry out epoxidation reaction.Compared with chlorohydrination, the advantage of peracetic acid method is that three-waste free pollution, steam consumption quantity are few, by-product acetic acid can utilize.But this method operational requirement is higher, and technology popularization difficulty is large, therefore limits its development.Can find out, seek a kind of Atom economy high, green non-pollution, development potentiality is larger, and the butylene oxide ring preparation method that can apply has realistic meaning very much.
It is the M41S molecular sieve of 2 nanometer to 10 nanometers that U.S.'s Mobile (Mobil) company in 1992 has synthesized channel diameter first, and this is the optimal candidate material of molecular sieve catalyst of new generation.M4IS series comprises three types, i.e. six side MCM41, cube MCM48 and lamellar compound.Wherein, about the research of MCM-41, become in recent years heat subject.This material is the representative raw material using non-crystalline state silicon oxide as hole wall substantially.
CN 1151739A is disclosed is a kind of method of vinyl catalyzing epoxyethane Hydrogenation for 1,2-butylene oxide ring of passing through.The method is taking barium sulfate, zirconium dioxide or titanium dioxide as carrier loaded palladium catalyst or the palladium catalyst of the rhenium-containing carrier hydrogenation reaction of carrying out, and this catalyzer is noble metal catalyst, expensive, and economy is not high.And taking HTS as catalyzer, the method that butylene oxide ring is prepared in catalyzing butene and hydrogen phosphide cumene oxidation is a kind of novel process, this raw materials technology is easy to get, and Atom economy is high, pollutes less, and development potentiality is large.
Summary of the invention
Technical problem to be solved by this invention is that prior art is seriously polluted, and quantity discharged is large, middle complicated operation, separating energy consumption geodetic problem.Provide a kind of new butylene epoxidation to prepare the method for butylene oxide ring, used catalyst environmental protection, better active, butylene oxide ring selectivity is high, reaction conditions gentleness, convenient operation, cost is low, can promote the use of in butylene epoxidation butylene oxide ring industrial production processed.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of butylene epoxidation is prepared the method for butylene oxide ring, taking hydrogen phosphide cumene as oxygenant, isopropyl benzene is solvent, butylene epoxidation is prepared butylene oxide ring, in the method taking HTS Ti-MCM-41 as catalyzer.
In the present invention, HTS preparation process is as follows: be that titanium source, tetraethoxy are silicon source by titanium tetrachloride, tetraethyl titanate or tetrabutyl titanate.Taking cetyl trimethylammonium bromide or Trimethyllaurylammonium bromide as template, by hydrothermal synthesis method synthesis of titanium silicon molecular sieve Ti-MCM-41.This catalyzer has the lot of documents can be with reference to preparation method, also can make by other method.
In the present invention, a kind of butylene epoxidation is prepared the method for butylene oxide ring, and taking HTS as catalyzer, the butylene of selecting is butene-1 or butene-2.Epoxidation reaction is carried out on fixed-bed reactor; Wherein the weight ratio of reaction raw materials butylene and hydrogen phosphide cumene is (1～15): 1, and hydrogen phosphide cumene feed weight air speed is 1.0～10.0h
-1, reaction pressure is counted 1.0～6.0MPa with gauge pressure, and temperature of reaction is under 50.0～130.0 DEG C of conditions, to react within 0.5～48 hour, to make butylene oxide ring.
Ti-MCM-41 catalyzer mean pore size is 2.0～10.0nm, and specific surface area is 700.0m
2/ g～1200m
2/ g, the surface coverage of active Ti is 10～50%.
The weight ratio of preferred reaction raw material butylene and hydrogen phosphide cumene is 2～5:1, and hydrogen phosphide cumene feed weight air speed is 1.0～4.0h
-1.Reaction pressure is 2.0～4.0Mpa.Temperature of reaction is 80.0～100.0 DEG C.Reaction times is 1～10 hour.
Preferably the cumene solution of the hydrogen phosphide cumene taking butylene and concentration expressed in percentage by weight as 30～80% is as reaction raw materials.
The method of preparing butylene oxide ring provided by the invention, has that Atom economy is high, green non-pollution, catalyst activity and good stability, the feature that butylene oxide ring selectivity is high.With respect to traditional method, overcome chlorohydrination seriously polluted, the problem such as peracetic acid method operational requirement is high, and technology popularization difficulty is large, and vinyl catalyzing epoxyethane hydrogenation catalyst is expensive, and raw material is easy to get, technique is simple, extends in suitability for industrialized production.
Under embodiment
The present invention is further elaborated by embodiment for face.
[embodiment 1]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 10%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 30wt%, all the other volumes are isopropyl benzene) is 1:1 with the weight ratio of butene-1; Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 1.0, and reactor pressure maintains 1.0MPa, and temperature of reaction is 50.0 DEG C, reacts cooling after 0.5h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 2]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 20%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 40wt%, all the other volumes are isopropyl benzene) is 1:2 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 2.0, and reactor pressure maintains 2.0MPa, and temperature of reaction is 70.0 DEG C, reacts cooling after 2h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 3]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 20%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 40wt%, all the other volumes are isopropyl benzene) is 1:2 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 1.0, and reactor pressure maintains 2.0MPa, and temperature of reaction is 80.0 DEG C, reacts cooling after 1h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 4]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 20%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 40wt%, all the other volumes are isopropyl benzene) is 1:2.5 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 2.0, and reactor pressure maintains 3.0MPa, and temperature of reaction is 90.0 DEG C, reacts cooling after 5h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 5]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 30%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 50wt%, all the other volumes are isopropyl benzene) is 1:5 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 4.0, and reactor pressure maintains 4.0MPa, and temperature of reaction is 100.0 DEG C, reacts cooling after 10h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 6]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 40%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 60wt%, all the other volumes are isopropyl benzene) is 1:7 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 5.0, and reactor pressure maintains 4.0MPa, and temperature of reaction is 100.0 DEG C, reacts cooling after 10h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 7]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 50%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 70wt%, all the other volumes are isopropyl benzene) is 1:9 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 7.0, and reactor pressure maintains 5.0MPa, and 110.0 DEG C of temperature of reaction are reacted cooling after 20h hour, take out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 8]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 50%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 80wt%, all the other volumes are isopropyl benzene) is 1:11 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 8.0, and reactor pressure maintains 6.0MPa, and temperature of reaction is 110.0 DEG C, reacts cooling after 30h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 9]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 50%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 50wt%, all the other volumes are isopropyl benzene) is 1:13 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 9.0, and reactor pressure maintains 3.0MPa, and temperature of reaction is 120.0 DEG C, reacts cooling after 40h hour, takes out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
[embodiment 10]
In the flat-temperature zone of fixed-bed reactor, take 8g HTS Ti-MCM-41 catalyzer (surface coverage of active Ti is 50%), hydrogen phosphide cumene (the hydrogen phosphide cumene oxidation solution that contains 50wt%, all the other volumes are isopropyl benzene) is 1:15 with the weight ratio of butene-1.Air in logical nitrogen replacement still, switches afterwards butene-1 and enters into tank reactor.Hydrogen phosphide cumene feed weight air speed is 10.0, and reactor pressure maintains 4.0MPa, and 130.0 DEG C of temperature of reaction are reacted cooling after 48h hour, take out reaction product and carry out gas-chromatography and chemical iodimetric analysis after cooling, and reaction result is in table 1.
Table 1 titanium-silicon molecular sieve catalyst evaluation result
| Embodiment | Hydrogen phosphide cumene transformation efficiency % | Butylene oxide ring selectivity % (to CHP) |
| Embodiment 1 | 90.37 | 86.57 |
| Embodiment 2 | 97.08 | 89.35 |
| Embodiment 3 | 99.02 | 89.53 |
| Embodiment 4 | 99.86 | 90.72 |
| Embodiment 5 | 99.12 | 90.25 |
| Embodiment 6 | 98.66 | 89.32 |
| Embodiment 7 | 98.52 | 86.67 |
| Embodiment 8 | 95.43 | 87.28 |
| Embodiment 9 | 94.25 | 86.55 |
| Embodiment 10 | 91.68 | 84.37 |
By the embodiment under different condition, can find out, the method method is prepared butylene oxide ring, and transformation efficiency is more than 90%, and butylene oxide ring selectivity, more than 80%, can be used in butylene oxide ring industry.
Claims (8)
1. a butylene epoxidation is prepared the method for butylene oxide ring, taking HTS as catalyzer, the cumene solution of the hydrogen phosphide cumene taking butylene and concentration expressed in percentage by weight as 30～80% is as reaction raw materials, wherein the weight ratio of reaction raw materials butylene and hydrogen phosphide cumene is (1～15): 1, and hydrogen phosphide cumene feed weight air speed is 1.0～10.0h
-1, reaction pressure is counted 1.0～6.0MPa with gauge pressure, and temperature of reaction is under 50.0～130.0 DEG C of conditions, to react within 0.5～48 hour, to make butylene oxide ring.
2. butylene epoxidation is prepared the method for butylene oxide ring according to claim 1, it is characterized in that butylene is butene-1 or the butene-2 of chemical grade or polymerization-grade.
3. method according to claim 1, is characterized in that selected titanium-silicon molecular sieve catalyst is Ti-MCM-41.
4. method according to claim 3, is characterized in that Ti-MCM-41 catalyzer mean pore size is 2.0～10.0nm, and specific surface area is 700.0m
2/ g～1200m
2/ g, the surface coverage of active Ti is 10～50%.
5. method according to claim 1, the weight ratio that it is characterized in that reaction raw materials butylene and hydrogen phosphide cumene is 2～5:1, hydrogen phosphide cumene feed weight air speed is 1.0～4.0h
-1.
6. method according to claim 1, is characterized in that reaction pressure is 2.0～4.0Mpa.
7. method according to claim 1, is characterized in that temperature of reaction is 80.0～100.0 DEG C.
8. method according to claim 1, is characterized in that the reaction times is 1～10 hour.
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| CN201410345616.2A CN104098532A (en) | 2014-07-18 | 2014-07-18 | Method for preparing epoxybutane through butene epoxidation |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105498832A (en) * | 2014-10-20 | 2016-04-20 | 中国石油化工股份有限公司 | Preparation method for catalyst used for preparing 1,2-epoxybutane through epoxidation of 1-butene |
| CN106279069A (en) * | 2015-08-10 | 2017-01-04 | 中国石油化工股份有限公司 | A kind of method preparing epoxy butane |
| CN113292518A (en) * | 2021-06-22 | 2021-08-24 | 中山大学 | Method for preparing epoxybutane by organic micromolecule green and efficient catalysis of butylene |
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| CN102941117A (en) * | 2012-11-13 | 2013-02-27 | 中国石油化工股份有限公司 | Regeneration method of titanium-silicon molecular sieve catalyst |
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2014
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| CN102941117A (en) * | 2012-11-13 | 2013-02-27 | 中国石油化工股份有限公司 | Regeneration method of titanium-silicon molecular sieve catalyst |
Non-Patent Citations (3)
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| 吴美玲: "Ti-MSU分子筛催化1-丁烯氧化制环氧丁烷的研究", 《聚氨酯工业》 * |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105498832A (en) * | 2014-10-20 | 2016-04-20 | 中国石油化工股份有限公司 | Preparation method for catalyst used for preparing 1,2-epoxybutane through epoxidation of 1-butene |
| CN105498832B (en) * | 2014-10-20 | 2018-12-28 | 中国石油化工股份有限公司 | The preparation method of the catalyst of 1,2- epoxy butane is prepared for 1- butylene epoxidation |
| CN106279069A (en) * | 2015-08-10 | 2017-01-04 | 中国石油化工股份有限公司 | A kind of method preparing epoxy butane |
| CN113292518A (en) * | 2021-06-22 | 2021-08-24 | 中山大学 | Method for preparing epoxybutane by organic micromolecule green and efficient catalysis of butylene |
| CN113292518B (en) * | 2021-06-22 | 2022-05-31 | 中山大学 | Method for preparing epoxybutane by organic micromolecule green and efficient catalysis of butylene |
| WO2022267081A1 (en) * | 2021-06-22 | 2022-12-29 | 中山大学 | Green and efficient method for catalyzing butene to prepare epoxybutane with organic small molecules |
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