CN104177314B - A kind of method preparing epoxy butane - Google Patents
A kind of method preparing epoxy butane Download PDFInfo
- Publication number
- CN104177314B CN104177314B CN201410345620.9A CN201410345620A CN104177314B CN 104177314 B CN104177314 B CN 104177314B CN 201410345620 A CN201410345620 A CN 201410345620A CN 104177314 B CN104177314 B CN 104177314B
- Authority
- CN
- China
- Prior art keywords
- epoxy butane
- cumyl hydroperoxide
- msu
- solute
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to a kind of method preparing epoxy butane, in the cumene solution of the cumyl hydroperoxide solute containing 25wt%, with cumyl hydroperoxide solute as oxidant, butylene oxide prepares epoxy butane, and catalyst is that to have HTS (herein red delete) the fixed bed reaction condition of three-dimensional open-framework be butylene and the mol ratio of cumyl hydroperoxide solute is (5.0～12.0): 1；Cumyl hydroperoxide feed weight air speed is 1.0～5.0h‑1, reaction pressure is 1.0～6.0MPa, and temperature is 60.0～120.0 DEG C.Catalyst is the HTS of three-dimensional open-framework, and molecular sieve exists hysteresis loop in low temperature nitrogen absorption and desorption isotherm, and average pore size is 2.0～8.0nm, and specific surface area is 650.0～1100.0m2/ g, this good catalyst activity, epoxy butane selectivity is high, can promote the use of in butylene epoxidation epoxy butane commercial production.
Description
Technical field
The present invention relates to a kind of method preparing epoxy butane, specifically with a kind of titanium silicon molecule with three-dimensional open-framework
Sieve is catalyst, the method that epoxy butane is prepared in catalyzing butene and cumyl hydroperoxide oxidation.
Background technology
Polyethers, in addition to can be as the base oil of novel synthetic lubricant fluid, be also the important source material producing polyurethane, and
Have froth breaking, breakdown of emulsion, disperse, permeate, the several functions such as emulsifying.What the monomer of synthesizing polyether had been developed the most have oxirane,
Expoxy propane, epoxy butane and oxolane etc..Owing to being limited by epoxy butane production technology, with epoxy butane for monomer institute
It is less that the polyethers of synthesis accounts for the market share.Epoxy butane from last century after the seventies develops development quickly, in the U.S.
The 80s and 90s in century, increase production with the speed of 10% every year, but at China's slower development.
Epoxy butane, in addition to some purposes with expoxy propane, also has the feature of self, can produce high added value
N-butyl alcohol or Merlon.In epoxy butane in addition to Isosorbide-5-Nitrae-epoxy butane, other two kinds of epoxy butanes can with butene-1 and
Butene-2 is directly synthesized as raw material, and wherein butene feedstock is easy to get, mainly separating obtained by C 4 fraction.
Industrial, epoxy butane derives from the side-product of production of propylene oxide and reclaims, raw through hypochlorous acid with cracking tail gas
During producing oxirane, expoxy propane, epoxy butane bottom product can be obtained.Traditional preparation method of 1,2-epoxy butane mainly has two
Kind.One is chlorohydrination, and this method is to prepare the traditional handicraft of low-carbon (LC) epoxide, and butylene and chlorine, water react generation methaform, then
Epoxy butane is prepared with liquid caustic soda or lime cream saponification.Chlorohydrination due to seriously polluted, trend on the verge of being replaced.Two is peracetic acid
Method, in two steps, one is that oxidation of acetaldehyde generates peracetic acid to peracetic acid method synthesizing butyl oxide linkage technique, and two is that peracetic acid is carried out with butylene
Epoxidation reaction.Compared with chlorohydrination, the advantage of peracetic acid method is three-waste free pollution, steam consumption quantity is few, by-product acetic acid available.
But the operation of this method requires higher, and Technique Popularizing difficulty is big, therefore limit its development.
It can be seen that it is high to seek a kind of Atom economy, green non-pollution, development potentiality is relatively big, the ring of energy popularization and application
Oxygen butane Preparation Method is to have very much realistic meaning.
CN 1151739A is disclosed that a kind of side being prepared 1,2-epoxy butane by vinyl oxirane catalytic hydrogenation
Method.The method is carrier loaded palladium catalyst or the palladium catalyst of rhenium-containing carrier with barium sulfate, zirconium dioxide or titanium dioxide
The hydrogenation reaction carried out, this catalyst is noble metal catalyst, and expensive, economy is the highest.And with HTS for urging
Agent, it is a kind of novel process, this raw materials technology that the method for epoxy butane is prepared in catalyzing butene and cumyl hydroperoxide oxidation
Being easy to get, Atom economy is high, pollutes few, and development potentiality is big.
Summary of the invention
It is an object of the invention to provide a kind of method preparing epoxy butane, the activity of used catalyst is preferable, epoxy
Butane selectivity is high, and reaction condition is gentle, it is simple to operation, can promote the use of butylene epoxidation epoxy butane commercial production
In.
For solving above-mentioned technical problem, the technical solution used in the present invention is as follows: a kind of method preparing epoxy butane, is
In the cumene solution of the cumyl hydroperoxide solute containing 25wt%, exist with cumyl hydroperoxide solute for oxidation
Agent, butylene oxide prepares epoxy butane, and in the method, catalyst is a kind of HTS with three-dimensional open-framework, this point
There is hysteresis loop in son sieve in low temperature nitrogen absorption and desorption isotherm, its average pore size is 2.0～8.0nm, and specific surface area is
650.0～1100.0m2/g.Fixed bed reaction condition be butylene with the mol ratio of cumyl hydroperoxide solute for (5.0～
12.0): 1；Cumyl hydroperoxide feed weight air speed is 1.0～5.0h-1, reaction pressure is 1.0～6.0MPa, and temperature is
60.0～120.0 DEG C.
In the present invention, the butylene of selection is butene-1 or butene-2.
In the present invention, the catalyst of selection is HTS.
In the present invention, the HTS of selection is Ti/MSU-1, Ti/MSU-2, Ti/MSU-3, Ti/MSU-4, Ti/
One in MSU-V, Ti/MSU-G, Ti/MSU-S or Ti/MSU-H；
In the present invention, HTS average pore size is 2.0～8.0nm, and specific surface area is 650.0～1100.0m2/g。
In the present invention, the epoxy butane of preparation is 1,2-epoxy butane or 2,3-epoxy butane.
In the present invention, for bar shaped or spherical after HTS molding.
The method preparing epoxy butane that the present invention provides, has Atom economy height, green non-pollution, catalyst activity
And good stability, the feature that epoxy butane selectivity is high.Relative to traditional method, overcome chlorohydrination seriously polluted, cross second
Acid system operation requires height, and Technique Popularizing difficulty is big, the problems such as vinyl oxirane catalytic hydrogenation catalyst is expensive, and former
Material is easy to get, technique is simple, extends in industrialized production.
Detailed description of the invention
Below by embodiment, the present invention is further elaborated.
Embodiment 1
(specific surface area is 1021.3m to weigh the 1.0g former powder of HTS Ti/MSU-1 respectively2/ g, average pore size is
2.1nm), and add a certain amount of quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure is tieed up
Holding at 2.0MPa, it is 80.0 DEG C that reaction temperature controls.Butene-1 and the isopropyl of the cumyl hydroperoxide solute containing 25wt%
Benzole soln mixes before reactor, and enters in fixed bed reactors in the way of upper entering and lower leaving.Its butene-1 and peroxidating
The mol ratio of hydrogen isopropylbenzene is 10.0:1, and cumyl hydroperoxide feed weight air speed is 1.0h-1.After question response carries out 2 hours,
With online gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selects
Selecting property the results are shown in Table 1.
Embodiment 2
(specific surface area is 1021.3m to weigh the 1.0g former powder of HTS Ti/MSU-1 respectively2/ g, average pore size is
2.1nm), and add a certain amount of quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure is tieed up
Holding at 2.0MPa, it is 80.0 DEG C that reaction temperature controls.Butene-2 and the isopropyl of the cumyl hydroperoxide solute containing 25wt%
Benzole soln mixes before reactor, and enters in fixed bed reactors in the way of upper entering and lower leaving.Its butene-2 and peroxidating
The mol ratio of hydrogen isopropylbenzene is 10.0:1, and cumyl hydroperoxide feed weight air speed is 1.0h-1.After question response carries out 2 hours,
With online gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 2,3-epoxy butane selects
Selecting property the results are shown in Table 1.
Embodiment 3
(specific surface area is 941.6m to weigh the HTS Ti/MSU-2 of 2.0g bar shaped2/ g, average pore size is
2.7nm), and add a certain amount of quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure is tieed up
Holding at 1.0MPa, it is 60.0 DEG C that reaction temperature controls.Butene-1 and the isopropyl of the cumyl hydroperoxide solute containing 25wt%
Benzole soln mixes before reactor, and enters in fixed bed reactors in the way of upper entering and lower leaving.Its butene-1 and peroxidating
The mol ratio of hydrogen isopropylbenzene is 5.0:1, and cumyl hydroperoxide feed weight air speed is 1.0h-1.After question response carries out 2 hours,
With online gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selects
Selecting property the results are shown in Table 1.
Embodiment 4
(specific surface area is 849.2m to weigh the HTS Ti/MSU-3 of 2.0g bar shaped2/ g, average pore size is
4.8nm), and add certain quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure maintains
At 3.0MPa, it is 80.0 DEG C that reaction temperature controls.Butene-1 and the isopropylbenzene of the cumyl hydroperoxide solute containing 25wt%
Solution mixes before reactor, and enters in the way of upper entering and lower leaving in fixed bed reactors, its butene-1 and hydrogen peroxide
The mol ratio of isopropylbenzene is 6.0:1, and cumyl hydroperoxide feed weight air speed is 2.0h-1.After question response carries out 2 hours, use
Online gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selects
Property the results are shown in Table 1.
Embodiment 5
(specific surface area is 887.6m to weigh HTS Ti/MSU-4 spherical for 2.0g2/ g, average pore size is
5.2nm), and add certain quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure maintains
At 4.0MPa, it is 100.0 DEG C that reaction temperature controls.Butene-1 and the isopropylbenzene of the cumyl hydroperoxide solute containing 25wt%
Solution mixes before reactor, and enters in the way of upper entering and lower leaving in fixed bed reactors, its butene-1 and hydrogen peroxide
The mol ratio of isopropylbenzene is 8.0:1, and cumyl hydroperoxide feed weight air speed is 3.0h-1.After question response carries out 2 hours, use
Online gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selects
Property the results are shown in Table 1.
Embodiment 6
(specific surface area is 1099.6m to weigh HTS Ti/MSU-V spherical for 2.0g2/ g, average pore size is
2.0nm), and add certain quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure maintains
At 4.0MPa, it is 100.0 DEG C that reaction temperature controls.Butene-1 and the isopropylbenzene containing 25wt% cumyl hydroperoxide solute are molten
Liquid mixes before reactor, and enters in the way of upper entering and lower leaving in fixed bed reactors, and its butene-1 is different with hydrogen peroxide
The mol ratio of propyl benzene is 8.0:1, and cumyl hydroperoxide feed weight air speed is 3.0h-1.After question response carries out 2 hours, it is used in
Line gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selectivity
The results are shown in Table 1.
Embodiment 7
(specific surface area is 922.5m to weigh the HTS Ti/MSU-G of 2.0g bar shaped2/ g, average pore size is
3.5nm), and add certain quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure maintains
At 6.0MPa, it is 80.0 DEG C that reaction temperature controls.Butene-1 and the cumene solution containing cumyl hydroperoxide solute are instead
Mix before answering device, and enter in the way of upper entering and lower leaving in fixed bed reactors, its butene-1 and cumyl hydroperoxide
Mol ratio is 10.0:1, and cumyl hydroperoxide feed weight air speed is 4.0h-1.After question response carries out 2 hours, use online gas phase
Chromatograph and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selectivity result is shown in
Table 1.
Embodiment 8
(specific surface area is 897.8m to weigh the HTS Ti/MSU-S of 2.0g bar shaped2/ g, average pore size is
3.8nm), and add certain quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure maintains
At 4.0MPa, it is 120.0 DEG C that reaction temperature controls.Butene-1 and the isopropylbenzene containing 25wt% cumyl hydroperoxide solute are molten
Liquid mixes before reactor, and enters in the way of upper entering and lower leaving in fixed bed reactors, and its butene-1 is different with hydrogen peroxide
The mol ratio of propyl benzene is 12.0:1, and cumyl hydroperoxide feed weight air speed is 5.0h-1.After question response carries out 2 hours, it is used in
Line gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selectivity
The results are shown in Table 1.
Embodiment 9
(specific surface area is 648.9m to weigh the HTS Ti/MSU-H of 2.0g bar shaped2/ g, average pore size is
8.0nm), and add certain quartz sand and be diluted, be subsequently placed in the flat-temperature zone of fixed bed reactors.System pressure maintains
At 4.0MPa, it is 80.0 DEG C that reaction temperature controls.Butene-1 and the isopropylbenzene containing 25wt% cumyl hydroperoxide solute are molten
Liquid mixes before reactor, and enters in the way of upper entering and lower leaving in fixed bed reactors, and its butene-1 is different with hydrogen peroxide
The mol ratio of propyl benzene is 10.0:1, and cumyl hydroperoxide feed weight air speed is 4.0h-1.After question response carries out 2 hours, it is used in
Line gas chromatogram and chemistry iodimetric analysis product, its cumyl hydroperoxide conversion ratio and 1,2-epoxy butane selectivity
The results are shown in Table 1.
Table 1 titanium-silicon molecular sieve catalyst evaluation result
| Embodiment | Cumyl hydroperoxide conversion ratio % | Epoxy butane selectivity % (to CHP) |
| Embodiment 1 | 98.3 | 96.5 |
| Embodiment 2 | 99.0 | 95.3 |
| Embodiment 3 | 91.0 | 93.5 |
| Embodiment 4 | 98.8 | 96.7 |
| Embodiment 5 | 99.5 | 98.6 |
| Embodiment 6 | 99.4 | 97.2 |
| Embodiment 7 | 99.2 | 96.5 |
| Embodiment 8 | 97.6 | 94.3 |
| Embodiment 9 | 98.3 | 92.1 |
As it can be seen from table 1 use the titanium-silicon molecular sieve catalyst of the present invention, to contain in the presence of isopropylbenzene solvent
25wt% cumyl hydroperoxide solute is oxidant, and butylene oxide prepares 1,2-epoxy butane or 2, in 3-epoxy butane, and mistake
The conversion ratio of hydrogen oxide isopropylbenzene can reach 99.5%, and the selectivity of 1,2-epoxy butane is up to 98.6%.This catalyst visible
Activity preferably, selectivity is higher, and reaction condition is gentle, has preferable technique effect.
Claims (5)
1. the method preparing epoxy butane, is characterized in that the isopropylbenzene at the cumyl hydroperoxide solute containing 25wt%
In solution, with cumyl hydroperoxide solute as oxidant, butylene oxide prepares epoxy butane, and catalyst is for having 3 D pore canal
The HTS of structure, fixed bed reaction condition be butylene with the mol ratio of cumyl hydroperoxide solute for (5.0～
12.0): 1；Cumyl hydroperoxide feed weight air speed is 1.0～5.0h-1, reaction pressure is 1.0～6.0MPa, and temperature is
60.0～120.0 DEG C, there is hysteresis loop in catalyst molecule sieve in low temperature nitrogen absorption and desorption isotherm, average pore size is
2.0～8.0nm, specific surface area is 650.0～1100.0m2/g。
2. the method for claim 1, it is characterized in that described catalyst Ti-si molecular sieves be Ti/MSU-1, Ti/MSU-2,
One in Ti/MSU-3, Ti/MSU-4, Ti/MSU-V, Ti/MSU-G, Ti/MSU-S or Ti/MSU-H.
3. the method for claim 1, is characterized in that selected butylene is butene-1 or butene-2.
4. the method for claim 1, is characterized in that prepared epoxy butane is 1,2-epoxy butane or 2,3-epoxy
Butane.
Method the most according to claim 1, it is characterised in that after selected catalyst Ti-si molecular sieves molding for bar shaped or
Spherical.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410345620.9A CN104177314B (en) | 2014-07-18 | 2014-07-18 | A kind of method preparing epoxy butane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410345620.9A CN104177314B (en) | 2014-07-18 | 2014-07-18 | A kind of method preparing epoxy butane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104177314A CN104177314A (en) | 2014-12-03 |
| CN104177314B true CN104177314B (en) | 2016-09-14 |
Family
ID=51958694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410345620.9A Active CN104177314B (en) | 2014-07-18 | 2014-07-18 | A kind of method preparing epoxy butane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104177314B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104774168B (en) * | 2015-04-01 | 2017-05-10 | 中石化上海工程有限公司 | Method for coproduction of dicumyl peroxide (DCP) and epoxybutane (CHPBO) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0795537A1 (en) * | 1996-03-12 | 1997-09-17 | ENICHEM S.p.A. | Process for the synthesis of 2-butene -1,4-diesters |
| CN101085763A (en) * | 2007-05-11 | 2007-12-12 | 湖南长岭石化科技开发有限公司 | Method for synthesizing 1,2-epoxy butane |
| CN101348472A (en) * | 2007-07-18 | 2009-01-21 | 中国石油化工股份有限公司 | Method for preparing epoxide |
| CN101643459A (en) * | 2008-08-07 | 2010-02-10 | 中国石油化工股份有限公司 | Method for preparing 1,2-butylene oxide |
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06211821A (en) * | 1993-01-13 | 1994-08-02 | Maruzen Petrochem Co Ltd | Method for epoxidizing olefin compound |
-
2014
- 2014-07-18 CN CN201410345620.9A patent/CN104177314B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0795537A1 (en) * | 1996-03-12 | 1997-09-17 | ENICHEM S.p.A. | Process for the synthesis of 2-butene -1,4-diesters |
| CN101085763A (en) * | 2007-05-11 | 2007-12-12 | 湖南长岭石化科技开发有限公司 | Method for synthesizing 1,2-epoxy butane |
| CN101348472A (en) * | 2007-07-18 | 2009-01-21 | 中国石油化工股份有限公司 | Method for preparing epoxide |
| CN101643459A (en) * | 2008-08-07 | 2010-02-10 | 中国石油化工股份有限公司 | Method for preparing 1,2-butylene oxide |
| 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)
| Title |
|---|
| Ti-MSU分子筛催化1-丁烯氧化制环氧丁烷的研究;吴美玲 等;《聚氨酯工业》;20140428;第29卷(第2期);第17-20页 * |
| Ti-MSU分子筛的合成、表征及其催化性能研究;吴美玲 等;《石油炼制与化工》;20140531;第45卷(第5期);第50-53页，第50页左栏引言，1.1实验原料，1.4浸渍法Ti-MSU分子筛的合成，第51页1.6催化性能评价，表1-2，第51页1.5催化剂表征，第52页图3 * |
| 介孔分子筛MSU-1的合成;李苑 等;《化学研究与应用》;20031031;第15卷(第5期);第688-690页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104177314A (en) | 2014-12-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI283661B (en) | Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes | |
| US10500567B2 (en) | Use of rhenium-containing supported heterogenous catalysts for the direct deoxy-dehydrated of glycerol to allyl alcohol | |
| CN104177314B (en) | A kind of method preparing epoxy butane | |
| CN105646225A (en) | Tung oil-based polyol and preparation method thereof | |
| CN103333042A (en) | Method for preparing pentene | |
| CN103342624A (en) | Preparation method of high purity cyclopentene | |
| CN102442979A (en) | Preparation method of epoxypropane | |
| CN104098532A (en) | Method for preparing epoxybutane through butene epoxidation | |
| CN104387343A (en) | Method for epoxidizing olefin | |
| CN107915579A (en) | The method that butadiene synthesizes 1,4 butanediols | |
| CN104557785B (en) | A kind of heterogeneous catalysis epoxidation vinyl benzene combines the method for preparing Styryl oxide and benzaldehyde | |
| CN106279069A (en) | A kind of method preparing epoxy butane | |
| CN105315235A (en) | Method used for realizing epoxidation of hydrogen peroxide ethylbenzene with propylene | |
| CN103333041B (en) | A kind of preparation method of positive amylene | |
| CN206318907U (en) | A kind of device for preparing expoxy propane | |
| CN104707591B (en) | A kind of oxide catalyst of ethanol conversion preparing isobutene and preparation method thereof | |
| CN104557782A (en) | Method for preparing epoxypropane from cumyl hydroperoxide and propylene | |
| CN107501053A (en) | A kind of green synthesis method by the step alcohol ether of alkene one | |
| CN104230855A (en) | Cumyl hydroperoxide and propylene epoxidation method | |
| CN102731256B (en) | Method for preparing glycol by conversing cellulose for inhibiting cyclic ether alcohol | |
| CN102731253B (en) | Method capable of inhibiting generation of cyclic ether alcohol and used for preparing glycol by catalytic conversion of cellulose | |
| CN110698435A (en) | Preparation method of epichlorohydrin | |
| CN102442978B (en) | Alkene epoxidation method | |
| CN109438393A (en) | A kind of epoxy plasticizer synthetic method | |
| CN104557779A (en) | Production method of epoxy propane |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |