CN104003960A - New method for synthesizing 1,2-epoxybutane - Google Patents
New method for synthesizing 1,2-epoxybutane Download PDFInfo
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- CN104003960A CN104003960A CN201410173356.5A CN201410173356A CN104003960A CN 104003960 A CN104003960 A CN 104003960A CN 201410173356 A CN201410173356 A CN 201410173356A CN 104003960 A CN104003960 A CN 104003960A
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- butylene
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- butylene oxide
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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
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention discloses a new method for synthesizing 1,2-epoxybutane. Catalytic epoxidation is carried out with a titanium silicalite molecular sieve as a catalyst and hydrogen peroxide as an oxidant to prepare 1,2-epoxybutane. The method has the advantages of simple process flow of the whole process, high reaction yield, low production cost and environmental protection.
Description
Technical field
The present invention relates to a kind of novel method of synthetic 1,2-butylene oxide ring, particularly relate to a kind of novel method by synthetic 1, the 2-butylene oxide ring of 1-butylene one step epoxidation.
Background technology
1,2-butylene oxide ring (BO), claim again oxybutylene, it is a kind of important organic synthesis raw material, the reference material of stratographic analysis etc. can be used for manufacturing organic synthesis intermediate, high molecular polymer, replacement acetone as the thinner of pyroxylin(e)finish, also can be used as the oxidation inhibitor of chlorine-containing compound, the corrosion inhibitor of producing vinyl chloride resin, tensio-active agent, gasoline dope etc.
Industrial 1, the main production method of 2-butylene oxide ring still adopts chlorohydrination technique so far, first with hypochlorous acid, makes 1-butylene chlorohydrination, then obtains 1,2-butylene oxide ring through epoxidation.While adopting synthetic 1, the 2-butylene oxide ring of this technique, need to consume a large amount of Cl
2, equipment corrosion is serious, and produces containing CaCl in producing
2waste water, waste residue with organic chloride, caused very big pollution to environment, do not meet the requirement of Green Chemistry and cleaner production, and therefore, along with the raising day by day of environmental protection requirement, this technique certainly will will be eliminated.
In recent years, the method for 1-butylene Direct Epoxidation generation 1,2-butylene oxide ring under catalyst action is causing people's concern.Adopt Direct Epoxidation method to produce 1,2-butylene oxide ring and not only optimized Production Flow Chart, also reduced environmental pollution.At present, substantially adopting hydrogen peroxide is that oxygen source carries out epoxidation reaction, the main deficiency of existence is that 1,2-butylene oxide ring selectivity is low, poor catalyst stability, can not continuous reaction etc.HTS shows excellent catalytic performance and good prospects for commercial application for take the epoxidation reaction that hydrogen peroxide is oxygenant.
Summary of the invention
The present invention from optimization technological process, improve reaction yield, improve catalyst stability, reduce production costs, the angle of energy-conserving and environment-protective, a kind of novel method of synthetic 1,2-butylene oxide ring has been proposed.
To achieve these goals, the present invention adopts following technical scheme:
A kind of synthetic 1, the novel method of 2-butylene oxide ring, it is characterized in that: a certain amount of catalyzer is packed in reactor, add again a certain amount of hydrogen peroxide and solvent, off-response device, pass into 1-butylene and get rid of air in reactor, continue to pass into 1-butylene and keep certain pressure in reactor to start reaction.After reaction certain hour, obtain 1,2-butylene oxide ring, sampling analysis.Described reaction conditions is: temperature of reaction is 40-60 ℃, and reaction pressure is 0.1-0.4Mpa, and the reaction times is 1-3h, and hydrogen peroxide concentration is 0.3-0.9mol/L.
Described reactor is a kind of in fixed-bed reactor, fluidized-bed reactor, pipeline reactor or their combination.
Described solvent is a kind of in methyl alcohol, acetonitrile, acetone or their mixture.
Described catalyzer is a kind of in titanium-silicon molecular sieve TS-1, TS-2, Ti-HMS, Ti-MWW or their mixture.
Described catalyst concn is 13-16g/L.
Beneficial effect of the present invention:
Adopt this one-step oxidation process synthetic 1,2-butylene oxide ring, the defects such as the equipment corrosion that chlorohydrination causes is serious, environmental pollution have not only been overcome, and whole process simple, pollution-free, can be continuously produced, the selectivity of 1,2-butylene oxide ring can reach more than 99%, and 1,2-butylene oxide ring can reach more than 90% the productive rate of hydrogen peroxide, is suitable for large-scale industrial production.
Embodiment
Embodiment 1: a kind of novel method of synthetic 1,2-butylene oxide ring comprises the following steps:
A certain amount of catalyst Ti-si molecular sieves TS-1 is packed in fixed-bed reactor, add again a certain amount of hydrogen peroxide and solvent methanol, off-response device, passes into 1-butylene and gets rid of air in reactor, continues to pass into 1-butylene and keeps certain pressure in reactor to start reaction.After reaction certain hour, obtain 1,2-butylene oxide ring, sampling analysis.Reaction conditions is: temperature of reaction is 50 ℃, and reaction pressure is 0.15Mpa, and the reaction times is 1.5h, and hydrogen peroxide concentration is 0.3mol/L, and catalyst concn is 14g/L.
Embodiment 2: a kind of novel method of synthetic 1,2-butylene oxide ring comprises the following steps:
A certain amount of catalyst Ti-si molecular sieves TS-2 is packed in fluidized-bed reactor, add again a certain amount of hydrogen peroxide and solvent acetonitrile, off-response device, passes into 1-butylene and gets rid of air in reactor, continues to pass into 1-butylene and keeps certain pressure in reactor to start reaction.After reaction certain hour, obtain 1,2-butylene oxide ring, sampling analysis.Reaction conditions is: temperature of reaction is 40 ℃, and reaction pressure is 0.2Mpa, and the reaction times is 1h, and hydrogen peroxide concentration is 0.4mol/L, and catalyst concn is 13g/L.
Embodiment 3: a kind of novel method of synthetic 1,2-butylene oxide ring comprises the following steps:
A certain amount of catalyst Ti-si molecular sieves Ti-HMS is packed in fluidized-bed reactor, add again a certain amount of hydrogen peroxide and solvent acetone, off-response device, passes into 1-butylene and gets rid of air in reactor, continues to pass into 1-butylene and keeps certain pressure in reactor to start reaction.After reaction certain hour, obtain 1,2-butylene oxide ring, sampling analysis.Reaction conditions is: temperature of reaction is 50 ℃, and reaction pressure is 0.3Mpa, and the reaction times is 2h, and hydrogen peroxide concentration is 0.5mol/L, and catalyst concn is 15g/L.
Embodiment 4: a kind of novel method of synthetic 1,2-butylene oxide ring comprises the following steps:
A certain amount of catalyst Ti-si molecular sieves Ti-MWW is packed in fixed-bed reactor, add again a certain amount of hydrogen peroxide and solvent methanol, off-response device, passes into 1-butylene and gets rid of air in reactor, continues to pass into 1-butylene and keeps certain pressure in reactor to start reaction.After reaction certain hour, obtain 1,2-butylene oxide ring, sampling analysis.Reaction conditions is: temperature of reaction is 60 ℃, and reaction pressure is 0.4Mpa, and the reaction times is 3h, and hydrogen peroxide concentration is 0.4mol/L, and catalyst concn is 14g/L.
Claims (5)
1. the novel method of synthetic 1, a 2-butylene oxide ring, comprises the following steps:
A certain amount of catalyzer is packed in reactor, then adds a certain amount of hydrogen peroxide and solvent, off-response device, pass into 1-butylene and get rid of air in reactor, continue to pass into 1-butylene and keep certain pressure in reactor to start reaction, after reaction certain hour, obtain 1,2-butylene oxide ring; Described reaction conditions is: temperature of reaction is 40-60 ℃, and reaction pressure is 0.1-0.4Mpa, and the reaction times is 1-3h, and hydrogen peroxide concentration is 0.3-0.9mol/L.
2. method according to claim 1, is characterized in that: described reactor is a kind of in fixed-bed reactor, fluidized-bed reactor, pipeline reactor or their combination.
3. method according to claim 1, is characterized in that: described solvent is a kind of in methyl alcohol, acetonitrile, acetone or their mixture.
4. method according to claim 1, is characterized in that: described catalyzer is a kind of in titanium-silicon molecular sieve TS-1, TS-2, Ti-HMS, Ti-MWW or their mixture.
5. method according to claim 1, is characterized in that: described catalyst concn is 13-16g/L.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410173356.5A CN104003960A (en) | 2014-04-28 | 2014-04-28 | New method for synthesizing 1,2-epoxybutane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410173356.5A CN104003960A (en) | 2014-04-28 | 2014-04-28 | New method for synthesizing 1,2-epoxybutane |
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| Publication Number | Publication Date |
|---|---|
| CN104003960A true CN104003960A (en) | 2014-08-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410173356.5A Pending CN104003960A (en) | 2014-04-28 | 2014-04-28 | New method for synthesizing 1,2-epoxybutane |
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| CN (1) | CN104003960A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104311512A (en) * | 2014-10-13 | 2015-01-28 | 东南大学 | Clean method for preparing 1,2-epoxybutane |
| CN109748886A (en) * | 2017-11-01 | 2019-05-14 | 中国石油化工股份有限公司 | Hydrogen peroxide oxidation butylene produces epoxy butane method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2014
- 2014-04-28 CN CN201410173356.5A patent/CN104003960A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| 王军民等: "《钛硅分子筛催化合成1 , 2-环氧丁烷》", 《精细化工中间体》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104311512A (en) * | 2014-10-13 | 2015-01-28 | 东南大学 | Clean method for preparing 1,2-epoxybutane |
| CN104311512B (en) * | 2014-10-13 | 2016-06-29 | 东南大学 | A kind of clean method for preparing of 1,2-epoxy butane |
| CN109748886A (en) * | 2017-11-01 | 2019-05-14 | 中国石油化工股份有限公司 | Hydrogen peroxide oxidation butylene produces epoxy butane method |
| CN109748886B (en) * | 2017-11-01 | 2022-04-05 | 中国石油化工股份有限公司 | Method for producing epoxybutane by oxydol butylene oxide |
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Application publication date: 20140827 |