CN108148030A - A kind of method that 1,5- pentanediols cyclodehydration prepares oxinane - Google Patents
A kind of method that 1,5- pentanediols cyclodehydration prepares oxinane Download PDFInfo
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- CN108148030A CN108148030A CN201810046623.0A CN201810046623A CN108148030A CN 108148030 A CN108148030 A CN 108148030A CN 201810046623 A CN201810046623 A CN 201810046623A CN 108148030 A CN108148030 A CN 108148030A
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- oxinane
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- C07—ORGANIC CHEMISTRY
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
The invention belongs to technical field of compound preparation, disclose a kind of method that 1,5 pentanediol cyclodehydrations prepare oxinane.This method is by 1,5 pentanediols are placed in the reaction kettle for being filled with carried heteropoly acid catalyst or carried heteropoly acid salt catalyst, cyclodehydration reaction is carried out under normal pressure, the distillate that reaction kettle top recovered (distilled) temperature is no more than 95 DEG C is collected, then rectifying is carried out to distillate and obtains product oxinane.The catalyst that preparation method of the present invention is reacted using carried heteropoly acid or its salt as 1,5 pentanediol cyclodehydration, reaction step are simple, reaction condition is mild, so as to reduce the requirement to consersion unit, safety in production hidden danger is reduced, there is higher industrialized popularization value.
Description
Technical field
The invention belongs to technical field of compound preparation, and in particular to a kind of 1,5-PD cyclodehydration prepares tetrahydrochysene pyrrole
The method muttered.
Background technology
Oxinane is a kind of fabulous ether epoxy of symmetry, and structural formula is, -49.2 DEG C of solidification point, boiling point
88 DEG C, index of refraction 1.4195（18.5℃）, -15 DEG C of flash-point；It can volatilize with steam, being soluble in many such as ethyl alcohol, oxinane has
Solvent；It divides relatively low at normal temperatures in being used as solvent, solvent loss rate is smaller, and particularly it is layered completely with water,
It is more suitable for commercial Application.
Traditional oxinane production technology is hydrogenated using dihydropyran, pentamethylene bromide and water are raw material in zinc oxide
Effect is lower to react, but dihydropyran is practical without industrial production, expensive；1, not only cost of material is high for pentamethylene bromide, and
And reaction produces a large amount of salts, pollutes environment, separation process is difficult.The patent of invention of Publication No. CN107376932A, it is open
A kind of copper-based hydrogenation catalyst and preparation method thereof and using it the method for oxinane is prepared, prepared in oxinane
Needed in journey using a large amount of dangerous gas-hydrogen, this requires process unit build will close to the source place of hydrogen, by
It is sex-limited bigger；And raw material tetrahydrofurfuryl alcohol has strong impulse, there is strong impulse effect to eyes, to skin and sticks
Film also has stimulation, and headache, dizziness, nausea etc. can be caused after contact, harmful to environment, and water body can be polluted,
Steam can form explosive mixture with air, meet open fire, high fever or oxidant contact, there is the risk for causing combustion explosion.Cause
This, requirement of this production method to equipment and environment is high.
In conclusion the method for preparing oxinane at present is less, can industrialized production method it is also less.
Invention content
It is miscellaneous more with support type it is an object of the present invention to provide a kind of method that 1,5-PD cyclodehydration prepares oxinane
The catalyst that acid or its salt are reacted as 1,5-PD cyclodehydration, reaction step is simple, and reaction condition is mild, so as to reduce
Requirement to consersion unit, reduces safety in production hidden danger, has higher industrialized popularization value.
To achieve the above object, the present invention uses following technical scheme：
The present invention provides a kind of method that 1,5-PD cyclodehydration prepares oxinane, and 1,5-PD is placed in and is filled with
In the reaction kettle of carried heteropoly acid catalyst or carried heteropoly acid salt catalyst, cyclodehydration reaction is carried out under normal pressure, is received
Collect the distillate that reaction kettle top recovered (distilled) temperature is no more than 95 DEG C, then rectifying is carried out to distillate and obtains product oxinane；
Reaction temperature in the reaction kettle is 170 ~ 260 DEG C, the reaction time is 30 ~ 90min.
Further, the ratio of the 1,5-PD and carried heteropoly acid catalyst or carried heteropoly acid salt catalyst
Example be（30~65）ml：1g.
Further, the load capacity of heteropoly acid is 10 ~ 25wt% in the carried heteropoly acid catalyst；The support type
The load capacity of heteropolyacid salt is 10 ~ 25wt% in heteropolyacid salt catalyst.
Further, the heteropoly acid in the carried heteropoly acid catalyst is in phosphorus heteropoly tungstic acid or silicotungstic heteropolyacid
One kind；Heteropolyacid salt in the carried heteropoly acid salt catalyst is selected from phosphorus heteropoly tungstic acid copper, silicotungstic heteropolyacid copper or phosphorus
One kind in heteropoly tungstic acid cerium.
Further, the carrier in the carried heteropoly acid catalyst or carried heteropoly acid salt catalyst is selected from silicon
One kind in diatomaceous earth, activated carbon, kaolin, molecular sieve, silica, zirconium dioxide or aluminium oxide；The molecular sieve is HY types
Or one kind in HZSM-5.
Compared with prior art, the beneficial effects of the present invention are：
1. the reaction step of preparation method of the present invention is simple, reaction pressure is normal pressure, and reaction temperature is 170 ~ 260 DEG C, reacts item
Part is mild, so as to reduce the requirement to consersion unit, reduces safety in production hidden danger, has higher industrialization promotion valency
Value；The by-product of preparation method of the present invention is few, and up to more than 98.0%, yield reaches as high as obtained product oxinane purity
87.4%。
2. the catalyst that the present invention is reacted using carried heteropoly acid or its salt as 1,5-PD cyclodehydration, is urged
It is high to change activity, stability is good, and service life is long, small to the pollution of the corrosion of equipment and environment in industrialized production, alleviates enterprise
The environmental protection pressure of industry.
3. required equipment is few in the preparation method of the present invention, industry amplification is simple, advantage of lower cost, technological investment compared with
It is small.
Specific embodiment
Following embodiment is not used to limit protection scope of the present invention for illustrating the present invention.It is unless otherwise specified, real
Apply the conventional means that technological means used in example is well known to those skilled in the art.
Carried heteropoly acid catalyst can be made by infusion process in the present invention, and step is as follows：Take a certain amount of heteropoly acid
It is dissolved in distilled water and obtains heteropoly acid aqueous solution, by carrier impregnation in heteropoly acid aqueous solution, volume of heteropoly acid aqueous solution etc.
It in the pore volume of carrier, then is placed in baking oven and activates 6~12h at 100~200 DEG C, heteropoly acid is made equably to be supported on carrier.
The preparation process of carried heteropoly acid salt catalyst is identical with carried heteropoly acid catalyst, and details are not described herein.
Rectifying in oxinane preparation method of the present invention is and optional in actual industrial production using batch fractionating
Use continuous rectification.
In the present invention 1,5- pentanediols cyclodehydration prepare oxinane main reaction formula it is as follows：
Embodiment one
In the flask equipped with short still, the 1,5-PD of 500ml and 15g phosphorus heteropoly tungstic acids copper/activated carbon catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid copper is 10wt% wherein in catalyst.Control reaction temperature
It is 170 DEG C to spend, 95 DEG C of control still head temperature, collects distillate, and 90min reactions terminate.By distillate using interval point
Section rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects tower top temperature and is 88 ± 1 DEG C and distillates
Object is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is 98.3wt%
, oxinane yield 83.1%.
Embodiment two
In the flask equipped with short still, the 1,5-PD of 200ml and 6g phosphorus heteropoly tungstic acids copper/kaolin catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid copper is 25wt% wherein in catalyst.Control reaction temperature
It is 260 DEG C to spend, 90 DEG C of control still head temperature, collects distillate, and 30min reactions terminate.By distillate using interval point
Section rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects tower top temperature and is 88 ± 1 DEG C and distillates
Object is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is 98.1wt%,
Oxinane yield 87.4%.
Embodiment three
In the flask equipped with short still, the 1,5-PD and 22g phosphorus heteropoly tungstic acids copper/zirconium dioxide that add in 1000ml are urged
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid copper is 22wt% wherein in catalyst.Control reaction
Temperature is 210 DEG C, 92 DEG C of control still head temperature, collects distillate, and 80min reactions terminate.By distillate using interval
Rectification and purification is segmented, under normal pressure, removes the light components such as moisture and by-product first, tower top temperature is collected and is 88 ± 1 DEG C and evaporate
It is oxinane to go out object, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is
98.6wt%, oxinane yield 80.9%.
Example IV
In the flask equipped with short still, the 1,5-PD of 1000ml and 23g phosphorus heteropoly tungstic acids/silica catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid is 17wt% wherein in catalyst.Controlling reaction temperature
It it is 200 DEG C, 92 DEG C of control still head temperature collects distillate, and 65min reactions terminate.Distillate is segmented using interval
Rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects the distillate that tower top temperature is 88 ± 1 DEG C
As oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane be 98.5wt%, four
Hydrogen pyrans yield 80.1%.
Embodiment five
In the flask equipped with short still, the 1,5-PD of 1000ml and 16g phosphorus heteropoly tungstic acids/kaolin catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid is 24wt% wherein in catalyst.Controlling reaction temperature
It it is 240 DEG C, 92 DEG C of control still head temperature collects distillate, and 50min reactions terminate.Distillate is segmented using interval
Rectification and purification removes the light components such as moisture and by-product first, and it is tetrahydrochysene pyrrole to collect the distillate that tower top temperature is 88 ± 1 DEG C
It mutters, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane be 98.1wt%, oxinane yield
80.7%。
Embodiment six
In the flask equipped with short still, the 1,5-PD of 1000ml and 24g phosphorus heteropoly tungstic acids/activated carbon catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid is 16wt% wherein in catalyst.Controlling reaction temperature
It it is 260 DEG C, 91 DEG C of control still head temperature collects distillate, and 40min reactions terminate.Distillate is segmented using interval
Rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects the distillate that tower top temperature is 88 ± 1 DEG C
As oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane be 98.0wt%, four
Hydrogen pyrans yield 82%.
Embodiment seven
In the flask equipped with short still, the 1,5-PD of 1000ml and 26g phosphorus heteropoly tungstic acids cerium/alumina catalyzation are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid cerium is 12wt% wherein in catalyst.Control reaction temperature
It is 220 DEG C to spend, 91 DEG C of control still head temperature, collects distillate, and 50min reactions terminate.By distillate using interval point
Section rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects tower top temperature and is 88 ± 1 DEG C and distillates
Object is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is 98.7wt%,
Oxinane yield 80.6%.
Embodiment eight
In the flask equipped with short still, the 1,5-PD of 1000ml and 25g phosphorus heteropoly tungstic acids cerium/HY type molecular sieves are added in
Catalyst carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid cerium is 14wt% wherein in catalyst.Control is anti-
It is 210 DEG C to answer temperature, 92 DEG C of control still head temperature, collects distillate, and 65min reactions terminate.Between distillate is used
It has a rest and is segmented rectification and purification, under normal pressure, remove the light components such as moisture and by-product first, it is 88 ± 1 DEG C to collect tower top temperature
Distillate is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is
98.0wt%, oxinane yield 82.3%.
Embodiment nine
In the flask equipped with short still, the 1,5-PD of 1000ml and 19g phosphorus heteropoly tungstic acids cerium/activated carbon catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of phosphorus heteropoly tungstic acid cerium is 22wt% wherein in catalyst.Control reaction temperature
It is 260 DEG C to spend, 91 DEG C of control still head temperature, collects distillate, and 45min reactions terminate.By distillate using interval point
Section rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects tower top temperature and is 88 ± 1 DEG C and distillates
Object is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is 98.3wt%,
Oxinane yield 84.6%.
Embodiment ten
In the flask equipped with short still, the 1,5-PD of 1000ml and 18g silicotungstic heteropolyacids/zirconia catalyst are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of silicotungstic heteropolyacid is 22wt% wherein in catalyst.Controlling reaction temperature
It it is 180 DEG C, 90 DEG C of control still head temperature collects distillate, and 78min reactions terminate.Distillate is segmented using interval
Rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects the distillate that tower top temperature is 88 ± 1 DEG C
As oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane be 98.2wt%, four
Hydrogen pyrans yield 70.3%.
Embodiment 11
In the flask equipped with short still, the 1,5-PD of 1000ml and 25g silicotungstic heteropolyacids/HZSM-5 catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of silicotungstic heteropolyacid is 15wt% wherein in catalyst.Controlling reaction temperature
It it is 210 DEG C, 93 DEG C of control still head temperature collects distillate, and 65min reactions terminate.Distillate is segmented using interval
Rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects the distillate that tower top temperature is 88 ± 1 DEG C
As oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane be 98.4wt%, four
Hydrogen pyrans yield 74.1%.
Embodiment 12
In the flask equipped with short still, the 1,5-PD of 1000ml and 17g silicotungstic heteropolyacids copper/diatomite catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of silicotungstic heteropolyacid copper is 22wt% wherein in catalyst.Control reaction temperature
It is 170 DEG C to spend, 90 DEG C of control still head temperature, collects distillate, and 82min reactions terminate.By distillate using interval point
Section rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects tower top temperature and is 88 ± 1 DEG C and distillates
Object is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is 98.0wt%,
Oxinane yield 80.6%.
Embodiment 13
In the flask equipped with short still, the 1,5-PD of 650ml and 10g silicotungstic heteropolyacids copper/diatomite catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of silicotungstic heteropolyacid copper is 14wt% wherein in catalyst.Control reaction temperature
It is 180 DEG C to spend, 91 DEG C of control still head temperature, collects distillate, and 62min reactions terminate.By distillate using interval point
Section rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects tower top temperature and is 88 ± 1 DEG C and distillates
Object is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is 98.2wt%,
Oxinane yield 78.6%.
Embodiment 14
In the flask equipped with short still, the 1,5-PD of 900ml and 30g silicotungstic heteropolyacids copper/diatomite catalysis are added in
Agent carries out cyclodehydration reaction under normal pressure, and the load capacity of silicotungstic heteropolyacid copper is 19wt% wherein in catalyst.Control reaction temperature
It is 200 DEG C to spend, 90 DEG C of control still head temperature, collects distillate, and 70min reactions terminate.By distillate using interval point
Section rectification and purification under normal pressure, removes the light components such as moisture and by-product first, collects tower top temperature and is 88 ± 1 DEG C and distillates
Object is oxinane, other heavy constituents higher than oxinane boiling point stay in tower reactor.The purity of oxinane is 98.3wt%,
Oxinane yield 79.1%.
The embodiment of the above, only presently preferred embodiments of the present invention, is only used to explain the present invention, not limit
The scope of the present invention processed, to those of ordinary skill in the art, certainly can be according to skill disclosed in this specification
Art content, makes other embodiments easily by way of replacing or changing, therefore all in the principle of the present invention and technique item
Changes and improvements that part is done etc. should all be included in scope of the present invention patent.
Claims (5)
1. a kind of method that 1,5-PD cyclodehydration prepares oxinane, which is characterized in that 1,5-PD is placed in dress
It is filled in the reaction kettle of carried heteropoly acid catalyst or carried heteropoly acid salt catalyst, it is anti-that cyclodehydration is carried out under normal pressure
Should, the distillate that reaction kettle top recovered (distilled) temperature is no more than 95 DEG C is collected, then rectifying is carried out to distillate and obtains product tetrahydrochysene
Pyrans；Reaction temperature in the reaction kettle is 170 ~ 260 DEG C, the reaction time is 30 ~ 90min.
2. the method that a kind of 1,5-PD cyclodehydration according to claim 1 prepares oxinane, which is characterized in that
The 1,5- pentanediols and the ratio of carried heteropoly acid catalyst or carried heteropoly acid salt catalyst are（30~65）ml：1g.
3. the method that a kind of 1,5-PD cyclodehydration according to claim 1 prepares oxinane, which is characterized in that
The load capacity of heteropoly acid is 10 ~ 25wt% in the carried heteropoly acid catalyst；It is miscellaneous in the carried heteropoly acid salt catalyst
The load capacity of multi-acid salt is 10 ~ 25wt%.
4. the method that a kind of 1,5-PD cyclodehydration according to claim 1 prepares oxinane, which is characterized in that
The one kind of heteropoly acid in phosphorus heteropoly tungstic acid or silicotungstic heteropolyacid in the carried heteropoly acid catalyst；The support type
Heteropolyacid salt in heteropolyacid salt catalyst in phosphorus heteropoly tungstic acid copper, silicotungstic heteropolyacid copper or phosphorus heteropoly tungstic acid cerium one
Kind.
5. the method that a kind of 1,5-PD cyclodehydration according to claim 1 prepares oxinane, which is characterized in that
Carrier in the carried heteropoly acid catalyst or carried heteropoly acid salt catalyst is selected from diatomite, activated carbon, kaolinite
One kind in soil, molecular sieve, silica, zirconium dioxide or aluminium oxide；The molecular sieve is one kind in HY types or HZSM-5.
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| CN201810046623.0A CN108148030B (en) | 2018-01-18 | 2018-01-18 | Method for preparing tetrahydropyran through dehydration and cyclization of 1, 5-pentanediol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108912079A (en) * | 2018-07-25 | 2018-11-30 | 铜仁学院 | A kind of method that fixed-bed catalytic prepares oxinane |
| CN111995600A (en) * | 2020-08-13 | 2020-11-27 | 北京振东光明药物研究院有限公司 | Nitrocapsia impurity compound, preparation method and application thereof |
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| CN1686610A (en) * | 2005-03-23 | 2005-10-26 | 江苏大学 | Preparation method of load type silicotungstic acid catalyst and its use in preparing tetrahydrofurane |
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| CN1272495A (en) * | 1999-04-29 | 2000-11-08 | 中国石油化工集团公司 | Method for preparing tetrahydrofuran by utilizing dehydration and cyclization of 1,4-butanediol |
| CN1686610A (en) * | 2005-03-23 | 2005-10-26 | 江苏大学 | Preparation method of load type silicotungstic acid catalyst and its use in preparing tetrahydrofurane |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108912079A (en) * | 2018-07-25 | 2018-11-30 | 铜仁学院 | A kind of method that fixed-bed catalytic prepares oxinane |
| CN111995600A (en) * | 2020-08-13 | 2020-11-27 | 北京振东光明药物研究院有限公司 | Nitrocapsia impurity compound, preparation method and application thereof |
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| CN108148030B (en) | 2022-03-29 |
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