CN103880781A - Continuous production method for preparing cyclohexene oxide through cyclohexene oxidation with hydrogen peroxide under normal pressure - Google Patents
Continuous production method for preparing cyclohexene oxide through cyclohexene oxidation with hydrogen peroxide under normal pressure Download PDFInfo
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- CN103880781A CN103880781A CN201210555892.2A CN201210555892A CN103880781A CN 103880781 A CN103880781 A CN 103880781A CN 201210555892 A CN201210555892 A CN 201210555892A CN 103880781 A CN103880781 A CN 103880781A
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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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- 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
Abstract
The present invention discloses a continuous production method for preparing cyclohexene oxide through cyclohexene oxidation with hydrogen peroxide under a normal pressure. According to the continuous production method, a reaction part and a separation part are provided, wherein the reaction part reactor comprises two continuous reactors connected in series and two switchable batch reactors connected in parallel, a quaternary ammonium heteropolyphosphatotungstate is adopted as a catalyst, hydrogen peroxide is adopted as an oxidant, preparation of cyclohexene oxide through cyclohexene oxidation is performed under a normal pressure condition, and the separation part is separating an oil phase and a water catalyst mixture through a separator after completing the reaction, wherein the oil phase is subjected to rectification so as to respectively separate the solvent, cyclohexene and cyclohexene oxide, the water catalyst mixture is filtered through a filter to obtain the catalyst, and the water phase is subjected to rectification to separate cyclohexene and cyclohexene oxide contained in the water phase. With the process, the continuous production of cyclohexene oxide through cyclohexene oxidation with phase transfer catalyst catalysis is achieved, and the whole process has characteristics of simpleness, easy operation and mild reaction condition.
Description
Technical field
The invention belongs to petrochemical industry, be specifically related under a kind of condition of normal pressure, take hydrogen peroxide as oxygen source, quaternary ammonium salt phosphor-tungstic heteropoly acid is the continuous production processes of catalyst rings hexene epoxy cyclohexane processed.
Technical background
Epoxy cyclohexane is a kind of important industrial chemicals and intermediate, and its purposes is very extensive, can be used for synthetic epoxy resin, surfactant, agricultural chemicals, sizing agent and macromolecular material etc.
The people such as Xi Zuwei develop reaction control phase transfer catalyst, [Reaction-Controlledphase-Transfer Catalysis for Propylene Epoxidation to Propylene Oxide.Science, 2001,292 (5519): 1139 ~ 1141.], in reaction process, be dissolved to the feature that embodies homogeneous catalyst in reaction system, reaction finishes to return to initial structure separates out and changes heterogeneous catalyst into from reaction system, is the new catalyst that is applicable to large-scale industrial application.CN1355067A discloses for the reaction control phase transfer catalyst of oxidizing reaction and oxidation reaction process thereof.CN1401640A discloses reaction control phase transfer catalyst catalysis epoxidation and has produced the method for epoxy cyclohexane, and tetrahydrobenzene reaches 96% to the transformation efficiency of hydrogen peroxide, and epoxy cyclohexane is 97% to the selectivity of tetrahydrobenzene.
The CN1161346C reaction-controlled phase transfer catalysis cyclohexene oxide epoxy cyclohexane patent processed of this seminar invention is for Industrial processes, but production process is intermittent reaction, exist inefficiency, reaction and separation processes process tediously long, can not meet and simplify production technique, save production cost and realize continuous production.
Therefore the present invention, in order to simplify production technique, save production cost and realize continuous production, provides the continuous production processes of a kind of normal pressure hydrogen peroxide oxidation tetrahydrobenzene epoxy cyclohexane processed.
Summary of the invention
The invention provides the continuous production processes of a kind of normal pressure hydrogen peroxide oxidation tetrahydrobenzene epoxy cyclohexane processed, reactive moieties is made up of with two changeable batch reactors in parallel two series connection flow reactors, this device can meet reaction control phase transfer catalyst catalyzed reaction feature, in flow reactor, carry out homogeneous catalysis epoxidation, in batch reactor, make epoxidation carry out completely, the catalyzer oxygen that loses activity is separated out from reaction system, by the switching realization response control phase-transfer catalysis epoxidation of cyclohexene epoxy cyclohexane serialization processed production process of two batch reactors.
Reaction process is normal pressure condensing reflux process, and reaction process heat release can displace by normal pressure condensing reflux, and the oxygen producing in reaction process can discharge by tail gas discharge system.After reaction finishes, isolate oil phase and water catalyst mix phase through separator, oil phase is deviate from respectively solvent, tetrahydrobenzene and epoxy cyclohexane through three rectifying.Solvent is deviate from rectifying, tetrahydrobenzene is capable of circulation continues to participate in reaction to reactor, and rectifying can obtain high-purity epoxy cyclohexane; Water catalyst mix separates water outlet and catalyzer through catalyst separation system mutually, water is through tetrahydrobenzene and epoxy cyclohexane in the recyclable water of rectifying, isolated catalyzer is capable of circulation is to be made up of with two changeable batch reactors in parallel two series connection flow reactors to continuing to participate in reactive moieties reactor during reactor converges, take quaternary ammonium salt phosphor-tungstic heteropoly acid as catalyzer, take hydrogen peroxide as oxygenant, under condition of normal pressure, carry out cyclohexene oxide and prepare epoxy cyclohexane.After finishing, reaction isolates oil phase and water catalyst mixture through separator, oil phase is isolated respectively solvent, tetrahydrobenzene, epoxy cyclohexane through rectifying, water catalyst mixture leaches catalyzer through strainer, and water goes out through rectifying separation the tetrahydrobenzene and the epoxy cyclohexane that in water, contain.
Technical scheme of the present invention is:
Successive reaction part is for to be made up of two chain of stirred tanks formula flow reactors, and rhythmic reaction part is made up of two changeable stirred-tank reactors in parallel, and sequential portion reactor and rhythmic reaction partial reaction device are by being composed in series a whole set of reactive moieties.
The reactor head of reactive moieties is provided with atmospheric pressure reflux condensing works and normal pressure tail gas discharge system, and condensing reflux temperature is between 5～-5 ℃, and exhaust emissions enters into surge tank after normal pressure condensing works, then by surge tank emptying after gas meter.
The reactor of reactive moieties is equipped with multistage temperature measurement and control instrument, pressure detecting system and explosion protection system.
In first step reactor R1, answer in device R2 material overflow to the second stage, and the second stage answers in device R2 material overflow to third stage R3.
Reactor volume scope is 1 ~ 1000L, first step reactor R1 and second stage reactor R2 volume ratio scope are between 1:1 ~ 2, first step reactor R1 and third stage reactor R3 volume ratio scope all between 1:1.5 ~ 5, two third stage reactor R3 volume ratios are 1:1.The molar ratio of tetrahydrobenzene and hydrogen peroxide is 1:1 ~ 10, and the mol ratio of hydrogen peroxide and quaternary ammonium salt phosphor-tungstic heteropoly acid is 100 ~ 1000:1.
Catalyzer is the quaternary ammonium salt phosphor-tungstic heteropoly acid with reaction control phase transition feature, and it consists of Q
mpW
po
4+3p, in formula, Q is cationic moiety, with [R
1r
2r
3r
4n
+] represent wherein R
1, R
2, R
3, R
4c
5~ C
20alkyl, cycloalkyl, the benzyl of straight or branched, or R
1r
2r
3n is pyridine and homologue thereof; 2≤m≤7, p=2,3,4.
The aqueous hydrogen peroxide solution that the oxygen source hydrogen peroxide concentration using is 15 ~ 70%.Stopper is selected from 2,6 ditertiary butyl p cresol, 2, a kind of or mixing in 6-dinitro-p-cresol, p-ten.-butylcatechol.
The solvent that reaction is used is selected from one or the mixed solvent in aromatic hydrocarbons, ester class, nitrile, halogenated hydrocarbon solvent.
Technique provided by the invention has realized Catalyzed By Phase-transfer Catalyst cyclohexene oxide to be prepared oxirane ring hexene and produces continuously, and a whole set of technique is simple, processing ease, reaction conditions gentleness.
Accompanying drawing explanation
Fig. 1 is the continuous production processes schematic flow sheet of normal pressure hydrogen peroxide oxidation tetrahydrobenzene epoxy cyclohexane processed.
Wherein in accompanying drawing 1, mark is as follows:
R1-first step reactor; R2-second stage reactor; R3-third stage reactor; E1-tail gas buffer tube 1; E2-tail gas buffer tube 2; E3-tail gas buffer tube 3; T1-tetrahydrobenzene rectifying tower; T2-solvent distillation tower; T3-epoxy cyclohexane rectifying tower; T4-water rectifying tower; V1-separator; V2-water-and-oil separator; G1-catalyst separation system.
Embodiment
Below by specific embodiment, the present invention is described further.
Embodiment 1
As shown in Figure 1,35% hydrogen peroxide feed rate is 2kg/h.Tetrahydrobenzene, solvent and catalyst mix slurry feed are 20.5kg/h,, in mixed slurry, tetrahydrobenzene feed rate is 5kg/h, and solvent toluene feed rate is 15kg/h, and catalyst charge amount is 0.5kg/h;
Stopper 2,6 ditertiary butyl p cresol add-on be 100,000 of tetrahydrobenzene add-on/;
It is 1:2 that the volume ratio of device R2 is answered in first step reactor R1 and the second stage, and it is 1:1.5 that second stage reactor R2 and the third stage answer the volume ratio of device R3, and two third stage reactor volumes are than being 1:1;
Material enters reacting rear material overflow to the second stage in first step reactor R1 and answers continuation reaction in device R2, answers in device R2 and forms the overflow of homogeneous reaction material to third stage reactor R3 in the second stage.Third stage reactor R3 is by the batch reactor composition of two changeable parallel connections, catalyzer is separated out from reaction system at third stage reactor R3, reactor R1, R2, R3 top are provided with atmospheric pressure reflux condensing works and normal pressure tail gas discharge system, condensing reflux temperature is at-5 ℃, exhaust emissions enters and enters into respectively tail gas buffer E1, tail gas buffer E2, tail gas buffer E3 after normal pressure condensing works, then emptying after cuvette.
Reaction finishes rear material and isolates oil phase and water catalyst mixture through separator V1, through tetrahydrobenzene rectifying tower TI, rectifying obtains tetrahydrobenzene to oil phase, tetrahydrobenzene is capable of circulation continues to participate in reaction to reactor R1, obtain solvent through solvent distillation tower T2 rectifying again, solvent is capable of circulation continues to participate in reaction to reactor R1, obtains high purity epoxy cyclohexane finally by crossing epoxy cyclohexane rectifying tower T3 rectifying.
Water catalyst mixture separates water outlet and catalyzer through catalyst separation system G1, water reclaims tetrahydrobenzene and the epoxy cyclohexane in water through water rectifying tower T4, water rectifying tower T4 tower top is by tetrahydrobenzene and water azeotropic extraction tetrahydrobenzene and water mixture, and tetrahydrobenzene and water mixture are isolated tetrahydrobenzene and water through water-and-oil separator V2.
Concrete reaction result is in table 1.
Table 1
The present invention includes reactive moieties, separate part.Reactive moieties reactor is to be made up of with two changeable batch reactors in parallel two series connection flow reactors, take quaternary ammonium salt phosphor-tungstic heteropoly acid as catalyzer, take hydrogen peroxide as oxygenant, carries out cyclohexene oxide and prepare epoxy cyclohexane under condition of normal pressure.Separate part is to isolate oil phase and water catalyst mixture through separator after reaction finishes, oil phase is isolated respectively solvent, tetrahydrobenzene, epoxy cyclohexane through rectifying, water catalyst mixture leaches catalyzer through strainer, and water goes out through rectifying separation the tetrahydrobenzene and the epoxy cyclohexane that in water, contain.Technique provided by the invention has realized Catalyzed By Phase-transfer Catalyst cyclohexene oxide to be prepared oxirane ring hexene and produces continuously, and a whole set of technique is simple, processing ease, reaction conditions gentleness.
Claims (9)
1. a continuous production method for normal pressure hydrogen peroxide oxidation tetrahydrobenzene epoxy cyclohexane processed, is characterized in that:
Reactive moieties reactor is to be made up of with two changeable batch reactors in parallel two series connection flow reactors,
After being series at two series connection flow reactors after the batch reactor parallel connection of two changeable parallel connections; Take quaternary ammonium salt phosphor-tungstic heteropoly acid as catalyzer, take hydrogen peroxide as oxygenant, under condition of normal pressure, carry out cyclohexene oxide and prepare epoxy cyclohexane; After finishing, reaction isolates oil phase and water catalyst mixture through separator, oil phase is isolated respectively solvent, tetrahydrobenzene, epoxy cyclohexane through rectifying, water catalyst mixture leaches catalyzer through strainer, and water goes out through rectifying separation the tetrahydrobenzene and the epoxy cyclohexane that in water, contain.
2. it is characterized in that in accordance with the method for claim 1:
Reaction unit comprises reactive moieties, separate part,
Reactive moieties reactor is to be made up of with two changeable batch reactors in parallel two series connection flow reactors, after being series at two series connection flow reactors after the batch reactor parallel connection of two changeable parallel connections;
Separate part comprises separation of oil part and water catalyst mixture separate part, and separation of oil part comprises tetrahydrobenzene rectifying tower, solvent distillation tower, the epoxy cyclohexane rectifying tower of series connection successively; Water catalyst mixture separate part comprises catalyst separation system, the water rectifying tower of series connection successively;
Tetrahydrobenzene, catalyzer, hydrogen peroxide, solvent are added in first step reactor by the entrance that feeds in raw material, first step reactor lower part or bottom are provided with material outlet, the material outlet on first step reactor top is connected with the entrance of second stage reactor bottom, the material outlet on reactor top, the second stage is connected with the entrance of third stage reactor bottom, and the material outlet on third stage reactor top is connected with the material inlet of separator;
First step reactor and second stage reactor are two series connection flow reactors, third stage reactor is the batch reactor of two changeable parallel connections, be equipped with atmospheric pressure reflux condensing works on first step reactor, second stage reactor, third stage reactor top, atmospheric pressure reflux condensing works top is provided with pneumatic outlet, pneumatic outlet is connected with tail gas buffer material inlet, the outlet of tail gas buffer and a coated lycopene;
The oil phase outlet of separator is connected with tetrahydrobenzene rectifying tower middle part material inlet, and the water catalyst mixture outlet of separator is connected with catalyst separation system entrance; The material outlet of tetrahydrobenzene rectifier bottoms is connected with the material inlet at solvent distillation tower middle part, and the material outlet of tetrahydrobenzene rectifier is connected with first step reactor content entrance; The material outlet of solvent distillation tower bottom is connected with the material inlet at epoxy cyclohexane rectifying tower middle part, and the material outlet on solvent distillation tower top is connected with first step reactor content entrance; The material outlet of epoxy cyclohexane rectifier bottoms is connected with a storage tank, and the material outlet on solvent distillation tower top is connected with an epoxy cyclohexane storage tank;
The catalyst outlet of catalyst separation system bottom is connected with first step reactor content entrance, the outlet of catalyst separation system water is connected with the material inlet at water rectifying tower middle part, water rectifier is connected with a water-and-oil separator material inlet, the oil phase of water-and-oil separator exports a road and is connected with the material inlet of water rectifying tower middle part or bottom, another road tetrahydrobenzene outlet is connected with first step reactor content entrance, water outlet and a coated lycopene of water-and-oil separator, water rectifier bottoms is connected with an epoxy cyclohexane storage tank;
Be equipped with gas backstreaming condenser in tetrahydrobenzene rectifying tower, solvent distillation tower, epoxy cyclohexane rectifying tower, water rectifier.
3. according to the method described in claim 1 or 2, it is characterized in that:
The reaction process of reactor is normal pressure condensing reflux process, the reactor head of reactive moieties is provided with atmospheric pressure reflux condensing works and normal pressure tail gas discharge system, condensing reflux temperature is between 5～-5 ℃, exhaust emissions enters into surge tank after normal pressure condensing works, then is entered in cuvette by surge tank.
4. according to the method described in claim 1 or 2, it is characterized in that:
After reaction finishes, isolate oil phase and water catalyst mixture through separator, oil phase is deviate from respectively solvent, tetrahydrobenzene and epoxy cyclohexane through three rectifying; Solvent is deviate from rectifying, tetrahydrobenzene is capable of circulation continues to participate in reaction to first step reactor, and rectifying can obtain pure epoxy cyclohexane; Water catalyst mixture separates water outlet and catalyzer through separator, and water is through tetrahydrobenzene and epoxy cyclohexane in the recyclable water of rectifying, and isolated catalyzer is capable of circulation continues to participate in reaction to first step reactor.
5. according to the method described in claim 1 or 2, it is characterized in that:
The reactor of reactive moieties is equipped with multistage temperature measurement and control instrument, pressure detecting system and explosion protection system.
6. according to the method described in claim 1 or 2, it is characterized in that:
Two series connection flow reactors and the thereafter batch reactor of two changeable parallel connections of series connection, reactor volume scope is 1 ~ 1000L, first step reactor and second stage reactor volume than scope be between 1:1 ~ 2, first step reactor and third stage reactor volume proportional range all between 1:1.5 ~ 5, two third stage reactor volumes are than being 1:1.
7. it is characterized in that in accordance with the method for claim 1:
In reactor, the molar ratio of tetrahydrobenzene and hydrogen peroxide is 1:1 ~ 10, and the mol ratio of hydrogen peroxide and quaternary ammonium salt phosphor-tungstic heteropoly acid is 100 ~ 1000:1.
8. it is characterized in that in accordance with the method for claim 1:
Catalyzer is the quaternary ammonium salt phosphor-tungstic heteropoly acid with reaction control phase transition feature, and it consists of Q
mpW
po
4+3p, in formula, Q is cationic moiety, R
1r
2r
3n is pyridine and homologue thereof or with [R
1r
2r
3r
4n
+] represent wherein R
1, R
2, R
3, R
4c
5~ C
20alkyl, cycloalkyl, the benzyl of straight or branched; 2≤m≤7, p=2,3 or 4;
The aqueous hydrogen peroxide solution that the oxygen source hydrogen peroxide concentration using is 15 ~ 70%.
9. it is characterized in that in accordance with the method for claim 1:
In reaction system, be added with stopper, stopper is selected from 2,6 ditertiary butyl p cresol, 2, one or two or more kinds mixing in 6-dinitro-p-cresol, p-ten.-butylcatechol; The mass ratio of stopper and tetrahydrobenzene is 1:1000 ~ 10000; The solvent that reaction is used is selected from one or two or more kinds mixed solvent in normal hexane, hexanaphthene, benzene, toluene, ethylbenzene, ethyl acetate, trioctyl phosphate, tributyl phosphate, acetonitrile, ethylene dichloride, chloroform solvent; The mass ratio of solvent and tetrahydrobenzene is 1 ~ 100:1.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111841644A (en) * | 2020-08-27 | 2020-10-30 | 郑州大学 | Metal-organic complex immobilized phosphotungstic acid catalyst for synthesizing epoxy cyclohexane |
| CN112142689A (en) * | 2020-11-26 | 2020-12-29 | 中化学科学技术研究有限公司 | Method and system for preparing cyclohexene oxide by using cyclohexene |
| CN112920143A (en) * | 2019-12-06 | 2021-06-08 | 中国科学院大连化学物理研究所 | Reaction device for controlling dehydration in phase transfer catalytic reaction process |
| CN113444058A (en) * | 2020-03-26 | 2021-09-28 | 常州强力先端电子材料有限公司 | Continuous preparation method of alicyclic epoxy compound |
| CN113717130A (en) * | 2021-10-08 | 2021-11-30 | 中化学科学技术研究有限公司 | Continuous production device and method of epoxy cyclohexane |
| CN115106024A (en) * | 2022-07-04 | 2022-09-27 | 山东飞扬化工有限公司 | Mixed flow reactor, mixed flow reaction equipment and method for producing carbonic ester by using mixed flow reactor and mixed flow reaction equipment |
| CN115106024B (en) * | 2022-07-04 | 2024-04-16 | 山东飞扬化工有限公司 | Mixed flow reactor and mixed flow reaction equipment and method for producing carbonic ester by using same |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112920143A (en) * | 2019-12-06 | 2021-06-08 | 中国科学院大连化学物理研究所 | Reaction device for controlling dehydration in phase transfer catalytic reaction process |
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| CN113717130A (en) * | 2021-10-08 | 2021-11-30 | 中化学科学技术研究有限公司 | Continuous production device and method of epoxy cyclohexane |
| CN113717130B (en) * | 2021-10-08 | 2024-04-05 | 中化学科学技术研究有限公司 | Continuous production method of epoxycyclohexane |
| CN115106024A (en) * | 2022-07-04 | 2022-09-27 | 山东飞扬化工有限公司 | Mixed flow reactor, mixed flow reaction equipment and method for producing carbonic ester by using mixed flow reactor and mixed flow reaction equipment |
| CN115106024B (en) * | 2022-07-04 | 2024-04-16 | 山东飞扬化工有限公司 | Mixed flow reactor and mixed flow reaction equipment and method for producing carbonic ester by using same |
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