CN109293600A - A method of residual hydrogen dioxide in removal epoxychloropropane oil reservoir - Google Patents
A method of residual hydrogen dioxide in removal epoxychloropropane oil reservoir Download PDFInfo
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- CN109293600A CN109293600A CN201811340527.3A CN201811340527A CN109293600A CN 109293600 A CN109293600 A CN 109293600A CN 201811340527 A CN201811340527 A CN 201811340527A CN 109293600 A CN109293600 A CN 109293600A
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- oil reservoir
- epoxychloropropane
- removal
- residual hydrogen
- reaction
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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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
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
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- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention discloses a kind of methods of residual hydrogen dioxide in removal epoxychloropropane oil reservoir, the described method includes: in fixed bed reactors, the solid of reproducibility is added, reaction oil reservoir is at the uniform velocity added in the fixed bed reactors by metering pump, the reaction oil reservoir and the solid of the reproducibility is allowed to come into full contact with；The reaction oil reservoir is obtained by chloropropene reacts under heteropolyacid catalyst with hydrogen peroxide；The reaction oil reservoir includes chloropropene, epoxychloropropane, hydrogen peroxide.Operation of the present invention is simple, does not introduce new impurity, is easy to industrializing implementation, has ensured that chloropropene and the hydrogen peroxide Direct Epoxidation under heteropolyacid catalyst catalysis prepare the safety of epoxychloropropane technique.
Description
Technical field
The invention belongs to organic chemistry fileds, more particularly to residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir
Method.
Background technique
Chinese CN101987838A patent proposes decomposition meeting and raw material during reaction due to hydrogen peroxide
Chloropropene gas forms explosive mixture, and patent uses zirconium oxide formula oxygen analyzer, Zirconium oxide oxygen sensor is configured at reaction
Above device gas phase, the oxygen concentration of gas phase is monitored on-line, the model the control of reactor oxygen concentration of gas phase 0%~6%
In enclosing.The patent proposes that within this range, the mixed gas in reactor will not explode, and effectively eliminate reactor gas phase
Fire risk.Explosion hazard in above-mentioned patent research reaction process, but do not consider post-reaction treatment process
In can still remain a small amount of unreacted hydrogen peroxide, still have potential explosion hazard.Existing literature related post-processing with patent
The introduction of aspect is extremely limited, at present it is not yet found that removing the report of residual hydrogen dioxide method in oil reservoir.
It is reacted to obtain reaction oil reservoir under heteropolyacid catalyst with hydrogen peroxide by excessive chloropropene in the prior art, this is anti-
Excessive chloropropene should be selected as solvent without the other solvents of use, the oil reservoir after reaction is in addition to product epoxychloropropane
Also contain a large amount of chloropropene and the unreacted hydrogen peroxide of minimal amount, epoxychloropropane liquid, needs to reaction in order to obtain
Oil reservoir afterwards carries out normal pressure and vacuum distillation, and during distillation, a small amount of hydrogen peroxide can decompose and generate oxygen, with
Chloropropene forms explosive mixture, endangers production safety.
Accordingly, it is desirable to provide a kind of remove residual hydrogen dioxide in epoxychloropropane oil reservoir before reaction oil reservoir distillation
Method is to solve the above problems.
Summary of the invention
The object of the present invention is to provide one kind to pass through chloropropene and the hydrogen peroxide direct ring under heteropolyacid catalyst catalysis
Oxidation prepares the safety method of epoxychloropropane, and specifically purpose is to provide a kind of epoxychloropropane oil obtained from the reactions above
The new method of residual hydrogen dioxide is removed in layer.
The method of hydrogen peroxide is washed to the oil reservoir after reaction in conventional removal oil reservoir, takes a small amount of peroxidating out of
Hydrogen, but due to the characteristic reacted of the present invention, reacts in oil reservoir that there are a large amount of chloropropenes to make the density of oil reservoir very close to water
Density, washing can generate serious emulsion.Therefore, it is necessary to find other methods to handle in present invention reaction oil reservoir
Hydrogen peroxide.Discovery is constantly attempted by the present inventor using some metals and its chlorate and certain sodium salts as reducing agent
It can achieve and decompose hydrogen peroxide remaining in oil reservoir, but do not introduce the effect of new impurity again.Also with fixation
Bed reactor can achieve the purpose of volume production.
Technical scheme is as follows:
A method of residual hydrogen dioxide in removal epoxychloropropane oil reservoir is added certain in fixed bed reactors
Measurer has the solid of reproducibility, and at a certain temperature, reaction oil reservoir is at the uniform velocity added admittedly by metering pump according to certain flow velocity
In fixed bed reactor, the solid of reaction oil reservoir and reproducibility is allowed to come into full contact with, remaining hydrogen peroxide can aoxidize in oil reservoir
Reduction reaction and be removed, place to go rate > 95% of hydrogen peroxide, removal effect is good.
Above-mentioned fixed bed reactors are the glass or stainless steel fixed bed reactors of jacketed heat preservation, bed (reduction up and down
Property solid upper and lower) filling inert filler；
Reaction oil reservoir described in above scheme is obtained by chloropropene reacts under heteropolyacid catalyst with hydrogen peroxide；Instead
Answering oil reservoir includes chloropropene, epoxychloropropane, hydrogen peroxide etc.；
Oil reservoir residual hydrogen dioxide content described in above scheme is 0.1%~1%；
Solid described in above scheme with reproducibility includes Mg, Al, Cu, FeCl2、SnCl2、Na2S2O3、Na2SO3
One or more of equal reducing substances；
The quality of the solid for the reproducibility being added in above scheme is react oil reservoir quality 3%~20%, preferably
8%~10%；
Reaction temperature described in above scheme is 10~40 DEG C, preferably 20~30 DEG C；
Metering flow rate pump described in above scheme is 1~10g/min, preferably 1~4g/min.
The present invention uses fixed bed reactors, provides residual hydrogen dioxide in the simple removal epoxychloropropane oil reservoir of one kind
Method redox reaction occurs, reaches oil removing by contacting the remaining hydrogen peroxide of oil reservoir with the substance of reproducibility
The purpose of a small amount of hydrogen peroxide is remained in layer, the removal rate of residual hydrogen dioxide is 95% or more in oil reservoir.Operation of the present invention letter
It is single, new impurity is not introduced, is easy to industrializing implementation, has ensured that chloropropene and hydrogen peroxide are straight under heteropolyacid catalyst catalysis
Connect the safety that epoxidation prepares epoxychloropropane technique.
Specific embodiment
Embodiment 1
The preparation method of epichlorohydrin reaction oil reservoir: throwing chloropropene 400g in 1000ml four-hole boiling flask, and phosphorus molybdenum is miscellaneous more
Acid catalyst 20g is warming up to 40 DEG C under stirring, 35% hydrogen peroxide 80g is added dropwise in constant pressure separatory funnel, is added dropwise within 4 hours
It finishes, keeps the temperature 2 hours.Reaction is finished, and is down to room temperature, is poured into stratification in separatory funnel, separates oil reservoir, water layer and catalyst,
The oil reservoir separated is the reaction oil reservoir.
The operating method of residual hydrogen dioxide in removal reaction oil reservoir: the glass fixed bed reaction kept the temperature using jacketed
Device, internal diameter 3cm, height 80cm, inside filling 20gNa2SO3Solid, upper and lower part are filled with inert filler, and entrainment is used
30 DEG C of recirculated water temperature control, metering pump is with the flow velocity of 1g/min from reactor top at the uniform velocity by epoxidation reaction oil reservoir 400g (peroxide
Change hydrogen 0.5%) it injects in reactor, reactor lower end connects receiving bottle and receives feed liquid.The content of hydrogen peroxide is in feed liquid
0.0110%, the removal rate of residual hydrogen dioxide is 97.8% in oil reservoir.
Embodiment 2
The stainless steel fixed bed reactors kept the temperature using jacketed, internal diameter 3cm, height 80cm, inside filling 20gNa2SO3
Solid, upper and lower part are filled with inert filler, entrainment use 30 DEG C of recirculated water temperature control, metering pump with the flow velocity of 1g/min from
Reactor top at the uniform velocity injects the epoxidation reaction oil reservoir 400g (hydrogen peroxidase 10 .5%) prepared in embodiment 1 in reactor,
Reactor lower end connects receiving bottle and receives feed liquid.The content of hydrogen peroxide is 0.0130% in feed liquid, remains peroxidating in oil reservoir
The removal rate of hydrogen is 97.4%.
Embodiment 3
The stainless steel fixed bed reactors kept the temperature using jacketed, internal diameter 3cm, height 80cm, inside filling 5gNa2SO3Gu
Body, upper and lower part are filled with inert filler, and entrainment uses 30 DEG C of recirculated water temperature control, and metering pump is with the flow velocity of 1g/min from anti-
Device top is answered at the uniform velocity to inject the epoxidation reaction oil reservoir 400g (hydrogen peroxidase 10 .5%) prepared in embodiment 1 in reactor, instead
Device lower end connection receiving bottle is answered to receive feed liquid.The content of hydrogen peroxide is 0.0150% in feed liquid, residual hydrogen dioxide in oil reservoir
Removal rate be 97.0%.
Embodiment 4-10
Experimentation is with embodiment 1, except that the reducing substances type used and additional amount difference, acquired results are such as
Under:
Embodiment 11-16
Experimentation is with embodiment 1, except that the quality of epoxidation reaction oil reservoir and wherein residual hydrogen dioxide
Content is different, and acquired results are as follows:
| Embodiment | Oil reservoir quality/g | Hydrogen peroxide content/% before handling | Receive feed liquid hydrogen peroxide content/% | Removal rate/% |
| 11 | 600 | 0.1 | 0.0042 | 95.8 |
| 12 | 500 | 0.3 | 0.0108 | 96.4 |
| 13 | 400 | 0.4 | 0.0100 | 97.5 |
| 14 | 300 | 0.6 | 0.0102 | 98.3 |
| 15 | 200 | 0.8 | 0.0120 | 98.5 |
| 16 | 100 | 1.0 | 0.0170 | 98.3 |
Embodiment 17-24
Experimentation is with embodiment 1, except that the temperature of reaction and flow velocity difference, acquired results are as follows:
| Embodiment | Temperature/DEG C | Flow velocity/gmin-1 | Receive feed liquid content of hydrogen peroxide/% | Removal rate/% |
| 17 | 10 | 3 | 0.0225 | 95.5 |
| 18 | 20 | 4 | 0.0160 | 96.8 |
| 19 | 25 | 5 | 0.0140 | 97.2 |
| 20 | 30 | 7 | 0.0115 | 97.7 |
| 21 | 30 | 6 | 0.0085 | 98.3 |
| 22 | 35 | 8 | 0.0060 | 98.8 |
| 23 | 40 | 5 | 0.0090 | 98.2 |
| 24 | 40 | 10 | 0.0120 | 97.6 |
Comparative example 1
The oil reservoir (hydrogen peroxidase 10 .5%) after 400g epoxidation reaction is added in 500ml four-hole boiling flask, adds at 30 DEG C
Enter 40g deionized water, stir 10min, be subsequently poured into the separatory funnel of 500ml, stand, it is unknown to emulsify more serious and layering
It is aobvious, it washs 2 times, by the oil reservoir sample presentation of washing, the content for measuring residual hydrogen dioxide in oil reservoir is 0.1585%, calculates oil-yielding stratum
The wash-off rate of middle residual hydrogen dioxide is 68.3%.
Comparative example 2
Experimentation and condition are with embodiment 1, except that the reducing substances used is changed to Na2S was remained in oil reservoir
The removal rate of hydrogen oxide is 97.7%.Gas chromatography-mass spectrometry analysis is carried out to the oil reservoir after reaction and shows isobutyl mercaptan impurity
It generates, content 0.5%.
This comparative example 2 explanation uses Na2S is reacted as reducing agent, and new impurity is entered to oil reservoir, will be influenced
The purity of final epoxychloropropane product.Therefore, and not all conventional reduction substance is all adapted for carrying out technical effect of the invention.
Content of the present invention is not limited in embodiment content of the present invention.
Specific case used herein is expounded structure of the invention and embodiment, the explanation of above embodiments
It is merely used to help understand the core idea of the present invention.It should be pointed out that for those skilled in the art,
Without departing from the principles of the invention, can be with several improvements and modifications are made to the present invention, these improvement and modification are also fallen
Enter in the protection scope of the claims in the present invention.
Claims (10)
1. a kind of method of residual hydrogen dioxide in removal epoxychloropropane oil reservoir, which is characterized in that the described method includes:
In fixed bed reactors, the solid of reproducibility is added, the fixed bed is at the uniform velocity added by metering pump in reaction oil reservoir
In reactor, the reaction oil reservoir and the solid of the reproducibility is allowed to come into full contact with；The reaction oil reservoir is chloropropene and peroxide
Obtained by change hydrogen reacts under heteropolyacid catalyst；The reaction oil reservoir includes chloropropene, epoxychloropropane, hydrogen peroxide.
2. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as described in claim 1, which is characterized in that
The solid of the reproducibility is Mg, Al, Cu, FeCl2、SnCl2、Na2S2O3、Na2SO3One or more of.
3. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as described in claim 1, which is characterized in that
The content of the reaction oil reservoir residual hydrogen dioxide is 0.1%~1%.
4. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as described in claim 1, which is characterized in that
The quality of the solid of the reproducibility is the 3%~20% of the reaction oil reservoir quality.
5. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as claimed in claim 4, which is characterized in that
The quality of the solid of the reproducibility is the 8%~10% of the reaction oil reservoir quality.
6. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as described in claim 1, which is characterized in that
Reaction temperature is 10 DEG C~40 DEG C.
7. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as claimed in claim 6, which is characterized in that
Reaction temperature is 20 DEG C~30 DEG C.
8. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as described in claim 1, which is characterized in that
The metering flow rate pump is 1g/min~10g/min.
9. the method for residual hydrogen dioxide in a kind of removal epoxychloropropane oil reservoir as claimed in claim 8, which is characterized in that
The metering flow rate pump is 1g/min~4g/min.
10. the method for residual hydrogen dioxide, feature exist in a kind of removal epoxychloropropane oil reservoir as described in claim 1
In the fixed bed reactors are the glass or stainless steel fixed bed reactors of jacketed heat preservation, and bed is filled with inertia up and down
Filler.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811340527.3A CN109293600B (en) | 2018-11-12 | 2018-11-12 | Method for removing residual hydrogen peroxide in epoxy chloropropane oil layer |
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|---|---|---|---|
| CN201811340527.3A CN109293600B (en) | 2018-11-12 | 2018-11-12 | Method for removing residual hydrogen peroxide in epoxy chloropropane oil layer |
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| CN109293600B CN109293600B (en) | 2020-11-06 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111774064A (en) * | 2019-04-04 | 2020-10-16 | 中国石油化工股份有限公司 | Catalyst for decomposing hydrogen peroxide in epoxidation reaction product of 3-chloropropene and hydrogen peroxide |
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| JP2015130844A (en) * | 2014-01-15 | 2015-07-23 | 株式会社片山化学工業研究所 | Decomposition treatment method for hydrogen peroxide |
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Address after: 222065 room 316, building 2, Jiangsu Avenue SME Park, Xuwei New District, Lianyungang City, Jiangsu Province Patentee after: JIANGSU RUIHENG NEW MATERIAL TECHNOLOGY Co.,Ltd. Patentee after: Jiangsu Yangnong Chemical Group Co.,Ltd. Patentee after: JIANGSU RUIXIANG CHEMICAL Co.,Ltd. Address before: 225009 No. 39, Wenfeng Road, Yangzhou, Jiangsu Patentee before: Jiangsu Yangnong Chemical Group Co.,Ltd. Patentee before: JIANGSU RUIXIANG CHEMICAL Co.,Ltd. Patentee before: JIANGSU RUIHENG NEW MATERIAL TECHNOLOGY Co.,Ltd. |
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Address after: 222065 No.28, Shihua 7th Road, Lianyungang City, Jiangsu Province Patentee after: JIANGSU RUIHENG NEW MATERIAL TECHNOLOGY Co.,Ltd. Patentee after: Jiangsu Yangnong Chemical Group Co.,Ltd. Patentee after: JIANGSU RUIXIANG CHEMICAL Co.,Ltd. Address before: 222065 room 316, building 2, Jiangsu Avenue SME Park, Xuwei New District, Lianyungang City, Jiangsu Province Patentee before: JIANGSU RUIHENG NEW MATERIAL TECHNOLOGY Co.,Ltd. Patentee before: Jiangsu Yangnong Chemical Group Co.,Ltd. Patentee before: JIANGSU RUIXIANG CHEMICAL Co.,Ltd. |