CN109734589A - A kind of method for improving of epoxychloropropane tail gas safe - Google Patents
A kind of method for improving of epoxychloropropane tail gas safe Download PDFInfo
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- CN109734589A CN109734589A CN201910065880.3A CN201910065880A CN109734589A CN 109734589 A CN109734589 A CN 109734589A CN 201910065880 A CN201910065880 A CN 201910065880A CN 109734589 A CN109734589 A CN 109734589A
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- tail gas
- epoxychloropropane
- chloropropene
- improving
- catalyst
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- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000007789 gas Substances 0.000 claims abstract description 49
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 17
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011964 heteropoly acid Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 239000001119 stannous chloride Substances 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- 238000013517 stratification Methods 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims 3
- 150000001336 alkenes Chemical class 0.000 claims 1
- 239000012043 crude product Substances 0.000 claims 1
- 239000004641 Diallyl-phthalate Substances 0.000 abstract description 13
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract description 12
- 238000004880 explosion Methods 0.000 abstract description 7
- 238000005516 engineering process Methods 0.000 abstract description 3
- DFLCZDIXTAAMLZ-UHFFFAOYSA-N phthalic acid;sodium Chemical compound [Na].OC(=O)C1=CC=CC=C1C(O)=O DFLCZDIXTAAMLZ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HQWKKEIVHQXCPI-UHFFFAOYSA-L disodium;phthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C([O-])=O HQWKKEIVHQXCPI-UHFFFAOYSA-L 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- OWXJKYNZGFSVRC-UHFFFAOYSA-N 1-chloroprop-1-ene Chemical class CC=CCl OWXJKYNZGFSVRC-UHFFFAOYSA-N 0.000 description 1
- MZPBNFLTHBUURE-UHFFFAOYSA-N C=CC.[Cl] Chemical group C=CC.[Cl] MZPBNFLTHBUURE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- -1 anti- Should part Chemical compound 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000003486 chemical etching Methods 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
The invention belongs to field of chemical technology, it is related to a kind of method for improving of epoxychloropropane tail gas safe, more specifically, it is related to during a kind of hydrogen peroxide Direct Epoxidation prepares epoxychloropropane, its reaction end gas contains a small amount of chloropropene, oxygen and nitrogen, and there are explosion limits between chloropropene and oxygen, in order to eliminate potential danger, tail gas after reaction is passed into phthalic acid sodium water solution with pressure, so that it is reacted with the chloropropene in tail gas and generates diallyl phthalate, not only it had ensured the essential safety of technique but also had generated the higher diallyl phthalate of added value, VOC emission is reduced simultaneously.
Description
Technical field
The invention belongs to field of chemical technology, are related to a kind of method for improving of epoxychloropropane tail gas safe, more
During preparing epoxychloropropane in particular it relates to a kind of hydrogen peroxide Direct Epoxidation, reaction end gas contains a small amount of chlorine
Propylene, oxygen and nitrogen, and there are explosion limits between chloropropene and oxygen, in order to eliminate potential danger, after reaction
Tail gas is passed into the phthalic acid sodium water solution of pressurization, so that it is reacted with the chloropropene in tail gas and is generated O-phthalic
Diallyl phthalate had not only ensured the essential safety of technique but also had generated the higher diallyl phthalate of added value, simultaneously
Reduce VOC emission.
Background technique
Epoxychloropropane (ECH) and diallyl phthalate are all important fine chemical product and organic centre
Body, purposes are very extensive.Epoxychloropropane is mainly used for preparing epoxy resin, using epoxychloropropane and bisphenol-A as raw material
Epoxy resin obtained has the characteristics that caking property is strong, chemical stability is good, excellent in cushion effect, resistant to chemical etching.ECH can also
With for manufacture glycerol, nitroglycerine, glass reinforced plastic, chlorohydrin rubber, electrical isolation product, and medicine, pesticide, plasticizer and
The common raw material of the products such as ion exchange resin.Diallyl phthalate (DAP) monomer energy under initiator and heat effect
Radical-type polymerization is carried out, diallyl phthalate resin, referred to as " DAP " resin are generated.The resin electric insulation is good, surely
It is qualitative good, wet-heat resisting, can -66 DEG C~180 DEG C be used for a long time, be widely used in aircraft, ship, electronic products terminal plate,
Switch, converter, electronic device etc..
The method for producing epoxychloropropane in the world at present is mainly chlorohydrination, and the epoxychloropropane of chlorohydrination preparation accounts for entirely
90% or more of ball epoxychloropropane yield, its main feature is that mature production technology, stable operation, but can produce in process of production
Raw a large amount of calcium chloride and organic chloride sewage, and raw material chlorine has very strong corrosivity, the serious damage of Yi Yinqi equipment
It is bad.Therefore, there is an urgent need to seek cleaning procedure to be substituted, the study route of most industrial prospect is with hydrogen peroxide at present
For oxygen source, chloropropene Direct Epoxidation prepares epoxychloropropane, which has the advantages that atom utilization is high, environmental-friendly,
Meet the demand for development of Green Chemistry.
But it is invalid containing uncooled raw material chloropropene, the hydrogen peroxide to get off in the epoxychloropropane tail gas of peroxide passivation preparation
Decompose the oxygen generated and the inert nitrogen gas being passed through.With the rising of reaction process tail gas oxygen content, in a certain instantaneous meeting
Reach chloropropene-oxygen explosion limit, brings immeasurable danger to reaction unit.
Patent CN101987838A is proposed during reaction since the decomposition of hydrogen peroxide can be with raw material chloropropene
Gas forms explosive mixture, has risk of explosion, which proposes, controls oxygen concentration of gas phase in the range of 0%~6%,
Mixed gas will not explode, and effectively elimination reaction device gas phase can fire risk.
(it is big that Guo Chong chloropropene Direct Epoxidation produces the East China epoxychloropropane process dangerous Journal of Sex Research [D] science and engineering to document
Learn, 2011.) " chloropropene-oxygen-nitrogen " explosion limit ternary diagram is depicted, and the mixing of working condition ternary is estimated by figure
The limiting oxygen concentration of gas is 10.95%.
Patent CN105712955A provides a kind of process flow of preparing epoxy chloropropane by epoxidation of propylene chloride, including anti-
Should part, separate section and vent gas treatment part, but its vent gas treatment part be only simply provided condenser and it is secondary plus
Pressure condensation storage tank, the chloropropene pressurization condensation return system that will escape out, this operation energy consumption is higher and chloropropene can not quilt completely
It is condensed back, there are explosion dangers.
The simple process of explosion hazard and tail gas in above-mentioned patent and literature research reaction process, but do not consider
The situation undesirable to the volatilization of a large amount of chloropropenes in the actual production process, condensation effect, though condensation effect can achieve by
The reflux of chloropropene total condensation, this will need to consume a large amount of energy, and production cost increases substantially, and industrial production is not practical,
Especially requirement of the country to environmental protection now is higher and higher, it is desirable that and the content of volatile organic matter is less than 1ppm in tail gas, therefore,
The content requirement of tail gas chloropropene is increasingly stringenter, simple condensation has been unable to reach requirement, and needing thoroughly will be in tail gas
Chloropropene reacts away, and the chloropropene in tail gas is passed into the phthalic acid sodium water solution of pressurization by the present invention, improves reaction
Temperature, increase intermolecular collision, the reaction time can be greatly shortened.
Summary of the invention
The problem of epoxychloropropane vent gas treatment being not directed to the technical problem to be solved by the present invention is to the prior art, this
Invention provides a kind of new method that epoxychloropropane tail gas safe is promoted.
The present invention provides a kind of method for improving of epoxychloropropane tail gas safe, and the tail gas after epoxidation reaction is passed through
Into the sodium phthalate reactant aqueous solution device of pressurization, so that it is reacted with the chloropropene in tail gas and generate phthalic acid
Diallyl had not only ensured the essential safety of technique but also had generated the higher diallyl phthalate of added value, subtracted simultaneously
Few VOC emission.
Technical scheme is as follows:
A kind of method for improving of epoxychloropropane tail gas safe, specifically includes the following steps:
(1) heteropolyacid catalyst and raw material chloropropene are added in the reaction flask equipped with reflux condensing tube, and logical nitrogen
It is protected, hydrogen peroxide is added dropwise dropwise, under the effect of the catalyst, it is thick that chloropropene generation epoxidation reaction obtains epoxychloropropane
Product；
(2) tail gas escaped from reflux condensing tube is passed into equipped with catalyst, phthalic anhydride and sodium hydroxide water
In the pressurized reactor of solution, react chloropropene with sodium phthalate, to remove the chloropropene in tail gas；
Catalyst described in above-mentioned steps (2) is one kind or several of tertiary amine, quaternary ammonium salt, liquefied ammonia, stannous chloride, sulfonic acid
Kind；
The quality of sodium hydroxide described in above-mentioned steps (2) is 0.3~2 times of chloropropene quality, phthalic anhydride
Quality be 0.6~4 times of chloropropene quality, the quality of catalyst is the 2%~20% of chloropropene quality；
Reaction temperature described in above-mentioned steps (2) is 80~150 DEG C, reaction time 0.5-1h；
Pressurized reactor described in above-mentioned steps (2), reaction pressure are 0.1~1.0MPa；
The invention has the advantages that providing a kind of method for improving of epoxychloropropane tail gas safe, the preparation of epoxychloropropane
Process cleans, efficient, no three wastes generate.By the sodium phthalate reactant aqueous solution that the tail gas after reaction is passed into pressurization
In device, so that it is reacted with the chloropropene in tail gas and generate diallyl phthalate, chloropropene removal rate is greater than 99%,
Not only it had ensured the safety of technique but also had generated the higher diallyl phthalate of added value, while having reduced VOC emission.
Specific embodiment
Embodiment 1
The preparation process of epoxychloropropane: chloropropene 310g, catalyst phosphato-molybdic heteropolyacid are thrown in 1000ml reaction flask
15g, logical nitrogen are protected, and 45 DEG C are warming up under stirring, and 35%HP is added dropwise, and drop finishes within 4 hours, and 80gHP, reflux heat preservation are added dropwise altogether
2h.Reaction is finished, and is slightly cooled to 36 DEG C, is poured into stratification in separatory funnel, separates oil reservoir, water layer and catalyst, the yield of ECH
It is 91.7%, the volume fraction of chloropropene is 15% in tail gas, and the volume fraction of oxygen is 6%, and the volume fraction of nitrogen is
79%.
The absorption process of tail gas chloropropene: above-mentioned tail gas is passed into equipped with 28g phthalic anhydride and 14g sodium hydroxide
Aqueous solution pressurized reactor in, reactor pressure 0.5MPa, catalyst is copper chloride, dosage 1.0g, at 100 DEG C
Reaction 0.5 hour, the removal rate of chloropropene are 99.8%, and the yield of diallyl phthalate is up to 89%.
Embodiment 2-6
Reaction condition is with embodiment 1, the difference is that the type of catalyst, dosage are different, acquired results are as follows:
Embodiment 7-11
Reaction condition is with embodiment 1, the difference is that the dosage of phthalic anhydride, sodium hydroxide is different, acquired results are such as
Under:
Embodiment 12-17
Reaction condition is with embodiment 1, the difference is that the temperature reacted, time and reactor pressure difference, acquired results are such as
Under:
Content of the present invention is not limited in embodiment content of the present invention.Specific case used herein is to this
Inventive structure and embodiment are expounded, and core of the invention that the above embodiments are only used to help understand is thought
Think.It should be pointed out that for those skilled in the art, without departing from the principle of the present invention, may be used also
With several improvements and modifications are made to the present invention, these improvements and modifications also fall within the scope of protection of the claims of the present invention.
Claims (8)
1. a kind of method for improving of epoxychloropropane tail gas safe, which is characterized in that specifically includes the following steps: (1) will be miscellaneous
Polyacid catalyst and raw material chloropropene are added in the reaction flask equipped with reflux condensing tube, and logical nitrogen is protected, and is dripped dropwise
Add hydrogen peroxide, under the effect of the catalyst, chloropropene occurs epoxidation reaction and obtains epoxychloropropane crude product；(2) will from return
It is anti-that the tail gas of stream condenser pipe evolution is passed into the reactor with pressure equipped with catalyst, phthalic anhydride and sodium hydrate aqueous solution
It answers, removes the chloropropene in tail gas.
2. the method for improving of epoxychloropropane tail gas safe according to claim 1, which is characterized in that above-mentioned steps
(2) catalyst described in is the one or more of tertiary amine, quaternary ammonium salt, liquefied ammonia, stannous chloride, sulfonic acid.
3. the method for improving of epoxychloropropane tail gas safe according to claim 1, which is characterized in that above-mentioned steps
(2) quality of the sodium hydroxide described in is 0.3~2 times of chloropropene quality, and the quality of phthalic anhydride is chloropropene matter
0.6~4 times of amount, the quality of catalyst are the 2%~20% of chloropropene quality.
4. the method for improving of epoxychloropropane tail gas safe according to claim 1, which is characterized in that above-mentioned steps
(2) reaction temperature described in is 80~150 DEG C, reaction time 0.5-1 hour.
5. the method for improving of epoxychloropropane tail gas safe according to claim 1, which is characterized in that above-mentioned steps
(2) reactor with pressure described in, reaction pressure are 0.1~1.0MPa.
6. the method for improving of epoxychloropropane tail gas safe according to claim 1, which is characterized in that epoxychloropropane
Preparation process: chloropropene 310g, catalyst phosphato-molybdic heteropolyacid 15g are thrown in 1000ml reaction flask, logical nitrogen protected, stirred
It mixes down and is warming up to 45 DEG C, 35%HP is added dropwise, drop finishes within 4 hours, and 80gHP, reflux heat preservation 2h are added dropwise altogether, and reaction is finished, and is slightly cooled to 36
DEG C, stratification in separatory funnel is poured into, oil reservoir, water layer and catalyst are separated.
7. the method for improving of epoxychloropropane tail gas safe according to claim 6, which is characterized in that chlorine third in tail gas
The volume fraction of alkene is 15%, and the volume fraction of oxygen is 6%, and the volume fraction of nitrogen is 79%.
8. the method for improving of epoxychloropropane tail gas safe according to claim 7, which is characterized in that by above-mentioned tail gas
It is passed into the reactor with pressure of the aqueous solution equipped with 28g phthalic anhydride and 14g sodium hydroxide, reactor pressure is
0.5MPa, catalyst are copper chloride, and dosage 1.0g reacts 0.5 hour at 100 DEG C.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113509811A (en) * | 2020-04-10 | 2021-10-19 | 中国石油化工股份有限公司 | Method and system for treating tail gas containing chloropropene and oxygen |
| CN113856407A (en) * | 2021-10-28 | 2021-12-31 | 山东新龙集团有限公司 | Method for treating tail gas in process of preparing epoxy chloropropane by oxidation method |
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Cited By (3)
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| CN113509811A (en) * | 2020-04-10 | 2021-10-19 | 中国石油化工股份有限公司 | Method and system for treating tail gas containing chloropropene and oxygen |
| CN113509811B (en) * | 2020-04-10 | 2022-11-29 | 中国石油化工股份有限公司 | Method and system for treating tail gas containing chloropropene and oxygen |
| CN113856407A (en) * | 2021-10-28 | 2021-12-31 | 山东新龙集团有限公司 | Method for treating tail gas in process of preparing epoxy chloropropane by oxidation method |
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Application publication date: 20190510 |