CN105523943B - Ethylenediamine wastewater recycling process - Google Patents
Ethylenediamine wastewater recycling process Download PDFInfo
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Abstract
The present invention relates to a kind of ethylenediamine (EDA) wastewater recycling process, mainly solves the problem of EDA rate of recovery present in prior art is low, and wastewater treatment containing amine is costly.Waste water of the invention by containing a small amount of entrainer and EDA in EDA recovery towers compression rectification processing dehydrating tower, entrainer removes with water from tower top enters split-phase groove split-phase, organic phase is recycled to dehydrating tower (mainly comprising entrainer) as entrainer, waste water phase (primary aqueous) enters the remaining entrainer of high-efficient coalescence separator separation and is recycled to dehydrating tower, waste water goes to post-process, dehydrating tower kettle liquid and EDA recovery tower bottoms are mixed into EDA product towers, overhead extraction entrainer and a small amount of EDA deliver to EDA recovery towers, side take-off EDA products below EDA products tower top, reach the EDA and entrainer effectively reclaimed in waste water, reduce the technical scheme of wastewater treatment expense, preferably solves the problem, available in EDA technique productions.
Description
Technical field
The present invention relates to a kind of ethylenediamine wastewater recycling process, specifically, monoethanolamine (MEA) catalytic ammoniation method production second
Wastewater recycling process in diamines technique.
Background technology
Ethylenediamine (EDA) is the organic base with amidine functional group, has the characteristics of surface-active, is chemically active essence
Detail mesosome, medicine intermediate.EDA is soluble in water, generates ethylenediamine hydrate, is soluble in ethanol and methanol, is slightly soluble in ether,
Insoluble in benzene.EDA purposes is quite varied, have in the industries such as organic compound, high-molecular compound, medicine, dyestuff, agricultural chemicals compared with
More applications, it is a kind of important fine-chemical intermediate of domestic urgently import, available for preparing epoxy curing agent, metal
Chelating agent EDTA, paper wetting hardening agent, lubrication oil stabilizer, agriculture chemicals fungicide, thiofide, dye fixing agent and
Other fine chemistry industry additives.Domestic market EDA relies primarily on import, ethylenediamine is turned into domestic few in number several
One of well sold and in short supply industrial chemicals.
MEA catalytic ammoniation methods are a kind of ethylenediamine Green Manufacturing Technologies of cleaning, using Ni, Co base catalyst, in hydrogen
Reduce in atmosphere, reaction generation ethylenediamine under condition of high voltage.The companies such as BASF, AkzoNobel, DOW use this technique, and
There is monopoly position, Dalian Inst of Chemicophysics, Chinese Academy of Sciences and Xi'an modern chemistry research institute are also carried out on international market
The correlative study of the technique.
MEA process key reaction equation is as follows：
NH2CH2CH2OH+NH3→NH2CH2CH2NH2+H2O
While a series of side reactions occur, and generation diethylenetriamine (DETA), piperazine (PIP), triethylene diamine (TEDA),
The accessory substances such as hydroxyethyl piperazine (HEP).
It is as follows to generate DETA reaction equations：
NH2CH2CH2OH+NH2CH2CH2NH2→H2NCH2CH2NHCH2CH2NH2+H2O
It is as follows to generate PIP reaction equations：
NH2CH2CH2OH+NH2CH2CH2NH2→C4H10N2+H2O+NH3
It is as follows to generate TEDA reaction equations：
2NH2CH2CH2OH+NH2CH2CH2NH2→C6H12N2+2H2O+2NH3
It is as follows to generate HEP reaction equations：
3NH2CH2CH2OH→C6H14N2O+2H2O+NH3
From the point of view of above main side effect, reaction generates water, and product and accessory substance are highly soluble in water, wherein EDA,
TEDA, PIP can form crystalline hydrate with water.And EDA products, PIP products have strict demand, such as BASF public affairs to water content
Department requires that water content is less than 0.5wt% in ethylenediamine product.The separation of the crystallization water and free water uses azeotropic distillation process mostly.
The dehydrating agent that CN103159629A is used is one or two or more kinds of mixture in benzene, diisopropyl ester, hexamethylene.《Chemistry
Engineering》03 phase in 2012《The separation and simulation of the direct cyclisation product of ethylenediamine》It is proposed to remove mixed solution by entrainer of toluene
In ethylenediamine and the crystallization water intermittent azeotropic rectifying method, finally obtain mass fraction be 96.79% piperazine and 98.26% 3
Ethylene diamine product, and using water as extractant, realize the recycling of entrainer.Because entrainer and water form azeotropic mixture water removal
During, entrainer such as benzene, toluene also forms azeotropic mixture with ethylenediamine, and ethylenediamine and water are difficult clearly to be separated, tower overhead gas
A small amount of ethylenediamine is mixed with phase, because ethylenediamine is soluble in water, after condensing split-phase, ethylenediamine almost all enters waste water phase,
Part entrainer can also enter waste water phase, and direct discharging of waste water will lose ethylenediamine and entrainer, and increase wastewater treatment
Expense.
The present invention provides the recovery process of ethylenediamine waste water, effectively reclaims EDA and entrainer in waste water, reduces waste water
Processing cost, improve ethylenediamine product quality.
The content of the invention
The present invention provides ethylenediamine (EDA) wastewater recycling process, mainly solves the EDA rate of recovery present in prior art
It is low, the problem of wastewater treatment containing amine is costly.When being used for ethylenediamine (EDA) Sewage treatment using technical scheme, tool
There is the advantages of EDA rate of recovery is high, and the expense of wastewater treatment containing amine is low.
In order to solve the above technical problems, the technical solution adopted by the present invention is：
One kind is used for ethylenediamine method for reclaiming waste water, it is characterised in that dehydrating tower contains a small amount of entrainer and EDA (second two
Amine) waste water into the processing of EDA recovery towers compression rectification, entrainer and water remove from tower top enters split-phase groove split-phase, organic phase
Dehydrating tower is recycled to (mainly comprising entrainer) to separate into high-efficient coalescence separator as entrainer, waste water phase (primary aqueous)
Remaining entrainer is recycled to dehydrating tower, and waste water goes to post-process, and dehydrating tower kettle liquid and EDA recovery tower bottoms are mixed into EDA products
Tower, overhead extraction entrainer and a small amount of EDA deliver to EDA recovery towers, EDA products tower top lower section side take-off EDA products.
In above-mentioned technical proposal, it is preferable that dehydration tower top split-phase groove organic phase goes after the remaining water of separator separation to make
Flowed back for dehydrating tower；
Preferably, rectifying column has 20-100 block theoretical trays；
Preferably, dehydrating tower operating pressure is 0.05-0.5MPaA, and tower top temperature is 60-100 DEG C；
Preferably, it is 35~50 DEG C to be dehydrated tower top split-phase groove phase separation temperature；
Preferably, EDA recovery towers operating pressure is 0.2-0.8MPaA, and tower top temperature is 120-180 DEG C；
Preferably, EDA products tower operating pressure is 0.01-0.5MPaA, and tower top temperature is 50-100 DEG C.
Preferably, 1-10 block theories Board position extraction EDA products below EDA products tower top.
Preferably, separator is high-efficient coalescence separator；It is highly preferred that there is one or more inside high-efficient coalescence separator
Taper Coalescence filter core structure.
Dehydration tower top split-phase groove organic phase goes after the remaining water of high-efficient coalescence separator separation to flow back as dehydrating tower.
Traditional filtering separation device, such as gravity settler, inclined plate type separator, corrugated plate dst separator, whirlwind point
Only just have when dispersed phase drop is more than 150 μm, 60 μm, 20 μm, 10 μm and 10 μm from device, and traditional filtering coalescer
Effect.Under normal circumstances, the diameter of entrained drip is both greater than 15 μm in these equipment, to isolate the drop that diameter is less than 10 μm,
Need to use profit high-efficient coalescence separator.
Taper Coalescence filter core structure is used inside high-efficient coalescence separator, fluid flows from inside to outside.Water-oil separating efficiency
Height, cost is low, occupies little space.Dissociate oil content as little as 5-15ppm in the aqueous phase discharged after high-efficient coalescence separator processing.With
Traditional settling tank or filter is compared, and efficient coagulation type hydrocarbon liquid recovery technology can provide Zhuo for process water or extraction water system
Particle and hydrocarbon liquid recyclability more, as little as 0.5 micron of particulate matter is effectively removed, its internal taper for using unique design gathers
Filter core is tied, fluid is flowed from inside to outside, and free hydrocarbon can be reduced to 5-15ppm level by single agglomeration process, without
Secondary separation process.Even for the amine liquid in oil plant, petrochemical plant, and natural gas processing plant, acid water, chilled water (chw) Cargo Oil field
Stable emulsifying hydrocarbon liquid, efficient coagulation type hydrocarbon liquid recovery technology can also provide up to 99.98% separative efficiency in recovered water.
Coalescence technology is removed water in oil to be used to remove substantially all immiscible dispersing liquids in process fluid.Removed water in oil
Coalescer is intercepted using special filter material is less than micron-sized entrained drip.The technology is designed using unique taper Coalescence filter core,
Conical design uses specific fiber geometries and surface properties, can promote fluid Uniform Flow, at utmost reduction pair
The turbulent flow and high flow rate that removal effect interferes, can be by fluid by single agglomeration process when fluid flows from inside to outside
Middle free water content is reduced to 5-15ppm level, without secondary separation process.
EDA recovery towers use compression rectification, operating pressure 0.2-0.8MPaA, preferably 0.45-0.8MPaA, press herein
In the range of power, EDA and water azeotropic disappear, and light component rises to tower top, heavy constituent EDA to tower reactor, waterborne while rise to tower top,
Azeotropic mixture is formed with entrainer, carries entrainer secretly.
Rectifying column is every kind of to be can be designed to fill the packed tower of structured packing or dumped packing or be provided with valve plate,
Sieve plate, double pass tray, the plate column of bubble cap plate or Thorman tray.
Brief description of the drawings
The liquid ammonia process for caustic soda purification that Fig. 1 is the present invention produces ethylenediamine process flow diagram.
In Fig. 1, R101 is catalytic ammoniation reactor, and X101 is ammonia recovery system, and T101 is dehydrating tower, and T102 returns for EDA
Tower is received, T103 is EDA product towers, and D101 is dehydrating tower split-phase groove, and D102 is EDA recovery tower split-phase grooves, and E-101 is dehydration tower top
Condenser, S101 are separator (being removed water in oil), and S102 is separator (oil removing in water), and 1 is reaction product, after 2 is recovery ammonia
Reaction product, 3 be dehydrating tower waste water, and 4 be supplement entrainer, and 5 be dehydrating tower kettle liquid, and 6 be EDA recovery overhead extractions, and 7 are back
Entrainer (containing a small amount of EDA) is received, 8 be waste water (going to post-process), and 10 be EDA product overhead extractions, and 11 be EDA products, and 12 are
MEA, PIP, DETA, TEDA etc. mixed liquor.
Entering R101 after liquefied ammonia and MEA heating and gasifyings, reaction product (logistics 1) enters ammonia recovery system X101 recovery ammonia,
The mixture (logistics 2) containing MEA is dehydrated into dehydrating tower T101 azeotropic distillations after reclaiming ammonia, and tower overhead gas passes through condenser E-
After 101 enter dehydrating tower split-phase groove D101 standing (time of repose was more than 60 minutes) split-phases, organic phase enters efficient coarse separation
Device (removes water) S101 and further removes residual water in oil, remove the organic phase after residual water and flowed back as dehydrating tower T101, waste water
(logistics 3) and residual water enter EDA recovery towers T102 (supplement entrainer (logistics 4) is added to reflux pipeline), compression rectification, tower
Produced Liquid (logistics 6) is pushed up mainly containing entrainer and a small amount of water and EDA, is delivered to quiet into EDA recovery tower T102 split-phase grooves D102
After putting (time of repose was more than 60 minutes) split-phase, aqueous phase (removes water) S102 into high-efficient coalescence separator and further reclaims folder in oil
Band agent, after reclaiming entrainer and organic phase (mainly containing entrainer and be micro water and EDA) merging (logistics 7) be recycled to dehydration
Tower split-phase groove D101, waste water phase 8 (entrainer and EDA containing denier) go to post-process, dehydrating tower T101 kettle liquids (logistics 5) and
EDA recovery tower T102 kettle liquids (logistics 9), which merge, delivers to EDA product tower T103, and overhead extraction liquid (logistics 10, it is main to include entrainment
Agent and EDA) deliver to EDA recovery tower T102, tower top lateral line discharging (logistics 11) is EDA products, kettle liquid (logistics 12) can continue into
Row later separation obtains PIP, DETA, TEDA, AEEA, AEP, HEP, oligomer, and heavy constituent and mixes amine and reclaim unreacted
MEA, it is recycled to reactor.
Below by embodiment, the present invention is further elaborated, but these embodiments are not anyway to this hair
Bright scope is construed as limiting.
Embodiment
【Embodiment 1】
Entering R101 after liquefied ammonia and MEA heating and gasifyings, reaction product (logistics 1) enters ammonia recovery system X101 recovery ammonia,
The mixture (logistics 2) containing MEA is dehydrated into dehydrating tower T101 azeotropic distillations after reclaiming ammonia, and tower overhead gas passes through condenser E-
After 101 enter dehydrating tower split-phase groove D101 standing (time of repose was more than 60 minutes) split-phases, organic phase enters efficient coarse separation
Device (removes water) S101 and further removes residual water in oil, remove the organic phase after residual water and flowed back as dehydrating tower T101, waste water
(logistics 3) and residual water enter EDA recovery towers T102 (supplement entrainer (logistics 4) is added to reflux pipeline), compression rectification, tower
Produced Liquid (logistics 6) is pushed up mainly containing entrainer and a small amount of water and EDA, is delivered to quiet into EDA recovery tower T102 split-phase grooves D102
After putting (time of repose was more than 60 minutes) split-phase, aqueous phase (removes water) S102 into high-efficient coalescence separator and further reclaims folder in oil
Band agent, after reclaiming entrainer and organic phase (mainly containing entrainer and be micro water and EDA) merging (logistics 7) be recycled to dehydration
Tower split-phase groove D101, waste water phase 8 (entrainer and EDA containing denier) go to post-process, dehydrating tower T101 kettle liquids (logistics 5) and
EDA recovery tower T102 kettle liquids (logistics 9), which merge, delivers to EDA product tower T103, and overhead extraction liquid (logistics 10, it is main to include entrainment
Agent and EDA) deliver to EDA recovery tower T102, tower top lateral line discharging (logistics 11) is EDA products, kettle liquid (logistics 12) can continue into
Row later separation obtains PIP, DETA, TEDA, AEEA, AEP, HEP, oligomer, and heavy constituent and mixes amine and reclaim unreacted
MEA, it is recycled to reactor.
Wherein, entrainer is toluene.
Dehydrating tower T101 theoretical cam curves are 25, operating pressure 0.07MPaA, and tower top temperature is 88.7 DEG C, is dehydrated tower top
Split-phase groove phase separation temperature is 40 DEG C.
EDA recovery tower T102 theoretical cam curves are 50, operating pressure 0.45MPaA, and tower top temperature is 148 DEG C.Press herein
Under power, EDA and water azeotropic disappear, and light component rises to tower top, heavy constituent EDA to tower reactor, waterborne while rise to tower top, with folder
Band dosage form carries entrainer secretly into azeotropic mixture.
EDA product towers theoretical cam curve is 50, operating pressure 0.03MPaA, and tower top temperature is 68.7 DEG C.EDA product towers
The theoretical Board position extraction EDA products in the 8th piece of top lower section, 91.5 DEG C of side take-off temperature.EDA product purities >=99.8wt%, have
Machine impurity≤0.1wt%, water content≤0.1wt%, APHA≤15.
Taper Coalescence filter core structure is used inside high-efficient coalescence separator, fluid flows from inside to outside.Water-oil separating efficiency
Height, cost is low, occupies little space.Entrainer toluene level of dissociating in the aqueous phase discharged after high-efficient coalescence separator is handled is low
To 10ppm.
Ethylenediamine product yield >=99.5%, the EDA rate of recovery >=99.6% in waste water, entrainer toluene recovery rate >=
99.9%.
【Embodiment 2】
Embodiment and embodiment 1 are identical.
Wherein, entrainer is hexamethylene.
Dehydrating tower T101 theoretical cam curves are 40, operating pressure 0.05MPaA, and tower top temperature is 79.5 DEG C, is dehydrated tower top
Split-phase groove phase separation temperature is 45 DEG C.
EDA recovery tower T102 theoretical cam curves are 65, operating pressure 0.50MPaA, and tower top temperature is 152 DEG C.Press herein
Under power, EDA and water azeotropic disappear, and light component rises to tower top, heavy constituent EDA to tower reactor, waterborne while rise to tower top, with folder
Band dosage form carries entrainer secretly into azeotropic mixture.
EDA product towers theoretical cam curve is 70, operating pressure 0.05MPaA, and tower top temperature is 82.3 DEG C.EDA product towers
The theoretical Board position extraction EDA products in the 8th piece of top lower section, 102.3 DEG C of side take-off temperature.EDA product purities >=99.9wt%, have
Machine impurity≤0.1wt%, APHA≤10.
Ethylenediamine product yield >=99.5%, the EDA rate of recovery >=99.5% in waste water, the entrainer hexamethylene rate of recovery >=
99.8%.
【Comparative example 1】
As different from Example 1, there is no EDA recovery towers, EDA product towers product is directly from overhead extraction.
EDA product purities=95.2wt%, organic impurities (toluene)=4.8wt%, APHA ＞ 30, ethylenediamine product yield
≤ 70%.
【Comparative example 2】
As different from Example 1, EDA products tower product is not provided with side take-off directly from overhead extraction.
EDA product purities=95.2wt%, organic impurities (toluene)=4.8wt%, APHA ＞ 30.
Ethylenediamine product yield >=99.5%, the EDA rate of recovery >=99.6% in waste water, entrainer toluene recovery rate >=
99.6%.
Claims (6)
1. one kind is used for ethylenediamine method for reclaiming waste water, it is characterised in that：Enter R101 after liquefied ammonia and MEA heating and gasifyings, react
Product stream 1 enters ammonia recovery system X101 recovery ammonia, and the mixture stream passes 2 containing MEA enter dehydrating tower T101 after recovery ammonia
Azeotropic distillation is dehydrated, and tower overhead gas is stood by condenser E-101 into dehydrating tower split-phase groove D101, and time of repose was more than 60 minutes
After split-phase, organic phase enters in oil the high-efficient coalescence separator S101 removed water and further removes residual water, after removing residual water
Organic phase flows back as dehydrating tower T101, and supplement entrainer logistics 4 is added to reflux pipeline, and waste water streams 3 and residual water enter
EDA recovery tower T102, compression rectification, overhead extraction liquid logistics 6 mainly containing entrainer and a small amount of water and EDA, are delivered into EDA
Recovery tower T102 split-phase grooves D102 is stood, and after more than 60 minutes split-phases of time of repose, aqueous phase enters in oil the efficient coalescence removed water
Separator S102 further reclaims entrainer, reclaims entrainer and the mainly organic phase containing entrainer and for micro water and EDA
Logistics 7 after merging is recycled to dehydrating tower split-phase groove D101, and the waste water phase 8 of entrainer and EDA containing denier goes to post-process,
Dehydrating tower T101 kettle liquids logistics 5 and EDA recovery tower T102 kettle liquids logistics 9, which merge, delivers to EDA product tower T103, main to include entrainment
EDA recovery tower T102 are delivered in agent and EDA overhead extraction liquid logistics 10, and tower top lateral line discharging logistics 11 is EDA products, kettle liquid thing
Stream 12 can proceed with later separation and obtain the mixed amine of PIP, DETA, TEDA, AEEA, AEP, HEP, oligomer, and heavy constituent and return
Unreacted MEA is received, is recycled to reactor；
Wherein, waste water material 3 is dehydrating tower waste water.
2. according to claim 1 be used for ethylenediamine method for reclaiming waste water, it is characterised in that dehydrating tower T101 operating pressures
For 0.05-0.5MPa, tower top temperature is 60-100 DEG C.
3. according to claim 1 be used for ethylenediamine method for reclaiming waste water, it is characterised in that EDA recovery towers T102 operation pressures
Power is 0.2-0.8MPa, and tower top temperature is 120-180 DEG C.
4. according to claim 1 be used for ethylenediamine method for reclaiming waste water, it is characterised in that EDA product towers T103 operation pressures
Power is 0.01-0.5MPa, and tower top temperature is 50-100 DEG C.
5. according to claim 1 be used for ethylenediamine method for reclaiming waste water, it is characterised in that 1- below EDA products tower top
10 pieces of theoretical Board position extraction EDA products.
6. it is used for ethylenediamine method for reclaiming waste water according to claim any one of 1-5, it is characterised in that efficiently coalescence point
From there is one or more taper Coalescence filter core structure inside device.
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| CN106187784A (en) * | 2016-07-19 | 2016-12-07 | 湖州晨曦环保科技有限公司 | A kind of method reclaiming tetramethylethylenediamine from methylamino production process |
| CN108623474A (en) * | 2017-03-15 | 2018-10-09 | 汉鸿泰诺化学（上海）有限公司 | It is a kind of to purify N, N, N, the method for N- tetramethyl-1,3-propane diamines using azeotropic distillation |
| CN112827439A (en) * | 2021-01-26 | 2021-05-25 | 盐城仁恒化工有限公司 | Ethylene diamine recycling pretreatment device and pretreatment recycling method |
| CN112619585A (en) * | 2021-01-26 | 2021-04-09 | 盐城仁恒化工有限公司 | Liquid ethylenediamine recycling pretreatment equipment and pretreatment recycling method |
| WO2024002740A1 (en) | 2022-06-29 | 2024-01-04 | Basf Se | Method for manufacture of ethyleneamines |
| WO2024002748A1 (en) | 2022-06-29 | 2024-01-04 | Basf Se | Method for manufacture of ethyleneamines |
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| CN101723837A (en) * | 2009-12-10 | 2010-06-09 | 西安近代化学研究所 | Method for purifying ethylenediamine |
| CN103159629A (en) * | 2011-12-09 | 2013-06-19 | 中国科学院大连化学物理研究所 | Separation method for azeotrope of ethylene diamine and water |
| CN103539675A (en) * | 2013-10-21 | 2014-01-29 | 西安近代化学研究所 | Separation method of ethylenediamine and water azeotrope |
| CN103772205A (en) * | 2012-10-25 | 2014-05-07 | 中国石油化工股份有限公司 | Method for separating ethidene diamine and water |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101723837A (en) * | 2009-12-10 | 2010-06-09 | 西安近代化学研究所 | Method for purifying ethylenediamine |
| CN103159629A (en) * | 2011-12-09 | 2013-06-19 | 中国科学院大连化学物理研究所 | Separation method for azeotrope of ethylene diamine and water |
| CN103772205A (en) * | 2012-10-25 | 2014-05-07 | 中国石油化工股份有限公司 | Method for separating ethidene diamine and water |
| CN103539675A (en) * | 2013-10-21 | 2014-01-29 | 西安近代化学研究所 | Separation method of ethylenediamine and water azeotrope |
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