CN106187784A - A kind of method reclaiming tetramethylethylenediamine from methylamino production process - Google Patents
A kind of method reclaiming tetramethylethylenediamine from methylamino production process Download PDFInfo
- Publication number
- CN106187784A CN106187784A CN201610567604.3A CN201610567604A CN106187784A CN 106187784 A CN106187784 A CN 106187784A CN 201610567604 A CN201610567604 A CN 201610567604A CN 106187784 A CN106187784 A CN 106187784A
- Authority
- CN
- China
- Prior art keywords
- tetramethylethylenediamine
- liquid
- methylamino
- caustic soda
- production process
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 title claims abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 67
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 22
- 239000007787 solid Substances 0.000 claims abstract description 10
- 239000002910 solid waste Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 230000018044 dehydration Effects 0.000 claims abstract description 6
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 6
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003912 environmental pollution Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000001932 seasonal effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009270 solid waste treatment Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of method reclaiming tetramethylethylenediamine from methylamino production process, comprise the following steps: a). put into a certain amount of solid waste detecting tetramethylethylenediamine salt content in a kettle., it is subsequently adding liquid caustic soda, liquid caustic soda concentration is 30% ~ 50%, tetramethylethylenediamine salt is 1:0.7 ~ 4.3 with the molar ratio example of liquid caustic soda, and reaction temperature is 0 100 DEG C；B). after the tetramethylethylenediamine that fully dissociates, distill out aqueous tetramethylethylenediamine solution, add solid sodium hydroxide the most in the solution, be fully layered stand-by after dehydration；C). the upper strata tetramethylethylenediamine liquid in step b) is directly injected into rectification in rectifying column, i.e. can get tetramethylethylenediamine.Present invention process is fairly simple, workable, and working environment toxic is little, and the tetramethylethylenediamine response rate is high, reduces the production cost of methylamino.
Description
Technical field
The present invention relates to a kind of method reclaiming tetramethylethylenediamine from methylamino production process.
Background technology
Tetramethylethylenediamine is important chemical industry raw material, and due to the chemical property that it is special, it is the most miscible with water, with
Acidic materials form salt etc., and it is multiple at medicine, pesticide, spice, rubber, fuel, daily use chemicals, food, beverage, surfactant etc.
The application in field is quite varied, along with the fast development of Chinese national economy, the most day by day increases the demand of tetramethylethylenediamine
Add.Therefore, the recovery of tetramethylethylenediamine is particularly significant.
A certain amount of waste water produced in production operation, i.e. contains tetramethylethylenediamine or tetramethylethylenediamine salt,
If not processing or dealing with improperly, serious environmental pollution can be caused, it is necessary to administered；It addition, cause the waste of raw material, make
Production cost is greatly improved.Therefore, in the urgent need to the tetramethylethylenediamine recovery technology of a kind of simple economy.
Recovery to tetramethylethylenediamine, traditional handicraft has the recovery method of its analog pyridine, takes benzene evaporation real
Existing, owing to benzene is volatile, high toxicity, the feature such as inflammable and explosive, it is easy to cause environmental pollution and operational hazards.And the ice of benzene
Point is higher, and recovery process is big by seasonal effect, and yield is low, and cost recovery is higher.Chinese patent CN1268612C give one
Using alkali, sodium salt, sulfate etc. cooks separating medium, saltout recovery pyridine and the technology of homologue thereof, but substantial amounts of salt after saltouing
Need to process, containing a certain amount of water and salt in pyridine liquid, bring difficulty to rectification.Additionally Chinese patent CN1370770A introduces
A kind of from pyridine solution through repeatedly distilling and be dried, final acquisition water content solution below 10% carries out rectification and obtains
The recovery technology of pyridine.The method through repeatedly distilling and to be dried, and causes energy consumption high, and the unfavorable factors such as operational ton is big reclaim
Cost is of a relatively high.Take a broad view of above technology, all there is certain deficiency, bring inconvenience to production.
Raw material is made at methylamino production process tetramethylethylenediamine to be used.Production operation to produce a certain amount of solid
Body garbage.These solid waste typically contain tetramethylethylenediamine or tetramethylethylenediamine salt, if do not process or
Deal with improperly, serious environmental pollution can be caused, it is necessary to administered；It addition, cause the waste of raw material, make production cost significantly
Improve.Therefore, in the urgent need to the tetramethylethylenediamine recovery technology of a kind of simple economy.
Summary of the invention
In order to overcome the deficiency of above-mentioned prior art, it is an object of the invention to provide one can be at low cost from tetramethyl
Ethylenediamine salt or containing reclaiming tetramethylethylenediamine in tetramethylethylenediamine waste water, can ensure that again recovery product quality meets methylamine
The method of base manufacturing technique requirent, thus effectively prevent and treat environmental pollution, improve raw material availability, reduce production cost.
In order to realize above-mentioned purpose, present invention employs following technical scheme:
A kind of method reclaiming tetramethylethylenediamine from methylamino production process, comprises the following steps:
A). put into a certain amount of solid waste detecting tetramethylethylenediamine salt content in a kettle., be subsequently adding liquid
Alkali, liquid caustic soda concentration is 30% ~ 50%, and tetramethylethylenediamine salt is 1:0.7 ~ 4.3 with the molar ratio example of liquid caustic soda, and reaction temperature is
0-100℃；
B). after the tetramethylethylenediamine that fully dissociates, distill out aqueous tetramethylethylenediamine solution, add the most in the solution
It is layered stand-by after solid sodium hydroxide, fully dehydration；
C). the upper strata tetramethylethylenediamine liquid in step b) is directly injected into rectification in rectifying column, i.e. can get tetramethyl second two
Amine.
Preferably: apply mechanically when the azeotropic liquid that in described step c), rectification produces is with lower batch reaction fluid dewatering, rectification
Apply mechanically when the low boiling liquid produced is with lower batch reaction liquid rectification.
Preferably: described tetramethylethylenediamine salt is 1:1.6 ~ 3 with the molar ratio example of liquid caustic soda, reaction temperature
It it is 60 ~ 90 DEG C.
Preferably: the lower floor's liquid caustic soda in described step b) squeezes into reservoir, standby lower batch processing solid waste is used.
Present invention process is fairly simple, workable, and working environment toxic is little, and the tetramethylethylenediamine response rate is high,
Reduce the production cost of methylamino.And base in Solid Waste Treatment and follow-up waste water tetramethylethylenediamine removal process
This three-waste free discharge, the most pollution-free to periphery river etc., save environmental pollution improvement's expense.
Specific implementation method:
Being described further the technical solution of the present invention below in conjunction with embodiment, these embodiments are it is not intended that to skill
The restriction of art scheme.
Embodiment 1
In 500ml reactor, put into the solid waste 350g detecting content, put into 50% liquid caustic soda 280g, be warmed up to 80 DEG C, fill
After dividing the tetramethylethylenediamine that dissociates, distill out aqueous tetramethylethylenediamine solution, calculate according to the water yield in solution, add 120g
It is layered after solid sodium hydroxide, fully dehydration.Lower floor's liquid caustic soda is used for lower batch of solids treatment.Upper strata tetramethylethylenediamine liquid enters rectification
Tower rectification.
After fraction before having collected 120 DEG C, start to collect 121 DEG C of tails, it is thus achieved that qualified tetramethylethylenediamine 178g,
Yield 71.2%
Embodiment 2
In 500L reactor, put into the solid waste 320Kg detecting content, put into 50% liquid caustic soda 260Kg, be warmed up to 50 DEG C,
Fully dissociate after tetramethylethylenediamine, distill out aqueous tetramethylethylenediamine solution, calculate according to the water yield in solution, add
It is layered after 120Kg solid sodium hydroxide, fully dehydration.Lower floor's liquid caustic soda is used for lower batch of solids treatment.Upper strata tetramethylethylenediamine liquid
Enter rectifying column rectification.
Fraction before collecting 120 DEG C is dehydrated again with lower batch reaction liquid, and after collecting 121 DEG C, the qualified fraction of moisture obtains
Obtain acceptable industrial tetramethylethylenediamine.Obtain industry tetramethylethylenediamine 169Kg, yield 73.9%
Embodiment 3
In 2000L reactor, put into solid waste 900Kg, detect its tetramethylethylenediamine salt content, put into 30% liquid caustic soda
1400Kg, is warmed up to 70 DEG C, after the tetramethylethylenediamine that fully dissociates, distills out aqueous tetramethylethylenediamine solution, according to molten
In liquid, the water yield calculates, and adds 700Kg solid sodium hydroxide, is fully layered after dehydration.Lower floor's liquid caustic soda is used for lower batch of solids treatment.On
Layer tetramethylethylenediamine liquid enters rectifying column rectification.
Fraction before collecting 120 DEG C is dehydrated again with lower batch reaction liquid, and after collecting 121 DEG C, the qualified fraction of moisture obtains
Obtain acceptable industrial tetramethylethylenediamine.Obtain industry tetramethylethylenediamine 460Kg, yield 71.6%.
The plurality of advantages such as it is simple that the method for the present invention has technique, easy to operate, and the tetramethylethylenediamine response rate is high.Pass through
After process, solid waste takes up room, the material Han amine salt is recycled in waste water, reduces the production cost of methylamino, simultaneously
Reduce the COD in waste water so that waste water can be with qualified discharge.The tetramethylethylenediamine response rate reaches more than 70%, and herein
Reason removal process, discharges without three industrial wastes substantially, environmentally friendly.
Claims (4)
1. the method reclaiming tetramethylethylenediamine from methylamino production process, it is characterised in that: comprise the following steps:
A). put into a certain amount of solid waste detecting tetramethylethylenediamine salt content in a kettle., be subsequently adding liquid
Alkali, liquid caustic soda concentration is 30% ~ 50%, and tetramethylethylenediamine salt is 1:0.7 ~ 4.3 with the molar ratio example of liquid caustic soda, and reaction temperature is
0-100℃；
B). after the tetramethylethylenediamine that fully dissociates, distill out aqueous tetramethylethylenediamine solution, add the most in the solution
It is layered stand-by after solid sodium hydroxide, fully dehydration；
C). the upper strata tetramethylethylenediamine liquid in step b) is directly injected into rectification in rectifying column, i.e. can get tetramethyl second two
Amine.
A kind of method reclaiming tetramethylethylenediamine from methylamino production process the most according to claim 1, its feature
Be: in described step c) rectification produce azeotropic liquid with lower batch reaction fluid dewatering time apply mechanically, rectification produce low boiling liquid and under
Apply mechanically during batch reaction liquid rectification.
A kind of method reclaiming tetramethylethylenediamine from methylamino production process the most according to claim 1, its feature
It is: described tetramethylethylenediamine salt is 1:1.6 ~ 3 with the molar ratio example of liquid caustic soda, and reaction temperature is 60 ~ 90 DEG C.
A kind of method reclaiming tetramethylethylenediamine from methylamino production process the most according to claim 1, its feature
Being: the lower floor's liquid caustic soda in described step b) squeezes into reservoir, standby lower batch processing solid waste is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610567604.3A CN106187784A (en) | 2016-07-19 | 2016-07-19 | A kind of method reclaiming tetramethylethylenediamine from methylamino production process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610567604.3A CN106187784A (en) | 2016-07-19 | 2016-07-19 | A kind of method reclaiming tetramethylethylenediamine from methylamino production process |
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| Publication Number | Publication Date |
|---|---|
| CN106187784A true CN106187784A (en) | 2016-12-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610567604.3A Pending CN106187784A (en) | 2016-07-19 | 2016-07-19 | A kind of method reclaiming tetramethylethylenediamine from methylamino production process |
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| CN (1) | CN106187784A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134563A (en) * | 2018-08-08 | 2019-01-04 | 河北威远生物化工有限公司 | A kind of catalysis synthesizing technology of emamectin benzoate key intermediate |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1370770A (en) * | 2001-02-27 | 2002-09-25 | 天津药业集团有限公司 | Pyridine recovering process |
| CN1867539A (en) * | 2003-10-17 | 2006-11-22 | 巴斯福股份公司 | Method for the distillative separation of mixtures containing ethyleneamines |
| WO2007079944A1 (en) * | 2006-01-11 | 2007-07-19 | Dsm Ip Assets B.V. | Process for isolation of an organic amine |
| CN105523943A (en) * | 2014-10-24 | 2016-04-27 | 中国石油化工股份有限公司 | Ethylenediamine waste water recovery technology |
-
2016
- 2016-07-19 CN CN201610567604.3A patent/CN106187784A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1370770A (en) * | 2001-02-27 | 2002-09-25 | 天津药业集团有限公司 | Pyridine recovering process |
| CN1867539A (en) * | 2003-10-17 | 2006-11-22 | 巴斯福股份公司 | Method for the distillative separation of mixtures containing ethyleneamines |
| US20070043217A1 (en) * | 2003-10-17 | 2007-02-22 | Basf Aklengesellschaft | Method for the distillative separation of mixtures containing ethyleneamines |
| WO2007079944A1 (en) * | 2006-01-11 | 2007-07-19 | Dsm Ip Assets B.V. | Process for isolation of an organic amine |
| CN105523943A (en) * | 2014-10-24 | 2016-04-27 | 中国石油化工股份有限公司 | Ethylenediamine waste water recovery technology |
Non-Patent Citations (2)
| Title |
|---|
| MONCHAK, M. M.等: "Copper(I) halide complexes with N,N"-diallyl-N,N,N",N"-tetramethylethylenediaminium (L2+). Synthesis and crystal structures of the complexes [L0.5CuCl2], [L0.5CuCl0.72Br1.28], and [L0.5CuBr2]", 《RUSSIAN JOURNAL OF COORDINATION CHEMISTRY》 * |
| 段行信: "《实用精细有机合成手册》", 31 January 2000, 化学工业出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109134563A (en) * | 2018-08-08 | 2019-01-04 | 河北威远生物化工有限公司 | A kind of catalysis synthesizing technology of emamectin benzoate key intermediate |
| CN109134563B (en) * | 2018-08-08 | 2020-09-15 | 河北威远生物化工有限公司 | Catalytic synthesis process of methylamino abamectin key intermediate |
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Application publication date: 20161207 |