CN1332153A - preparation method of tetraacetylethylenediamine - Google Patents
preparation method of tetraacetylethylenediamine Download PDFInfo
- Publication number
- CN1332153A CN1332153A CN 01122955 CN01122955A CN1332153A CN 1332153 A CN1332153 A CN 1332153A CN 01122955 CN01122955 CN 01122955 CN 01122955 A CN01122955 A CN 01122955A CN 1332153 A CN1332153 A CN 1332153A
- Authority
- CN
- China
- Prior art keywords
- preparation
- tetraacetyl ethylene
- quadrol
- ethylenediamine
- ethylene diamine
- 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.)
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- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000004821 distillation Methods 0.000 claims abstract description 10
- WNYIBZHOMJZDKN-UHFFFAOYSA-N n-(2-acetamidoethyl)acetamide Chemical compound CC(=O)NCCNC(C)=O WNYIBZHOMJZDKN-UHFFFAOYSA-N 0.000 claims abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940090181 propyl acetate Drugs 0.000 claims abstract description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229940043232 butyl acetate Drugs 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- WYGJTQGGQYPSQV-UHFFFAOYSA-N 3,4-diacetylhex-3-ene-2,5-dione Chemical group CC(=O)C(C(C)=O)=C(C(C)=O)C(C)=O WYGJTQGGQYPSQV-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 7
- 239000012024 dehydrating agents Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- -1 amine compounds Chemical class 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A preparation method of tetraacetylethylenediamine, belonging to the technical field of preparation of amine compounds in organic chemistry. The tetraacetylethylenediamine is prepared by two-step synthesis, wherein in the first step, ethylenediamine and acetic acid react to generate diacetyl ethylenediamine and water in the presence of a dehydrating agent, the water generated by the reaction is distilled out through a distillation tower along with the dehydrating agent, in the second step, diacetyl ethylenediamine and acetic anhydride react to generate tetraacetylethylenediamine in the presence of a catalyst, the dehydrating agent can be butyl acetate or ethyl acetate, propyl acetate and the like, the catalyst can be concentrated sulfuric acid or concentrated phosphoric acid and concentrated hydrochloric acid, the molar ratio of the ethylenediamine to the acetic acid can be 1: 1-4, and the molar ratio of the ethylenediamine to the acetic anhydride can be 1: 2-4. The invention completes two-step synthesis in one reaction kettle, has simple and reasonable process, greatly reduces the cost of raw materials, and has the advantages of low equipment investment, relatively simple production process, good product quality, low batching cost and the like.
Description
Technical field
The present invention relates to a kind of preparation method of tetraacetyl ethylene diamine, belong to the preparing technical field of aminated compounds in the organic chemistry.
Background technology
Tetraacetyl ethylene diamine (TAED) is a kind of bleach-activating agent.Its existence can make SPC-D, and Sodium peroxoborate reacts at low temperatures, improves the washing effect of washing composition.The production of existing tetraacetyl ethylene diamine mainly contains two kinds of continuous processing and single stage method, it mainly is anhydrous acetic acid and quadrol to be continuously flowed in the reactor by metering react that continuous processing is produced, reacted product continuously flows out from discharge port, though producing, continuous processing has advantages such as output is big, quality is good, but requirement height to production unit, the operational path complexity, scale of investment is big, the suitability for industrialized production of incompatible general producer.It mainly is with Acetyl Chloride 98Min. or quadrol and aceticanhydride direct reaction generation tetraacetyl ethylene diamine that single stage method is produced, though this method synthesis technique is comparatively simple, but because of aceticanhydride raw material consumption more and on the high side, make the raw materials cost of tetraacetyl ethylene diamine of generation higher, product does not have competitive power on market.
Summary of the invention
It is simpler to the purpose of this invention is to provide a kind of operational path, and the batching cost is low, the preparation method of the tetraacetyl ethylene diamine of good product quality.
The present invention is the preparation method of tetraacetyl ethylene diamine, it is characterized in that described tetraacetyl ethylene diamine is synthetic and make by two steps, the first step is under the condition that has dewatering agent to exist, quadrol and acetic acidreaction are generated diacetyl ethylenediamine and water, and the water that reaction produces steams by distillation tower with dewatering agent; Second step was under the condition that has catalyzer to exist, and diacetyl ethylenediamine and aceticanhydride reaction are generated tetraacetyl ethylene diamine; Described dewatering agent can be butylacetate or ethyl acetate, propyl acetate etc.; Described catalyzer can be the vitriol oil or strong phosphoric acid, concentrated hydrochloric acid; The mol ratio of described quadrol and acetate can be 1: 1～and 4; The mol ratio of described quadrol and aceticanhydride can be 1: 2～and 4.
The add-on of described dewatering agent can be 2～3 times of quadrol weight.Described dewatering agent can be butylacetate.
The mol ratio of described quadrol and acetate can be 1: 2～and 2.5.
When described quadrol and acetic acidreaction, temperature of reaction can be 120～125 ℃, and the tower top temperature of distillation tower can be 90～105 ℃.
The add-on of described catalyzer can be 1～2% of quadrol weight.
Described catalyzer can be 85% the vitriol oil.
The mol ratio of described quadrol and aceticanhydride can be 1: 2～and 2.5.
When described diacetyl ethylenediamine and aceticanhydride reaction, temperature of reaction can be 150～160 ℃, and the tower top temperature of distillation tower can be 118～120 ℃.
The present invention finished for two steps in a reactor synthetic, the technology advantages of simple, and aceticanhydride only is used for the building-up reactions in second step, its consumption significantly reduces, second go on foot the also recyclable building-up reactions that is used for the first step of acetic acid by-product that generates in the reaction simultaneously, raw materials cost is reduced greatly, overcome continuous process route complexity in the prior art, the drawback that the single stage method raw materials cost is high, the present invention has that low equipment investment, production technique are simple relatively, good product quality, batching low cost and other advantages, is fit to the suitability for industrialized production of medium-sized and small enterprises.
The specific embodiment
Embodiment 1
In the 500ml four-hole bottle, add earlier SILVER REAGENT ethylenediamine 30 grams, add butyl acetate and take off Aqua 60 grams are stirring dropping SILVER REAGENT acetic acid 66 grams under the cooling, and this moment, reaction temperature should Be not more than 120 ℃, stir, heat up, dehydration, the reaction temperature in the reactor is controlled at 120～125 ℃, the tower top temperature of destilling tower is controlled at 90～105 ℃, so that dehydrating agent and water can be from distillations Cat head steams, and acetic acid then is back to continuation and second in the reactor because of the backflow effect of destilling tower Diamine reactant is according to distillation cat head temperature control reaction speed, when the top temperature reaches more than 118 ℃ The time, reaction namely comes to an end, and then distillation and recovery dehydrating agent, can after dehydrating agent has reclaimed See the diacetyl ethylenediamine (DADE) that has generated white in the bottle.
After finishing, first step reaction adds SILVER REAGENT aceticanhydride 150 grams and 85% by dropping funel SPA catalyst 0.2ml finishes, and heats up, and this moment, the still temperature should be controlled at about 150 ℃, Reflux and carried out depickling 1 hour in 1 hour, the top temperature is taken off Bi Huiliu 0.5 less than 120 ℃ during depickling Hour, so operate three times, when the still temperature more than 155 ℃, be anti-when not having acid to steam Should finish, reactant liquor is through cooling, and crystallization is filtered, and oven dry namely obtains tetraacetyl ethylene diamine (TAED) about 95 grams, the product yield is 83.3%. It contains by liquid chromatography for measuring Amount is 99.5%.
Embodiment 2:
Other conditions among the embodiment 1 are constant, adopt ethylenediamine, acetic acid, the vinegar of technical grade Acid anhydride is made reaction raw materials, and the product yield of the tetraacetyl ethylene diamine that obtains after the reaction (TAED) is 83.3%, content is 99.2%.
Embodiment 3:
Other conditions among the embodiment 1 are constant, and the consumption of aceticanhydride is increased to 210 grams, reaction After the product yield of the tetraacetyl ethylene diamine (TAED) that obtains be 86.5%, content is 99.5%.
Claims (9)
1. the preparation method of a tetraacetyl ethylene diamine, it is characterized in that described tetraacetyl ethylene diamine is synthetic and make by two steps, the first step is under the condition that has dewatering agent to exist, quadrol and acetic acidreaction are generated diacetyl ethylenediamine and water, and the water that reaction produces steams by distillation tower with dewatering agent; Second step was under the condition that has catalyzer to exist, and diacetyl ethylenediamine and aceticanhydride reaction are generated tetraacetyl ethylene diamine; Described dewatering agent can be butylacetate or ethyl acetate, propyl acetate; Described catalyzer can be the vitriol oil or strong phosphoric acid, concentrated hydrochloric acid; The mol ratio of described quadrol and acetate can be 1: 1～and 4; The mol ratio of described quadrol and aceticanhydride can be 1: 2～and 4.
2. by the preparation method of the described tetraacetyl ethylene diamine of claim 1, the add-on that it is characterized in that described dewatering agent can be 2～3 times of quadrol weight.
3. by the preparation method of claim 1 or 2 described tetraacetyl ethylene diamines, it is characterized in that described dewatering agent can be butylacetate.
4. by the preparation method of the described tetraacetyl ethylene diamine of claim 1, it is characterized in that the mol ratio of described quadrol and acetate can be 1: 2～2.5.
5. by the preparation method of claim 1 or 4 described tetraacetyl ethylene diamines, when it is characterized in that described quadrol and acetic acidreaction, temperature of reaction can be 120～125 ℃, and the tower top temperature of distillation tower can be 90～105 ℃.
6. by the preparation method of the described tetraacetyl ethylene diamine of claim 1, it is characterized in that the add-on of described catalyzer can be 1～2% of quadrol weight.
7. by the preparation method of the described tetraacetyl ethylene diamine of claim 1, it is characterized in that described catalyzer can be 85% the vitriol oil.
8. by the preparation method of the described tetraacetyl ethylene diamine of claim 1, it is characterized in that the mol ratio of described quadrol and aceticanhydride can be 1: 2～2.5.
9. by the preparation method of claim 1 or 8 described tetraacetyl ethylene diamines, when it is characterized in that the reaction of described diacetyl ethylenediamine and aceticanhydride, temperature of reaction can be 150～160 ℃, and the tower top temperature of distillation tower can be 118～120 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01122955 CN1332153A (en) | 2001-07-17 | 2001-07-17 | preparation method of tetraacetylethylenediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01122955 CN1332153A (en) | 2001-07-17 | 2001-07-17 | preparation method of tetraacetylethylenediamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1332153A true CN1332153A (en) | 2002-01-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01122955 Pending CN1332153A (en) | 2001-07-17 | 2001-07-17 | preparation method of tetraacetylethylenediamine |
Country Status (1)
| Country | Link |
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| CN (1) | CN1332153A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004002942A1 (en) * | 2002-06-27 | 2004-01-08 | Zhejiang Jinke Chemistry Co., Ltd | Method of preparing tetraacetylethylenediamine |
| CN101891644A (en) * | 2009-11-19 | 2010-11-24 | 华东理工大学 | Method for synthesizing tetraacetyl ethylene diamine |
| CN101481322B (en) * | 2009-01-19 | 2012-08-08 | 浙江金科日化原料有限公司 | Method for catalytic synthesis of diacetyl ethylenediamine |
| CN109097887A (en) * | 2018-06-29 | 2018-12-28 | 吴江市乾通纺织科技有限公司 | A kind of production method of spandex fabric hollow-out fabric |
-
2001
- 2001-07-17 CN CN 01122955 patent/CN1332153A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004002942A1 (en) * | 2002-06-27 | 2004-01-08 | Zhejiang Jinke Chemistry Co., Ltd | Method of preparing tetraacetylethylenediamine |
| CN101481322B (en) * | 2009-01-19 | 2012-08-08 | 浙江金科日化原料有限公司 | Method for catalytic synthesis of diacetyl ethylenediamine |
| CN101891644A (en) * | 2009-11-19 | 2010-11-24 | 华东理工大学 | Method for synthesizing tetraacetyl ethylene diamine |
| CN109097887A (en) * | 2018-06-29 | 2018-12-28 | 吴江市乾通纺织科技有限公司 | A kind of production method of spandex fabric hollow-out fabric |
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