CN102260175A - Method for synthesizing 2-aminoethyl(ethyl)amine - Google Patents
Method for synthesizing 2-aminoethyl(ethyl)amine Download PDFInfo
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- CN102260175A CN102260175A CN2011101516521A CN201110151652A CN102260175A CN 102260175 A CN102260175 A CN 102260175A CN 2011101516521 A CN2011101516521 A CN 2011101516521A CN 201110151652 A CN201110151652 A CN 201110151652A CN 102260175 A CN102260175 A CN 102260175A
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- Prior art keywords
- ethylethylenediamine
- reaction
- alcohol
- sodium
- quadrol
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- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title abstract description 11
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 16
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011734 sodium Substances 0.000 claims abstract description 12
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 10
- -1 sodium alkoxide Chemical class 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000011230 binding agent Substances 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 230000035484 reaction time Effects 0.000 claims abstract description 3
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 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 21
- 238000010189 synthetic method Methods 0.000 claims description 17
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 238000010612 desalination reaction Methods 0.000 claims description 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 2
- 229960003750 ethyl chloride Drugs 0.000 abstract 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000008030 elimination Effects 0.000 description 5
- 238000003379 elimination reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- PNLOGXOGWOPPEV-UHFFFAOYSA-N 4-amino-2-methylbutanamide Chemical compound NC(=O)C(C)CCN PNLOGXOGWOPPEV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 241000370738 Chlorion Species 0.000 description 1
- 238000007167 Hofmann rearrangement reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- GUTBHOXHMJMIQV-UHFFFAOYSA-N amino ethyl sulfate Chemical compound CCOS(=O)(=O)ON GUTBHOXHMJMIQV-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- SMSRCGPDNDCXFR-CYWZMYCQSA-N cefbuperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]1(OC)C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 SMSRCGPDNDCXFR-CYWZMYCQSA-N 0.000 description 1
- 229960001817 cefbuperazone Drugs 0.000 description 1
- GCFBRXLSHGKWDP-XCGNWRKASA-N cefoperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 GCFBRXLSHGKWDP-XCGNWRKASA-N 0.000 description 1
- 229960004682 cefoperazone Drugs 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- UCKZMPLVLCKKMO-LHLIQPBNSA-N cephamycin Chemical class S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](C)[C@]21OC UCKZMPLVLCKKMO-LHLIQPBNSA-N 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- IVBHGBMCVLDMKU-GXNBUGAJSA-N piperacillin Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 IVBHGBMCVLDMKU-GXNBUGAJSA-N 0.000 description 1
- 229960002292 piperacillin Drugs 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种N-乙基乙二胺的合成方法，以乙二胺和氯乙烷为原料，醇为溶剂，醇钠为缚酸剂，在高压釜中进行取代反应，反应压力为0.2～2MPa，反应温度为40～80℃，反应时间为3～6小时；乙二胺与氯乙烷的摩尔比为1.45～3.1∶1，氯乙烷与缚酸剂的摩尔比为1∶1.09～1.4；所得反应产物依次经除盐、精馏，得N-乙基乙二胺。采用本发明的方法合成N-乙基乙二胺，具有工艺简洁、易分离、收率高等特点。
The invention discloses a method for synthesizing N-ethylethylenediamine. Using ethylenediamine and ethyl chloride as raw materials, alcohol as a solvent, and sodium alkoxide as an acid-binding agent, the substitution reaction is carried out in an autoclave, and the reaction pressure is 0.2~2MPa, the reaction temperature is 40~80°C, the reaction time is 3~6 hours; the molar ratio of ethylenediamine to ethyl chloride is 1.45~3.1:1, and the molar ratio of ethyl chloride to acid-binding agent is 1: 1.09 to 1.4; the resulting reaction product is desalted and rectified in turn to obtain N-ethylethylenediamine. The method for synthesizing N-ethylethylenediamine has the characteristics of simple process, easy separation, high yield and the like.
Description
Technical field
The present invention relates to a kind of synthetic method of organic compound, particularly a kind of synthetic method of N-ethylethylenediamine.
Background technology
N-ethylethylenediamine (being called for short NEED) molecular formula is H
2NCH
2CH
2NHCH
2CH
3, structural formula is shown in S-1; Colourless transparent liquid, proportion 0.837, refractive index 1.4385,128-130 ℃ of boiling range (101.325KPa), 50 ℃ of flash-points, soluble in water.N-ethylethylenediamine (NEED) is the important intermediate of synthetic many antibiotic medicines, the cefoperazone of cephalosporins, and one of basic raw material of the cefbuperazone of the piperacillin of penicillins and cephamycin derivative is exactly the N-ethylethylenediamine.
The comprehensive literature report, following method is mainly adopted in the preparation of N-ethylethylenediamine at present:
(1) be raw material with ethamine and aminoethyl sulfuric acid, water is solvent, and sodium hydroxide is acid binding agent.Reaction finishes the back distillation and reclaims excessive ethamine, adds 40% sodium hydroxide solution again and tell oily matter in residuum, and all the other liquid are used extracted with diethyl ether again, combining extraction liquid and oily matter, and fractionation is collected cut, productive rate about 40% at 126-132 ℃ then.Reaction formula is shown in S-2.This method productive rate only about 40%, and ethamine consumption about 10 times of theoretical consumption normally.It is also comparatively dangerous to carry out distillation procedure with ether, easier generation security incident when envrionment temperature is high especially, be unfavorable for scale operation (Shandong Normal University's journal, 1998,13 (1): 112-113, Gao Zhanting).
(2) with thanomin, thionyl chloride and ethamine are raw material, and toluene is solvent, and sodium hydroxide is acid binding agent.Elder generation's thanomin and thionyl chloride react the generation chloroethylamine hydrochloride, separate through ethamine ammonia and obtain NEED.Reaction formula is shown in S-3.Thionyl chloride is highly toxic substance and pungency is arranged in the thanomin route method, meet water and emit poisonous sulfurous gas and hydrogenchloride, and in reaction process, have aquatic paired aftertreatment bring certain trouble (the Shanghai chemical industry, 2004,8:19-20, Yi Ting).
(3) generate acrylamide by vinyl cyanide through hydrolysis, acrylamide and ethamine generation addition reaction generate β-aminoethyl propionic acid amide then, obtain the N-ethylethylenediamine by the Hofmann rearrangement reaction at last.Reaction formula is shown in S-4.This reaction is carried out in two steps, causes the prolongation of whole process time, is unfavorable for the carrying out that produce, and the synthetic control of intermediate product β-aminoethyl propionic acid amide difficult (the Tianjin chemical industry, 2003,17 (6): 27-28, Qian Ling).
(4) be raw material with acetate and quadrol, methyl alcohol is solvent, and 5%Pd/C is a catalyzer, under the atmosphere of hydrogen, carry out in autoclave, reaction pressure is 7bar, reacted 4 hours down at 100 ℃, the transformation efficiency of quadrol is 40.9%, and the selectivity of N-ethylethylenediamine is approximately 78.9%.Should use expensive catalysts in the acetate route method, taller pressure ring is operated in the border, and reaction conditions is comparatively harsh.
Summary of the invention
The technical problem to be solved in the present invention provides the synthetic method of the N-ethylethylenediamine that a kind of technology is succinct, easily separated, yield is high.
In order to solve the problems of the technologies described above, the invention provides a kind of synthetic method of N-ethylethylenediamine, with quadrol and monochloroethane is raw material, alcohol is solvent, sodium alkoxide is an acid binding agent, carries out substitution reaction in autoclave, and reaction pressure is 0.2～2Mpa, temperature of reaction is 40～80 ℃, and the reaction times is 3～6 hours; The mol ratio of quadrol and monochloroethane is 1.45～3.1: 1, and the mol ratio of monochloroethane and acid binding agent is 1: 1.09～1.4;
The gained reaction product gets the N-ethylethylenediamine successively through desalination, rectifying.
Improvement as the synthetic method of N-ethylethylenediamine of the present invention: quadrol is 1: 2～5 with the mass ratio of alcohol.
Further improvement as the synthetic method of N-ethylethylenediamine of the present invention: alcohol is the lower aliphatic monohydroxy-alcohol, and described sodium alkoxide is a lower aliphatic monobasic sodium alkoxide.
Further improvement as the synthetic method of N-ethylethylenediamine of the present invention: the lower aliphatic monohydroxy-alcohol is methyl alcohol, ethanol or Virahol; Lower aliphatic monobasic sodium alkoxide is sodium methylate, sodium ethylate or sodium isopropylate.
Reaction scheme of the present invention is as follows:
The mass spectrum of gained N-ethylethylenediamine of the present invention as shown in Figure 1.
The advantage of production method of the present invention is as follows:
1. introducing alcohol is solvent, and sodium alkoxide is an acid binding agent, synthetic under anhydrous condition, has alleviated the burden of aftertreatment, good product selectivity, and technological process is simple, the product yield height.
2. reaction solution mainly contains solvent methanol, and in addition raw material quadrol and product N-ethylethylenediamine also have polysubstituted by product, and above-mentioned each component all can not form azeotrope, can it be separated by conventional rectification.
3. reclaim solvent alcohol and excessive raw material quadrol by rectifying, and separation obtains product N-ethylethylenediamine.Recycle solvent alcohol and excessive quadrol, improve solvent and utilization ratio of raw materials, reduced production cost as far as possible.
4. the solubleness (19g/L) of sodium-chlor in alcohol by with alcohol being the concentration that solvent reduces chlorion, reduces the corrosion to stainless steel equipment much smaller than the solubleness in water (360g/L).
Description of drawings
Below in conjunction with accompanying drawing the specific embodiment of the present invention is described in further detail.
Fig. 1 is the mass spectrum of N-ethylethylenediamine of the present invention.
Embodiment
The synthetic method of embodiment 1, N-ethylethylenediamine:
In the autoclave of band stirring temperature measuring equipment, add quadrol 110g (1.6mol), methyl alcohol 550g, sodium methylate 60g (1.12mol) is pressed into monochloroethane 52g (0.8mol) behind the kettle cover that closes; Be warming up to 40 ℃ in 1h, this moment, pressure was 0.5Mpa.Keep this thermotonus 6h to finish reaction, having reacted pressure is 0.3Mpa.
With the sodium-chlor elimination in the reaction solution, get filtrate rectifying after reaction finishes, collect 128-130 ℃ of cut, get product N-ethylethylenediamine 49.3g, yield 69.89%.
Collect 62-64 ℃ of cut, be methyl alcohol, the rate of recovery is 84.26%; Collect 114-118 ℃ of cut, be quadrol, the rate of recovery is 58.25%, 2 all recyclable utilization.
The synthetic method of embodiment 2, N-ethylethylenediamine:
In the autoclave of band stirring temperature measuring equipment, add quadrol 110g (1.6mol), methyl alcohol 220g, sodium methylate 47.5g (0.88mol) is pressed into monochloroethane 52g (0.8mol) behind the kettle cover that closes, be warming up to 60 ℃ in 1h, and this moment, pressure was 0.7Mpa.Keep this thermotonus 3h to finish reaction, having reacted pressure is 0.36Mpa.
With the sodium-chlor elimination in the reaction solution, get filtrate rectifying after reaction finishes, collect 128-130 ℃ of cut, get product N-ethylethylenediamine 43.2g, yield 61.25%.
Simultaneously, collect solvent methanol and excessive quadrol, 2 the rate of recovery is respectively 84.54% and 58.12%.
The synthetic method of embodiment 3, N-ethylethylenediamine:
In the autoclave of band stirring temperature measuring equipment, add quadrol 110g (1.6mol), methyl alcohol 550g, sodium methylate 52g (0.96mol) is pressed into monochloroethane 52g (0.8mol) behind the kettle cover that closes, be warming up to 80 ℃ in 1h, and this moment, pressure was 1.2Mpa.Keep this thermotonus 4h to finish reaction, having reacted pressure is 0.5Mpa.
With the sodium-chlor elimination in the reaction solution, get filtrate rectifying after reaction finishes, collect 128-130 ℃ of cut, get product N-ethylethylenediamine 42.9g, yield 60.82%.
Simultaneously, collect solvent methanol and excessive quadrol, 2 the rate of recovery is respectively 86.65% and 59.02%.
The synthetic method of embodiment 4, N-ethylethylenediamine:
In the autoclave of band stirring temperature measuring equipment, add quadrol 110g (1.6mol), methyl alcohol 550g, sodium methylate 65g (1.2mol) is pressed into monochloroethane 69g (1.1mol) behind the kettle cover that closes, be warming up to 40 ℃ in 1h, and this moment, pressure was 0.6Mpa.Keep this thermotonus 4h to finish reaction, having reacted pressure is 0.3Mpa.
With the sodium-chlor elimination in the reaction solution, get filtrate rectifying after reaction finishes, collect 128-130 ℃ of cut, get product N-ethylethylenediamine 66.3g, yield 68.35%.
Simultaneously, collect solvent methanol and excessive quadrol, 2 the rate of recovery is respectively 84.45% and 58.55%.
The synthetic method of embodiment 5, N-ethylethylenediamine:
In the autoclave of band stirring temperature measuring equipment, add quadrol 110g (1.6mol), methyl alcohol 330g, sodium methylate 33g (0.6mol) is pressed into monochloroethane 34.5g (0.53mol) behind the kettle cover that closes; Be warming up to 40 ℃ in 1h, this moment, pressure was 0.45Mpa.Keep this thermotonus 4h to finish reaction, having reacted pressure is 0.3Mpa.
With the sodium-chlor elimination in the reaction solution, get filtrate rectifying after reaction finishes, collect 128-130 ℃ of cut, get product N-ethylethylenediamine 33.6g, yield 71.90%.
Simultaneously, collect solvent methanol and excessive quadrol, 2 the rate of recovery is respectively 84.65% and 58.34%.
What more than enumerate only is several specific embodiment of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be arranged.All distortion that those of ordinary skill in the art can directly derive or associate from content disclosed by the invention all should be thought protection scope of the present invention.
Claims (4)
1.N-the synthetic method of ethylethylenediamine is characterized in that: with quadrol and monochloroethane is raw material, and alcohol is solvent, sodium alkoxide is an acid binding agent, carries out substitution reaction in autoclave, and reaction pressure is 0.2～2Mpa, temperature of reaction is 40～80 ℃, and the reaction times is 3～6 hours; The mol ratio of described quadrol and monochloroethane is 1.45～3.1: 1, and the mol ratio of described monochloroethane and acid binding agent is 1: 1.09～1.4;
The gained reaction product gets the N-ethylethylenediamine successively through desalination, rectifying.
2. the synthetic method of N-ethylethylenediamine according to claim 1 is characterized in that: described quadrol is 1: 2～5 with the mass ratio of alcohol.
3. the synthetic method of N-ethylethylenediamine according to claim 1 and 2 is characterized in that: described alcohol is the lower aliphatic monohydroxy-alcohol, and described sodium alkoxide is a lower aliphatic monobasic sodium alkoxide.
4. the synthetic method of N-ethylethylenediamine according to claim 3 is characterized in that: described lower aliphatic monohydroxy-alcohol is methyl alcohol, ethanol or Virahol; Described lower aliphatic monobasic sodium alkoxide is sodium methylate, sodium ethylate or sodium isopropylate.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102816071A (en) * | 2012-08-25 | 2012-12-12 | 太原理工大学 | Synthesis method of N-ethyl ethylene diamine |
| CN103012156A (en) * | 2012-12-13 | 2013-04-03 | 浙江大学 | Preparation method of N,N-diethylethylenediamine |
| CN108069836A (en) * | 2017-12-19 | 2018-05-25 | 山东博苑医药化学有限公司 | It is a kind of to prepare three (3,6- dioxaheptyls）The new method of amine |
| CN109134274A (en) * | 2018-10-15 | 2019-01-04 | 太原科技大学 | A method of separation ethylenediamine and n-ethylethylenediamine mixed solution |
| CN116102429A (en) * | 2022-12-27 | 2023-05-12 | 沈阳化工研究院有限公司 | Process method for continuously synthesizing N-ethyl ethylenediamine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1120059A (en) * | 1978-01-30 | 1982-03-16 | Karel F. Bernady | Process for preparing n-ethylethylenediamine |
-
2011
- 2011-06-08 CN CN2011101516521A patent/CN102260175B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102816071A (en) * | 2012-08-25 | 2012-12-12 | 太原理工大学 | Synthesis method of N-ethyl ethylene diamine |
| CN102816071B (en) * | 2012-08-25 | 2014-05-07 | 太原理工大学 | Synthesis method of N-ethyl ethylene diamine |
| CN103012156A (en) * | 2012-12-13 | 2013-04-03 | 浙江大学 | Preparation method of N,N-diethylethylenediamine |
| CN103012156B (en) * | 2012-12-13 | 2014-11-26 | 浙江大学 | Preparation method of N,N-diethylethylenediamine |
| CN108069836A (en) * | 2017-12-19 | 2018-05-25 | 山东博苑医药化学有限公司 | It is a kind of to prepare three (3,6- dioxaheptyls）The new method of amine |
| CN108069836B (en) * | 2017-12-19 | 2021-04-13 | 山东博苑医药化学股份有限公司 | Novel method for preparing tri (3, 6-dioxaheptyl) amine |
| CN109134274A (en) * | 2018-10-15 | 2019-01-04 | 太原科技大学 | A method of separation ethylenediamine and n-ethylethylenediamine mixed solution |
| CN109134274B (en) * | 2018-10-15 | 2021-01-15 | 太原科技大学 | Method for separating ethylenediamine and N-ethyl ethylenediamine mixed solution |
| CN116102429A (en) * | 2022-12-27 | 2023-05-12 | 沈阳化工研究院有限公司 | Process method for continuously synthesizing N-ethyl ethylenediamine |
| CN116102429B (en) * | 2022-12-27 | 2025-01-28 | 沈阳化工研究院有限公司 | A process for continuously synthesizing N-ethylethylenediamine |
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| CN102260175B (en) | 2013-11-20 |
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