CN102180797A - Synthesis method of N,N-diethyl isopropylamine - Google Patents
Synthesis method of N,N-diethyl isopropylamine Download PDFInfo
- Publication number
- CN102180797A CN102180797A CN2011100646871A CN201110064687A CN102180797A CN 102180797 A CN102180797 A CN 102180797A CN 2011100646871 A CN2011100646871 A CN 2011100646871A CN 201110064687 A CN201110064687 A CN 201110064687A CN 102180797 A CN102180797 A CN 102180797A
- Authority
- CN
- China
- Prior art keywords
- diethyl isopropylamine
- reaction
- diethylamine
- synthetic method
- isopropylamine
- 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
Links
Images
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of N,N-diethyl isopropylamine. The synthesis method comprises the following steps of: making diethylamine and isopropyl chloride serving as raw materials react in a high-pressure kettle in the absence of a solvent and a catalyst at the reaction temperature of 100-200 DEG C under the reaction pressure of 0.2-1.1 Mpa for 4-10 hours, wherein the molar ratio of the diethylamine to the isopropyl chloride is (2-5):1; and adding an inorganic alkaline solution into an obtained reaction product until the pH is 11.5-13.5, separating liquid and fractionating to obtain the N,N-diethyl isopropylamine. The synthesis method of N,N-diethyl isopropylamine has the characteristics of environmental friendliness, simple process, high yield and the like.
Description
Technical field
The present invention relates to a kind of synthetic method of organic compound, particularly N, the synthetic method of N – diethyl Isopropylamine.
Background technology
N, (N, N-Diethylisopropylamine), its molecular formula is C to N – diethyl Isopropylamine
7H
17N, its structural formula shown in S-1,107.5 ~ 108.0 ℃ of boiling points, the wide industrial purposes is arranged, being a kind of important fine chemical material, also is important medicine, pesticide intermediate, quaternary ammonium compound intermediate simultaneously, can be used to make medical narcotic, pesticide herbicide etc.
S-1
S-2
S-3
S-4
S-5
The comprehensive literature report, present N, N, following several method is adopted in the preparation of-diethyl Isopropylamine: 1, with nickel be catalyzer, adopt the reaction of triethyl silicane and N-ethoxymethyl Diisopropylamine to generate triethyl silicon ether, by-product N simultaneously, N,-diethyl Isopropylamine, yield is lower than 50%, and reaction formula is shown in S-2.This method Atom economy is poor, and target product yield is low, separation difficulty, and need to use than expensive catalysts, the production cost height is unsuitable for suitability for industrialized production.2, the hydrochloride of acetone and diethylamine is a reductive agent with the sodium borohydride in Virahol, reduction amination obtains N, N ,-diethyl Isopropylamine crude product, solvent is removed in distillation, use the benzene extracting impurities after adding the dilute hydrochloric acid acidifying, again through obtaining N, N, the pure product of-diethyl Isopropylamine after sodium hydroxide solution neutralization, benzene extraction and the rectifying, total recovery is 20 ~ 80%, and reaction formula is shown in S-3.3, in benzene solvent, N, N-diethylformamide and phosgene react and obtain inferior amine salt, and the Yu Geshi reagent react obtains N again, N, and-diethyl Isopropylamine, total recovery is about 80 ~ 90%, reaction formula is shown in S-4.This method has adopted hypertoxic raw material phosgene and solvent benzol, and is seriously polluted, has potential safety hazard, and simultaneously Grignard reagent instability, price are higher, are not suitable for industry and amplify.4, with glycerine be solvent, diethylamine and isopropyl bromide obtain N after carrying out atmospheric pressure reflux reaction 72h, N, and-diethyl Isopropylamine, yield is about 60%, reaction formula is shown in S-5.This method expensive raw material price, the production cost height, the use of solvent has increased the product separation difficulty, the recovery set difficulty, the while long reaction time, yield is low, and by product is many, is difficult to realize suitability for industrialized production.
Summary of the invention
The technical problem that invention will solve provides a kind of environmental friendliness, technology is simple, yield is high N, N, the synthetic method of-diethyl Isopropylamine.
In order to solve the problems of the technologies described above, the invention provides a kind of N, N, the synthetic method of-diethyl Isopropylamine: with diethylamine and isopropyl chloride is raw material, react in autoclave under solvent-free, catalyst-free condition, temperature of reaction is 100 ~ 200 ℃, and reaction pressure is 0.2 ~ 1.1Mpa, reaction times is 4 ~ 10 hours, the mol ratio 2 ~ 5:1 of diethylamine and isopropyl chloride;
In the reaction product (forming) of gained, add inorganic base aqueous solution until PH=11.5 ~ 13.5, through obtaining N, N-diethyl Isopropylamine after separatory and the rectifying by reaction solution and solid product.
As N of the present invention, the improvement of the synthetic method of N-diethyl Isopropylamine: the mass concentration of mineral alkali is 10 ~ 30% in the inorganic base aqueous solution.
As N of the present invention, the further improvement of the synthetic method of N-diethyl Isopropylamine: mineral alkali is sodium hydroxide or potassium hydroxide.
N of the present invention, N, the synthetic method of-diethyl Isopropylamine is earlier put into autoclave with diethylamine and isopropyl chloride, is heated to certain temperature then and reacts, add after the end in the alkali lye with after obtain product.Synthetic method of the present invention, its synthetic route is as follows:
N of the present invention, N, the synthetic method of-diethyl Isopropylamine has following advantage:
(1), this method carries out under solvent-free, catalyst-free condition, the reaction cleaning is polluted fewly, has reduced the pressure of wastewater treatment.
(2), this method raw material availability height, flow process is short, and is simple to operate, compares cost with other technologies and reduces greatly.
(3), these method raw material sources are extensive, cheap, the reaction conditions gentleness, the yield height, aftertreatment is simple, is applicable to suitability for industrialized production.
Description of drawings
Below in conjunction with accompanying drawing the specific embodiment of the present invention is described in further detail.
Fig. 1 is N of the present invention, the mass spectrum of N-diethyl Isopropylamine.
Embodiment
Embodiment 1, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 58.6g(0.8mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 100 ℃ for several times, and pressure is 0.2MPa.Keep finishing reaction behind this thermotonus 4h.
In the reaction product of gained, add the NaOH aqueous solution (mass concentration is 10%) until PH=13.5, tell and be positioned at upper organic phase and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 36.4g, yield are 79.2%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 2, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 58.6g(0.8mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 150 ℃ for several times, and pressure is 0.6MPa.Keep finishing reaction behind this thermotonus 6h.
In the reaction product of gained, add the KOH aqueous solution (mass concentration is 20%) until PH=13.5, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 37.4g, yield are 81.2%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 3, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 58.6g(0.8mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 140 ℃ for several times, and pressure is 0.5MPa.Keep finishing reaction behind this thermotonus 8h.
In the reaction product of gained, add the KOH aqueous solution (mass concentration is 30%) until PH=11.5, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 39.3g, yield are 85.4%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 4, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 87.9g(1.2mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 120 ℃ for several times, and pressure is 0.5MPa.Keep finishing reaction behind this thermotonus 5h.
In the reaction product of gained, add the NaOH aqueous solution (mass concentration is 20%) until PH=12.0, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 41.5g, yield are 90.2%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 5, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 87.9g(1.2mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 150 ℃ for several times, and pressure is 0.6MPa.Keep finishing reaction behind this thermotonus 8h.
In the reaction product of gained, add the KOH aqueous solution (mass concentration is 10%) until PH=13.5, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 42.1g, yield are 91.6%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 6, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 87.9g(1.2mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 180 ℃ for several times, and pressure is 0.8MPa.Keep finishing reaction behind this thermotonus 6h.
In the reaction product of gained, add the NaOH aqueous solution (mass concentration is 30%) until PH=13, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 40.2g, yield are 87.4%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 7, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 117.2g(1.6mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 120 ℃ for several times, and pressure is 0.5MPa.Keep finishing reaction behind this thermotonus 5h.
In the reaction product of gained, add the KOH aqueous solution (mass concentration is 20%) until PH=11.5, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 40.8g, yield are 88.6%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 8, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 117.2g(1.6mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 180 ℃ for several times, and pressure is 0.8MPa.Keep finishing reaction behind this thermotonus 8h.
In the reaction product of gained, add the NaOH aqueous solution (mass concentration is 10%) until PH=13, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 42.2g, yield are 91.8%, purity is 99%, and products therefrom is correct through characterizing structure.
Embodiment 9, a kind of N, N, the synthetic method of-diethyl Isopropylamine:
In the autoclave of band stirring temperature measuring equipment, add diethylamine 146.5g(2.0mol), isopropyl chloride 31.4g(0.4mol), kettle cover closes.Use N
2Leak detection and displaced air are warming up to 200 ℃ for several times, and pressure is 1.1MPa.Keep finishing reaction behind this thermotonus 10h.
In the reaction product of gained, add KOH solution (mass concentration is 30%) until PH=13.5, tell the organic phase that is positioned at the upper strata and carry out rectifying, collect 107.5 ~ 108.0 ℃ of cuts, get product N, N ,-diethyl Isopropylamine 41.3g, yield are 89.8%, purity is 99%, and products therefrom is correct through characterizing structure.
Comparative Examples 1, according to the method 4 of being informed in the above-mentioned background technology, substitute isopropyl bromide with isopropyl chloride, all the other are with this method 4, and are specific as follows:
With 78.5g isopropyl chloride, 94.9g quadrol and after 50g glycerine mixes, be heated to backflow, reaction 72h stopped reaction adds potassium hydroxide and is alkalescence until solution, tell upper oil phase, 108 ℃ of cuts are collected in rectifying, get product N, N ,-diethyl Isopropylamine 40.3g, yield are 35%.
At last, it is also to be noted that what more than enumerate only is several specific embodiments 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 (3)
1. N, the synthetic method of N-diethyl Isopropylamine, it is characterized in that: with diethylamine and isopropyl chloride is raw material, under solvent-free, catalyst-free condition, in autoclave, react, temperature of reaction is 100 ~ 200 ℃, reaction pressure is 0.2 ~ 1.1Mpa, and the reaction times is 4 ~ 10 hours, the mol ratio 2 ~ 5:1 of described diethylamine and isopropyl chloride;
In the reaction product of gained, add inorganic base aqueous solution until PH=11.5 ~ 13.5, through obtaining N, N-diethyl Isopropylamine after separatory and the rectifying.
2. N according to claim 1, the synthetic method of N-diethyl Isopropylamine is characterized in that: the mass concentration of mineral alkali is 10 ~ 30% in the described inorganic base aqueous solution.
3. N according to claim 2, the synthetic method of N-diethyl Isopropylamine is characterized in that: described mineral alkali is sodium hydroxide or potassium hydroxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100646871A CN102180797A (en) | 2011-03-17 | 2011-03-17 | Synthesis method of N,N-diethyl isopropylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100646871A CN102180797A (en) | 2011-03-17 | 2011-03-17 | Synthesis method of N,N-diethyl isopropylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102180797A true CN102180797A (en) | 2011-09-14 |
Family
ID=44567113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011100646871A Pending CN102180797A (en) | 2011-03-17 | 2011-03-17 | Synthesis method of N,N-diethyl isopropylamine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102180797A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1325842A (en) * | 2000-05-26 | 2001-12-12 | 中国石油化工集团公司 | Process for synthesizing diisopropylamine |
| US20040204611A1 (en) * | 2003-04-10 | 2004-10-14 | Peter Lappe | Process for preparing N-methyldialkylamines from secondary dialkylamines and formaldehyde |
| CN101638370A (en) * | 2009-08-18 | 2010-02-03 | 浙江大学 | Synthesizing method of N,N-diisopropyl butylamine |
| CN101759571A (en) * | 2010-01-28 | 2010-06-30 | 浙江大学 | Preparation method of N,N-diisopropylethylamine |
| CN101928222A (en) * | 2010-07-08 | 2010-12-29 | 浙江大学 | Synthesis method of N, N, N', N'-tetraisopropyl ethylene diamine |
-
2011
- 2011-03-17 CN CN2011100646871A patent/CN102180797A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1325842A (en) * | 2000-05-26 | 2001-12-12 | 中国石油化工集团公司 | Process for synthesizing diisopropylamine |
| US20040204611A1 (en) * | 2003-04-10 | 2004-10-14 | Peter Lappe | Process for preparing N-methyldialkylamines from secondary dialkylamines and formaldehyde |
| CN101638370A (en) * | 2009-08-18 | 2010-02-03 | 浙江大学 | Synthesizing method of N,N-diisopropyl butylamine |
| CN101759571A (en) * | 2010-01-28 | 2010-06-30 | 浙江大学 | Preparation method of N,N-diisopropylethylamine |
| CN101928222A (en) * | 2010-07-08 | 2010-12-29 | 浙江大学 | Synthesis method of N, N, N', N'-tetraisopropyl ethylene diamine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101759571B (en) | Preparation method of N,N-diisopropylethylamine | |
| KR101661531B1 (en) | Process for production of aromatic alcohol or heterocyclic aromatic alcohol | |
| KR101102574B1 (en) | A preparative method for 1,4-disubstituted cyclohexane derivatives | |
| CN101928222B (en) | Synthesis method of N, N, N', N'-tetraisopropyl ethylene diamine | |
| CN101811942B (en) | Synthesizing method for 1,2-dimethoxy benzene | |
| CN101260045A (en) | Mono-methylation method for amines compounds | |
| CN102076652B (en) | High-purity n-ethylmethylamine and process for preparing same | |
| CN102260175B (en) | Method for synthesizing 2-aminoethyl(ethyl)amine | |
| CN102746161A (en) | Method for synthesizing 1,8-terpene diamine | |
| CN101638370B (en) | Synthesizing method of N,N-diisopropyl butylamine | |
| CN102180797A (en) | Synthesis method of N,N-diethyl isopropylamine | |
| CN105198710B (en) | The synthetic method of one inter-species tert-butyl phenol | |
| CN103497157A (en) | 2-imidazolidone synthesis method | |
| CN102786427B (en) | Synthetic method of bis-(2-dimethylaminoethyl)ether | |
| CN102161623B (en) | Synthesis method of alkylhydroxyethylimide | |
| CN103922945B (en) | Method for synthesizing bis(2-dialkyl aminoethyl)ether | |
| CN103664654A (en) | Industrial production method of high-purity sulfuric acid terbutaline | |
| CN102531844A (en) | Preparation method of difluoroethanol | |
| CN104262160A (en) | Method for preparing 2-nitro-2-methyl-1-propanol | |
| CN104672093B (en) | A kind of preparation method of bicyclo-propyl methylamine | |
| CN104326936B (en) | The synthetic method of trans N-ethyl-N-(2 '-alkyl phenyl)-2-butylene acid amides | |
| CN103449975A (en) | Method for synthesizing m-tert-butylphenol from p-tert-butyl benzene halide | |
| CN103755575A (en) | Ether amine preparation method | |
| CN112375045B (en) | Synthetic method of piperazine | |
| CN114907219B (en) | Method for preparing monoisopropanolamine and diisopropanolamine by cracking triisopropanolamine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20110914 |
|
| RJ01 | Rejection of invention patent application after publication |