CN101328129B - Preparation of 3-methoxy propanamine - Google Patents
Preparation of 3-methoxy propanamine Download PDFInfo
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- CN101328129B CN101328129B CN2008101201483A CN200810120148A CN101328129B CN 101328129 B CN101328129 B CN 101328129B CN 2008101201483 A CN2008101201483 A CN 2008101201483A CN 200810120148 A CN200810120148 A CN 200810120148A CN 101328129 B CN101328129 B CN 101328129B
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Abstract
The invention discloses a method for synthesizing a chemical intermediate, in particular to a method for preparing 3-methoxy propylamine by taking 3-methoxy propanol as a raw material. The method takes the 3-methoxy propanol as the raw material and takes Cu-Co/Al2O3-diatomite as a catalyst. At certain pressure and certain temperature, the 3-methoxy propanol is driven into a preheater and is mixed with ammonia gas and hydrogen; the mixture is preheated and vaporized and enters a fixed-bed reactor for reaction, the material after reaction is subjected to condensation and cooling, the gas and the liquid are separated, the 3-methoxy propylamine as the product is produced, and the system materials can be recycled. The method has the advantages of simple technique process, high rate of conversion, good selectivity, a few side products, simple and concise separating flow, low energy and raw material consumption and low production cost of the product.
Description
Technical field
The present invention relates to a kind of chemical synthesis process of pesticide intermediate, especially a kind of is the preparation method of the 3 methoxypropyl amine of raw material with the 3-methoxypropanol.
Background technology
3 methoxypropyl amine is a kind of pesticide herbicide midbody and pharmaceutical-chemical intermediate, purposes: medicine intermediate, and dyestuff intermediate, oil is anticorrosion, clean-out system etc.Molecular formula: C
4H
11NO, molecular weight are 89.14, English name: 3-Metho * ypropylamine.Its physical property is: density, 0.873; Fusing point ,-65 ℃; Boiling point, 117-118 ℃; Specific refractory power, 1.4165-1.4185; Flash-point, 48 ℃.As the midbody of a kind of novel agrochemical, medicine, its production also is in the starting stage, and the preparation method also is in and gropes the development phase.
Summary of the invention
To the deficiency in the present production technology of 3 methoxypropyl amine, it is high that the present invention proposes a kind of transformation efficiency, and selectivity is good, and by product is few, and flow process is simple, and production cost is low, is fit to the preparation method of industrial 3 methoxypropyl amine.
The present invention is achieved through following technical proposals:
A kind of preparation method of 3 methoxypropyl amine is characterized in that comprising the steps:
(1) is raw material with the 3-methoxypropanol, and pumps into preheater to the 3-methoxypropanol, with ammonia, hydrogen mixing preheating vaporization;
(2) preheating vaporization back gets into reactor drum, with Cu-Co/Al
2O
3-zeyssatite is catalyzer, and control pressure is normal pressure～5.0Mpa, and temperature is 50～360 ℃, and pure liquid hourly space velocity is 0.1～3.0h
-1, ammonia alcohol mol ratio is 1.0～15.0: 1, and hydrogen alcohol mol ratio is 0.1～10.0: 1, and catalyst levels is 0.05～3.0m
3Alcohol/(hrm
3Catalyzer) reacts under the condition;
Wherein, the composition of catalyzer (weight ratio) is: Cu is 0.1～50.0%, and Co is 0.5～60.0%, and Ru is 0.001～0.1%, and Mg is 0.001～5.7%, and Cr is 0.01～15.0%, and all the other are Al
2O
3With one of diatomaceous mixture or both;
3) reacting rear material is through condensation cooling, gas-liquid separation, and gas phase gets into the reactor cycles utilization through circulation;
Liquid phase gets into rectifying tower and separates the purification 3 methoxypropyl amine, can get product; The ammonia of separating, 3-methoxypropanol turn back to feed system, get into reactor drum again, react with hydrogen, ammonia and the 3-methoxypropanol of replenishing entering.
As preferably, the Cu-Co/Al described in the preparation method of above-mentioned a kind of 3 methoxypropyl amine
2O
3The composition of-zeyssatite catalyzer (weight ratio) is: Cu is 5.0～25.0%, and Co is 5.0～30.0%, and Ru is 0.01～0.3%, and Mg is 0.05～1.0%, and Cr is 0.1～5.0%, and all the other are Al
2O
3With one of diatomaceous mixture or both.
As preferably, the operation condition described in the preparation method of above-mentioned a kind of 3 methoxypropyl amine is: pressure: 0.3～1.5Mpa, and temperature: 120～220 ℃, pure liquid hourly space velocity: 0.5～2.0h
-1, ammonia alcohol mol ratio: 4.0～10.0: 1, hydrogen alcohol mol ratio: 0.5～5.0: 1, catalyst levels: 0.4～2.0m
3Alcohol/(hrm
3Catalyzer).
As preferably, the preparation procedures system described in the preparation method of above-mentioned a kind of 3 methoxypropyl amine is carried out closed cycle, material recycle.
The technical solution adopted for the present invention to solve the technical problems.The preparation method of this 3 methoxypropyl amine is a raw material with the 3-methoxypropanol, at Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer; Fixed-bed reactor are adopted in this reaction, carry out in vapour phase, adopt the continous way process.The 3-methoxypropanol by volume pump squeeze into preheater and with ammonia, hydrogen mixing preheating after vaporization back get into the fixed-bed reactor reaction, reacting rear material is through condensation cooling, gas-liquid separation; Gas phase is utilized through the recycle compressor compression cycle, and liquid phase gets into rectifying tower and separates purification: 3 methoxypropyl amine is as the product extraction; Ammonia, 3-methoxypropanol turn back to feed system, and replenish a certain amount of hydrogen, ammonia and 3-methoxypropanol, to keep the mol ratio of above-mentioned ammonia, hydrogen, isooctyl alcohol; Minor by-products two-(3-methoxy-propyl) amine (abbreviation diamines) or through the back of purifying as by-product sale or return synthetic feed system circulation and continue generation in order to suppress by product; Waste water purifies to the emission standard discharging.
The effect that the present invention is useful is: with the 3-methoxypropanol is the synthetic 3 methoxypropyl amine of raw material continuous catalysis ammonification dehydration.Present method technical process is simple, and transformation efficiency is high, and selectivity is good, and by product is few, and separation process is simple and clear, and energy consumption, raw material consumption are low, and the products production cost is low.
Embodiment
Below in conjunction with embodiment the present invention is further described.
Embodiment 1: this 3 methoxypropyl amine (C
4H
11NO) preparation method:
At first prepare catalyzer:
Industrial Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer, is numbered Al, and the composition of catalyzer (weight ratio) is: Cu is 0.5%, and Co is 20.0%, and Ru is 0.05%, and Mg is 0.07%, and Cr is 0.5%, and all the other are Al
2O
3Respectively account for 50% mixture with zeyssatite.
Industrial Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer, is numbered A2, and the composition of catalyzer (weight ratio) is: Cu is 3.0%, and Co is 1.0%, and Ru is 0.05%, and Mg is 0.1%, and Cr is 2.0%, and all the other are Al
2O
3Respectively account for 50% mixture with zeyssatite.
Industrial Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer, is numbered A3, and the composition of catalyzer (weight ratio) is: Cu is 15.0%, and Co is 10.0%, and Ru is 0.1%, and Mg is 1.0%, and Cr is 2.0%, and all the other are Al
2O
3Account for 30% with zeyssatite account for 70% mixture.
Industrial Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer, is numbered A4, and the composition of catalyzer (weight ratio) is: Cu is 25.0%, and Co is 40.0%, and Ru is 0.01%, and Mg is 3.0%, and Cr is 5.0%, and all the other are Al
2O
3Account for 20% with zeyssatite account for 80% mixture.
Industrial Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer, is numbered A5, and the composition of catalyzer (weight ratio) is: Cu is 40.0%, and Co is 30.0%, and Ru is 0.1%, and Mg is 4.0%, and Cr is 10.0%, and all the other are Al
2O
3Account for 60% with zeyssatite account for 40% mixture.
Industrial Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer, is numbered A6, and the composition of catalyzer (weight ratio) is: Cu is 5.0%, and Co is 25.0%, and Ru is 0.03%, and Mg is 5.0%, and Cr is 4.0%, and all the other are Al
2O
3Respectively account for 50% mixture with zeyssatite.
Industrial Cu-Co/Al
2O
3-zeyssatite catalyzer is a catalyzer, is numbered A7, and the composition of catalyzer (weight ratio) is: Cu is 35.0%, and Co is 5.0%, and Ru is 0.05%, and Mg is 5.0%, and Cr is 4.0%, and all the other are Al
2O
3Respectively account for 50% mixture with zeyssatite.
1) be raw material with the 3-methoxypropanol,, with the industrial Cu-Co/Al of the said preparation of patent ZL200310122670.2
2O
3-zeyssatite catalyzer is a catalyzer.
2), this is reflected at vapour phase and carries out, and adopts the continous way process, its concrete operations condition is pressure: 0.9Mpa, temperature: 150 ℃, pure liquid hourly space velocity: 0.5h
-1, ammonia alcohol mol ratio: 8.0, hydrogen alcohol mol ratio: 1.5.
3), the 3-methoxypropanol by volume pump squeeze into preheater and with ammonia, hydrogen mixing preheating after vaporization back get into the fixed-bed reactor reaction, reacting rear material is through condensation cooling, gas-liquid separation; Gas phase is utilized through the recycle compressor compression cycle, and liquid phase gets into rectifying tower and separates purification: 3 methoxypropyl amine is as the product extraction; Ammonia, 3-methoxypropanol turn back to feed system, and replenish a certain amount of hydrogen, ammonia and 3-methoxypropanol, to keep the mol ratio of above-mentioned ammonia, hydrogen, 3-methoxypropanol; Minor by-products two-(3-methoxy-propyl) amine (abbreviation diamines) or through the back of purifying as by-product sale or return synthetic feed system circulation and continue generation in order to suppress by product; Waste water purifies to the emission standard discharging.
Embodiment 2---embodiment 9: with the diameter of packing into of catalyzer among the embodiment 1 is 32 * 3.5mm, the stainless steel reactor of length 1500mm.The stainless steel temperature-measuring casing of ∮ 8 * 1mm is set in the reactor drum, and catalyst packing height is 880mm, and loaded catalyst is 585ml.Reaction raw materials is to go out under enterprising, gets into the separator vapor phase ammonia, hydrogen discharge from the separator top, bottom liquid phases timing sampling through condensation cooling back from the effusive material of reactor bottom.Form with gas chromatographic analysis, concrete reaction conditions and result are listed in the table below.
Reaction conditions and result
Can know by data in the last table, under present inventor's processing condition, react that the result all has higher transformation efficiency and selectivity preferably.
Embodiment 11 ... Embodiment 15: according to example 2～10 said devices, flow process and catalyzer, the loadings of catalyzer is that 585ml carries out 240 hours stable service tests.Reaction pressure: 0.9MPa, temperature: 180 ℃, pure liquid hourly space velocity: 0.5h
-1, ammonia alcohol mol ratio: 8.0, hydrogen alcohol mol ratio: 1.5.Form with liquid-phase chromatographic analysis, concrete reaction conditions and result are listed in the table below.
240 hours stable service tests
Can be known that by last table data under these processing condition, the transformation efficiency of reaction is higher than 70%, selectivity is higher than 80%, and catalyzer has stability preferably simultaneously.
Claims (4)
1. the preparation method of a 3 methoxypropyl amine is characterized in that comprising the steps:
(1) is raw material with the 3-methoxypropanol, and pumps into preheater to the 3-methoxypropanol, with ammonia, hydrogen mixing preheating vaporization;
(2) preheating vaporization back gets into reactor drum, with Cu-Co/Al
2O
3-zeyssatite is catalyzer, and control pressure is normal pressure～5.0Mpa, and temperature is 50～360 ℃, and pure liquid hourly space velocity is 0.1～3.0h
-1, ammonia alcohol mol ratio is 1.0～15.0: 1, and hydrogen alcohol mol ratio is 0.1～10.0: 1, and catalyst levels is 0.05～3.0m
3Alcohol/hrm
3React under the condition of catalyzer;
Wherein, consisting of of catalyzer: Cu is 0.1～50.0%, and Co is 0.5～60.0%, and Ru is 0.001～0.1%, and Mg is 0.001～5.7%, and Cr is 0.01～15.0%, and all the other are Al
2O
3With one of diatomaceous mixture or both, aforementioned proportion is a weight ratio;
3) reacting rear material is through condensation cooling, gas-liquid separation, and gas phase gets into the reactor cycles utilization through circulation;
Liquid phase gets into rectifying tower and separates the purification 3 methoxypropyl amine, can get product; The ammonia of separating, 3-methoxypropanol turn back to feed system, get into reactor drum again, react with hydrogen, ammonia and the 3-methoxypropanol of replenishing entering.
2. the preparation method of a kind of 3 methoxypropyl amine according to claim 1 is characterized in that: described Cu-Co/Al
2O
3Consisting of of-zeyssatite catalyzer: Cu is 5.0～25.0%, and Co is 5.0～30.0%, and Ru is 0.01～0.3%, and Mg is 0.05～1.0%, and Cr is 0.1～5.0%, and all the other are Al
2O
3With one of diatomaceous mixture or both, aforementioned proportion is a weight ratio.
3. the preparation method of a kind of 3 methoxypropyl amine according to claim 1, it is characterized in that: described operation condition is: pressure: 0.3～1.5Mpa, temperature: 120～220 ℃, pure liquid hourly space velocity: 0.5～2.0h
-1, ammonia alcohol mol ratio: 4.0～10.0: 1, hydrogen alcohol mol ratio: 0.5～5.0: 1, catalyst levels: 0.4～2.0m
3Alcohol/hrm
3Catalyzer.
4. the preparation method of a kind of 3 methoxypropyl amine according to claim 1 is characterized in that: described preparation procedures system implementation closed cycle, material recycle.
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| CN109678734B (en) * | 2018-12-27 | 2021-12-21 | 浙江工业大学 | Method for preparing 2-methoxy ethylamine by directly catalyzing and aminating ethylene glycol monomethyl ether |
| CN109761819B (en) * | 2019-01-23 | 2021-12-21 | 浙江新化化工股份有限公司 | Continuous preparation method of N, N-dimethylpropylamine |
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Non-Patent Citations (4)
| Title |
|---|
| .《2-乙基己醇氨化脱水合成2-乙基己胺工艺研究》.《化学反应工程与工艺》.2004,第20卷(第2期),157－160页. |
| 兰昭洪 |
| 胡健 |
| 胡健;兰昭洪;.《2-乙基己醇氨化脱水合成2-乙基己胺工艺研究》.《化学反应工程与工艺》.2004,第20卷(第2期),157-160页. * |
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