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Low pressure process for manufacture of 3-dimethylaminopropylamine (dmapa)

A technology of dimethylaminopropylamine and dimethylaminopropionitrile, applied in the field of preparing dimethylaminopropylamine

Inactive Publication Date: 2006-03-15
SOLUTIA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The methods described above would not meet stringent industrial requirements for producing this compound in synthetically acceptable yields, such as high yields >99% to a by-product-free product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]Start the caustic preparation with distilled water that has been boiled to remove dissolved carbon dioxide. About 25% by weight caustic solution was prepared in 100 g batches. Add caustic (KOH, NaOH, etc.) to degassed water (about 60 mL) with stirring. After the caustic is completely dissolved, add water to make the solution reach a total weight of 100g. Filter this solution and store in an airtight container until use to allow it to absorb CO from the air 2 least.

Embodiment 2

Embodiment 2: Hydrogenation method

[0045] One liter autoclave reactor equipped with twin turbine blades, dispersimax-type agitator, coils extending to the bottom of the reactor, transfer fluid circulation from a temperature controlled bath for temperature control, sintered stainless steel sampling valve below liquid level for hydrogen Reaction with 3-(dimethylamino)propionitrile. Add hydrogen from a steel cylinder equipped with a pressure gauge and a regulator, and add hydrogen to the reactor when the pressure drops below the set pressure. This hydrogen flows through a mass flow meter. 3-(Dimethylamino)propionitrile (Acros) was pumped into the autoclave using an Isco model 500D syringe pump. The autoclave was charged with 37.5 g of sponge nickel catalyst (Degussa MC502) and iron and chromium were added to facilitate the hydrogenation reaction (this catalyst contains about 85% nickel, 10% aluminum, 2% chromium and 2% iron). The catalyst was washed 3 times with water and 3...

Embodiment 3

Example 3: Hydrogenation of DMAPN with Sponge Nickel and Addition of Different Alkali Metal Hydroxides

[0050] A set of experiments was performed to determine the effect of adding various alkali metal hydroxides to the sponge nickel catalyst on the hydrogenation carried out in the same manner as detailed in Examples 1 and 2. In place of the 50% by weight sodium hydroxide and 50% by weight potassium hydroxide caustic solution specified in Example 2, an aqueous alkali metal hydroxide solution was used in the amounts listed in Table 2. After the number of reaction cycles listed in Table 2, samples were taken for gas chromatographic analysis. The amount of DMAPN remaining and the amount of various secondary amine by-products produced are recorded. These conditions and results are clearly listed in Table 2.

cycle

[0051] Tables 1 and 2 clearly show that high DMAPN conversions are achieved using such alkali metal hydroxides as KOH, CsOH and KOH / NaOH mixtures follo...

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PUM

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Abstract

An improved process for the production of 3-dimethylaminopropylamine in high purity from N,N-dimethylaminopropionitrile utilizing a low pressure hydrogenation process is described. The basic process comprises contacting the nitrile with hydrogen at low pressure in the presence of a catalyst under conditions sufficient to effect the conversion of the nitrile to the primary amine product.

Description

[0001] This application is a continuation-in-part of Application Serial No. 10 / 327,765 filed December 23, 2002 and claims priority from that application. technical field [0002] The present invention generally relates to the preparation of dimethylaminopropylamine (DMAPA) using dimethylaminopropionitrile (DMAPN) by hydrogenation. More particularly, the present invention relates to the preparation of dimethylaminopropylamine from dimethylaminopropionitrile with exceptional selectivity by the low pressure hydrogenation of diamines using sponge (Raney®) type catalysts and alkali metal hydroxide solutions. In particular, a process for the low pressure hydrogenation of DMAPN to DMAPA at low temperatures using a sponge nickel catalyst and a 50% / 50% by weight mixture of sodium hydroxide and potassium hydroxide is disclosed. Background technique [0003] N,N-Dimethylaminopropylamine (DMAPA, N,N-dimethyl-1,3-diaminopropane, 3-dimethylaminopropylamine) is an important intermediate fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/48
CPCC07C209/48C07C211/08
Inventor G·J·瓦德B·C·布兰查德
Owner SOLUTIA INC
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