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Process for producing dicyanonorbornane and zerovalent-nickel complex catalyst

A technology of coordination compound and norbornane, which is applied in the field of production of dicyanonorbornane, to achieve the effect of reducing coloring over time

Active Publication Date: 2009-05-27
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, 2,5(6)-diaminomethyl-bicyclo[2,2,1]heptane (hereinafter referred to as NBDA) obtained by catalytic hydrogenation using DCN obtained by the method described in Patent Document 4 as a raw material is known. ) has a very significant property of coloring over time

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] In a 50ml glass round bottom flask equipped with a stirrer, a thermometer, a nitrogen inlet, and a condenser, 1.07g (4.5mmol) nickel chloride hexahydrate and 0.60g (9.2mmol) zinc, 8.90g (28.7mmol) ) TPP and 26.5 g (22.2 mmol) of CNN purified by a known method containing 0.2% by weight of triphenyl phosphate, and nitrogen substitution in the gas phase were reliably carried out to obtain a tetrakis (triphenyl phosphite) nickel catalyst. Then, 307.0 g (2.58 mol) of CNN, 90.0 g of toluene, and the above-mentioned obtained catalyst were synthesized in a 1 L glass flat-bottom separable flask equipped with a stirrer, a thermometer, a nitrogen inlet, a hydrogen cyanide inlet, and a condenser. The liquid was fully replaced with nitrogen in the gas phase at room temperature, and then the temperature was raised to 60°C. Then, 69.13 g (2.66 mol) of liquid hydrogen cyanide was supplied over 3.5 hours to carry out a hydrogen cyanation reaction to obtain 480.7 g of crude DCN.

[0060...

Embodiment 2

[0063] Using TPP containing 0.6 weight% of triphenyl phosphate, it tested similarly to Example 1. The above-mentioned TPP is refined by a known method. As a result, the obtained DCN was analyzed to contain 0.08% by weight of triphenylphosphate. Although the NBDA obtained by using this DCN contained 0.04% by weight of phenol, it was stored in a light-shielding container at room temperature (25 to 35°C) for 1 month, and the result of time-dependent coloring was confirmed. APHA = 10 or less, and no time-dependent coloring was observed. The experimental results are shown in Table 1.

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PUM

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Abstract

The present invention is to provide a process for producing dicyanonorbornane characterized by causing hydrogen cyanide to undergo addition reaction with cyanonorbornene (bicyclo[2.2.1]-5-heptene-2-carbonitrile) in the presence of a zerovalent nickel complex catalyst which is produced by using a phosphite represented by P (x) (y) (z) (wherein P is a phosphorus atom, and x, y and z are each OR, where R represents an aryl group having not more than 18 carbon atoms) as a ligand to reduce a nickel halide with at least one metal selected among zinc, cadmium, beryllium, aluminum, iron and cobalt, wherein the phosphite is one which has a phosphate content of 1.0 weight % or lower based on the whole phosphitem to produce the zerovalent nickel complex catalyst.

Description

technical field [0001] The present invention relates to a kind of preparation method of dicyano norbornane. In addition, the invention also relates to a zero-valent nickel coordination compound catalyst. Background technique [0002] At present, as the manufacture method that obtains dicyano norbornane (hereinafter referred to as DCN.) by the hydrocyanation of cyano norbornene (hereinafter referred to as CNN.), for example, the following methods are known: [0003] 1) A method using a cobalt carbonyl catalyst and triphenylphosphine as a catalyst system (see Patent Document 1). [0004] 2) A method using a zerovalent nickel complex catalyst and a Lewis acid as a catalyst system (see Patent Documents 2 and 3). [0005] However, the above methods 1) and 2) have low yields, use expensive catalysts, and involve purification steps for isolating coordination compounds, so there are problems of low yields and complicated operability. [0006] In view of this, a new method for the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/10B01J31/22C07C255/47C07B61/00
CPCB01J2531/847C07C209/48C07C253/10B01J31/185C07C2102/42B01J2231/32C07C2602/42C07C211/19C07C255/47B01J31/22
Inventor 深津典彦森尻博之岛川千年德永幸一小林诚一
Owner MITSUI CHEM INC
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