Hydrocyanation method for ethylenically unsaturated organic compounds

An organic compound, hydrocyanation technology, applied in the field of hydrocyanation, can solve problems such as polluting equipment

Inactive Publication Date: 2002-01-30
RHODIA POLYAMIDE INTERMEDIATES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this deposit during the operation of the method is that it contaminates the equipment and requires periodic cleaning or steps for separating and removing the deposit

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0139] Embodiment 11) prepare Ni / TSTPP catalytic solution

[0140] will be 500cm 3 350 mmol of an aqueous solution of trisulfonated triphenylphosphine (TSTPP) sodium salt was added to a 1 liter round bottom glass flask equipped with a magnetic stir bar and an upward reflux condenser; the solution was degassed. Subsequently, under stirring and under argon flow, 21.40 g (78 mmol) of Ni(cyclooctadiene) were added 2 , then add 350cm 3 Pre-degassed o-xylene.

[0141] The mixture was heated at 45°C for 15 hours. After cooling, the two-phase system was separated by settling and the dark red aqueous phase was discharged. Through analysis and determination, its nickel content is 134mmol / kg. 2) Isomerization of 2-methyl-3-butenenitrile

[0142] The following ingredients were added to a 2 liter glass reactor flushed with hydrogen and stirred by a turbine:

[0143] 2-Methyl-3-butenenitrile (2M3BN): 770g (9.50mol)

[0144] - Catalytic solution: 250cm 3 (39.5mmol Ni and 175.5mmol T...

Embodiment 2

[0153] will be 35cm 3 As in Example 1, the aqueous suspension described in §2 was added to 150 cm 3 In a glass reactor flushed with argon and equipped with an automatic suction turbine. While stirring (1200 rpm) at 50°C, 0.265 ml of hydrocyanic acid was injected into the reactor head space at a constant flow rate for 1 hour via a syringe thermostated at -10°C. After injecting HCN and returning to room temperature, the mixture was kept stirring in a closed vessel for 1 hour, then the headspace of the reactor was flushed with a flow of argon for about 1 hour. Through such treatment, a homogeneous aqueous solution is obtained: the solution has no obvious sediment after standing. For Millipore Millex-HV  The sample that filter (Hydrophilic PVDF, 0.45 μ m) leaches adopts elemental analysis and polarization analysis to carry out quantitative measurement of total nickel and nickel (II) respectively, obtains following result: [Ni]=129mmol / kg and [Ni(II) )]=38mmol / kg([Ni 0 ]=91mm...

Embodiment 3

[0155] will be 35cm 3 As in Example 1, the aqueous suspension described in §2 was added to 150 cm 3 In a glass reactor flushed with argon and equipped with an automatic suction turbine. While stirring (1200 rpm) at 70°C, 0.265 ml of hydrocyanic acid was injected at a constant flow rate into the reactor headspace for 1 hour via a syringe thermostated at -10°C. After injecting HCN, returning to room temperature, the mixture was kept stirring in a closed vessel for 1 hour, and then, the headspace of the reactor was flushed with a flow of argon for about 1 hour. Through such treatment, a homogeneous aqueous solution is obtained: the solution has no obvious sediment after standing. For Millipore Millex-HV  The sample that filter (Hydrophilic PVDF, 0.45 μm) leaches adopts elemental analysis and polarization analysis to carry out quantitative measurement of total nickel and nickel (II) respectively, obtains following result: [Ni]=122mmol / kg and [Ni(II) )]=30mmol / kg([Ni 0 ]=92mm...

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PUM

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Abstract

The invention concerns a hydrocyanation method for ethylenically unsaturated organic compounds in particular to obtain nitriles, and more particularly hydrocyanation of substituted diolefins or of olefins for producing dinitriles, and/or the isomerization of nitriles obtained by hydrocyanation. The invention more particularly concerns hydrocyanation catalysed by a nickel-based compound. Thus the catalyst used in said production method is treated in output with hydrogen cyanide to recover and re-dissolve the nickel precipitated in the form of nickel hydroxide. The method enables to regenerate and prolong the life span of a catalyst charge. Moreover, it enables to reduce pollution in the installations using said method.

Description

technical field [0001] The present invention relates to a process for the hydrocyanation of ethylenically unsaturated organic compounds, especially for the preparation of nitriles, more particularly, the present invention relates to a process for the hydrocyanation of dienes or substituted alkenes for the production of dinitriles and / or by Process for the isomerization of nitriles obtained during hydrocyanation. [0002] More specifically, the present invention relates to processes for hydrocyanation catalyzed by nickel-based compounds. Background technique [0003] French Patent 1,599,761 discloses a process for the preparation of nitriles by adding hydrocyanic acid to an organic compound having at least one olefinic double bond in the presence of a nickel catalyst and a triaryl phosphite. The reaction can be carried out with or without the presence of a solvent. [0004] When solvents are used in the prior art processes, hydrocarbons such as benzene or xylene, or nitrile...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/28B01J31/24B01J31/40C07B61/00C07C253/10C07C253/30C07C255/03C07C255/07C07C255/12
CPCB01J2231/52B01J2531/847C07C253/10C07C253/30B01J31/2404B01J31/403B01J31/24B01J2531/96B01J31/4053B01J2231/343Y02P20/584C07C255/07
Inventor P·布拉廷P·克库瑞特M·赫瑟尔
Owner RHODIA POLYAMIDE INTERMEDIATES
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