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Hydrocyanation process with reduced yield losses

By using a catalyst precursor composition of zero-valent nickel and multidentate phosphorus-containing ligands in the hydrocyanation reaction to control the reaction conditions, the adverse impact of 2-pentenenitrile on the catalyst efficiency was solved and the yield of adiponitrile was improved. efficiency and product purity, simplifying the process and reducing costs.

Active Publication Date: 2009-07-15
INVISTA TEXTILES (U K) LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when using nickel catalysts derived from monodentate phosphite ligands, such as Ni[P(OC 6 h 5 ) 3 ] 4 In the process of hydrocyanation of 3PN and 4PN, U.S. Patent 3,564,040 believes that the presence of 2PN is detrimental to catalyst efficiency even at low concentrations, and the production of 2PN is undesirable because they constitute yield loss as well as catalyst poison

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0195] Ligand "A" of Example 1 may be prepared by any suitable synthetic means known in the art. For example, 3,3'-diisopropyl-5,5',6,6'-tetramethyl-2,2'-linked Phenol, said U.S. Published Patent Application 2003 / 0100802 is incorporated herein by reference, wherein 4-methylthymol can be present in a copper chlorohydroxide-TMEDA complex (TMEDA is N, N, N', N'-tetramethylethylenediamine) and air for oxidative coupling with substituted biphenols.

[0196] For example, o-cresol chlorophosphite (C 7 h 7 O) 2 PC1, said US Published Patent Application 2004 / 0106815 is hereby incorporated by reference. For the selective formation of this chlorophosphite, anhydrous triethylamine and o-cresol can be added separately and simultaneously in a controlled manner to PCl dissolved in a suitable solvent under temperature-controlled conditions. 3 middle.

[0197] For example, according to the method disclosed in US Pat. Reaction of biphenols to form the desired ligand "A," said US Patent 6...

Embodiment 2

[0237] Use Ligand "A" and use ZnCl 2 As a Lewis acid cocatalyst, the continuous hydrocyanation process of the present invention is demonstrated.

[0238] Target reaction rate = 1.6 x 10 -4 moles of HCN / L-s

[0239] Temperature = 50°C

[0240] Mole % of 2PN feed = 20.6%

[0241] The target feed rates for the reaction components are as follows.

[0242] Reagent Feed rate, g / hr HCN a 0.29 3, 4PN (3PN+4PN) 0.94 2PN 0.25 Ni catalyst, calculated as Ni metal 0.0013 total ligand b 0.027 wxya 2 Co-catalyst 0.0020

[0243] Notes: a HCN other than PN solvents. b Mixture of ligand "A" and the corresponding monodentate phosphite as described above.

[0244] The total feed molar ratio of 2PN to all unsaturated nitriles was about 0.21, while the total feed molar ratio of HCN to all unsaturated nitriles was about 0.70.

[0245] Average GC analysis of reaction products withdrawn from 49 to 53 hours after the onset of continuous...

Embodiment 3

[0261] Using Ligand "B" shown below and using FeCl 2 As a Lewis acid cocatalyst, the continuous hydrocyanation process of the present invention is demonstrated.

[0262]

[0263] Ligand "B"

[0264] target reaction rate = 1.6 x 10 -4 moles of HCN / L-s

[0265] Temperature = 50°C

[0266] Mole % of 2PN feed = 15.4%

[0267] The target feed rates for the reaction components are as follows.

[0268] Reagent Feed rate, g / hr HCN a 0.29 3, 4PN (3PN+4PN) 0.95 2PN 0.175 Ni catalyst, calculated as Ni metal 0.0013 total ligand b 0.029 FeCl 2 Co-catalyst 0.0019

[0269] Notes: a HCN other than PN solvents. b Mixture of ligand "B" and the corresponding monodentate phosphite as described above.

[0270] The total feed molar ratio of 2PN relative to all unsaturated nitriles was about 0.15, while the total feed molar ratio of HCN relative to all unsaturated nitriles was about 0.80.

[0271] Average GC ana...

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Abstract

The invention provides a hydrocyanation process for the production of adiponitrile and other dinitriles having six carbon atoms, the process comprising: a) forming a reaction mixture in the presence of at least one Lewis acid, said reaction mixture comprising ethylenically unsaturated nitrites having five carbon atoms, hydrogen cyanide, and a catalyst precursor composition, by continuously feeding ethylenically unsaturated nitrites, hydrogen cyanide, and a catalyst precursor composition; b) controlling X and Z, wherein X is the overall feed molar ratio of 2-pentenenitriles to all unsaturated nitrites and Z is the overall feed molar ratio of hydrogen cyanide to all unsaturated nitrites, by selecting a value for X in the range from about 0.001 to about 0.5, and a value for Z in the range from about 0.5 / 1 to about 0.99 / 1, such that the value of quotient Q, Formula (I), wherein Q is in the range from about 0.2 to about 10, wherein 3PN is 3- pentenenitriles and 4PN is 4-pentenenitrile; and c) withdrawing a reaction product mixture comprising adiponitrile; wherein the ratio of the concentration of 2-pentenenitriles to the concentration of 3-pentenenitriles in the reaction mixture is from about 0.2 / 1 to about 10 / 1; wherein the catalyst precursor composition comprises a zero-valent nickel and at least one multidentate phosphorus-containing ligand; wherein the multidentate phosphorus-containing ligand is selected from the group consisting of a phosphite, a phosphonite, a phosphinite, a phosphine, and a mixed phosphorus-containing ligand or a combination of such members; and wherein the multidentate phosphorus-containing ligand gives acceptable results according to at least one protocol of the 2- Pentenenitrile Hydrocyanation Test Method.

Description

[0001] Cross References to Related Applications [0002] This application is related to commonly assigned application numbers 60 / 830,864, 60 / 830,869, 60 / 830,970, 60 / 830,865, and 60 / 830,986, filed concurrently on July 14, 2006. technical field [0003] This invention relates to the hydrocyanation of ethylenically unsaturated nitriles containing 5 carbon atoms to produce adiponitrile (ADN) and other dinitriles. More specifically, the present invention relates to the use of catalyst precursor compositions to convert 3-pentenenitrile (3PN) and / or 4-pentenenitrile (4PN) and optionally 2 - A process for the hydrocyanation of pentenenitrile (2PN), said catalyst precursor composition comprising zerovalent nickel and at least one multidentate phosphorus-containing ligand. Background technique [0004] Hydrocyanation catalyst systems have been described, especially in connection with the hydrocyanation of ethylenically unsaturated compounds. For example, it can be used for the hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/10C07C255/04
CPCC07C253/10C07C255/04
Owner INVISTA TEXTILES (U K) LTD