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Separating a solvent from a nickel catalyst by distillation

一种催化剂、蒸发溶剂的技术，应用在催化剂至少部分分离领域，能够解决催化剂毒物、产率损失、不利催化剂效率等问题

Active Publication Date: 2016-04-27
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 hydrocyanating 3PN and 4PN, U.S. Patent No. 3,564,040 pointed out that the presence of 2PN, even at low concentrations, is not conducive to catalyst efficiency and the production of 2PN is undesirable because of the presence of 2PN and produces yield losses as well as catalyst poisons

Method used

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  • Separating a solvent from a nickel catalyst by distillation
  • Separating a solvent from a nickel catalyst by distillation
  • Separating a solvent from a nickel catalyst by distillation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0379] Example 1: Use of cis-2-pentenenitrile in simulated distillation.

[0380] Four reaction mixtures of pentenenitrile and hydrocyanation catalyst were prepared to simulate the composition of the distillation column bottoms in the distillation column used to separate the extraction solvent from the catalyst extracted into the solvent. The catalyst is a complex of zerovalent nickel with a bidentate phosphite ligand of the formula:

[0381]

[0382] Each reaction mixture included approximately 51 wt. % trans-3-pentenenitrile, 0.4 wt. % 2-methyl-3-butenenitrile, and 575 ppm nickel. The weight ratio of nickel to bidentate phosphite ligand is 0.017.

[0383] Various amounts of cis-2-pentenenitrile were included in each reaction mixture. The first reaction mixture included an amount of cis-2-pentenenitrile such that the ratio of trans-3-pentenenitrile to cis-2-pentenenitrile (T3PN / C2PN) was 3. The second reaction mixture included an amount of cis-2-pentenenitrile such that...

Embodiment 2

[0386] Example 2: Use of trans-2-pentenenitrile in simulated distillation.

[0387] Example 1 was repeated except that trans-2-pentenenitrile was substituted for cis-2-pentenenitrile and at least some of the ratio of trans-3-pentenenitrile to 2-pentenenitrile was changed . Specifically, the first reaction mixture included an amount of trans-2-pentenenitrile such that the ratio of trans-3-pentenenitrile to trans-2-pentenenitrile (T3PN / T2PN) was 2.6. The second reaction mixture included an amount of trans-2-pentenenitrile such that the ratio of trans-3-pentenenitrile to trans-2-pentenenitrile (T3PN / T2PN) was 4.5. The third reaction mixture included an amount of trans-2-pentenenitrile such that the ratio of trans-3-pentenenitrile to trans-2-pentenenitrile (T3PN / T2PN) was 7. The fourth reaction mixture included an amount of trans-2-pentenenitrile such that the ratio of trans-3-pentenenitrile to trans-2-pentenenitrile (T3PN / T2PN) was 15.

[0388] As in the procedure of Example 1...

Embodiment 4

[0394] Example 4: Inhibition of the formation of 2M3BN in a distillation column.

[0395] This example demonstrates the suppression of 2M3BN formation in a distillation column during the continuous production of adiponitrile.

[0396] Hydrogen cyanide, 3-pentenenitrile, and a catalyst solution are continuously fed into the hydrocyanation reactor to continuously produce adiponitrile. The catalyst solution contained zerovalent nickel and a bidentate phosphite ligand of the formula shown in Example 1 . The reaction product effluent from the hydrocyanation reactor was then extracted with cyclohexane to form a light phase and a heavy phase. The light phase contained cyclohexane, catalyst and a portion of residual pentenenitriles. The heavy phase contains adiponitrile, a portion of residual pentenenitriles, and catalyst degradation products.

[0397] The light phase is continuously distilled in a distillation column including a reboiler. The fluid in the reboiler containing cata...

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Abstract

A solvent is at least partially separated from a catalyst. The catalyst comprises nickel and a bidentate phosphorus-containing ligand. The method for separation involves distilling a catalyst solution. The ratio of 2-pentenenitrile to 3-pentenenitrile in distillation column bottoms is controlled to reduce the amount of 3-pentenenitrile which is isomerized to form 2-methyl-3-butenenitrile. Isomerization of 3-pentenenitrile to 2-methyl-3-butenenitrile, and subsequent isomerization of 2-methyl-3-butenenitrile to 2-methyl-2-butenenitrile, and / or hydrocyanation of 2-methyl-3-butenenitrile to methylglutaronitrile represents a loss in adiponitrile yield in a process for making adiponitrile.

Description

technical field [0001] The present invention relates to a process for at least partial separation of solvent from catalysts comprising nickel and bidentate phosphorus-containing ligands by distillation. Background technique [0002] Adiponitrile (ADN) is a commercially important and versatile intermediate in the industrial production of nylon polyamides useful for forming films, fibers, and molded articles. ADN can be produced by hydrocyanation of 1,3-butadiene (BD) in the presence of transition metal complexes containing various phosphorus-containing ligands. For example, catalysts comprising zerovalent nickel and monodentate phosphorus-containing ligands are well documented in the prior art; see, eg, U.S. Pat. Nos. 3,496,215; 3,631,191; 3,655,723; and 3,766,237; , C.A., McKinney, R.J., Seidel, W.C., Druliner, J.D. and Stevens, W.R., Advances in Catalysis, 1985, p. 33 Vol., pp. 1-46. Also disclosed are improvements in the hydrocyanation of ethylenically unsaturated compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/07C07C253/34
CPCB01J38/02C07C253/10C07C253/34C07C255/04C07C255/07B01D3/143B01J31/185
Inventor 苏迪尔·N·V·K·阿基詹姆斯·迈克尔·加纳威廉·J·滕托马斯·E·沃斯
Owner INVISTA TEXTILES (U K) LTD
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