Invista North America S.a.r.l.

E.i. Dupont De Nemours and Company

John Joseph Ostermaier

Gregory S Kirby

Sourav Kumar Sengupta

Alan Martin Allgeier

Bruce Edwin Murphree

Vinay Medhekar

Leon S Scott

Colin S Slaten

Richard P Beatty

Thomas A Micka

Keith Whiston

Joan Fraga-Dubreuil

Willie Jon Barnette

James Bernard Sieja

George Crumbaugh Russell, Iii

Michael C Quinn, Iii

Michael L Bourgeois

James Hastings

As described herein, nickel treated with sulfur provides a surprisingly effective source of nickel atoms for generating nickel-phosphorus-containing ligand complexes useful as hydrocyanation catalysts.

Metal-ligand catalyst formation

Nickel-metal-containing solids for use in manufacturing nickel metal complexes are disclosed. The nickel-metal-containing solids are made by reducing basic nickel carbonates. By varying the molar ratios of carbonates and bicarbonates to nickel salts, the methods provide basic nickel carbonates that produce superior nickel metal-containing solids that react more effectively with phosphorous-containing ligands. The phosphorous containing ligands can be both monodentate and bidentate phosphorous-containing ligands.

Nickel metal compositions and nickel complexes derived from basic nickel carbonates

The present invention relates to a method of preparing a nickel complex including nickel and at least one phosphorus-containing ligand by reacting at least a portion of a nickel metal with at least one phosphorus-containing ligand. The nickel metal is prepared from a nickel composition including nickel(II).

Preparing a nickel phosphorus ligand complex

Nickel(II) compositions for use in manufacturing nickel metal (Ni(0)) compositions, and specifically to methods of making basic nickel carbonates used to produce nickel metal compositions are disclosed. By varying the molar ratios of carbonates and bicarbonates to nickel salts, the methods provide basic nickel carbonates that produce superior nickel metal-containing solids that are well-suited to forming nickel-ligand complexes with phosphorus-containing ligands. The phosphorus-containing ligands can be monodentate or bidentate phosphorus-containing ligands.

Nickel compositions for preparing nickel metal and nickel complexes

These disclosures relate to preparing nickel metal (Ni(0)) suited for use in catalyst systems, such as nickel complexes with phosphorus-containing ligands, useful to catalyze the hydrocyanation of ethylenically unsaturated compounds. The methods described herein can include use of steam during reduction of nickel.

Calcination and reduction process including a fluidizing bed reactor

Nickel compositions for use in manufacturing nickel metal compositions, and specifically to methods of making basic nickel carbonates used to produce nickel metal compositions are disclosed. By varying the molar ratios of carbonates and bicarbonates to nickel salts, the methods provide basic nickel carbonates that produce superior nickel-containing solids that react more effectively with phosphorous-containing ligands. The phosphorous containing ligands can be both monodentate and bidentate phosphorous-containing ligands.

A process and apparatus for reacting deleterious impurities contained in adiponitrile (ADN) comprises feeding ADN and an ozone containing gas into a co-current plug flow reactor containing static mixer elements, to oxidize at least a portion of the impurities, thereby producing a reactor discharge, which is processed to produce an ozone-treated ADN product.

Process for improving adiponitrile quality

A process for improving the recovery of solid triphenylboron-pyridine compound (TPBP), while retaining desirable particle characteristics comprises the addition of an acid to neutralize at least a portion of the alkali contained in the aqueous mother liquor. By adjusting the pH of the product slurry to between about 8.5 and about 12, it is possible to increase product recovery by more than 10%, while maintaining desirable particle characteristics.

Process for making triphenylboron-pyridine compound

A process for producing solid triphenylboron-pyridine (TPBP) spherical particles by separately feeding into a vigorously agitated reaction zone (i) a stream of pyridine and a (ii) stream comprising a solution of sodium hydroxide adduct of triphenylboron (TPBA) whereby the total concentration of TPBA in the combined feed streams is in the range of from 1 wt % to 6 wt %, and simultaneously removing a product stream from said reaction zone and recovering the triphenylboron-pyridine (TPBP) particles.

Process for making solid triphenylboron-pyridine or its adduct

The invention relates to the field of separation by distillation of 6-aminocapronitrile (ACN) and hexamethylenediamine (HMD) from a mixture containing ACN, HMD, tetrahydrozaepine (THA), adiponitrile (ADN) and low boilers (LB). A method for producing a distillate stream comprising HMD is disclosed, which is suitable for the production of Nylon-6,6. The tails stream from the distillation of the mixture can be further distilled to produce a distillate containing ACN and THA, which is particularly suitable for use in the production of caprolactam and Nylon-6 from the caprolactam. Process conditions of the method of the invention disfavor the production of 2-cyanocyclopentylideneirnine (CPI).

Separation of 6-aminocapronitrile and hexamethylenediamine from a mixture comprising hexamethylenediamine, 6-aminocapronitrile and tetrahydroazepine

The invention relates to the field of production of lactams from aminonitriles, and in particular to the production of &#x3b5;-caprolactam by the vapor phase hydrolytic cyclization of 6-aminocapronitrile. A crude liquid caprolactam comprising &#x3b5;-caprolactam (CL), 6-aminocapronitrile (ACN) and water obtained from a vapor phase cyclization reaction of ACN is contacted with hydrogen in the presence of a hydrogenation catalyst to convert the ACN in the crude liquid caprolactam to a product comprising hexamethylenediamine (HMD) and hexamethyleneimine (HMI). Tetrahydroazepine (THA) in the crude liquid caprolactam is converted to HMI during this hydrogenation. The HMD and HMI have lower boiling points compared to ACN and thus they are more easily separated from CL in the subsequent distillation operations. Thus a process to make CL from ACN with fewer distillation stages, and with lower pressure drop and lower base temperature, is accomplished.

Method for making caprolactam from impure 6-aminocapronitrile

The invention relates to the field of separation by distillation of 6-aminocapronitrile (ACN) and hexamethylenediamine (HMD) from a mixture comprising ACN, HMD, tetrahydroazepine (THA), adiponitrile (ADN) and low boilers (LB). Also disclosed is a method for producing a distillate stream comprising HMD; a side draw stream comprising ACN, THA and low levels of dimers of ACN and HMD; and a tails stream comprising ACN, THA and substantially higher levels of dimers of ACN and HMD than found in the side draw stream. The side draw stream is particularly suitable for use in the production of caprolactam since the low levels of dimers of ACN and HMD do not greatly affect the catalyst life in the caprolactam production process. The tails stream can be further distilled to produce a tails distillate stream comprising ACN and THA, which can be recycled back to the first distillation column, further increasing recovery of ACN from the feed stream. Process conditions of the method of the invention disfavor the production of 2-cyanocyclopentylideneimine (CPI).

Lactams, in particular &#x3b5;-caprolactam, are produced by the hydrolytic cyclization of aminonitriles, in particular 6-aminocapronitrile, in the vapor phase in a plurality of adiabatic fixed bed reaction zones arranged in succession wherein at least a portion of the heat of the exothermic reaction is removed between each of the successive reaction zones. Conducting the reaction in such a manner requires less capital for the reactor itself. It has also been found that the product exiting such a reaction system can be directly fed to a distillation unit without the need of additional cooling or storing.

Process for making caprolactam

Process for making both ACN and HMD from partial hydrogenation of ADN by using a combination of distillations resulting in the formation of a mixture of HMD and THA that can be hydrogenated to produce a mixture of HMD and HMI that can be separated easily by simple distillation.

Process for producing hexamethylenediamine and aminocapronitrile from adiponitrile, wherein the hexamethylenediamine contains less than 100 ppm tetrahydroazepine

A method for recovering hexamethylene diamine (HMD) from a mixture comprising HMD, 6-aminocapronitrile (ACN) tetrahydroazepine (THA), and adiponitrile (ADN) is disclosed. The method includes introducing the mixture into a first distillation column, separating as a group the HMD, ACN and at least a portion of the THA as distillate from the ADN. The first distillation column is operated at a temperature and pressure to minimize isomerization of the ADN into 2-cyanocyclopentylideneimine(CPI). The distillate of the first distillation column is introduced into a subsequent distillation column and the HMD is separated from the ACN and THA.

Growing community of inventors

Orange, TX, United States of America

John Joseph Ostermaier