Patents by Inventor Larry E. Moerbe
Larry E. Moerbe has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 9169197Abstract: An improved multi-reaction zone process provides improved nitrile product quality and yield. In a first reaction zone, 1,3-butadiene is reacted with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles comprising 3-pentenenitrile and 2-methyl-3-butenenitrile. In a second reaction zone, 2-methyl-3-butenenitrile, recovered from the first reaction zone, is isomerized to 3-pentenenitrile. In a third reaction zone, 3-pentenenitrile recovered from the first and second reaction zones is reacted with hydrogen cyanide in the presence of a catalyst and a Lewis acid to produce adiponitrile. Unwanted production and build-up of dinitriles, including methylglutaronitrile, in the first reaction zone for the hydrocyanation of 1,3-butadiene is prevented by limiting the flow of Lewis acid into the first reaction zone.Type: GrantFiled: June 16, 2011Date of Patent: October 27, 2015Assignee: INVISTA NORTH AMERICA S.A. R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 9133108Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. Phenolic compounds, such as phenol and cresols, are present as a catalyst impurity or as a catalyst degradation product. Phenolic compounds are removed during the nitrile manufacturing process.Type: GrantFiled: June 16, 2011Date of Patent: September 15, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 9133107Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process, which separates catalyst degradation products and reaction byproducts, such as mononitriles having 9 carbon atoms, from the catalyst.Type: GrantFiled: June 16, 2011Date of Patent: September 15, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 9051241Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The 1,3-butadiene feed includes a small amount of tertiary-butylcatechol. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process.Type: GrantFiled: June 16, 2011Date of Patent: June 9, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 9051242Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. Both reactions take place in the presence of a catalyst comprising zero valent nickel and a phosphorus-containing ligand. The ligand is partially degraded by hydrolysis or oxidation. Phosphorus-containing ligand degradation products are removed during the production of 3-pentenenitrile and adiponitrile.Type: GrantFiled: June 16, 2011Date of Patent: June 9, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 9045391Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process, which separates catalyst degradation products and reaction byproduct from the catalyst.Type: GrantFiled: June 16, 2011Date of Patent: June 2, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 9040735Abstract: The present invention relates to a process for hydrocyanating 3-pentenenitrile. The process can include feeding 3-pentenenitrile and HCN to a hydrocyanation reaction zone that includes a Lewis acid promoter, nickel, and a phosphorus-containing ligand. In various embodiments, the process can also include controlling water concentration within the hydrocyanation reaction zone sufficient to maintain a high activity of the ligand catalyst complex while recycling at least a portion of the ligand catalyst complex.Type: GrantFiled: October 4, 2012Date of Patent: May 26, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Sudhir Aki, Wyatte E. Allen, Mark Anstrom, Charles Nelson Campbell, II, Tseng Chao, James E. McIntosh, Larry E. Moerbe, Bruce Edwin Murphree, Mark D. Rogers, William J. Tenn, III, Thomas E. Vos, Michael W. Wensing
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Patent number: 9040733Abstract: An improved multi-reaction zone process provides for improved nitrile product quality and yield. In a first reaction zone, 1,3-butadiene is reacted with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles comprising 3-pentenenitrile and 2-methyl-3-butenenitrile. In a second reaction zone, 2-methyl-3-butenenitrile, recovered from the first reaction zone, is isomerized to 3-pentenenitrile. In an optional third reaction zone, 3-pentenenitrile recovered from the first and second reaction zones is reacted with hydrogen cyanide in the presence of a catalyst and a Lewis acid to produce adiponitrile. A portion of the first catalyst is purified and recycled. Zero valent nickel is added to the purified first catalyst before it is recycled.Type: GrantFiled: June 16, 2011Date of Patent: May 26, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 9040734Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. The reaction of 1,3-butadiene with hydrogen cyanide to produce 3-pentenenitrile also produces small amounts of dinitrile compounds, including adiponitrile (ADN) and methylglutaronitrile (MGN). Methylglutaronitrile is removed to provide an adiponitrile-enriched stream, which is used in a catalyst purification step.Type: GrantFiled: June 16, 2011Date of Patent: May 26, 2015Assignee: INVISTA North America S.a r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Patent number: 8937198Abstract: A hydrocyanation reaction is used to react 1,3-butadiene with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles, as well as reaction byproducts, such as methylglutaronitrile (MGN). The effluent from the hydrocyanation reaction is distilled in a particular manner to produce a pentenenitrile-enriched stream, a catalyst-enriched stream and a stream enriched in methylglutaronitrile (MGN). At least a portion of the catalyst enriched stream may be recycled to the hydrocyanation reaction. 3-pentenenitrile may be recovered and, optionally, further reacted with HCN to make adiponitrile (ADN).Type: GrantFiled: June 16, 2011Date of Patent: January 20, 2015Assignee: INVISTA North America S.a.r.l.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20140235887Abstract: The present invention relates to a process for hydrocyanating 3-pentenenitrile. The process can include feeding 3-pentenenitrile and HCN to a hydrocyanation reaction zone that includes a Lewis acid promoter, nickel, and a phosphorus-containing ligand. In various embodiments, the process can also include controlling water concentration within the hydrocyanation reaction zone sufficient to maintain a high activity of the ligand catalyst complex while recycling at least a portion of the ligand catalyst complex.Type: ApplicationFiled: October 4, 2012Publication date: August 21, 2014Applicant: INVISTA NORTH AMERICA S.A R.L.Inventors: Sudhir Aki, Wyatte E. Allen, Mark Anstrom, Charles Nelson Campbell, Tseng Chao, James E. Mcintosh, Larry E. Moerbe, Bruce Edwin Murphree, Mark D. Rogers, William J. Tenn, Thomas E. Vos, Michael W. Wensing
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Publication number: 20130267728Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. Both reactions take place in the presence of a catalyst comprising zero valent nickel and a phosphorus-containing ligand. The ligand is partially degraded by hydrolysis or oxidation. Phosphorus-containing ligand degradation products are removed during the production of 3-pentenenitrile and adiponitrile.Type: ApplicationFiled: June 16, 2011Publication date: October 10, 2013Applicant: INVISTA NORTH AMERICA S.A R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130211122Abstract: An improved multi-reaction zone process provides for improved nitrile product quality and yield. In a first reaction zone, 1,3-butadiene is reacted with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles comprising 3-pentenenitrile and 2-methyl-3-butenenitrile. In a second reaction zone, 2-methyl-3-butenenitrile, recovered from the first reaction zone, is isomerized to 3-pentenenitrile. In an optional third reaction zone, 3-pentenenitrile recovered from the first and second reaction zones is reacted with hydrogen cyanide in the presence of a catalyst and a Lewis acid to produce adiponitrile. A portion of the first catalyst is purified and recycled. Zero valent nickel is added to the purified first catalyst before it is recycled.Type: ApplicationFiled: June 16, 2011Publication date: August 15, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130211125Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The 1,3-butadiene feed includes a small amount of tertiary-butylcatechol. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process.Type: ApplicationFiled: June 16, 2011Publication date: August 15, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130211124Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. Phenolic compounds, such as phenol and cresols, are present as a catalyst impurity or as a catalyst degradation product. Phenolic compounds are removed during the nitrile manufacturing process.Type: ApplicationFiled: June 16, 2011Publication date: August 15, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130211127Abstract: An improved multi-reaction zone process provides improved nitrile product quality and yield. In a first reaction zone, 1,3-butadiene is reacted with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles comprising 3-pentenenitrile and 2-methyl-3-butenenitrile. In a second reaction zone, 2-methyl-3-butenenitrile, recovered from the first reaction zone, is isomerized to 3-pentenenitrile. In a third reaction zone, 3-pentenenitrile recovered from the first and second reaction zones is reacted with hydrogen cyanide in the presence of a catalyst and a Lewis acid to produce adiponitrile. Unwanted production and build-up of dinitriles, including methylglutaronitrile, in the first reaction zone for the hydrocyanation of 1,3-butadiene is prevented by limiting the flow of Lewis acid into the first reaction zone.Type: ApplicationFiled: June 16, 2011Publication date: August 15, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L. Three Little Falls CentreInventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130211123Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process, which separates catalyst degradation products and reaction byproducts, such as mononitriles having 9 carbon atoms, from the catalyst.Type: ApplicationFiled: June 16, 2011Publication date: August 15, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130211121Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide. The catalyst for the reaction of 1,3-butadiene with hydrogen cyanide to make 3-pentenenitrile is recycled. At least a portion of the recycled catalyst is purified by an extraction process, which separates catalyst degradation products and reaction byproduct from the catalyst.Type: ApplicationFiled: June 16, 2011Publication date: August 15, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130211126Abstract: Adiponitrile is made by reacting 3-pentenenitrile with hydrogen cyanide. The 3-pentenenitrile is made by reacting 1,3-butadiene with hydrogen cyanide and by isomerizing 2-methyl-3-butenenitrile. The reaction of 1,3-butadiene with hydrogen cyanide to produce 3-pentenenitrile also produces small amounts of dinitrile compounds, including adiponitrile (ADN) and methylglutaronitrile (MGN). Methylglutaronitrile is removed to provide an adiponitrile-enriched stream, which is used in a catalyst purification step.Type: ApplicationFiled: June 16, 2011Publication date: August 15, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: Larry E. Moerbe, Tseng H. Chao
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Publication number: 20130150610Abstract: A hydrocyanation reaction is used to react 1,3-butadiene with hydrogen cyanide in the presence of a catalyst to produce pentenenitriles, as well as reaction byproducts, such as methylglutaronitrile (MGN). The effluent from the hydrocyanation reaction is distilled in a particular manner to produce a pentenenitrile-enriched stream, a catalyst-enriched stream and a stream enriched in methylglutaronitrile (MGN). At least a portion of the catalyst enriched stream may be recycled to the hydrocyanation reaction. 3-pentenenitrile may be recovered and, optionally, further reacted with HCN to make adiponitrile (ADN).Type: ApplicationFiled: June 16, 2011Publication date: June 13, 2013Applicant: INVISTA NORTH AMERICA S.A.R.L.Inventors: Larry E. Moerbe, Tseng H. Chao