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公开(公告)号:US09296768B2
公开(公告)日:2016-03-29
申请号:US14404037
申请日:2013-05-24
Applicant: INVISTA NORTH AMERICA S.A.R.L.
Inventor: William J. Tenn, III
IPC: C07F15/00 , C07F9/40 , C07F15/04 , C07F9/6574 , C07F9/145 , B01J31/18 , B01J31/22 , C07C253/10
CPC classification number: C07F9/06 , B01J31/185 , B01J31/2221 , B01J2231/322 , B01J2231/70 , B01J2531/847 , C07C253/10 , C07C253/30 , C07F9/145 , C07F9/4006 , C07F9/65744 , C07F15/04
Abstract: The invention provides a method of forming a phosphonate diester compound from a ligand hydrolysis product (LHP) of a phosphite ligand used in a nickel-phosphite hydrocyanation catalyst, such as for conversion of 3-pentenenitrile to adiponitrile, which serves to eliminate acidic LHP compound for a hydrocyanation reaction milieu where the acidic LHP can catalyze further catalyst ligand destruction. The invention further provides phosphonate disester compounds prepared by alkylation of diarylphosphite LHP in the presence of a nickel-phosphite catalyst comprising a bidentate ligand, and a continuous hydrocyanation process for production of adiponitrile wherein catalyst ligand breakdown is inhibited through inactivation of ligand hydrolysis products towards further breakdown. A method of stabilizing a hydrocyanation catalyst is provided.
Abstract translation: 本发明提供了一种由亚磷酸氢氰化催化剂中使用的亚磷酸酯配位体的配体水解产物(LHP)形成膦酸二酯化合物的方法,例如用于将3-戊烯腈转化成己二腈,其用于消除酸性LHP化合物 对于氢化反应环境,其中酸性LHP可以催化另外的催化剂配体破坏。 本发明还提供了在含有二齿配位体的亚磷酸二氢镍催化剂的存在下烷基化亚磷酸二氢钠LHP制备的膦酸酯二酯化合物,以及用于生产己二腈的连续氢氰化方法,其中通过使配体水解产物失活而进一步抑制催化剂配体分解 分解。 提供了一种稳定氢氰化催化剂的方法。
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公开(公告)号:US20150148556A1
公开(公告)日:2015-05-28
申请号:US14404037
申请日:2013-05-24
Applicant: INVISTA NORTH AMERICA S.A.R.L.
Inventor: William J. Tenn, III
IPC: C07F9/40 , C07F15/04 , C07C253/10 , B01J31/22 , C07F9/145
CPC classification number: C07F9/06 , B01J31/185 , B01J31/2221 , B01J2231/322 , B01J2231/70 , B01J2531/847 , C07C253/10 , C07C253/30 , C07F9/145 , C07F9/4006 , C07F9/65744 , C07F15/04
Abstract: The invention provides a method of forming a phosphonate diester compound from a ligand hydrolysis product (LHP) of a phosphite ligand used in a nickel-phosphite hydrocyanation catalyst, such as for conversion of 3-pentenenitrile to adiponitrile, which serves to climinate acidic LHP compound for a hydrocyanation reaction milieu where the acidic LHP can catalyze further catalyst ligand destruction. The invention further provides phosphonate disester compounds prepared by alkylation of diarylphosphite LHP in the presence of a nickel-phosphite catalyst comprising a bidentate ligand, and a continuous hydrocyanation process for production of adiponitrile wherein catalyst ligand breakdown is inhibited through inactivation of ligand hydrolysis products towards further breakdown. A method of stabilizing a hydrocyanation catalyst is provided.
Abstract translation: 本发明提供了一种由亚磷酸氢氰化催化剂中使用的亚磷酸酯配位体的配位体水解产物(LHP)形成膦酸二酯化合物的方法,例如将3-戊烯腈转化成己二腈,其用于酸化LHP化合物 对于氢化反应环境,其中酸性LHP可以催化另外的催化剂配体破坏。 本发明还提供了在含有二齿配位体的亚磷酸二氢镍催化剂的存在下烷基化亚磷酸二氢钠LHP制备的膦酸酯二酯化合物,以及用于生产己二腈的连续氢氰化方法,其中通过使配体水解产物失活而进一步抑制催化剂配体分解 分解。 提供了一种稳定氢氰化催化剂的方法。
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公开(公告)号:US10035756B2
公开(公告)日:2018-07-31
申请号:US15320904
申请日:2015-06-25
Applicant: INVISTA NORTH AMERICA S.A.R.L.
Inventor: William J. Tenn, III
IPC: C07C209/48 , C07C253/10 , C07C253/34
CPC classification number: C07C209/48 , C07C253/10 , C07C253/34 , Y02P20/125 , Y02P20/582 , C07C211/12 , C07C255/04
Abstract: Phosphorus-containing ligands are recovered from mixtures comprising 3-pentenenitrile (3PN) and adiponitrile (ADN), using liquid-liquid extraction. ADN is produced by hydrocyanation of 3PN. The ADN is hydrogenated to produce a hexamethyiene diamine (HMD) and at least one byproduct including bis-hexamethylene triamine (BHMT) or 1,2-diaminocyclohexane. At least a portion of the HMD product or byproduct is used to enhance the liquid-liquid extraction to recover phosphorus-containing ligand.
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4.
公开(公告)号:US09011691B2
公开(公告)日:2015-04-21
申请号:US14367149
申请日:2012-11-20
Applicant: INVISTA North America S.a.r.l.
Inventor: William J. Tenn, III , Sudhir N. V. K. Aki , Tseng H. Chao , Thomas E. Vos
IPC: B01D11/04 , C07F9/02 , C07F15/04 , C07F9/145 , C07F9/6574
CPC classification number: C07F9/145 , B01D11/0426 , B01D11/0457 , B01J31/185 , B01J31/26 , B01J31/4053 , C07F9/65746 , C07F15/04 , Y02P20/582
Abstract: Disclosed herein are methods for recovering diphosphite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are treatments to enhance extractability of the diphosphite-containing compounds.
Abstract translation: 本文公开了使用液 - 液萃取从包含有机单腈和有机二腈的混合物中回收含二亚磷酸酯化合物的方法。 还公开了用于提高含二亚磷酸酯化合物的提取性的处理。
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公开(公告)号:US20140378693A1
公开(公告)日:2014-12-25
申请号:US14367149
申请日:2012-11-20
Applicant: INVISTA North America S.a.r.l.
Inventor: William J. Tenn, III
IPC: C07F9/145 , C07F15/04 , C07F9/6574
CPC classification number: C07F9/145 , B01D11/0426 , B01D11/0457 , B01J31/185 , B01J31/26 , B01J31/4053 , C07F9/65746 , C07F15/04 , Y02P20/582
Abstract: Disclosed herein are methods for recovering diphosphite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are treatments to enhance extractability of the diphosphite-containing compounds.
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公开(公告)号:US09040735B2
公开(公告)日:2015-05-26
申请号:US14346882
申请日:2012-10-04
Applicant: INVISTA NORTH AMERICA S.A.R.L.
Inventor: 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
IPC: C07C253/00 , C07C253/08 , C07C253/18 , C07C253/10
CPC classification number: C07C253/18 , C07C253/10 , Y02P20/584 , C07C255/04
Abstract: 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.
Abstract translation: 本发明涉及一种氢氰化3-戊烯腈的方法。 该方法可以包括将3-戊烯腈和HCN加入到包含路易斯酸促进剂,镍和含磷配体的氢化氰化反应区中。 在各种实施方案中,该方法还可以包括控制氢氰化反应区内的水浓度足以维持配体催化剂复合物的高活性,同时再循环至少一部分配体催化剂络合物。
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公开(公告)号:US09834505B2
公开(公告)日:2017-12-05
申请号:US14404068
申请日:2013-05-24
Applicant: INVISTA NORTH AMERICA S.A.R.L.
Inventor: Sudhir Aki , William J. Tenn, III , Thomas E. Vos
IPC: C07C253/30 , C07F9/40 , C07F9/6574 , C07F9/145 , C07F15/04
CPC classification number: C07C253/30 , C07F9/145 , C07F9/4006 , C07F9/65744 , C07F15/04
Abstract: A process of stabilizing a bidentate or tridentate phosphorus-based phosphite ester ligand or mixture thereof in a hydrocyanation reaction milieu comprising water, wherein the ligand or ligand mixture comprises one or more of (i) a bidentate biphosphite ligand of formula (III), (R12—X12) (R13—X13) P—X14—Y—X24—P(X22—R22) (X23—R23) or (ii) a tridentate triphosphite ligand of formula (IIIA) (R12—X12) (R13—X13) P—X14—Y—X32—P(X34—R34)—(X33—Y2—R24—P(X23—R23)—(X22—R22) where each X is oxygen or a bond and each Y is an optionally substituted C6-C20 arylene group, comprising admixing the bidentate and/or tridentate with a stabilizing amount of one or more monodentate phosphite ligand of formula P(X1—R1)(X2—R2)(X3—R3) where each X is oxygen or a bond, wherein the monodentate ligand has a rate of hydrolysis greater than the rate of hydrolysis of the bidentate or tridentate ligand in the presence of water in a hydrocyanation reaction milieu, and thereby preserve concentrations and proportions of the bidentate and/or tridentate ligand(s) in the ligand blend.
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8.
公开(公告)号:US09133226B2
公开(公告)日:2015-09-15
申请号:US14367159
申请日:2012-11-20
Applicant: INVISTA North America S.a.r.l.
Inventor: William J. Tenn, III
CPC classification number: C07F15/045 , B01D11/0426 , B01D11/0457 , B01J23/755 , B01J31/185 , B01J31/26 , B01J31/4053 , C07F9/141 , C07F9/145 , C07F9/65746 , Y02P20/582
Abstract: Disclosed herein are methods for recovering diphosphite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are pre-treatments to enhance extractability of the diphosphite-containing compounds.
Abstract translation: 本文公开了使用液 - 液萃取从包含有机单腈和有机二腈的混合物中回收含二亚磷酸酯化合物的方法。 还公开了用于提高含二亚磷酸盐化合物的提取性的预处理。
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9.
公开(公告)号:US20140350280A1
公开(公告)日:2014-11-27
申请号:US14367156
申请日:2012-11-20
Applicant: INVISTA North America S.a.r.l.
Inventor: William J. Tenn, III
IPC: C07F9/6574 , C07F9/141 , C07F9/145
CPC classification number: C07F9/65746 , B01D11/0426 , B01D11/0457 , B01J31/185 , B01J31/4053 , B01J2531/847 , C07F9/141 , C07F9/145 , Y02P20/582 , Y02P20/584
Abstract: Disclosed herein are methods for recovering diphosphite-containing compounds from mixtures comprising organic mononitriles and organic dinitriles, using liquid-liquid extraction. Also disclosed are treatments to enhance extractability of the diphosphite-containing compounds.
Abstract translation: 本文公开了使用液 - 液萃取从包含有机单腈和有机二腈的混合物中回收含二亚磷酸酯化合物的方法。 还公开了用于提高含二亚磷酸酯化合物的提取性的处理。
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