CA2291486A1 - Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst - Google Patents

Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst Download PDF

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Publication number
CA2291486A1
CA2291486A1 CA002291486A CA2291486A CA2291486A1 CA 2291486 A1 CA2291486 A1 CA 2291486A1 CA 002291486 A CA002291486 A CA 002291486A CA 2291486 A CA2291486 A CA 2291486A CA 2291486 A1 CA2291486 A1 CA 2291486A1
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CA
Canada
Prior art keywords
group
zinc
compound
catalyst
reduction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002291486A
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English (en)
French (fr)
Inventor
Hubert Mimoun
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Firmenich SA
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Individual
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Filing date
Publication date
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Publication of CA2291486A1 publication Critical patent/CA2291486A1/en
Abandoned legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213—Complexes without C-metal linkages
    • B01J2531/0216—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/26—Zinc
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
    • C07C2602/28—Hydrogenated naphthalenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
CA002291486A 1998-04-01 1999-02-25 Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst Abandoned CA2291486A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH778/98 1998-04-01
CH77898 1998-04-01
PCT/IB1999/000329 WO1999050211A1 (en) 1998-04-01 1999-02-25 Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst

Publications (1)

Publication Number Publication Date
CA2291486A1 true CA2291486A1 (en) 1999-10-07

Family

ID=4194974

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002291486A Abandoned CA2291486A1 (en) 1998-04-01 1999-02-25 Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst

Country Status (10)

Country Link
US (3) US6245952B1 (https=)
EP (1) EP0986527B1 (https=)
JP (1) JP4169801B2 (https=)
CN (1) CN1208295C (https=)
AT (1) ATE239685T1 (https=)
CA (1) CA2291486A1 (https=)
DE (1) DE69907589T2 (https=)
ES (1) ES2198886T3 (https=)
IL (1) IL133270A (https=)
WO (1) WO1999050211A1 (https=)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69812385T2 (de) * 1997-09-09 2004-02-05 Firmenich S.A. Enatioselektive reduktion von ketonen mit einem system aus silanmittel / metallischer verbindung / chiralem ligand
ES2198886T3 (es) * 1998-04-01 2004-02-01 Firmenich Sa Reduccion de compuestos carbonilados por un silano en presencia de un catalizador de zinc.
JP2002516828A (ja) * 1998-06-01 2002-06-11 アンソニー・ジェイ・バービスカー 局所経皮治療
US7955611B2 (en) 2000-01-03 2011-06-07 International Flora Technologies Ltd. Binding and rinse-off of quaternary ammonium compounds for cosmetic and personal care applications
DE10238114A1 (de) * 2002-08-21 2004-03-04 Bayer Ag Optisch aktive Diamine und deren Anwendung in katalytischen Prozessen
JP4962924B2 (ja) * 2005-03-04 2012-06-27 学校法人東京理科大学 光学活性アルコールの製造方法
JP5179430B2 (ja) * 2009-02-27 2013-04-10 国立大学法人名古屋大学 光学活性アルコールの製造方法
CN101844957B (zh) * 2010-03-30 2012-10-24 杭州师范大学 一种α, β-不饱和酮羰基还原成亚甲基的方法
EP2935492B1 (fr) * 2012-12-20 2016-10-26 Bluestar Silicones France SAS Article présentant des propriétés antisalissures et destiné à être utilisé dans des applications aquatiques en particulier marines
JP6023897B2 (ja) * 2012-12-20 2016-11-09 ブルースター・シリコーンズ・フランス・エスアエス 室温におけるエラストマーへの加硫に適したオルガノポリシロキサン組成物及び新規のオルガノポリシロキサン重縮合触媒
EP2935490B1 (fr) 2012-12-20 2022-12-21 ELKEM SILICONES France SAS Composition organopolysiloxanique vulcanisable a température ambiante en élastomère et nouveaux catalyseurs de polycondensation d'organopolysiloxanes
FR2999980A1 (fr) * 2012-12-20 2014-06-27 Bluestar Silicones France Article presentant des proprietes antisalissures et destine a etre utilise dans des applications aquatiques en particulier marines
EP3145961A4 (en) * 2014-05-21 2018-06-27 Dow Corning Corporation Zinc containing catalysts, methods for preparing the catalysts, and compositions containing the catalysts
JP6514568B2 (ja) * 2015-05-19 2019-05-15 東ソー・ファインケム株式会社 ジアルキル亜鉛部分加水分解物含有溶液及びこの溶液を用いる酸化亜鉛薄膜の製造方法
US9776179B2 (en) 2015-11-18 2017-10-03 Provivi, Inc. Production of fatty olefin derivatives via olefin metathesis
JP7153937B2 (ja) 2017-02-17 2022-10-17 プロビビ インコーポレイテッド オレフィンメタセシスによるフェロモンおよび関連材料の合成方法
EP3438158B1 (de) 2017-08-01 2020-11-25 Evonik Operations GmbH Herstellung von sioc-verknüpften polyethersiloxanen
AU2021283190A1 (en) 2020-06-01 2022-12-15 Provivi, Inc. Synthesis of pheromone derivatives via Z-selective olefin metathesis
CN116390927A (zh) * 2020-11-27 2023-07-04 弗门尼舍有限公司 在锌催化剂存在下通过硅烷进行的还原
CN116874350A (zh) * 2023-07-10 2023-10-13 福建桦智工程技术有限公司 一种使用不饱和酯连续还原制备叶醇的工艺
CN118221704A (zh) * 2024-03-29 2024-06-21 福州大学 一种用于催化不饱和酰胺选择性还原的锌催化剂及其应用

Family Cites Families (8)

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Publication number Priority date Publication date Assignee Title
US3061424A (en) 1957-02-06 1962-10-30 Wacker Chemie Gmbh Method of reducing organometallic compounds
GB8902228D0 (en) * 1989-02-01 1989-03-22 Ici Plc Carbodiimide-isocyanurate rigid foams
US5227538A (en) * 1990-11-21 1993-07-13 Massachusetts Institute Of Technology Catalytic asymmetric reduction of ketones using metal catalysts
US5220020A (en) 1990-11-21 1993-06-15 Massachusetts Institute Of Technology Catalytic reduction of organic carbonyls using metal catalysts
US5449736A (en) * 1993-07-16 1995-09-12 Research Foundation Of The State Of New York Water soluble phosphorylated polysiloxanes
WO1996012694A1 (fr) * 1994-10-19 1996-05-02 Firmenich S.A. Procede pour la preparation d'alcools
DE69812385T2 (de) * 1997-09-09 2004-02-05 Firmenich S.A. Enatioselektive reduktion von ketonen mit einem system aus silanmittel / metallischer verbindung / chiralem ligand
ES2198886T3 (es) * 1998-04-01 2004-02-01 Firmenich Sa Reduccion de compuestos carbonilados por un silano en presencia de un catalizador de zinc.

Also Published As

Publication number Publication date
JP4169801B2 (ja) 2008-10-22
EP0986527B1 (en) 2003-05-07
DE69907589D1 (de) 2003-06-12
CN1262667A (zh) 2000-08-09
US20010034464A1 (en) 2001-10-25
ATE239685T1 (de) 2003-05-15
ES2198886T3 (es) 2004-02-01
IL133270A0 (en) 2001-04-30
JP2002503259A (ja) 2002-01-29
IL133270A (en) 2006-06-11
EP0986527A1 (en) 2000-03-22
CN1208295C (zh) 2005-06-29
US6533960B2 (en) 2003-03-18
US20030171210A1 (en) 2003-09-11
US6245952B1 (en) 2001-06-12
WO1999050211A1 (en) 1999-10-07
DE69907589T2 (de) 2004-03-25
US6770588B2 (en) 2004-08-03

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Legal Events

Date Code Title Description
EEER Examination request
FZDE Discontinued