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GB1199351A - Improvements in the Preparation of Nitroxides - Google Patents

Improvements in the Preparation of Nitroxides

Info

Publication number
GB1199351A
GB1199351A GB1083668A GB1083668A GB1199351A GB 1199351 A GB1199351 A GB 1199351A GB 1083668 A GB1083668 A GB 1083668A GB 1083668 A GB1083668 A GB 1083668A GB 1199351 A GB1199351 A GB 1199351A
Authority
GB
United Kingdom
Prior art keywords
amine
nitroxides
preparation
oxyl
oxidizing
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.)
Expired
Application number
GB1083668A
Inventor
Donald Peter Young
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BP Chemicals Ltd
BP Chemicals UK Ltd
Original Assignee
BP Chemicals Ltd
BP Chemicals UK Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BP Chemicals Ltd, BP Chemicals UK Ltd filed Critical BP Chemicals Ltd
Priority to GB1083668A priority Critical patent/GB1199351A/en
Publication of GB1199351A publication Critical patent/GB1199351A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/24—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,199,351. Preparation of nitroxides. BP CHEMICALS (U.K.) Ltd. 12 Feb., 1969 [6 March, 1968], No. 10836/68. Heading C2C. Nitroxides of the general formulµ wherein R<SP>1</SP>-R<SP>6</SP> represent the same or different alkyl groups and n is from 1 to 17, are prepared by oxidizing the corresponding amine to the N-hydroxy amine by reaction with aqueous hydrogen peroxide in the presence of permolybdic or pertungstic acid or a salt thereof as catalyst, and subsequently oxidizing the N- hydroxy amine to the corresponding nitroxide by means of another oxidizing agent, e.g. molecular oxygen or ferricyanide ion. The primary oxidation is preferably performed at room temperature using 1-1À5 moles H 2 O 2 / mole amine and the aqueous solution contains a small amount of sodium ethylenediamine tetraacetate. The resulting reaction mixture is preferably heated to a temperature up to 100‹ C. and then cooled before carrying out the second oxidation step. Examples detail the preparation of 2,2,6,6 - tetramethylpiperidine - 1 - oxyl, 2,2,5,5 - tetramethylpyrrolidine - 1 - oxyl, and t.-butyl t.-pentyl nitroxide.
GB1083668A 1968-03-06 1968-03-06 Improvements in the Preparation of Nitroxides Expired GB1199351A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1083668A GB1199351A (en) 1968-03-06 1968-03-06 Improvements in the Preparation of Nitroxides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1083668A GB1199351A (en) 1968-03-06 1968-03-06 Improvements in the Preparation of Nitroxides

Publications (1)

Publication Number Publication Date
GB1199351A true GB1199351A (en) 1970-07-22

Family

ID=9975219

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1083668A Expired GB1199351A (en) 1968-03-06 1968-03-06 Improvements in the Preparation of Nitroxides

Country Status (1)

Country Link
GB (1) GB1199351A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488403A2 (en) * 1990-11-30 1992-06-03 GREAT LAKES CHEMICAL ITALIA S.r.l. Process for the preparation of nitroxyl radicals of sterically hindered amines
NL1000396C2 (en) * 1995-05-18 1996-11-19 Avebe Coop Verkoop Prod Method for the recovery or recirculation of stable nitroxide radicals.
US5728872A (en) * 1994-06-27 1998-03-17 Lutz Riemenschneider Stabilized acrylic acid compositions
EP0866060A2 (en) * 1997-03-18 1998-09-23 Hüls Aktiengesellschaft Process for the preparation of 1,2,3,6-tetrahydro-2,2,6,6,-tetramethylpyridin-N-oxyl
US5998661A (en) * 1998-06-15 1999-12-07 The United States Of America As Represented By The Secretary Of The Army Preparations of organic nitro compounds through mixed oxidizing agents
US6255448B1 (en) 1995-02-07 2001-07-03 Atofina Polymerization in the presence of a β-substituted nitroxide radical
US6262179B1 (en) 1995-02-07 2001-07-17 Atofina Process for the manufacture of a composition comprising a vinylaromatic polymer and a rubber by polymerization in the presence of a stable free radical
US6538141B1 (en) * 1999-01-08 2003-03-25 Atofina Method for preparing nitroxides

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0488403A2 (en) * 1990-11-30 1992-06-03 GREAT LAKES CHEMICAL ITALIA S.r.l. Process for the preparation of nitroxyl radicals of sterically hindered amines
EP0488403A3 (en) * 1990-11-30 1992-09-23 Enichem Synthesis S.P.A. Process for the preparation of nitroxyl radicals of sterically hindered amines
US5728872A (en) * 1994-06-27 1998-03-17 Lutz Riemenschneider Stabilized acrylic acid compositions
US6255448B1 (en) 1995-02-07 2001-07-03 Atofina Polymerization in the presence of a β-substituted nitroxide radical
US6262179B1 (en) 1995-02-07 2001-07-17 Atofina Process for the manufacture of a composition comprising a vinylaromatic polymer and a rubber by polymerization in the presence of a stable free radical
NL1000396C2 (en) * 1995-05-18 1996-11-19 Avebe Coop Verkoop Prod Method for the recovery or recirculation of stable nitroxide radicals.
WO1996036621A1 (en) * 1995-05-18 1996-11-21 Coöperatieve Verkoop- En Produktievereniging Van Aardappelmeel En Derivaten Avebe B.A. Method for recovering or recirculating stable nitroxide radicals
EP0866060A2 (en) * 1997-03-18 1998-09-23 Hüls Aktiengesellschaft Process for the preparation of 1,2,3,6-tetrahydro-2,2,6,6,-tetramethylpyridin-N-oxyl
EP0866060A3 (en) * 1997-03-18 1998-10-21 Hüls Aktiengesellschaft Process for the preparation of 1,2,3,6-tetrahydro-2,2,6,6,-tetramethylpyridin-N-oxyl
US6452016B1 (en) 1997-03-18 2002-09-17 Degussa-Huels Aktiengesellschaft Process for the preparation of 1,2,3,6-tetrahydro-2,2,6,6-tetramethylpyridine N-oxide
US5998661A (en) * 1998-06-15 1999-12-07 The United States Of America As Represented By The Secretary Of The Army Preparations of organic nitro compounds through mixed oxidizing agents
US6538141B1 (en) * 1999-01-08 2003-03-25 Atofina Method for preparing nitroxides

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee