CA2835868C - Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders - Google Patents

Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders Download PDF

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Publication number
CA2835868C
CA2835868C CA2835868A CA2835868A CA2835868C CA 2835868 C CA2835868 C CA 2835868C CA 2835868 A CA2835868 A CA 2835868A CA 2835868 A CA2835868 A CA 2835868A CA 2835868 C CA2835868 C CA 2835868C
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quinone methide
secondary amine
tert
phenyl
group
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French (fr)
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CA2835868A1 (en
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Jonathan MASERE
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ChampionX LLC
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Nalco Co LLC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C07B63/04—Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/20—Use of additives, e.g. for stabilisation
    • 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
    • C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C07D295/04—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 substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/112—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C07D295/116—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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C08F2/40—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation using retarding agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
CA2835868A 2011-06-13 2012-06-11 Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders Active CA2835868C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US13/158,958 US8884038B2 (en) 2011-06-13 2011-06-13 Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders
US13/158,958 2011-06-13
PCT/US2012/041823 WO2012173909A2 (en) 2011-06-13 2012-06-11 Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders

Publications (2)

Publication Number Publication Date
CA2835868A1 CA2835868A1 (en) 2012-12-20
CA2835868C true CA2835868C (en) 2018-03-13

Family

ID=47292360

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2835868A Active CA2835868C (en) 2011-06-13 2012-06-11 Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders

Country Status (12)

Country Link
US (2) US8884038B2 (https=)
EP (1) EP2718254B1 (https=)
JP (1) JP5918362B2 (https=)
KR (1) KR101951903B1 (https=)
CN (1) CN103619797B (https=)
BR (2) BR112013031103B1 (https=)
CA (1) CA2835868C (https=)
ES (1) ES2633763T3 (https=)
MX (1) MX355215B (https=)
SG (1) SG194960A1 (https=)
TW (1) TWI596087B (https=)
WO (1) WO2012173909A2 (https=)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8901362B2 (en) * 2012-02-02 2014-12-02 General Electric Company Methods and compositions for styrene inhibition via in situ generation of quinone methides
DE102013204950A1 (de) 2013-03-20 2014-09-25 Evonik Industries Ag Verfahren und Zusammensetzung zur Inhibierung der Polymerisation von Cyclopentadienverbindungen
CN104341281A (zh) * 2014-06-29 2015-02-11 浙江大学 2,6-二叔丁基-4-(2-甲氧基苯亚甲基)-2,5-环己二烯-1-酮及其制备法
WO2016061120A1 (en) 2014-10-14 2016-04-21 Ecolab Usa Inc. Reducing polymer fouling and agglomeration in acrylate/methacrylate processes
JP6730303B2 (ja) 2015-03-18 2020-07-29 エコラブ ユーエスエイ インク ビニルモノマーの重合を阻害するための安定した親油性ヒドロキシルアミン化合物の使用
US9957209B2 (en) 2015-03-31 2018-05-01 Ecolab Usa Inc. Use of quinone methides as antipolymerants for vinylic monomers
KR102616836B1 (ko) 2015-04-20 2023-12-20 에코랍 유에스에이 인코퍼레이티드 불포화 단량체에 대한 방오제로서의 입체 장애 하이드로퀴논
US11180578B2 (en) 2018-07-13 2021-11-23 Ecolab Usa Inc. Polymerization inhibitor and retarder compositions with amine stabilizer
EP3820836A1 (en) 2018-07-13 2021-05-19 Ecolab USA, Inc. Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers
CN116553996A (zh) * 2023-07-07 2023-08-08 吉林金海化工新材料有限公司 一种阻聚剂及其应用

Family Cites Families (23)

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US2459597A (en) 1945-05-16 1949-01-18 Gulf Research Development Co Di-alkylated mono-hydroxy phenol
US3257321A (en) 1960-09-01 1966-06-21 Ethyl Corp 3, 5-dialkyl-4-hydroxybenzyl chloride
US3390198A (en) 1965-12-16 1968-06-25 Koppers Co Inc Tertiary-butyl-5-methyl catechol as polymerization inhibitor for hot styrene
US3660505A (en) 1969-08-27 1972-05-02 Exxon Research Engineering Co Hindered alkenyl phenols from quinone methide
US4003800A (en) 1976-01-02 1977-01-18 Gulf Research & Development Company Styrene purification process
US4032547A (en) 1976-02-23 1977-06-28 Gulf Research & Development Company Quinone alkide synthesis system
US4409408A (en) 1982-09-24 1983-10-11 Atlantic Richfield Company Inhibiting polymerization of vinyl aromatic monomers
US5446220A (en) 1994-08-24 1995-08-29 Betz Laboratories, Inc. Methods for inhibiting vinyl aromatic monomer polymerization
US5583247A (en) * 1995-04-14 1996-12-10 Ciba-Geigy Corporation 7-substituted quinone methides as inhibitors for unsaturated monomers
US5616774A (en) 1995-04-14 1997-04-01 Ciba-Geigy Corporation Inhibition of unsaturated monomers with 7-aryl quinone methides
EP0744392A1 (en) * 1995-05-26 1996-11-27 Ciba-Geigy Ag A new one-pot process for the preparation of 7-aryl-2,6-disubstituted quinone methides
FR2746098B1 (fr) * 1996-03-14 1998-04-30 Composes propynyl biaromatiques
US6024894A (en) 1998-03-25 2000-02-15 Betzdearborn Inc. Compositions and methods for inhibiting vinyl aromatic monomer polymerization
ES2292487T3 (es) * 1999-12-03 2008-03-16 Chemtura Corporation Composicion y metodo para inhibir la polimerizacion y el crecimiento polimerico.
US7045647B2 (en) 2000-10-16 2006-05-16 Uniroyal Chemical Company, Inc. Blends of quinone alkide and nitroxyl compounds and polymerization inhibitors
ES2247332T3 (es) 2001-03-20 2006-03-01 Ciba Specialty Chemicals Holding Inc. Composiciones ignifugantes.
US6926820B2 (en) 2002-09-20 2005-08-09 G.E. Betz, Inc. Inhibition of viscosity increase and fouling in hydrocarbon streams including unsaturation
US6818027B2 (en) 2003-02-06 2004-11-16 Ecoem, L.L.C. Organically clean biomass fuel
WO2004083156A1 (ja) 2003-03-17 2004-09-30 Hakuto Co., Ltd. 芳香族ビニル化合物の重合抑制剤および重合抑制方法
US20080132726A1 (en) * 2006-11-30 2008-06-05 Vinod Kumar Rai Process for the production of quinone methide
DE102007052891A1 (de) * 2007-11-02 2009-05-07 Evonik Degussa Gmbh Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren
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Also Published As

Publication number Publication date
MX355215B (es) 2018-04-10
EP2718254A2 (en) 2014-04-16
CN103619797A (zh) 2014-03-05
US20150060727A1 (en) 2015-03-05
WO2012173909A3 (en) 2013-03-21
WO2012173909A2 (en) 2012-12-20
SG194960A1 (en) 2013-12-30
ES2633763T3 (es) 2017-09-25
JP5918362B2 (ja) 2016-05-18
MX2013013687A (es) 2014-01-08
US20120313036A1 (en) 2012-12-13
EP2718254A4 (en) 2015-04-01
JP2014525898A (ja) 2014-10-02
CN103619797B (zh) 2015-02-04
CA2835868A1 (en) 2012-12-20
KR101951903B1 (ko) 2019-02-25
BR112013031103A2 (pt) 2016-12-06
US8884038B2 (en) 2014-11-11
US9447002B2 (en) 2016-09-20
KR20140041729A (ko) 2014-04-04
BR122019013055B1 (pt) 2019-12-17
TWI596087B (zh) 2017-08-21
BR112013031103B1 (pt) 2020-04-22
EP2718254B1 (en) 2017-05-10
TW201307277A (zh) 2013-02-16

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