JP2014525898A5 - - Google Patents
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- Publication number
- JP2014525898A5 JP2014525898A5 JP2014515897A JP2014515897A JP2014525898A5 JP 2014525898 A5 JP2014525898 A5 JP 2014525898A5 JP 2014515897 A JP2014515897 A JP 2014515897A JP 2014515897 A JP2014515897 A JP 2014515897A JP 2014525898 A5 JP2014525898 A5 JP 2014525898A5
- Authority
- JP
- Japan
- Prior art keywords
- secondary amine
- methide
- phenyl
- tert
- quinone methide
- 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.)
- Granted
Links
- -1 3,5-disubstituted-4-hydroxybenzaldehyde Chemical class 0.000 claims description 25
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 11
- 150000003335 secondary amines Chemical class 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000001247 metal acetylides Chemical class 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/158,958 | 2011-06-13 | ||
| 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 |
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2014525898A JP2014525898A (ja) | 2014-10-02 |
| JP2014525898A5 true JP2014525898A5 (cg-RX-API-DMAC10.html) | 2015-05-14 |
| JP5918362B2 JP5918362B2 (ja) | 2016-05-18 |
Family
ID=47292360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014515897A Active JP5918362B2 (ja) | 2011-06-13 | 2012-06-11 | ７―アセチレンキノンメチド誘導体の合成及びそのビニル重合遅延剤としての用途 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8884038B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2718254B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP5918362B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR101951903B1 (cg-RX-API-DMAC10.html) |
| CN (1) | CN103619797B (cg-RX-API-DMAC10.html) |
| BR (2) | BR112013031103B1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2835868C (cg-RX-API-DMAC10.html) |
| ES (1) | ES2633763T3 (cg-RX-API-DMAC10.html) |
| MX (1) | MX355215B (cg-RX-API-DMAC10.html) |
| SG (1) | SG194960A1 (cg-RX-API-DMAC10.html) |
| TW (1) | TWI596087B (cg-RX-API-DMAC10.html) |
| WO (1) | WO2012173909A2 (cg-RX-API-DMAC10.html) |
Families Citing this family (10)
| 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 |
| SG11201703031PA (en) | 2014-10-14 | 2017-05-30 | Ecolab Usa Inc | Reducing polymer fouling and agglomeration in acrylate/methacrylate processes |
| ES2912329T3 (es) | 2015-03-18 | 2022-05-25 | Ecolab Usa Inc | El uso de compuestos de hidroxilamina lipófilos estables para inhibir la polimerización de monómeros de vinilo |
| US9957209B2 (en) | 2015-03-31 | 2018-05-01 | Ecolab Usa Inc. | Use of quinone methides as antipolymerants for vinylic monomers |
| TWI624480B (zh) | 2015-04-20 | 2018-05-21 | 藝康美國公司 | 供不飽和單體用作防污劑之受阻對苯二酚 |
| TW202005938A (zh) | 2018-07-13 | 2020-02-01 | 美商藝康美國公司 | 具有胺穩定劑之聚合抑制劑及阻滯劑組合物 |
| KR102763208B1 (ko) | 2018-07-13 | 2025-02-04 | 에코랍 유에스에이 인코퍼레이티드 | 비닐계 단량체에 대한 항파울런트로서의 산소화 아민 및 퀴논 메티드의 조성물 |
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5616774A (en) | 1995-04-14 | 1997-04-01 | Ciba-Geigy Corporation | Inhibition of unsaturated monomers with 7-aryl quinone methides |
| US5583247A (en) | 1995-04-14 | 1996-12-10 | Ciba-Geigy Corporation | 7-substituted quinone methides as inhibitors for unsaturated monomers |
| 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 |
| DE60036018T2 (de) * | 1999-12-03 | 2008-04-30 | Chemtura Corporation, Middlebury | Zusammensetzungen und verfahren zur inhibierung der polymerisierung und polymerwachstums |
| US7045647B2 (en) | 2000-10-16 | 2006-05-16 | Uniroyal Chemical Company, Inc. | Blends of quinone alkide and nitroxyl compounds and polymerization inhibitors |
| CN1282695C (zh) | 2001-03-20 | 2006-11-01 | 西巴特殊化学品控股有限公司 | 阻燃剂组合物 |
| 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 |
| CN100522902C (zh) | 2003-03-17 | 2009-08-05 | 伯东株式会社 | 芳香族乙烯基化合物的聚合抑制剂以及聚合抑制方法 |
| 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 |
| US8247593B2 (en) | 2008-05-13 | 2012-08-21 | Nalco Company | Process for preparing substituted 7-cyano quinone methides |
| US7651635B1 (en) * | 2009-02-05 | 2010-01-26 | Nalco Company | Polymer inhibition of vinyl aromatic monomers using a quinone methide/alkyl hydroxylamine combination |
-
2011
- 2011-06-13 US US13/158,958 patent/US8884038B2/en active Active
-
2012
- 2012-06-08 TW TW101120626A patent/TWI596087B/zh active
- 2012-06-11 EP EP12799844.1A patent/EP2718254B1/en active Active
- 2012-06-11 CA CA2835868A patent/CA2835868C/en active Active
- 2012-06-11 KR KR1020147000886A patent/KR101951903B1/ko active Active
- 2012-06-11 ES ES12799844.1T patent/ES2633763T3/es active Active
- 2012-06-11 MX MX2013013687A patent/MX355215B/es active IP Right Grant
- 2012-06-11 JP JP2014515897A patent/JP5918362B2/ja active Active
- 2012-06-11 SG SG2013084413A patent/SG194960A1/en unknown
- 2012-06-11 BR BR112013031103A patent/BR112013031103B1/pt active IP Right Grant
- 2012-06-11 CN CN201280029046.5A patent/CN103619797B/zh active Active
- 2012-06-11 BR BR122019013055A patent/BR122019013055B1/pt active IP Right Grant
- 2012-06-11 WO PCT/US2012/041823 patent/WO2012173909A2/en not_active Ceased
-
2014
- 2014-10-29 US US14/527,495 patent/US9447002B2/en active Active
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