JP6118347B2 - 現場生成キノンメチドによるスチレン抑制方法及び組成物 - Google Patents
現場生成キノンメチドによるスチレン抑制方法及び組成物 Download PDFInfo
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- JP6118347B2 JP6118347B2 JP2014555737A JP2014555737A JP6118347B2 JP 6118347 B2 JP6118347 B2 JP 6118347B2 JP 2014555737 A JP2014555737 A JP 2014555737A JP 2014555737 A JP2014555737 A JP 2014555737A JP 6118347 B2 JP6118347 B2 JP 6118347B2
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Links
- 238000000034 method Methods 0.000 title claims description 38
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 36
- 239000000203 mixture Substances 0.000 title claims description 28
- 230000002401 inhibitory effect Effects 0.000 title claims description 12
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title description 9
- 238000011065 in-situ storage Methods 0.000 title description 3
- 239000000178 monomer Substances 0.000 claims description 46
- 229920002554 vinyl polymer Polymers 0.000 claims description 33
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- -1 di-tert-butylhydroxybenzyl alcohol Chemical compound 0.000 claims description 21
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
- 230000018044 dehydration Effects 0.000 claims description 16
- 238000006297 dehydration reaction Methods 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 14
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical group CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 13
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000005418 aryl aryl group Chemical group 0.000 claims description 4
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical class O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical group 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- JYOCWMVETLTCNF-UHFFFAOYSA-N 1-[hydroxy(2-hydroxypropyl)amino]propan-2-ol Chemical group CC(O)CN(O)CC(C)O JYOCWMVETLTCNF-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical group CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/364,554 | 2012-02-02 | ||
| US13/364,554 US8901362B2 (en) | 2012-02-02 | 2012-02-02 | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
| PCT/US2013/024297 WO2013116611A1 (en) | 2012-02-02 | 2013-02-01 | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015505579A JP2015505579A (ja) | 2015-02-23 |
| JP2015505579A5 JP2015505579A5 (enExample) | 2016-03-17 |
| JP6118347B2 true JP6118347B2 (ja) | 2017-04-19 |
Family
ID=47741287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014555737A Active JP6118347B2 (ja) | 2012-02-02 | 2013-02-01 | 現場生成キノンメチドによるスチレン抑制方法及び組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8901362B2 (enExample) |
| EP (1) | EP2809634B1 (enExample) |
| JP (1) | JP6118347B2 (enExample) |
| KR (1) | KR101660610B1 (enExample) |
| CN (1) | CN104105680A (enExample) |
| BR (1) | BR112014018620A8 (enExample) |
| CA (1) | CA2862034A1 (enExample) |
| SG (1) | SG11201404399SA (enExample) |
| TW (1) | TWI558750B (enExample) |
| WO (1) | WO2013116611A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9206268B2 (en) * | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
| KR102091718B1 (ko) * | 2016-02-13 | 2020-03-20 | 도르프 케탈 케미칼즈 (인디아) 프라이비트 리미티드 | 비닐 방향족 모노머의 중합의 조절 및 억제를 위한 조성물, 및 이의 사용 방법 |
| TWI826485B (zh) | 2018-07-13 | 2023-12-21 | 美商藝康美國公司 | 作為乙烯系單體之防垢劑之含氧胺及醌甲基化物之組合物 |
| CN112533902B (zh) | 2018-07-13 | 2025-03-14 | 埃科莱布美国股份有限公司 | 抑制单体聚合的包含氮氧化物抑制剂、醌甲基化物阻滞剂和胺稳定剂的组合物 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3925488A (en) | 1971-05-24 | 1975-12-09 | Ethyl Corp | Process for the production of 1,3,5-trimethy-2,4,6-tris(3,5-di-tert-alkyl-4-hydroxybenzyl)benzene |
| US4032547A (en) | 1976-02-23 | 1977-06-28 | Gulf Research & Development Company | Quinone alkide synthesis system |
| TW225522B (enExample) * | 1992-02-24 | 1994-06-21 | Ciba Geigy Ag | |
| US5254760A (en) | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US5470440A (en) | 1994-04-19 | 1995-11-28 | Betz Laboratories, Inc. | Method 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 |
| US6409887B1 (en) | 1996-07-15 | 2002-06-25 | Aah Marks And Company Limited | Polymerization inhibitor |
| US6024894A (en) | 1998-03-25 | 2000-02-15 | Betzdearborn Inc. | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
| US6376728B1 (en) * | 2000-06-20 | 2002-04-23 | Hercules Incorporated | Method, composition and mixture for inhibiting monomer polymerization |
| US6388155B1 (en) | 2000-08-01 | 2002-05-14 | Abb Lummus Global Inc. | Styrene dehydrogenation reactor effluent treatment |
| JP4248875B2 (ja) * | 2000-10-16 | 2009-04-02 | ケムチュア コーポレイション | 重合抑制剤としての、キノンアルカイドとニトロキシル化合物の混合物 |
| US6960279B2 (en) * | 2002-05-06 | 2005-11-01 | Fina Technology, Inc. | Method for stabilizing vinyl aromatic monomers using selected polymerization inhibitors and polymers prepared therewith |
| US6926820B2 (en) | 2002-09-20 | 2005-08-09 | G.E. Betz, Inc. | Inhibition of viscosity increase and fouling in hydrocarbon streams including unsaturation |
| JP4790414B2 (ja) * | 2003-03-17 | 2011-10-12 | 伯東株式会社 | 芳香族ビニル化合物の重合抑制剤および重合抑制方法 |
| US7128826B2 (en) | 2003-07-31 | 2006-10-31 | General Electric Company | Polymerization inhibitor for styrene dehydrogenation units |
| GB0521319D0 (en) * | 2005-10-20 | 2005-11-30 | A H Marks And Company Ltd | Method |
| DE102007052891A1 (de) * | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren |
| US8298440B2 (en) * | 2010-06-03 | 2012-10-30 | General Electric Company | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
| GB201011594D0 (en) * | 2010-07-09 | 2010-08-25 | Nufarm Uk Ltd | Retarder composition |
| US20120217444A1 (en) * | 2011-02-28 | 2012-08-30 | Shengxia Liu | Composition and method for inhibiting premature polymerization |
| US8884038B2 (en) * | 2011-06-13 | 2014-11-11 | Nalco Company | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
| US9090526B2 (en) * | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
| US9206268B2 (en) * | 2011-09-16 | 2015-12-08 | General Electric Company | Methods and compositions for inhibiting polystyrene formation during styrene production |
-
2012
- 2012-02-02 US US13/364,554 patent/US8901362B2/en not_active Expired - Fee Related
-
2013
- 2013-01-24 TW TW102102707A patent/TWI558750B/zh not_active IP Right Cessation
- 2013-02-01 CN CN201380007842.3A patent/CN104105680A/zh active Pending
- 2013-02-01 KR KR1020147021068A patent/KR101660610B1/ko not_active Expired - Fee Related
- 2013-02-01 JP JP2014555737A patent/JP6118347B2/ja active Active
- 2013-02-01 WO PCT/US2013/024297 patent/WO2013116611A1/en not_active Ceased
- 2013-02-01 EP EP13705321.1A patent/EP2809634B1/en not_active Not-in-force
- 2013-02-01 CA CA2862034A patent/CA2862034A1/en not_active Abandoned
- 2013-02-01 SG SG11201404399SA patent/SG11201404399SA/en unknown
- 2013-02-01 BR BR112014018620A patent/BR112014018620A8/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20140119054A (ko) | 2014-10-08 |
| EP2809634B1 (en) | 2018-01-31 |
| KR101660610B1 (ko) | 2016-09-27 |
| SG11201404399SA (en) | 2014-08-28 |
| US8901362B2 (en) | 2014-12-02 |
| BR112014018620A2 (enExample) | 2017-06-20 |
| WO2013116611A1 (en) | 2013-08-08 |
| TW201336907A (zh) | 2013-09-16 |
| EP2809634A1 (en) | 2014-12-10 |
| CA2862034A1 (en) | 2013-08-08 |
| CN104105680A (zh) | 2014-10-15 |
| BR112014018620A8 (pt) | 2017-07-11 |
| JP2015505579A (ja) | 2015-02-23 |
| TWI558750B (zh) | 2016-11-21 |
| US20130204053A1 (en) | 2013-08-08 |
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