TWI558750B - 藉由醌甲基化物之原位生成而用於抑制苯乙烯之方法及組合物 - Google Patents
藉由醌甲基化物之原位生成而用於抑制苯乙烯之方法及組合物 Download PDFInfo
- Publication number
- TWI558750B TWI558750B TW102102707A TW102102707A TWI558750B TW I558750 B TWI558750 B TW I558750B TW 102102707 A TW102102707 A TW 102102707A TW 102102707 A TW102102707 A TW 102102707A TW I558750 B TWI558750 B TW I558750B
- Authority
- TW
- Taiwan
- Prior art keywords
- composition
- weight
- vinyl monomer
- monomer
- amount
- Prior art date
Links
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 38
- 239000000203 mixture Substances 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 24
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title description 9
- 230000005764 inhibitory process Effects 0.000 title description 4
- 238000011065 in-situ storage Methods 0.000 title description 3
- 239000000178 monomer Substances 0.000 claims description 45
- 229920002554 vinyl polymer Polymers 0.000 claims description 31
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- -1 alkyl aryl sulfonic acid 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 19
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 230000018044 dehydration Effects 0.000 claims description 12
- 238000006297 dehydration reaction Methods 0.000 claims description 12
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical group CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 11
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 11
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 150000001875 compounds Chemical class 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
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 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 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 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
- 239000002253 acid Substances 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
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 description 13
- 229920000642 polymer Polymers 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002360 preparation method Methods 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
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 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
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 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
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- HCUWXYBKPSKTAB-UHFFFAOYSA-N 4-benzylidene-2,6-ditert-butylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC1=CC=CC=C1 HCUWXYBKPSKTAB-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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/364,554 US8901362B2 (en) | 2012-02-02 | 2012-02-02 | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201336907A TW201336907A (zh) | 2013-09-16 |
| TWI558750B true TWI558750B (zh) | 2016-11-21 |
Family
ID=47741287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW102102707A TWI558750B (zh) | 2012-02-02 | 2013-01-24 | 藉由醌甲基化物之原位生成而用於抑制苯乙烯之方法及組合物 |
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 |
| JP6530868B2 (ja) * | 2016-02-13 | 2019-06-12 | ドルフ ケタール ケミカルズ （インディア）プライヴェート リミテッド | ビニル芳香族モノマーの重合を制御及び阻害するための組成物及びその使用方法 |
| US10869444B2 (en) | 2018-07-13 | 2020-12-22 | Ecolab Usa Inc. | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers |
| EP3820846B1 (en) | 2018-07-13 | 2024-01-03 | Ecolab USA, Inc. | Composition for inhibiting monomer polymerization comprising a nitroxide inhibitor, a quinone methide retarder and an amine stabilizer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW225522B (enExample) * | 1992-02-24 | 1994-06-21 | Ciba Geigy Ag | |
| TW394786B (en) * | 1995-04-14 | 2000-06-21 | Ciba Sc Holding Ag | A stabilized monomer composition and a stabilizer mixture |
Family Cites Families (21)
| 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 |
| 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 |
| 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 |
| KR100812038B1 (ko) * | 2000-10-16 | 2008-03-10 | 유니로얄 캐미칼 캄파니, 인크. | 중합 억제제로서 퀴논 알키드와 니트록실 화합물의 블렌드물 |
| 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 |
| 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 |
| 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 |
| US9090526B2 (en) * | 2011-06-13 | 2015-07-28 | Nalco Company | Synergistic combination for inhibiting polymerization of vinyl monomers |
| US8884038B2 (en) * | 2011-06-13 | 2014-11-11 | Nalco Company | Synthesis of 7-acetyleno quinone methide derivatives and their application as vinylic polymerization retarders |
| 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 KR KR1020147021068A patent/KR101660610B1/ko not_active Expired - Fee Related
- 2013-02-01 WO PCT/US2013/024297 patent/WO2013116611A1/en not_active Ceased
- 2013-02-01 CA CA2862034A patent/CA2862034A1/en not_active Abandoned
- 2013-02-01 JP JP2014555737A patent/JP6118347B2/ja active Active
- 2013-02-01 EP EP13705321.1A patent/EP2809634B1/en not_active Not-in-force
- 2013-02-01 CN CN201380007842.3A patent/CN104105680A/zh active Pending
- 2013-02-01 SG SG11201404399SA patent/SG11201404399SA/en unknown
- 2013-02-01 BR BR112014018620A patent/BR112014018620A8/pt not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW225522B (enExample) * | 1992-02-24 | 1994-06-21 | Ciba Geigy Ag | |
| TW394786B (en) * | 1995-04-14 | 2000-06-21 | Ciba Sc Holding Ag | A stabilized monomer composition and a stabilizer mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101660610B1 (ko) | 2016-09-27 |
| EP2809634A1 (en) | 2014-12-10 |
| US8901362B2 (en) | 2014-12-02 |
| JP2015505579A (ja) | 2015-02-23 |
| BR112014018620A2 (enExample) | 2017-06-20 |
| TW201336907A (zh) | 2013-09-16 |
| EP2809634B1 (en) | 2018-01-31 |
| US20130204053A1 (en) | 2013-08-08 |
| WO2013116611A1 (en) | 2013-08-08 |
| KR20140119054A (ko) | 2014-10-08 |
| SG11201404399SA (en) | 2014-08-28 |
| BR112014018620A8 (pt) | 2017-07-11 |
| CN104105680A (zh) | 2014-10-15 |
| CA2862034A1 (en) | 2013-08-08 |
| JP6118347B2 (ja) | 2017-04-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |