JP2018513258A5 - - Google Patents
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- JP2018513258A5 JP2018513258A5 JP2017554871A JP2017554871A JP2018513258A5 JP 2018513258 A5 JP2018513258 A5 JP 2018513258A5 JP 2017554871 A JP2017554871 A JP 2017554871A JP 2017554871 A JP2017554871 A JP 2017554871A JP 2018513258 A5 JP2018513258 A5 JP 2018513258A5
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- JP
- Japan
- Prior art keywords
- tetramethylpiperidine
- oxide
- independently
- polymerization
- compound
- 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.)
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- -1 hydroquinone compound Chemical class 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 14
- 238000006116 polymerization reaction Methods 0.000 claims 10
- 230000002401 inhibitory effect Effects 0.000 claims 9
- FAPCFNWEPHTUQK-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)[NH+]1[O-] FAPCFNWEPHTUQK-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 150000002430 hydrocarbons Chemical class 0.000 claims 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- RVWUHFFPEOKYLB-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CC1(C)CCCC(C)(C)[NH+]1[O-] RVWUHFFPEOKYLB-UHFFFAOYSA-N 0.000 claims 2
- HVZQOGWWUPCQPC-UHFFFAOYSA-N 4-butoxy-2,2,6,6-tetramethylpiperidine Chemical compound CCCCOC1CC(C)(C)NC(C)(C)C1 HVZQOGWWUPCQPC-UHFFFAOYSA-N 0.000 claims 2
- WUPMXOQNNJYCHX-UHFFFAOYSA-N 4-ethoxy-2,2,6,6-tetramethyl-1-oxidopiperidin-1-ium Chemical compound CCOC1CC(C)(C)[NH+]([O-])C(C)(C)C1 WUPMXOQNNJYCHX-UHFFFAOYSA-N 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 238000005194 fractionation Methods 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 claims 1
- WEVQLTIEFPKGFU-UHFFFAOYSA-N 5-hydroxy-6-oxo-1,2-dihydroindole-2-carboxylic acid Chemical compound O=C1C(O)=CC2=CC(C(=O)O)NC2=C1 WEVQLTIEFPKGFU-UHFFFAOYSA-N 0.000 claims 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N Phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- 229950000688 Phenothiazine Drugs 0.000 claims 1
- 238000005865 alkene metathesis reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229910021386 carbon form Inorganic materials 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 230000003111 delayed Effects 0.000 claims 1
- 239000002283 diesel fuel Substances 0.000 claims 1
- 239000000295 fuel oil Substances 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 238000004642 transportation engineering Methods 0.000 claims 1
- 0 *c(cc(c1c2****1)O)c2O Chemical compound *c(cc(c1c2****1)O)c2O 0.000 description 1
Claims (13)
- R3が、アルキルである、請求項1または2に記載の方法。
- X1、X2、及びX3が独立して、−O−、または、−C(H)(R4)−であり、かつ、X1、X2、及びX3のうちの少なくとも1つが、−C(H)(R4)−であり、Z1、Z2、Z3、及びZ4が独立して、−O−、または、−C(H)(R4)−であり、かつ、Z1、Z2、Z3、及びZ4のうちの少なくとも2つが、−C(H)(R4)−である、請求項2または3に記載の方法。
- R1、R2、及びR3が独立して、アルキルであり、または、独立して、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、もしくはオクチルであり、または、独立して、メチル、エチル、プロピル、または、ブチルである、請求項1に記載の方法。
- R1、R2、及びR3が、メチルである、請求項1に記載の方法。
- 前記炭化水素流が、エチレン、プロピレン、アセチレン、ブタジエン、またはそれらの組合せを含有する、請求項1〜6のいずれか1項に記載の方法。
- 前記方法が、製造、精製、もしくは貯蔵プロセスの間の不飽和化合物の重合を安定化及び阻害する、または、前記方法が、一次分画プロセス、軽留分分画、プロセスガス圧縮、ブタジエン抽出、プロパン脱水素化、ディーゼル及び石油燃料安定化、オレフィンメタセシス、スチレン精製において、不飽和化合物の重合を安定化及び阻害するか、もしくは、エチレン性不飽和種を含む樹脂及び組成物の重合を遅延させる、請求項1〜7のいずれか1項に記載の方法。
- 前記プロセスが、ブタジエン抽出、または、スチレン精製である、請求項8に記載の方法。
- 前記炭化水素流を、式1のヒドロキノンと組合せたニトロキシド化合物と接触させることをさらに含み、
前記ニトロキシド化合物が、2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−メトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−エトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−プロポキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ブトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、もしくはそれらの組合せであるか、または、前記ニトロキシド化合物が、2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ブトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、もしくはそれらの組合せであるか、または、前記ニトロキシド化合物が、4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシドを含む、請求項1〜9のいずれか1項に記載の方法。 - 前記重合阻害組成物が、フェノール、アルキル化フェノール、ニトロフェノール、ニトロソフェノール、キノン、キノンエーテル、キノンメチド、アミン、ヒドロキシルアミン、またはフェノチアジンから選択される付加的重合阻害剤をさらに含む、請求項11に記載の重合阻害組成物。
- ニトロキシド化合物をさらに含み、
前記ニトロキシド化合物が、2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−メトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−エトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−プロポキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ブトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、もしくはそれらの組合せであるか、または、前記ニトロキシド化合物が、2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、4−ブトキシ−2,2,6,6−テトラメチルピペリジン−1−オキシド、もしくはそれらの組合せであるか、または、前記ニトロキシド化合物が、4−ヒドロキシ−2,2,6,6−テトラメチルピペリジン−1−オキシドを含む、請求項11または12に記載の重合阻害組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562150022P | 2015-04-20 | 2015-04-20 | |
US62/150,022 | 2015-04-20 | ||
PCT/US2016/028239 WO2016172076A1 (en) | 2015-04-20 | 2016-04-19 | Sterically hindered hydroquinones as antifoulants for unsaturated monomers |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2018513258A JP2018513258A (ja) | 2018-05-24 |
JP2018513258A5 true JP2018513258A5 (ja) | 2019-05-30 |
JP6843067B2 JP6843067B2 (ja) | 2021-03-17 |
Family
ID=57128251
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017554871A Active JP6843067B2 (ja) | 2015-04-20 | 2016-04-19 | 不飽和モノマー類の重合を阻害する方法 |
Country Status (12)
Country | Link |
---|---|
US (1) | US10155705B2 (ja) |
EP (1) | EP3289046A4 (ja) |
JP (1) | JP6843067B2 (ja) |
KR (1) | KR102616836B1 (ja) |
CN (1) | CN107532083A (ja) |
AR (1) | AR104327A1 (ja) |
BR (1) | BR112017022431B1 (ja) |
CA (1) | CA2982465C (ja) |
RU (1) | RU2746125C2 (ja) |
SA (1) | SA517390157B1 (ja) |
TW (1) | TWI624480B (ja) |
WO (1) | WO2016172076A1 (ja) |
Families Citing this family (6)
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WO2020014606A1 (en) | 2018-07-13 | 2020-01-16 | Ecolab Usa Inc. | Compositions of oxygenated amines and quinone methides as antifoulants for vinylic monomers |
US11180578B2 (en) | 2018-07-13 | 2021-11-23 | Ecolab Usa Inc. | Polymerization inhibitor and retarder compositions with amine stabilizer |
KR20210068020A (ko) | 2018-09-28 | 2021-06-08 | 에코랍 유에스에이 인코퍼레이티드 | 아미노-퀴논 중합방지제 및 이의 사용 방법 |
KR20210006634A (ko) | 2019-07-09 | 2021-01-19 | 에스케이이노베이션 주식회사 | 윤활 조성물 및 이를 이용한 공중합체의 제조 방법 |
TW202114976A (zh) | 2019-10-11 | 2021-04-16 | 美商藝康美國公司 | 醌甲基化物及銨鹽抗聚合劑組合物及方法 |
KR20210106092A (ko) | 2020-02-20 | 2021-08-30 | 에스케이이노베이션 주식회사 | 에틸렌-카르복실산 공중합체의 제조 방법 |
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DE102013204950A1 (de) | 2013-03-20 | 2014-09-25 | Evonik Industries Ag | Verfahren und Zusammensetzung zur Inhibierung der Polymerisation von Cyclopentadienverbindungen |
US9399622B2 (en) | 2013-12-03 | 2016-07-26 | Ecolab Usa Inc. | Nitroxide hydroxylamine and phenylenediamine combinations as polymerization inhibitors for ethylenically unsaturated monomer processes |
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2016
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- 2016-04-19 KR KR1020177031676A patent/KR102616836B1/ko active IP Right Grant
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