JP6503294B2 - パラ−キシレンおよびテレフタル酸の生成方法 - Google Patents

パラ−キシレンおよびテレフタル酸の生成方法 Download PDF

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JP6503294B2
JP6503294B2 JP2015532075A JP2015532075A JP6503294B2 JP 6503294 B2 JP6503294 B2 JP 6503294B2 JP 2015532075 A JP2015532075 A JP 2015532075A JP 2015532075 A JP2015532075 A JP 2015532075A JP 6503294 B2 JP6503294 B2 JP 6503294B2
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triflate
catalyst
otf
solvent
ethylene
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JP2015531786A (ja
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エヌ. マスノ,マコト
エヌ. マスノ,マコト
エル. スミス,ライアン
エル. スミス,ライアン
ビッセル,ジョン
フォスター,マーク
ビー. スミス,パトリック
ビー. スミス,パトリック
エー. ハカル,デニス
エー. ハカル,デニス
ジェイ. スターク,エドマンド
ジェイ. スターク,エドマンド
アール. ハントン,ダニエル
アール. ハントン,ダニエル
ドミトラスク,アディーナ
ブルーン,キャサリン
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マイクロマイダス,インコーポレイテッド
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    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
    • C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
    • C07C2/865—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an ether
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    • C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
    • C07C2/44—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion of conjugated dienes only
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    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
JP2015532075A 2012-09-14 2013-09-13 パラ−キシレンおよびテレフタル酸の生成方法 Active JP6503294B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201261701276P 2012-09-14 2012-09-14
US61/701,276 2012-09-14
US13/838,761 US8889938B2 (en) 2012-03-15 2013-03-15 Methods of producing para-xylene
US13/838,761 2013-03-15
PCT/US2013/059660 WO2014043468A1 (en) 2012-09-14 2013-09-13 Methods of producing para-xylene and terephthalic acid

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JP2015531786A JP2015531786A (ja) 2015-11-05
JP6503294B2 true JP6503294B2 (ja) 2019-04-17

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KR (1) KR20150055014A (OSRAM)
CN (1) CN104918901A (OSRAM)
AR (1) AR092565A1 (OSRAM)
BR (1) BR112015005701A2 (OSRAM)
HK (1) HK1212674A1 (OSRAM)
IN (1) IN2015DN02933A (OSRAM)
MX (1) MX2015003313A (OSRAM)
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Families Citing this family (24)

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Publication number Priority date Publication date Assignee Title
US9260359B2 (en) 2011-09-16 2016-02-16 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid
US8889938B2 (en) 2012-03-15 2014-11-18 Micromidas, Inc. Methods of producing para-xylene
US10392317B2 (en) 2012-09-14 2019-08-27 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid
SG11201507352YA (en) 2013-03-14 2015-10-29 Micromidas Inc Methods for purifying 5-(halomethyl)furfural
US20140296600A1 (en) * 2013-04-01 2014-10-02 University Of Delaware Production of para-xylene by catalytically reacting 2,5-dimethylfuran and ethylene in a solvent
BR112016005974B8 (pt) 2013-09-20 2022-12-06 Micromidas Inc Métodos para produção de 5-(halometil) furfural
TW201609681A (zh) * 2014-05-12 2016-03-16 微麥得斯公司 自5-(鹵甲基)糠醛製造化合物之方法
CN106565396B (zh) * 2015-10-12 2019-04-12 中国石油化工股份有限公司 环加成生产芳烃的方法
KR102394356B1 (ko) * 2015-10-23 2022-05-04 에스케이케미칼 주식회사 디메틸테레프탈레이트의 제조 방법
CN108473666A (zh) 2015-12-11 2018-08-31 埃维昂矿泉水有限公司 具有可为生物来源的抗结晶共聚单体的pet聚合物
CN108884012B (zh) 2016-02-26 2022-04-15 荷兰应用自然科学研究组织Tno 来自呋喃类化合物的芳香族化合物
EP3210979A1 (en) 2016-02-26 2017-08-30 Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO Aromatic compounds from furanics
KR101949431B1 (ko) * 2016-11-04 2019-02-19 한국과학기술연구원 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 파라자일렌의 제조방법
CN108117478B (zh) * 2016-11-29 2021-02-05 中国科学院大连化学物理研究所 1,4-环己烷二甲醇或1,4-环己烷二甲酸的制备方法
CN108117489B (zh) * 2016-11-29 2020-10-16 中国科学院大连化学物理研究所 一种由巴豆醛和甲醛制备酯的方法
TWI630192B (zh) * 2017-07-28 2018-07-21 遠東新世紀股份有限公司 Method for preparing alkylbenzene
KR102394369B1 (ko) * 2017-11-27 2022-05-04 에스케이케미칼 주식회사 디메틸테레프탈레이트의 제조방법
KR102024755B1 (ko) * 2018-01-22 2019-11-04 한국과학기술연구원 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 디알킬 테레프탈레이트의 제조방법
CN111217659B (zh) * 2018-11-27 2021-04-16 中国科学院大连化学物理研究所 一种由异戊二烯和甲基对苯醌制备2,6-二甲基萘的方法
CN111004078B (zh) * 2019-12-24 2021-03-26 北京化工大学 一种生物基对二甲苯的制备方法
KR20240012491A (ko) * 2021-05-21 2024-01-29 차이나 페트로리움 앤드 케미컬 코포레이션 바이오매스 전환에 의해 p-크실렌을 제조하는 방법
CN115385771B (zh) * 2021-05-21 2024-05-28 中国石油化工股份有限公司 一种对二甲苯的制备方法
CN116374965B (zh) * 2023-02-08 2024-12-24 浙江健立化学有限公司 一种非均相催化合成双氟磺酰亚胺锂关键中间体的方法
CN119143147B (zh) 2023-06-15 2026-04-21 中国石油化工股份有限公司 P修饰的金属掺杂mww分子筛及其制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003055280A (ja) * 2001-08-17 2003-02-26 Nippon Petrochemicals Co Ltd 縮合環含有化合物の製法
JPWO2009110402A1 (ja) * 2008-03-03 2011-07-14 東レ株式会社 パラキシレンの製造方法
US8314267B2 (en) * 2009-06-26 2012-11-20 Uop Llc Carbohydrate route to para-xylene and terephthalic acid
JP5299972B2 (ja) * 2009-12-04 2013-09-25 独立行政法人産業技術総合研究所 フラン類の製造方法
US9260359B2 (en) * 2011-09-16 2016-02-16 Micromidas, Inc. Methods of producing para-xylene and terephthalic acid

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JP2015531786A (ja) 2015-11-05
CN104918901A (zh) 2015-09-16
TW201425272A (zh) 2014-07-01
IN2015DN02933A (OSRAM) 2015-09-18
AR092565A1 (es) 2015-04-22
KR20150055014A (ko) 2015-05-20
MX2015003313A (es) 2015-07-14
BR112015005701A2 (pt) 2017-07-04
HK1212674A1 (zh) 2016-06-17
EP2895446A1 (en) 2015-07-22

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