KR20150055014A - 파라-자일렌 및 테레프탈산의 제조 방법 - Google Patents

파라-자일렌 및 테레프탈산의 제조 방법 Download PDF

Info

Publication number
KR20150055014A
KR20150055014A KR1020157009382A KR20157009382A KR20150055014A KR 20150055014 A KR20150055014 A KR 20150055014A KR 1020157009382 A KR1020157009382 A KR 1020157009382A KR 20157009382 A KR20157009382 A KR 20157009382A KR 20150055014 A KR20150055014 A KR 20150055014A
Authority
KR
South Korea
Prior art keywords
otf
catalyst
solvent
alkyl
triflate
Prior art date
Application number
KR1020157009382A
Other languages
English (en)
Korean (ko)
Inventor
마코토 엔. 마스노
마코토 엔. 마스노
리안 엘. 스미스
존 비셀
마크 포스터
패트릭 비. 스미스
데니스 에이. 허클
에드문드 제이. 스타크
다니엘 알. 헨톤
아디나 두미트라스쿠
캐서린 브룬
Original Assignee
마이크로마이다스, 인코포레이티드
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US13/838,761 external-priority patent/US8889938B2/en
Application filed by 마이크로마이다스, 인코포레이티드 filed Critical 마이크로마이다스, 인코포레이티드
Publication of KR20150055014A publication Critical patent/KR20150055014A/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/02—Monocyclic hydrocarbons
    • C07C15/067—C8H10 hydrocarbons
    • C07C15/08—Xylenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
    • 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
    • C07C2/46—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/56—Addition to acyclic hydrocarbons
    • C07C2/58—Catalytic processes
    • C07C2/62—Catalytic processes with acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C07C2/867—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 aldehyde or a ketone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • C07C49/14—Acetylacetone, i.e. 2,4-pentanedione
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • 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
    • C07C51/265—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 having alkyl side chains which are oxidised to carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/26—1,4 - Benzenedicarboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • C07C2521/08—Silica
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of rare earths
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2523/24—Chromium, molybdenum or tungsten
    • C07C2523/28—Molybdenum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
    • C07C2523/72—Copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/10—Chlorides
    • C07C2527/11—Hydrogen chloride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/122—Compounds comprising a halogen and copper
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
    • C07C2527/126—Aluminium chloride
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/16—Phosphorus; Compounds thereof containing oxygen
    • C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
    • C07C2527/173—Phosphoric acid or other acids with the formula Hn+2PnO3n+1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/14—Phosphorus; Compounds thereof
    • C07C2527/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C07C2527/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
    • C07C2527/19—Molybdenum
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/025—Sulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides

Landscapes

  • Chemical & Material Sciences (AREA)
  • 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)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
KR1020157009382A 2012-09-14 2013-09-13 파라-자일렌 및 테레프탈산의 제조 방법 KR20150055014A (ko)

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 2013-03-15
US13/838,761 US8889938B2 (en) 2012-03-15 2013-03-15 Methods of producing para-xylene
PCT/US2013/059660 WO2014043468A1 (en) 2012-09-14 2013-09-13 Methods of producing para-xylene and terephthalic acid

Publications (1)

Publication Number Publication Date
KR20150055014A true KR20150055014A (ko) 2015-05-20

Family

ID=50278710

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020157009382A KR20150055014A (ko) 2012-09-14 2013-09-13 파라-자일렌 및 테레프탈산의 제조 방법

Country Status (11)

Country Link
EP (1) EP2895446A1 (de)
JP (1) JP6503294B2 (de)
KR (1) KR20150055014A (de)
CN (1) CN104918901A (de)
AR (1) AR092565A1 (de)
BR (1) BR112015005701A2 (de)
HK (1) HK1212674A1 (de)
IN (1) IN2015DN02933A (de)
MX (1) MX2015003313A (de)
TW (1) TW201425272A (de)
WO (1) WO2014043468A1 (de)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170047802A (ko) * 2015-10-23 2017-05-08 에스케이케미칼주식회사 디메틸테레프탈레이트의 제조 방법
KR20170054230A (ko) * 2015-10-12 2017-05-17 차이나 페트로리움 앤드 케미컬 코포레이션 방향족 탄화수소, p-자일렌 및 테레프탈산의 제조 방법
KR20180049984A (ko) * 2016-11-04 2018-05-14 한국과학기술연구원 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 파라자일렌의 제조방법
KR20190061128A (ko) * 2017-11-27 2019-06-05 에스케이케미칼 주식회사 디메틸테레프탈레이트의 제조방법
KR20190089304A (ko) * 2018-01-22 2019-07-31 한국과학기술연구원 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 디알킬 테레프탈레이트의 제조방법

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112014006237A2 (pt) 2011-09-16 2017-04-11 Micromidas Inc método para produzir para-xileno, uso do para-xileno, método para produzir ácido tereftálico, método para produzir um composto
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
CN109020930A (zh) 2013-03-14 2018-12-18 微麦德斯公司 5-(卤代甲基)糠醛的提纯方法
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
EP3046914B1 (de) 2013-09-20 2022-09-21 Origin Materials Operating, Inc. Verfahren zur herstellung von 5-(halomethyl)furfural
EP3142997A1 (de) 2014-05-12 2017-03-22 Micromidas, Inc. Verfahren zur herstellung von verbindungen aus 5-(halomethyl)furfural
US11028221B2 (en) 2015-12-11 2021-06-08 SOCIETE ANONYME DES EAUX MINERALES D'EVIAN et en abrégé “S.A.E.M.E” PET polymer with an anti-crystallization comonomer that can be bio-sourced
EP3915970A1 (de) 2016-02-26 2021-12-01 Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO Aromatische verbindungen aus furanen
EP3210979A1 (de) 2016-02-26 2017-08-30 Nederlandse Organisatie voor toegepast- natuurwetenschappelijk onderzoek TNO Aromatische verbindungen aus furanen
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
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
TWI630192B (zh) * 2017-07-28 2018-07-21 遠東新世紀股份有限公司 Method for preparing alkylbenzene
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
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

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
WO2009110402A1 (ja) * 2008-03-03 2009-09-11 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
BR112014006237A2 (pt) * 2011-09-16 2017-04-11 Micromidas Inc método para produzir para-xileno, uso do para-xileno, método para produzir ácido tereftálico, método para produzir um composto

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170054230A (ko) * 2015-10-12 2017-05-17 차이나 페트로리움 앤드 케미컬 코포레이션 방향족 탄화수소, p-자일렌 및 테레프탈산의 제조 방법
KR20170047802A (ko) * 2015-10-23 2017-05-08 에스케이케미칼주식회사 디메틸테레프탈레이트의 제조 방법
KR20180049984A (ko) * 2016-11-04 2018-05-14 한국과학기술연구원 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 파라자일렌의 제조방법
KR20190061128A (ko) * 2017-11-27 2019-06-05 에스케이케미칼 주식회사 디메틸테레프탈레이트의 제조방법
KR20190089304A (ko) * 2018-01-22 2019-07-31 한국과학기술연구원 실리카에 담지된 헤테로폴리산 촉매 및 이를 이용한 디알킬 테레프탈레이트의 제조방법

Also Published As

Publication number Publication date
BR112015005701A2 (pt) 2017-07-04
AR092565A1 (es) 2015-04-22
JP2015531786A (ja) 2015-11-05
HK1212674A1 (zh) 2016-06-17
TW201425272A (zh) 2014-07-01
WO2014043468A1 (en) 2014-03-20
CN104918901A (zh) 2015-09-16
IN2015DN02933A (de) 2015-09-18
EP2895446A1 (de) 2015-07-22
MX2015003313A (es) 2015-07-14
JP6503294B2 (ja) 2019-04-17

Similar Documents

Publication Publication Date Title
KR20150055014A (ko) 파라-자일렌 및 테레프탈산의 제조 방법
US10125060B2 (en) Methods of producing para-xylene and terephthalic acid
JP6003643B2 (ja) アルキル化反応用触媒及び該触媒を用いたアルキル芳香族炭化水素化合物の製造方法
WO2017054321A1 (zh) 由乙二醇单甲醚直接制备乙二醇二甲醚并联产乙二醇的方法
WO2015023918A2 (en) Methods of producing alkylfurans
RU2421440C2 (ru) Способ получения диенов гидродимеризацией
US10414742B2 (en) Methods of producing alkylfurans
KR950001674B1 (ko) 알킬치환 방향족 탄화수소의 제조방법
US10392317B2 (en) Methods of producing para-xylene and terephthalic acid
US10364210B2 (en) Diamine compounds, dinitro compounds and other compounds, and methods of producing thereof and uses related thereof
CN103261154B (zh) 具有双(三氟甲磺酰基)乙基的化合物和酸催化剂及其制造方法
US20190031633A1 (en) Low pressure, high temperature process for forming 2,5-furandicarboxylic acid dialkyl ester
KR101004369B1 (ko) 방향족 요오드화 화합물의 제조 방법
JP6330806B2 (ja) 不飽和酸エステル又は不飽和酸の製造方法
CN102964224B (zh) 芳香族底物的烷氧基烷基化方法
WO2020215812A1 (zh) 一种2-烷基呋喃制4，4'-二烷基联苯的方法
KR101906435B1 (ko) 4,4’-디포르밀디페닐알칸의 제조 방법
CN101250092A (zh) 一种羟基芳香醚的合成方法
CN111417641A (zh) 二卤代二苯甲酮的新的环加合物前体及其制备
JP2015059098A (ja) 有機化合物の製造方法
JP2015077552A (ja) 還元反応用触媒組成物、１，６−ヘキサンジオールの製造方法、アミノベンゼン化合物の製造方法

Legal Events

Date Code Title Description
WITN Withdrawal due to no request for examination