CA2876153A1 - Process for production of adipic acid from 1,6-hexanediol - Google Patents

Process for production of adipic acid from 1,6-hexanediol Download PDF

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Publication number
CA2876153A1
CA2876153A1 CA2876153A CA2876153A CA2876153A1 CA 2876153 A1 CA2876153 A1 CA 2876153A1 CA 2876153 A CA2876153 A CA 2876153A CA 2876153 A CA2876153 A CA 2876153A CA 2876153 A1 CA2876153 A1 CA 2876153A1
Authority
CA
Canada
Prior art keywords
hexanediol
catalyst
support
oxygen
zirconia
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.)
Abandoned
Application number
CA2876153A
Other languages
English (en)
French (fr)
Inventor
Eric L. Dias
Vincent J. Murphy
James A.W. Shoemaker
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Archer Daniels Midland Co
Original Assignee
Rennovia Inc
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
Application filed by Rennovia Inc filed Critical Rennovia Inc
Publication of CA2876153A1 publication Critical patent/CA2876153A1/en
Abandoned legal-status Critical Current

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    • 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
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/42—Platinum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/48—Silver or gold
    • B01J23/52—Gold
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/652—Chromium, molybdenum or tungsten
    • B01J23/6527—Tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/615—100-500 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/64—Pore diameter
    • B01J35/647—2-50 nm
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/64—Pore diameter
    • B01J35/651—50-500 nm
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/50—Use of additives, e.g. for stabilisation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/66—Silver or gold
    • B01J23/68—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/683—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum or tungsten
    • B01J23/687—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum or tungsten with tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/19—Catalysts containing parts with different compositions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Nanotechnology (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2876153A 2012-06-11 2013-06-11 Process for production of adipic acid from 1,6-hexanediol Abandoned CA2876153A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261658364P 2012-06-11 2012-06-11
US61/658,364 2012-06-11
PCT/US2013/045096 WO2013188348A2 (en) 2012-06-11 2013-06-11 Process for production of adipic acid from 1,6-hexanediol

Publications (1)

Publication Number Publication Date
CA2876153A1 true CA2876153A1 (en) 2013-12-19

Family

ID=48656277

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2876153A Abandoned CA2876153A1 (en) 2012-06-11 2013-06-11 Process for production of adipic acid from 1,6-hexanediol

Country Status (15)

Country Link
US (3) US9035094B2 (https=)
EP (2) EP2858748B1 (https=)
JP (1) JP6209603B2 (https=)
KR (1) KR20150018877A (https=)
CN (2) CN111454144B (https=)
AR (1) AR091409A1 (https=)
AU (1) AU2013274530B2 (https=)
BR (1) BR112014030857B1 (https=)
CA (1) CA2876153A1 (https=)
EA (1) EA201492252A1 (https=)
HK (1) HK1210087A1 (https=)
MX (1) MX2014015180A (https=)
SA (1) SA113340632B1 (https=)
SG (2) SG10201604678PA (https=)
WO (1) WO2013188348A2 (https=)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR089707A1 (es) 2012-01-18 2014-09-10 Rennovia Inc Proceso para la produccion de hexametilendiamina a partir de materiales que contienen carbohidratos y compuestos intermedios para la misma
US8946411B2 (en) 2012-02-23 2015-02-03 Rennovia, Inc. Production of caprolactam from adipic acid
AU2013274530B2 (en) 2012-06-11 2017-09-28 Rennovia, Inc. Process for production of adipic acid from 1,6-hexanediol
US8986637B2 (en) * 2012-11-30 2015-03-24 Johnson Matthey Public Limited Company Bimetallic catalyst
JP2017537920A (ja) 2014-12-02 2017-12-21 レノビア インコーポレイテッド ５−ヒドロキシメチルフルフラールから２，５−ビスヒドロキシメチルフラン、２，５−ビス−ヒドロキシメチルテトラヒドロフラン、１，６−ヘキサンジオールおよび１，２，６−ヘキサントリオールを生成する工程
EP3402787A4 (en) 2016-01-13 2019-11-27 Stora Enso Oyj PROCESS FOR THE PREPARATION OF 2,5-FURANDIC ACETIC ACID AND INTERMEDIATES AND DERIVATIVES THEREOF
EP3652161A1 (en) 2017-07-12 2020-05-20 Stora Enso Oyj Purified 2,5-furandicarboxylic acid pathway products
KR102504661B1 (ko) * 2017-08-18 2023-02-27 차이나 페트로리움 앤드 케미컬 코포레이션 중질 방향족 화합물로 경질 방향족 화합물을 제조하기 위한 촉매 및 이의 제조 방법과 용도
WO2019047113A1 (en) * 2017-09-07 2019-03-14 Rhodia Operations PROCESS FOR OXIDATION OF ALCOHOLS
CN116726913A (zh) * 2023-02-01 2023-09-12 北京化工大学 一种用于生物质甘油氧化制备甘油酸的高效催化剂的制备方法及其应用

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3739020A (en) * 1969-05-13 1973-06-12 Nat Distillers Chem Corp Preparation of carboxylic acids
DE2407146A1 (de) * 1974-02-15 1975-09-04 Erdoelchemie Gmbh Verfahren zur herstellung von dicarbonsaeuren
US4400468A (en) * 1981-10-05 1983-08-23 Hydrocarbon Research Inc. Process for producing adipic acid from biomass
US5128291A (en) * 1990-12-11 1992-07-07 Wax Michael J Porous titania or zirconia spheres
CA2103876A1 (en) * 1992-08-27 1994-02-28 Stuart Leon Soled Group viii metal containing tungsten oxide silica modified zirconia as acid catalyst
JP4075292B2 (ja) * 2000-07-24 2008-04-16 トヨタ自動車株式会社 パティキュレート浄化触媒
US7119225B1 (en) * 2000-08-18 2006-10-10 E. I. Du Pont De Nemours And Company Gold catalyst for selective oxidation
AU2000267914A1 (en) * 2000-08-18 2002-03-04 E.I. Du Pont De Nemours And Company Gold catalyst for selective oxidation
EP1581339A2 (en) * 2002-12-20 2005-10-05 Honda Giken Kogyo Kabushiki Kaisha Methods for the preparation of catalysts for hydrogen generation
US7125536B2 (en) * 2004-02-06 2006-10-24 Millennium Inorganic Chemicals, Inc. Nano-structured particles with high thermal stability
JP2005330225A (ja) * 2004-05-20 2005-12-02 Nippon Shokubai Co Ltd カルボン酸及び／又はその塩の製造方法
DE102007025444A1 (de) * 2007-05-31 2008-12-11 Süd-Chemie AG VAM-Schalenkatalysator, Verfahren zu dessen Herstellung sowie dessen Verwendung
US8669397B2 (en) * 2009-06-13 2014-03-11 Rennovia, Inc. Production of adipic acid and derivatives from carbohydrate-containing materials
EP2390247A1 (en) 2010-05-26 2011-11-30 Netherlands Organisation for Scientific Research (Advanced Chemical Technologies for Sustainability) Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde
US9770705B2 (en) * 2010-06-11 2017-09-26 Rennovia Inc. Oxidation catalysts
US8366907B2 (en) * 2010-08-02 2013-02-05 Battelle Memorial Institute Deoxygenation of fatty acids for preparation of hydrocarbons
AU2013274530B2 (en) 2012-06-11 2017-09-28 Rennovia, Inc. Process for production of adipic acid from 1,6-hexanediol

Also Published As

Publication number Publication date
CN111454144A (zh) 2020-07-28
HK1210087A1 (en) 2016-04-15
AR091409A1 (es) 2015-02-04
EA201492252A1 (ru) 2015-05-29
AU2013274530A1 (en) 2015-01-22
BR112014030857B1 (pt) 2021-06-22
JP2015525229A (ja) 2015-09-03
SG10201604678PA (en) 2016-07-28
US20160074835A1 (en) 2016-03-17
EP2858748B1 (en) 2018-04-11
WO2013188348A3 (en) 2014-03-20
CN104364010B (zh) 2020-02-11
US9035094B2 (en) 2015-05-19
CN111454144B (zh) 2024-11-15
CN104364010A (zh) 2015-02-18
EP2858748A2 (en) 2015-04-15
SG11201408289UA (en) 2015-01-29
MX2014015180A (es) 2015-02-17
AU2013274530B2 (en) 2017-09-28
EP3363537A1 (en) 2018-08-22
WO2013188348A2 (en) 2013-12-19
US20170226038A1 (en) 2017-08-10
JP6209603B2 (ja) 2017-10-04
BR112014030857A2 (pt) 2017-06-27
KR20150018877A (ko) 2015-02-24
SA113340632B1 (ar) 2015-12-06
US20130331606A1 (en) 2013-12-12
US10077226B2 (en) 2018-09-18
EP3363537B1 (en) 2021-10-20

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