CN103228626B - 由5-羟甲基-2-糠醛制备己内酯、己内酰胺、2，5-四氢呋喃-二甲醇、1，6-己二醇或1，2，6-己三醇的方法 - Google Patents

由5-羟甲基-2-糠醛制备己内酯、己内酰胺、2，5-四氢呋喃-二甲醇、1，6-己二醇或1，2，6-己三醇的方法 Download PDF

Info

Publication number
CN103228626B
CN103228626B CN201180036114.6A CN201180036114A CN103228626B CN 103228626 B CN103228626 B CN 103228626B CN 201180036114 A CN201180036114 A CN 201180036114A CN 103228626 B CN103228626 B CN 103228626B
Authority
CN
China
Prior art keywords
hexanetriol
hexanediol
catalyst
dimethanol
tetrahydrofuran
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.)
Expired - Fee Related
Application number
CN201180036114.6A
Other languages
English (en)
Chinese (zh)
Other versions
CN103228626A (zh
Inventor
约翰尼斯·杰拉尔德斯·德弗里斯
泰迪
皮姆·华特·潘
I·V·美利恩·卡布雷拉
H·J·黑列斯
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.)
NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH (ADVANCED CHEMICAL TECHNOLOGIES FOR SUSTAINABILITY)
Original Assignee
NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH (ADVANCED CHEMICAL TECHNOLOGIES FOR SUSTAINABILITY)
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 NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH (ADVANCED CHEMICAL TECHNOLOGIES FOR SUSTAINABILITY) filed Critical NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH (ADVANCED CHEMICAL TECHNOLOGIES FOR SUSTAINABILITY)
Publication of CN103228626A publication Critical patent/CN103228626A/zh
Application granted granted Critical
Publication of CN103228626B publication Critical patent/CN103228626B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/04—Seven-membered rings not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C07D201/02—Preparation of lactams
    • C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyrane Compounds (AREA)
CN201180036114.6A 2010-05-26 2011-03-23 由5-羟甲基-2-糠醛制备己内酯、己内酰胺、2，5-四氢呋喃-二甲醇、1，6-己二醇或1，2，6-己三醇的方法 Expired - Fee Related CN103228626B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10163881.5 2010-05-26
EP10163881A EP2390247A1 (en) 2010-05-26 2010-05-26 Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde
PCT/NL2011/050200 WO2011149339A1 (en) 2010-05-26 2011-03-23 Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran-dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde

Publications (2)

Publication Number Publication Date
CN103228626A CN103228626A (zh) 2013-07-31
CN103228626B true CN103228626B (zh) 2016-08-03

Family

ID=42797300

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201180036114.6A Expired - Fee Related CN103228626B (zh) 2010-05-26 2011-03-23 由5-羟甲基-2-糠醛制备己内酯、己内酰胺、2，5-四氢呋喃-二甲醇、1，6-己二醇或1，2，6-己三醇的方法

Country Status (8)

Country Link
US (1) US9199961B2 (https=)
EP (2) EP2390247A1 (https=)
JP (1) JP6327853B2 (https=)
CN (1) CN103228626B (https=)
BR (1) BR112012029996B1 (https=)
CA (1) CA2800797C (https=)
ES (1) ES2727436T3 (https=)
WO (1) WO2011149339A1 (https=)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011149839A1 (en) 2010-05-24 2011-12-01 Tandus Flooring, Inc. Textile backing formed from recycled 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
US8884036B2 (en) 2011-12-30 2014-11-11 E I Du Pont De Nemours And Company Production of hydroxymethylfurfural from levoglucosenone
EP2797866A4 (en) * 2011-12-30 2015-08-05 Du Pont PROCESS FOR THE PREPARATION OF 1,6-HEXANEDIOL
US8865940B2 (en) 2011-12-30 2014-10-21 E I Du Pont De Nemours And Company Process for preparing 1,6-hexanediol
BR112014015994A2 (pt) * 2011-12-30 2018-05-22 Du Pont processo.
JP2015503569A (ja) * 2011-12-30 2015-02-02 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ ヘキサンジオールを生成するための方法
US8889912B2 (en) 2011-12-30 2014-11-18 E I Du Pont De Nemours And Company Process for preparing 1,6-hexanediol
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
JP6168044B2 (ja) * 2012-03-09 2017-07-26 宇部興産株式会社 テトラヒドロフラン化合物の製造方法
EP2644585A1 (en) 2012-03-30 2013-10-02 Rheinisch-Westfälisch-Technische Hochschule Aachen Method for the production of aliphatic alcohols and/or their ethers
US8846985B2 (en) 2012-04-27 2014-09-30 E I Du Pont De Nemours And Company Production of alpha, omega-diols
US9018423B2 (en) 2012-04-27 2015-04-28 E I Du Pont De Nemours And Company Production of alpha, omega-diols
US8859826B2 (en) 2012-04-27 2014-10-14 E I Du Pont De Nemours And Company Production of alpha, omega-diols
AU2013274530B2 (en) 2012-06-11 2017-09-28 Rennovia, Inc. Process for production of adipic acid from 1,6-hexanediol
FR2995897B1 (fr) * 2012-09-27 2014-10-10 Roquette Freres Procede de synthese de 2,5-di(hydroxymethyl)furane et de 2,5-di(hydroxymethyl)tetrahydrofurane par hydrogenation selective de furane-2,5-dialdehyde
WO2014152366A1 (en) * 2013-03-14 2014-09-25 Pronghorn Renewables Llc Method and catalyst for the production of alcohols, diols, cyclic ethers and other products from pentose and hexose sugars
CN105658700B (zh) * 2013-10-22 2018-07-10 英派尔科技开发有限公司 用于产生尼龙6的化合物和方法
WO2015060827A1 (en) * 2013-10-22 2015-04-30 Empire Technology Development Llc Methods and compounds for producing nylon 6,6
CN105658616A (zh) 2013-10-25 2016-06-08 英派尔科技开发有限公司 产生二羰基化合物的方法
EA201691459A1 (ru) 2014-01-27 2016-12-30 Ренновия Инк. Преобразование фруктозосодержащего исходного сырья в hmf-содержащий продукт
RU2016141809A (ru) * 2014-04-10 2018-05-10 Арчер Дэниелс Мидлэнд Компани Синтез R-глюкозидов сахароспиртов, восстановленных сахароспиртов и фурановых производных восстановленных сахароспиртов
JP2017513841A (ja) * 2014-04-10 2017-06-01 アーチャー−ダニエルズ−ミッドランド カンパニー 還元糖アルコール、フラン誘導体の合成
CN111205173A (zh) * 2014-05-12 2020-05-29 威尔迪亚公司 来自生物质精制的经氧化分子的氢化
WO2016043589A1 (en) * 2014-09-19 2016-03-24 Rijksuniversiteit Groningen Method for reducing hydroxymethylfurfural (hmf)
CN107074761B (zh) * 2014-10-30 2020-04-14 东丽株式会社 ε-己内酰胺的制造方法
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
CN104591369A (zh) * 2014-12-23 2015-05-06 南京林业大学 一种用于促使过氧化氢产生羟基自由基的复合药剂及其应用
GB201506701D0 (en) 2015-04-20 2015-06-03 Univ York Method for converting waste lignocellulosic materials derived from converting lignocellulose to ethanol into levoglucosenone
CN106866360B (zh) * 2015-12-10 2020-09-04 中国科学院大连化学物理研究所 一种5-羟甲基糠醛催化转化制备1,6-己二醇的方法
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
CN111777578B (zh) * 2020-07-15 2022-06-24 烟台大学 5-羟甲基糠醛加氢制备2,5-二羟甲基四氢呋喃的方法
DE102021209234A1 (de) 2021-08-23 2023-02-23 Continental Reifen Deutschland Gmbh Verfahren zum Herstellen von nachhaltigeren Verbundmaterialien zur Verwendung bei der Herstellung von Fahrzeugreifen
CN117229123A (zh) * 2023-08-14 2023-12-15 中科国生(杭州)科技有限公司 一种1,2,6-己三醇的制备方法
KR20250076198A (ko) * 2023-11-22 2025-05-29 한국생산기술연구원 루테늄 담지 알루미나 촉매, 그의 제조방법 및 그를 이용한 연속식 테트라하이드로퓨란 다이메탄올(thfdm) 제조장치
CN120754873B (zh) * 2025-09-10 2025-12-02 陕西开达化工有限责任公司 糠醛加氢胺化制糠胺催化剂及其制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3070633A (en) * 1958-09-10 1962-12-25 Merck & Co Inc Process for producing 1, 6-hexanediol
US4400468A (en) * 1981-10-05 1983-08-23 Hydrocarbon Research Inc. Process for producing adipic acid from biomass
JP2003321427A (ja) * 2002-04-30 2003-11-11 Toyota Motor Corp アミド化合物およびアミノ化合物の製造方法
CN101528725A (zh) * 2006-10-18 2009-09-09 巴斯夫欧洲公司 由二元醇生产内酯的方法

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3064008A (en) 1962-11-13 I i i i i i
US3000880A (en) 1961-09-19 Production of epsilon caprolactams
US3083236A (en) 1958-09-10 1963-03-26 Merck & Co Inc Hydrogenation of 5-hydroxy-methyl furfural
US3025306A (en) 1960-05-31 1962-03-13 Union Carbide Corp Process for the production of epsiloncaprolactones and carboxylic acids
US3317563A (en) 1963-12-26 1967-05-02 Celanese Corp Preparation of epsilon-caprolactone
JPS5268422A (en) 1975-12-03 1977-06-07 Yokogawa Hokushin Electric Corp Two-color electrostatic recording apparatus
JPS5524107A (en) 1978-08-09 1980-02-21 Asahi Chem Ind Co Ltd Preparation of lactone
JPS5925383B2 (ja) 1979-03-30 1984-06-16 シャープ株式会社 半導体装置
US4324710A (en) * 1980-10-02 1982-04-13 The Firestone Tire & Rubber Company Naturally occurring thermoplastic resins as a substitute for various petroleum-derived materials in rubber stocks
JPS5925383A (ja) 1982-07-30 1984-02-09 Nippon Shirika Kogyo Kk 亜臭素酸およびその塩によるラクトンの製造法
JPS6148509A (ja) 1984-08-13 1986-03-10 Nippon Steel Corp 転炉炉口付着物加熱切削除去方法
US5451673A (en) * 1993-04-23 1995-09-19 The United States Of America As Represented By The Secretary Of Agriculture Films fabricated from mixtures of pectin and starch
DE19510438A1 (de) * 1995-03-22 1996-09-26 Basf Ag Verfahren zur Herstellung von 1,4-Butandiol und Tetrahydrofuran aus Furan
US6300496B1 (en) * 1999-10-06 2001-10-09 Union Carbide Chemicals & Plastics Technology Corporation Processes for producing epsilon caprolactams
BRPI0506942B1 (pt) 2004-01-19 2015-07-28 Dsm Ip Assets B.V. Síntese bioquímica de ácido 6-amino capróico
JP2008502728A (ja) 2004-06-10 2008-01-31 ボード、オブ、トラスティーズ、オブ、ミシガン、ステイト、ユニバーシティ リジンからのカプロラクタムの合成
US7393963B2 (en) * 2004-12-10 2008-07-01 Archer-Daniels-Midland Company Conversion of 2,5-(hydroxymethyl)furaldehyde to industrial derivatives, purification of the derivatives, and industrial uses therefor
AU2008205169B2 (en) 2007-01-05 2012-02-02 Novartis Ag Imidazole derivatives as kinesin spindle protein inhibitors (Eg-5)
WO2009154566A1 (en) * 2008-06-18 2009-12-23 Agency For Science, Technology And Research Production of hydroxymethylfurfural
JP5209426B2 (ja) * 2008-09-22 2013-06-12 富士フイルム株式会社 １，２，４−オキサジアゾール誘導体の製造方法
JP2010208968A (ja) 2009-03-09 2010-09-24 Daicel Chem Ind Ltd 表面金固定化触媒によるラクトンの製造方法
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3070633A (en) * 1958-09-10 1962-12-25 Merck & Co Inc Process for producing 1, 6-hexanediol
US4400468A (en) * 1981-10-05 1983-08-23 Hydrocarbon Research Inc. Process for producing adipic acid from biomass
JP2003321427A (ja) * 2002-04-30 2003-11-11 Toyota Motor Corp アミド化合物およびアミノ化合物の製造方法
CN101528725A (zh) * 2006-10-18 2009-09-09 巴斯夫欧洲公司 由二元醇生产内酯的方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemoselective Hydrogenolysis of Tetrahydropyran-2-methanol to 1,6-Hexanediol over Rhenium-Modified Carbon-Supported Rhodium Catalysts;Kaiyou Chen，等;《ChemCatChem 》;20100415;第2卷;第548页Scheme 1 *
ORGANOTINS AS ETHERJFICATION CATALYSTS. III. ETHRRIFICATIONS AND HYDRO-HYDROXY-ELIMINATIONS PROMOTED BY BUTYLTIN TRICHLORIDE;Daniele MARTON，等;《Tetrahedron》;19891231;第45卷(第22期);第7103页表格2中第12项 *

Also Published As

Publication number Publication date
JP6327853B2 (ja) 2018-05-23
WO2011149339A1 (en) 2011-12-01
CA2800797C (en) 2019-04-16
BR112012029996B1 (pt) 2021-10-26
ES2727436T3 (es) 2019-10-16
JP2013531638A (ja) 2013-08-08
CN103228626A (zh) 2013-07-31
US9199961B2 (en) 2015-12-01
CA2800797A1 (en) 2011-12-01
US20130137863A1 (en) 2013-05-30
EP2576506A1 (en) 2013-04-10
EP2390247A1 (en) 2011-11-30
BR112012029996A2 (pt) 2021-05-04
EP2576506B1 (en) 2019-03-06

Similar Documents

Publication Publication Date Title
CN103228626B (zh) 由5-羟甲基-2-糠醛制备己内酯、己内酰胺、2，5-四氢呋喃-二甲醇、1，6-己二醇或1，2，6-己三醇的方法
Valentini et al. Formic acid, a biomass-derived source of energy and hydrogen for biomass upgrading
Chen et al. How catalysts and experimental conditions determine the selective hydroconversion of furfural and 5-hydroxymethylfurfural
Mariscal et al. Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels
Yan et al. Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals
US10195592B2 (en) Zirconium-based metal-organic frameworks as catalyst for transfer hydrogenation
CN103193736B (zh) 一种催化加氢合成γ-戊内酯的方法
CN103450940B (zh) 一种由生物质衍生物制备航空煤油和柴油的方法
Bunrit et al. Photo–thermo-dual catalysis of levulinic acid and levulinate ester to γ-valerolactone
US20110263880A1 (en) Efficient method for preparing 2,5-dimethylfuran
CN105330523A (zh) 以生物质资源为原料制备环戊酮的方法
US20130296579A1 (en) PROCESS FOR PREPARATION OF gamma-VALEROLACTONE VIA CATALYTIC HYDROGENATION OF LEVULINIC ACID
US10189764B2 (en) Hydrogenation of oxygenated molecules from biomass refining
CN106279075A (zh) 一种催化5‑羟甲基糠醛制备2,5‑二甲基呋喃的方法
CN110283147A (zh) 甲酸供氢、非贵金属负载氮杂碳催化5-hmf转移氢化制备2,5-呋喃二甲醇的方法
JP6057376B2 (ja) ヒドロキシメチルフルフラール及び／又はフルフラールの還元方法
EP3774753B1 (en) Conversion of 1,2,5,6-hexanetetrol (hto) to tetrahydrofuran dicarboxylic acid (thfdca)
Wei et al. Chemoselective hydrogenation of biomass-derived 5-hydroxymethylfurfural into furanyl diols
CN105254599A (zh) 一种以糠醛为原料制备γ-丁内酯的方法
CN102872897B (zh) 一种糠醇液相催化加氢制1,5-戊二醇的催化剂及其制备方法与应用
CN101870695B (zh) 一种3-(2-氯乙基)-6,7,8,9-四氢9-羟基-2-甲基四氢-吡啶[1,2-α]嘧啶-4-酮的制备方法
EP3023479A1 (en) Process for the deoxygenation of alcohols and use thereof
CN104860825B (zh) 一种催化转化乳酸制备丙酮酸酯的方法
CN102050711A (zh) 一种丙烯醛的制备方法
CN117624077B (zh) 一种催化合成环己亚胺的方法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20160803

CF01 Termination of patent right due to non-payment of annual fee