JP2015506943A5 - - Google Patents
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- Publication number
- JP2015506943A5 JP2015506943A5 JP2014553332A JP2014553332A JP2015506943A5 JP 2015506943 A5 JP2015506943 A5 JP 2015506943A5 JP 2014553332 A JP2014553332 A JP 2014553332A JP 2014553332 A JP2014553332 A JP 2014553332A JP 2015506943 A5 JP2015506943 A5 JP 2015506943A5
- Authority
- JP
- Japan
- Prior art keywords
- reduction catalyst
- hydrogen
- heterogeneous reduction
- hexanediol
- furfural substrate
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims 32
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims 28
- 239000003054 catalyst Substances 0.000 claims 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 239000000758 substrate Substances 0.000 claims 14
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims 9
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 6
- 150000001720 carbohydrates Chemical class 0.000 claims 6
- 229910052721 tungsten Inorganic materials 0.000 claims 6
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims 5
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical group OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims 5
- 229910052772 Samarium Inorganic materials 0.000 claims 5
- 239000002184 metal Substances 0.000 claims 5
- 229910052751 metal Inorganic materials 0.000 claims 5
- 229910052702 rhenium Inorganic materials 0.000 claims 5
- 229910052727 yttrium Inorganic materials 0.000 claims 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 2
- 229930091371 Fructose Natural products 0.000 claims 2
- 239000005715 Fructose Substances 0.000 claims 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 2
- 229910021536 Zeolite Inorganic materials 0.000 claims 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 2
- 239000008103 glucose Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 239000010457 zeolite Substances 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261588093P | 2012-01-18 | 2012-01-18 | |
| US61/588,093 | 2012-01-18 | ||
| PCT/US2013/021315 WO2013109477A1 (en) | 2012-01-18 | 2013-01-11 | Process for production of hexamethylenediamine from 5 - hydroxymethylfurfural |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015506943A JP2015506943A (ja) | 2015-03-05 |
| JP2015506943A5 true JP2015506943A5 (enExample) | 2016-03-03 |
| JP6253203B2 JP6253203B2 (ja) | 2017-12-27 |
Family
ID=47605786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014553332A Expired - Fee Related JP6253203B2 (ja) | 2012-01-18 | 2013-01-11 | ５−ヒドロキシメチルフルフラールからのヘキサメチレンジアミンの生成方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (7) | US8853458B2 (enExample) |
| EP (2) | EP2804848B1 (enExample) |
| JP (1) | JP6253203B2 (enExample) |
| KR (1) | KR20140113706A (enExample) |
| CN (2) | CN106008163B (enExample) |
| AR (1) | AR089707A1 (enExample) |
| AU (2) | AU2013210005B2 (enExample) |
| BR (1) | BR112014017585B1 (enExample) |
| CA (1) | CA2860886A1 (enExample) |
| EA (1) | EA025555B1 (enExample) |
| HK (1) | HK1204318A1 (enExample) |
| IN (1) | IN2014DN06596A (enExample) |
| MX (1) | MX336933B (enExample) |
| MY (1) | MY165219A (enExample) |
| SA (2) | SA115360430B1 (enExample) |
| SG (3) | SG10201913670TA (enExample) |
| WO (1) | WO2013109477A1 (enExample) |
| ZA (2) | ZA201405258B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101930540B1 (ko) | 2009-05-07 | 2019-03-15 | 게노마티카 인코포레이티드 | 아디페이트, 헥사메틸렌디아민 및 6-아미노카프로산의 생합성을 위한 미생물 및 방법 |
| WO2013101977A1 (en) | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Production of tetrahydrofuran-2, 5-dimethanol from isosorbide |
| US8981130B2 (en) | 2011-12-30 | 2015-03-17 | E I Du Pont De Nemours And Company | Process for the production of hexanediols |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8962894B2 (en) | 2011-12-30 | 2015-02-24 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| WO2013101970A1 (en) | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Production of 5-hydroxymethyl-2-furfural from levoglucosenone |
| CA2860886A1 (en) * | 2012-01-18 | 2013-07-25 | Rennovia, Inc. | Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor |
| US8846985B2 (en) | 2012-04-27 | 2014-09-30 | 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 |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US9611241B2 (en) | 2014-01-27 | 2017-04-04 | Rennovia Inc. | Conversion of fructose-containing feedstocks to HMF-containing product |
| GB2540895A (en) | 2014-05-12 | 2017-02-01 | Virdia Inc | Hydrogenation of oxygenated molecules from biomass refining |
| WO2015175528A1 (en) * | 2014-05-12 | 2015-11-19 | Micromidas, Inc. | Methods of producing compounds from 5-(halomethyl)furfural |
| SG10201914057PA (en) | 2014-12-02 | 2020-03-30 | Archer Daniels Midland Co | Process for production of 2,5-bis-hydroxymethylfuran, 2,5-bis-hydroxymethyltetrahydrofuran, 1,6-hexanediol and 1,2,6-hexanetriol from 5-hydroxymethylfurfural |
| 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 |
| US20200270190A1 (en) * | 2015-12-17 | 2020-08-27 | Shell Oil Company | Hydrogenation or hydrogenolysis of an oxygenate |
| SG11201805514VA (en) | 2016-01-13 | 2018-07-30 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
| CN110997647A (zh) | 2017-07-12 | 2020-04-10 | 斯道拉恩索公司 | 纯化的2,5-呋喃二甲酸途径产物 |
| CN110935447B (zh) * | 2018-09-25 | 2021-12-07 | 中国科学院大连化学物理研究所 | 一种用于甘油水溶液氢解制1,3-丙二醇的催化剂及其制备方法 |
| CN109678654B (zh) * | 2019-01-24 | 2021-11-09 | 嘉兴学院 | 一种5-羟甲基糠醛加氢直接生产1,2,6-己三醇的方法 |
| CN110420637B (zh) * | 2019-08-06 | 2020-10-02 | 北京化工大学 | 一种W改性载体负载金属Pd制备复合型催化剂的方法及其应用 |
| CN110981691B (zh) * | 2019-12-16 | 2021-01-15 | 北京大学 | 一种利用单糖合成1,6-己二醇的方法 |
| CN111072490A (zh) * | 2019-12-16 | 2020-04-28 | 中国科学院大连化学物理研究所 | 一种基于Ni基催化剂的己二醛制备己二胺的方法 |
| JP7324721B2 (ja) * | 2020-02-12 | 2023-08-10 | 株式会社ダイセル | １，４－アンヒドロエリスリトール水素化分解触媒、及び前記触媒を使用した１，３－ブタンジオールの製造方法 |
| 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 |
| CN115353449B (zh) * | 2022-08-12 | 2024-02-20 | 东莞理工学院 | 二价钐单电子还原试剂、制备方法及其应用 |
| WO2025109585A2 (en) | 2024-03-27 | 2025-05-30 | Inv Nylon Chemicals Americas, Llc | Diamine synthesis process |
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| GB600871A (en) | 1945-10-17 | 1948-04-21 | Walter Norman Haworth | Improvements relating to the manufacture of 5-hydroxymethyl 2-furfural |
| GB591858A (en) | 1944-05-30 | 1947-09-01 | Walter Norman Haworth | Improvements relating to the manufacture of 5-hydroxy-methyl furfural or levulinic acid |
| US2082025A (en) * | 1933-04-13 | 1937-06-01 | Quaker Oats Co | Method for the reduction of furfural and furan derivatives |
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| US6518440B2 (en) | 2001-03-05 | 2003-02-11 | Gene E. Lightner | Hydroxymethylfurfural derived from cellulose contained in lignocellulose solids |
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| KR101930540B1 (ko) | 2009-05-07 | 2019-03-15 | 게노마티카 인코포레이티드 | 아디페이트, 헥사메틸렌디아민 및 6-아미노카프로산의 생합성을 위한 미생물 및 방법 |
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| WO2013101970A1 (en) | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Production of 5-hydroxymethyl-2-furfural from levoglucosenone |
| WO2013101977A1 (en) | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Production of tetrahydrofuran-2, 5-dimethanol from isosorbide |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| CA2860886A1 (en) | 2012-01-18 | 2013-07-25 | Rennovia, Inc. | Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates therefor |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8846985B2 (en) | 2012-04-27 | 2014-09-30 | 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 |
| US9035094B2 (en) | 2012-06-11 | 2015-05-19 | Rennovia, Inc. | Process for production of adipic acid from 1,6-hexanediol |
| WO2014004867A1 (en) | 2012-06-28 | 2014-01-03 | Shell Oil Company | Methods for hydrothermal digestion of cellulosic biomass solids in the presence of a distributed slurry catalyst |
| US8946458B2 (en) | 2012-08-15 | 2015-02-03 | Virent, Inc. | Catalysts for hydrodeoxygenation of oxygenated hydrocarbons |
| 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 |
| US20140275638A1 (en) | 2013-03-15 | 2014-09-18 | Wisconsin Alumni Research Foundation | Method for preparing triols and diols from biomass-derived reactants |
-
2013
- 2013-01-11 CA CA2860886A patent/CA2860886A1/en active Pending
- 2013-01-11 EP EP13701538.4A patent/EP2804848B1/en active Active
- 2013-01-11 AR ARP130100095A patent/AR089707A1/es unknown
- 2013-01-11 KR KR1020147021436A patent/KR20140113706A/ko not_active Withdrawn
- 2013-01-11 EP EP18197934.5A patent/EP3466919B1/en active Active
- 2013-01-11 HK HK15104804.1A patent/HK1204318A1/xx unknown
- 2013-01-11 SG SG10201913670TA patent/SG10201913670TA/en unknown
- 2013-01-11 MY MYPI2014002099A patent/MY165219A/en unknown
- 2013-01-11 US US13/739,975 patent/US8853458B2/en active Active
- 2013-01-11 MX MX2014008638A patent/MX336933B/es active IP Right Grant
- 2013-01-11 JP JP2014553332A patent/JP6253203B2/ja not_active Expired - Fee Related
- 2013-01-11 SG SG11201404098XA patent/SG11201404098XA/en unknown
- 2013-01-11 IN IN6596DEN2014 patent/IN2014DN06596A/en unknown
- 2013-01-11 CN CN201610345494.6A patent/CN106008163B/zh active Active
- 2013-01-11 BR BR112014017585-3A patent/BR112014017585B1/pt active IP Right Grant
- 2013-01-11 EA EA201491289A patent/EA025555B1/ru not_active IP Right Cessation
- 2013-01-11 AU AU2013210005A patent/AU2013210005B2/en not_active Ceased
- 2013-01-11 SG SG10201700153WA patent/SG10201700153WA/en unknown
- 2013-01-11 WO PCT/US2013/021315 patent/WO2013109477A1/en not_active Ceased
- 2013-01-11 CN CN201380005573.7A patent/CN104066710B/zh active Active
- 2013-01-12 SA SA115360430A patent/SA115360430B1/ar unknown
- 2013-01-12 SA SA113340200A patent/SA113340200B1/ar unknown
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2014
- 2014-05-29 US US14/290,869 patent/US9035109B2/en active Active
- 2014-07-17 ZA ZA2014/05258A patent/ZA201405258B/en unknown
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2015
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- 2015-04-15 US US14/687,894 patent/US20160068470A1/en not_active Abandoned
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2016
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2017
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