JP6327853B2 - ５−ヒドロキシメチル−２−フルフラルデヒドから、カプロラクトン、カプロラクタム、２、５−テトラヒドロフラン−ジメタノール、１、６−ヘキサンジオール又は１、２、６−ヘキサントリオールの製造 - Google Patents
５−ヒドロキシメチル−２−フルフラルデヒドから、カプロラクトン、カプロラクタム、２、５−テトラヒドロフラン−ジメタノール、１、６−ヘキサンジオール又は１、２、６−ヘキサントリオールの製造 Download PDFInfo
- Publication number
- JP6327853B2 JP6327853B2 JP2013512556A JP2013512556A JP6327853B2 JP 6327853 B2 JP6327853 B2 JP 6327853B2 JP 2013512556 A JP2013512556 A JP 2013512556A JP 2013512556 A JP2013512556 A JP 2013512556A JP 6327853 B2 JP6327853 B2 JP 6327853B2
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- JP
- Japan
- Prior art keywords
- hexanediol
- catalyst
- hexanetriol
- hydrogenation
- caprolactone
- 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.)
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 title claims description 71
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 50
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 title claims description 46
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 title claims description 44
- 238000004519 manufacturing process Methods 0.000 title claims description 30
- YCZZQSFWHFBKMU-UHFFFAOYSA-N [5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OCC1CCC(CO)O1 YCZZQSFWHFBKMU-UHFFFAOYSA-N 0.000 title claims description 17
- 239000003054 catalyst Substances 0.000 claims description 104
- 238000005984 hydrogenation reaction Methods 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 66
- 238000006243 chemical reaction Methods 0.000 claims description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 39
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims description 33
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 28
- 239000010948 rhodium Substances 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 26
- 239000000377 silicon dioxide Substances 0.000 claims description 19
- 229910052703 rhodium Inorganic materials 0.000 claims description 18
- 230000002378 acidificating effect Effects 0.000 claims description 16
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 229930091371 Fructose Natural products 0.000 claims description 12
- 239000005715 Fructose Substances 0.000 claims description 12
- 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 description 12
- 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 description 10
- -1 dimethanol 1,2,6-hexane triol Chemical compound 0.000 claims description 10
- 239000008103 glucose Substances 0.000 claims description 10
- ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 claims description 10
- 229910052702 rhenium Inorganic materials 0.000 claims description 10
- 239000007868 Raney catalyst Substances 0.000 claims description 9
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 9
- WCJIUQVBQSTBDE-UHFFFAOYSA-N [Rh].[Re] Chemical compound [Rh].[Re] WCJIUQVBQSTBDE-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 8
- 239000002028 Biomass Substances 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 229920002472 Starch Polymers 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 6
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- 235000019698 starch Nutrition 0.000 claims description 6
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- 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 description 5
- 238000005342 ion exchange Methods 0.000 claims description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 claims description 3
- 238000005580 one pot reaction Methods 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000001868 cobalt Chemical class 0.000 claims 1
- 150000002815 nickel Chemical class 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 27
- 239000001257 hydrogen Substances 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 23
- 239000003446 ligand Substances 0.000 description 19
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- 239000002904 solvent Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
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- 239000002994 raw material Substances 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 238000007273 lactonization reaction Methods 0.000 description 11
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002105 nanoparticle Substances 0.000 description 9
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- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 244000005700 microbiome Species 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229910052707 ruthenium Inorganic materials 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000010457 zeolite Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 229910021536 Zeolite Inorganic materials 0.000 description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229920000557 Nafion® Polymers 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
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- 239000002243 precursor Substances 0.000 description 5
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- 241001120493 Arene Species 0.000 description 1
- NJQFCQXFOHVYQJ-PMACEKPBSA-N BF 4 Chemical compound C1([C@@H]2CC(=O)C=3C(O)=C(C)C4=C(C=3O2)[C@H](C(C)C)C2=C(O4)C(C)=C(C(C2=O)(C)C)OC)=CC=CC=C1 NJQFCQXFOHVYQJ-PMACEKPBSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical class O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- QLSOZHFOFHARBJ-UHFFFAOYSA-N [3-(diphenylphosphanylmethyl)phenyl]methyl-diphenylphosphane Chemical compound C=1C=CC(CP(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 QLSOZHFOFHARBJ-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 108090000637 alpha-Amylases Proteins 0.000 description 1
- 102000004139 alpha-Amylases Human genes 0.000 description 1
- 229940024171 alpha-amylase Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- VJVNWXUZZOBHRZ-UHFFFAOYSA-N benzene phosphoric acid Chemical compound P(=O)(O)(O)O.P(=O)(O)(O)O.P(=O)(O)(O)O.C1=CC=CC=C1 VJVNWXUZZOBHRZ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- UWZJZOZIQUQJEE-UHFFFAOYSA-N hexane-1,2,6-triol Chemical compound OCCCCC(O)CO.OCCCCC(O)CO UWZJZOZIQUQJEE-UHFFFAOYSA-N 0.000 description 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- ZRLVUNNBSSUWAC-UHFFFAOYSA-M hydrogen sulfate;tetraoctylazanium Chemical compound OS([O-])(=O)=O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC ZRLVUNNBSSUWAC-UHFFFAOYSA-M 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 150000002772 monosaccharides Chemical group 0.000 description 1
- GZPHDJXXLCGMTI-UHFFFAOYSA-N n-methyl-1-[3-(methylaminomethyl)phenyl]methanamine Chemical compound CNCC1=CC=CC(CNC)=C1 GZPHDJXXLCGMTI-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- WQIQNKQYEUMPBM-UHFFFAOYSA-N pentamethylcyclopentadiene Chemical compound CC1C(C)=C(C)C(C)=C1C WQIQNKQYEUMPBM-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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)
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 (3)
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| JP2013531638A JP2013531638A (ja) | 2013-08-08 |
| JP2013531638A5 JP2013531638A5 (enExample) | 2016-07-07 |
| JP6327853B2 true JP6327853B2 (ja) | 2018-05-23 |
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|---|---|
| US (1) | US9199961B2 (enExample) |
| EP (2) | EP2390247A1 (enExample) |
| JP (1) | JP6327853B2 (enExample) |
| CN (1) | CN103228626B (enExample) |
| BR (1) | BR112012029996B1 (enExample) |
| CA (1) | CA2800797C (enExample) |
| ES (1) | ES2727436T3 (enExample) |
| WO (1) | WO2011149339A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 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. |
| US8962894B2 (en) | 2011-12-30 | 2015-02-24 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| CN104024197A (zh) | 2011-12-30 | 2014-09-03 | 纳幕尔杜邦公司 | 己二醇的制备方法 |
| CN104066710B (zh) | 2012-01-18 | 2016-06-29 | 莱诺维亚公司 | 从5-羟甲基糠醛产生六亚甲基二胺的方法 |
| 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 |
| 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 |
| KR20150018877A (ko) | 2012-06-11 | 2015-02-24 | 레노비아 인코포레이티드 | 1,6-헥산디올로부터 아디프산의 제조방법 |
| 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 |
| US9988491B2 (en) | 2013-10-22 | 2018-06-05 | Empire Technology Development Llc | Methods and compounds for producing nylon 6,6 |
| 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 |
| US10131610B2 (en) | 2013-10-25 | 2018-11-20 | Empire Technology Development Llc | Methods of producing dicarbonyl compounds |
| US9611241B2 (en) | 2014-01-27 | 2017-04-04 | Rennovia Inc. | Conversion of fructose-containing feedstocks to HMF-containing product |
| SG11201608429TA (en) * | 2014-04-10 | 2016-11-29 | Archer Daniels Midland Co | Synthesis of r-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols |
| KR20160143760A (ko) * | 2014-04-10 | 2016-12-14 | 아처 다니엘 미드랜드 캄파니 | 환원 당 알코올, 퓨란 유도체의 합성 |
| EP3142966B1 (en) * | 2014-05-12 | 2020-01-29 | Virdia, Inc. | Hydrogenation of oxygenated molecules from biomass refining |
| WO2016043589A1 (en) * | 2014-09-19 | 2016-03-24 | Rijksuniversiteit Groningen | Method for reducing hydroxymethylfurfural (hmf) |
| CA2966147A1 (en) * | 2014-10-30 | 2016-05-06 | Toray Industries, Inc. | Method for producing .epsilon.-caprolactam |
| TW201636096A (zh) * | 2014-12-02 | 2016-10-16 | 瑞諾維亞公司 | 自５－羥甲基糠醛產生己三醇之方法 |
| 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 |
| SG11201913469PA (en) | 2017-07-12 | 2020-01-30 | 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 |
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|---|---|---|---|---|
| US3000880A (en) | 1961-09-19 | Production of epsilon caprolactams | ||
| US3064008A (en) | 1962-11-13 | I i i i i i | ||
| US3083236A (en) | 1958-09-10 | 1963-03-26 | Merck & Co Inc | Hydrogenation of 5-hydroxy-methyl furfural |
| US3070633A (en) | 1958-09-10 | 1962-12-25 | Merck & Co Inc | Process for producing 1, 6-hexanediol |
| 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 |
| US4400468A (en) * | 1981-10-05 | 1983-08-23 | Hydrocarbon Research Inc. | Process for producing adipic acid from biomass |
| 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 |
| JP4276406B2 (ja) * | 2002-04-30 | 2009-06-10 | トヨタ自動車株式会社 | アミド化合物およびアミノ化合物の製造方法 |
| CN1926240B (zh) | 2004-01-19 | 2010-06-02 | 帝斯曼知识产权资产管理有限公司 | 6-氨基己酸的生物化学合成 |
| EP2301919A1 (en) | 2004-06-10 | 2011-03-30 | Board of Trustees of Michigan State University | Synthesis of caprolactam from lysine |
| 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 |
| WO2008046790A1 (de) * | 2006-10-18 | 2008-04-24 | Basf Se | Verfahren zur herstellung von lactonen aus diolen |
| EP2106399A2 (en) | 2007-01-05 | 2009-10-07 | Novartis AG | Imidazole derivatives as kinesin spindle protein inhibitors (eg-5) |
| JP5432994B2 (ja) * | 2008-06-18 | 2014-03-05 | エージェンシー フォー サイエンス， テクノロジー アンド リサーチ | ヒドロキシメチルフルフラールの産生方法 |
| 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 |
-
2010
- 2010-05-26 EP EP10163881A patent/EP2390247A1/en not_active Withdrawn
-
2011
- 2011-03-23 WO PCT/NL2011/050200 patent/WO2011149339A1/en not_active Ceased
- 2011-03-23 ES ES11712049T patent/ES2727436T3/es active Active
- 2011-03-23 CN CN201180036114.6A patent/CN103228626B/zh active Active
- 2011-03-23 US US13/699,934 patent/US9199961B2/en active Active
- 2011-03-23 EP EP11712049.3A patent/EP2576506B1/en active Active
- 2011-03-23 JP JP2013512556A patent/JP6327853B2/ja active Active
- 2011-03-23 CA CA2800797A patent/CA2800797C/en active Active
- 2011-03-23 BR BR112012029996-4A patent/BR112012029996B1/pt active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| CA2800797A1 (en) | 2011-12-01 |
| CN103228626B (zh) | 2016-08-03 |
| EP2576506B1 (en) | 2019-03-06 |
| WO2011149339A1 (en) | 2011-12-01 |
| CN103228626A (zh) | 2013-07-31 |
| BR112012029996A2 (pt) | 2021-05-04 |
| US9199961B2 (en) | 2015-12-01 |
| US20130137863A1 (en) | 2013-05-30 |
| BR112012029996B1 (pt) | 2021-10-26 |
| EP2576506A1 (en) | 2013-04-10 |
| EP2390247A1 (en) | 2011-11-30 |
| CA2800797C (en) | 2019-04-16 |
| JP2013531638A (ja) | 2013-08-08 |
| ES2727436T3 (es) | 2019-10-16 |
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