CA2800797C - Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran-dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde - Google Patents
Preparation of caprolactone, caprolactam, 2,5-tetrahydrofuran-dimethanol, 1,6-hexanediol or 1,2,6-hexanetriol from 5-hydroxymethyl-2-furfuraldehyde Download PDFInfo
- Publication number
- CA2800797C CA2800797C CA2800797A CA2800797A CA2800797C CA 2800797 C CA2800797 C CA 2800797C CA 2800797 A CA2800797 A CA 2800797A CA 2800797 A CA2800797 A CA 2800797A CA 2800797 C CA2800797 C CA 2800797C
- Authority
- CA
- Canada
- Prior art keywords
- hexanediol
- hexanetriol
- 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.)
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 title claims abstract description 80
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 title claims abstract description 57
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 title claims abstract description 49
- YCZZQSFWHFBKMU-UHFFFAOYSA-N [5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OCC1CCC(CO)O1 YCZZQSFWHFBKMU-UHFFFAOYSA-N 0.000 title claims abstract description 23
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 title claims abstract 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 50
- 238000002360 preparation method Methods 0.000 title description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 68
- ROTONRWJLXYJBD-UHFFFAOYSA-N oxan-2-ylmethanol Chemical compound OCC1CCCCO1 ROTONRWJLXYJBD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims description 106
- 238000006243 chemical reaction Methods 0.000 claims description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 16
- 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 12
- 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 12
- 239000007868 Raney catalyst Substances 0.000 claims description 11
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 11
- 239000008103 glucose Substances 0.000 claims description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 8
- WCJIUQVBQSTBDE-UHFFFAOYSA-N [Rh].[Re] Chemical compound [Rh].[Re] WCJIUQVBQSTBDE-UHFFFAOYSA-N 0.000 claims description 7
- 229920002472 Starch Polymers 0.000 claims description 6
- 239000008107 starch Substances 0.000 claims description 6
- 235000019698 starch Nutrition 0.000 claims description 6
- 150000001720 carbohydrates Chemical class 0.000 claims description 5
- 235000014633 carbohydrates Nutrition 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 238000005580 one pot reaction Methods 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 150000002503 iridium Chemical class 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003303 ruthenium Chemical class 0.000 claims description 2
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 2
- 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
- 150000001875 compounds Chemical class 0.000 abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- 239000010948 rhodium Substances 0.000 description 30
- 239000000377 silicon dioxide Substances 0.000 description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- 239000003446 ligand Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 229910052703 rhodium Inorganic materials 0.000 description 15
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 14
- 239000010457 zeolite Substances 0.000 description 14
- 230000002378 acidificating effect Effects 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 13
- 229910021536 Zeolite Inorganic materials 0.000 description 12
- 239000012876 carrier material Substances 0.000 description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 239000002105 nanoparticle Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 229910052681 coesite Inorganic materials 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 229910052906 cristobalite Inorganic materials 0.000 description 8
- 244000005700 microbiome Species 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229910052702 rhenium Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229910052682 stishovite Inorganic materials 0.000 description 8
- 229910052905 tridymite Inorganic materials 0.000 description 8
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- 235000012239 silicon dioxide Nutrition 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 6
- 238000004172 nitrogen cycle Methods 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- -1 tetrahydro-2H-pyran-2-yl Chemical group 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 5
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 5
- 229920000557 Nafion® Polymers 0.000 description 5
- 235000010724 Wisteria floribunda Nutrition 0.000 description 5
- 239000002253 acid Substances 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
- 238000005470 impregnation Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002028 Biomass Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000004472 Lysine Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 150000001721 carbon Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
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- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 4
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910002535 CuZn Inorganic materials 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
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- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
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- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 description 2
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- 102100022624 Glucoamylase Human genes 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
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- 238000006606 decarbonylation reaction Methods 0.000 description 2
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- 125000000524 functional group Chemical group 0.000 description 2
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- HBVFXTAPOLSOPB-UHFFFAOYSA-N nickel vanadium Chemical compound [V].[Ni] HBVFXTAPOLSOPB-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
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- 239000003586 protic polar solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
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- 229910052723 transition metal Inorganic materials 0.000 description 2
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- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 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
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- 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
- 230000009286 beneficial effect Effects 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
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000002860 competitive effect Effects 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
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- 229930007927 cymene Natural products 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
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- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000003869 genetically modified organism Nutrition 0.000 description 1
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- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 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
- NLGDHEASMIZIBP-UHFFFAOYSA-N hexane-1,6-diol hexane-1,2,6-triol Chemical compound OCCCCCCO.OCCCCC(O)CO NLGDHEASMIZIBP-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
- ZRLVUNNBSSUWAC-UHFFFAOYSA-M hydrogen sulfate;tetraoctylazanium Chemical compound OS([O-])(=O)=O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC ZRLVUNNBSSUWAC-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- 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
- 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
- 239000002245 particle Substances 0.000 description 1
- 230000037361 pathway Effects 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
- 125000005538 phosphinite group Chemical group 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
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- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 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
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- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 239000012056 semi-solid material Substances 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 238000004627 transmission electron microscopy Methods 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
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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 (2)
| Publication Number | Publication Date |
|---|---|
| CA2800797A1 CA2800797A1 (en) | 2011-12-01 |
| CA2800797C true CA2800797C (en) | 2019-04-16 |
Family
ID=42797300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2800797A Active CA2800797C (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 |
Country Status (8)
| Country | Link |
|---|---|
| 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) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8669297B2 (en) | 2010-05-24 | 2014-03-11 | 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 |
| EP2797904A4 (en) * | 2011-12-30 | 2015-08-05 | Du Pont | PREPARATION 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 |
| WO2013101970A1 (en) | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Production of 5-hydroxymethyl-2-furfural from levoglucosenone |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8981130B2 (en) | 2011-12-30 | 2015-03-17 | E I Du Pont De Nemours And Company | Process for the production of hexanediols |
| EP2797866A4 (en) * | 2011-12-30 | 2015-08-05 | Du Pont | PROCESS FOR THE PREPARATION OF 1,6-HEXANEDIOL |
| HK1204318A1 (en) * | 2012-01-18 | 2015-11-13 | Archer-Daniels-Midland Company | Process for production of hexamethylenediamine from 5 - hydroxymethylfurfural |
| WO2013133208A1 (ja) * | 2012-03-09 | 2013-09-12 | 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 |
| US8846984B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of α,ω-diols |
| US8859826B2 (en) | 2012-04-27 | 2014-10-14 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| EP2858748B1 (en) | 2012-06-11 | 2018-04-11 | 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 |
| US9982094B2 (en) | 2013-10-22 | 2018-05-29 | Empire Technology Development Llc | Compounds and methods for producing nylon 6 |
| CN105658612A (zh) | 2013-10-22 | 2016-06-08 | 英派尔科技开发有限公司 | 用于生产尼龙6,6的方法和化合物 |
| 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 |
| SG11201606169PA (en) | 2014-01-27 | 2016-08-30 | Rennovia Inc | Conversion of fructose-containing feedstocks to hmf-containing product |
| US20170029393A1 (en) * | 2014-04-10 | 2017-02-02 | Archer Daniels Midland Company | Synthesis of r-glucosides, sugar alcohols, reduced sugar alcohols, and furan derivatives of reduced sugar alcohols |
| SG11201608426PA (en) * | 2014-04-10 | 2016-11-29 | Archer Daniels Midland Co | Synthesis of reduced sugar alcohols, furan derivatives |
| 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) |
| US10196352B2 (en) * | 2014-10-30 | 2019-02-05 | Toray Industries, Inc. | Method for producing epsilon-caprolactam |
| BR112017009754B1 (pt) | 2014-12-02 | 2021-09-14 | Archer-Daniels-Midland Company | Processo para a preparação de 2,5-bis-hidroximetilfurano, 1,2,6-hexanotriol, e 1,6- exanodiol a partir de 5- hidroximetilfurfural |
| 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 |
| BR112018014278B1 (pt) | 2016-01-13 | 2022-07-12 | Stora Enso Oyj | Processos para a preparação de ácido 2,5-furandicarboxílico e intermediários e derivados dos mesmos |
| 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 | ||
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| 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 |
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| 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 |
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| 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 |
| WO2005068643A2 (en) | 2004-01-19 | 2005-07-28 | Dsm Ip Assets B.V. | Biochemical synthesis of 6-amino caproic acid |
| WO2005123669A1 (en) | 2004-06-10 | 2005-12-29 | 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 |
| CA2674318A1 (en) | 2007-01-05 | 2008-07-17 | Novartis Ag | Cyclized derivatives as eg-5 inhibitors |
| 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 |
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2010
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- 2011-03-23 CN CN201180036114.6A patent/CN103228626B/zh active Active
- 2011-03-23 JP JP2013512556A patent/JP6327853B2/ja active Active
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|---|---|
| EP2576506A1 (en) | 2013-04-10 |
| JP6327853B2 (ja) | 2018-05-23 |
| ES2727436T3 (es) | 2019-10-16 |
| CA2800797A1 (en) | 2011-12-01 |
| CN103228626A (zh) | 2013-07-31 |
| US20130137863A1 (en) | 2013-05-30 |
| US9199961B2 (en) | 2015-12-01 |
| CN103228626B (zh) | 2016-08-03 |
| EP2390247A1 (en) | 2011-11-30 |
| WO2011149339A1 (en) | 2011-12-01 |
| BR112012029996B1 (pt) | 2021-10-26 |
| BR112012029996A2 (pt) | 2021-05-04 |
| JP2013531638A (ja) | 2013-08-08 |
| EP2576506B1 (en) | 2019-03-06 |
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