CA2931554C - Mono- and dialkyl ethers of furan-2,5-dimethanol and (tetra-hydrofuran-2,5-diyl)dimethanol and amphiphilic derivatives thereof - Google Patents
Mono- and dialkyl ethers of furan-2,5-dimethanol and (tetra-hydrofuran-2,5-diyl)dimethanol and amphiphilic derivatives thereof Download PDFInfo
- Publication number
- CA2931554C CA2931554C CA2931554A CA2931554A CA2931554C CA 2931554 C CA2931554 C CA 2931554C CA 2931554 A CA2931554 A CA 2931554A CA 2931554 A CA2931554 A CA 2931554A CA 2931554 C CA2931554 C CA 2931554C
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- CA
- Canada
- Prior art keywords
- methyl
- process according
- tetrahydrofuran
- fdm
- mono
- 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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- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 title claims abstract description 57
- YCZZQSFWHFBKMU-UHFFFAOYSA-N [5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OCC1CCC(CO)O1 YCZZQSFWHFBKMU-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 150000001346 alkyl aryl ethers Chemical class 0.000 title abstract description 3
- 150000001983 dialkylethers Chemical class 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 49
- 230000008569 process Effects 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 239000012038 nucleophile Substances 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 52
- 239000003341 Bronsted base Substances 0.000 claims description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 34
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 23
- -1 alkyl lithium Chemical compound 0.000 claims description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 17
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 16
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 150000001350 alkyl halides Chemical class 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 11
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 239000007818 Grignard reagent Substances 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 47
- 238000003786 synthesis reaction Methods 0.000 abstract description 33
- 230000015572 biosynthetic process Effects 0.000 abstract description 31
- 238000002360 preparation method Methods 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- 238000003756 stirring Methods 0.000 description 61
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 54
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 52
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- 239000000741 silica gel Substances 0.000 description 34
- 229910002027 silica gel Inorganic materials 0.000 description 34
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical group OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 229910052786 argon Inorganic materials 0.000 description 26
- 239000004810 polytetrafluoroethylene Substances 0.000 description 26
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 26
- 229910052684 Cerium Inorganic materials 0.000 description 20
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 20
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000012267 brine Substances 0.000 description 18
- 101150041968 CDC13 gene Proteins 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- 229920001971 elastomer Polymers 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- NJLAGDPRCAPJIF-MHSJTTIKSA-N (8S)-1',3',9-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-1,4',5',8',9'-pentone Chemical compound COc1cc(=O)c2c(c1=O)c(=O)c1=C(O)[C@]3(CCc4cc5cc(\C=C\C=C\C)[nH]c(=O)c5c(O)c34)C(O)=c1c2=O NJLAGDPRCAPJIF-MHSJTTIKSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 10
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 10
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 10
- 238000012800 visualization Methods 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 150000002334 glycols Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 7
- 238000006266 etherification reaction Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003880 polar aprotic solvent Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 6
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006073 displacement reaction Methods 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- QJIQQUHELIPPML-UHFFFAOYSA-N [5-(octadecoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCCCCCCCCCCCCCC)OCC1=CC=C(O1)CO QJIQQUHELIPPML-UHFFFAOYSA-N 0.000 description 3
- WASHTJLXUGBPDV-UHFFFAOYSA-N [5-(octadecoxymethyl)furan-2-yl]methyl trifluoromethanesulfonate Chemical compound FC(S(=O)(=O)OCC=1OC(=CC1)COCCCCCCCCCCCCCCCCCC)(F)F WASHTJLXUGBPDV-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000006264 debenzylation reaction Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 3
- LLWRXQXPJMPHLR-UHFFFAOYSA-N methylazanium;iodide Chemical compound [I-].[NH3+]C LLWRXQXPJMPHLR-UHFFFAOYSA-N 0.000 description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- WCNKULSYBFSDRF-HDICACEKSA-N (2S,5R)-2,5-bis(hexoxymethyl)oxolane Chemical compound C(CCCCC)OC[C@@H]1O[C@@H](CC1)COCCCCCC WCNKULSYBFSDRF-HDICACEKSA-N 0.000 description 2
- QTTQWWFHVDQVPM-UHFFFAOYSA-N 2,5-bis(dodecoxymethyl)furan Chemical compound CCCCCCCCCCCCOCC1=CC=C(COCCCCCCCCCCCC)O1 QTTQWWFHVDQVPM-UHFFFAOYSA-N 0.000 description 2
- OUCUZRKXZKSWLD-UHFFFAOYSA-N 2,5-bis(hexoxymethyl)furan Chemical compound CCCCCCOCC1=CC=C(COCCCCCC)O1 OUCUZRKXZKSWLD-UHFFFAOYSA-N 0.000 description 2
- HFLFOIQILRBILM-UHFFFAOYSA-N 2,5-bis(octadecoxymethyl)furan Chemical compound C(CCCCCCCCCCCCCCCCC)OCC=1OC(=CC1)COCCCCCCCCCCCCCCCCCC HFLFOIQILRBILM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WKJYBARSSHPINT-UHFFFAOYSA-N 2-amino-1-ethoxyethanol Chemical class CCOC(O)CN WKJYBARSSHPINT-UHFFFAOYSA-N 0.000 description 2
- 239000007848 Bronsted acid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- GCXLHYPYUXENAH-UHFFFAOYSA-N [5-(dodecoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCCCCCCCC)OCC1=CC=C(O1)CO GCXLHYPYUXENAH-UHFFFAOYSA-N 0.000 description 2
- OOVOSGURXWZGJD-UHFFFAOYSA-N [5-(dodecoxymethyl)furan-2-yl]methyl hydrogen sulfate Chemical compound S(=O)(=O)(OCC=1OC(=CC1)COCCCCCCCCCCCC)O OOVOSGURXWZGJD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000013461 intermediate chemical Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- CFSVRRKPLZTRQM-RNPORBBMSA-N (2R,5S)-2,5-bis(dodecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCC)OC[C@@H]1O[C@@H](CC1)COCCCCCCCCCCCC CFSVRRKPLZTRQM-RNPORBBMSA-N 0.000 description 1
- GKGRPKVJALYQLW-ZRKBJOGQSA-N (2R,5S)-2,5-bis(octadecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCCCCCCCC)OC[C@@H]1O[C@@H](CC1)COCCCCCCCCCCCCCCCCCC GKGRPKVJALYQLW-ZRKBJOGQSA-N 0.000 description 1
- CFSVRRKPLZTRQM-KYJUHHDHSA-N (2S,5S)-2,5-bis(dodecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCC)OC[C@H]1O[C@@H](CC1)COCCCCCCCCCCCC CFSVRRKPLZTRQM-KYJUHHDHSA-N 0.000 description 1
- WCNKULSYBFSDRF-ROUUACIJSA-N (2S,5S)-2,5-bis(hexoxymethyl)oxolane Chemical compound C(CCCCC)OC[C@H]1O[C@@H](CC1)COCCCCCC WCNKULSYBFSDRF-ROUUACIJSA-N 0.000 description 1
- GKGRPKVJALYQLW-COCZKOEFSA-N (2S,5S)-2,5-bis(octadecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCCCCCCCC)OC[C@H]1O[C@@H](CC1)COCCCCCCCCCCCCCCCCCC GKGRPKVJALYQLW-COCZKOEFSA-N 0.000 description 1
- PAJXWJFQRRBGBC-UHFFFAOYSA-N 2-[2-[[5-(octadecoxymethyl)furan-2-yl]methylamino]ethylamino]ethanol Chemical compound C(CCCCCCCCCCCCCCCCC)OCC1=CC=C(O1)CNCCNCCO PAJXWJFQRRBGBC-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910004727 OSO3H Inorganic materials 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- RRRAPUDYGHVTEV-LYCTWNKOSA-M S(=O)(=O)(OC[C@H]1O[C@H](CC1)COCCCCCC)[O-].[K+] Chemical compound S(=O)(=O)(OC[C@H]1O[C@H](CC1)COCCCCCC)[O-].[K+] RRRAPUDYGHVTEV-LYCTWNKOSA-M 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- WYTQKXGSLVRFSB-UHFFFAOYSA-N [5-(hexoxymethyl)furan-2-yl]methanamine Chemical compound CCCCCCOCC1=CC=C(CN)O1 WYTQKXGSLVRFSB-UHFFFAOYSA-N 0.000 description 1
- WEPZQMOMPHLUFJ-UHFFFAOYSA-N [5-(hexoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCC)OCC1=CC=C(O1)CO WEPZQMOMPHLUFJ-UHFFFAOYSA-N 0.000 description 1
- BNBJSBCAOLHRMC-UHFFFAOYSA-N [5-(hexoxymethyl)furan-2-yl]methyl trifluoromethanesulfonate Chemical compound FC(S(=O)(=O)OCC=1OC(=CC1)COCCCCCC)(F)F BNBJSBCAOLHRMC-UHFFFAOYSA-N 0.000 description 1
- 239000012773 agricultural material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 208000013409 limited attention Diseases 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003864 primary ammonium salts Chemical class 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361918239P | 2013-12-19 | 2013-12-19 | |
| US61/918,239 | 2013-12-19 | ||
| PCT/US2014/070021 WO2015094970A1 (en) | 2013-12-19 | 2014-12-12 | Mono- and dialkyl ethers of furan-2,5-dimethanol and (tetra-hydrofuran-2,5-diyl)dimethanol and amphiphilic derivatives thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2931554A1 CA2931554A1 (en) | 2015-06-25 |
| CA2931554C true CA2931554C (en) | 2020-10-13 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2931554A Active CA2931554C (en) | 2013-12-19 | 2014-12-12 | Mono- and dialkyl ethers of furan-2,5-dimethanol and (tetra-hydrofuran-2,5-diyl)dimethanol and amphiphilic derivatives thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9670174B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3083576A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6396462B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102100539B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN105814030A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2014366334B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2931554C (cg-RX-API-DMAC7.html) |
| HK (1) | HK1226391A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2016007952A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2015094970A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014134716A1 (en) | 2013-03-08 | 2014-09-12 | The University Of British Columbia | Substituted organofluoroborates as imaging agents |
| CA2931552A1 (en) * | 2013-12-19 | 2015-06-25 | Archer Daniels Midland Company | Sulfonates of furan-2,5-dimethanol and (tetrahydrofuran-2,5-diyl)dimethanol and derivatives thereof |
| ES2965441T3 (es) | 2015-04-14 | 2024-04-15 | Du Pont | Procedimientos para producir ácido 2,5-furandicarboxílico y derivados del mismo |
| DE102016009798A1 (de) | 2016-08-12 | 2018-02-15 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| DE102016009800A1 (de) | 2016-08-12 | 2018-02-15 | Henkel Ag & Co. Kgaa | Wasch- und Reinigungsmittel mit anionischen Tensiden aus nachwachsenden Rohstoffen |
| DE102017008071A1 (de) * | 2017-08-28 | 2019-02-28 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| DE102017008072A1 (de) * | 2017-08-28 | 2019-02-28 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| DE102017008073A1 (de) * | 2017-08-28 | 2019-02-28 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| CA3118223A1 (en) | 2018-12-18 | 2020-06-25 | Provincial Health Services Authority | Dual mode 18f-labelled theranostic compounds and uses thereof |
| BR112021022103A2 (pt) | 2019-05-10 | 2021-12-28 | Unilever Ip Holdings Bv | Tensoativo à base de furano, composição de lavagem de roupas, produto de lavagem de roupas e composição para limpeza manual de louças |
| EP4176028A1 (en) | 2020-07-06 | 2023-05-10 | Unilever IP Holdings B.V. | Irritation mitigating surfactants |
| CN114163407B (zh) * | 2020-09-11 | 2023-10-24 | 中国科学院宁波材料技术与工程研究所 | 抑制或杀灭微生物的呋喃环类成分、含其的制品及其应用 |
| KR102665866B1 (ko) | 2021-11-08 | 2024-05-14 | 한국생산기술연구원 | 테트라히드로퓨란-2,5-디메탄올을 사용한 테트라히드로퓨란-2,5-디에스터의 제조 및 분리 정제 방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178261A3 (en) * | 1984-10-10 | 1986-12-30 | Sandoz Ag | Substituted 2-furanyl or 5-oxo-2-furanyl-alkoxy phosphoryl alkyl cyclimmonium salts |
| US4619917A (en) * | 1985-07-18 | 1986-10-28 | Sandoz Pharm. Corp. | Substituted 2-furanyl- or 5-oxo-2-furanyl methoxy phosphoryl alkyl cyclimmonium salts |
| ES2010568A6 (es) * | 1988-08-04 | 1989-11-16 | Uriach & Cia Sa J | Procedimiento para la obtencion de derivados 2,5-disustituidos de tetrahidrofurano. |
| US5208352A (en) * | 1992-04-02 | 1993-05-04 | Sandoz Ltd. | Process for preparing the R- and S-isomers of 2-hydroxy-methyl-2-octadecyloxymethyl-tetrahydrofuran and their use in preparing stereoisomers of pharmacologically active compounds |
| JP4419761B2 (ja) * | 2004-09-06 | 2010-02-24 | ダイソー株式会社 | スピロ骨格を持つキラルな相間移動触媒およびその製造法、並びにそれを用いた不斉触媒反応。 |
| DE102005023588A1 (de) * | 2005-05-18 | 2006-11-23 | Grünenthal GmbH | Salze substituierter Allophansäureester und deren Verwendung in Arzneimitteln |
| JO3240B1 (ar) * | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| US8669383B2 (en) * | 2010-12-16 | 2014-03-11 | Archer Daniels Midland Company | Preparation of aminomethyl furans and alkoxymethyl furan derivatives from carbohydrates |
-
2014
- 2014-12-12 WO PCT/US2014/070021 patent/WO2015094970A1/en not_active Ceased
- 2014-12-12 MX MX2016007952A patent/MX2016007952A/es unknown
- 2014-12-12 CA CA2931554A patent/CA2931554C/en active Active
- 2014-12-12 HK HK16114626.5A patent/HK1226391A1/zh unknown
- 2014-12-12 CN CN201480067612.0A patent/CN105814030A/zh active Pending
- 2014-12-12 AU AU2014366334A patent/AU2014366334B2/en active Active
- 2014-12-12 JP JP2016530946A patent/JP6396462B2/ja active Active
- 2014-12-12 KR KR1020167018816A patent/KR102100539B1/ko active Active
- 2014-12-12 EP EP14871772.1A patent/EP3083576A4/en not_active Withdrawn
- 2014-12-12 US US15/038,066 patent/US9670174B2/en active Active
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2017
- 2017-04-28 US US15/581,613 patent/US20170233358A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2014366334A1 (en) | 2016-06-02 |
| US9670174B2 (en) | 2017-06-06 |
| JP6396462B2 (ja) | 2018-09-26 |
| AU2014366334B2 (en) | 2018-01-18 |
| EP3083576A1 (en) | 2016-10-26 |
| HK1226391A1 (zh) | 2017-09-29 |
| MX2016007952A (es) | 2016-09-09 |
| KR102100539B1 (ko) | 2020-04-13 |
| JP2017501123A (ja) | 2017-01-12 |
| US20170233358A1 (en) | 2017-08-17 |
| CN105814030A (zh) | 2016-07-27 |
| CA2931554A1 (en) | 2015-06-25 |
| EP3083576A4 (en) | 2017-08-02 |
| US20160297785A1 (en) | 2016-10-13 |
| KR20160098382A (ko) | 2016-08-18 |
| WO2015094970A1 (en) | 2015-06-25 |
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