DE112004000754T5 - Hydrierung von chemisch deriviertem 1,3-Propandiol - Google Patents
Hydrierung von chemisch deriviertem 1,3-Propandiol Download PDFInfo
- Publication number
- DE112004000754T5 DE112004000754T5 DE112004000754T DE112004000754T DE112004000754T5 DE 112004000754 T5 DE112004000754 T5 DE 112004000754T5 DE 112004000754 T DE112004000754 T DE 112004000754T DE 112004000754 T DE112004000754 T DE 112004000754T DE 112004000754 T5 DE112004000754 T5 DE 112004000754T5
- Authority
- DE
- Germany
- Prior art keywords
- alumina
- silica
- propanediol
- carbon
- color
- 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.)
- Withdrawn
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 45
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 title claims abstract description 44
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 229920000166 polytrimethylene carbonate Polymers 0.000 title claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 62
- 239000000126 substance Substances 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 34
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 20
- 239000000377 silicon dioxide Substances 0.000 claims description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 19
- -1 clays Inorganic materials 0.000 claims description 18
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 14
- 241001550224 Apha Species 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 8
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052702 rhenium Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 4
- 235000014692 zinc oxide Nutrition 0.000 claims description 4
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 claims description 4
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 3
- 239000005751 Copper oxide Substances 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910000431 copper oxide Inorganic materials 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- DZQBLSOLVRLASG-UHFFFAOYSA-N iridium;methane Chemical compound C.[Ir] DZQBLSOLVRLASG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- YFKIWUQBRSMPMZ-UHFFFAOYSA-N methane;nickel Chemical compound C.[Ni] YFKIWUQBRSMPMZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 229910000018 strontium carbonate Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 2
- 229910044991 metal oxide Inorganic materials 0.000 claims 2
- 150000004706 metal oxides Chemical class 0.000 claims 2
- 239000010948 rhodium Substances 0.000 claims 2
- 239000012530 fluid Substances 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 19
- 238000010998 test method Methods 0.000 description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 239000002243 precursor Substances 0.000 description 10
- 230000009467 reduction Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 229910001868 water Inorganic materials 0.000 description 7
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000001728 nano-filtration Methods 0.000 description 2
- 238000005325 percolation Methods 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 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 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- 108010065027 Propanediol Dehydratase Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- DJYPJBAHKUBLSS-UHFFFAOYSA-M sodium;hydron;terephthalate Chemical compound [Na+].OC(=O)C1=CC=C(C([O-])=O)C=C1 DJYPJBAHKUBLSS-UHFFFAOYSA-M 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/90—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound using hydrogen only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46822303P | 2003-05-06 | 2003-05-06 | |
| US60/468,223 | 2003-05-06 | ||
| US10/634,666 US7084311B2 (en) | 2003-05-06 | 2003-08-05 | Hydrogenation of chemically derived 1,3-propanediol |
| US10/634,666 | 2003-08-05 | ||
| PCT/US2004/014040 WO2004101468A2 (en) | 2003-05-06 | 2004-05-05 | Hydrogenation of chemically derived 1,3-propanediol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE112004000754T5 true DE112004000754T5 (de) | 2006-03-30 |
Family
ID=33423708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE112004000754T Withdrawn DE112004000754T5 (de) | 2003-05-06 | 2004-05-05 | Hydrierung von chemisch deriviertem 1,3-Propandiol |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7084311B2 (enExample) |
| JP (1) | JP4642028B2 (enExample) |
| CA (1) | CA2522681A1 (enExample) |
| DE (1) | DE112004000754T5 (enExample) |
| WO (1) | WO2004101468A2 (enExample) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7323539B2 (en) * | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
| US7342142B2 (en) | 2003-05-06 | 2008-03-11 | E.I. Du Pont De Nemours And Company | Hydrogenation of polytrimethylene ether glycol |
| US7745668B2 (en) * | 2003-05-06 | 2010-06-29 | E. I. Du Pont De Nemours And Company | Processes for reducing color in polytrimethylene ether glycol polymers |
| US7888405B2 (en) | 2004-01-30 | 2011-02-15 | E. I. Du Pont De Nemours And Company | Aliphatic-aromatic polyesters, and articles made therefrom |
| US20080103217A1 (en) * | 2006-10-31 | 2008-05-01 | Hari Babu Sunkara | Polyether ester elastomer composition |
| US7074969B2 (en) * | 2004-06-18 | 2006-07-11 | E.I. Du Pont De Nemours And Company | Process for preparation of polytrimethylene ether glycols |
| US7396896B2 (en) * | 2004-12-21 | 2008-07-08 | E.I. Dupont De Nemours And Company | Poly(trimethylene terephthalate) composition and shaped articles prepared therefrom |
| US20060189711A1 (en) * | 2005-02-23 | 2006-08-24 | Ng Howard C | Silicon-containing polytrimethylene homo- or copolyether composition |
| US7629396B2 (en) * | 2005-02-23 | 2009-12-08 | E.I. Du Pont De Nemours And Company | Silicon-containing polytrimethylene homo- for copolyether composition |
| US7282159B2 (en) * | 2005-02-25 | 2007-10-16 | E.I. Dupont De Nemours And Company | Process for heat transfer utilizing a polytrimethylene ether glycol or polytrimethylene ether ester glycol based heat transfer fluid |
| US7476344B2 (en) * | 2005-02-25 | 2009-01-13 | E.I. Du Pont De Nemours | Electrical apparatuses containing polytrimethylene homo- or copolyether glycol based electrical insulation fluids |
| US7413677B2 (en) * | 2005-02-25 | 2008-08-19 | E. I. Du Pont De Nemours And Company | Process for heat transfer utilizing a polytrimethylene homo- or copolyether glycol based heat transfer fluid |
| BRPI0608827A2 (pt) * | 2005-04-21 | 2016-11-08 | Shell Int Research | processo para a hidrogenação de aldeídos, catalisador de hidrogenação, e, processo para preparar um catalisador |
| US7244790B2 (en) * | 2005-05-02 | 2007-07-17 | E.I. Du Pont De Nemours And Company | Thermoplastic elastomer blend, method of manufacture and use thereof |
| US20060247378A1 (en) * | 2005-05-02 | 2006-11-02 | Sunkara Hari B | Thermoplastic elastomer blend, method of manufacture and use thereof |
| US7157607B1 (en) | 2005-08-16 | 2007-01-02 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
| US7161045B1 (en) | 2005-08-16 | 2007-01-09 | E. I. Du Pont De Nemours And Company | Process for manufacture of polytrimethylene ether glycol |
| US7357985B2 (en) * | 2005-09-19 | 2008-04-15 | E.I. Du Pont De Nemours And Company | High crimp bicomponent fibers |
| US20070129524A1 (en) * | 2005-12-06 | 2007-06-07 | Sunkara Hari B | Thermoplastic polyurethanes comprising polytrimethylene ether soft segments |
| US20070129503A1 (en) * | 2005-12-07 | 2007-06-07 | Kurian Joseph V | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) molded, shaped articles |
| US20070128459A1 (en) * | 2005-12-07 | 2007-06-07 | Kurian Joseph V | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) films |
| US7666501B2 (en) * | 2005-12-07 | 2010-02-23 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) bi-constituent filaments |
| US7388115B2 (en) * | 2006-01-20 | 2008-06-17 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
| US7164046B1 (en) | 2006-01-20 | 2007-01-16 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
| US20070203371A1 (en) * | 2006-01-23 | 2007-08-30 | Sunkara Hari B | Process for producing polytrimethylene ether glycol |
| BRPI0709821A2 (pt) * | 2006-04-13 | 2011-07-26 | Shell Int Research | processo para a hirogenaÇço de um aldeÍdo |
| JP5258756B2 (ja) * | 2006-05-17 | 2013-08-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | パーソナルケア組成物 |
| US20080039582A1 (en) * | 2006-07-28 | 2008-02-14 | Hari Babu Sunkara | Polytrimethylene ether-based polyurethane ionomers |
| US20080175875A1 (en) * | 2006-09-25 | 2008-07-24 | Hari Babu Sunkara | Cosmetic compositions |
| US7531593B2 (en) | 2006-10-31 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Thermoplastic elastomer blend composition |
| US20080108845A1 (en) * | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
| US20080135662A1 (en) * | 2006-12-06 | 2008-06-12 | Chang Jing C | Melt-spun elastoester multifilament yarns |
| US7714174B2 (en) * | 2007-03-27 | 2010-05-11 | E. I. Du Pont De Nemours And Company | Lower-color polytrimethylene ether glycol using hydride compounds |
| US7943792B2 (en) * | 2007-04-02 | 2011-05-17 | Inventure Chemical Inc. | Production of biodiesel, cellulosic sugars, and peptides from the simultaneous esterification and alcoholysis/hydrolysis of materials with oil-containing substituents including phospholipids and peptidic content |
| WO2008122029A1 (en) * | 2007-04-02 | 2008-10-09 | Inventure Chemical, Inc. | Simultaneous esterification and alcohol ysis/hydrolysis of oil-containing materials with cellulosic and peptidic content |
| US20090043016A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043019A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043021A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US7855244B2 (en) * | 2007-08-06 | 2010-12-21 | E.I. Du Pont De Nemours And Company | Flame retardant polytrimethylene terephthalate composition |
| US20090043017A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| CN101842469A (zh) * | 2007-08-24 | 2010-09-22 | 纳幕尔杜邦公司 | 润滑油组合物 |
| CN101784643A (zh) * | 2007-08-24 | 2010-07-21 | 纳幕尔杜邦公司 | 润滑油组合物 |
| CN101802149A (zh) * | 2007-08-24 | 2010-08-11 | 纳幕尔杜邦公司 | 润滑油组合物 |
| US8703681B2 (en) | 2007-08-24 | 2014-04-22 | E I Du Pont De Nemours And Company | Lubrication oil compositions |
| AU2008293753A1 (en) * | 2007-08-24 | 2009-03-05 | E. I. Du Pont De Nemours And Company | Lubrication oil compositions |
| KR101465290B1 (ko) * | 2007-10-09 | 2014-11-26 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 탈취 조성물 |
| US7919017B2 (en) * | 2007-11-12 | 2011-04-05 | E. I. Du Pont De Nemours And Company | Electrical insulation fluids for use in electrical apparatus |
| US20090197781A1 (en) * | 2008-01-31 | 2009-08-06 | Hari Babu Sunkara | Wellbore Fluids Comprising Poly(trimethylene ether) glycol Polymers |
| EP2100972A1 (en) * | 2008-03-13 | 2009-09-16 | BIOeCON International Holding N.V. | Process for converting polysaccharides in a molten salt hydrate |
| US7777085B2 (en) * | 2008-10-01 | 2010-08-17 | Inventure Chemical, Inc. | Method for conversion of oil-containing algae to 1,3-propanediol |
| AU2009303596A1 (en) * | 2008-10-16 | 2010-04-22 | E. I. Du Pont De Nemours And Company | Flame retardant poly(trimethylene terephthalate) composition |
| AU2009330405A1 (en) | 2008-12-15 | 2010-07-01 | E. I. Du Pont De Nemours And Company | Polymerization of aliphatic-aromatic copolyetheresters |
| JP2012512278A (ja) | 2008-12-15 | 2012-05-31 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 引裂き強さを向上させたコポリエステル |
| KR20110112339A (ko) | 2008-12-15 | 2011-10-12 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 인열 강도가 증진된 코폴리에스테르 |
| WO2010075023A1 (en) | 2008-12-15 | 2010-07-01 | E. I. Du Pont De Nemours And Company | Copolyesters with enhanced tear strength |
| WO2010077937A1 (en) | 2008-12-17 | 2010-07-08 | E. I. Du Pont De Nemours And Company | Reduction of whitening of poly(trimethylene terephthalate) parts by solvent exposure |
| US20100152411A1 (en) | 2008-12-17 | 2010-06-17 | E.I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) with reduced whitening |
| WO2010077905A1 (en) | 2008-12-17 | 2010-07-08 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) polymer blends that have reduced whitening |
| JP2012513523A (ja) * | 2008-12-23 | 2012-06-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリ（トリメチレンエーテル）グリコールのアクリル酸エステルおよびメタクリル酸エステル |
| BRPI0914407A2 (pt) * | 2008-12-23 | 2015-10-20 | Du Pont | "processo, material cerâmico, artigo de couro, pano tecido ou não tecido, material de revestimento, formulação do produto de cuidado pessoal e tinta" |
| US8207372B2 (en) * | 2008-12-23 | 2012-06-26 | E I Du Pont De Nemours And Company | Process for the production of acrylic and methacrylic esters of poly(trimethylene ether) glycol |
| US20110313125A1 (en) | 2009-03-03 | 2011-12-22 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) pellets with reduced oligomers and method to measure oligomer reduction |
| US20100227960A1 (en) | 2009-03-03 | 2010-09-09 | E.I. Du Pont De Nemours And Company | Process of making a poly(trimethylene terephthalate) resin having low cyclic dimer content, and compositions and articles therefrom |
| JP2012519755A (ja) | 2009-03-03 | 2012-08-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 金属層を有する熱可塑性成形物品 |
| US8415015B2 (en) | 2009-04-30 | 2013-04-09 | E I Du Pont De Nemours And Company | Matting agent composition containing polytrimethylene ether diol and use thereof |
| US20110112331A1 (en) * | 2009-11-09 | 2011-05-12 | E.I. Du Pont De Nemours And Company | Method for phase separation of polytrimethylene ether glycol in salt solution |
| WO2011062600A1 (en) | 2009-11-19 | 2011-05-26 | E. I. Du Pont De Nemours And Company | Polycondensation with a kneader reactor |
| EP2643383A1 (en) | 2010-11-22 | 2013-10-02 | E.I. Du Pont De Nemours And Company | Block copolymers comprising poly(1,3-trimethylene terephthalate) and poly(1,3-trimethylene 2,6-naphthalate) |
| US8247526B2 (en) | 2010-12-20 | 2012-08-21 | E I Du Pont De Nemours And Company | Process for the preparation of polyalkylene ether glycol |
| JP5936244B2 (ja) * | 2011-04-26 | 2016-06-22 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | ポリトリメチレンエーテルグリコールを調製する方法 |
| US8759559B2 (en) | 2012-04-18 | 2014-06-24 | E I Du Pont De Nemours And Company | Processes for preparing polytrimethylene ether glycol esters |
| WO2020006043A1 (en) | 2018-06-28 | 2020-01-02 | Dupont Industrial Biosciences Usa, Llc | Spun yarn comprising polyester staple fibre and fabric comprising the same |
| CN112047883B (zh) * | 2019-06-06 | 2024-04-19 | 上海特化医药科技有限公司 | 顺苯磺酸阿曲库铵的制备方法 |
| CN111744486B (zh) * | 2020-07-10 | 2023-03-14 | 深圳圣图科技发展有限公司 | 加氢催化剂及其制备方法和1,3-丁二醇的生产方法 |
| CN113101937A (zh) * | 2021-04-25 | 2021-07-13 | 厦门大学 | 掺杂型混价态铜催化剂及其制备方法和应用 |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2520733A (en) | 1946-08-26 | 1950-08-29 | Shell Dev | Polymers of trimethylene glycol |
| US3326985A (en) | 1964-12-29 | 1967-06-20 | Shell Oil Co | Polytrimethylene glycol |
| JPS511403A (en) * | 1974-06-18 | 1976-01-08 | Toyo Boseki | Echirengurikooruno seiseiho |
| US4213000A (en) | 1979-05-29 | 1980-07-15 | E. I. Du Pont De Nemours And Company | Reducing color formers in 1,4-butanediol |
| JPS60178834A (ja) * | 1984-02-25 | 1985-09-12 | Mitsubishi Petrochem Co Ltd | 高純度エチレングリコール類の製造方法 |
| JPH0635404B2 (ja) * | 1985-02-27 | 1994-05-11 | 三菱化成株式会社 | 粗１，４−ブタンジオ−ルの精製方法 |
| US4885410A (en) | 1987-11-27 | 1989-12-05 | Gaf Corporation | Hydrogenation catalyst |
| DE3917645A1 (de) | 1988-06-23 | 1989-12-28 | Henkel Kgaa | Verfahren zum abtrennen von farbstoffen und/oder geruchsstoffen aus reduktionsstabile wertprodukte enthaltenden fermenterbruehen |
| DE3926136A1 (de) * | 1989-08-08 | 1991-02-14 | Degussa | Verfahren zur herstellung von 1,3-propandiol |
| DE4038192A1 (de) * | 1990-11-30 | 1992-06-04 | Degussa | Verfahren zur herstellung von 1,3-propandiol |
| DE4132663C2 (de) * | 1991-10-01 | 1993-10-14 | Degussa | Verfahren zum Herstellen von 1,3-Propandiol durch Hydrieren von Hydroxypropionaldehyd |
| DE4138981A1 (de) * | 1991-11-27 | 1993-06-03 | Degussa | Verfahren zur herstellung von 3-hydroxyalkanalen |
| DE4138982A1 (de) * | 1991-11-27 | 1993-06-03 | Degussa | Verfahren zur herstellung von 3-hydroxyalkanalen |
| DE4218282A1 (de) * | 1992-06-03 | 1993-12-09 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| DE4222708A1 (de) * | 1992-07-10 | 1994-01-13 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| JP3175360B2 (ja) * | 1992-12-10 | 2001-06-11 | 三菱化学株式会社 | １，４−ブタンジオールの精製方法 |
| DE4342345C2 (de) | 1993-12-11 | 1998-10-22 | Merck Patent Gmbh | Entfärbung von Fermentationslösungen |
| US5981808A (en) * | 1994-09-30 | 1999-11-09 | Shell Oil Company | Cobalt-catalyzed process for preparing 1, 3-propanediol from etylene oxide |
| US5527973A (en) | 1994-12-16 | 1996-06-18 | Kelsey; Donald R. | Purification of 1,3-propanediol |
| US5686276A (en) | 1995-05-12 | 1997-11-11 | E. I. Du Pont De Nemours And Company | Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism |
| US5633362A (en) | 1995-05-12 | 1997-05-27 | E. I. Du Pont De Nemours And Company | Production of 1,3-propanediol from glycerol by recombinant bacteria expressing recombinant diol dehydratase |
| US5786524A (en) * | 1996-05-30 | 1998-07-28 | Shell Oil Company | Process for preparation of 1,3-propanediol via hydrogenation of 3-hydroxypropanal |
| US6111137A (en) | 1996-12-20 | 2000-08-29 | Mitsui Chemicals, Inc. | Purification process of lactic acid |
| JPH10265418A (ja) * | 1997-01-23 | 1998-10-06 | Mitsubishi Chem Corp | 粗１，４−ブタンジオールの精製方法 |
| DE19703383A1 (de) * | 1997-01-30 | 1998-08-06 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| US5962745A (en) * | 1997-02-14 | 1999-10-05 | E. I. Du Pont De Nemours And Company | Process for preparing 3-hydroxyalkanals |
| KR20010013907A (ko) * | 1997-06-18 | 2001-02-26 | 메리 이. 보울러 | 3-히드록시프로피온알데히드의 수소화에 의한1,3-프로판디올의 제조 방법 |
| US5986145A (en) * | 1997-08-22 | 1999-11-16 | Shell Oil Company | Purification of 3-hydroxy-propanal |
| US6235948B1 (en) | 1998-08-18 | 2001-05-22 | E. I. Du Pont De Nemours And Company | Process for the purification of 1,3-propanediol |
| BR9913475A (pt) * | 1998-09-04 | 2001-08-14 | Du Pont | Processo para a produção de 1,3-propanodiol |
| DE19840277A1 (de) * | 1998-09-04 | 2000-03-09 | Degussa | Verfahren zur Reduzierung des Gehalts an Acetalen oder Ketalen in alkoholischen Reaktionsgemischen |
| US6245844B1 (en) | 1998-09-18 | 2001-06-12 | E. I. Du Pont De Nemours And Company | Nucleating agent for polyesters |
| US6191321B1 (en) * | 1998-09-30 | 2001-02-20 | Shell Oil Company | Process for preparing 1,3-propanediol from methyl 3-hydroxypropionate |
| US5945570A (en) * | 1998-10-29 | 1999-08-31 | Arhancet; Juan Pedro | Catalyst and process for preparing 1,3-propanediol |
| US6350895B1 (en) * | 1999-03-26 | 2002-02-26 | E. I. Du Pont De Nemours And Company | Transesterification process using yttrium and samarium compound catalystis |
| US6331264B1 (en) * | 1999-03-31 | 2001-12-18 | E. I. Du Pont De Nemours And Company | Low emission polymer compositions |
| US6277289B1 (en) * | 1999-07-01 | 2001-08-21 | E. I. Du Pont De Nemours And Company | Treatment of aqueous aldehyde waste streams |
| US6342646B1 (en) * | 1999-07-30 | 2002-01-29 | E. I. Du Pont De Nemours And Company | Catalytic hydrogenation of 3-hydroxypropanal to 1,3-propanediol |
| US6284930B1 (en) * | 1999-07-30 | 2001-09-04 | E.I. Du Pont De Nemours And Company | Process for the preparation of 3-hydroxypropanal |
| JP5283298B2 (ja) * | 1999-08-25 | 2013-09-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ジ（１，３−プロピレングリコール）低レベル含有ポリ（トリメチレンテレフタレート）の調製 |
| US6720459B2 (en) | 1999-12-17 | 2004-04-13 | E. I. Du Pont Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| DE60028086T2 (de) | 1999-12-17 | 2006-12-21 | E.I. Dupont De Nemours And Co., Wilmington | Herstellung von polytrimethylene ether glycol und copolymere davon |
| US6255442B1 (en) * | 2000-02-08 | 2001-07-03 | E. I. Du Pont De Nemours And Company | Esterification process |
| US6353062B1 (en) * | 2000-02-11 | 2002-03-05 | E. I. Du Pont De Nemours And Company | Continuous process for producing poly(trimethylene terephthalate) |
| US6972346B2 (en) * | 2002-11-01 | 2005-12-06 | Shell Oil Company | Solid acid catalyzed reactive stripping of impurities formed during the production of 1, 3-propanediol |
| CN1321959C (zh) | 2003-02-24 | 2007-06-20 | 国际壳牌研究有限公司 | 通过蒸馏纯化1,3－丙二醇 |
| US20040211729A1 (en) * | 2003-04-25 | 2004-10-28 | Sunkara Hari Babu | Processes for recovering oligomers of glycols and polymerization catalysts from waste streams |
| US7323539B2 (en) * | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
| US20040225107A1 (en) * | 2003-05-06 | 2004-11-11 | Sunkara Hari Babu | Polytrimethylene ether glycol with excellent quality from biochemically-derived 1,3-propanediol |
| US7009082B2 (en) | 2003-05-06 | 2006-03-07 | E.I. Du Pont De Nemours And Company | Removal of color bodies from polytrimethylene ether glycol polymers |
| US7342142B2 (en) * | 2003-05-06 | 2008-03-11 | E.I. Du Pont De Nemours And Company | Hydrogenation of polytrimethylene ether glycol |
-
2003
- 2003-08-05 US US10/634,666 patent/US7084311B2/en not_active Expired - Fee Related
-
2004
- 2004-05-05 CA CA002522681A patent/CA2522681A1/en not_active Abandoned
- 2004-05-05 JP JP2006532799A patent/JP4642028B2/ja not_active Expired - Fee Related
- 2004-05-05 DE DE112004000754T patent/DE112004000754T5/de not_active Withdrawn
- 2004-05-05 WO PCT/US2004/014040 patent/WO2004101468A2/en not_active Ceased
-
2005
- 2005-08-12 US US11/203,029 patent/US7038092B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007500214A (ja) | 2007-01-11 |
| JP4642028B2 (ja) | 2011-03-02 |
| WO2004101468A2 (en) | 2004-11-25 |
| US7038092B2 (en) | 2006-05-02 |
| CA2522681A1 (en) | 2004-11-25 |
| US20050272962A1 (en) | 2005-12-08 |
| US7084311B2 (en) | 2006-08-01 |
| US20040225161A1 (en) | 2004-11-11 |
| WO2004101468A3 (en) | 2005-07-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE112004000754T5 (de) | Hydrierung von chemisch deriviertem 1,3-Propandiol | |
| JP4908218B2 (ja) | 生化学的に誘導された１，３−プロパンジオールの水素化 | |
| DE60028086T2 (de) | Herstellung von polytrimethylene ether glycol und copolymere davon | |
| DE69817356T2 (de) | Verfahren zur herstellung von 1,3-propandiol durch hydrierung von 3-hydroxypropanal | |
| DE4218282A1 (de) | Verfahren zur Herstellung von 1,3-Propandiol | |
| EP2417088B1 (de) | Verfahren zur herstellung von 1,6-hexandiol | |
| EP1113034B1 (de) | Mit isomeren Nonanolen abgeschlossene Polyester, Verfahren zu ihrer Herstellung und ihre Verwendung als Weichmacher | |
| EP2244996B2 (de) | Verfahren zur herstellung von 6-hydroxycapronsäureestern | |
| US7342142B2 (en) | Hydrogenation of polytrimethylene ether glycol | |
| EP1003803A1 (de) | Verfahren zur herstellung von polytetrahydrofuran mit niedriger farbzahl | |
| EP1370600A1 (de) | Verfahren zur aufarbeitung von polyetheralkoholen | |
| DE69636943T2 (de) | Verfahren zur Herstellung von Etherverbindungen | |
| EP1326819B1 (de) | Farbzahlverbesserung von mehrwertigen alkoholen durch hydrierung | |
| EP1889825A1 (de) | Verfahren zur Herstellung von 1,2-Propandiol | |
| CN100448826C (zh) | 化学衍生1,3-丙二醇的氢化 | |
| CN100475761C (zh) | 聚三亚甲基醚二醇的氢化 | |
| DE10325264A1 (de) | Hochreine Polyalkylenglykole und Verfahren zur Herstellung | |
| DE10334489A1 (de) | Verfahren zur hydrierenden Zersetzung von Ammoniumformiaten in polyolhaltigen Reaktionsgemischen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| R119 | Application deemed withdrawn, or ip right lapsed, due to non-payment of renewal fee |
Effective date: 20121201 |