SK281399B6 - Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov - Google Patents
Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov Download PDFInfo
- Publication number
- SK281399B6 SK281399B6 SK389-97A SK38997A SK281399B6 SK 281399 B6 SK281399 B6 SK 281399B6 SK 38997 A SK38997 A SK 38997A SK 281399 B6 SK281399 B6 SK 281399B6
- Authority
- SK
- Slovakia
- Prior art keywords
- cobalt
- group
- acetate
- process according
- hydroformylation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 33
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 66
- 239000010941 cobalt Substances 0.000 claims abstract description 66
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 35
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000003839 salts Chemical group 0.000 claims abstract description 12
- 229910021478 group 5 element Inorganic materials 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- NCYWEOAYLCHMDJ-UHFFFAOYSA-M tetraoctylphosphanium;acetate Chemical compound CC([O-])=O.CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC NCYWEOAYLCHMDJ-UHFFFAOYSA-M 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 239000004254 Ammonium phosphate Substances 0.000 claims 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims 1
- 235000019289 ammonium phosphates Nutrition 0.000 claims 1
- JRHRMSCDQNLWJY-UHFFFAOYSA-M benzyl(trimethyl)phosphanium;acetate Chemical compound CC([O-])=O.C[P+](C)(C)CC1=CC=CC=C1 JRHRMSCDQNLWJY-UHFFFAOYSA-M 0.000 claims 1
- LXTKCTMGEWVPTB-UHFFFAOYSA-N butylazanium;acetate Chemical compound CC(O)=O.CCCCN LXTKCTMGEWVPTB-UHFFFAOYSA-N 0.000 claims 1
- 238000007037 hydroformylation reaction Methods 0.000 abstract description 53
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract description 7
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 abstract description 6
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 40
- AKXKFZDCRYJKTF-UHFFFAOYSA-N 3-Hydroxypropionaldehyde Chemical compound OCCC=O AKXKFZDCRYJKTF-UHFFFAOYSA-N 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000000605 extraction Methods 0.000 description 28
- 239000000047 product Substances 0.000 description 22
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000005984 hydrogenation reaction Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000010410 layer Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- -1 cyclic hemiacetal Chemical class 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 238000004064 recycling Methods 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000006286 aqueous extract Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000001868 cobalt Chemical class 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- SMTUJUHULKBTBS-UHFFFAOYSA-N benzyl(trimethyl)azanium;methanolate Chemical compound [O-]C.C[N+](C)(C)CC1=CC=CC=C1 SMTUJUHULKBTBS-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000003550 marker Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TWWBIMNLBUYJKB-UHFFFAOYSA-N phosphanyl acetate Chemical compound CC(=O)OP TWWBIMNLBUYJKB-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 2
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CFUSADRNVKTODB-UHFFFAOYSA-N 2-(2,2-dimethylbutyl)-2-methyloxirane Chemical compound CCC(C)(C)CC1(C)CO1 CFUSADRNVKTODB-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- ONNUYWHIJSKABC-UHFFFAOYSA-N 2-methylpropoxybenzene Chemical compound CC(C)COC1=CC=CC=C1 ONNUYWHIJSKABC-UHFFFAOYSA-N 0.000 description 1
- SPXXVGQMQJYJJO-UHFFFAOYSA-N 2-prop-2-enyloxirane Chemical compound C=CCC1CO1 SPXXVGQMQJYJJO-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- DMFFPWIZNUMJNS-UHFFFAOYSA-M benzyl(tributyl)azanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 DMFFPWIZNUMJNS-UHFFFAOYSA-M 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003965 capillary gas chromatography Methods 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
-
- 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
- C07C29/136—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 of >C=O containing groups, e.g. —COOH
- C07C29/14—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 of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—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 of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/316,673 US5463145A (en) | 1994-09-30 | 1994-09-30 | Process for preparing 1,3-propanediol |
| US08/316,661 US5545765A (en) | 1994-09-30 | 1994-09-30 | Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic quaternary arsonium salt promoter |
| PCT/EP1995/003868 WO1996010550A1 (en) | 1994-09-30 | 1995-09-28 | Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK38997A3 SK38997A3 (en) | 1997-11-05 |
| SK281399B6 true SK281399B6 (sk) | 2001-03-12 |
Family
ID=26980535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK389-97A SK281399B6 (sk) | 1994-09-30 | 1995-09-28 | Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0783475B1 (cs) |
| JP (1) | JP3779729B2 (cs) |
| KR (1) | KR100393706B1 (cs) |
| CN (1) | CN1089083C (cs) |
| AT (1) | ATE174319T1 (cs) |
| AU (1) | AU689963B2 (cs) |
| BR (1) | BR9509054A (cs) |
| CA (1) | CA2201305C (cs) |
| CZ (1) | CZ289381B6 (cs) |
| DE (1) | DE69506573T2 (cs) |
| DK (1) | DK0783475T3 (cs) |
| ES (1) | ES2125665T3 (cs) |
| FI (1) | FI971267L (cs) |
| HU (1) | HUT77463A (cs) |
| MX (1) | MX9702278A (cs) |
| MY (1) | MY112931A (cs) |
| NO (1) | NO307561B1 (cs) |
| NZ (1) | NZ294240A (cs) |
| PL (1) | PL181433B1 (cs) |
| RU (1) | RU2149156C1 (cs) |
| SK (1) | SK281399B6 (cs) |
| TR (1) | TR199501190A2 (cs) |
| TW (1) | TW442458B (cs) |
| WO (1) | WO1996010550A1 (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69506574T2 (de) * | 1994-09-30 | 1999-06-17 | Shell Internationale Research Maatschappij B.V., Den Haag/S'gravenhage | Verfahren zur herstellung von 1,3-alkandiolen und 3-hydroxyaldehyden |
| JP2003528065A (ja) * | 2000-03-22 | 2003-09-24 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | １，３−ジオールを調製するための方法 |
| DE10065176A1 (de) * | 2000-12-23 | 2002-06-27 | Degussa | Katalysator und Verfahren zur Herstellung von niedrigviskosen und farbreduzierten isocyanuratgruppenhaltigen Polyisocyanaten |
| US6586643B2 (en) * | 2001-05-18 | 2003-07-01 | Shell Oil Company | One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a N-heterocyclic ligand |
| TW592819B (en) * | 2001-05-18 | 2004-06-21 | Kevin Dale Allen | One-step production of 1,3-propanediol from ethylene oxide and syngas with a cobalt-iron catalyst |
| TW593239B (en) * | 2001-06-04 | 2004-06-21 | Kevin Dale Allen | One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a phospholanoalkane ligand |
| US7056439B2 (en) * | 2003-05-06 | 2006-06-06 | Tate & Lyle Ingredidents Americas, Inc. | Process for producing 1, 3-propanediol |
| AR071269A1 (es) * | 2007-12-19 | 2010-06-09 | Shell Int Research | Proceso para elaborar un betahidroxialdehido |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3456017A (en) * | 1965-10-21 | 1969-07-15 | Shell Oil Co | Glycol production |
| US3463819A (en) * | 1965-10-21 | 1969-08-26 | Shell Oil Co | Glycol production |
| US3687981A (en) * | 1968-01-17 | 1972-08-29 | Du Pont | Process for making a dioxane |
| CA1279657C (en) * | 1986-08-20 | 1991-01-29 | Mark A. Murphy | Process for making 1,3-glycols from epoxides |
| US4973741A (en) * | 1989-06-29 | 1990-11-27 | Eastman Kodak Company | Difunctional products from ethylene oxide and synthesis gas |
| RU2038844C1 (ru) * | 1990-05-04 | 1995-07-09 | Юнион Карбайд Кемикалз Энд Пластикс Текнолоджи Корпорейшн | Каталитическая композиция для гидроформилирования этиленоксида, способ ее получения и способ получения 1,3-пропандиола и 3-гидроксипропионового альдегида |
| JP3571720B2 (ja) * | 1993-02-05 | 2004-09-29 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | １，３−ジオール及び３−ヒドロキシアルデヒドを作るための方法 |
| US5256827A (en) * | 1993-02-05 | 1993-10-26 | Shell Oil Company | Process for making 3-hydroxypropanal and 1,3-propanediol |
| WO1996010551A1 (en) * | 1994-09-30 | 1996-04-11 | Shell Internationale Research Maatschappij B.V. | Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes |
| DE69506574T2 (de) * | 1994-09-30 | 1999-06-17 | Shell Internationale Research Maatschappij B.V., Den Haag/S'gravenhage | Verfahren zur herstellung von 1,3-alkandiolen und 3-hydroxyaldehyden |
-
1995
- 1995-09-28 BR BR9509054A patent/BR9509054A/pt not_active IP Right Cessation
- 1995-09-28 EP EP95934652A patent/EP0783475B1/en not_active Expired - Lifetime
- 1995-09-28 CN CN95195315A patent/CN1089083C/zh not_active Expired - Fee Related
- 1995-09-28 DE DE69506573T patent/DE69506573T2/de not_active Expired - Fee Related
- 1995-09-28 KR KR1019970702071A patent/KR100393706B1/ko not_active Expired - Fee Related
- 1995-09-28 AT AT95934652T patent/ATE174319T1/de not_active IP Right Cessation
- 1995-09-28 ES ES95934652T patent/ES2125665T3/es not_active Expired - Lifetime
- 1995-09-28 MY MYPI95002897A patent/MY112931A/en unknown
- 1995-09-28 JP JP51140196A patent/JP3779729B2/ja not_active Expired - Fee Related
- 1995-09-28 MX MX9702278A patent/MX9702278A/es unknown
- 1995-09-28 CZ CZ1997943A patent/CZ289381B6/cs not_active IP Right Cessation
- 1995-09-28 RU RU97106785A patent/RU2149156C1/ru not_active IP Right Cessation
- 1995-09-28 HU HU9702306A patent/HUT77463A/hu unknown
- 1995-09-28 FI FI971267A patent/FI971267L/fi unknown
- 1995-09-28 CA CA002201305A patent/CA2201305C/en not_active Expired - Fee Related
- 1995-09-28 WO PCT/EP1995/003868 patent/WO1996010550A1/en not_active Ceased
- 1995-09-28 SK SK389-97A patent/SK281399B6/sk unknown
- 1995-09-28 NZ NZ294240A patent/NZ294240A/xx unknown
- 1995-09-28 AU AU36993/95A patent/AU689963B2/en not_active Ceased
- 1995-09-28 PL PL95319438A patent/PL181433B1/pl unknown
- 1995-09-28 DK DK95934652T patent/DK0783475T3/da active
- 1995-09-29 TR TR95/01190A patent/TR199501190A2/xx unknown
-
1996
- 1996-02-08 TW TW085101552A patent/TW442458B/zh not_active IP Right Cessation
-
1997
- 1997-03-25 NO NO971420A patent/NO307561B1/no unknown
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