SK281399B6 - Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov - Google Patents

Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov Download PDF

Info

Publication number: SK281399B6
Authority: SK; Slovakia
Prior art keywords: cobalt; group; acetate; process according; hydroformylation
Prior art date: 1994-09-30

Application number

SK389-97A

Other languages

English (en)

Slovak (sk)

Other versions

SK38997A3 (en

Inventor

Juan Pedro Arhancet

Thomas Clayton Forschner

Joseph Broun Powell

Thomas Carl Semple

Lynn Henry Slaugh

Terry Blane Thomason

Paul Richard Weider

Original Assignee

Shell Internationale Research Maatschappij B. V.

Priority date (The priority date 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 date listed.)

1994-09-30

Filing date

1995-09-28

Publication date

2001-03-12

1994-09-30 Priority claimed from US08/316,661 external-priority patent/US5545765A/en

1994-09-30 Priority claimed from US08/316,673 external-priority patent/US5463145A/en

1995-09-28 Application filed by Shell Internationale Research Maatschappij B. V. filed Critical Shell Internationale Research Maatschappij B. V.

1997-11-05 Publication of SK38997A3 publication Critical patent/SK38997A3/sk

2001-03-12 Publication of SK281399B6 publication Critical patent/SK281399B6/sk

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)

SK389-97A 1994-09-30 1995-09-28 Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov SK281399B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
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
US08/316,673 US5463145A (en)	1994-09-30	1994-09-30	Process for preparing 1,3-propanediol
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)

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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)	FI971267A0 (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)

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SK281565B6 (sk) *	1994-09-30	2001-05-10	Shell Internationale Research Maatschappij B. V.	Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov
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
US6750373B2 (en) *	2001-05-18	2004-06-15	Shell Oil Company	One-step production of 1, 3-propanediol from ethylene oxide and syngas with a cobalt-iron catalyst
TW593238B (en) *	2001-05-18	2004-06-21	Kevin Dale Allen	One-step production of 1,3-propanediol from ethylene oxide and syngas with a catalyst with a N-heterocyclic ligand
US6576802B2 (en) *	2001-06-04	2003-06-10	Shell Oil Company	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
WO2009079551A1 (en) *	2007-12-19	2009-06-25	Shell Oil Company	Heterogeneous promotion of oxirane hydroformylation

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US3463819A (en) *	1965-10-21	1969-08-26	Shell Oil Co	Glycol production
US3456017A (en) *	1965-10-21	1969-07-15	Shell Oil Co	Glycol production
US3687981A (en) *	1968-01-17	1972-08-29	Du Pont	Process for making a dioxane
ZA875926B (en) *	1986-08-20	1988-02-15	Hoechst Celanese Corporation	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
US5256827A (en) *	1993-02-05	1993-10-26	Shell Oil Company	Process for making 3-hydroxypropanal and 1,3-propanediol
EP0682650B1 (en) *	1993-02-05	1998-05-20	Shell Internationale Researchmaatschappij B.V.	Process for making 1,3-diols and 3-hydroxyaldehydes
SK281565B6 (sk) *	1994-09-30	2001-05-10	Shell Internationale Research Maatschappij B. V.	Spôsob prípravy 1,3-alkándiolov a 3-hydroxyaldehydov
CN1064345C (zh) *	1994-09-30	2001-04-11	国际壳牌研究有限公司	制备1,3－链烷二醇和3－羟基醛的方法

1995
- 1995-09-28 MY MYPI95002897A patent/MY112931A/en unknown
- 1995-09-28 AT AT95934652T patent/ATE174319T1/de not_active IP Right Cessation
- 1995-09-28 NZ NZ294240A patent/NZ294240A/xx unknown
- 1995-09-28 CZ CZ1997943A patent/CZ289381B6/cs not_active IP Right Cessation
- 1995-09-28 EP EP95934652A patent/EP0783475B1/en not_active Expired - Lifetime
- 1995-09-28 PL PL95319438A patent/PL181433B1/pl unknown
- 1995-09-28 DK DK95934652T patent/DK0783475T3/da active
- 1995-09-28 RU RU97106785A patent/RU2149156C1/ru not_active IP Right Cessation
- 1995-09-28 FI FI971267A patent/FI971267A0/fi unknown
- 1995-09-28 CN CN95195315A patent/CN1089083C/zh not_active Expired - Fee Related
- 1995-09-28 CA CA002201305A patent/CA2201305C/en not_active Expired - Fee Related
- 1995-09-28 KR KR1019970702071A patent/KR100393706B1/ko not_active Expired - Fee Related
- 1995-09-28 JP JP51140196A patent/JP3779729B2/ja not_active Expired - Fee Related
- 1995-09-28 BR BR9509054A patent/BR9509054A/pt not_active IP Right Cessation
- 1995-09-28 WO PCT/EP1995/003868 patent/WO1996010550A1/en not_active Ceased
- 1995-09-28 AU AU36993/95A patent/AU689963B2/en not_active Ceased
- 1995-09-28 ES ES95934652T patent/ES2125665T3/es not_active Expired - Lifetime
- 1995-09-28 MX MX9702278A patent/MX9702278A/es unknown
- 1995-09-28 SK SK389-97A patent/SK281399B6/sk unknown
- 1995-09-28 HU HU9702306A patent/HUT77463A/hu unknown
- 1995-09-28 DE DE69506573T patent/DE69506573T2/de not_active Expired - Fee Related
- 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

Also Published As

Publication number	Publication date
JPH10507165A (ja)	1998-07-14
PL319438A1 (en)	1997-08-04
CA2201305C (en)	2007-09-11
TW442458B (en)	2001-06-23
WO1996010550A1 (en)	1996-04-11
FI971267A7 (fi)	1997-03-26
PL181433B1 (pl)	2001-07-31
CN1089083C (zh)	2002-08-14
MX9702278A (es)	1997-06-28
RU2149156C1 (ru)	2000-05-20
FI971267L (fi)	1997-03-26
NO307561B1 (no)	2000-04-25
HUT77463A (hu)	1998-05-28
NZ294240A (en)	1998-12-23
EP0783475B1 (en)	1998-12-09
NO971420L (no)	1997-03-25
EP0783475A1 (en)	1997-07-16
ATE174319T1 (de)	1998-12-15
CN1161685A (zh)	1997-10-08
AU689963B2 (en)	1998-04-09
BR9509054A (pt)	1998-06-23
AU3699395A (en)	1996-04-26
KR100393706B1 (ko)	2003-11-20
FI971267A0 (fi)	1997-03-26
ES2125665T3 (es)	1999-03-01
DE69506573D1 (de)	1999-01-21
TR199501190A2 (tr)	1996-06-21
DE69506573T2 (de)	1999-06-17
JP3779729B2 (ja)	2006-05-31
MY112931A (en)	2001-10-31
NO971420D0 (no)	1997-03-25
CZ94397A3 (cs)	1998-02-18
CZ289381B6 (cs)	2002-01-16
DK0783475T3 (da)	1999-08-16
SK38997A3 (en)	1997-11-05
CA2201305A1 (en)	1996-04-11

Publication	Publication Date	Title
US5463145A (en)	1995-10-31	Process for preparing 1,3-propanediol
RU2142934C1 (ru)	1999-12-20	Способ получения 1,3-алкандиолов и 3-гидроксиальдегидов
US5463146A (en)	1995-10-31	Process for preparing 1,3-propanediol
US5463144A (en)	1995-10-31	Process for preparing 1,3-propanediol
US5723389A (en)	1998-03-03	Process for preparing alkanediols
US5563302A (en)	1996-10-08	Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic phosphine oxide promoter
US5731478A (en)	1998-03-24	Process for preparing alkanediols
US5585528A (en)	1996-12-17	Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic tertiary amine promoter
US5545767A (en)	1996-08-13	Process for preparing 1,3-propanediol
US5545765A (en)	1996-08-13	Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic quaternary arsonium salt promoter
US5576471A (en)	1996-11-19	Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic dihydroxyarene promoter
SK38997A3 (en)	1997-11-05	Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes
US5545766A (en)	1996-08-13	Cobalt-catalyzed process for preparing 1,3-propanediol using a lipophilic bidentate phosphine promotor
US6376720B1 (en)	2002-04-23	Cobalt-catalyzed process for preparing 1,3-propanediol
MXPA97002278A (en)	1997-06-01	Process for preparing 1, 3-alcanodioles y3-hidroxialdehi
JP3698438B2 (ja)	2005-09-21	１，３−アルカンジオールと３−ヒドロキシアルデヒドの調製方法
US6376724B1 (en)	2002-04-23	Cobalt-catalyzed process for preparing 1,3-propanediol
US6323374B1 (en)	2001-11-27	Cobalt-catalyzed process for preparing 1,3-propanediol
CA2201304C (en)	2007-06-26	Process for preparing 1,3-alkanediols and 3-hydroxyaldehydes
US20030032845A1 (en)	2003-02-13	Hydroformylation of ethylene oxide
SA96160544B1 (ar)	2006-05-20	طريقة لتحضير 3.1-الكان ديولات و 3-هيدروكسي الدهيدات 1.3-alkanediols and 3- hydroxyaldehydes
MXPA98007262A (en)	1999-10-14	Process for preparing 1,3-propanod