NO310406B1 - Fremgangsmåter for fremstilling av C3-C6aldehyder - Google Patents
Fremgangsmåter for fremstilling av C3-C6aldehyder Download PDFInfo
- Publication number
- NO310406B1 NO310406B1 NO19973306A NO973306A NO310406B1 NO 310406 B1 NO310406 B1 NO 310406B1 NO 19973306 A NO19973306 A NO 19973306A NO 973306 A NO973306 A NO 973306A NO 310406 B1 NO310406 B1 NO 310406B1
- Authority
- NO
- Norway
- Prior art keywords
- catalyst
- hydroformylation
- rhodium
- olefins
- acetylene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 144
- 150000001299 aldehydes Chemical class 0.000 title claims abstract description 93
- 239000010948 rhodium Substances 0.000 claims abstract description 184
- 239000003054 catalyst Substances 0.000 claims abstract description 171
- 150000001336 alkenes Chemical class 0.000 claims abstract description 103
- 239000000203 mixture Substances 0.000 claims abstract description 97
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 89
- 230000008569 process Effects 0.000 claims abstract description 82
- 239000005977 Ethylene Substances 0.000 claims abstract description 74
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 73
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 69
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 69
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 claims abstract description 41
- 150000001993 dienes Chemical class 0.000 claims abstract description 32
- 150000001298 alcohols Chemical class 0.000 claims abstract description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 230000001955 cumulated effect Effects 0.000 claims abstract description 13
- 239000011574 phosphorus Substances 0.000 claims abstract description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 135
- 238000007037 hydroformylation reaction Methods 0.000 claims description 131
- 150000001875 compounds Chemical class 0.000 claims description 123
- 238000003786 synthesis reaction Methods 0.000 claims description 110
- 230000015572 biosynthetic process Effects 0.000 claims description 109
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 98
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 54
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 52
- 239000003446 ligand Substances 0.000 claims description 51
- 238000005984 hydrogenation reaction Methods 0.000 claims description 38
- 230000036961 partial effect Effects 0.000 claims description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 30
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims description 29
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 27
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 26
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- 238000005882 aldol condensation reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 abstract description 10
- 239000000543 intermediate Substances 0.000 abstract description 4
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 163
- 239000000243 solution Substances 0.000 description 74
- 239000000047 product Substances 0.000 description 68
- 229910052739 hydrogen Inorganic materials 0.000 description 47
- 239000001257 hydrogen Substances 0.000 description 42
- 238000002474 experimental method Methods 0.000 description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 33
- 238000010521 absorption reaction Methods 0.000 description 31
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 28
- 230000000875 corresponding effect Effects 0.000 description 28
- 238000004064 recycling Methods 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 25
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 23
- 239000012071 phase Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 239000000376 reactant Substances 0.000 description 20
- 239000007788 liquid Substances 0.000 description 19
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
- 238000011084 recovery Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000001361 allenes Chemical class 0.000 description 15
- 150000002430 hydrocarbons Chemical class 0.000 description 15
- 230000009849 deactivation Effects 0.000 description 14
- 239000007791 liquid phase Substances 0.000 description 14
- 238000000926 separation method Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 230000007306 turnover Effects 0.000 description 13
- 150000001335 aliphatic alkanes Chemical class 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- -1 ethylene, propylene, butenes Chemical class 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000004817 gas chromatography Methods 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 230000008901 benefit Effects 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000011069 regeneration method Methods 0.000 description 9
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 239000002574 poison Substances 0.000 description 8
- 231100000614 poison Toxicity 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000872 buffer Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 7
- 239000011241 protective layer Substances 0.000 description 7
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- AMXBISSOONGENB-UHFFFAOYSA-N acetylene;ethene Chemical group C=C.C#C AMXBISSOONGENB-UHFFFAOYSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000006851 Roelen carbonylation reaction Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000012619 stoichiometric conversion Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- 239000003345 natural gas Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000004230 steam cracking Methods 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000001311 chemical methods and process Methods 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000004868 gas analysis Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 230000002427 irreversible effect Effects 0.000 description 3
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 150000003283 rhodium Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 2
- 238000003889 chemical engineering Methods 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- ZXKWUYWWVSKKQZ-UHFFFAOYSA-N cyclohexyl(diphenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZXKWUYWWVSKKQZ-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 description 2
- HXUARCOTWDKZOU-UHFFFAOYSA-N dioctyl(phenyl)phosphane Chemical compound CCCCCCCCP(CCCCCCCC)C1=CC=CC=C1 HXUARCOTWDKZOU-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000007210 heterogeneous catalysis Methods 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000011068 loading method Methods 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
- 238000002156 mixing Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical class CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 2
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 2
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
- 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
- UAXNXOMKCGKNCI-UHFFFAOYSA-N 1-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 UAXNXOMKCGKNCI-UHFFFAOYSA-N 0.000 description 1
- IDEYZABHVQLHAF-XQRVVYSFSA-N 2-Methyl-2-pentenal Chemical compound CC\C=C(\C)C=O IDEYZABHVQLHAF-XQRVVYSFSA-N 0.000 description 1
- IDEYZABHVQLHAF-UHFFFAOYSA-N 2-Methyl-2-pentenal Natural products CCC=C(C)C=O IDEYZABHVQLHAF-UHFFFAOYSA-N 0.000 description 1
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 1
- SFUCQIUDZBXOOP-UHFFFAOYSA-N 4-bis(4-cyanophenyl)phosphanylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1P(C=1C=CC(=CC=1)C#N)C1=CC=C(C#N)C=C1 SFUCQIUDZBXOOP-UHFFFAOYSA-N 0.000 description 1
- GOEGBJDTWXTPHP-UHFFFAOYSA-N 4-diphenylphosphanyl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 GOEGBJDTWXTPHP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 101100135641 Caenorhabditis elegans par-3 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- 238000012565 NMR experiment Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- LKSFJNGLRHVLIF-UHFFFAOYSA-O O=C[Rh]P(c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound O=C[Rh]P(c1ccccc1)(c1ccccc1)c1ccccc1 LKSFJNGLRHVLIF-UHFFFAOYSA-O 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 208000034809 Product contamination Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 238000010685 alcohol synthesis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- AASUFOVSZUIILF-UHFFFAOYSA-N diphenylmethanone;sodium Chemical compound [Na].C=1C=CC=CC=1C(=O)C1=CC=CC=C1 AASUFOVSZUIILF-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 239000003574 free electron Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- KEJVUXJFDYXFSK-UHFFFAOYSA-N octyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCCCC)C1=CC=CC=C1 KEJVUXJFDYXFSK-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical compound P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- 231100000817 safety factor Toxicity 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- DMEUUKUNSVFYAA-UHFFFAOYSA-N trinaphthalen-1-ylphosphane Chemical compound C1=CC=C2C(P(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 DMEUUKUNSVFYAA-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/11—Purification; Separation; Use of additives by absorption, i.e. purification or separation of gaseous hydrocarbons with the aid of liquids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1487—Removing organic compounds
-
- 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
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37532495A | 1995-01-18 | 1995-01-18 | |
| US08/375,432 US5516965A (en) | 1995-01-18 | 1995-01-18 | Unsaturates recovery and recycle process |
| US08/375,434 US5520722A (en) | 1995-01-18 | 1995-01-18 | Multiunsaturates removal process |
| PCT/EP1996/000268 WO1996022266A1 (en) | 1995-01-18 | 1996-01-17 | Hydroformylation of a multi-component feed stream |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO973306D0 NO973306D0 (no) | 1997-07-17 |
| NO973306L NO973306L (no) | 1997-09-16 |
| NO310406B1 true NO310406B1 (no) | 2001-07-02 |
Family
ID=27409241
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19973306A NO310406B1 (no) | 1995-01-18 | 1997-07-17 | Fremgangsmåter for fremstilling av C3-C6aldehyder |
| NO20005945A NO311351B1 (no) | 1995-01-18 | 2000-11-24 | Fremgangsmåte for fremstilling av en tilförselsström som er nyttig i en prosess for fremstilling av C3-C6aldehyder |
| NO20005944A NO311350B1 (no) | 1995-01-18 | 2000-11-24 | Fremgangsmåter for utvinning av ureagerte umettede hydrokarboner fra en utlöpsström i en prosess for fremstilling avC3-C6aldehyder |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20005945A NO311351B1 (no) | 1995-01-18 | 2000-11-24 | Fremgangsmåte for fremstilling av en tilförselsström som er nyttig i en prosess for fremstilling av C3-C6aldehyder |
| NO20005944A NO311350B1 (no) | 1995-01-18 | 2000-11-24 | Fremgangsmåter for utvinning av ureagerte umettede hydrokarboner fra en utlöpsström i en prosess for fremstilling avC3-C6aldehyder |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0804400B1 (zh) |
| JP (1) | JPH11501903A (zh) |
| KR (1) | KR19980701462A (zh) |
| CN (1) | CN1175940A (zh) |
| AT (1) | ATE236111T1 (zh) |
| AU (1) | AU4621196A (zh) |
| BR (1) | BR9606979A (zh) |
| CA (1) | CA2209473A1 (zh) |
| DE (1) | DE69627133T2 (zh) |
| DZ (1) | DZ1972A1 (zh) |
| ES (1) | ES2196138T3 (zh) |
| IL (1) | IL116785A0 (zh) |
| MY (1) | MY119899A (zh) |
| NO (3) | NO310406B1 (zh) |
| WO (1) | WO1996022266A1 (zh) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6090987A (en) * | 1998-07-06 | 2000-07-18 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US6541586B2 (en) | 1999-01-19 | 2003-04-01 | Exxonmobil Research And Engineering Company | Polymerization processes for using dilute multicomponent feeds (LAW624) |
| US6156872A (en) * | 1999-01-19 | 2000-12-05 | Exxon Research And Engineering Co. | Paraffin-soluble polymers and copolymers |
| JP2001213832A (ja) * | 2000-01-31 | 2001-08-07 | Mitsubishi Chemicals Corp | アルデヒドの製造方法 |
| JP2001213835A (ja) * | 2000-02-01 | 2001-08-07 | Mitsubishi Chemicals Corp | アルデヒドの製造方法 |
| JP2001213833A (ja) * | 2000-02-01 | 2001-08-07 | Mitsubishi Chemicals Corp | アルデヒドの製造方法 |
| JP2001213834A (ja) * | 2000-02-01 | 2001-08-07 | Mitsubishi Chemicals Corp | アルデヒドの製造方法 |
| US20100069679A1 (en) * | 2008-09-12 | 2010-03-18 | Eastman Chemical Company | Acetylene tolerant hydroformylation catalysts |
| US9284387B2 (en) | 2012-09-24 | 2016-03-15 | Exxonmobil Chemical Patents Inc. | Hydroamination of aldehyde-containing macromonomers |
| WO2014047256A1 (en) | 2012-09-24 | 2014-03-27 | Exxonmobil Chemical Patents Inc. | Catalytic hydroformylation of vinyl terminated polyolefins |
| GB201604608D0 (en) * | 2016-03-18 | 2016-05-04 | Johnson Matthey Davy Technologies Ltd | Process |
| RU2737189C1 (ru) * | 2019-12-18 | 2020-11-25 | Федеральное государственное бюджетное учреждение науки Институт проблем химической физики Российской Академии наук (ФГБУН ИПХФ РАН) | Способ получения пропаналя гидроформилированием этилена в разбавленных газовых потоках |
| JP2022547456A (ja) * | 2020-07-30 | 2022-11-14 | エルジー・ケム・リミテッド | ヒドロホルミル化方法 |
| CN113816839B (zh) * | 2021-09-23 | 2024-02-02 | 中国成达工程有限公司 | 一种乙炔双氢甲酰化合成丁二醛的方法 |
| CN115925526B (zh) * | 2022-12-30 | 2024-06-18 | 万华化学集团股份有限公司 | 一种超临界合成气氢甲酰化反应的循环工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1042618A (fr) * | 1949-09-12 | 1953-11-03 | Ici Ltd | Perfectionnements relatifs à la fabrication de composés organiques oxygénés |
| CH422746A (fr) * | 1963-11-11 | 1966-10-31 | Ajinomoto Kk | Procédé de fabrication d'un acétal de B-formyl-propionate |
| JPS6048489B2 (ja) * | 1976-05-25 | 1985-10-28 | 日産化学工業株式会社 | 不純物を含有するモノオレフインのオキソ化方法 |
| GB8529244D0 (en) * | 1985-11-27 | 1986-01-02 | British Petroleum Co Plc | Chemical process |
-
1996
- 1996-01-16 IL IL11678596A patent/IL116785A0/xx unknown
- 1996-01-17 AU AU46211/96A patent/AU4621196A/en not_active Abandoned
- 1996-01-17 ES ES96901758T patent/ES2196138T3/es not_active Expired - Lifetime
- 1996-01-17 AT AT96901758T patent/ATE236111T1/de not_active IP Right Cessation
- 1996-01-17 CN CN96192029A patent/CN1175940A/zh active Pending
- 1996-01-17 EP EP96901758A patent/EP0804400B1/en not_active Expired - Lifetime
- 1996-01-17 DE DE69627133T patent/DE69627133T2/de not_active Expired - Fee Related
- 1996-01-17 WO PCT/EP1996/000268 patent/WO1996022266A1/en active IP Right Grant
- 1996-01-17 BR BR9606979A patent/BR9606979A/pt not_active Application Discontinuation
- 1996-01-17 CA CA002209473A patent/CA2209473A1/en not_active Abandoned
- 1996-01-17 JP JP8522056A patent/JPH11501903A/ja active Pending
- 1996-01-17 DZ DZ960013A patent/DZ1972A1/fr active
- 1996-01-17 KR KR1019970704852A patent/KR19980701462A/ko not_active Application Discontinuation
- 1996-01-18 MY MYPI96000185A patent/MY119899A/en unknown
-
1997
- 1997-07-17 NO NO19973306A patent/NO310406B1/no unknown
-
2000
- 2000-11-24 NO NO20005945A patent/NO311351B1/no unknown
- 2000-11-24 NO NO20005944A patent/NO311350B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11501903A (ja) | 1999-02-16 |
| ATE236111T1 (de) | 2003-04-15 |
| CN1175940A (zh) | 1998-03-11 |
| NO5945A (no) | 1997-09-16 |
| MY119899A (en) | 2005-08-30 |
| NO973306D0 (no) | 1997-07-17 |
| NO973306L (no) | 1997-09-16 |
| IL116785A0 (en) | 1996-05-14 |
| WO1996022266A1 (en) | 1996-07-25 |
| EP0804400B1 (en) | 2003-04-02 |
| CA2209473A1 (en) | 1996-07-25 |
| EP0804400A1 (en) | 1997-11-05 |
| AU4621196A (en) | 1996-08-07 |
| KR19980701462A (ko) | 1998-05-15 |
| NO5944A (no) | 1997-09-16 |
| BR9606979A (pt) | 1997-11-04 |
| NO311351B1 (no) | 2001-11-19 |
| NO20005944D0 (no) | 2000-11-24 |
| ES2196138T3 (es) | 2003-12-16 |
| DE69627133T2 (de) | 2004-01-08 |
| DZ1972A1 (fr) | 2002-07-20 |
| NO20005945D0 (no) | 2000-11-24 |
| DE69627133D1 (de) | 2003-05-08 |
| NO311350B1 (no) | 2001-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5675041A (en) | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide, hydrogen, ethylene, and acetylene | |
| US4287369A (en) | Hydroformylation of alkenes to aldehydes | |
| US6049011A (en) | Hydroformylation process | |
| EP0016286B1 (en) | Hydroformylation process | |
| US5520722A (en) | Multiunsaturates removal process | |
| EP1733003B1 (en) | Propylene hydroformylation | |
| US10155710B1 (en) | Processes for making C3 products from ethylene and syngas using hydroformylation strategies | |
| CN102056872B (zh) | 通过加氢甲酰化从含c4的烃流分离1-丁烯的方法 | |
| NO310406B1 (no) | Fremgangsmåter for fremstilling av C3-C6aldehyder | |
| EP0096987B1 (en) | Hydroformylation process | |
| KR100823358B1 (ko) | 탄소 원자수 ２ 내지 ８의 올레핀의 히드로포르밀화 방법 | |
| NO173232B (no) | Fremgangsmaate for gjenvinning av absorberbare komponenterfra en gass-stroem | |
| EP0804398B1 (en) | Hydroformylation process | |
| EP1390334B1 (en) | Hydroformylation process | |
| AU2002302781A1 (en) | Hydroformylation process | |
| EP3445739A1 (en) | Process | |
| US5516965A (en) | Unsaturates recovery and recycle process | |
| US5600017A (en) | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide hydrogen ethylene and acetylene-(LAW072) | |
| MXPA97005493A (en) | Hydroformilation of a food stream of multiple components | |
| WO2024123510A1 (en) | Process of controlling heavies in a recycle catalyst stream |