DE4400837A1 - Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol - Google Patents
Verfahren zur Herstellung von n-Butyraldehyd und/oder n-ButanolInfo
- Publication number
- DE4400837A1 DE4400837A1 DE4400837A DE4400837A DE4400837A1 DE 4400837 A1 DE4400837 A1 DE 4400837A1 DE 4400837 A DE4400837 A DE 4400837A DE 4400837 A DE4400837 A DE 4400837A DE 4400837 A1 DE4400837 A1 DE 4400837A1
- Authority
- DE
- Germany
- Prior art keywords
- elements
- catalyst
- reaction
- liquid phase
- process stage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 240
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 title claims abstract description 221
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 title claims abstract description 162
- 230000008569 process Effects 0.000 title claims abstract description 129
- 238000002360 preparation method Methods 0.000 title claims description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 194
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 192
- 239000003054 catalyst Substances 0.000 claims abstract description 173
- 150000002084 enol ethers Chemical class 0.000 claims abstract description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- 239000003446 ligand Substances 0.000 claims abstract description 48
- 239000007791 liquid phase Substances 0.000 claims abstract description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 230000000737 periodic effect Effects 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 230000007062 hydrolysis Effects 0.000 claims description 59
- 238000006460 hydrolysis reaction Methods 0.000 claims description 59
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 58
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 56
- 238000006317 isomerization reaction Methods 0.000 claims description 52
- 238000005984 hydrogenation reaction Methods 0.000 claims description 48
- 239000007789 gas Substances 0.000 claims description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 39
- 239000010949 copper Substances 0.000 claims description 38
- 229910052802 copper Inorganic materials 0.000 claims description 38
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 36
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 35
- -1 Arylalkyl phosphine Chemical compound 0.000 claims description 34
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000002815 homogeneous catalyst Substances 0.000 claims description 33
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 31
- 239000012071 phase Substances 0.000 claims description 30
- 229910052763 palladium Inorganic materials 0.000 claims description 27
- 239000010457 zeolite Substances 0.000 claims description 27
- 229910052702 rhenium Inorganic materials 0.000 claims description 22
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 22
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 20
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000012429 reaction media Substances 0.000 claims description 18
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 17
- 229910052759 nickel Inorganic materials 0.000 claims description 17
- 229910052707 ruthenium Inorganic materials 0.000 claims description 16
- 150000002500 ions Chemical class 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910021536 Zeolite Inorganic materials 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 13
- 239000000377 silicon dioxide Substances 0.000 claims description 13
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 12
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000003624 transition metals Chemical class 0.000 claims description 11
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- 239000012876 carrier material Substances 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052741 iridium Inorganic materials 0.000 claims description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 7
- 150000007517 lewis acids Chemical class 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 239000004408 titanium dioxide Substances 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 238000004061 bleaching Methods 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 claims description 2
- 150000004715 keto acids Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003282 rhenium compounds Chemical class 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 2
- 241001295925 Gegenes Species 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 150000004697 chelate complex Chemical class 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 2
- 239000007792 gaseous phase Substances 0.000 abstract 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 abstract 1
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 abstract 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 29
- 238000004821 distillation Methods 0.000 description 28
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 27
- 239000007788 liquid Substances 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 24
- 239000002184 metal Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 21
- 150000002739 metals Chemical class 0.000 description 21
- 239000007795 chemical reaction product Substances 0.000 description 20
- 150000001298 alcohols Chemical class 0.000 description 19
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000000376 reactant Substances 0.000 description 11
- 239000007848 Bronsted acid Substances 0.000 description 10
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 241001026509 Kata Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- DVSSQJKZHTWMOS-UHFFFAOYSA-N 1-but-2-enoxybutane Chemical compound CCCCOCC=CC DVSSQJKZHTWMOS-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 238000007037 hydroformylation reaction Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000012495 reaction gas Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 235000010215 titanium dioxide Nutrition 0.000 description 8
- CQJQTXVQMQMNBT-UHFFFAOYSA-N 1-but-3-en-2-yloxybutane Chemical compound CCCCOC(C)C=C CQJQTXVQMQMNBT-UHFFFAOYSA-N 0.000 description 7
- 229920001429 chelating resin Polymers 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 229910017052 cobalt Inorganic materials 0.000 description 6
- 239000010941 cobalt Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 150000003003 phosphines Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- GCRUYRFHWGPWHJ-UHFFFAOYSA-N 1-but-1-enoxybutane Chemical compound CCCCOC=CCC GCRUYRFHWGPWHJ-UHFFFAOYSA-N 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 150000002823 nitrates Chemical class 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229910052711 selenium Inorganic materials 0.000 description 5
- 239000011669 selenium Substances 0.000 description 5
- 230000007306 turnover Effects 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000003245 coal Substances 0.000 description 4
- 230000000536 complexating effect Effects 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 150000002028 dodecanols Chemical class 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 238000007172 homogeneous catalysis Methods 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 150000002892 organic cations Chemical class 0.000 description 4
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000007700 distillative separation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000007210 heterogeneous catalysis Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 3
- 239000000391 magnesium silicate Substances 0.000 description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 description 3
- 235000019792 magnesium silicate Nutrition 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 229910052901 montmorillonite Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 230000036647 reaction Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- HOXGZVUCAYFWGR-KQQUZDAGSA-N (3e,5e)-octa-1,3,5-triene Chemical compound CC\C=C\C=C\C=C HOXGZVUCAYFWGR-KQQUZDAGSA-N 0.000 description 2
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- DQBLWVOFEZVBFT-UHFFFAOYSA-N 1-but-3-enoxybutane Chemical compound CCCCOCCC=C DQBLWVOFEZVBFT-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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- 239000002738 chelating agent Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- OLFCLHDBKGQITG-UHFFFAOYSA-N chromium(3+) nickel(2+) oxygen(2-) Chemical compound [Ni+2].[O-2].[Cr+3] OLFCLHDBKGQITG-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- INPLXZPZQSLHBR-UHFFFAOYSA-N cobalt(2+);sulfide Chemical compound [S-2].[Co+2] INPLXZPZQSLHBR-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- ZXKWUYWWVSKKQZ-UHFFFAOYSA-N cyclohexyl(diphenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZXKWUYWWVSKKQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- KHQXDNILONPNNV-UHFFFAOYSA-N dibutyl(2-dibutylphosphanylethyl)phosphane Chemical compound CCCCP(CCCC)CCP(CCCC)CCCC KHQXDNILONPNNV-UHFFFAOYSA-N 0.000 description 1
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
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- 150000002009 diols Chemical class 0.000 description 1
- BVQAWSJMUYMNQN-UHFFFAOYSA-N dipyridophenazine Chemical compound C1=CC=C2C3=NC4=CC=CC=C4N=C3C3=CC=CN=C3C2=N1 BVQAWSJMUYMNQN-UHFFFAOYSA-N 0.000 description 1
- MWVXFEZPEPOQRE-UHFFFAOYSA-N ditert-butyl(2-ditert-butylphosphanylethyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CCP(C(C)(C)C)C(C)(C)C MWVXFEZPEPOQRE-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WHNGQRQJGDUZPJ-UHFFFAOYSA-N hexyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCC)C1=CC=CC=C1 WHNGQRQJGDUZPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000001145 hydrido group Chemical group *[H] 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- RZTYOSHPZXUMFE-UHFFFAOYSA-N lead palladium Chemical compound [Pd].[Pb] RZTYOSHPZXUMFE-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
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- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
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- 239000002808 molecular sieve Substances 0.000 description 1
- TVWWSIKTCILRBF-UHFFFAOYSA-N molybdenum trisulfide Chemical compound S=[Mo](=S)=S TVWWSIKTCILRBF-UHFFFAOYSA-N 0.000 description 1
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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- 229910052762 osmium Inorganic materials 0.000 description 1
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- 230000001590 oxidative effect Effects 0.000 description 1
- OOSUVFMPZZUMMJ-UHFFFAOYSA-N oxoplatinum oxorhodium Chemical compound O=[Rh].O=[Pt] OOSUVFMPZZUMMJ-UHFFFAOYSA-N 0.000 description 1
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- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 150000004707 phenolate Chemical class 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
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- DBJYYRBULROVQT-UHFFFAOYSA-N platinum rhenium Chemical compound [Re].[Pt] DBJYYRBULROVQT-UHFFFAOYSA-N 0.000 description 1
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- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003281 rhenium Chemical class 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HISNRBVYBOVKMB-UHFFFAOYSA-N stibonium Chemical class [SbH4+] HISNRBVYBOVKMB-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical class C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- VTKQLVHDZYRENE-UHFFFAOYSA-N tricyclopentyl phosphite Chemical compound C1CCCC1OP(OC1CCCC1)OC1CCCC1 VTKQLVHDZYRENE-UHFFFAOYSA-N 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- MOSFSEPBWRXKJZ-UHFFFAOYSA-N tridecylphosphane Chemical compound CCCCCCCCCCCCCP MOSFSEPBWRXKJZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- SJHCUXCOGGKFAI-UHFFFAOYSA-N tripropan-2-yl phosphite Chemical compound CC(C)OP(OC(C)C)OC(C)C SJHCUXCOGGKFAI-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/32—Preparation of ethers by isomerisation
-
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4400837A DE4400837A1 (de) | 1994-01-14 | 1994-01-14 | Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol |
| JP51884095A JPH09508109A (ja) | 1994-01-14 | 1995-01-12 | ｎ−ブチルアルデヒドおよび／またはｎ−ブタノールの製造方法 |
| CN95191229A CN1040204C (zh) | 1994-01-14 | 1995-01-12 | 正丁醛和/或正丁醇的制备方法 |
| DE59503924T DE59503924D1 (de) | 1994-01-14 | 1995-01-12 | VERFAHREN ZUR HERSTELLUNG VON n-BUTYRALDEHYD UND/ODER n-BUTANOL |
| ES95906933T ES2122538T3 (es) | 1994-01-14 | 1995-01-12 | Procedimiento para la obtencion de n-butiraldehido y/o n-butanol. |
| EP19950906933 EP0739332B1 (de) | 1994-01-14 | 1995-01-12 | VERFAHREN ZUR HERSTELLUNG VON n-BUTYRALDEHYD UND/ODER n-BUTANOL |
| RU96116892A RU2135456C1 (ru) | 1994-01-14 | 1995-01-12 | Способ получения н-бутиральдегида и/или н-бутанола |
| PCT/EP1995/000114 WO1995019334A1 (de) | 1994-01-14 | 1995-01-12 | VERFAHREN ZUR HERSTELLUNG VON n-BUTYRALDEHYD UND/ODER n-BUTANOL |
| KR1019960703760A KR100335040B1 (ko) | 1994-01-14 | 1995-01-12 | N-부티르알테히드및/또는n-부탄올의제조방법 |
| US08/676,185 US5705707A (en) | 1994-01-14 | 1995-01-12 | Preparation of n-butyraldehyde and/or n-butanol |
| CA 2180982 CA2180982A1 (en) | 1994-01-14 | 1995-01-12 | Process for producing n-butyraldehyde and/or n-butanol |
| TW84100276A TW314509B (OSRAM) | 1994-01-14 | 1995-01-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4400837A DE4400837A1 (de) | 1994-01-14 | 1994-01-14 | Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4400837A1 true DE4400837A1 (de) | 1995-07-20 |
Family
ID=6507859
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4400837A Withdrawn DE4400837A1 (de) | 1994-01-14 | 1994-01-14 | Verfahren zur Herstellung von n-Butyraldehyd und/oder n-Butanol |
| DE59503924T Expired - Lifetime DE59503924D1 (de) | 1994-01-14 | 1995-01-12 | VERFAHREN ZUR HERSTELLUNG VON n-BUTYRALDEHYD UND/ODER n-BUTANOL |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59503924T Expired - Lifetime DE59503924D1 (de) | 1994-01-14 | 1995-01-12 | VERFAHREN ZUR HERSTELLUNG VON n-BUTYRALDEHYD UND/ODER n-BUTANOL |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5705707A (OSRAM) |
| EP (1) | EP0739332B1 (OSRAM) |
| JP (1) | JPH09508109A (OSRAM) |
| KR (1) | KR100335040B1 (OSRAM) |
| CN (1) | CN1040204C (OSRAM) |
| CA (1) | CA2180982A1 (OSRAM) |
| DE (2) | DE4400837A1 (OSRAM) |
| ES (1) | ES2122538T3 (OSRAM) |
| RU (1) | RU2135456C1 (OSRAM) |
| TW (1) | TW314509B (OSRAM) |
| WO (1) | WO1995019334A1 (OSRAM) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996007630A1 (de) * | 1994-09-03 | 1996-03-14 | Basf Aktiengesellschaft | Verfahren zur herstellung von n-butyraldehyd und/oder n-butanol |
| WO1998041494A1 (de) * | 1997-03-17 | 1998-09-24 | Basf Aktiengesellschaft | Verfahren zur herstellung von n-butyraldehyd und/oder n-butanol |
| WO1998012164A3 (de) * | 1996-09-17 | 1999-04-01 | Basf Ag | VERFAHREN ZUR HERSTELLUNG VON n-BUTYLALKYLETHERN |
| WO1998012165A3 (de) * | 1996-09-17 | 1999-07-22 | Basf Ag | Verfahren zur herstellung von alkoxybutenen |
| EP1000919A1 (de) * | 1998-11-11 | 2000-05-17 | Basf Aktiengesellschaft | Verfahren zur Herstellung substituierter Butene |
| EP1382383A1 (de) * | 2002-07-15 | 2004-01-21 | Basf Aktiengesellschaft | Strukturierte Katalysator-Schüttung |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19622497A1 (de) | 1996-06-05 | 1997-12-11 | Basf Ag | Verfahren zur Herstellung von Tetrahydrofuran aus Dialkoxybutenen |
| DE19725873A1 (de) * | 1997-06-18 | 1998-12-24 | Basf Ag | Verfahren zur Herstellung von Butenylethern |
| DE19725872A1 (de) | 1997-06-18 | 1998-12-24 | Basf Ag | Verfahren zur Herstellung von Butenylethern |
| DE19838449A1 (de) * | 1998-08-25 | 2000-03-02 | Basf Ag | Verfahren zur Abtrennung von 1,3-Butadien und Wasser aus Stoffgemischen enthaltend 1,3-Butadien, 1-n-Butoxybuten-2, 3-n-Butoxybuten-1, n-Butanol, Di-n-butylether und Wasser |
| GB9823853D0 (en) | 1998-10-30 | 1998-12-23 | Bp Chem Int Ltd | A process for making n-butyl esters from butadiene |
| GB9823980D0 (en) * | 1998-11-02 | 1998-12-30 | Bp Chem Int Ltd | A process for making n-butyl ethers of glycols |
| GB9828338D0 (en) * | 1998-12-22 | 1999-02-17 | Bp Chem Int Ltd | A process for making butyraldehyde from butadiene |
| KR20060021358A (ko) * | 2003-06-16 | 2006-03-07 | 더 유니버시티 오브 서던 미시시피 리서치 파운데이션 | 부타디엔 첨가 산물 유도체의 통합적 제조 방법 |
| JP2009046469A (ja) * | 2007-07-26 | 2009-03-05 | Chiba Univ | 光学活性アリル化合物類の製造方法 |
| CN102015670B (zh) * | 2008-05-01 | 2013-06-19 | 可乐丽股份有限公司 | 乙烯基醚类化合物的制备方法 |
| CN102816049A (zh) * | 2012-08-09 | 2012-12-12 | 西安近代化学研究所 | 3，3，3-三氟丙醇的制备方法 |
| SG11201901336RA (en) * | 2016-09-23 | 2019-04-29 | Basf Se | Method for providing a fixed catalyst bed containing a doped structured shaped catalyst body |
| WO2018054759A1 (de) * | 2016-09-23 | 2018-03-29 | Basf Se | Verfahren zur aktivierung eines katalysatorfestbetts, das monolithische katalysatorformkörper enthält oder aus monolithischen katalysatorformkörpern besteht |
| CN116747909B (zh) * | 2023-06-14 | 2025-09-19 | 山东海科创新研究院有限公司 | 铱-铼双金属络合固载型催化剂及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE821202C (de) * | 1949-03-29 | 1951-11-15 | Chemische Werke Huels G M B H | Verfahren zur Herstellung von Butyraldehyd |
| US2922822A (en) * | 1957-01-08 | 1960-01-26 | Exxon Research Engineering Co | Production of methyl butenyl ethers |
| FR82549E (fr) * | 1961-11-13 | 1964-02-28 | Monsanto Chemicals | Procédé de production d'éthers aromatiques |
| DE2550902A1 (de) * | 1975-11-13 | 1977-05-26 | Texaco Ag | Verfahren zur herstellung von 3-alkoxibuten-1 und alkyl-trans-butylaether |
| DE2751766A1 (de) * | 1977-11-19 | 1979-05-23 | Basf Ag | Verfahren zur isomerisierung von 3-buten-1-ol-verbindungen zu den entsprechenden 2-buten-1-ol-verbindungen |
| US4731486A (en) * | 1986-11-18 | 1988-03-15 | Union Carbide Corporation | Hydroformylation using low volatile phosphine ligands |
| GB8702654D0 (en) * | 1987-02-06 | 1987-03-11 | Davy Mckee Ltd | Process |
| WO1991003449A1 (en) * | 1989-09-05 | 1991-03-21 | Gaf Chemicals Corporation | Isomerization of alk-2-enyl ethers |
-
1994
- 1994-01-14 DE DE4400837A patent/DE4400837A1/de not_active Withdrawn
-
1995
- 1995-01-12 RU RU96116892A patent/RU2135456C1/ru active
- 1995-01-12 US US08/676,185 patent/US5705707A/en not_active Expired - Lifetime
- 1995-01-12 WO PCT/EP1995/000114 patent/WO1995019334A1/de not_active Ceased
- 1995-01-12 EP EP19950906933 patent/EP0739332B1/de not_active Expired - Lifetime
- 1995-01-12 DE DE59503924T patent/DE59503924D1/de not_active Expired - Lifetime
- 1995-01-12 CN CN95191229A patent/CN1040204C/zh not_active Expired - Fee Related
- 1995-01-12 CA CA 2180982 patent/CA2180982A1/en not_active Abandoned
- 1995-01-12 ES ES95906933T patent/ES2122538T3/es not_active Expired - Lifetime
- 1995-01-12 JP JP51884095A patent/JPH09508109A/ja not_active Ceased
- 1995-01-12 KR KR1019960703760A patent/KR100335040B1/ko not_active Expired - Fee Related
- 1995-01-13 TW TW84100276A patent/TW314509B/zh active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996007630A1 (de) * | 1994-09-03 | 1996-03-14 | Basf Aktiengesellschaft | Verfahren zur herstellung von n-butyraldehyd und/oder n-butanol |
| US5892125A (en) * | 1994-09-03 | 1999-04-06 | Basf Aktiengesellschaft | Preparation of n-butyraldehyde and/or n-butanol |
| WO1998012164A3 (de) * | 1996-09-17 | 1999-04-01 | Basf Ag | VERFAHREN ZUR HERSTELLUNG VON n-BUTYLALKYLETHERN |
| WO1998012165A3 (de) * | 1996-09-17 | 1999-07-22 | Basf Ag | Verfahren zur herstellung von alkoxybutenen |
| WO1998041494A1 (de) * | 1997-03-17 | 1998-09-24 | Basf Aktiengesellschaft | Verfahren zur herstellung von n-butyraldehyd und/oder n-butanol |
| EP1000919A1 (de) * | 1998-11-11 | 2000-05-17 | Basf Aktiengesellschaft | Verfahren zur Herstellung substituierter Butene |
| EP1382383A1 (de) * | 2002-07-15 | 2004-01-21 | Basf Aktiengesellschaft | Strukturierte Katalysator-Schüttung |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59503924D1 (de) | 1998-11-19 |
| JPH09508109A (ja) | 1997-08-19 |
| EP0739332B1 (de) | 1998-10-14 |
| US5705707A (en) | 1998-01-06 |
| RU2135456C1 (ru) | 1999-08-27 |
| ES2122538T3 (es) | 1998-12-16 |
| WO1995019334A1 (de) | 1995-07-20 |
| CN1138849A (zh) | 1996-12-25 |
| CN1040204C (zh) | 1998-10-14 |
| CA2180982A1 (en) | 1995-07-20 |
| EP0739332A1 (de) | 1996-10-30 |
| TW314509B (OSRAM) | 1997-09-01 |
| KR100335040B1 (ko) | 2002-11-27 |
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