ES2566377T3 - Procedimiento de preparación de 2-alquenales 3-sustituidos, en particular prenal - Google Patents
Procedimiento de preparación de 2-alquenales 3-sustituidos, en particular prenal Download PDFInfo
- Publication number
- ES2566377T3 ES2566377T3 ES12788570.5T ES12788570T ES2566377T3 ES 2566377 T3 ES2566377 T3 ES 2566377T3 ES 12788570 T ES12788570 T ES 12788570T ES 2566377 T3 ES2566377 T3 ES 2566377T3
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- Prior art keywords
- alkyl
- hydrogen
- formula
- aryl
- alkenol
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 81
- 238000002360 preparation method Methods 0.000 title claims description 11
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 title description 28
- 239000003446 ligand Substances 0.000 claims abstract description 83
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 74
- 239000001257 hydrogen Substances 0.000 claims abstract description 73
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 51
- 230000003197 catalytic effect Effects 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 239000011541 reaction mixture Substances 0.000 claims abstract description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 14
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 3
- -1 halogen anions Chemical class 0.000 claims description 87
- 239000003054 catalyst Substances 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052707 ruthenium Inorganic materials 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000002504 iridium compounds Chemical class 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000003003 phosphines Chemical class 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000006850 spacer group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 238000005555 metalworking Methods 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract description 2
- JAZCEXBNIYKZDI-UHFFFAOYSA-N [Ir+] Chemical class [Ir+] JAZCEXBNIYKZDI-UHFFFAOYSA-N 0.000 abstract description 2
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 49
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 33
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 23
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 20
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 238000001816 cooling Methods 0.000 description 16
- 238000010992 reflux Methods 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 12
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 12
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 12
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 7
- 229910052741 iridium Inorganic materials 0.000 description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 101150024701 PPH3 gene Proteins 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 6
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 5
- 239000012041 precatalyst Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 description 3
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 3
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- FHDQNOXQSTVAIC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCN1C=C[N+](C)=C1 FHDQNOXQSTVAIC-UHFFFAOYSA-M 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NSPPRYXGGYQMPY-UHFFFAOYSA-N 3-Methylbuten-2-ol-1 Natural products CC(C)C(O)=C NSPPRYXGGYQMPY-UHFFFAOYSA-N 0.000 description 2
- 241001120493 Arene Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- DTHIOPUFUOMHAY-POHAHGRESA-N cis-isogeraniol Chemical compound CC(C)=CC\C=C(\C)CCO DTHIOPUFUOMHAY-POHAHGRESA-N 0.000 description 2
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 2
- 239000004913 cyclooctene Substances 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229960001545 hydrotalcite Drugs 0.000 description 2
- 229910001701 hydrotalcite Inorganic materials 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 150000004693 imidazolium salts Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
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- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical class [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by 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
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161563635P | 2011-11-25 | 2011-11-25 | |
| EP11190852.1A EP2597081A1 (en) | 2011-11-25 | 2011-11-25 | Process for preparing 3-substituted 2-alkenals, in particular prenal |
| EP11190852 | 2011-11-25 | ||
| US201161563635P | 2011-11-25 | ||
| PCT/EP2012/073422 WO2013076226A1 (en) | 2011-11-25 | 2012-11-23 | Process for preparing 3-substituted 2-alkenals, in particular prenal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2566377T3 true ES2566377T3 (es) | 2016-04-12 |
Family
ID=45218300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12788570.5T Active ES2566377T3 (es) | 2011-11-25 | 2012-11-23 | Procedimiento de preparación de 2-alquenales 3-sustituidos, en particular prenal |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9000227B2 (cg-RX-API-DMAC7.html) |
| EP (2) | EP2597081A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6091516B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN103958451B (cg-RX-API-DMAC7.html) |
| ES (1) | ES2566377T3 (cg-RX-API-DMAC7.html) |
| IN (1) | IN2014CN04686A (cg-RX-API-DMAC7.html) |
| MX (1) | MX348373B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013076226A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104926631A (zh) * | 2015-05-30 | 2015-09-23 | 吉林众鑫化工集团有限公司 | 一种以3-甲基-3-丁烯基-1醇制备异戊醛的方法 |
| CN110368937B (zh) * | 2019-08-09 | 2022-02-22 | 中触媒新材料股份有限公司 | 一种3-甲基-2-丁烯-1-醇合成异戊烯醛的方法 |
| EP4081505A1 (en) | 2019-12-23 | 2022-11-02 | DSM IP Assets B.V. | Dehydrogenation process |
| WO2025257295A1 (en) * | 2024-06-13 | 2025-12-18 | Firmenich Sa | Process for preparing carbonyl compounds |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1061045A (en) * | 1963-11-28 | 1967-03-08 | Ici Ltd | Dehydrogenation of alcohols |
| JPS57192326A (en) * | 1981-05-19 | 1982-11-26 | Sagami Chem Res Center | Preparation of unsaturated carbonyl compound |
| FR2537576B1 (fr) * | 1982-12-08 | 1987-07-10 | Rhone Poulenc Sa | Procede d'oxydation d'alcools en composes carbonyles correspondants |
| DE19722567A1 (de) | 1997-05-28 | 1998-12-03 | Basf Ag | Verfahren zur kontinuierlichen technischen Herstellung ungesättigter aliphatischer Aldehyde in einem Rohrbündelreaktor |
| JP4101346B2 (ja) * | 1998-02-18 | 2008-06-18 | ダイセル化学工業株式会社 | 酸化触媒系及びそれを用いた酸化方法 |
| JP4197890B2 (ja) * | 2001-05-24 | 2008-12-17 | 興和創薬株式会社 | 第一級アリルアルコール類の酸化方法 |
| JP4140213B2 (ja) * | 2001-06-20 | 2008-08-27 | 三菱化学株式会社 | カルボニル化合物の製造方法 |
| JP4110844B2 (ja) * | 2002-06-10 | 2008-07-02 | 三菱化学株式会社 | ヒドロキシアルデヒド類の製造方法 |
| JP4089310B2 (ja) | 2002-06-28 | 2008-05-28 | 三菱化学株式会社 | ルテニウム錯体触媒の分離方法 |
| WO2008037693A1 (de) | 2006-09-26 | 2008-04-03 | Basf Se | Kontinuierliches verfahren zur herstellung von citral |
| JP2008214289A (ja) | 2007-03-06 | 2008-09-18 | Mitsubishi Chemicals Corp | カルボニル化合物の製造方法 |
| US20100130758A1 (en) * | 2007-03-09 | 2010-05-27 | Kiyotomi Kaneda | Method for producing carbonyl compound |
| DE102008011767B4 (de) | 2008-02-28 | 2012-07-26 | Basf Se | Verfahren zur Herstellung von olefinisch ungesättigten Carbonylverbindungen durch oxidative Dehydrierung von Alkoholen |
| WO2010032770A1 (ja) | 2008-09-19 | 2010-03-25 | 昭和電工株式会社 | アルコールの水素移動反応に用いる触媒、その製造方法、及びカルボニル基含有化合物の製造方法 |
| JP2010184877A (ja) | 2009-02-10 | 2010-08-26 | Mitsubishi Chemicals Corp | カルボニル化合物の製造方法 |
| US8367875B2 (en) | 2010-02-11 | 2013-02-05 | Basf Se | Process for the preparation of m-substituted alkyltoluenes by isomerization with ionic liquids as catalysts |
| US8450534B2 (en) | 2010-03-24 | 2013-05-28 | Basf Se | Process for preparing 4-cyclohexyl-2-methyl-2-butanol |
| US8609903B2 (en) | 2010-04-01 | 2013-12-17 | Basf Se | Process for preparing hydroxy-substituted aromatic aldehydes |
| US8697834B2 (en) | 2010-05-31 | 2014-04-15 | Basf Se | Polyalkylenepolyamines by homogeneously catalyzed alcohol amination |
| US8741988B2 (en) | 2010-06-15 | 2014-06-03 | Basf Se | Use of cyclic carbonates in epoxy resin compositions |
| US8901350B2 (en) | 2010-06-29 | 2014-12-02 | Basf Se | Process for the preparation of formic acid |
| US8791297B2 (en) | 2010-06-29 | 2014-07-29 | Basf Se | Process for preparing formic acid by reaction of carbon dioxide with hydrogen |
| US8877965B2 (en) | 2010-06-29 | 2014-11-04 | Basf Se | Process for preparing formic acid by reaction of carbon dioxide with hydrogen |
| US8563787B2 (en) | 2010-10-05 | 2013-10-22 | Basf Se | Preparation of homoallyl alcohols in the presence of noncovalently supported ionic liquid phase catalysts under gas-phase reaction conditions |
| US8563781B2 (en) | 2010-10-07 | 2013-10-22 | Basf Se | Process for preparing ketones, in particular macrocyclic ketones |
| US20120157711A1 (en) | 2010-12-21 | 2012-06-21 | Basf Se | Process for preparing formic acid by reacting carbon dioxide with hydrogen |
| US8957260B2 (en) | 2011-02-07 | 2015-02-17 | Basf Se | Process for the oxidation of mesitol |
| US8912361B2 (en) | 2011-03-08 | 2014-12-16 | Basf Se | Process for preparing di-, tri- and polyamines by homogeneously catalyzed alcohol amination |
| US9193666B2 (en) | 2011-03-08 | 2015-11-24 | Basf Se | Process for preparing alkanolamines by homogeneously catalyzed alcohol amination |
| US8785693B2 (en) | 2011-03-08 | 2014-07-22 | Basf Se | Process for the preparation of primary amines by homogeneously catalyzed alcohol amination |
| US8637709B2 (en) | 2011-03-08 | 2014-01-28 | Basf Se | Process for the preparation of primary amines by homogeneously catalyzed alcohol amination |
| US8648031B2 (en) | 2011-06-30 | 2014-02-11 | Basf Se | Macrocyclic lactones |
| US8410293B2 (en) | 2011-06-30 | 2013-04-02 | Basf Se | Process for the preparation of cyclic enol ethers |
| US20130012739A1 (en) | 2011-07-07 | 2013-01-10 | Basf Se | Process for preparing formic acid by reacting carbon dioxide with hydrogen |
| US8703994B2 (en) | 2011-07-27 | 2014-04-22 | Basf Se | Process for preparing formamides and formic esters |
| US9056812B2 (en) | 2011-09-16 | 2015-06-16 | Basf Se | Process for preparing 4-cyclohexyl-2-methyl-2-butanol |
| US20130090496A1 (en) | 2011-10-07 | 2013-04-11 | Basf Se | Process for preparing formic acid by reacting carbon dioxide with hydrogen |
| US8877977B2 (en) | 2011-11-25 | 2014-11-04 | Basf Se | Synthesis of polyalkylenepolyamines having a low color index by homogeneously catalyzed alcohol amination in the presence of hydrogen |
-
2011
- 2011-11-25 EP EP11190852.1A patent/EP2597081A1/en not_active Withdrawn
-
2012
- 2012-11-23 CN CN201280057414.7A patent/CN103958451B/zh not_active Expired - Fee Related
- 2012-11-23 ES ES12788570.5T patent/ES2566377T3/es active Active
- 2012-11-23 WO PCT/EP2012/073422 patent/WO2013076226A1/en not_active Ceased
- 2012-11-23 MX MX2014005869A patent/MX348373B/es active IP Right Grant
- 2012-11-23 US US14/360,323 patent/US9000227B2/en not_active Expired - Fee Related
- 2012-11-23 IN IN4686CHN2014 patent/IN2014CN04686A/en unknown
- 2012-11-23 JP JP2014542839A patent/JP6091516B2/ja not_active Expired - Fee Related
- 2012-11-23 EP EP12788570.5A patent/EP2782895B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| IN2014CN04686A (cg-RX-API-DMAC7.html) | 2015-09-18 |
| EP2782895A1 (en) | 2014-10-01 |
| MX2014005869A (es) | 2014-06-23 |
| JP2015504436A (ja) | 2015-02-12 |
| CN103958451A (zh) | 2014-07-30 |
| CN103958451B (zh) | 2016-03-02 |
| MX348373B (es) | 2017-06-06 |
| JP6091516B2 (ja) | 2017-03-08 |
| EP2597081A1 (en) | 2013-05-29 |
| US20140323770A1 (en) | 2014-10-30 |
| US9000227B2 (en) | 2015-04-07 |
| WO2013076226A1 (en) | 2013-05-30 |
| EP2782895B1 (en) | 2016-02-24 |
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