JP2002501490A - 転移水素化方法及び触媒 - Google Patents
転移水素化方法及び触媒Info
- Publication number
- JP2002501490A JP2002501490A JP54445198A JP54445198A JP2002501490A JP 2002501490 A JP2002501490 A JP 2002501490A JP 54445198 A JP54445198 A JP 54445198A JP 54445198 A JP54445198 A JP 54445198A JP 2002501490 A JP2002501490 A JP 2002501490A
- Authority
- JP
- Japan
- Prior art keywords
- group
- catalyst
- formula
- optionally substituted
- hydrogen
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 128
- 238000000034 method Methods 0.000 title claims abstract description 41
- 238000009901 transfer hydrogenation reaction Methods 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 239000000852 hydrogen donor Substances 0.000 claims abstract description 34
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- 239000003446 ligand Substances 0.000 claims abstract description 14
- 150000002466 imines Chemical class 0.000 claims abstract description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims abstract description 10
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 10
- 239000010948 rhodium Substances 0.000 claims abstract description 10
- 150000004985 diamines Chemical class 0.000 claims abstract description 8
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract description 8
- 150000001414 amino alcohols Chemical class 0.000 claims abstract description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000019253 formic acid Nutrition 0.000 claims abstract description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 152
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- -1 pentadienyl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000007975 iminium salts Chemical class 0.000 claims description 7
- 150000003335 secondary amines Chemical group 0.000 claims description 7
- 230000000707 stereoselective effect Effects 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001735 carboxylic acids Chemical group 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 150000003138 primary alcohols Chemical class 0.000 claims description 4
- 238000005292 vacuum distillation Methods 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002169 ethanolamines Chemical class 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 27
- 230000003197 catalytic effect Effects 0.000 abstract description 6
- 150000002739 metals Chemical class 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 137
- 239000000243 solution Substances 0.000 description 101
- 229910052757 nitrogen Inorganic materials 0.000 description 69
- 229960004592 isopropanol Drugs 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 29
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 25
- 238000005984 hydrogenation reaction Methods 0.000 description 25
- 238000002360 preparation method Methods 0.000 description 24
- 230000007306 turnover Effects 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 150000003284 rhodium compounds Chemical class 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- 239000002585 base Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229910052786 argon Inorganic materials 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 11
- 125000004429 atom Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 6
- 230000010354 integration Effects 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DLNKOYKMWOXYQA-VXNVDRBHSA-N (+)-norephedrine Chemical compound C[C@@H](N)[C@@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-VXNVDRBHSA-N 0.000 description 4
- WAPNOHKVXSQRPX-SSDOTTSWSA-N (R)-1-phenylethanol Chemical compound C[C@@H](O)C1=CC=CC=C1 WAPNOHKVXSQRPX-SSDOTTSWSA-N 0.000 description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 description 3
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 2
- JAAJQSRLGAYGKZ-SNVBAGLBSA-N (1r)-1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2[C@H](O)CCCC2=C1 JAAJQSRLGAYGKZ-SNVBAGLBSA-N 0.000 description 2
- ULSIYEODSMZIPX-MRVPVSSYSA-N (1s)-2-amino-1-phenylethanol Chemical compound NC[C@@H](O)C1=CC=CC=C1 ULSIYEODSMZIPX-MRVPVSSYSA-N 0.000 description 2
- GEJJWYZZKKKSEV-KGLIPLIRSA-N (1s,2r)-2-amino-1,2-diphenylethanol Chemical compound C1([C@H](O)[C@H](N)C=2C=CC=CC=2)=CC=CC=C1 GEJJWYZZKKKSEV-KGLIPLIRSA-N 0.000 description 2
- WAPNOHKVXSQRPX-ZETCQYMHSA-N (S)-1-phenylethanol Chemical compound C[C@H](O)C1=CC=CC=C1 WAPNOHKVXSQRPX-ZETCQYMHSA-N 0.000 description 2
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 2
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 2
- HHAISVSEJFEWBZ-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(C(F)(F)F)C=C1 HHAISVSEJFEWBZ-UHFFFAOYSA-N 0.000 description 2
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 150000002504 iridium compounds Chemical class 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229960005335 propanol Drugs 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000000565 sulfonamide group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- LOPKSXMQWBYUOI-DTWKUNHWSA-N (1r,2s)-1-amino-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@@H](N)[C@@H](O)CC2=C1 LOPKSXMQWBYUOI-DTWKUNHWSA-N 0.000 description 1
- GEJJWYZZKKKSEV-UONOGXRCSA-N (1r,2s)-2-amino-1,2-diphenylethanol Chemical compound C1([C@@H](O)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 GEJJWYZZKKKSEV-UONOGXRCSA-N 0.000 description 1
- JAAJQSRLGAYGKZ-JTQLQIEISA-N (1s)-1,2,3,4-tetrahydronaphthalen-1-ol Chemical compound C1=CC=C2[C@@H](O)CCCC2=C1 JAAJQSRLGAYGKZ-JTQLQIEISA-N 0.000 description 1
- LOPKSXMQWBYUOI-BDAKNGLRSA-N (1s,2r)-1-amino-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@H](N)[C@H](O)CC2=C1 LOPKSXMQWBYUOI-BDAKNGLRSA-N 0.000 description 1
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 description 1
- DDUBOVLGCYUYFX-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=CC=C1Cl DDUBOVLGCYUYFX-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
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- C07B31/00—Reduction in general
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- 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
- C07C29/143—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 ketones
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0073—Rhodium compounds
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- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
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- B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式(1)の化合物の転移水素化により、式(2)の化合物; [式中、 Xは、CR3R4、NR5、(NR5R6)+Q-、O、又はSを表し; R1、R2、R3、R4、R5、及びR6は、それぞれ独立して、水素原子、置換さ れていてもよいヒドロカルビル、過ハロゲン化ヒドロカルビル、又は置換されて いてもよいヘテロサイクリル基を表し、1個以上のR1&R2、R1&R3、R2& R4、R3&R4、R1&R5、R2&R6、及びR5&R6は、置換されていてもよい (1個又は複数個の)環を形成するように結合していてもよく; Q-はアニオンを表す]を製造する方法であって、 前記方法は、式(1)の化合物を触媒の存在下で水素供与体と反応させることを 含み、前記触媒は、一般式: [式中、 R7は、置換されていてもよいシクロペンタジエニル基を表し; Aは、−NR8−、−NR9−、−NHR8、又は−NR8R9を表し、式中、R8 は、H、C(O)R10、SO2R10、C(O)NR10R14、C(S)NR10R14 、C(=NR-14)SR15、又はC(=NR14)OR15であり、R9とR10は、そ れぞれ独立して、置換されていてもよいヒドロカルビル、過ハロゲン化ヒドロカ ルビル、又は置換されていてもよいヘテロサイクリル基を表し、R14とR15は、 それぞれ独立して、水素又はR10の定義と同様の基であり; Bは、−O−、−OH、OR11、−S−、−SH、SR11、−NR11−、−N R12−、−NHR12、又は−NR11R12を表し、式中、R12は、H、C(O)R13 、SO2R13、C(O)NR13R16、C(S)NR13R16、C(=NR16)S R17、又はC(=NR16)OR17であり、R11とR13は、それぞれ独立して、置 換されていてもよいヒドロカルビル、過ハロゲン化ヒドロカルビル、又は置換さ れていてもよいヘテロサイクリル基を表し、R16とR17は、それぞれ独立して、 水素又はR13の定義と同様の基であり; Eは、リンク基を表し; Mは、転移水素化を触媒できる金属を表し; Yは、アニオン基、塩基性配位子、又は空位を表し; ただし、Yが空位でないときは、A又はBの少なくとも一つが水素原子を有す る]を有することを特徴とする転移水素化方法。 2.式(1)の化合物が、ケトン、イミン、又はイミニウム塩である、請求項 1に記載の方法。 3.Mが、VIII族の遷移金属、特にルテニウム、ロジウム、又はイリジウムで ある、請求項1又は2に記載の方法。 4.R7が、3〜5個の置換基、好ましくは5個の置換基で置換されたシクロ ペンタジエニル基、特にペンタメチルシクロペンタジエニル基である、請求項1 〜3のいずれか1項に記載の方法。 5.A−E−Bが、アミノアルコール又はジアミン、好ましくは、置換されて いてもよい2−アミノエタノール、置換されていてもよい3−アミノプロパノー ル、及び置換されていてもよいエチレンジアミンから選ばれるもの、又は、これ らから誘導されるものである、請求項1〜4のいずれか1項に記載の方法。 6.A又はBのいずれかが、アシル又はスルホニル基、好ましくはトルエンス ルホニル、メタンスルホニル、トリフルオロメタンスルホニル、又はアセチル基 を有する、請求項5に記載の方法。 7.A−E−Bが、以下の一つである、又は以下の一つから誘導されるもので ある、請求項5に記載の方法。 8.式(1)の化合物がプロキラル、触媒がキラルで、鏡像異性体的及び/又 はジアステレオマー的に純粋な形態の触媒を使用することにより、式(1)の化 合物が不斉水素化される、前記請求項のいずれかに記載の方法。 9.A−E−Bが少なくとも1個の立体特異中心を含む、請求項8に記載の方 法。 10.水素供与体が、水素、第一級及び第二級アルコール類、第一級及び第二 級アミン類、カルボン酸類及びそれらのエステル類及びアミン塩類、容易に脱水 素可能な炭化水素類、クリーン還元剤類、及びそれらの任意の組合せから選ばれ る、請求項1〜9のいずれか1項に記載の方法。 11.水素供与体が、プロパン−2−オール、ブタン−2−オール、又はトリ エチルアミンとギ酸の混合物である、請求項10に記載の方法。 12.水素供与体の脱水素による生成物が、真空蒸留によって除去される、請 求項1〜11のいずれか1項に記載の方法。 13.式(1)のケトンが、A−E−Bがアミノアルコールである又はアミノ アルコールから誘導される触媒の存在下で転移水素化される、請求項1〜12の いずれか1項に記載の方法。 14.式(1)のイミン又はイミニウム塩が、A−E−BがN−トシルジアミ ンである又はN−トシルジアミンから誘導される触媒の存在下で転移水素化され る、請求項1〜12のいずれか1項に記載の方法。 15.プロセスが、少なくとも8.0のpKaを有する塩基の存在下で実施さ れる、前記請求項のいずれか1項に記載の方法。 16.一般式: [式中、 R7は、置換されていてもよいシクロペンタジエニル基を表し; Aは、−NR8−、−NR9−、−NHR8、又は−NR8R9を表し、式中、R8 は、H、C(O)R10、SO2R10、C(O)NR10R14、C(S)NR10R14 、C(=NR14)SR15、又はC(=NR14)OR15であり、R9とR10は、そ れぞれ独立して、置換されていてもよいヒドロカルビル、過ハロゲン化ヒドロカ ルビル、又は置換されていてもよいヘテロサイクリル基を表し、R14とR15は、 -それぞれ独立して、水素又はR10の定義と同様の基であり; Bは、−O−、−OH、OR11、−S−、−SH、SR11、−NR11−、−N R12−、−NHR12、又は−NR11R12を表し、式中、R12は、H、C(O)R13 、SO2R13、C(O)NR13R16、C(S)NR13R16、C(=NR16)S R17、又はC(=NR16)OR17であり、R11とR13は、それぞれ独立して、置 換されていてもよいヒドロカルビル、過ハロゲン化ヒドロカルビル、又は置換さ れていてもよいヘテロサイクリル基を表し、R16とR17は、それぞれ独立して、 水素又はR13の定義と同様の基であり; Eは、リンク基を表し; Mは、転移水素化を触媒できる金属を表し; Yは、アニオン基、塩基性配位子、又は空位を表し; ただし、(i)Yが空位でないときは、A又はBの少なくとも一つが水素原子 を有し、(ii)Bが−O−又は−OHを表すときは、Bはカルボキシレート基の 一部ではない]の触媒。 17.Mが、VIII族の遷移金属、特にルテニウム、ロジウム、又はイリジウム である、請求項16に記載の触媒。 18.R7が、3〜5個の置換基、好ましくは5個の置換基で置換されたシク ロペンタジエニル基、特にペンタメチルシクロペンタジエニル基である、請求項 16又は17に記載の触媒。 19.A−E−Bが、アミノアルコール又はジアミン、好ましくは、置換され ていてもよい2−アミノエタノール、置換されていてもよい3−アミノプロパノ ール、又は、これらから誘導されるものである、請求項16〜18のいずれか1 項に記載の触媒。 20.A又はBのいずれか又は両方が、アミノ基の場合、アシル又はスルホニ ル基、好ましくはトルエンスルホニル、メタンスルホニル、トリフルオロメタン スルホニル、又はアセチル基、特にトリフルオロアセチル又はp−トルエンスル ホニル基を有する、請求項19に記載の触媒。 21.A−E−Bが、以下の一つである、又は以下の一つから誘導されるもの である、請求項19に記載の触媒。 22.触媒がキラル、及びその分割体である、請求項16〜21のいずれか1 項に記載の触媒。 23.A−E−Bが少なくとも1個の立体特異中心を含む、請求項22に記載 の触媒。 24.金属シクロペンタジエニルハライド錯体を、式A−E−Bの化合物、又 はそれが誘導されうるプロトン化された同等物と反応させることを含む、請求項 16〜23のいずれか1項に記載の触媒の調製方法。
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GBGB9706321.8A GB9706321D0 (en) | 1997-03-26 | 1997-03-26 | Catalytic hydrogenation |
PCT/GB1998/000862 WO1998042643A1 (en) | 1997-03-26 | 1998-03-20 | Transfer hydrogenation process and catalyst |
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JP (1) | JP4090078B2 (ja) |
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HU (1) | HU226707B1 (ja) |
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1997
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- 1998-03-20 DE DE69807199T patent/DE69807199T2/de not_active Expired - Lifetime
- 1998-03-20 EP EP98912610A patent/EP0971865B1/en not_active Expired - Lifetime
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Also Published As
Publication number | Publication date |
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CA2284777C (en) | 2007-07-17 |
IL131913A (en) | 2004-05-12 |
CA2284777A1 (en) | 1998-10-01 |
NO994677L (no) | 1999-11-24 |
KR20010005633A (ko) | 2001-01-15 |
CZ337499A3 (cs) | 1999-12-15 |
CN1257468A (zh) | 2000-06-21 |
CN1130324C (zh) | 2003-12-10 |
AU6739198A (en) | 1998-10-20 |
US20020156282A1 (en) | 2002-10-24 |
DE69807199T2 (de) | 2003-05-08 |
HU226707B1 (en) | 2009-07-28 |
WO1998042643A1 (en) | 1998-10-01 |
GB9706321D0 (en) | 1997-05-14 |
US6372931B1 (en) | 2002-04-16 |
JP4090078B2 (ja) | 2008-05-28 |
CZ296027B6 (cs) | 2005-12-14 |
DK0971865T3 (da) | 2002-12-09 |
IL131913A0 (en) | 2001-03-19 |
EP0971865B1 (en) | 2002-08-14 |
NO994677D0 (no) | 1999-09-24 |
PT971865E (pt) | 2002-11-29 |
KR100599466B1 (ko) | 2006-07-12 |
AU739341B2 (en) | 2001-10-11 |
US6545188B2 (en) | 2003-04-08 |
ES2182288T3 (es) | 2003-03-01 |
EP0971865A1 (en) | 2000-01-19 |
MX9908650A (es) | 2000-04-30 |
ATE222223T1 (de) | 2002-08-15 |
DE69807199D1 (de) | 2002-09-19 |
HUP0002058A2 (hu) | 2000-10-28 |
NO312663B1 (no) | 2002-06-17 |
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