PL179441B1 - Sposób uwodorniania co najmniej jednej grupy C=N- zawartej w iminie PL PL - Google Patents
Sposób uwodorniania co najmniej jednej grupy C=N- zawartej w iminie PL PLInfo
- Publication number
- PL179441B1 PL179441B1 PL95310965A PL31096595A PL179441B1 PL 179441 B1 PL179441 B1 PL 179441B1 PL 95310965 A PL95310965 A PL 95310965A PL 31096595 A PL31096595 A PL 31096595A PL 179441 B1 PL179441 B1 PL 179441B1
- Authority
- PL
- Poland
- Prior art keywords
- alkyl
- phenyl
- benzyl
- acid
- imine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 91
- 150000002466 imines Chemical class 0.000 title claims abstract description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 67
- 239000001257 hydrogen Substances 0.000 claims abstract description 64
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 24
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 19
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011541 reaction mixture Substances 0.000 claims abstract description 17
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 12
- 229910001509 metal bromide Inorganic materials 0.000 claims abstract description 6
- 229910001510 metal chloride Inorganic materials 0.000 claims abstract description 6
- 229910001511 metal iodide Inorganic materials 0.000 claims abstract description 6
- 239000012442 inert solvent Substances 0.000 claims abstract description 5
- -1 3-oxapentylene Chemical group 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 51
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 30
- 239000003446 ligand Substances 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 27
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000004658 ketimines Chemical class 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 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 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910004013 NO 2 Inorganic materials 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 150000004705 aldimines Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000001993 dienes Chemical class 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 6
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 229910001513 alkali metal bromide Inorganic materials 0.000 claims 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims 2
- 229910001516 alkali metal iodide Inorganic materials 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 26
- 230000035484 reaction time Effects 0.000 description 20
- 150000002431 hydrogen Chemical class 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 235000011054 acetic acid Nutrition 0.000 description 16
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 16
- 230000003287 optical effect Effects 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910000831 Steel Inorganic materials 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000010959 steel Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011261 inert gas Substances 0.000 description 6
- 150000003003 phosphines Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-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
- 239000012018 catalyst precursor Substances 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
- 150000004694 iodide salts Chemical class 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 3
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 3
- CUZLJOLBIRPEFB-UHFFFAOYSA-N 1-methoxypropan-2-one Chemical compound COCC(C)=O CUZLJOLBIRPEFB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 150000001649 bromium compounds Chemical class 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 229940106681 chloroacetic acid Drugs 0.000 description 3
- 125000002704 decyl group Chemical group [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])* 0.000 description 3
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001400 nonyl 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])[H] 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- RFXWSCVCWQKXAL-UHFFFAOYSA-N (3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P)=C1 RFXWSCVCWQKXAL-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 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 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
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- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
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- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/52—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of imines or imino-ethers
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
Applications Claiming Priority (2)
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| CH30994 | 1994-02-02 | ||
| PCT/EP1995/000221 WO1995021151A1 (en) | 1994-02-02 | 1995-01-21 | Process for the hydrogenation of imines |
Publications (2)
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| PL310965A1 PL310965A1 (en) | 1996-01-22 |
| PL179441B1 true PL179441B1 (pl) | 2000-09-29 |
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| PL95310965A PL179441B1 (pl) | 1994-02-02 | 1995-01-21 | Sposób uwodorniania co najmniej jednej grupy C=N- zawartej w iminie PL PL |
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| FR2750423B1 (fr) * | 1996-06-28 | 1998-08-14 | Rhone Poulenc Chimie | Procede d'hydrogenation asymetrique d'un compose cetonique |
| DE19645549A1 (de) * | 1996-11-05 | 1998-05-07 | Bayer Ag | Verfahren zur Herstellung von 2-Methyl-2,4-diaminopentan |
| US6017918A (en) * | 1998-08-06 | 2000-01-25 | Warner-Lambert Company | Phenyl glycine compounds and methods of treating atherosclerosis and restenosis |
| US6284795B1 (en) | 1998-09-04 | 2001-09-04 | Warner-Lambert Company | Sulfonamide compounds and methods of treating atherosclerosis and restenosis |
| DE19933611A1 (de) * | 1999-07-17 | 2001-01-18 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von Aminen durch homogen katalysierte reduktive Aminierung von Carbonylverbindungen |
| GB9920285D0 (en) | 1999-08-27 | 1999-10-27 | Johnson Matthey Plc | Improved catalytic process |
| US7667228B2 (en) * | 2003-07-22 | 2010-02-23 | Idemitsu Kosan Co., Ltd. | Metal complex compound and organic electroluminescent device using same |
| DE102004012438A1 (de) * | 2004-03-12 | 2005-09-29 | Degussa Ag | Verfahren zur Herstellung von enantiomerenangereicherten Ferrocenylliganden |
| ITMI20050158A1 (it) * | 2005-02-04 | 2006-08-05 | Univ Degli Studi Milano | 1,4-bis-difosfino-z-2-buteni, 1,4-disostituiti otticamente puri in qualita' di leganti chirali per la catalisi omogenea stereocontrollata con complessi di metalli di tyransizione |
| WO2006108562A1 (en) | 2005-04-08 | 2006-10-19 | Dsm Ip Assets B.V. | Manufacture of lactones |
| WO2006108636A1 (en) | 2005-04-15 | 2006-10-19 | Dsm Ip Assets B.V. | Manufacture of thiolactones |
| CA2605159C (en) * | 2005-04-20 | 2014-05-27 | Umicore Ag & Co. Kg | Diphosphines and metal complexes |
| DE102005052588A1 (de) | 2005-11-02 | 2007-05-10 | Grünenthal GmbH | Verfahren zur Herstellung substituierter Dimethyl-(3-aryl-butyl)-amin-Verbindungen mittels homogener Katalyse |
| US20070213540A1 (en) * | 2006-03-09 | 2007-09-13 | Degussa Ag | Process for the hydrogenation of imines |
| JP2011518150A (ja) * | 2008-04-17 | 2011-06-23 | ユナイテッド・フォスフォラス・リミテッド | イミンの水素化 |
| MX2010014510A (es) * | 2008-06-27 | 2011-02-22 | Merck Frosst Canada Ltd | Sintesis de aminas quirales. |
| RU2371919C1 (ru) * | 2008-08-06 | 2009-11-10 | Закрытое акционерное общество "АЛЬФА-ТЭК" | Способ борьбы с грибковыми и бактериальными заболеваниями сельскохозяйственных растений |
| EP2202236A1 (en) | 2008-12-23 | 2010-06-30 | Solvias AG | Chiral ligands |
| EP2363388A1 (en) * | 2010-03-02 | 2011-09-07 | DSM IP Assets B.V. | Process for the production of chiral amines |
| CN101857612B (zh) * | 2010-06-11 | 2016-03-23 | 南京工业大学 | 一类手性双膦配体及其铱复合催化剂、制备方法及在不对称氢化合成(s)-异丙甲草胺中的应用 |
| CN102951980A (zh) * | 2011-08-23 | 2013-03-06 | 中国中化股份有限公司 | 一种亚胺不对称催化加氢的方法 |
| CN102950025B (zh) * | 2011-08-23 | 2014-09-10 | 中国中化股份有限公司 | 一种亚胺不对称加氢催化剂及其用途 |
| US9199930B2 (en) | 2012-09-06 | 2015-12-01 | Council Of Scientific And Industrial Research | Process for the preparation of (S)-2-ethyl-N-(1-methoxypropan-2-yl)-6-methyl aniline |
| CN104557563B (zh) * | 2013-10-22 | 2017-04-26 | 中国石油化工股份有限公司 | 一种合成(r)‑1‑苯基丁胺的方法 |
| PT108303A (pt) | 2015-03-20 | 2016-09-20 | Sapec Agro S A | Processo de produção de (s)-metolacloro |
| CN109422602A (zh) * | 2017-08-29 | 2019-03-05 | 中国科学院大连化学物理研究所 | 一种不对称氢化亚胺制备手性胺的方法 |
| EP4003957B1 (en) * | 2019-07-25 | 2024-04-17 | Medichem, S.A. | Process for the synthesis of n-alkyl-4-pyridinamines |
| EP4584253A1 (en) * | 2022-09-07 | 2025-07-16 | Adama Agan Ltd. | Process for the preparation of dimethenamid |
| GB202216812D0 (en) | 2022-11-10 | 2022-12-28 | Univ Court Univ St Andrews | Process |
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| DE2825543A1 (de) * | 1978-06-10 | 1979-12-13 | Bayer Ag | N-substituierte halogenacetanilide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3262501D1 (en) * | 1981-10-16 | 1985-04-11 | Ciba Geigy Ag | N-(1'-methyl-2'-methoxyethyl)-n-chloroacetyl-2-ethyl-6-methyl aniline as a herbicide |
| EP0115470B1 (de) * | 1983-01-25 | 1986-12-17 | Ciba-Geigy Ag | Optisch aktives N-(1'-Methyl-2'-methoxyethyl)-N-chloracetyl-2,6-di-methylanilin als Herbizid |
| FR2550201B1 (fr) * | 1983-08-05 | 1986-02-28 | Charbonnages Ste Chimique | Ligands phosphores chiraux, leur procede de fabrication a partir d'aminoacides naturels et leur application a la catalyse de reactions de synthese enantioselective |
| EP0256982B1 (de) * | 1986-08-04 | 1991-08-28 | Ciba-Geigy Ag | Verfahren zur Herstellung von optisch aktiven sekundären Arylaminen |
| US4705877A (en) * | 1987-02-25 | 1987-11-10 | Dow Corning Corporation | Novel aminohydrocarbyl-substituted ketoximosilanes |
| US5011995A (en) * | 1987-07-28 | 1991-04-30 | Ciba-Geigy Corporation | Process for the preparation of optically active secondary amines |
| EP0384086A1 (en) * | 1989-02-10 | 1990-08-29 | BP Chimie Société Anonyme | Synthesis of hydrocarbyl amines |
| US5198561A (en) * | 1989-06-22 | 1993-03-30 | Monsanto Company | Ruthenium-BINAP asymmetric hydrogenation catalyst |
| US5112999A (en) | 1989-09-18 | 1992-05-12 | Ciba-Geigy Corporation | Iridium complexes, process for their preparation and their use |
| US5250731A (en) * | 1992-03-17 | 1993-10-05 | E. I. Du Pont De Nemours And Company | Preparation of optically active hydrazines and amines |
| DE59309554D1 (de) | 1992-04-02 | 1999-06-10 | Novartis Ag | Ferrocenyldiphosphine als Liganden für homogene Katalysatoren |
| UA51652C2 (uk) * | 1995-06-08 | 2002-12-16 | Новартіс Аг | Спосіб гідрування імінів |
| HRP960302A2 (en) * | 1995-07-26 | 1998-04-30 | Ciba Geigy Ag | Process for the hydrogenation of imines |
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- 1995-01-21 DK DK95906339T patent/DK0691949T3/da not_active Application Discontinuation
- 1995-01-21 CZ CZ19952856A patent/CZ287162B6/cs not_active IP Right Cessation
- 1995-01-21 SK SK1366-95A patent/SK281759B6/sk not_active IP Right Cessation
- 1995-01-21 DE DE69505312T patent/DE69505312T2/de not_active Expired - Lifetime
- 1995-01-21 BR BR9505836A patent/BR9505836A/pt not_active IP Right Cessation
- 1995-01-21 KR KR1019950704200A patent/KR100355255B1/ko not_active Expired - Lifetime
- 1995-01-21 HU HU9502851A patent/HU219731B/hu unknown
- 1995-01-21 CN CN95190058A patent/CN1117727C/zh not_active Expired - Lifetime
- 1995-01-21 EP EP95906339A patent/EP0691949B1/en not_active Expired - Lifetime
- 1995-01-21 WO PCT/EP1995/000221 patent/WO1995021151A1/en not_active Ceased
- 1995-01-21 ES ES95906339T patent/ES2123953T3/es not_active Expired - Lifetime
- 1995-01-21 AT AT95906339T patent/ATE172184T1/de active
- 1995-01-31 IL IL11249295A patent/IL112492A/xx not_active IP Right Cessation
- 1995-02-01 HR HR950046A patent/HRP950046B1/xx not_active IP Right Cessation
- 1995-02-01 ZA ZA95781A patent/ZA95781B/xx unknown
-
1997
- 1997-09-10 US US08/926,835 patent/US6822118B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR100355255B1 (ko) | 2002-12-31 |
| CN1117727C (zh) | 2003-08-13 |
| CZ287162B6 (en) | 2000-10-11 |
| ATE172184T1 (de) | 1998-10-15 |
| HUT75955A (en) | 1997-05-28 |
| WO1995021151A1 (en) | 1995-08-10 |
| DE69505312T2 (de) | 1999-04-08 |
| JP3833699B2 (ja) | 2006-10-18 |
| PL310965A1 (en) | 1996-01-22 |
| SK136695A3 (en) | 1996-02-07 |
| HU9502851D0 (en) | 1995-12-28 |
| ES2123953T3 (es) | 1999-01-16 |
| DK0691949T3 (da) | 1999-06-23 |
| CN1123024A (zh) | 1996-05-22 |
| ZA95781B (en) | 1995-08-02 |
| CZ285695A3 (en) | 1996-03-13 |
| HRP950046A2 (en) | 1997-06-30 |
| DE69505312D1 (de) | 1998-11-19 |
| HU219731B (hu) | 2001-07-30 |
| KR960700995A (ko) | 1996-02-24 |
| US6822118B1 (en) | 2004-11-23 |
| SK281759B6 (sk) | 2001-07-10 |
| TW272141B (enExample) | 1996-03-11 |
| RU2150464C1 (ru) | 2000-06-10 |
| AU1456695A (en) | 1995-08-21 |
| EP0691949B1 (en) | 1998-10-14 |
| EP0691949A1 (en) | 1996-01-17 |
| BR9505836A (pt) | 1996-02-27 |
| IL112492A (en) | 1999-12-31 |
| HRP950046B1 (en) | 2000-12-31 |
| JPH08508753A (ja) | 1996-09-17 |
| AU677753B2 (en) | 1997-05-01 |
| IL112492A0 (en) | 1995-03-30 |
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