JPS648619B2 - - Google Patents
Info
- Publication number
- JPS648619B2 JPS648619B2 JP55045768A JP4576880A JPS648619B2 JP S648619 B2 JPS648619 B2 JP S648619B2 JP 55045768 A JP55045768 A JP 55045768A JP 4576880 A JP4576880 A JP 4576880A JP S648619 B2 JPS648619 B2 JP S648619B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- methyl
- formula
- weight
- catalyst
- 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 claims description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000005984 hydrogenation reaction Methods 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000011572 manganese Substances 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052793 cadmium Inorganic materials 0.000 claims description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052779 Neodymium Inorganic materials 0.000 claims description 3
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 3
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 3
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000003974 aralkylamines Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000009835 boiling Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 150000001728 carbonyl compounds Chemical class 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 8
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- ZZSXZEFWZXSQPX-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-2-methylprop-2-enal Chemical compound O=CC(C)=CC1=CC=C(C(C)(C)C)C=C1 ZZSXZEFWZXSQPX-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- GTXJQSYVXLUOCW-GOOCMWNKSA-N (2r,6s)-2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine Chemical compound C=1C=CC=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 GTXJQSYVXLUOCW-GOOCMWNKSA-N 0.000 description 4
- PLYTVAFAKDFFKM-UHFFFAOYSA-N 3,4-dimethylmorpholine Chemical compound CC1COCCN1C PLYTVAFAKDFFKM-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- -1 alicyclic carbonyl compound Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 239000001496 (E)-2-methyl-3-phenylprop-2-enal Substances 0.000 description 3
- VLUMOWNVWOXZAU-VQHVLOKHSA-N (e)-2-methyl-3-phenylprop-2-enal Chemical compound O=CC(/C)=C/C1=CC=CC=C1 VLUMOWNVWOXZAU-VQHVLOKHSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VLUMOWNVWOXZAU-UHFFFAOYSA-N 2-methyl-3-phenylprop-2-enal Chemical compound O=CC(C)=CC1=CC=CC=C1 VLUMOWNVWOXZAU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- FTQCEUWIHCOHCE-UHFFFAOYSA-N 2,3-dimethylazepane Chemical compound CC1CCCCNC1C FTQCEUWIHCOHCE-UHFFFAOYSA-N 0.000 description 2
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 2
- GDYFTBPYBQUEOT-UHFFFAOYSA-N 2-benzyl-3-methylbutanal Chemical compound CC(C)C(C=O)CC1=CC=CC=C1 GDYFTBPYBQUEOT-UHFFFAOYSA-N 0.000 description 2
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 2
- IDWRJRPUIXRFRX-UHFFFAOYSA-N 3,5-dimethylpiperidine Chemical compound CC1CNCC(C)C1 IDWRJRPUIXRFRX-UHFFFAOYSA-N 0.000 description 2
- SSWAKZIHXNIMGR-UHFFFAOYSA-N 4-(4-tert-butylphenyl)but-3-en-2-one Chemical compound CC(=O)C=CC1=CC=C(C(C)(C)C)C=C1 SSWAKZIHXNIMGR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 2
- 239000011814 protection agent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MCFOSGGZTOIPQI-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2-methylpropan-1-ol Chemical compound CC(C)C(O)C1=CC=C(C(C)(C)C)C=C1 MCFOSGGZTOIPQI-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- YUECWFQZARZQHS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,3-dimethylazepane Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC(C)C1C YUECWFQZARZQHS-UHFFFAOYSA-N 0.000 description 1
- PNPAYADWLSERQE-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]-3,5-dimethylpiperidine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CC(C)CC(C)C1 PNPAYADWLSERQE-UHFFFAOYSA-N 0.000 description 1
- BFOGXYCMWPFIKQ-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]pyrrolidine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCC1 BFOGXYCMWPFIKQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ATTVJWQVBUVDOP-UHFFFAOYSA-N 2,2,4-trimethylazetidine Chemical compound CC1CC(C)(C)N1 ATTVJWQVBUVDOP-UHFFFAOYSA-N 0.000 description 1
- UFLFSJVTFSZTKX-UHFFFAOYSA-N 2,2-dimethylmorpholine Chemical compound CC1(C)CNCCO1 UFLFSJVTFSZTKX-UHFFFAOYSA-N 0.000 description 1
- RPSYMAMREDJAES-UHFFFAOYSA-N 2,5-dimethylmorpholine Chemical compound CC1COC(C)CN1 RPSYMAMREDJAES-UHFFFAOYSA-N 0.000 description 1
- LPNZFNBNRWCBKA-UHFFFAOYSA-N 2,6-diethylmorpholine Chemical compound CCC1CNCC(CC)O1 LPNZFNBNRWCBKA-UHFFFAOYSA-N 0.000 description 1
- GTXJQSYVXLUOCW-UHFFFAOYSA-N 2,6-dimethyl-4-(2-methyl-3-phenylpropyl)morpholine Chemical compound C=1C=CC=CC=1CC(C)CN1CC(C)OC(C)C1 GTXJQSYVXLUOCW-UHFFFAOYSA-N 0.000 description 1
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
- ZMMRSGRBWHYARO-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)butanal Chemical compound CCC(C=O)C1=CC=C(C(C)C)C=C1 ZMMRSGRBWHYARO-UHFFFAOYSA-N 0.000 description 1
- NOWXSWMFTGXVSR-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-2-methylpropanal Chemical compound CC(C)(C)C1=CC=C(C(C)(C)C=O)C=C1 NOWXSWMFTGXVSR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
- ROPNSYBZOVTZBB-UHFFFAOYSA-N 2-benzylbutanal Chemical compound CCC(C=O)CC1=CC=CC=C1 ROPNSYBZOVTZBB-UHFFFAOYSA-N 0.000 description 1
- BOCRJYUZWIOMOJ-UHFFFAOYSA-N 2-benzylidenebutanal Chemical compound CCC(C=O)=CC1=CC=CC=C1 BOCRJYUZWIOMOJ-UHFFFAOYSA-N 0.000 description 1
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 description 1
- RGNFMQJLAOONTP-UHFFFAOYSA-N 2-ethylmorpholine Chemical compound CCC1CNCCO1 RGNFMQJLAOONTP-UHFFFAOYSA-N 0.000 description 1
- MPHJYKZNGMSGNF-UHFFFAOYSA-N 2-methyl-3-(4-methylphenyl)prop-2-enal Chemical compound O=CC(C)=CC1=CC=C(C)C=C1 MPHJYKZNGMSGNF-UHFFFAOYSA-N 0.000 description 1
- SGVBCLGVIOFAFT-UHFFFAOYSA-N 2-methyl-3-(4-methylphenyl)propanal Chemical compound O=CC(C)CC1=CC=C(C)C=C1 SGVBCLGVIOFAFT-UHFFFAOYSA-N 0.000 description 1
- CWDFCXFZGFPHBG-UHFFFAOYSA-N 2-methyl-3-(4-propan-2-yloxyphenyl)prop-2-enal Chemical compound CC(C)OC1=CC=C(C=C(C)C=O)C=C1 CWDFCXFZGFPHBG-UHFFFAOYSA-N 0.000 description 1
- PHQTUXNCTKTFQY-UHFFFAOYSA-N 2-methyl-3-(4-propan-2-yloxyphenyl)propanal Chemical compound CC(C)OC1=CC=C(CC(C)C=O)C=C1 PHQTUXNCTKTFQY-UHFFFAOYSA-N 0.000 description 1
- YCAMGBSPHGCQDC-UHFFFAOYSA-N 2-methyl-3-(4-propan-2-ylphenyl)prop-2-enal Chemical compound CC(C)C1=CC=C(C=C(C)C=O)C=C1 YCAMGBSPHGCQDC-UHFFFAOYSA-N 0.000 description 1
- LTZKHYYXQWNXPU-UHFFFAOYSA-N 2-methyl-3-phenylpropan-1-ol Chemical compound OCC(C)CC1=CC=CC=C1 LTZKHYYXQWNXPU-UHFFFAOYSA-N 0.000 description 1
- HEPHYCJJLAUKSB-UHFFFAOYSA-N 2-methyl-3-phenylpropanal Chemical compound O=CC(C)CC1=CC=CC=C1 HEPHYCJJLAUKSB-UHFFFAOYSA-N 0.000 description 1
- OMRSFUWBMSYOFJ-UHFFFAOYSA-N 2-methyl-4-[3-(4-propan-2-ylphenyl)butyl]morpholine Chemical compound C1=CC(C(C)C)=CC=C1C(C)CCN1CC(C)OCC1 OMRSFUWBMSYOFJ-UHFFFAOYSA-N 0.000 description 1
- MXTNFIYGTWARIN-UHFFFAOYSA-N 2-methylprop-2-enylbenzene Chemical group CC(=C)CC1=CC=CC=C1 MXTNFIYGTWARIN-UHFFFAOYSA-N 0.000 description 1
- YBRAVTNTXVZNMD-UHFFFAOYSA-N 3,3,5-trimethylazepane Chemical compound CC1CCNCC(C)(C)C1 YBRAVTNTXVZNMD-UHFFFAOYSA-N 0.000 description 1
- MDKHWJFKHDRFFZ-UHFFFAOYSA-N 3,5-dimethylmorpholine Chemical compound CC1COCC(C)N1 MDKHWJFKHDRFFZ-UHFFFAOYSA-N 0.000 description 1
- ZFIVSZPVPRXMEF-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)-2-methylpropanal Chemical compound C1=CC(CC(C)C=O)=CC=C1C1CCCCC1 ZFIVSZPVPRXMEF-UHFFFAOYSA-N 0.000 description 1
- JYUQMOHDWHFCAS-UHFFFAOYSA-N 3-(4-cyclopentylphenyl)-2-methylpropanal Chemical compound C1=CC(CC(C)C=O)=CC=C1C1CCCC1 JYUQMOHDWHFCAS-UHFFFAOYSA-N 0.000 description 1
- BNBBFUJNMYQYLA-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methylprop-2-enal Chemical compound COC1=CC=C(C=C(C)C=O)C=C1 BNBBFUJNMYQYLA-UHFFFAOYSA-N 0.000 description 1
- ZCPSKKFTJPQADI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methylpropan-1-ol Chemical compound COC1=CC=C(CC(C)CO)C=C1 ZCPSKKFTJPQADI-UHFFFAOYSA-N 0.000 description 1
- VLFBSPUPYFTTNF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-methylpropanal Chemical compound COC1=CC=C(CC(C)C=O)C=C1 VLFBSPUPYFTTNF-UHFFFAOYSA-N 0.000 description 1
- QLFDFCKDRVCCME-UHFFFAOYSA-N 3-(4-propan-2-ylphenyl)but-2-enal Chemical compound CC(C)C1=CC=C(C(C)=CC=O)C=C1 QLFDFCKDRVCCME-UHFFFAOYSA-N 0.000 description 1
- HQQPOVNESMNPNH-UHFFFAOYSA-N 3-(4-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=C(C(C)CC=O)C=C1 HQQPOVNESMNPNH-UHFFFAOYSA-N 0.000 description 1
- ABNHNQRXESLZRK-UHFFFAOYSA-N 3-(4-tert-butylphenyl)but-2-enal Chemical compound O=CC=C(C)C1=CC=C(C(C)(C)C)C=C1 ABNHNQRXESLZRK-UHFFFAOYSA-N 0.000 description 1
- NKZPGPZCKPODMT-UHFFFAOYSA-N 3-(4-tert-butylphenyl)butanal Chemical compound O=CCC(C)C1=CC=C(C(C)(C)C)C=C1 NKZPGPZCKPODMT-UHFFFAOYSA-N 0.000 description 1
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 1
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 1
- IEARORYJISZKGK-UHFFFAOYSA-N 3-phenylbut-2-enal Chemical compound O=CC=C(C)C1=CC=CC=C1 IEARORYJISZKGK-UHFFFAOYSA-N 0.000 description 1
- MYHGOWDLVRDUFA-UHFFFAOYSA-N 3-phenylbutanal Chemical compound O=CCC(C)C1=CC=CC=C1 MYHGOWDLVRDUFA-UHFFFAOYSA-N 0.000 description 1
- QWNKGUFEJXENIX-UHFFFAOYSA-N 4-(4-tert-butylphenyl)butan-2-one Chemical compound CC(=O)CCC1=CC=C(C(C)(C)C)C=C1 QWNKGUFEJXENIX-UHFFFAOYSA-N 0.000 description 1
- KWHPWBXOLZTZMJ-UHFFFAOYSA-N 4-ethylpiperidine Chemical compound CCC1CCNCC1 KWHPWBXOLZTZMJ-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229910017493 Nd 2 O 3 Inorganic materials 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 229930008407 benzylideneacetone Natural products 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum oxide Inorganic materials [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- PLDDOISOJJCEMH-UHFFFAOYSA-N neodymium oxide Inorganic materials [O-2].[O-2].[O-2].[Nd+3].[Nd+3] PLDDOISOJJCEMH-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- KTUFCUMIWABKDW-UHFFFAOYSA-N oxo(oxolanthaniooxy)lanthanum Chemical compound O=[La]O[La]=O KTUFCUMIWABKDW-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- FRNOGLGSGLTDKL-UHFFFAOYSA-N thulium atom Chemical compound [Tm] FRNOGLGSGLTDKL-UHFFFAOYSA-N 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792914646 DE2914646A1 (de) | 1979-04-11 | 1979-04-11 | Verfahren zur herstellung von aralkylaminen |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS55143966A JPS55143966A (en) | 1980-11-10 |
JPS648619B2 true JPS648619B2 (de) | 1989-02-14 |
Family
ID=6068053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4576880A Granted JPS55143966A (en) | 1979-04-11 | 1980-04-09 | Manufacture of aralkylamine |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS55143966A (de) |
DE (1) | DE2914646A1 (de) |
-
1979
- 1979-04-11 DE DE19792914646 patent/DE2914646A1/de not_active Withdrawn
-
1980
- 1980-04-09 JP JP4576880A patent/JPS55143966A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
DE2914646A1 (de) | 1980-11-13 |
JPS55143966A (en) | 1980-11-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Debenneville et al. | The behavior of aliphatic aldehydes in the Leuckart-Wallach reaction | |
HU198437B (en) | Process for producing mono- or bis-carbonyl-compounds | |
JPS6141612B2 (de) | ||
JPH0321547B2 (de) | ||
US3932518A (en) | Methylation of cyclohexanone with simultaneous dehydrogenation | |
US4346239A (en) | Process for the preparation of 2-methylene aldehydes | |
JPS61109782A (ja) | 1‐アルキル‐又は1‐シクロアルキル‐ピペラジンの製法 | |
US4212972A (en) | Preparation of cis-2,6-dimethylmorpholine | |
US4283534A (en) | Reductive alkylation of nitrogen heterocycles | |
US4384116A (en) | Process for the preparation of morpholine and piperidine derivatives | |
JPS648619B2 (de) | ||
US5166443A (en) | Preparation of 2,2-disubstituted pentane-1,5-diamines | |
HU184829B (en) | Process for preparing cys-2,6-dimethyl-morpholine | |
US4001250A (en) | Process for preparing 4-amino-2,2,6,6-tetramethyl piperidine | |
US5907065A (en) | Method of producing β-isophorone by the isomerization of α-isophorone | |
US4677230A (en) | Preparation of 2-methyl-2-alkenals | |
EP0127835B1 (de) | Verfahren zur Herstellung von Ketonen | |
JPH0772159B2 (ja) | N,n−ジメチルアミンの製造方法 | |
JPH06104641B2 (ja) | α−(アルキルシクロヘキシルオキシ)−β−アルカノールの製造法 | |
JP2639496B2 (ja) | ジモルホリノジエチルエーテル化合物の製造方法 | |
JP5248851B2 (ja) | 2−(1−ヒドロキシアルキル)シクロアルカノンとその脱水体の混合物との製造方法 | |
CA2155722A1 (en) | Preparation of 4,4'-(oxydi-2,1-ethanediyl)bis-morpholine and hydroxyethoxyethyl morpholine | |
JP4138873B2 (ja) | ピペリジノペンタナミン類、その製造および触媒としての使用 | |
JP2002516301A (ja) | シクロペンタノンの製造方法 | |
US5739400A (en) | Preparation of O-(2-hydroxyalkyl)oximes |