DE2914646A1 - Verfahren zur herstellung von aralkylaminen - Google Patents
Verfahren zur herstellung von aralkylaminenInfo
- Publication number
- DE2914646A1 DE2914646A1 DE19792914646 DE2914646A DE2914646A1 DE 2914646 A1 DE2914646 A1 DE 2914646A1 DE 19792914646 DE19792914646 DE 19792914646 DE 2914646 A DE2914646 A DE 2914646A DE 2914646 A1 DE2914646 A1 DE 2914646A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- methyl
- phenyl
- carbon atoms
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001412 amines Chemical class 0.000 title abstract description 11
- 239000000543 intermediate Substances 0.000 title description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- 238000006268 reductive amination reaction Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 10
- 239000011701 zinc Substances 0.000 claims abstract description 8
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003974 aralkylamines Chemical class 0.000 claims abstract description 4
- 229910052793 cadmium Inorganic materials 0.000 claims abstract description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 7
- 150000002910 rare earth metals Chemical class 0.000 claims description 7
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 3
- 229910001404 rare earth metal oxide Inorganic materials 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 101100006373 Arabidopsis thaliana CHX5 gene Proteins 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- -1 aromatic amines Amines Chemical class 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 239000012043 crude product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical class CC1CNCC(C)O1 HNVIQLPOGUDBSU-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
- 239000000706 filtrate Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 4
- 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 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 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 2
- 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 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
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-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
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite 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
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- 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
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- NEGMHFICHFPWAG-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,2,4-trimethylazetidine Chemical group C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C(C)CC1(C)C NEGMHFICHFPWAG-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
- 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
- FTQCEUWIHCOHCE-UHFFFAOYSA-N 2,3-dimethylazepane Chemical compound CC1CCCCNC1C FTQCEUWIHCOHCE-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
- 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
- GDYFTBPYBQUEOT-UHFFFAOYSA-N 2-benzyl-3-methylbutanal Chemical compound CC(C)C(C=O)CC1=CC=CC=C1 GDYFTBPYBQUEOT-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
- KJPOFYCAOFHEAD-UHFFFAOYSA-N 2-benzylidene-3-methylbutanal Chemical compound CC(C)C(C=O)=CC1=CC=CC=C1 KJPOFYCAOFHEAD-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
- VLUMOWNVWOXZAU-UHFFFAOYSA-N 2-methyl-3-phenylprop-2-enal Chemical compound O=CC(C)=CC1=CC=CC=C1 VLUMOWNVWOXZAU-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
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 description 1
- MDKHWJFKHDRFFZ-UHFFFAOYSA-N 3,5-dimethylmorpholine Chemical compound CC1COCC(C)N1 MDKHWJFKHDRFFZ-UHFFFAOYSA-N 0.000 description 1
- FJJVYRDTFIFEKG-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)-2-methylprop-2-enal Chemical compound C1=CC(C=C(C=O)C)=CC=C1C1CCCCC1 FJJVYRDTFIFEKG-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
- YGDADIFJHVZWGC-UHFFFAOYSA-N 3-(4-cyclopentylphenyl)-2-methylprop-2-enal Chemical compound C1=CC(C=C(C=O)C)=CC=C1C1CCCC1 YGDADIFJHVZWGC-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
- 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
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- WZAUPIMRPCXXBK-UHFFFAOYSA-N O=CC(C)=CC1=CC=CC=C1.O=CC(C)=CC1=CC=CC=C1 Chemical compound O=CC(C)=CC1=CC=CC=C1.O=CC(C)=CC1=CC=CC=C1 WZAUPIMRPCXXBK-UHFFFAOYSA-N 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052775 Thulium Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 229930008407 benzylideneacetone Natural products 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas 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
- 239000007791 liquid phase Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000012243 magnesium silicates Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 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
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-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
- 239000000575 pesticide Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KZKCOVQRXJUGDG-UHFFFAOYSA-N praseodymium Chemical compound [Pr][Pr] KZKCOVQRXJUGDG-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring 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
- 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)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792914646 DE2914646A1 (de) | 1979-04-11 | 1979-04-11 | Verfahren zur herstellung von aralkylaminen |
US06/130,448 US4283534A (en) | 1979-04-11 | 1980-03-14 | Reductive alkylation of nitrogen heterocycles |
CA348,296A CA1128938A (en) | 1979-04-11 | 1980-03-24 | Preparation of aralkylamines |
DE8080101856T DE3060242D1 (en) | 1979-04-11 | 1980-04-08 | Process for the preparation of heterocyclic tertiary aralkyl amines |
EP80101856A EP0017893B1 (de) | 1979-04-11 | 1980-04-08 | Verfahren zur Herstellung von heterocyclischen tertiären Aralkylaminen |
AT80101856T ATE768T1 (de) | 1979-04-11 | 1980-04-08 | Verfahren zur herstellung von heterocyclischen tertiaeren aralkylaminen. |
JP4576880A JPS55143966A (en) | 1979-04-11 | 1980-04-09 | Manufacture of aralkylamine |
HU80860A HU183120B (en) | 1979-04-11 | 1980-04-09 | Process for preparing aralkylamines |
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 (1)
Publication Number | Publication Date |
---|---|
DE2914646A1 true DE2914646A1 (de) | 1980-11-13 |
Family
ID=6068053
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19792914646 Withdrawn DE2914646A1 (de) | 1979-04-11 | 1979-04-11 | Verfahren zur herstellung von aralkylaminen |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS55143966A (enrdf_load_stackoverflow) |
DE (1) | DE2914646A1 (enrdf_load_stackoverflow) |
-
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 |
---|---|
JPS648619B2 (enrdf_load_stackoverflow) | 1989-02-14 |
JPS55143966A (en) | 1980-11-10 |
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Legal Events
Date | Code | Title | Description |
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8130 | Withdrawal |