NL8006493A - Werkwijze voor de bereiding van secundaire aminen. - Google Patents

Werkwijze voor de bereiding van secundaire aminen. Download PDF

Info

Publication number: NL8006493A
Authority: NL; Netherlands
Prior art keywords: rhodium; compound; catalyst; ammonia; process according
Prior art date: 1980-02-22

Application number

NL8006493A

Other languages

English (en)

Dutch (nl)

Original Assignee

Grace W R & Co

Priority date (The priority date 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 date listed.)

1980-02-22

Filing date

1980-11-28

Publication date

1981-09-16

1980-11-28 Application filed by Grace W R & Co filed Critical Grace W R & Co

1981-09-16 Publication of NL8006493A publication Critical patent/NL8006493A/nl

Links

238000004519 manufacturing process Methods 0.000 title description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
238000000034 method Methods 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 30
239000010948 rhodium Substances 0.000 claims description 30
239000003054 catalyst Substances 0.000 claims description 29
229910052703 rhodium Inorganic materials 0.000 claims description 29
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 27
-1 nitro, sulfo Chemical group 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 23
150000003335 secondary amines Chemical class 0.000 claims description 21
229910021529 ammonia Inorganic materials 0.000 claims description 18
239000003446 ligand Substances 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
229910001868 water Inorganic materials 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 12
150000003284 rhodium compounds Chemical class 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 9
150000001336 alkenes Chemical class 0.000 claims description 9
229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Chemical group CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
230000003197 catalytic effect Effects 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical class [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000003283 rhodium Chemical class 0.000 claims description 6
229910003450 rhodium oxide Inorganic materials 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
150000003568 thioethers Chemical class 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 1
229940087654 iron carbonyl Drugs 0.000 claims 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 15
150000003512 tertiary amines Chemical class 0.000 description 10
239000003153 chemical reaction reagent Substances 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000002904 solvent Substances 0.000 description 7
235000014113 dietary fatty acids Nutrition 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
150000003141 primary amines Chemical class 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000002243 precursor Substances 0.000 description 4
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000005902 aminomethylation reaction Methods 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000007789 gas Substances 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 3
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-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
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
XINCECQTMHSORG-UHFFFAOYSA-N Isoamyl isovalerate Chemical compound CC(C)CCOC(=O)CC(C)C XINCECQTMHSORG-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
125000002877 alkyl aryl group Chemical group 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
125000003710 aryl alkyl group Chemical group 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
235000013844 butane Nutrition 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
238000003442 catalytic alkylation reaction Methods 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
125000001302 tertiary amino group Chemical group 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
QQHQTCGEZWTSEJ-UHFFFAOYSA-N 1-ethenyl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C=C)C=C1 QQHQTCGEZWTSEJ-UHFFFAOYSA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
IOTQTOFPEVQVPG-UHFFFAOYSA-N 1-pentylcyclohexene Chemical compound CCCCCC1=CCCCC1 IOTQTOFPEVQVPG-UHFFFAOYSA-N 0.000 description 1
HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
PRBXPAHXMGDVNQ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]acetic acid Chemical compound OCCOCCOCC(O)=O PRBXPAHXMGDVNQ-UHFFFAOYSA-N 0.000 description 1
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
XCSGHNKDXGYELG-UHFFFAOYSA-N 2-phenoxyethoxybenzene Chemical compound C=1C=CC=CC=1OCCOC1=CC=CC=C1 XCSGHNKDXGYELG-UHFFFAOYSA-N 0.000 description 1
BMJMPMPRZVKSLC-UHFFFAOYSA-N 3-methyl-1-[2-(3-methylbutoxy)ethoxy]butane Chemical compound CC(C)CCOCCOCCC(C)C BMJMPMPRZVKSLC-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
GQWAOUOHRMHSHL-UHFFFAOYSA-N 4-ethenyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(C=C)C=C1 GQWAOUOHRMHSHL-UHFFFAOYSA-N 0.000 description 1
AXPZDYVDTMMLNB-UHFFFAOYSA-N Benzyl ethyl ether Chemical compound CCOCC1=CC=CC=C1 AXPZDYVDTMMLNB-UHFFFAOYSA-N 0.000 description 1
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-VCOUNFBDSA-N Decaline Chemical compound C=1([C@@H]2C3)C=C(OC)C(OC)=CC=1OC(C=C1)=CC=C1CCC(=O)O[C@H]3C[C@H]1N2CCCC1 PXXNTAGJWPJAGM-VCOUNFBDSA-N 0.000 description 1
AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
CKOYRRWBOKMNRG-UHFFFAOYSA-N Furfuryl acetate Chemical compound CC(=O)OCC1=CC=CO1 CKOYRRWBOKMNRG-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
KVOZXXSUSRZIKD-UHFFFAOYSA-N Prop-2-enylcyclohexane Chemical compound C=CCC1CCCCC1 KVOZXXSUSRZIKD-UHFFFAOYSA-N 0.000 description 1
KFNNIILCVOLYIR-UHFFFAOYSA-N Propyl formate Chemical compound CCCOC=O KFNNIILCVOLYIR-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
JANBFCARANRIKJ-UHFFFAOYSA-N bis(3-methylbutyl) benzene-1,2-dicarboxylate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1C(=O)OCCC(C)C JANBFCARANRIKJ-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000013522 chelant Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013581 critical reagent Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
239000004913 cyclooctene Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
229960001826 dimethylphthalate Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940069096 dodecene Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003759 ester based solvent Substances 0.000 description 1
LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000008394 flocculating agent Substances 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
RTIAQOLKVLAEAU-UHFFFAOYSA-N hexan-3-yl acetate Chemical compound CCCC(CC)OC(C)=O RTIAQOLKVLAEAU-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
229940117955 isoamyl acetate Drugs 0.000 description 1
PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 description 1
FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
WBGPDYJIPNTOIB-UHFFFAOYSA-N n,n-dibenzylethanamine Chemical compound C=1C=CC=CC=1CN(CC)CC1=CC=CC=C1 WBGPDYJIPNTOIB-UHFFFAOYSA-N 0.000 description 1
CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
IDFANOPDMXWIOP-UHFFFAOYSA-N n,n-dimethylpentan-1-amine Chemical compound CCCCCN(C)C IDFANOPDMXWIOP-UHFFFAOYSA-N 0.000 description 1
OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
BBDGYADAMYMJNO-UHFFFAOYSA-N n-butyl-n-ethylbutan-1-amine Chemical compound CCCCN(CC)CCCC BBDGYADAMYMJNO-UHFFFAOYSA-N 0.000 description 1
NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
YAOULQGDLCJSSG-UHFFFAOYSA-N perchloric acid hydrochloride Chemical compound Cl(=O)(=O)(=O)O.Cl YAOULQGDLCJSSG-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229930015698 phenylpropene Natural products 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
LCAWZYUJRNVLIG-UHFFFAOYSA-K rhodium(3+);triperchlorate Chemical compound [Rh+3].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O LCAWZYUJRNVLIG-UHFFFAOYSA-K 0.000 description 1
YWFDDXXMOPZFFM-UHFFFAOYSA-H rhodium(3+);trisulfate Chemical compound [Rh+3].[Rh+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O YWFDDXXMOPZFFM-UHFFFAOYSA-H 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

NL8006493A 1980-02-22 1980-11-28 Werkwijze voor de bereiding van secundaire aminen. NL8006493A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/123,822 US4317932A (en)	1980-02-22	1980-02-22	Preparation of secondary amines
US12382280		1980-02-22

Publications (1)

Publication Number	Publication Date
NL8006493A true NL8006493A (nl)	1981-09-16

Family

ID=22411099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8006493A NL8006493A (nl)	1980-02-22	1980-11-28	Werkwijze voor de bereiding van secundaire aminen.

Country Status (10)

Country	Link
US (1)	US4317932A (it)
BE (1)	BE887629A (it)
DE (1)	DE3106108A1 (it)
ES (1)	ES499656A0 (it)
FI (1)	FI70204C (it)
FR (1)	FR2476641B1 (it)
GB (1)	GB2070010B (it)
IT (1)	IT1141109B (it)
NL (1)	NL8006493A (it)
SE (1)	SE453494B (it)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2113210B (en) *	1981-12-15	1985-10-23	Mitsubishi Petrochemical Co	Catalytic process for preparing alkyl tertiary amines
DE3228719A1 (de) *	1982-07-31	1984-02-02	Bayer Ag, 5090 Leverkusen	3-aminomethyl-l-(3-aminopropyl-l-methyl)-4-methylcyclohexan, verfahren zu seiner herstellung und seine verwendung
DE3822038A1 (de) *	1988-06-30	1990-03-01	Hoechst Ag	Verfahren zur herstellung von 3(4),8(9)-bis-(aminomethyl)-tricyclo (5.2.1.0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))-decan
GB9010784D0 (en) *	1990-05-14	1990-07-04	Shell Int Research	Process for the preparation of a secondary amine
US5349109A (en) *	1991-06-04	1994-09-20	The Board Of Regents Of The University Of Oklahoma	Molybdenum-catalyzed amination of olefins
US5773567A (en) *	1996-06-17	1998-06-30	Exxon Chemical Patents Inc	Carboxylic amide-containing polymers for use as fuel or lubricating oil additives and processes for their preparation
DE19737053A1 (de) *	1997-08-26	1999-03-04	Hoechst Ag	Einstufiges Verfahren zur Herstellung von Aminen

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2381472A (en) *	1940-11-13	1945-08-07	Sinclair Refining Co	Production of organic compounds containing nitrogen
US2417893A (en) *	1944-10-12	1947-03-25	Sinclair Refining Co	Production of nitriles and amines
US2497310A (en) *	1946-01-03	1950-02-14	Du Pont	Synthesis of amines
GB891067A (en) *	1959-06-05	1962-03-07	Basf Ag	Improvements in the production of alcohols and amines
US3383426A (en) *	1963-09-09	1968-05-14	Exxon Research Engineering Co	Hydroformylation process for polymers
FR1494136A (fr) *	1966-05-17	1967-09-08	Auxiliaire De L Inst Francais	Procédé de modification des polymères insaturés par réaction avec l'oxyde de carbone, et produits obtenus
US3513200A (en) *	1968-11-25	1970-05-19	Union Oil Co	Preparation of tertiary amines
US3758586A (en) *	1970-03-16	1973-09-11	Du Pont	Catalytic addition of secondary aliphatic amines to ethylene in presence of rhodium or iridium salts
US3947458A (en) *	1970-12-22	1976-03-30	Monsanto Company	Preparation of amines
US3776981A (en) *	1971-02-03	1973-12-04	Shell Oil Co	Hydroformylated block copolymers
US3726926A (en) *	1971-03-19	1973-04-10	Grace W R & Co	Process for preparing n-alkylamines
FR2211002A5 (it) *	1972-12-20	1974-07-12	Rhone Progil
US4107079A (en) *	1973-09-10	1978-08-15	Rhone-Poulenc Industries	Insoluble metallic complexes and catalysts therefrom
FR2324615A2 (fr) *	1974-07-04	1977-04-15	Rhone Progil	Procede de preparation d'amines tertiaires
US4119652A (en) *	1974-08-29	1978-10-10	Monsanto Company	Catalytic asymmetric hydrogenation
US4130590A (en) *	1976-06-21	1978-12-19	Monsanto Company	Production of unsaturated amines
US4250115A (en) *	1978-12-20	1981-02-10	Uop Inc.	Preparation of tertiary amines
US4179469A (en) *	1978-12-20	1979-12-18	Uop Inc.	Preparation of amines

1980
- 1980-02-22 US US06/123,822 patent/US4317932A/en not_active Expired - Lifetime
- 1980-11-28 NL NL8006493A patent/NL8006493A/nl not_active Application Discontinuation
- 1980-12-03 IT IT26425/80A patent/IT1141109B/it active
- 1980-12-18 FR FR808026970A patent/FR2476641B1/fr not_active Expired
- 1980-12-23 SE SE8009106A patent/SE453494B/sv unknown
- 1980-12-30 FI FI804064A patent/FI70204C/fi not_active IP Right Cessation
1981
- 1981-02-19 DE DE19813106108 patent/DE3106108A1/de not_active Ceased
- 1981-02-20 ES ES499656A patent/ES499656A0/es active Granted
- 1981-02-20 GB GB8105487A patent/GB2070010B/en not_active Expired
- 1981-02-20 BE BE0/203880A patent/BE887629A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI70204C (fi)	1986-09-15
GB2070010A (en)	1981-09-03
GB2070010B (en)	1984-04-04
FR2476641A1 (fr)	1981-08-28
ES8202845A1 (es)	1982-02-01
FI70204B (fi)	1986-02-28
BE887629A (fr)	1981-06-15
FR2476641B1 (fr)	1985-07-26
DE3106108A1 (de)	1982-01-07
IT1141109B (it)	1986-10-01
SE453494B (sv)	1988-02-08
ES499656A0 (es)	1982-02-01
US4317932A (en)	1982-03-02
SE8009106L (sv)	1981-08-23
FI804064L (fi)	1981-08-23
IT8026425A0 (it)	1980-12-03

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-08-03	BA	A request for search or an international-type search has been filed
1987-11-02	BB	A search report has been drawn up
1987-12-01	BC	A request for examination has been filed
1989-04-17	DNT	Communications of changes of names of applicants whose applications have been laid open to public inspection	Free format text: GRACE & CO.-CONN. W.R. -
1997-08-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8006490A (nl)	1981-09-16	Werkwijze voor de bereiding van polymeer polyamine/ /amide.
NL8006673A (nl)	1981-09-16	Werkwijze voor het alkyleren van een polyamine.
US3670029A (en)	1972-06-13	Preparation of unsaturated ethers
Blann et al.	2007	Ethylene tetramerisation: Subtle effects exhibited by N-substituted diphosphinoamine ligands
RU2275349C2 (ru)	2006-04-27	Способ получения высших линейных альфа-олефинов и/или алкилразветвленных альфа-олефинов, композиция на их основе (варианты)
US3110747A (en)	1963-11-12	Homogeneous hydrogenation catalysis
US3824221A (en)	1974-07-16	Metallated polymers
NL8006493A (nl)	1981-09-16	Werkwijze voor de bereiding van secundaire aminen.
Jung et al.	2023	Cooperative initiation in a dinuclear indium complex for CO2 epoxide copolymerization
US4297481A (en)	1981-10-27	Process of forming polymeric polyamine/amide
Azizov et al.	2015	Oligomerization of the ethylene in the presence of new heterogenized Zr-containing complex catalytic systems
Jiang et al.	2025	A stable acyl cobalt-based catalyst with exceptionally elevated activity for the carbonylation of epoxides into β-lactones
JPH08239396A (ja)	1996-09-17	レニウムとアルミニウムとの新規化合物、その調製および触媒としてのその使用
KR20240089328A (ko)	2024-06-20	에틸렌의 사량체화를 위한 크로뮴 포스핀일 아이소인돌 아미딘 복합체
JP3654269B2 (ja)	2005-06-02	α−オレフィンの低重合方法
KR20240108434A (ko)	2024-07-09	에틸렌의 사량체화를 위한 크롬 포스피닐 하이드로이소인돌 아미딘 착물
JP3882836B2 (ja)	2007-02-21	α−オレフィン低重合体の製造方法
Barbier-Baudry et al.	2001	New Trends in Organolanthanide Hydride Chemistry
RU2556640C1 (ru)	2015-07-10	Каталитическая система процесса тримеризации этилена в 1-гексен с использованием катализаторов с разветвленным углеводородным скелетом
WO2022133594A1 (en)	2022-06-30	Methods for hydroaminoalkylation of olefins and group 4 metal complexes useful in such methods
Deelman	1994	Lanthanide mediated activation of CH and CX bonds
Eijsink	2017	Activation of nitriles by a ruthenium pincer complex
WO2017069475A1 (ko)	2017-04-27	올레핀 올리고머의 연속 제조 방법
WO2015155666A2 (en)	2015-10-15	Freeze-drying of organoaluminum co-catalyst compositions and transition metal complex catalyst compositions