FI70204C - Foerfarande foer framstaellning av sekundaera aminer - Google Patents

Foerfarande foer framstaellning av sekundaera aminer Download PDF

Info

Publication number: FI70204C
Authority: FI; Finland
Prior art keywords: rhodium; compound; olefin; catalyst; reaction
Prior art date: 1980-02-22

Application number

FI804064A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI70204B (fi

FI804064L (fi

Inventor

Felek Jachimowicz

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

1980-12-30

Publication date

1986-09-15

1980-12-30 Application filed by Grace W R & Co filed Critical Grace W R & Co

1981-08-23 Publication of FI804064L publication Critical patent/FI804064L/fi

1986-02-28 Application granted granted Critical

1986-02-28 Publication of FI70204B publication Critical patent/FI70204B/fi

1986-09-15 Publication of FI70204C publication Critical patent/FI70204C/fi

Links

QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 36
-1 olefin compound Chemical class 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 31
239000003054 catalyst Substances 0.000 claims description 30
238000000034 method Methods 0.000 claims description 30
229910052703 rhodium Inorganic materials 0.000 claims description 28
239000010948 rhodium Substances 0.000 claims description 27
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 24
150000003335 secondary amines Chemical class 0.000 claims description 22
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
229910021529 ammonia Inorganic materials 0.000 claims description 17
239000003446 ligand Substances 0.000 claims description 16
150000001336 alkenes Chemical class 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 12
150000003284 rhodium compounds Chemical class 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
229910001868 water Inorganic materials 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 9
229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 claims description 6
229910003450 rhodium oxide Inorganic materials 0.000 claims description 6
150000003283 rhodium Chemical class 0.000 claims description 5
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
150000001450 anions Chemical class 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 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
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000003636 chemical group Chemical group 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 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
150000005673 monoalkenes Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
239000000047 product Substances 0.000 description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
150000003512 tertiary amines Chemical class 0.000 description 10
239000001257 hydrogen Substances 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
239000000376 reactant Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
238000005902 aminomethylation reaction Methods 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000000126 substance Substances 0.000 description 4
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 3
CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
150000001298 alcohols Chemical class 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
LLVUBGQEALYPBE-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1.C1CCC=CC1 LLVUBGQEALYPBE-UHFFFAOYSA-N 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
239000004615 ingredient Substances 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
238000001556 precipitation Methods 0.000 description 3
239000002243 precursor Substances 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-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
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 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
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
125000002723 alicyclic group Chemical group 0.000 description 2
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 2
125000000217 alkyl 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
DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-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
229910052799 carbon Inorganic materials 0.000 description 2
238000003442 catalytic alkylation reaction Methods 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-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
150000002170 ethers Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
125000000623 heterocyclic group Chemical group 0.000 description 2
150000002430 hydrocarbons Chemical class 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
229940095102 methyl benzoate Drugs 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 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
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001302 tertiary amino group Chemical group 0.000 description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
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
MQGIBEAIDUOVOH-UHFFFAOYSA-N 1-[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOCCOCCCC MQGIBEAIDUOVOH-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
HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-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
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
IKCQWKJZLSDDSS-UHFFFAOYSA-N 2-formyloxyethyl formate Chemical compound O=COCCOC=O IKCQWKJZLSDDSS-UHFFFAOYSA-N 0.000 description 1
PWNZQSUHTOQNEK-UHFFFAOYSA-N 2-methyl-1-[2-(2-methylpropoxy)ethoxy]propane Chemical compound CC(C)COCCOCC(C)C PWNZQSUHTOQNEK-UHFFFAOYSA-N 0.000 description 1
DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-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
AXPZDYVDTMMLNB-UHFFFAOYSA-N Benzyl ethyl ether Chemical compound CCOCC1=CC=CC=C1 AXPZDYVDTMMLNB-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 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
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-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
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
CKOYRRWBOKMNRG-UHFFFAOYSA-N Furfuryl acetate Chemical compound CC(=O)OCC1=CC=CO1 CKOYRRWBOKMNRG-UHFFFAOYSA-N 0.000 description 1
241000243251 Hydra Species 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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 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
JKRZOJADNVOXPM-UHFFFAOYSA-N Oxalic acid dibutyl ester Chemical compound CCCCOC(=O)C(=O)OCCCC JKRZOJADNVOXPM-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
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
230000002411 adverse Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 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
235000014121 butter Nutrition 0.000 description 1
229930188620 butyrolactone Natural products 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910002090 carbon oxide Inorganic materials 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
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
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 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
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
150000001983 dialkylethers Chemical class 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
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
XLGKKDZDZBIMRD-UHFFFAOYSA-N dimethyl phenyl phosphite Chemical compound COP(OC)OC1=CC=CC=C1 XLGKKDZDZBIMRD-UHFFFAOYSA-N 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
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
230000000694 effects Effects 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
238000000605 extraction Methods 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000008394 flocculating agent Substances 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
150000004678 hydrides 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
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification 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
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
NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
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 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
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000011368 organic material Substances 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
229930015698 phenylpropene Natural products 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000768 polyamine Polymers 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
239000004094 surface-active agent Substances 0.000 description 1
238000010189 synthetic 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
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
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
238000005406 washing Methods 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)

FI804064A 1980-02-22 1980-12-30 Foerfarande foer framstaellning av sekundaera aminer FI70204C (fi)

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 (3)

Publication Number	Publication Date
FI804064L FI804064L (fi)	1981-08-23
FI70204B FI70204B (fi)	1986-02-28
FI70204C true FI70204C (fi)	1986-09-15

Family

ID=22411099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI804064A FI70204C (fi)	1980-02-22	1980-12-30	Foerfarande foer framstaellning av sekundaera aminer

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
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
NL8006493A (nl)	1981-09-16
FI804064L (fi)	1981-08-23
IT8026425A0 (it)	1980-12-03

Legal Events

Date	Code	Title	Description
1996-07-11	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: W R GRACE & CO -CONN

Publication	Publication Date	Title
US3670029A (en)	1972-06-13	Preparation of unsaturated ethers
FI68805B (fi)	1985-07-31	Alkylering av polyaminer
US3676481A (en)	1972-07-11	Catalytic isomerization of 2-methyl-3-butenenitrile to linear pentenenitriles in the presence of certain metal salt and/or tri(hydrocarbyl)boron promoters
US3110747A (en)	1963-11-12	Homogeneous hydrogenation catalysis
US3513200A (en)	1970-05-19	Preparation of tertiary amines
US3501546A (en)	1970-03-17	Preparation of paraffinic hydrocarbons from acyclic,monohydric,primary alkanols and aldehydes having up to 24 carbon atoms with a catalyst consisting of palladium dispersed on titanium dioxide
SE444440B (sv)	1986-04-14	Forfarande for framstellning av polymer polyamin/amid
US3725498A (en)	1973-04-03	Recyclable liquid aluminum chloride and bromide complexes
FI70204C (fi)	1986-09-15	Foerfarande foer framstaellning av sekundaera aminer
US3887627A (en)	1975-06-03	Preparation of unsaturated alcohols and ethers
FI67872C (fi)	1985-06-10	Foerfarande foer framstaellning av polymer polyamin/amid
US4260844A (en)	1981-04-07	Nickel complexes in diol solvents and their use as oligomerization catalyst precursors
US5196622A (en)	1993-03-23	Alkene addition process
US4337363A (en)	1982-06-29	Process for the preparation of 3-(4-methyl-3-cyclohexen-1-yl) butyraldehyde
US4472522A (en)	1984-09-18	Ethylene oligomerization process
US4503279A (en)	1985-03-05	Ethylene oligomerization process
US3646116A (en)	1972-02-29	Direct production of esters from ethylene and methanol
CA2443707C (en)	2011-07-05	Nickel-containing ethylene oligomerization catalyst and use thereof
EP0024761A1 (en)	1981-03-11	Process for the preparation of alcohols or aldehydes, alcohols or aldehydes prepared by this process and stabilized compositions suitable for use in the said process
US3391212A (en)	1968-07-02	Process for the preparation of olefins
CN103787935A (zh)	2014-05-14	硫氮杂原子配体的制备及该配体的应用
US4377499A (en)	1983-03-22	Nickel complexes in diol solvents and their use as oligomerization catalyst precursors
US4054605A (en)	1977-10-18	Unsaturated amino alcohols
US4472534A (en)	1984-09-18	Slurry phase syngas process
US5233114A (en)	1993-08-03	Alkene addition process