CA1244044A - Preparation de composes organometalliques contenant des metaux alcalino-terreux - Google Patents
Preparation de composes organometalliques contenant des metaux alcalino-terreuxInfo
- Publication number
- CA1244044A CA1244044A CA000467622A CA467622A CA1244044A CA 1244044 A CA1244044 A CA 1244044A CA 000467622 A CA000467622 A CA 000467622A CA 467622 A CA467622 A CA 467622A CA 1244044 A CA1244044 A CA 1244044A
- Authority
- CA
- Canada
- Prior art keywords
- magnesium
- alkaline earth
- earth metal
- group
- hydrocarbon
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 alkaline earth metal organometallic compounds Chemical class 0.000 title claims abstract description 132
- 229910052784 alkaline earth metal Inorganic materials 0.000 title claims abstract description 78
- 238000002360 preparation method Methods 0.000 title claims abstract description 46
- 239000011777 magnesium Substances 0.000 claims abstract description 91
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 84
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 84
- 239000002904 solvent Substances 0.000 claims abstract description 84
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 83
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 78
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000007788 liquid Substances 0.000 claims abstract description 56
- 150000001298 alcohols Chemical class 0.000 claims abstract description 52
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims abstract description 30
- BSOBCTSRZNBQLW-UHFFFAOYSA-N barium;2-methyl-1-(2-methylpentoxy)pentane Chemical compound [Ba].CCCC(C)COCC(C)CCC BSOBCTSRZNBQLW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 7
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 4
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 65
- 150000004703 alkoxides Chemical class 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 42
- 229910052788 barium Inorganic materials 0.000 claims description 41
- 239000011575 calcium Substances 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 39
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims description 37
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- 229910052791 calcium Inorganic materials 0.000 claims description 34
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 30
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical group CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 29
- XHGWKWPYPAJRRL-UHFFFAOYSA-N magnesium;2-methyl-1-(2-methylpentoxy)pentane Chemical compound [Mg].CCCC(C)COCC(C)CCC XHGWKWPYPAJRRL-UHFFFAOYSA-N 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 27
- 229910052751 metal Inorganic materials 0.000 claims description 24
- 239000002184 metal Substances 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 21
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 claims description 21
- 150000004796 dialkyl magnesium compounds Chemical class 0.000 claims description 20
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 19
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 16
- VCTCXZDCRFISFF-UHFFFAOYSA-N magnesium;butane;butane Chemical compound [Mg+2].CCC[CH2-].CC[CH-]C VCTCXZDCRFISFF-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- JENCOQNWECEFQI-UHFFFAOYSA-N azanide;barium(2+) Chemical compound [NH2-].[NH2-].[Ba+2] JENCOQNWECEFQI-UHFFFAOYSA-N 0.000 claims description 11
- ZKSADANYBSWZAB-UHFFFAOYSA-N CCCCCC[Mg]CCCCCC Chemical compound CCCCCC[Mg]CCCCCC ZKSADANYBSWZAB-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 9
- 150000002902 organometallic compounds Chemical class 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 239000011591 potassium Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 8
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- ABOURYZTLJUMQZ-UHFFFAOYSA-N calcium;2-methylpropan-1-olate Chemical compound [Ca+2].CC(C)C[O-].CC(C)C[O-] ABOURYZTLJUMQZ-UHFFFAOYSA-N 0.000 claims description 7
- BWKDLDWUVLGWFC-UHFFFAOYSA-N calcium;azanide Chemical compound [NH2-].[NH2-].[Ca+2] BWKDLDWUVLGWFC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- OBQMXSRYRJKXSD-UHFFFAOYSA-N barium(2+);2-methylpropan-1-olate Chemical compound [Ba+2].CC(C)C[O-].CC(C)C[O-] OBQMXSRYRJKXSD-UHFFFAOYSA-N 0.000 claims description 6
- MLJSMQKGZQNIKR-UHFFFAOYSA-N barium;3-(2-ethylhexoxymethyl)heptane Chemical compound [Ba].CCCCC(CC)COCC(CC)CCCC MLJSMQKGZQNIKR-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- CVPGMAAATOZCID-UHFFFAOYSA-N magnesium;2-ethoxyethanolate Chemical group [Mg+2].CCOCC[O-].CCOCC[O-] CVPGMAAATOZCID-UHFFFAOYSA-N 0.000 claims description 6
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 5
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 230000000536 complexating effect Effects 0.000 claims description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 5
- GVXMDIQVPQUJQW-UHFFFAOYSA-N CC(COCC(CCC)C)CCC.[K] Chemical compound CC(COCC(CCC)C)CCC.[K] GVXMDIQVPQUJQW-UHFFFAOYSA-N 0.000 claims description 4
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 4
- YHNWUQFTJNJVNU-UHFFFAOYSA-N magnesium;butane;ethane Chemical compound [Mg+2].[CH2-]C.CCC[CH2-] YHNWUQFTJNJVNU-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- QCHSJPKDWOFACC-UHFFFAOYSA-N 2-Ethyl-4-methyl-1-pentanol Chemical compound CCC(CO)CC(C)C QCHSJPKDWOFACC-UHFFFAOYSA-N 0.000 claims description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 3
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 claims description 3
- UJBFEFNJELQOGG-UHFFFAOYSA-N 2-ethyl-5-methyloctan-1-ol Chemical compound CCCC(C)CCC(CC)CO UJBFEFNJELQOGG-UHFFFAOYSA-N 0.000 claims description 3
- UKFQWAVMIMCNEH-UHFFFAOYSA-N 2-ethylpentan-1-ol Chemical compound CCCC(CC)CO UKFQWAVMIMCNEH-UHFFFAOYSA-N 0.000 claims description 3
- LCFKURIJYIJNRU-UHFFFAOYSA-N 2-methylhexan-1-ol Chemical compound CCCCC(C)CO LCFKURIJYIJNRU-UHFFFAOYSA-N 0.000 claims description 3
- XXGQZBCLBORFOQ-UHFFFAOYSA-N CC(COCC(CCC)C)CCC.[Li] Chemical compound CC(COCC(CCC)C)CCC.[Li] XXGQZBCLBORFOQ-UHFFFAOYSA-N 0.000 claims description 3
- RGPSRYWDFHAWOT-UHFFFAOYSA-N CCCCCCCC[Mg]CCCC Chemical compound CCCCCCCC[Mg]CCCC RGPSRYWDFHAWOT-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 3
- 239000012263 liquid product Substances 0.000 claims description 3
- ORPJQHHQRCLVIC-UHFFFAOYSA-N magnesium;propan-2-olate Chemical compound CC(C)O[Mg]OC(C)C ORPJQHHQRCLVIC-UHFFFAOYSA-N 0.000 claims description 3
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 3
- YLQLIQIAXYRMDL-UHFFFAOYSA-N propylheptyl alcohol Chemical compound CCCCCC(CO)CCC YLQLIQIAXYRMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 claims description 3
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 2
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 claims description 2
- UIIJZQVROQHLAP-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-yloxy)butane;sodium Chemical compound [Na].CCC(C)(C)OC(C)(C)CC UIIJZQVROQHLAP-UHFFFAOYSA-N 0.000 claims description 2
- YYUGBYFBCFRGNZ-UHFFFAOYSA-N 4,6-dimethylheptan-2-ol Chemical compound CC(C)CC(C)CC(C)O YYUGBYFBCFRGNZ-UHFFFAOYSA-N 0.000 claims description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 2
- ZDVJGWXFXGJSIU-UHFFFAOYSA-N 5-methylhexan-2-ol Chemical compound CC(C)CCC(C)O ZDVJGWXFXGJSIU-UHFFFAOYSA-N 0.000 claims description 2
- DTLACFULCCPJNE-UHFFFAOYSA-N CC(COCC(CCC)C)CCC.[Na] Chemical compound CC(COCC(CCC)C)CCC.[Na] DTLACFULCCPJNE-UHFFFAOYSA-N 0.000 claims description 2
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical compound CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 2
- WCXRGQPXPCQKSJ-UHFFFAOYSA-N barium(2+);2-ethoxyethanolate Chemical compound CCOCCO[Ba]OCCOCC WCXRGQPXPCQKSJ-UHFFFAOYSA-N 0.000 claims description 2
- SIELYZXZPWSAPS-UHFFFAOYSA-N calcium;2-methyl-1-(2-methylpentoxy)pentane Chemical compound [Ca].CCCC(C)COCC(C)CCC SIELYZXZPWSAPS-UHFFFAOYSA-N 0.000 claims description 2
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims description 2
- XMAFBJJKWTWLJP-UHFFFAOYSA-N lithium;butan-2-olate Chemical compound [Li+].CCC(C)[O-] XMAFBJJKWTWLJP-UHFFFAOYSA-N 0.000 claims description 2
- PKMBLJNMKINMSK-UHFFFAOYSA-N magnesium;azanide Chemical compound [NH2-].[NH2-].[Mg+2] PKMBLJNMKINMSK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 2
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- KXDANLFHGCWFRQ-UHFFFAOYSA-N magnesium;butane;octane Chemical compound [Mg+2].CCC[CH2-].CCCCCCC[CH2-] KXDANLFHGCWFRQ-UHFFFAOYSA-N 0.000 claims 3
- KYOVRSHPTHPHGT-UHFFFAOYSA-N calcium;3-(2-ethylhexoxymethyl)heptane Chemical compound [Ca].CCCCC(CC)COCC(CC)CCCC KYOVRSHPTHPHGT-UHFFFAOYSA-N 0.000 claims 2
- ZNQOETZUGRUONW-UHFFFAOYSA-N 1-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOC(C)O ZNQOETZUGRUONW-UHFFFAOYSA-N 0.000 claims 1
- BNHGVULTSGNVIX-UHFFFAOYSA-N 1-(2-ethoxyethoxy)ethanol Chemical compound CCOCCOC(C)O BNHGVULTSGNVIX-UHFFFAOYSA-N 0.000 claims 1
- WKRHHSKAXNEKGY-UHFFFAOYSA-N 1-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOC(C)O WKRHHSKAXNEKGY-UHFFFAOYSA-N 0.000 claims 1
- KTVKQTNGWVJHFL-UHFFFAOYSA-N 2-ethylchromen-4-one Chemical compound C1=CC=C2OC(CC)=CC(=O)C2=C1 KTVKQTNGWVJHFL-UHFFFAOYSA-N 0.000 claims 1
- LIHXZLRIMPZNAB-UHFFFAOYSA-N 3-(2-ethylhexoxymethyl)heptane;magnesium Chemical compound [Mg].CCCCC(CC)COCC(CC)CCCC LIHXZLRIMPZNAB-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- KSHXPKRIYDNNTA-UHFFFAOYSA-N barium;2-methyl-4-(4-methylpentan-2-yloxy)pentane Chemical compound [Ba].CC(C)CC(C)OC(C)CC(C)C KSHXPKRIYDNNTA-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000010668 complexation reaction Methods 0.000 claims 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- HAUKUGBTJXWQMF-UHFFFAOYSA-N lithium;propan-2-olate Chemical compound [Li+].CC(C)[O-] HAUKUGBTJXWQMF-UHFFFAOYSA-N 0.000 claims 1
- KLMLLDCNCXMBRK-UHFFFAOYSA-N magnesium;2-hexoxyethanolate Chemical compound [Mg+2].CCCCCCOCC[O-].CCCCCCOCC[O-] KLMLLDCNCXMBRK-UHFFFAOYSA-N 0.000 claims 1
- HFTSQAKJLBPKBD-UHFFFAOYSA-N magnesium;butan-1-olate Chemical compound [Mg+2].CCCC[O-].CCCC[O-] HFTSQAKJLBPKBD-UHFFFAOYSA-N 0.000 claims 1
- FDOIUSSCASVIGM-UHFFFAOYSA-N potassium;2-methylbutan-2-ol Chemical compound [K+].CCC(C)(C)O FDOIUSSCASVIGM-UHFFFAOYSA-N 0.000 claims 1
- 238000007614 solvation Methods 0.000 claims 1
- 229910052712 strontium Inorganic materials 0.000 claims 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract description 63
- 238000002156 mixing Methods 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 abstract description 7
- 150000003138 primary alcohols Chemical class 0.000 abstract description 5
- 239000004711 α-olefin Substances 0.000 abstract description 5
- 150000001993 dienes Chemical class 0.000 abstract description 2
- 125000002734 organomagnesium group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 98
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 238000007792 addition Methods 0.000 description 28
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910052744 lithium Inorganic materials 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- 229940093475 2-ethoxyethanol Drugs 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000003849 aromatic solvent Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 229960005235 piperonyl butoxide Drugs 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- RUSXXJKVMARGOF-UHFFFAOYSA-N cyclohexane;heptane Chemical compound C1CCCCC1.CCCCCCC RUSXXJKVMARGOF-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
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- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- HLTMUYBTNSVOFY-UHFFFAOYSA-N pentylcyclohexane Chemical compound CCCCCC1CCCCC1 HLTMUYBTNSVOFY-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical class [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/68—Preparation of metal alcoholates
- C07C29/70—Preparation of metal alcoholates by converting hydroxy groups to O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/28—Metal alcoholates
- C07C31/30—Alkali metal or alkaline earth metal alcoholates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/062—Al linked exclusively to C
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55191783A | 1983-11-15 | 1983-11-15 | |
| US551,917 | 1983-11-15 | ||
| US06/655,226 US4634786A (en) | 1984-09-27 | 1984-09-27 | Hydrocarbon and chlorinated hydrocarbon-soluble magnesium dialkoxides |
| US655,226 | 1984-09-27 | ||
| US669,675 | 1984-11-08 | ||
| US06/669,675 US4555498A (en) | 1983-11-15 | 1984-11-08 | Preparation of certain alkaline earth metal organometallic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1244044A true CA1244044A (fr) | 1988-11-01 |
Family
ID=27415633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000467622A Expired CA1244044A (fr) | 1983-11-15 | 1984-11-13 | Preparation de composes organometalliques contenant des metaux alcalino-terreux |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0162908A4 (fr) |
| AU (1) | AU3741185A (fr) |
| CA (1) | CA1244044A (fr) |
| IT (1) | IT1199223B (fr) |
| WO (1) | WO1985002176A1 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8521431D0 (en) * | 1985-08-28 | 1985-10-02 | Shell Int Research | Spherical magnesium alkoxide particles |
| US4751318A (en) * | 1986-05-09 | 1988-06-14 | Stauffer Chemical Company | Method of making organic solvent soluble zinc alkoxy alkoxides |
| US4837190A (en) * | 1986-05-09 | 1989-06-06 | Akzo America Inc. | Organic solvent soluble polyvalent metal alkoxy alkoxides |
| US4698323A (en) * | 1986-09-29 | 1987-10-06 | Stauffer Chemical Company | Transition metal catalyst component containing magnesium alkoxy alkoxides |
| CA1328460C (fr) * | 1988-09-30 | 1994-04-12 | Conrad William Kamienski | Traitement de masse de matieres cellulosiques |
| EP0369533A3 (fr) * | 1988-11-14 | 1991-07-24 | Akzo N.V. | Alkoxydes métalliques solubilisés dans un solvant alkoxyalkanol |
| US6359088B1 (en) * | 1998-10-01 | 2002-03-19 | The Goodyear Tire & Rubber Company | Calcium-based catalyst system |
| EP1582523A1 (fr) * | 2004-04-02 | 2005-10-05 | Ludwig-Maximilians-Universität München | Procédé de préparation de composés organomagnésiens |
| DE102010030230A1 (de) | 2009-06-18 | 2010-12-30 | Chemetall Gmbh | Konzentrierte Lösungen von Erdalkalimetallalkoxiden in aprotischen Lösungmitteln und Verfahren zu deren Herstellung |
| BR112013007703B1 (pt) | 2010-09-30 | 2018-10-23 | Chemetall Gmbh | soluções concentradas de complexo de magnésio, de baixa viscosidade, para a produção de catalisadores de polimerização e processo para a sua produção |
| WO2014064233A1 (fr) | 2012-10-25 | 2014-05-01 | Rockwood Lithium GmbH | Solutions concentrées faiblement visqueuses d'alcoxydes de métaux alcalino-terreux dans des solvants aprotiques et procédé pour les préparer |
| PL3619219T3 (pl) | 2014-08-12 | 2024-04-02 | Albemarle Germany Gmbh | Roztwory alkoholanów metali ziem alkalicznych o niskiej lepkości w aprotycznych rozpuszczalnikach, sposób ich wytwarzania i ich zastosowanie do wytwarzania katalizatorów Zieglera-Natty |
| CN112723580A (zh) * | 2019-10-29 | 2021-04-30 | 中国石油化工股份有限公司 | 一种降低含氯有机废液中氯含量的方法和处理含氯有机废液的方法 |
| US11986814B2 (en) | 2021-03-16 | 2024-05-21 | Shandong Jianzhu University | Preparation method of embedded alkaline earth metal oxide solid alkali and application thereof in biodiesel production |
| CN113019352A (zh) * | 2021-03-16 | 2021-06-25 | 山东建筑大学 | 一种嵌入式碱土金属氧化物固体碱的制备方法及其在生物柴油生产中的应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3094546A (en) * | 1960-07-14 | 1963-06-18 | Stauffer Chemical Co | Processes for preparing organometallic compounds |
| BE629687A (fr) * | 1962-03-20 | |||
| US3541149A (en) * | 1963-03-13 | 1970-11-17 | Exxon Research Engineering Co | Crystalline organolithium-tertiary chelating polyamine complexes |
| US3317437A (en) * | 1963-04-08 | 1967-05-02 | Nat Distillers Chem Corp | Process for the production of alfin catalysts |
| US3644602A (en) * | 1968-08-05 | 1972-02-22 | Fmc Corp | Process for producing trialkyl phosphates |
| DE1806549B2 (de) * | 1968-11-02 | 1974-06-12 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur Herstellung von Magnesium-Alkohol-Verbindungen |
| DE2261386C3 (de) * | 1972-12-15 | 1975-08-28 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von Magnesium und Aluminium-Alkoxiden |
| US3971833A (en) * | 1973-07-02 | 1976-07-27 | Dynamit Nobel Aktiengesellschaft | Method for the preparation of alcohol-free alkali and alkaline earth metal alcoholates |
| US3903019A (en) * | 1973-07-16 | 1975-09-02 | Gen Tire & Rubber Co | Preparation of solution polymers using a barium di-tert alkoxide and a di-butyl magnesium catalyst complex |
| US3846385A (en) * | 1973-07-16 | 1974-11-05 | Gen Tire & Rubber Co | Preparation of solution polymers using a barium di-tert alkoxide and a di-butyl magnesium catalyst complex |
| US4092268A (en) * | 1974-06-05 | 1978-05-30 | Compagnie Generale Des Etablissements Michelin, Raison Sociale Michelin & Cie | Catalytic composition |
| US4020115A (en) * | 1975-07-07 | 1977-04-26 | The General Tire & Rubber Company | Alkaline barium alcoholates |
| US4133824A (en) * | 1977-08-17 | 1979-01-09 | Texas Alkyls, Inc. | Organo-magnesium complexes and process for their preparation |
| US4297240A (en) * | 1980-02-25 | 1981-10-27 | The General Tire & Rubber Company | Solution polymerization |
| US4260519A (en) * | 1980-04-22 | 1981-04-07 | The General Tire & Rubber Company | Preparation of barium-alkoxide salts |
-
1984
- 1984-11-13 EP EP19850900283 patent/EP0162908A4/fr not_active Withdrawn
- 1984-11-13 AU AU37411/85A patent/AU3741185A/en not_active Abandoned
- 1984-11-13 WO PCT/US1984/001855 patent/WO1985002176A1/fr not_active Application Discontinuation
- 1984-11-13 CA CA000467622A patent/CA1244044A/fr not_active Expired
- 1984-11-15 IT IT49173/84A patent/IT1199223B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0162908A1 (fr) | 1985-12-04 |
| IT8449173A1 (it) | 1986-05-15 |
| EP0162908A4 (fr) | 1986-04-15 |
| AU3741185A (en) | 1985-06-03 |
| WO1985002176A1 (fr) | 1985-05-23 |
| IT8449173A0 (it) | 1984-11-15 |
| IT1199223B (it) | 1988-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |