DE3854948T2 - Verfahren zur Herstellung von organobimetallischen Verbindungen - Google Patents

Verfahren zur Herstellung von organobimetallischen Verbindungen

Info

Publication number: DE3854948T2
Authority: DE; Germany
Prior art keywords: meli; thf; lithium; methyllithium; mol
Prior art date: 1987-03-30
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 - Fee Related

Application number

DE3854948T

Other languages

German (de)

English (en)

Other versions

DE3854948D1 (de

Inventor

Robert Charles Morrison

Terry Lee Rathman

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lithium Corp of America Inc

Original Assignee

Lithium Corp of America Inc

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.)

1987-03-30

Filing date

1988-03-29

Publication date

1996-11-14

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21860596&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DE3854948(T2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-03-29 Application filed by Lithium Corp of America Inc filed Critical Lithium Corp of America Inc

1996-03-14 Publication of DE3854948D1 publication Critical patent/DE3854948D1/de

1996-11-14 Application granted granted Critical

1996-11-14 Publication of DE3854948T2 publication Critical patent/DE3854948T2/de

2008-03-30 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 51
230000008569 process Effects 0.000 title claims description 26
238000002360 preparation method Methods 0.000 title claims description 11
150000001875 compounds Chemical class 0.000 title description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 338
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims abstract description 232
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 169
239000000203 mixture Substances 0.000 claims abstract description 74
229910052744 lithium Inorganic materials 0.000 claims abstract description 66
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 252
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical group ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 108
238000006243 chemical reaction Methods 0.000 claims description 71
229940050176 methyl chloride Drugs 0.000 claims description 56
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 52
239000011777 magnesium Substances 0.000 claims description 46
229910052751 metal Inorganic materials 0.000 claims description 42
239000002184 metal Substances 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 36
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 34
239000002879 Lewis base Substances 0.000 claims description 33
-1 alicyclic hydrocarbons Chemical class 0.000 claims description 33
229930195733 hydrocarbon Natural products 0.000 claims description 32
150000007527 lewis bases Chemical class 0.000 claims description 32
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 28
239000004215 Carbon black (E152) Substances 0.000 claims description 27
150000002430 hydrocarbons Chemical class 0.000 claims description 27
229910052749 magnesium Inorganic materials 0.000 claims description 24
125000002524 organometallic group Chemical group 0.000 claims description 24
KZLUHGRPVSRSHI-UHFFFAOYSA-N dimethylmagnesium Chemical compound C[Mg]C KZLUHGRPVSRSHI-UHFFFAOYSA-N 0.000 claims description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
239000011734 sodium Substances 0.000 claims description 20
229910052708 sodium Inorganic materials 0.000 claims description 19
150000002739 metals Chemical class 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
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 16
229910052783 alkali metal Inorganic materials 0.000 claims description 15
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 14
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
150000001340 alkali metals Chemical class 0.000 claims description 10
150000008282 halocarbons Chemical class 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 8
150000002902 organometallic compounds Chemical class 0.000 claims description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
229910052782 aluminium Inorganic materials 0.000 claims description 7
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
229910052725 zinc Inorganic materials 0.000 claims description 7
239000011701 zinc Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
229910052788 barium Inorganic materials 0.000 claims description 4
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
239000011575 calcium Substances 0.000 claims description 4
229910052791 calcium Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
239000011591 potassium Substances 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
150000005840 aryl radicals Chemical class 0.000 claims description 3
150000001805 chlorine compounds Chemical group 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000004045 organic chlorine compounds Chemical group 0.000 claims description 2
241000349731 Afzelia bipindensis Species 0.000 claims 2
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 claims 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
238000004519 manufacturing process Methods 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
238000002474 experimental method Methods 0.000 description 40
238000005481 NMR spectroscopy Methods 0.000 description 34
239000000047 product Substances 0.000 description 33
239000002244 precipitate Substances 0.000 description 28
238000004448 titration Methods 0.000 description 26
239000007789 gas Substances 0.000 description 24
238000004458 analytical method Methods 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000001914 filtration Methods 0.000 description 18
239000003849 aromatic solvent Substances 0.000 description 17
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 17
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 17
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
239000006185 dispersion Substances 0.000 description 16
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
238000012360 testing method Methods 0.000 description 16
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
238000003786 synthesis reaction Methods 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 13
150000001350 alkyl halides Chemical class 0.000 description 12
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 12
239000006184 cosolvent Substances 0.000 description 12
239000002002 slurry Substances 0.000 description 11
238000000354 decomposition reaction Methods 0.000 description 10
239000007787 solid Substances 0.000 description 10
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 7
238000003756 stirring Methods 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
238000006263 metalation reaction Methods 0.000 description 6
229940102396 methyl bromide Drugs 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
238000002479 acid--base titration Methods 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
229960003750 ethyl chloride Drugs 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
230000009257 reactivity Effects 0.000 description 5
YZSKZXUDGLALTQ-UHFFFAOYSA-N [Li][C] Chemical class [Li][C] YZSKZXUDGLALTQ-UHFFFAOYSA-N 0.000 description 4
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000003860 storage Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
238000004364 calculation method Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
229910001502 inorganic halide Inorganic materials 0.000 description 3
DLPASUVGCQPFFO-UHFFFAOYSA-N magnesium;ethane Chemical compound [Mg+2].[CH2-]C.[CH2-]C DLPASUVGCQPFFO-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
238000001479 atomic absorption spectroscopy Methods 0.000 description 2
238000010276 construction Methods 0.000 description 2
238000011109 contamination Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000004820 halides Chemical group 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
YNXURHRFIMQACJ-UHFFFAOYSA-N lithium;methanidylbenzene Chemical compound [Li+].[CH2-]C1=CC=CC=C1 YNXURHRFIMQACJ-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002245 particle Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000005057 refrigeration Methods 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
238000005979 thermal decomposition reaction Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
QHPDOSBUCVHCQK-UHFFFAOYSA-N C(C)(C)C1=CC=CC=C1.C(C)C1=CC=CC=C1.C1(=CC=CC=C1)C.C1=CC=CC=C1 Chemical compound C(C)(C)C1=CC=CC=C1.C(C)C1=CC=CC=C1.C1(=CC=CC=C1)C.C1=CC=CC=C1 QHPDOSBUCVHCQK-UHFFFAOYSA-N 0.000 description 1
UNCRKDFOOFDWDK-UHFFFAOYSA-N CCCCC[Mg]CCCCC Chemical compound CCCCC[Mg]CCCCC UNCRKDFOOFDWDK-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
229910000975 Carbon steel Inorganic materials 0.000 description 1
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical class [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
101150117004 atg18 gene Proteins 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229940038926 butyl chloride Drugs 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000010962 carbon steel Substances 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000010959 commercial synthesis reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000000484 continuous-wave nuclear magnetic resonance spectroscopy Methods 0.000 description 1
RUSVQJZOFBUGJZ-UHFFFAOYSA-N cumene toluene Chemical compound CC1=CC=CC=C1.C1(=CC=CC=C1)C.C(C)(C)C1=CC=CC=C1 RUSVQJZOFBUGJZ-UHFFFAOYSA-N 0.000 description 1
ODKWSPNUCDMUDN-UHFFFAOYSA-N cumene;toluene Chemical compound CC1=CC=CC=C1.CC(C)C1=CC=CC=C1 ODKWSPNUCDMUDN-UHFFFAOYSA-N 0.000 description 1
125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
HASGOCLZFTZSTN-UHFFFAOYSA-N cyclohexane;hexane Chemical compound CCCCCC.C1CCCCC1 HASGOCLZFTZSTN-UHFFFAOYSA-N 0.000 description 1
VGHOWOWLIXPTOA-UHFFFAOYSA-N cyclohexane;toluene Chemical compound C1CCCCC1.CC1=CC=CC=C1 VGHOWOWLIXPTOA-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000005661 deetherification reaction Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
150000004796 dialkyl magnesium compounds Chemical class 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
ATZBPOVXVPIOMR-UHFFFAOYSA-N dimethylmercury Chemical compound C[Hg]C ATZBPOVXVPIOMR-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
MPTVOJQMOKMTNP-UHFFFAOYSA-N ethylbenzene;toluene Chemical compound CC1=CC=CC=C1.CCC1=CC=CC=C1 MPTVOJQMOKMTNP-UHFFFAOYSA-N 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012847 fine chemical Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
229910000856 hastalloy Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000012332 laboratory investigation Methods 0.000 description 1
XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
239000002923 metal particle Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000005070 sampling Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
HUOOSYTUUYDSLM-UHFFFAOYSA-N tert-butylbenzene toluene Chemical compound C1(=CC=CC=C1)C.C(C)(C)(C)C1=CC=CC=C1 HUOOSYTUUYDSLM-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005303 weighing Methods 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
- 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
- C07F1/04—Sodium 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DE3854948T 1987-03-30 1988-03-29 Verfahren zur Herstellung von organobimetallischen Verbindungen Expired - Fee Related DE3854948T2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US3163987A	1987-03-30	1987-03-30

Publications (2)

Publication Number	Publication Date
DE3854948D1 DE3854948D1 (de)	1996-03-14
DE3854948T2 true DE3854948T2 (de)	1996-11-14

Family

ID=21860596

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DE3854948T Expired - Fee Related DE3854948T2 (de)	1987-03-30	1988-03-29	Verfahren zur Herstellung von organobimetallischen Verbindungen
DE3856437T Expired - Fee Related DE3856437T2 (de)	1987-03-30	1988-03-29	Verfahren zur Herstellung von metallorganischen Verbindungen

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DE3856437T Expired - Fee Related DE3856437T2 (de)	1987-03-30	1988-03-29	Verfahren zur Herstellung von metallorganischen Verbindungen

Country Status (5)

Country	Link
US (1)	US4976886A (2)
EP (2)	EP0285374B1 (2)
JP (2)	JPS63258480A (2)
AT (2)	ATE197154T1 (2)
DE (2)	DE3854948T2 (2)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5171467A (en) *	1990-03-06	1992-12-15	Fmc Corporation	Synthesis of organometallic/organobimetallic compositions
US5211888A (en) *	1991-07-26	1993-05-18	Fmc Corporation	Catalyzed hydrocarbyllithium process
US5340507A (en) *	1991-07-26	1994-08-23	Fmc Corporation	Catalyzed hydrocarbyllithium process
DE4237884C1 (de) *	1992-11-10	1994-07-07	Metallgesellschaft Ag	Pulverförmiger, nicht pyrophorer Methyllithiumetherat-Komplex und Verfahren zu seiner Herstellung, sowie seine Verwendung
DE4424222C1 (de) *	1994-07-09	1995-09-14	Metallgesellschaft Ag	Gelöstes Methyllithium enthaltendes Synthesemittel sowie Verfahren zu deren Herstellung
EP0753520B1 (de)	1995-07-11	2001-10-17	Chemetall GmbH	Gelöstes Methyllithium enthaltendes Synthesemittel
US7005083B2 (en) *	2000-08-08	2006-02-28	Sqm Lithium Specialties Limited Partnership, Llp	Process for the preparation of alkyllithium compounds
DE10162332A1 (de) *	2001-12-18	2003-07-03	Chemetall Gmbh	Verfahren zur Herstellung von Alkyllithiumverbindungen unter vermindertem Druck
EP1510510A1 (en) *	2002-05-31	2005-03-02	Banyu Pharmaceutical Co., Ltd.	Method of substituent introduction through halogen-metal exchange reaction
US6861011B1 (en) *	2003-11-07	2005-03-01	Chemetall Foote Corporation	Process for preparing methyllithium
EP1582523A1 (en) *	2004-04-02	2005-10-05	Ludwig-Maximilians-Universität München	Method of preparing organomagnesium compounds
DE102004043501A1 (de) *	2004-09-06	2006-03-09	Chemetall Gmbh	Methyllithium/Lithiumbromid enthaltendes Synthesemittel und Verfahren zu dessen Herstellung
CN101331140B (zh) *	2005-10-14	2015-05-06	凯密特尔有限责任公司	含有二有机基镁的合成试剂的制备方法

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3197516A (en) *	1962-02-09	1965-07-27	Lithium Corp	Stable solutions of aryllithium compounds
DE1190462B (de) *	1963-06-21	1965-04-08	Wasagchemie Ag	Verfahren zur Herstellung von Triorganosilyl- und Triorganogermanylverbindungen
US3446860A (en) *	1967-06-29	1969-05-27	Foote Mineral Co	Method of making phenyllithium
US3822219A (en) *	1970-07-23	1974-07-02	Gulf Resources & Chem Corp	Catalyst composition
US3716495A (en) *	1970-09-02	1973-02-13	Phillips Petroleum Co	Polymerization initiator composition and use thereof
US3766280A (en) *	1970-10-28	1973-10-16	Lithium Corp	Diorganomagnesium reagents and methods of preparing same
US3886089A (en) *	1973-11-14	1975-05-27	Foote Mineral Co	Dilithio alkane catalyst compositions and method for the preparation thereof
US4213880A (en) *	1975-09-11	1980-07-22	The Dow Chemical Company	Hydrocarbon solutions of organomagnesium compounds
US4128501A (en) *	1977-06-24	1978-12-05	Texas Alkyls, Inc.	Process for the preparation of organo-magnesium complexes
US4222969A (en) *	1979-04-05	1980-09-16	Texas Alkyls, Inc.	Hydrocarbon soluble magnesium compositions of high magnesium content
US4207207A (en) *	1979-01-17	1980-06-10	Texas Alkyls, Inc.	Hydrocarbon soluble magnesium compositions of high magnesium content
JPS5626893A (en) *	1979-08-09	1981-03-16	Asahi Chem Ind Co Ltd	Hydrocarbon solution containing organo-magnesium compound, and its preparation
US4299781A (en) *	1980-05-12	1981-11-10	Texas Alkyls, Inc.	Organomagnesium solutions of low viscosity
US4429054A (en) *	1982-07-09	1984-01-31	Lithium Corporation Of America	Hydrocarbon solvent solutions of complexes of isopropyllithium and ethyllithium
US4678614A (en) *	1985-11-27	1987-07-07	Lithium Corporation Of America, Inc.	Hydrocarbon-soluble organometallic complexes of magnesium and alkali metals and method of producing same

1988
- 1988-02-25 US US07/160,388 patent/US4976886A/en not_active Expired - Lifetime
- 1988-03-29 DE DE3854948T patent/DE3854948T2/de not_active Expired - Fee Related
- 1988-03-29 AT AT95108551T patent/ATE197154T1/de not_active IP Right Cessation
- 1988-03-29 EP EP88302787A patent/EP0285374B1/en not_active Expired - Lifetime
- 1988-03-29 EP EP95108551A patent/EP0673941B1/en not_active Expired - Lifetime
- 1988-03-29 DE DE3856437T patent/DE3856437T2/de not_active Expired - Fee Related
- 1988-03-29 AT AT88302787T patent/ATE133673T1/de not_active IP Right Cessation
- 1988-03-30 JP JP63074899A patent/JPS63258480A/ja active Granted
1991
- 1991-10-18 JP JP3333821A patent/JPH0532673A/ja active Granted

Also Published As

Publication number	Publication date
JPH059437B2 (2)	1993-02-04
EP0285374B1 (en)	1996-01-31
DE3854948D1 (de)	1996-03-14
EP0673941A2 (en)	1995-09-27
US4976886A (en)	1990-12-11
ATE133673T1 (de)	1996-02-15
ATE197154T1 (de)	2000-11-15
JPH0532673A (ja)	1993-02-09
DE3856437D1 (de)	2000-11-30
JPH0565516B2 (2)	1993-09-17
EP0285374A2 (en)	1988-10-05
DE3856437T2 (de)	2001-06-07
EP0673941B1 (en)	2000-10-25
EP0285374A3 (en)	1991-06-05
EP0673941A3 (en)	1995-11-15
JPS63258480A (ja)	1988-10-25

Legal Events

Date	Code	Title	Description
1997-03-06	8364	No opposition during term of opposition
2005-01-05	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE2755004C2 (de)	1985-03-28	Zusammensetzung bestehend aus Di-n-butylmagnesium, Diäthylmagnesium und Kohlenwasserstoff-Lösungsmittel und Verfahren zu deren Herstellung
DE69812172T2 (de)	2003-08-28	Magnesium-,halogen- und alkoxy-enthaldendes produkt
DE3905857C2 (de)	1997-06-12	Mono- und bimetallische Organoamid-Zusammensetzungen und Verfahren zu ihrer Herstellung
DE3856437T2 (de)	2001-06-07	Verfahren zur Herstellung von metallorganischen Verbindungen
DE69321331T2 (de)	1999-05-20	Verfahren zur Herstellung von Pentafluorphenylmagnesiumderivaten unter Verwendung von Pentafluorbenzol
DE69327203T2 (de)	2000-05-11	Verfahren zur Herstellung von Metallocenen
US4299781A (en)	1981-11-10	Organomagnesium solutions of low viscosity
US5626798A (en)	1997-05-06	Aryllithium products and processes
DE2826498C2 (de)	1986-04-30	Verfahren zur Herstellung eines in Kohlenwasserstoffen löslicher Organomagnesiumkomplexes
DE69226005T2 (de)	1998-12-03	Katalytisches Verfahren zur Herstellung von Hydrocarbyllithiumverbindungen
DE3028478C2 (de)	1982-06-24	Kohlenwasserstofflösliche Isopropylmagnesiumverbindungen, Verfahren zu ihrer Herstellung und Lösungen derselben in Kohlenwasserstoffen
DE3853490T2 (de)	1995-08-24	Ätherfreie organometallische Amidverbindungen.
US5141667A (en)	1992-08-25	Preparation of organometallic and organobimetallic compounds
DE19808570C1 (de)	1999-03-04	Benzylmagnesiumhalogenide oder Allylmagnesiumhalogenide enthaltende Synthesemittel und Verfahren zu deren Herstellung
DE4424222C1 (de)	1995-09-14	Gelöstes Methyllithium enthaltendes Synthesemittel sowie Verfahren zu deren Herstellung
DE3943841C2 (de)	2000-07-13	Bimetallische Organoamid-Zusammensetzungen und Verfahren zu ihrer Herstellung
DE10146233C1 (de)	2002-10-02	Verfahren zur Herstellung von reinen Aryllithiumverbindungen und deren Verwendung
EP0991655B1 (de)	2002-09-11	Verfahren zur herstellung von organoalkalimetallverbindungen
US3524870A (en)	1970-08-18	Preparation of aluminum monohydride diethoxide
DE19821304C1 (de)	1999-09-23	Verfahren zur Herstellung von Alkalimetallalkoholaten
DE68916044T2 (de)	1994-11-10	Verfahren zur Chlordephenylierung von Phenylsilanen.
DE1643905C3 (de)	1973-10-04	Verfahren zur Herstellung von Organolithium oder Organomagnesium aminosihciumverbindungen
US2862944A (en)	1958-12-02	Process for the preparation of high purity alkyltin compounds
DE2615351C2 (de)	1986-07-24	Organomagnesiumkomplexe und Verfahren zu ihrer Herstellung
DE69806604T2 (de)	2003-03-27	Viskositätsverringerung von organomagnesiumlösungen