CN1875078A - 制备甲基锂的方法 - Google Patents
制备甲基锂的方法 Download PDFInfo
- Publication number
- CN1875078A CN1875078A CNA2004800325084A CN200480032508A CN1875078A CN 1875078 A CN1875078 A CN 1875078A CN A2004800325084 A CNA2004800325084 A CN A2004800325084A CN 200480032508 A CN200480032508 A CN 200480032508A CN 1875078 A CN1875078 A CN 1875078A
- Authority
- CN
- China
- Prior art keywords
- lithium
- dispersion
- methf
- metal
- sky
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 12
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 85
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims abstract description 73
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims abstract description 44
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 66
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 44
- 241000349731 Afzelia bipindensis Species 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 229940050176 methyl chloride Drugs 0.000 claims description 21
- 239000003849 aromatic solvent Substances 0.000 claims description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 abstract description 93
- 239000002635 aromatic organic solvent Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 58
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 52
- 239000007788 liquid Substances 0.000 description 47
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 46
- 229910052751 metal Inorganic materials 0.000 description 41
- 239000002184 metal Substances 0.000 description 41
- 239000007789 gas Substances 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 29
- 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 description 27
- 229910052708 sodium Inorganic materials 0.000 description 27
- 239000011734 sodium Substances 0.000 description 27
- 229910052786 argon Inorganic materials 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- 238000009472 formulation Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000000523 sample Substances 0.000 description 20
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 19
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 238000012546 transfer Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000010586 diagram Methods 0.000 description 6
- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- -1 methyl halide Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241001609030 Brosme brosme Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000002525 ultrasonication Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000002879 Lewis base Substances 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000007527 lewis bases Chemical class 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000010742 number 1 fuel oil Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000002896 organic halogen compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000001979 organolithium group Chemical group 0.000 description 2
- 238000013404 process transfer Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000009730 ganji Substances 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- YNXURHRFIMQACJ-UHFFFAOYSA-N lithium;methanidylbenzene Chemical compound [Li+].[CH2-]C1=CC=CC=C1 YNXURHRFIMQACJ-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000013528 metallic particle Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000000207 volumetry Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
- C01D15/00—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
- C07F1/02—Lithium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
实施例 | 产品 | 分散剂 | 平均颗粒大小,微米 | 最小颗粒大小,微米 | 最人颗粒大小,微米 |
1a | nbh | 2 | 52.69 | 0.375 | 282.1 |
1b | nbh | 4 | 33.62 | 0.375 | 234.1 |
1c | nbh | 2 | 50.64 | 0.375 | 309.6 |
1d | nbh | 4 | 31.66 | 0.375 | 92.09 |
2a | nbc | 5 | 51.77 | 0.721 | 234.1 |
2b | nbc | 4 | 33.89 | 0.721 | 213.2 |
2c | nbc | 3 | 38.71 | 0.721 | 213.2 |
2d | nbc | 5 | 45.66 | 0.375 | 282.1 |
3a | sbc | 1 | 42 | 0.5 | 213.2 |
3b | sbc | 2 | 44.28 | 0.7 | 234.1 |
3c | sbc | 4 | 48.88 | 0.721 | 256.8 |
3d | sbc | 5 | 45.76 | 0.721 | 213.2 |
溶剂 | 醚 | 0天 | 15天 | 30天 |
异丙苯 | 2×MeTHF3×MeTHF4×MeTHF | 2.87%2.92%2.87%3.00%2.80%2.89% | 2.86%,0.02%2.90%,0.04%/天3.00%,-2.96%,0.09%/天2.82%,-2.82%,0.16%/天 | 3.00%,-2.93%,-3.00%,-3.02%,-2.81%,-2.86%,0.03%/天 |
乙苯 | 2×MeTHF3×MeTHF4×MeTHF | 2.90%2.98%3.01%2.95%2.94%2.97% | 3.07%,-2.96%,0.05%/天2.99%,0.05%/天2.96%,-3.04%,-2.99%,- | 2.98%,-2.98%,-2.94%,0.07%2.95%,-2.94%,-2.98%,- |
甲苯 | 2×MeTHF3×MeTHF4×MeTHF | 3.00%2.95%2.86%2.97%2.92%2.90% | 2.82%,0.43%/天2.95%,-2.88%,-2.98%,-2.65%,0.66%/天2.87%,0.07%/天 | 2.89%,0.12%/天2.93%,0.02%/天2.81%,0.06%/天2.96%,-2.55%,0.41%/天2.89%,0.01%/天 |
甲苯 | 2×THF | 2.88%2.80% | 2.88%,-2.76%,0.10%/天 | 2.72%,0.18%/天2.77%,0.034%/天 |
异丙苯 | 2×THF | 2.98%2.99% | 3.20%,-3.02%,- | 3.04%,-3.00%,- |
MeTHF | MeTHF | 2.94%2.82% | 2.84%,0.24%/天2.72%,025%/天 | 2.78%,0.16%/天2.69%,0.15%/天 |
溶剂 | 醚 | 0天 | 15天 | 30天 |
异丙苯 | 2×MeTHF3×MeTHF4×MeTHF | 2.87%2.92%2.87%3.00%2.80%2.89% | 2.64%,0.53%2.85%,0.16%/天2.68%,0.44%/天2.82%,0.40%/天2.52%,0.67%/天2.59%,0.69%/天 | 2.69%,0.19%/天2.82%,0.14%/天2.59%,0.31%/天2.74%,0.26%/天2.10%,0.69%/天2.33%,0.59%/天 |
乙苯 | 2×MeTHF3×MeTHF4×MeTHF | 2.90%2.98%3.01%2.95%2.94%2.97% | 2.92%,0.13%/天2.93%,0.11%/天2.73%,0.66%/天2.76%,0.46%/天2.63%,0.75%/天2.62%,0.84%/天 | 2.68%,0.32%/天2.83%,0.16%/天2.49%,0.56%/天2.63%,0.35%/天2.12%,0.90%/天2.30%,0.73%/天 |
甲苯 | 2×MeTHF3×MeTHF4×MeTHF | 3.00%2.95%2.86%2.97%2.92%2.90% | 2.24%,1.81%/天2.91%,0.10%/天1.72%,2.85%/天2.74%,0.53%/天1.06%,4.55%/天2.32%,1.43%/天 | 1.81%,1.28%/天3.03%,-0.59%,2.56%/天2.07%,0.98%/天0%,1.54%,1.51%/天 |
甲苯 | 2×THF | 2.88%2.80% | 1.44%,3.30%/天2.38%,1.07%/天 | 0.60%,2.55%/天1.41%,1.60%/天 |
异丙苯 | 2×THF | 2.95%2.99% | 2.69%,0.42%/天2.90%,0.17%/天 | 2.54%,0.48%/天2.84%,0.17%/天 |
MeTHF | MeTHF | 2.94%2.82% | 2.01%,2.25%/天1.96%,2.18%/天 | 1.09%,1.85%/天1.36%,1.72%/天 |
Claims (6)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/703,768 | 2003-11-07 | ||
US10/703,768 US6861011B1 (en) | 2003-11-07 | 2003-11-07 | Process for preparing methyllithium |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1875078A true CN1875078A (zh) | 2006-12-06 |
CN100584847C CN100584847C (zh) | 2010-01-27 |
Family
ID=34194951
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200480032508A Active CN100584847C (zh) | 2003-11-07 | 2004-09-22 | 制备甲基锂的方法 |
Country Status (12)
Country | Link |
---|---|
US (1) | US6861011B1 (zh) |
EP (1) | EP1682627B1 (zh) |
JP (1) | JP4457112B2 (zh) |
KR (1) | KR100726836B1 (zh) |
CN (1) | CN100584847C (zh) |
AU (1) | AU2004289971B2 (zh) |
BR (1) | BRPI0416025B1 (zh) |
CA (1) | CA2544197C (zh) |
ES (1) | ES2493415T3 (zh) |
IL (1) | IL175216A (zh) |
WO (1) | WO2005047415A1 (zh) |
ZA (1) | ZA200603344B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105153202A (zh) * | 2015-08-10 | 2015-12-16 | 宜兴市昌吉利化工有限公司 | 一种甲基锂溶液及其制备方法 |
CN114212766A (zh) * | 2021-11-04 | 2022-03-22 | 湖南金硅科技有限公司 | 一种补锂改性硅材料及其制备方法和应用 |
CN116284060A (zh) * | 2023-05-22 | 2023-06-23 | 研峰科技(北京)有限公司 | 一种有机锂试剂丁基锂的安全生产工艺 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4976886A (en) * | 1987-03-30 | 1990-12-11 | Lithium Corporation Of America | Preparation of organometallic and organobimetallic compounds |
US5141667A (en) * | 1987-03-30 | 1992-08-25 | Fmc Corporation | Preparation of organometallic and organobimetallic compounds |
US5149889A (en) * | 1988-05-04 | 1992-09-22 | Metallgesellschaft Aktiengesellschaft | Composition for use in organolithium synthesis reactions |
US5100575A (en) * | 1989-09-08 | 1992-03-31 | Fmc Corporation | Thermally stable, reactive organometallic compositions containing copper |
US5171467A (en) * | 1990-03-06 | 1992-12-15 | Fmc Corporation | Synthesis of organometallic/organobimetallic compositions |
US5340507A (en) * | 1991-07-26 | 1994-08-23 | Fmc Corporation | Catalyzed hydrocarbyllithium process |
US5523447A (en) * | 1995-06-07 | 1996-06-04 | Fmc Corporation | Organolithium process |
-
2003
- 2003-11-07 US US10/703,768 patent/US6861011B1/en not_active Expired - Lifetime
-
2004
- 2004-09-22 AU AU2004289971A patent/AU2004289971B2/en active Active
- 2004-09-22 CN CN200480032508A patent/CN100584847C/zh active Active
- 2004-09-22 ES ES04788940.7T patent/ES2493415T3/es active Active
- 2004-09-22 BR BRPI0416025A patent/BRPI0416025B1/pt active IP Right Grant
- 2004-09-22 CA CA002544197A patent/CA2544197C/en active Active
- 2004-09-22 JP JP2006539480A patent/JP4457112B2/ja active Active
- 2004-09-22 EP EP04788940.7A patent/EP1682627B1/en active Active
- 2004-09-22 KR KR1020067008752A patent/KR100726836B1/ko active IP Right Grant
- 2004-09-22 WO PCT/US2004/031211 patent/WO2005047415A1/en active Application Filing
- 2004-09-22 ZA ZA200603344A patent/ZA200603344B/en unknown
-
2006
- 2006-04-26 IL IL175216A patent/IL175216A/en active IP Right Grant
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105153202A (zh) * | 2015-08-10 | 2015-12-16 | 宜兴市昌吉利化工有限公司 | 一种甲基锂溶液及其制备方法 |
CN114212766A (zh) * | 2021-11-04 | 2022-03-22 | 湖南金硅科技有限公司 | 一种补锂改性硅材料及其制备方法和应用 |
CN114212766B (zh) * | 2021-11-04 | 2024-02-13 | 湖南金硅科技有限公司 | 一种补锂改性硅材料及其制备方法和应用 |
CN116284060A (zh) * | 2023-05-22 | 2023-06-23 | 研峰科技(北京)有限公司 | 一种有机锂试剂丁基锂的安全生产工艺 |
Also Published As
Publication number | Publication date |
---|---|
EP1682627A1 (en) | 2006-07-26 |
WO2005047415A1 (en) | 2005-05-26 |
CN100584847C (zh) | 2010-01-27 |
AU2004289971A1 (en) | 2005-05-26 |
ES2493415T3 (es) | 2014-09-11 |
IL175216A (en) | 2012-02-29 |
BRPI0416025B1 (pt) | 2015-11-24 |
CA2544197C (en) | 2010-03-09 |
JP4457112B2 (ja) | 2010-04-28 |
KR20060107767A (ko) | 2006-10-16 |
EP1682627A4 (en) | 2009-08-05 |
KR100726836B1 (ko) | 2007-06-11 |
AU2004289971B2 (en) | 2008-09-18 |
IL175216A0 (en) | 2006-09-05 |
CA2544197A1 (en) | 2005-05-26 |
ZA200603344B (en) | 2007-07-25 |
US6861011B1 (en) | 2005-03-01 |
EP1682627B1 (en) | 2014-08-06 |
BRPI0416025A (pt) | 2007-01-02 |
JP2007513080A (ja) | 2007-05-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1079212C (zh) | 制备类胡萝卜素组合物的方法 | |
CN1789783A (zh) | 用于贮存和输送气体的离子液体基混合物 | |
CN1097069C (zh) | 含有填料的聚四氟乙烯粒状粉末及其制造方法 | |
CN1812859A (zh) | 生产金属化合物的方法和设备 | |
CN87105842A (zh) | 带可分解涂层的颗粒肥料及其制备方法 | |
CN1202052C (zh) | 用硅烷剂/金属化合物/手性配位体实施酮的对映体选择性还原反应 | |
CN1723239A (zh) | 用来制备在聚合物中具有改善了的层离性的纳米复合材料添加剂的方法 | |
CN1031089A (zh) | 悬浮乳液聚合制备不溶于其单体或共聚单体组合物的聚合物和共聚物的方法 | |
CN1545518A (zh) | 新的水滑石,它的合成和应用 | |
CN1875078A (zh) | 制备甲基锂的方法 | |
CN1075086C (zh) | 含有填充物的聚四氟乙烯粒状粉末及其制造方法 | |
CN1080933A (zh) | 适合于使乙烯聚合和共聚成为超高分子聚乙烯的催化剂体系的制备方法 | |
CN1344677A (zh) | 附聚和交换锂的x和lsx沸石的制备方法 | |
CN1309730C (zh) | 粉末状痕量元素及其制备方法和设备 | |
CN1252821A (zh) | 聚四氟乙烯粒状粉末及其制造方法 | |
CN1714047A (zh) | 金属氟化物材料的生产方法 | |
JP2005097249A (ja) | オルガノハロシランの製造方法 | |
CN1040596A (zh) | 防止聚合物结垢的方法 | |
CN1034700A (zh) | 氧化铝细粒的制备方法以及由此制得的产品 | |
CN1043234C (zh) | 制备乙烯-丙烯共聚物的方法 | |
CN1109574A (zh) | 回收和输送高粘稠石油产品的方法 | |
CN1680387A (zh) | 羟基苯丙酸酯的制备方法 | |
CN1129165A (zh) | 搅拌造粒机 | |
CN1763054A (zh) | 一种三苯基氯化锡的原料组分、生产方法及其用途 | |
CN1011971B (zh) | α-烯烃的聚合方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1096421 Country of ref document: HK |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee |
Owner name: ROCKWOOD LITHIUM INC. Free format text: FORMER NAME: CHEMETALL FOOTE CORP. |
|
CP01 | Change in the name or title of a patent holder |
Address after: North Carolina Patentee after: Rockwood Lithium Address before: North Carolina Patentee before: Chemetall Foote Corp. |
|
REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1096421 Country of ref document: HK |