JPS6323997B2 - - Google Patents
Info
- Publication number
- JPS6323997B2 JPS6323997B2 JP2161280A JP2161280A JPS6323997B2 JP S6323997 B2 JPS6323997 B2 JP S6323997B2 JP 2161280 A JP2161280 A JP 2161280A JP 2161280 A JP2161280 A JP 2161280A JP S6323997 B2 JPS6323997 B2 JP S6323997B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- mol
- complex
- component
- organomagnesium
- 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
- 239000011777 magnesium Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 150000002430 hydrocarbons Chemical group 0.000 claims description 14
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- -1 aluminum compound Chemical class 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 150000002901 organomagnesium compounds Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 150000002367 halogens Chemical group 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000002734 organomagnesium group Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 2
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 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 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- QFCVQKSWGFVMTB-UHFFFAOYSA-N trihexoxyalumane Chemical compound [Al+3].CCCCCC[O-].CCCCCC[O-].CCCCCC[O-] QFCVQKSWGFVMTB-UHFFFAOYSA-N 0.000 description 1
- ZFYVMCFENKKDFG-UHFFFAOYSA-N trioctoxyalumane Chemical compound [Al+3].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] ZFYVMCFENKKDFG-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [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
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2161280A JPS56118087A (en) | 1980-02-25 | 1980-02-25 | Preparation of organic magnesium-aluminum complex |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2161280A JPS56118087A (en) | 1980-02-25 | 1980-02-25 | Preparation of organic magnesium-aluminum complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56118087A JPS56118087A (en) | 1981-09-16 |
| JPS6323997B2 true JPS6323997B2 (enExample) | 1988-05-18 |
Family
ID=12059859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2161280A Granted JPS56118087A (en) | 1980-02-25 | 1980-02-25 | Preparation of organic magnesium-aluminum complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56118087A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0517276Y2 (enExample) * | 1986-08-05 | 1993-05-10 |
-
1980
- 1980-02-25 JP JP2161280A patent/JPS56118087A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56118087A (en) | 1981-09-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0346475B2 (enExample) | ||
| Kawachi et al. | Boron–metal exchange reaction of silylboranes with organometallic reagents: a new route to arylsilyl anions | |
| WO1983000140A1 (fr) | Nouveaux procedes de production d'hydrure de silicium | |
| GB1561730A (en) | Organometallic halides their preparation and use | |
| CN114478351A (zh) | 一种合成α-烷基取代吲哚-3-甲醛类化合物的方法 | |
| JPS6323997B2 (enExample) | ||
| JP2711770B2 (ja) | エーテルを含まない有機金属アミド組成物 | |
| Grovenstein Jr et al. | Phenyl migration during preparation of Grignard reagents | |
| US3597488A (en) | Process for making grignard reagents | |
| Fujisawa et al. | A convenient coupling reaction of allyl alcohols with grignard reagents using 1-chloro-2-methyl-N, N-tetramethylenepropenylamine | |
| EP0525880A1 (en) | Catalytic alkylation process | |
| US1946255A (en) | Preparation of carboxylic acids | |
| Wagner et al. | Mechanisms of photochemical reactions in solution: LXXX. Photolytic dehydrometalation of Grignard compounds | |
| EP0145551A2 (en) | Process for the preparation of alpha, beta-unsaturated ketones | |
| JPS6212770B2 (enExample) | ||
| US20080188671A1 (en) | Method for Producing 2-Formylfuran-4-Boronic Acid by the Metalation of 4-Halofurfural Acetals in the Presence of Suitable Boronic Acid Esters or Anhydrides | |
| WO1997045433A1 (en) | Process for the preparation of benzyl-metal compounds and process for the preparation of 4-phenyl-1-butenes by the use of the same | |
| JP3840810B2 (ja) | β−ケトアルデヒアルカリ塩の製造方法 | |
| JPS60130592A (ja) | アルキニルシリル化合物の製造方法 | |
| RU2153500C1 (ru) | Способ получения дифенилди[(1-этил-1-алюмоциклопент-3-ил)метил ]силана | |
| JP4040707B2 (ja) | ベンジル金属化合物の製造方法 | |
| JP2538447B2 (ja) | N−tert−ブチルジアルキルシリルマレイミドの製造方法 | |
| JPH04225987A (ja) | 金属化1−アルキンおよび置換アルキンの製造方法 | |
| Roberts et al. | Dihydrotrimethylsiloxyaluminum | |
| JPH029889A (ja) | アルキルハロジシラン調製方法 |