DE1157616B - Verfahren zur Herstellung von Tetraalkylblei - Google Patents
Verfahren zur Herstellung von TetraalkylbleiInfo
- Publication number
- DE1157616B DE1157616B DEST17583A DEST017583A DE1157616B DE 1157616 B DE1157616 B DE 1157616B DE ST17583 A DEST17583 A DE ST17583A DE ST017583 A DEST017583 A DE ST017583A DE 1157616 B DE1157616 B DE 1157616B
- Authority
- DE
- Germany
- Prior art keywords
- ether
- lead
- electrolysis
- phase
- tetrahydrofuran
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000004519 manufacturing process Methods 0.000 title description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 100
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 83
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 65
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 43
- 238000005868 electrolysis reaction Methods 0.000 claims description 41
- 239000012071 phase Substances 0.000 claims description 38
- 239000003792 electrolyte Substances 0.000 claims description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000007818 Grignard reagent Substances 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 19
- 150000004795 grignard reagents Chemical class 0.000 claims description 19
- ZXHQLEQLZPJIFG-UHFFFAOYSA-N 1-ethoxyhexane Chemical compound CCCCCCOCC ZXHQLEQLZPJIFG-UHFFFAOYSA-N 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 15
- 239000012074 organic phase Substances 0.000 claims description 15
- 150000001350 alkyl halides Chemical class 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 150000001983 dialkylethers Chemical group 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003827 glycol group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000012552 review Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 75
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical group CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 41
- XOOGZRUBTYCLHG-UHFFFAOYSA-N tetramethyllead Chemical compound C[Pb](C)(C)C XOOGZRUBTYCLHG-UHFFFAOYSA-N 0.000 description 33
- 239000011133 lead Substances 0.000 description 29
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 28
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000011777 magnesium Substances 0.000 description 18
- 229910052749 magnesium Inorganic materials 0.000 description 17
- -1 tetraethyl lead Chemical class 0.000 description 17
- 229940050176 methyl chloride Drugs 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 229910001629 magnesium chloride Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 8
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 229960003750 ethyl chloride Drugs 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 238000013459 approach Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 150000002611 lead compounds Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- DNHVXYDGZKWYNU-UHFFFAOYSA-N lead;hydrate Chemical compound O.[Pb] DNHVXYDGZKWYNU-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VRGUHZVPXCABAX-UHFFFAOYSA-N methyllead Chemical compound [Pb]C VRGUHZVPXCABAX-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- HQUNMWUTHYTUPO-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)ethoxy]hexane Chemical compound CCCCCCOCCOCCOCC HQUNMWUTHYTUPO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229930186657 Lat Natural products 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IMNRJGSQCGFPHL-UHFFFAOYSA-N benzene;oxolane Chemical class C1CCOC1.C1=CC=CC=C1 IMNRJGSQCGFPHL-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- OLOAJSHVLXNSQV-UHFFFAOYSA-N diethyl(dimethyl)plumbane Chemical compound CC[Pb](C)(C)CC OLOAJSHVLXNSQV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 108010013049 tetrain Proteins 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/24—Lead compounds
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/13—Organo-metallic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Metallurgy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1521160A | 1960-03-15 | 1960-03-15 | |
| US35078A US3118825A (en) | 1960-03-15 | 1960-06-09 | Electrochemical process for the production of organometallic compounds |
| US3544060A | 1960-06-13 | 1960-06-13 | |
| US35441A US3155602A (en) | 1960-03-15 | 1960-06-13 | Preparation of organic lead compounds |
| US67178A US3298939A (en) | 1960-03-15 | 1960-11-04 | Electrolytic preparation of organolead compounds |
| US79845A US3164537A (en) | 1960-03-15 | 1960-12-30 | Recovery of tetraalkyl lead from electrolytic reaction mixtures |
| US8526761A | 1961-01-27 | 1961-01-27 | |
| US457802A US3399199A (en) | 1965-05-21 | 1965-05-21 | Nitroalkyl-piperazines |
| US54778066A | 1966-05-05 | 1966-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1157616B true DE1157616B (de) | 1963-11-21 |
Family
ID=27577975
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST17583A Pending DE1157616B (de) | 1960-03-15 | 1961-03-15 | Verfahren zur Herstellung von Tetraalkylblei |
| DE1620004A Expired DE1620004C3 (de) | 1960-03-15 | 1966-05-20 | N-0-Phenyl-2-nitropropyi)-Piperazien, dessen Metallsalze und solche Verbindungen enthaltendes Schädlingsbekämpfungsmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1620004A Expired DE1620004C3 (de) | 1960-03-15 | 1966-05-20 | N-0-Phenyl-2-nitropropyi)-Piperazien, dessen Metallsalze und solche Verbindungen enthaltendes Schädlingsbekämpfungsmittel |
Country Status (15)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3256161A (en) * | 1961-02-13 | 1966-06-14 | Nalco Chemical Co | Manufacture of tetramethyl lead |
| US3312605A (en) * | 1961-02-13 | 1967-04-04 | Nalco Chemical Co | Preparation of organo metallic compounds |
| US3408273A (en) * | 1964-03-11 | 1968-10-29 | Nalco Chemical Co | Organic lead recovery from electrolytes by steam and azeotropic distillation |
| DE1250441B (de) * | 1964-05-11 | 1967-09-21 | Ethyl Corporation, Baton Rouge, La. (V. St. A.) | Verfahren zur Herstellung von Alkyl-vinyl-bleiverbindungen |
| US3359291A (en) * | 1964-10-05 | 1967-12-19 | Nalco Chemical Co | Purification of tetraalkyl lead |
| US3380899A (en) * | 1964-10-16 | 1968-04-30 | Nalco Chemical Co | Electrolytic preparation and recovery of tetraalkyl lead compounds |
| US3522156A (en) * | 1964-10-21 | 1970-07-28 | Ethyl Corp | Production of hydrocarbon lead compounds |
| BE671841A (US07122603-20061017-C00045.png) * | 1964-11-05 | |||
| US3403983A (en) * | 1965-01-11 | 1968-10-01 | Mallinckrodt Chemical Works | Steam distillation of metal values in solution |
| US3372098A (en) * | 1965-01-21 | 1968-03-05 | Nalco Chemical Co | Process for recovering solvents from electrolytes |
| US3458410A (en) * | 1965-07-30 | 1969-07-29 | Nalco Chemical Co | Purification of ethers |
| US3393137A (en) * | 1965-12-14 | 1968-07-16 | Nalco Chemical Co | Solvent recovery process |
| US3409518A (en) * | 1966-01-06 | 1968-11-05 | Nalco Chemical Co | Organic halide recovery |
| US3450608A (en) * | 1966-03-09 | 1969-06-17 | Nalco Chemical Co | Purification of ethers |
| JPH03502929A (ja) * | 1988-09-06 | 1991-07-04 | ザ ルブリゾル コーポレーション | ニトロ基含有アミンおよびそれを含有する燃料組成物 |
| US9145341B2 (en) * | 2012-11-19 | 2015-09-29 | Technion Research & Development Foundation Limited | Process of preparing Grignard reagent |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1201049A (fr) * | 1957-07-31 | 1959-12-28 | Nat Aluminate Corp | Procédé de préparation de composés organiques du plomb |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2535190A (en) * | 1949-04-01 | 1950-12-26 | Ethyl Corp | Manufacture of alkyllead compounds |
| US2777867A (en) * | 1953-08-03 | 1957-01-15 | Ethyl Corp | Recovery of alkyllead compounds |
| NL202273A (US07122603-20061017-C00045.png) * | 1954-11-26 | |||
| US2944948A (en) * | 1956-02-06 | 1960-07-12 | Ethyl Corp | Method of purifying organometallic complexes and their use in the preparation of organolead compounds |
| BE590453A (US07122603-20061017-C00045.png) * | 1959-05-06 | |||
| US2960450A (en) * | 1959-10-16 | 1960-11-15 | Ethyl Corp | Organo manganese compounds |
| US3028319A (en) * | 1960-02-01 | 1962-04-03 | Ethyl Corp | Manufacture of magnesium organo compounds |
-
0
- NL NL262356D patent/NL262356A/xx unknown
- LU LU39891D patent/LU39891A1/xx unknown
-
1960
- 1960-06-09 US US35078A patent/US3118825A/en not_active Expired - Lifetime
- 1960-06-13 US US35441A patent/US3155602A/en not_active Expired - Lifetime
- 1960-11-04 US US67178A patent/US3298939A/en not_active Expired - Lifetime
- 1960-12-30 US US79845A patent/US3164537A/en not_active Expired - Lifetime
-
1961
- 1961-03-15 GB GB9445/61A patent/GB984421A/en not_active Expired
- 1961-03-15 DE DEST17583A patent/DE1157616B/de active Pending
-
1966
- 1966-05-05 US US547780A patent/US3584050A/en not_active Expired - Lifetime
- 1966-05-17 IL IL25803A patent/IL25803A/xx unknown
- 1966-05-17 SE SE7011413A patent/SE379040B/xx unknown
- 1966-05-17 SE SE6606793A patent/SE375521B/xx unknown
- 1966-05-18 NO NO163070A patent/NO115641B/no unknown
- 1966-05-18 GB GB22126/66A patent/GB1142337A/en not_active Expired
- 1966-05-20 DK DK258666AA patent/DK125262B/da unknown
- 1966-05-20 BR BR179699/66A patent/BR6679699D0/pt unknown
- 1966-05-20 AT AT1227268A patent/AT314092B/de not_active IP Right Cessation
- 1966-05-20 BE BE681371D patent/BE681371A/xx not_active IP Right Cessation
- 1966-05-20 AT AT481966A patent/AT288340B/de not_active IP Right Cessation
- 1966-05-20 DE DE1620004A patent/DE1620004C3/de not_active Expired
- 1966-05-20 IT IT11441/66A patent/IT986753B/it active
- 1966-05-20 FI FI661331A patent/FI51171C/fi active
- 1966-05-20 NL NL6606997.A patent/NL159975C/xx not_active IP Right Cessation
- 1966-05-23 CH CH119169A patent/CH534121A/de not_active IP Right Cessation
- 1966-05-23 CH CH739566A patent/CH490318A/de not_active IP Right Cessation
- 1966-05-23 CH CH119269A patent/CH505551A/de not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1201049A (fr) * | 1957-07-31 | 1959-12-28 | Nat Aluminate Corp | Procédé de préparation de composés organiques du plomb |
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