GB949925A - Process for preparing organometal compounds - Google Patents
Process for preparing organometal compoundsInfo
- Publication number
- GB949925A GB949925A GB43603/62A GB4360362A GB949925A GB 949925 A GB949925 A GB 949925A GB 43603/62 A GB43603/62 A GB 43603/62A GB 4360362 A GB4360362 A GB 4360362A GB 949925 A GB949925 A GB 949925A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- tetra
- methyl
- metal
- catholyte
- 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
- 150000001875 compounds Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- 229940100198 alkylating agent Drugs 0.000 abstract 3
- 239000002168 alkylating agent Substances 0.000 abstract 3
- -1 glycol ethers Chemical class 0.000 abstract 3
- 229910052751 metal Inorganic materials 0.000 abstract 3
- 239000002184 metal Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052785 arsenic Inorganic materials 0.000 abstract 2
- 229910052797 bismuth Inorganic materials 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 abstract 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 238000005868 electrolysis reaction Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- WFCLYEAZTHWNEH-UHFFFAOYSA-N ethylthiocyanate Chemical compound CCSC#N WFCLYEAZTHWNEH-UHFFFAOYSA-N 0.000 abstract 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229910052745 lead Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 abstract 1
- 229940116357 potassium thiocyanate Drugs 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- RJPPYCZKYVZXFJ-UHFFFAOYSA-M triethyl(phenyl)phosphanium;iodide Chemical compound [I-].CC[P+](CC)(CC)C1=CC=CC=C1 RJPPYCZKYVZXFJ-UHFFFAOYSA-M 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth 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)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Abstract
Metal alkyls are made electrolytically by making the selected metal consisting of As, Sb, Pb, Bi, or An the cathode, and using as alkylating agent either (a) an ester, in which the carbon chain is 1-70 C atoms, and the acid has a pKa value in water of less than 6, or (b) an "onium" salt which is weakly acid or basic, and is dissolved in a non-hydroxylic catholyte which has a higher reduction potential than the alkylating agent, e.g. amines, nitriles, sulphones, glycol ethers, ketones, ethers, carboxyamides, or alkyl thio cyanates. The process avoids the use of alkylating agents containing another metal. Suitable esters are, lower alkyl halides, sulphates, phosphates, and carboxylates. "Onium" salts include tetra-ethyl ammonium iodide, tetra benzyl arsonium bromide, and ethyl triphenyl phosphonium iodide. Preferably a permeable diaphragm is used, the anolyte being sodium carbonate solution. The catholyte may also include a conducting salt. Electrolysis is effected at 20-70 DEG C., at 4-30 V., and at current densities up to 1 A.S.Cm. Examples of solvents include acetonitrile, hexa methyl phosphoramide, N-methyl caprolactam, acetone, and ethyl thiocyanate. Conducting salts include alkali metal or alkaline earth halide compounds, e.g. lithium bromide, triethyl phenyl phosphonium iodide, and potassium thiocyanate. In examples, tetra and tri ethyl and methyl compounds of lead, tin, arsenic and bismuth are described. Specification 814,609 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US156128A US3197392A (en) | 1961-11-30 | 1961-11-30 | Process for preparing organometal compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB949925A true GB949925A (en) | 1964-02-19 |
Family
ID=22558222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43603/62A Expired GB949925A (en) | 1961-11-30 | 1962-11-19 | Process for preparing organometal compounds |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3197392A (en) |
| DE (2) | DE1240082B (en) |
| FR (1) | FR1361323A (en) |
| GB (1) | GB949925A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1297605B (en) * | 1964-06-23 | 1969-06-19 | Du Pont | Process for the electrolytic production of tetraalkylene lead |
| CN114525527A (en) * | 2022-01-24 | 2022-05-24 | 安徽师范大学 | Electrochemical synthesis method of sultam derivative |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6511298A (en) * | 1964-10-13 | 1966-04-14 | ||
| US3344048A (en) * | 1964-10-26 | 1967-09-26 | Ethyl Corp | Electrolytic preparation of vinyllead compounds |
| US3432409A (en) * | 1965-06-10 | 1969-03-11 | Du Pont | Electrolytic process for making tetraalkylammonium polybromides |
| US3362889A (en) * | 1966-02-24 | 1968-01-09 | Du Pont | Distillation of tetramethyl lead-acetonitrile azeotrope with thermal stabilizer |
| US3546083A (en) * | 1967-03-06 | 1970-12-08 | Monsanto Co | Polymerization of olefinic compounds and catalysts therefor |
| US3442768A (en) * | 1967-12-21 | 1969-05-06 | Du Pont | Process for recovering tetramethyl lead and azeotropes formed therein |
| US3497428A (en) * | 1968-03-28 | 1970-02-24 | Nalco Chemical Co | Preparation of organo metallic compounds |
| US3622476A (en) * | 1969-10-09 | 1971-11-23 | Continental Oil Co | Cathodic process for the preparation of tetraalkyl lead compounds |
| US4250000A (en) * | 1979-03-26 | 1981-02-10 | Stauffer Chemical Company | Electrochemical process for metal alkoxides |
| US20080173551A1 (en) * | 2003-12-11 | 2008-07-24 | Joshi Ashok V | Electrolytic Method to Make Alkali Alcoholates |
| US7918986B2 (en) * | 2003-12-11 | 2011-04-05 | Ceramatec, Inc. | Electrolytic method to make alkali alcoholates using ceramic ion conducting solid membranes |
| US7824536B2 (en) * | 2003-12-11 | 2010-11-02 | Ceramatec, Inc. | Electrolytic method to make alkali alcoholates using ceramic ion conducting solid membranes |
| US8075758B2 (en) * | 2003-12-11 | 2011-12-13 | Ceramatec, Inc. | Electrolytic method to make alkali alcoholates using ion conducting alkali electrolyte/separator |
| US20080173540A1 (en) * | 2003-12-11 | 2008-07-24 | Joshi Ashok V | Electrolytic Cell for Producing Alkali Alcoholates |
| JP4955015B2 (en) * | 2005-12-20 | 2012-06-20 | セラマテック・インク | Electrolytic process of sodium hypochlorite production using Na ion conductive ceramic membrane |
| EP1976815B1 (en) * | 2006-01-11 | 2012-06-27 | Ceramatec, Inc. | Synthesis of biodiesel using alkali ion conductive ceramic membranes |
| WO2008124047A1 (en) * | 2007-04-03 | 2008-10-16 | Ceramatec, Inc. | Electrochemical process to recycle aqueous alkali chemicals using ceramic ion conducting solid membranes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA531827A (en) * | 1956-10-16 | Calingaert George | Process for making hydrocarbon-lead compounds | |
| US1539297A (en) * | 1923-07-02 | 1925-05-26 | Gen Motors Corp | Method for producing lead compounds |
| DE1114816B (en) * | 1957-06-12 | 1961-10-12 | Dr Dr E H Karl Ziegler | Process and apparatus for the production of tetraethyl lead |
| BE569921A (en) * | 1957-07-31 | |||
| BE590453A (en) * | 1959-05-06 |
-
1961
- 1961-11-30 US US156128A patent/US3197392A/en not_active Expired - Lifetime
-
1962
- 1962-11-19 GB GB43603/62A patent/GB949925A/en not_active Expired
- 1962-11-29 FR FR916988A patent/FR1361323A/en not_active Expired
- 1962-11-29 DE DEP30669A patent/DE1240082B/en active Pending
- 1962-11-29 DE DEP37329A patent/DE1246734B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1297605B (en) * | 1964-06-23 | 1969-06-19 | Du Pont | Process for the electrolytic production of tetraalkylene lead |
| CN114525527A (en) * | 2022-01-24 | 2022-05-24 | 安徽师范大学 | Electrochemical synthesis method of sultam derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1246734B (en) | 1967-08-10 |
| FR1361323A (en) | 1964-05-22 |
| DE1240082B (en) | 1967-05-11 |
| US3197392A (en) | 1965-07-27 |
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