US2859231A - Manufacture of alkyllead compounds - Google Patents

Manufacture of alkyllead compounds Download PDF

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US2859231A
US2859231A US556051A US55605155A US2859231A US 2859231 A US2859231 A US 2859231A US 556051 A US556051 A US 556051A US 55605155 A US55605155 A US 55605155A US 2859231 A US2859231 A US 2859231A
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lead
reaction
compounds
parts
employed
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Sidney M Blitzer
Tillmon H Pearson
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Ethyl Corp
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Ethyl Corp
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Priority to BE553653D priority Critical patent/BE553653A/xx
Priority to NL213250D priority patent/NL213250A/xx
Priority to NL98814D priority patent/NL98814C/xx
Application filed by Ethyl Corp filed Critical Ethyl Corp
Priority to US556051A priority patent/US2859231A/en
Priority to GB37369/56A priority patent/GB824849A/en
Priority to FR1168218D priority patent/FR1168218A/fr
Priority to DEE13448A priority patent/DE1123323B/de
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    • 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

Definitions

  • This invention relates to a process for the manufacture of tetrahydrocarbon lead compounds. More particularly, the invention is directed to a new and novel process for the manufacture of tetraalkyllead compounds, of which tetraethyllead is the most important.
  • an object of the present invention to provide a new reaction process for manufacturing the tetrahydrocarbonlead compounds, the process overcoming the prior dilficulties and providing other unanticipated benefits. More particularly, an object of the invention is to provide a process which realizes a conversion of lead to tetraethyllead in greater proportions than heretofore provided. Even more specific an object is to provide a process which does not require the use of metallic sodium or other alkali metal. In addition, an object is to provide a process which does not require the use of metallic lead or organic chlorides. A still further object especially of preferred embodiments, is to provide a new reaction process wherein certain lead compounds are reacted with alkyl compounds of active metals.
  • the organic lead salts employed in conducting this invention comprise lead compounds wherein lead is attached to at least one carbon-containing organic radical through an intermediate atom of oxygen or sulfur, that is, a chalkogen.
  • Lead salts of recognized organo acids not having a carboxylic acid grouping, but having strongly acidic hydrogen, are efiective in this process.
  • the lead salts employed in this invention comprise lead carboxylates, lead thiocarboxylates, lead phenates and lead thiophenates. of such leadsalts comprise alkanoic, cycloalkanoic, carboxyaromatic and phenolic radicals.
  • a group III-A metal alkylating agent is reacted with a neutral lead salt of an aliphatic carboxylic acid having from one to about 21 carbon atoms in the aliphatic radical.
  • the lead salt employed will be dictated by a number of factors, primarily economics, inasmuch as they all appear to be.
  • the preferred lead compounds are lead salts of low molecular weight carboxylic acids, especially the lead acetates.
  • Another class of organic lead salts particularly suitable in this invention comprise the lead salts of the so-called naphthenic acids having from six to about twenty-five carbon atoms in each organic radical.
  • the organic portion of the lead salt can contain other elements besides carbon and hydrogen, in particular oxygen.
  • the aromatic radicals can be substituted with other elements including oxygen, nitrogen, sulfur, providing that the substituent is not effective in degrading the metal alkyl reagent.
  • the alkylmetal reactants used in the process are chosen in accordance with the desired tetrahydrocarbonlead product and may be selected from a large number of materials of high but varying effectiveness.
  • the alkylmetal compounds suitably used are preferably derivatives of a metal having an electrode potential of more than 0.3 volt, including for example group I-A metals such as lithium and sodium, group II metals such as beryllium, magnesium, zinc and cadmium, and group III-A metals such as boron and the aluminumtype metals.
  • group I-A metals such as lithium and sodium
  • group II metals such as beryllium, magnesium, zinc and cadmium
  • group III-A metals such as boron and the aluminumtype metals.
  • the fully alkylsubstituted compounds of polyvalent metals are preferred, but alkyl compounds of monovalent active metals, and the partially alkylated derivatives of the polyvalent metals are also suitable.
  • a particular feature of the process of the invention is the employment of lead organo acid salts to produce tetrahydrocarbon lead, or more particularly, tetraalkyllead products. Such materials have not been heretofore produced from lead organo acid salts.
  • a further unexpected advantage of preferred embodiments of the process of the present invention is the transfer of all the alkyl groups of certain polyalkylmetal alkylating agents reacted, into the tetraalkylead product.
  • the organic portion like.
  • alkylating compounds having fromone to about eight carbon atoms-- in each alkyl group are reacted with lead salts of aliphatic acids.
  • lead salts are the lead alkapoates havingone -to 2l carbon atoms in- -e ach-acidic radical:
  • aromatic lead salts which can be employed, typical examples-include lead phenate, lead thiophenate, lead" pounds ofaluminum type metals, VlZ., aluminum, gal-- lium; and indium in grOup III-A of the periodic table, the" alkylaluminum reactants being particularly preferred;
  • trialkylaluminum compounds having a total of 3 to 24 carhon-atoms in the alkyl radicals, the alkyl radicals being norm-al'or branched chain groups.
  • group IIIA-metalalkyl-compounds which can be reacted'with the lea'd organo-acid s'alts are trimethylaluminum, triethylaluminum,-methyldiethylaluminum, tripropylaluminum,
  • a further highly effective class of alkylating reactants for the process are the alkylzinc compoundsya's well "as certain other alkylcompounds of divalent-metals; Both 1 monoand dialkylderivatives are suitable, but the most efiicient process employsa dialkylzinc-compound,-eachalkyl group having, preferably, at-least-oneand; u'p-to Also among-the suitable alkylating eight carbon atoms.
  • agents are the alkyl-zinc hydrides, alkylrzinc halides.
  • the alkyl zinc reagents employedin reacting ,withthe lead:organoacid salt further include the-identically ,di.;
  • alkyl substituted compounds such as,diisopropylzinc,-;di-
  • dialkylzincs having dissimilar alkyl substituents are frequently desirably employed such as methylethylzinc, ethyl-npropyl zinc, isopropyl-n-butylzinc, isobutyl-3,3-dimethylbutylzinc, n-heptyl-n-octyl zinc and others,
  • the proeess is not: confined to the dihydrocarbon zinc com pounds, it having been discovered that monoalkylzinc compeundsare highly eflfectivet;
  • Illustrative examples of such monoalkyl substituted zinc compounds are ethylzinc bromide, ethylzinc chloride, ethylzinc iodide, n-buty
  • organozinc compoundbe 1a purified andvisolated zinc compound, but, in certain instances, reaction, product mix tures having uncertain amounts'of alkylzinc bonds are employable as reagents.
  • metallic zinc can be reacted with 'diethylsulfatetoyield a partially" ethylated zinc-solid that is, thosecompounds having ,more, than, one metal in the compound ,are employable, typical specimens being the-conjplxes-having an alkali metal therein.
  • the rela.- tively pure-monoalkyl compounds'ofthe alkali metals can be employed, 1 although' these compounds generally are dis-advantageous withrespect. to reaction efficiency because or their normally solid, insoluble character, where'- as-manyof the other materials suitable are normally liquids at ,reaction conditions;
  • Typical of the alkyl alkali or alkaline earth metalcompounds suitable in the proc--' ess are; ethyllithium, ethyl sodium, as well as the alkyl compounds having as low asone or up to about eight carbonatomsinthe alkyl radicals.
  • the latter-- group of alkyl compounds includes not only the simple" compounds having only one boron atom in the molecule, but also --thealkyl-substitute derivatives-of diborane B H
  • alkylboroncompounds are triethylborine, triisobutylborine, trimethylborine, trimethyldL; borane,-tri-n-propylborine, et a1.
  • the alkylboron materials be fully alkyl substituted; butother substituents on the base:
  • the unreacted lead is in highly active form as lead metal and is ideally suited for employment in g the commercial process employing sodium-lead alloy 7 or inthat which proposes the reaction of-metallic lead with-3 an 'alkylating- :agent in the presence of magnesium and-a-catalyst.
  • the lead soproduced by this. invention can be: treated; and convertedagain to a lead salt of an organicacid and, employed in making an. alkyllead.
  • a more or less generally applicable reaction procedure is initiated by providing a finely divided lead salt and feeding it into a suitable solvent or suspending medium in a stirred reaction-vessel, said vessel being equipped with means for supplying and removing heat and .introduction of liquids.
  • the vessel is preferably equipped to handle moderate pressures in a sealed system, in many instances, atmospheric pressure operations being fully suitable.
  • the non-lead alkylmetal reactant which may be diluted with a solvent or carrying medium.
  • the reaction proceeds at moderate temperature and as the addition of the alkylmetal reactant proceeds mild refrigeration is applied to the reaction system until all the reactants are blended.
  • external heating can be applied for a moderately long period of time after which the contents of the vessel'are cooled to a convenient handling temperature and discharged into a recovery system.
  • the recovery system employedi depends partly upon the nature of the tetraalkyllead compounds produced and the nature of the by-product metal compound.
  • non-lead alkylmetal reactants such as for example sodium aluminu'rn tetraethyl
  • a two phase reaction system may result and in such instances the reaction is enhanced by employing such reactants in finely divided form and maintaining v eflicient agitation.
  • the non-lead alkylmetal may be a liquid substantially insoluble in any other liquid phase present. In such instances several liquid phases will be present.
  • the tetraalkyllead compound itself as the inert diluent.
  • the recovery of products is simplified and particularly in a continuous operation the materials handling problem and purificationis minimized.
  • This is particularly advantageous when employing non-lead alkylmetal compounds which' are soluble in tetraalkyllead compounds, such a system, however, can also be employed when reacting certain of the mixed alkylmetal compounds or complexes such as for example the sodium fluoridealuminum triethyl complex, the aluminum alkyl hydrides, aluminum sesquihalides, alkylzinc halides, and sodium zinc triethyl.
  • Example I The equipment employed in the present example consisted of a stirred reaction vessel equipped with cooling and heating means as well as means for introducing the reactants to the reaction zone. To this reaction vessel was added 17.1 parts of finely pulverized and dried lead diacetate. The reaction vessel was purged with dry nitrogen gas and 100 parts of toluene was added followed by the addition of 4.09 parts of triethylaluminum. The suspension was stirred for a period of about 0.5 hour at which time the reaction temperature was slowly increased by external heating means to the reflux temperature of the solvent (110 C.) and maintained there for an additional period of 1 hour. At this time the reaction vessel was cooled to room temperature and the mixture was then filtered to remove the solid constituents.
  • Example II I e The procedure of Example I is repeated except that stoichiometric amounts of triethylgallium and lead diacetate are reacted in the presence of cyclohexane at atmospheric pressure and at a reaction temperature of about to 95 C. for about 3 hours. A high yield of tetraethyllead is obtained.
  • Tetraethyllead is again prepared in high yield by reacting triethylindium with essentially a stoichiometric amount of lead tetraacetate in the presence of benzene as a dispersing medium under reflux conditions for a reaction time of about 2% hours.
  • Example IV Example I is repeated essentially as described with the exception that 15.5 parts of lead tetraacetate and 4.0 parts of triethylaluminum were employed. The reaction temperature was maintained between 0 and 10 C. for a total reaction time of 2.5 hours and at the end of which time the reaction mixture was worked up in an identical manner to that of Example I. A yield of tetra;
  • trioctylgallium, trimethylindium and triethylindium areemployed in the process. of. the above examples equally as goodyieldsqof the. corresponding tetraorganolead compounds are obtained.
  • ExampleV The equipment employedin, this example was essentially, as, described in Example ,I.v
  • To the reaction vessel was added 22.8 parts of. lead-diacetate and 50 parts of anhydrous toluene.
  • The, suspension was vigorously stirred under a nitrogen atmosphere and5.8. parts of sodium aluminum.
  • tetraethyl was introduced into the reaction zone.
  • the reactionmixture was heated to the reflux temperature (110 C.) and maintained there for a period of about 3'hours.
  • the temperature was reduced to room temperature andthe reaction mixture worked up in an identical manner to that of Example I to recover the tetraethyllead in a 73.5 yield based on the quantity of sodium aluminum tetraethyl employed.
  • Example VI The procedure of Example V is repeated except that stoichiometric, quantities ofleadtetraacetate andsodium aluminum tetraethyl are employed as the reactants. At a reaction temperature of about 85 -95 C. a high yield of 'tetraethyllead'is obtained after a reaction periodof' about'4 hours. No metallic lead was formed.
  • alkyl metal complex compounds such as lithium aluminum tetraethyl, sodium aluminum tetrabutyl, sodium gallium tetraethyl, potassium gallium tetraethyl and sodium indium tetraethyl areemployed 'in the processes of'Examples ;V and VI.
  • Example VII Again employing'the procedure of Example I, tetraethyllead is obtained in high yield when diethylaluminumhydride is reacted with lead diacetate in essentially stoichiometric quantities in'a toluene reactionmedium.
  • the reaction i con-ducted at the reflux temperature of toluene (110 C.) for a reaction period of about 6 hours.
  • Example VIII The procedure of Example I is again repeated except that 44 parts'of methylaluminumdihydride and 325 parts of lead diacetate are'suspended in 100 parts of benzene in the reaction vessel. The reaction is conducted for a period of about 8 hours at a reaction temperature of 50 C. and the tetramethyllead recovered therefrom in the manner of Example I. An excellent yield of tetramethyllead is obtained.
  • Example IX In a similar processes is shown in Example I, 247.5 parts of ethylaluminum sesquichloride are introduced into thereaction vessel which contain 150 parts of xylene. The mixture is stirred ata rapid rate during the addition of 443 parts of lead tetraacetate, the reaction and the introduction being conducted under a blanket of dried and purified nitrogen. The reaction mixture is maintained at a temperature of about 90 C. for a total reaction time of about 3 hours at the end of which time the temperature is reduced to room temperature and the reaction mixture subjected to the separation steps described ingExample I. A high yield of tetraethyllead is obtained.
  • Example X Excellent. yields. of. tetrabutyllead are; obtained when stoichiometric quantities of-sodium aluminum tributyle hydride and. lead: p al'mitate are: employed; in a similar process .to. thatzofzExampleiI. Thereaction is conducted aha-temperature .ofiabontg40f C. for. a reactiontimeof about:8 hoursand theproduct isrecovered in themanner. of Example I.
  • Example XI This example demonstrates the suitability of employing the complex salts of the alkylmetal compounds with sodiumlluoride in the process of this invention.
  • the equipment and procedures employed were similar to those ofExample-Lexcept that 156 parts of sodium aluminum triethylfiuoride and- 325 parts of lead diacetate in the presence of. ZOOparts -of cyclohexane were employed'as the reactants.
  • the reaction was conducted at a temperatureof about 100 C. fora period ofabout 4 hours. At the conclusion ofthe reaction the temperature was reduced toroom temperatureand the reaction mixture subjected to air-actionation process as described in ample I. An excellent yield of tetraethyllead was obtained.
  • The-sodium. fluoride formed as; aby -product in this process is recovered for use in the formation of addi: tional sodium aluminum triethylfluoride.
  • Example 'XII Example. I is repeated essentially as described with the exception that tetraethylleadis employed as-the diluent and the reaction temperature is to C.
  • the process- is conducted continuously by the continuous feeding of the triethylaluminum and lead diacetate to the reactor and withdrawing a slurry of solids in tetraethyllead from the reactor while leaving a heel of tetraethyllead suificient to maintain the fluidity V of the reaction mixture.
  • Example XIII The process of'Example I was repeated except that 40.4 parts ofleaddistearate and'4.'1 parts of triethylaluminum were reacted together in 100 parts toluene at reflux temperature. A 81% yield of tetraethyllead'was obtained.
  • Example XIV' The suitability of usingsalts containing Pb-S bonding Example XV When the procedure of Example I is again repeated but employing 321.8 parts of lead phenolate and 98 parts of triisobutylaluminum. in alphamethyl naphthalene a solvent'themesults obtained'are similar to those of Example I. A high yield of tetraisobutyllead 'is ob ained.
  • Example X VI The process of Example I is repeatedexce'pt that a mixed alkylaluminum compound is employed. Thus, stoichiometric quantities of methyldiethylaluminum and lead tetraacetate are employed in the procedure of Example I to give an excellent yield of alkylated lead products including tetramethyllead, tetraethyllead, methyltriethyllead, dimethyldiethyllead, and trimethylethyllead.
  • non-lead alkymetal compound is a compound of an aluminum type metal.
  • Other alkylmetal compounds of polyvalent metals are also frequently efiectively used as shown by the following examples.
  • Example X VII A reaction vessel, provided with a vapor outlet and an internal agitator, was carefully dried and flushed several times with dry nitrogen. To the reaction space was added while agitating 40 parts of dry toluene, 11.5 parts of anhydrous lead diacetate and 4.32 partsof diethyl zinc. The foregoing charge ratio is equivalent to equimolal proportions of the lead acetate and diethylzinc.
  • reaction mixture Immediately on adding the diethyl zinc, the reaction mixture turned black and heat was evolved, showing that thereaction started immediately; Stirring was continued, after charging all components, for a one-hour period. At that time the temperature was raised to about 110 C., or enough to cause vaporization and-refluxing of the toluene from an overhead condenser. This refluxing was continued for an additional period of aboutone hour.
  • the reacted mixture was inserted or poured into a volumetric calibrated container, and diluted to approximately twice the volume with benzene solvent. Aliquot portions of the reaction mixture were then analyzed and a yield of about 90 percent tetraethyllead was found.
  • the tetraethyllead is recoverable as a relatively pure product by filtration of the organic layer from the reaction product mixture, and by vacuum distillation or fractionation of the several components thereof.
  • Example XVIII The procedure followed in Example XVII is repeated, except that about 7.8 parts of lead tetraacetate is used in place of the lead diacetate. A good yield of tetraethyllead from the lead tetraacetate converted is obtained.
  • Example XIX Lead diacetate and ethylzinc hydride, in the proportions of about 24 parts of lead diacetate to parts of ethylzinc hydride are reacted together in the presence of a substantial amount of benzene as a reaction medium. A high conversion of the lead diacetate to a good yield of tetraethyllead is obtained.
  • the solid was mixed with lead diacetate in the proportions of 100 parts of solids and 75 parts of lead diacetate, in the presence of about'50 parts of toluene. After heating for about one hour at refluxing conditions, a production of about 20 parts of tetraethyllead was produced.
  • Example XXI Sodium ethyl and lead diacetate are fed to a reaction vessel in approximately 2 to 1 molal proportions, concurrently with sufficient aromatic solvent to provide a thin slurry. The mixture is heated with stirring at about C. for about three hours. A high conversion of the lead diacetate and a good yield of tetraethyllead are provided,
  • Example XXII Lead diisobutyrate, 300 parts, and triethylborine, 100 parts, are reacted in the presence of about 500 parts of ethylbenzene at atmospheric pressure and with continuous stirring at C. After continuing the reaction for several hours, a good conversion of the lead diisobutyrate and a high yield of tetraethyllead are obtained.
  • a lead organo acid salt can be employed sequentially with an inorganic lead salt, for example, lead sulfide or lead oxide, used in proportion sufiiciently to react some, but not all, of the alkyl groups of a polyalkyl metal compound, as is illustrated in the following examples.
  • an inorganic lead salt for example, lead sulfide or lead oxide
  • Example XXIII About 60 parts by weight of dry toluene was charged to a reaction vessel, and then about 12.3 parts of dry, powdered lead oxide. About 4.2 parts of triethylaluminum was charged, and the reaction mixture was heated to refluxing temperature and heating, with stirring, continued for 2.5 hours, and then about 6.3 parts of lead diacetate was added and the reaction continued for an additional hour. A conversion of 70 percent of the ethyl groups to tetraethyllead was obtained, or about 10 percent more than realized by reacting lead oxide solely.
  • a more preferred operation is to supply the lead source in the form of a double salt between the lead organo acid aaaaa l.
  • Example XXIV To 'a solution of 0.3 mole of lead acetate in about 25 parts 'of'water was added 0.3- mole of lead oxide and 100 parts of "benzene. The-mixture washeated to'distillofi the benzene-water azeotrope leaving a white'amorphouspowder which was washed-witbpetroleum ether and dried. Theproduct was identified as the double salt, lead acetate lead oxide.
  • the pressure employed in the reaction vessel is not critical and usually ranges between aboutatrnospheric pressure and the autogenous pressure created by the carrier liquid at the temperature employed.
  • the temperature required to initiate the self-sustaining reaction of this invention varies with the alkyllead compound being produced and the non-lead alkylmetal compound-being-reacted. In general it is-preferred to employ temperature conditions under which the reactants and-products'are stable. Towards this end thermal stabilizers well known to the art, such as'for example naphthalene'and styrene, can be employed to permitthe use of high reaction temperatures without concomitant de-.
  • composition of the alkyllead compounds Generally temperaturesbetween--about 20 to200 C. and' preferably between about 25" and C. can be employed to initiate or conduct the present operation.
  • a processfor manufacturing tetraalkyllead'compounds which comprises reacting in an inert carrierliqni'd a lead salb of an organic-acid wherein lead is attachedto carbonthrou-gh an-intermediate chalkogematom selected I from the group consisting ofoxygen and sulfurand wherein said-organic acidcontains from l te-25 carbon atoms'inclusive with'an alkyl metal compound of a metal having an electrode potential of more than 0.3 volt,-and
  • each. alkyl groupof said alkyl metal compound ⁇ containsup to 8 carbonatoms inclusive.
  • Process ofclaim l-whereinsaid lead salt is a.salt of an acid selected from the group consisting of alkanoic', carboxyaromatic, and phenolic acids.

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US556051A 1955-12-29 1955-12-29 Manufacture of alkyllead compounds Expired - Lifetime US2859231A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
BE553653D BE553653A (de) 1955-12-29
NL213250D NL213250A (de) 1955-12-29
NL98814D NL98814C (de) 1955-12-29
US556051A US2859231A (en) 1955-12-29 1955-12-29 Manufacture of alkyllead compounds
GB37369/56A GB824849A (en) 1955-12-29 1956-12-06 Manufacture of alkyllead compounds
FR1168218D FR1168218A (fr) 1955-12-29 1956-12-19 Fabrications de composés plomb-alkyle
DEE13448A DE1123323B (de) 1955-12-29 1956-12-29 Verfahren zur Herstellung von Tetraalkylbleiverbindungen

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US556051A US2859231A (en) 1955-12-29 1955-12-29 Manufacture of alkyllead compounds

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DE (1) DE1123323B (de)
FR (1) FR1168218A (de)
GB (1) GB824849A (de)
NL (2) NL98814C (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2955124A (en) * 1957-02-27 1960-10-04 Ethyl Corp Manufacture of organolead compounds
US3465012A (en) * 1967-07-27 1969-09-02 Inst Silikon & Fluorkarbonchem Process for alkylating,alkenylating and arylating lead compounds
US3488369A (en) * 1967-07-06 1970-01-06 Ethyl Corp Process for the production of hydrocarbonlead compounds
US3671561A (en) * 1969-01-07 1972-06-20 Schering Ag Method of making hexaorganodiplumbanes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938180A (en) * 1931-06-23 1933-12-05 Shell Dev Process for the manufacture of organic metallo compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1705723A (en) * 1926-10-15 1929-03-19 Du Pont Process of producing tetra-ethyl lead

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938180A (en) * 1931-06-23 1933-12-05 Shell Dev Process for the manufacture of organic metallo compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2955124A (en) * 1957-02-27 1960-10-04 Ethyl Corp Manufacture of organolead compounds
US3488369A (en) * 1967-07-06 1970-01-06 Ethyl Corp Process for the production of hydrocarbonlead compounds
US3465012A (en) * 1967-07-27 1969-09-02 Inst Silikon & Fluorkarbonchem Process for alkylating,alkenylating and arylating lead compounds
US3671561A (en) * 1969-01-07 1972-06-20 Schering Ag Method of making hexaorganodiplumbanes

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NL213250A (de)
BE553653A (de)
DE1123323B (de) 1962-02-08
FR1168218A (fr) 1958-12-05
GB824849A (en) 1959-12-09

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