US2535235A - Manufacture of tetraalkyllead - Google Patents

Manufacture of tetraalkyllead Download PDF

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Publication number
US2535235A
US2535235A US30191A US3019148A US2535235A US 2535235 A US2535235 A US 2535235A US 30191 A US30191 A US 30191A US 3019148 A US3019148 A US 3019148A US 2535235 A US2535235 A US 2535235A
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US
United States
Prior art keywords
lead
alloy
tetraalkyllead
magnesium
per cent
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 - Lifetime
Application number
US30191A
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English (en)
Inventor
Shapiro Hymin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ethyl Corp
Original Assignee
Ethyl Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DENDAT878645D priority Critical patent/DE878645C/de
Application filed by Ethyl Corp filed Critical Ethyl Corp
Priority to US30191A priority patent/US2535235A/en
Priority to US30192A priority patent/US2535236A/en
Priority to GB12560/49A priority patent/GB668561A/en
Priority to FR986329D priority patent/FR986329A/fr
Application granted granted Critical
Publication of US2535235A publication Critical patent/US2535235A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/24—Lead compounds

Definitions

  • This invention relates to a catalytic process for the manufacture of tetraalkyllead from magnesium-lead alloy and certain of the alkyl halides. More particularly, it relates to a process for reacting a magnesium-lead alloy with an alkyl halide selected from the group consisting of chlorides, bromides, iodides in the presence of selected catalysts to form a tetraalkyllead.
  • This is accomplished in my invention by reacting certain alkyl halides with magnesium-lead alloy in the presence of as illustrated by the following Temp. MgiPb 102E501 Tr (CgH)4Pb 2Mg0lz It is to be noted that in the above equation, .no lead in the alloy is converted to metallic lead as contrasted with over '75 per cent lead converted from the alloy to finely divided metal in the present commercial operations? 25 methyl diphenyl amine.
  • the coordinating atom is either oxygen or nitrogen.
  • amines such as trialkyl amines, such as triethyl amine, tripropyl amine, tributyl amine, alkyl phenyl amines, such as dimethyi phenyl amine, diethyl phenyl amine, and Also, amines such as pyridine have been successfully used.
  • alkyl or aromatic ammonium iodides such as trimethylphenyl ammonium iodide, tetrabutyl ammonium iodide, and tetraethyl ammonium corresponding tetraalkylleadcompounds, such as the monochloro derivatives of methane, ethane, propane, butane, and pentane, as well as the corresponding bromides and iodides.
  • alkyl or aromatic ammonium iodides such as trimethylphenyl ammonium iodide, tetrabutyl ammonium iodide, and tetraethyl ammonium corresponding tetraalkylleadcompounds, such as the monochloro derivatives of methane, ethane, propane, butane, and pentane, as well as the corresponding bromides and iodides.
  • My process can be carried out at temperatures up to 150 C. although the preferred range is'80 responding to MgzPb (19.01 per cent Mg by weight), but good yields are obtainable with a magnesium content varying from 18 to 22 per cent by weight. As the magnesium content varies outside of this range inferior results are obtained, and furthermore, the alloy is more difficult to crush preparatory to using.
  • the time for the reaction can also be varied over a wide range. In closed bomb operations, the reaction time has been varied between two.
  • catalyst can also be varied within wide limits, i. e., between 1 and per cent by'weight of the are ordinary commercial grades.
  • My invention is further illustrated by the following example: grams of MgzPb alloy, 20 grams of ethyl chloride and 5 grams of ethyl ether catalyst were introduced into a tumbled bomb.
  • the alloy comprising about 19 per cent by weight magnesium, was first ground in a chipmunk crusher to a particle size varying from four to 100 mesh, substantially three-quar- ,tcrs'of the ground alloy being in the range of four to 40-mesh.
  • the ethyl chloride and the ether The materials are charged into the bomb preferably in the order: alloy, ethyl chloride, and ethyl ether.
  • the bomb was then closed off and tumbled for six hours at 80 C.
  • the reaction is exothermic and cooling is employed after the reaction is under way in order to maintain the desired temperature.
  • the temperature was controlled by the controlling of the temperature of the bath in which the bomb was immersed.
  • cooling water suitably a pplied can be used.
  • the pressure in this experiment reached a maximum of 80 pounds per square inch.
  • the bomb was cooled and the product analyzed for tetra- ,ethyllead.
  • the product can bedistilled in vacuum or in the presence of steam to recover the tetraalkyllead product.
  • an analysis showed that 6.07 grams of tetraethyllead were produced, which entitled Summary of Experiments.
  • results of twenty-three additional experiments conducted in a similar manner are also tabulated in the table.
  • 10 grams of MgzPb alloy, comprising about 19 per cent by weight magnesium was used.
  • the twenty-four examples illustrate results obtained with different alkyl halides added in varying amounts, different catalysts added in varying amounts, and different operating conditions with tetraalkyllead yield varying from 25 to 85 per cent by weight based on the lead input.
  • Column 1 gives the example number; Columns 2, 3 and 4..refer to the alkyl halide; Column 2, the name, Column 3, the theories, and Column 4, the grams charged. The theories are the ratio of alkyl halide charged to the theoretical amount required for the lead to be completely reacted.
  • Columns 5, 6, and '7 refer to the conditions of operation; Column 5, to the length of time the reactants remained in the bomb; Column 6, to the temperature maintained during reaction, and Column 7, to the pressure in pounds per square inch. The pressure in the experiments tabulated was not controlled, but was the pressure resulting from the materials charged at the temperature under which the bomb was maintained.
  • Colis equivalent to per cent by weight, based on umns 8, 9, and 10 relate to the catalyst used, Column 8 to the name; Column 10 to the grams charged, and Column 9 the per cent by weight of catalyst based on alloy charged.
  • Columns 11 and 12 relate to the tetraalkyl product; Column 11, to the grams recovered, and Column 12 to the percentage yield based on the lead in the alloy charged.
  • my catalyst is an organic, chemical coordination catalyst which is defined in the above terms.
  • a process for making tetraalkyllead comprising alkylating lead in an alloy consisting of lead and magnesium in the preseuce of an alkylating catalyst containing an atom which chemieally coordinates with magnesium.
  • a process for making tetraalkyllead comprising reacting a lower alkyl halide with an alloy consistingot lead and magnesium in the presence of a catalyst selected from the group consisting of aliphatic hydrocarbyl ethers, tertiary hydrocarbyl amines and tetrahydrocarbyl ammonium iodides.
  • a process for making tetraalkyllead comprising reacting a lower alkyl halide with an alloy consisting of lead and magnesium in the presence of an aliphatic hydrocarbyl ether.
  • a process for making tetraethyllead comprising reacting an ethyl halide with an alloy consisting of about 18 to 22 per cent by weight magnesium and about 78 to 82 per cent by weight lead in the presence of a lower dialkyl ether.
  • a process for making tetraethyllead comprising reacting thyl chloride with an alloy consisting of about 18 to 22 per cent by weight magnesium and about 78 to 82 per cent by weight lead in the presence of diethyl ether.
  • a process for making tetraethyllead comprising reacting ethyl chloride with an alloy consisting of about 19 per cent by weight magnesium and about 81 per cent by weight lead in the presence of diethyl ether.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US30191A 1948-05-29 1948-05-29 Manufacture of tetraalkyllead Expired - Lifetime US2535235A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DENDAT878645D DE878645C (de) 1948-05-29 Verfahren zur Herstellung von Tetraalkylblei
US30191A US2535235A (en) 1948-05-29 1948-05-29 Manufacture of tetraalkyllead
US30192A US2535236A (en) 1948-05-29 1948-05-29 Preparation of tetraalkyllead
GB12560/49A GB668561A (en) 1948-05-29 1949-05-11 Improvements in or relating to the manufacture of tetraalykllead
FR986329D FR986329A (fr) 1948-05-29 1949-05-19 Perfectionnements à la préparation de plomb tétra-alkyle

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US30191A US2535235A (en) 1948-05-29 1948-05-29 Manufacture of tetraalkyllead

Publications (1)

Publication Number Publication Date
US2535235A true US2535235A (en) 1950-12-26

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Family Applications (1)

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US30191A Expired - Lifetime US2535235A (en) 1948-05-29 1948-05-29 Manufacture of tetraalkyllead

Country Status (4)

Country Link
US (1) US2535235A (de)
DE (1) DE878645C (de)
FR (1) FR986329A (de)
GB (1) GB668561A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3457288A (en) * 1966-04-13 1969-07-22 Ppg Industries Inc Process for manufacturing tetraorganolead compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2000069A (en) * 1932-05-24 1935-05-07 Du Pont Preparation of lead alkyls

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2000069A (en) * 1932-05-24 1935-05-07 Du Pont Preparation of lead alkyls

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3457288A (en) * 1966-04-13 1969-07-22 Ppg Industries Inc Process for manufacturing tetraorganolead compounds

Also Published As

Publication number Publication date
FR986329A (fr) 1951-07-30
GB668561A (en) 1952-03-19
DE878645C (de) 1953-04-23

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