US1559405A - Process of making tetra-alkyl lead - Google Patents
Process of making tetra-alkyl lead Download PDFInfo
- Publication number
- US1559405A US1559405A US592598A US59259822A US1559405A US 1559405 A US1559405 A US 1559405A US 592598 A US592598 A US 592598A US 59259822 A US59259822 A US 59259822A US 1559405 A US1559405 A US 1559405A
- Authority
- US
- United States
- Prior art keywords
- lead
- ethyl
- tetra
- alkyl
- catalyst
- 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
Links
- 238000000034 method Methods 0.000 title description 24
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000003638 chemical reducing agent Substances 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 238000003747 Grignard reaction Methods 0.000 description 9
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 9
- 230000009467 reduction Effects 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001350 alkyl halides Chemical class 0.000 description 5
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 229910000528 Na alloy Inorganic materials 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- JUUVKOUSGRIGLL-UHFFFAOYSA-N diethyllead Chemical compound CC[Pb]CC JUUVKOUSGRIGLL-UHFFFAOYSA-N 0.000 description 4
- -1 ethyl acetate) Chemical class 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 229910000978 Pb alloy Inorganic materials 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001351 alkyl iodides Chemical class 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 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
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDQHJGWPOQNCMI-UHFFFAOYSA-N tetrabutylplumbane Chemical group CCCC[Pb](CCCC)(CCCC)CCCC KDQHJGWPOQNCMI-UHFFFAOYSA-N 0.000 description 1
- XOOGZRUBTYCLHG-UHFFFAOYSA-N tetramethyllead Chemical group C[Pb](C)(C)C XOOGZRUBTYCLHG-UHFFFAOYSA-N 0.000 description 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
- 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 of pro- 10 ducing a tetra-alkyl lead, and comprises treating a lead-sodium alloy (for example, an alloy in which the ratio of lead to sodium is indicated by the formula PbNa with an alkyl halidein the presence of a catalyst of the type used for the Grignard synthesis, adding-water to the mixture thus formed, and maintaining the resulting lead compound for an apcpreciable time at a temperature above
- a lead-sodium alloy for example, an alloy in which the ratio of lead to sodium is indicated by the formula PbNa with an alkyl halidein the presence of a catalyst of the type used for the Grignard synthesis
- the alkyl halide used in the process is preferably an alkyl bromide or an alkyl iodide.
- the lead-sodium alloy used should pref,- erably be ground to increase the area of its surface.
- Catalysts of the type used for the Grignard synthesis include such organic' compounds as contain a tertiary basic nitrogen atom (for example, dimethylaniline, triethylamine and pyridine), esters (such as ethyl acetate), ethers, etc. Any of these Grignard catalysts may be used to promote the reaction'between lead and alkyl halide, but I preferto use for this purpose the tertiary amines. I,
- a lead-sodium alloy corresponding to the formula PbNa is mixed with pyridine and ehtyl bromide, and the mixture heated while slowly adding water equivalent to the sodium content of the lead alloy;
- the essential feature of the reaction is the formation of the lead ethyl bromide complex, which upon reduction in the presence of ethyl bromide yields diethyl lead; this material being unstable above approximately 20 0;, breaks down with the formation of tetra ethyl lead and metallic lead.
- the pyridine or other catalyst of the type used in the Grignard synthesis apparently serves to accelerate some combination or reactionbetween the lead and the alkyl bromide;
- the water used as the source of hydrogen may be so small in amount as to 'bealso regarded as a catalyst, for-it has been found that'the amount of water neces sary can be as little as 20% of that required to combine with the sodium present, as the water is continuously regenerated during the progress of the reduction by a secondary reaction between the sodium hydroxide and the hydrobromic or hydriodic acid formed. This was not true when using the tetra sodlum lead alloy, as in that case sufiicient water must be added to desti'oy the excess sodium present.
- r y new procedure may be illustrated by the following example I
- One hundred and sixty parts of coarsely -(10 mesh) ground alloy containing about 29 parts of sodium and 131 parts of lead are mixed at room'temperaturefwith 135 parts of ethyl bromide and 19.2 parts (all parts by weight) of triethylamine.
- the mixture is then placed in a bath whose temperature can be controlled. 4 parts of water are then added slowly to the mixture with con stant stirring, the rate of addition being controlled so that this amount of water is added in 16 hours, the temperature being 'held below 35 C.
- the reaction takes place smoothly, with evolution of heat.
- a large ex cessof water 200 cc.
- the lead tetra-ethyl is steam distilled off.
- the optimum temperature for the reaction appears to be 30 C., although temperatures as low as 5 C. and as high as 35 C. have been employed successfull
- the nascent hydrogen for this reduc tion may be furnished in various ways other than by the action of an alkali-metal on Water, this latter method, however, being preferred. As indicated by the specific example given above, it is not necessary to convert the lead into a lead-alkyl halide combination or complex before starting the reduction of the latter; in fact a considerable sav ing in time is effected by allowing these two reactions to proceed concurrently.
- the process of producing tetra-ethyl lead which comprises treating lead with an ethyl halide in the presence of a catalyst of the type used for the Grignard synthesis, subjecting the resulting mixture to the action of a-sufiicient quantity of a reducing agent to produce di-ethyl lead, and converting the latter by heat into tetra-ethyl lead, the quantity of said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
- the process of producing tetra-ethyl lead which comprises treating lead with an ethyl halide under conditions controlled to produce a lead-ethyl halide combination, subjecting the resulting mixture to the action of a sufficient quantity of a reducing agent to effect reduction to (ii-ethyl lead, and converting the latter by heat into tetra-ethyl lead, the quantity of, said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
- the process of producing tetra-ethyl lead which comprises treating a lead-sodium alloy in which the proportion of sodium is at least two atoms, and less than four atoms, for each atom of lead, with ethyl bromide and a catalyst of the type used for the Grignard synthesis, gradually adding water to the reaction mass until the lead-ethyl bromide mixture is converted to di-ethyl lead, and causing the temperature of the mixture to rise above 20 C. for a suflicient time to effect the conversion of di-ethyl lead to tetra-ethyl lead.
- the step which comprises mixing an alloy having the composition PbNa With an alkyl halide and a catalyst of the type used for the Grignardsynthesis, to form a lead-alkyl halide mixture intimately associated with sodium.
- the step which comprises mixing coarsely ground PbNa with ethyl bromide and a tertiary amine to form a lead-ethyl bromide mixture intimately associatedwith sodium.
- tetra- 18 In the process of producing tetraethyl lead, the step which comprises subjecting to the action of a reducing agent a lead-ethyl halide mixture obtainable by treating lead with an ethyl halide in the presence of a catalyst of the type used to the Grignard synthesis, the quantity of sai j; reducing agent being substantially less than '35 the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
- the step which comprises sub- 40 jecting to the action of areducing agent a lead-ethyl bromide mixture obtainable byv treating lead with ethyl bromide in the presence of a catalyst of the type used for the Grignard synthesis, the quantity of said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Oct. 27, 1925.
1,559,405 PATENT OFFICE.
WILLIAM S. CALCOTT, OF PENNSGROVE, JERSEY, ASSIGNOR TO E. I DU PONT DE NEMOURS & COMPANY, OF WILMI INGTON,
DELAWARE.
.- No Drawing.
To all whom it may concern;
Be it known that I, WILLIAM S. CALCOTT,
a citizen of the United States, and a resident of Pennsgrove, in the county of Salem and State of New Jersey, have invented a certain new and useful Process of Making Tetra-Alkyl Lead, of which the following is a specification. 7
This invention relates to a process of pro- 10 ducing a tetra-alkyl lead, and comprises treating a lead-sodium alloy (for example, an alloy in which the ratio of lead to sodium is indicated by the formula PbNa with an alkyl halidein the presence of a catalyst of the type used for the Grignard synthesis, adding-water to the mixture thus formed, and maintaining the resulting lead compound for an apcpreciable time at a temperature above The alkyl derivatives with which this invention is.chiefly concerned are the combi nations of lead with alkyls having from one to four carbon atoms, namely with methyl, ethyl, nand iso-p'ropyl, and nand iso-butyl.
The alkyl halide used in the process is preferably an alkyl bromide or an alkyl iodide. y
The lead-sodium alloy used should pref,- erably be ground to increase the area of its surface.
Catalysts of the type used for the Grignard synthesis include such organic' compounds as contain a tertiary basic nitrogen atom (for example, dimethylaniline, triethylamine and pyridine), esters (such as ethyl acetate), ethers, etc. Any of these Grignard catalysts may be used to promote the reaction'between lead and alkyl halide, but I preferto use for this purpose the tertiary amines. I,
My invention .will be explained by de. scribing its application to the manufacture of tetra-ethyl lead (i. e., lead-tetraethide, Pb(C H this product being considered of most importance.
According to one proposed method of making tetra-ethyl lead, a lead-sodium alloy corresponding to the formula PbNa is mixed with pyridine and ehtyl bromide, and the mixture heated while slowly adding water equivalent to the sodium content of the lead alloy; The mechanism of this reaction, which yields tetra-ethyl lead, was not DELAWARE, A CORPORATION or gnocnss or MAKING TETRA-ALKYL LEAD.
Application filed October 5, 1922. Serial No. 592,598.
known. I have now discovered that it is unnecessary to have the lead alloyed with such an amount of sodium as to corresopnd V i to the formula PbNa any sodium in excess of an amount corres onding to .PbNa bemg not onlysuper uous, but also detrimental with respect to the progress of the reaction.
As is shown by these equations the essential feature of the reaction is the formation of the lead ethyl bromide complex, which upon reduction in the presence of ethyl bromide yields diethyl lead; this material being unstable above approximately 20 0;, breaks down with the formation of tetra ethyl lead and metallic lead.
The pyridine or other catalyst of the type used in the Grignard synthesis apparently serves to accelerate some combination or reactionbetween the lead and the alkyl bromide; The water used as the source of hydrogen may be so small in amount as to 'bealso regarded as a catalyst, for-it has been found that'the amount of water neces sary can be as little as 20% of that required to combine with the sodium present, as the water is continuously regenerated during the progress of the reduction by a secondary reaction between the sodium hydroxide and the hydrobromic or hydriodic acid formed. This was not true when using the tetra sodlum lead alloy, as in that case sufiicient water must be added to desti'oy the excess sodium present. r y new procedure may be illustrated by the following example I One hundred and sixty parts of coarsely -(10 mesh) ground alloy containing about 29 parts of sodium and 131 parts of lead are mixed at room'temperaturefwith 135 parts of ethyl bromide and 19.2 parts (all parts by weight) of triethylamine. The mixture is then placed in a bath whose temperature can be controlled. 4 parts of water are then added slowly to the mixture with con stant stirring, the rate of addition being controlled so that this amount of water is added in 16 hours, the temperature being 'held below 35 C. The reaction takes place smoothly, with evolution of heat. When the reaction is complete, as shown by the absence of alloyjifi a test portion, a large ex cessof water (200 cc.) is added, and the lead tetra-ethyl is steam distilled off.
The optimum temperature for the reaction appears to be 30 C., although temperatures as low as 5 C. and as high as 35 C. have been employed successfull Although in the preferred em iment of my invention the reduction of t e leadalkyl-halide mixture is brought about by the nascent hydrogen resulting from the action of an alkali-metal on water, my invention maybe said, generically, to comprise effecting the reduction of the lead-alkyl halide mixture by bringing into contact therewith preferably an amount of a reducing agent equivalent to not more than one-half of the lead used, but which in any case is substantially less than the equivalent of four atoms of nascent hydrogen for each molecule of the lead present in the reaction mix- =ture. The nascent hydrogen for this reduc tion may be furnished in various ways other than by the action of an alkali-metal on Water, this latter method, however, being preferred. As indicated by the specific example given above, it is not necessary to convert the lead into a lead-alkyl halide combination or complex before starting the reduction of the latter; in fact a considerable sav ing in time is effected by allowing these two reactions to proceed concurrently.
' Where the product desired is lead tetramethyl (Pb (CH lead tetra-propyl Pb C H,),), or lead tetra-butyl PbiC,H,) the directions of the specific example (supra) may be followed except that instead of ethyl bromide a stoichiometrically equivalent quantity of methyl, propyl, or butyl, bromide, as the case may be, is used.
I claim:
1. The process of producing a tetra-alkyl lead which comprises treating lead with an alkyl halide in the presence of a catalyst of the type used for the Grignard synthesis, and subjecting the mixture to the action of a suflicient quantity of a reducing agent to effect reduction to a lead dialkyl, and converting the latter by heat into tetra-alkyl lead, the quantity of said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
2. The process of producing a tetra-alkyl lead which comprises treating lead with an alkyl halide under conditions controlled to produce a lead-alkyl halide combination, subjecting the resulting mixture to the action of a suflicient quantity of a reducing agent to produce a lead dialkyl, and con"- verting the latter by heat into tetra-alkyl lead, the quantity of said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
3. A process of the kind set forth in claim 1 in which the catalyst is a tertiary amine.
4. A process of the kind set forth in claim 1 in which the reducing agent is hydrogen generated in situ by the action of an alkalimetal on water.
5. The process of producing tetra-ethyl lead which comprises treating lead with an ethyl halide in the presence of a catalyst of the type used for the Grignard synthesis, subjecting the resulting mixture to the action of a-sufiicient quantity of a reducing agent to produce di-ethyl lead, and converting the latter by heat into tetra-ethyl lead, the quantity of said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
6. The process of producing tetra-ethyl lead which comprises treating lead with an ethyl halide under conditions controlled to produce a lead-ethyl halide combination, subjecting the resulting mixture to the action of a sufficient quantity of a reducing agent to effect reduction to (ii-ethyl lead, and converting the latter by heat into tetra-ethyl lead, the quantity of, said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
7. A rocess of the kind set forth in claim 5 in which the catalyst is a tertiary amine.
8. A process of the kind set forth in claim 5 in which the reducing agent is hydrogen generated in situ by the action of an alkalimetal on water.
9. A process of the kind set forth in claim 1 in which the catalyst is dimethylaniline.
10. A process of the kind set forth in claim 5 in which the catalyst is dimethylaniline.
11. The process of producing tetra-ethyl lead which comprises treating a lead-sodium alloy in which the proportion of sodium is at least two atoms, and less than four atoms, for each atom of lead, with ethyl bromide and a catalyst of the type used for the Grignard synthesis, gradually adding water to the reaction mass until the lead-ethyl bromide mixture is converted to di-ethyl lead, and causing the temperature of the mixture to rise above 20 C. for a suflicient time to effect the conversion of di-ethyl lead to tetra-ethyl lead.
12. A process of the kind set forth in claim 11 in which the catalyst is an organic compound containing a tertiary basic nitroen atom.
13. The process of producing tetra-ethyl 0., then adding a large excess of water, and heating the resulting mixture sufiiciently to distill off tetra-ethyl lead.
14. In the process of producing a tetraalkyl lead, the step which comprises mixing an alloy having the composition PbNa With an alkyl halide and a catalyst of the type used for the Grignardsynthesis, to form a lead-alkyl halide mixture intimately associated with sodium.
15. In the process of producing tetraethyl lead, the step which comprises mixing coarsely ground PbNa with ethyl bromide and a tertiary amine to form a lead-ethyl bromide mixture intimately associatedwith sodium.
16. In the process of producing tetra- 18. In the process of producing tetraethyl lead, the step which comprises subjecting to the action of a reducing agent a lead-ethyl halide mixture obtainable by treating lead with an ethyl halide in the presence of a catalyst of the type used to the Grignard synthesis, the quantity of sai j; reducing agent being substantially less than '35 the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
19. In the process of producing tetraethyl lead, the stepwhich comprises sub- 40 jecting to the action of areducing agent a lead-ethyl bromide mixture obtainable byv treating lead with ethyl bromide in the presence of a catalyst of the type used for the Grignard synthesis, the quantity of said reducing agent being substantially less than the equivalent of four atoms of nascent hydrogen, for each molecule of the lead used.
20. A process of the kind set forth in claim 11 in which the catalyst is dimethylaniline.
In testimony whereof I afiix my signature.
' WILLIAM S. OALCOTT.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US592598A US1559405A (en) | 1922-10-05 | 1922-10-05 | Process of making tetra-alkyl lead |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US592598A US1559405A (en) | 1922-10-05 | 1922-10-05 | Process of making tetra-alkyl lead |
Publications (1)
Publication Number | Publication Date |
---|---|
US1559405A true US1559405A (en) | 1925-10-27 |
Family
ID=24371326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US592598A Expired - Lifetime US1559405A (en) | 1922-10-05 | 1922-10-05 | Process of making tetra-alkyl lead |
Country Status (1)
Country | Link |
---|---|
US (1) | US1559405A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2464398A (en) * | 1946-03-12 | 1949-03-15 | Du Pont | Manufacturing tetraethyl lead |
US2653159A (en) * | 1949-12-24 | 1953-09-22 | Ethyl Corp | Manufacture of tetraethyllead |
US2848471A (en) * | 1956-11-14 | 1958-08-19 | C I P Compagnia Italiana Petro | Preparation of tetraethyl lead |
US3281442A (en) * | 1963-07-05 | 1966-10-25 | Du Pont | Process for making tetramethyl lead |
US3400143A (en) * | 1965-05-17 | 1968-09-03 | Du Pont | Process for making tetramethyl lead |
US3401188A (en) * | 1965-08-05 | 1968-09-10 | Du Pont | Process for making tetramethyl lead |
-
1922
- 1922-10-05 US US592598A patent/US1559405A/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2464398A (en) * | 1946-03-12 | 1949-03-15 | Du Pont | Manufacturing tetraethyl lead |
US2653159A (en) * | 1949-12-24 | 1953-09-22 | Ethyl Corp | Manufacture of tetraethyllead |
US2848471A (en) * | 1956-11-14 | 1958-08-19 | C I P Compagnia Italiana Petro | Preparation of tetraethyl lead |
US3281442A (en) * | 1963-07-05 | 1966-10-25 | Du Pont | Process for making tetramethyl lead |
US3400143A (en) * | 1965-05-17 | 1968-09-03 | Du Pont | Process for making tetramethyl lead |
US3401188A (en) * | 1965-08-05 | 1968-09-10 | Du Pont | Process for making tetramethyl lead |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US1559405A (en) | Process of making tetra-alkyl lead | |
US1622228A (en) | Process of making organic lead compounds | |
US2666776A (en) | Production of organic silicon compounds | |
US1945183A (en) | Manufacture of alkoxy derivatives of phosphorous acid chlorides | |
US2763665A (en) | Process for the manufacture of levulinic acid esters | |
US1645389A (en) | Production of a tetra-alkyl lead | |
US3053874A (en) | Process for the production of cyanoalkylfluorosilane | |
US2247821A (en) | Manufacture of trialkyl borons | |
US3759986A (en) | Esters of 2,2-dimethyl-5-(aryloxy)-1-pentanols | |
Clemo et al. | XXX.—The cis-trans ethenoid transformation | |
US1717961A (en) | Process for the production of lead tetra-alkyl | |
US1946256A (en) | Preparation of carboxylic acids | |
US1550940A (en) | Process of synthesizing lead tetra-alkyis | |
US2535190A (en) | Manufacture of alkyllead compounds | |
US2082568A (en) | Vinylethinyl derivatives and processes for producing same | |
US1946255A (en) | Preparation of carboxylic acids | |
US1661809A (en) | Process of making tetra-alkyl lead | |
US3401189A (en) | Tetramethyl lead manufacture | |
US1658544A (en) | Process of making lead alkyls | |
US2260800A (en) | Process of making tertiary butyl malonic acid | |
US2535191A (en) | Manufacture of alkyllead compounds | |
US3397241A (en) | Process for the economical preparation of br3 organoboron compounds | |
US2558207A (en) | Manufacture of alkyllead compounds | |
US2591509A (en) | Manufacture of alkyl lead compounds | |
US1664021A (en) | Process of manufacturing tetra-ethyl lead |