US1661809A - Process of making tetra-alkyl lead - Google Patents
Process of making tetra-alkyl lead Download PDFInfo
- Publication number
- US1661809A US1661809A US701641A US70164124A US1661809A US 1661809 A US1661809 A US 1661809A US 701641 A US701641 A US 701641A US 70164124 A US70164124 A US 70164124A US 1661809 A US1661809 A US 1661809A
- Authority
- US
- United States
- Prior art keywords
- lead
- ethyl
- chloride
- alkyl
- tetra
- 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 17
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical group CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 18
- 229960003750 ethyl chloride Drugs 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910045601 alloy Inorganic materials 0.000 description 11
- 239000000956 alloy Substances 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 150000001348 alkyl chlorides Chemical class 0.000 description 10
- 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 8
- 239000000203 mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 229910000528 Na alloy Inorganic materials 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- -1 alkyl chlor Chemical compound 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 241000861718 Chloris <Aves> Species 0.000 description 2
- 229910000978 Pb alloy Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VLZZXGOEDAYHOI-UHFFFAOYSA-N ethyllead Chemical compound CC[Pb] VLZZXGOEDAYHOI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000005275 alloying Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012021 ethylating agents Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 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 the production of a tetra-alkyl lead, and comprises, as a new process, loy with an alkyl chloride and a neutral 5 hydroxylic compound (preferably functioning catalytically) which is soluble in said chloride, and preferably in the resence of another catalyst and of an inert iluent.
- Theaddition 0 alcohol orwater may be made entirely in the beginning, or in portions from time to time as thereaction proceeds. This latter proas a mode of control for obtaining a smooth reaction, particularly when thereaction is carried out on a large scale andv is, therefore, more liable to so 5 den and disastrous temperature surges.
- a salt or hydroxide such as potassium carbonate, potassium hydroxide, sod1um chlcride, or a salt ofa metal whose hydroxide s insoluble or only slight] soluble, such as magnesiumfand calcium 0 lorides.
- the hydroxylic compound used seems to act as a true catalyst, being continually regenerated during the progress of the reduction b a secondary reaction between the sodium ydroxide (or alcoholate) and the hydrochlori'c acid formed. This accounts for the effectiveness of the small proportion of hydroxylic compound used.
- an additional catalyst such as an additional catalyst, such catalyst is preferably of the type used for the Grignard synthesis, such for example as tertiary amines dimethylaniline, pyridine, etc), esters (et yl acetate), ethers, etc.
- I claim! 1 The process of producing a tetra-alkvl lead from a lead alloy and an alkyl chloride, which compri'sestreat' one atomic proportion'of lead, alloyed with two atomic proportions of a monovalent element capable of liberating hydro en from water, with an alkyl chloride in t e presence of less than 5.1 molecular percentage, based upon said' chloride, of a neutral hydroxylic compound soluble in the alkyl chloride.
- the process of producing tetra-ethyl lead which comprises inducing a reaction between an alloy of the formula PbNa ethyl chloride, and water in an amount less than 4 percent based upon the weight of the ethyl chloride and recovering the tetraethyl lead forme 9.
- the process of producing tetra-ethyl lead which comprises'inducin a reaction between an alloy of the formula PbNa, ethyl chloride, and water and amount less than 4 percent based upon the weight of 'the ethyl chloride, and recovering the tetra-ethyl lead formed.
- the process of producing tetra-ethyl lead which comprises gradually adding a neutral .hydroxylic compound soluble in ethyl chloride to a mixture containing the lead-sodium allog Pbll'a and ethyl chloride, the amount of ydroxylic compound prescut at any one time inthe reaction mixture bein just sufficient to enable the combination etween the lead and' the eth l chloride to proceed, by the addition of the liydroxylic compound at such a rate that excessive evolution of free hydrogen is avoided.
- the processof producing tetra-ethyl lead which comprises gradually addin water to a mixture containing ethyl c oride and the alloy PbNa the amount of water present at any one time in the reaction mixture being not substantially in excess of that required to enable the combination between the lead and the ethyl chloride to rooeed actively, by the addition of the hy oxylic compound at such a rate that excessive evolution of free hydrogen is avoided 14.
- the process of producing tetra-ethyl lead which comprises gradually adding water and ethyl alcohol to a mixture containing ethyl chloride and the alloy PbNa the amount of water and alcohol added amounting to between 0.2 and 1 percent, based upon the weight of ethyl chloride present.
- Process of making an alkyl compound of a metal of the second sub-group .of the fourth periodic group comprising alloying the metal with a highly electro-positive metal, and treating the alloy under reaction conditions with an alkylating agent in the presence of a hydrocarbon liquid.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
45 cedure may serve Patented Mar. 6, 1928.
umrao STATES KENNETH r. MONROE,
mmouns a couranr, or
warm.
F PENNS GROVE, NEW JERSEY, ASSIGNOR. TO E. I. 1) PORT DE WILMINGTON, DELAWARE, CORPORATE O1 DELA- PROCESS OF MAKING .l!1i'J.IBiAfALKYIl'a LEAD.
No Drawing.
This invention relates to the production of a tetra-alkyl lead, and comprises, as a new process, loy with an alkyl chloride and a neutral 5 hydroxylic compound (preferably functioning catalytically) which is soluble in said chloride, and preferably in the resence of another catalyst and of an inert iluent.
As I have pointed out in my U. S Patent 1,645,389, dated October 23, 1927, the synthesis of lead-alkyls from leadso dium alloy and an alkyl bromide is promoted by the ad diti'o'n of water either per se or in a diluted state. I have now discovered that the syn thesis of lead-alkyls from lead sodium alloy and an alkyl' chloride resembles the bromide synthesis in this respect, despite the lesser chemical reactivity of the chloride, and have made the additional discover that the water may be replaced, either who y or in part, by
another neutral'hydroxylic compound, such' Y ethyl or propyl alcohol.
These hydroxylic compounds (water, al-.
cohol, etc.) have a great influence on the course of the reaction, being in fact essential from a practical manufacturing standpoint.
If highly purified alkyl chloride (or bromide) is l lnermitted to react with pure lead sodium 11 oy the yield of lead alkyl is negligible under the same conditions which re- Sult in a substantialyield when alkyl chloride (or bromide) containing an appreciable amount (for example 0.4% based on the weight of a l halide) of. water or an alcofl hol is used. On the'other hand the presence of anexcessive initial amount (for example 4.0%) of water or an alcohol causes excessive side-reaction (for example, the evolu-, tion of hydrogen) and. causes a diminution in yield from that obtained when an optimum amount is present. Theaddition 0 alcohol orwater may be made entirely in the beginning, or in portions from time to time as thereaction proceeds. This latter proas a mode of control for obtaining a smooth reaction, particularly when thereaction is carried out on a large scale andv is, therefore, more liable to so 5 den and disastrous temperature surges. It
. has also been found desirable to assist in the control of the reaction on thelarger scale by p dilution of the liquid reaction mass with an inert miscible liquid; such liqmd may be,
for example, benzene or other mer t hydro- 1 1 Application filed mar 25; 1924. s mi No. 701,641.
the interaction ofa lead-sodium al- O.'4% alcohol and water. 5 cc. additions. ethyl alcohol were then added. The tube steam distillation. 2 cc.
and maintained at carbon which is miscible with" the alkyl chlor de'used.
The invention may be illustrated by thefollowmg examples:
(1) 106 grams very pure lead-sodium alloy contalmng 14.6% sodium (the compositlon of the alloy being expressible as a mixture of 44v parts of PbNa with 56 parts of P bNa was placed in a steel tube with 60 cc. hlghly purified ethyl chloride. The tube was closed and placed in an oil bath where 1t was rotated while the temperature was gradually raised to C. and maintained at 80 U. for eight hours. The tube was then removed, cooled, opened and the contents thoroughly extracted with dry, alcohol-free ether. On filtration and evaporatron of the other only a vanishingly small yield cc.) of lead tetra-ethyl was ob-. tamed.
(2) 106 rams very pure lead-sodium al loy contalnmg 14.6% sodium was laced in a steel tube with 60 cc. highly pur' ed ethylchloride to which 1 cc. absolute ethyl alcohol had been added. The. tube was then closed and placed in an oil bath where itwas rotated while the temperature was raised gradually to 80 C. and maintained at 80 C. for eight hours. The tube was then i'emoved, cooled, opened, and the contents thoroughly extracted withdry, alcohol-free ether. On fil ration and evaporation of the ether 15 cc. lead tetra-ethylwere obtained. V (3) 100 grams lead-sodium alloy contain mg 14.6% sodium were placed 111- 8. steel tube with 130 cc. ethyl chloride containin was close placed in an oil bath, and-ro- I 'tat ed while the tem erature was 'gradua y f raised to 65 C. an -ma intained at 65 C. for 48 hours. The tube was then openedand the excess ethyl chloride and lead tetra-. ethyl separated from the residual lead by lead tetra-ethyl were obtained. I
(4) 100 grams lead-sodium alloy contain ing.14.6% sodium were placed in a steel tube with 00c; ethyl chloride containing'0.4% alcohol" and water. The tube was closed,
laced in an oil bath, and-rotated while the .106 temperature was gradually raised-to 65 C,
I 0.. or 48 hours. {The tiibe'was-then opened and the excess ethylchloride and lead tetra-ethyl separated from the residual lead by steam distillation. 19 cc. lead tetra-ethyl were obtained.
The reaction us' an ethyl chloride, as will have appeared 111 the above examples, is preferably carried out at a temperature above 60 C. as compared with the temperature of 2530 C. which gave best results with ethyl bromide as described in my said copending application. It is to be understood, however, that my invention is not limited to working at any particular temperature or temperatures.
. lecu ar percentage of a neutral h lea sodium a Instead of water or alcohol per se aid the reaction, I may use, as above indicated, water or alcohol diluted by dissolving therein a salt or hydroxide such as potassium carbonate, potassium hydroxide, sod1um chlcride, or a salt ofa metal whose hydroxide s insoluble or only slight] soluble, such as magnesiumfand calcium 0 lorides.
The hydroxylic compound used seems to act as a true catalyst, being continually regenerated during the progress of the reduction b a secondary reaction between the sodium ydroxide (or alcoholate) and the hydrochlori'c acid formed. This accounts for the effectiveness of the small proportion of hydroxylic compound used. K
ereit is found desirable'to use an additional catalyst, such catalyst is preferably of the type used for the Grignard synthesis, such for example as tertiary amines dimethylaniline, pyridine, etc), esters (et yl acetate), ethers, etc.
I claim! 1. The process of producing a tetra-alkvl lead from a lead alloy and an alkyl chloride, which compri'sestreat' one atomic proportion'of lead, alloyed with two atomic proportions of a monovalent element capable of liberating hydro en from water, with an alkyl chloride in t e presence of less than 5.1 molecular percentage, based upon said' chloride, of a neutral hydroxylic compound soluble in the alkyl chloride.
2. The process of producing a tetra-alkyl lead from a lead alloy and an alkyl chloride, which com rises treating one atomic proportion of lea alloyed with two atomic proportions of .a monovalent element capable of liberating hydrogen from water, with an alkyl. chloride in the presence of from about 0.5 to 1.3 molecular percentage, based upon said chloride, 'of a neutral hydroxylic compound soluble in the alkyl chloride.
e process of roducing a tetra-alkyl lead from alead-sodihm alloy having a sodium "content of about 14.6 percent and an a l chloridewhich comprises ,treatin the lloy with the alkyl chlori e in the. resence of from about 0.5 to 1.3 modroxylio compound, soluble insaid chlori e, to enable the combination.
between the lead and the alkyl chloride to proceed, by the addition of the hydroxylic compound at such a' 7. A process as defined in claim 3 in which A the alkyl of the alkyl chloride contains from 1 to 4 carbon atoms.
8. The process of producing tetra-ethyl lead which comprises inducing a reaction between an alloy of the formula PbNa ethyl chloride, and water in an amount less than 4 percent based upon the weight of the ethyl chloride and recovering the tetraethyl lead forme 9. The process of producing tetra-ethyl lead which comprises'inducin a reaction between an alloy of the formula PbNa, ethyl chloride, and water and amount less than 4 percent based upon the weight of 'the ethyl chloride, and recovering the tetra-ethyl lead formed.
10. The process of producing tetra-ethyl lead which comprises maintaining, at a temperature above 60 0., a mixture containing an alloy of the formula PbNa ethyl chloride, and from about 0.2 to 2 waterbased upon the weight of ethyl chloalcohol in an .0 percent of ride present, until the reaction is about completed.
which a mixture of water and ethyl alcohol is used in place of water.
12. The process of producing tetra-ethyl lead which comprises gradually adding a neutral .hydroxylic compound soluble in ethyl chloride to a mixture containing the lead-sodium allog Pbll'a and ethyl chloride, the amount of ydroxylic compound prescut at any one time inthe reaction mixture bein just sufficient to enable the combination etween the lead and' the eth l chloride to proceed, by the addition of the liydroxylic compound at such a rate that excessive evolution of free hydrogen is avoided.
The processof producing tetra-ethyl lead which comprises gradually addin water to a mixture containing ethyl c oride and the alloy PbNa the amount of water present at any one time in the reaction mixture being not substantially in excess of that required to enable the combination between the lead and the ethyl chloride to rooeed actively, by the addition of the hy oxylic compound at such a rate that excessive evolution of free hydrogen is avoided 14. The process of producing tetra-ethyl lead which comprises gradually ad water to a mixture containing ethyl c oride and the alloy PbNa,, the amount of water present at any one time in the reaction mix- -ceed actively, by the addition of the hydroxylic compound at such a rate that excessive evolution of vfree hydrogen is avoided, and maintaining the reaction mixture at a temperature above 60 (3., throughout the major part of the reaction period.
15. The process of producing tetra-ethyl lead which comprises gradually adding water and ethyl alcohol to a mixture containing ethyl chloride and the alloy PbNa the amount of water and alcohol added amounting to between 0.2 and 1 percent, based upon the weight of ethyl chloride present.
16. A process as set forth in claim 13in which ethyl alcohol replaces at least a substantial part of the water which is added to the mixture of ethyl chloride and lead-so- 'dium alloy.
17. Process of making an alkyl compound of a metal of the second sub-group .of the fourth periodic group, comprising alloying the metal with a highly electro-positive metal, and treating the alloy under reaction conditions with an alkylating agent in the presence of a hydrocarbon liquid.
18. The process of making a lead ethyl which comprises reacting a lead-sodium-alloy with an ethylating agent in the presence of a hydrocarbon liquid.
19. The process of claim 18 in which the hydrocarbon liquid is a lower hydrocarbon of the benzene series.
In testimony whereof affix my signature.
KENNETH P. MONROE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US701641A US1661809A (en) | 1924-03-25 | 1924-03-25 | Process of making tetra-alkyl lead |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US701641A US1661809A (en) | 1924-03-25 | 1924-03-25 | Process of making tetra-alkyl lead |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1661809A true US1661809A (en) | 1928-03-06 |
Family
ID=24818126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US701641A Expired - Lifetime US1661809A (en) | 1924-03-25 | 1924-03-25 | Process of making tetra-alkyl lead |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1661809A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2464398A (en) * | 1946-03-12 | 1949-03-15 | Du Pont | Manufacturing tetraethyl lead |
| US2535191A (en) * | 1949-07-28 | 1950-12-26 | Hthyl Corp | Manufacture of alkyllead compounds |
| US2535192A (en) * | 1949-07-28 | 1950-12-26 | Ethyl Corp | Manufacture of alkyllead compounds |
| US3281442A (en) * | 1963-07-05 | 1966-10-25 | Du Pont | Process for making tetramethyl lead |
-
1924
- 1924-03-25 US US701641A patent/US1661809A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2464398A (en) * | 1946-03-12 | 1949-03-15 | Du Pont | Manufacturing tetraethyl lead |
| US2535191A (en) * | 1949-07-28 | 1950-12-26 | Hthyl Corp | Manufacture of alkyllead compounds |
| US2535192A (en) * | 1949-07-28 | 1950-12-26 | Ethyl Corp | Manufacture of alkyllead compounds |
| US3281442A (en) * | 1963-07-05 | 1966-10-25 | Du Pont | Process for making tetramethyl lead |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US1661809A (en) | Process of making tetra-alkyl lead | |
| US1622228A (en) | Process of making organic lead compounds | |
| DE943644C (en) | Process for the production of potassium, rubidium or cesium borohydride | |
| US2270109A (en) | Manufacture of methyl and ethyl lead compounds | |
| US2414058A (en) | Method of making lead alkyls | |
| US2915542A (en) | Preparation of dimethylaluminum hydride | |
| US2621200A (en) | Liquid ammonia process for forming hydrocarbonlead compounds | |
| US2247821A (en) | Manufacture of trialkyl borons | |
| US3053874A (en) | Process for the production of cyanoalkylfluorosilane | |
| US1559405A (en) | Process of making tetra-alkyl lead | |
| US3151930A (en) | Method for preparing lithium borohydride | |
| US1611695A (en) | Manufacture of lead alkyl compounds | |
| US3072698A (en) | Quaternary ammonium aluminum hydrides | |
| US1645389A (en) | Production of a tetra-alkyl lead | |
| US3362996A (en) | N-(2-(2-aminoethylthio)ethyl)ethylene-diamine and method of preparation | |
| US3401189A (en) | Tetramethyl lead manufacture | |
| US2558207A (en) | Manufacture of alkyllead compounds | |
| US1622233A (en) | Process of producing alkyl compound of lead | |
| GB1062464A (en) | Improvements in or relating to the manufacture of onium salt complex compounds | |
| US2894803A (en) | Method for the preparation of monobromopentaborane-9 | |
| US2065113A (en) | Process of producing lower aliphatic amino alcohols | |
| US2084710A (en) | Method for the production of alkyl chlorides from alkyl ethers | |
| US3112989A (en) | Method for preparing metal compounds | |
| US2575323A (en) | Manufacture of organolead compounds | |
| US2562856A (en) | Manufacture of alkyllead compounds |