US1724640A - Stabilization of tetraalkyl lead and compositions containing the same - Google Patents
Stabilization of tetraalkyl lead and compositions containing the same Download PDFInfo
- Publication number
- US1724640A US1724640A US286706A US28670628A US1724640A US 1724640 A US1724640 A US 1724640A US 286706 A US286706 A US 286706A US 28670628 A US28670628 A US 28670628A US 1724640 A US1724640 A US 1724640A
- Authority
- US
- United States
- Prior art keywords
- lead
- tetra
- composition
- grams
- stabilization
- 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
- 239000000203 mixture Substances 0.000 title description 34
- 230000006641 stabilisation Effects 0.000 title description 6
- 238000011105 stabilization Methods 0.000 title description 6
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 14
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- -1 aliphatic amines Chemical class 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001347 alkyl bromides Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229910052736 halogen Chemical class 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- XOOGZRUBTYCLHG-UHFFFAOYSA-N tetramethyllead Chemical compound C[Pb](C)(C)C XOOGZRUBTYCLHG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 101100513046 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) eth-1 gene Proteins 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical group 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/103—Liquid carbonaceous fuels containing additives stabilisation of anti-knock agents
Definitions
- This invention relates to the stabilization of tetra alkyl lead, unmixed with anything but its normal impurities, and to the stabilization of tetra alkyl lead compositions containing hydrocarbons and halogen derivatives of hydrocarbons. More particularly our invention relates to the stabilization of tetra alkyl lead and compositions containing tetra alkyl lead by the addition thereto of 10 small amounts of aliphatic amines or derlvatives of aliphatic amines.
- An object of our invention is the stabilization of tetra alkyl lead compounds and compositions containing these compounds. Other objects will appear as the descrlptlon proceeds.
- ⁇ Ve have discovered that decomposition of tetra alkyl lead compounds, and compositions containing the same, can be prevented by the introduction into these compounds or compositions, of aliphatic primary, secondary, or tertiary amines, or derivatives of these, such as the tetra alkyl ammonium hydroxides, and alkyl substituted hydroxyl amines.
- Example 1 -5O grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed together. To this mixture is added diethylamine, either anhydrous or as water solution, in amounts up to one gram.
- Example 2 50 grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed to gether. To this mixture is addedmono-methlyamine, either anhydrous or as water solution, in amounts up to one gram.
- Example 3 -50 grams of tetra methyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-ehlor-naphthalene are mixed 1928. Serial No. 286,706.
- methylhydroxylamine either anhydrous or as water solution, in amounts upto one gram.
- Example 4.5O grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed together. To this mixture is added tetraethyl-ammonium hydroxide, either anhydrous or as water solution, in amounts up to one gram.
- Example 5.5O grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed together. To this mixture is added triethylamine, either anhydrous or as Water solution, in amounts up to one gram.
- a composition comprising tetra alkyl lead and an aliphatic base.
- a composition comprising tetra alkyl lead and an alky l amine.
- a composition comprising tetra alkyl lead and dimethylamine.
- a composition comprising tetra alkyl llOead, an alkyl bromide, and an aliphatic ase.
- a composition comprising tetra alkyl lead, ethylene dibromide, a chlorinated aromatic hydrocarbon, and an aliphatic base.
- a composition comprising tetra alkyl lead, ethylene dibromide, a chlor-naphtha- 105 lene, and an aliphatic base.
- a composition comprising lead, ethylene dibromide, monothale-ne, and an aliphatic base.
- a composition comprising 5 lead and an aliphatic base.
- a composition comprising lead and an alkyl amine.
- a composition comprising lead and dimethylaminc.
- a composition comprising lead,.an alkyl bromide, and a base.
- a composition comprising tetra alkyl chlor-naphtetra ethyl tetra ethyl tetra ethyl tetra ethyl n aliphatic tetra ethyl lead, ethylene dibromide, a chlorinated aro- 15 matic hydrocarbon, and an aliphatic base.
- composition comprising lead, ethylene dibromide, lenc, and an aliphatic base.
- composition comprising lead, ethylene dibromide, monothalene, and an aliphatic base.
- a composition comprising tetra ethyl lead, an alkyl bromide, and an alkylami'nc.
- a composition comprising tetra ethyl lead, ethylene dibromide, a chlorinated aromatic hydrocarbon, and an alkylamine.
- a composition comprising tetra ethyl lead, ethylene dibromidc, a chlorinated aromatic hydrocarbon and dimethylamine.
- a composition comprising tetra ethyl lead, ethylene dibromide, a chlor-naphthalene, and dimethylamine.
- a composition comprising tetra eth 1 lead, ethylene dibror'nide, mono-chlor-nap 1- thalene, and dimethylamine.
- a composition comprising tetra alkyl lead, halogen derivatives of hydrocarbons, and an aliphatic amine.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Aug. 13, 1929.
UNITED STATES PATENT OFFICE.
WILLIAM S. CALCOTT. OF PENNS GROVE, AND ALFRED E. PARMELEE, F CARNEYS POINT, NEW JERSEY, ASSIGNORS TO E.
WILMINGTON, DELAWARE,
I. DU PONT DE NEMOURS 8: COMPANY, OF
A CORPORATION OF DELAWARE.
STABILIZATION OF TETRAALKYL LEAD AND COMPOSITIONS CONTAINING THE SAME.
No Drawing. Application filed June 19,
This invention relates to the stabilization of tetra alkyl lead, unmixed with anything but its normal impurities, and to the stabilization of tetra alkyl lead compositions containing hydrocarbons and halogen derivatives of hydrocarbons. More particularly our invention relates to the stabilization of tetra alkyl lead and compositions containing tetra alkyl lead by the addition thereto of 10 small amounts of aliphatic amines or derlvatives of aliphatic amines.
It is known that ordinarily commercial tetra alkyl lead, particularly tetra ethyl lead, decomposes slowly on standing, with the formation of a precipitate, and that this decomposition is accelerated in these compounds when they contain such organic sub stances as halogen derivatives of hydrocarbons.
An object of our invention is the stabilization of tetra alkyl lead compounds and compositions containing these compounds. Other objects will appear as the descrlptlon proceeds.
\Ve have discovered that decomposition of tetra alkyl lead compounds, and compositions containing the same, can be prevented by the introduction into these compounds or compositions, of aliphatic primary, secondary, or tertiary amines, or derivatives of these, such as the tetra alkyl ammonium hydroxides, and alkyl substituted hydroxyl amines.
B way of description of our invention, the ollowing illustrative examples are given, but it will be understood that other embodiments exist and may be practiced without departing from the spirit of the invention:
Example 1.--5O grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed together. To this mixture is added diethylamine, either anhydrous or as water solution, in amounts up to one gram.
Example 2.50 grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed to gether. To this mixture is addedmono-methlyamine, either anhydrous or as water solution, in amounts up to one gram.
Example 3.-50 grams of tetra methyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-ehlor-naphthalene are mixed 1928. Serial No. 286,706.
together. To this mixture is added methylhydroxylamine, either anhydrous or as water solution, in amounts upto one gram.
Example 4.5O grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed together. To this mixture is added tetraethyl-ammonium hydroxide, either anhydrous or as water solution, in amounts up to one gram.
Example 5.5O grams of tetra ethyl lead, 45 grams of ethylene dibromide, and 5 grams of mono-chlor-naphthalene are mixed together. To this mixture is added triethylamine, either anhydrous or as Water solution, in amounts up to one gram.
The solutions prepared according to the foregoing illustrative examples will remain stable indefinitely under the conditions ordinarily employed for the storage of tetra ethyl lead and mixtures containing the same.
It will be understood, of course, that either tetra ethyl lead or tetra methyl lead may be included in any one of the foregoing illustrative examples. \Ve have found that these, solutions so prepared will remain stable indefinitely under the conditions ordinarily employed for the storage of tetra alkyl lead compounds and the compositions containing these compounds.
As many apparently widely different embodiments of this invention may be made without departing from the spirit thereof, it is to be understood that we .do not intend to limit ourselves to the specific embodiments thereof except as indicated in the appended claims.
We claim:
1. A composition comprising tetra alkyl lead and an aliphatic base.
2. A composition comprising tetra alkyl lead and an alky l amine.
3. A composition comprising tetra alkyl lead and dimethylamine.
4. A composition comprising tetra alkyl llOead, an alkyl bromide, and an aliphatic ase.
5. A composition comprising tetra alkyl lead, ethylene dibromide, a chlorinated aromatic hydrocarbon, and an aliphatic base.
6. A composition comprising tetra alkyl lead, ethylene dibromide, a chlor-naphtha- 105 lene, and an aliphatic base.
7. A composition comprising lead, ethylene dibromide, monothale-ne, and an aliphatic base.
/ 8. A composition comprising 5 lead and an aliphatic base.
9. A composition comprising lead and an alkyl amine.
10. A composition comprising lead and dimethylaminc.
11. A composition comprising lead,.an alkyl bromide, and a base.
12. A composition comprising tetra alkyl chlor-naphtetra ethyl tetra ethyl tetra ethyl tetra ethyl n aliphatic tetra ethyl lead, ethylene dibromide, a chlorinated aro- 15 matic hydrocarbon, and an aliphatic base.
13. A. composition comprising lead, ethylene dibromide, lenc, and an aliphatic base. i 14. A composition comprising lead, ethylene dibromide, monothalene, and an aliphatic base.
tetra ethyl a chlor-naphthatetra ethyl chlor-naph- 15. A composition comprising tetra ethyl lead, an alkyl bromide, and an alkylami'nc.
16. A composition comprising tetra ethyl lead, ethylene dibromide, a chlorinated aromatic hydrocarbon, and an alkylamine.
17. A composition comprising tetra ethyl lead, ethylene dibromidc, a chlorinated aromatic hydrocarbon and dimethylamine.
18. A composition comprising tetra ethyl lead, ethylene dibromide, a chlor-naphthalene, and dimethylamine.
19. A composition comprising tetra eth 1 lead, ethylene dibror'nide, mono-chlor-nap 1- thalene, and dimethylamine.
20. A composition comprising tetra alkyl lead, halogen derivatives of hydrocarbons, and an aliphatic amine.
In testimony whereof we atiix our signatures.
WILLIAM S. CALCOTT. ALFRED E. PARMELEE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US286706A US1724640A (en) | 1928-06-19 | 1928-06-19 | Stabilization of tetraalkyl lead and compositions containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US286706A US1724640A (en) | 1928-06-19 | 1928-06-19 | Stabilization of tetraalkyl lead and compositions containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1724640A true US1724640A (en) | 1929-08-13 |
Family
ID=23099815
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US286706A Expired - Lifetime US1724640A (en) | 1928-06-19 | 1928-06-19 | Stabilization of tetraalkyl lead and compositions containing the same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1724640A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2618612A (en) * | 1950-06-01 | 1952-11-18 | Standard Oil Dev Co | Concentrated lead fluids |
| US2653589A (en) * | 1946-07-20 | 1953-09-29 | Kraus Alphonse | Booster device for internalcombustion engines |
| US2758916A (en) * | 1951-07-09 | 1956-08-14 | Phillips Petroleum Co | Fuel compositions |
| US3133097A (en) * | 1962-06-08 | 1964-05-12 | Ethyl Corp | Stable lead alkyl compositions and a method for preparing the same |
-
1928
- 1928-06-19 US US286706A patent/US1724640A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2653589A (en) * | 1946-07-20 | 1953-09-29 | Kraus Alphonse | Booster device for internalcombustion engines |
| US2618612A (en) * | 1950-06-01 | 1952-11-18 | Standard Oil Dev Co | Concentrated lead fluids |
| US2758916A (en) * | 1951-07-09 | 1956-08-14 | Phillips Petroleum Co | Fuel compositions |
| US3133097A (en) * | 1962-06-08 | 1964-05-12 | Ethyl Corp | Stable lead alkyl compositions and a method for preparing the same |
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