US2555891A - Conversion of hexaalkyldilead to tetraalkyllead - Google Patents
Conversion of hexaalkyldilead to tetraalkyllead Download PDFInfo
- Publication number
- US2555891A US2555891A US158346A US15834650A US2555891A US 2555891 A US2555891 A US 2555891A US 158346 A US158346 A US 158346A US 15834650 A US15834650 A US 15834650A US 2555891 A US2555891 A US 2555891A
- Authority
- US
- United States
- Prior art keywords
- hexaalkyldilead
- tetraalkyllead
- conversion
- tetraethyllead
- hexaethyldilead
- 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
- 238000006243 chemical reaction Methods 0.000 title description 7
- 238000000034 method Methods 0.000 claims description 8
- 150000001351 alkyl iodides Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 20
- DTTVFKVGEOETRX-UHFFFAOYSA-N triethyllead Chemical compound CC[Pb](CC)CC.CC[Pb](CC)CC DTTVFKVGEOETRX-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000007669 thermal treatment Methods 0.000 description 3
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical class CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- -1 magnesium Chemical compound 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001256 steam distillation Methods 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 catalytic conversion of hexaalkyldilead to tetraalkyllead. It particularly relates to the conversion of hexaethyldilead, formed as a by-product in certain processes for making tetraethyllead, to tetraethyllead. It is, however, useful in converting other hexaalkyldileads, such as hexamethyldilead, hexapropyldilead and hexabutyldilead, to the corresponding tetraalkylleads.
- hexaalkyldileads can be converted to the corresponding tetraalkyllead products, with an efiiciency greater than that predicted by the theoretical equation above for the thermal treatment, by treating hexaethyldilead, at temperatures substantially below 80 0., even room temperature, with certain alkyl halides. Furthermore. the reaction of our invention proceeds without the formation of gaseous decomposition products.
- alkyl halide catalysts of our invention are the alkyl iodides and bromides, particularly the lower alkyl halides such as methyl, ethyl, propyl and butyl iodides and the corresponding bromides. Also by alkyl halides we do not mean to limit our invention to monohalides since polyhalides, such as dibromoethane, dibromopropane, dibromobutane and the corresponding dibromoiodides also can be used.
- the time for the catalytic conversion of hexaalkyldilead varies between one-tenth to three hours and the temperature normally employed is from 20 C. to 100 C.
- the amount of catalyst employed varies from 5 to per cent of the hexaethyldilead being converted.
- a process for converting hexaalkyldilead into tetraalkyllead comprising treating said hexaalkyldilead with a material selected from the group consisting of alkyl iodides and alkyl bromides.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented June 5, 1951 CONVERSION OF HEXAALKYLDILEAD TO TETRAALKYLLEAD Ivar T. Krchn, Royal Oak, and Hymin Shapiro, Detroit, Mich, assignors to Ethyl Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application April 26, 1950, Serial No. 158,346
3 Claims.
This invention relates to the catalytic conversion of hexaalkyldilead to tetraalkyllead. It particularly relates to the conversion of hexaethyldilead, formed as a by-product in certain processes for making tetraethyllead, to tetraethyllead. It is, however, useful in converting other hexaalkyldileads, such as hexamethyldilead, hexapropyldilead and hexabutyldilead, to the corresponding tetraalkylleads.
Certain processes for making tetraethyllead. particularly those involving reducing metals other than sodium, such as magnesium, tend to form substantial quantities of hexaethyldilead in addition to or in place of the more important tetraethyllead product. Hexaethyldilead can be converted in part to tetraalkyllead by thermal treatment at temperatures above 80 C. as illustrated by the following equation:
It should be noted that based on the lead the theoretical conversion of hexaalkyldilead to tetraalkyllead is only 75 per cent. However, thermal treatment does not give the theoretical yield because to 40 per cent is lost to gaseous decomposition products which have little value. For example, in processes for making tetraethyllead, the tetraethyllead, by one method, is recovered from the other reaction products by steam distillation at about 100 C. At this temperature the hexaethyldilead present yields only 75 per cent of the theoretical yield of tetraethyllead, 25 per cent of gaseous decomposition products being formed. Thus a substantial amount of potential tetraethyllead is lost.
We have discovered that hexaalkyldileads can be converted to the corresponding tetraalkyllead products, with an efiiciency greater than that predicted by the theoretical equation above for the thermal treatment, by treating hexaethyldilead, at temperatures substantially below 80 0., even room temperature, with certain alkyl halides. Furthermore. the reaction of our invention proceeds without the formation of gaseous decomposition products.
The alkyl halide catalysts of our invention are the alkyl iodides and bromides, particularly the lower alkyl halides such as methyl, ethyl, propyl and butyl iodides and the corresponding bromides. Also by alkyl halides we do not mean to limit our invention to monohalides since polyhalides, such as dibromoethane, dibromopropane, dibromobutane and the corresponding dibromoiodides also can be used.
The time for the catalytic conversion of hexaalkyldilead varies between one-tenth to three hours and the temperature normally employed is from 20 C. to 100 C. The amount of catalyst employed varies from 5 to per cent of the hexaethyldilead being converted.
Our invention can be further understood by referring to the following working example.
To 5.8? grams of hexaethyldilead was added 1.7 grams of ethyl iodide. The mixture was heated for one and one-half hours at a temperature between and C. At the end of this period, analysis showed that 5.046 grams, or 98 per cent of the theoretical yield, of tetraethyllead was obtained. When ethyl bromide was substituted for ethyl iodide equally good yields were obtained. Likewise in a similar test dibromoethane converted over 9-8 per cent of the hexaethyldilead to tetraethyllead.
We claim:
1. A process for converting hexaalkyldilead into tetraalkyllead comprising treating said hexaalkyldilead with a material selected from the group consisting of alkyl iodides and alkyl bromides.
2. The process of claim 1 in which the material treated is hexaethyldilead.
3. The process of claim 2 in which the catalyst is an alkyl iodide.
IVAR T. KROHN HYMIN SHAPIRO.
No references cited.
Claims (1)
1. A PROCESS FOR CONVERTING HEXAALKYLDILEAD INTO TETRAALKYLLEAD COMPRISING TREATING SAID HEXAALKYLIDILEAD WITH A MATERIAL SELECTED FROM THE GROUP CONSISTING OF ALKYL IODIDES AND ALKYL BROMINDES.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US158346A US2555891A (en) | 1950-04-26 | 1950-04-26 | Conversion of hexaalkyldilead to tetraalkyllead |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US158346A US2555891A (en) | 1950-04-26 | 1950-04-26 | Conversion of hexaalkyldilead to tetraalkyllead |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2555891A true US2555891A (en) | 1951-06-05 |
Family
ID=22567705
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US158346A Expired - Lifetime US2555891A (en) | 1950-04-26 | 1950-04-26 | Conversion of hexaalkyldilead to tetraalkyllead |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2555891A (en) |
-
1950
- 1950-04-26 US US158346A patent/US2555891A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
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