US1939255A - Process of oxidizing hydrocarbons - Google Patents
Process of oxidizing hydrocarbons Download PDFInfo
- Publication number
- US1939255A US1939255A US118824A US11882426A US1939255A US 1939255 A US1939255 A US 1939255A US 118824 A US118824 A US 118824A US 11882426 A US11882426 A US 11882426A US 1939255 A US1939255 A US 1939255A
- Authority
- US
- United States
- Prior art keywords
- hydrocarbons
- oxidation
- aldehydes
- acids
- produce
- 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
- 229930195733 hydrocarbon Natural products 0.000 title description 18
- 150000002430 hydrocarbons Chemical class 0.000 title description 18
- 238000000034 method Methods 0.000 title description 9
- 230000001590 oxidative effect Effects 0.000 title description 3
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 10
- 230000003647 oxidation Effects 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 239000007800 oxidant agent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910001868 water Inorganic materials 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- C07C27/10—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons
Definitions
- This invention relates to improvements in process of oxidizing hydrocarbons, and refers more particularly to the production therefrom of alcohol, aldehydes, carboxylic acids and other oxidation compounds.
- the object of the present invention is to retard this oxidation of the hydrocarbons in such a way as to produce from the hydrocarbons the alcohols, aldehydes or acids heretofore referred to. I accomplish this by adding to the hydrocarbons while subjected to the treatment with air or other" oxidizing agent a combustion retarding substance such as tetra-ethyl lead which so slows up the velocity of combustion that appreciable percentages of valuable products are derived due to the reaction of air, oxygen, ozone, or any other .gaseous oxidizing agent.
- a combustion retarding substance such as tetra-ethyl lead which so slows up the velocity of combustion that appreciable percentages of valuable products are derived due to the reaction of air, oxygen, ozone, or any other .gaseous oxidizing agent.
- One method of carrying out the invention is to add to the gasoline small percentages of tetraethyl lead, vaporizing the same in a heated coil or other suitable receptacle, while adding thereto regulated quantities of a gaseous oxidizing agent such as air.
- a fraction of 1% of tetra-ethyl lead may be added to a given quantity of gasoline or other hydrocarbon treated, and the gasoline heated under atmospheric pressure to a temperature of upwards of 600 F.
- To this gaseous mixture may be added 25% by volume of air or other oxidizing agent. The air may be added in such quantities as to produce exothermic reaction.
- the products pass into a suitable water condenser and receiver where they are separated out in the usual way by fractional distillation.
- heavier oils may be treated, as for example, fuel oils, petroleums or solids may be distilled off, and the vapors therefrom treated in the manner heretofore described.
- lighter products may be treated, as for example, natural gas or gases made from thermo distillation of coal or other carbonaceous material.
- the temperaturesunder which these various products will be treated will depend of course, upon the result desired, and also the character of the material being subjected to reaction.
- the process may be carried out at atmospheric pressure or under vacuum. In certain cases it may be carried on under superatmospherlc pressure, but in such cases care should be taken to regulate the oxidizing agent so as to avoid explosive mixtures.
- a process for producing alcohols, aldehydes, and acids from hydrocarbons consisting in subso jecting such hydrocarbons while heated to a temperature upwards of 600 F. to the action of an oxidizing agent to produce substantial oxidation thereof, retarding the oxidation by the addition of tetra-ethyl lead, and limiting the o5 extent of oxidation to produce alcohols, aldehydes and acids.
- a process for treating hydrocarbons to produce alcohols, aldehydes, and acids comprising adding to the hydrocarbon while at a temperature upwards of 600 F. an oxidizing agent in such quantity as will produce an exothermic reaction,
- a process for treating hydrocarbons to produce alcohols, aldehydes, and acids comprising adding to the hydrocarbon while at a temperaso ture upwards of 600- F. an oxidizing agent in such quantity as will produce an exothermic reaction, showing up the velocity of combustion by the invorporation of less than 1% by volume of tetra-ethyl lead in the hydrocarbon undergoing treatment, and limiting the extent of oxidation to produce alcohols, aldehydes and acids.
- a process for producing alcohols, aldehydes and acids from hydrocarbons which comprises subjecting the hydrocarbons while heated to oxidizing temperature to the action of an oxidizing agent to produce substantial oxidation thereof, adding tetra-ethyl lead to the'hydrocarbons undergoing treatment to decrease the velocity of the oxidation reaction, and limiting the 96 extent of oxidation to produce alcohols, aldehydes and acids.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Dec. 12, 1933 UNITED STATES PATENT OFFICE No Drawing. -Application June 26, 1926, Serial No. 118,824. Renewed May 20, 1930 4 Claims.
This invention relates to improvements in process of oxidizing hydrocarbons, and refers more particularly to the production therefrom of alcohol, aldehydes, carboxylic acids and other oxidation compounds.
In the normal oxidation of hydrocarbons with air, the velocity of the reaction is so high, that the end products formed are carbon-dioxide, carbon-monoxide and water.
The object of the present invention is to retard this oxidation of the hydrocarbons in such a way as to produce from the hydrocarbons the alcohols, aldehydes or acids heretofore referred to. I accomplish this by adding to the hydrocarbons while subjected to the treatment with air or other" oxidizing agent a combustion retarding substance such as tetra-ethyl lead which so slows up the velocity of combustion that appreciable percentages of valuable products are derived due to the reaction of air, oxygen, ozone, or any other .gaseous oxidizing agent.
One method of carrying out the invention is to add to the gasoline small percentages of tetraethyl lead, vaporizing the same in a heated coil or other suitable receptacle, while adding thereto regulated quantities of a gaseous oxidizing agent such as air.
In carrying out the process, a fraction of 1% of tetra-ethyl lead may be added to a given quantity of gasoline or other hydrocarbon treated, and the gasoline heated under atmospheric pressure to a temperature of upwards of 600 F. To this gaseous mixture may be added 25% by volume of air or other oxidizing agent. The air may be added in such quantities as to produce exothermic reaction. After the treatment, the products pass into a suitable water condenser and receiver where they are separated out in the usual way by fractional distillation.
Instead of treating gasoline in this manner, heavier oils may be treated, as for example, fuel oils, petroleums or solids may be distilled off, and the vapors therefrom treated in the manner heretofore described.
Instead of treating the heavier products, lighter products may be treated, as for example, natural gas or gases made from thermo distillation of coal or other carbonaceous material. The temperaturesunder which these various products will be treated, will depend of course, upon the result desired, and also the character of the material being subjected to reaction. The process may be carried out at atmospheric pressure or under vacuum. In certain cases it may be carried on under superatmospherlc pressure, but in such cases care should be taken to regulate the oxidizing agent so as to avoid explosive mixtures.
I claim as my invention:
1. A process for producing alcohols, aldehydes, and acids from hydrocarbons consisting in subso jecting such hydrocarbons while heated to a temperature upwards of 600 F. to the action of an oxidizing agent to produce substantial oxidation thereof, retarding the oxidation by the addition of tetra-ethyl lead, and limiting the o5 extent of oxidation to produce alcohols, aldehydes and acids.
2. A process for treating hydrocarbons to produce alcohols, aldehydes, and acids comprising adding to the hydrocarbon while at a temperature upwards of 600 F. an oxidizing agent in such quantity as will produce an exothermic reaction,
slowing up the velocity of combustion by the in-- corporation of a quantity of tetra-ethyl lead in the hydrocarbon undergoing treatment, and limiting the extent of oxidation to produce alcohols, aldehydes and acids.
3. A process for treating hydrocarbons to produce alcohols, aldehydes, and acids comprising adding to the hydrocarbon while at a temperaso ture upwards of 600- F. an oxidizing agent in such quantity as will produce an exothermic reaction, showing up the velocity of combustion by the invorporation of less than 1% by volume of tetra-ethyl lead in the hydrocarbon undergoing treatment, and limiting the extent of oxidation to produce alcohols, aldehydes and acids.
4. A process for producing alcohols, aldehydes and acids from hydrocarbons which comprises subjecting the hydrocarbons while heated to oxidizing temperature to the action of an oxidizing agent to produce substantial oxidation thereof, adding tetra-ethyl lead to the'hydrocarbons undergoing treatment to decrease the velocity of the oxidation reaction, and limiting the 96 extent of oxidation to produce alcohols, aldehydes and acids.
GUSTAV EGLOFF.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US118824A US1939255A (en) | 1926-06-26 | 1926-06-26 | Process of oxidizing hydrocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US118824A US1939255A (en) | 1926-06-26 | 1926-06-26 | Process of oxidizing hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1939255A true US1939255A (en) | 1933-12-12 |
Family
ID=22380957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US118824A Expired - Lifetime US1939255A (en) | 1926-06-26 | 1926-06-26 | Process of oxidizing hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1939255A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2552278A (en) * | 1949-03-22 | 1951-05-08 | Monsanto Chemicals | Liquid phase oxidation |
-
1926
- 1926-06-26 US US118824A patent/US1939255A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2552278A (en) * | 1949-03-22 | 1951-05-08 | Monsanto Chemicals | Liquid phase oxidation |
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