US1110925A - Process of manufacturing olefins and their oxidation products. - Google Patents
Process of manufacturing olefins and their oxidation products. Download PDFInfo
- Publication number
- US1110925A US1110925A US70217612A US1912702176A US1110925A US 1110925 A US1110925 A US 1110925A US 70217612 A US70217612 A US 70217612A US 1912702176 A US1912702176 A US 1912702176A US 1110925 A US1110925 A US 1110925A
- Authority
- US
- United States
- Prior art keywords
- olefins
- oxidation products
- oxidation
- treatment
- paraflins
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G9/00—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
- C10G9/34—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils by direct contact with inert preheated fluids, e.g. with molten metals or salts
- C10G9/36—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils by direct contact with inert preheated fluids, e.g. with molten metals or salts with heated gases or vapours
- C10G9/38—Thermal non-catalytic cracking, in the absence of hydrogen, of hydrocarbon oils by direct contact with inert preheated fluids, e.g. with molten metals or salts with heated gases or vapours produced by partial combustion of the material to be cracked or by combustion of another hydrocarbon
Definitions
- the principal objects of my invention are to devise a practical method of manufacturing olefins from mineral oils and also to devise a practical method of manufacturing sfilcohols, aldehydes and fatty acids thererom.
- the invention consists in the hereinafter described treatment of mineral oil to obtain a large proportion of olefins therefrom.
- the liquid product resultin from the treatment "of crude oil by t e so-called cracking process is a mixture consisting almost wholly of araflins with a comparatively small uant ty of olefins.
- the liquid product resu ting from the treatment of crude oil by a process invented by me and described in my co-pending application Ser. No. 696,891, filed May 13, 1912, is a mixture consisting of paraflins with a considerable proportion of olefins.
- my said process consists in forcing the crude oil to and through an atomizer on the inlet side of a coil of pipe of uniform diameter kept at a substantially cherry red temperature, the oil being thoroughly commingled at the atomizer with steam under a considerable pressure, say about one-hundred pounds per uare inch, the quantity of steam being that o a column of water substantially equal to or greater than the volume of the oil.
- the product resulting from the treatment just described is itself submitted to the same treatment; that is, the condensate resulting from the passing of the crude oil through a lon hot coil under the conditions above state is again passed through such a coil under substantiall the same conditions. In conse uence of this repeated operation, the resulting product contains a very large. percentage o olefins.
- a strong oxidizing agent such as chromic acidv or alkaline permanganate of potassium may be used.
- the result of the reaction of these last mentioned reagents upon the olefins is to convert them into alcohols, aldehydes and acids.
- Hypochlorous acid unites also with the olefins to form chlorhydrins which can be converted into corresponding oxids, as for instance, by heating with a solution of causti soda or other caustic alkali.
- hydrochloric acid may be used as a substitute for sulfuric acid and constitutes an equivalent therefor, but in such case, hydrochloric ether is formed instead of sulfonic ether, and such hydrochloric ether is immediately converted into alcohols in the same manner as the sulfonic ether.
- hydrochloric acid may be used as a substitute for sulfuric acid and constitutes an equivalent therefor, but in such case, hydrochloric ether is formed instead of sulfonic ether, and such hydrochloric ether is immediately converted into alcohols in the same manner as the sulfonic ether.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Combustion & Propulsion (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
CHARLIES J. GREENSTREET, 0F WEBSTER GROVES, MISSOURI.
PROCESS OF MANUFACTURING OLEFINS AND THEIR OXIDATION PRODUCTS.
1,110,925. No Drawing.
Specification of Letters Patent. Application filed June 7, 1912. Serial No.702,176.
Patented Sept, 15, 191%.
dation Products, of which the following is a specification.
The principal objects of my invention are to devise a practical method of manufacturing olefins from mineral oils and also to devise a practical method of manufacturing sfilcohols, aldehydes and fatty acids thererom.
The invention consists in the hereinafter described treatment of mineral oil to obtain a large proportion of olefins therefrom.
It also consists in the oxidation of olefin to obtain alcohols, aldehydes and acids therefrom. It also consists in the steps and processes hereinafter more fully described.
The liquid product resultin from the treatment "of crude oil by t e so-called cracking process is a mixture consisting almost wholly of araflins with a comparatively small uant ty of olefins. The liquid product resu ting from the treatment of crude oil by a process invented by me and described in my co-pending application Ser. No. 696,891, filed May 13, 1912, is a mixture consisting of paraflins with a considerable proportion of olefins. As more fully described in said application, my said process consists in forcing the crude oil to and through an atomizer on the inlet side of a coil of pipe of uniform diameter kept at a substantially cherry red temperature, the oil being thoroughly commingled at the atomizer with steam under a considerable pressure, say about one-hundred pounds per uare inch, the quantity of steam being that o a column of water substantially equal to or greater than the volume of the oil. In order to increase the production of olefin, the product resulting from the treatment just described is itself submitted to the same treatment; that is, the condensate resulting from the passing of the crude oil through a lon hot coil under the conditions above state is again passed through such a coil under substantiall the same conditions. In conse uence of this repeated operation, the resulting product contains a very large. percentage o olefins.
Whether the mixture of paraflins and olefins is obtained by the cracking process or by my said process, or otherwise, sulfuric acid is added thereto in suflicient quantity to convert the olefins into the corresponding sulfonlc ethers. Water is then added to convert such ethers into the corresponding alco hols. In the meanwhile, the paraflins remain unchanged. For some purposes, it may be unnecessary to separate the paraflins from the alcohols. Usually, however, it will be desirable to separate the parafiins from the alcohols; and in order-to accomplish such separation, the mixture is subjected to the process of fractional distillation. Fractional distillation 'is especially available for such separation by reason of the fact that, whereas plefins and paraflins of substantially the same specific gravity distil at nearly the same temperatures, there is a very wide difference in the distillation points of paraflins and the corresponding olefins on the one side compared with the alcohols derived therefrom on the other. Thus, while the olefin C l-I' distils at a temperature of one hundred and twenty-three degrees ccntigrade, the
corresponding alcohol C,H,,,O distils at a temperature of from one hundred and eight to one hundred and ninety degrees centlgrade.
When it is desired to convert the olefins of the mixture into the aldehydes or acids,
a strong oxidizing agent, such as chromic acidv or alkaline permanganate of potassium may be used. The result of the reaction of these last mentioned reagents upon the olefins is to convert them into alcohols, aldehydes and acids. Hypochlorous acid unites also with the olefins to form chlorhydrins which can be converted into corresponding oxids, as for instance, by heating with a solution of causti soda or other caustic alkali.
It is noted that whether-the olefins are treated with sulfuric acid or with by 0- chlorous acid or with chromic acid or aliialine permanganate of potassium, the general result in each case is an oxidation of the olefin. It is further noted that (with the exception of hypochlorous acid) all of these reagents efi'ect a direct oxidation of the olefins, that is, oxidation with a single reagent, whereas treatment with hypochlorous acid indirectly brings about oxidation, that is, treatment with hypochlorous acid produces an intermediate compound which requires an additional reagent to effect oxi-- [continuous pipe at a substantially dation thereof by substitution. These reagents react to produce diiferent specific results; and the choice of a reagent will depend to a certain extent upon the product desired. Instead of the reagents specified,
their proper chemical equivalents may be substituted therefor. For instance hydrochloric acid may be used as a substitute for sulfuric acid and constitutes an equivalent therefor, but in such case, hydrochloric ether is formed instead of sulfonic ether, and such hydrochloric ether is immediately converted into alcohols in the same manner as the sulfonic ether. Likewise, it is obvious that the presence of the paraflins is not of any.
impphrtance in the treatment of the olefins.
at I claim as my invention and desire 'to secure by Letters Patent is:
1.' The p'ocess of manufacturmg olefins 4 which consists in forcing mineral 011 commingled with steam through a long coil of heat and repeating the operation upon the result ing product. 2. The process of treating crude oil which consists in forcing it oommmgled with steam through a lon continuous coil of pipeat a substantially c err red heat, and oxidizing the olefin in 'ents of the resulting product. v 3. The process of treating crude oil which consists in forcing it commingled with steam through a long continuous coil of pipe at a substantialliyi cherry red heat, oxidizin the olefin ingl'e 'ents of the resulting pr uct, and separating the oxidation product by fractional disti ation..
Signed at St. Louis, Missouri, this 5th day. ofJune, 1912. I
CHARLES J. GREENSTREET.
Witnesses:
Amna'r H. Cnorssm'r, M. A, S am/mu.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70217612A US1110925A (en) | 1912-06-07 | 1912-06-07 | Process of manufacturing olefins and their oxidation products. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US70217612A US1110925A (en) | 1912-06-07 | 1912-06-07 | Process of manufacturing olefins and their oxidation products. |
Publications (1)
Publication Number | Publication Date |
---|---|
US1110925A true US1110925A (en) | 1914-09-15 |
Family
ID=3179113
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US70217612A Expired - Lifetime US1110925A (en) | 1912-06-07 | 1912-06-07 | Process of manufacturing olefins and their oxidation products. |
Country Status (1)
Country | Link |
---|---|
US (1) | US1110925A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE765126C (en) * | 1940-06-30 | 1953-03-02 | Ruhrchemie Ag | Process for the production of high molecular weight fatty acids |
US2944011A (en) * | 1956-12-10 | 1960-07-05 | Sun Oil Co | Sweetening hydrocarbons with dried chromium oxide |
US3281484A (en) * | 1963-10-17 | 1966-10-25 | Phillips Pctroleum Company | Process for removing trace olefins from paraffin hydrocarbon containing streams |
-
1912
- 1912-06-07 US US70217612A patent/US1110925A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE765126C (en) * | 1940-06-30 | 1953-03-02 | Ruhrchemie Ag | Process for the production of high molecular weight fatty acids |
US2944011A (en) * | 1956-12-10 | 1960-07-05 | Sun Oil Co | Sweetening hydrocarbons with dried chromium oxide |
US3281484A (en) * | 1963-10-17 | 1966-10-25 | Phillips Pctroleum Company | Process for removing trace olefins from paraffin hydrocarbon containing streams |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2198651A (en) | Organic compound | |
JP2016540780A (en) | Hydroformylation process | |
US1110925A (en) | Process of manufacturing olefins and their oxidation products. | |
US1724761A (en) | Process of hydrogenating crotonic aldehyde | |
EP0805138A1 (en) | Process for the hydroformylation of olefinic unsaturated compounds | |
EP1294670A1 (en) | Method for producing hydroformylation products of olefins with 2 to 8 carbon atoms | |
US2403743A (en) | Cyclic butadiene process | |
US2167203A (en) | Process of manufacture of ketones and alcohols from olefins | |
US2028267A (en) | Manufacturing ketones | |
DE741152C (en) | Process for the preparation of 1,3-diolefins with branched chain | |
DE102009004655B4 (en) | Process for the preparation of aldehydes | |
US1704732A (en) | Manufacture of valuable organic products | |
RU2556859C1 (en) | Method of producing isoprene by catalytic dehydrogenation of isoamylenes in adiabatic reactor | |
US2618649A (en) | Production of esters of products from oxo synthesis | |
US1754656A (en) | Method of chlorinating unsaturated hydrocarbons | |
US2690993A (en) | Separation of organic acids from oxygenated organic compounds by azeotropic distillation with water | |
DE3049543A1 (en) | METHOD FOR THE CONTINUOUS PRODUCTION OF 3-ALKYL-BUTEN-1-ALEN | |
US2188254A (en) | Concentration of aqueous alkene halohydrin solutions | |
DE870856C (en) | Process for the production of formamides or amines | |
US833095A (en) | Derivative of pinene and process of making same. | |
US1516756A (en) | Producing aromatic substances from petroleum | |
US583719A (en) | Johann carl wilhelm ferdinand tiemann | |
DE921934C (en) | Process for the production of aldehydes | |
US1844211A (en) | Setts | |
US1912484A (en) | Method of treating mixtures of partially oxidized hydrocarbons |