US1305790A - forrest - Google Patents
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- US1305790A US1305790A US1305790DA US1305790A US 1305790 A US1305790 A US 1305790A US 1305790D A US1305790D A US 1305790DA US 1305790 A US1305790 A US 1305790A
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- distillates
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- hydrocarbons
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- Prior art date
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- 239000000047 product Substances 0.000 description 36
- 150000002430 hydrocarbons Chemical class 0.000 description 32
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 22
- 235000019198 oils Nutrition 0.000 description 22
- 239000002253 acid Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000012260 resinous material Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 229940079938 Nitrocellulose Drugs 0.000 description 6
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2S,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6S)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2R,3R,4S,5R,6S)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 239000012263 liquid product Substances 0.000 description 6
- 229920001220 nitrocellulos Polymers 0.000 description 6
- 238000000197 pyrolysis Methods 0.000 description 6
- KMUONIBRACKNSN-UHFFFAOYSA-N Potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 4
- 229950006485 Pyroxylin Drugs 0.000 description 4
- 229920001800 Shellac Polymers 0.000 description 4
- KIEOKOFEPABQKJ-UHFFFAOYSA-N Sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 4
- 238000010306 acid treatment Methods 0.000 description 4
- 239000010426 asphalt Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012262 resinous product Substances 0.000 description 4
- 239000004208 shellac Substances 0.000 description 4
- 229940113147 shellac Drugs 0.000 description 4
- 235000013874 shellac Nutrition 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 240000006523 Abies balsamea Species 0.000 description 2
- 235000007173 Abies balsamea Nutrition 0.000 description 2
- 239000004857 Balsam Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000015912 Impatiens biflora Nutrition 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- 229940057007 Petroleum distillate Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000002649 leather substitute Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000013379 molasses Nutrition 0.000 description 2
- 150000002926 oxygen Chemical class 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- -1 polymethylenes Polymers 0.000 description 2
- 230000001105 regulatory Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052572 stoneware Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
Definitions
- the object of our invention is to provide balsamic and resinous products by the action of nitric acid upon the unsaturated hydrocarbons of the distillates from petroleum or from the native solid bitumens.
- distillates are composed of both saturated and unsaturated hydrocarbons and as a means of difierentiating between these two classes of substances they may be treated with sulfuric acid, first with ordinary 66 acidand finally with fuming sulfuric acid. That portion which is unacted upon by such acid treatment consists of the saturated hydrocarbons and that portion which is acted upon constitutes the unsaturated hydrocarbons as referred to in this specification. It is this unsaturated portion which is the source of the materials we have discovered.
- the unsaturated portion consists of olefins, naphthenes, polymethylenes, and the sulfur, nitrogen and oxygen derivatives thereof, while the saturated portion consists of liquid pa-raffins.
- distillates which are composed largely of saturated paraflin hydrocarbons and we preferably select that distillate which contains the highest amount of unsaturated bodies. It is found that "the distillates obtained by the destructive distillation of asphaltic petroleum or of the solid asphalts are preferable for our purpose and the distillate obtained in the destructive distillation of gilsoni'te is especially desirable. WVe will therefore confine our illustration of our method for the production of these substances to the distillates from the destructive distillation of gilsonite. "Such distillates may be obtained by any of the methods of distillation in common use Patented June 3, 1919.
- distillates have a wide range of boiling points, say from 150 F. to 700 F. and while it is sometimes desirable to proceed with such a combination of substances it is generally more desirable to select some fraction or combination of fractions thereof, say that below 400 F. or between 400 F. and 600 F. or even narrower fractions, say between 550 and 600 F. We may also select specific fractions and recombine them in new proportions and thereby obtain superior results.
- the material produced from the lower boiling fraction is softer than that produced from the higher fractions, and the selection of the proper fraction permits of the possibility of producing products varying in hardness from a soft balsam like material to a hard resin.
- it is intended to produce three grades which are respectively soft, medium and hard, all of which are of light color and are completely soluble in methyl, ethyl and higher alcohols, acetone and the higher ketones, while at the same time they are insoluble or virtually so in petroleum ether and in carbon disulfid.
- nitric acid (6. ⁇ 1. 43 B.) while the oil is stirred in any convenient way to assist mixing.
- concentration of nitric acid employed may be varied to adapt itself to the nature of the particular hydrocarbons or fractions thereof under treatment and may contain from 5 to 10% HNO up to the possible maximum.
- the addition of acid to oil causes a rise in temperature. This should not be allowed to exceed say 200 F. Any desired temperature between 200 F. and 220 F. may be maintained by regulating the rate of addition of acid to oil. However, we have found it advantageous to add the acid to the oil so slowly that the heat of reaction is wholly or almost wholly dissipated, the desired temperature (200 F .220 F.,) being maintained by the application of heat from the outside. The reaction is stopped, i. e. no more acid added, when approximately 100 parts by volume of acid have been added to 200 parts by weight of oil.
- the main reaction product, where fractions between 400 and 600 F. are employed is a light yellow plastic semi-solid resin.
- a suitable distillate may be obtained from the various fractions of the gilsonite distillate, and the same statement holds good with distillates of other bitumens.
- the reac tion mixture is cooled to 507 5 F., when the resinous matter separates and may be removed, or the reaction mixture may be poured into cold water and the products separated in this way.
- the resulting resinous mass is removed, and agitated thoroughly with hot water using several fresh wash waters, in order to remove free nitric acid and soluble and emulsifiable impurities.
- This washing is preferably assisted by the addition to the wash waters, of very small amounts of ammonia, or sodium carbonate, or of chalk in suspension, afterward washing entirely free of these substances.
- WVe also prefer in the case of products obtained from gilsonite fractions above 600 F. to further use an extremely dilute hot solution of sodium or potassium bichromate as wash water.
- This reagent also seems to impart a slight increased degree of solidity to the resin. To take care to remove this reagent by thorough washing with hot water.
- balsamic and resinous materials which consists in slowly and gradually adding nitric acid (or oXids of nitrogen derived therefrom) to distillates of native bitumens which contain a relatively high proportion of unsaturated and reactive liquid hydrocarbons the quantity of acid added being considerably less than the quantity of distillate and separating the balsamic resinous materials thus formed from the residual liquid product.
- balsamic and resinous materials which consists in adding nitric acid (or oXids of nitrogen derived therefrom) to distillates of native bitumens which contain a relatively high proportion of unsaturated and reactive liquid hydrocarbons; separating the balsamic and resinous materials thus formed from the residual liquid product; and treating with a soluble bichromate to harden and bleach the product.
- balsamic and resinous materials which consists in adding nitric acid very slowly to distillates of native bitumens with maintenance of a temperature between 200 F. and 220 E, and with agitation and thorough mixing, and then separating the bituminous and resinous materials thus formed from the residual liquid product.
- a balsamic or resinous material resulting from the reaction of nitric acid or oxids of nitrogen derived therefrom upon the unsaturated and reactive distillates of native bitumens, characterized by'being soluble in alcohol and acetone, but insoluble in petroleum ether or carbon disulfid.
Description
UNITED STATES PATENT OFFICE.
JERSEY, ASSIG-NORS TO THE BARBER, ASPHALT PAVING COMPANY, OF PHILADEL- PI'IIA, PENNSYLVANIA, A CORPORATION OF WEST VIRGINIA.
MANUFACTURE OF RESINOUS PRODUCTS.
No Drawing.
To all whom it may concern:
Be it known that we, CHARLES N. FORREST and JOSEPH V. Mines, citizens of the United States of America, residing in Rahway, county of Union, and State of New Jersey, and Perth Amboy, county of Middlesex, and State of New Jersey, respectively, have in vented certain new and useful Improvements in the Manufacture of Resinous Proclucts, of which the following is a specification.
The object of our invention is to provide balsamic and resinous products by the action of nitric acid upon the unsaturated hydrocarbons of the distillates from petroleum or from the native solid bitumens.
All such distillates are composed of both saturated and unsaturated hydrocarbons and as a means of difierentiating between these two classes of substances they may be treated with sulfuric acid, first with ordinary 66 acidand finally with fuming sulfuric acid. That portion which is unacted upon by such acid treatment consists of the saturated hydrocarbons and that portion which is acted upon constitutes the unsaturated hydrocarbons as referred to in this specification. It is this unsaturated portion which is the source of the materials we have discovered. The unsaturated portion consists of olefins, naphthenes, polymethylenes, and the sulfur, nitrogen and oxygen derivatives thereof, while the saturated portion consists of liquid pa-raffins. It is not desirable to select for this purpose any distillates which are composed largely of saturated paraflin hydrocarbons and we preferably select that distillate which contains the highest amount of unsaturated bodies. It is found that "the distillates obtained by the destructive distillation of asphaltic petroleum or of the solid asphalts are preferable for our purpose and the distillate obtained in the destructive distillation of gilsoni'te is especially desirable. WVe will therefore confine our illustration of our method for the production of these substances to the distillates from the destructive distillation of gilsonite. "Such distillates may be obtained by any of the methods of distillation in common use Patented June 3, 1919.
Application filed December 31, 1917. Serial No. 209,706.
for destructively distilling oils, as the desirability of any distillate for our purpose is inherent in the original substance rather than being due to the particular method by which it is distilled in the first instance.
lVhile the treatment of the liquid hydrocarbons with sulfuric acid, as hereinbefore described, will differentiate between the saturated and unsaturated hydrocarbons, it is not desirable to isolate the latter class of hydrocarbons by such means for the purpose of this invention. In fact it is most undesirable to do so because the sulfuric acid treatment carbonizes the oil and also produces sulfonic bodies which are undesirable for our purpose. On the contrary we proceed with the mixed hydrocarbons, since those of the saturated class are inert and can be separated from our new product after it is formed by our process from the unsaturated hydrocarbons in the presence of the saturated hydrocarbons.
It is to be understood that such distillates have a wide range of boiling points, say from 150 F. to 700 F. and while it is sometimes desirable to proceed with such a combination of substances it is generally more desirable to select some fraction or combination of fractions thereof, say that below 400 F. or between 400 F. and 600 F. or even narrower fractions, say between 550 and 600 F. We may also select specific fractions and recombine them in new proportions and thereby obtain superior results.
This is because the material produced from the lower boiling fraction is softer than that produced from the higher fractions, and the selection of the proper fraction permits of the possibility of producing products varying in hardness from a soft balsam like material to a hard resin. In general, however, it is intended to produce three grades which are respectively soft, medium and hard, all of which are of light color and are completely soluble in methyl, ethyl and higher alcohols, acetone and the higher ketones, while at the same time they are insoluble or virtually so in petroleum ether and in carbon disulfid.
Our new products are also insoluble in water and dilute mineral acids. They are softened slightly by moderate heat, say below 212 F. and intumesce and carbonize rather than melt at temperatures at which common resin (colophony) asphalt and similar substances safely melt.
The special utility of our products lies in their capacity to combine or mix with pyroxylin in all proportions in the presence of a mutual solvent and the consequent utili zation of such mixtures as lacquer, leather dressings and in the production of artificial leather, which usually consist of a coating of nitro-cellulose products and nitrated vegetable oils on woven or felted fabrics. They are also a substitute for shellac in many, if not all, commercial applications, especially if some pyroxylin be added.
In preparing our new products we select a suitable fraction or combination of fractions of the distillate from gilsonite and place it in an iron, stoneware'or other vessel immune to nitric acid, which vessel is provided with a jacket through which steam or hot water may be circulated for heating purposes, or cold water for cooling purposes, and then adjust the temperature of the oil to about 200 F.
To the oil is then added slowly in small increments, dilute nitric acid (6. {1. 43 B.) while the oil is stirred in any convenient way to assist mixing. The "olume of acid dropped at any one time upon the oil should not exceed the ratio of 1 to 2500, and may advantageously be less, as the reaction is an exothermic one and may proceed with considerable violence if not handled cautiously. The concentration of nitric acid employed may be varied to adapt itself to the nature of the particular hydrocarbons or fractions thereof under treatment and may contain from 5 to 10% HNO up to the possible maximum.
The addition of acid to oil causes a rise in temperature. This should not be allowed to exceed say 200 F. Any desired temperature between 200 F. and 220 F. may be maintained by regulating the rate of addition of acid to oil. However, we have found it advantageous to add the acid to the oil so slowly that the heat of reaction is wholly or almost wholly dissipated, the desired temperature (200 F .220 F.,) being maintained by the application of heat from the outside. The reaction is stopped, i. e. no more acid added, when approximately 100 parts by volume of acid have been added to 200 parts by weight of oil. The main reaction product, where fractions between 400 and 600 F. are employed is a light yellow plastic semi-solid resin.
If, instead of using the fraction of gilsonitedistillate below 600 F., higher fractions be used, for example, a suitable distillate may be obtained from the various fractions of the gilsonite distillate, and the same statement holds good with distillates of other bitumens.
l/Ve have found the above process may be assisted, or, in fact, carried out by blowing oxids of nitrogen through the oils in question,-but we prefer to use nitric acid in the manner shown.
After the reaction is completed, the reac tion mixture is cooled to 507 5 F., when the resinous matter separates and may be removed, or the reaction mixture may be poured into cold water and the products separated in this way. In any case, the resulting resinous mass is removed, and agitated thoroughly with hot water using several fresh wash waters, in order to remove free nitric acid and soluble and emulsifiable impurities. This washing is preferably assisted by the addition to the wash waters, of very small amounts of ammonia, or sodium carbonate, or of chalk in suspension, afterward washing entirely free of these substances.
WVe also prefer in the case of products obtained from gilsonite fractions above 600 F. to further use an extremely dilute hot solution of sodium or potassium bichromate as wash water. This reagent also seems to impart a slight increased degree of solidity to the resin. To take care to remove this reagent by thorough washing with hot water.
WVhen handling a product obtained by the action of nitric acid, as above, on distillates below say 600 F., then we use a stronger solution of sodium or potassium bichromate than we use in the case of the products prepared from the fractions of the gilsonite distillate above 600 F. To be specific we may use in the latter case seven (7) parts (2. g. l Ta Cr O to 10000 of water and fourteen (14) parts HCl (sp. gr. 1.2). In the former case we use a l020% solution of l Ta Cr O containing 210% I-ICl (sp. gr. 1.20). The use of this increased concentration of Na cr o in the former case exerts a bleaching action on the resin and renders it pale yellow. Thorough washing with hot water is then employed to remove all traces of bichromate and acid. The material is then dried.
l/Vhen proceeding with the distillate from gilsonite, which contains not more than 25% of saturated hydrocarbons, the yield of our product by the method described amounts to add to hydrocarbon distillates, a mixture of nitric and sulfuric acid, until the acid mixture amounts to three parts added to one part of petroleum distillate. Such process diifers from that here described, in that the resulting product is solid, or semi-solid, while our products range from soft to hard, the softer products resembling molasses in consistency. Again our products are virtually insoluble in petroleum ether, and in carbon disulfid, while the products of the process just named are thus soluble, a distinction which is particularly useful when our products are used as a substitute for shellac.
Having thus described our invention, we claim:
1. The process of obtaining balsamic and resinous materials which consists in slowly and gradually adding nitric acid (or oXids of nitrogen derived therefrom) to distillates of native bitumens which contain a relatively high proportion of unsaturated and reactive liquid hydrocarbons the quantity of acid added being considerably less than the quantity of distillate and separating the balsamic resinous materials thus formed from the residual liquid product.
2. The process of obtaining balsamic and resinous materials which consists in adding nitric acid (or oXids of nitrogen derived therefrom) to distillates of native bitumens which contain a relatively high proportion of unsaturated and reactive liquid hydrocarbons; separating the balsamic and resinous materials thus formed from the residual liquid product; and treating with a soluble bichromate to harden and bleach the product.
3. The process of obtaining balsamic and resinous materials which consists in adding nitric acid very slowly to distillates of native bitumens with maintenance of a temperature between 200 F. and 220 E, and with agitation and thorough mixing, and then separating the bituminous and resinous materials thus formed from the residual liquid product.
4. A balsamic or resinous material resulting from the reaction of nitric acid or oxids of nitrogen derived therefrom upon the unsaturated and reactive distillates of native bitumens, characterized by'being soluble in alcohol and acetone, but insoluble in petroleum ether or carbon disulfid.
In testimony whereof, We have hereunto signed our names at Philadelphia, Pennsylvana, this twenty-eighth day of December, 191
CHARLES N. FORREST. JOSEPH V. MEIGS.
Witnesses:
JAMES H. BELL, E. L. FULLERTON.
Copies of this patent may be obtained for five cents each, by addressing the Commissioner of Patents, Washington, D. 0.
Publications (1)
Publication Number | Publication Date |
---|---|
US1305790A true US1305790A (en) | 1919-06-03 |
Family
ID=3373317
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US1305790D Expired - Lifetime US1305790A (en) | forrest |
Country Status (1)
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US (1) | US1305790A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2478243A (en) * | 1946-06-03 | 1949-08-09 | Union Oil Co | Process of nitrating olefins |
US2597753A (en) * | 1950-04-20 | 1952-05-20 | Commercial Solvents Corp | Production of nitroparaffins |
-
0
- US US1305790D patent/US1305790A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2478243A (en) * | 1946-06-03 | 1949-08-09 | Union Oil Co | Process of nitrating olefins |
US2597753A (en) * | 1950-04-20 | 1952-05-20 | Commercial Solvents Corp | Production of nitroparaffins |
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