US2246973A - Treatment of wood tar distillate - Google Patents
Treatment of wood tar distillate Download PDFInfo
- Publication number
- US2246973A US2246973A US298918A US29891839A US2246973A US 2246973 A US2246973 A US 2246973A US 298918 A US298918 A US 298918A US 29891839 A US29891839 A US 29891839A US 2246973 A US2246973 A US 2246973A
- Authority
- US
- United States
- Prior art keywords
- oil
- inhibitor
- gasoline
- distillation
- oxidizing agent
- 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
- 239000011276 wood tar Substances 0.000 title description 2
- 239000003112 inhibitor Substances 0.000 description 41
- 239000000047 product Substances 0.000 description 18
- 238000004821 distillation Methods 0.000 description 16
- 239000007800 oxidant agent Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000003209 petroleum derivative Substances 0.000 description 9
- 239000002023 wood Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000011269 tar Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000004040 coloring Methods 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011121 hardwood Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000218685 Tsuga Species 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C3/00—Working-up pitch, asphalt, bitumen
- C10C3/02—Working-up pitch, asphalt, bitumen by chemical means reaction
Definitions
- This invention rel-ates to the treatment of wood tar distillate. More particularly it concerns a new and improved inhibitor oil and a method of preparing the same.
- inhibitor oil insoluble viscous material commonly termed settled tar, which is usually separated into various fractions by distillation at reduced pressure.
- One of these fractions having an atmospheric boiling range of roughly 220-320 C., is known as inhibitor oil, and finds extensive use as a stabilizing agent for preventing gum formation in gasoline and like petroleum products.
- inhibitor oil as ordinarily prepared develops after standing an appreciable proportion of dark reddish-brown coloring material of unknown c nstitution, which lessens its desirability as an inhibitor.
- an object of the present invention is to provide a method of treating inhibitor oil to remove therefrom much of the objectionable dark reddish-brown coloring material.
- This object is obtained by subjecting the inhibitor oil to the action of an oxidizing agent and thereafter separating the substantially unoxidized fraction from the oxidized material, suitably by distillation.
- the product so obtained is a straw-colored oil which has an inhibiting power at least equal to that of ordinary inhibitor oil, and, even after long standing, develops very little reddish-brown coloring material.
- it is completely soluble in gasoline, as determined by the usual method. That is: three milliliters of the oil in a centrifuge tube are diluted to 100 milliliters with reference gasoline, and the sample is shaken thoroughly for ten minutes, and then centrifuged for ten minutes, after which the volume of the oil layer remaining is measured to determine the percentage of insoluble material.
- the oxidizing agent appears to attack preferentially the dark reddish-brown coloring materials and gasoline-insoluble bodies in the inhibitor oil, and to convert them to non-volatile tar-like substances from which the inhibitor oil can be separated by distillation or other means.
- any oxidizing agent is operable in the invention.
- inorganic oxidizing agents and particularly gaseous or volatile liquid inorganic agents, such as oxygen, air, and hydrogen peroxide, are to be preferred because of the fact they leave no residue in the treated oil.
- the inhibitor oil and a small proportion, usually 0.5 to 2.0 per cent, of the oxidizing agent are mixed and the mixture is stirred at a temperature of 20-50 C. for several hours, after which it is heated to a temperature of 120 C., for one or two hours.
- the oxidizing agent and oil may be allowed to react under other conditions of time and temperature, preferably within the range 20-120 C. without departing from the invention.
- the resulting mixture is distilled, preferably though not necessarily at reduced pressure, to recover the purified inhibitor oil as a yellow liquid, which dissolves completely in cracked gasoline (according to the solubility test pre-- viously outlined), and when present therein in a small proportion, e. g. 0.01 to 0.1 per cent by weight, effectively retards gum formation.
- Treatment according to the invention may also be accomplished by exposing the inhibitor oil in the vapor state to the action of the oxidizing agent, as during the distillation operation.
- Example 1 A sample of inhibitor oil prepared by the vacuum distillation of hardwood settled tar, having an atmospheric boiling range of 230 C.- 297" C., a specific gravity of 1.093 at 15.6 C./ 15.6 C., and a color drop value of 22 (A. S. T. M. D-l5634T), was treated according to the invention.
- a sample of the oil was placed in a closed iron pressure vessel and oxygen passed into the container until a gauge pressure of pounds per square inch wa reached. The gas inlet was then closed and the vessel heated at 100 C. for three hours, during which time the gas pressure rose to pounds and then gradually dropped to 100 pounds.
- the resultant treated oil was removed and distilled at reduced pressure, the distillate being a yellow-colored inhibitor oil. having a color drop value of 30, which did not change appreciably even on long standing. A small proportion of tarry residue was left in the still.
- Example 2 The untreated inhibitor oil of Example 1 was heated at a temperature of 100 C. for one hour mine water.
- Example 3 A charge of ordinary inhibitor oil was heated at a temperature of 70 to 90 C. for 24 hours, during which time air was blown continuously through the hot oil. The product was then vacuum distilled, the distillate being a light-yellow inhibitor oil as in the receding examples.
- Example 5 In a series of tests, ordinary inhibitor oil was mixed with a small proportion of each of the following oxidizing agents: nitric acid, aqueous potassium permanganate, manganese dioxide, yellow mercuric oxide, mercuric acetate, potassium chlorate, sulfuric acid, and saturated bro- Each test sample was heated at a temperature of 40 C. for to hours followed by a further heating at 100 to 120 C. for two hours, and was then distilled at reduced pressure. In every instance, the distillate was a stable light-colored inhibitor oil having gasoline gum-inhibiting properties at least equal to those of ordinary inhibitor oil.
- the process of the invention is applicable to the treatment of inhibitor oil as prepared from settled tar from the destruction distillation of any ligno-cellulosic substance, particularly hardwoods, such as birch and maple, as'well as softer woods such as hemlock, and other like materials, including peat and rotten wood.
- the process is ordinarily'applied to the inhibitor oil itself, or to a mixture of all the fractions obtained by distilling settled tar under reduced pressure, excluding the lowest boiling fraction which essentially comprises methanol products, water, and acetic acid.
- the method which comprises subjecting the inhibitor oil derived from the tarry products of wood distillation to the action of an oxidizing agent, and separating the substantially unoxidized fraction from the tarry oxidation products, the product so obtained being light-colored, miscible with gasoline, and eifective as an inhibitor in preventing -gum formation in gasoline and like petroleum products.
- the method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation which comprises subjecting the said oil to the action of a small proportion of an oxidizing agent, and distilling the treated product, to recover as distillate a light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
- the methodof treating the inhibitor oil derived by distillation from the tarry products of wood distillation which comprises subjecting the said oil to the action of a small proportion of an inorganic oxidizing agent and distilling the resulting product, to recover as distillate a lightcolored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
- the method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation which comprises subjecting the said oil to the action of a small proportion of a gaseous inorganic oxidizing agent, and distilling the resulting product, to recover as distillate a light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
- the method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation which comprises subjecting the said oil to the action of a small proportion of a volatile liquid inorganic oxidizing agent, and distilling the resulting product, to recover as distillate a light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
- the method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation which comprises heating the said oil at a temperature between 70 and C. and passing air therethrough, and thereafter distilling the treated oil to recover as distillate a. light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum forma: tion ingasoline and like petroleum products.
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- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
Patented June 24, 1941 TREATMENT OF WOOD TAR DISTILLATE Alfred A. Camilli, Crystal Falls, and Malcolm K. Johnston, Marquette, Mich., assignors to Cliffs Dow Chemical Company, Marquette, Mich, a
corporation of Michigan Application October 11, 1939,
N Drawing.
Serial No. 298,918
8 Claims.
This invention rel-ates to the treatment of wood tar distillate. More particularly it concerns a new and improved inhibitor oil and a method of preparing the same.
In the destructive distillation of wood, there is obtained, in addition to pyroligneous acid, an insoluble viscous material commonly termed settled tar, which is usually separated into various fractions by distillation at reduced pressure. One of these fractions, having an atmospheric boiling range of roughly 220-320 C., is known as inhibitor oil, and finds extensive use as a stabilizing agent for preventing gum formation in gasoline and like petroleum products. Unfortunately, however, inhibitor oil as ordinarily prepared develops after standing an appreciable proportion of dark reddish-brown coloring material of unknown c nstitution, which lessens its desirability as an inhibitor.
In view of this disadvantage, an object of the present invention is to provide a method of treating inhibitor oil to remove therefrom much of the objectionable dark reddish-brown coloring material.
This object is obtained by subjecting the inhibitor oil to the action of an oxidizing agent and thereafter separating the substantially unoxidized fraction from the oxidized material, suitably by distillation. The product so obtained is a straw-colored oil which has an inhibiting power at least equal to that of ordinary inhibitor oil, and, even after long standing, develops very little reddish-brown coloring material. In addition, it is completely soluble in gasoline, as determined by the usual method. That is: three milliliters of the oil in a centrifuge tube are diluted to 100 milliliters with reference gasoline, and the sample is shaken thoroughly for ten minutes, and then centrifuged for ten minutes, after which the volume of the oil layer remaining is measured to determine the percentage of insoluble material.
The exact nature of the chemical reaction occurring during the oxidative treatment according to the invention is not understood. However, the oxidizing agent appears to attack preferentially the dark reddish-brown coloring materials and gasoline-insoluble bodies in the inhibitor oil, and to convert them to non-volatile tar-like substances from which the inhibitor oil can be separated by distillation or other means.
In so far as we have been able to determine, any oxidizing agent is operable in the invention.
However, inorganic oxidizing agents, and particularly gaseous or volatile liquid inorganic agents, such as oxygen, air, and hydrogen peroxide, are to be preferred because of the fact they leave no residue in the treated oil.
In a preferred mode of operating, the inhibitor oil and a small proportion, usually 0.5 to 2.0 per cent, of the oxidizing agent are mixed and the mixture is stirred at a temperature of 20-50 C. for several hours, after which it is heated to a temperature of 120 C., for one or two hours. However, the oxidizing agent and oil may be allowed to react under other conditions of time and temperature, preferably within the range 20-120 C. without departing from the invention. After the oxidation treatment, the resulting mixture is distilled, preferably though not necessarily at reduced pressure, to recover the purified inhibitor oil as a yellow liquid, which dissolves completely in cracked gasoline (according to the solubility test pre-- viously outlined), and when present therein in a small proportion, e. g. 0.01 to 0.1 per cent by weight, effectively retards gum formation.
Treatment according to the invention may also be accomplished by exposing the inhibitor oil in the vapor state to the action of the oxidizing agent, as during the distillation operation.
The following examples will illustrate the invention but are not to be construed as limiting its scope.
Example 1 A sample of inhibitor oil prepared by the vacuum distillation of hardwood settled tar, having an atmospheric boiling range of 230 C.- 297" C., a specific gravity of 1.093 at 15.6 C./ 15.6 C., and a color drop value of 22 (A. S. T. M. D-l5634T), was treated according to the invention. A sample of the oil was placed in a closed iron pressure vessel and oxygen passed into the container until a gauge pressure of pounds per square inch wa reached. The gas inlet was then closed and the vessel heated at 100 C. for three hours, during which time the gas pressure rose to pounds and then gradually dropped to 100 pounds. The resultant treated oil was removed and distilled at reduced pressure, the distillate being a yellow-colored inhibitor oil. having a color drop value of 30, which did not change appreciably even on long standing. A small proportion of tarry residue was left in the still.
Example 2 The untreated inhibitor oil of Example 1 was heated at a temperature of 100 C. for one hour mine water.
under oxygen maintained at a constant pressure of 20 pounds gauge, and was then vacuum distilled. A light-yellow inhibitor oil was obtained.
Example 3 Example 4 A charge of ordinary inhibitor oil was heated at a temperature of 70 to 90 C. for 24 hours, during which time air was blown continuously through the hot oil. The product was then vacuum distilled, the distillate being a light-yellow inhibitor oil as in the receding examples.
Example 5 In a series of tests, ordinary inhibitor oil was mixed with a small proportion of each of the following oxidizing agents: nitric acid, aqueous potassium permanganate, manganese dioxide, yellow mercuric oxide, mercuric acetate, potassium chlorate, sulfuric acid, and saturated bro- Each test sample was heated at a temperature of 40 C. for to hours followed by a further heating at 100 to 120 C. for two hours, and was then distilled at reduced pressure. In every instance, the distillate was a stable light-colored inhibitor oil having gasoline gum-inhibiting properties at least equal to those of ordinary inhibitor oil.
It is to-be understood that the process of the invention is applicable to the treatment of inhibitor oil as prepared from settled tar from the destruction distillation of any ligno-cellulosic substance, particularly hardwoods, such as birch and maple, as'well as softer woods such as hemlock, and other like materials, including peat and rotten wood. The process is ordinarily'applied to the inhibitor oil itself, or to a mixture of all the fractions obtained by distilling settled tar under reduced pressure, excluding the lowest boiling fraction which essentially comprises methanol products, water, and acetic acid. However, it is also within the scope of the invention to treat "settled tar or other substance containing the inhibitor oil with an oxidizing agent, and thereafter to distill the treated product to separate the improved light-colored stable inhibitor oil of the invention.
Other modes of applying the principle of the invention may be employed instead of those explained, change being made as regards the details disclosed, provided the method or product stated in any of the following claims, or the equivalent thereof, be employed.
We claim:
1. The method which comprises subjecting the inhibitor oil derived from the tarry products of wood distillation to the action of an oxidizing agent, and separating the substantially unoxidized fraction from the tarry oxidation products, the product so obtained being light-colored, miscible with gasoline, and eifective as an inhibitor in preventing -gum formation in gasoline and like petroleum products.
2. The method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation, which comprises subjecting the said oil to the action of a small proportion of an oxidizing agent, and distilling the treated product, to recover as distillate a light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
3. The methodof treating the inhibitor oil derived by distillation from the tarry products of wood distillation, which comprises subjecting the said oil to the action of a small proportion of an inorganic oxidizing agent and distilling the resulting product, to recover as distillate a lightcolored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
4. The method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation, which comprises subjecting the said oil to the action of a small proportion of a gaseous inorganic oxidizing agent, and distilling the resulting product, to recover as distillate a light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
5. The method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation, which comprises subjecting the said oil to the action of a small proportion of a volatile liquid inorganic oxidizing agent, and distilling the resulting product, to recover as distillate a light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum formation in gasoline and like petroleum products.
6. The method of treating the inhibitor oil derived by distillation from the tarry products of wood distillation which comprises heating the said oil at a temperature between 70 and C. and passing air therethrough, and thereafter distilling the treated oil to recover as distillate a. light-colored oil, miscible with gasoline, and effective as an inhibitor in preventing gum forma: tion ingasoline and like petroleum products.
'7. In a method of treating the mixture of all the fractions obtained by distilling settled tar" under reduced pressure except the lowest boiling fraction essentially comprising methanol prod ucts, water, and acetic acid, said mixture of fractions containing inhibitor oil, the steps which comprise subjecting the said mixture to the action of an oxidizing agent, and thereafter fractionally distilling the treated mixture to recover the fraction having an atmospheric boiling range of 220 C. to 320 C., this fraction being a lightcolored oil, miscible with gasoline, and effective as an inhibitor for preventing gum formation in gasoline and like petroleum products.
8. The method of treating the tarry mixture derived from the destructive distillation of wood and known as settled tar, said mixture containing inhibitor oil, which comprises subjecting the said mixture to the action of an oxidizing agent, and thereafter fractionally distilling the treated mixture to recover the fraction having an atmospheric boiling range of 220 to 320 C., the said fraction being a light-colored oil, miscible with gasoline, and effective as an inhibitor for preventing gum formation in gasoline and like petroleum products.
ALFRED A. CAMlH-LI. MALCOLM K. JOHNSTON.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US298918A US2246973A (en) | 1939-10-11 | 1939-10-11 | Treatment of wood tar distillate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US298918A US2246973A (en) | 1939-10-11 | 1939-10-11 | Treatment of wood tar distillate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2246973A true US2246973A (en) | 1941-06-24 |
Family
ID=23152548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US298918A Expired - Lifetime US2246973A (en) | 1939-10-11 | 1939-10-11 | Treatment of wood tar distillate |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2246973A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2908719A (en) * | 1959-10-13 | Recovery of dialkyl ethers of s-alkyl- | ||
| US2964569A (en) * | 1956-11-29 | 1960-12-13 | Universal Oil Prod Co | Production of a concentrate of dimethyl ethers of 5-alkylpyrogallols |
| US3046217A (en) * | 1959-05-15 | 1962-07-24 | United States Steel Corp | Method of preparing improved wood preservative from coal tar creosote |
| US3864096A (en) * | 1973-01-04 | 1975-02-04 | Universal Oil Prod Co | Process for converting cellulose |
| US3864097A (en) * | 1973-01-15 | 1975-02-04 | Universal Oil Prod Co | Process for converting cellulose |
-
1939
- 1939-10-11 US US298918A patent/US2246973A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2908719A (en) * | 1959-10-13 | Recovery of dialkyl ethers of s-alkyl- | ||
| US2964569A (en) * | 1956-11-29 | 1960-12-13 | Universal Oil Prod Co | Production of a concentrate of dimethyl ethers of 5-alkylpyrogallols |
| US3046217A (en) * | 1959-05-15 | 1962-07-24 | United States Steel Corp | Method of preparing improved wood preservative from coal tar creosote |
| US3864096A (en) * | 1973-01-04 | 1975-02-04 | Universal Oil Prod Co | Process for converting cellulose |
| US3864097A (en) * | 1973-01-15 | 1975-02-04 | Universal Oil Prod Co | Process for converting cellulose |
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