US2164774A - Process of nitrating methane - Google Patents
Process of nitrating methane Download PDFInfo
- Publication number
- US2164774A US2164774A US184386A US18438638A US2164774A US 2164774 A US2164774 A US 2164774A US 184386 A US184386 A US 184386A US 18438638 A US18438638 A US 18438638A US 2164774 A US2164774 A US 2164774A
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- US
- United States
- Prior art keywords
- methane
- nitric acid
- reactants
- nitrating
- reaction
- 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.)
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title description 62
- 238000000034 method Methods 0.000 title description 17
- 230000000802 nitrating effect Effects 0.000 title description 10
- 238000006243 chemical reaction Methods 0.000 description 19
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 18
- 229910017604 nitric acid Inorganic materials 0.000 description 18
- 239000000376 reactant Substances 0.000 description 17
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000012808 vapor phase Substances 0.000 description 7
- 238000006396 nitration reaction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- -1 methane or ethane Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000005297 pyrex Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241001579016 Nanoa Species 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/243—Tubular reactors spirally, concentrically or zigzag wound
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
- B01J19/0013—Controlling the temperature of the process
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/26—Nozzle-type reactors, i.e. the distribution of the initial reactants within the reactor is effected by their introduction or injection through nozzles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00099—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor the reactor being immersed in the heat exchange medium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00105—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling
- B01J2219/00108—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling involving reactant vapours
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
Definitions
- This invention relates to the nitration of methane for formation of nitromethane.
- my method of nitration of methane includes passing the reactants through the 20 heated reaction zone at high velocity and at pres- I sures from atmospheric pressure to about 800 lbs.
- Said mixture of nitric acid vapor and methane may be maintained in the proportion of from about 2 to 40 mols CH4 per mol of HNOa,- preferably 1 mol HNO: to 10 mols of CH4.
- This mixtufe is' then passed, at a velocity represented by a contact time with reaction vessel, of about 0.005 to 1.0 second, depending upon the temperature of the reaction zone, into and through a reaction zone or apparatus, preferably comprised of a tube of Pyrex glass or any suitable metal lined with gold or platinum, maintained at a temperature within the range of about 375 C. to
- I represents a tube through which is passed methane, heated, for example, to about 500-700 C. by a heater (not shown), passing into receiver 2, which surrounds and heats platinum pipe 3, through which passes dilute nitric acid, e. g. of 35-40% concentration.
- the .methane passes then into Pyrex glass coiled tube 4, and mixes with the vapors of nitric acid escaping from the end of the tube 3,,the mixture then passing through the remainder of coil 4 immersed in a bath of molten salt mixture comprising equal parts of KNOa and NaNOa, maintained at a temperature of, for example, 5
- the bath of molten salt, Ll contained many suitable vessel, l2,'is maintained atthe desired temperature by direct heating, submerged electrical heating units, or in any suitable manner.
- I maintain a pressure upon the reactants of about lbs. to about 800 lbs.
- the process of nitrating methane which includes producing contact between methane and nitric acid in a non-ferrous vessel at reaction temperature, both reactants being in the vapor phase, the time of contact in the reaction zone between the reactants being from about 0.005 to about 1.0 second and the reactants under superatmospheric pressure, rapidly removing the reaction mixture from the zone of reaction and cooling it.
- the process of nitrating methane which includes producing contact between methane and nitric acid at a temperature between about 375 C. and about 550 C., in a non-ferrous vessel, both reactants being in the vapor phase, the time of contact in the reaction zone between the reactants being from about 0.005 to about 1.0 second and the reactants under a pressure within the range of atmospheric to about 800 pounds, rapidly removing the reaction mixture from the zone of reaction and cooling it.
- the process of nitrating methane which includes producing contact between methane and nitric acid at a temperature of about 450 C. in a: non-ferrous vessel, both reactants being in the vapor phase, the time of contact in the reaction zone between the reactants being from about 0.005 to about 1.0 second and the reactants being under a pressure within the range of atmospheric to about 800 pounds, rapidly removing the reaction mixture from the zone of reaction and cooling it.
- the process of nitrating methane which in- ,cludes producing contact between methane and nitric acid in a non-ferrous vessel, in the molar ratio of 1 nitric acid to 1'7 of methane, at a temperature of about 460 C., a contact time between the reactants of about .0.l0,second, the reactants being in the vapor phase and under a pressure of about 100 lbs., rapidly removing the reaction mixture from the zone of reaction and cooling it.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Jy 4, 1939. G. K. LANDON PROCESS OF NITRATING METHANE Filed Jan; 11, 1938 METHANE VAPORIZING a MIXING cumaaa PLAT! UM. fuss MO LTEN SALT BATH QONDENSER ECEIVER INVENTOR ATTORNEY Patented July 4, 1939 o rr sr George K. Landon, Wilmington, DeL, assignmto Hercules Powder Company, Wilmington, Del., a corporation of Delaware Application January 11, 1938, Serial No. 184,386
'7 Claims. (01. 260-644) This invention relates to the nitration of methane for formation of nitromethane.
Heretofore it has been known to nitrate paraflin hydrocarbons having from 3 to 8 carbon 5 atoms, e. g. according to the process disclosed in United- States Letters Patent No. 1,967,667. No
attempt was made to use hydrocarbons having,
more than 8 carbon atoms, nor to use the simple hydrocarbons, such as methane or ethane, which 10 have only primary carbon atoms. Later, it was disclosed in United States Letters Patent No.
" 2,071,122 that, by altering the conditions of nitration, ethane could be nitrated.
I have found that methane may be nit irated,
15 by the use of aqueous nitric acid, very simply and at good yields, by the use of the process, in ac- I cordance with this invention.
Specifically, my method of nitration of methane includes passing the reactants through the 20 heated reaction zone at high velocity and at pres- I sures from atmospheric pressure to about 800 lbs.
necessary for its formation; hence it is essential that it be removed from the hot zone very 5 rapidly.
In nitration of ethane, the best yield is obtained at a reaction temperature of about 352 C. and a contact time of the reactants at this temperature of about 9.7 seconds. Attempts to use the above conditions in nitrating methane were unsuccessful.
The method, heretofore used, of vaporizing nitric acid by bubbling the hydrocarbon through a body of nitric acid held at constant tempera- 45 ture makes it difiicult, if not impossible, to feed to the reaction zone anything except a constant boiling mixture. High'pressures are impossible,
because vaporization is prevented unless the nitric acid be raised to a temperature dangerous from the explosive point of view. My improved method avoids these disadvantages.
Furthermore, I have found that, in the nitration of methane, the presence of stainless steel causes decomposition of the nitromethane 55 formed, resulting in extremely low yields. My
improved process avoids this decomposition by the use of apparatus in which the product comes into contact with no ferrous metal, for example, apparatus of glass, glass-lined, gold, platinum, or gold-lined or platinum-lined apparatus, and produces nitromethane at satisfactory yields.
As a specific example of the carrying out of my process I pass methane, preheated to a temperature of, for example, about 500 to about 700 C., into a small chamber, through which passes a small diameter tube carrying aqueous nitric acid under pressure, said tube being preferably constructed of platinum or gold, or lined and coated therewith, said nitric acid thus being converted into vapor and escaping from the extremity of said tube into the heated methane and mixing therewith.
Said mixture of nitric acid vapor and methane may be maintained in the proportion of from about 2 to 40 mols CH4 per mol of HNOa,- preferably 1 mol HNO: to 10 mols of CH4. This mixtufe is' then passed, at a velocity represented by a contact time with reaction vessel, of about 0.005 to 1.0 second, depending upon the temperature of the reaction zone, into and through a reaction zone or apparatus, preferably comprised of a tube of Pyrex glass or any suitable metal lined with gold or platinum, maintained at a temperature within the range of about 375 C. to
about 550 0., preferably about 4(10" C. to 460 0., 80
a contact time of 0.10 second and a pressure of 100 lbs. gauge, I obtained nitromethane at a yield of 45.8%, based upon the HNOa consumed.
Further to explain the process in accordance with my invention, reference is made to the accompanying drawing in which I represents a tube through which is passed methane, heated, for example, to about 500-700 C. by a heater (not shown), passing into receiver 2, which surrounds and heats platinum pipe 3, through which passes dilute nitric acid, e. g. of 35-40% concentration. The .methane passes then into Pyrex glass coiled tube 4, and mixes with the vapors of nitric acid escaping from the end of the tube 3,,the mixture then passing through the remainder of coil 4 immersed in a bath of molten salt mixture comprising equal parts of KNOa and NaNOa, maintained at a temperature of, for example, 5
440-460 C., thence through condenser 5 and to receiver 6, where theliquid products, mainly nitromethane and nitric acid, collect and may be drawn off via valve 1 and pipe 8, while the gas products, mainly unreacted methane and nitrogen oxides, pass off via valve and pipe ID for recovery or waste. a
The bath of molten salt, Ll, contained many suitable vessel, l2,'is maintained atthe desired temperature by direct heating, submerged electrical heating units, or in any suitable manner.
Preferably, I maintain a pressure upon the reactants of about lbs. to about 800 lbs.
What I claim and desire to protect by Letters Patent is:
1. The process of nitrating methane, which includes producing contact between methane and nitric acid in a non-ferrous vessel at reaction temperature, both reactants being in the vapor phase, the time of contact in the reaction zone between the reactants being from about 0.005 to about 1.0 second and the reactants under superatmospheric pressure, rapidly removing the reaction mixture from the zone of reaction and cooling it.
2. The process of nitrating methane, which includes producing contact between methane and nitric acid at a temperature between about 375 C. and about 550 C., in a non-ferrous vessel, both reactants being in the vapor phase, the time of contact in the reaction zone between the reactants being from about 0.005 to about 1.0 second and the reactants under a pressure within the range of atmospheric to about 800 pounds, rapidly removing the reaction mixture from the zone of reaction and cooling it.
3. The process of nitrating methane, which includes producing contact between methane and nitric acid at a temperature of about 450 C. in a: non-ferrous vessel, both reactants being in the vapor phase, the time of contact in the reaction zone between the reactants being from about 0.005 to about 1.0 second and the reactants being under a pressure within the range of atmospheric to about 800 pounds, rapidly removing the reaction mixture from the zone of reaction and cooling it.
4. The process of nitrating' methane, which includes producing contact between methane and nitric acid at a temperature of about 4;60 C'. in a non-ferrous vessel, both reactants being in the vapor phase, the time of contact in the reaction zone between the reactants being about 0.10 sec- 0nd and the reactants being under pressure of about 100 pounds, rapidly removing the reaction mixture from the zone of reaction and cooling it.
5. The process of nitrating methane, which in- ,cludes producing contact between methane and nitric acid in a non-ferrous vessel, in the molar ratio of 1 nitric acid to 1'7 of methane, at a temperature of about 460 C., a contact time between the reactants of about .0.l0,second, the reactants being in the vapor phase and under a pressure of about 100 lbs., rapidly removing the reaction mixture from the zone of reaction and cooling it.
6. The process of nitrating methane which includes producing contact between methane and nitric acid while in the vapor phase in a vessel having a non-ferrous inner surface and at reaction temperature for a period of time within the range of about 0.005 second to about 1.0 second,
rapidly removing the reaction mixture from the reaction zone, and cooling it.
7. The process of nitrating methane which includesvprodueing contact between methane and nitric acid in the vapor phase in a vessel having a non-ferrous inner surface and at a temperature within the range of about 375 C. to about 550 C. for a periodof time within the range of about 0.005 second to about 1.0 second, rapidly removing the reaction mixture from the reaction zone and cooling it.
GEORGE K. LANDON.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US184386A US2164774A (en) | 1938-01-11 | 1938-01-11 | Process of nitrating methane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US184386A US2164774A (en) | 1938-01-11 | 1938-01-11 | Process of nitrating methane |
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US2164774A true US2164774A (en) | 1939-07-04 |
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US184386A Expired - Lifetime US2164774A (en) | 1938-01-11 | 1938-01-11 | Process of nitrating methane |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE950006C (en) * | 1952-07-08 | 1956-10-04 | Hoechst Ag | Process for the nitration of hydrocarbons |
US2885447A (en) * | 1954-08-27 | 1959-05-05 | Union Oil Co | Method for conducting exothermic vapor-phase reactions |
EP0017559A1 (en) * | 1979-03-28 | 1980-10-15 | Societe Chimique De La Grande Paroisse, Azote Et Produits Chimiques | A gas-phase hydrocarbon nitration pressure reactor |
US4329523A (en) * | 1980-09-02 | 1982-05-11 | International Minerals & Chemical Corp. | Process for the nitration of methane |
US4626607A (en) * | 1984-01-27 | 1986-12-02 | Societe Chimique De La Grande Pariosse, Azote Et Produits Chimiques | Process and installation for manufacturing nitromethane |
WO2010076580A1 (en) * | 2006-09-21 | 2010-07-08 | Mariana Arce-Osuna | Iris digester-evaporator interface |
-
1938
- 1938-01-11 US US184386A patent/US2164774A/en not_active Expired - Lifetime
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE950006C (en) * | 1952-07-08 | 1956-10-04 | Hoechst Ag | Process for the nitration of hydrocarbons |
US2885447A (en) * | 1954-08-27 | 1959-05-05 | Union Oil Co | Method for conducting exothermic vapor-phase reactions |
EP0017559A1 (en) * | 1979-03-28 | 1980-10-15 | Societe Chimique De La Grande Paroisse, Azote Et Produits Chimiques | A gas-phase hydrocarbon nitration pressure reactor |
US4518811A (en) * | 1979-03-28 | 1985-05-21 | Societe Chimique De La Grande Paroisse - Azote Et Products Chimiques | Reactor for nitration of hydrocarbons in the gaseous phase under pressure |
US4329523A (en) * | 1980-09-02 | 1982-05-11 | International Minerals & Chemical Corp. | Process for the nitration of methane |
US4626607A (en) * | 1984-01-27 | 1986-12-02 | Societe Chimique De La Grande Pariosse, Azote Et Produits Chimiques | Process and installation for manufacturing nitromethane |
WO2010076580A1 (en) * | 2006-09-21 | 2010-07-08 | Mariana Arce-Osuna | Iris digester-evaporator interface |
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