US3162686A - Preparation of lower tetraalkyl quaternary ammonium nitrates - Google Patents
Preparation of lower tetraalkyl quaternary ammonium nitrates Download PDFInfo
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- US3162686A US3162686A US795867A US79586759A US3162686A US 3162686 A US3162686 A US 3162686A US 795867 A US795867 A US 795867A US 79586759 A US79586759 A US 79586759A US 3162686 A US3162686 A US 3162686A
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- Prior art keywords
- quaternary ammonium
- tetraalkyl quaternary
- halide
- preparation
- nitric acid
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- Expired - Lifetime
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- 238000002360 preparation method Methods 0.000 title claims description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 title description 15
- -1 AMMONIUM HALIDE Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical group OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 16
- 229910017604 nitric acid Inorganic materials 0.000 description 16
- 229910002651 NO3 Inorganic materials 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 150000004820 halides Chemical class 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 2
- WVZHBKZLCQVYPH-UHFFFAOYSA-M trimethyl(propan-2-yl)azanium;bromide Chemical compound [Br-].CC(C)[N+](C)(C)C WVZHBKZLCQVYPH-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PHZIPOUUBUJFKZ-UHFFFAOYSA-N [N+](=O)([O-])[O-].C[N+](C(C)C)(C)C Chemical compound [N+](=O)([O-])[O-].C[N+](C(C)C)(C)C PHZIPOUUBUJFKZ-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- DZMOBTVBSRALSJ-UHFFFAOYSA-N diethyl(dimethyl)azanium;nitrate Chemical compound [O-][N+]([O-])=O.CC[N+](C)(C)CC DZMOBTVBSRALSJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
Definitions
- This invention relates to a process for the preparation of a quaternary ammonium nitrate and more particularly to the preparation of a lower tetraalkyl quaternary ammonium nitrate.
- Lower tetraalkyl quaternary ammonium nitrates have aroused considerable interest in the field of rocket propulsion. These compounds are used primarily as components of liquid rocket fuels, particularly in liquid monopropellants where they contribute to both the oxidizing components and the fuel component.
- the most common method for the preparation of these compounds consists of reacting a tetraalkyl quaternary ammonium halide with silver nitrate in an aqueous solution. In this process the silver nitrate reacts with the tetraalkyl quaternary ammonium forming tetraalkyl quaternary ammonium nitrate and an insoluble silver halide whichprecipitates out and is separated by filtration. Since such agprocess consumes both silver and the halide, it is costly and thus economically impractical for a large scale operation.
- an object of this invention to provide an efiicient process for the preparation of a lower tetraalkyl quaternary ammonium nitrate.
- a further object is to provide a process which does not require expensive reactants and is adaptable to a large scale operation.
- a lower tetraalkyl quaternary ammonium halide with nitric acid in the presence of an unsubstituted branched-chained alkanol having from 4 to 6 carbon atoms.
- the tetraalkyl ammonium halide reacts with the acid and is converted to the nitrate salt.
- the hydrogen halide formed by the reaction of the nitric acid and the tetraalkyl quaternary ammonium halide reacts with the alcohol diluent to form water and an alkyl halide.
- R R R and R represent an alkyl radical having from 1 to 4 carbon atoms may be thus prepared.
- Illustrative examples of these compounds, which are finding wide utility as liquid rocket fuels, are tetramethyl ammonium nitrate, trimethylisopropyl ammonium nitrate, and diethyldimethyl ammonium nitrate.
- a corresponding lower tetraalkyl quaternary ammonium halide is used as a reactant.
- the halide has a total of from 4 to 7 carbon atoms and a general formula:
- R R Rz Ri
- R R R and R represent a lower alkyl radical of from 1 to 4 carbon atoms as described above and X represents a halogen selected from the group consisting of bromine and chlorine.
- a bromide salt is preferred.
- These halide reactants may be prepared by known suitable methods, such as by the reaction of a tertiary amine with a monoalkyl halide.
- a diluent of a branch-chained alkanol having from 4 to 6 carbon atoms such as isopropyl, secondary butyl, tertiary butyl, secondary amyl and the like is used.
- Tertiary butyl alcohol is preferred due to the marked advantage in reactivity obtained when this alcohol is used.
- the reactants may be added together in any convenient manner and the reaction takes places smoothly. Usually room temperature is suflicient for the reaction, but sometimes the rapidity of the reaction can be increased by heating the reaction mixture slightly. Usually it is preferred to add the tetraalkyl quaternary ammonium halide to the alkanol in such proportions that a solution containing from 10 to 35 percent by Weight of the halide is obtained. About 15 to 25 percent concentration is preferred. After the tetraalkyl quaternary ammonium halide is dissolved in the alcohol, the nitric acid is then added slowly to the solution.
- At least a stoichiometric amount of nitric acid is required to convert all of the halide to the nitrate form. It has been found advantageous to use a slight stoichiometric excess of the nitric acid, i.e., about 1.1 to 1.2 moles of the acid per mole of the quaternary ammonium halide.
- the nitric acid most conveniently used is the commercially available concentrated nitric acid which contains around 70 Weight percent of the acid. However, other concentrations of the acid of from about 60 weight percent to weight percent may be used.
- the tetraalkyl quaternary ammonium nitrate formed by the reaction of the nitric acid with the halide is insoluble in the reaction mixture and will precipitate out.
- the solid product is recovered from the solution by conventional means.
- the unreacted alkanol, by-product alkyl bromide, and the major portion of the water may be removed by distillation.
- the residue from such distillation may then be purified by washing with a liquid, such as acetone which is not a solvent for the desired product but a solvent for the other constituents in the reacted mass.
- the tetraalkyl ammonium nitrate may then be recovered by filtration and dried.
- Example I In 10 milliliters of tertiary butyl alcohol, 1.8 grams of trimethylisopropyl ammonium bromide were dissolved. To this solution of the tetramethylisopropyl ammonium bromide, 0.6 milliliter of 70 Weight percent nitric acid was added. The mixture was subjected to a mild agitation for about 5 minutes and then distilled to remove a major portion of the liquid from the reacted mass. The distillation residue obtained was slurried with a small quantity of acetone and then filtered. The filtered prodnot was further washed with acetone and vacuum dried to obtain the tetramethylisopropyl ammonium nitrate.
- Example II To milliliters of tertiary butyl alcohol, 15.4 grams of tetramethyl ammonium bromide were added. The tetramethyl ammonium bromide was dissolved in the alcohol and then 7.2 milliliters of 70 percent nitric acid was slowly intermixed. The mixture was stirred and warmed gently to about 60 C. After 30 minutes, the reaction mass was subjected to distillation to remove a major portion of the liquid. As the liquid portion of the reaction mass was removed, a precipitate of the product appeared in the residue. After a major portion of the liquid had been removed, the residue was cooled which precipitated more product. The product was recovered by filtration, washed with acetone, and vacuum dried. The tetrarnethyl ammonium nitrate was recovered in an amount of 10.6 grams which was equivalent to a yield of about 80 percent.
- tetraalkyl quaternary ammonium chloride or bromide having a total of from 4 to 7 carbon atoms may be reacted with nitric acid and the corresponding tetraalkyl quaternary ammonium nitrate obtained.
- tertiary butyl alcohol other branch-chained alcohols having from 4 to 6 carbon atoms may be used in place of tertiary butyl alcohol.
- a process for the preparation of a lower tetraalkyl quaternary ammonium nitrate which comprises intermixing a tetraalkyl quaternary ammonium halide having a total of 7 carbon atoms and the general formula:
- R R R and R represent an alkyl radical having from 1 to 4 carbon atoms and X represents a halogen selected from the group consisting of chlorine and bromine with nitric acid in the presence of an unsubstituted branched-chain alkanol having from 4 to 6 carbon atoms to react the tetraalkyl quaternary ammonium halide with the nitric acid thereby to directly precipitate said lower tctraalkyl quaternary ammonium nitrate in the reaction mixture, and recovering the so-precipitated tetraalkyl quaternary ammonium nitrate formed from the reaction mass.
- R1 R2 Ra ⁇ R4 where R R R and R represent a lower alkyl radical having from 1 to 4 carbon atoms and X represents a halogen selected from the group consisting of chlorine and bromine in an unsubstituted branched-chain alkanol having from 4 to 6 carbon atoms to form a solution containing from 10 to 35 weight percent of the halide, intermixing nitric acid with the solution to react the acid with the tetraalkyl quaternary ammonium halide thereby to directly precipitate said lower tetraalkyl quaternary ammonium nitrate in the reaction mixture, and recovering the so-precipitated tetraalkyl quaternary ammonium nitrate formed by the reaction from the reaction mass.
- R R R and R represent a lower alkyl radical having from 1 to 4 carbon atoms and X represents a halogen selected from the group consisting of chlorine and bromine in an unsubstituted branched-
- tetraalkyl quaternary ammonium halide solution contains from 15 to 25 weight percent of the halide and the nitric acid is intermixed in slightly stoichiometric excess as an aqueous solution containing from to weight percent of the acid.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United- States Patent Delaware No Drawing. Filed Feb. 26, 1959, Ser. No. 795,867
Claims. (Cl. 260--567.6)
This invention relates to a process for the preparation of a quaternary ammonium nitrate and more particularly to the preparation of a lower tetraalkyl quaternary ammonium nitrate.
Lower tetraalkyl quaternary ammonium nitrates have aroused considerable interest in the field of rocket propulsion. These compounds are used primarily as components of liquid rocket fuels, particularly in liquid monopropellants where they contribute to both the oxidizing components and the fuel component. The most common method for the preparation of these compounds consists of reacting a tetraalkyl quaternary ammonium halide with silver nitrate in an aqueous solution. In this process the silver nitrate reacts with the tetraalkyl quaternary ammonium forming tetraalkyl quaternary ammonium nitrate and an insoluble silver halide whichprecipitates out and is separated by filtration. Since such agprocess consumes both silver and the halide, it is costly and thus economically impractical for a large scale operation.
It is, therefore, an object of this invention to provide an efiicient process for the preparation of a lower tetraalkyl quaternary ammonium nitrate. A further object is to provide a process which does not require expensive reactants and is adaptable to a large scale operation.
The above and other objects are attained according to the invention by intermixiug a lower tetraalkyl quaternary ammonium halide with nitric acid in the presence of an unsubstituted branched-chained alkanol having from 4 to 6 carbon atoms. In the presence of the branched chained alkanol, the tetraalkyl ammonium halide reacts with the acid and is converted to the nitrate salt. The hydrogen halide formed by the reaction of the nitric acid and the tetraalkyl quaternary ammonium halide reacts with the alcohol diluent to form water and an alkyl halide.
Lower tetraalkyl quaternary ammonium nitrates having a total of from 4 to 7 carbon atoms and a general formula:
where R R R and R represent an alkyl radical having from 1 to 4 carbon atoms may be thus prepared. Illustrative examples of these compounds, which are finding wide utility as liquid rocket fuels, are tetramethyl ammonium nitrate, trimethylisopropyl ammonium nitrate, and diethyldimethyl ammonium nitrate.
In the preparation of the nitrate a corresponding lower tetraalkyl quaternary ammonium halide is used as a reactant. The halide has a total of from 4 to 7 carbon atoms and a general formula:
R R: Rz Ri where R R R and R represent a lower alkyl radical of from 1 to 4 carbon atoms as described above and X represents a halogen selected from the group consisting of bromine and chlorine. A bromide salt is preferred. These halide reactants may be prepared by known suitable methods, such as by the reaction of a tertiary amine with a monoalkyl halide.
In carrying out the reaction of the tetraalkyl quaternary ammonium halide with the nitric acid, a diluent of a branch-chained alkanol having from 4 to 6 carbon atoms, such as isopropyl, secondary butyl, tertiary butyl, secondary amyl and the like is used. Tertiary butyl alcohol is preferred due to the marked advantage in reactivity obtained when this alcohol is used.
In the presence of the alcohol diluent, the reactants may be added together in any convenient manner and the reaction takes places smoothly. Usually room temperature is suflicient for the reaction, but sometimes the rapidity of the reaction can be increased by heating the reaction mixture slightly. Usually it is preferred to add the tetraalkyl quaternary ammonium halide to the alkanol in such proportions that a solution containing from 10 to 35 percent by Weight of the halide is obtained. About 15 to 25 percent concentration is preferred. After the tetraalkyl quaternary ammonium halide is dissolved in the alcohol, the nitric acid is then added slowly to the solution. At least a stoichiometric amount of nitric acid is required to convert all of the halide to the nitrate form. It has been found advantageous to use a slight stoichiometric excess of the nitric acid, i.e., about 1.1 to 1.2 moles of the acid per mole of the quaternary ammonium halide. The nitric acid most conveniently used is the commercially available concentrated nitric acid which contains around 70 Weight percent of the acid. However, other concentrations of the acid of from about 60 weight percent to weight percent may be used.
The tetraalkyl quaternary ammonium nitrate formed by the reaction of the nitric acid with the halide is insoluble in the reaction mixture and will precipitate out. After the reaction has had time to go essentially to completion the solid product is recovered from the solution by conventional means. For example, the unreacted alkanol, by-product alkyl bromide, and the major portion of the water may be removed by distillation. The residue from such distillation may then be purified by washing with a liquid, such as acetone which is not a solvent for the desired product but a solvent for the other constituents in the reacted mass. The tetraalkyl ammonium nitrate may then be recovered by filtration and dried.
The following examples further illustrate the invention but are not to be construed as limiting it thereto.
Example I In 10 milliliters of tertiary butyl alcohol, 1.8 grams of trimethylisopropyl ammonium bromide were dissolved. To this solution of the tetramethylisopropyl ammonium bromide, 0.6 milliliter of 70 Weight percent nitric acid was added. The mixture was subjected to a mild agitation for about 5 minutes and then distilled to remove a major portion of the liquid from the reacted mass. The distillation residue obtained was slurried with a small quantity of acetone and then filtered. The filtered prodnot was further washed with acetone and vacuum dried to obtain the tetramethylisopropyl ammonium nitrate.
Example II To milliliters of tertiary butyl alcohol, 15.4 grams of tetramethyl ammonium bromide were added. The tetramethyl ammonium bromide was dissolved in the alcohol and then 7.2 milliliters of 70 percent nitric acid was slowly intermixed. The mixture was stirred and warmed gently to about 60 C. After 30 minutes, the reaction mass was subjected to distillation to remove a major portion of the liquid. As the liquid portion of the reaction mass was removed, a precipitate of the product appeared in the residue. After a major portion of the liquid had been removed, the residue was cooled which precipitated more product. The product was recovered by filtration, washed with acetone, and vacuum dried. The tetrarnethyl ammonium nitrate was recovered in an amount of 10.6 grams which was equivalent to a yield of about 80 percent.
Analysis of the product obtained showed that it contained 35.1 percent carbon, 80.8 percent hydrogen and 20.3 percent nitrogen. Theoretical proportions of tetramethyl ammonium nitrate are 35.3 percent carbon, 8.88 percent hydrogen and 20.3 percent nitrogen.
In a manner similar to that described above other tetraalkyl quaternary ammonium chloride or bromide having a total of from 4 to 7 carbon atoms may be reacted with nitric acid and the corresponding tetraalkyl quaternary ammonium nitrate obtained. Also in place of tertiary butyl alcohol other branch-chained alcohols having from 4 to 6 carbon atoms may be used in place of tertiary butyl alcohol.
What is claimed is:
1. A process for the preparation of a lower tetraalkyl quaternary ammonium nitrate, which comprises intermixing a tetraalkyl quaternary ammonium halide having a total of 7 carbon atoms and the general formula:
where R R R and R represent an alkyl radical having from 1 to 4 carbon atoms and X represents a halogen selected from the group consisting of chlorine and bromine with nitric acid in the presence of an unsubstituted branched-chain alkanol having from 4 to 6 carbon atoms to react the tetraalkyl quaternary ammonium halide with the nitric acid thereby to directly precipitate said lower tctraalkyl quaternary ammonium nitrate in the reaction mixture, and recovering the so-precipitated tetraalkyl quaternary ammonium nitrate formed from the reaction mass.
2, A process for the preparation of a lower tetraalkyl formula:
R1 R2 Ra \R4 where R R R and R represent a lower alkyl radical having from 1 to 4 carbon atoms and X represents a halogen selected from the group consisting of chlorine and bromine in an unsubstituted branched-chain alkanol having from 4 to 6 carbon atoms to form a solution containing from 10 to 35 weight percent of the halide, intermixing nitric acid with the solution to react the acid with the tetraalkyl quaternary ammonium halide thereby to directly precipitate said lower tetraalkyl quaternary ammonium nitrate in the reaction mixture, and recovering the so-precipitated tetraalkyl quaternary ammonium nitrate formed by the reaction from the reaction mass.
3. A process according to claim 2 wherein the tetraalkyl quaternary ammonium halide solution contains from 15 to 25 weight percent of the halide and the nitric acid is intermixed in slightly stoichiometric excess as an aqueous solution containing from to weight percent of the acid.
4. A process according to claim 3 wherein the unsubstituted branched-chain alkanol is tertiary butyl alcohol.
5. A process according to claim 4 wherein the tetraalkyl quaternary ammonium halide is trimethylisopropyl ammonium bromide.
References Cited in the file of this patent FOREIGN PATENTS 73 ea Brit i g- 5s
Claims (1)
1. A PROCESS FOR THE PREPARATION OF A LOWER TETRAALKYL QUATERNARY AMMONIUM NITRATE, WHICH COMPRISES INTERMIXING A TETRAALKYL QUATERNARY AMMONIUM HALIDE HAVING A TOTAL OF 7 CARBON ATOMS AND THE GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US795867A US3162686A (en) | 1959-02-26 | 1959-02-26 | Preparation of lower tetraalkyl quaternary ammonium nitrates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US795867A US3162686A (en) | 1959-02-26 | 1959-02-26 | Preparation of lower tetraalkyl quaternary ammonium nitrates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3162686A true US3162686A (en) | 1964-12-22 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US795867A Expired - Lifetime US3162686A (en) | 1959-02-26 | 1959-02-26 | Preparation of lower tetraalkyl quaternary ammonium nitrates |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3162686A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140238328A1 (en) * | 2012-11-02 | 2014-08-28 | Afton Chemical Corporation | Fuel additive for improved performance in direct fuel injected engines |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB735631A (en) * | 1950-09-27 | 1955-08-24 | Milton Antiseptic Ltd | Improvements relating to the preparation of quaternary ammonium compounds |
-
1959
- 1959-02-26 US US795867A patent/US3162686A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB735631A (en) * | 1950-09-27 | 1955-08-24 | Milton Antiseptic Ltd | Improvements relating to the preparation of quaternary ammonium compounds |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140238328A1 (en) * | 2012-11-02 | 2014-08-28 | Afton Chemical Corporation | Fuel additive for improved performance in direct fuel injected engines |
| US9458400B2 (en) * | 2012-11-02 | 2016-10-04 | Afton Chemical Corporation | Fuel additive for improved performance in direct fuel injected engines |
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