WO2017023487A1 - Processes for synthesizing methoxy alkylether quaternary ammonium bromides - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
Definitions
- Methoxy alkylether quaternary ammonium bromides are known to be good complexing agents for use in flow cell batteries.
- current commercial processes for synthesis of methoxy alkylether quaternary ammonium bromides utilize methoxy alkylbromide as a starting material. See, for example, "Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System" By Toshiki Nokami et al, Org. Process Res.
- This invention meets the above-described needs by providing processes for producing methoxy alkylether quaternary ammonium halides, which processes comprise combining components comprising a secondary amine, a first alcohol, an alkali or alkaline metal carbonate, and paraformaldehyde or formaldehyde to form a first combination; heating the first combination to about 20 to 1 30 degrees C; maintaining the first combination at about 20 to 130 degrees C for about 0.5 to 72 hours; distilling light components comprising at least a portion of the first alcohol from the first combination; distilling and recovering a methoxyalkyl ammonium compound from the first combination; combining the recovered methoxyalkyl ammonium compound, an alkly halide, and a second alcohol to form a second combination; heating the second combination to about 20 to 200 degrees C; maintaining the second combination at about 20 to 200 degrees C for about 0.5 to 72 hours; and distilling light components comprising at least a portion of the second alcohol from the second combination, thereby producing a methoxy alky
- this invention provides processes comprising combining pyrrolodine, methanol, potassium carbonate, and paraformaldehyde to form a first combination; heating the first combination to about 20 to 1 30 degrees C; maintaining the first combination at about 20 to 130 degrees C for about 0.5 to 72 hours; distilling light components comprising methanol from the first combination; distilling and recovering N-methoxymethyl pyrrolidium from the first combination; combining the N-methoxymethyl pyrrolidium, butyl bromide, and methanol to form a second
- heating the second combination to about 20 to 200 degrees C;
- methoxymethyl-N-butylpyrrolidinium bromide can be recrystallized in acetone, or other suitable solvent.
- this invention provides processes comprising combining a methoxyalkyl tertiary amine, an alkly halide, and a C-
- this invention provides processes comprising:
- methoxyalkyl ammonium compound, an alkly halide, and a second alcohol to form a second combination (h) heating the second combination to about 20 to 200 degrees C; (i) maintaining the second combination at about 20 to 200 degrees C for about 0.5 to 72 hours; and (j) distilling light components comprising at least a portion of the second alcohol from the second combination, thereby producing a methoxy alkylether quaternary ammonium halide.
- distilling light components comprising at least a portion of the second alcohol from the second combination, thereby producing a methoxy alkylether quaternary ammonium halide.
- methoxy alkylether quaternary ammonium halides are produced by first combining a secondary amine, a first alcohol, preferably a
- -C8 alcohol an alkali or alkaline metal carbonate, and paraformaldehyde or formaldehyde in a first container.
- the contents of the first container are heated to about 20 to 1 30 degrees C, or from about 40 to 90 degrees C, or from about 40 to 45 degrees C, in the presence of an inert gas, and held at about 20 to 130 degrees C, or in a narrower temperature range, for about 0.5 to 72 hours, or from about 0.5 to 1 0 hours, or from about 1 to 2 hours.
- the light components comprising the first alcohol are distilled off under reduced pressure.
- the first alcohol can be recovered and re-used in processes of this invention.
- produced methoxyalkyl ammonium compound is distilled off, preferably at reduced pressure.
- the recovered methoxyalkyl ammonium compound is combined with an alkyl halide and a second alcohol in a second container.
- the first and second containers can be the same or different containers.
- the contents of the second container are heated to about 20 to 200 degrees C in the presence of an inert gas and held at about 20 to 200 degrees C for about 0.5 to 72 hours, or for about 4 to 6 hours.
- the light components comprising MeOH are distilled off under reduced pressure.
- the MeOH can be re-used in processes of this invention. After the distillation, the produced N-methoxymethyl-N-butylpyrrolidium bromide remains in the second container.
- Suitable secondary amines for use in processes of this invention include, without limitation, aliphatic, cyclic, and aromatic secondary amine compounds. Given the teachings of this specification, those skilled in the art have the necessary
- a non-limiting list of some suitable secondary amines includes pyrrolidine, morpholine, piperidine, imidazole, dimethylamine, methyethylamine, methylpropylamine, methylbutylamine, ethylpropylamine and ethylbutylamine.
- -Cs alcohols are preferred.
- the first and second alcohols can be the same or different.
- a non-limiting list of some suitable alcohols includes methanol, ethanol, propanol, butanol and pentanol.
- alkali or alkaline metal carbonates suitable for use in producing a desired methoxy alkylether quaternary ammonium halide.
- a non-limiting list of some suitable carbonates includes potassium carbonate and sodium carbonate.
- inert gases suitable for use in producing a desired methoxy alkylether quaternary ammonium halide A non-limiting list of some suitable inert gases includes nitrogen, helium, and argon.
- alkyl halides suitable for use in producing a desired methoxy alkylether quaternary ammonium halide.
- a non-limiting list of some suitable alkyl halides includes methyl bromide, ethyl bromide, propyl bromide, butyl bromide, pentyl bromide, hexyl bromide, methyl chloride, ethyl chloride, propyl chloride, butyl chloride, pentyl chloride, and hexyl chloride.
- Processes of this invention are suitable for synthesizing many different methoxy alkylether quaternary ammonium bromides. Following are some non-limiting examples of processes according to this invention and the resulting methoxy alkylether quaternary ammonium bromides, in which Ri and R2 are alkyl groups, which can be straight or branched, and are preferably C-
- Heavy hydrocarbon solvents in particular Cs-Ci 6 alkanes, may be utilized in processes according to this invention as deemed suitable.
- suitable heavy hydrocarbon solvents include tetradecane and decane.
- reactor A The contents of reactor A were heated to a temperature within the range of 40-45 degrees C under nitrogen protection.
- the temperature of the contents of reactor A was maintained at a temperature within the range of 40-45 degrees C for 2 hours.
- the light components comprising MeOH, were distilled off under reduced pressure for reuse.
- N-methoxymethyl pyrrolidium was distilled off under reduced pressure.
- N-methoxymethyl-N-butylpyrrolidium bromide was filtered and dried. [0017] If needed, the N-methoxymethyl-N-butylpyrrolidium bromide could be recrystallized in acetone.
- Processes according to this invention are advantageous over prior processes, particularly because the inventors discovered how to synthesize methoxy alkylether uaternary ammonium halides from a methoxy alkyl tertiary amine and an alkyl halide,
- methoxy alkyl halides instead of from an alkyl tertiary amine and a methoxy alkly halide.
- the cost of methoxy alkyl halides, in particular of methoxy alkyl bromides, can be such that processes that require them are not commercially feasible.
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Abstract
Processes for synthesizing methoxy alkylether quaternary ammonium halides from methoxy alkyl tertiary amines and alkyl halides are provided.
Description
Processes for Synthesizing
Methoxy Alkylether Quaternary Ammonium Bromides
BACKGROUND
[0001] Methoxy alkylether quaternary ammonium bromides are known to be good complexing agents for use in flow cell batteries. However, current commercial processes for synthesis of methoxy alkylether quaternary ammonium bromides utilize methoxy alkylbromide as a starting material. See, for example, "Synthesis of Ionic Liquids Equipped with 2-Methoxyethoxymethyl/Methoxymethyl Groups Using a Simple Microreactor System" By Toshiki Nokami et al, Org. Process Res. Dev., 2014, 18 (1 1 ), pp 1367-1371 , and "Quaternary ammonium salt ionic liquid, its preparation and application" by Zhou, Mingjie et al, Faming Zhuanii Shenqing, 102887827, 23 Jan 2013. The required methoxy alkylbromide is a relatively expensive component. It would benefit the industry if methoxy alkylether quaternary ammonium bromides could be provided at a more commercially acceptable cost.
[0002] Therefore, there is a need for processes for synthesizing methoxy alkylether quaternary ammonium bromides that do not require use of methoxy alkylbromide and which provide methoxy alklyether quaternary ammonium bromides at a more
commercially acceptable cost than is currently available.
THE INVENTION
[0003] This invention meets the above-described needs by providing processes for producing methoxy alkylether quaternary ammonium halides, which processes comprise combining components comprising a secondary amine, a first alcohol, an alkali or alkaline metal carbonate, and paraformaldehyde or formaldehyde to form a first combination; heating the first combination to about 20 to 1 30 degrees C; maintaining the first combination at about 20 to 130 degrees C for about 0.5 to 72 hours; distilling light components comprising at least a portion of the first alcohol from the first combination; distilling and recovering a methoxyalkyl ammonium compound from the first combination; combining the recovered methoxyalkyl ammonium compound, an alkly halide, and a second alcohol to form a second combination; heating the second combination to about 20 to 200 degrees C; maintaining the second combination at
about 20 to 200 degrees C for about 0.5 to 72 hours; and distilling light components comprising at least a portion of the second alcohol from the second combination, thereby producing a methoxy alkylether quaternary ammonium halide. If desired, the methoxy alkylether quaternary ammonium halide can be recrystallized in acetone, or other suitable solvent. The first and second alcohols can be the same alcohol, or different alcohols.
[0004] In one application, this invention provides processes comprising combining pyrrolodine, methanol, potassium carbonate, and paraformaldehyde to form a first combination; heating the first combination to about 20 to 1 30 degrees C; maintaining the first combination at about 20 to 130 degrees C for about 0.5 to 72 hours; distilling light components comprising methanol from the first combination; distilling and recovering N-methoxymethyl pyrrolidium from the first combination; combining the N-methoxymethyl pyrrolidium, butyl bromide, and methanol to form a second
combination; heating the second combination to about 20 to 200 degrees C;
maintaining the second combination at reflux for about 0.5 to 72 hours; and distilling light components comprising methanol from the second combination, thereby producing methoxymethyl-N-butylpyrrolidinium bromide. If desired, the
methoxymethyl-N-butylpyrrolidinium bromide can be recrystallized in acetone, or other suitable solvent.
[0005] In another application, this invention provides processes comprising combining a methoxyalkyl tertiary amine, an alkly halide, and a C-| -Cs alcohol to form a
combination; heating the combination to reflux; maintaining the combination at reflux for about 0.5 to 72 hours; and distilling light components comprising at least a portion of the C-| -C8 alcohol from the combination, thereby producing a methoxy alkylether quaternary ammonium halide.
[0006] In yet another application, this invention provides processes comprising:
(a) combining components comprising a secondary amine, a first alcohol, an alkali or alkaline metal carbonate, a Cs-Ci 6 hydrocarbon, and paraformaldehyde or
formaldehyde to form a first combination; (b) heating the first combination to about 20 to
130 degrees C; (c) maintaining the first combination at about 20 to 130 degrees C for about 0.5 to 72 hours; (d) distilling light components comprising at least a portion of the first alcohol from the first combination; (e) distilling and recovering a methoxyalkyl ammonium compound from the first combination; (f) recovering a composition
comprising at least some of any unused portion of the alkali or alkaline metal carbonate and at least some of the Cs-Ci 6 hydrocarbon; (g) combining the recovered
methoxyalkyl ammonium compound, an alkly halide, and a second alcohol to form a second combination; (h) heating the second combination to about 20 to 200 degrees C; (i) maintaining the second combination at about 20 to 200 degrees C for about 0.5 to 72 hours; and (j) distilling light components comprising at least a portion of the second alcohol from the second combination, thereby producing a methoxy alkylether quaternary ammonium halide. Further provided are such processes wherein at least a portion of the alkali or alkaline metal carbonate in (a) is recovered and re-used from (f) of a previously run process having the same features.
Detailed Description
[0007] In processes of this invention, methoxy alkylether quaternary ammonium halides are produced by first combining a secondary amine, a first alcohol, preferably a
C-| -C8 alcohol, an alkali or alkaline metal carbonate, and paraformaldehyde or formaldehyde in a first container. The contents of the first container are heated to about 20 to 1 30 degrees C, or from about 40 to 90 degrees C, or from about 40 to 45 degrees C, in the presence of an inert gas, and held at about 20 to 130 degrees C, or in a narrower temperature range, for about 0.5 to 72 hours, or from about 0.5 to 1 0 hours, or from about 1 to 2 hours. Then the light components comprising the first alcohol are distilled off under reduced pressure. The first alcohol can be recovered and re-used in processes of this invention. Then produced methoxyalkyl ammonium compound is distilled off, preferably at reduced pressure. The recovered methoxyalkyl ammonium compound is combined with an alkyl halide and a second alcohol in a second container. The first and second containers can be the same or different containers. The contents of the second container are heated to about 20 to 200 degrees C in the presence of an inert gas and held at about 20 to 200 degrees C for about 0.5 to 72 hours, or for about 4 to 6 hours. Then the light components comprising MeOH are distilled off under reduced pressure. The MeOH can be re-used in processes of this invention. After the distillation, the produced N-methoxymethyl-N-butylpyrrolidium bromide remains in the second container. If desired, the produced N-methoxymethyl-N-butylpyrrolidium bromide can be recrystallized in acetone.
[0008] Suitable secondary amines for use in processes of this invention include, without limitation, aliphatic, cyclic, and aromatic secondary amine compounds. Given the teachings of this specification, those skilled in the art have the necessary
knowledge to select a secondary amine suitable for use in producing a desired methoxy alkylether quaternary ammonium halide. A non-limiting list of some suitable secondary amines includes pyrrolidine, morpholine, piperidine, imidazole, dimethylamine, methyethylamine, methylpropylamine, methylbutylamine, ethylpropylamine and ethylbutylamine.
[0009] Given the teachings of this specification, those skilled in the art have the necessary knowledge to select alcohols suitable for use in producing a desired methoxy alkylether quaternary ammonium halide. C-| -Cs alcohols are preferred. The first and second alcohols can be the same or different. A non-limiting list of some suitable alcohols includes methanol, ethanol, propanol, butanol and pentanol.
[0010] Given the teachings of this specification, those skilled in the art have the necessary knowledge to select alkali or alkaline metal carbonates suitable for use in producing a desired methoxy alkylether quaternary ammonium halide. A non-limiting list of some suitable carbonates includes potassium carbonate and sodium carbonate.
[0011] Given the teachings of this specification, those skilled in the art have the necessary knowledge to select inert gases suitable for use in producing a desired methoxy alkylether quaternary ammonium halide. A non-limiting list of some suitable inert gases includes nitrogen, helium, and argon.
[0012] Given the teachings of this specification, those skilled in the art have the necessary knowledge to select alkyl halides suitable for use in producing a desired methoxy alkylether quaternary ammonium halide. A non-limiting list of some suitable alkyl halides includes methyl bromide, ethyl bromide, propyl bromide, butyl bromide, pentyl bromide, hexyl bromide, methyl chloride, ethyl chloride, propyl chloride, butyl chloride, pentyl chloride, and hexyl chloride.
[0013] Processes of this invention are suitable for synthesizing many different methoxy alkylether quaternary ammonium bromides. Following are some non-limiting examples of processes according to this invention and the resulting methoxy alkylether quaternary ammonium bromides, in which Ri and R2 are alkyl groups, which can be straight or branched, and are preferably C-|-Cs.
[0014] Heavy hydrocarbon solvents, in particular Cs-Ci 6 alkanes, may be utilized in processes according to this invention as deemed suitable. Without limiting this invention, suitable heavy hydrocarbon solvents include tetradecane and decane.
EXAMPLES
[0015] The following examples are illustrative of the principles of this invention. It is understood that this invention is not limited to any one specific embodiment exemplified herein, whether in the examples or the remainder of this patent application.
EXAMPLE 1.
[0016] In accordance with this invention, the following procedure was used to synthesize N-methoxymethyl-N-butylpyrrolidium bromide:
1 . Pyrrolodine (1 mol), methanol (2mol), potassium carbonate (1 mol),
paraformaldehyde (1 mol) and tetradecane (100ml) were charged to reactor A.
2. The contents of reactor A were heated to a temperature within the range of 40-45 degrees C under nitrogen protection.
3. The temperature of the contents of reactor A was maintained at a temperature within the range of 40-45 degrees C for 2 hours.
4. The light components, comprising MeOH, were distilled off under reduced pressure for reuse.
5. N-methoxymethyl pyrrolidium was distilled off under reduced pressure.
6. The residual potassium carbonate in tetradecane was reserved for reuse, as desired.
7. The N-methoxymethyl pyrrolidium (1 mol), butyl bromide (1 mol) and methanol were charged to reactor B.
8. The contents of reactor B were heated to reflux under nitrogen protection.
9. The contents of reactor B were maintained at reflux for 6 hours.
10. Decane was added to the reactor B.
1 1 . The light components, comprising MeOH, were distilled off under reduced pressure for reuse.
12. Thus, N-methoxymethyl-N-butylpyrrolidium bromide was precipitated in Decane.
13. The N-methoxymethyl-N-butylpyrrolidium bromide was filtered and dried.
[0017] If needed, the N-methoxymethyl-N-butylpyrrolidium bromide could be recrystallized in acetone.
[0018] Processes according to this invention are advantageous over prior processes, particularly because the inventors discovered how to synthesize methoxy alkylether uaternary ammonium halides from a methoxy alkyl tertiary amine and an alkyl halide,
instead of from an alkyl tertiary amine and a methoxy alkly halide. The cost of methoxy alkyl halides, in particular of methoxy alkyl bromides, can be such that processes that require them are not commercially feasible.
[0019] It is to be understood that the reactants and components referred to by chemical name or formula anywhere in the specification or claims hereof, whether referred to in the singular or plural, are identified as they exist prior to being combined with or coming into contact with another substance referred to by chemical name or chemical type (e.g., another reactant, a solvent, or etc.). It matters not what chemical changes, transformations and/or reactions, if any, take place in the resulting
combination or solution or reaction medium as such changes, transformations and/or reactions are the natural result of bringing the specified reactants and/or components together under the conditions called for pursuant to this disclosure. Thus the reactants and components are identified as ingredients to be brought together in connection with performing a desired chemical reaction or in forming a combination to be used in conducting a desired reaction. Accordingly, even though the claims hereinafter may refer to substances, components and/or ingredients in the present tense ("comprises", "is", etc.), the reference is to the substance, component or ingredient as it existed at the time just before it was first contacted, combined, blended or mixed with one or more other substances, components and/or ingredients in accordance with the present disclosure. Whatever transformations, if any, which occur in situ as a reaction is conducted is what the claim is intended to cover. Thus the fact that a substance, component or ingredient may have lost its original identity through a chemical reaction or transformation during the course of contacting, combining, blending or mixing
operations, if conducted in accordance with this disclosure and with the application of common sense and the ordinary skill of a chemist, is thus wholly immaterial for an accurate understanding and appreciation of the true meaning and substance of this disclosure and the claims thereof. As will be familiar to those skilled in the art, the terms "combined", "combining", and the like as used herein mean that the components that are "combined" or that one is "combining" are put into a container with each other. Likewise a "combination" of components means the components having been put together in a container.
[0020] While the present invention has been described in terms of one or more preferred embodiments, it is to be understood that other modifications may be made without departing from the scope of the invention, which is set forth in the claims below.
Claims
1 . A process comprising:
- combining components comprising a secondary amine, a first alcohol, an alkali or alkaline metal carbonate, and paraformaldehyde or formaldehyde to form a first combination;
- heating the first combination to about 20 to 130 degrees C;
- maintaining the first combination at about 20 to 130 degrees C for about 0.5 to about 72 hours;
- distilling light components comprising at least a portion of the first alcohol from the first combination;
- distilling and recovering a methoxyalkyl ammonium compound from the first combination;
- combining the recovered methoxyalkyl ammonium compound, an alkly halide, and a second alcohol to form a second combination;
- heating the second combination to about 20 to 200 degrees C;
- maintaining the second combination at about 20 to 200 degrees C for about 0.5 to about 72 hours; and
- distilling light components comprising at least a portion of the second alcohol from the second combination,
thereby producing a methoxy alkylether quaternary ammonium halide.
2. A process according to claim 1 wherein the secondary amine comprises pyrrolidine.
3. A process according to claim 1 wherein the first alcohol comprises a C-| -Cs alcohol and the second alcohol comprises a C-| -Cs alcohol.
4. A process according to claim 1 wherein the first alcohol and the second alcohol are the same.
5. A process according to claim 1 wherein the first alcohol and the second alcohol are different.
6. A process according to claim 1 wherein the first alcohol comprises methanol, ethanol, propanol, or butanol and wherein the second alcohol comprises methanol, ethanol, propanol, or butanol.
7. A process according to claim 1 wherein the alkali or alkaline metal carbonate comprises potassium carbonate.
8. A process according to claim 1 wherein the alkyl halide comprises methyl bromide, ethyl bromide, propyl bromide, butyl bromide, pentyl bromide, hexyl bromide, methyl chloride, ethyl chloride, propyl chloride, butyl chloride, pentyl chloride, or hexyl chloride.
9. A process according to claim 1 wherein the alkyl halide comprises butyl bromide.
10. A process comprising:
- combining pyrrolodine, methanol, potassium carbonate, and paraformaldehyde to form a first combination;
- heating the first combination to about 20 to 130 degrees C;
- maintaining the first combination at about 20 to 130 degrees C for about 0.5 to about 72 hours;
- distilling light components comprising methanol from the first combination;
- distilling and recovering N-methoxymethyl pyrrolidium from the first
combination;
- combining the N-methoxymethyl pyrrolidium, butyl bromide, and methanol to form a second combination;
- heating the second combination to about 20 to 200 degrees C;
- maintaining the second combination at reflux for about 4 to 10 hours; and
- distilling light components comprising methanol from the second combination, thereby producing methoxymethyl-N-butylpyrrolidium bromide.
1 1 . A process comprising:
- combining a methoxyalkyl tertiary amine, an alkly halide, and a C-| -Cs alcohol to form a combination;
- heating the combination to reflux;
- maintaining the combination at reflux for about 0.5 to 72 hours; and
- distilling light components comprising at least a portion of the C-| -Cs alcohol from the combination,
thereby producing a methoxy alkylether quaternary ammonium halide.
12. A process comprising:
(a) combining components comprising a secondary amine, a first alcohol, an alkali or alkaline metal carbonate, a Cs-Ci 6 hydrocarbon, and paraformaldehyde or formaldehyde to form a first combination;
(b) heating the first combination to about 20 to 1 30 degrees C;
(c) maintaining the first combination at about 20 to 130 degrees C for about 0.5 to 72 hours;
(d) distilling light components comprising at least a portion of the first alcohol from the first combination;
(e) distilling and recovering a methoxyalkyl ammonium compound from the first combination;
(f) recovering a composition comprising at least some of any unused portion of the alkali or alkaline metal carbonate and at least some of the C8-C16 hydrocarbon;
(g) combining the recovered methoxyalkyl ammonium compound, an alkly halide, and a second alcohol to form a second combination;
(h) heating the second combination to about 20 to 200 degrees C;
(i) maintaining the second combination at about 20 to 200 degrees C for about 0.5 to 72 hours; and
(j) distilling light components comprising at least a portion of the second alcohol from the second combination,
thereby producing a methoxy alkylether quaternary ammonium halide.
3. A process according to claim 12 wherein at least a portion of the alkali or alkaline metal carbonate in (a) is recovered and re-used from (f) of a previously run process having the same features as claim 1 2.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1642894A1 (en) * | 2003-07-01 | 2006-04-05 | Otsuka Chemical Company, Limited | Quaternary ammonium salt, electrolyte, and electrochemical device |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1642894A1 (en) * | 2003-07-01 | 2006-04-05 | Otsuka Chemical Company, Limited | Quaternary ammonium salt, electrolyte, and electrochemical device |
Non-Patent Citations (2)
| Title |
|---|
| GERTRUDE MAUD ROBINSON ET AL: "Researches on Pseudo-Bases. Part IV. A New Synthesis of Tertiary Amines of the Form RCH2NR1R2", JOURNAL OF THE CHEMICAL SOCIETY. TRANSACTIONS, vol. 123, 1 January 1923 (1923-01-01), pages 532 - 543, XP055300312 * |
| T. D. STEWART ET AL: "THE BASE STRENGTH OF ALPHA-ALKOXYL AMINES. THE EFFECT OF OXYGEN ON THE BASICITY OF AMINES", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 48, no. 6, 1 June 1926 (1926-06-01), US, pages 1642 - 1655, XP055300122, ISSN: 0002-7863, DOI: 10.1021/ja01417a028 * |
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