WO2001064622A2 - Process for the preparation of a dry suspension of an ammonium halide - Google Patents

Process for the preparation of a dry suspension of an ammonium halide Download PDF

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Publication number
WO2001064622A2
WO2001064622A2 PCT/EP2001/001985 EP0101985W WO0164622A2 WO 2001064622 A2 WO2001064622 A2 WO 2001064622A2 EP 0101985 W EP0101985 W EP 0101985W WO 0164622 A2 WO0164622 A2 WO 0164622A2
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WIPO (PCT)
Prior art keywords
dry
amine
halide
process according
suspension
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PCT/EP2001/001985
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French (fr)
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WO2001064622A3 (en
Inventor
Auke Gerardus Talma
Gerard Smit
Lambertus Gerhardus Johannus Olde Hanter
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Akzo Nobel N.V.
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Priority to AU2001240646A priority Critical patent/AU2001240646A1/en
Publication of WO2001064622A2 publication Critical patent/WO2001064622A2/en
Publication of WO2001064622A3 publication Critical patent/WO2001064622A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/65—Metal complexes of amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton

Definitions

  • This invention pertains to a process for the preparation of a dry suspension of an ammonium halide.
  • a dry powder can also be obtained from the aqueous solution by (spray-)drying the solution to obtain a dry powder of the hygroscopic quaternary ammonium halide, which can be subsequently dispersed in an inert dry solvent to obtain a dry suspension.
  • the process contains at least two reaction steps and, more significantly, contains a stage wherein the ammonium halide is in an aqueous medium.
  • Such media are extremely corrosive, which lead to the necessity to use unusual and expensive materials for making the equipment, or otherwise the (spray-)drying apparatus will be seriously damaged as a result and need regular cleaning and repair.
  • the process gives amine halide-containing waste water as a side- product, which leads to environmental problems.
  • a process was found for the preparation of a dry suspension of an ammonium halide, comprising the step of intimately mixing a dry amine with a dry halide donor in a dry, inert solvent, not being ether, under an inert atmosphere, in a first vessel to a suspension, after which the suspension, which is essentially free from unreacted amine and halide donor, is continuously transferred to a second vessel for collecting said suspension.
  • the term "essentially free from” means that the amount of unreacted amine and halide donor is so low that no salt is formed in the gasphase of the second vessel.
  • the amount of unreacted amine or halide donor is less than 5% by weight of the added reactant. More preferably they are present in an amount less than 1% by weight, and most preferably in an amount less than 0,5% by weight, all based on the amount of the added reactants.
  • the intimate mixing is preferably done in the chamber of a centrifugal pump that acts as the first vessel, to prevent loss of the gases, in order to generate a proper suspension, and to prevent salt formation in the gas phase, which can give rise to the formation of a spray, and can give blockage of the system.
  • the dry amine may be any amine compound or mixture of amine compounds suitable for the preparation of ammonium salts.
  • Preferred amine compounds useful in this invention have at least one alkyl substituent, but may contain as many as three alkyl substituents on the nitrogen atom.
  • the alkyl substituents of the amine may form ring systems, in particular a monocyclic or bicyclic ring.
  • one or two of the substituents may be of an aromatic nature, such as aryl groups, but this is not preferred.
  • the alkyl and aryl groups may be further substituted with additional groups, for instance, with alkyl and/or aryl groups.
  • the amine compound substituents may contain one or more hetero atoms, in particular nitrogen and/or oxygen. In order to obtain an ionic liquid with acceptable viscosity, however, the substituents preferably are limited to types with fewer than 30, preferably fewer than 20 carbon atoms.
  • Such compounds may be represented by the formula:
  • R 1-3 are independently selected from H, with the proviso that not all three of R ⁇ are H, and linear or branched C ⁇ -30 hydrocarbyl, optionally containing further O and/or N atoms, while Ri and R 2 may be linked to form a cyclic structure.
  • Suitable amine compounds include trialkyl amines, such as t methyl amine, triethyl amine, tri-n-propyl amine, t isopropyl amine, tributyl amine, and t cyclohexyl amine, mono- and di-methyl amines, dibutyl amine, N,N-dimethylethyl amine, N,N-dimethylpropyl amine, N,N-diethylmethyl amine.
  • trialkyl amines such as t methyl amine, triethyl amine, tri-n-propyl amine, t isopropyl amine, tributyl amine, and t cyclohexyl amine, mono- and di-methyl amines, dibutyl amine, N,N-dimethylethyl amine, N,N-dimethylpropyl amine, N,N-diethylmethyl amine.
  • guanidine substituted guanidines, pyridine, substituted pyridines, picolines, lutidines, piperazines, quinolines, pipehdines, N-alkyl imidazoles, and N-alkyl imidazolines.
  • the process of this invention is especially useful for dry amine with a boiling point lower than 140°C, since salts thereof most easily form a spray. These amines cannot properly be used in conventional processes because of the formation of salt in the gas phase.
  • the dry amine therefore, preferably is selected from trimethyl amine, dimethyl amine, methyl amine, triethyl amine, diethyl amine, ethyl amine, and mixtures thereof.
  • the halide donor is selected from hydrohalic acids, halo substituted methanes, and mixtures thereof. Halo substituted alkyls with more than one carbon atom were found to react with the amines at an unfavorable rate.
  • the halo atoms in these compounds are selected from chioro, bromo, iodo, and fluoro. Preferred is the use of monochloro or monobromo compounds such as HCI, HBr, CH 3 CI and CH 3 Br. More preferred as a halide donor is dry hydrochloric acid.
  • dry means that the amine and the halide donor contain less than 5 wt.% water, preferably less than 1 wt.%.
  • the process is preferably performed in an alkane with a boiling point >65°C
  • the dry solvent contains less than 5 wt % water, preferably less than 1 wt %
  • the alkane may be branched or unbranched Preferred alka ⁇ es are heptane or octane, or a mixture thereof
  • the process can be performed in any suitable pump connected to a hold vessel
  • the process is performed in a centrifugal type of pump at atmospheric pressure to a pressure of 50 MPa, or more
  • the process is performed in the chamber of a centrifugal pump
  • the process is usually performed adiabatically at a temperature below about 100°C, and preferably is performed at reflux temperature in order to remove the excess heat of reaction
  • reaction is further performed under an inert dry atmosphere
  • an inert atmosphere is secured by a commonly used inert gas, such as nitrogen, argon,
  • any mixing method that prevents the formation of lumps is suitable Examples of suitable mixing methods are centrifugal pumps, high- shear, (lnter-)M ⁇ g, ultra-Turrax, and ultrasonic homogenization methods Other methods that are equally effective in preventing the formation of lumps can also be used
  • the dry suspension of an ammonium hahde can be used for various applications, such as in disinfectants, fertilizers, and pharmaceutical intermediates, and preferably for making ionic liquids
  • the suspension of the invention is further subjected to a reaction step wherein the dry suspension of the ammonium halide is reacted with a metal halide to obtain a dry ionic liquid
  • the solvent should be immiscible with the ionic liquid
  • the preferred alkanes are immiscible with the ionic liquids and therefore are very useful as solvent
  • the advantage of this method is that the amine salt needs not to be isolated as a dry powder, making the material with its corrosive character easy and straightforward to handle, and eliminating several processing steps such as filtration, drying, and solid charging to the reactor for the ionic liquids synthesis.
  • the metal halide is preferably selected from iron thhalide, copper monohalide, zinc dihalide, aluminum trihalide, alkyl aluminum dihalide, and dialkyl aluminum halide. Most preferably, the metal halide is aluminum trichloride.
  • Methods of making ionic liquids from the dry suspensions of ammonium halides are known in the art, for instance from European application 98203051. However, the solvent used therein is ether, which is excluded from the present invention. Other reaction conditions disclosed therein for making ionic liquids are incorporated by reference.
  • ionic liquid is used to denominate all materials that are liquid at a temperature below 100°C at atmospheric pressure and are fused salt compositions comprising a mixture of a metal halide and an alkyl-containing amine salt.
  • the ionic liquid is liquid at temperatures below 60°C, more preferably below 30°C, at atmospheric pressure.
  • a double walled 3-I reactor equipped with a 6-blade impeller stirrer of 1/3 diameter of the vessel, a heating/cooling system, a reflux condenser, and a thermometer was charged with 1.1 kg of n-heptane.
  • the reactor was purged with dry nitrogen.
  • the reactor contained also an external liquid loop with a centrifugal type of circulation pump.
  • the reactor was stirred gently in order to obtain an as clear as possible upper layer from which the circulation flow of 300 l/hr was taken.
  • the salt was formed immediately in the chamber of the pump and was discharged into the reactor, in which it settled.
  • the solvent was allowed to warm to reflux temperature by the heat of the reaction. In this manner a 17 wt.% suspension of trimethyl amine hydrochloride was obtained. This suspension could be used without further purification..
  • the circulation flow was stopped and to the reactor, containing the suspension, aluminum trichloride was added until the molar ratio TMA.HCI to AICI 3 was 1 :1.9.
  • the reactor was stirred until all solid AICl 3 has been disappeared.
  • the circulation of ionic liquid and solvent was started again in order to clean the circulation system from the TMA.HCI solids. After separation of the ionic liquid and the solvent, the bottom layer was discharged as ionic liquid and the upper solvent layer could be re-used in a next batch.
  • Example 2 The same procedure as described in Examplel was followed, but instead of trimethyl amine gas, triethyl amine (liquid) (238 g) was used. The triethyl amine was also fed to the chamber of the pump. In this manner a 22 wt.% suspension of triethyl amine hydrochloride was obtained, to which aluminum trichloride was added as described in Example 1 to obtain the ionic liquid of TEA.HCI and AICI 3 .
  • trimethyl amine gas triethyl amine (liquid) (238 g) was used.
  • the triethyl amine was also fed to the chamber of the pump. In this manner a 22 wt.% suspension of triethyl amine hydrochloride was obtained, to which aluminum trichloride was added as described in Example 1 to obtain the ionic liquid of TEA.HCI and AICI 3 .

Abstract

The invention pertains to a process for the preparation of a dry suspension of an ammonium halide, comprising the step of intimately mixing a dry amine with a dry halide donor in a dry, inert solvent, not being ether, under an inert atmosphere, in a first vessel to a suspension, after which the suspension, which is essentially free from unreacted amine and halide donor, is continuously transferred to a second vessel for collecting said suspension.

Description

PROCESS FOR THE PREPARATION OF A DRY SUSPENSION OF AN AMMONIUM HALIDE
This invention pertains to a process for the preparation of a dry suspension of an ammonium halide.
Processes for the preparation of (aqueous) amine salt solutions are known, int. al. from DD241591 , RO65420, JP 08217730, and JP 08319259, wherein an aqueous solution of an amine derivative is reacted with an aqueous solution of an acid, for instance aqueous hydrochloric acid, to obtain an aqueous solution of a quaternary ammonium halide. Dry quaternary ammonium halide salts are also known. A common procedure is disclosed in Organic Synthesis Collective. Volume I, 2nd edition, page 531 , where dry gases are reacted in the gas phase. This procedure has the disadvantage that the salt is formed in the gas phase as a fine spray, which leads to problems with blockages of linings connected to the system and with handling of the solid, which is not free-floating and forms a solid mass. A dry powder can also be obtained from the aqueous solution by (spray-)drying the solution to obtain a dry powder of the hygroscopic quaternary ammonium halide, which can be subsequently dispersed in an inert dry solvent to obtain a dry suspension.
This method, however, suffers from a number of drawbacks. The process contains at least two reaction steps and, more significantly, contains a stage wherein the ammonium halide is in an aqueous medium. Such media are extremely corrosive, which lead to the necessity to use unusual and expensive materials for making the equipment, or otherwise the (spray-)drying apparatus will be seriously damaged as a result and need regular cleaning and repair. Further, the process gives amine halide-containing waste water as a side- product, which leads to environmental problems.
Therefore, there is a serious need to prevent aqueous solutions at any stage of this process. The present invention provides a solution to this problem. According to the present invention, a process was found for the preparation of a dry suspension of an ammonium halide, comprising the step of intimately mixing a dry amine with a dry halide donor in a dry, inert solvent, not being ether, under an inert atmosphere, in a first vessel to a suspension, after which the suspension, which is essentially free from unreacted amine and halide donor, is continuously transferred to a second vessel for collecting said suspension.
The term "essentially free from" means that the amount of unreacted amine and halide donor is so low that no salt is formed in the gasphase of the second vessel. Preferably, the amount of unreacted amine or halide donor is less than 5% by weight of the added reactant. More preferably they are present in an amount less than 1% by weight, and most preferably in an amount less than 0,5% by weight, all based on the amount of the added reactants.
The intimate mixing is preferably done in the chamber of a centrifugal pump that acts as the first vessel, to prevent loss of the gases, in order to generate a proper suspension, and to prevent salt formation in the gas phase, which can give rise to the formation of a spray, and can give blockage of the system. The dry amine may be any amine compound or mixture of amine compounds suitable for the preparation of ammonium salts. Preferred amine compounds useful in this invention have at least one alkyl substituent, but may contain as many as three alkyl substituents on the nitrogen atom. The alkyl substituents of the amine may form ring systems, in particular a monocyclic or bicyclic ring. Also, one or two of the substituents may be of an aromatic nature, such as aryl groups, but this is not preferred. The alkyl and aryl groups may be further substituted with additional groups, for instance, with alkyl and/or aryl groups. Also, the amine compound substituents may contain one or more hetero atoms, in particular nitrogen and/or oxygen. In order to obtain an ionic liquid with acceptable viscosity, however, the substituents preferably are limited to types with fewer than 30, preferably fewer than 20 carbon atoms. Such compounds may be represented by the formula:
N-R, R/ 3 2 , wherein
R1-3 are independently selected from H, with the proviso that not all three of R^ are H, and linear or branched Cι-30 hydrocarbyl, optionally containing further O and/or N atoms, while Ri and R2 may be linked to form a cyclic structure.
Typical examples of suitable amine compounds include trialkyl amines, such as t methyl amine, triethyl amine, tri-n-propyl amine, t isopropyl amine, tributyl amine, and t cyclohexyl amine, mono- and di-methyl amines, dibutyl amine, N,N-dimethylethyl amine, N,N-dimethylpropyl amine, N,N-diethylmethyl amine. guanidine, substituted guanidines, pyridine, substituted pyridines, picolines, lutidines, piperazines, quinolines, pipehdines, N-alkyl imidazoles, and N-alkyl imidazolines.
The process of this invention is especially useful for dry amine with a boiling point lower than 140°C, since salts thereof most easily form a spray. These amines cannot properly be used in conventional processes because of the formation of salt in the gas phase. The dry amine therefore, preferably is selected from trimethyl amine, dimethyl amine, methyl amine, triethyl amine, diethyl amine, ethyl amine, and mixtures thereof.
The halide donor is selected from hydrohalic acids, halo substituted methanes, and mixtures thereof. Halo substituted alkyls with more than one carbon atom were found to react with the amines at an unfavorable rate. The halo atoms in these compounds are selected from chioro, bromo, iodo, and fluoro. Preferred is the use of monochloro or monobromo compounds such as HCI, HBr, CH3CI and CH3Br. More preferred as a halide donor is dry hydrochloric acid.
The term "dry" means that the amine and the halide donor contain less than 5 wt.% water, preferably less than 1 wt.%. The process is preferably performed in an alkane with a boiling point >65°C The dry solvent contains less than 5 wt % water, preferably less than 1 wt % The alkane may be branched or unbranched Preferred alkaπes are heptane or octane, or a mixture thereof
The process can be performed in any suitable pump connected to a hold vessel Preferably, the process is performed in a centrifugal type of pump at atmospheric pressure to a pressure of 50 MPa, or more Most preferably, the process is performed in the chamber of a centrifugal pump The process is usually performed adiabatically at a temperature below about 100°C, and preferably is performed at reflux temperature in order to remove the excess heat of reaction
The reaction is further performed under an inert dry atmosphere An inert atmosphere is secured by a commonly used inert gas, such as nitrogen, argon,
It is necessary to intimately mix the suspension formed in order to prevent the formation of lumps Any mixing method that prevents the formation of lumps is suitable Examples of suitable mixing methods are centrifugal pumps, high- shear, (lnter-)Mιg, ultra-Turrax, and ultrasonic homogenization methods Other methods that are equally effective in preventing the formation of lumps can also be used
The dry suspension of an ammonium hahde can be used for various applications, such as in disinfectants, fertilizers, and pharmaceutical intermediates, and preferably for making ionic liquids When ionic liquids are made, the suspension of the invention is further subjected to a reaction step wherein the dry suspension of the ammonium halide is reacted with a metal halide to obtain a dry ionic liquid The solvent should be immiscible with the ionic liquid The preferred alkanes are immiscible with the ionic liquids and therefore are very useful as solvent The advantage of this method is that the amine salt needs not to be isolated as a dry powder, making the material with its corrosive character easy and straightforward to handle, and eliminating several processing steps such as filtration, drying, and solid charging to the reactor for the ionic liquids synthesis.
For making ionic liquids the metal halide is preferably selected from iron thhalide, copper monohalide, zinc dihalide, aluminum trihalide, alkyl aluminum dihalide, and dialkyl aluminum halide. Most preferably, the metal halide is aluminum trichloride. Methods of making ionic liquids from the dry suspensions of ammonium halides are known in the art, for instance from European application 98203051. However, the solvent used therein is ether, which is excluded from the present invention. Other reaction conditions disclosed therein for making ionic liquids are incorporated by reference.
The term "ionic liquid" is used to denominate all materials that are liquid at a temperature below 100°C at atmospheric pressure and are fused salt compositions comprising a mixture of a metal halide and an alkyl-containing amine salt. Preferably, the ionic liquid is liquid at temperatures below 60°C, more preferably below 30°C, at atmospheric pressure.
The invention is further illustrated by the following examples.
Example 1
A double walled 3-I reactor equipped with a 6-blade impeller stirrer of 1/3 diameter of the vessel, a heating/cooling system, a reflux condenser, and a thermometer was charged with 1.1 kg of n-heptane. The reactor was purged with dry nitrogen. The reactor contained also an external liquid loop with a centrifugal type of circulation pump. The reactor was stirred gently in order to obtain an as clear as possible upper layer from which the circulation flow of 300 l/hr was taken. To the pump were fed 140 g (= 52.9 I) of trimethyl amine gas and 86 g (= 53 I) of dry hydrochloric acid gas. The salt was formed immediately in the chamber of the pump and was discharged into the reactor, in which it settled. The solvent was allowed to warm to reflux temperature by the heat of the reaction. In this manner a 17 wt.% suspension of trimethyl amine hydrochloride was obtained. This suspension could be used without further purification.. The circulation flow was stopped and to the reactor, containing the suspension, aluminum trichloride was added until the molar ratio TMA.HCI to AICI3 was 1 :1.9. The reactor was stirred until all solid AICl3 has been disappeared. Then during a short time the circulation of ionic liquid and solvent was started again in order to clean the circulation system from the TMA.HCI solids. After separation of the ionic liquid and the solvent, the bottom layer was discharged as ionic liquid and the upper solvent layer could be re-used in a next batch.
Example 2
The same procedure as described in Examplel was followed, but instead of trimethyl amine gas, triethyl amine (liquid) (238 g) was used. The triethyl amine was also fed to the chamber of the pump. In this manner a 22 wt.% suspension of triethyl amine hydrochloride was obtained, to which aluminum trichloride was added as described in Example 1 to obtain the ionic liquid of TEA.HCI and AICI3.

Claims

Claims:
1. A process for the preparation of a dry suspension of an ammonium halide. comprising the step of intimately mixing a dry amine with a dry halide donor in a dry, inert solvent, not being ether, under an inert atmosphere, in a first vessel to form a suspension, after which the suspension, which is essentially free from unreacted amine and halide donor, is continuously transferred to a second vessel for collecting said suspension.
2. The process according to claim 1 wherein the mixing is performed in the chamber of a centrifugal pump.
3. The process according to claim 1 or 2 wherein the dry amine has a boiling point lower than 140°C.
4. The process according to claim 3 wherein the dry amine is trimethyl amine, dimethyl amine, methyl amine, triethyl amine, diethyl amine, ethyl amine, or a mixture thereof and the dry halide donor is dry hydrochloric acid.
5. The process according to any one of claims 1-4 wherein the solvent is an alkane with a boiling point >65°C, preferably heptane or octane, or a mixture thereof.
6. The process according to any one of claims 1-5 wherein the process of intimately mixing the dry amine with the dry halide donor in the dry, inert solvent is performed in a closed reaction chamber at atmospheric pressure to a pressure of 50 MPa.
7. The process according to any one of claims 1-6 wherein the process is performed at reflux temperature.
8. The process according to any one of claims 1-7 wherein the process is performed adiabatically.
9. The process according to any one of claims 1-8 wherein the process is followed by a reaction step wherein the dry suspension of the quaternary ammonium halide is reacted with a metal halide to obtain a dry ionic liquid.
10. The process according to claim 9 wherein the metal halide is selected from iron trihalide, copper monohalide, zinc dihalide, aluminum trihalide, alkyl aluminum dihalide, and dialkyl aluminum halide.
11. The process according to claim 9 wherein the metal halide is aluminum trichloride.
PCT/EP2001/001985 2000-03-01 2001-02-20 Process for the preparation of a dry suspension of an ammonium halide WO2001064622A2 (en)

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EP00200736.7 2000-03-01

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003089389A3 (en) * 2002-04-22 2004-03-18 Chevron Phillips Chemical Co Method for manufacturing ionic liquid catalysts
US7259284B2 (en) 2000-05-31 2007-08-21 Chevron Phillips Chemical Company, Lp Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts
US7309805B2 (en) 2003-10-31 2007-12-18 Chevron Phillips Chemical Company Lp Method and system to contact an ionic liquid catalyst with oxygen to improve a chemical reaction
US7351780B2 (en) 2002-04-22 2008-04-01 Chevron Phillips Chemical Company, Lp Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts
US7951889B2 (en) 2003-10-31 2011-05-31 Chevron Phillips Chemical Company Lp Method and system to add high shear to improve an ionic liquid catalyzed chemical reaction
CN106560467A (en) * 2016-06-27 2017-04-12 宁夏海诚电化信息科技有限公司 Trimethylamine hydrochloride production process

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US1303624A (en) * 1917-09-21 1919-05-13 Du Pont Process of producing anilin hydrochlorid.
US1929950A (en) * 1929-09-14 1933-10-10 Dow Chemical Co Amine hydrohalide manufacture
US5824832A (en) * 1996-07-22 1998-10-20 Akzo Nobel Nv Linear alxylbenzene formation using low temperature ionic liquid
EP0989134A1 (en) * 1998-09-11 2000-03-29 Akzo Nobel N.V. Process for the in situ preparation of an ionic liquid
WO2000041809A1 (en) * 1999-01-15 2000-07-20 Bp Chemicals Limited Ionic liquid catalyst for alkylation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1303624A (en) * 1917-09-21 1919-05-13 Du Pont Process of producing anilin hydrochlorid.
US1929950A (en) * 1929-09-14 1933-10-10 Dow Chemical Co Amine hydrohalide manufacture
US5824832A (en) * 1996-07-22 1998-10-20 Akzo Nobel Nv Linear alxylbenzene formation using low temperature ionic liquid
EP0989134A1 (en) * 1998-09-11 2000-03-29 Akzo Nobel N.V. Process for the in situ preparation of an ionic liquid
WO2000041809A1 (en) * 1999-01-15 2000-07-20 Bp Chemicals Limited Ionic liquid catalyst for alkylation

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7259284B2 (en) 2000-05-31 2007-08-21 Chevron Phillips Chemical Company, Lp Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts
WO2003089389A3 (en) * 2002-04-22 2004-03-18 Chevron Phillips Chemical Co Method for manufacturing ionic liquid catalysts
US6984605B2 (en) 2002-04-22 2006-01-10 Chevron Phillips Chemical Company, Lp Method for manufacturing ionic liquid catalysts
US7351780B2 (en) 2002-04-22 2008-04-01 Chevron Phillips Chemical Company, Lp Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts
US7615598B2 (en) 2002-04-22 2009-11-10 Chevron Phillips Chemical Company Lp Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts
US7309805B2 (en) 2003-10-31 2007-12-18 Chevron Phillips Chemical Company Lp Method and system to contact an ionic liquid catalyst with oxygen to improve a chemical reaction
US7951889B2 (en) 2003-10-31 2011-05-31 Chevron Phillips Chemical Company Lp Method and system to add high shear to improve an ionic liquid catalyzed chemical reaction
US8163856B2 (en) 2003-10-31 2012-04-24 Chevron Phillips Chemical Company Lp Method and system to add high shear to improve an ionic liquid catalyzed chemical reaction
CN106560467A (en) * 2016-06-27 2017-04-12 宁夏海诚电化信息科技有限公司 Trimethylamine hydrochloride production process

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