WO2015011728A1 - Method for producing alkenone ethers - Google Patents

Method for producing alkenone ethers Download PDF

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Publication number
WO2015011728A1
WO2015011728A1 PCT/IN2014/000487 IN2014000487W WO2015011728A1 WO 2015011728 A1 WO2015011728 A1 WO 2015011728A1 IN 2014000487 W IN2014000487 W IN 2014000487W WO 2015011728 A1 WO2015011728 A1 WO 2015011728A1
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WO
WIPO (PCT)
Prior art keywords
formula
alkyl group
halogen atom
substituted
compound
Prior art date
Application number
PCT/IN2014/000487
Other languages
French (fr)
Inventor
Prabhu BALAJI
Kapil Kumar
Rahul Saxena
Rajdeep Anand
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Srf Limited
Priority date (The priority date 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 date listed.)
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Publication date
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Publication of WO2015011728A1 publication Critical patent/WO2015011728A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives

Definitions

  • the present invention relates to a process for the synthesis of alkenone ethers.
  • alkenone ethers such as 4-alkoxy-l, 1 , l-trifluoro-3-butenone, are building blocks and important precursors for chemical synthesis of agrochemicals or pharmaceuticals.
  • the U.S. Patent No. 5,708,175 provides a process for the preparation of halogenated alkenone ethers by reacting an acid chloride with vinyl ether in the presence of a base at a very low temperature ranging from 2°C to 5°C.
  • the U.S. Patent No. 7,057,079 provides a process for production of alkenones from vinyl ethers and acid halides or acid anhydrides in the presence of "onium" salt of carboxylic acid.
  • the U.S. Patent No. 7,405,328 provides a two-step method for production of alkenones comprising addition of carboxylic acid halides to vinyl ethers in the absence of acid- capturing agent and at high temperatures up to 150°C.
  • the U.S Patent No. 8,440,865 provides a two-step process for preparation of alkenone providing a halogenated precursor of the alkenone and eliminating the hydrogen halide from said precursor to form the alkenone by a thermolysis treatment selected from the group consisting of a thermolysis carried out at a temperature from greater than 90°C to 120°C, a flash thermolysis, vacuum thermolysis carried out at a temperature from 60°C to 140°C, and thermolysis Under stripping with inert gas.
  • the present invention now makes available an improved process for the preparation of alkenone ethers, in particular concerning the selectivity and the yield of the production, whereby, amongst others, separation of the product can be simplified and yield loss is minimized.
  • the present invention further obviates stringent reaction conditions such as very low reaction temperatures and multiple steps.
  • Another object of the present invention is to provide a process for the preparation of alkenone ether of Formula I having purity greater than 98%.
  • the present invention relates to a process for the synthesis of alkenone ethers.
  • the present invention provides a process for preparation of alkenone ether of Formula I, comprising:
  • R l -C(0)-CH CH-OR 2 Formula I wherein R 1 represents a Ci-Cio alkyl group which is substituted by at least one halogen atom; R represents aryl, substituted aryl, or a Cj-Cio alkyl group which is optionally substituted by at least one halogen atom;
  • X represents fluorine, chlorine, iodine or bromine
  • R 1 represents a Ci-C 10 alkyl group which is substituted by at least one halogen atom and R 2 represents aryl, substituted aryl, or a Ci-C 10 alkyl group which is optionally substituted by at least one halogen atom
  • the present invention provides a process for preparation of alkenone ether of Formula I having purity greater than 98%, comprising:
  • R 1 represents a Q-Cio alkyl group which is substituted by at least one halogen atom
  • R represents aryl, substituted aryl, or a Ci-Qo alkyl group which is optionally substituted by at least one halogen
  • X represents fluorine, chlorine, iodine or bromine
  • R 1 represents a Ci-C 10 alkyl group which is substituted by at least one halogen atom and R 2 represents aryl, substituted aryl, or a Ci-Cio alkyl group which is optionally substituted by at least one halogen atom
  • the Gas chromatography is carried out with Agilent technologies-6820 with FID detector.
  • the present invention provides a process for preparation of alkenone ether of Formula I, comprising:
  • R 1 -C(0)-CH CH-OR 2
  • R 1 represents a Ci-Cio alkyl group which is substituted by at least one halogen atom
  • R represents aryl, substituted aryl, or a Ci-Cio alkyl group which is optionally substituted by at least one halogen atom
  • Formula II Formula III wherein X represents fluorine, chlorine, iodine or bromine; R 1 represents a Ci-C 10 alkyl group which is substituted by at least one halogen atom and R 2 represents aryl, substituted aryl, or a Q-Cio alkyl group which is optionally substituted by at least one halogen atom;
  • step a) isolating alkenone ether of Formula I, wherein step a) is carried out at a pressure of at least about 3 kg/cm or more.
  • the present invention provides a process for preparation of alkenone ether of Formula I having purity greater than 98%, comprising:
  • R 1 represents a Q-Qo alkyl group which is substituted by at least one halogen atom
  • R represents aryl, substituted aryl, or a Ci-Cio alkyl group which is optionally substituted by at least one halogen atom
  • R 1 -C(0)X CH 2 C(H)-OR 2
  • Formula II Formula III wherein X represents fluorine, chlorine, iodine or bromine;
  • R 1 represents a C t -Cio alkyl group which is substituted by at least one halogen atom and
  • R represents aryl, substituted aryl, or a Ci-Ci 0 alkyl group which is optionally substituted by at least one halogen atom;
  • alkyl as used therein, includes straight chain, branched chain and cyclic groups. Thus, typically alkyl groups are methyl, ethyl, n-propyl, isopropyl and cyclopropyl.
  • the halogen may be selected from fluorine, chlorine, bromine and iodine.
  • the reaction of compound of Formula II and compound of Formula III may optionally take place in the presence of base.
  • the base may be an organic base or inorganic base.
  • the organic base may be selected from a nitrogen-containing heterocyclic compound such as pyridine, quinolone or picoline and mixture thereof; a tertiary base such as triethylamine, dimethylaniline, diethylaniline or 4-dimethylaminopyridine and mixture thereof.
  • the inorganic base may be selected from alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or cesium hydroxide and mixture thereof; alkali metal carbonates such as sodium carbonate, potassium carbonate or cesium carbonate and mixture thereof; alkali metal bicarbonate such as sodium bicarbonate or potassium bicarbonate and mixture thereof; alkaline metal hydroxides such as calcium hydroxide, magnesium hydroxide or barium hydroxide and mixture thereof; alkaline metal carbonates such as calcium carbonate, magnesium carbonate or barium carbonate and mixture thereof.
  • the reaction of compound of Formula II and compound of Formula III may optionally take place in the presence of organic solvent.
  • the organic solvent may be selected from aromatic hydrocarbon such as benzene, toluene or xylene and mixture thereof; an aliphatic hydrocarbon such as pentane or hexane and mixture thereof; a halogenated hydrocarbon such as methylene chloride, chloroform, ethylene chloride or carbon tetrachloride and mixture thereof; an ether such as diethyl ether, dibutyl ether, tetrahydrofuran or dioxane and mixture thereof.
  • reaction of compound of Formula II and Formula III is carried out at a pressure of
  • reaction of compound of Formula II and Formula III may be carried out a temperature of about 5°C to about 80°C, for example at about 5°C to about 60°C for about 5 minutes to about 3 hours, for example for about 15 minutes to about 1 hour.
  • the compound of Formula I is isolated by any of the methods in the art, for example, evaporation, decantation, distillation, filtration or layer separation and mixture thereof.
  • the compound of Formula I has a purity greater than 98% by gas chromatography. While the present invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention. EXAMPLES
  • Ethyl vinyl ether (60 g) and triethyl amine (28 g) were taken in an autoclave.
  • the vessel was cooled to 10°C to 15°C and the contents were stirred.
  • the trifluoroacetyl fluoride (99 g) was added in parts to the vessel through dip line from the stainless steel cylinder at 30°C to 40°C and 5 to 10 kg/cm 2 pressure.
  • the contents were stirred for 30 minutes and the reactor pressure drops to 0.25 to 0.5 kg/cm .
  • the excess of trifluoroacetyl fluoride was removed and the contents were washed with water.
  • the organic layer is separated, concentrated to obtain the title product.

Abstract

The present invention relates to a process for the synthesis of alkenone ethers.

Description

METHOD FOR PRODUCING ALKENONE ETHERS
FIELD OF THE INVENTION
The present invention relates to a process for the synthesis of alkenone ethers.
BACKGROUND OF THE INVENTION
The alkenone ethers, such as 4-alkoxy-l, 1 , l-trifluoro-3-butenone, are building blocks and important precursors for chemical synthesis of agrochemicals or pharmaceuticals.
The U.S. Patent No. 5,708,175 provides a process for the preparation of halogenated alkenone ethers by reacting an acid chloride with vinyl ether in the presence of a base at a very low temperature ranging from 2°C to 5°C.
The U.S. Patent No. 7,057,079 provides a process for production of alkenones from vinyl ethers and acid halides or acid anhydrides in the presence of "onium" salt of carboxylic acid. The U.S. Patent No. 7,405,328 provides a two-step method for production of alkenones comprising addition of carboxylic acid halides to vinyl ethers in the absence of acid- capturing agent and at high temperatures up to 150°C.
The U.S Patent No. 8,440,865 provides a two-step process for preparation of alkenone providing a halogenated precursor of the alkenone and eliminating the hydrogen halide from said precursor to form the alkenone by a thermolysis treatment selected from the group consisting of a thermolysis carried out at a temperature from greater than 90°C to 120°C, a flash thermolysis, vacuum thermolysis carried out at a temperature from 60°C to 140°C, and thermolysis Under stripping with inert gas.
The present invention now makes available an improved process for the preparation of alkenone ethers, in particular concerning the selectivity and the yield of the production, whereby, amongst others, separation of the product can be simplified and yield loss is minimized. The present invention further obviates stringent reaction conditions such as very low reaction temperatures and multiple steps.
OBJECTS OF THE INVENTION
It is an object of the present invention to provide a process for the preparation of alkenone ether of Formula I:
R1-C(0)-CH=CH-OR2 Formula I
Another object of the present invention is to provide a process for the preparation of alkenone ether of Formula I having purity greater than 98%.
SUMMARY OF THE INVENTION
The present invention relates to a process for the synthesis of alkenone ethers.
In one aspect, the present invention provides a process for preparation of alkenone ether of Formula I, comprising:
Rl-C(0)-CH=CH-OR2 Formula I wherein R1 represents a Ci-Cio alkyl group which is substituted by at least one halogen atom; R represents aryl, substituted aryl, or a Cj-Cio alkyl group which is optionally substituted by at least one halogen atom;
a) reacting a compound of Formula II and compound of Formula III, and R1-C(0)X CH2=C(H)-OR2
Formula II Formula III
wherein X represents fluorine, chlorine, iodine or bromine; R1 represents a Ci-C10 alkyl group which is substituted by at least one halogen atom and R2 represents aryl, substituted aryl, or a Ci-C10 alkyl group which is optionally substituted by at least one halogen atom; b) isolating alkenone ether of Formula I, wherein step a) is carried out at a pressure of at least about 3 kg/cm or more.
In second aspect, the present invention provides a process for preparation of alkenone ether of Formula I having purity greater than 98%, comprising:
R'-QC -Cf^CH-OR2
Formula I
wherein R1 represents a Q-Cio alkyl group which is substituted by at least one halogen atom; R represents aryl, substituted aryl, or a Ci-Qo alkyl group which is optionally substituted by at least one halogen; a) reacting a compound of Formula II and compound of Formula III, and
R1-C(0)X CH2=C(H)-OR2
Formula II Formula III
wherein X represents fluorine, chlorine, iodine or bromine; R1 represents a Ci-C10 alkyl group which is substituted by at least one halogen atom and R2 represents aryl, substituted aryl, or a Ci-Cio alkyl group which is optionally substituted by at least one halogen atom; b) isolating alkenone ether of Formula I having purity greater than 98%, wherein step a) is carried out at a pressure of at least about 3 kg/cm2 or more.
The Gas chromatography is carried out with Agilent technologies-6820 with FID detector.
DETAILED DESCRIPTION OF THE INVENTION
In an embodiment, the present invention provides a process for preparation of alkenone ether of Formula I, comprising:
R1-C(0)-CH=CH-OR2 Formula I wherein R1 represents a Ci-Cio alkyl group which is substituted by at least one halogen atom; R represents aryl, substituted aryl, or a Ci-Cio alkyl group which is optionally substituted by at least one halogen atom; a) reacting a compound of Formula II and compound of Formula III, and
Rl-C(0)X CH2=C(H)-OR2
Formula II Formula III wherein X represents fluorine, chlorine, iodine or bromine; R1 represents a Ci-C10 alkyl group which is substituted by at least one halogen atom and R2 represents aryl, substituted aryl, or a Q-Cio alkyl group which is optionally substituted by at least one halogen atom;
b) isolating alkenone ether of Formula I, wherein step a) is carried out at a pressure of at least about 3 kg/cm or more. In another embodiment, the present invention provides a process for preparation of alkenone ether of Formula I having purity greater than 98%, comprising:
R'-C^-CH^H-OR2
Formula I wherein R1 represents a Q-Qo alkyl group which is substituted by at least one halogen atom; R represents aryl, substituted aryl, or a Ci-Cio alkyl group which is optionally substituted by at least one halogen atom; a) reacting a compound of Formula II and compound of Formula III, and
R1-C(0)X CH2=C(H)-OR2 Formula II Formula III wherein X represents fluorine, chlorine, iodine or bromine; R1 represents a Ct-Cio alkyl group which is substituted by at least one halogen atom and R represents aryl, substituted aryl, or a Ci-Ci0 alkyl group which is optionally substituted by at least one halogen atom; b) isolating alkenone ether of Formula I having purity greater than 98%, wherein step a) is carried out at a pressure of at least about 3 kg/cm or more.
Unless specifically limited otherwise, the term "alkyl" as used therein, includes straight chain, branched chain and cyclic groups. Thus, typically alkyl groups are methyl, ethyl, n-propyl, isopropyl and cyclopropyl. The halogen may be selected from fluorine, chlorine, bromine and iodine.
The reaction of compound of Formula II and compound of Formula III may optionally take place in the presence of base. The base may be an organic base or inorganic base. The organic base may be selected from a nitrogen-containing heterocyclic compound such as pyridine, quinolone or picoline and mixture thereof; a tertiary base such as triethylamine, dimethylaniline, diethylaniline or 4-dimethylaminopyridine and mixture thereof. The inorganic base may be selected from alkali metal hydroxides such as sodium hydroxide, potassium hydroxide or cesium hydroxide and mixture thereof; alkali metal carbonates such as sodium carbonate, potassium carbonate or cesium carbonate and mixture thereof; alkali metal bicarbonate such as sodium bicarbonate or potassium bicarbonate and mixture thereof; alkaline metal hydroxides such as calcium hydroxide, magnesium hydroxide or barium hydroxide and mixture thereof; alkaline metal carbonates such as calcium carbonate, magnesium carbonate or barium carbonate and mixture thereof.
The reaction of compound of Formula II and compound of Formula III may optionally take place in the presence of organic solvent. The organic solvent may be selected from aromatic hydrocarbon such as benzene, toluene or xylene and mixture thereof; an aliphatic hydrocarbon such as pentane or hexane and mixture thereof; a halogenated hydrocarbon such as methylene chloride, chloroform, ethylene chloride or carbon tetrachloride and mixture thereof; an ether such as diethyl ether, dibutyl ether, tetrahydrofuran or dioxane and mixture thereof.
The reaction of compound of Formula II and Formula III is carried out at a pressure of
9 9
at least about 3 kg/cm or more, for example, at a pressure of about 3 kg/cm to about 15 kg/cm .
The reaction of compound of Formula II and Formula III may be carried out a temperature of about 5°C to about 80°C, for example at about 5°C to about 60°C for about 5 minutes to about 3 hours, for example for about 15 minutes to about 1 hour.
The compound of Formula I is isolated by any of the methods in the art, for example, evaporation, decantation, distillation, filtration or layer separation and mixture thereof. The compound of Formula I has a purity greater than 98% by gas chromatography. While the present invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention. EXAMPLES
Example 1 Preparation of 4-Ethoxy-l,l,l-trifluoro-3-buten-2-one
Ethyl vinyl ether (60 g) and triethyl amine (28 g) were taken in an autoclave. The vessel was cooled to 10°C to 15°C and the contents were stirred. The trifluoroacetyl fluoride (99 g) was added in parts to the vessel through dip line from the stainless steel cylinder at 30°C to 40°C and 5 to 10 kg/cm2 pressure. The contents were stirred for 30 minutes and the reactor pressure drops to 0.25 to 0.5 kg/cm . The excess of trifluoroacetyl fluoride was removed and the contents were washed with water. The organic layer is separated, concentrated to obtain the title product.
Yield (%): 86.2
Purity (%): 98.2

Claims

We claim:
1. A process for preparation of alkenone ether of Formula I, comprising:
R'-C(0)-CH=CH-OR2 Formula I wherein R1 represents a CpCio alkyl group which is substituted by at least one halogen atom; R represents aryl, substituted aryl, or a Cj-Cio alkyl group which is optionally substituted by at least one halogen atom;
a) reacting a compound of Formula II and compound of Formula III, and
Rl-C(0)X CH2=C(H)-OR2
Formula II Formula III wherein X represents fluorine, chlorine, iodine or bromine; R1 represents a Ci-C10 alkyl group which is substituted by at least one halogen atom and R2 represents aryl, substituted aryl, or a Ci-C10 alkyl group which is optionally substituted by at least one halogen atom; b) isolating alkenone ether of Formula I, wherein step a) is carried out at a pressure of at least about 3 kg/cm or more.
2. A process for preparation of alkenone ether of Formula I having purity greater than 98%, comprising:
R'-C(0)-CH=CH-OR2 Formula I wherein R1 represents a d-Qo alkyl group which is substituted by at least one halogen atom; R represents aryl, substituted aryl, or a Q-Cio alkyl group which is optionally substituted by at least one halogen atom; a) reacting a compound of Formula II and compound of Formula III, and
R'-C(0)X CH2=C(H)-OR2
Formula II Formula III wherein X represents fluorine, chlorine, iodine or bromine; R1 represents a Ci-Cjo alkyl group which is substituted by at least one halogen atom and R2 represents aryl, substituted aryl, or a Q-Cio alkyl group which is optionally substituted by at least one halogen atom. b) isolating alkenone ether of Formula I having purity greater than 98%, wherein step a) is carried out at a pressure of at least about 3 kg/cm2 or more.
3. The process of claim 1 or 2, wherein step a) takes place in the presence of organic base or inorganic base.
4. The process of claim 3, wherein the organic base is selected from pyridine, quinolone, picoline, triethylamine, dimethylaniline, diethylaniline or 4- dimethylaminopyridine and mixture thereof.
5. The process of claim 3, wherein the inorganic base is selected from sodium hydroxide, potassium hydroxide, cesium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, potassium bicarbonate, calcium hydroxide, magnesium hydroxide, barium hydroxide, calcium carbonate, magnesium carbonate or barium carbonate and mixture thereof.
6. The process of claim 1 or 2, wherein step a) takes place in the presence of organic solvent selected from benzene, toluene, xylene, pentane, hexane, methylene chloride, chloroform, ethylene chloride, carbon tetrachloride, diethyl ether, dibutyl ether, tetrahydrofuran or dioxane and mixture thereof. The process of claim 1 , wherein the compound of Formula I has a purity greater than 98% by gas chromatography.
The process of claim 1 or 2, wherein step a) is carried out at the temperature of about 5°C to about 80°C.
PCT/IN2014/000487 2013-07-26 2014-07-23 Method for producing alkenone ethers WO2015011728A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2224/DEL/2013 2013-07-26
IN2224DE2013 2013-07-26

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5708175A (en) 1995-05-26 1998-01-13 Ishihara Sangyo Kaisha Ltd. Process for producing 4-trifluoromethylnicotinic acid
US7057079B2 (en) 2002-02-08 2006-06-06 Solvay Fluor Und Derivate Gmbh Method of synthesizing alkenone compounds
US7405328B2 (en) 2003-06-06 2008-07-29 Solvay Fluor Gmbh Method for producing alkenone ethers
WO2011003854A1 (en) * 2009-07-06 2011-01-13 Solvay Sa Process for the manufacture of halogenated precursors of alkenones in the presence of a solvent
US8440865B2 (en) 2009-07-06 2013-05-14 Solvay Sa Process for the manufacture of alkenones

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5708175A (en) 1995-05-26 1998-01-13 Ishihara Sangyo Kaisha Ltd. Process for producing 4-trifluoromethylnicotinic acid
US7057079B2 (en) 2002-02-08 2006-06-06 Solvay Fluor Und Derivate Gmbh Method of synthesizing alkenone compounds
US7405328B2 (en) 2003-06-06 2008-07-29 Solvay Fluor Gmbh Method for producing alkenone ethers
WO2011003854A1 (en) * 2009-07-06 2011-01-13 Solvay Sa Process for the manufacture of halogenated precursors of alkenones in the presence of a solvent
US8440865B2 (en) 2009-07-06 2013-05-14 Solvay Sa Process for the manufacture of alkenones

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