WO2015118561A1 - Processes for producing 1,1,1,5,5,5 hexafluoroacetyl acetone - Google Patents

Processes for producing 1,1,1,5,5,5 hexafluoroacetyl acetone Download PDF

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Publication number
WO2015118561A1
WO2015118561A1 PCT/IN2015/000073 IN2015000073W WO2015118561A1 WO 2015118561 A1 WO2015118561 A1 WO 2015118561A1 IN 2015000073 W IN2015000073 W IN 2015000073W WO 2015118561 A1 WO2015118561 A1 WO 2015118561A1
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Prior art keywords
acid
acetone
hexafluoroacetyl
alkyl
alkali metal
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PCT/IN2015/000073
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French (fr)
Inventor
Hanuman GUPTA
Charu Gupta
Kapil Kumar
Rahul Saxena
Rajdeep Anand
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Srf Limited
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Publication of WO2015118561A1 publication Critical patent/WO2015118561A1/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 preparation of 1,1,1,5,5,5- hexafluoroacetyl acetone.
  • the 1,1,1,5,5,5-hexafluoroacetyl acetone has significant role for pharmaceutical, agrochemical and electronic products.
  • U.S. Patent Nos. 6,392,101 and 6,384,286 disclose processes for producing 1,1,1,5,5,5-hexafluoroacetyl acetone involving reaction of 1,1,1 trifluoroacetone and ester of trifluoroacetic acid, followed by the addition of water and 24% sulfuric acid 20 to obtain an dihydrate intermediate. Further, this dihydrate intermediate is purified to obtain 1,1,1,5,5,5-hexafluoroacetyl acetone. The multistep work-up and many process operations of the reaction results in poor yield. Additionally, poor recovery of hydrate from aqueous solution results in high effluent load.
  • Japanese Patent Application No. 2001261607 discloses the process for 25 producingl,l,l,5,5,5-hexafluoroacetyl acetone by hydrolysis of 1,1,1,5,5,5- hexafluoroacetyl acetone metal complex and dehydration of the resulting 1,1,1,5,5,5-hexafluoroacetyl acetone dihydrate.
  • Chinese Patent No. 102260151 provides a process for the preparation of 1,1,1, 5,5, 5-hexafluoroacetylacetone which comprises of reaction of trifluoroacetic anhydride with trifluoroacetoacetate in the presence of a catalyst.
  • the main objective of the present invention is to provide a process for preparation of 1 , 1, 1 ,5,5,5-hexafluoroacetyl acetone.
  • An aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
  • alkyl is C1-C4 alkyl group
  • step b) contacting the product obtained from step a) with an acid
  • steps a), b) and c) are carried out under anhydrous conditions.
  • Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
  • alkyl is C1-C4 alkyl group
  • steps a) and b) are carried out in one pot.
  • Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
  • alkyl is Q-C 4 alkyl group
  • steps a) and b) are carried out in one pot under anhydrous conditions.
  • An aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
  • alkyl is C1-C4 alkyl group
  • step b) contacting the product obtained from step a) with an acid
  • steps a), b) and c) are carried out under anhydrous conditions.
  • Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
  • alkyl is C1-C4 alkyl group
  • steps a) and b) are carried out in one pot.
  • Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
  • alkyl is C1-C4 alkyl group
  • steps a) and b) are carried out in one pot under anhydrous conditions.
  • the reaction of 1,1,1 trifluoro acetone and alkyl trifluoroacetate is carried out in the presence of a base.
  • the reaction is carried out under anhydrous conditions.
  • the base is selected from alkali metal, alkali metal alkoxide and alkali metal hydride or mixture thereof.
  • the alkali metal may be selected from sodium, potassium, rubidium and cesium.
  • the alkali metal alkoxide may be selected from sodium methoxide, sodium ethoxide, potassium methoxide and potassium ethoxide.
  • the alkali metal hydride may be selected from sodium hydride and potassium hydride.
  • the reaction of 1 , 1 , 1 trifluoro acetone and alkyl trifluoroacetate in the presence of a base may be carried out at a temperature range of about 0°C to about 100°C, for example, about 10°C to about 70°C.
  • the reaction may take place in presence an aprotic organic solvent selected from the group consisting of methyl tert butyl ether, monoglyme, diglyme, cyclohexane, toluene, xylene, diethyl ether, diisopropyl ether and dioxane or mixtures thereof.
  • the reaction of 1,1,1 trifluoro acetone and alkyl trifluoroacetate is carried out in the presence of a base to provide an alkali metal salt of 1,1,1,5,5,5- hexafluoroacetyl acetone.
  • the alkali metal salt of 1,1,1,5,5,5-hexafluoroacetyl acetone may be isolated from the reaction mixture or may be carried on to next step without isolation.
  • alkyl represents CpC 4 alkyl group.
  • the "one pot” means step a) and b) are carried out in the same reaction pot/vessel, essentially without isolating the intermediate obtained from step a).
  • the "anhydrous condition" means condition which contain no water.
  • the alkali metal salt of 1,1,1,5,5,5-hexafluoroacetyl acetone is treated with an acid to obtain 1,1,1,5,5,5 hexafluoroacetyl acetone.
  • the treatment with an acid is carried out under anhydrous conditions.
  • An acid may be selected from an inorganic acid or an organic acid.
  • An inorganic acid may be selected from hydrochloric acid, sulphuric acid and chlorosulfonic acid or mixture thereof.
  • An organic acid may be selected from trifluoroacetic acid, methane sulfonic acid and p-toluene sulfonic acid or mixture thereof.
  • An acid may be in anhydrous solution form or in gaseous form.
  • the treatment of 1,1,1,5,5,5-hexafluoroacetyl acetone treated with an acid may be carried out at a temperature range of about 0°C to about 60°C.
  • the treatment of 1,1,1,5,5,5-hexafluoroacetyl acetone treated with an acid may be carried out in presence of an aprotic solvent, for example, hexane, cyclohexane, toluene xylene, mono glyme, diglyme and dioxane or mixtures thereof.
  • the 1,1,1,5,5,5-hexafluoroacetyl acetone is isolated from the reaction mixture by any of the methods in the art, for example, evaporation, distillation, crystallization, filtration and layer separation or mixture thereof.
  • the 1,1,1,5,5,5-hexafluoroacetyl acetone obtained by process disclosed in present invention, has high purity about 98% to about 99%.
  • the present invention may be carried out in continuous mode.
  • the sodium ethoxide (122 g) and toluene (215 g) were taken together in a round bottom flask.
  • a mixture of 1,1,1-trifluoroacetone (200 g) and ethyl trifluoroacetate (280 g) was added to the reaction flask at 20°C to 30 °C.
  • the reaction mixture was stirred and monitored for 6 hours.
  • the toluene was distilled off from the reaction mixture partially to obtain sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone.
  • the sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone was filtered, dried under vacuum.
  • the anhydrous sulphuric acid (438 g, 98%) was added to the reaction vessel and sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone was added to the reaction vessel at 30°C to 40°C. The reaction mass was stirred for three hours and title compound was distilled.
  • the sodium ethoxide (66 g) and toluene (145 g) were taken together in a round bottom flask.
  • a mixture of 1,1,1-trifluoroacetone (100 g) and ethyl trifluoroacetate (140 g) was added to the reaction flask at 20°C to 30 °C.
  • the reaction mixture was stirred and monitored for 6 hours.
  • the toluene was distilled off from the reaction mixture partially to obtain sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone suspended in toluene.
  • the anhydrous sulphuric acid (220 g, 98%) was added to the reaction vessel to containing suspended sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone at 30°C to 40°C.
  • the reaction mass was stirred for three hours and title compound was distilled.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a process for preparation of 1,1,1,5,5,5-hexafluoroacetyl acetone.

Description

PROCESSES FOR PRODUCING 1,1,1,5,5,5 HEXAFLUOROACETYL ACETONE
5 FIELD OF INVENTION
The present invention relates to a process for preparation of 1,1,1,5,5,5- hexafluoroacetyl acetone.
BACKGROUND OF THE INVENTION
10 The 1,1,1,5,5,5-hexafluoroacetyl acetone has significant role for pharmaceutical, agrochemical and electronic products.
A. Henne et al., J. Amer. Chem. Soc, Vol. 69, pp. 1819-1820 (1947) discloses a process for preparing 1,1,1,5,5,5-hexafluoroacetyl acetone which involves a copper complex and hydrogen sulphide in ether. A very similar process is disclosed in U.S. 15 Patent No. 6,046,364. The processes disclosed in prior art have many disadvantages like poor yield and industrially non-compliant due to high effluent load.
U.S. Patent Nos. 6,392,101 and 6,384,286 disclose processes for producing 1,1,1,5,5,5-hexafluoroacetyl acetone involving reaction of 1,1,1 trifluoroacetone and ester of trifluoroacetic acid, followed by the addition of water and 24% sulfuric acid 20 to obtain an dihydrate intermediate. Further, this dihydrate intermediate is purified to obtain 1,1,1,5,5,5-hexafluoroacetyl acetone. The multistep work-up and many process operations of the reaction results in poor yield. Additionally, poor recovery of hydrate from aqueous solution results in high effluent load.
Japanese Patent Application No. 2001261607 discloses the process for 25 producingl,l,l,5,5,5-hexafluoroacetyl acetone by hydrolysis of 1,1,1,5,5,5- hexafluoroacetyl acetone metal complex and dehydration of the resulting 1,1,1,5,5,5-hexafluoroacetyl acetone dihydrate. Chinese Patent No. 102260151 provides a process for the preparation of 1,1,1, 5,5, 5-hexafluoroacetylacetone which comprises of reaction of trifluoroacetic anhydride with trifluoroacetoacetate in the presence of a catalyst. Although, these processes involves cheap raw materials, but suffer in terms of multistep work-up and many process operations which result in poor yield.
Thus, there is a need in the art for an economically viable, energy efficient and high output alternative way to prepare 1,1,1,5,5,5 tetrafluoro acetyl acetone.
OBJECTIVE OF THE INVENTION
The main objective of the present invention is to provide a process for preparation of 1 , 1, 1 ,5,5,5-hexafluoroacetyl acetone.
SUMMARY OF THE INVENTION
An aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base,
wherein "alkyl" is C1-C4 alkyl group
b) contacting the product obtained from step a) with an acid, and
c) isolating the 1,1,1,5,5,5 hexafluoroacetyl acetone from the step b) reaction mixture, wherein steps a), b) and c) are carried out under anhydrous conditions.
Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base, wherein "alkyl" is C1-C4 alkyl group and
b) contacting the product obtained from step a) with an acid to obtain 1,1,1,5,5,5 hexafluoroacetyl acetone, wherein steps a) and b) are carried out in one pot.
Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base, wherein "alkyl" is Q-C4 alkyl group and
b) contacting the product obtained from step a) with an acid to obtain 1,1,1,5,5,5 hexafluoroacetyl acetone, wherein steps a) and b) are carried out in one pot under anhydrous conditions.
DETAILED DESCRIPTION OF THE INVENTION
An aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base,
wherein "alkyl" is C1-C4 alkyl group
b) contacting the product obtained from step a) with an acid, and
c) isolating the 1,1,1,5,5,5 hexafluoroacetyl acetone from the step b) reaction mixture, wherein steps a), b) and c) are carried out under anhydrous conditions.
Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base, wherein "alkyl" is C1-C4 alkyl group and
b) contacting the product obtained from step a) with an acid to obtain 1,1,1,5,5,5 hexafluoroacetyl acetone, wherein steps a) and b) are carried out in one pot.
Another aspect of the present invention provides a process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising:
a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base, wherein "alkyl" is C1-C4 alkyl group and
b) contacting the product obtained from step a) with an acid to obtain 1,1,1,5,5,5 hexafluoroacetyl acetone, wherein steps a) and b) are carried out in one pot under anhydrous conditions.
The reaction of 1,1,1 trifluoro acetone and alkyl trifluoroacetate is carried out in the presence of a base. The reaction is carried out under anhydrous conditions. The base is selected from alkali metal, alkali metal alkoxide and alkali metal hydride or mixture thereof. The alkali metal may be selected from sodium, potassium, rubidium and cesium. The alkali metal alkoxide may be selected from sodium methoxide, sodium ethoxide, potassium methoxide and potassium ethoxide. The alkali metal hydride may be selected from sodium hydride and potassium hydride. The reaction of 1 , 1 , 1 trifluoro acetone and alkyl trifluoroacetate in the presence of a base may be carried out at a temperature range of about 0°C to about 100°C, for example, about 10°C to about 70°C. The reaction may take place in presence an aprotic organic solvent selected from the group consisting of methyl tert butyl ether, monoglyme, diglyme, cyclohexane, toluene, xylene, diethyl ether, diisopropyl ether and dioxane or mixtures thereof. The reaction of 1,1,1 trifluoro acetone and alkyl trifluoroacetate is carried out in the presence of a base to provide an alkali metal salt of 1,1,1,5,5,5- hexafluoroacetyl acetone. The alkali metal salt of 1,1,1,5,5,5-hexafluoroacetyl acetone may be isolated from the reaction mixture or may be carried on to next step without isolation.
The "alkyl" represents CpC4 alkyl group.
The "one pot" means step a) and b) are carried out in the same reaction pot/vessel, essentially without isolating the intermediate obtained from step a).
The "anhydrous condition" means condition which contain no water.
The alkali metal salt of 1,1,1,5,5,5-hexafluoroacetyl acetone is treated with an acid to obtain 1,1,1,5,5,5 hexafluoroacetyl acetone. The treatment with an acid is carried out under anhydrous conditions. An acid may be selected from an inorganic acid or an organic acid. An inorganic acid may be selected from hydrochloric acid, sulphuric acid and chlorosulfonic acid or mixture thereof. An organic acid may be selected from trifluoroacetic acid, methane sulfonic acid and p-toluene sulfonic acid or mixture thereof. An acid may be in anhydrous solution form or in gaseous form. The treatment of 1,1,1,5,5,5-hexafluoroacetyl acetone treated with an acid may be carried out at a temperature range of about 0°C to about 60°C. The treatment of 1,1,1,5,5,5-hexafluoroacetyl acetone treated with an acid may be carried out in presence of an aprotic solvent, for example, hexane, cyclohexane, toluene xylene, mono glyme, diglyme and dioxane or mixtures thereof.
The 1,1,1,5,5,5-hexafluoroacetyl acetone is isolated from the reaction mixture by any of the methods in the art, for example, evaporation, distillation, crystallization, filtration and layer separation or mixture thereof.
The 1,1,1,5,5,5-hexafluoroacetyl acetone, obtained by process disclosed in present invention, has high purity about 98% to about 99%.
The present invention may be carried out in continuous mode.
The following examples are given by way of illustration of the present disclosure and should not be construed to limit the scope of present disclosure. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the subject matter.
EXAMPLES
1: Preparation of l,l.l»5,5,5-hexafluoroacetyl acetone
The sodium ethoxide (122 g) and toluene (215 g) were taken together in a round bottom flask. A mixture of 1,1,1-trifluoroacetone (200 g) and ethyl trifluoroacetate (280 g) was added to the reaction flask at 20°C to 30 °C. The reaction mixture was stirred and monitored for 6 hours. The toluene was distilled off from the reaction mixture partially to obtain sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone. The sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone was filtered, dried under vacuum. The anhydrous sulphuric acid (438 g, 98%) was added to the reaction vessel and sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone was added to the reaction vessel at 30°C to 40°C. The reaction mass was stirred for three hours and title compound was distilled.
Yield: 316 g
2: Preparation of 1,1,1,5,5,5-hexafluoroacetyl acetone
The sodium ethoxide (66 g) and toluene (145 g) were taken together in a round bottom flask. A mixture of 1,1,1-trifluoroacetone (100 g) and ethyl trifluoroacetate (140 g) was added to the reaction flask at 20°C to 30 °C. The reaction mixture was stirred and monitored for 6 hours. The toluene was distilled off from the reaction mixture partially to obtain sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone suspended in toluene. The anhydrous sulphuric acid (220 g, 98%) was added to the reaction vessel to containing suspended sodium salt of 1,1,1,5,5,5-hexafluoroacetyl acetone at 30°C to 40°C. The reaction mass was stirred for three hours and title compound was distilled.
Yield: 167 g
Purity: 98.5%

Claims

We claim:
1. A process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising: a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base,
wherein "alkyl" is C C4 alkyl group
b) contacting the product obtained from step a) with an acid, and c) isolating the 1,1,1,5,5,5 hexafluoroacetyl acetone from the step b) reaction mixture, wherein steps a), b) and c) are carried out under anhydrous conditions.
2. The process according to claim 1, wherein step a) base is selected from alkali metal, alkali metal alkoxide and alkali metal hydride or mixture thereof.
3. The process according to claim 2, where in the alkali metal is selected from sodium, potassium, rubidium and cesium; the alkali metal alkoxide is selected from sodium methoxide, sodium ethoxide, potassium methoxide and potassium ethoxide and the alkali metal hydride is selected from sodium hydride and potassium hydride.
4. A process for producing 1,1,1 ,5,5,5 hexafluoroacetyl acetone comprising: a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base, wherein "alkyl" is Ci-C4 alkyl group, and b) contacting the product obtained from step a) with an acid to obtain
1,1,1,5,5,5 hexafluoroacetyl acetone, wherein steps a) and b) are carried out in one pot.
5. A process for producing 1,1,1,5,5,5 hexafluoroacetyl acetone comprising: a) reacting 1,1,1 trifluoro acetone with alkyl trifluoroacetate in the presence of a base, wherein "alkyl" is C1 -C4 alkyl group, and b) contacting the product obtained from step a) with an acid to obtain 1,1,1,5,5,5 hexafluoroacetyl acetone, wherein steps a) and b) are carried out in one pot under anhydrous conditions.
6. The process according to claims 1, 4 and 5, wherein an acid is selected from an inorganic acid or an organic acid.
7. The process according to claim 6, wherein an inorganic acid is selected from hydrochloric acid, sulphuric acid and chlorosulfonic acid or mixture thereof; an organic acid may be selected from trifiuoroacetic acid, methane sulfonic acid and p-toluene sulfonic acid or mixture thereof.
8. The process according to claims 1, 4 and 5, wherein an acid may be in anhydrous solution form or in gaseous form.
9. The process according to claims 1, wherein 1,1,1,5,5,5-hexafluoroacetyl acetone is isolated from the reaction mixture by evaporation, distillation, crystallization, filtration and layer separation or mixture thereof.
PCT/IN2015/000073 2014-02-06 2015-02-06 Processes for producing 1,1,1,5,5,5 hexafluoroacetyl acetone WO2015118561A1 (en)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020010373A1 (en) * 2000-01-05 2002-01-24 Takeo Komata Process for purifying 1,1,1,5,5,5-hexafluoroacetylacetone

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020010373A1 (en) * 2000-01-05 2002-01-24 Takeo Komata Process for purifying 1,1,1,5,5,5-hexafluoroacetylacetone

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HENNE A L ET AL: "The Alkaline Condensation of Fluorinated Esters with Esters and Ketones", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, [NOT]AMERICAN CHEMICAL SOCIETY|, vol. 69, no. 7, 1 January 1947 (1947-01-01), pages 1819 - 1820, XP002347795, ISSN: 0002-7863, DOI: 10.1021/JA01199A075 *

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