Title of Invention | A PROCESS FOR SYNTHESIS OF PARA PROPOXY ETHYL BENZOATE |
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Abstract | The present invention relates to a new product para propoxy ethyl benzoate and its synthesis, which comprises the process of etherification of ethyl paraben in various solvents using n-propyl iodine or n-propyl bromide as etherification agent in the presence of bases like sodium hydroxide or potassium hydroxide and isolating the inorganic halides by filtration and removal of unreacted ethyl paraben after the recovery of the solvent by distillation and washing with alkali solution. |
Full Text | FORM - 2 THE PATENT ACT. 1970 (39 of 1970) PROVISIONAL SPECIFICATION [SECTION 10 ; RULE 1 3] PARA PROPOXY ETHYL BENZOATE AND SYNTHESIS THEREOF GUJARAT ORGANICS LIMITED, AN INDIAN COMPANY INCORPORATED UNDER THE COMPANIES ACT, 1956 HAVING ITS OFFICE AT PLOT NO 127/1,. G.I.D.C. ESTATE, ANKLESHWAR - 393 002, DIST BHARUCH, GUJARAT STATE, INDIA. THE FOLLOWING SPECIFICATIONS PARTICULARLY DESCRIBES THE NATURE OF THIS INVENTION :- The present invention relates to a new product, Viz Para Propoxy Ethyl Benzoate or p - n - Propoxy Ethyl Benzoate (PPEB), its synthesis and its purification. The present invention discloses the synthesis, characterization of Para Propoxy Ethyl Benzoate. The present compound has commercial application as external electron donor in Poly Propylene manufacturing. The present invention also discloses the synthesis of Para Propoxy Ethyl Benzoate by esterification of p-Hydroxy Benzoic Acid with Ethanol in the presence of Sulphonic Acid followed by recovery of excess ethanol by distillation. The residual material is purified in water by neutralization using a base Viz Sodium Bicarbonate / Sodium Hydroxide / Potassium Hydroxide / Sodium Carbonate in the dilute solution in water. In the preferred embodiment, the process of esterification is carried out in the presence of an Aryl Sulphonic Acid e.g. Para Toluene sulphonic Acid. The process of esterification can also be carried out in the presence of an Alkyl Sulphonic Acid e.g. Methane Sulphonic Acid. Hydrochloric Acid can also be used as a catalyst in the process of esterification, polymer Sulphonic Acid e.g. Ion Exchange Resins like Indion 850/ Duolite 368 can also be used as a catalyst in the process of esterification. Dry Ethyl Paraben obtained from the above process is etherified using halogenated Propyl derivatives (CI, Br and I) in the presence of a base such as NaOH or KOH in a solvent VizO.D.C.B., Methyl Iso Butyl Ketone, Diethyl Formamide and Dimethyl Formamide. According to this invention, Para Propoxy Ethyl Benzoate has the following structure Further according to this invention, the process for manufacturing Para Propoxy Ethyl Benzoate comprises of the following steps (a) Etherification of Ethyl Paraben in liquid Formamide reacting it with n - Propyl Halide (Br or I) in the presence of Alkali Hydroxide. (b) Isolation of resulting inorganic Halide by filtration. (c) Recovery of solvent by distillation. (d) Removal of unreacted Ethyl Paraben. In the above step (a) firstly Ethyl Paraben is dissolved in liquid Formamide; secondly alkali Hydroxide is slowly added to the above solution in the first sub step under stirring; thirdly n - Propyl Halide is added to the above solution in the second sub step under stirring. The reaction temperature is maintained between 30°C - 75°C throughout. Further in the said step liquid Formamide is N, N- Dimethyl Formamide or N, N - Diethyl Formamide or Methyl Iso Butyl Ketone or Ortho Di Chloro Benzene; etherification reagent is n - Propyl Bromide or n - Propyl Iodide; and moisture content of said distilled Para Propoxy Ethyl Benzoate is in the range of 1 50 -200 ppm. In the step (d) unreacted Ethyl Paraben is removed by washing the reaction mass with alkali hydroxide or alkali carbonate solution or alkali bicarbonate solution and the resultant product is purified by distillation. The following reaction illustrates the invention The present invention is illustrated with the following additional examples. The above stated reaction as also below examples are only illustrative and in no way limit the scope of invention. EXAMPLE - 1 Charge N, N - Dimethyl Formamide (1.88 Kg.), Ethyl Paraben (2.0 Kg.) followed by the addition of Sodium Hydroxide (0.480 Kg.). Stir the contents for 4.0 hours. Then add n - Propyl Bromide (2.38Kg.) to convert Ethyl Paraben into Para Propoxy Ethyl Benzoate. Maintain the reaction at 30°C - 75°C to complete the reaction. Monitor the progress of the reaction on TLC. After completion of the reaction filter the solid Sodium Bromide and collect the Mother Liquor containing N, N -Dimethyl Formamide and Para Propoxy Ethyl Benzoate. Distill out the N, N - Dimethyl Formamide under vacuum at 95°C - 100°C/0.5 - 1.0 mm of Hg and recover N, N - Dimethyl Formamide (1.78 Kg.) Add water to the residue. Separate the upper organic layer. Wash the organic layer with 5% KOH solution or 5% NaHCO3 solution or 5% Sodium Carbonate solution. Then wash the organic layer with water (250 ml). Distill the organic layer under vacuum at 110°C - 120°C / 0.5 - 1.0 mm of Hg. Weight of Para Propoxy Ethyl Benzoate = 2.00 Kg. Yield = 83.19% (Theory) G.C. Purity = 99.4% Para Propoxy Benzoic Acid = 0.04 % Moisture Content = 200 ppm EXAMPLE - 2 Charge N, N - Diethyl Formamide (1.88 Kg.), Ethyl Paraben (2.0Kg.) followed by the addition of Potassium Hydroxide (0.680 Kg.). Stir the contents for 6.0 hours. Then add n - Propyl Bromide (2.38 Kg.) to convert Ethyl Paraben to Para Propoxy Ethyl Benzoate. Maintain the reaction at 30°C - 75°C to complete the reaction. Monitor the progress of the reaction on TLC. After completion of the reaction filter the solid Potassium Bromide and collect the Mother Liquor containing N, N - Diethyl Formamide and Para Propoxy Ethyl Benzoate. Distill out the N, N - Diethyl Formamide under vacuum at 95°C -100°C/0.1 - 1.0 mm of Hg and recover N, N - Diethyl Formamide (1.8 Kg. approx.). Add water to the residue. Separate the upper organic layer. Then wash the organic layer with 5% KOH solution or 5% NaHC03 solution or 5% Sodium Carbonate solution (200 ml). Then wash the organic layer with water (200 ml). Distill the organic layer under vacuum at 110°C - 1 20°C / 0.1 -1.0 mm of Hg. Weight of Para Propoxy Ethyl Benzoate = 2.25 Kg. % Yield = 90% (Theory) G.C. Purity = 99.3% Para Iso Propoxy Benzoic Acid = 0.03% Moisture Content = 150 ppm EXAMPLE - 3 Charge N, N - Diethyl Formamide (1.9 Kg.), Ethyl Paraben (2.0 Kg.) followed by the slow addition of Sodium Hydroxide (0.480 Kg.). Stir the contents for 6.0 hours. Then add n - Propyl Bromide (2.38Kg.) to convert Ethyl Paraben to Para Propoxy Ethyl Benzoate. Maintain the reaction at 30°C - 75°C to complete the reaction. Monitor the progress of the reaction on TLC. After completion of the reaction filter the solid Sodium Bromide and collect the Mother Liquor containing N, N -Diethyl Formamide and Para Propoxy Ethyl Benzoate. Distill out the N, N - Diethyl Formamide under vacuum at 100°C / 1.0 mm of Hg and recover N, N - Diethyl Formamide (1.7 Kg.) Add water to the residue. Separate the upper organic layer. Wash the organic layer with 5% NaOH solution or 5% NaHC03 solution or 5% Sodium Carbonate solution or 5% KOH solution (200 ml). Then wash the organic layer with water (250 ml). Distill the organic layer under vacuum at 110°C - 120°C / 0.5 -1.0 mm of Hg. Weight of Para Propoxy Ethyl Benzoate = 2.30 Kg. Yield = 92% (Theory) G.C. Purity = 99.3% Para Iso Propoxy Benzoic Acid = 0.03% Moisture Content = 1 50 ppm EXAMPLE - 4 Charge N, N - Diethyl Formamide (1.9 Kg.), Ethyl Paraben (2.0 Kg.) followed by the addition of Sodium Hydroxide (0.480 Kg.). Stir the contents for 4.0 hours. Then add n - Propyl Iodide (3.0 Kg.) to convert Ethyl Paraben to Para Propoxy Ethyl Benzoate. Maintain the reaction at 30°C - 75°C to complete the reaction. Monitor the progress of the reaction on TLC. After completion of the reaction filter the solid Sodium Iodide and collect the Mother Liquor containing N, N - Diethyl Formamide and Para Propoxy Ethyl Benzoate. Distill out the N, N -Diethyl Formamide under vacuum at 95°C -100°C/ 10 mm of Hg and recover N, N - Diethyl Formamide (1.70 Kg. app.). Add water to the residue separate the upper organic layer. Then wash the organic layer with 5% NaOH solution or 5% NaHC03 solution or 5% Sodium Carbonate solution or 5% KOH solution (200 ml). Then wash the organic layer with water (250 ml). Distill the organic layer under vacuum at 110°C - 1 20°C / 0.5 - 1.0 mm of Hg. Weight of Para Propoxy Ethyl Benzoate = 2.2 Kg. % Yield = 88% (Theory) G.C. Purity = 99.3% Para Iso Propoxy Benzoic Acid = 0.03% Moisture Content =180 ppm EXAMPLE - 5 Charge Ortho Di Chloro Benzene (1.9 Kg.), Ethyl Paraben (2.0 Kg.) followed by the slow addition of Sodium Hydroxide (0.480 Kg.). Stir the contents for 6.0 hours. Then add n - Propyl Bromide (2.38 Kg.) to convert Ethyl Paraben to Para Propoxy Ethyl Benzoate. Maintain the reaction at 30°C - 75°C to complete the reaction. Monitor the progress of the reaction on TLC. After completion of the reaction filter the solid Sodium Bromide and collect the Mother Liquor containing Ortho Di Chloro Benzene and Para Propoxy Ethyl Benzoate. Distill out the Ortho Di Chloro Benzene under vacuum at 100°C /0.1 - 1.0 mm of Hg and recover Ortho Di Chloro Benzene (1.70 Kg. app.). Then add water (200 ml) to the residue separate the upper organic layer. Then wash the organic layer with 5% NaOH solution (200 ml). Then wash the organic layer with water (250 ml). Distill the organic layer under vacuum at 110°C - 120°C / 0.1 - 1.0 mm of Hg. Weight of Para Propoxy Ethyl Benzoate = 2.37 Kg. % Yield = 94.8% (Theory) G.C. Purity = 99.20% Para Iso Propoxy Benzoic Acid = 0.04% Moisture Content = 1 50 ppm EXAMPLE - 6 Charge Methyl Iso Butyl Ketone (1.9 Kg.), Ethyl Paraben (2.0 Kg.) followed by the slow addition of Sodium Hydroxide (0.480 Kg.). Stir the contents for 6.0 hours. Then add n - Propyl Bromide to convert Ethyl Paraben to Para Propoxy Ethyl Benzoate. Maintain the reaction at 30°C - 75°C to complete the reaction. Monitor the progress of the reaction on TLC. After completion of the reaction, filter the solid Sodium Bromide and collect the Mother Liquor containing Methyl Iso Butyl Ketone and Para Propoxy Ethyl Benzoate. Distill out the Methyl Iso Butyl Ketone (1.70 Kg. approx.). Add water to the residue. Separate the upper organic layer. Then wash the organic layer with 5% NaOH solution (200 ml). Then wash the organic layer with water (200 ml). Distill the organic layer under vacuum at 110°C - 120°C / 0.1 - 1.0 mm of Hg. Weight of Para Propoxy Ethyl Benzoate = 2.30 Kg. % Yield - 92% (Theory) G.C. Purity = 99.4% Para Iso Propoxy Benzoic Acid = 0.02% Moisture Content = 175 ppm ADVANTAGES 1. The present inventions synthesizes new product Para Propoxy Ethyl Benzoate with very low Para Propoxy Benzoic Acid impurity (less than 0.1%) 2. The present invention synthesizes Para Propoxy Ethyl Benzoate of 99.3% to 99.4% G.C. Purity. 3. The present invention is an economical method for producing the new product Para Propoxy Ethyl Benzoate. |
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Patent Number | 268998 | |||||||||
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Indian Patent Application Number | 2101/MUM/2007 | |||||||||
PG Journal Number | 40/2015 | |||||||||
Publication Date | 02-Oct-2015 | |||||||||
Grant Date | 28-Sep-2015 | |||||||||
Date of Filing | 24-Oct-2007 | |||||||||
Name of Patentee | GUJARAT ORGANICS LTD. | |||||||||
Applicant Address | PLOT NO. 127/1,GIDC ESTATE,ANKLESHWAR 393002,DIST BHARUCH | |||||||||
Inventors:
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PCT International Classification Number | C07C67/00 | |||||||||
PCT International Application Number | N/A | |||||||||
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PCT Conventions:
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