Title of Invention

A PROCESS OF MANUFACTURING SODIUM SALICYLATE

Abstract A PROCESS OF MANUFACTURING SODIUM SALICYLATE
Full Text FORM 2
THE PATENTS ACT. 1970 (39 OF 1970)
COMPLETE SPECIFICATION
[SECTION 10; RULE 13]
"A PROCESS OF MANUFACTURING SODIUM SALICYLATE"
GUJRAT ORGANICS LIMITED, AN INDIAN COMPANY INCORPORATED UNDER THE COMPANIES ACT, 1956 HAVING ITS OFFICE AT PLOT NO. 127/1, GIDC ESTATE, ANKLESHWAR 393 002, DIST.BHARUCH, GUJARAT STATE, INDIA.
THE FOLLOWING SPECIFICATION PARTICULARLY DESCRIBES THE NATURE OF THIS INVENTION AND THE MANNER IN WHICH IT IS TO BE PERFORMED: -
7 JUL 2005

The present invention relates to a process of manufacturing Sodium Salicylate.
The prior art (faith et. Al., Industrial Chemicals (Wiles New York, 3r Ed. 1965)) discloses a method of manufacturing Sodium Salicylate by reacting Sodium phenoxide with Carbon Dioxide under pressure and dry conditions. Sodium Salicylate is isolated after carrying out the following steps viz. dissolution in water, carbon treatment, filtration, chilling, filtering and vacuum drying to obtain Sodium Salicylate in 60% - 65% yield. Along with the desired product, some unwanted isomeric sodium salts are also present.
Another prior art (Sidgwick, Ewbank, J. Chem. Soc. (1992)) describes preparation of Sodium Salicylate from Salicylic Acid. Salicylic Acid is reacted with Sodium Hydroxide in water and the formed Sodium Salicylate solution is chilled to produce Sodium Salicylate Hexahydrate Crystals (Sodium Salicylate along with six molecules of water), which are dried under vacuum at 100°C to furnish Sodium Salicylate in 60% - 65% Yield. This also contains certain unwanted isomeric Sodium salts. The sample prepared as per the above procedures does not pass the British Pharmacopoeia (B.P.2001) Specification.

The present invention obviates these drawbacks by manufacturing Sodium Salicylate with a better yield and making the reaction more economical as compared to other known reactions.
The present invention relates to a process of preparing Sodium Salicylate comprising of reacting Salicylic Acid with Sodium methoxide in the presence of organic solvent.
In a preferred embodiment, the present invention relates to a process of manufacturing Sodium Salicylate using methanolic solution of Sodium Methoxide.
Salicylic acid is suspended in methanolic solution of Sodium Methoxide in mixed xylene/ o-dichloro benzene/ o-xylene/ monochloro benzene or a mixture thereof and heated, preferably to 65°C with stirring. Sodium Salicylate is isolated by cooling the reaction mixture, filtering, washing with cold methanol and drying at 80°C, to obtain Sodium Salicylate in 95 % yield. The sample passes B.P. 2001.
In a more preferred embodiment, the present invention relates to a process of manufacturing Sodium Salicylate using methanolic solution in
25% w/v.

Alternatively, Sodium Methoxide Solid / Dry Powder is used in the process of manufacturing Sodium Salicylate.
The invention will now be described with reference to the following examples. The examples are only illustrative and in no way limit the scope of the invention.
EXAMPLE-1
Charge Salicylic Acid (100 gm) with o-dichloro benzene (500 ml) followed by the addition of Sodium methoxide (135 ml, 25% w/v solution in methanol). Heat the reaction mixture to 65°C with stirring for 8 hours. Cool the contents to 30°C and adjust to pH 7 by adding Salicylic Acid. Distil methanol, cool the contents to 30°C and filter the product. Wash it with 10 ml cold methanol and dry the wet cake at 80°C till we obtain a constant weight. The product obtained has a dry weight of 110 gms in 95% yield. Further, it passes both IP-1996 and B.P-2001 Specifications.


EXAMPLE-2
Charge Salicylic Acid (100 gm) with mixed xylene (500 ml) followed by Sodium methoxide (135 ml, 25% w/v sodium methoxide solution). Heat the reaction mass to 65°C and continue to stir, maintaining it at the same temperature for 6 hours. Cool the contents to 30°C and adjust to pH 7 by adding Salicylic Acid. Distil methanol, cool the contents to 30°C and filter the product. Wash it with cold methanol. Dry the wet cake at 80°C till we obtain a constant weight. The product obtained has a dry weight of 110 gms in 95% yield. Further, it passes IP-1996 and B.P-2001 Specifications.
EXAMPLE-3
Charge Salicylic Acid (100 gm) with o-xylene (500 ml) followed by Sodium methoxide (135 ml, 25% w/v sodium methoxide solution). Heat the reaction mass to 65°C and continue to stir, maintaining at 65°C for 6 hours. Cool the content to 30°C and adjust to pH 7 by adding Salicylic Acid. Distil 120 ml methanol. Cool the contents to 30°C and filter the product Wash the cake with cold methanol. Dry the wet cake at 80°C till we obtained a constant weight. The product obtained has a dry weight of

110 gms in 95% yield. Further, it passes IP-1996 and B.P-2001 Specifications.
EXAMPLE-4
Charge Salicylic Acid (100 gm) with Para xylene (500 ml) followed by Sodium methoxide (135 ml, 25% w/v sodium methoxide solution). Heat the reaction mass to 65°C and continue to stir, maintaining the temperature at 65°C for 6 hours. Cool the contents to 30°C and adjust to pH 7 by adding Salicylic Acid. Distil 120 ml methanol. Cool the contents to 30°C and filter the product. Wash the cake with cold methanol. Dry the wet cake at 80°C till we obtain a constant weight. The product obtained has a dry weight of 110 gms in 95% yield. Further, it passes IP-1996 and B.P.-2001 Specifications.
EXAMPLE-5
Charge Salicylic Acid (100 gm) with mono chloro benzene (500 ml) followed by Sodium methoxide (135 ml, 25% w/v sodium methoxide solution). Heat the reaction mass to 65°C and continue to stir, maintaining temperature at 65°C for 6 hours. Cool the contents to 30°C and adjust to pH 7 by adding Salicylic Acid. Distil 120 ml methanol. Cool the contents

to 30°C and filter the product. Wash it with cold methanol. Dry the wet cake at 80°C till constant weight. The product obtained has a dry weight of 110 gms in 95% yield. Further, it passes IP-1996 and B.P-2001 Specifications.

We Claim:
1. A process of preparing Sodium Salicylate comprising of reacting Salicylic Acid with Sodium methoxide in the presence of at least an organic solvent at a temperature of 65°C for about 6 hours and cooling the reaction mixture to 30°C.
2. A process of preparing Sodium Salicylate as claimed in Claim 1, wherein Salicylic Acid is reacted with methanolic solution of Sodium methoxide.
3. A process of preparing Sodium Salicylate as claimed in Claim 1, wherein the organic solvent is mixed xylene or o-dichloro benzene or o-xylene or monochloro benzene or a mixture of either of them.
4. A process of preparing Sodium Salicylate as claimed in Claim 2, wherein the concentration of methanolic solution is 25% w/v.
5. A process of preparing Sodium Salicylate as claimed in Claim 1, wherein Sodium methoxide is in a solid form.


6. A process of preparing Sodium Salicylate as claimed in Claim 1, wherein Sodium methoxide is dry.
7. A process of preparing Sodium Salicylate as claimed in Claim 1, wherein the resultant mixture is further distilled and dried at 80°C.
8. A process of preparing Sodium Salicylate as herein described with reference to the examples (1-5) accompanying the specification.
Dated this 10th day of March 2004.
Himanshu Wasudeo Kane Applicants" Patent Agent
To:
The Controller of Patents,
The Patent Office,
Mumbai 400 013.

Documents:

260-mum-2003-abstract(7-7-2005).doc

260-mum-2003-abstract(7-7-2005).pdf

260-mum-2003-cancelled pages(7-7-2005).pdf

260-mum-2003-claims(granted)-(7-7-2005).doc

260-mum-2003-claims(granted)-(7-7-2005).pdf

260-mum-2003-correspondence(12-5-2006).pdf

260-mum-2003-correspondence(ipo)-(13-3-2005).pdf

260-mum-2003-form 1(10-3-2003).pdf

260-mum-2003-form 2(granted)-(7-7-2005).doc

260-mum-2003-form 2(granted)-(7-7-2005).pdf

260-mum-2003-form 3(10-3-2003).pdf

260-mum-2003-form 5(10-3-2004).pdf

260-mum-2003-other document(21-8-2003).pdf


Patent Number 203930
Indian Patent Application Number 260/MUM/2003
PG Journal Number 20/2007
Publication Date 18-May-2007
Grant Date 01-Nov-2006
Date of Filing 10-Mar-2003
Name of Patentee GUJRAT ORGANICS LIMITED
Applicant Address PLOT NO. 127/1, GIDC ESTATE, ANKLESHWAR 393 002
Inventors:
# Inventor's Name Inventor's Address
1 DR. BHIKSHANDARKOVIL PARTHASARATHI CHANDRASEKHAR, DR. RAJESH KUMAR PATHAK BOTH ARE INDIA CITIZEN, PLOT NO. 127/1, GIDC ESTATE, ANKLESHWAR 393 002
PCT International Classification Number N/A
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA