Indian Patents. 271110:"A PROCESS FOR MANUFACTURE OF POLYCOSANOL FROM SUGAR CANE PRESS MUD"

Title of Invention	"A PROCESS FOR MANUFACTURE OF POLYCOSANOL FROM SUGAR CANE PRESS MUD"
Abstract	The present invention provides a novel method for the manufacture and isolation of polycosanol comprising of primary aliphatic alcohols having 24 to 34 carbon atoms, such as tetracosanol, pentacosanol, hexacosanol, heptacosanol. octacosanol, nanocosanol, triacontanol, from fatty waxes of sugar cane press mud in sugar industry.

Full Text	FORM 2 THE PATENTS ACT, 1970 (39 OF 1970) & THE PATENT RULES, 2003 COMPLETE SPECIFICATION (See section 10 and rule 13) 1 TITLE OF THE INVENTION An efficient extractive hydrolytic multiphase process for manufacture and simultaneous isolation of polycosanol comprising of a mixture of primary aliphatic higher alcohols of having 20 to 34 carbon atoms from sugar cane and sugar cane press mud and other materials obtained in sugar cane processing. 2. APPLICANT (a) NAME : The Godavari Sugar Mills Ltd. (b) NATIONALITY : INDIA (c) ADDRESS : Fazalbhoy Bldg., 45/47, Mahatma Gandhi Road, Fort, Mumbai-400 001. 3. PREAMBLE TO THE DESCRIPTION The following specification particularly describes and ascertains the invention and the manner in which it is to be performed. ABSTRACT The present invention provides a novel method for the manufacture and isolation of polycosanol comprising of primary aliphatic alcohols having 24 to 34 carbon atoms, such as tetracosanol, pentacosanol, hexacosanol, heptacosanol. octacosanol, nanocosanol, triacontanol, from fatty waxes of sugar cane press mud in sugar industry. DESCRIPTION FIELD OF INVENTION The present invention provides a novel and efficient method for manufacture and isolation of primary aliphatic alcohols, having 24 to 34 carbon atoms, from sugar cane press mud or other materials in sugar industry by multiphase extractive hydrolysis technique. Included in the present invention is the composition of the matter, referred to herein as "polycosanol" produced by the method of this invention. The polycosanol composition is comprised of the primary aliphatic alcohols such as tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol. nanocosanol. triacontanol. BACKGROUND OF THE INVENTION Polycosanols are a class of primary aliphatic alcohols having 20 to 40 (C20-C40) carbon atoms with terminal hydroxyl group. They are widely distributed in germs, kernels and other components of nuts, seeds, fruits and cereals (Kawanishi et a/.(1991) J. Amer. Oil Chemist Soc. 68: 869-872), in Greek olive oils (Dimitrios et til. (1983) Grasas Aceites 34: 402-404) and in apple wax (Belding et al. (1993) Hertscience 28: 90). Polycosanols are also present, in very small amounts (less than 0.1%), in wheat grain, in the form of the long chain alkyl esters of fatty acids. The major compounds present in wheat grain include, palmitoyl hexacosanol and arachidoyl-, palmitoyl- and behenoyl tetracosanol (Ohnishi etal. (1986) Cereal Chem 63: 193- 196). Polycosanol compositions isolated from sugar cane have been shown to lower cholesterol levels in both animal and human models. (Menedez et al. (2000) Br. J. Clin. Pharmacol. 50: 255-262: Arruzazabala et al. Braz. J. Med. Biol. Res. 33:835-840 ; Crespo et al. (1999) Int. J. Clin. Pharmacol. 19 : 117-127 : Gouni-Berthold and Berthold (2002) Am. Heart J. 143: 356-365: Alcocer et al. (1999) Int. J. Tissue React 21: 85-92). Sugar cane provides a major natural source of commercial polycosanol products (AH et al. (1979) Egypt J. Pharm. Sci. 18: 93-99). The long chain aliphatic alcohols are located primarily in the fatty waxes of sugar cane, with octacosanol being the predominant compound (Nagata et al. (1994) Breeding Sci. 44: 427-429) Polycosanol compositions isolated from rice bran wax have been formulated with phytosterol from vegetable oil and used for reducing cholesterol levels. The primary aliphatic alcohol profile of this material is approximately 23-33% of total polycosanol. Polycosanol(s) and polycosanolic acids have also been reported to be effective as nutritional and therapeutic preparations for the prevention and treatment of aging and related conditions, such as atherosclerosis, hypertension, diabetes, tumors, obesity, overweight, hypertriglyceridemia, hypercholesterolemia, as well as other conditions. (Pistolesi, WO02/052955 (2001)). The polycosanol compositions isolated from sugar cane showed a significant benefit in hypercholesterolemia postmenopausal women (Mirkin el al. (2001) Int. J. Clin. Pharmacol. 21: 31-41) It has been proposed that polycosanol compositions isolated from sugar cane could potentially provide a new treatment for cardiovascular diseases with equal or better clinical output than simvastatin, pravastatin, lovastatin,probucol and acipimox. (Janikula (2002) Altern. Med. Rev. 7: 203-217). There are a numerous other reported uses of individual polycosanols and mixtures thereof in the literature. Bertholet has described a method for preparing polycosanol compositions by means of the saponification of plant waxes from rice bran wax, carnauba wax and jojoba oil. (Bertholet, U. S. Pat. No. 5,159, 124 (1991)). The sugar cane wax can be extracted directly with a supercritical fluid, an organic solvent or an alcohol (Inada etal. (1986) U. S. Pat. No. 4,714. 791). A mixture of higher primary aliphatic alcohols, having from 24 to 34 carbon atoms has been obtained by saponification of sugar cane wax obtained separately by solvent extraction. (Laguna el al. (1996) U. S. Pat. No. 5.856, 316). The saponification reaction described included melting the sugar cane wax, forming a homogeneous phase with an alkaline earth hydroxide (5-30%), followed by extraction with an organic solvent and recrystallizing polycosanols from an organic solvent. Bee wax also contains a significant quantity of long chain primary alcohols in both the free and esterified forms. In the method reported by Henzandez el al., U. S. Pat. No. 6.465. 526 (2000). the saponification reaction was performed in the homogeneous phase using a 4-7: 1 wax: base ratio. After the hydrolysis reaction, the polycosanols were extracted with organic solvent, which was further treated to recover a product that contained 80-98% total polycosanols. The polycosanols in the bee wax have also been extracted directly with organic solvent without saponification. (Perez. U. S. Pat. No. 6.225. 354 (1999) ). U. S. Pat. No. 6.822. 004 (2003) describes the composition of matter isolated by solvent extraction following hydrolysis of the Ericerus Pela wax and further purification via extraction of the polycosanols under basic conditions with an organic solvent. In this embodiment, the composition of matter is comprised of approximately 75-100% of the long chain primary aliphatic alcohols. United States Patent 5159124 (1991) describes a process for obtaining compounds from waxes, when insoluble material is formed by the process, comprising saponifying a wax dissolved in an organic water-immiscible solvent with an alkali and thereby obtaining a mixture of saponified and unsaponified compounds in the solvent. All these processes involve separate steps of isolation of the waxes and hydrolysis of the isolated waxes. United States Patent 5856316 (1996) describes a process of extraction of polycosanol by saponification of the waxes followed by solid liquid extraction to extract the polycosanols into the organic solvent. The extraction of waxes into organic solvent is a very slow process and needs a large quantity of solvent to effectively handle the raw material. The subsequent handling of raw material and the extract in multiple stages leads to substantial losses of organic solvents, and reduced yields of the product adding to the cost of the final product. An object of the present invention is to extract primary normal aliphatic higher alcohols in an industrially advantageous manner while overcoming the disadvantages of the prior art. The method of the present invention is based on the extractive hydrolysis of the waxes present in the sugar cane press mud and other materials available in sugar industry in the presence of a multi phase system involving an aqueous phase with mineral acidic or alkaline or alkali metal hydroxide and an organic solvent for simultaneous extraction of higher primary aliphatic alcohols released by the hydrolysis/saponification reaction of the waxes. It is an objective of this invention to provide a mixture of higher primary aliphatic alcohols, referred to herein as "polycosanol(s)"" having a unique chemical composition profile comprising tetracosanol. pentacosanol, hexacosanol. heptacosanol, octacosanol. nanocosanol. triacontanol. SUMMARY OF THE INVENTION The present invention describes a noval and efficient process of manufacture and isolation of primary aliphatic fatty alcohols, having 24 to 30 carbon atoms, from the press mud obtained from sugar industry by an extractive hydrolysis process in a multiphase system. Included in the present invention is the composition of matter, referred to herein as "polycosanol" produced by the method of this invention. The polycosanol composition is comprised of primary aliphatic alcohols such as tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol. nanocosanol, triacontanol. DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an extractive hydrolysis reaction process for manufacture and isolation of primary aliphatic higher alcohols having 24 to 30 carbon atoms with terminal hydroxy group from press mud and other materials of sugar industry comprising the steps a) Extractive hydrolysis of the fatty waxes in the press mud of sugar industry in a multiphase system involving an aqueous solution of acid or an alkali and an organic solvent to obtain an extract of higher primary long chain aliphatic alcohols in the organic phase. b) Concentration of the organic solvent phase by removal of solvent followed by isolation and purification of polycosanol by known methods. The raw material press mud is sugarcane as such, sugarcane juice obtained by milling or diffusion of sugarcanes. residues or bagasses from milling or diffusion of sugarcanes to obtain sugarcane juice, dried sugarcane leaves, scums, precipitates or press mud or filter cakes from clarification process of sugarcane juice by liming, carbonating, sulfiting or phosphating, clarified sugarcane juice from the liming, and molasses. An aqueous solution is selected from mineral acidic group such as sulphuric acid, hydrochloric acid or mixtures there of or an alkaline earth metal hydroxide. NaOH, KOH. Ba(OH)2 and Ca(OH)2 or mixtures thereof, preferably KOH, is mixed with an organic solvent selected from the group comprising of benzene, toluene and xylene, cumene. ethyl benzene or the mixtures thereof, with suspended raw solid or semisolid material and vigorously stirred in a multiphase system to bring in the intimate contact all the three phases where in the fatty waxes from the press mud are hydrolysed and the polycosanols so released as the product of the reaction are extracted into the organic solvent at a temperature in the range 25-150 °C. limited by the boiling point of the solvent or solvent system, for 4-25 hours The reaction mixture is then brought to room temperature and the organic phase is separated from the other constituents of the reaction mixture. The mushy solid or semisolid cake retains all of the water and the organic phase layer containing the desired and extracted higher primary aliphatic alcohols is washed with water to remove water soluble impurities. The fatty acid byproducts of the reaction are soluble in the aqueous layer and the polycosanol alcohol product remains in the organic layer. The organic phase is then treated with charcoal to remove color of the solution and then subjected to evaporation to concentrate the organic extract of polycosanols. Afterwards, the mixture is successively crystallized using the solvents selected from the group comprising methanol, chloroform, ethanol, ethyl acetate and toluene, preferably with ethyl acetate to obtain a high purity of primary long chain aliphatic higher alcohols referred to as 'polycosanol comprised of tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nanocosanol, triacontanol. The procedure of this invention for obtaining the natural mixture of higher primary aliphatic alcohols from press mud has some advantages compared to prior art procedures. One of these advantages is related with the shorter reaction and extraction time because of simultaneous operation. Other advantages of this invention are related to the practical yield of 2.6 %, reduced number of operations and reduced use of solvents for recovery of product. Another advantage of the procedure relates to the purity of the product that can be obtained (more than 80 %), which is significantly higher than the purity of polycosanols obtained by the prior art methods. Thus, the method of the present invention is simple and appropriate for large-scale industrial production. The following examples illustrate various aspects and the scope of the invention. EXAMPLE 1: Potassium hydroxide solution (15 %) is heated with 3 liter of toluene to 85 °C and 200 gm of press mud, a settled waste obtained as a result of sedimentation after sulphitation process of sugarcane juice, was added with vigorous stirring. The hydrolysis/saponification reaction was allowed to proceed for 6 hours at 95 °C .The reaction mixture was cooled to room temperature and filtered. The aqueous solution used in the saponification is retained by press mud or filter cake. The organic toluene phase separated form the reaction mass was washed with water, treated with charcoal to remove color of the organic phase extract solution and concentrated by evaporation to 20 % of original volume to obtain a crude polycosanol which is crystallized with methanol to yield 79.5 % pure 3.02 gm polycosanol. EXAMPLE 2: Sodium hydroxide solution (10 %) is heated with 3.5 liter of xylene at 60 °C and 225 gm of pressmud, a settled waste obtained as a result of sedimentation before processing of sugarcane juice, was added with vigorous stirring . The saponification reaction was allowed to proceed for 7.5 hours at 80 °C. The reaction mixture was cooled to room temperature and filtered, maximum water used in saponification is retained by pressmud or filter cake. The organic layer (3.22 1) separated was washed with water, treated with charcoal to remove color and concentrated by evaporation to obtain a crude polycosanol (82 % yield) which is crystallized with mixture of chloroform and methanol to 99 % pure 2.25 gm polycosanol. EXAMPLE 3: An acidic hydrolysis of dried cane leaves (350 gm), done by hydrochlororic acid (45 gm in 500 ml water), is heated with 3.5 liter of toluene at60°C with continuous stirring. The saponification reaction was allowed to proceed for 19 hours at 60 °C. The reaction mixture was cooled to room temperature and filtered, maximum water used in saponification is retained by pressmud or filter cake. The toluene layer separated was washed with dilute alkali followed by water, treated with charcoal to remove color and concentrated by evaporation to obtain a crude polycosanol which is crystallized with ethyl acetate to yield 80 % of pure polycosanol. EXAMPLE 4: Aquous sulphuric acid solution (4 %) is heated with 2 liter of toluene at 60 °C and 350 gm of press mud, a solid waste obtained as a result of sedimentation of particles in sugarcane juice after liming, was added with stirring. The saponification reaction was allowed to proceed for 15 hours at 90 °C. The reaction mixture was cooled to room temperature and filtered, maximum water used in saponification is retained by pressmud or filter cake. The organic layer separated was washed with dilute alkali followed by water, treated with charcoal to remove color and concentrated by evaporation to obtain a crude polycosanol which is crystallized with chloroform to yield 3.6 gm of 78 % pure polycosanol. CLAIMS: We claim: 1. An efficient extractive hydrolytic multiphase process for manufacture and simultaneous isolation of polycosanol comprising of a mixture of primary aliphatic higher alcohols of having 20 to 34 carbon atoms from sugar cane and sugar cane press mud and other materials obtained in sugar cane processing, comprising of the steps: a. Alkaline or acidic hydrolysis of the solid and semisolid fatty waxes of the sugar cane press mud in a multiphase system of solid material, an aqueous solution and an organic solvent phase at a temperature in the range 25-150 °C limited by the boiling point of the organic solvent system and simultaneous extraction of crude polycosanol into an organic solvent. b. Concentration, isolation and purification of polycosanol by known methods. 2. A process according to Claim-1, wherein the raw sugarcane press mud material is selected from sugarcane as such, sugarcane juice obtained by milling or diffusion of sugarcanes, residues or bagasses from milling or diffusion of sugarcanes to obtain sugarcane juice, dried sugarcane leaves, scums, precipitate or press mud, filter cakes from clarification process of sugarcane juice by liming, carbonating, sulfiting or phosphating, clarified sugarcane juice from the liming, and molasses. 3. The process as in Claim-1 for extractive hydrolysis of the said fatty waxes of the fatty alcohols and fatty acids in three-phase systems wherein aqueous solution of mineral acids such as sulphuric acid or hydrochloric acid or mixtures there of or an alkali base is selected from a group of alkali or alkaline earth metal hydroxides such as NaOH, KOH, Ba(OH)2 and Ca(OH) 2 or mixtures there of. 4. The process as in Claim-1. wherein hydrolysis is by the alkaline base preferably KOH. 5. The process as in Claim-1 for extractive hydrolysis of the said fatty waxes of the fatty alcohols and fatty acids in the raw material in three-phase systems wherein an organic solvent is selected from a group of aliphatic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, petroleum ethers or mixtures there of. 6. The process as in Claim-1. wherein the organic solvent is preferably an aromatic hydrocarbon selected from the group comprising of benzene, toluene, xylene, cumene, ethyl benzene or an aliphatic hydrocarbon such as hexane. heptane, isooctane. octane, isobutyl ether, or mixtures there of. 7. The process as in Claim-1 wherein the extractive hydrolysis of the fatty waxes in the raw material is preferably carried out in the temperature range 25-125 °C. limited by the boiling point of the solvent in the three phase system or that of the solvent mixtures under given conditions of pressure for a period of 2-24 hours. 8. The process according to Claim-1 wherein polycosanol is recovered from the organic solvent by concentration and crystallization from the concentrated extract and after separation of other impurities by known methods. 9. The process according to Claim-1 wherein the said polycosanol product consists of mixture of long chain aliphatic primary alcohols comprising of tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nanocosanol, triacontanol. Dated this 1st day of September 2005 FOR THE GODAVARI SUGAR MILLS LTD. Signature Name Designation :Samir S. Somaiya :Executive Director

Full Text

FORM 2
THE PATENTS ACT, 1970
(39 OF 1970)
&
THE PATENT RULES, 2003
COMPLETE SPECIFICATION
(See section 10 and rule 13)
1 TITLE OF THE INVENTION
An efficient extractive hydrolytic multiphase process for manufacture and simultaneous isolation of polycosanol comprising of a mixture of primary aliphatic higher alcohols of having 20 to 34 carbon atoms from sugar cane and sugar cane press mud and other materials obtained in sugar cane processing.
2. APPLICANT
(a) NAME : The Godavari Sugar Mills Ltd.
(b) NATIONALITY : INDIA
(c) ADDRESS : Fazalbhoy Bldg., 45/47, Mahatma Gandhi Road, Fort, Mumbai-400 001.
3. PREAMBLE TO THE DESCRIPTION
The following specification particularly describes and ascertains the invention and the manner in which it is to be performed.

ABSTRACT
The present invention provides a novel method for the manufacture and isolation of polycosanol comprising of primary aliphatic alcohols having 24 to 34 carbon atoms, such as tetracosanol, pentacosanol, hexacosanol, heptacosanol. octacosanol, nanocosanol, triacontanol, from fatty waxes of sugar cane press mud in sugar industry.
DESCRIPTION
FIELD OF INVENTION
The present invention provides a novel and efficient method for manufacture and isolation of primary aliphatic alcohols, having 24 to 34 carbon atoms, from sugar cane press mud or other materials in sugar industry by multiphase extractive hydrolysis technique. Included in the present invention is the composition of the matter, referred to herein as "polycosanol" produced by the method of this invention. The polycosanol composition is comprised of the primary aliphatic alcohols such as tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol. nanocosanol. triacontanol.
BACKGROUND OF THE INVENTION
Polycosanols are a class of primary aliphatic alcohols having 20 to 40 (C20-C40) carbon atoms with terminal hydroxyl group. They are widely distributed in germs, kernels and other components of nuts, seeds, fruits and cereals (Kawanishi et a/.(1991) J. Amer. Oil Chemist Soc. 68: 869-872), in Greek olive oils (Dimitrios et til. (1983) Grasas Aceites 34: 402-404) and in apple wax (Belding et al. (1993) Hertscience 28: 90). Polycosanols are also present, in very small amounts (less than 0.1%), in wheat grain, in the form of the long chain alkyl esters of fatty acids. The major compounds present in wheat grain include, palmitoyl hexacosanol and arachidoyl-, palmitoyl- and behenoyl tetracosanol (Ohnishi etal. (1986) Cereal Chem 63: 193- 196).
Polycosanol compositions isolated from sugar cane have been shown to lower cholesterol levels in both animal and human models. (Menedez et al. (2000) Br. J. Clin. Pharmacol. 50: 255-262: Arruzazabala et al. Braz. J. Med. Biol. Res. 33:835-840 ; Crespo et al. (1999) Int. J. Clin. Pharmacol. 19 : 117-127 : Gouni-Berthold and Berthold (2002) Am. Heart J. 143: 356-365: Alcocer et al. (1999) Int. J. Tissue React 21: 85-92).
Sugar cane provides a major natural source of commercial polycosanol products (AH et al. (1979) Egypt J. Pharm. Sci. 18: 93-99). The long chain aliphatic alcohols are located primarily in the fatty waxes of sugar cane, with octacosanol being the predominant compound (Nagata et al. (1994) Breeding Sci. 44: 427-429)

Polycosanol compositions isolated from rice bran wax have been formulated with phytosterol from vegetable oil and used for reducing cholesterol levels. The primary aliphatic alcohol profile of this material is approximately 23-33% of total polycosanol.
Polycosanol(s) and polycosanolic acids have also been reported to be effective as nutritional and therapeutic preparations for the prevention and treatment of aging and related conditions, such as atherosclerosis, hypertension, diabetes, tumors, obesity, overweight, hypertriglyceridemia, hypercholesterolemia, as well as other conditions. (Pistolesi, WO02/052955 (2001)).
The polycosanol compositions isolated from sugar cane showed a significant benefit in hypercholesterolemia postmenopausal women (Mirkin el al. (2001) Int. J. Clin. Pharmacol. 21: 31-41)
It has been proposed that polycosanol compositions isolated from sugar cane could potentially provide a new treatment for cardiovascular diseases with equal or better clinical output than simvastatin, pravastatin, lovastatin,probucol and acipimox. (Janikula (2002) Altern. Med. Rev. 7: 203-217). There are a numerous other reported uses of individual polycosanols and mixtures thereof in the literature.
Bertholet has described a method for preparing polycosanol compositions by means of the saponification of plant waxes from rice bran wax, carnauba wax and jojoba oil. (Bertholet, U. S. Pat. No. 5,159, 124 (1991)).
The sugar cane wax can be extracted directly with a supercritical fluid, an organic solvent or an alcohol (Inada etal. (1986) U. S. Pat. No. 4,714. 791).
A mixture of higher primary aliphatic alcohols, having from 24 to 34 carbon atoms has been obtained by saponification of sugar cane wax obtained separately by solvent extraction. (Laguna el al. (1996) U. S. Pat. No. 5.856, 316). The saponification reaction described included melting the sugar cane wax, forming a homogeneous phase with an alkaline earth hydroxide (5-30%), followed by extraction with an organic solvent and recrystallizing polycosanols from an organic solvent.
Bee wax also contains a significant quantity of long chain primary alcohols in both the free and esterified forms. In the method reported by Henzandez el al., U. S. Pat. No. 6.465. 526 (2000). the saponification reaction was performed in the homogeneous phase using a 4-7: 1 wax: base ratio. After the hydrolysis reaction, the polycosanols were extracted with organic solvent, which was further treated to recover a product that contained 80-98% total polycosanols.
The polycosanols in the bee wax have also been extracted directly with organic solvent without saponification. (Perez. U. S. Pat. No. 6.225. 354 (1999) ).
U. S. Pat. No. 6.822. 004 (2003) describes the composition of matter isolated by solvent extraction following hydrolysis of the Ericerus Pela wax and further purification via

extraction of the polycosanols under basic conditions with an organic solvent. In this embodiment, the composition of matter is comprised of approximately 75-100% of the long chain primary aliphatic alcohols.
United States Patent 5159124 (1991) describes a process for obtaining compounds from waxes, when insoluble material is formed by the process, comprising saponifying a wax dissolved in an organic water-immiscible solvent with an alkali and thereby obtaining a mixture of saponified and unsaponified compounds in the solvent.
All these processes involve separate steps of isolation of the waxes and hydrolysis of the isolated waxes. United States Patent 5856316 (1996) describes a process of extraction of polycosanol by saponification of the waxes followed by solid liquid extraction to extract the polycosanols into the organic solvent. The extraction of waxes into organic solvent is a very slow process and needs a large quantity of solvent to effectively handle the raw material. The subsequent handling of raw material and the extract in multiple stages leads to substantial losses of organic solvents, and reduced yields of the product adding to the cost of the final product.
An object of the present invention is to extract primary normal aliphatic higher alcohols in an industrially advantageous manner while overcoming the disadvantages of the prior art.
The method of the present invention is based on the extractive hydrolysis of the waxes present in the sugar cane press mud and other materials available in sugar industry in the presence of a multi phase system involving an aqueous phase with mineral acidic or alkaline or alkali metal hydroxide and an organic solvent for simultaneous extraction of higher primary aliphatic alcohols released by the hydrolysis/saponification reaction of the waxes.
It is an objective of this invention to provide a mixture of higher primary aliphatic alcohols, referred to herein as "polycosanol(s)"" having a unique chemical composition profile comprising tetracosanol. pentacosanol, hexacosanol. heptacosanol, octacosanol. nanocosanol. triacontanol.

SUMMARY OF THE INVENTION
The present invention describes a noval and efficient process of manufacture and isolation of primary aliphatic fatty alcohols, having 24 to 30 carbon atoms, from the press mud obtained from sugar industry by an extractive hydrolysis process in a multiphase system. Included in the present invention is the composition of matter, referred to herein as "polycosanol" produced by the method of this invention. The polycosanol composition is comprised of primary aliphatic alcohols such as tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol. nanocosanol, triacontanol.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to an extractive hydrolysis reaction process for manufacture and isolation of primary aliphatic higher alcohols having 24 to 30 carbon atoms with terminal hydroxy group from press mud and other materials of sugar industry comprising the steps
a) Extractive hydrolysis of the fatty waxes in the press mud of sugar industry in a multiphase system involving an aqueous solution of acid or an alkali and an organic solvent to obtain an extract of higher primary long chain aliphatic alcohols in the organic phase.
b) Concentration of the organic solvent phase by removal of solvent followed by isolation
and purification of polycosanol by known methods.
The raw material press mud is sugarcane as such, sugarcane juice obtained by milling or diffusion of sugarcanes. residues or bagasses from milling or diffusion of sugarcanes to obtain sugarcane juice, dried sugarcane leaves, scums, precipitates or press mud or filter cakes from clarification process of sugarcane juice by liming, carbonating, sulfiting or phosphating, clarified sugarcane juice from the liming, and molasses.
An aqueous solution is selected from mineral acidic group such as sulphuric acid, hydrochloric acid or mixtures there of or an alkaline earth metal hydroxide. NaOH, KOH. Ba(OH)2 and Ca(OH)2 or mixtures thereof, preferably KOH, is mixed with an organic solvent selected from the group comprising of benzene, toluene and xylene, cumene. ethyl benzene or the mixtures thereof, with suspended raw solid or semisolid material and vigorously stirred in a multiphase system to bring in the intimate contact all the three phases where in the fatty waxes from the press mud are hydrolysed and the polycosanols so released as the product of the reaction are extracted into the organic solvent at a temperature in the range 25-150 °C. limited by the boiling point of the solvent or solvent system, for 4-25 hours
The reaction mixture is then brought to room temperature and the organic phase is separated from the other constituents of the reaction mixture. The mushy solid or semisolid cake retains all of the water and the organic phase layer containing the desired and extracted higher primary aliphatic alcohols is washed with water to remove water

soluble impurities. The fatty acid byproducts of the reaction are soluble in the aqueous layer and the polycosanol alcohol product remains in the organic layer. The organic phase is then treated with charcoal to remove color of the solution and then subjected to evaporation to concentrate the organic extract of polycosanols. Afterwards, the mixture is successively crystallized using the solvents selected from the group comprising methanol, chloroform, ethanol, ethyl acetate and toluene, preferably with ethyl acetate to obtain a high purity of primary long chain aliphatic higher alcohols referred to as 'polycosanol comprised of tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nanocosanol, triacontanol.
The procedure of this invention for obtaining the natural mixture of higher primary aliphatic alcohols from press mud has some advantages compared to prior art procedures. One of these advantages is related with the shorter reaction and extraction time because of simultaneous operation. Other advantages of this invention are related to the practical yield of 2.6 %, reduced number of operations and reduced use of solvents for recovery of product. Another advantage of the procedure relates to the purity of the product that can be obtained (more than 80 %), which is significantly higher than the purity of polycosanols obtained by the prior art methods. Thus, the method of the present invention is simple and appropriate for large-scale industrial production.
The following examples illustrate various aspects and the scope of the invention.
EXAMPLE 1:
Potassium hydroxide solution (15 %) is heated with 3 liter of toluene to 85 °C and 200 gm of press mud, a settled waste obtained as a result of sedimentation after sulphitation process of sugarcane juice, was added with vigorous stirring. The hydrolysis/saponification reaction was allowed to proceed for 6 hours at 95 °C .The reaction mixture was cooled to room temperature and filtered. The aqueous solution used in the saponification is retained by press mud or filter cake. The organic toluene phase separated form the reaction mass was washed with water, treated with charcoal to remove color of the organic phase extract solution and concentrated by evaporation to 20 % of original volume to obtain a crude polycosanol which is crystallized with methanol to yield 79.5 % pure 3.02 gm polycosanol.
EXAMPLE 2:
Sodium hydroxide solution (10 %) is heated with 3.5 liter of xylene at 60 °C and 225 gm of pressmud, a settled waste obtained as a result of sedimentation before processing of sugarcane juice, was added with vigorous stirring . The saponification reaction was allowed to proceed for 7.5 hours at 80 °C. The reaction mixture was cooled to room temperature and filtered, maximum water used in saponification is retained by pressmud or filter cake. The organic layer (3.22 1) separated was washed with water, treated with charcoal to remove color and concentrated by evaporation to obtain a crude polycosanol (82 % yield) which is crystallized with mixture of chloroform and methanol to 99 % pure 2.25 gm polycosanol.

EXAMPLE 3:
An acidic hydrolysis of dried cane leaves (350 gm), done by hydrochlororic acid (45 gm
in 500 ml water), is heated with 3.5 liter of toluene at60°C with continuous stirring. The saponification reaction was allowed to proceed for 19 hours at 60 °C. The reaction mixture was cooled to room temperature and filtered, maximum water used in saponification is retained by pressmud or filter cake. The toluene layer separated was washed with dilute alkali followed by water, treated with charcoal to remove color and concentrated by evaporation to obtain a crude polycosanol which is crystallized with ethyl acetate to yield 80 % of pure polycosanol.
EXAMPLE 4:
Aquous sulphuric acid solution (4 %) is heated with 2 liter of toluene at 60 °C and 350 gm of press mud, a solid waste obtained as a result of sedimentation of particles in sugarcane juice after liming, was added with stirring. The saponification reaction was allowed to proceed for 15 hours at 90 °C. The reaction mixture was cooled to room temperature and filtered, maximum water used in saponification is retained by pressmud or filter cake. The organic layer separated was washed with dilute alkali followed by water, treated with charcoal to remove color and concentrated by evaporation to obtain a crude polycosanol which is crystallized with chloroform to yield 3.6 gm of 78 % pure polycosanol.

CLAIMS:
We claim:
1. An efficient extractive hydrolytic multiphase process for manufacture and
simultaneous isolation of polycosanol comprising of a mixture of primary aliphatic
higher alcohols of having 20 to 34 carbon atoms from sugar cane and sugar cane press
mud and other materials obtained in sugar cane processing, comprising of the steps:
a. Alkaline or acidic hydrolysis of the solid and semisolid fatty waxes of the sugar
cane press mud in a multiphase system of solid material, an aqueous solution and
an organic solvent phase at a temperature in the range 25-150 °C limited by the
boiling point of the organic solvent system and simultaneous extraction of crude
polycosanol into an organic solvent.
b. Concentration, isolation and purification of polycosanol by known methods.
2. A process according to Claim-1, wherein the raw sugarcane press mud material is selected from sugarcane as such, sugarcane juice obtained by milling or diffusion of sugarcanes, residues or bagasses from milling or diffusion of sugarcanes to obtain sugarcane juice, dried sugarcane leaves, scums, precipitate or press mud, filter cakes from clarification process of sugarcane juice by liming, carbonating, sulfiting or phosphating, clarified sugarcane juice from the liming, and molasses.
3. The process as in Claim-1 for extractive hydrolysis of the said fatty waxes of the fatty alcohols and fatty acids in three-phase systems wherein aqueous solution of mineral acids such as sulphuric acid or hydrochloric acid or mixtures there of or an alkali base is selected from a group of alkali or alkaline earth metal hydroxides such as NaOH, KOH, Ba(OH)2 and Ca(OH) 2 or mixtures there of.
4. The process as in Claim-1. wherein hydrolysis is by the alkaline base preferably KOH.
5. The process as in Claim-1 for extractive hydrolysis of the said fatty waxes of the fatty alcohols and fatty acids in the raw material in three-phase systems wherein an organic solvent is selected from a group of aliphatic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, petroleum ethers or mixtures there of.
6. The process as in Claim-1. wherein the organic solvent is preferably an aromatic
hydrocarbon selected from the group comprising of benzene, toluene, xylene, cumene,
ethyl benzene or an aliphatic hydrocarbon such as hexane. heptane, isooctane. octane,
isobutyl ether, or mixtures there of.
7. The process as in Claim-1 wherein the extractive hydrolysis of the fatty waxes in the raw material is preferably carried out in the temperature range 25-125 °C. limited by the boiling point of the solvent in the three phase system or that of the solvent mixtures under given conditions of pressure for a period of 2-24 hours.

8. The process according to Claim-1 wherein polycosanol is recovered from the organic solvent by concentration and crystallization from the concentrated extract and after separation of other impurities by known methods.
9. The process according to Claim-1 wherein the said polycosanol product consists of mixture of long chain aliphatic primary alcohols comprising of tetracosanol, pentacosanol, hexacosanol, heptacosanol, octacosanol, nanocosanol, triacontanol.
Dated this 1st day of September 2005
FOR THE GODAVARI SUGAR MILLS LTD.

Signature
Name
Designation

:Samir S. Somaiya :Executive Director

Documents:

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Patent Number

271110

Indian Patent Application Number

1058/MUM/2005

PG Journal Number

06/2016

Publication Date

05-Feb-2016

Grant Date

03-Feb-2016

Date of Filing

01-Sep-2005

Name of Patentee

GODAVARI BIOREFINERIES LTD

Applicant Address

SOMAIY BHAVAN, 45/47, MAHATMA GANDHI ROAD, FORT,MUMBAI-400 001, MAHARASHTRA,INDIA

Inventors:

#	Inventor's Name	Inventor's Address
1	SOMAIYA, SAMIR S.	"PADMANABH", 10, M. L. DHANUKAR MARG MUMBAI-400 026
2	GAIKAR, V.G.	703-A, DHANANJAY APARTMENT, OFF VEERA DESAI ROAD, NEAR CHITRALEKHA, ANDHERI (W), MUMBAI-400 053
3	SRIVASTAVA, SANGEETA	1001, BHASKARA, TIFR COLONY, COLABA, MUMBAI-400 005
4	GHAG, SHAILESH	402, 4TH FLOOR, BHARATI APARTMENT CO-OPERATIVE HOUSING SOCIETY, NR. MUMBAI POONA ROAD, KALWA (W), THANE - 400 605

PCT International Classification Number

C07D7/00

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA