Title of Invention

A NOVEL KETENE OLIGOMER FROM ALIPHATIC NON-POLAR AMINO ACIDS AND A PROCESS FOR THE PREPARATION THEREOF

Abstract

This invention concerns a novel ketene oligomer of the general formula [R1R2C=C=O]n, where "n" is an integer in the range of 10 to 16; R1 and R2 are hydrogen atoms or alkyl groups having carbon chain length in the range of 1 to 4; R≠R2 or R. More particularly, the present invention relates to linear ketene oligomers of molecular weight in the range of 500 - 1000 having polyketene structure. The invention further provides a process for the preparation of the novel ketene oligomer from aliphatic non-polar amino acids in presence of transition metal impregnated activated carbon as catalyst. The oligomer of the present invention find enormous application for providing eco-friendly solutions in respect of a range of environmental pollution problems, because it acts as a strong chelator for transition metals to produce an effective reusable complex for inactivating wide spectrum of anaerobes and aerobes in the environment.

Full Text

FIELD OF INVENTION The present invention relates to a novel ketene oligomer from aliphatic non-polar amino acids and a process for the preparation thereof. Mopre particularly, the invention relates to a novel ketene oligomer of the general formula [R1R2C=C=O]n, where 'n' is an integer in the range of 10 to 16; R1 and R2 are hydrogen atoms or alkyl groups having carbon chain length in the range of 1 to 4; R1=R2 or R1-R2. More particularly, the present invention relates to linear ketene oligomers of molecular weight in the range of 500 - 1000. The invention further provides a process for the preparation of the novel ketene oligomer from aliphatic non-polar amino acids containing only carbon, hydrogen, nitrogen and oxygen. The oligomer of the present invention is envisaged to find enormous application for providing eco-friendly solutions in respect of a range of environmental pollution problems, because it acts as a strong chelator for transition metals to produce an effective reusable complex for inactivating wide spectrum of anaerobes and aerobes in the environment. The same feature also enables the product to find potential application in pharmaceutical industries. The product may also be used as a delivery system for drugs through microencapsulation. BACKGROUND OF THE INVENTION AND DESCRIPTION OF PRIOR ART Conventionally Ketenes are derivatives of carboxylic acid, which contains two consecutive double bonds (C=C=O), as reported by Egret et al. (European Polymer Journal, 38, 1953 - 1961, 2002). Ketene and its polymer constitute a class of compounds of great interest in organic synthesis as well as in polymer science. In Polymer chemistry, the term 'monomer (smallest repeating unit of polymers)' is defined as "a substance composed of molecules which can undergo polymerization, thereby contributing constitutional units to the essential structure of a polymer molecule". The term 'oligomer' can be defined as "a substance composed of molecules of intermediate relative molecular mass, the structure of which essentially comprises a small plurality of units derived, actually or conceptually from molecules of lower relative molecular mass (usually less than thirty monomer units)". 'Polymer' is "a substance composed of molecules of high relative molecular mass, the structure of which essentially comprises the multiple repeatition of units derived, actually or conceptually, from molecules of low relative molecular mass". Generally Ketene polymers are synthesized using ketenes and disubstituted ketenes by a suitable initiator system such as sodium naphthalene, dimethyl formamide, butyl lithium, ethyl magnesium bromide or triethylaluminium in toluene, which results in a high molecular weight, as reported by Zarras and Vogl (Progress in polymer science, 16, 173-201, 1991) and Egret et al. (European Polymer Journal, 38, 1953 -1961, 2002). According to Zarras and Vogl (Progress in polymer science, 16, 173 - 201, 1991), ketene can be polymerized as three structural units (polyester, polyketene and polyacetal). The propagating anion may form either on the carbon or on the oxygen atoms, generating either a carbanion or an enolate anion. Polyketene are obtained by carbon-carbon addition. Polyacetal structures are formed by carbon-oxygen addition, while mixed addition gives the ester structure. The polymerization of ketene generally yields ester and acetal type polymers and not polyketene, as reported by Olah et al. (Journal of American chemical society, 9123-9124, 1989). Staudinger (US Patent 3,249,589) synthesized the first ketene polymer using dimethyl ketene in presence of trimethyl amine as a catalyst. In 1937, Wiezevich and Gleason (US2,103,505) reported the ketene polymers having the ester structures. The dimer of ketene, cyclobutane 1:3 dione was used as the starting material in presence of small amounts of catalyst such as mineral acids or metallic salts. Then, linear crystalline polymers of ketenes having the general formula R1R2C=C=O wherein RI and R2 are the same or different alkyl, aryl or alkyl aryl groups, in which polymers have a polyacetalic structure with the inherent viscosity of 0.21 dL/g was invented by Montedison SPA group (GB1,014,659). In continuation of the research, Montedison SPA group (GB987370) further synthesized high molecular crystalline polymers of the same type (R1R2C=C=O) where 'R1 & R2' can be cycloalkyl or an alkyl-aryl group. In 1960s Natta et al. (Journal of American chemical society, 82, 4742, 1960) greatly contributed in the field of ketene synthesis by way of inventing high molecular weight linear polymers, having general formula R2C=C=O wherein 'R' is an alkyl group containing from one to six carbon atoms, a cycloalkyl or an alkyl-aryl group. Natta et al. (US3,249,589) prepared ketene polymers by the polymerization of the monomer in the presence of a catalyst having the general formula AIR'nXm ['R' represents an alkyl, aryl, cycloalkyl or alkoxy group or a hydrogen atom, 'X' is a halogen atom, 'm1 is 0, 1, 2 or 3 and 'n' is (3 - m)] or addition complexes of compounds of said formula particularly with organic oxygen containing bases, such as ethers, their dimmers or mixtures of them. According to Natta et al. (Journal of American chemical society, 82, 4742, 1960) the polymerization of ketene generally gives polyketone - ester mixed type polymers with very high molecular weight. After Natta et at. many groups came into existence of the synthesis of ketene polymers. German company named Wacker - chemie G.m.b.H (GB933.148), provided a process for the manufacture of diketene polymers by polymerizing di-ketene into a highly polymeric diketene in a liquid organic solvent containing a hydroxyl group in the presence of an alkaline catalyst. Thermally stable, macromolecular, highly crystalline high melting disubstituted ketene polymers of ester structure with inherent viscosity of 0.25 to 1.1 dL/g in tetralin at 145°C was prepared by cash et al. (US3,321,441). in presence of strongly basic catalyst (butyl lithium). Jorge (US4304767) invented polymers of di-ketene acetals and polyols of ortho ester structure having high molecular weight of 200,000. In the year 1989 the polymer research again focused into the synthesis of ketene polymers having polyketene structure and the process for its synthesis. Olah et al. (Journal of American chemical society, 111, 9123 - 9124, 1989) and Khemani & Wudl (Journal of American chemical society, 111, 9124 - 9125, 1989) claimed the synthesis of polyketene with very high molecular weight. They used acetyl chloride as the starting material for the synthesis of polyketene in presence of 10 mol % of lewis acid halide (AICI3, FeCI3, ZnCI2, TiCI4, BF4, SbCI5) catalyst. To be used as a strong chelating agent for transition metals polyketene structure is preferable than the ester and acetal structure especially with the molecular weight of 500 The use of an insoluble supported catalyst in the polymer synthesis is an attractive approach since it allows simple isolation of the desired compound, easy elimination of by products & excess reagents, facile separation & recovery of the material and efficient reuse of the catalyst. Ketene oligomer synthesis using an insoluble supported catalyst such as activated carbon was not yet developed. An efficient impregnation of metals onto activated carbon can provide immense application in the field of organic and polymer synthesis. In our co-pending Indian patent application (320 DEL 2004) we provided a process for the preparation of transition metal impregnated activated carbon. The preparation of the materials involves the use of metal complexes in the form of acetyl acetonates, pyridine, picoline, hexafluoroacetyl acetone oxime of Cu, Co, Ni and insitu impregnation of the same on activated carbon having surface area of 392 - 430 m2/g; average pore diameter of 35.28 - 37.20 °A; Bulk density of 0.56 - 0.62 g/cc and a composition of Carbon 37.96 - 39.36%; Hydrogen 2.46 - 3.41%; Nitrogen 0.5 - 0.71% followed by curing at optimized temperatures. The relative percentage of the transition metal based complex impregnated in the activated carbon is in the range of 0.25% w/w to that of the total carbon matrix. In view of the foregoing, the hitherto known ketene polymer and the known processes for their preparation are associated with the following limitations: 1. If the molecular weight of the substance goes beyond 1000 then its chelating property will be decreased. Therefore Ketene oligomers or polymers known in the prior art are not suitable to be used as a strong chelating agent for transition metals which forms a water insoluble transition metal complex. 2. Monomers used in the prior art are not naturally occurring monomer, it needs to be synthesized, therefore it affects the cost of the process and as well as its productivity. 3. Catalyst mentioned in the prior art are not supported in an insoluble support, therefore it limits the reuse after two - three times. No prior art is available on ketene oligomer having the polyketene structure with the molecular weight 500 - 1000 having the general formula [R1R2C=C=O]n, where 'n' is an integer in the range of 10 to 16; RI and R2 are hydrogen atoms or alkyl groups having carbon chain length in the range of 1 to 4; R^R2 or Ri*R2. Further, no prior art is available for the usage of amino acid as the starting material and the transition metal impregnated activated carbon as the catalyst for the synthesis of ketene oligomers. OBJECTIVES OF THE INVENTION The main objective of the present invention is to provide a novel ketene oligomer from aliphatic non-polar amino acids for industrial applications, which obviates the limitations as stated above. Another objective of the present invention is to provide a process for the preparation of a novel ketene oligomer from aliphatic non-polar amino acid containing carbon, nitrogen, hydrogen & oxygen. Yet another objective is the usage of transition metal impregnated activated carbon having the following characteristics Surface area of 392 - 430 m2/g; Average pore diameter of 35.28 - 37.20 °A; Bulk density of 0.56 - 0.62 g/ccComposition: Carbon 37.96 - 39.36%; Hydrogen 2.46 - 3.41%; Nitrogen 0.5 - 0.71% The relative percentage of the transition metal based complex impregnated in the activated carbon is in the range of 0.25% w/w to that of the total carbon matrix. Still another objective is to use solvent as initiator instead of a separate initiator in the reactions. The present invention finally leads to the formation of liquid oligomers of ketene having the molecular weight of 500 - 1000 and also a novel & easy process for its production. SUMMARY OF THE INVENTION Accordingly the present invention provides a novel ketene oligomer of the general formula [RiR2C=C=O]n, where 'n' is an integer in the range of 10 to 16; RI and R2 are hydrogen atoms or alkyl groups having carbon chain length in the range of 1 to 4; Ri=R2 or Ri*R2. The present invention further provides a process for the preparation of ketene oligomer from aliphatic non-polar amino acids which comprises: i. dissolving aliphatic non-polar amino acid containing only carbon, hydrogen, nitrogen and oxygen in 10-100 times by weight of water to form an amino acid solution, ii. adding to the amino acid solution, as obtained in step(i) 50-500 times by weight of alcohol to form a reaction mixture, iii. passing the reaction mixture, as obtained in step (ii) through a column packed with 100-600 times by weight of transition metal impregnated activated carbon, having characteristics such as herein described, based on the weight of amino acid, at a temperature in the range of 20 to 60°C for a retention time of 10 -150 min. and collecting the resulting solution at the outlet, iv. subjecting the resultant solution, as obtained in step (iii), to conventional separation to obtain viscous ketene oligomer liquid, v. optionally subjecting the ketene oligomer liquid, as formed in step (iv), to nonpolar solvent extraction by known method to obtain purer form of ketene oligomer liquid. In an embodiment of the present invention, the molecular weight of the ketene oligomer may be in the range of 500 -1000. In another embodiment of the present invention, the viscosity of the ketene oligomer may be in the range of 0.02 - 0.12 dL/g. In yet another embodiment of the present invention, the ketene oligomer is insoluble in water. In yet another embodiment of the present invention, the ketene oligomer decomposes at a temperature in the range of 230°C - 250°C. In still another embodiment of the present invention, the aliphatic non-polar amino acid used may be selected from glycine, alanine, valine, leucine, either individually or in any combination. In yet another embodiment of the present invention, the solvent used may be selected from methanol, isopropyl alcohol, either individually or in any combination. In still another embodiment of the present invention, the conventional separation used may be such as solar evaporation, vacuum distillation. In yet another embodiment of the present invention, the non-polar solvent used may be selected from chloroform, dichloromethane, either individually or in any combination. In still another embodiment of the present invention, the amount of non-polar solvent used for the extraction may be in the range of 200 - 500 times of the weight of the ketene oligomer. DETAILED DESCRIPTION OF THE INVENTION Aliphatic non-polar amino acid containing only carbon, hydrogen, nitrogen and oxygen is dissolved in 10-100 times by weight of water to form an amino acid solution. And 50-500 times by weight of alcohol is added to this solution to form a reaction mixture. The resulting solution is passed through a column packed with 100-600 times by weight of transition metal impregnated activated carbon based on the weight of amino acid, at the temperature range of20to60°C. The process for the preparation of transition metal impregnated activated carbon is provided in our co-pending Indian patent application (320 DEL 2004). The preparation process is as follows: The use of metal complexes in the form of acetyl acetonates, pyridine, picoline, hexafluoroacetyl acetone oxime of Cu, Co, Ni and insitu impregnation of the same on activated carbon having surface area of 392 - 430 m2/g; average pore diameter of 35.28 37.20 °A; Bulk density of 0.56 - 0.62 g/cc and a composition of Carbon 37.96 - 39.36%; Hydrogen 2.46 - 3.41%; Nitrogen 0.5 - 0.71% followed by curing at optimized temperatures. The relative percentage of the transition metal based complex impregnated in the activated carbon is in the range of 0.25% w/w to that of the total carbon matrix. The flow rate is maintained in such a way that the retention time ranges between 10-150 min. The solution collected at the outlet is subjected to conventional separation such as solar evaporation or vacuum distillation, whereby the alcohol escapes leaving behind the ketene oligomer of the present invention. The product may be contaminated with unreacted nonpolar amino acid. Hence the ketene oligomer solution is optionally subjected to non-polar solvent extraction. This extraction involves treating the solution with 200 - 500 times by weight of a non-polar solvent based on the weight of the oligomer liquid followed by conventional separation. Purer form of the oligomer solution is obtained by repeating the extraction process. The final product is a liquid of ketene oligomer of the general formula [R1R2C=C=O]n, where 'n' is an integer in the range of 10 to 16; RI and R2 are hydrogen atoms or alkyl groups having carbon chain length in the range of 1 to 4; Ri=R2 or Ri*R2. The characteristics of the oligomer are as follows: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Elemental compositions (%): Carbon 70.76 Hydrogen 9.49 Oxygen 15.86 Attenuated Total Reflectance - Fourier transformer Infrared spectroscopy (ATR-FTIR): The ATR-FTIR spectrum of the oligomer was scanned in between 4000 - 1000 cm"1. The CH stretching vibration of methyl group shows at 2959.27 cm"1. The asymmetrical stretching and symmetrical stretching vibration of methylene group occur, respectively at 2929.97 and 2860.41 cm"1. The asymmetrical bending vibration of methyl is overlapped with the scissoring vibration of the methylene groups and appears at 1380 cm"1. The multiple bands at 1300 - 1100 cm"1 region is as a result of C-C-C stretching and bending in the C-C(=O)-C group. The vibration at 1719.54 cm"1 shows the presence of C=O stretching of ketonic group which confirms the presence of ketonic structure in the oligomer. 13C NMR The 13C, NMR spectrum was taken using CDCI3 as solvent. The a-methyl carbon resonances are assigned around 5 10.8 - 14.0 ppm. The shift around 5 22 - 38 ppm can be assigned to methylene groups present in the oligomer chains. The spectral regions around 5 128-133 ppm is due to the presence of -C=C- group present in the monomer. The quaternary carbon of ketene oligomers are resonances at 5 193 ppm shows the presence of C=O stretching of ketonic group which confirms the presence of ketonic structure in the oligomer. The triplet at 5 77.0 is the solvent CDCI3 peak. Distortionless Enhancement by Polarization Transfer (DEPT) NMR DEPT spectrum distinguishes between a CH3 group, a CH2 group and a CH group. The - CH2 resonances are assigned with the help of DEPT-135. The resonances, which are present in the 13C spectrum and absent in the DEPT spectrum are assigned to quaternary carbons. From this spectrum, it is evident that the signals around 8 193 ppm refer to the quaternary carbon. Proton NMR Proton NMR is studied in order to identify the complete structure of the oligomer. The spectral regions of 5 0.8 - 1.8 ppm are complex and these can be assigned to the aliphatic carbons in the main chain of the oligomers. Almost all the peaks on expansion also shows a complicated figure, so 1H - 13C cosy HETCOR 2D NMR was taken which correlates 13C nuclei directly attached to protons. 1H - 13C COSY HETCOR (Heteronuclear chemical shift correlation) NMR 2D HETCOR NMR enables unambiguous assignments of various resonance signals in 13C and 1H NMR spectra. The crosspeaks 1,2 centered at 10.83/0.9, 13.85/0.82 are assigned to methyl group present at the end of the oligomer chain. The backbone methylene groups showed sensitivity to various configurational sequences resulting in crosspeaks 3,4,5,6 centered at 22.85/1.26, 23.73/1.38, 28.85/1.26, 30.33/1.32. The -C=C- in ketene oligomers are centered at 128.8/7.65 & 130.91/7.46. The peak of 13C, which is not crossed any 1H peak can be considered as quaternary carbon, which lies at 8 193 ppm. 14NNMRand15NNMR As the starting material of the reaction has got nitrogen atom, in order to confirm the absence of nitrogen in the oligomers the 14N NMR and 1SN NMR was scanned upto 2000 times. This does not shows any presence of nitrogen. This result is in addition support to the CHNO analysis, which also tells the absence of nitrogen atom. Thermal Degradation (TGA) Ketene oligomers are relatively stable and degradation occurs only at about 230°C - 250°C at nitrogen atmosphere. The inventiveness of the invention lies in providing ketene oligomer of molecular weight in the range of 500-1000 from aliphatic non-polar amino acids using transition metal impregnated activated carbon. The invention is further described by the following examples, which are provided by way of illustration only and should therefore not be construed to limit the scope of the present invention. 10 Example 1 40 mg of glycine was dissolved in 1.00 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 0.5 ml/min, which is maintained at the temperature of 30°C. After 45 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction as follows: About 7 ml of Chloroform was added to the solution in a separating funnel and extracted the ketene oligomer in the chloroform layer. Then the chloroform layer was separated and left for evaporation. The clear liquid of ketene oligomer weighing 22.0 mg (55 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.022 dl_/g Example 2 50 mg of glycine was dissolved in 1.25 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 0.5 ml/min, which is maintained at the temperature of 30°C. After 45 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 31.3 mg (62.6 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble 11 Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.024 dL/g Example 3 60 mg of glycine was dissolved in 1.5 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 0.5 ml/min, which is maintained at the temperature of 30°C. After 45 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 32.0 mg (53.3 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.022 dL/g Example 4 50 mg of glycine was dissolved in 1.25 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 0.5 ml/min, which is maintained at the temperature of 20°C. After 45 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 24.1 mg (48.2 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble 12 Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.021 dL/g Example 5 50 mg of glycine was dissolved in 1.25 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 0.5 ml/min, which is maintained at the temperature of 50°C. After 45 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 34.1 mg (68.2 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.032 dL/g Example 6 50 mg of glycine was dissolved in 1.25 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 0.5 ml/min, which is maintained at the temperature of 60°C. After 45 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 33.8 mg (67.6 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble 13 Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.034 dL/g Example 7 50 mg of glycine was dissolved in 1.25 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 75 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 36.7 mg (73.4 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.033 dL/g Example 8 50 mg of glycine was dissolved in 1.25 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 12 g of activated carbon at a flow rate of 1.0 ml/min, which is maintained at the temperature of 50°C. After 23 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 22.6 mg (45.2 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble 14 Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.023 dL/g Example 9 50 mg of glycine was dissolved in 1.25 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 23 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 140 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 40.5 mg (81 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.033 dL/g Example 10 50 mg of glycine was dissolved in 3.5 ml of water and made upto 250 ml with ethanol. It was passed through the spiral reactor packed with 23 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 140 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 36.2 mg (72.4 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble 15 Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.038 dL/g Example 11 50 mg of glycine was dissolved in 4.8 ml of water and made upto 250 ml with isopropyl alcohol. It was passed through the spiral reactor packed with 23 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 140 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 28.5 mg (57 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.043 dL/g Example 12 50 mg of alanine was dissolved in 1.4 ml of water and made upto 250 ml with methanol. It was passed through the spiral reactor packed with 23 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 140 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 37.4 mg (74.8 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble 16 Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.061 dL/g Example 13 50 mg of valine was dissolved in 1.7 ml of water and made upto 250ml with methanol. It was passed through the spiral reactor packed with 23 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 140 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 32 mg (64 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.091 dL/g Example 14 50 mg of leucine was dissolved in 2.0 ml of water and made upto 250ml with methanol. It was passed through the spiral reactor packed with 23 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 140 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 31.1 mg (62.2 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble 17 Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.116 dL/g Example 15 50 mg of iso-leucine was dissolved in 2.0 ml of water and made upto 250ml with methanol. It was passed through the spiral reactor packed with 23 g of activated carbon at a flow rate of 0.3 ml/min, which is maintained at the temperature of 50°C. After 140 min the solution at the outlet of the reactor was collected in a conical flask and was vacuum distilled to obtain a liquid ketene oligomer. The solution was further purified by chloroform extraction. The clear liquid of ketene oligomer weighing 31.2 mg (62.4 %) was collected after evaporation and stored. The oligomer was then subjected to characterization study and was found to exhibit the following characteristics: Nature Viscous liquid Solubility: Water Insoluble Alcohols Soluble Non-polar solvents Soluble Aromatic and aliphatic hydrocarbons Soluble Inherent viscosity 0.104 dL/g ADVANTAGES Following are the main advantages of the present invention: 1. The process is simple. No extra costly arrangement is required. 2. The process uses non-toxic substance as the starting material for the process. 3. Aliphatic non-polar amino acids, which form the raw materials for the present invention, may be also sourced from solid wastes generated by different processing industries, such as tanning industry. Hence the process suggests an option for economical utilization of solid wastes, which would otherwise add to environmental pollution problem. 4. The product of the present invention is a strong chelating ligand for transition metals and the resulting complexes are effective reusable substances for inactivating wide spectrum of anaerobes and aerobes 5. Used as a delivery system for drugs through microencapsulation. We Claim: 1. A novel ketene oligomer having a molecular weight in the range of 500 to 1000 represented by the general formula [R1R2C=C=O]n, where 'n' is an integer in the range of 10 to 16 and R1 and R2 are hydrogen atoms or alkyl groups having carbon chain length in the range of 1 to 4. 2. A novel ketene oligomer as claimed in claim 1, wherein the viscosity of the said oligomer is in the range of 0.02 - 0.12 dL/g. 3. A novel ketene oligomer as claimed in claim 1, wherein the said oligomer is insoluble in water and decomposes at a temperature in the range of 230 to 250 degree C. 4. A process for the preparation of novel ketene oligomer as claimed in claim 1, comprises: a) dissolving aliphatic non-polar amino acid containing only carbon, hydrogen, nitrogen and oxygen in 10 to 100 times by weight of water to form an amino acid solution, b) adding 50 to 500 times by weight of alcohol to the amino acid solution as obtained in step(a) to form a reaction mixture, c) passing the reaction mixture as obtained in step (b) through a column packed with 100 to 600 times by weight of transition metal impregnated activated carbon, having characteristics such as herein described, based on the weight of amino acid, at a temperature in the range of 20 to 60°C for a period of 10 to 150 min and collecting the resulting solution at the outlet, d) separating the resultant solution as obtained in step (c), by conventional method to obtain viscous ketene oligomer liquid, e) optionally, subjecting the ketene oligomer liquid as formed in step (d), to nonpolar solvent extraction by known method to obtain pure form of ketene oligomer liquid. 5. The process as claimed in claim 4, wherein the aliphatic non-polar amino acid used is selected from glycine, alanine, valine, leucine, isoleucine either individually or in any combination. 6. The process as claimed in claim 4, wherein the solvent used is selected from methanol, ethanol, isopropyl alcohol, either individually or in any combination. 7. The process as claimed in claim 4, wherein the conventional separation method is solar evaporation, vacuum distillation. 8. The process as claimed in claim 4, wherein the non-polar solvent used is selected from chloroform, dichloromethane, either individually or in any combination. 9. The process as claimed in claim 4, wherein the amount of non-polar solvent used for the extraction is in the range of 200 to 500 times of the weight of the ketene oligomer.

Documents:

393-del-2007-abstract.pdf

393-del-2007-Claims-(12-12-2012).pdf

393-del-2007-claims.pdf

393-del-2007-Correspondence Others-(12-12-2012).pdf

393-del-2007-Correspondence Others-(26-08-2008).pdf

393-del-2007-correspondence-others.pdf

393-del-2007-Description (Complete)-(12-12-2012).pdf

393-del-2007-description (complete).pdf

393-del-2007-form-1.pdf

393-del-2007-Form-18-(26-08-2008).pdf

393-del-2007-form-2.pdf

393-del-2007-Form-3-(12-12-2012).pdf

393-del-2007-form-3.pdf

393-del-2007-form-5.pdf