Title of Invention

PROCESS FOR THE PREPARATION OF NONANE

Abstract i) Reacting Dihydroxyacetone phosphate (DHAP) with 3-Phosphoglyceraldehyde (3PGA) in the presence of ADOLASE to produce Fructose-1, 6-b isphosphate; i i ) Reacting said Fructose-1 ,6—b i sphosphate with spinach fructose Phosphstase to produce Fructose-l-Phosphate (FTP); iii) Reacting the said Fructose-l-Phosphate (FIP) with 3PGA in the presence of NaOH (1M concentration) to produce 2,3,4,6,7 ,8-hexahydroxy-5-oxo-nonanedial-bisphosphate (HONAP) ; i v ) The said 2,3,4,6,7 , 8-hexahydoxy-5-oxononanedial — bisphosphate is reacted in the presence of spinach fructose Phosphatase to produce 2,3,4,6,7,8-hexahydroxy-5~oxo-nonanedial (HONA); and v ) The said 2,3,4,6,7, B~hexahydroxy-5-oxo-nonanedial (HONA) is subjected to a series of hydrogenation to produce Nunone .
Full Text The present invention relates to the production of a nine-carbon hydrocarbon, Nonane.
This invention particularly relates to conversion of 3-phosphoglyceraldehyde (3PGA) into Nonane.
Here we describe a method involving multiple steps where the 3PGA can be converted to a nine-carbon hydrocarbon Nonane, which may act as fuel in internal combustion engines. We have employed standard organic reaction catalysts or catalysts of biological origins (spinach aldolase/spinach fructose phosphatase) in achieving the required chemical conversion steps;.
This invention provides a novel process for the preparation of 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial-bisphosphate (HONBP) starting from compound 3-phosphoglyceraldehyde (3 PGA), in a manner as shown in Fig.l of the accompanying drawings. The new compound (HONBP) is obtained by reaction of compound Dihydroxyacetone phosphate (DHAP) with 3-phosphoglyceraldeh.yde (3PGA) in the presence of spinach aldolase. This will produce a compound Fructose-1,6-bisphosphate. The compound Fructose-1,6-bisphosphate is converted into Fructose-1-Phosphate (F1P) by using spinach fructose phosphatase. The compound Fructose-1-Phosphate is reacted with 3PGA in the presence of NaOH (1M concentration) to produce the compound 2,3,4,6,7,8-hexahydroxy-5-oxo nonanedial-bisphosphate (HONBP).
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This invention provides a process for the preparation of Nonane, comprised of the following steps:
i) Reacting Dihydroxyacetone phosphate (DHAP) with 3-Phosphoglyceraldehyde (3PGA) in the presence of spinach aldolase to produce Fructose-1,6-bisphosphate;
iii) Reacting the said Fructose-1,6-bisphosphate with spinach fructose Phosphatase to produce Fructose-1-Phosphate (F1P);
iii) Reacting the said Fructose-1-Phosphate (F1P) with 3PGA in the presence of 1M NaOH to produce 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial-bisphosphate (HONBP);
iv) The said 2,3,4,6,7,8-hexahydroxy-5-oxo-nonanedial-bisphosphate is Phosphatase to produce 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nbnanedial (HONA);
v) The said 2, 3,, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial (HONA) is
then subjected to a series of hydrogenation to produce phosphate.—
In the reactions mentioned above, the first step, Dihydroxyacetone phosphate (DHAP) and 3-PGA is converted into Fructose-1,6-bisphosphate. Dihydroxyacetone phosphate is generated from 3-PGA by the action of spinach triose phosphate isomerase as a separate reaction step. In the second step Fructose-1,6-bisphosphate is converted into Fructose-1-phosphate (F1P) using
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spinach fructose phosphatase. In the step(iii) , the F1P and 3PGA are converted into a new compound 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial-bisphosphate (HONBP) The step 3, is an aldol condensation step between a phosphoaldehyde and phosphoketone and is catalyzed by 1M sodium hydroxide (NaOH). In the step 4, HONBP is converted into 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial (HONA) by a mixture of spinach fructose/sedoheptulose phosphatse. In the step 5, under acidic condition HONA is subjected to a series of rigorous hydrogenation. The multiple sub-steps employed in step 5 have been elucidated. The isomerization of DHAP from 3-PGA and reactions depicted in steps 1 and 2 are well known reactions in carbohydrate chemistry, biochemistry and biotechnology.
The step 3, represent a novel reaction. The reactants and products were isolated and analyzed using thin layer chromatography (TLC) and paper chromatography to identify the compounds. The spot corresponding to a new product was isolated and subjected to elemental analysis that was determined to be C9H20O15P2
The presence of phosphoric acid groups was verified (using titration methods). The envisaged chemical compound 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonane dial-1,9-bisphosphate is consistent with aldol condensation and with results of the elemental analysis. The presence of the aldehyde and the ketone groups are consistent with the experimental analysis using Fehling's and Benedicts reagent.
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The step 4 involves conversion of HONBP into HONA using a mixture of phosphatase derived from plant sources. This also involves a novel reaction and two novel compounds and were detected using thin layer chromatographic (TLC) methods. Although the TLC shows two different spots but in elemental analysis they clearly show difference as one of them shows elemental composition as C4H20O15P2 and the other C9H18O9 In step 5, HONA was subjected to rigorous hydrogenation in four steps. Under acidic conditions the compound HONA was subjected to hydrogenation in presence of Zn(Hg) .which was followed by NaBR* followed by LiAl H4 in acidic-ether and di-isobutyl aluminium hydride (DIBAH) followed by once again with Zn(Hg) catalyst under acidic condition. The product in the reaction mixture was identified as hydrocarbon Nonane, using different analytical techniques.
The sugars: 3-phosphoglyceraldehyde (3PGA), Dihydroxyacetone phosphate (DHAP), Fructose-1,6-bisphosphosphate, Fructose-I-phosphate (F1P) and solvents such as Ethyl-acetate, methanol, toluene, glacial acetic acid were procured in a manner known per se.
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WE CLAIM:





I. A process for the preparation of Nonane which comprises the following steps:
i) Reacting Dihydroxyacetone phosphate (DHAP) with 3-
-Phosphoglyceraldehyde (3PGA) in the presence of Aldolase to produce Fructose-1,6-

bisphosphate;
ii) Reacting said Fructose-1,6-bisphosphate with spinach fructose Phosphatase to produce Fructose-1-Phosphate (F1P);
iii) Reacting the said Fructose-1-Phosphate (F1P) with 3PGA in the presence of NaOH (1M concentration) to produce 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial-bisphosphate (HONAP);
iv) The said 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial-bisphosphate is reacted in the presence of spinach fructose Phosphatase to produce 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonanedial (HONA); and
v) The said 2,3,4,6,7,8-hexahydroxy-5-oxo-nonanedial (HONA) is subjected to a series of hydrogenation to produce Nonane.
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2. A process as claimed in claim 1 wherein said step i) is carried out in the
presence of a catalyst or catalyst of biological origin
3. A process as claimed in claim 1 wherein said step iii) is carried out as an
aldol condensation in the presence of sodium hydroxide (1 M concentration).

4. A process as claimed in claim 1 wherein said step(v) is carried out by
subjecting 2, 3, 4, 6, 7, 8-hexahydroxy-5-oxo-nonancdial (HONA) to successive
hydrogenation in the presence of Zn(Hg), NaBH4, LiAIH4 , DIBAH, and again Zn(Hg).
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5. A process for the preparation of Nonane as described herein and as illustrated in the
reaction scheme accompanying the provisional specification.
i) Reacting Dihydroxyacetone phosphate (DHAP) with 3-Phosphoglyceraldehyde (3PGA) in the presence of ADOLASE to produce Fructose-1, 6-b isphosphate;
i i ) Reacting said Fructose-1 ,6—b i sphosphate with
spinach fructose Phosphstase to produce Fructose-l-Phosphate (FTP);
iii) Reacting the said Fructose-l-Phosphate (FIP) with 3PGA in the presence of NaOH (1M concentration) to produce 2,3,4,6,7 ,8-hexahydroxy-5-oxo-nonanedial-bisphosphate (HONAP) ;
i v ) The said 2,3,4,6,7 , 8-hexahydoxy-5-oxononanedial —
bisphosphate is reacted in the presence of spinach fructose
Phosphatase to produce 2,3,4,6,7,8-hexahydroxy-5~oxo-nonanedial
(HONA); and
v ) The said 2,3,4,6,7, B~hexahydroxy-5-oxo-nonanedial (HONA) is subjected to a series of hydrogenation to produce
Nunone .


Documents:

00236-cal-2000-abstract.pdf

00236-cal-2000-claims.pdf

00236-cal-2000-correspondence.pdf

00236-cal-2000-description(complete).pdf

00236-cal-2000-description(provisional).pdf

00236-cal-2000-drawings.pdf

00236-cal-2000-form-1.pdf

00236-cal-2000-form-13.pdf

00236-cal-2000-form-18.pdf

00236-cal-2000-form-2.pdf

00236-cal-2000-form-26.pdf

00236-cal-2000-form-3.pdf

00236-cal-2000-form-5.pdf

00236-cal-2000-letters patent.pdf

236-cal-2000-description (provisional).pdf

236-cal-2000-granted-abstract.pdf

236-cal-2000-granted-drawings.pdf

236-cal-2000-granted-form 2.pdf

236-cal-2000-granted-specification.pdf


Patent Number 208193
Indian Patent Application Number 236/CAL/2000
PG Journal Number 29/2007
Publication Date 20-Jul-2007
Grant Date 19-Jul-2007
Date of Filing 20-Apr-2000
Name of Patentee RABINDRA NATH GHOSH
Applicant Address ANANYA 3, CHANDIGARH MAIN ROAD, P.O. MADHYAYGRAM, DIST. NORTH 24 PGS.
Inventors:
# Inventor's Name Inventor's Address
1 SANJOY KUMAR BHATTACHARYA 24455 LAKESHORE BLVD. APT 1804E EUCLID, OHIO 44123,
2 RABINDRA NATH GHOSH ANANYA 3, CHANDIGARH MAIN ROAD, P.O. MADHYAMGRAM, DIST. NORTH 24 PGS.
PCT International Classification Number C07E 9/14
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA