pentylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 500-ml shaking flask were charged an inorganic medium containing 6.2 g/l disodium hydrogen phosphate, 3 g/l potassium dihydrogen phosphate, 1.0 g/l ammonium chloride, 0.5 g/l sodium chloride, and 3 ml/l trace components solution and 50 ml of a medium having a composition of 1.0 g/l polypeptone (Nihon Pharmaceutical Co., Ltd.), and 1.0 g/l D-glucose. ANTIFOAM PE-M was added to the resultant mixture in the same manner as in Example 2 in a concentration of 0.5 ml/l. The obtained mixture was sterilized at high temperature and high pressure and cooled to room temperature to prepare a medium. Thereafter, n-amylbenzene, i.e. an alkane, was added thereto as a substrate so as to make a concentration of 6 mM. Also, 5-(vinylphenyl)pentane, i.e. an alkane, was further added thereto so as to make a concentration of 0.8 mM. YN21M strain, one of the novel microorganisms of the present invention, was inoculated in this shaking flask and cultured with shaking at 30° C. at 125 strokes/min. After 40 hours, the cells were recovered by centrifugation and PHA was extracted in the same manner as that in Example 1 and the obtained PHA was weighed. As a result, the polymer dry weight (PDW) was found to be 0.72 g/l. Further, the structure determination of the obtained PHA by 1H-NMR in the same manner as that in Example 1 gave a monomer unit ratio of 3-hydroxy-5-phenylvaleric acid of 80.7 mol %. Also, the monomer unit ratio of 3-hydroxy-5-(4-vinylphenyl) valeric acid was found to be 15.3 mol %. From the above, it was confirmed that PHA including a 3-hydroxy-5-phenylvalerate unit and 3-hydroxy-5-(4-vinylphenyl) valerate unit could be synthesized from n-amylbenzene and vinylphenylpentane by the YN21M strain. were charged an inorganic medium to prepare a medium YN21M strain, one of the novel microorganisms of the present invention, was inoculated in this shaking flask cultured with shaking at 30° C. at 125 strokes/min the cells were recovered by centrifugation and PHA was extracted in the same manner as that in Example 1 As a result, the polymer dry weight (PDW)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Running Reaction 2 at a 25% conversion of n-undecane gives the desired molar ratios of n-pentylbenzene and n-undecane in the synthetic JP-8 surrogate for mass and energy balance purposes:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Running Reaction 2 at a 25% conversion of n-undecane gives the desired molar ratios of n-pentylbenzene and n-undecane in the synthetic JP-8 surrogate for mass and energy balance purposes:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: All cyclohexylbenzene hydroperoxide cleavage reactions were carried out in a 100 mL round bottom flask equipped with a magnetic stir bar. Generally, about 14 g of crude oxidation product (see Example I), 0.4 g of internal standard (n-pentylbenzene), 0.05-0.5 g of catalyst and, optionally, about 10 mL of solvent were charged to the vessel. The reactor contents were stirred at room temperature to about 60° C. for about 30 minutes to about 2 hours, then sampled for analysis by gas liquid chromatography (glc). The product yields are corrected for the fact that only 90% of the hydroperoxide in the CHBHP feed is the correct hydroperoxide, i.e. ##STR2## Other isomeric hydroperoxides are incapable of cleavage to give the desired ultimate products, phenol and cyclohexanone. equipped with a magnetic stir bar sampled for analysis by gas liquid chromatography (glc) The product yields

Conditions: temp:550.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Cyclodehydrogenation was carried out in the same way as Example 1 except that n-amylbenzene (a reagent produced by Tokyo Kasei K.K., purity: 98.9%) was used in place of n-butylbenzene, and that it was gasified in a nitrogen stream and introduced into the catalyst layer maintained at 550° C., at LHSV of 0.085. The conversion ratio of n-amylbenzene was 95.5%. Also, 1-methylnaphthalene was obtained at a selectivity of 72.1%, while naphthalene was obtained at a selectivity of 11.4%. produced by Tokyo Kasei K.K introduced into the catalyst layer

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: First, 3-cyanophenylacetic acid (3 g, 0.019 mol) is heated under reflux in thionyl chloride (50 ml) for 90 minutes. The excess thionyl chloride is then removed by distillation and the residual acid chloride added in one portion to a solution. 1-phenylpentane (2.76 g, 0,019 moles) in methylene chloride (10 ml). Anhydrous aluminum chloride (2.98 g) is added in small portions over 10 minutes. The reaction mixture is then heated under reflux for 1 hour, cooled and poured into a mixture of ice water (250 ml) and concentrated hydrochloric acid (50 ml). The mixture is extracted with ether (2×100 ml). The ether extracts are dried over magnesium sulfate, filtered, and evaporated to dryness. The residue is chromatographed on silica (hexane: ethyl acetate at 90:10 ) to yield 3-(4-pentylphenacyl) benzonitrile (1.13 g, m.p. 73° C.). This nitrile is heated under reflux in a mixture of 75% sulfuric acid (8 g) and acetic acid (8 g) for 90 minutes. The reaction mixture is then diluted with water (100 ml) and extracted with ether (2×75 ml). The ether extracts are dried over magnesium sulfate, filtered, and evaporated to dryness. The residue is recrystallized from heptane to provide 3-(4-pentylphenacyl)benzoic acid (0.97 g), m.p. 109°-111° C., which was identified by IR and NMR spectroscopy. The excess thionyl chloride is then removed by distillation the residual acid chloride added in one portion to a solution The reaction mixture is then heated under reflux for 1 hour cooled The mixture is extracted with ether (2×100 ml) The ether extracts are dried over magnesium sulfate filtered evaporated to dryness The residue is chromatographed on silica (hexane: ethyl acetate at 90:10 )

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Succinic anhydride (8.6 g; 0.1 mole) is reacted with pentylbenzene (100 ml) and aluminum chloride (29 g; 0.22 mole) and the product isolated by the manner described in Example 3. Recrystallization from aqueous ethanol gives 3-(4-n-pentylbenzoyl)propanoic acid (17 g) as colorless crystals, m.p. 98°-100° C. the product isolated by the manner Recrystallization from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Glutaric anhydride (10 g; 0.1mole) is reacted with pentylbenzene (100 ml) and aluminum chloride (29 g; 0.22 mole) at room temperature for 4 hours. The reaction mixture is poured into a mixture of ice-water (500 ml) and concentrated hydrochloric acid (50 ml) with vigorous stirring. The crude product is collected by filtration and recrystallized from aqueous ethanol to give 4-(4-n-pentylbenzoyl)butanoic acid (16.2 g) as colorless crystals, m.p. 104°-106° C. The crude product is collected by filtration recrystallized from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Adipic acid monomethyl ester (35 g; 0.44 mole) is converted to the acid chloride with thionyl chloride (50 g) in a manner analogous to that described in Example 1. This product is reacted with pentylbenzene (400 ml) and aluminum chloride (80 g) and the reaction product isolated as a colorless oil (25 g; b.p. 165°-174° C. @0.15 mm) and identified as methyl 5-(4-n-pentylbenzoyl) pentanoate. This ester (5 g; 0.017 mole) is hydrolysed with sodium hydroxide in aqueous ethanol and the product isolated as in Example 1. Recrystallization from aqueous ethanol gives 5-(4-n-pentylbenzoyl)pentanoic acid (4.0 g) as colorless crystals, m.p. 84°-86° C. the reaction product isolated as a colorless oil (25 g; b.p. 165°-174° C. @0.15 mm) the product isolated as in Example 1 Recrystallization from aqueous ethanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: All cyclohexylbenzene hydroperoxide cleavage reactions were carried out in a 100 mL round bottom flask equipped with a magnetic stir bar. Generally, about 14 g of crude oxidation product (see Example I), 0.4 of internal standard (n-pentylbenzene), 0.1-3.0 g of catalyst and about 10 ml of solvent were charged to the vessel. The reactor contents were stirred at room temperature up to about 70° C. for 30 minutes to about 2 hours, then sampled for analysis by gas liquid chromatography (glc). The product yields are corrected for the fact that only 90% of the hydroperoxide in the CHBHP feed is the correct hydroperoxide, i.e. ##STR3## Other isomeric hydroperoxides are incapable of cleavage to give the desired ultimate products, phenol and cyclohexanone. equipped with a magnetic stir bar sampled for analysis by gas liquid chromatography (glc) The product yields