cyclododecanol

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

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

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

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

Procedure: Further, in a Drafted Report, page 68, of the 24th “Progress in Reaction and Synthesis” Sympodium, Nov. 5 to 6, 1998, a hydrogenation reaction of an epoxycyclododecadiene in the presence of a palladium catalyst carried on a carbon material is reported. In this case, the target cyclododecanol was produced at a yield of 5%. Further, in a Drafted Report, page 68, of the 24th “Progress in Reaction and Synthesis” Sympodium, Nov

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

Procedure: In a reaction example shown in this report, when epoxycyclododecadiene is subjected to a reduction reaction with a hydrogen gas in the presence of a palladium catalyst carried on γ-alumina under a reduced pressure of 1.3 MPa at a reaction temperature of 90° C., cyclododecanol is obtained at a yield of 20%. In the report, a palladium catalyst carried on titania and a palladium catalyst carried on silica were employed. In each case, the yield of the cyclododecanol was less than 20%. carried on γ-alumina under a reduced pressure of 1.3 MPa at a reaction temperature of 90° C.

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

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

Procedure: Further, Neftekhimiya, 16 (1), 114-119 (1976) discloses a catalytic reaction of 1,2-epoxy-5,9-cyclododecadiene with hydrogen in the presence of a palladium-carried catalyst at a reaction temperature of 140° C. under a hydrogen gas pressure of 8,106 kPa (80 atmospheres). In this reaction, epoxycyclododecane was produced in a yield of 49.5%, cyclododecanol in a yield of 33.3%, and cyclododecanone in a yield of 3.4%. at a reaction temperature of 140° C. In this reaction

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

Procedure: Further, Neftekhimiya, 16 (1), 114-119 (1976) discloses a catalytic reaction of 1,2-epoxy-5,9-cyclododecadiene with hydrogen in the presence of a palladium-carried catalyst at a reaction temperature of 140° C. under a hydrogen gas pressure of 8,106 kPa (80 atmospheres). In this reaction, epoxycyclododecane was produced in a yield of 49.5%, cyclododecanol in a yield of 33.3%, and cyclododecanone in a yield of 3.4%. at a reaction temperature of 140° C. In this reaction

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an SUS-made autoclave having an inner volume of 100 ml and equipped with a stirrer, 20 g (0.112 mol) of 1,2-epoxy-5,9-cyclododecadiene and 0.08 g of a 5 mass % Pt/C catalyst (50% hydrous product, produced by N.E. Chemcat Corporation; 0.0102 mmol as platinum atom) were added and after pressurizing to 5 MPa with hydrogen at room temperature, heated to a temperature of 70° C. Under the same pressure, the contents were heated with stirring until the hydrogen absorption did not occur. After the completion of reaction, the reaction solution was cooled to room temperature, the catalyst was removed by filtration and the resulting reaction solution was analyzed. The analysis of the reaction solution was performed by gas chromatography. As a result, 1,2-epoxy-5,9-cyclododecadiene was 100% consumed and epoxycyclododecane (hereinafter referred to as “ECD”) was produced in a yield of 99.6 mol %. Also, as by-products, cyclododecanone (hereinafter referred to as “CDON”) was produced in 0.04 mol %, cyclododecanol (hereinafter referred to as “CDOL”) was produced in 0.20 mol % and cyclododecane (hereinafter referred to as “CDAN”) was produced in 0.04 mol %. equipped with a stirrer Under the same pressure, the contents were heated After the completion of reaction the reaction solution was cooled to room temperature the catalyst was removed by filtration the resulting reaction solution consumed was produced in a yield of 99.6 mol %

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 22.82 g (0.15 mol) p-hydroxybenzoic acid methyl ester, 55.30 g (0.30 mol) cyclododecanol and 28 mg (0.1 mmol) tetraisopropyl orthotitanate are placed under argon in a round-bottom flask with distillation bridge. The mixture is stirred and heated to 160° C. within one hour. On reaching this temperature the pressure is reduced to 900 mbar and during the further course of the reaction to 800 mbar, during which time methanol is removed by distillation. Stirring is continued for 5 hours at this temperature. A further 0.05 ml tetraisopropyl orthotitanate are added and the reaction mixture is stirred for a further 20 hours at 170° C. under normal pressure. The residue undergoes column chromatography (silica gel 60, 0040-0.063 mm, Merck). An n-hexane/acetone mixture (5:1) is used as eluent. The product obtained in this way is freed from adhering cyclododecanol under high vacuum at 140° C. The residue is recrystallised in acetone. 5.9 g (13%) in the form of colourless crystals are obtained: is removed by distillation Stirring A further 0.05 ml tetraisopropyl orthotitanate are added the reaction mixture is stirred for a further 20 hours at 170° C. under normal pressure The product obtained in this way at 140° C The residue is recrystallised in acetone 5.9 g (13%) in the form of colourless crystals are obtained

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

Procedure: 6-aminohexanoic acid hydrochloride (0.1 mol) was treated with thionyl chloride (0.2 mol) at 40° C. until the mixture became homogeneous. The excess thionyl chloride was then removed under reduced pressure, a solution of cyclododecanol (0.1 mol) in dry dimethyl formamide (100 ml) was added to the residue, and the resultant mixture was heated at 90%. After 1 hour at this temperature, the solvent was evaporated under reduced pressure, the residue was dried, and by-product hydrogen chloride removed. The crude compound was dissolved in water, triethyl amine (0.15 mol) was added to the solution, and the resultant mixture was extracted with diethyl ether. The ethereal phase was dried over anhydrous Na2SO4, solvent evaporated, and the crude product was allowed to stir in a CO2 atmosphere for 1 hour. Traces of triethyl amine were removed upon standing over a vessel containing sulfuric acid under vacuum, and the product crystallised from toluene. The excess thionyl chloride was then removed under reduced pressure the solvent was evaporated under reduced pressure the residue was dried by-product hydrogen chloride removed The crude compound was dissolved in water the resultant mixture was extracted with diethyl ether The ethereal phase was dried over anhydrous Na2SO4, solvent evaporated Traces of triethyl amine were removed upon standing over a vessel containing sulfuric acid under vacuum the product crystallised from toluene

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

Procedure: 6-aminohexanoic acid hydrochloride (0.1 mol) was treated with thionyl chloride (0.2 mol) at 40° C. until the mixture became homogeneous. The excess thionyl chloride was then removed under reduced pressure, a solution of cyclododecanol (0.1 mol) in dry dimethyl formamide (100 ml) was added to the residue, and the resultant mixture was heated at 90%. After 1 hour at this temperature, the solvent was evaporated under reduced pressure, the residue was dried, and by-product hydrogen chloride removed. The crude compound was dissolved in water, triethyl amine (0.15 mol) was added to the solution, and the resultant mixture was extracted with diethyl ether. The ethereal phase was dried over anhydrous Na2SO4, solvent evaporated, and the crude product was allowed to stir in a CO2 atmosphere for 1 hour. Traces of triethyl amine were removed upon standing over a vessel containing sulfuric acid under vacuum, and the product crystallised from toluene. The excess thionyl chloride was then removed under reduced pressure the solvent was evaporated under reduced pressure the residue was dried by-product hydrogen chloride removed The crude compound was dissolved in water the resultant mixture was extracted with diethyl ether The ethereal phase was dried over anhydrous Na2SO4, solvent evaporated Traces of triethyl amine were removed upon standing over a vessel containing sulfuric acid under vacuum the product crystallised from toluene