2,6,10,15,19,23-hexamethyltetracosane

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dehydrosqualene prepared above was placed in a one liter Parr pressure reactor and 1.1 g of 5% Pd/C was added. The vessel was sealed and evacuated under house vacuum for twenty minutes (ca. 20 ton) and then pressurized with hydrogen gas up to 950 psi. The reaction is initially exothermic. After the initial exothermic stage of the reaction was complete the reaction temperature was maintained at 40° C. by external heating and later at 60° C. Hydrogen gas was added as needed to maintain the reaction rate. After 47 hours the reaction was judged complete by GCMS analysis so the crude reaction product was filtered through a silica gel pad 3 inches in diameter×3 inches high and the silica gel was washed with 550 mL 5% ethyl acetate in hexanes. After removal of the solvent by rotary evaporation the crude squalane weighed 332.6 g. The product was distilled in 3 batches using a Kugelrohr bulb to bulb apparatus to give 282.4 g squalane (83.4% yield over both steps). was added The vessel was sealed evacuated under house vacuum for twenty minutes (ca. 20 ton) by external heating and later at 60° C Hydrogen gas was added to maintain the reaction rate so the crude reaction product was filtered through a silica gel pad 3 inches in diameter×3 inches high the silica gel was washed with 550 mL 5% ethyl acetate in hexanes After removal of the solvent by rotary evaporation the crude squalane The product was distilled in 3 batches

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dehydrosqualene prepared above was placed in a one liter Parr pressure reactor and 1.1 g of 5% Pd/C was added. The vessel was sealed and evacuated under house vacuum for twenty minutes (ca. 20 ton) and then pressurized with hydrogen gas up to 950 psi. The reaction is initially exothermic. After the initial exothermic stage of the reaction was complete the reaction temperature was maintained at 40° C. by external heating and later at 60° C. Hydrogen gas was added as needed to maintain the reaction rate. After 47 hours the reaction was judged complete by GCMS analysis so the crude reaction product was filtered through a silica gel pad 3 inches in diameter×3 inches high and the silica gel was washed with 550 mL 5% ethyl acetate in hexanes. After removal of the solvent by rotary evaporation the crude squalane weighed 332.6 g. The product was distilled in 3 batches using a Kugelrohr bulb to bulb apparatus to give 282.4 g squalane (83.4% yield over both steps). was added The vessel was sealed evacuated under house vacuum for twenty minutes (ca. 20 ton) by external heating and later at 60° C Hydrogen gas was added to maintain the reaction rate so the crude reaction product was filtered through a silica gel pad 3 inches in diameter×3 inches high the silica gel was washed with 550 mL 5% ethyl acetate in hexanes After removal of the solvent by rotary evaporation the crude squalane The product was distilled in 3 batches

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

Procedure: In a 300 ml autoclave were placed 20 g of 2,6,10,15,19,23-hexamethyltetracosane-10,15-diol, 40 ml of n-heptane, 0.4 ml of acetic acid and 0.4 g of 5 % palladium on active carbon and the mixture was hydrogenated at 200° C under a hydrogen pressure of 100 kg/cm2 for 15 hours to give squalane quantitatively. was hydrogenated at 200° C under a hydrogen for 15 hours

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

Procedure: Then in 300 ml autoclave were placed 20 g of the distilled 2,6,10,15,19,23-hexamethyltetracosane-10,15-diol, 40 ml of glacial acetic acid and 1 g of 5 % palladium on active carbon and the mixture was hydrogenated at 200° C under a hydrogen pressure of 100 kg/cm2 for 10 hours. The catalyst was filtered off, the reaction mixture and the acetic acid was distilled off to afford squalane in 100 % conversion ratio, which was distilled through a packed column to give 14.2 g of the purified squalane. was hydrogenated at 200° C under a hydrogen for 10 hours The catalyst was filtered off the reaction mixture and the acetic acid was distilled off

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

Procedure: To 100 ml of n-heptane was dissolved 50 g of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol which was prepared in the same manner as in example 5 and 2.5 g of 3 % palladium on active carbon was added. The mixture was hydrogenated at 50° C under a hydrogen pressure of 3 ~ 5 kg/cm2. The product was subjected to dehydration, hydrogenation and distillation in the same manner as in example 4 to give 40.6 g of squalane. was added was hydrogenated at 50° C under a hydrogen The product was subjected to dehydration, hydrogenation and distillation in the same manner as in example 4

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

Procedure: To 100 ml of n-heptane was dissolved 50 g of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol which was prepared in the same manner as in example 5 and 2.5 g of 3 % palladium on active carbon was added. The mixture was hydrogenated at 50° C under a hydrogen pressure of 3 ~ 5 kg/cm2. The product was subjected to dehydration, hydrogenation and distillation in the same manner as in example 4 to give 40.6 g of squalane. was added was hydrogenated at 50° C under a hydrogen The product was subjected to dehydration, hydrogenation and distillation in the same manner as in example 4

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

Procedure: The formulations of SLP in an emulsion of squalane in water, soybean oil in water and hexadecane in water were prepared according to the method described in Example 1.

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

Procedure: As the oligomer (D) represented by the formula: ##STR2## When m is 0 and R is ##STR3## is a hydrogenated product of polyisoprene. For obtaining a hydrogenated product of polyisoprene, it can be easily produced by carrying out anion polymerization of isoprene in a cyclohexane solution under the copresence of sec-butyl lithium catalyst and then hydrogenating the polymer in the presence of a nickel naphthenate catalyst. On the other hand, when m is 1, n and pare 2, and R is ##STR4## it is squalane obtained by hydrogenation of squalene with a nickel catalyst. Squalene which is a starting material of squalane is contained in liver oil of a deep sea shark, and it can be obtained by subjecting the unsaponified product of shark liver oil to fractional distillation, deacidification and further to fractional distillation in the presence of metallic sodium, or condensing farnesyl chloride or farnesyl bromide in the presence of metallic magnesium, or carrying out Wittig reaction on transgeraniol acetone. can be easily produced

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

Procedure: Ethynylation of 194 g of citronelliodene acetone was carried out with acetylene in the same manner as in example 20 except that citronellidene acetone was used in place of pseudoionone and 278 g of a crude product was thus obtained. This product was subjected to oxydative-coupling, hydrogenation and hydrogenolysis in sequence in the same manner as in example 20 and squalane was thus obtained in a yield of 36.3 % from citronellidene acetone to squalane. was thus obtained

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

Procedure: In a 2-l. three-necked and round-bottomed flask were placed 220 g of 3,7,11-trimethyl-6,10-dien-1-in-3-ol, 1 g of copper acetate, 20.2 ml of pyridine and 440 ml of n-heptane. The mixture was stirred at temperatures of 60°~70°C for 5 hours by passing oxygen. The reaction mixture was washed with a 3N-H2SO4 -solution and then with a 10 % aqueous sodium chloride solution respectively three times and the n-heptane was distilled off to give 348 g of a crude product. A 100 g portion of this crude product was placed in a 500 ml autoclave and 200 ml of n-heptane, 1.8 g of nickel catalyst supported on diatomaceous earth which is roughly the same amount as that of nickel and 3.6 g of silica-alumina (alumina: 28~30 %) were added thereto. The mixture was subjected to hydrogenolysis at a temperature of 200°C under a hydrogen pressure of 100~20 kg/cm2 with stirring for 16 hours. After filtering off the catalyst and distilling off the n-heptane, the residue was distilled off at 202° - 208°C under reduced pressure of 0.3 - 0.4 mmHg to give 45.0 g of squalane. three-necked and round-bottomed flask were placed The reaction mixture was washed with a 3N-H2SO4 -solution with a 10 % aqueous sodium chloride solution respectively three times and the n-heptane was distilled off to give 348 g of a crude product were added was subjected to hydrogenolysis at a temperature of 200°C under a hydrogen with stirring for 16 hours After filtering off the catalyst distilling off the n-heptane the residue was distilled off at 202° - 208°C under reduced pressure of 0.3 - 0.4 mmHg

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

Procedure: A tubular reactor of 2.0 cm in inner diameter and 10 cm in length was packed with 20 g of carrier-supported nickel catalyst. Hydrogenation was carried out by feeding into the reactor the 50 wt % squalene solution in isooctane and hydrogen gas to obtain a squalane solution in isooctane. Samples were taken out for 30 hours after the temperature was stabilized at 210° C.

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

Procedure: A tubular reactor of 1.2 cm in inner diameter and 10 cm in length was packed with 10 g of carrier-supported nickel catalyst. Hydrogenation was carried out by feeding into the reactor the n-hexane solution of squalene and hydrogen gas to obtain a squalane solution in n-hexane. Samples were taken out for 30 hours after the temperature was stabilized at 200° C.