(3-methyl-2-bicyclo[2.2.1]heptanyl)methanol

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

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

Procedure: The same procedure of Example 12 was repeated except that 2-hydroxymethyl-3-methylnorbornane was dehydrated at a reaction temperature of 330° C., and that a product containing 59% 2,3-dimethyl-2-norbornene, and 31% 3-methyl-2-methylenenorbornane was obtained, to obtain 98 g of a fraction having a boiling point of 124° to 127° C./0.2 mmHg. was dehydrated at a reaction temperature of 330° C.

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

Procedure: In accordance with the same procedures as those conducted in Example 26, 2,200 g of a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo-[2.2.1]heptane and 2,3-dimethylbicyclo[2.2.1]hept-2-ene was obtained. The obtained product was placed into a 5 liter four-necked flask in combination with 45 g of boron trifluoride diethyl etherate. The dimerization was conducted for 5 hours under stirring at 10° C. After the reaction mixture was washed with a dilute aqueous solution of NaOH and a saturated aqueous solution of sodium chloride, the unreacted olefin was removed by distillation, and a reaction mixture of the dimerization of the raw material was obtained. The dimer of the olefin in an amount of 1,500 g was placed into a 2 liter autoclave and heated at 300° C. for 7 hours under stirring. After the reaction mixture was cooled, 30 g of a nickel/diatomaceous earth catalyst for hydrogenation (manufactured by NIKKI CHEMICAL Co., Ltd.; “N-113”) was added, and the hydrogenation was conducted (the hydrogen pressure: 30 kg/cm2; the reaction temperature: 250° C.; the reaction time: 5 hours). After the reaction was completed, the catalyst was removed by filtration. The filtrate was rectified under a reduced pressure, and 155 g of methylcyclopentylmethyl-dimethylbicyclo[2.2.1]heptane was obtained as a fraction having a boiling point in the range of 127 to 130° C./68 mmHg. The results of the measurements of the properties and the traction coefficient of the fluid are shown in Table 9.

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

Procedure: Into an atmospheric reaction tube of the flow type made of quartz and having an outer diameter of 20 mm and a length of 500 mm, 20 g of γ-alumina (manufactured by NIKKI CHEMICAL Co., Ltd.; “N612”) was placed. The dehydration was conducted at a reaction temperature of 285° C. and a weight hourly space velocity (WHSV) of 1.1 hr−1, and 490 g of a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethyl-bicyclo[2.2.1]hept-2-ene was obtained. was conducted at a reaction temperature of 285° C.

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

Procedure: Into an atmospheric reaction tube of the flow type made of quartz and having an outer diameter of 20 mm and a length of 500 mm, 20 g of γ-alumina (manufactured by NIKKI CHEMICAL Co., Ltd.; “N612N”) was placed. The dehydration was conducted at a reaction temperature of 285° C. at a weight hourly space velocity (WHSV) of 1.1 hr−1, and 490 g of a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethyl-bicyclo[2.2.1]hept-2-ene was obtained. was conducted at a reaction temperature of 285° C. at a weight hourly space velocity (WHSV) of 1.1 hr

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

Procedure: Into an atmospheric reaction tube of the flow type made of quartz and having an outer diameter of 20 mm and a length of 500 mm, 20 g of γ-alumina (manufactured by NIKKI CHEMICAL Co., Ltd.; “N612N”) was placed. The dehydration was conducted at a reaction temperature of 285° C. and a weight hourly space velocity (WHSV) of 1.1 hr−1, and 490 g of a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethyl-bicyclo[2.2.1]hept-2-ene was obtained. was conducted at a reaction temperature of 285° C.

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

Procedure: Into an atmospheric reaction tube of the flow type made of quartz and having an outer diameter of 20 mm and a length of 500 mm, 20 g of γ-alumina (manufactured by NIKKI CHEMICAL Co., Ltd.; “N612N”) was placed. The dehydration was conducted at a reaction temperature of 285° C. and a weight hourly space velocity (WHSV) of 1.1 hr−1, and 490 g of a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethyl-bicyclo[2.2.1]hept-2-ene was obtained. was conducted at a reaction temperature of 285° C.

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

Procedure: In a 3 L four-necked flask were placed 820 g of benzene and 53 g of concentrated sulfuric acid, to which 428 g of the dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethylbicyclo[2.2.1]hept-2-ene as main ingredients was added dropwise over 3 hours to perform alkylation. The reaction mixture was washed with a dilute aqueous NaOH solution and with a saturated aqueous sodium chloride solution. After the removal of unreacted benzene by distillation, the washed mixture was placed in a 2 L autoclave together with 18 g of a nickel/diatomaceous earth hydrogenation catalyst (N-113, manufactured by Nikki Chemical Co., Ltd.) and was hydrogenated (hydrogen pressure: 2 MPa, reaction temperature: 250° C., reaction time: 8 hours). After completion of the reaction, the catalyst was removed by filtration and the filtrate was distilled under reduced pressure to obtain 210 g of the desired cyclohexyl-dimethylbicyclo[2.2.1]heptane (Fluid D). The results of the measurements of the properties and the traction coefficient are shown in Table 1, from which it will be appreciated that the traction coefficient is low. In a 3 L four-necked flask were placed was added dropwise over 3 hours The reaction mixture was washed with a dilute aqueous NaOH solution and with a saturated aqueous sodium chloride solution After the removal of unreacted benzene by distillation (hydrogen pressure: 2 MPa, reaction temperature: 250° C., reaction time: 8 hours) After completion of the reaction the catalyst was removed by filtration the filtrate was distilled under reduced pressure

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

Procedure: Next, in an atmospheric reaction tube of a flow type made of quartz and having an outer diameter of 20 mm and a length of 500 mm, 20 g of γ-alumina (N612, manufactured by Nikki Chemical Co., Ltd.) was placed. The dehydration was conducted at a reaction temperature of 285° C. and a weight hourly space velocity (WHSV) of 1.1 hr−1, so that a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethylbicyclo[2.2.1]hept-2-ene was obtained in an amount of 490 g. was conducted at a reaction temperature of 285° C.

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

Procedure: Next, in an atmospheric reaction tube of a flow type made of quartz and having an outer diameter of 20 mm and a length of 500 mm, 20 g of γ-alumina (N612, manufactured by Nikki Chemical Co., Ltd.) was placed. The dehydration was conducted at a reaction temperature of 285° C. and a weight hourly space velocity (WHSV) of 1.1 hr−1, so that a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo[2.2.1]heptane and 2,3-dimethylbicyclo[2.2.1]hept-2-ene was obtained in an amount of 490 g. was conducted at a reaction temperature of 285° C.

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

Procedure: The same procedure of Example 12 was repeated except that 2-hydroxymethyl-3-methylnorbornane was dehydrated at a reaction temperature of 330° C., and that a product containing 59% 2,3-dimethyl-2-norbornene, and 31% 3-methyl-2-methylenenorbornane was obtained, to obtain 98 g of a fraction having a boiling point of 124° to 127° C./0.2 mmHg. was dehydrated at a reaction temperature of 330° C.

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

Procedure: In accordance with the same procedures as those conducted in Example 26, 2,200 g of a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo-[2.2.1]heptane and 2,3-dimethylbicyclo[2.2.1]hept-2-ene was obtained. The obtained product was placed into a 5 liter four-necked flask in combination with 45 g of boron trifluoride diethyl etherate. The dimerization was conducted for 5 hours under stirring at 10° C. After the reaction mixture was washed with a dilute aqueous solution of NaOH and a saturated aqueous solution of sodium chloride, the unreacted olefin was removed by distillation, and a reaction mixture of the dimerization of the raw material was obtained. The dimer of the olefin in an amount of 1,500 g was placed into a 2 liter autoclave and heated at 300° C. for 7 hours under stirring. After the reaction mixture was cooled, 30 g of a nickel/diatomaceous earth catalyst for hydrogenation (manufactured by NIKKI CHEMICAL Co., Ltd.; “N-113”) was added, and the hydrogenation was conducted (the hydrogen pressure: 30 kg/cm2; the reaction temperature: 250° C.; the reaction time: 5 hours). After the reaction was completed, the catalyst was removed by filtration. The filtrate was rectified under a reduced pressure, and 155 g of methylcyclopentylmethyl-dimethylbicyclo[2.2.1]heptane was obtained as a fraction having a boiling point in the range of 127 to 130° C./68 mmHg. The results of the measurements of the properties and the traction coefficient of the fluid are shown in Table 9.