butyl octadecanoate

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

Procedure: Specific examples of the lubricants used in the present invention include (all trade names): NAA-102, castor oil hardened fatty acid, NAA-42, CATION SA, NIMINE L-201, NONION E-208, ANON BF, ANON LG, butyl stearate, butyl laurate, and erucic acid, all of which are produced by NOF Corp.; oleic acid produced by Kanto Kagaku; FAL-205 and FAL-123 produced by Takemoto Oil & Fat Co., Ltd.; NGELB OL produced by New Japan Chemical Co., Ltd.; TA-3 produced by Shin-Etsu Chemical Co., Ltd.; ARMIDE P produced by Lion-Armer Co., Ltd.; DUOMINE TDO produced by Lion Corp.; BA-41G produced by The Nisshin Oil Mills, Ltd.; PROFUAN 2012 E, NEW POLE PE61, and IONET MS-400 produced by Sanyo Chemical Industries, Ltd. all of which are produced by NOF Corp

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

Procedure: Examples of lubricating agents which can be used in the present invention are commercially available under the trade names of NAA-102, NAA-415, NAA-312, NAA-160, NAA-180, NAA-174, NAA-175, NAA-222, NAA-34, NAA-35, NAA-171, NAA-122, NAA-142, NAA-160, NAA-173K, Castor oil-cured fatty acid, NAA-42, NAA-44, Cation SA, Cation MA, Cation AB, Cation BB, Nymeen L-201, Nymeen L-202, Nymeen S-202, Nonion E-208, Nonion P-208, Nonion S-207, Nonion K-204, Nonion NS-202, Nonion NS-210, Nonion HS-206, Nonion L-2, Nonion S-2, Nonion S-4, Nonion O-2, Nonion LP-20R, Nonion PP-40R, Nonion SP-60R, Nonion OP-80R, Nonion OP-85R, Nonion LT-221, Nonion ST-221, Nonion OT-221, Monoguri MB, Nonion DS-60, Anon BF, Anon LG, Butyl stearate, butyl laurate, and erucic acid (produced by Nippon Oils and Fats Co.); Oleic acid produced by Kanto Chemical Co., Ltd.; FAL-205, FAL-123 produced by Takemoto Yushi Co., Ltd.; Enujerubu LO, Enujerubu IPM, and Sansosyzer E4030 (produced by Shin Nihon Rika Co., Ltd.); TA-3, KF-96, KF-96L, KF-96H, KF-410, KF-420 KF-965, KF-54, KF-50, KF-56, KF-907, KF-851, X-22-819, X-22-822, KF-905, KF-700,-KF-393, KF-857, KF-860 , KF-865, X-22-980, KF-101, KF-102, KF-103, X-22-3710, X-22-3715, KF-910, and KF-3935 (produced by Shin-Etsu Chemical Co., Ltd.); Armide P, Armide C, and Armoslip CP (produced by Lion Ahmer Co., Ltd.); Duomin TDO produced by Lion Fat and Oil Co., Ltd.; BA-41G produced by Nisshin Oil Mill Ltd.; Profan 2012E, Newpole PE61, Ionet MS-400, Ionet MO-200, Ionet DL-200, Ionet DS-300, Ionet DS-300, Ionet DS-1000, and Ionet DO-200 (produced by Sanyo Kasei Co., Ltd.).

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

Procedure: Specific examples of the lubricants used in the present invention include (all trade names): NAA-102, castor oil hardened fatty acid, NAA-42, CATION SA, NIMINE L-201, NONION E-208, ANON BF, ANON LG, butyl stearate, butyl laurate, and erucic acid, all of which are produced by NOF Corp.; oleic acid produced by Kanto Kagaku; FAL-205 and FAL-123 produced by Takemoto Oil & Fat Co., Ltd.; NGELB OL produced by New Japan Chemical Co., Ltd.; TA-3 produced by Shin-Etsu Chemical Co., Ltd.; ARMIDE P produced by Lion-Armer Co., Ltd.; DUOMINE TDO produced by Lion Corp.; BA-41G produced by The Nisshin Oil Mills, Ltd.; PROFUAN 2012 E, NEW POLE PE61, and IONET MS-400 produced by Sanyo Chemical Industries, Ltd. all of which are produced by NOF Corp

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

Procedure: Examples of lubricating agents which can be used in the present invention are commercially available under the trade names of NAA-102, NAA-415, NAA-312, NAA-160, NAA-180, NAA-174, NAA-175, NAA-222, NAA-34, NAA-35, NAA-171, NAA-122, NAA-142, NAA-160, NAA-173K, Castor oil-cured fatty acid, NAA-42, NAA-44, Cation SA, Cation MA, Cation AB, Cation BB, Nymeen L-201, Nymeen L-202, Nymeen S-202, Nonion E-208, Nonion P-208, Nonion S-207, Nonion K-204, Nonion NS-202, Nonion NS-210, Nonion HS-206, Nonion L-2, Nonion S-2, Nonion S-4, Nonion O-2, Nonion LP-20R, Nonion PP-40R, Nonion SP-60R, Nonion OP-80R, Nonion OP-85R, Nonion LT-221, Nonion ST-221, Nonion OT-221, Monoguri MB, Nonion DS-60, Anon BF, Anon LG, Butyl stearate, butyl laurate, and erucic acid (produced by Nippon Oils and Fats Co.); Oleic acid produced by Kanto Chemical Co., Ltd.; FAL-205, FAL-123 produced by Takemoto Yushi Co., Ltd.; Enujerubu LO, Enujerubu IPM, and Sansosyzer E4030 (produced by Shin Nihon Rika Co., Ltd.); TA-3, KF-96, KF-96L, KF-96H, KF-410, KF-420 KF-965, KF-54, KF-50, KF-56, KF-907, KF-851, X-22-819, X-22-822, KF-905, KF-700,-KF-393, KF-857, KF-860 , KF-865, X-22-980, KF-101, KF-102, KF-103, X-22-3710, X-22-3715, KF-910, and KF-3935 (produced by Shin-Etsu Chemical Co., Ltd.); Armide P, Armide C, and Armoslip CP (produced by Lion Ahmer Co., Ltd.); Duomin TDO produced by Lion Fat and Oil Co., Ltd.; BA-41G produced by Nisshin Oil Mill Ltd.; Profan 2012E, Newpole PE61, Ionet MS-400, Ionet MO-200, Ionet DL-200, Ionet DS-300, Ionet DS-300, Ionet DS-1000, and Ionet DO-200 (produced by Sanyo Kasei Co., Ltd.).

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

Procedure: An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired butyl methanesulfonate (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50° C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with butyl methanesulfonate to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted butyl methanesulfonate, a 51% reduction.

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired butyl methanesulfonate (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50° C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with butyl methanesulfonate to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted butyl methanesulfonate, a 51% reduction. originally charged to the reaction)

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

Procedure: Such lubricating agents which can be used in the present invention are commercially available under the trade names of NAA-102, NAA-415, NAA-312, NAA-160, NAA-180, NAA-174, NAA-175, NAA-222,.NAA-34, NAA-35, NAA-171, NAA-122, NAA-142, NAA-160, NAA-173K, Castor oil-cured fatty acid, NAA-42, NAA-44, Cation SA, Cation MA, Cation AB, Cation BB, Nymeen L-201, Nymeen L-202, Nymeen S-202, Nonion E-208, Nonion P-208, Nonion S-207, Nonion K-204, Nonion NS-202, Nonion NS-210, Nonion HS-206, Nonion L-2, Nonion S-2, Nonion S-4, Nonion 0-2, Nonion LP-20R, Nonion PP-40R, Nonion SP-60R, Nonion OP-80R, Nonion OP-85R, Nonion LT-221, Nonion ST-221, Nonion OT-221, Monoguri MB, Nonion DS-60, Anon BF, Anon LG, Butyl stearate, Butyl laurate, and erucic acid (which are produced by Nihon Yushi Co., Ltd.); Oleic acid produced by Kanto Chemical Co., Ltd.; FAL-205, FAL-123 produced by Takemoto Yubou Co., Ltd.; Enujerubu LO, Enujorubu IPM, and Sansosyzer E4030 (which are produced by Shin Nihon Rika Co., Ltd.); TA-3, KF-96, KF-96L, KF-96H, KF-410, KF-420, KF-965, KF-54, KF-50, KF-56, KF-907, KF-851, X-22-819, X-22-822, KF-905, KF-700, KF-393, KF-857, KF-860, KF-865, X-22-980, KF-101, KF-102, KF-103, X-22-3710, X-22-3715, KF-910, and KF-3935 (which are produced by Shinetsu Chemical Co., Ltd.); Armide P, Armide C, and Armoslip CP (which are produced by Lion Ahmer Co., Ltd.); Duomin TDO produced by Lion Yushi Co., Ltd.; BA-41G produced by Nisshin Seiyu Co., Ltd.; Profan 2012E, Newpole PE61, Ionet MS-400, Ionet MO-200, Ionet DL-200, Ionet DS-300, Ionet DS-300, Ionet DS-1000, and Ionet DO-200 (which are produced by Sanyo Kasei Co., Ltd.).

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

Procedure: Such lubricating agents which can be used in the present invention are commercially available under the trade names of NAA-102, NAA-415, NAA-312, NAA-160, NAA-180, NAA-174, NAA-175, NAA-222,.NAA-34, NAA-35, NAA-171, NAA-122, NAA-142, NAA-160, NAA-173K, Castor oil-cured fatty acid, NAA-42, NAA-44, Cation SA, Cation MA, Cation AB, Cation BB, Nymeen L-201, Nymeen L-202, Nymeen S-202, Nonion E-208, Nonion P-208, Nonion S-207, Nonion K-204, Nonion NS-202, Nonion NS-210, Nonion HS-206, Nonion L-2, Nonion S-2, Nonion S-4, Nonion 0-2, Nonion LP-20R, Nonion PP-40R, Nonion SP-60R, Nonion OP-80R, Nonion OP-85R, Nonion LT-221, Nonion ST-221, Nonion OT-221, Monoguri MB, Nonion DS-60, Anon BF, Anon LG, Butyl stearate, Butyl laurate, and erucic acid (which are produced by Nihon Yushi Co., Ltd.); Oleic acid produced by Kanto Chemical Co., Ltd.; FAL-205, FAL-123 produced by Takemoto Yubou Co., Ltd.; Enujerubu LO, Enujorubu IPM, and Sansosyzer E4030 (which are produced by Shin Nihon Rika Co., Ltd.); TA-3, KF-96, KF-96L, KF-96H, KF-410, KF-420, KF-965, KF-54, KF-50, KF-56, KF-907, KF-851, X-22-819, X-22-822, KF-905, KF-700, KF-393, KF-857, KF-860, KF-865, X-22-980, KF-101, KF-102, KF-103, X-22-3710, X-22-3715, KF-910, and KF-3935 (which are produced by Shinetsu Chemical Co., Ltd.); Armide P, Armide C, and Armoslip CP (which are produced by Lion Ahmer Co., Ltd.); Duomin TDO produced by Lion Yushi Co., Ltd.; BA-41G produced by Nisshin Seiyu Co., Ltd.; Profan 2012E, Newpole PE61, Ionet MS-400, Ionet MO-200, Ionet DL-200, Ionet DS-300, Ionet DS-300, Ionet DS-1000, and Ionet DO-200 (which are produced by Sanyo Kasei Co., Ltd.).

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

Procedure: Such lubricating agents which can be used in the present invention are commercially available under the trade names of NAA-102, NAA-415, NAA-312, NAA-160, NAA-180, NAA-174, NAA-175, NAA-222,.NAA-34, NAA-35, NAA-171, NAA-122, NAA-142, NAA-160, NAA-173K, Castor oil-cured fatty acid, NAA-42, NAA-44, Cation SA, Cation MA, Cation AB, Cation BB, Nymeen L-201, Nymeen L-202, Nymeen S-202, Nonion E-208, Nonion P-208, Nonion S-207, Nonion K-204, Nonion NS-202, Nonion NS-210, Nonion HS-206, Nonion L-2, Nonion S-2, Nonion S-4, Nonion 0-2, Nonion LP-20R, Nonion PP-40R, Nonion SP-60R, Nonion OP-80R, Nonion OP-85R, Nonion LT-221, Nonion ST-221, Nonion OT-221, Monoguri MB, Nonion DS-60, Anon BF, Anon LG, Butyl stearate, Butyl laurate, and erucic acid (which are produced by Nihon Yushi Co., Ltd.); Oleic acid produced by Kanto Chemical Co., Ltd.; FAL-205, FAL-123 produced by Takemoto Yubou Co., Ltd.; Enujerubu LO, Enujorubu IPM, and Sansosyzer E4030 (which are produced by Shin Nihon Rika Co., Ltd.); TA-3, KF-96, KF-96L, KF-96H, KF-410, KF-420, KF-965, KF-54, KF-50, KF-56, KF-907, KF-851, X-22-819, X-22-822, KF-905, KF-700, KF-393, KF-857, KF-860, KF-865, X-22-980, KF-101, KF-102, KF-103, X-22-3710, X-22-3715, KF-910, and KF-3935 (which are produced by Shinetsu Chemical Co., Ltd.); Armide P, Armide C, and Armoslip CP (which are produced by Lion Ahmer Co., Ltd.); Duomin TDO produced by Lion Yushi Co., Ltd.; BA-41G produced by Nisshin Seiyu Co., Ltd.; Profan 2012E, Newpole PE61, Ionet MS-400, Ionet MO-200, Ionet DL-200, Ionet DS-300, Ionet DS-300, Ionet DS-1000, and Ionet DO-200 (which are produced by Sanyo Kasei Co., Ltd.).

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

Procedure: Specific examples of the lubricants used in the present invention include (all trade names): NAA-102, castor oil hardened fatty acid, NAA-42, CATION SA, NIMINE L-201, NONION E-208, ANON BF, ANON LG, butyl stearate, butyl laurate, and erucic acid, all of which are produced by NOF Corp.; oleic acid produced by Kanto Kagaku; FAL-205 and FAL-123 produced by Takemoto Oil & Fat Co., Ltd.; NGELB OL produced by New Japan Chemical Co., Ltd.; TA-3 produced by Shin-Etsu Chemical Co., Ltd.; ARMIDE P produced by Lion-Armer Co., Ltd.; DUOMINE TDO produced by Lion Corp.; BA-41G produced by The Nisshin Oil Mills, Ltd.; PROFUAN 2012 E, NEW POLE PE61, and IONET MS-400 produced by Sanyo Chemical Industries, Ltd. all of which are produced by NOF Corp

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

Procedure: Examples of lubricating agents which can be used in the present invention are commercially available under the trade names of NAA-102, NAA-415, NAA-312, NAA-160, NAA-180, NAA-174, NAA-175, NAA-222, NAA-34, NAA-35, NAA-171, NAA-122, NAA-142, NAA-160, NAA-173K, Castor oil-cured fatty acid, NAA-42, NAA-44, Cation SA, Cation MA, Cation AB, Cation BB, Nymeen L-201, Nymeen L-202, Nymeen S-202, Nonion E-208, Nonion P-208, Nonion S-207, Nonion K-204, Nonion NS-202, Nonion NS-210, Nonion HS-206, Nonion L-2, Nonion S-2, Nonion S-4, Nonion O-2, Nonion LP-20R, Nonion PP-40R, Nonion SP-60R, Nonion OP-80R, Nonion OP-85R, Nonion LT-221, Nonion ST-221, Nonion OT-221, Monoguri MB, Nonion DS-60, Anon BF, Anon LG, Butyl stearate, butyl laurate, and erucic acid (produced by Nippon Oils and Fats Co.); Oleic acid produced by Kanto Chemical Co., Ltd.; FAL-205, FAL-123 produced by Takemoto Yushi Co., Ltd.; Enujerubu LO, Enujerubu IPM, and Sansosyzer E4030 (produced by Shin Nihon Rika Co., Ltd.); TA-3, KF-96, KF-96L, KF-96H, KF-410, KF-420 KF-965, KF-54, KF-50, KF-56, KF-907, KF-851, X-22-819, X-22-822, KF-905, KF-700,-KF-393, KF-857, KF-860 , KF-865, X-22-980, KF-101, KF-102, KF-103, X-22-3710, X-22-3715, KF-910, and KF-3935 (produced by Shin-Etsu Chemical Co., Ltd.); Armide P, Armide C, and Armoslip CP (produced by Lion Ahmer Co., Ltd.); Duomin TDO produced by Lion Fat and Oil Co., Ltd.; BA-41G produced by Nisshin Oil Mill Ltd.; Profan 2012E, Newpole PE61, Ionet MS-400, Ionet MO-200, Ionet DL-200, Ionet DS-300, Ionet DS-300, Ionet DS-1000, and Ionet DO-200 (produced by Sanyo Kasei Co., Ltd.).