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Dehydrating condensation agent having property of accumulating at interface with water UPDATE

外国特許コード F110005472
整理番号 K05325WO
掲載日 2011年9月6日
出願国 アメリカ合衆国
出願番号 58894005
公報番号 20070135632
公報番号 7462715
出願日 平成17年1月31日(2005.1.31)
公報発行日 平成19年6月14日(2007.6.14)
公報発行日 平成20年12月9日(2008.12.9)
国際出願番号 JP2005001733
国際公開番号 WO2005075442
国際出願日 平成17年1月31日(2005.1.31)
国際公開日 平成17年8月18日(2005.8.18)
優先権データ
  • 特願2004-033284 (2004.2.10) JP
  • 2005WO-JP01733 (2005.1.31) WO
発明の名称 (英語) Dehydrating condensation agent having property of accumulating at interface with water UPDATE
発明の概要(英語) (US7462715)
The present invention provides a 1,3,5-triazine compound represented by the following formula I: This compound can be synthesized easily and more economically and can be used as a dehydrating condensing agent having the property of accumulating at a water interface.
In the case where carboxylic acid, amine, alcohol or other reaction substrate is amphiphilic, when mixing the dehydrating condensing agent of the present invention, which is amphiphilic, and the substrate to form various molecular aggregate phase including micelles in an aqueous solution, the substrate and the dehydrating condensing agent can be accumulated at the water interface.
As a result, the concentration of the substrate increases locally at the water interface, and condensation reaction can be performed extremely efficiently.
特許請求の範囲(英語) [claim1]
1. A 1,3,5-triazine compound represented by the following formula I:
wherein R1 and R2 are each independently a methyl group, an ethyl group, a hydroxyalkyl group having 2 to 5 carbon atoms, -- (CH2CH2O)mR6 (where m is an integer of 1 to 120, and R6 is a hydrogen atom, a methyl group, an ethyl group, or a propyl group), -- (CH2CH2NR7)mH (where m is an integer of 1 to 120, and R7 is an alkyl group having 2 to 5 carbon atoms, an N,N-dialkylaminoethyl group or -- CH2CH2N+(CH3)3), -- CH2CH2SO3-, -- CH2CH2N+(CH3)3, or an alkyl group having 6 to 20 carbon atoms, but both R1 and R2 are not alkyl groups having 6 to 20 carbon atoms at the same time;
one or two of R3, R4 and R5 are methyl groups, and the remaining R3, R4 and R5 are each independently -- CH2COO -- CnH2n+1, -- CnH2n+1, or -- C6H4-p-CnH2n+1, where n is an integer of 6 to 20, and -- CnH2n+1 is linear;
and X- is a halide ion, a triflate anion, a nitrate ion, a sulfate ion, a hydrogensulfate ion, a sulfonate ion, a tetrafluoroborate ion, or a perchlorate ion.
[claim2]
2. The compound of claim 1, wherein at least one of R1 and R2 is a methyl group or an ethyl group.
[claim3]
3. The compound of claim 1, wherein n is 12 to 16.
[claim4]
4. A method for producing a 1,3,5-triazine compound represented by the following formula I':
wherein R1 and R2are each independently a methyl group, an ethyl group, a hydroxyalkyl group having 2 to 5 carbon atoms, -- (CH2CH2O)mR6 (where m is an integer of 1 to 120, and R6 is a hydrogen atom, a methyl group, an ethyl group, or a propyl group), -- (CH2CH2NR7)mH (where m is an integer of 1 to 120, and R7 is an alkyl group having 2 to 5 carbon atoms, an N,N-dialkylaminoethyl group or -- CH2CH2N+(CH3)3), -- CH2CH2SO3-, -- CH2CH2N+(CH3)3, or an alkyl group having 6 to 20 carbon atoms, but both R1 and R2 are not alkyl groups having 6 to 20 carbon atoms at the same time;
one or two of R3, R4 and R5 are methyl groups, and the remaining R3, R4 and R5 are each independently -- CH2COO -- CnH2n+1, -- CnH2n+1, or -- C6H4-p-CnH2n+1, where n is an integer of 6 to 20, and -- CnH2n+1 is linear;
and X- is an triflate anion, comprising:obtaining triflate by mixing a compound represented by the following formula II and trifluoromethanesulfonic anhydride in an organic solvent:
wherein R1 and R2 are each independently a methyl group, an ethyl group, a hydroxyalkyl group having 2 to 5 carbon atoms, -- (CH2CH2O)mR6 (where m is an integer of 1 to 120, and R is a hydrogen atom, a methyl group, an ethyl group, or a propyl group), -- (CH2CH2NR7)mH (where m is an integer of 1 to 120, and R7 is an alkyl group having 2 to 5 carbon atoms, an N,N-dialkylaminoethyl group or -- CH2CH2N+(CH3)3), -- CH2CH2SO3-, -- CH2CH2N+(CH3)3, or an alkyl group having 6 to 20 carbon atoms, but both R1 and R2 are not alkyl groups having 6 to 20 carbon atoms at the same time;
and
mixing the obtained triflate and a tertiary amine represented by the following formula III in an appropriate organic solvent:
wherein one or two of R3, R4 and R5 are methyl groups, and the remaining R3, R4 and R5 are each independently -- CH2COO -- CnH2n+1, -- CnH2n+1, or -- C6H4-p-CnH2n+1, where n is an integer of 6 to 20, and -- CnH2n+1 is linear.
[claim5]
5. A method for producing a 1,3,5-triazine compound represented by the following formula I'':
wherein R1 and R2 are each independently a methyl group, an ethyl group, a hydroxyalkyl group having 2 to 5 carbon atoms, -- (CH2CH2O)mR6 (where m is an integer of 1 to 120, and R6 is a hydrogen atom, a methyl group, an ethyl group, or a propyl group), -- (CH2CH2NR7)mH (where m is an integer of 1 to 120, and R7 is an alkyl group having 2 to 5 carbon atoms, an N,N-dialkylaminoethyl group or -- CH2CH2N+(CH3)3), -- CH2CH2SO3-, -- CH2CH2N+(CH3)3, or an alkyl group having 6 to 20 carbon atoms, but both R1 and R2 are not alkyl groups having 6 to 20 carbon atoms at the same time;
one or two of R3, R4 and R5 are methyl groups, and the remaining R3, R4 and R5 are each independently -- CH2COO -- CnH2n+1, -- CnH2n+1, or -- C6H4-p-CnH2n+1, where n is an integer of 6 to 20, and -- CnH2n+1 is linear;
and X- is a halide ion, comprising:mixing a compound represented by the following formula IV and a tertiary amine represented by the following formula III in an appropriate solvent:
wherein R1 and R2 are each independently a methyl group, an ethyl group, a hydroxyalkyl group having 2 to 5 carbon atoms, -- (CH2CH2O)mR6 (where m is an integer of 1 to 120, and R6 is a hydrogen atom, a methyl group, an ethyl group, or a propyl group), -- (CH2CH2NR7)mH (where m is an integer of 1 to 120, and R7 is an alkyl group having 2 to 5 carbon atoms, an N,N-dialkylaminoethyl group or -- CH2CH2N+(CH3)3), -- CH2CH2SO3-, -- CH2CH2N+(CH3)3, or an alkyl group having 6 to 20 carbon atoms, but both R1 and R2 are not alkyl groups having 6 to 20 carbon atoms at the same time;
and X is a halogen atom;
wherein one or two of R3, R4 and R5 are methyl groups, and the remaining R3, R4 and R5 are each independently -- CH2COO -- CnH2n+1, -- CnH2n+1, or -- C6H4-p-CnH2n+1, where n is an integer of 6 to 20, and -- CnH2n+1 is linear.
[claim6]
6. A method for producing a carboxylic acid derivative, comprising: mixing a carboxylic acid and a compound having a nucleophilic functional group in an aqueous solution in the presence of a 1,3,5-triazine compound represented by the following formula I:
wherein R1 and R2 are each independently a methyl group, an ethyl group, a hydroxyalkyl group having 2 to 5 carbon atoms, -- (CH2CH2O)mR6 (where m is an integer of 1 to 120, and R6 is a hydrogen atom, a methyl group, an ethyl group, or a propyl group), -- (CH2CH2NR7)mH (where m is an integer of 1 to 120, and R7 is an alkyl group having 2 to 5 carbon atoms, an N,N-dialkylaminoethyl group or -- CH2CH2N+(CH3)3), -- CH2CH2SO3-, -- CH2CH2N+(CH3)3, or an alkyl group having 6 to 20 carbon atoms, but both R1 and R2 are not alkyl groups having 6 to 20 carbon atoms at the same time;
one or two of R3, R4 and R5 are methyl groups, and the remaining R3, R4 and R5 are each independently -- CH2COO -- CnH2n+1, -- CnH2n+1, or -- C6H4-p-CnH2n+1, where n is integer of 6 to 20, and -- CnH2n+1 is linear;
and X- is a halide ion, a triflate anion, a nitrate ion, a sulfate ion, a hydrogensulfate ion, a sulfonate ion, a tetrafluoroborate ion, or a perchlorate ion.
[claim7]
7. The method of claim 6, wherein the carboxylic acid is a fatty acid having 6 to 20 carbon atoms.
[claim8]
8. The method of claim 7, wherein the carboxylic acid is a fatty acid having 8 to 18 carbon atoms.
[claim9]
9. The method of claim 6, wherein at least one of R1 and R2 in the formula I is a methyl group or an ethyl group.
[claim10]
10. The method of claim 6, wherein n in the formula I is 12 to 16.
[claim11]
11. The method of claim 6, wherein the compound having a nucleophilic functional group is a primary amine compound or a secondary amine compound.
[claim12]
12. A method for producing a carboxylic acid derivative, comprising mixing: a carboxylic acid;
a compound having a nucleophilic functional group;a compound represented by the following formula IV;
and
a tertiary amine represented by the following formula III in an aqueous solution:
wherein R1 and R2 are each independently a methyl group, an ethyl group, a hydroxyalkyl group having 2 to 5 carbon atoms, -- (CH2CH2O)mR6 (where m is an integer of 1 to 120, and R6 is a hydrogen atom, a methyl group, an ethyl group, or a propyl group), -- (CH2CH2NR7)mH (where m is an integer of 1 to 120, and R7 is an alkyl group having 2 to 5 carbon atoms, an N,N-dialkylaminoethyl group or -- CH2CH2N+(CH3)3), -- CH2CH2SO3-, -- CH2CH2N+(CH3)3, or an alkyl group having 6 to 20 carbon atoms, but both R1 and R2 are not alkyl groups having 6 to 20 carbon atoms at the same time;
and X is a halogen atom,
wherein one or two of R3, R4 and R5 are methyl groups, and the remaining R3, R4 and R5 are each independently -- CH2COO -- CnH2n+1, -- CnH2n+1, or -- C6H4-p-CnH2n+1, where n is an integer of 6 to 20, and -- CnH2n+1 is linear.
[claim13]
13. The method of claim 12, wherein the carboxylic acid is a fatty acid having 6 to 20 carbon atoms.
[claim14]
14. The method of claim 13, wherein the carboxylic acid is a fatty acid having 8 to 18 carbon atoms.
[claim15]
15. The method of claim 12, wherein at least one of R1 and R2 in the formula I is a methyl group or an ethyl group.
[claim16]
16. The method of claim 12, wherein n in the formula III is 12 to 16.
[claim17]
17. The method of claim 12, wherein the compound having a nucleophilic functional group is a primary amine compound or secondary amine compound.
[claim18]
18. The method of claim 12, wherein the compound having a nucleophilic functional group is an alcohol compound.
  • 発明者/出願人(英語)
  • KUNISHIMA MUNETAKA
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
国際特許分類(IPC)
米国特許分類/主・副
  • C07C067/08
  • C07C231/02
  • C07D251/46
参考情報 (研究プロジェクト等) PRESTO Conversion and Control by Advanced Chemistry AREA
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