JP2012531450A - アミノ基を有する有機酸のアシル化のための連続的方法 - Google Patents
アミノ基を有する有機酸のアシル化のための連続的方法 Download PDFInfo
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- JP2012531450A JP2012531450A JP2012518032A JP2012518032A JP2012531450A JP 2012531450 A JP2012531450 A JP 2012531450A JP 2012518032 A JP2012518032 A JP 2012518032A JP 2012518032 A JP2012518032 A JP 2012518032A JP 2012531450 A JP2012531450 A JP 2012531450A
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- 125000003277 amino group Chemical group 0.000 title claims abstract description 95
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 68
- 238000010924 continuous production Methods 0.000 title claims abstract description 7
- 235000005985 organic acids Nutrition 0.000 title abstract description 20
- 230000010933 acylation Effects 0.000 title description 7
- 238000005917 acylation reaction Methods 0.000 title description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 275
- 239000002253 acid Substances 0.000 claims abstract description 104
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 61
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 45
- 150000001408 amides Chemical class 0.000 claims abstract description 42
- 229910052751 metal Inorganic materials 0.000 claims abstract description 30
- 239000002184 metal Substances 0.000 claims abstract description 30
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 24
- 230000006181 N-acylation Effects 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 122
- 239000011541 reaction mixture Substances 0.000 claims description 88
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 68
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- 239000000203 mixture Substances 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- -1 alkali metal salt Chemical class 0.000 claims description 28
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 6
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 claims description 6
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 235000021355 Stearic acid Nutrition 0.000 claims description 5
- 235000011054 acetic acid Nutrition 0.000 claims description 5
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 5
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- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 4
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- XSXIVVZCUAHUJO-HZJYTTRNSA-N (11Z,14Z)-icosadienoic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-HZJYTTRNSA-N 0.000 claims description 3
- OOJGMLFHAQOYIL-SQIWNDBBSA-N (2e,4e)-hexadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C(O)=O OOJGMLFHAQOYIL-SQIWNDBBSA-N 0.000 claims description 3
- GGAUUQHSCNMCAU-ZXZARUISSA-N (2s,3r)-butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C[C@H](C(O)=O)[C@H](C(O)=O)CC(O)=O GGAUUQHSCNMCAU-ZXZARUISSA-N 0.000 claims description 3
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Abstract
R1−COOH (I)
[式中、R1は、水素または炭素原子数1〜50の場合により置換された炭化水素残基を表す]
で表されるカルボン酸の少なくとも一種と、次式(II)
R2NH−A−X (II)
[式中、
Aは、炭素原子数1〜50の場合により置換された炭化水素残基を表し、
Xは、酸基またはそれの金属塩を表し、そして
R2は、水素、炭素原子数1〜50の場合により置換された炭化水素残基、または式−A−X(式中、Aも、Xも、互いに独立して、上記の意味を有する)の基を表す]
で表される少なくとも一つのアミノ基を有する有機酸の少なくとも一種とを、モノモード−マイクロ波アプリケータのマイクロ波の伝播方向にその長軸がある反応管中でマイクロ波照射下に反応させてアミドとする、方法である。
Description
R1−COOH (I)
[式中、R1は、水素または炭素原子数1〜50の場合により置換された炭化水素残基を表す]
で表されるカルボン酸の少なくとも一種と、次式(II)
R2NH−A−X (II)
[式中、
Aは、炭素原子数1〜50の場合により置換された炭化水素残基を表し、
Xは、酸基またはそれの金属塩を表し、そして
R2は、水素、炭素原子数1〜50の場合により置換された炭化水素残基、または式−A−Xの基を表し、ここでA並びにXは、互いに独立して、上記の意味を有する]
で表される少なくとも一つのアミノ基を有する有機酸の少なくとも一種とを、モノモード−マイクロ波アプリケータのマイクロ波の伝播方向にその長軸がある反応管中でマイクロ波照射下に反応させてアミドとする、方法である。
更に、本発明の方法は、アリール基R1が、一つまたはそれ以上の、例えば二つまたは三つのヒドロキシル基及び/またはヒドロキシアルキル基を有する芳香族カルボン酸アミドの製造に特に適している。この際、相当するカルボン酸(I)と、特に多くても当モル量の式(II)のアミノ基を有する有機酸との反応において、カルボキシル基のアミド化が選択的に起こり、フェノール性OH基のアミノリシスは起こらない。
本発明の方法に従いアミド化するために好適なカルボン酸(I)は、例えばギ酸、酢酸、プロピオン酸、酪酸、イソ酪酸、ペンタン酸、イソペンタン酸、ピバリン酸、アクリル酸、メタクリル酸、クロトン酸、2,2−ジメチルアクリル酸、マレイン酸、フマル酸、イタコン酸、ケイ皮酸及びメトキシケイ皮酸、コハク酸、ブタンテトラカルボン酸、フェニル酢酸、(2−ブロモフェニル)酢酸、(メトキシフェニル)酢酸、(ジメトキシフェニル)酢酸、2−フェニルプロピオン酸、3−フェニルプロピオン酸、3−(4−ヒドロキシフェニル)プロピオン酸、4−ヒドロキシフェノキシ酢酸、ヘキサン酸、シクロヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、ネオノナン酸、デカン酸、ネオデカン酸、ウンデカン酸、ネオウンデカン酸、ドデカン酸、トリデカン酸、イソトリデカン酸、テトラデカン酸、12−メチルトリデカン酸、ペンタデカン酸、13−メチルテトラデカン酸、12−メチルテトラデカン酸、ヘキサデカン酸、14−メチルペンタデカン酸、ヘプタデカン酸、15−メチルヘキサデカン酸、14−メチルヘキサデカン酸、オクタデカン酸、イソオクタデカン酸、イコサン酸、ドコサン酸及びテトラコサン酸、ミリストレイン酸、パルミトレイン酸、ヘキサデカジエン酸、デルタ−9−cis−ヘプタデセン酸、オレイン酸、ペトロセリン酸、バクセン酸、リノール酸、リノレン酸、ガドレイン酸、ゴンド酸、イコサジエン酸、アラキドン酸、セトレイン酸、エルカ酸、ドコサジエン酸及びテトラコセン酸、ドデセニルコハク酸及びオクタデセニルコハク酸、及び不飽和脂肪酸から製造可能なダイマー脂肪酸、並びにこれらの混合物である。更に、天然油脂から、例えば綿実油、ココナッツ油、ピーナッツ油、サフラワー油、マイズ油、パーム核油、ナタネ油、オリーブ油、カラシ油、ダイズ油、ヒマワリ油並びに獣脂油、骨油、及び魚油から得られるカルボン酸混合物も適している。本発明の方法のためのカルボン酸またはカルボン酸混合物としては、トール油脂肪酸並びに樹脂酸及びナフテン酸も同様に適している。本発明方法に従うアミド化に適した更に別のカルボン酸(I)は、例えば安息香酸、フタル酸、イソフタル酸; ナフタレンカルボン酸、ピリジンカルボン酸及びナフタレンジカルボン酸の各種異性体、トリメリット酸、トリメシン酸、ピロメリット酸及びメリト酸; メトキシ安息香酸、ヒドロキシ安息香酸、ヒドロキシメチル安息香酸、ヒドロキシメトキシ安息香酸、ヒドロキシジメトキシ安息香酸、ヒドロキシイソフタル酸、ヒドロキシナフタレンカルボン酸、ヒドロキシピリジンカルボン酸、ヒドロキシメチルピリジンカルボン酸、及びヒドロキシキノリンカルボン酸の各種異性体; 並びにo−トリル酸、m−トリル酸、p−トリル酸、o−エチル安息香酸、m−エチル安息香酸、p−エチル安息香酸、o−プロピル安息香酸、m−プロピル安息香酸、p−プロピル安息香酸及び3,4−ジメチル安息香酸である。様々なアリール−及び/またはアルキルアリールカルボン酸の混合物も同様に適している。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、1.6kgのメチルタウリン(10モル)を4Lの水−イソプロパノール混合物(3:2体積割合)中に溶解し、そして2.0kgのラウリン酸(10モル)と混合した。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、2リットルの水中に溶解した1.0kgのグリシン酸ナトリウム(27モル)を3.2kgの酢酸(107モル)と混合した。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、1.2kgのグリシンNa塩(12モル)を3.5リットルの水−イソプロパノール混合物(2:2体積割合)中に溶解し、そして2.65kgのステアリン酸(9.3モル)と混合した。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、1.45kgの4−アミノ安息香酸(10.5モル)及び2.25kgのココナッツ脂肪酸(10.5モル)を加温下に5Lのイソプロパノール中に溶解した。こうして得られた混合物を、35barの作業圧下に連続的に3.5L/hで反応管中にポンプ輸送して通し、1.6kWのマイクロ波出力にかけた。そのうち87%が反応物によって吸収された。照射域中での反応混合物の滞留時間は約49秒間であった。反応管の末端で、反応混合物は281℃の温度を有していた。
R1−COOH (I)
[式中、R1は、水素または炭素原子数1〜50の場合により置換された炭化水素残基を表す]
で表されるカルボン酸の少なくとも一種と、次式(II)
R2NH−A−X (II)
[式中、
Aは、炭素原子数1〜50の場合により置換された炭化水素残基を表し、
Xは、酸基またはそれの金属塩を表し、そして
R2は、水素、炭素原子数1〜50の場合により置換された炭化水素残基、または式−A−Xの基を表し、ここでA並びにXは、互いに独立して、上記の意味を有する]
で表される少なくとも一つのアミノ基を有する有機酸の少なくとも一種とを、モノモード−マイクロ波アプリケータのマイクロ波の伝播方向にその長軸がある反応管中でマイクロ波照射下に反応させてアミドとする、方法である。
更に、本発明の方法は、アリール基R1が、一つまたはそれ以上の、例えば二つまたは三つのヒドロキシル基及び/またはヒドロキシアルキル基を有する芳香族カルボン酸アミドの製造に特に適している。この際、相当するカルボン酸(I)と、特に多くても当モル量の式(II)のアミノ基を有する有機酸との反応において、カルボキシル基のアミド化が選択的に起こり、フェノール性OH基のアミノリシスは起こらない。
本発明の方法に従いアミド化するために好適なカルボン酸(I)は、例えばギ酸、酢酸、プロピオン酸、酪酸、イソ酪酸、ペンタン酸、イソペンタン酸、ピバリン酸、アクリル酸、メタクリル酸、クロトン酸、2,2−ジメチルアクリル酸、マレイン酸、フマル酸、イタコン酸、ケイ皮酸及びメトキシケイ皮酸、コハク酸、ブタンテトラカルボン酸、フェニル酢酸、(2−ブロモフェニル)酢酸、(メトキシフェニル)酢酸、(ジメトキシフェニル)酢酸、2−フェニルプロピオン酸、3−フェニルプロピオン酸、3−(4−ヒドロキシフェニル)プロピオン酸、4−ヒドロキシフェノキシ酢酸、ヘキサン酸、シクロヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、ネオノナン酸、デカン酸、ネオデカン酸、ウンデカン酸、ネオウンデカン酸、ドデカン酸、トリデカン酸、イソトリデカン酸、テトラデカン酸、12−メチルトリデカン酸、ペンタデカン酸、13−メチルテトラデカン酸、12−メチルテトラデカン酸、ヘキサデカン酸、14−メチルペンタデカン酸、ヘプタデカン酸、15−メチルヘキサデカン酸、14−メチルヘキサデカン酸、オクタデカン酸、イソオクタデカン酸、イコサン酸、ドコサン酸及びテトラコサン酸、ミリストレイン酸、パルミトレイン酸、ヘキサデカジエン酸、デルタ−9−cis−ヘプタデセン酸、オレイン酸、ペトロセリン酸、バクセン酸、リノール酸、リノレン酸、ガドレイン酸、ゴンド酸、イコサジエン酸、アラキドン酸、セトレイン酸、エルカ酸、ドコサジエン酸及びテトラコセン酸、ドデセニルコハク酸及びオクタデセニルコハク酸、及び不飽和脂肪酸から製造可能なダイマー脂肪酸、並びにこれらの混合物である。更に、天然油脂から、例えば綿実油、ココナッツ油、ピーナッツ油、サフラワー油、マイズ油、パーム核油、ナタネ油、オリーブ油、カラシ油、ダイズ油、ヒマワリ油並びに獣脂油、骨油、及び魚油から得られるカルボン酸混合物も適している。本発明の方法のためのカルボン酸またはカルボン酸混合物としては、トール油脂肪酸並びに樹脂酸及びナフテン酸も同様に適している。本発明方法に従うアミド化に適した更に別のカルボン酸(I)は、例えば安息香酸、フタル酸、イソフタル酸; ナフタレンカルボン酸、ピリジンカルボン酸及びナフタレンジカルボン酸の各種異性体、トリメリット酸、トリメシン酸、ピロメリット酸及びメリト酸; メトキシ安息香酸、ヒドロキシ安息香酸、ヒドロキシメチル安息香酸、ヒドロキシメトキシ安息香酸、ヒドロキシジメトキシ安息香酸、ヒドロキシイソフタル酸、ヒドロキシナフタレンカルボン酸、ヒドロキシピリジンカルボン酸、ヒドロキシメチルピリジンカルボン酸、及びヒドロキシキノリンカルボン酸の各種異性体; 並びにo−トリル酸、m−トリル酸、p−トリル酸、o−エチル安息香酸、m−エチル安息香酸、p−エチル安息香酸、o−プロピル安息香酸、m−プロピル安息香酸、p−プロピル安息香酸及び3,4−ジメチル安息香酸である。様々なアリール−及び/またはアルキルアリールカルボン酸の混合物も同様に適している。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、1.6kgのメチルタウリン(10モル)を4Lの水−イソプロパノール混合物(3:2体積割合)中に溶解し、そして2.0kgのラウリン酸(10モル)と混合した。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、2リットルの水中に溶解した1.0kgのグリシン酸ナトリウム(27モル)を3.2kgの酢酸(107モル)と混合した。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、1.2kgのグリシンNa塩(12モル)を3.5リットルの水−イソプロパノール混合物(2:2体積割合)中に溶解し、そして2.65kgのステアリン酸(9.3モル)と混合した。
攪拌機、内部温度計及び均圧管を備えた10Lビュッヒ攪拌オートクレーブ中で、1.45kgの4−アミノ安息香酸(10.5モル)及び2.25kgのココナッツ脂肪酸(10.5モル)を加温下に5Lのイソプロパノール中に溶解した。こうして得られた混合物を、35barの作業圧下に連続的に3.5L/hで反応管中にポンプ輸送して通し、1.6kWのマイクロ波出力にかけた。そのうち87%が反応物によって吸収された。照射域中での反応混合物の滞留時間は約49秒間であった。反応管の末端で、反応混合物は281℃の温度を有していた。
Claims (23)
- アミノ基を有する有機酸のN−アシル化のための連続的方法であって、次式(I)
R1−COOH (I)
[式中、R1は、水素、または炭素原子数1〜50の場合により置換された炭化水素残基を表す]
で表されるカルボン酸の少なくとも一種と、次式(II)
R2NH−A−X (II)
[式中、
Aは、炭素原子数1〜50の場合により置換された炭化水素残基を表し、
Xは、酸基またはそれの金属塩を表し、そして
R2は、水素、炭素原子数1〜50の場合により置換された炭化水素残基、または式−A−Xの基を表し、ここでAも、Xも、互いに独立して、上記の意味を有する]
で表される少なくとも一つのアミノ基を有する有機酸の少なくとも一種とを、モノモード−マイクロ波アプリケータのマイクロ波の伝播方向にその長軸がある反応管中でマイクロ波照射下に反応させてアミドとする、上記方法。 - マイクロ波による反応混合物の照射を、導波管を介してマイクロ波発生器に接続された中空導体の内部でマイクロ波に対しほぼ透明な反応管中で行う、請求項1の方法。
- マイクロ波アプリケータが中空共振器として構成される、請求項1及び2の一つまたはそれ以上の方法。
- マイクロ波アプリケータが反射型中空共振器として構成される、請求項1〜3の一つまたはそれ以上の方法。
- 反応管が、中空導体の中央対称軸に軸状に整列されている、請求項1〜4の一つまたはそれ以上の方法。
- 反応混合物の照射が、マイクロ波の同軸変換を備えた空洞共振器中で行われる、請求項1〜5の一つまたはそれ以上の方法。
- 空洞共振器がE01nモードで稼働され、この際nは1〜200の整数である、請求項1〜6の一つまたはそれ以上の方法。
- 空洞共振器中に定在波が形成される、請求項1〜7の一つまたはそれ以上の方法。
- 反応物がマイクロ波照射によって150〜500℃の温度に加熱される、請求項1〜8の一つまたはそれ以上の方法。
- マイクロ波照射が大気圧よりも高い圧力下に行われる、請求項1〜9の一つまたはそれ以上の方法。
- R1が、炭素原子数2〜30の場合により置換された脂肪族炭化水素残基である、請求項1〜10の一つまたはそれ以上の方法。
- R1が、少なくとも一つのC=C二重結合を含む、炭素原子数2〜30の場合により置換された脂肪族炭化水素残基である、請求項1〜11の一つまたはそれ以上の方法。
- R1が、炭素原子数1、2、3または4の飽和アルキル基である、請求項1〜11の一つまたはそれ以上の方法。
- R1が、炭素原子数2〜4の場合により置換されたアルケニル基を表す、請求項1〜12の一つまたはそれ以上の方法。
- R1が、(4n+2)π電子を有する場合により置換された環状全共役系であり、ここでnは1、2、3、4または5である、請求項1〜10の一つまたはそれ以上の方法。
- 式Iのカルボン酸が、ギ酸、酢酸、プロピオン酸、酪酸、イソ酪酸、ペンタン酸、イソペンタン酸、ピバリン酸、アクリル酸、メタクリル酸、クロトン酸、2,2−ジメチルアクリル酸、マレイン酸、フマル酸、イタコン酸、ケイ皮酸、メトキシケイ皮酸、コハク酸、ブタンテトラカルボン酸、フェニル酢酸、(2−ブロモフェニル)酢酸、(メトキシフェニル)酢酸、(ジメトキシフェニル)酢酸、2−フェニルプロピオン酸、3−フェニルプロピオン酸、3−(4−ヒドロキシフェニル)プロピオン酸、4−ヒドロキシフェノキシ酢酸、ヘキサン酸、シクロヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、ネオノナン酸、デカン酸、ネオデカン酸、ウンデカン酸、ネオウンデカン酸、ドデカン酸、トリデカン酸、テトラデカン酸、12−メチルトリデカン酸、ペンタデカン酸、13−メチルテトラデカン酸、12−メチルテトラデカン酸、ヘキサデカン酸、14−メチルペンタデカン酸、ヘプタデカン酸、15−メチルヘキサデカン酸、14−メチルヘキサデカン酸、オクタデカン酸、イソオクタデカン酸、イコサン酸、ドコサン酸、テトラコサン酸、ミリストレイン酸、パルミトレイン酸、ヘキサデカジエン酸、デルタ−9−cis−ヘプタデセン酸、オレイン酸、ペトロセリン酸、バクセン酸、リノール酸、リノレン酸、ガドレイン酸、ゴンド酸、イコサジエン酸、アラキドン酸、セトレイン酸、エルカ酸、ドコサジエン酸及びテトラコセン酸、ドデセニルコハク酸、オクタデセニルコハク酸; 綿実油、ココナッツ油、ピーナッツ油、サフラワー油、マイズ油、パーム核油、ナタネ油、オリーブ油、カラシ油、ダイズ油、ヒマワリ油、獣油、骨油、及び魚油から得られるカルボン酸混合物、トール油脂肪酸、樹脂酸及びナフテン酸、安息香酸、フタル酸、イソフタル酸; ナフタレンカルボン酸、ピリジンカルボン酸及びナフタレンジカルボン酸の各種異性体; トリメリット酸、トリメシン酸、ピロメリット酸及びメリト酸; メトキシ安息香酸、ヒドロキシ安息香酸、ヒドロキシメチル安息香酸、ヒドロキシメトキシ安息香酸、ヒドロキシジメトキシ安息香酸、ヒドロキシイソフタル酸、ヒドロキシナフタレンカルボン酸、ヒドロキシピリジンカルボン酸、ヒドロキシメチルピリジンカルボン酸、ヒドロキシキノリンカルボン酸の各種異性体; o−トリル酸、m−トリル酸、p−トリル酸、o−エチル安息香酸、m−エチル安息香酸、p−エチル安息香酸、o−プロピル安息香酸、m−プロピル安息香酸、p−プロピル安息香酸及び3,4−ジメチル安息香酸から選択される、請求項1〜10の一つまたはそれ以上の方法。
- Aが、炭素原子数1〜12の脂肪族基及び炭素原子数5〜12の芳香族基から選択される、請求項1〜16の一つまたはそれ以上の方法。
- R2が、H、炭素原子数2〜18の場合により置換された脂肪族基、場合により置換されたC6〜C12アリール基、環員数5〜12の場合により置換されたヘテロ芳香族基、または式−A−Xの基からなる群から選択され、ここで
Aは、炭素原子数1〜50の場合により置換された炭化水素基を表し、そして
Xは、酸基またはそれの金属塩を表す、
請求項1〜17の一つまたはそれ以上の方法。 - Xが、カルボン酸、スルホン酸及びホスホン酸からなる群から選択される、請求項1〜18の一つまたはそれ以上の方法。
- Xが、酸基のアルカリ金属塩またはアルカリ土類金属塩を表す、請求項1〜19の一つまたはそれ以上の方法。
- 式(II)の少なくとも一つのアミノ基を有する有機酸が、α−アミノカルボン酸、β−アミノスルホン酸、アミノメチレンホスホン酸及びこれらの金属塩から選択される、請求項1〜20の一つまたはそれ以上の方法。
- カルボン酸(I)と、アミノ基を有する有機酸(II)とを、それぞれカルボキシル基及びアミノ基のモル当量を基準にして20:1〜1:20のモル比で反応させる、請求項1〜21の一つまたはそれ以上の方法。
- 塩基性触媒の存在下に行われる、請求項1〜22の一つまたはそれ以上の方法。
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