JP6595472B2 - N−アシルアミノ酸塩を調製するためのプロセス - Google Patents
N−アシルアミノ酸塩を調製するためのプロセス Download PDFInfo
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- JP6595472B2 JP6595472B2 JP2016536289A JP2016536289A JP6595472B2 JP 6595472 B2 JP6595472 B2 JP 6595472B2 JP 2016536289 A JP2016536289 A JP 2016536289A JP 2016536289 A JP2016536289 A JP 2016536289A JP 6595472 B2 JP6595472 B2 JP 6595472B2
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- amino acid
- fatty acid
- salt
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- acid salt
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
200mLのParr社製ステンレス鋼製反応装置にラウリン酸メチル(70.0g、0.315mol)、グリシンナトリウム(31.0g、0.317mol)、ナトリウムメトキシド(30重量%メタノール溶液、10.8g、0.060mol、ラウリン酸メチルの量を基準として19モル%)を仕込み、メタノール(50g、出発物質の仕込み量を基準として33重量%)を加える。反応装置を密閉し、130℃に(50psigで)加熱し、200rpmで5時間撹拌する。反応混合物を室温に冷却し、圧力をゆっくりと開放する。得られた粉末を結晶皿に移し、一夜乾燥させることによって残留メタノールを除去する。水を加えて所望の濃度のN−ラウリルグリシン塩の水性混合物を得る。
1.溶媒としてエタノールまたはIPAを使用。反応をエタノールまたはイソプロパノール中で行い、次いで水性N−ラウリルグリシン塩混合物から余剰溶媒を除去(100℃、大気圧で約1時間)する。この方法は、溶媒を除去するために、ラウリルグリシンナトリウムに対する水を1.8:1(w:w)と少なくすることが必要である。
2.共沸剤としてエタノールまたはIPAを使用。反応をメタノール中で行うが、共沸(大気圧中、100℃で約2時間)溶媒としてほぼ等モル量のエタノールまたはイソプロパノールを加える。この方法は、溶媒を除去するために、ラウリルグリシンナトリウムに対する水を約2.5:1(w:w)として使用する。
3.水によるストリッピング。反応をメタノール中で行い、水のみを使用してメタノールをストリッピング(大気圧中、100℃で約2時間)する。この方法は、メタノールを除去するために、ラウリルグリシンナトリウムに対する水を約7:1(w:w)として使用する。
200mLのParr社製ステンレス鋼製反応装置にラウリン酸メチル(70.0g、0.315mol)、グリシンナトリウム(31.0g、0.317mol)、ナトリウムメトキシド(30重量%メタノール溶液、10.8g、0.060mol、ラウリン酸メチルの量を基準として19モル%)を仕込み、メタノール(50g、出発物質の仕込み量を基準として33重量%)を加える。反応装置を密閉して130℃に(50psigで)加熱し、200rpmで5時間撹拌する。反応混合物を室温に冷却し、圧力をゆっくりと開放する。
Steposol(登録商標)C−42(ラウリン酸メチル/ミリスチン酸メチル混合物)および表3に特定したアミノ酸の塩を使用し、全体として、上に記載したN−アシルグリシン塩を製造するための手順に従った。
Claims (10)
- C12〜C14N−アシルグリシン塩を含む組成物を製造するために、C12〜C14脂肪酸のメチルエステルを、前記メチルエステルの量を基準として少なくとも10モル%のC1〜C4アルコキシド触媒の存在下に、少なくとも5psigの圧力でアルカリ金属グリシン塩と反応させることを含むプロセス。
- 前記触媒がナトリウムメトキシド/メタノールである、請求項1に記載のプロセス。
- 前記触媒が12〜50モル%の範囲の量で使用される、請求項1に記載のプロセス。
- 前記反応が5psig〜50psigの範囲の圧力で行われる、請求項1に記載のプロセス。
- 前記反応が、グリセリンおよびプロピレングリコールからなる群から選択されるポリオールの存在下に行われる、請求項1に記載のプロセス。
- 前記反応が65℃〜200℃の範囲の温度で行われる、請求項1に記載のプロセス。
- 前記反応が、前記メチルエステルの量を基準として1〜200重量%の添加されたアルコール溶媒の存在下に行われる、請求項1に記載のプロセス。
- 前記反応が、40〜80重量%の前記アルコール溶媒の存在下に行われる、請求項7に記載のプロセス。
- 前記C12〜C14N−アシルグリシン塩組成物のC1〜C4アルコールスラリーを生成し、前記C12〜C14N−アシルグリシン塩を前記スラリーから回収し、前記C12〜C14N−アシルグリシン塩を乾燥させることにより、前記組成物中の未反応の出発物質から前記C12〜C14N−アシルグリシン塩を単離する、請求項1に記載のプロセス。
- 圧力が5psig〜30psigの範囲であり、温度が65℃〜100℃の範囲である、請求項1に記載のプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201361867500P | 2013-08-19 | 2013-08-19 | |
US61/867,500 | 2013-08-19 | ||
PCT/US2014/050219 WO2015026538A1 (en) | 2013-08-19 | 2014-08-07 | Process for preparing n-acyl amino acid salts |
Publications (2)
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JP2016528284A JP2016528284A (ja) | 2016-09-15 |
JP6595472B2 true JP6595472B2 (ja) | 2019-10-23 |
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JP2016536289A Active JP6595472B2 (ja) | 2013-08-19 | 2014-08-07 | N−アシルアミノ酸塩を調製するためのプロセス |
Country Status (9)
Country | Link |
---|---|
US (1) | US9593072B2 (ja) |
EP (1) | EP3036214B1 (ja) |
JP (1) | JP6595472B2 (ja) |
CN (1) | CN105531256B (ja) |
AR (1) | AR097387A1 (ja) |
BR (1) | BR112016003494B1 (ja) |
ES (1) | ES2670770T3 (ja) |
SG (1) | SG11201600835RA (ja) |
WO (1) | WO2015026538A1 (ja) |
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KR101880791B1 (ko) * | 2015-10-08 | 2018-07-20 | 주식회사 엘지생활건강 | 아실 글리시네이트 또는 이의 염의 합성 방법 및 이를 사용한 인체 세정제 조성물 |
CN106076192A (zh) * | 2016-06-30 | 2016-11-09 | 江南大学 | 一种制备脂肪酰基氨基酸类表面活性剂的方法 |
WO2019119337A1 (en) * | 2017-12-21 | 2019-06-27 | Rhodia Operations | Method for preparing primary diamines by kolbe electrolysis coupling reaction |
CN109369439B (zh) * | 2018-12-06 | 2021-04-16 | 盐城工学院 | 一种n-酰基氨基酸型表面活性剂的制备方法 |
CN112048048B (zh) * | 2020-09-16 | 2021-10-15 | 南京工业大学 | 一种聚氨酯发泡材料及其制备方法 |
CN112079761B (zh) * | 2020-09-22 | 2021-12-24 | 陕西科技大学 | 一种双酰胺非离子表面活性剂及其合成方法和应用 |
KR20230109149A (ko) | 2020-12-01 | 2023-07-19 | 바스프 에스이 | N-아실 아미노산 염을 포함하는 계면활성제 용액의 제조 방법 |
KR102464655B1 (ko) * | 2020-12-31 | 2022-11-07 | 노승호 | 알라닌계 계면활성제 조성물 및 이를 포함하는 인체 세정용 조성물 |
CN112812031B (zh) * | 2021-01-28 | 2023-01-31 | 常州大学 | 一种n-酰基氨基酸型表面活性剂的制备方法 |
CN116601139A (zh) * | 2021-06-08 | 2023-08-15 | 宝洁公司 | N-酰基氨基酸表面活性剂及其衍生物 |
MX2023006324A (es) * | 2021-06-08 | 2023-06-12 | Procter & Gamble | Mezclas de n-acil alaninatos y otros surfactantes de n-acil aminoacido y derivados de estos. |
CN115703716A (zh) * | 2021-08-03 | 2023-02-17 | Hg生化有限公司 | 生产氨基酸基表面活性剂的方法 |
CN114989030B (zh) * | 2022-07-06 | 2024-04-19 | 江苏东南纳米材料有限公司 | 一种n-月桂酰肌氨酸钠的制备方法 |
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-
2014
- 2014-08-07 EP EP14755276.4A patent/EP3036214B1/en active Active
- 2014-08-07 BR BR112016003494-5A patent/BR112016003494B1/pt active IP Right Grant
- 2014-08-07 ES ES14755276.4T patent/ES2670770T3/es active Active
- 2014-08-07 WO PCT/US2014/050219 patent/WO2015026538A1/en active Application Filing
- 2014-08-07 JP JP2016536289A patent/JP6595472B2/ja active Active
- 2014-08-07 SG SG11201600835RA patent/SG11201600835RA/en unknown
- 2014-08-07 CN CN201480045382.8A patent/CN105531256B/zh active Active
- 2014-08-19 AR ARP140103113A patent/AR097387A1/es active IP Right Grant
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2016
- 2016-02-05 US US15/017,465 patent/US9593072B2/en active Active
Also Published As
Publication number | Publication date |
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US9593072B2 (en) | 2017-03-14 |
WO2015026538A1 (en) | 2015-02-26 |
AR097387A1 (es) | 2016-03-09 |
CN105531256A (zh) | 2016-04-27 |
JP2016528284A (ja) | 2016-09-15 |
CN105531256B (zh) | 2017-11-07 |
BR112016003494B1 (pt) | 2021-02-09 |
BR112016003494A2 (pt) | 2020-04-14 |
EP3036214A1 (en) | 2016-06-29 |
ES2670770T3 (es) | 2018-06-01 |
SG11201600835RA (en) | 2016-03-30 |
EP3036214B1 (en) | 2018-02-28 |
US20160152555A1 (en) | 2016-06-02 |
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