公开(公告)号：US09593072B2

公开(公告)日：2017-03-14

申请号：US15017465

申请日：2016-02-05

Applicant: STEPAN COMPANY

Inventor： Bing Wang ,  Gregory P. Dado

IPC: C07C231/02 ,  C07D233/64 ,  C07D207/16 ,  C07C233/47

CPC classification number: C07C231/02 ,  C07C233/47 ,  C07D207/16 ,  C07D233/64 ,  C07C237/22

Abstract: N-Acyl amino acid salt compositions and an improved process for making them from fatty alkyl esters are disclosed. The process comprises reacting a fatty alkyl ester with an amino acid salt in the presence of an alkoxide catalyst at a pressure of at least 5 psig. At least 10 mole percent of catalyst is used based on the amount of fatty alkyl ester used as a reactant. Pressure and a minimum level of alkoxide catalyst are needed to give high fatty alkyl ester conversions and good yields of the desired N-acyl amino acid salt. The resulting N-acyl amino acid salt compositions have low color, an acceptable level of fatty acid soaps, and a small proportion of di-acylated by-products. Single-phase mixtures produced by combining various amino acid salts with glycinates, or by using an excess of either the fatty alkyl ester or amino acid salt, promote high conversions when the mixtures are reacted to give the desired N-acyl amino acid salt.

Abstract translation: 公开了N-酰基氨基酸盐组合物和由脂肪烷基酯制备它们的改进方法。 该方法包括在烷氧基催化剂存在下，在至少5psig的压力下使脂肪烷基酯与氨基酸盐反应。 基于用作反应物的脂肪烷基酯的量，使用至少10摩尔％的催化剂。 需要压力和最低水平的醇盐催化剂以产生高脂肪烷基酯转化率和所需N-酰基氨基酸盐的良好产率。 所得N-酰基氨基酸盐组合物具有低颜色，可接受水平的脂肪酸皂和少量二酰化副产物。 通过将各种氨基酸盐与甘氨酸盐组合或通过使用过量的脂肪烷基酯或氨基酸盐产生的单相混合物在混合物反应得到所需的N-酰基氨基酸盐时促进高转化率。

公开(公告)号：US20150126776A1

公开(公告)日：2015-05-07

申请号：US14411971

申请日：2013-06-27

Applicant: Stepan Company

Inventor： Bing Wang ,  Gregory P Dado

IPC: C07C233/91 ,  C07C231/10

CPC classification number: C07C233/91 ,  C07C231/02 ,  C07C231/10 ,  C07C233/47

Abstract: Improved processes for making an N-acyl amino acid salt from a fatty alkyl ester or a polyol ester are disclosed. Each process uses a polyol selected from glycerin or propylene glycol in an amount effective to keep the reaction mixture fluid until conversion to the N-acyl amino acid salt reaches the desired level of completion. In one process, a fatty alkyl ester reacts with an amino acid salt in the presence of glycerin or propylene glycol to produce an N-acyl amino acid salt. In another process, a polyol ester reacts with the amino acid salt in the presence of added glycerin or propylene glycol to produce the N-acyl amino acid salt. We surprisingly found that an effective amount of glycerin or propylene glycol minimizes or eliminates reaction mixture solidification or foaming, reduces color, and minimizes the level of di- and tripeptide by-products. In a related process, water is added when conversion of the amino acid salt to the N-acyl amino acid salt is in the range of 50 to 90 mole %. Water addition improves processability, advances conversion without producing excessive soap, and helps to ensure that the N-acyl amino acid salt will have low color and a small proportion of by-products.

Abstract translation: 公开了从脂肪烷基酯或多元醇酯制备N-酰基氨基酸盐的改进方法。 每个方法使用选自甘油或丙二醇的多元醇，其量可以有效地保持反应混合物流体，直到转化成N-酰基氨基酸盐达到所需的完成水平。 在一个过程中，脂肪烷基酯在甘油或丙二醇的存在下与氨基酸盐反应以产生N-酰基氨基酸盐。 在另一方法中，多元醇酯在加入的甘油或丙二醇的存在下与氨基酸盐反应以产生N-酰基氨基酸盐。 我们惊奇地发现，有效量的甘油或丙二醇使反应混合物固化或发泡最小化或消除，减少颜色，并使二肽和三肽副产物的水平最小化。 在相关方法中，当氨基酸盐转化为N-酰基氨基酸盐时，加入水是在50至90摩尔％的范围内。 添加水可改善加工性能，不会产生过量的肥皂进行转化，有助于确保N-酰基氨基酸盐具有低颜色和少量的副产物。

公开(公告)号：US20160152555A1

公开(公告)日：2016-06-02

申请号：US15017465

申请日：2016-02-05

Applicant: STEPAN COMPANY

Inventor： Bing Wang ,  Gregory P. Dado

IPC: C07C231/02 ,  C07C233/47

CPC classification number: C07C231/02 ,  C07C233/47 ,  C07D207/16 ,  C07D233/64 ,  C07C237/22

Abstract: N-Acyl amino acid salt compositions and an improved process for making them from fatty alkyl esters are disclosed. The process comprises reacting a fatty alkyl ester with an amino acid salt in the presence of an alkoxide catalyst at a pressure of at least 5 psig. At least 1 0 mole percent of catalyst is used based on the amount of fatty alkyl ester used as a reactant. Pressure and a minimum level of alkoxide catalyst are needed to give high fatty alkyl ester conversions and good yields of the desired N-acyl amino acid salt. The resulting N-acyl amino acid salt compositions have low color, an acceptable level of fatty acid soaps, and a small proportion of di-acylated by-products. Single-phase mixtures produced by combining various amino acid salts with glycinates, or by using an excess of either the fatty alkyl ester or amino acid salt, promote high conversions when the mixtures are reacted to give the desired N-acyl amino acid salt.

Abstract translation: 公开了N-酰基氨基酸盐组合物和由脂肪烷基酯制备它们的改进方法。 该方法包括在烷氧基催化剂存在下，在至少5psig的压力下使脂肪烷基酯与氨基酸盐反应。 基于用作反应物的脂肪烷基酯的量，使用至少10摩尔％的催化剂。 需要压力和最低水平的醇盐催化剂以产生高脂肪烷基酯转化率和所需N-酰基氨基酸盐的良好产率。 所得N-酰基氨基酸盐组合物具有低颜色，可接受水平的脂肪酸皂和少量二酰化副产物。 通过将各种氨基酸盐与甘氨酸盐组合或通过使用过量的脂肪烷基酯或氨基酸盐产生的单相混合物在混合物反应得到所需的N-酰基氨基酸盐时促进高转化率。

公开(公告)号：US09156777B2

公开(公告)日：2015-10-13

申请号：US14411971

申请日：2013-06-27

Applicant: Stepan Company

Inventor： Bing Wang ,  Gregory P Dado

IPC: C07C233/91 ,  C07C231/02 ,  C07C231/10

CPC classification number: C07C233/91 ,  C07C231/02 ,  C07C231/10 ,  C07C233/47

Abstract: Improved processes for making an N-acyl amino acid salt from a fatty alkyl ester or a polyol ester are disclosed. Each process uses a polyol selected from glycerin or propylene glycol in an amount effective to keep the reaction mixture fluid until conversion to the N-acyl amino acid salt reaches the desired level of completion. In one process, a fatty alkyl ester reacts with an amino acid salt in the presence of glycerin or propylene glycol to produce an N-acyl amino acid salt. In another process, a polyol ester reacts with the amino acid salt in the presence of added glycerin or propylene glycol to produce the N-acyl amino acid salt. We surprisingly found that an effective amount of glycerin or propylene glycol minimizes or eliminates reaction mixture solidification or foaming, reduces color, and minimizes the level of di- and tripeptide by-products. In a related process, water is added when conversion of the amino acid salt to the N-acyl amino acid salt is in the range of 50 to 90 mole %. Water addition improves processability, advances conversion without producing excessive soap, and helps to ensure that the N-acyl amino acid salt will have low color and a small proportion of by-products.

Abstract translation: 公开了从脂肪烷基酯或多元醇酯制备N-酰基氨基酸盐的改进方法。 每个方法使用选自甘油或丙二醇的多元醇，其量可以有效地保持反应混合物流体，直到转化成N-酰基氨基酸盐达到所需的完成水平。 在一个过程中，脂肪烷基酯在甘油或丙二醇的存在下与氨基酸盐反应以产生N-酰基氨基酸盐。 在另一方法中，多元醇酯在加入的甘油或丙二醇的存在下与氨基酸盐反应以产生N-酰基氨基酸盐。 我们惊奇地发现，有效量的甘油或丙二醇使反应混合物固化或发泡最小化或消除，减少颜色，并使二肽和三肽副产物的水平最小化。 在相关方法中，当氨基酸盐转化为N-酰基氨基酸盐时，加入水是在50至90摩尔％的范围内。 添加水可改善加工性能，不会产生过量的肥皂进行转化，有助于确保N-酰基氨基酸盐具有低颜色和少量的副产物。