(US10590064) Crystals of alanine N-acetic acid precursors, process to prepare them and their use 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(US10590064) Crystals of alanine N-acetic acid precursors, process to prepare them and their use
公开号/公开日
US10590064 US20170334833 / 2020-03-17 2017-11-23
申请号/申请日
US15/538,559 / 2015-12-21
发明人
BOUWMAN ALBERTUS JACOBUS MARIAJONGEN HUBERTUS JOHANNESDOPPEN ROY GÉRARDHEUS MARTINSCHOMAKER ELWIN;
申请人
NOURYON CHEMICALS INTERNATIONAL;
主分类号
IPC分类号
C07C-227/26 C07C-231/24 C07C-237/06 C07C-253/30 C07C-253/34 C07C-255/25
摘要
(US10590064) The present invention relates to alanine N-acetic acid precursors of formula (i) COOM-CH(CH3)—NH—(CH2CN), wherein M is hydrogen (alanine N-monoacetonitrile), or (ii) COOM-CH(CH3)—N—(CH2CN)2, wherein 0 to 50% of all M is sodium or potassium and 50 to 100% of all M is hydrogen (alanine N,N-diacetonitrile and its partial sodium or potassium salts) comprising L-alanine to D-alanine in a range of from 75:25 to 50:50 (L:D), or (iii) COOM-CH(CH3)—N—(CH2CONH2)2, wherein M is hydrogen (alanine N,N-diacetamide), in the form of crystals, and relates to a process to prepare these precursors and their use, especially to give MGMA or MGDA.
机翻摘要
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地址
代理人
(US10590064) Lorenz & Kopf, LLP
代理机构
;
优先权号
2014EP-0200045 2015WO-EP80837
主权利要求
(US10590064) The invention claimed is: 1. An alanine N-acetic acid precursor selected from the group consisting of:   (a) alanine N-monoacetonitrile of formula COOM-CH(CH3)—NH—(CH2CN), wherein M is hydrogen, said alanine N-monoacetonitrile showing X-ray diffraction reflections at 28=13.3; 20.3; 21.4; 21.9; 24.0 with an accuracy of ±0.1,   (b) alanine N,N-diacetonitrile and its partial sodium salts of formula COOM-CH(CH3)—N—(CH2CN)2, wherein greater than 0 to 50% of all M is sodium and 50 to less than 100% of all M is hydrogen comprising L-alanine N,N-diacetonitrile to D-alanine N,N-diacetonitrile, or their respective partial sodium salts, in a range of from 75:25 to 50:50 (L:D), said alanine N,N-diacetonitrile partial sodium salts showing X-ray diffraction reflections at 28=7.1; 10.8; 14.3; 14.8; 18.2; 20.7; 21.0; 23.3 with an accuracy of ±0.1, and   (c) alanine N,N-diacetamide of formula COOM-CH(CH3)—N—(CH2CONH2)2, wherein M is hydrogen,    and wherein the precursors is in the form of crystals that exhibit interference in monochromatic X-ray diffraction which fulfills the Bragg equation 2d sin θ=nλ. 2. The alanine N-monoacetonitrile or alanine N,N-diacetamide precursor of claim 1 comprising L-alanine N-monoacetonitrile to D-alanine N-monoacetonitrile, or, L-alanine N,N-diacetamide to D-alanine N,N-diacetamide, respectively, in a range of from 75:25 to 50:50 (L:D). 3. Process to prepare the precursors according to claim 1, comprising:   a first step providing an aqueous solution of the alanine N-acetic acid precursor;   optionally for the alanine N monoacetonitrile or alanine N,N diacetamide precursor, a second step ensuring the alanine is at least partly racemized, one step after the other in random order or simultaneously, and   a third step allowing the aqueous solution to crystallize. 4. Process of claim 3, wherein in the first step the alanine N-acetic acid precursor is made by reacting alanine or partially neutralized alanine with 0.8-2.4 molar equivalents of formaldehyde and 0.8-2.4 molar equivalents of hydrogen cyanide, wherein the reaction takes place by simultaneous dosing of both the formaldehyde and the hydrogen cyanide, or by dosing at least 40% of the amount of formaldehyde before dosing of the hydrogen cyanide is started. 5. Process according to claim 3, wherein the second step includes a concentrating step that is carried out until the solution has a concentration of equal to or more than 15 wt % to up to or equal to 80 wt % of the precursor, based on the weight of the aqueous solution. 6. Process according to claim 3, wherein the third step comprises crystallization by allowing the solution to stand for an extended period of time and/or cooling and/or seeding. 7. Process according to claim 3, wherein the third step comprises crystallization by spraying the aqueous solution of the second step on seeding crystals. 8. Process according to claim 3, wherein the third step is performed at a temperature of below 40° C. 9. Process according to claim 3, wherein the process is a continuous process. 10. Process for preparing methylglycine N-acetic acid (MGMA) or methylglycine N,N-diacetic acid (MGDA) comprising the steps of adding together the precursors of claim 1 and an alkali metal salt in an aqueous solution and heating this solution to a temperature of at least 80° C. 11. The alanine N-acetic acid precursor in crystal form of claim 1 that is alanine N-monoacetonitrile showing X-ray diffraction reflections at 2θ=13.3; 20.3; 21.4; 21.9; 24.0 with an accuracy of ±0.1. 12. The alanine N-acetic acid precursor in crystal form of claim 1 that is alanine N,N-diacetonitrile showing X-ray diffraction reflections at 2θ=6.9; 10.2; 13.8; 14.1; 16.5; 17.3; 19.3 with an accuracy of ±0.1. 13. The alanine N-acetic acid precursor in crystal form of claim 1 that is alanine N,N-diacetonitrile sodium salt showing X-ray diffraction reflections at 2θ=7.1; 10.8; 14.3; 14.8; 18.2; 20.7; 21.0; 23.3 with an accuracy of ±0.1. 14. The alanine N-acetic acid precursor in crystal form of claim 1 that is D,L-alanine diacetonitrile having the X-ray powder diffractogram of FIG. 1. 15. The alanine N-acetic acid precursor in crystal form of claim 1 that is D,L-alanine monoacetonitrile having the X-ray powder diffractogram of FIG. 2. 16. The alanine N-acetic acid precursor in crystal form of claim 1 that is D,L-alanine diacetonitrile sodium salt having the X-ray powder diffractogram of FIG. 3.
法律状态
GRANTED
专利类型码
B2 A1
国别省市代码
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