JP2021526523A - 固体メチルグリシンジアセテート(mgda)アルカリ金属塩を製造する方法、及び固体粒子 - Google Patents
固体メチルグリシンジアセテート(mgda)アルカリ金属塩を製造する方法、及び固体粒子 Download PDFInfo
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- JP2021526523A JP2021526523A JP2020566631A JP2020566631A JP2021526523A JP 2021526523 A JP2021526523 A JP 2021526523A JP 2020566631 A JP2020566631 A JP 2020566631A JP 2020566631 A JP2020566631 A JP 2020566631A JP 2021526523 A JP2021526523 A JP 2021526523A
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- alkali metal
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- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000007787 solid Substances 0.000 title claims abstract description 27
- 229910052783 alkali metal Inorganic materials 0.000 title claims abstract description 21
- -1 Alkali Metal Salts Chemical class 0.000 title claims abstract description 17
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 title claims description 3
- 239000002245 particle Substances 0.000 title description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 239000002002 slurry Substances 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- PDIZYYQQWUOPPK-UHFFFAOYSA-N acetic acid;2-(methylamino)acetic acid Chemical compound CC(O)=O.CC(O)=O.CNCC(O)=O PDIZYYQQWUOPPK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 239000012452 mother liquor Substances 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 26
- 239000013078 crystal Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- IVWWFWFVSWOTLP-YVZVNANGSA-N (3'as,4r,7'as)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3ah-[1,3]dioxolo[4,5-c]pyran]-7'-one Chemical compound C([C@@H]1OC(O[C@@H]1C1=O)(C)C)O[C@]21COC(C)(C)O2 IVWWFWFVSWOTLP-YVZVNANGSA-N 0.000 claims 1
- 238000010586 diagram Methods 0.000 abstract 1
- CIEZZGWIJBXOTE-UHFFFAOYSA-N 2-[bis(carboxymethyl)amino]propanoic acid Chemical compound OC(=O)C(C)N(CC(O)=O)CC(O)=O CIEZZGWIJBXOTE-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 239000011734 sodium Substances 0.000 description 13
- 239000008187 granular material Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000013618 particulate matter Substances 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910017488 Cu K Inorganic materials 0.000 description 1
- 229910017541 Cu-K Inorganic materials 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- XYUPSBLFPTWJLC-VKHMYHEASA-N N-(carboxymethyl)-L-alanine Chemical compound OC(=O)[C@H](C)NCC(O)=O XYUPSBLFPTWJLC-VKHMYHEASA-N 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000007561 laser diffraction method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Abstract
Description
(A)50〜90℃の範囲の温度を有する前記MGDA塩の40〜60重量%水溶液を準備する工程、
(B)固体塩(a)を添加する工程、
(C)得られたスラリーを、工程(B)において添加した塩(a)が少なくとも部分的に溶解するまで加熱する工程、
(D)塩(a)を結晶化させる工程、
(E)母液から結晶塩(a)を取り出す工程
を含む方法に関する。
[CH3-CH(COO)-N(CH2-COO)2]M3-xHx (I)
(式中、
Mは、同じ又は異なるアルカリ金属カチオン、例えば、リチウム、ナトリウム、カリウム、ルビジウム、セシウムのカチオン、及び上記のうちの少なくとも2種の組合せから選択される)
による化合物から選択される。アルカリ金属カチオンの好ましい例は、ナトリウム及びカリウム、並びにナトリウムとカリウムの組合せである。
X線粉末回折計測定を、Bruker AXS(Karlsruhe)製のD8 Advance(登録商標)回折計で行った。Cu-Kを用いた反射において、一次側及び二次側で可変絞り調節を用いてα線を測定した。測定範囲は、2°〜80°の2シータ、ステップ幅は0.01°、角度ステップ当たりの測定時間は3.6秒であった。Bruker optics製ソフトウェアTOPASに基づき、(a)の2種の多形形態の相対量を決定した。
成分(a.2):MGDA-Na3(ラセミ型)、40重量%水溶液として供給、pH:13。
工程(A.1):オーバーヘッドスターラー、温度測定デバイス及び冷却器を備えた2Lの4つ口丸底フラスコに、545gの溶液に相当する成分(a.1)の40重量%溶液420mlを投入し、90℃に加熱した。
工程(A.2):オーバーヘッドスターラー、温度測定デバイス及び冷却器を備えた2Lの4つ口丸底フラスコに、545gの溶液に相当する成分(a.2)の40重量%溶液420mlを投入し、90℃に加熱した。
工程(A.3):オーバーヘッドスターラー、温度測定デバイス及び冷却器を備えた2Lの4つ口丸底フラスコに、545gの溶液に相当する成分(a.1)の40重量%溶液420mlを投入し、70℃に加熱した。
(SP.1)、(SP.2)、(SP.3)、及びC-(SP.4)のサンプルを7日間、35℃及び相対湿度70%で保存することにより、吸湿量を決定できる。重量増加が吸湿量に対応する。
Claims (8)
- 固体メチルグリシンジアセテート(MGDA)アルカリ金属塩(a)を製造する方法であって、
(A)50〜90℃の範囲の温度を有する前記MGDA塩の40〜60重量%水溶液を準備する工程、
(B)固体塩(a)を添加する工程、
(C)得られたスラリーを、工程(B)において添加した塩(a)が少なくとも部分的に溶解するまで加熱する工程、
(D)塩(a)を結晶化させる工程、及び
(E)母液から結晶塩(a)を取り出す工程
を含む、方法。 - 工程(C)において、得られたスラリーを透明な溶液が得られるまで加熱する、請求項1に記載の方法。
- 工程(E)が、ろ過によって、又は遠心分離器を用いて行われる、請求項1又は2に記載の方法。
- 塩(a)が、一般式(I)
[CH3-CH(COO)-N(CH2-COO)2]M3-xHx (I)
(式中、
Mは、同じ又は異なるアルカリ金属カチオンから選択され、
式中のxは、0〜1.0の範囲である)
による化合物から選択される、請求項1から3のいずれか一項に記載の方法。 - 工程(D)において、温度を20〜90℃低下させる、請求項1から4のいずれか一項に記載の方法。
- 塩(a)において、L-エナンチオマーが、0〜40%の範囲の鏡像体過剰率で存在する、請求項1から5のいずれか一項に記載の方法。
- 工程(D)からの母液の全て、又は一部をメチルグリシンジアセテート(MGDA)アルカリ金属塩(a)の水溶液に添加し、その濃度を35〜60重量%に調節する追加の工程(E)を含む、請求項1から6のいずれか一項に記載の方法。
- 工程(C)と(D)の間に、(a)の種晶が添加される、請求項1から7のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP18175104 | 2018-05-30 | ||
EP18175104.1 | 2018-05-30 | ||
PCT/EP2019/063042 WO2019228849A1 (en) | 2018-05-30 | 2019-05-21 | Process for making solid methylglycine diacetate (mgda) alkali metal salt, and solid particles |
Publications (1)
Publication Number | Publication Date |
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JP2021526523A true JP2021526523A (ja) | 2021-10-07 |
Family
ID=62492467
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JP2020566631A Pending JP2021526523A (ja) | 2018-05-30 | 2019-05-21 | 固体メチルグリシンジアセテート(mgda)アルカリ金属塩を製造する方法、及び固体粒子 |
Country Status (6)
Country | Link |
---|---|
US (1) | US12006277B2 (ja) |
EP (1) | EP3802481A1 (ja) |
JP (1) | JP2021526523A (ja) |
CN (1) | CN112166102A (ja) |
BR (1) | BR112020022158A2 (ja) |
WO (1) | WO2019228849A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2020127349A1 (en) * | 2018-12-21 | 2020-06-25 | Nouryon Chemicals International B.V. | Crumbly phase composition of methylglycine n,n diacetic acid |
CN115175895A (zh) * | 2020-02-20 | 2022-10-11 | 巴斯夫欧洲公司 | 制备固体甲基甘氨酸二乙酸碱金属盐的方法 |
WO2024046786A1 (en) * | 2022-08-29 | 2024-03-07 | Basf Se | Process for preparing a solid composition comprising at least one aminocarboxylate complexing agent |
Citations (1)
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WO2017102483A1 (en) * | 2015-12-17 | 2017-06-22 | Basf Se | Process for making a crystalline alkali metal salt of a complexing agent, and crystalline complexing agent |
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FR2756675B1 (fr) | 1996-11-29 | 1999-02-19 | Bardin Etablissements | Dispositif de detection et de mesure de defaut sur lignes d'alimentation electrique |
DE19649681A1 (de) | 1996-11-29 | 1998-06-04 | Basf Ag | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
DE102005021056A1 (de) | 2005-05-06 | 2006-11-09 | Basf Ag | Verfahren zur Isolierung von Methylglycinnitril-N,N-diacetonitrilen aus einem wässrigen Rohgemisch |
DE102009038951A1 (de) | 2009-08-26 | 2011-03-03 | Inprotec Ag | Verfahren zur Herstellung eines kristallinen Feststoffes aus Glycin-N,N-diessigsäure-Derivaten mit hinreichend geringer Hygroskopizität |
US8754026B2 (en) | 2010-09-27 | 2014-06-17 | Basf Se | Process for producing granules comprising one or more complexing agent salts |
US9227915B2 (en) * | 2011-05-03 | 2016-01-05 | Basf Se | Process for the preparation of a crystalline L-MGDA trialkali metal salt |
MX2013012811A (es) | 2011-05-03 | 2014-02-10 | Basf Se | Procedimiento para preparar una sal trialcalinometalica cristalina de l-mgda. |
JP7098644B2 (ja) | 2017-02-24 | 2022-07-11 | ビーエーエスエフ ソシエタス・ヨーロピア | 固体メチルグリシン二酢酸(mgda)アルカリ金属塩の製造方法、及び固体粒子 |
-
2019
- 2019-05-21 EP EP19724519.4A patent/EP3802481A1/en active Pending
- 2019-05-21 US US17/059,540 patent/US12006277B2/en active Active
- 2019-05-21 CN CN201980035724.0A patent/CN112166102A/zh active Pending
- 2019-05-21 JP JP2020566631A patent/JP2021526523A/ja active Pending
- 2019-05-21 BR BR112020022158-9A patent/BR112020022158A2/pt unknown
- 2019-05-21 WO PCT/EP2019/063042 patent/WO2019228849A1/en unknown
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WO2017102483A1 (en) * | 2015-12-17 | 2017-06-22 | Basf Se | Process for making a crystalline alkali metal salt of a complexing agent, and crystalline complexing agent |
Non-Patent Citations (1)
Title |
---|
平山令明, 有機化合物結晶作製ハンドブック, JPN6014035600, 2008, pages 17 - 23, ISSN: 0005052508 * |
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Publication number | Publication date |
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US20210206712A1 (en) | 2021-07-08 |
BR112020022158A2 (pt) | 2021-01-26 |
WO2019228849A1 (en) | 2019-12-05 |
CN112166102A (zh) | 2021-01-01 |
EP3802481A1 (en) | 2021-04-14 |
US12006277B2 (en) | 2024-06-11 |
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