FI122829B - Menetelmä kelatointiaineiden seoksen valmistamiseksi - Google Patents
Menetelmä kelatointiaineiden seoksen valmistamiseksi Download PDFInfo
- Publication number
- FI122829B FI122829B FI20105622A FI20105622A FI122829B FI 122829 B FI122829 B FI 122829B FI 20105622 A FI20105622 A FI 20105622A FI 20105622 A FI20105622 A FI 20105622A FI 122829 B FI122829 B FI 122829B
- Authority
- FI
- Finland
- Prior art keywords
- maleate
- acid
- lanthanum
- diethanolamine
- aspartic acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000002738 chelating agent Substances 0.000 title description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 37
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 37
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 19
- 235000003704 aspartic acid Nutrition 0.000 claims description 18
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 18
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 18
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 14
- 150000002602 lanthanoids Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- AMSHPZWQWXOVTH-UHFFFAOYSA-N 2,3-diethoxybutanedioic acid Chemical compound CCOC(C(O)=O)C(C(O)=O)OCC AMSHPZWQWXOVTH-UHFFFAOYSA-N 0.000 claims description 7
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001341 alkaline earth metal compounds Chemical class 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- KDEPHUOMBPVSRY-AHUNZLEGSA-H (Z)-but-2-enedioate lanthanum(3+) Chemical compound [La+3].[La+3].[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O KDEPHUOMBPVSRY-AHUNZLEGSA-H 0.000 claims description 2
- 229910017569 La2(CO3)3 Inorganic materials 0.000 claims description 2
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001413 alkali metal ion Chemical group 0.000 claims description 2
- 229910001420 alkaline earth metal ion Chemical group 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical group [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- NZPIUJUFIFZSPW-UHFFFAOYSA-H lanthanum carbonate Chemical compound [La+3].[La+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O NZPIUJUFIFZSPW-UHFFFAOYSA-H 0.000 claims description 2
- 229960001633 lanthanum carbonate Drugs 0.000 claims description 2
- CZMAIROVPAYCMU-UHFFFAOYSA-N lanthanum(3+) Chemical class [La+3] CZMAIROVPAYCMU-UHFFFAOYSA-N 0.000 claims description 2
- NFGMTENHSQDVJW-UHFFFAOYSA-K lanthanum(3+);octanoate Chemical compound [La+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O NFGMTENHSQDVJW-UHFFFAOYSA-K 0.000 claims description 2
- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 claims description 2
- ICAKDTKJOYSXGC-UHFFFAOYSA-K lanthanum(iii) chloride Chemical compound Cl[La](Cl)Cl ICAKDTKJOYSXGC-UHFFFAOYSA-K 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- CDHWCJMYBKNDSW-DKWTVANSSA-N (2S)-2-aminobutanedioic acid butanedioic acid Chemical compound OC(=O)CCC(O)=O.N[C@@H](CC(O)=O)C(O)=O CDHWCJMYBKNDSW-DKWTVANSSA-N 0.000 claims 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims 1
- YIKPWSKEXRZQIY-UHFFFAOYSA-N butanedioic acid;ethane-1,2-diamine Chemical compound NCCN.OC(=O)CCC(O)=O.OC(=O)CCC(O)=O YIKPWSKEXRZQIY-UHFFFAOYSA-N 0.000 claims 1
- JCXNPKNKZALDRK-UHFFFAOYSA-N butanedioic acid;ethene Chemical compound C=C.C=C.OC(=O)CCC(O)=O JCXNPKNKZALDRK-UHFFFAOYSA-N 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229960005261 aspartic acid Drugs 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000011976 maleic acid Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- -1 1,2-dicarboxyethoxy Chemical group 0.000 description 8
- NXQLETUDPAVCIE-WNQIDUERSA-N C(C)OC(C(C(=O)O)OCC)C(=O)O.N[C@@H](CC(=O)O)C(=O)O Chemical compound C(C)OC(C(C(=O)O)OCC)C(=O)O.N[C@@H](CC(=O)O)C(=O)O NXQLETUDPAVCIE-WNQIDUERSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- 239000001384 succinic acid Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000004076 pulp bleaching Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BZZLZISANHDNBA-ODZAUARKSA-N (Z)-but-2-enedioic acid ethane-1,2-diamine Chemical compound NCCN.OC(=O)\C=C/C(O)=O BZZLZISANHDNBA-ODZAUARKSA-N 0.000 description 1
- KJXMXCRSMLOXBM-UHFFFAOYSA-N 2,3-diethylbutanedioic acid Chemical compound CCC(C(O)=O)C(CC)C(O)=O KJXMXCRSMLOXBM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052692 Dysprosium Inorganic materials 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 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 1
- 229910052779 Neodymium Inorganic materials 0.000 description 1
- 229910052777 Praseodymium Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001509 aspartic acid derivatives Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- CUHPRGKYCZJTSQ-UHFFFAOYSA-N diethyl butanediperoxoate Chemical compound CCOOC(=O)CCC(=O)OOCC CUHPRGKYCZJTSQ-UHFFFAOYSA-N 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002601 lanthanoid compounds Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000005474 octanoate group Chemical class 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C229/24—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 more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
-
- 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
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/10—Formation of amino groups in compounds containing carboxyl groups with simultaneously increasing the number of carbon atoms in the carbon skeleton
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- 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
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
-
- 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
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- 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
- C07C229/26—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 more than one amino group bound to the carbon skeleton, e.g. lysine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20105622A FI122829B (fi) | 2010-06-02 | 2010-06-02 | Menetelmä kelatointiaineiden seoksen valmistamiseksi |
| RU2012154341/04A RU2551285C2 (ru) | 2010-06-02 | 2011-05-31 | Способ получения смеси хелатирующих агентов |
| ES11728021T ES2531186T3 (es) | 2010-06-02 | 2011-05-31 | Proceso para preparar una mezcla de agentes quelantes |
| US13/639,575 US9090536B2 (en) | 2010-06-02 | 2011-05-31 | Process for the preparation of a mixture of chelating agents |
| EP11728021.4A EP2576499B1 (de) | 2010-06-02 | 2011-05-31 | Verfahren für die zubereitung einer mischung aus chelatbildnern |
| BR112012030778-9A BR112012030778B1 (pt) | 2010-06-02 | 2011-05-31 | Processo para a preparação de uma mistura de agentes quelantes |
| PL11728021T PL2576499T3 (pl) | 2010-06-02 | 2011-05-31 | Sposób otrzymywania mieszaniny środków chelatujących |
| CN201180025787.1A CN102933544B (zh) | 2010-06-02 | 2011-05-31 | 螯合剂混合物的制备方法 |
| PCT/FI2011/050504 WO2011151517A2 (en) | 2010-06-02 | 2011-05-31 | Process for the preparation of a mixture of chelating agents |
| CA2801340A CA2801340C (en) | 2010-06-02 | 2011-05-31 | Process for the preparation of a mixture of chelating agents |
| CL2012003352A CL2012003352A1 (es) | 2010-06-02 | 2012-11-29 | Proceso para la preparacion de una mezcla de dietoxi succinato de acido aspartico y un aminoacido que comprende hacer reaccionar maleato con dietanolamina en condiciones alcalinas en presencia de catalizador lantanoide |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI20105622A FI122829B (fi) | 2010-06-02 | 2010-06-02 | Menetelmä kelatointiaineiden seoksen valmistamiseksi |
| FI20105622 | 2010-06-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI20105622A0 FI20105622A0 (fi) | 2010-06-02 |
| FI20105622L FI20105622L (fi) | 2011-12-03 |
| FI122829B true FI122829B (fi) | 2012-07-31 |
Family
ID=42308080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI20105622A FI122829B (fi) | 2010-06-02 | 2010-06-02 | Menetelmä kelatointiaineiden seoksen valmistamiseksi |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9090536B2 (de) |
| EP (1) | EP2576499B1 (de) |
| CN (1) | CN102933544B (de) |
| BR (1) | BR112012030778B1 (de) |
| CA (1) | CA2801340C (de) |
| CL (1) | CL2012003352A1 (de) |
| ES (1) | ES2531186T3 (de) |
| FI (1) | FI122829B (de) |
| PL (1) | PL2576499T3 (de) |
| RU (1) | RU2551285C2 (de) |
| WO (1) | WO2011151517A2 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447370B (zh) * | 2014-04-03 | 2015-09-23 | 石家庄开发区德赛化工有限公司 | 一种亚氨基二琥珀酸盐螯合剂的制备方法 |
| BR112017006799B1 (pt) | 2014-10-17 | 2021-11-23 | Halliburton Energy Services, Inc | Método de tratamento de uma formação subterrânea, processo para a síntese de um composto, e, sistema para realizar o método |
| RU2585020C1 (ru) * | 2015-06-16 | 2016-05-27 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Тверской государственный университет" | Способ получения комплексообразующего сорбента |
| WO2018004606A1 (en) | 2016-06-30 | 2018-01-04 | Halliburton Energy Services, Inc. | Sulfonated iminodialkanoic acids formed from an iminodialkylnitrile and a sultone and methods for use thereof |
| CN107162748A (zh) * | 2017-06-13 | 2017-09-15 | 山东远联化工有限公司 | 一种增效剂yl‑101及其应用 |
| RU2761831C2 (ru) * | 2017-06-30 | 2021-12-13 | Кемира Ойй | Способ получения смеси хелатообразующих агентов, смесь хелатообразующих агентов и способы ее применения |
| CA3067494A1 (en) | 2017-06-30 | 2019-01-03 | Kemira Oyj | Process for the preparation of a mixture of chelating agents, mixture of chelating agents and methods of using them |
| CN111393313A (zh) * | 2020-04-16 | 2020-07-10 | 河北协同环保科技股份有限公司 | 一种亚氨基二琥珀酸盐生产中提高转化率的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1710552A1 (ru) * | 1990-04-28 | 1992-02-07 | Тверской государственный университет | Способ получени солей комплексонов |
| JPH09143132A (ja) | 1995-11-21 | 1997-06-03 | Fuji Photo Film Co Ltd | アミン類とα， β−不飽和化合物の付加生成物の製造方法 |
| FI112075B (fi) * | 1996-05-30 | 2003-10-31 | Kemira Chemicals Oy | N-bis- tai N-tris-[(1,2-dikarboksyyli-etoksi)-etyyli]amiinijohdannaiset, niiden valmistus ja käyttö |
| FI105932B (fi) * | 1996-05-30 | 2000-10-31 | Kemira Chemicals Oy | Menetelmä korkeasaanto- tai kierrätysmassan valkaisemiseksi |
| FI106258B (fi) * | 1998-03-09 | 2000-12-29 | Kemira Chemicals Oy | Menetelmiä N-bis-[2-(1,2-dikarboksi-etoksi)-etyyli]amiinijohdannaisen valmistamiseksi sekä menetelmien tuotteet ja niiden käytöt |
| FI117392B (fi) | 1999-03-02 | 2006-09-29 | Kemira Oyj | Monivaiheinen valkaisumenetelmä kemiallisen selluloosamassan valkaisemiseksi |
| EP1086944B1 (de) * | 1999-09-03 | 2005-05-25 | Nippon Shokubai Co., Ltd. | Zusammensetzung von Aminosäurederivaten und Verfahren zur Herstellung von einem Aminosäurederivat |
-
2010
- 2010-06-02 FI FI20105622A patent/FI122829B/fi active
-
2011
- 2011-05-31 EP EP11728021.4A patent/EP2576499B1/de active Active
- 2011-05-31 CN CN201180025787.1A patent/CN102933544B/zh not_active Expired - Fee Related
- 2011-05-31 US US13/639,575 patent/US9090536B2/en not_active Expired - Fee Related
- 2011-05-31 WO PCT/FI2011/050504 patent/WO2011151517A2/en not_active Ceased
- 2011-05-31 PL PL11728021T patent/PL2576499T3/pl unknown
- 2011-05-31 RU RU2012154341/04A patent/RU2551285C2/ru active
- 2011-05-31 ES ES11728021T patent/ES2531186T3/es active Active
- 2011-05-31 CA CA2801340A patent/CA2801340C/en active Active
- 2011-05-31 BR BR112012030778-9A patent/BR112012030778B1/pt not_active IP Right Cessation
-
2012
- 2012-11-29 CL CL2012003352A patent/CL2012003352A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102933544B (zh) | 2014-09-17 |
| CN102933544A (zh) | 2013-02-13 |
| CL2012003352A1 (es) | 2013-07-12 |
| PL2576499T3 (pl) | 2015-04-30 |
| US20130204035A1 (en) | 2013-08-08 |
| RU2551285C2 (ru) | 2015-05-20 |
| ES2531186T3 (es) | 2015-03-11 |
| FI20105622A0 (fi) | 2010-06-02 |
| RU2012154341A (ru) | 2014-07-20 |
| BR112012030778A2 (pt) | 2017-12-05 |
| EP2576499B1 (de) | 2014-12-03 |
| CA2801340C (en) | 2017-06-27 |
| FI20105622L (fi) | 2011-12-03 |
| EP2576499A2 (de) | 2013-04-10 |
| BR112012030778B1 (pt) | 2018-07-31 |
| CA2801340A1 (en) | 2011-12-08 |
| US9090536B2 (en) | 2015-07-28 |
| WO2011151517A3 (en) | 2012-03-22 |
| WO2011151517A2 (en) | 2011-12-08 |
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