AU2012343935A1 - Method for producing and purifying salts of acrylamido-2-methylpropane sulfonic acid - Google Patents
Method for producing and purifying salts of acrylamido-2-methylpropane sulfonic acid Download PDFInfo
- Publication number
- AU2012343935A1 AU2012343935A1 AU2012343935A AU2012343935A AU2012343935A1 AU 2012343935 A1 AU2012343935 A1 AU 2012343935A1 AU 2012343935 A AU2012343935 A AU 2012343935A AU 2012343935 A AU2012343935 A AU 2012343935A AU 2012343935 A1 AU2012343935 A1 AU 2012343935A1
- Authority
- AU
- Australia
- Prior art keywords
- salt
- acrylamido
- process according
- methylpropanesulfonic acid
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 73
- QENRKQYUEGJNNZ-UHFFFAOYSA-N 2-methyl-1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical class CC(C)C(S(O)(=O)=O)NC(=O)C=C QENRKQYUEGJNNZ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 6
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 6
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims abstract description 5
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 20
- 238000002425 crystallisation Methods 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 159000000000 sodium salts Chemical class 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- -1 alkali metal salt Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 35
- 239000000047 product Substances 0.000 description 19
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 239000012535 impurity Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- BGIVXKVLORRHQX-UHFFFAOYSA-N 2-methylprop-1-ene-1-sulfonic acid Chemical compound CC(C)=CS(O)(=O)=O BGIVXKVLORRHQX-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920006158 high molecular weight polymer Polymers 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- MRXVCTWDXRBVLW-UHFFFAOYSA-N prop-2-enoylsulfamic acid Chemical compound OS(=O)(=O)NC(=O)C=C MRXVCTWDXRBVLW-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- GASMGDMKGYYAHY-UHFFFAOYSA-N 2-methylidenehexanamide Chemical compound CCCCC(=C)C(N)=O GASMGDMKGYYAHY-UHFFFAOYSA-N 0.000 description 1
- WTEXTEJRYNLGNC-UHFFFAOYSA-N 2-methylidenepropane-1,3-disulfonic acid Chemical compound OS(=O)(=O)CC(=C)CS(O)(=O)=O WTEXTEJRYNLGNC-UHFFFAOYSA-N 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BRXCDHOLJPJLLT-UHFFFAOYSA-N butane-2-sulfonic acid Chemical compound CCC(C)S(O)(=O)=O BRXCDHOLJPJLLT-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
- C07C309/15—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton the nitrogen atom of at least one of the amino groups being part of any of the groups, X being a hetero atom, Y being any atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11191117 | 2011-11-29 | ||
| EP11191117.8 | 2011-11-29 | ||
| PCT/EP2012/073791 WO2013079507A2 (de) | 2011-11-29 | 2012-11-28 | Verfahren zur herstellung und aufreinigung von salzen der acrylamido-2-methyl-propansulfonsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2012343935A1 true AU2012343935A1 (en) | 2014-07-03 |
Family
ID=47227809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012343935A Abandoned AU2012343935A1 (en) | 2011-11-29 | 2012-11-28 | Method for producing and purifying salts of acrylamido-2-methylpropane sulfonic acid |
Country Status (13)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748904A (zh) * | 2015-11-20 | 2017-05-31 | 中国石油化工股份有限公司 | 一种2-丙烯酰胺基-2-甲基丙磺酸盐类单体的制备及应用 |
| CN105693562A (zh) * | 2015-12-29 | 2016-06-22 | 四川光亚聚合物化工有限公司 | 一种2-丙烯酰胺基-2-甲基丙磺酸粗品的精制方法 |
| CN110857280B (zh) * | 2018-08-22 | 2022-06-03 | 潍坊金石环保科技有限公司 | 一种2-丙烯酰胺基-2-甲基丙磺酸盐的制备方法 |
| FR3114095B1 (fr) * | 2020-09-11 | 2023-07-14 | Snf Sa | Polymère d’acide 2-acrylamido-2-méthylpropane sulfonique ou de ses sels |
| FR3146690A1 (fr) | 2023-03-13 | 2024-09-20 | Snf Sa | Fluide de fracturation comprenant un polymère d’une forme cristalline du sel de sodium de l’acide 2-acrylamido-2-methylpropane sulfonique et procédé de fracturation hydraulique |
| FR3146689A1 (fr) | 2023-03-13 | 2024-09-20 | Snf Sa | Procédé de récupération assistée d’hydrocarbures utilisant un polymère d’une forme cristalline du sel de sodium de l’acide 2-acrylamido-2-methylpropane sulfonique |
| FR3146680A1 (fr) | 2023-03-13 | 2024-09-20 | Snf Sa | Forme cristalline du sel de sodium de l’acide 2-acrylamido-2-methylpropane sulfonique |
| FR3146679A1 (fr) * | 2023-03-13 | 2024-09-20 | Snf Sa | Forme cristalline du sel de potassium de l’acide 2-acrylamido-2-methylpropane sulfonique |
| FR3146673A1 (fr) | 2023-03-13 | 2024-09-20 | Snf Sa | Procédé de traitement d’une suspension de particules solides dans l’eau utilisant un polymère d’une forme cristalline du sel de sodium de l’acide 2-acrylamido-2-methylpropane sulfonique |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128631A (en) * | 1977-02-16 | 1978-12-05 | General Mills Chemicals, Inc. | Method of imparting lubricity to keratinous substrates and mucous membranes |
| FR2384751A1 (fr) * | 1977-03-23 | 1978-10-20 | Francaise Coop Pharma | Nouveaux derives de la taurine a activite neuro-musculaire renforcee |
| JPS54106427A (en) * | 1978-02-09 | 1979-08-21 | Nitto Chem Ind Co Ltd | Purification of 2-acrylamide-2-methylpropane sulfonic acid |
| JPS56103145A (en) * | 1980-01-21 | 1981-08-18 | Nissei Kagaku Kogyosho:Kk | Preparation of amide compound containing vinyl group |
| US4650614A (en) | 1980-02-21 | 1987-03-17 | Medtronic, Inc. | Refining of reaction grade 2-acrylamido-2-methylpropane sulfonic acid |
| JPS5973560A (ja) * | 1982-06-15 | 1984-04-25 | Nippon Paint Co Ltd | 重合性スルホベタイン化合物ならびにその製法 |
| JPS58225056A (ja) | 1982-06-24 | 1983-12-27 | Mitsui Toatsu Chem Inc | アミドアルカンスルホン酸誘導体の製造方法 |
| US4911855A (en) * | 1989-01-30 | 1990-03-27 | Gencorp Inc. | High magnetic strength magnets containing a flexible acrylate-amps binder |
| RO104626B1 (ro) * | 1989-05-03 | 1994-09-20 | Inst Chimii Macromolecular | Procedeu de purificare a monomerului acid 2-acriiamido-2- metilpropan-1-sulfonic |
| JPH0377860A (ja) * | 1989-08-21 | 1991-04-03 | Nissei Kagaku Kogyo Kk | ２―アクリルアミド―２―メチルプロパンスルホン酸の精製方法 |
| FI930345L (fi) * | 1991-06-03 | 1993-01-27 | Lubrizol Corp | Foerfarande foer framstaellning av renat akrylamidosulfonsyramonomerderivat |
| JP4178909B2 (ja) * | 2002-10-24 | 2008-11-12 | 東亞合成株式会社 | アクリルアミドアルカンスルホン酸溶液の製造方法 |
| JP2008071725A (ja) * | 2006-09-15 | 2008-03-27 | Sumitomo Bakelite Co Ltd | イオン伝導性電解質及び該イオン伝導性電解質を用いた二次電池 |
| JP4989241B2 (ja) * | 2007-01-29 | 2012-08-01 | 静岡県公立大学法人 | ［１８ｆ］標識化合物及びその製造方法、並びに［１８ｆ］標識リポソーム及び［１８ｆ］標識リポソーム製剤の製造方法 |
| CN101066940B (zh) * | 2007-06-06 | 2010-09-22 | 厦门长天企业有限公司 | 2-丙烯酰胺基-2-甲基丙磺酸的制备方法 |
| US8247601B2 (en) | 2007-12-06 | 2012-08-21 | Toagosei Co., Ltd. | 2-acrylamide-2-methylpropanesulfonic acid and process for producing the same |
| JP5609043B2 (ja) * | 2009-08-26 | 2014-10-22 | 東ソー株式会社 | 微粒径陰イオン交換樹脂及びその製造法、並びにそれを用いたジクロロブテンの製造方法 |
| CN102781921B (zh) * | 2009-08-28 | 2015-08-12 | 3M创新有限公司 | 包含可聚合离子液体混合物的组合物和制品及固化方法 |
-
2012
- 2012-11-28 EP EP12791486.9A patent/EP2785686B1/de not_active Not-in-force
- 2012-11-28 AU AU2012343935A patent/AU2012343935A1/en not_active Abandoned
- 2012-11-28 CA CA2857230A patent/CA2857230A1/en not_active Abandoned
- 2012-11-28 KR KR1020147014396A patent/KR20140099461A/ko not_active Ceased
- 2012-11-28 BR BR112014012918A patent/BR112014012918A2/pt not_active IP Right Cessation
- 2012-11-28 ES ES12791486.9T patent/ES2654554T3/es active Active
- 2012-11-28 MY MYPI2014001544A patent/MY165005A/en unknown
- 2012-11-28 JP JP2014543872A patent/JP6231010B2/ja not_active Expired - Fee Related
- 2012-11-28 WO PCT/EP2012/073791 patent/WO2013079507A2/de active Application Filing
- 2012-11-28 MX MX2014006249A patent/MX351176B/es active IP Right Grant
- 2012-11-28 CN CN201280068065.9A patent/CN104066714B/zh not_active Expired - Fee Related
- 2012-11-28 RU RU2014126224A patent/RU2619462C2/ru not_active IP Right Cessation
-
2014
- 2014-06-25 ZA ZA2014/04666A patent/ZA201404666B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX351176B (es) | 2017-10-04 |
| EP2785686B1 (de) | 2017-10-18 |
| WO2013079507A2 (de) | 2013-06-06 |
| JP6231010B2 (ja) | 2017-11-15 |
| RU2014126224A (ru) | 2016-01-27 |
| WO2013079507A3 (de) | 2013-08-22 |
| ZA201404666B (en) | 2015-12-23 |
| BR112014012918A2 (pt) | 2017-06-13 |
| CN104066714A (zh) | 2014-09-24 |
| MY165005A (en) | 2018-02-28 |
| KR20140099461A (ko) | 2014-08-12 |
| JP2015504441A (ja) | 2015-02-12 |
| CA2857230A1 (en) | 2013-06-06 |
| CN104066714B (zh) | 2016-10-26 |
| ES2654554T3 (es) | 2018-02-14 |
| MX2014006249A (es) | 2014-08-01 |
| RU2619462C2 (ru) | 2017-05-16 |
| EP2785686A2 (de) | 2014-10-08 |
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