JPH0474159A - Production of 2-acrylamido-2-methylpropanesulfonic acid - Google Patents
Production of 2-acrylamido-2-methylpropanesulfonic acidInfo
- Publication number
- JPH0474159A JPH0474159A JP18445990A JP18445990A JPH0474159A JP H0474159 A JPH0474159 A JP H0474159A JP 18445990 A JP18445990 A JP 18445990A JP 18445990 A JP18445990 A JP 18445990A JP H0474159 A JPH0474159 A JP H0474159A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- acrylonitrile
- organic carboxylic
- carboxylic acid
- anhydride
- 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.)
- Granted
Links
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Acrylamido-2-methylpropane sulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 title 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 2
- 229920002972 Acrylic fiber Polymers 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 229920000867 polyelectrolyte Polymers 0.000 abstract 1
Classifications
-
- 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
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
Abstract
PURPOSE: To improve the purity and yield by reacting acrylonitrile with nitric acid and isobutylene in the presence of a specific compound in carrying out the aforementioned reaction and obtaining the subject compound useful as a polyelectrolyte for coloring improver, etc., of acrylic fiber.
CONSTITUTION: Acrylonitrile is reacted with sulfuric acid at ≥95% concentration and isobutylene in the presence of an organic carboxylic acid or an anhydride thereof at -10 to +70°C, preferably 30-50°C to afford the objective compound. Formic acid, acetic acid, oxalic acid, acrylic acid, etc., are cited as the organic carboxylic acid and acetic anhydride, etc., are used as the organic carboxylic acid anhydride. The organic carboxylic acid, etc., are added in an amount of 0.01-5.0 pts.wt., preferably 0.05-0.5 pt.wt. based on 100 pts.wt. acrylonitrile. The acrylonitrile is preferably used in an amount of ≥4.0 mol based on 1 mol sulfuric acid.
COPYRIGHT: (C)1992,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2184459A JP2551209B2 (en) | 1990-07-12 | 1990-07-12 | Method for producing 2-acrylamido-2-methylpropanesulfonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2184459A JP2551209B2 (en) | 1990-07-12 | 1990-07-12 | Method for producing 2-acrylamido-2-methylpropanesulfonic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0474159A true JPH0474159A (en) | 1992-03-09 |
| JP2551209B2 JP2551209B2 (en) | 1996-11-06 |
Family
ID=16153524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2184459A Expired - Lifetime JP2551209B2 (en) | 1990-07-12 | 1990-07-12 | Method for producing 2-acrylamido-2-methylpropanesulfonic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2551209B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102952052A (en) * | 2011-08-30 | 2013-03-06 | 中国石油化工股份有限公司 | Synthesis method of 2-acrylamide-2-methylpropanesulfonic acid (AMPS) |
| CN104230764A (en) * | 2014-09-03 | 2014-12-24 | 巨野县中海化工有限公司 | Preparation method of 2-acrylamide-2-methyl propanesulfonic acid |
| CN105461599A (en) * | 2014-09-03 | 2016-04-06 | 中国石油化工股份有限公司 | Acrylamide monomer and preparation method therefor |
| CN105601546A (en) * | 2016-01-29 | 2016-05-25 | 寿光市荣晟新材料有限公司 | Synthesizing method of 2-acrylamide-2-methylpropane sulfonic acid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54163524A (en) * | 1978-06-12 | 1979-12-26 | Nitto Chem Ind Co Ltd | Production of high-purity 2-acrylamide-2- methylpropanesulfonic acid |
| JPS6147458A (en) * | 1984-07-27 | 1986-03-07 | Allied Colloids Ltd | Manufacture of sulfonic acid |
-
1990
- 1990-07-12 JP JP2184459A patent/JP2551209B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54163524A (en) * | 1978-06-12 | 1979-12-26 | Nitto Chem Ind Co Ltd | Production of high-purity 2-acrylamide-2- methylpropanesulfonic acid |
| JPS6147458A (en) * | 1984-07-27 | 1986-03-07 | Allied Colloids Ltd | Manufacture of sulfonic acid |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102952052A (en) * | 2011-08-30 | 2013-03-06 | 中国石油化工股份有限公司 | Synthesis method of 2-acrylamide-2-methylpropanesulfonic acid (AMPS) |
| CN104230764A (en) * | 2014-09-03 | 2014-12-24 | 巨野县中海化工有限公司 | Preparation method of 2-acrylamide-2-methyl propanesulfonic acid |
| CN105461599A (en) * | 2014-09-03 | 2016-04-06 | 中国石油化工股份有限公司 | Acrylamide monomer and preparation method therefor |
| CN105461599B (en) * | 2014-09-03 | 2017-11-07 | 中国石油化工股份有限公司 | A kind of acrylamide monomer and preparation method thereof |
| CN105601546A (en) * | 2016-01-29 | 2016-05-25 | 寿光市荣晟新材料有限公司 | Synthesizing method of 2-acrylamide-2-methylpropane sulfonic acid |
| CN105601546B (en) * | 2016-01-29 | 2017-10-24 | 寿光市荣晟新材料有限公司 | A kind of synthetic method of the methyl propane sulfonic acid of 2 acrylamido 2 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2551209B2 (en) | 1996-11-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
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| EXPY | Cancellation because of completion of term |