DE2547107A1 - Verfahren zur herstellung von n,n-bisacrylamidoessigsaeuren - Google Patents
Verfahren zur herstellung von n,n-bisacrylamidoessigsaeurenInfo
- Publication number
- DE2547107A1 DE2547107A1 DE19752547107 DE2547107A DE2547107A1 DE 2547107 A1 DE2547107 A1 DE 2547107A1 DE 19752547107 DE19752547107 DE 19752547107 DE 2547107 A DE2547107 A DE 2547107A DE 2547107 A1 DE2547107 A1 DE 2547107A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sulfuric acid
- bisacrylamidoacetic
- acrylonitrile
- water
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000007513 acids Chemical class 0.000 title claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 35
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 12
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 10
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 229940107700 pyruvic acid Drugs 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- LVKKFNORSNCNPP-UHFFFAOYSA-N 2,2-bis(prop-2-enoylamino)acetic acid Chemical compound C=CC(=O)NC(C(=O)O)NC(=O)C=C LVKKFNORSNCNPP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000005457 ice water Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 2
- ITKBBJFGFCCPSG-UHFFFAOYSA-N 2,2-bis(2-methylprop-2-enoylamino)acetic acid Chemical compound CC(=C)C(=O)NC(C(O)=O)NC(=O)C(C)=C ITKBBJFGFCCPSG-UHFFFAOYSA-N 0.000 claims 1
- KYGMEOXEBUXIJO-UHFFFAOYSA-N 2,2-bis(prop-2-enoylamino)propanoic acid Chemical compound CC(C(=O)O)(NC(C=C)=O)NC(C=C)=O KYGMEOXEBUXIJO-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 238000001632 acidimetric titration Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- -1 diethyl-bisacrylamidoacetic acid Chemical compound 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7420220A FR2274606A1 (fr) | 1974-06-11 | 1974-06-11 | Procede de fabrication des acides n,n-bis-acrylamidoacetiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2547107A1 true DE2547107A1 (de) | 1977-05-05 |
Family
ID=9139906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752547107 Withdrawn DE2547107A1 (de) | 1974-06-11 | 1975-10-21 | Verfahren zur herstellung von n,n-bisacrylamidoessigsaeuren |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE2547107A1 (https=) |
| FR (1) | FR2274606A1 (https=) |
-
1974
- 1974-06-11 FR FR7420220A patent/FR2274606A1/fr active Granted
-
1975
- 1975-10-21 DE DE19752547107 patent/DE2547107A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2274606B1 (https=) | 1976-10-15 |
| FR2274606A1 (fr) | 1976-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |