DE2508559A1 - Verfahren zur herstellung von methylolacrylamiden - Google Patents
Verfahren zur herstellung von methylolacrylamidenInfo
- Publication number
- DE2508559A1 DE2508559A1 DE19752508559 DE2508559A DE2508559A1 DE 2508559 A1 DE2508559 A1 DE 2508559A1 DE 19752508559 DE19752508559 DE 19752508559 DE 2508559 A DE2508559 A DE 2508559A DE 2508559 A1 DE2508559 A1 DE 2508559A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- ion exchange
- column
- acrylamide
- minutes
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 METHYLOL ACRYLAMIDES Chemical class 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical class OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000010924 continuous production Methods 0.000 claims 1
- 239000011159 matrix material Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- LUOPFCDZQGKIDO-UHFFFAOYSA-N 2-(hydroxymethyl)prop-2-enamide Chemical class NC(=O)C(=C)CO LUOPFCDZQGKIDO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- SFUUDZYXHNYCTM-UHFFFAOYSA-N 2-methylprop-2-enamide;prop-2-enamide Chemical compound NC(=O)C=C.CC(=C)C(N)=O SFUUDZYXHNYCTM-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 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
- C07C233/16—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 singly-bound oxygen atoms
-
- 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
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US446980A US3887618A (en) | 1974-02-28 | 1974-02-28 | Use of weak base resins as catalysts for the methylolation of acrylamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2508559A1 true DE2508559A1 (de) | 1975-09-04 |
Family
ID=23774528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752508559 Pending DE2508559A1 (de) | 1974-02-28 | 1975-02-27 | Verfahren zur herstellung von methylolacrylamiden |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3887618A (enExample) |
| JP (1) | JPS50117715A (enExample) |
| DE (1) | DE2508559A1 (enExample) |
| FR (1) | FR2262659A1 (enExample) |
| GB (1) | GB1479105A (enExample) |
| NL (1) | NL7502332A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007090475A3 (de) * | 2006-02-09 | 2008-03-20 | Evonik Roehm Gmbh | Wässrige n-methylolmethacrylamid-methacrylamid-mischung |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52100418A (en) * | 1976-02-17 | 1977-08-23 | Mitsui Toatsu Chem Inc | Purification of acrylamide aqueous solution |
| DE2807659A1 (de) * | 1978-02-23 | 1979-09-06 | Basf Ag | Verfahren zur herstellung von n-substituierten carbonsaeureamiden |
| DE3414525A1 (de) * | 1984-04-17 | 1985-10-24 | Wacker-Chemie GmbH, 8000 München | Verfahren zur herstellung von waessrigen n-methylol(meth)acrylamid-loesungen |
| TW226364B (enExample) * | 1991-04-12 | 1994-07-11 | Nitto Chemical Industry Co Ltd | |
| JP4678790B2 (ja) * | 1994-09-16 | 2011-04-27 | 三菱レイヨン株式会社 | Ｎ−メチロールアクリルアミド結晶の製造方法 |
| US6001325A (en) * | 1996-11-26 | 1999-12-14 | Fmc Corporation | Process for removing acids from lithium salt solutions |
| CN101462978B (zh) * | 2007-12-17 | 2012-06-27 | 天津市化学试剂研究所 | 一种n-羟甲基丙烯酰胺及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2760977A (en) * | 1953-06-03 | 1956-08-28 | Research Corp | N-alkylol unsaturated amides |
| US2864861A (en) * | 1956-06-05 | 1958-12-16 | American Cyanamid Co | Preparation of methylolacrylamide |
| US2864862A (en) * | 1956-08-30 | 1958-12-16 | American Cyanamid Co | Methylolacrylamide |
| US3064050A (en) * | 1961-01-03 | 1962-11-13 | American Cyanamid Co | Process for the preparation of methylolacrylamide |
-
1974
- 1974-02-28 US US446980A patent/US3887618A/en not_active Expired - Lifetime
-
1975
- 1975-01-30 GB GB4194/75A patent/GB1479105A/en not_active Expired
- 1975-02-27 DE DE19752508559 patent/DE2508559A1/de active Pending
- 1975-02-27 NL NL7502332A patent/NL7502332A/xx unknown
- 1975-02-27 JP JP50023494A patent/JPS50117715A/ja active Pending
- 1975-02-28 FR FR7506443A patent/FR2262659A1/fr not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007090475A3 (de) * | 2006-02-09 | 2008-03-20 | Evonik Roehm Gmbh | Wässrige n-methylolmethacrylamid-methacrylamid-mischung |
| US8057698B2 (en) | 2006-02-09 | 2011-11-15 | Evonik Röhm Gmbh | Aqueous N-methylolmethacrylamide-methacrylamide mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7502332A (nl) | 1975-09-01 |
| US3887618A (en) | 1975-06-03 |
| GB1479105A (en) | 1977-07-06 |
| FR2262659A1 (enExample) | 1975-09-26 |
| JPS50117715A (enExample) | 1975-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |