TWI458697B - 製造ｎ－烷基（烷基）丙烯醯胺的方法 - Google Patents
製造ｎ－烷基（烷基）丙烯醯胺的方法 Download PDFInfo
- Publication number
- TWI458697B TWI458697B TW098126496A TW98126496A TWI458697B TW I458697 B TWI458697 B TW I458697B TW 098126496 A TW098126496 A TW 098126496A TW 98126496 A TW98126496 A TW 98126496A TW I458697 B TWI458697 B TW I458697B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- aqueous solution
- acrylamide
- meth
- propylamine
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 40
- 150000003926 acrylamides Chemical class 0.000 title description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 39
- 239000007864 aqueous solution Substances 0.000 claims description 37
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 150000002430 hydrocarbons Chemical class 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000356 contaminant Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical group CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- -1 hydrogen Sodium oxide Chemical class 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- 239000002585 base Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NMJORVOYSJLJGU-UHFFFAOYSA-N methane clathrate Chemical compound C.C.C.C.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O NMJORVOYSJLJGU-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/194,267 US8445723B2 (en) | 2008-08-19 | 2008-08-19 | Processes for producing N-alkyl (alkyl)acrylamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201010970A TW201010970A (en) | 2010-03-16 |
| TWI458697B true TWI458697B (zh) | 2014-11-01 |
Family
ID=41559492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW098126496A TWI458697B (zh) | 2008-08-19 | 2009-08-06 | 製造ｎ－烷基（烷基）丙烯醯胺的方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8445723B2 (https=) |
| EP (1) | EP2334635B1 (https=) |
| JP (1) | JP5954989B2 (https=) |
| KR (1) | KR101650593B1 (https=) |
| CN (1) | CN102131768B (https=) |
| AR (1) | AR073094A1 (https=) |
| AU (1) | AU2009283000B2 (https=) |
| CA (1) | CA2732115C (https=) |
| CL (1) | CL2009001563A1 (https=) |
| MY (1) | MY178900A (https=) |
| NZ (1) | NZ590925A (https=) |
| RU (1) | RU2501786C2 (https=) |
| TW (1) | TWI458697B (https=) |
| UA (1) | UA105497C2 (https=) |
| WO (1) | WO2010021956A2 (https=) |
| ZA (1) | ZA201100929B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008054612A1 (de) * | 2008-12-15 | 2010-06-17 | Evonik Röhm Gmbh | Verfahren zur Herstellung von N-Isopropyl(meth)acrylamid |
| DE102011089363A1 (de) * | 2011-12-21 | 2013-06-27 | Evonik Röhm Gmbh | Verfahren zur Herstellung von N-Alkyl(meth)acrylamiden |
| CN112189004B (zh) | 2018-05-23 | 2023-12-15 | 赢创运营有限公司 | 制备酮基官能化的芳族(甲基)丙烯酸化产物的方法 |
| SG11202100238TA (en) | 2018-07-17 | 2021-02-25 | Evonik Operations Gmbh | Method for preparing c-h acidic (meth)acrylates |
| EP3599232A1 (de) | 2018-07-26 | 2020-01-29 | Evonik Operations GmbH | Verfahren zur herstellung von n-methyl(meth)acrylamid |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2311548A (en) * | 1939-04-28 | 1943-02-16 | Du Pont | Polymers of amides of alpha-methylene monocarboxylic acids |
| US4859796A (en) * | 1985-11-27 | 1989-08-22 | Norsolor | Reacting a (meth)acrylic anhydride with a diamine to form a n-dialkylaminoalkyl(meth)acrylamide |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2773063A (en) * | 1956-12-04 | Preparation of acrylamides | ||
| DE2809102C2 (de) * | 1978-03-03 | 1986-12-04 | Röhm GmbH, 6100 Darmstadt | Verfahren zur Herstellung von α,β-ungesättigen Carbonsäureamiden |
| DE3130508A1 (de) * | 1981-08-01 | 1983-02-17 | Röhm GmbH, 6100 Darmstadt | "verfahren zur herstellung von methacryl- und acrylamiden" |
| DE3412650A1 (de) | 1984-04-04 | 1985-10-17 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von hydroxyalkyl-acrylamiden und -methacrylamiden |
| JPH0651787B2 (ja) | 1985-01-10 | 1994-07-06 | 鐘淵化学工業株式会社 | アクリルアミド系オリゴマ−及びその製造法 |
| JP2001348367A (ja) * | 2000-06-05 | 2001-12-18 | Mitsubishi Rayon Co Ltd | Ｎ−置換不飽和アミドの精製方法 |
| US6527959B1 (en) * | 2001-01-29 | 2003-03-04 | Ondeo Nalco Company | Method of clarifying bayer process liquors using salicylic acid containing polymers |
| US7138472B2 (en) * | 2001-01-29 | 2006-11-21 | Nalco Company | High molecular weight polymers containing pendant salicylic acid groups for clarifying bayer process liquors |
| US6946854B2 (en) * | 2003-01-22 | 2005-09-20 | Matsushita Electric Industrial Co., Ltd. | Ramp arrangement and method for measuring the position of an actuator in a rotating media data storage device |
| DE10323699A1 (de) * | 2003-05-22 | 2004-12-09 | Röhm GmbH & Co. KG | Verfahren zur kontinuierlichen Herstellung von Alkylamino(meth)acrylamiden |
| FR2877003B1 (fr) | 2004-10-26 | 2007-01-05 | Arkema Sa | Procede ameliore de fabrication d'anhydride (meth) acrylique |
| JP2007230966A (ja) * | 2006-03-03 | 2007-09-13 | Kohjin Co Ltd | （メタ）アクリルアミドアルキルカルボン酸の製造方法 |
| DE102006029320B3 (de) | 2006-06-23 | 2007-10-11 | Röhm Gmbh | Verfahren zur kontinuierlichen Herstellung von ungesättigten Carbonsäureanhydriden |
| DE102006029318B3 (de) | 2006-06-23 | 2007-10-11 | Röhm Gmbh | Verfahren zur kontinuierlichen Herstellung von ungesättigten Carbonsäureanhydriden |
| DE102006060162A1 (de) | 2006-12-18 | 2008-06-19 | Evonik Röhm Gmbh | Verbessertes Verfahren zur Herstellung von ungesättigten Carbonsäureanhybriden |
-
2008
- 2008-08-19 US US12/194,267 patent/US8445723B2/en active Active
-
2009
- 2009-07-09 CL CL2009001563A patent/CL2009001563A1/es unknown
- 2009-08-06 TW TW098126496A patent/TWI458697B/zh active
- 2009-08-17 NZ NZ590925A patent/NZ590925A/en unknown
- 2009-08-17 RU RU2011105303/04A patent/RU2501786C2/ru active
- 2009-08-17 EP EP09791559.9A patent/EP2334635B1/en not_active Not-in-force
- 2009-08-17 MY MYPI2011000573A patent/MY178900A/en unknown
- 2009-08-17 WO PCT/US2009/053973 patent/WO2010021956A2/en not_active Ceased
- 2009-08-17 CN CN200980132293.6A patent/CN102131768B/zh active Active
- 2009-08-17 CA CA2732115A patent/CA2732115C/en active Active
- 2009-08-17 KR KR1020117003807A patent/KR101650593B1/ko active Active
- 2009-08-17 AU AU2009283000A patent/AU2009283000B2/en active Active
- 2009-08-17 JP JP2011523901A patent/JP5954989B2/ja active Active
- 2009-08-17 UA UAA201101925A patent/UA105497C2/uk unknown
- 2009-08-19 AR ARP090103195A patent/AR073094A1/es active IP Right Grant
-
2011
- 2011-02-04 ZA ZA2011/00929A patent/ZA201100929B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2311548A (en) * | 1939-04-28 | 1943-02-16 | Du Pont | Polymers of amides of alpha-methylene monocarboxylic acids |
| US4859796A (en) * | 1985-11-27 | 1989-08-22 | Norsolor | Reacting a (meth)acrylic anhydride with a diamine to form a n-dialkylaminoalkyl(meth)acrylamide |
Non-Patent Citations (1)
| Title |
|---|
| Drobnik et al. "Enzymatic Cleavage of Side Chains of Synthetic Water-Soluble Polymers" Makromolekulare Chemie, 1976, Vol. 177, pages 2833-2848. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20100048951A1 (en) | 2010-02-25 |
| RU2011105303A (ru) | 2012-09-27 |
| ZA201100929B (en) | 2011-10-26 |
| CA2732115C (en) | 2015-04-28 |
| WO2010021956A2 (en) | 2010-02-25 |
| US8445723B2 (en) | 2013-05-21 |
| UA105497C2 (uk) | 2014-05-26 |
| EP2334635A2 (en) | 2011-06-22 |
| AU2009283000B2 (en) | 2014-05-01 |
| CL2009001563A1 (es) | 2011-05-13 |
| KR101650593B1 (ko) | 2016-08-23 |
| CN102131768A (zh) | 2011-07-20 |
| KR20110044236A (ko) | 2011-04-28 |
| WO2010021956A3 (en) | 2010-06-03 |
| EP2334635B1 (en) | 2017-03-22 |
| CN102131768B (zh) | 2014-08-20 |
| MY178900A (en) | 2020-10-22 |
| JP5954989B2 (ja) | 2016-07-20 |
| AU2009283000A1 (en) | 2010-02-25 |
| NZ590925A (en) | 2012-06-29 |
| CA2732115A1 (en) | 2010-02-25 |
| RU2501786C2 (ru) | 2013-12-20 |
| TW201010970A (en) | 2010-03-16 |
| AR073094A1 (es) | 2010-10-13 |
| JP2012500273A (ja) | 2012-01-05 |
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