CA1074334A - Manufacture of concentrated aqueous (meth)-acrylamide solutions by catalytic addition of water to (meth) acrylonitrile - Google Patents
Manufacture of concentrated aqueous (meth)-acrylamide solutions by catalytic addition of water to (meth) acrylonitrileInfo
- Publication number
- CA1074334A CA1074334A CA197,533A CA197533A CA1074334A CA 1074334 A CA1074334 A CA 1074334A CA 197533 A CA197533 A CA 197533A CA 1074334 A CA1074334 A CA 1074334A
- Authority
- CA
- Canada
- Prior art keywords
- meth
- acrylonitrile
- water
- acrylamide
- nitrile
- 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.)
- Expired
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title abstract description 24
- 230000003197 catalytic effect Effects 0.000 title description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000002825 nitriles Chemical class 0.000 claims abstract description 19
- 150000001408 amides Chemical class 0.000 claims abstract description 11
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000007259 addition reaction Methods 0.000 claims 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims 1
- 229940117913 acrylamide Drugs 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 229940108928 copper Drugs 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 acrylonitrile Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 2
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 235000014987 copper Nutrition 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- QUQFTIVBFKLPCL-UHFFFAOYSA-L copper;2-amino-3-[(2-amino-2-carboxylatoethyl)disulfanyl]propanoate Chemical compound [Cu+2].[O-]C(=O)C(N)CSSCC(N)C([O-])=O QUQFTIVBFKLPCL-UHFFFAOYSA-L 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732320061 DE2320061C3 (de) | 1973-04-19 | Verfahren zur Herstellung einer acrylnitrilhaltigen, konzentrierten, wäßrigen Acrylamidlösung durch katalytische Wasseranlagerung an Acrylnitril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1074334A true CA1074334A (en) | 1980-03-25 |
Family
ID=5878743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA197,533A Expired CA1074334A (en) | 1973-04-19 | 1974-04-11 | Manufacture of concentrated aqueous (meth)-acrylamide solutions by catalytic addition of water to (meth) acrylonitrile |
Country Status (14)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5122790A (ja) * | 1974-08-16 | 1976-02-23 | Mitsubishi Chem Ind | Akuriruamidojugotaino seizohoho |
| CA1065893A (en) * | 1975-03-17 | 1979-11-06 | Ken Matsuda | Reactant solutions for hydration of acrylonitrile to produce acrylamide |
| US3997606A (en) * | 1975-12-03 | 1976-12-14 | Nalco Chemical Company | Method of producing dry acrylamide |
| US4188339A (en) * | 1977-10-19 | 1980-02-12 | Nitto Chemical Industry Co., Ltd. | Process for preparing acrylamide aqueous solution |
| JPS60170894U (ja) * | 1984-04-20 | 1985-11-12 | クロイ電機株式会社 | 地下室における報知装置 |
| GB8804424D0 (en) * | 1988-02-25 | 1988-03-23 | Allied Colloids Ltd | Process for producing unsaturated carboxylic acids |
| DE4221604A1 (de) * | 1992-07-01 | 1994-01-05 | Basf Ag | Verfahren zur Herstellung von 5-Cyanvaleriansäureamid |
| DE102008037207A1 (de) * | 2008-08-11 | 2010-02-18 | Evonik Röhm Gmbh | Verfahren und Feststoffbehälter zur Herstellung einer wässrigen Methacrylamidlösung |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1450748A (fr) * | 1965-07-13 | 1966-06-24 | Electrochimie Soc | Perfectionnements aux procédés d'obtention d'acrylamide |
| US3758578A (en) * | 1969-06-23 | 1973-09-11 | Dow Chemical Co | Hydration of nitriles to amides using cupreous catalysts |
| US3624154A (en) * | 1970-03-26 | 1971-11-30 | Dow Chemical Co | Concentration of aqueous acrylamide |
| US3679745A (en) * | 1970-04-22 | 1972-07-25 | American Cyanamid Co | Hydration of acrylonitrile |
| US3696152A (en) * | 1970-06-17 | 1972-10-03 | Dow Chemical Co | Hydration of nitriles to amides using heterogeneous cupreous catalysts |
-
1974
- 1974-04-10 US US05/459,457 patent/US3956387A/en not_active Expired - Lifetime
- 1974-04-11 CA CA197,533A patent/CA1074334A/en not_active Expired
- 1974-04-11 IN IN831/CAL/74A patent/IN139156B/en unknown
- 1974-04-16 CH CH520774A patent/CH589611A5/xx not_active IP Right Cessation
- 1974-04-18 JP JP49042783A patent/JPS5040520A/ja active Pending
- 1974-04-18 ZA ZA00742465A patent/ZA742465B/xx unknown
- 1974-04-18 AT AT321374A patent/AT331777B/de not_active IP Right Cessation
- 1974-04-18 SU SU2014992A patent/SU530640A3/ru active
- 1974-04-18 GB GB1692174A patent/GB1456427A/en not_active Expired
- 1974-04-18 IT IT50483/74A patent/IT1005993B/it active
- 1974-04-18 BR BR3103/74A patent/BR7403103D0/pt unknown
- 1974-04-19 NL NLAANVRAGE7405360,A patent/NL180660B/xx not_active Application Discontinuation
- 1974-04-19 FR FR7413741A patent/FR2226387B1/fr not_active Expired
- 1974-04-19 BE BE143432A patent/BE813974A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU6784174A (en) | 1975-10-16 |
| ZA742465B (en) | 1975-05-28 |
| FR2226387B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-04-27 |
| JPS5040520A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-04-14 |
| BE813974A (fr) | 1974-10-21 |
| ATA321374A (de) | 1975-12-15 |
| CH589611A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-15 |
| US3956387A (en) | 1976-05-11 |
| DE2320061B2 (de) | 1975-07-10 |
| DE2320061A1 (de) | 1974-11-07 |
| GB1456427A (en) | 1976-11-24 |
| BR7403103D0 (pt) | 1974-11-19 |
| NL180660B (nl) | 1986-11-03 |
| IN139156B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-15 |
| SU530640A3 (ru) | 1976-09-30 |
| NL7405360A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-10-22 |
| AT331777B (de) | 1976-08-25 |
| IT1005993B (it) | 1976-09-30 |
| FR2226387A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3725208A (en) | Process for purification of acrylic acid from aldehydes by distillation with a reagent | |
| US5672745A (en) | Method for the continuous preparation of methionine or methionine derivatives | |
| US4430162A (en) | Process for purification of crude acetonitrile | |
| CA1074334A (en) | Manufacture of concentrated aqueous (meth)-acrylamide solutions by catalytic addition of water to (meth) acrylonitrile | |
| CN110088085B (zh) | 制备甲硫氨酸的方法 | |
| EP0635484B1 (en) | Preparation process of acrylamide | |
| CA1107760A (en) | Hydration of acrylonitrile to acrylamide | |
| CA1184937A (en) | Process for purifying an aqueous solution of acrylamide | |
| EP1503982B1 (en) | Use of at least one carboxylic acid for increasing the yield of acetonitrile in ammoxidation of carboxylic acids to a mixture of nitriles | |
| US5534655A (en) | Process for preparing acrylamide | |
| IE42182B1 (en) | Process for the preparation of tetra-methylethylenediamine | |
| CN111004123A (zh) | 一种3-乙氧基丙酸乙酯的制备方法 | |
| JP3908803B2 (ja) | アクリルアミドの製造方法 | |
| US3962333A (en) | Process for the production of acrylamide and methacrylamide | |
| US4365090A (en) | Process for production of acrylamide | |
| US4271088A (en) | High selectivity cyanoalkylation process | |
| JP2562150B2 (ja) | シクロヘキシルヒドロペルオキシドを含有する反応混合物の後処理法 | |
| US3235600A (en) | Reduction of diaminocyclohexane concentration in crude hexamethylenedi-amine | |
| JPS581108B2 (ja) | アクリロニトリルの精製法 | |
| EP0099752B1 (en) | Production of n-t-alkylamides from t-olefins or t-alcohols | |
| JP2623810B2 (ja) | α―ヒドロキシイソ酪酸アミドの製造方法 | |
| JP3683916B2 (ja) | アクリルアミドの製造方法 | |
| EP0127396A2 (en) | Process and catalyst for the production of aromatic amines | |
| RU2827377C1 (ru) | Способ получения соединения на основе фталонитрила | |
| US2838560A (en) | Manufacture of acrylonitrile |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |