TW297019B - - Google Patents
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- Publication number
- TW297019B TW297019B TW083106771A TW83106771A TW297019B TW 297019 B TW297019 B TW 297019B TW 083106771 A TW083106771 A TW 083106771A TW 83106771 A TW83106771 A TW 83106771A TW 297019 B TW297019 B TW 297019B
- Authority
- TW
- Taiwan
- Prior art keywords
- water
- contact
- propylene
- acrylonitrile
- amine
- Prior art date
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 65
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 57
- 238000000746 purification Methods 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 36
- 239000011347 resin Substances 0.000 claims description 36
- 229920005989 resin Polymers 0.000 claims description 36
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 32
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 31
- 150000001412 amines Chemical class 0.000 claims description 22
- -1 ion ion Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 2
- FOPFTHBUEHEFIB-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;propanoic acid Chemical compound CCC(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O FOPFTHBUEHEFIB-UHFFFAOYSA-N 0.000 claims 1
- 229910052797 bismuth Inorganic materials 0.000 claims 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 125000005610 enamide group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 238000005486 sulfidation Methods 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 66
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 35
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- 238000006116 polymerization reaction Methods 0.000 description 15
- AMLFJZRZIOZGPW-NSCUHMNNSA-N (e)-prop-1-en-1-amine Chemical compound C\C=C\N AMLFJZRZIOZGPW-NSCUHMNNSA-N 0.000 description 14
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
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- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 12
- 150000003335 secondary amines Chemical group 0.000 description 12
- 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 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
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- 101000730643 Homo sapiens Zinc finger protein PLAGL1 Proteins 0.000 description 6
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- 102100032570 Zinc finger protein PLAGL1 Human genes 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
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- 241000196324 Embryophyta Species 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N N-acetyl-para-amino-phenol Natural products CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
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- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
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- 238000009434 installation Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
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- 239000000203 mixture Substances 0.000 description 3
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- 239000011733 molybdenum Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
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- 235000014676 Phragmites communis Nutrition 0.000 description 2
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- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
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- 238000004898 kneading Methods 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DGJFLIRBDQYRGG-UHFFFAOYSA-N n-methylmethanamine;propanenitrile Chemical compound CNC.CCC#N DGJFLIRBDQYRGG-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- ZXDZVVSOWQEMOD-UHFFFAOYSA-N nitric hydrazide Chemical compound NN[N+]([O-])=O ZXDZVVSOWQEMOD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000004391 petroleum recovery Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical compound CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 1
- SZUDEHNEMMJTCQ-UHFFFAOYSA-N prop-2-enenitrile;hydrate Chemical compound O.C=CC#N SZUDEHNEMMJTCQ-UHFFFAOYSA-N 0.000 description 1
- IJTSKYNDWDNYSK-UHFFFAOYSA-N propan-2-one;thiophene Chemical compound CC(C)=O.C=1C=CSC=1 IJTSKYNDWDNYSK-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N propylene dimer Chemical group CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- REAPNPHEZNJFRY-UHFFFAOYSA-M sodium;4-cyanopentanoate Chemical compound [Na+].N#CC(C)CCC([O-])=O REAPNPHEZNJFRY-UHFFFAOYSA-M 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 210000003954 umbilical cord Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
- C07C231/065—By hydration using metals or metallic ions as catalyst
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18298793 | 1993-07-23 | ||
| JP24103993 | 1993-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW297019B true TW297019B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1997-02-01 |
Family
ID=26501579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW083106771A TW297019B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-07-23 | 1994-07-25 |
Country Status (8)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69807406T2 (de) * | 1997-10-01 | 2003-04-24 | Nippon Shokubai Co. Ltd., Osaka | Verfahren zur Herstellung von Alkylamino-(meth)Acrylat und eine Vorrichtung dafür |
| US6346195B1 (en) * | 1998-07-10 | 2002-02-12 | U.S. Filter Corporation | Ion exchange removal of metal ions from wastewater |
| US6315906B1 (en) | 1998-07-10 | 2001-11-13 | United States Filter Corporation | Removing metal ions from wastewater |
| CN1207272C (zh) * | 1998-10-30 | 2005-06-22 | 催化蒸馏技术公司 | 从腈制备酰胺和/或酸 |
| US6306795B1 (en) | 1999-09-07 | 2001-10-23 | Cytec Technology Corp. | Stable highly active supported copper based catalysts |
| CN100375787C (zh) * | 2003-04-10 | 2008-03-19 | 大野绿水株式会社 | 使用了酶的高品质丙烯酰胺系聚合物的制造方法 |
| US7488423B2 (en) | 2005-08-02 | 2009-02-10 | Siemens Water Technologies Holding Corp. | System and method of slurry treatment |
| WO2007043466A1 (ja) * | 2005-10-07 | 2007-04-19 | Mitsui Chemicals, Inc. | アミド化合物の製造方法 |
| CN101505845A (zh) * | 2006-08-28 | 2009-08-12 | 西门子水处理技术公司 | 浆料处理体系和方法 |
| CN102199107B (zh) * | 2010-03-26 | 2014-03-26 | 中国石油化工股份有限公司 | 丙烯腈中丙烯醛的脱除方法 |
| CN102199105B (zh) * | 2010-03-26 | 2014-05-28 | 中国石油化工股份有限公司 | 高纯丙烯腈的制备方法 |
| WO2016098269A1 (ja) * | 2014-12-17 | 2016-06-23 | 三菱レイヨン株式会社 | アクリルアミド水溶液及びアクリルアミド系重合体の製造方法 |
| CN112225629B (zh) * | 2019-07-15 | 2023-06-06 | 中国石油化工股份有限公司 | 有机原料脱除噁唑、丙烯醛、氢氰酸的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2444589A (en) * | 1945-08-10 | 1948-07-06 | American Cyanamid Co | Purification of organic nitriles |
| US2622097A (en) * | 1950-11-13 | 1952-12-16 | American Cyanamid Co | Purification of acrylonitrile |
| US3962333A (en) * | 1970-12-14 | 1976-06-08 | Mitsui Toatsu Chemicals, Incorporated | Process for the production of acrylamide and methacrylamide |
| BE792366A (fr) * | 1971-12-06 | 1973-03-30 | Mitsui Toatsu Chemicals | Procede de raffinage d'une solution aqueuse d'acrylamide |
| BE792323A (fr) * | 1971-12-06 | 1973-03-30 | Mitsui Toatsu Chemicals | Procede de traitement de solutions aqueuses d'acrylamide |
| JPS6012344B2 (ja) * | 1973-06-05 | 1985-04-01 | 三井東圧化学株式会社 | アクリルアミド水溶液の処理方法 |
| US4188339A (en) * | 1977-10-19 | 1980-02-12 | Nitto Chemical Industry Co., Ltd. | Process for preparing acrylamide aqueous solution |
| US4177210A (en) * | 1978-07-05 | 1979-12-04 | The Dow Chemical Company | Hydration of acrylonitrile to acrylamide |
| JPS55157543A (en) * | 1979-05-28 | 1980-12-08 | Mitsui Toatsu Chem Inc | Purification of aqueous solution of acrylamide |
| GB2059952B (en) * | 1979-09-13 | 1983-07-20 | Mitsui Toatsu Chemicals | Purifying aqueous acrylamide solutions |
| JPS56133250A (en) * | 1980-03-24 | 1981-10-19 | Mitsui Toatsu Chem Inc | Purification of aqueous solution of acrylamide |
| JPS577452A (en) * | 1980-06-18 | 1982-01-14 | Mitsui Toatsu Chem Inc | Purification of aqueous acrylamide |
| GB2114118A (en) * | 1982-01-29 | 1983-08-17 | American Cyanamid Co | Method for removing aldehyde impurities in acrylonitrile and acrylamide |
-
1994
- 1994-07-13 US US08/274,453 patent/US5476883A/en not_active Expired - Lifetime
- 1994-07-15 AU AU67522/94A patent/AU660390B2/en not_active Ceased
- 1994-07-15 EP EP94305202A patent/EP0635484B1/en not_active Expired - Lifetime
- 1994-07-15 DE DE69403571T patent/DE69403571T2/de not_active Expired - Lifetime
- 1994-07-20 MY MYPI94001881A patent/MY111374A/en unknown
- 1994-07-22 KR KR1019940017768A patent/KR0153234B1/ko not_active Expired - Fee Related
- 1994-07-22 CN CN94108614A patent/CN1051992C/zh not_active Expired - Fee Related
- 1994-07-25 TW TW083106771A patent/TW297019B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| KR0153234B1 (ko) | 1998-12-01 |
| EP0635484A1 (en) | 1995-01-25 |
| AU660390B2 (en) | 1995-06-22 |
| MY111374A (en) | 1999-12-31 |
| CN1106793A (zh) | 1995-08-16 |
| DE69403571D1 (de) | 1997-07-10 |
| CN1051992C (zh) | 2000-05-03 |
| DE69403571T2 (de) | 1997-12-18 |
| AU6752294A (en) | 1995-02-16 |
| US5476883A (en) | 1995-12-19 |
| KR950003264A (ko) | 1995-02-16 |
| EP0635484B1 (en) | 1997-06-04 |
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