SK280401B6 - Spôsob výroby nitrilov kyseliny aminopropiónovej - Google Patents
Spôsob výroby nitrilov kyseliny aminopropiónovej Download PDFInfo
- Publication number
- SK280401B6 SK280401B6 SK778-94A SK77894A SK280401B6 SK 280401 B6 SK280401 B6 SK 280401B6 SK 77894 A SK77894 A SK 77894A SK 280401 B6 SK280401 B6 SK 280401B6
- Authority
- SK
- Slovakia
- Prior art keywords
- aminopropionic
- preparation
- ammonia
- acrylonitrile
- nitriles
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000008362 aminopropionitriles Chemical class 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 15
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 150000008360 acrylonitriles Chemical class 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000002825 nitriles Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 13
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 10
- -1 aminopropionitrile nitriles Chemical class 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HOYKPPXKLRXDBR-UHFFFAOYSA-N [O].[Co].[Co] Chemical compound [O].[Co].[Co] HOYKPPXKLRXDBR-UHFFFAOYSA-N 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BCGCCTGNWPKXJL-UHFFFAOYSA-N 3-(2-cyanoethoxy)propanenitrile Chemical compound N#CCCOCCC#N BCGCCTGNWPKXJL-UHFFFAOYSA-N 0.000 description 1
- SBAJRGRUGUQKAF-UHFFFAOYSA-N 3-(2-cyanoethylamino)propanenitrile Chemical compound N#CCCNCCC#N SBAJRGRUGUQKAF-UHFFFAOYSA-N 0.000 description 1
- GDIMNXJSMJSDSB-UHFFFAOYSA-N 3-amino-2-methylpropanenitrile Chemical compound NCC(C)C#N GDIMNXJSMJSDSB-UHFFFAOYSA-N 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-aminopropionic acid Natural products NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910000428 cobalt oxide Inorganic materials 0.000 description 1
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic 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 |
|---|---|---|---|
| DE4321273A DE4321273A1 (de) | 1993-06-28 | 1993-06-28 | Verfahren zur Herstellung von Aminopropionitrilen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK77894A3 SK77894A3 (en) | 1995-02-08 |
| SK280401B6 true SK280401B6 (sk) | 2000-01-18 |
Family
ID=6491285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK778-94A SK280401B6 (sk) | 1993-06-28 | 1994-06-27 | Spôsob výroby nitrilov kyseliny aminopropiónovej |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5434291A (cs) |
| EP (1) | EP0630886B1 (cs) |
| JP (1) | JP4001937B2 (cs) |
| CZ (1) | CZ289635B6 (cs) |
| DE (2) | DE4321273A1 (cs) |
| ES (1) | ES2115103T3 (cs) |
| SK (1) | SK280401B6 (cs) |
| ZA (1) | ZA944577B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101296899B (zh) * | 2005-09-15 | 2012-10-10 | 巴斯夫欧洲公司 | 生产β-氨基丙酸衍生物的方法 |
| CN102827031B (zh) * | 2012-08-31 | 2014-07-16 | 江苏兄弟维生素有限公司 | 一种β-氨基丙腈连续反应工艺 |
| TWI564279B (zh) * | 2015-11-26 | 2017-01-01 | 南亞塑膠工業股份有限公司 | 使用陽離子交換樹脂為催化劑的ｎ，ｎ’－雙（２－腈基乙基）－１，２－乙二胺製備方法。 |
| CN107473986B (zh) * | 2017-08-07 | 2019-09-10 | 杭州鑫富科技有限公司 | 一种β-氨基丙腈回收方法 |
| CN107935888B (zh) * | 2017-12-26 | 2020-04-07 | 浙江新和成股份有限公司 | 一种在超临界条件下制备3-氨基丙腈的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1992615A (en) * | 1931-09-10 | 1935-02-26 | Ig Farbenindustrie Ag | Amino nitrile and process of producing same |
| DE598185C (de) * | 1931-09-11 | 1934-06-07 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von Aminoverbindungen |
| US2401429A (en) * | 1942-08-31 | 1946-06-04 | Frederick E Kung | Process for the production of 2-amino-carboxylic acid nitriles |
| US2432511A (en) * | 1943-02-16 | 1947-12-16 | American Cyanamid Co | Stabilization of acrylonitrile |
| US2448013A (en) * | 1944-12-26 | 1948-08-31 | Upjohn Co | Preparation of beta-aminopropionitrile |
| GB642409A (en) * | 1946-05-14 | 1950-09-06 | American Cyanamid Co | Improvements in or relating to the preparation of guanamines |
| US2742491A (en) * | 1953-02-10 | 1956-04-17 | Merck & Co Inc | Preparation of beta-aminopropionitrile |
| US2819303A (en) * | 1953-04-06 | 1958-01-07 | Nopco Chem Co | Process for production of beta-alanine |
| DE1003740B (de) * | 1955-03-02 | 1957-03-07 | Basf Ag | Verfahren zur gleichzeitigen Herstellung von ª‰-Aminopropionsaeurenitril und Bis-(ª‰-cyanaethyl)-amin |
| US3174992A (en) * | 1962-05-21 | 1965-03-23 | Dow Chemical Co | Method for making aminonitriles |
| JPS5227138B2 (cs) * | 1973-07-30 | 1977-07-19 | ||
| US3935256A (en) * | 1974-09-06 | 1976-01-27 | Thompson-Hayward Chem. Co. | Process for the production of the calcium salt of pantothenic acid |
| US4211725A (en) * | 1977-11-10 | 1980-07-08 | Milliken Research Corporation | Nitrogen containing compositions |
| DE3825119A1 (de) * | 1988-07-23 | 1990-02-15 | Basf Ag | Verfahren zur gemeinschaftlichen herstellung von 3-dialkylaminopropionitrilen, bis-(2-cyanoethyl)-ether und gewuenschtenfalls ethylencyanhydrin |
| US5247120A (en) * | 1991-08-03 | 1993-09-21 | Basf Aktiengesellschaft | Preparation of aminopropionitriles |
-
1993
- 1993-06-28 DE DE4321273A patent/DE4321273A1/de not_active Withdrawn
-
1994
- 1994-06-01 US US08/251,334 patent/US5434291A/en not_active Expired - Lifetime
- 1994-06-17 CZ CZ19941501A patent/CZ289635B6/cs not_active IP Right Cessation
- 1994-06-20 EP EP94109478A patent/EP0630886B1/de not_active Expired - Lifetime
- 1994-06-20 ES ES94109478T patent/ES2115103T3/es not_active Expired - Lifetime
- 1994-06-20 DE DE59405751T patent/DE59405751D1/de not_active Expired - Lifetime
- 1994-06-27 SK SK778-94A patent/SK280401B6/sk not_active IP Right Cessation
- 1994-06-27 ZA ZA944577A patent/ZA944577B/xx unknown
- 1994-06-28 JP JP14624794A patent/JP4001937B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE59405751D1 (de) | 1998-05-28 |
| JPH0753495A (ja) | 1995-02-28 |
| EP0630886B1 (de) | 1998-04-22 |
| SK77894A3 (en) | 1995-02-08 |
| ES2115103T3 (es) | 1998-06-16 |
| US5434291A (en) | 1995-07-18 |
| EP0630886A1 (de) | 1994-12-28 |
| CZ150194A3 (en) | 1995-01-18 |
| ZA944577B (en) | 1995-12-27 |
| JP4001937B2 (ja) | 2007-10-31 |
| DE4321273A1 (de) | 1995-01-05 |
| CZ289635B6 (cs) | 2002-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20090627 |