KR20090121293A - 아미노 니트릴의 제조 방법 - Google Patents
아미노 니트릴의 제조 방법 Download PDFInfo
- Publication number
- KR20090121293A KR20090121293A KR1020097018179A KR20097018179A KR20090121293A KR 20090121293 A KR20090121293 A KR 20090121293A KR 1020097018179 A KR1020097018179 A KR 1020097018179A KR 20097018179 A KR20097018179 A KR 20097018179A KR 20090121293 A KR20090121293 A KR 20090121293A
- Authority
- KR
- South Korea
- Prior art keywords
- aan
- idan
- mixture
- crude
- amino 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.)
- Withdrawn
Links
- 125000005219 aminonitrile group Chemical group 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 44
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 11
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
- 239000011552 falling film Substances 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 53
- BSRDNMMLQYNQQD-UHFFFAOYSA-N iminodiacetonitrile Chemical compound N#CCNCC#N BSRDNMMLQYNQQD-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 28
- 229910021529 ammonia Inorganic materials 0.000 description 25
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 19
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 14
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 ethylene amide Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003381 stabilizer 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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/21—Monoamines
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07103285 | 2007-03-01 | ||
| EP07103285.8 | 2007-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090121293A true KR20090121293A (ko) | 2009-11-25 |
Family
ID=39365482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020097018179A Withdrawn KR20090121293A (ko) | 2007-03-01 | 2008-02-28 | 아미노 니트릴의 제조 방법 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8153845B2 (enExample) |
| EP (1) | EP2132164A1 (enExample) |
| JP (1) | JP2010520169A (enExample) |
| KR (1) | KR20090121293A (enExample) |
| CN (1) | CN101627005A (enExample) |
| WO (1) | WO2008104581A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE482923T1 (de) * | 2007-03-01 | 2010-10-15 | Basf Se | Herstellungsverfahren für ethylenamingemische |
| JP2010520167A (ja) * | 2007-03-01 | 2010-06-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 原料ａａｎからのエチレンアミンの製造方法 |
| EP2132162B1 (de) * | 2007-03-01 | 2011-06-22 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| JP5399270B2 (ja) * | 2007-03-01 | 2014-01-29 | ビーエーエスエフ ソシエタス・ヨーロピア | エチレンジアミンの製造方法 |
| JP2012512826A (ja) | 2008-12-19 | 2012-06-07 | ビーエーエスエフ ソシエタス・ヨーロピア | 純粋なトリエタノールアミン（ｔｅｏａ）の製造法 |
| IT1395127B1 (it) * | 2009-07-30 | 2012-09-05 | Saipem Spa | Procedimento per il recupero di ammoniaca da una corrente gassosa |
| CN103764617B (zh) * | 2011-08-31 | 2015-12-02 | 巴斯夫欧洲公司 | 通过使edfa和/或edmfa与hcn反应制备eddn和/或edmn的方法 |
| EP2751069B1 (de) * | 2011-08-31 | 2017-10-11 | Basf Se | Verfahren zur herstellung von eddn und/oder edmn |
| CN113402407A (zh) * | 2021-06-16 | 2021-09-17 | 上海蓝科石化环保科技股份有限公司 | 一种羟基乙腈氨化反应装置及工艺 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511487A (en) * | 1946-08-08 | 1950-06-13 | Du Pont | Synthesis of iminodiacetonitrile |
| US3988360A (en) * | 1973-11-15 | 1976-10-26 | W. R. Grace & Co. | Process for preparing iminodiacetonitrile |
| CA1061800A (en) * | 1975-09-08 | 1979-09-04 | Roger R. Gaudette | Process for preparing iminodiacetonitrile |
| US4404167A (en) * | 1979-05-14 | 1983-09-13 | Rozenfeld Iosif L | Protecting steel and ferrous metals against H2 S corrosion |
| JPH0621119B2 (ja) * | 1986-02-13 | 1994-03-23 | 三井東圧化学株式会社 | ポリエチレンポリアミンの製造方法 |
| US4661614A (en) * | 1986-03-06 | 1987-04-28 | Monsanto Company | Process for the preparation of iminodiacetonitrile |
| US4895971A (en) * | 1988-10-31 | 1990-01-23 | W. R. Grace & Co.-Conn. | Process for the production of iminodiacetonitrile |
| JP2642466B2 (ja) * | 1989-01-25 | 1997-08-20 | 三井東圧化学株式会社 | アミノアセトニトリルの製造方法 |
| US4948909A (en) * | 1989-08-14 | 1990-08-14 | Monsanto Company | Process for the preparation of iminodiacetonitrile and iminodiacetic acid |
| US5187301A (en) * | 1989-10-26 | 1993-02-16 | W. R. Grace & Co.-Conn. | Preparation of iminodiacetonitrile from glycolonitrile |
| US5079380A (en) * | 1990-05-23 | 1992-01-07 | W. R. Grace & Co.-Conn. | Adiabatic process for the preparation of glycinonitrile |
| JPH04202163A (ja) * | 1990-11-30 | 1992-07-22 | Mitsui Toatsu Chem Inc | エチレンアミン類の製造法 |
| DE10056840A1 (de) | 2000-11-16 | 2002-05-23 | Basf Ag | Verfahren zur Hydrierung von Nitrilen an Raney-Katalysatoren |
| EP2132162B1 (de) * | 2007-03-01 | 2011-06-22 | Basf Se | Verfahren zur herstellung von ethylenaminen |
| JP2010520167A (ja) * | 2007-03-01 | 2010-06-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 原料ａａｎからのエチレンアミンの製造方法 |
-
2008
- 2008-02-28 KR KR1020097018179A patent/KR20090121293A/ko not_active Withdrawn
- 2008-02-28 JP JP2009551209A patent/JP2010520169A/ja active Pending
- 2008-02-28 US US12/529,096 patent/US8153845B2/en not_active Expired - Fee Related
- 2008-02-28 WO PCT/EP2008/052412 patent/WO2008104581A1/de not_active Ceased
- 2008-02-28 EP EP08717209A patent/EP2132164A1/de not_active Withdrawn
- 2008-02-28 CN CN200880006358A patent/CN101627005A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008104581A1 (de) | 2008-09-04 |
| CN101627005A (zh) | 2010-01-13 |
| JP2010520169A (ja) | 2010-06-10 |
| US8153845B2 (en) | 2012-04-10 |
| US20100016625A1 (en) | 2010-01-21 |
| EP2132164A1 (de) | 2009-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20090831 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |