CA1119193A - Continuous cyanoethylation process - Google Patents
Continuous cyanoethylation processInfo
- Publication number
- CA1119193A CA1119193A CA000329897A CA329897A CA1119193A CA 1119193 A CA1119193 A CA 1119193A CA 000329897 A CA000329897 A CA 000329897A CA 329897 A CA329897 A CA 329897A CA 1119193 A CA1119193 A CA 1119193A
- Authority
- CA
- Canada
- Prior art keywords
- cyanoethylation
- reaction
- acrylonitrile
- reaction zone
- process according
- 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
- 238000007278 cyanoethylation reaction Methods 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 39
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 230000006872 improvement Effects 0.000 claims abstract description 15
- VTHRQKSLPFJQHN-UHFFFAOYSA-N 3-[2-(2-cyanoethoxy)ethoxy]propanenitrile Chemical compound N#CCCOCCOCCC#N VTHRQKSLPFJQHN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000006227 byproduct Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims 5
- 229920005554 polynitrile Polymers 0.000 claims 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 10
- -1 if used Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 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
- C07C253/00—Preparation of carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
-
- 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
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
-
- 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
- C07C255/23—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same unsaturated acyclic carbon skeleton
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91639378A | 1978-06-16 | 1978-06-16 | |
| US916,393 | 1978-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1119193A true CA1119193A (en) | 1982-03-02 |
Family
ID=25437200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000329897A Expired CA1119193A (en) | 1978-06-16 | 1979-06-15 | Continuous cyanoethylation process |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS554380A (enrdf_load_stackoverflow) |
| CA (1) | CA1119193A (enrdf_load_stackoverflow) |
| DE (1) | DE2924133A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2428626A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2023143B (enrdf_load_stackoverflow) |
| IT (1) | IT1121805B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140018567A1 (en) * | 2011-03-18 | 2014-01-16 | Lg Chem, Ltd. | Method for preparing dinitrile compound |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135725B1 (en) * | 1983-08-02 | 1989-03-08 | Tosoh Corporation | Process for producing polyamines |
| JPS60102154A (ja) * | 1983-11-07 | 1985-06-06 | フエジエル メグイエイ ガボナフオルガルミ エス マロミパリ バララツト | 澱粉質製品の製造法 |
| US5075507A (en) * | 1988-08-01 | 1991-12-24 | Air Products And Chemicals, Inc. | Process for the preparation of bis(aminopropyl)aliphatic glycols |
| US5081305A (en) * | 1988-10-13 | 1992-01-14 | Air Products And Chemicals, Inc. | Process for the preparation of bis(aminopropoxy)alkanes |
| JP2013075837A (ja) * | 2011-09-29 | 2013-04-25 | Fujifilm Corp | ニトリル化合物の製造方法 |
| US12131065B2 (en) | 2021-08-19 | 2024-10-29 | Micron Technology, Inc. | Memory device overhead reduction using artificial intelligence |
| US11989421B2 (en) | 2021-08-19 | 2024-05-21 | Micron Technology, Inc. | Adjustable data protection scheme using artificial intelligence |
| US11698858B2 (en) | 2021-08-19 | 2023-07-11 | Micron Technology, Inc. | Prediction based garbage collection |
| CN114632489A (zh) * | 2022-05-18 | 2022-06-17 | 山东海科新源材料科技股份有限公司 | 一种乙二醇双（丙腈）醚粗品合成方法及装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1054685A (enrdf_load_stackoverflow) * | 1963-04-20 | |||
| JPS5710869B2 (enrdf_load_stackoverflow) * | 1973-10-05 | 1982-03-01 |
-
1979
- 1979-06-15 IT IT23644/79A patent/IT1121805B/it active
- 1979-06-15 GB GB7921012A patent/GB2023143B/en not_active Expired
- 1979-06-15 JP JP7476579A patent/JPS554380A/ja active Granted
- 1979-06-15 DE DE19792924133 patent/DE2924133A1/de active Granted
- 1979-06-15 CA CA000329897A patent/CA1119193A/en not_active Expired
- 1979-06-18 FR FR7915517A patent/FR2428626A1/fr active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140018567A1 (en) * | 2011-03-18 | 2014-01-16 | Lg Chem, Ltd. | Method for preparing dinitrile compound |
| US9394242B2 (en) * | 2011-03-18 | 2016-07-19 | Lg Chem, Ltd. | Method for preparing dinitrile compound |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2428626B3 (enrdf_load_stackoverflow) | 1982-05-21 |
| IT7923644A0 (it) | 1979-06-15 |
| IT1121805B (it) | 1986-04-23 |
| DE2924133C2 (enrdf_load_stackoverflow) | 1989-08-24 |
| JPS554380A (en) | 1980-01-12 |
| GB2023143A (en) | 1979-12-28 |
| JPS638937B2 (enrdf_load_stackoverflow) | 1988-02-25 |
| GB2023143B (en) | 1982-11-03 |
| DE2924133A1 (de) | 1979-12-20 |
| FR2428626A1 (fr) | 1980-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |