CA1068723A - PROCESS FOR THE CONTINUOUS MANUFACTURE OF .alpha.-CYANO-ETHYLATED ALIPHATIC ALDEHYDES - Google Patents
PROCESS FOR THE CONTINUOUS MANUFACTURE OF .alpha.-CYANO-ETHYLATED ALIPHATIC ALDEHYDESInfo
- Publication number
- CA1068723A CA1068723A CA277,254A CA277254A CA1068723A CA 1068723 A CA1068723 A CA 1068723A CA 277254 A CA277254 A CA 277254A CA 1068723 A CA1068723 A CA 1068723A
- Authority
- CA
- Canada
- Prior art keywords
- acrylonitrile
- aldehyde
- alkali metal
- metal hydroxide
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 22
- 150000001299 aldehydes Chemical class 0.000 title claims description 20
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- -1 .alpha.-cyano-ethylated aliphatic aldehydes Chemical class 0.000 claims abstract description 20
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 10
- 238000010924 continuous production Methods 0.000 claims abstract description 5
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 18
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 claims description 5
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- HKJVKIURQSVEQB-UHFFFAOYSA-N 4,4-dimethyl-5-oxopentanenitrile Chemical compound O=CC(C)(C)CCC#N HKJVKIURQSVEQB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009183 running Effects 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000007278 cyanoethylation reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WZGRZLPEJDJMAI-UHFFFAOYSA-N 4-methyl-5-oxopentanenitrile Chemical compound O=CC(C)CCC#N WZGRZLPEJDJMAI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| DE2619580A DE2619580C2 (de) | 1976-05-04 | 1976-05-04 | Verfahren zur kontinuierlichen Herstellung a-cyanäthylierter, aliphatischer Aldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068723A true CA1068723A (en) | 1979-12-25 |
Family
ID=5976980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA277,254A Expired CA1068723A (en) | 1976-05-04 | 1977-04-28 | PROCESS FOR THE CONTINUOUS MANUFACTURE OF .alpha.-CYANO-ETHYLATED ALIPHATIC ALDEHYDES |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4102913A (enExample) |
| JP (1) | JPS52133921A (enExample) |
| CA (1) | CA1068723A (enExample) |
| DE (1) | DE2619580C2 (enExample) |
| ES (1) | ES458215A1 (enExample) |
| FR (1) | FR2361354A1 (enExample) |
| IT (1) | IT1083176B (enExample) |
| NL (1) | NL160246C (enExample) |
| SE (1) | SE440905B (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2353687A (en) * | 1942-11-18 | 1944-07-18 | Resinous Prod & Chemical Co | Cyanoaldehydes and process of producing them |
| US2409086A (en) * | 1943-05-01 | 1946-10-08 | Du Pont | Reaction products of nitriles and aldehydes |
-
1976
- 1976-05-04 DE DE2619580A patent/DE2619580C2/de not_active Expired
- 1976-06-02 NL NL7605963.A patent/NL160246C/xx not_active IP Right Cessation
-
1977
- 1977-04-25 US US05/790,202 patent/US4102913A/en not_active Expired - Lifetime
- 1977-04-26 JP JP4834777A patent/JPS52133921A/ja active Granted
- 1977-04-27 SE SE7704840A patent/SE440905B/xx unknown
- 1977-04-27 ES ES458215A patent/ES458215A1/es not_active Expired
- 1977-04-27 FR FR7712817A patent/FR2361354A1/fr active Granted
- 1977-04-28 CA CA277,254A patent/CA1068723A/en not_active Expired
- 1977-04-29 IT IT49201/77A patent/IT1083176B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| ES458215A1 (es) | 1978-02-16 |
| JPS5737588B2 (enExample) | 1982-08-10 |
| SE440905B (sv) | 1985-08-26 |
| SE7704840L (sv) | 1977-11-05 |
| FR2361354A1 (fr) | 1978-03-10 |
| JPS52133921A (en) | 1977-11-09 |
| FR2361354B1 (enExample) | 1979-03-02 |
| DE2619580B1 (de) | 1977-08-18 |
| DE2619580C2 (de) | 1978-03-30 |
| US4102913A (en) | 1978-07-25 |
| NL7605963A (nl) | 1977-11-08 |
| NL160246C (nl) | 1979-10-15 |
| IT1083176B (it) | 1985-05-21 |
| NL160246B (nl) | 1979-05-15 |
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