GB573456A - Production of vinyl cyanide - Google Patents
Production of vinyl cyanideInfo
- Publication number
- GB573456A GB573456A GB9066/44A GB906644A GB573456A GB 573456 A GB573456 A GB 573456A GB 9066/44 A GB9066/44 A GB 9066/44A GB 906644 A GB906644 A GB 906644A GB 573456 A GB573456 A GB 573456A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- vinyl cyanide
- condensate
- per cent
- added
- 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title abstract 6
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 5
- 230000002378 acidificating effect Effects 0.000 abstract 5
- 239000000463 material Substances 0.000 abstract 5
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 239000012043 crude product Substances 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 abstract 1
- 229940005991 chloric acid Drugs 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 238000002474 experimental method Methods 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229940093915 gynecological organic acid Drugs 0.000 abstract 1
- 239000004310 lactic acid Substances 0.000 abstract 1
- 235000014655 lactic acid Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 abstract 1
- 235000019799 monosodium phosphate Nutrition 0.000 abstract 1
- 229910017604 nitric acid Inorganic materials 0.000 abstract 1
- 230000009972 noncorrosive effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 abstract 1
- 235000009529 zinc sulphate Nutrition 0.000 abstract 1
- 239000011686 zinc sulphate Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/12—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for the production of vinyl cyanide, which comprises reacting acetylene with hydrogen cyanide at a temperature above the boiling point of vinyl cyanide and in the presence of a catalyst for the reaction, includes the step of condensing the vapours of vinyl cyanide resulting from the reaction and acidifying the condensate. The crude product may then be stored for a considerable time without decomposition occurring and better yields of the pure vinyl cyanide are obtained on distillation. To render the crude product acid, any of the common inorganic or organic acids such as sulphur dioxide or sulphurous acid, sulphuric acid, hydrochloric acid, nitric acid, chloric acid, phosphoric acid, acetic acid, oxalic acid, propionic acid, lactic acid, tartaric acid or glycollic acid may be used, as well as salts whose aqueous solutions have an acid reaction, for example sodium dihydrogen phosphate, zinc sulphate and aluminium chloride. Preferably, non-corrosive acidic materials are employed. Water may be added to the acidic material but preferably in amounts not more than 10 per cent to 15 per cent of the acidic material utilised. Acids such as sulphuric or nitric acids should be added as dilute solutions. The preferred amount of acid used should be such that a water extract obtained by shaking 10 volumes of the acidified condensate with 25 volumes of water at room temperature will have a pH below 4.6. The acidic material should preferably be introduced intermittently or continuously into the condensing apparatus though it is effective when added to the condensate receiver. If a gaseous acidic material is employed, it may be added to the gaseous reaction products at some point in the system before condensation has taken place. In an example, acetylene and hydrogen cyanide are reacted over a catalys consisting of sodium cyanide supported on activated carbon and the condensed reaction products collected in receivers containing glacial acetic acid. On subsequent distillation the recovered vinyl cyanide amounted to 66 per cent by weight of the condensate. A similar experiment in which the acid was omitted gave a recovery of only 10 per cent. German Specification 559,734 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US573456XA | 1943-05-20 | 1943-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB573456A true GB573456A (en) | 1945-11-21 |
Family
ID=22010010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9066/44A Expired GB573456A (en) | 1943-05-20 | 1944-05-12 | Production of vinyl cyanide |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB573456A (en) |
-
1944
- 1944-05-12 GB GB9066/44A patent/GB573456A/en not_active Expired
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