IL44209A - Process for the preparation of oxamide - Google Patents
Process for the preparation of oxamideInfo
- Publication number
- IL44209A IL44209A IL44209A IL4420974A IL44209A IL 44209 A IL44209 A IL 44209A IL 44209 A IL44209 A IL 44209A IL 4420974 A IL4420974 A IL 4420974A IL 44209 A IL44209 A IL 44209A
- Authority
- IL
- Israel
- Prior art keywords
- catalyst solution
- reaction
- oxygen
- oxamide
- gas
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 46
- 238000002360 preparation method Methods 0.000 title claims description 6
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 title abstract description 55
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 79
- 239000003054 catalyst Substances 0.000 claims abstract description 71
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000001301 oxygen Substances 0.000 claims abstract description 53
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 7
- 229910002651 NO3 Inorganic materials 0.000 claims abstract description 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910001431 copper ion Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 239000007789 gas Substances 0.000 claims description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 13
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229910017604 nitric acid Inorganic materials 0.000 claims description 11
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- -1 nitrate ions Chemical class 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 150000002815 nickel Chemical class 0.000 claims description 2
- XHTYLMIRTKBVHT-UHFFFAOYSA-N oxamide Chemical compound NC(=O)C(N)=O.NC(=O)C(N)=O XHTYLMIRTKBVHT-UHFFFAOYSA-N 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 1
- 159000000014 iron salts Chemical class 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 72
- 239000010949 copper Substances 0.000 description 25
- 238000010521 absorption reaction Methods 0.000 description 15
- 230000006698 induction Effects 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 238000007792 addition Methods 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002912 waste gas Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001503485 Mammuthus Species 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- MUQBUKGCVPYANP-UHFFFAOYSA-N formonitrile Chemical compound N#C.N#C MUQBUKGCVPYANP-UHFFFAOYSA-N 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- JCZMXVGQBBATMY-UHFFFAOYSA-N nitro acetate Chemical compound CC(=O)O[N+]([O-])=O JCZMXVGQBBATMY-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 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 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
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)
- Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732308941 DE2308941C3 (de) | 1973-02-23 | Verfahren zur Herstellung von Oxamid | |
| DE2402354A DE2402354C2 (de) | 1974-01-18 | 1974-01-18 | Verfahren zur Herstellung von Oxamid |
| DE2402352A DE2402352A1 (de) | 1974-01-18 | 1974-01-18 | Verfahren zur herstellung von oxamid |
| DE2403120A DE2403120C2 (de) | 1974-01-23 | 1974-01-23 | Verfahren zur Herstellung von Oxamid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44209A0 IL44209A0 (en) | 1974-05-16 |
| IL44209A true IL44209A (en) | 1977-03-31 |
Family
ID=27431647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44209A IL44209A (en) | 1973-02-23 | 1974-02-14 | Process for the preparation of oxamide |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3989753A (hu) |
| JP (1) | JPS5833220B2 (hu) |
| AR (1) | AR197756A1 (hu) |
| AT (1) | AT335416B (hu) |
| CA (1) | CA1026377A (hu) |
| CH (1) | CH590213A5 (hu) |
| CS (1) | CS184338B2 (hu) |
| DD (1) | DD110854A5 (hu) |
| FR (1) | FR2219153B1 (hu) |
| GB (1) | GB1458871A (hu) |
| HU (1) | HU170424B (hu) |
| IL (1) | IL44209A (hu) |
| IT (1) | IT1008262B (hu) |
| LU (1) | LU69446A1 (hu) |
| NL (1) | NL177400C (hu) |
| RO (1) | RO70980A (hu) |
| SE (1) | SE386665B (hu) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190318B (it) * | 1986-04-17 | 1988-02-16 | Enichem Anic Spa | Procedimento di purificazione della diamide dell'acido ossalico |
| IT1213401B (it) * | 1986-12-11 | 1989-12-20 | Enichem Anic Spa | Procedimento di purificazione della diamide dell'acido ossalico. |
| IT1255265B (it) * | 1992-05-22 | 1995-10-25 | Enichem Anic Srl | Produzione in continuo di ossamide per ossidazione catalitica di hcn |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037055A (en) * | 1960-04-28 | 1962-05-29 | Pure Oil Co | Preparation of oxamide |
| GB1084477A (en) * | 1965-08-02 | 1967-09-20 | Sagami Chem Res | Improvements in or relating to the preparation of cyanogen |
-
1974
- 1974-02-14 IL IL44209A patent/IL44209A/en unknown
- 1974-02-15 CS CS7400001122A patent/CS184338B2/cs unknown
- 1974-02-18 NL NLAANVRAGE7402197,A patent/NL177400C/xx not_active IP Right Cessation
- 1974-02-19 RO RO7477741A patent/RO70980A/ro unknown
- 1974-02-20 DD DD176712A patent/DD110854A5/xx unknown
- 1974-02-20 IT IT48511/74A patent/IT1008262B/it active
- 1974-02-20 CH CH237974A patent/CH590213A5/xx not_active IP Right Cessation
- 1974-02-21 AR AR252476A patent/AR197756A1/es active
- 1974-02-21 GB GB788674A patent/GB1458871A/en not_active Expired
- 1974-02-21 US US05/444,291 patent/US3989753A/en not_active Expired - Lifetime
- 1974-02-21 LU LU69446A patent/LU69446A1/xx unknown
- 1974-02-21 AT AT140274A patent/AT335416B/de not_active IP Right Cessation
- 1974-02-22 JP JP49020623A patent/JPS5833220B2/ja not_active Expired
- 1974-02-22 FR FR7406109A patent/FR2219153B1/fr not_active Expired
- 1974-02-22 CA CA193,293A patent/CA1026377A/en not_active Expired
- 1974-02-22 HU HUHO1650A patent/HU170424B/hu unknown
- 1974-02-22 SE SE7402352A patent/SE386665B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1458871A (en) | 1976-12-15 |
| FR2219153B1 (hu) | 1977-09-23 |
| ATA140274A (de) | 1976-07-15 |
| RO70980A (ro) | 1981-08-17 |
| CH590213A5 (hu) | 1977-07-29 |
| LU69446A1 (hu) | 1975-12-09 |
| IL44209A0 (en) | 1974-05-16 |
| JPS5833220B2 (ja) | 1983-07-18 |
| AU6585374A (en) | 1975-08-21 |
| NL177400B (nl) | 1985-04-16 |
| NL7402197A (hu) | 1974-08-27 |
| US3989753A (en) | 1976-11-02 |
| NL177400C (nl) | 1985-09-16 |
| AT335416B (de) | 1977-03-10 |
| AR197756A1 (es) | 1974-04-30 |
| CA1026377A (en) | 1978-02-14 |
| JPS5029516A (hu) | 1975-03-25 |
| IT1008262B (it) | 1976-11-10 |
| SE386665B (sv) | 1976-08-16 |
| DD110854A5 (hu) | 1975-01-12 |
| HU170424B (hu) | 1977-06-28 |
| CS184338B2 (en) | 1978-08-31 |
| FR2219153A1 (hu) | 1974-09-20 |
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