DE1593296A1 - Verfahren zur Herstellung von Ocalsaeure - Google Patents
Verfahren zur Herstellung von OcalsaeureInfo
- Publication number
- DE1593296A1 DE1593296A1 DE19661593296 DE1593296A DE1593296A1 DE 1593296 A1 DE1593296 A1 DE 1593296A1 DE 19661593296 DE19661593296 DE 19661593296 DE 1593296 A DE1593296 A DE 1593296A DE 1593296 A1 DE1593296 A1 DE 1593296A1
- Authority
- DE
- Germany
- Prior art keywords
- propylene
- nitric acid
- reaction
- acid
- oxalic acid
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 title description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 76
- 238000006243 chemical reaction Methods 0.000 claims description 46
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 41
- 229910017604 nitric acid Inorganic materials 0.000 claims description 39
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 39
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 39
- 235000006408 oxalic acid Nutrition 0.000 claims description 22
- 230000003647 oxidation Effects 0.000 claims description 15
- 238000007254 oxidation reaction Methods 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229940116315 oxalic acid Drugs 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000004675 formic acid derivatives Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000004280 Sodium formate Substances 0.000 description 1
- 241000656145 Thyrsites atun Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- QXDMQSPYEZFLGF-UHFFFAOYSA-L calcium oxalate Chemical compound [Ca+2].[O-]C(=O)C([O-])=O QXDMQSPYEZFLGF-UHFFFAOYSA-L 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940116316 dihydrate oxalic acid Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- -1 for example Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
- C07C51/275—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of hydrocarbyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR12311A FR1528569A (fr) | 1965-04-07 | 1965-04-07 | Préparation d'acide oxalique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1593296A1 true DE1593296A1 (de) | 1971-09-16 |
Family
ID=8575862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661593296 Withdrawn DE1593296A1 (de) | 1965-04-07 | 1966-04-07 | Verfahren zur Herstellung von Ocalsaeure |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3651135A (enrdf_load_stackoverflow) |
| BE (1) | BE679159A (enrdf_load_stackoverflow) |
| DE (1) | DE1593296A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1528569A (enrdf_load_stackoverflow) |
| GB (1) | GB1110474A (enrdf_load_stackoverflow) |
| LU (1) | LU50838A1 (enrdf_load_stackoverflow) |
| NL (1) | NL152841B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2017325040B2 (en) * | 2016-09-12 | 2021-03-11 | Tal Or Ecology Ltd. | Recovery of oxalic acid from industrial ferrous oxalate |
-
1965
- 1965-04-07 FR FR12311A patent/FR1528569A/fr not_active Expired
-
1966
- 1966-03-22 NL NL666603748A patent/NL152841B/xx not_active IP Right Cessation
- 1966-04-06 BE BE679159D patent/BE679159A/xx unknown
- 1966-04-06 LU LU50838A patent/LU50838A1/xx unknown
- 1966-04-07 DE DE19661593296 patent/DE1593296A1/de not_active Withdrawn
- 1966-04-07 GB GB15713/66A patent/GB1110474A/en not_active Expired
-
1969
- 1969-12-01 US US876220A patent/US3651135A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BE679159A (enrdf_load_stackoverflow) | 1966-10-06 |
| NL6603748A (enrdf_load_stackoverflow) | 1966-10-10 |
| LU50838A1 (enrdf_load_stackoverflow) | 1966-06-06 |
| NL152841B (nl) | 1977-04-15 |
| GB1110474A (en) | 1968-04-18 |
| FR1528569A (fr) | 1968-06-14 |
| US3651135A (en) | 1972-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |