DE1668783C3 - - Google Patents
Info
- Publication number
- DE1668783C3 DE1668783C3 DE19671668783 DE1668783A DE1668783C3 DE 1668783 C3 DE1668783 C3 DE 1668783C3 DE 19671668783 DE19671668783 DE 19671668783 DE 1668783 A DE1668783 A DE 1668783A DE 1668783 C3 DE1668783 C3 DE 1668783C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- propionic acid
- impurities
- urea
- hours
- 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 109
- 235000019260 propionic acid Nutrition 0.000 claims description 55
- 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 claims description 54
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 44
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 32
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 28
- 239000004202 carbamide Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 25
- 239000012535 impurity Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 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 16
- 235000019253 formic acid Nutrition 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 238000000605 extraction Methods 0.000 claims 3
- 150000002576 ketones Chemical class 0.000 claims 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- 210000002700 urine Anatomy 0.000 claims 2
- LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 claims 1
- LABTWGUMFABVFG-UHFFFAOYSA-N 1-propenyl methyl ketone Natural products CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 claims 1
- HLLSOEKIMZEGFV-UHFFFAOYSA-N 4-(dibutylsulfamoyl)benzoic acid Chemical compound CCCCN(CCCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 HLLSOEKIMZEGFV-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000257303 Hymenoptera Species 0.000 claims 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 150000007824 aliphatic compounds Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 231100000572 poisoning Toxicity 0.000 claims 1
- 230000000607 poisoning effect Effects 0.000 claims 1
- 239000012286 potassium permanganate Substances 0.000 claims 1
- 230000002035 prolonged effect Effects 0.000 claims 1
- 150000004672 propanoic acids Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 235000003441 saturated fatty acids Nutrition 0.000 claims 1
- 150000004671 saturated fatty acids Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000463 material Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Chemical compound [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- -1 propionic acid-urea-water Chemical compound 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000219495 Betulaceae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZCIBQBYQTHJFFP-UHFFFAOYSA-N C(CC)(=O)O.[S] Chemical compound C(CC)(=O)O.[S] ZCIBQBYQTHJFFP-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000012476 oxidizable substance Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60075166A | 1966-12-12 | 1966-12-12 | |
| US60073466A | 1966-12-12 | 1966-12-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1668783A1 DE1668783A1 (de) | 1972-01-27 |
| DE1668783B2 DE1668783B2 (de) | 1974-03-14 |
| DE1668783C3 true DE1668783C3 (enrdf_load_stackoverflow) | 1974-10-24 |
Family
ID=27083694
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671793712 Granted DE1793712A1 (de) | 1966-12-12 | 1967-11-07 | Verfahren zur Reinigung von Ameisensaeure |
| DE19671668783 Granted DE1668783B2 (de) | 1966-12-12 | 1967-11-07 | Verfahren zur Reinigung von Ameisensäure oder Propionsäure |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671793712 Granted DE1793712A1 (de) | 1966-12-12 | 1967-11-07 | Verfahren zur Reinigung von Ameisensaeure |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5141611B1 (enrdf_load_stackoverflow) |
| BE (1) | BE707783A (enrdf_load_stackoverflow) |
| DE (2) | DE1793712A1 (enrdf_load_stackoverflow) |
-
1967
- 1967-11-07 DE DE19671793712 patent/DE1793712A1/de active Granted
- 1967-11-07 DE DE19671668783 patent/DE1668783B2/de active Granted
- 1967-11-22 JP JP7482867A patent/JPS5141611B1/ja active Pending
- 1967-12-11 BE BE707783D patent/BE707783A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE1668783A1 (de) | 1972-01-27 |
| DE1793712A1 (de) | 1972-10-19 |
| DE1668783B2 (de) | 1974-03-14 |
| DE1793712C3 (enrdf_load_stackoverflow) | 1974-08-15 |
| DE1793712B2 (enrdf_load_stackoverflow) | 1974-01-03 |
| BE707783A (enrdf_load_stackoverflow) | 1968-06-11 |
| JPS5141611B1 (enrdf_load_stackoverflow) | 1976-11-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |