HU188168B - Process for producing fumaroic acid from wash water of outgases produced with oxidation of hydrocarbons - Google Patents
Process for producing fumaroic acid from wash water of outgases produced with oxidation of hydrocarbons Download PDFInfo
- Publication number
- HU188168B HU188168B HU821555A HU155582A HU188168B HU 188168 B HU188168 B HU 188168B HU 821555 A HU821555 A HU 821555A HU 155582 A HU155582 A HU 155582A HU 188168 B HU188168 B HU 188168B
- Authority
- HU
- Hungary
- Prior art keywords
- solution
- fumaric acid
- acid
- maleic acid
- isomerization
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 230000003647 oxidation Effects 0.000 title claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 5
- 239000002253 acid Substances 0.000 title description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 77
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 65
- 239000001530 fumaric acid Substances 0.000 claims abstract description 38
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 27
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 27
- 239000011976 maleic acid Substances 0.000 claims abstract description 27
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 19
- 239000012535 impurity Substances 0.000 claims abstract description 13
- 238000001914 filtration Methods 0.000 claims abstract description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 6
- 238000005201 scrubbing Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002912 waste gas Substances 0.000 claims description 4
- 239000012452 mother liquor Substances 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 abstract description 6
- 230000008025 crystallization Effects 0.000 abstract description 6
- 239000007789 gas Substances 0.000 abstract description 5
- 238000001035 drying Methods 0.000 abstract description 4
- 239000012467 final product Substances 0.000 abstract description 4
- 239000003643 water by type Substances 0.000 abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 3
- 238000004042 decolorization Methods 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 abstract description 2
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000009997 thermal pre-treatment Methods 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 238000010586 diagram Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229930192627 Naphthoquinone Natural products 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000002791 naphthoquinones Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 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 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000003226 decolorizating effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000010908 plant waste Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002351 wastewater Substances 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treating Waste Gases (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21766/81A IT1167537B (it) | 1981-05-18 | 1981-05-18 | Procedimento per la produzione di acido fumarico partendo da acque di lavaggio di gas esausti provenienti da ossidazione di idrocarburi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188168B true HU188168B (en) | 1986-03-28 |
Family
ID=11186557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU821555A HU188168B (en) | 1981-05-18 | 1982-05-17 | Process for producing fumaroic acid from wash water of outgases produced with oxidation of hydrocarbons |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5823641A (cs) |
| AU (1) | AU8380482A (cs) |
| BE (1) | BE893184A (cs) |
| BR (1) | BR8202862A (cs) |
| CS (1) | CS228927B2 (cs) |
| DE (1) | DE3213142A1 (cs) |
| FR (1) | FR2505822B1 (cs) |
| GB (1) | GB2098612B (cs) |
| HU (1) | HU188168B (cs) |
| IT (1) | IT1167537B (cs) |
| YU (1) | YU103882A (cs) |
| ZA (1) | ZA823068B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5929255A (en) * | 1996-07-11 | 1999-07-27 | Bp Amoco Corporation | Process for coproducing fumaric acid and maleic anhydride |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1321416A (fr) * | 1961-06-16 | 1963-03-22 | Scient Design Co | Procédé de préparation d'acide maléique de grande pureté |
-
1981
- 1981-05-18 IT IT21766/81A patent/IT1167537B/it active
-
1982
- 1982-04-08 DE DE19823213142 patent/DE3213142A1/de not_active Withdrawn
- 1982-05-04 ZA ZA823068A patent/ZA823068B/xx unknown
- 1982-05-14 BE BE0/208088A patent/BE893184A/fr not_active IP Right Cessation
- 1982-05-14 FR FR8208461A patent/FR2505822B1/fr not_active Expired
- 1982-05-14 GB GB8214088A patent/GB2098612B/en not_active Expired
- 1982-05-17 BR BR8202862A patent/BR8202862A/pt unknown
- 1982-05-17 CS CS823602A patent/CS228927B2/cs unknown
- 1982-05-17 YU YU01038/82A patent/YU103882A/xx unknown
- 1982-05-17 HU HU821555A patent/HU188168B/hu unknown
- 1982-05-18 AU AU83804/82A patent/AU8380482A/en not_active Abandoned
- 1982-05-18 JP JP57084683A patent/JPS5823641A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ZA823068B (en) | 1983-03-30 |
| JPS5823641A (ja) | 1983-02-12 |
| YU103882A (en) | 1985-04-30 |
| DE3213142A1 (de) | 1982-12-09 |
| IT8121766A0 (it) | 1981-05-18 |
| FR2505822A1 (fr) | 1982-11-19 |
| GB2098612A (en) | 1982-11-24 |
| BE893184A (fr) | 1982-08-30 |
| AU8380482A (en) | 1982-11-25 |
| IT1167537B (it) | 1987-05-13 |
| CS228927B2 (en) | 1984-05-14 |
| FR2505822B1 (fr) | 1985-09-06 |
| GB2098612B (en) | 1985-07-10 |
| BR8202862A (pt) | 1983-04-26 |
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