CH405277A - Procédé de fabrication de l'acide fumarique - Google Patents
Procédé de fabrication de l'acide fumariqueInfo
- Publication number
- CH405277A CH405277A CH791661A CH791661A CH405277A CH 405277 A CH405277 A CH 405277A CH 791661 A CH791661 A CH 791661A CH 791661 A CH791661 A CH 791661A CH 405277 A CH405277 A CH 405277A
- Authority
- CH
- Switzerland
- Prior art keywords
- sub
- bromine
- treatment
- carried out
- compound
- Prior art date
Links
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims description 36
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims description 28
- 239000001530 fumaric acid Substances 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 22
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 22
- 239000011976 maleic acid Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 11
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 9
- RZJISCZLORZZCA-UHFFFAOYSA-N azanium;cadmium;bromide Chemical compound [NH4+].[Br-].[Cd] RZJISCZLORZZCA-UHFFFAOYSA-N 0.000 claims description 8
- -1 peroxide compound Chemical class 0.000 claims description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- 229960001922 sodium perborate Drugs 0.000 claims description 2
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 7
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241001550224 Apha Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- RJYMRRJVDRJMJW-UHFFFAOYSA-L dibromomanganese Chemical compound Br[Mn]Br RJYMRRJVDRJMJW-UHFFFAOYSA-L 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4100860A | 1960-07-06 | 1960-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH405277A true CH405277A (fr) | 1966-01-15 |
Family
ID=21914215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH791661A CH405277A (fr) | 1960-07-06 | 1961-07-06 | Procédé de fabrication de l'acide fumarique |
Country Status (7)
-
1961
- 1961-07-03 BE BE605654A patent/BE605654A/fr unknown
- 1961-07-03 LU LU40348D patent/LU40348A1/xx unknown
- 1961-07-05 ES ES0268794A patent/ES268794A1/es not_active Expired
- 1961-07-06 GB GB2451461A patent/GB958694A/en not_active Expired
- 1961-07-06 SE SE703461A patent/SE313808B/xx unknown
- 1961-07-06 DE DE19611443109 patent/DE1443109C3/de not_active Expired
- 1961-07-06 CH CH791661A patent/CH405277A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1443109A1 (de) | 1968-10-24 |
| ES268794A1 (es) | 1961-12-16 |
| LU40348A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1961-09-04 |
| DE1443109B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-08-29 |
| SE313808B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-08-25 |
| DE1443109C3 (de) | 1975-04-30 |
| GB958694A (en) | 1964-05-21 |
| BE605654A (fr) | 1961-11-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2076674C (en) | Process for the accelerated production of stable solutions, in equilibrium, of peracetic acid in low concentrations | |
| EP1122249A1 (fr) | Procédé de fabrication d'un oxiranne | |
| CA1123441A (fr) | Procede de preparation du disulfure de benzothiazyle | |
| FR2486072A1 (fr) | Procede pour la fabrication de l'acide b-hydroxybutyrique et de ses oligocondensats | |
| CH405277A (fr) | Procédé de fabrication de l'acide fumarique | |
| CA1262805A (fr) | Procede de blanchiment de pates papetieres par le peroxyde d'hydrogene | |
| US7485758B2 (en) | Method for the production of phenol and acetone | |
| EP0084286B1 (fr) | Procédé perfectionné de fabrication de l'epsilon-caprolactone | |
| FR2717458A1 (fr) | Procédé de production de dioxyde de chlore. | |
| EP0349406B1 (fr) | Procédé de fabrication industrielle de solutions aqueuses d'acide glyoxylique | |
| CA2253768C (fr) | Generation de trifluorure de bore et d'acide sulfurique a partir d'hydrate de trifluorure de bore | |
| WO2000046192A1 (fr) | Procede de preparation de disulfure de tetramethylthiurame | |
| FR2516506A1 (fr) | Procede pour produire de l'acide glyoxylique par oxydation du glyoxal en solution aqueuse | |
| CH405278A (fr) | Procédé de fabrication d'acide fumarique blanc | |
| US4704476A (en) | Working up reaction mixtures containing cyclohexyl hydro-peroxide, cyclohexanol and cyclohexanone | |
| CA2168585A1 (fr) | Procede de preparation d'hydroperoxyde de cumene | |
| BE635230A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0726979B1 (fr) | Procede pour le blanchiment d'une pate a papier chimique | |
| FR2587705A1 (fr) | Procede pour la preparation de derives heterocycliques azotes aromatiques oxydes tels que le n-oxyde de pyridine | |
| WO1990000167A1 (fr) | Oxydation d'epoxy-alcools en epoxy-acides carboxyliques | |
| RU2221779C2 (ru) | Способ получения смеси сульфоксидов | |
| CH394155A (fr) | Procédé de fabrication de l'acide fumarique | |
| FR2577542A1 (fr) | Procede de preparation de chloroxyde de cuivre (ii) et chloroxyde de cuivre (ii) obtenu par ledit procede | |
| EP0179699A1 (fr) | Procédé de fabrication d'hydrate d'hydrazine | |
| BE378965A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |