CA1040659A - Production of hydroquinone - Google Patents
Production of hydroquinoneInfo
- Publication number
- CA1040659A CA1040659A CA243,700A CA243700A CA1040659A CA 1040659 A CA1040659 A CA 1040659A CA 243700 A CA243700 A CA 243700A CA 1040659 A CA1040659 A CA 1040659A
- Authority
- CA
- Canada
- Prior art keywords
- nitrobenzene
- hydroquinone
- reaction medium
- acid
- aqueous
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 238000004519 manufacturing process Methods 0.000 title description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 130
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000012429 reaction media Substances 0.000 claims abstract description 14
- 239000012431 aqueous reaction media Substances 0.000 claims abstract description 12
- 239000011260 aqueous acid Substances 0.000 claims abstract description 5
- 238000010521 absorption reaction Methods 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 36
- 230000007062 hydrolysis Effects 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 claims description 25
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 10
- 239000004615 ingredient Substances 0.000 claims description 10
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 9
- 229910052697 platinum Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 50
- 229960004337 hydroquinone Drugs 0.000 description 37
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000005984 hydrogenation reaction Methods 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229960004838 phosphoric acid Drugs 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000004254 Ammonium phosphate Substances 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001334 alicyclic compounds Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 2
- 235000019289 ammonium phosphates Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical class [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- -1 nitro- - Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JOKPITBUODAHEN-UHFFFAOYSA-N sulfanylideneplatinum Chemical compound [Pt]=S JOKPITBUODAHEN-UHFFFAOYSA-N 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/24—Sulfates of ammonium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/542,086 US3935283A (en) | 1972-06-29 | 1975-01-17 | Production of hydroquinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040659A true CA1040659A (en) | 1978-10-17 |
Family
ID=24162279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA243,700A Expired CA1040659A (en) | 1975-01-17 | 1976-01-16 | Production of hydroquinone |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5811413B2 (enrdf_load_stackoverflow) |
| BE (1) | BE833961A (enrdf_load_stackoverflow) |
| CA (1) | CA1040659A (enrdf_load_stackoverflow) |
| DE (1) | DE2601146C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2297827A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1493657A (enrdf_load_stackoverflow) |
| IT (1) | IT1060533B (enrdf_load_stackoverflow) |
| NL (1) | NL7511280A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015876A1 (de) * | 1979-03-01 | 1980-09-17 | Elprochine Ag | Verfahren zur Herstellung von Hydrochinon |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5232207B2 (enrdf_load_stackoverflow) * | 1971-09-10 | 1977-08-19 |
-
1975
- 1975-09-25 NL NL7511280A patent/NL7511280A/xx unknown
- 1975-09-29 BE BE160494A patent/BE833961A/xx not_active IP Right Cessation
- 1975-11-17 GB GB4043875A patent/GB1493657A/en not_active Expired
- 1975-12-19 FR FR7539013A patent/FR2297827A1/fr active Granted
-
1976
- 1976-01-05 IT IT4751576A patent/IT1060533B/it active
- 1976-01-07 JP JP51001345A patent/JPS5811413B2/ja not_active Expired
- 1976-01-14 DE DE19762601146 patent/DE2601146C3/de not_active Expired
- 1976-01-16 CA CA243,700A patent/CA1040659A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2601146B2 (de) | 1980-02-14 |
| IT1060533B (it) | 1982-08-20 |
| DE2601146C3 (de) | 1980-10-09 |
| FR2297827B1 (enrdf_load_stackoverflow) | 1979-01-19 |
| NL7511280A (nl) | 1976-07-20 |
| BE833961A (fr) | 1976-01-16 |
| DE2601146A1 (de) | 1976-07-22 |
| JPS5191217A (enrdf_load_stackoverflow) | 1976-08-10 |
| FR2297827A1 (fr) | 1976-08-13 |
| JPS5811413B2 (ja) | 1983-03-02 |
| GB1493657A (en) | 1977-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4431486A (en) | Azeotropic distillation of hydroxyacetic acid | |
| US5264624A (en) | Process for the recovery of adipic acid | |
| CA1040659A (en) | Production of hydroquinone | |
| US3530186A (en) | Process for the preparation of catechol and 2,2' - dihydroxydiphenylamine or lower alkyl ethers thereof | |
| EP0041837B1 (en) | Process for the purification of p-aminophenol | |
| CA1188325A (en) | Process for preparing a methyl phenol | |
| US4067905A (en) | Preparation of 2-amino-n-butanol | |
| US4233245A (en) | Preparation of tris(hydroxymethyl)aminomethane | |
| US3862247A (en) | Hydrolysis of para-aminophenol | |
| US3935283A (en) | Production of hydroquinone | |
| US4180687A (en) | Reaction of formaldehyde in butynediol | |
| US2157391A (en) | Catalytic reduction of nitro compounds | |
| US6689921B2 (en) | Preparation of biphenols by oxidative coupling of alkylphenols using a recyclable copper catalyst | |
| US4656279A (en) | Process for production of decahydroisoquinoline | |
| PL243580B1 (pl) | Sposób otrzymywania soli z kationem denatonium | |
| US2513132A (en) | Preparation of amino alcohols | |
| EP0298289B1 (en) | A process for the preparation of hydroxybenzoic acid | |
| US4532352A (en) | Separation of aniline and p-fluoroaniline | |
| JP2713014B2 (ja) | カプロラクタムの製法 | |
| DE69410898T2 (de) | Verfahren zur herstellung von n,n,-disubstituiertem aminophenol | |
| US4270010A (en) | Hydroquinone by hydrolysis of p-aminophenol or salts | |
| US2971980A (en) | Preparation of para-nitrobenzaldehyde and para-nitrobenzoic acid | |
| EP0321158B1 (en) | Production of m-aminophenol | |
| EP0027004A1 (en) | Method for producing unsymmetrical diphenylamines | |
| US3984466A (en) | Hydrolysis of 3,5-diamino benzoic acid to produce alpha-resorcylic acid |