CA1118791A - Recovery of para-aminophenol - Google Patents
Recovery of para-aminophenolInfo
- Publication number
- CA1118791A CA1118791A CA000339247A CA339247A CA1118791A CA 1118791 A CA1118791 A CA 1118791A CA 000339247 A CA000339247 A CA 000339247A CA 339247 A CA339247 A CA 339247A CA 1118791 A CA1118791 A CA 1118791A
- Authority
- CA
- Canada
- Prior art keywords
- para
- aminophenol
- aromatic amine
- solution
- upper layer
- 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
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title claims abstract description 182
- 238000011084 recovery Methods 0.000 title claims abstract description 10
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 63
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000000243 solution Substances 0.000 claims abstract description 32
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 239000002244 precipitate Substances 0.000 claims abstract description 16
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims abstract description 15
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical class CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003929 acidic solution Substances 0.000 claims abstract description 13
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 6
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 16
- 150000004992 toluidines Chemical class 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- -1 mixed toluidenes Chemical compound 0.000 abstract description 12
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract description 9
- 235000011130 ammonium sulphate Nutrition 0.000 abstract description 9
- 239000012045 crude solution Substances 0.000 abstract description 5
- 239000012429 reaction media Substances 0.000 abstract description 2
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 230000008569 process Effects 0.000 description 15
- 239000012535 impurity Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 230000029936 alkylation Effects 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 2
- QUGODTRVZDNSRF-UHFFFAOYSA-N 4-n-(2,3-dimethylphenyl)benzene-1,4-diamine Chemical compound CC1=CC=CC(NC=2C=CC(N)=CC=2)=C1C QUGODTRVZDNSRF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229940032296 ferric chloride Drugs 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005188 flotation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229960004838 phosphoric acid Drugs 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical class CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- VWNMIDRTNPTBJH-UHFFFAOYSA-N 4-n-(2-methylphenyl)benzene-1,4-diamine Chemical compound CC1=CC=CC=C1NC1=CC=C(N)C=C1 VWNMIDRTNPTBJH-UHFFFAOYSA-N 0.000 description 1
- SKSQPNSNZNEATE-UHFFFAOYSA-N C1(=C(C(=CC=C1)C)C)NC1=CC=C(C=C1)NC1=C(C(=CC=C1)C)C.C1(=C(C=CC=C1)NC1=CC=C(C=C1)NC1=C(C=CC=C1)C)C.C1(=CC=CC=C1)NC1=CC=C(C=C1)NC1=CC=CC=C1 Chemical compound C1(=C(C(=CC=C1)C)C)NC1=CC=C(C=C1)NC1=C(C(=CC=C1)C)C.C1(=C(C=CC=C1)NC1=CC=C(C=C1)NC1=C(C=CC=C1)C)C.C1(=CC=CC=C1)NC1=CC=C(C=C1)NC1=CC=CC=C1 SKSQPNSNZNEATE-UHFFFAOYSA-N 0.000 description 1
- 101000635799 Homo sapiens Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Proteins 0.000 description 1
- 102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 229960000355 copper sulfate Drugs 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 1
- IEECXTSVVFWGSE-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Fe+3] IEECXTSVVFWGSE-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical class [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/958,868 US4224247A (en) | 1978-11-08 | 1978-11-08 | Recovery of para-aminophenol |
| US958,868 | 1978-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1118791A true CA1118791A (en) | 1982-02-23 |
Family
ID=25501394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000339247A Expired CA1118791A (en) | 1978-11-08 | 1979-11-06 | Recovery of para-aminophenol |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4224247A (enExample) |
| JP (1) | JPS5569544A (enExample) |
| BE (1) | BE879853A (enExample) |
| CA (1) | CA1118791A (enExample) |
| CH (1) | CH644088A5 (enExample) |
| DE (1) | DE2945140A1 (enExample) |
| FR (2) | FR2440940A1 (enExample) |
| GB (1) | GB2036018B (enExample) |
| GR (1) | GR68186B (enExample) |
| IT (1) | IT1164134B (enExample) |
| NL (1) | NL7907957A (enExample) |
| SE (2) | SE7909028L (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4256669A (en) * | 1978-11-08 | 1981-03-17 | Mallinckrodt, Inc. | Para-aminophenol derivatives |
| FR2811670B1 (fr) * | 2000-07-13 | 2004-05-14 | Rhodia Chimie Sa | Stabilisation de compositions polymeriques, organosiliciques ou silicone |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2053785A (en) * | 1933-06-02 | 1936-09-08 | Goodrich Co B F | Antioxidants |
| US2048823A (en) * | 1933-06-02 | 1936-07-28 | Goodrich Co B F | Antioxidant |
| US2087199A (en) * | 1934-02-08 | 1937-07-13 | Wingfoot Corp | Age resistor |
| US3418373A (en) * | 1965-04-12 | 1968-12-24 | Monsanto Co | Preparation of aromatic diamine mixtures |
| US3383416A (en) * | 1965-07-08 | 1968-05-14 | Roland G. Benner | Process for preparing aminophenol |
| US3432460A (en) * | 1968-02-19 | 1969-03-11 | Goodyear Tire & Rubber | Antiozonants |
| BE757391A (fr) * | 1969-10-16 | 1971-04-13 | Howard Hall & Cy | Purification de p-aminophenol |
| JPS5344531A (en) * | 1976-10-05 | 1978-04-21 | Mitsui Toatsu Chem Inc | Purification of p-aminophenol |
| US4139562A (en) * | 1978-03-13 | 1979-02-13 | Mitsui Toatsu Chemicals, Inc. | Process for purifying crude p-aminophenol |
| US4256669A (en) * | 1978-11-08 | 1981-03-17 | Mallinckrodt, Inc. | Para-aminophenol derivatives |
-
1978
- 1978-11-08 US US05/958,868 patent/US4224247A/en not_active Expired - Lifetime
-
1979
- 1979-10-30 NL NL7907957A patent/NL7907957A/nl not_active Application Discontinuation
- 1979-10-31 SE SE7909028A patent/SE7909028L/ not_active Application Discontinuation
- 1979-11-03 GR GR60411A patent/GR68186B/el unknown
- 1979-11-05 IT IT50741/79A patent/IT1164134B/it active
- 1979-11-06 BE BE0/197988A patent/BE879853A/fr not_active IP Right Cessation
- 1979-11-06 GB GB7938459A patent/GB2036018B/en not_active Expired
- 1979-11-06 CA CA000339247A patent/CA1118791A/en not_active Expired
- 1979-11-07 CH CH996779A patent/CH644088A5/de not_active IP Right Cessation
- 1979-11-07 JP JP14491179A patent/JPS5569544A/ja active Pending
- 1979-11-08 DE DE19792945140 patent/DE2945140A1/de not_active Withdrawn
- 1979-11-08 FR FR7927584A patent/FR2440940A1/fr active Granted
-
1980
- 1980-02-28 FR FR8004476A patent/FR2443453A1/fr active Granted
-
1985
- 1985-01-22 SE SE8500289A patent/SE8500289D0/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BE879853A (fr) | 1980-03-03 |
| GB2036018A (en) | 1980-06-25 |
| US4224247A (en) | 1980-09-23 |
| GB2036018B (en) | 1983-03-02 |
| SE8500289L (sv) | 1985-01-22 |
| FR2440940A1 (fr) | 1980-06-06 |
| IT1164134B (it) | 1987-04-08 |
| FR2443453B1 (enExample) | 1984-01-20 |
| CH644088A5 (de) | 1984-07-13 |
| DE2945140A1 (de) | 1980-05-29 |
| NL7907957A (nl) | 1980-05-12 |
| SE7909028L (sv) | 1980-05-09 |
| FR2443453A1 (fr) | 1980-07-04 |
| GR68186B (enExample) | 1981-11-09 |
| JPS5569544A (en) | 1980-05-26 |
| SE8500289D0 (sv) | 1985-01-22 |
| FR2440940B1 (enExample) | 1984-01-20 |
| IT7950741A0 (it) | 1979-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |