CA1139317A - Methode de preparation de p-aminophenol - Google Patents

Methode de preparation de p-aminophenol

Info

Publication number: CA1139317A
Authority: CA; Canada
Prior art keywords: alumina; catalyst; platinum; nitrobenzene; gamma
Prior art date: 1979-04-27
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

Application number

CA000350576A

Other languages

English (en)

Inventor

Thomas J. Dunn

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mallinckrodt Inc

Original Assignee

Mallinckrodt Inc

Priority date (The priority date 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 date listed.)

1979-04-27

Filing date

1980-04-24

Publication date

1983-01-11

1980-04-24 Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc

1983-01-11 Application granted granted Critical

1983-01-11 Publication of CA1139317A publication Critical patent/CA1139317A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 26
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title claims abstract description 12
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 64
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 37
239000003054 catalyst Substances 0.000 claims abstract description 37
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims abstract description 36
229910052697 platinum Inorganic materials 0.000 claims abstract description 30
238000002360 preparation method Methods 0.000 claims abstract description 7
239000012431 aqueous reaction media Substances 0.000 claims abstract description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 11
FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 8
229910001593 boehmite Inorganic materials 0.000 claims description 6
238000001354 calcination Methods 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
238000000151 deposition Methods 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 9
238000011084 recovery Methods 0.000 abstract description 6
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract description 4
239000002253 acid Substances 0.000 abstract description 4
230000000202 analgesic effect Effects 0.000 abstract description 2
230000003197 catalytic effect Effects 0.000 abstract description 2
229960005489 paracetamol Drugs 0.000 abstract description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229910001679 gibbsite Inorganic materials 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
230000007704 transition Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
229910002706 AlOOH Inorganic materials 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229910021502 aluminium hydroxide Inorganic materials 0.000 description 2
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
KZNNRLXBDAAMDZ-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane trihydrate Chemical compound O.O.O.O=[Al]O[Al]=O KZNNRLXBDAAMDZ-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000002407 reforming Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- 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
- 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
- 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
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Physics & Mathematics (AREA)
Thermal Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CA000350576A 1979-04-27 1980-04-24 Methode de preparation de p-aminophenol Expired CA1139317A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3377879A	1979-04-27	1979-04-27
US33,778		1979-04-27

Publications (1)

Publication Number	Publication Date
CA1139317A true CA1139317A (fr)	1983-01-11

Family

ID=21872387

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000350576A Expired CA1139317A (fr)	1979-04-27	1980-04-24	Methode de preparation de p-aminophenol

Country Status (17)

Country	Link
JP (1)	JPS55145644A (fr)
BE (1)	BE882994A (fr)
CA (1)	CA1139317A (fr)
DE (1)	DE3015881A1 (fr)
DK (1)	DK173680A (fr)
ES (1)	ES490886A0 (fr)
FI (1)	FI801264A7 (fr)
FR (1)	FR2455029A1 (fr)
GB (1)	GB2048263B (fr)
GR (1)	GR67288B (fr)
IT (1)	IT1128522B (fr)
LU (1)	LU82401A1 (fr)
NL (1)	NL8002325A (fr)
NO (1)	NO149472C (fr)
PH (1)	PH14780A (fr)
PT (1)	PT71098A (fr)
SE (1)	SE8002783L (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE18547T1 (de) *	1982-01-29	1986-03-15	Mallinckrodt Inc	Verfahren zur herstellung von p-aminophenolen und alkylsubstituierten p-aminophenolen.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3265735A (en) *	1964-06-15	1966-08-09	Frontier Chemical Company	Manufacture of para-chloroaniline and para-aminophenol

1980
- 1980-04-09 GR GR61627A patent/GR67288B/el unknown
- 1980-04-14 PH PH23893A patent/PH14780A/en unknown
- 1980-04-14 SE SE8002783A patent/SE8002783L/xx not_active Application Discontinuation
- 1980-04-15 PT PT71098A patent/PT71098A/pt unknown
- 1980-04-15 GB GB8012453A patent/GB2048263B/en not_active Expired
- 1980-04-21 FI FI801264A patent/FI801264A7/fi not_active Application Discontinuation
- 1980-04-22 NL NL8002325A patent/NL8002325A/nl not_active Application Discontinuation
- 1980-04-22 IT IT48483/80A patent/IT1128522B/it active
- 1980-04-23 DK DK173680A patent/DK173680A/da active IP Right Grant
- 1980-04-24 CA CA000350576A patent/CA1139317A/fr not_active Expired
- 1980-04-24 DE DE19803015881 patent/DE3015881A1/de not_active Withdrawn
- 1980-04-25 BE BE0/200383A patent/BE882994A/fr not_active IP Right Cessation
- 1980-04-25 NO NO801221A patent/NO149472C/no unknown
- 1980-04-25 ES ES490886A patent/ES490886A0/es active Granted
- 1980-04-25 FR FR8009431A patent/FR2455029A1/fr active Pending
- 1980-04-25 LU LU82401A patent/LU82401A1/de unknown
- 1980-04-26 JP JP5608680A patent/JPS55145644A/ja active Pending

Also Published As

Publication number	Publication date
GB2048263B (en)	1983-05-25
IT8048483A0 (it)	1980-04-22
SE8002783L (sv)	1980-10-28
DK173680A (da)	1980-10-28
IT1128522B (it)	1986-05-28
FR2455029A1 (fr)	1980-11-21
GB2048263A (en)	1980-12-10
FI801264A7 (fi)	1981-01-01
NO149472B (no)	1984-01-16
DE3015881A1 (de)	1980-11-06
GR67288B (fr)	1981-06-29
NL8002325A (nl)	1980-10-29
PT71098A (en)	1980-05-01
NO801221L (no)	1980-10-28
BE882994A (fr)	1980-08-18
ES8102087A1 (es)	1980-12-16
PH14780A (en)	1981-12-09
JPS55145644A (en)	1980-11-13
LU82401A1 (de)	1980-07-31
ES490886A0 (es)	1980-12-16
NO149472C (no)	1984-04-25

Legal Events

Date	Code	Title	Description
2000-01-11	MKEX	Expiry

Publication	Publication Date	Title
AU650334B2 (en)	1994-06-16	Process for the preparation of a catalyst or catalyst precursor
AU668445B2 (en)	1996-05-02	Process for the synthesis of compositions based on mixed zirconium and cerium oxides, compositions thus obtained and uses of the latter
CA2181273C (fr)	2007-09-25	Procede pour la preparation d'un catalyseur utilise pour la conversion de gaz synthetiques
EP0736326B1 (fr)	2001-08-08	Catalyseurs Fischer-Tropsch contenant du fer et du cobalt
US7939462B2 (en)	2011-05-10	Composition based on cerium and zirconium oxides having a specific surface which is stable between 900° c and 1000° c method for the production and use thereof as a catalyst
US4273680A (en)	1981-06-16	Supported non-ferrous group VIII aluminate coprecipitated hydrogenation catalysts and process for their preparation
JPS6049135B2 (ja)	1985-10-31	二重多孔度を有する球状体及びその製造法
US4307248A (en)	1981-12-22	Process for hydrogenating organic compounds by use of non-ferrous group VIII aluminum coprecipitated catalysts
CA2841803A1 (fr)	2013-01-17	Procede de production de composites constitues d'oxyde d'aluminium et d'oxydes mixtes de cerium/zirconium
KR20000048863A (ko)	2000-07-25	구리/크롬 촉매 용도에 적합한 크롬 비함유 촉매의 제조 방법 및 이것의 용도
JP3389412B2 (ja)	2003-03-24	改良された低級炭化水素用水蒸気改質触媒
McVicker et al.	1983	Properties of aluminum-fluoride catalysts prepared by the fluoridation of aluminum oxide with trifluoromethane
KR100874678B1 (ko)	2008-12-18	Ｎｉ/ｔｉｏ2 수소화 촉매
JP3497202B2 (ja)	2004-02-16	不飽和化合物の選択的水素化のための触媒および方法並びに該触媒の製造法
EP2301663B1 (fr)	2021-06-16	Catalyseur pour la synthèse de fischer-tropsch et méthode de fabrication d'hydrocarbures
US4263225A (en)	1981-04-21	Hydrogenation process using supported nickel-cobalt-silica coprecipitated catalyst
US4264529A (en)	1981-04-28	Method for preparing p-aminophenol
US4318829A (en)	1982-03-09	Non-ferrous group VIII aluminum coprecipitated hydrogenation catalysts
EP0029675B1 (fr)	1984-03-14	Catalyseurs d'hydrogénation formés d'un coprécipité d'aluminium et d'un métal non ferreux du groupe VIII, procédé de préparation de ces catalyseurs, et leur utilisation dans des procédés d'hydrogénation
CA1140910A (fr)	1983-02-08	Catalyseurs supportes de l'hydrogenation, a base de cobalt et de silice coprecipites
JPS63123445A (ja)	1988-05-27	ヒドロゲルから作成した水添処理触媒の製造方法および製造された触媒
JP3310666B2 (ja)	2002-08-05	比表面積と多孔度の高い金属酸化物の合成方法、得られる酸化物、並びに該酸化物を含有する触媒
US4273939A (en)	1981-06-16	Process for hydrogenating organic compounds by use of non-ferrous group VIII aluminum coprecipitated catalysts
JPH06134305A (ja)	1994-05-17	耐熱性触媒およびその使用方法
JP3730792B2 (ja)	2006-01-05	炭化水素の異性化方法