LU82401A1 - Verfahren zur herstellung von p-aminophenol - Google Patents

Verfahren zur herstellung von p-aminophenol Download PDF

Info

Publication number: LU82401A1
Authority: LU; Luxembourg
Prior art keywords: platinum; catalyst; alumina; nitrobenzene; hydrogenation
Prior art date: 1979-04-27

Application number

LU82401A

Other languages

German (de)

English (en)

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

1980-04-25

Publication date

1980-07-31

1980-04-25 Application filed by Mallinckrodt Inc filed Critical Mallinckrodt Inc

1980-07-31 Publication of LU82401A1 publication Critical patent/LU82401A1/de

Links

PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 title claims description 38
238000004519 manufacturing process Methods 0.000 title description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 66
239000003054 catalyst Substances 0.000 claims description 40
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 36
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 32
229910052697 platinum Inorganic materials 0.000 claims description 28
238000000034 method Methods 0.000 claims description 22
238000005984 hydrogenation reaction Methods 0.000 claims description 13
FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 7
229910001593 boehmite Inorganic materials 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
238000001354 calcination Methods 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000012431 aqueous reaction media Substances 0.000 claims description 3
238000000151 deposition Methods 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
238000011084 recovery Methods 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
230000007704 transition Effects 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229910052593 corundum Inorganic materials 0.000 description 2
239000010431 corundum Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000004682 monohydrates Chemical class 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
150000004684 trihydrates Chemical class 0.000 description 2
229910002706 AlOOH Inorganic materials 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
208000029618 autoimmune pulmonary alveolar proteinosis Diseases 0.000 description 1
VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910001679 gibbsite Inorganic materials 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
239000002609 medium Substances 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
229910052763 palladium Inorganic materials 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000002407 reforming Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000005979 thermal decomposition reaction Methods 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)

LU82401A 1979-04-27 1980-04-25 Verfahren zur herstellung von p-aminophenol LU82401A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3377879A	1979-04-27	1979-04-27
US3377879		1979-04-27

Publications (1)

Publication Number	Publication Date
LU82401A1 true LU82401A1 (de)	1980-07-31

Family

ID=21872387

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU82401A LU82401A1 (de)	1979-04-27	1980-04-25	Verfahren zur herstellung von p-aminophenol

Country Status (17)

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

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/en 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
CA1139317A (en)	1983-01-11
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 (da)	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
ES490886A0 (es)	1980-12-16
NO149472C (no)	1984-04-25

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