NL8100356A - Regioselectieve bereiding van alfa- en beta-naftol. - Google Patents

Regioselectieve bereiding van alfa- en beta-naftol. Download PDF

Info

Publication number: NL8100356A
Authority: NL; Netherlands
Prior art keywords: acid; naphthalene; naphthol; hydrogen peroxide; pentafluoride
Prior art date: 1979-10-05

Application number

NL8100356A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ugine Kuhlmann

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.)

1979-10-05

Filing date

1981-01-26

Publication date

1982-08-16

1981-01-26 Application filed by Ugine Kuhlmann filed Critical Ugine Kuhlmann

1982-08-16 Publication of NL8100356A publication Critical patent/NL8100356A/nl

Links

JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title claims description 7
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 74
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 20
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 16
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 15
238000000034 method Methods 0.000 claims description 11
239000003930 superacid Substances 0.000 claims description 11
229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 8
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 8
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 8
230000033444 hydroxylation Effects 0.000 claims description 7
238000005805 hydroxylation reaction Methods 0.000 claims description 7
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 claims description 4
229910015900 BF3 Inorganic materials 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
AOLPZAHRYHXPLR-UHFFFAOYSA-I pentafluoroniobium Chemical compound F[Nb](F)(F)(F)F AOLPZAHRYHXPLR-UHFFFAOYSA-I 0.000 claims 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
230000000640 hydroxylating effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000000463 material Substances 0.000 description 9
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 9
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000005457 ice water Substances 0.000 description 5
150000004780 naphthols Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
-1 aryl peroxides Chemical class 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IXPAAHZTOUOJJM-UHFFFAOYSA-N sulfuryl chloride fluoride Chemical compound FS(Cl)(=O)=O IXPAAHZTOUOJJM-UHFFFAOYSA-N 0.000 description 3
238000011282 treatment Methods 0.000 description 3
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
239000003513 alkali Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
241000231258 Suillus granulatus Species 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
QBEZHXMLBPSPCU-UHFFFAOYSA-N hydrogen peroxide;1-propan-2-ylnaphthalene Chemical class OO.C1=CC=C2C(C(C)C)=CC=CC2=C1 QBEZHXMLBPSPCU-UHFFFAOYSA-N 0.000 description 1
150000004680 hydrogen peroxides Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010410 layer Substances 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000005002 naphthylamines Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000002861 polymer material Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by oxidation reactions introducing directly hydroxy groups on a =CH-group belonging to a six-membered aromatic ring with the aid of other oxidants than molecular oxygen or their mixtures with molecular oxygen

Landscapes

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

NL8100356A 1979-10-05 1981-01-26 Regioselectieve bereiding van alfa- en beta-naftol. NL8100356A (nl)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US8215279		1979-10-05
US06/082,152 US4419528A (en)	1979-10-05	1979-10-05	Regioselective preparation of α- or β-naphthol
FR8100716		1981-01-16
FR8100716A FR2498179A1 (fr)	1979-10-05	1981-01-16	Preparation regioselective de l'a- et du b-naphtol
DE3102305A DE3102305C2 (de)	1979-10-05	1981-01-24	Verfahren zur Herstellung von α- oder β-Naphthol durch regioselektive Hydroxylierung von Naphthalin mit Wasserstoffperoxid
DE3102305		1981-01-24

Publications (1)

Publication Number	Publication Date
NL8100356A true NL8100356A (nl)	1982-08-16

Family

ID=27189102

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8100356A NL8100356A (nl)	1979-10-05	1981-01-26	Regioselectieve bereiding van alfa- en beta-naftol.

Country Status (8)

Country	Link
US (1)	US4419528A (fr)
JP (1)	JPS57123131A (fr)
BE (1)	BE887201A (fr)
CA (1)	CA1176662A (fr)
DE (1)	DE3102305C2 (fr)
FR (1)	FR2498179A1 (fr)
GB (1)	GB2090827B (fr)
NL (1)	NL8100356A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2548179B1 (fr) *	1983-06-29	1986-06-20	Ugine Kuhlmann	Procede de preparation d'amino-phenols par hydroxylation d'anilines en milieu superacide au moyen du peroxyde d'hydrogene
US4814521A (en) *	1985-06-07	1989-03-21	Kureha Kagaku Kogyo Kabushiki Kaisha	Process for producing 2,6-dihydroxynaphthalene and 2,6-diacetoxynaphthalene
DE3774035D1 (de) *	1986-07-29	1991-11-28	Mitsubishi Gas Chemical Co	Verfahren zur herstellung von pech, verwertbar zur herstellung von kohlenstoffkoerpern.
EP0867424B1 (fr) *	1997-03-27	2000-12-13	Council of Scientific and Industrial Research	Procédé pour la préparation d'alpha et de bèta naphtol par hydroxylation de naphtalène mettant en oeuvre un complexe d'un métal de transition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3407237A (en) *	1965-11-08	1968-10-22	Universal Oil Prod Co	Preparation of hydroxylated aromatic compounds
US3600447A (en) *	1965-12-20	1971-08-17	Universal Oil Prod Co	Preparation of hydroxylated aromatic compounds
US3453332A (en) *	1967-11-29	1969-07-01	Universal Oil Prod Co	Hydroxylation of aromatic compounds
US3816545A (en) *	1971-02-16	1974-06-11	Universal Oil Prod Co	Hydroxylation of aromatic compounds
US3839467A (en) *	1972-08-31	1974-10-01	Universal Oil Prod Co	Preparation of hydroxylated aromatic compounds
JPS5217015B2 (fr) *	1973-01-31	1977-05-12
DE2410758C3 (de) *	1974-03-06	1981-01-08	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von mehrwertigen substituierten Phenolen bzw. Monoäthern mehrwertiger Phenole durch Kernhydroxylierung von Phenolen oder Phenoläthern
DE2410742C3 (de) *	1974-03-06	1981-01-08	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von Brenzkatechin und Hydrochinon durch Kernhydroxylierung von Phenol

1979
- 1979-10-05 US US06/082,152 patent/US4419528A/en not_active Expired - Lifetime
1981
- 1981-01-13 GB GB8100992A patent/GB2090827B/en not_active Expired
- 1981-01-16 FR FR8100716A patent/FR2498179A1/fr not_active Withdrawn
- 1981-01-21 JP JP56006559A patent/JPS57123131A/ja active Pending
- 1981-01-23 BE BE0/203571A patent/BE887201A/fr not_active IP Right Cessation
- 1981-01-24 DE DE3102305A patent/DE3102305C2/de not_active Expired
- 1981-01-26 CA CA000369273A patent/CA1176662A/fr not_active Expired
- 1981-01-26 NL NL8100356A patent/NL8100356A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA1176662A (fr)	1984-10-23
FR2498179A1 (fr)	1982-07-23
DE3102305A1 (de)	1982-08-26
US4419528A (en)	1983-12-06
DE3102305C2 (de)	1985-08-22
JPS57123131A (en)	1982-07-31
BE887201A (fr)	1981-07-23
GB2090827A (en)	1982-07-21
GB2090827B (en)	1984-10-03

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-03-01	BV	The patent application has lapsed

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Vittimberga et al.	1970	Peroxide-initiated decarbonylation of 9-carbazolylacetaldehyde. Possible free-radical displacement
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