CA1270849A - Preparation de 2,6-diacetoxynaphtalene tres pur - Google Patents

Preparation de 2,6-diacetoxynaphtalene tres pur

Info

Publication number: CA1270849A
Authority: CA; Canada
Prior art keywords: acid; naphthalenediol; diacetoxynaphthalene; naphthalene; reaction
Prior art date: 1985-09-20
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 - Fee Related

Application number

CA000510823A

Other languages

English (en)

Inventor

Takashi Yamauchi

Takayuki Tanonaka

Hiroyuki Enari

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.)

Kureha Corp

Original Assignee

Kureha Corp

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.)

1985-09-20

Filing date

1986-06-04

Publication date

1990-06-26

1986-06-04 Application filed by Kureha Corp filed Critical Kureha Corp

1990-06-26 Application granted granted Critical

1990-06-26 Publication of CA1270849A publication Critical patent/CA1270849A/fr

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 39
JTUIDPCUTRXCPW-UHFFFAOYSA-N (6-acetyloxynaphthalen-2-yl) acetate Chemical compound C1=C(OC(C)=O)C=CC2=CC(OC(=O)C)=CC=C21 JTUIDPCUTRXCPW-UHFFFAOYSA-N 0.000 title claims abstract description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 63
MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 claims abstract description 57
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 52
239000000203 mixture Substances 0.000 claims abstract description 26
150000007522 mineralic acids Chemical class 0.000 claims abstract description 13
DXIUSVDANCIIAR-UHFFFAOYSA-N 2-[6-(2-hydroxypropan-2-yl)naphthalen-2-yl]propan-2-ol Chemical compound C1=C(C(C)(C)O)C=CC2=CC(C(C)(O)C)=CC=C21 DXIUSVDANCIIAR-UHFFFAOYSA-N 0.000 claims abstract description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 8
239000011973 solid acid Substances 0.000 claims abstract description 8
230000001590 oxidative effect Effects 0.000 claims abstract description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 33
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 22
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
230000021736 acetylation Effects 0.000 claims description 7
238000006640 acetylation reaction Methods 0.000 claims description 7
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
239000003456 ion exchange resin Substances 0.000 claims description 2
229920003303 ion-exchange polymer Polymers 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
230000000397 acetylating effect Effects 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 37
239000000243 solution Substances 0.000 description 20
239000002904 solvent Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
239000012452 mother liquor Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
229920000728 polyester Polymers 0.000 description 7
238000011084 recovery Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
239000012047 saturated solution Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
GWLLTEXUIOFAFE-UHFFFAOYSA-N 2,6-diisopropylnaphthalene Chemical compound C1=C(C(C)C)C=CC2=CC(C(C)C)=CC=C21 GWLLTEXUIOFAFE-UHFFFAOYSA-N 0.000 description 4
229920000106 Liquid crystal polymer Polymers 0.000 description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
230000002349 favourable effect Effects 0.000 description 4
230000004927 fusion Effects 0.000 description 4
229960004337 hydroquinone Drugs 0.000 description 4
239000010410 layer Substances 0.000 description 4
-1 naphtha-lene compound Chemical class 0.000 description 4
229940075566 naphthalene Drugs 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000004042 decolorization Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000000977 initiatory effect Effects 0.000 description 2
239000004973 liquid crystal related substance Substances 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000006277 sulfonation reaction Methods 0.000 description 2
AFPSJXJNWUOEGK-UHFFFAOYSA-N 2,6-bis(2-hydroperoxypropan-2-yl)naphthalene Chemical compound C1=C(C(C)(C)OO)C=CC2=CC(C(C)(OO)C)=CC=C21 AFPSJXJNWUOEGK-UHFFFAOYSA-N 0.000 description 1
YFTPFMCYSXCTRZ-UHFFFAOYSA-N 2-[1-(2-hydroxypropan-2-yl)naphthalen-2-yl]propan-2-ol Chemical compound C1=CC=CC2=C(C(C)(C)O)C(C(C)(O)C)=CC=C21 YFTPFMCYSXCTRZ-UHFFFAOYSA-N 0.000 description 1
LEARFTRDZQQTDN-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)phenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=C(C(C)(C)O)C=C1 LEARFTRDZQQTDN-UHFFFAOYSA-N 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000010543 cumene process Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
229920006351 engineering plastic Polymers 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Polyesters Or Polycarbonates (AREA)
Catalysts (AREA)

CA000510823A 1985-09-20 1986-06-04 Preparation de 2,6-diacetoxynaphtalene tres pur Expired - Fee Related CA1270849A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP60208372A JPH06719B2 (ja)	1985-09-20	1985-09-20	高純度な２，６−ジアセトキシナフタレンの製造法
JP208372/85		1985-09-20

Publications (1)

Publication Number	Publication Date
CA1270849A true CA1270849A (fr)	1990-06-26

Family

ID=16555193

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000510823A Expired - Fee Related CA1270849A (fr)	1985-09-20	1986-06-04	Preparation de 2,6-diacetoxynaphtalene tres pur

Country Status (2)

Country	Link
JP (1)	JPH06719B2 (fr)
CA (1)	CA1270849A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS63310839A (ja) *	1987-06-12	1988-12-19	Mitsui Petrochem Ind Ltd	ヒドロキシナフタレンの製造方法
JPH01164922A (ja) *	1987-12-21	1989-06-29	Matsushita Electric Ind Co Ltd	配向膜

1985
- 1985-09-20 JP JP60208372A patent/JPH06719B2/ja not_active Expired - Lifetime
1986
- 1986-06-04 CA CA000510823A patent/CA1270849A/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JPS6270339A (ja)	1987-03-31
JPH06719B2 (ja)	1994-01-05

Legal Events

Date	Code	Title	Description
1993-12-27	MKLA	Lapsed

Publication	Publication Date	Title
CA1270849A (fr)	1990-06-26	Preparation de 2,6-diacetoxynaphtalene tres pur
US3526666A (en)	1970-09-01	Synthesis of 2-hydroxy-4-alkoxybenzophenones
US4814521A (en)	1989-03-21	Process for producing 2,6-dihydroxynaphthalene and 2,6-diacetoxynaphthalene
US5399772A (en)	1995-03-21	Method of producing A 2,4'-dihydroxydiphenylsulfone
US4159389A (en)	1979-06-26	Process for the production of dicumyl peroxide
GB2176188A (en)	1986-12-17	Process for producing 2,6-naphthalenediol and 2,6-diacetoxynaphthalene
CA1253884A (fr)	1989-05-09	Preparation de 2,6-naphtalenediol
US4906790A (en)	1990-03-06	Method of oxidizing secondary alkyl substituted naphtalenes and a process of producing isopropylnaphthols
GB2104892A (en)	1983-03-16	A process for producing phloroglucin
EP0267761B1 (fr)	1992-01-29	Procédé pour la fabrication de 4,4'-dihydroxybiphényl
US3953526A (en)	1976-04-27	Synthesis of hydroquinone
US5545760A (en)	1996-08-13	Process for making fluorenones
KR950009481B1 (ko)	1995-08-23	1,4-비스(4-하이드록시벤조일)벤젠의 제조방법
CA1267911A (fr)	1990-04-17	Methode de preparation d'acide 6-hydroxy-2-naphtoique
JPH03258739A (ja)	1991-11-19	２，６―ナフタレンジオールの製造方法
US3373210A (en)	1968-03-12	Process for the production of alkylphenols
US2989566A (en)	1961-06-20	Manufacture of oxygen-containing organic compounds
JPH06211729A (ja)	1994-08-02	フルオレノンの製造方法
CN114426463B (zh)	2024-05-28	制备间苯二酚的方法
EP0318591B1 (fr)	1993-08-18	Procede de preparation de dihydroxynaphtalene
CA1304755C (fr)	1992-07-07	Procede pour la production de dihydroxynaphtalenes
JPH0470290B2 (fr)	1992-11-10
GB2192632A (en)	1988-01-20	Process for producing 2,6-dihydroxynaphthalene
JP2970161B2 (ja)	1999-11-02	２−アルキルレゾルシノールの製造法
JP3200470B2 (ja)	2001-08-20	アルキルテトラリンの製造方法