JPH0124138B2 - - Google Patents

Info

Publication number: JPH0124138B2
Authority: JP; Japan
Prior art keywords: acenaphthenes; acenaphthylenes; metal; peroxide; reaction
Prior art date: 1981-10-20
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

Application number

JP16635781A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5869823A (ja

Inventor

Motohiko Yoshikawa

Koichi Takase

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.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co Ltd

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.)

1981-10-20

Filing date

1981-10-20

Publication date

1989-05-10

1981-10-20 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1981-10-20 Priority to JP16635781A priority Critical patent/JPS5869823A/ja

1983-04-26 Publication of JPS5869823A publication Critical patent/JPS5869823A/ja

1989-05-10 Publication of JPH0124138B2 publication Critical patent/JPH0124138B2/ja

Status Granted legal-status Critical Current

Links

238000000034 method Methods 0.000 claims description 25
150000001240 acenaphthylenes Chemical class 0.000 claims description 14
150000001239 acenaphthenes Chemical class 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
150000004972 metal peroxides Chemical class 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 9
UPWOEMHINGJHOB-UHFFFAOYSA-N oxo(oxocobaltiooxy)cobalt Chemical compound O=[Co]O[Co]=O UPWOEMHINGJHOB-UHFFFAOYSA-N 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 4
DRZNOPRRQNUPSF-UHFFFAOYSA-N 1-bromo-1,2-dihydroacenaphthylene Chemical compound C1=CC(C(Br)C2)=C3C2=CC=CC3=C1 DRZNOPRRQNUPSF-UHFFFAOYSA-N 0.000 claims description 3
ANIXIIYQBGBGRI-UHFFFAOYSA-N 1-chloro-1,2-dihydroacenaphthylene Chemical compound C1=CC(C(Cl)C2)=C3C2=CC=CC3=C1 ANIXIIYQBGBGRI-UHFFFAOYSA-N 0.000 claims description 3
CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 claims description 3
-1 nickel peroxide Chemical class 0.000 claims description 3
239000002994 raw material Substances 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
229910044991 metal oxide Inorganic materials 0.000 description 6
150000004706 metal oxides Chemical class 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
229910001385 heavy metal Inorganic materials 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000008929 regeneration Effects 0.000 description 3
238000011069 regeneration method Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000005708 Sodium hypochlorite Substances 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
238000007033 dehydrochlorination reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000001308 synthesis method Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JJENRBJFTBKLOV-UHFFFAOYSA-N 1,2,2-tribromo-1H-acenaphthylene Chemical compound BrC1C(C=2C=CC=C3C=CC=C1C=23)(Br)Br JJENRBJFTBKLOV-UHFFFAOYSA-N 0.000 description 1
UUOJQDOCFHDSBH-UHFFFAOYSA-N 1,2,2-trichloro-1h-acenaphthylene Chemical compound C1=CC(C(C2Cl)(Cl)Cl)=C3C2=CC=CC3=C1 UUOJQDOCFHDSBH-UHFFFAOYSA-N 0.000 description 1
SGVYNSUGXGDLGL-UHFFFAOYSA-N 1,2-dichloroacenaphthylene Chemical group C1=CC(C(Cl)=C2Cl)=C3C2=CC=CC3=C1 SGVYNSUGXGDLGL-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
GJVBRRZHNXEIID-UHFFFAOYSA-N 2,2-dibromo-1H-acenaphthylene Chemical compound BrC1(CC2=CC=CC3=CC=CC1=C23)Br GJVBRRZHNXEIID-UHFFFAOYSA-N 0.000 description 1
NZHXMSNRVKBDMH-UHFFFAOYSA-N 2,2-dichloro-1h-acenaphthylene Chemical compound C1=CC(C(Cl)(Cl)C2)=C3C2=CC=CC3=C1 NZHXMSNRVKBDMH-UHFFFAOYSA-N 0.000 description 1
QQTNONSQLWTQPU-UHFFFAOYSA-N 5,6-dichloro-1,2-dihydroacenaphthylene Chemical compound C1CC2=CC=C(Cl)C3=C2C1=CC=C3Cl QQTNONSQLWTQPU-UHFFFAOYSA-N 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
229910000361 cobalt sulfate Inorganic materials 0.000 description 1
229940044175 cobalt sulfate Drugs 0.000 description 1
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000004821 distillation Methods 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
238000004817 gas chromatography Methods 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
230000036541 health Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
229910000464 lead oxide Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000005486 naphthalic acid group Chemical class 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000012856 packing Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP16635781A 1981-10-20 1981-10-20 アセナフチレン類の製造方法 Granted JPS5869823A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP16635781A JPS5869823A (ja)	1981-10-20	1981-10-20	アセナフチレン類の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16635781A JPS5869823A (ja)	1981-10-20	1981-10-20	アセナフチレン類の製造方法

Publications (2)

Publication Number	Publication Date
JPS5869823A JPS5869823A (ja)	1983-04-26
JPH0124138B2 true JPH0124138B2 (fr)	1989-05-10

Family

ID=15829881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16635781A Granted JPS5869823A (ja)	1981-10-20	1981-10-20	アセナフチレン類の製造方法

Country Status (1)

Country	Link
JP (1)	JPS5869823A (fr)

1981
- 1981-10-20 JP JP16635781A patent/JPS5869823A/ja active Granted

Also Published As

Publication number	Publication date
JPS5869823A (ja)	1983-04-26

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