JPS6126794B2 - - Google Patents

Info

Publication number: JPS6126794B2
Authority: JP; Japan
Prior art keywords: cobalt; formula; methanol; acid; aromatic carboxylic
Prior art date: 1978-05-15
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

JP5653178A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54148756A (en

Inventor

Akinobu Yoshisato

Teizo Yamaji

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.)

Teijin Ltd

Original Assignee

Teijin 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.)

1978-05-15

Filing date

1978-05-15

Publication date

1986-06-21

1978-05-15 Application filed by Teijin Ltd filed Critical Teijin Ltd

1978-05-15 Priority to JP5653178A priority Critical patent/JPS54148756A/ja

1979-11-21 Publication of JPS54148756A publication Critical patent/JPS54148756A/ja

1986-06-21 Publication of JPS6126794B2 publication Critical patent/JPS6126794B2/ja

Status Granted legal-status Critical Current

Links

-1 cobalt salt compound Chemical class 0.000 claims description 19
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 101
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluenecarboxylic acid Natural products CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 26
239000013078 crystal Substances 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000010941 cobalt Substances 0.000 description 12
229910017052 cobalt Inorganic materials 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
239000003960 organic solvent Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
150000001869 cobalt compounds Chemical class 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
150000001868 cobalt Chemical class 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 description 3
239000002274 desiccant Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000003973 paint Substances 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000005809 transesterification reaction Methods 0.000 description 3
REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012159 carrier gas Substances 0.000 description 2
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
239000012456 homogeneous solution Substances 0.000 description 2
230000006698 induction Effects 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
239000003446 ligand Substances 0.000 description 2
238000000034 method Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000004448 titration Methods 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
TWADJGWUKGOPFG-UHFFFAOYSA-N 2-methoxy-5-methyl-1,3-diphenylbenzene Chemical compound COC1=C(C=2C=CC=CC=2)C=C(C)C=C1C1=CC=CC=C1 TWADJGWUKGOPFG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-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
239000002202 Polyethylene glycol Substances 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 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
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940011182 cobalt acetate Drugs 0.000 description 1
ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 1
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
KPUNOVLMCQQCSK-UHFFFAOYSA-N diazomethane;ethoxyethane Chemical compound C=[N+]=[N-].CCOCC KPUNOVLMCQQCSK-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 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
150000008282 halocarbons Chemical class 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000000243 solution Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000013585 weight reducing agent Substances 0.000 description 1

Landscapes

Paints Or Removers (AREA)

JP5653178A 1978-05-15 1978-05-15 Cobaltous salt of aromatic carboxylic acid Granted JPS54148756A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP5653178A JPS54148756A (en)	1978-05-15	1978-05-15	Cobaltous salt of aromatic carboxylic acid

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5653178A JPS54148756A (en)	1978-05-15	1978-05-15	Cobaltous salt of aromatic carboxylic acid

Publications (2)

Publication Number	Publication Date
JPS54148756A JPS54148756A (en)	1979-11-21
JPS6126794B2 true JPS6126794B2 (fr)	1986-06-21

Family

ID=13029669

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5653178A Granted JPS54148756A (en)	1978-05-15	1978-05-15	Cobaltous salt of aromatic carboxylic acid

Country Status (1)

Country	Link
JP (1)	JPS54148756A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02157396A (ja) *	1988-12-06	1990-06-18	Touzai Yuatsu Kk	地中配管工事の方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS61130382A (ja) *	1984-11-30	1986-06-18	Nippon Soda Co Ltd	被覆用組成物、その被覆方法および被覆鋼材

1978
- 1978-05-15 JP JP5653178A patent/JPS54148756A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02157396A (ja) *	1988-12-06	1990-06-18	Touzai Yuatsu Kk	地中配管工事の方法

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Publication number	Publication date
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JPS6126794B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=13029669

Family Applications (1)

Country Status (1)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

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