JPH0569826B2 - - Google Patents

Info

Publication number: JPH0569826B2
Authority: JP; Japan
Prior art keywords: carboxylic acid; benzyl; group; reaction; acid
Prior art date: 1989-02-28
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 - Lifetime

Application number

JP1048943A

Other languages

English (en)

Japanese (ja)

Other versions

JPH02225470A (ja

Inventor

Takeshi Masuda

Naoki Kano

Shozo Miura

Natsuo Sawa

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.)

Shikoku Chemicals Corp

Original Assignee

Shikoku Chemicals 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.)

1989-02-28

Filing date

1989-02-28

Publication date

1993-10-01

1989-02-28 Application filed by Shikoku Chemicals Corp filed Critical Shikoku Chemicals Corp

1989-02-28 Priority to JP1048943A priority Critical patent/JPH02225470A/ja

1989-09-05 Priority to CA000610304A priority patent/CA1337428C/fr

1989-09-06 Priority to KR1019890012841A priority patent/KR970005532B1/ko

1989-09-06 Priority to EP89309024A priority patent/EP0358484B1/fr

1989-09-06 Priority to DE68916725T priority patent/DE68916725T2/de

1989-09-06 Priority to US07/403,460 priority patent/US5021584A/en

1990-09-07 Publication of JPH02225470A publication Critical patent/JPH02225470A/ja

1993-10-01 Publication of JPH0569826B2 publication Critical patent/JPH0569826B2/ja

Status Granted legal-status Critical Current

Links

RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 44
-1 imidazole compound Chemical class 0.000 claims description 34
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 27
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
235000019445 benzyl alcohol Nutrition 0.000 claims description 9
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 6
125000005907 alkyl ester group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
230000002194 synthesizing effect Effects 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
150000001735 carboxylic acids Chemical class 0.000 description 7
238000010438 heat treatment Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 5
229940073608 benzyl chloride Drugs 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
229910001854 alkali hydroxide Inorganic materials 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000003472 neutralizing effect Effects 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
238000005292 vacuum distillation Methods 0.000 description 3
PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
150000002460 imidazoles Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BWYQCNUKLXIXOK-UHFFFAOYSA-M 1,3-dibenzylimidazol-1-ium;chloride Chemical compound [Cl-].C1=C[N+](CC=2C=CC=CC=2)=CN1CC1=CC=CC=C1 BWYQCNUKLXIXOK-UHFFFAOYSA-M 0.000 description 1
150000004963 1-benzylimidazoles Chemical class 0.000 description 1
JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 1
ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000005185 salting out Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001308 synthesis method Methods 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

Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP1048943A 1988-09-06 1989-02-28 １―ベンジルイミダゾール化合物の合成方法 Granted JPH02225470A (ja)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
JP1048943A JPH02225470A (ja)	1989-02-28	1989-02-28	１―ベンジルイミダゾール化合物の合成方法
CA000610304A CA1337428C (fr)	1988-09-06	1989-09-05	Methode de preparation de derives de 1-benzylimidazole; nouveau compose
KR1019890012841A KR970005532B1 (ko)	1988-09-06	1989-09-06	1-벤질이미다졸 화합물의 제조 방법 및 신규 화합물
EP89309024A EP0358484B1 (fr)	1988-09-06	1989-09-06	Procédé de préparation de 1-benzylimidazole et son composé
DE68916725T DE68916725T2 (de)	1988-09-06	1989-09-06	Verfahren zur Herstellung von 1-Benzylimidazol und dessen Verbindung.
US07/403,460 US5021584A (en)	1988-09-06	1989-09-06	Process for preparation of 1-benzylimidazole compound

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP1048943A JPH02225470A (ja)	1989-02-28	1989-02-28	１―ベンジルイミダゾール化合物の合成方法

Publications (2)

Publication Number	Publication Date
JPH02225470A JPH02225470A (ja)	1990-09-07
JPH0569826B2 true JPH0569826B2 (fr)	1993-10-01

Family

ID=12817360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1048943A Granted JPH02225470A (ja)	1988-09-06	1989-02-28	１―ベンジルイミダゾール化合物の合成方法

Country Status (1)

Country	Link
JP (1)	JPH02225470A (fr)

1989
- 1989-02-28 JP JP1048943A patent/JPH02225470A/ja active Granted

Also Published As

Publication number	Publication date
JPH02225470A (ja)	1990-09-07

Legal Events

Date	Code	Title	Description
2004-06-22	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2005-06-14	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2006-05-30	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2007-05-29	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2008-04-24	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20081001 Year of fee payment: 15
2008-04-30	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20091001 Year of fee payment: 16
2009-02-28	EXPY	Cancellation because of completion of term
2009-05-01	FPAY	Renewal fee payment (event date is renewal date of database)	Free format text: PAYMENT UNTIL: 20091001 Year of fee payment: 16

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