Title:
NITRATION OR CARBOXYLATION CATALYSTS
Document Type and Number:
WIPO Patent Application WO/1998/030329
Kind Code:
A1
Abstract:
At least one functional group selected between nitro and carboxyl groups can be introduced into a substrate by bringing the substrate into contact with at least one reactant selected from among (i) nitrogen oxides and (ii) carbon monoxide/oxygen mixtures in the presence of an imide compound represented by general formula (1), wherein R?1� and R?2� are each hydrogen, halogeno, alkyl, aryl or cycloalkyl, or alternatively they may be united to form a double bond or an aromatic or nonaromatic ring; W is O or OH; and n is 1 to 3, (e.g., N-hydroxy-phthalimide). The nitrogen oxides include compounds for the general formula: N�x?O�y? (such as N�2?O�3? and NO�2?), and the substrate includes compounds bearing methyne carbon atoms, such as adamantane, and aromatic compounds having a methyl or methylene group at the position adjacent to the aromatic ring. Such a process enables efficient nitration or carboxylation even under relatively mild conditions.
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Inventors:
ISHII YASUTAKA (JP)
NAKANO TATSUYA (JP)
SAKAGUCHI SATOSHI (JP)
NAKANO TATSUYA (JP)
SAKAGUCHI SATOSHI (JP)
Application Number:
PCT/JP1998/000079
Publication Date:
July 16, 1998
Filing Date:
January 13, 1998
Export Citation:
Assignee:
DAICEL CHEM (JP)
ISHII YASUTAKA (JP)
NAKANO TATSUYA (JP)
SAKAGUCHI SATOSHI (JP)
ISHII YASUTAKA (JP)
NAKANO TATSUYA (JP)
SAKAGUCHI SATOSHI (JP)
International Classes:
B01J31/02; C07B41/08; C07B43/02; C07C45/36; C07C51/10; C07C61/28; C07C62/06; C07C69/00; C07C201/08; C07C205/04; C07C205/05; C07C205/06; C07C205/18; C07C205/55; C07C211/35; C07C211/37; C07C215/42; C07C229/50; C07C233/10; C07C233/14; C07C233/23; C07C233/41; C07C233/52; C07C233/58; C07C233/62; C07C235/40; C07C235/82; C07C237/24; C07C265/10; C07C271/24; B01J31/22; (IPC1-7): B01J31/02; B01J31/26; C07C201/08; C07C51/10; C07C61/28; C07C211/35; C07C265/10; C07C205/55; C07C62/06; C07C271/24; C07B43/02; C07B41/08
Foreign References:
| JPH0774168B2 | 1995-08-09 | |||
| JPS5692847A | 1981-07-27 | |||
| JPS5671075A | 1981-06-13 | |||
| JPH09143109A | 1997-06-03 | |||
| JPH09278675A | 1997-10-28 |
Other References:
GILARDI R., ET AL.: "STRUCTURE OF 1-ANIMO-3,5,7,-TRINITROADAMANTANE.", ACTA CRYSTALLOGRAPHICA SECTION C. CRYSTAL STRUCTURE COMMUNICATIONS, MUNKSGAARD, COPENHAGEN, DK, vol. C47., no. 09., 1 January 1991 (1991-01-01), DK, pages 1914 - 1916., XP000901387, ISSN: 0108-2701, DOI: 10.1107/S0108270191001853
ZAJAC W W, WALTERS T R, WOODS J M: "1-AMINO-3,5,7-TRINITROADAMANTANE: AN UNEXPECTED OXIDATION PRODUCT OF 1,3,5,7-TETRAAMINOADAMANTANE. AN IMPROVED SYNTHESIS OF 1,3,5,7-TETRANITROADAMANTANE", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 54, no. 10, 1 January 1989 (1989-01-01), US, pages 2468 - 2471, XP001008036, ISSN: 0022-3263, DOI: 10.1021/jo00271a049
KHIL'CHEVSKII A N, ET AL.: "REACTION OF ADAMANTANE AND ADAMANTANE- AND BICYCLO(3.3.1)NONANE-TYPE CARBOXYLIC ACIDS WITH ACETONITRILE IN LIQUID BROMINE", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. 32, no. 07, 1 January 1966 (1966-01-01), MOSCOW, RU, pages 1022 - 1024, XP001007124, ISSN: 0514-7492
MELLA M, ET AL.: "OXIDATIVE FUNCTIONALIZATION OF ADAMANTANE AND SOME OF ITS DERIVATIVES IN SOLUTION", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 61, no. 04, 23 February 1996 (1996-02-23), US, pages 1413 - 1422, XP001007247, ISSN: 0022-3263, DOI: 10.1021/jo951645y
STEPANOV F N, ET AL.: "ADAMANTANE AND ITS DERIVATIVES VIII. SYNTHESIS AND ACID HYDROLYSIS OF TRI- AND TETRA-SUBSTITUTED ACYLAMINO DERIVATIVES OF ADAMANTANE", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. 02, no. 09, 1 January 1966 (1966-01-01), MOSCOW, RU, pages 1612 - 1615, XP001007122, ISSN: 0514-7492
VISHNEVSKII E. N., ET AL.: "NITRATION OF ADAMANTANE BY NITROGEN DIOXIDE.", JOURNAL OF ORGANIC CHEMISTRY OF THE USSR = ZHURNAL ORGANICHESKOI KHIMII, M A I K NAUKA - INTERPERIODICA, RU, vol. 32., no. 07., 1 January 1996 (1996-01-01), RU, pages 1030 - 1035., XP002910951, ISSN: 0022-3271
See also references of EP 0897747A4
ZAJAC W W, WALTERS T R, WOODS J M: "1-AMINO-3,5,7-TRINITROADAMANTANE: AN UNEXPECTED OXIDATION PRODUCT OF 1,3,5,7-TETRAAMINOADAMANTANE. AN IMPROVED SYNTHESIS OF 1,3,5,7-TETRANITROADAMANTANE", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 54, no. 10, 1 January 1989 (1989-01-01), US, pages 2468 - 2471, XP001008036, ISSN: 0022-3263, DOI: 10.1021/jo00271a049
KHIL'CHEVSKII A N, ET AL.: "REACTION OF ADAMANTANE AND ADAMANTANE- AND BICYCLO(3.3.1)NONANE-TYPE CARBOXYLIC ACIDS WITH ACETONITRILE IN LIQUID BROMINE", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. 32, no. 07, 1 January 1966 (1966-01-01), MOSCOW, RU, pages 1022 - 1024, XP001007124, ISSN: 0514-7492
MELLA M, ET AL.: "OXIDATIVE FUNCTIONALIZATION OF ADAMANTANE AND SOME OF ITS DERIVATIVES IN SOLUTION", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 61, no. 04, 23 February 1996 (1996-02-23), US, pages 1413 - 1422, XP001007247, ISSN: 0022-3263, DOI: 10.1021/jo951645y
STEPANOV F N, ET AL.: "ADAMANTANE AND ITS DERIVATIVES VIII. SYNTHESIS AND ACID HYDROLYSIS OF TRI- AND TETRA-SUBSTITUTED ACYLAMINO DERIVATIVES OF ADAMANTANE", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. 02, no. 09, 1 January 1966 (1966-01-01), MOSCOW, RU, pages 1612 - 1615, XP001007122, ISSN: 0514-7492
VISHNEVSKII E. N., ET AL.: "NITRATION OF ADAMANTANE BY NITROGEN DIOXIDE.", JOURNAL OF ORGANIC CHEMISTRY OF THE USSR = ZHURNAL ORGANICHESKOI KHIMII, M A I K NAUKA - INTERPERIODICA, RU, vol. 32., no. 07., 1 January 1996 (1996-01-01), RU, pages 1030 - 1035., XP002910951, ISSN: 0022-3271
See also references of EP 0897747A4
Attorney, Agent or Firm:
Kuwata, Mitsuo (10th floor 3-19, Nishitemma 6-chome, Kita-k, Osaka-shi Osaka 530, JP)
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