US4132715A
Expired / Lapsed
US
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Process for the production of maleimides
Assignee: Novartis Corp
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Filing: 1977-03-30
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Granted: 1979-01-02
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Expires: 1997-03-30
Abstract
Abstract There is described a process for the production of maleimides, particularly N-substituted maleimides or N,N'-bis-maleimides, by isomerization of the corresponding isoimides in the presence of specific catalysts, such as mixtures of phenol and triethylamine. Maleimides of high purity and in good to very good yields under mild conditions and with the use of small amounts of catalyst are obtained by the process according to the invention.
Inventors
- 👤 Martin Roth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 20:06
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/44; C07D207/444; C07D207/448; C07D207/452; C07D307/00; C07D307/02; C07D307/34
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
414 words
Process for the production of an imide of the formula I ##STR22## wherein n represents the number 1 or 2, Q represents, if n is 1, phenyl, 1-naphthyl, 2-naphtyl, or said phenyl or said naphthyl groups substituted by 1 to 3 moieties selected from the group consisting of halogen, hydroxyl, alkyl of 1 to 8 carbon atoms, halogenoalkyl of 1 to 3 carbon atoms, alkylthio of 1 to 4 carbon atoms, N,N-dialkylamino of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenoxy, alkoxycarbonyl of 2 to 5 carbon atoms; --SO 2 Y, --NHCOY, ##STR23## where Y is phenyl or alkyl of 1 to 4 carbon atoms, Y 1 is hydrogen, phenyl, naphthyl or alkyl of 1 to 8 carbon atoms and Y 2 is hydrogen or alkyl of 1 to 8 carbon atoms; cyano and nitro; and, if n is 2, Q represents 1,3-phenylene, 1,4-phenylene 1,2-naphthylene, 1,8-naphthylene or 2,3-naphthylene; or said phenylene or naphthylene substituted by 1 to 3 moieties selected from the group given for substituting phenyl or naphthyl for Q when n is 1; or a group of the formulae ##STR24## whereby X represents the bridge member --O--, --S--, --S-S--, --SO 2 --, --CH 2 --, --CO-- or ##STR25## which process comprises converting an isoimide of the formula II ##STR26## wherein Q and n have the meanings given under the formula I, in the presence of a compound of the formula III m--oh).sub.z (III) and of a teriary amine of the formula IV or V ##STR27## wherein z represents the number 1 or 2, m represents an integer from 2 to 6, M represents, where z is 1, phenyl, naphthyl or said phenyl substituted by 1 to 3 moieties selected from the group consisting of nitro, hydroxyl, alkyl of 1 to 4 carbon atoms and halogen, or a group ##STR28## where z is 2, a group ##STR29## R 1 and R 2 independently of one another represent an alkyl group having 1 to 16 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or benzyl, R 3 represents an alkyl group having 1 to 16 carbon atoms, phenyl, benzyl or phenylethyl, and R 4 represents methyl or ethyl, at a temperature of about 0-80° C., to an imide of the formula I, and wherein the compound of formula III and the tertiary amine of formula IV or V are each used in amount of 0.2 to 10 mol %, relative to the isoimide of formula II.
Claim 2
Dependent Claim
414 words
Process for the production of an imide of the formula I ##STR22## wherein n represents the number 1 or 2, Q represents, if n is 1, phenyl, 1-naphthyl, 2-naphtyl, or said phenyl or said naphthyl groups substituted by 1 to 3 moieties selected from the group consisting of halogen, hydroxyl, alkyl of 1 to 8 carbon atoms, halogenoalkyl of 1 to 3 carbon atoms, alkylthio of 1 to 4 carbon atoms, N,N-dialkylamino of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenoxy, alkoxycarbonyl of 2 to 5 carbon atoms; --SO 2 Y, --NHCOY, ##STR23## where Y is phenyl or alkyl of 1 to 4 carbon atoms, Y 1 is hydrogen, phenyl, naphthyl or alkyl of 1 to 8 carbon atoms and Y 2 is hydrogen or alkyl of 1 to 8 carbon atoms; cyano and nitro; and, if n is 2, Q represents 1,3-phenylene, 1,4-phenylene 1,2-naphthylene, 1,8-naphthylene or 2,3-naphthylene; or said phenylene or naphthylene substituted by 1 to 3 moieties selected from the group given for substituting phenyl or naphthyl for Q when n is 1; or a group of the formulae ##STR24## whereby X represents the bridge member --O--, --S--, --S-S--, --SO 2 --, --CH 2 --, --CO-- or ##STR25## which process comprises converting an isoimide of the formula II ##STR26## wherein Q and n have the meanings given under the formula I, in the presence of a compound of the formula III m--oh).sub.z (III) and of a teriary amine of the formula IV or V ##STR27## wherein z represents the number 1 or 2, m represents an integer from 2 to 6, M represents, where z is 1, phenyl, naphthyl or said phenyl substituted by 1 to 3 moieties selected from the group consisting of nitro, hydroxyl, alkyl of 1 to 4 carbon atoms and halogen, or a group ##STR28## where z is 2, a group ##STR29## R 1 and R 2 independently of one another represent an alkyl group having 1 to 16 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or benzyl, R 3 represents an alkyl group having 1 to 16 carbon atoms, phenyl, benzyl or phenylethyl, and R 4 represents methyl or ethyl, at a temperature of about 0-80° C., to an imide of the formula I, and wherein the compound of formula III and the tertiary amine of formula IV or V are each used in amount of 0.2 to 10 mol %, relative to the isoimide of formula II.
Claim 3
Dependent Claim
64 words
Process according to claim 1, wherein there is used an isoimide of the formula II in which n represents the number 1, and Q represents the 1- or 2-naphthyl group or a phenyl group which is substituted by 1 or 2 halogen atoms, an alkyl or alkoxy group each having 1-4 carbon atoms in the alkyl moieties, a trifluoromethyl, sulphamoyl, nitro or cyano group.
Claim 4
Dependent Claim
26 words
Process according to claim 1, wherein there is used an isoimide of the formula II in which n represents the number 1, and Q represents phenyl.
Claim 5
Dependent Claim
39 words
Process according to claim 1, wherein there is used an isoimide of the formula II in which n represents the number 2, and Q represents the 1,3-phenylene group, the 4,4'-diphenyl ether group, the 4,4'-diphenylsulphone group or the 4,4'-diphenylmethane group.
Claim 6
Dependent Claim
21 words
Process according to claim 1, wherein the employed compound of the formula III is nitrophenol, α-naphthol, 2,2-bis-(4-hydroxyphenyl)-propane and phenol or N-hydroxysuccinimide.
Claim 7
Dependent Claim
14 words
Process according to claim 1, wherein the tertiary amine used is 1,2-bis-(dimethylamino)-ethane or triethylamine.
Claim 8
Dependent Claim
19 words
Process according to claim 1, wherein the conversion is performed at a temperature of about 10 to 40° C.
Claim 9
Dependent Claim
28 words
Process according to claim 2 wherein said phenyl group is substituted by alkyl of 1 to 2 carbon atoms or by alkoxy of 1 to 2 carbon atoms.
Claim 10
Dependent Claim
11 words
Process according to claim 4 wherein Q represents the 4,4'-diphenylmethane group.
Claim 11
Dependent Claim
15 words
Process according to claim 5 wherein the compound for formula III is phenol or N-hydroxysuccinimide.
Claim 12
Dependent Claim
40 words
Process according to claim 1 wherein the compound of formula III and the tertiary amine of formula IV or V are each used in the amounts of about 2 to 7 mol %, relative to the isoimide of formula II.
References Cited (Backward Citations)
US2980694A
Cited
US3855239A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-01-01 | 1982-07-03 | 1983-01-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-01-01 | 1986-07-03 | 1987-01-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-01-01 | 1990-07-03 | 1991-01-02 | $7700.00 | Window Closed / Lapsed |