US4130577A
Expired / Lapsed
US
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Process for preparing α, α-dimethylbenzyl isocyanates
Assignee: SDS Biotech Corp
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Filing: 1977-10-25
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Granted: 1978-12-19
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Expires: 1997-10-25
Abstract
Abstract Process for preparing alpha , alpha -dimethylbenzyl isocyanate or its derivatives which comprises reacting the corresponding organic halide in an anhydrous condition in the presence of a specified catalyst with an alkali metal cyanate in an aprotic solvent which forms no salt with a hydrogen halide.
Inventors
- 👤 Nobuyuki Nagato
- 👤 Taketoshi Naito
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 18:24
CPC Classifications
C; C07; C07C; C07C263/00
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
151 words
A process for preparing α,α-dimethylbenzyl isocyanate or its ring-substituted derivatives of the formula ##STR12## wherein Y is a halogen atom or an alkyl, haloalkyl or alkoxy group each having 1 to 4 carbon atoms and n is an integer of 0, 1 or 2, which comprises reacting an α,α-dimethylbenzyl halide or its ring-substituted derivative of the formula ##STR13## wherein X is chlorine or bromine, and Y and n are as defined above, with an alkali metal cyanate in an organic solvent in a substantially anhydrous condition at a temperature of between 0° C. and 150° C. in the presence of, as a catalyst, at least one member selected from the group consisting of metallic V, Mn, Co, Zn, Pd and Sn and oxides and mineral acid salts or carboxylic acid salts of these metals, said organic solvent being an aprotic solvent which forms no salt or adduct with a hydrogen halide.
Claim 2
Dependent Claim
151 words
A process for preparing α,α-dimethylbenzyl isocyanate or its ring-substituted derivatives of the formula ##STR12## wherein Y is a halogen atom or an alkyl, haloalkyl or alkoxy group each having 1 to 4 carbon atoms and n is an integer of 0, 1 or 2, which comprises reacting an α,α-dimethylbenzyl halide or its ring-substituted derivative of the formula ##STR13## wherein X is chlorine or bromine, and Y and n are as defined above, with an alkali metal cyanate in an organic solvent in a substantially anhydrous condition at a temperature of between 0° C. and 150° C. in the presence of, as a catalyst, at least one member selected from the group consisting of metallic V, Mn, Co, Zn, Pd and Sn and oxides and mineral acid salts or carboxylic acid salts of these metals, said organic solvent being an aprotic solvent which forms no salt or adduct with a hydrogen halide.
Claim 3
Dependent Claim
21 words
The process of claim 1 wherein the reaction is carried out at a temperature of between 20° C. and 80° C.
Claim 4
Dependent Claim
28 words
The process of claim 1 wherein the molar ratio of the starting α,α-dimethylbenzyl halide or its ring-substituted derivative to the alkali metal cyanate ranges from 1:0.8 to 1:4.
Claim 5
Dependent Claim
28 words
The process of claim 1 wherein the molar ratio of the starting α,α-dimethylbenzyl halide or its ring-substituted derivative to the alkali metal cyanate ranges from 1:1 to 1:2.
Claim 6
Dependent Claim
30 words
The process of claim 1 wherein the reaction is carried out under such a condition that the water content of the starting reaction mixture does not exceed 0.5% by weight.
Claim 7
Dependent Claim
28 words
The process of claim 1 wherein the amount of the catalyst ranges from 0.01 to 30 mole % based on the starting α,α-dimethylbenzyl halide or its ring-substituted derivative.
Claim 8
Dependent Claim
28 words
The process of claim 1 wherein the amount of the catalyst ranges from 0.5 to 10 mole % based on the starting α,α-dimethylbenzyl halide or its ring-substituted derivative.
Claim 9
Dependent Claim
39 words
The process of claim 1 wherein the reaction is carried out in the copresence of at least one promotor selected from the group consisting of trimethylamine, triethylamine, N-monomethylaniline, N,N-diethylaniline, pyridine, picoline, methylethylpyridine, N-methylpiperidine, N-ethylpiperidine, N,N'-dimethylpiperazine, N,N'-diethylpiperazine, N-methylmorpholine and N-ethylmorpholine.
Claim 10
Dependent Claim
21 words
The process of claim 8 wherein the amount of the promotor does not exceed 2 moles per mole of the catalyst.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-18 | 1982-06-19 | 1982-12-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-18 | 1986-06-19 | 1986-12-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-18 | 1990-06-19 | 1990-12-19 | $7700.00 | Window Closed / Lapsed |