US4056547A
Expired / Lapsed
US
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Process for the preparation of organic isocyanate compounds
Assignee: Kao Corp
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Filing: 1976-09-24
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Granted: 1977-11-01
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Expires: 1996-09-24
Abstract
Abstract A process for preparing organic isocyanate compounds characterized by reacting a chloromethyl group-containing compound having the formula: (X).sub.n RCH.sub.2 Cl wherein X, which can be the same or different, is chlorine, alkyl, cycloalkyl, alkenyl, phenyl, chloromethylphenyl or chloromethyl, n is 0 or an integer of 1 to 3, and R is an aromatic hydrocarbon radical or an olefin radical, With an alkali cyanate, in the presence of a catalyst composition comprising (a) a cuprous salt in an amount of 0.1 to 20% by weight, based on said chloromethyl group-containing compound, and (b) a tertiary amine compound or quaternary ammonium compound in an amount equivalent to 0.05 to 1.25 gram atoms of nitrogen per gram mole of said cuprous salt, in a high-boiling-point solvent having a dieelectric constant (ε) not higher than 20, at a reaction temperature of 150° to 250° C, for 0.1 to 10 hours.
Inventors
- 👤 Yoshiaki Tanaka
- 👤 Susumu Handa
- 👤 Atsushi Nishibata
- 👤 Sadashi Ueda
- 👤 Yoshiaki Inamoto
- 👤 Masahiro Saito
- 👤 Fumio Tanimoto
- 👤 Hisao Kitano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 19:21
CPC Classifications
C; C07; C07C; C07C263/00
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
240 words
A process for preparing organic isocyanates which comprises reacting at a temperature of from 150° to 250° C, for from 0.1 to 10 hours, an alkali metal or ammonium cyanate, or mixture thereof, with a compound having the formula (X).sub.n RCH.sub.2 Cl wherein X is chlorine, alkyl, cycloalkyl, alkenyl, phenyl, chloromethylphenyl or chloromethyl, n is zero or an integer of from 1 to 3 and R is an aromatic hydrocarbon radical, and X can be the same or different when n is more than 1, in the presence of a catalyst composition consisting essentially of (a) from 0.1 to 20 weight percent, based on the weight of said compound, of a cuprous salt selected from the group consisting of cuprous chloride, cuprous bromide, cuprous thiocyanate, cuprous cyanate and mixtures thereof, and (b) a nitrogen compound selected from the group consisting of triethylene diamine, pyridine, ethylpyridine, lutidine, collidine, trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, trihexylamine, tri-higher-alkylamines, dimethylbenzylamine, methyldibenzylamine, tribenzylamine, dimethylnaphthylamine, N-methylpiperidine, N-methylmorpholine, N-butylmorpholine, N,N'-dimethylpiperazine, tetramethylammonium chloride, tetraethylammonium chloride, trimethylbenzylammonium chloride, dimethylbenzyl-higher-alkyl-ammonium chloride, tetramethylammonium bromide, tetraethylammonium bromide, trimethylbenzylammonium bromide, 1,8-diazabicyclo[ 5.4.0]-7-undecene and mixtures thereof, in an amount of said nitrogen compound equivalent to from 0.05 to 1.25 gram atoms of nitrogen per gram mole of said cuprous salt, and in a solvent, or mixture of solvents, having a dielectric constant (ε) of ≦ 20, which are free of active hydrogen atoms and which have a boiling point of from 150° to 400° C.
Claim 2
Dependent Claim
240 words
A process for preparing organic isocyanates which comprises reacting at a temperature of from 150° to 250° C, for from 0.1 to 10 hours, an alkali metal or ammonium cyanate, or mixture thereof, with a compound having the formula (X).sub.n RCH.sub.2 Cl wherein X is chlorine, alkyl, cycloalkyl, alkenyl, phenyl, chloromethylphenyl or chloromethyl, n is zero or an integer of from 1 to 3 and R is an aromatic hydrocarbon radical, and X can be the same or different when n is more than 1, in the presence of a catalyst composition consisting essentially of (a) from 0.1 to 20 weight percent, based on the weight of said compound, of a cuprous salt selected from the group consisting of cuprous chloride, cuprous bromide, cuprous thiocyanate, cuprous cyanate and mixtures thereof, and (b) a nitrogen compound selected from the group consisting of triethylene diamine, pyridine, ethylpyridine, lutidine, collidine, trimethylamine, triethylamine, tripropylamine, tributylamine, triamylamine, trihexylamine, tri-higher-alkylamines, dimethylbenzylamine, methyldibenzylamine, tribenzylamine, dimethylnaphthylamine, N-methylpiperidine, N-methylmorpholine, N-butylmorpholine, N,N'-dimethylpiperazine, tetramethylammonium chloride, tetraethylammonium chloride, trimethylbenzylammonium chloride, dimethylbenzyl-higher-alkyl-ammonium chloride, tetramethylammonium bromide, tetraethylammonium bromide, trimethylbenzylammonium bromide, 1,8-diazabicyclo[ 5.4.0]-7-undecene and mixtures thereof, in an amount of said nitrogen compound equivalent to from 0.05 to 1.25 gram atoms of nitrogen per gram mole of said cuprous salt, and in a solvent, or mixture of solvents, having a dielectric constant (ε) of ≦ 20, which are free of active hydrogen atoms and which have a boiling point of from 150° to 400° C.
Claim 3
Dependent Claim
17 words
A process as claimed in claim 1 in which said cyanate is sodium cyanate or potassium cyanate.
Claim 4
Dependent Claim
14 words
A process as claimed in claim 2 in which said compound is benzyl chloride.
Claim 5
Dependent Claim
14 words
A process as claimed in claim 2 in which said compound is allyl chloride.
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) | 1980-10-31 | 1981-05-02 | 1981-11-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-31 | 1985-05-02 | 1985-11-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-31 | 1989-05-02 | 1989-11-01 | $7700.00 | Window Closed / Lapsed |