US3933925A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hydrolysis of toluene diamines to produce methyl resorcinols
Assignee: Beazer East Inc
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Filing: 1975-01-17
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Granted: 1976-01-20
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Expires: 1995-01-17
Abstract
Abstract Methyl resorcinols are produced by the hydrolysis of toluene diamines in an aqueous excess of ammonium bisulfate. The reactants are contacted at an elevated temperature for a period of time sufficient to hydrolyze the toluene diamines to methyl resorcinols. The methyl resorcinols so produced are separated from the reaction mixture. The ammonium sulfate is regenerated to ammonium bisulfate by removing the water and thermally decomposing the by-product ammonium sulfate at an elevated temperature.
Inventors
- 👤 Nicholas P. Greco
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:13
CPC Classifications
A; A61; A61Q; A61Q5/00; A61K; A61K8/00; A61K8/18; A61K8/30; A61K8/33; A61K8/34; A61K8/347; A61Q17/00; A61Q17/005; A61Q19/00; C; C01; C01C; C01C1/00; C01C1/24; C07; C07C; C07C37/00; C07C37/01; C07C37/045; C07C37/05
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
90 words
A method of making methyl resorcinol comprising: a. contacting toluene diamine with ammomium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of toluene diamine and 40 to 120 moles of water per mole of toluene diamine and that is at a temperature of 200° to 300°C. for a period of one-half to eight hours to hydrolyze said toluene diamine to methyl resorcinol, b. cooling said hydrolysis reaction mixture, and c. extracting said methyl resorcinol from said solution with a water-immiscible organic solvent.
Claim 2
Independent Claim
90 words
A method of making methyl resorcinol comprising: a. contacting toluene diamine with ammomium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of toluene diamine and 40 to 120 moles of water per mole of toluene diamine and that is at a temperature of 200° to 300°C. for a period of one-half to eight hours to hydrolyze said toluene diamine to methyl resorcinol, b. cooling said hydrolysis reaction mixture, and c. extracting said methyl resorcinol from said solution with a water-immiscible organic solvent.
Claim 3
Dependent Claim
41 words
The method of claim 1 wherein the solution from which the methyl resorcinol has been extracted is maintained at a temperature of 200° to 260°C. for an additional period of time to hydrolyze residual of said toluene diamine to methyl resorcinol.
Claim 4
Independent Claim
141 words
The method of making methyl resorcinol comprising: a. contacting toluene diamine with ammonium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of toluene diamine and 40 to 120 moles of water per mole of toluene diamine and that is at a temperature of 200° to 260°C. for a period of one-half to eight hours to hydrolyze said toluene diamine to methyl resorcinol. b. cooling said hydrolysis reaction mixture, c. extracting said methyl resorcinol from said solution with an inert water-immiscible organic solvent, thereafter d. evaporating the water from said solution to obtain a residue consisting essentially of ammonium sulfate and ammonium bisulfate, and e. heating said residue to an elevated temperature of 210° to 450°C. to convert said ammonium sulfate to ammonium bisulfate for reuse to hydrolyze more toluene diamine to methyl resorcinol.
Claim 5
Independent Claim
141 words
The method of making methyl resorcinol comprising: a. contacting toluene diamine with ammonium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of toluene diamine and 40 to 120 moles of water per mole of toluene diamine and that is at a temperature of 200° to 260°C. for a period of one-half to eight hours to hydrolyze said toluene diamine to methyl resorcinol. b. cooling said hydrolysis reaction mixture, c. extracting said methyl resorcinol from said solution with an inert water-immiscible organic solvent, thereafter d. evaporating the water from said solution to obtain a residue consisting essentially of ammonium sulfate and ammonium bisulfate, and e. heating said residue to an elevated temperature of 210° to 450°C. to convert said ammonium sulfate to ammonium bisulfate for reuse to hydrolyze more toluene diamine to methyl resorcinol.
Claim 6
Independent Claim
90 words
A method of making 4-methyl resorcinol comprising: a. contacting 2,4-toluene diamine with ammonium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of 2,4-toluene diamine and 40 to 120 moles of water per mole of 2,4-toluene diamine and that is at a temperature of 200° to 300°C. for a period of one-half to eight hours to hydrolyze said 2,4-toluene diamine to 4-methyl resorcinol, b. cooling said hydrolysis reaction mixture, and c. extracting said 4-methyl resorcinol from said solution with a water-immiscible organic solvent.
Claim 7
Independent Claim
90 words
A method of making 4-methyl resorcinol comprising: a. contacting 2,4-toluene diamine with ammonium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of 2,4-toluene diamine and 40 to 120 moles of water per mole of 2,4-toluene diamine and that is at a temperature of 200° to 300°C. for a period of one-half to eight hours to hydrolyze said 2,4-toluene diamine to 4-methyl resorcinol, b. cooling said hydrolysis reaction mixture, and c. extracting said 4-methyl resorcinol from said solution with a water-immiscible organic solvent.
Claim 8
Dependent Claim
41 words
The method of claim 4 wherein the solution from which the 4-methyl resorcinol has been extracted is maintained at a temperature of 200° to 260°C. for an additional period of time to hydrolyze residual of said toluene diamine to 4-methyl resorcinol.
Claim 9
Independent Claim
92 words
A method of making 2-methyl resorcinol comprising: a. contacting 2,6 toluene diamine with ammonium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of toluene diamine and 40 to 120 moles of water per mole of toluene diamine and that is at a temperature of 200° to 300°C. for a period of one-half to eight hours to hydrolyze said 2,6-toluene diamine to 2 -methyl resorcinol, b. cooling said hydrolysis reaction mixture, and c. extracting said 2-methyl resorcinol from said solution with a water-immiscible organic solvent.
Claim 10
Independent Claim
92 words
A method of making 2-methyl resorcinol comprising: a. contacting 2,6 toluene diamine with ammonium bisulfate in an aqueous solution that contains 4 to 12 moles of ammonium bisulfate per mole of toluene diamine and 40 to 120 moles of water per mole of toluene diamine and that is at a temperature of 200° to 300°C. for a period of one-half to eight hours to hydrolyze said 2,6-toluene diamine to 2 -methyl resorcinol, b. cooling said hydrolysis reaction mixture, and c. extracting said 2-methyl resorcinol from said solution with a water-immiscible organic solvent.
Claim 11
Dependent Claim
41 words
The method of claim 6 wherein the solution from which the 2-methyl resorcinol has been extracted is maintained at a temperature of 200° to 260°C. for an additional period of time to hydrolyze residual of said toluene diamine to 2-methyl resorcinol.
References Cited (Backward Citations)
US2665313A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-19 | 1979-07-21 | 1980-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-19 | 1983-07-21 | 1984-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-19 | 1987-07-21 | 1988-01-20 | $7700.00 | Window Closed / Lapsed |