US4251459A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of N-(2-mercaptoethyl)alkanamides
Assignee: Dow Chemical Co
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Filing: 1979-07-11
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Granted: 1981-02-17
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Expires: 1999-07-11
Abstract
Abstract The title compounds are prepared by the reaction of a 2-alkyl-2-oxazoline with hydrogen sulfide in a continuous process wherein both reactants are maintained in the liquid phase throughout the reaction by the use of superatmospheric pressure. This continuous process reduces the reaction time substantially compared to prior art process and also reduces the quantity of by-products.
Inventors
- 👤 Kim G. Bargeron
- 👤 Thad S. Hormel
- 👤 David K. Winegardner
- 👤 Bruce G. Lovelace
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 06:24
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01; C07C233/16
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
112 words
In a process for preparing an N-(2-mercaptoethyl)alkanamide represented by the formula ##STR3## wherein R is alkyl and R 1 -R 4 are each independently hydrogen, lower alkyl, hydroxy-substituted lower alkyl or phenyl by reacting a 2-alkyl-2-oxazoline with hydrogen sulfide under essentially anhydrous conditions, the improvement comprising reacting in a continuous process, the hydrogen sulfide with the 2-alkyl-2-oxazoline in a molar ratio from at least about 1.0 to about 1.2 moles of hydrogen sulfide per mole of the oxazoline, wherein both the reactants are maintained in the liquid phase throughout the reaction by the application of superatmospheric pressure and the reaction temperature is in the range from about 100° to about 185° C.
Claim 2
Dependent Claim
112 words
In a process for preparing an N-(2-mercaptoethyl)alkanamide represented by the formula ##STR3## wherein R is alkyl and R 1 -R 4 are each independently hydrogen, lower alkyl, hydroxy-substituted lower alkyl or phenyl by reacting a 2-alkyl-2-oxazoline with hydrogen sulfide under essentially anhydrous conditions, the improvement comprising reacting in a continuous process, the hydrogen sulfide with the 2-alkyl-2-oxazoline in a molar ratio from at least about 1.0 to about 1.2 moles of hydrogen sulfide per mole of the oxazoline, wherein both the reactants are maintained in the liquid phase throughout the reaction by the application of superatmospheric pressure and the reaction temperature is in the range from about 100° to about 185° C.
Claim 3
Dependent Claim
28 words
The process as described in claim 1 wherein the 2-alkyl-2-oxazoline and the hydrogen sulfide reactant are premixed in the specified ratio prior to the occurrence of substantial reaction.
Claim 4
Dependent Claim
23 words
The process as described in claim 2 wherein the reaction temperature is in the range from about 135° C. to about 165° C.
Claim 5
Dependent Claim
14 words
The process as described in claim 3 wherein the 2-alkyl-2-oxazoline is 2-methyl-2-oxazoline or 2-ethyl-2-oxazoline.
Claim 6
Dependent Claim
21 words
The process as described in claim 4 wherein the reaction pressure is in the range from about 550 to 900 psig.
Claim 7
Dependent Claim
23 words
The process as described in claim 2 wherein the reaction temperature is in the range from about 115° C. to about 160° C.
References Cited (Backward Citations)
US4086274A
Cited
US4086273A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-02-17 | 1984-08-18 | 1985-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-17 | 1988-08-18 | 1989-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-17 | 1992-08-18 | 1993-02-17 | $7700.00 | Window Closed / Lapsed |