Patent US4132740A successfully refreshed from Google Patents.
US4132740A
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US
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Preparation of carboranyl sulfides
Assignee: United States Department of the Army
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Filing: 1972-10-03
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Granted: 1979-01-02
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Expires: 1992-10-03
Abstract
Abstract Carboranylmethyl alkyl sulfides are disclosed along with a process for prration which process involves reacting decaborane with the propargyl alkyl sulfide in cyclohexane.
Inventors
- 👤 Royland D. Shoults
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:12
CPC Classifications
C; C07; C07C; C07C321/00; C07F; C07F5/00; C07F5/02; C07F5/027
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
351 words
A process for preparation of carboranylmethyl alkyl sulfides comprising: (a) combining a predetermined amount of decaborane with a predetermined amount of cyclohexane to form a mixture in a suitable reaction container that is provided with means for heating, means for cooling, and means for stirring, said container being equipped with a condenser and means for venting of gaseous reaction products; (b) stirring said decaborane and cyclohexane until most of the decaborane is dissolved; (c) adding a predetermined amount, including an excess of the theoretical amount, of a propargyl alkyl sufide to said mixture, said propargyl alkyl sulfide having the formula: HC.tbd.CCH 2 SR, where R equals an alkyl group having from 2 to 10 carbon atoms; (d) refluxing said mixture having said propargyl alkyl sulfide added thereto at a predetermined temperature range and for a predetermined period of time while reacting is accomplished and venting of gaseous reaction products, including hydrogen, is accomplished, said reacting forming a crude reaction product in solution; (e) cooling said crude reaction product in solution; (f) transferring said crude reaction product in solution to a suitable container for separating said crude reaction product; (g) washing said crude reaction product in solution a plurality of times with a 10% potassium hydroxide solution and followed by washing a plurality of times with a solution selected from water and saline solution to thereby effect separating of said crude reaction product that has been washed; (h) transferring the separated and washed crude reaction product in solution to a distillation assembly; (i) distilling the volatile materials, including any excess propargyl alkyl sulfide, until a temperature of about 110° C. is reached, and thereafter, continue distilling the remaining volatiles while gradually reducing the pressure to about 1 mm and while gradually reducing the temperature to about 100° C.; and (j) separating the reaction product by further distilling at a reduced pressure of about 0.5 mm and at a temperature from about 110° C. to about 160° C., said reaction product being a carboranylmethyl alkyl sulfide having the structure: ##STR5## where R equals an alkyl group having from 2 to 10 carbon atoms.
Claim 2
Dependent Claim
351 words
A process for preparation of carboranylmethyl alkyl sulfides comprising: (a) combining a predetermined amount of decaborane with a predetermined amount of cyclohexane to form a mixture in a suitable reaction container that is provided with means for heating, means for cooling, and means for stirring, said container being equipped with a condenser and means for venting of gaseous reaction products; (b) stirring said decaborane and cyclohexane until most of the decaborane is dissolved; (c) adding a predetermined amount, including an excess of the theoretical amount, of a propargyl alkyl sufide to said mixture, said propargyl alkyl sulfide having the formula: HC.tbd.CCH 2 SR, where R equals an alkyl group having from 2 to 10 carbon atoms; (d) refluxing said mixture having said propargyl alkyl sulfide added thereto at a predetermined temperature range and for a predetermined period of time while reacting is accomplished and venting of gaseous reaction products, including hydrogen, is accomplished, said reacting forming a crude reaction product in solution; (e) cooling said crude reaction product in solution; (f) transferring said crude reaction product in solution to a suitable container for separating said crude reaction product; (g) washing said crude reaction product in solution a plurality of times with a 10% potassium hydroxide solution and followed by washing a plurality of times with a solution selected from water and saline solution to thereby effect separating of said crude reaction product that has been washed; (h) transferring the separated and washed crude reaction product in solution to a distillation assembly; (i) distilling the volatile materials, including any excess propargyl alkyl sulfide, until a temperature of about 110° C. is reached, and thereafter, continue distilling the remaining volatiles while gradually reducing the pressure to about 1 mm and while gradually reducing the temperature to about 100° C.; and (j) separating the reaction product by further distilling at a reduced pressure of about 0.5 mm and at a temperature from about 110° C. to about 160° C., said reaction product being a carboranylmethyl alkyl sulfide having the structure: ##STR5## where R equals an alkyl group having from 2 to 10 carbon atoms.
Claim 3
Dependent Claim
72 words
The process of claim 1 wherein said predetermined amount of decaborane is about 1 mole; said predetermined amount of cyclohexane is about 500 milliliters; said predetermined amount of said propargyl alkyl sulfide including an excess of the theoretical amount is about 1.35 moles; and said refluxing is accomplished at said predetermined temperature range of about 85° C. to about 87° C. and for said predetermined period of time of about 29 hours.
Claim 4
Dependent Claim
26 words
The process of claim 2 wherein said propargyl alkyl sulfide is propargyl ethyl sulfide and said reaction product is carboranylmethyl ethyl sulfide having the structure: ##STR6##
Claim 5
Dependent Claim
22 words
The process of claim 1 wherein said propargyl alkyl sulfide is propargyl propyl sulfide and said reaction product is carboranylmethyl propyl sulfide.
Claim 6
Dependent Claim
22 words
The process of claim 1 wherein said propargyl alkyl sulfide is propargyl isopropyl sulfide and said reaction product is carboranylmethyl isopropyl sulfide.
Claim 7
Dependent Claim
22 words
The process of claim 1 wherein said propargyl alkyl sulfide is propargyl butyl sulfide and said reaction product is carboranylmethyl butyl sulfide.
Claim 8
Dependent Claim
22 words
The process of claim 1 wherein said propargyl alkyl sulfide is propargyl butyl sulfide and said reaction product is carboranylmethyl isobutyl sulfide.
References Cited (Backward Citations)
US3674853A
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 |