Patent JPS56106646A successfully refreshed from Google Patents.
US4327233A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method for producing carbocyclic compounds from cyclic sulfide
Assignee: United States Department of Commerce
•
Filing: 1981-03-26
•
Granted: 1982-04-27
•
Expires: 2001-03-26
Abstract
Abstract A method is provided for producing a carbocyclic compound by contacting an organic compound containing a 4-8 membered cyclic sulfide with ozone, in the vapor phase, and recovering a product containing a 3-7 membered carbocyclic ring.
Inventors
- 👤 Richard I. Martinez
- 👤 John T. Herron
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 16:25
CPC Classifications
C; C07; C07C; C07C1/00; C07C1/32; C07C1/321; C07C1/322; C07C2601/00; C07C2601/04
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
112 words
A method for producing a carbocyclic compound, which comprises contacting an organic compound containing a 4-8 membered cyclic sulfide moiety and having the formula ##STR10## wherein A is a moiety containing a divalent 3-7 carbon alkylene bridge whose two termini are joined to a sulfur atom to form said cyclic sulfide moiety, with ozone, in the vapor phase, and recovering from the resultant reaction mixture a product containing a 3-7 membered carbocyclic ring formed by extrusion of said sulfur atom and joining of said two termini through a carbon-carbon single bond; wherein substantially no non-sulfur-containing compound having olefinic unsaturation instead of said 3-7 membered carbocyclic ring is produced in said reaction mixture.
Claim 2
Independent Claim
112 words
A method for producing a carbocyclic compound, which comprises contacting an organic compound containing a 4-8 membered cyclic sulfide moiety and having the formula ##STR10## wherein A is a moiety containing a divalent 3-7 carbon alkylene bridge whose two termini are joined to a sulfur atom to form said cyclic sulfide moiety, with ozone, in the vapor phase, and recovering from the resultant reaction mixture a product containing a 3-7 membered carbocyclic ring formed by extrusion of said sulfur atom and joining of said two termini through a carbon-carbon single bond; wherein substantially no non-sulfur-containing compound having olefinic unsaturation instead of said 3-7 membered carbocyclic ring is produced in said reaction mixture.
Claim 3
Dependent Claim
59 words
The method of claim 1, wherein A is a moiety having the formula ##STR11## wherein each of R 1 -R 14 , independently is H or C 1-6 alkyl, or any two or more of R 1 -R 14 form an alkyl-substituted or unsubstituted fused, bridged or spirocyclic ring; and k,m,n and p are each independently 0 or 1.
Claim 4
Dependent Claim
40 words
The method of claim 1, wherein A is --(CR 15 R 16 ) q --, wherein R 15 and R 16 are each independently H or C 1 6 alkyl; and q is an integer of from 3 to 7.
Claim 5
Dependent Claim
14 words
The method of claim 1, wherein said divalent alkylene bridge is a 4-carbon bridge.
Claim 6
Dependent Claim
9 words
The method of claim 2, wherein K=1 and n=n=p=0.
Claim 7
Dependent Claim
7 words
The method of claim 3, wherein q=4.
Claim 8
Dependent Claim
11 words
The method of claim 3, wherein R 15 =R 16 =H.
Claim 9
Dependent Claim
23 words
The method of claim 1, wherein said organic compound is thiolane, and said product is cyclobutane; and wherein substantially no ethylene is produced.
Claim 10
Dependent Claim
19 words
The method of claim 1, wherein said contacting is effected at a temperature of from 0° to 125° C.
Claim 11
Dependent Claim
14 words
The method of claim 9, wherein said temperature is from 12° to 30° C.
Claim 12
Dependent Claim
40 words
The method of claim 1, wherein said ozone is supplied as a mixture of from 1 to 10% ozone in oxygen, and the total initial pressure of said cyclic sulfide and said ozone-oxygen mixture is from 0.1 to 100 Torr.
Claim 13
Dependent Claim
16 words
The method of claim 11, wherein said total initial pressure is from 1 to 10 Torr.
Claim 14
Dependent Claim
24 words
The method of claim 1, wherein the molar ratio of ozone to cyclic sulfide-containing compound in said contacting step is from 0.5 to 20.
Claim 15
Dependent Claim
13 words
The method of claim 13, wherein said ratio is from 2 to 10.
Claim 16
Independent Claim
69 words
A method of producing cyclobutane, which comprises contacting thiolane with ozone, in the vapor phase, at a temperature of from 0° to 125° C., and recovering the resultant cyclobutane; wherein said ozone is supplied as a mixture of from 1 to 10% ozone in oxygen, and the total initial pressure of thiolane and said ozone-oxygen mixture is from 0.1 to 100 Torr.; and wherein substantially no ethylene is produced.
Claim 17
Independent Claim
69 words
A method of producing cyclobutane, which comprises contacting thiolane with ozone, in the vapor phase, at a temperature of from 0° to 125° C., and recovering the resultant cyclobutane; wherein said ozone is supplied as a mixture of from 1 to 10% ozone in oxygen, and the total initial pressure of thiolane and said ozone-oxygen mixture is from 0.1 to 100 Torr.; and wherein substantially no ethylene is produced.
Claim 18
Dependent Claim
14 words
The method of claim 15, wherein said temperature is from 12° to 30° C.
Claim 19
Dependent Claim
16 words
The method of claim 15, wherein said total initial pressure is from 1 to 10 Torr.
Claim 20
Dependent Claim
19 words
The method of claim 15, wherein the molar ratio of ozone to cyclic sulfide is from 2 to 10.
References Cited (Backward Citations)
US2414880A
Cited
US2753380A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-04-26 | 1985-10-26 | 1986-04-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-04-26 | 1989-10-26 | 1990-04-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-04-26 | 1993-10-26 | 1994-04-27 | $7700.00 | Window Closed / Lapsed |