US3894059A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the oxidation of olefines
Assignee: Costain Petrocarbon Ltd
•
Filing: 1973-04-30
•
Granted: 1975-07-08
•
Expires: 1993-04-30
Abstract
Abstract Processes are provided for the oxidation of olefinically unsaturated compounds to oxirane compounds, vic-glycols and vichalohydrins in which the olefinically unsaturated compound, carbon dioxide water and hypohalite are brought into intimate contact so as to form vic-halohydrin, and if desired, exposing the vic-halohydrin to aqueous bicarbonate so as to form oxirane compound and/or vic-glycol. Bicarbonate is formed as by-product in the production of vic-halohydrin and this bicarbonate may be used to convert the vic-halohydrin to oxirane compound or vicglycol. Also carbon dioxide is formed as by-product during the conversion and this is advantageously used to provide carbon dioxide required for the production of the vic-halohydrin. Similarly, the hypohalite is conveniently formed by electrolysis of metal halide derived as by-product of the conversion of vichalohydrin to oxirane compound or vic-glycol.
Inventors
- 👤 Thillyampalam Selvaratnam
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 04:51
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/64; C07C29/66; C07D; C07D301/00; C07D301/02; C07D301/24; C07D301/26
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
13 words
A PROCESS FOR THE PRODUCTION OF AN OXIRANE COMPOUND COMPRISING THE STEPS OF:
Claim 2
Dependent Claim
13 words
A PROCESS FOR THE PRODUCTION OF AN OXIRANE COMPOUND COMPRISING THE STEPS OF:
Claim 3
Dependent Claim
43 words
REACTING AT A TEMPERATURE NOT GREATER THAN 10*C. BUT ABOVE THE FREEZING TEMPERATURE OF THE SYSTEM AN OLEFINICALLY UNSATURAED COMPOUND, CARBONDIOXIDE, WATER AND A HYPOHALITE IN QUANTITIES SUFFICIENT TO PRODUCE AN AQUEOUS PRODUCT MIXTURE COMPRISING SUBSTANTIALLY EQUIMOLAR QUANTITIES OF BICARBONATE AND VIC-HALOHYDRIN, AN
Claim 4
Dependent Claim
43 words
REACTING AT A TEMPERATURE NOT GREATER THAN 10*C. BUT ABOVE THE FREEZING TEMPERATURE OF THE SYSTEM AN OLEFINICALLY UNSATURAED COMPOUND, CARBONDIOXIDE, WATER AND A HYPOHALITE IN QUANTITIES SUFFICIENT TO PRODUCE AN AQUEOUS PRODUCT MIXTURE COMPRISING SUBSTANTIALLY EQUIMOLAR QUANTITIES OF BICARBONATE AND VIC-HALOHYDRIN, AN
Claim 5
Dependent Claim
28 words
HEATING AT LEAST A PORTION OF SAID AQUEOUS PRODUCT MIXTURE TO A TEMPERATURE RESULTING REACTION TOGETHER OF SAID VIC-HALOHYDRIN AND SAID AQUEOUS BICARBONATE TO FORM AN OXIRANE COMPOUND.
Claim 6
Dependent Claim
28 words
HEATING AT LEAST A PORTION OF SAID AQUEOUS PRODUCT MIXTURE TO A TEMPERATURE RESULTING REACTION TOGETHER OF SAID VIC-HALOHYDRIN AND SAID AQUEOUS BICARBONATE TO FORM AN OXIRANE COMPOUND.
Claim 7
Dependent Claim
29 words
heating at least a portion of said aqueous product mixture to a temperature resulting in reaction together of said vic-halohydrin and said aqueous bicarbonate to form an oxirane compound.
Claim 8
Dependent Claim
29 words
heating at least a portion of said aqueous product mixture to a temperature resulting in reaction together of said vic-halohydrin and said aqueous bicarbonate to form an oxirane compound.
Claim 9
Dependent Claim
32 words
A process according to claim 1 in which at least part of the carbon dioxide used in said reacting step comprises carbon dioxide evolved from the reaction mixture during said heating step.
Claim 10
Dependent Claim
14 words
A process according to claim 1 in which the hypohalite is a metal hypohalite.
Claim 11
Dependent Claim
31 words
A process according to claim 1 in which the bicarbonate is metal bicarbonate and the hypohalite is metal hypohalite formed by electrolysis of aqueous metal halide formed during said heating step.
Claim 12
Dependent Claim
22 words
A process according to claim 1 in which said heating step is carried out at a temperature of from 50*C to 115*C.
Claim 13
Dependent Claim
24 words
A process according to claim 1 in which said heating step is carried out at a pressure of from 0.5 to 2.0 Kg/cm2 absolute.
Claim 14
Dependent Claim
50 words
A process according to claim 1 in which oxirane compound formed as a result of reaction between vic-halohydrin and aqueous bicarbonate is stripped from the reaction mixture with the aid of carbon dioxide formed in situ as a result of the reaction and/or with steam and/or with olefinically unsaturated compound.
Claim 15
Dependent Claim
15 words
A process according to claim 1 in which the temperature is from -15*C to +10*C.
Claim 16
Dependent Claim
15 words
A process according to claim 1 in which the temperature is from +5*C to +10*C.
Claim 17
Dependent Claim
33 words
A process according to claim 1 in which the contacting of the olefinically unsaturated compound, carbon dioxide, water and hypohalite is carried out at a pressure of from 1.5 to 5.0 Kg/cm2 absolute.
Claim 18
Dependent Claim
30 words
A process according to claim 1 in which a substantially equimolar gaseous mixture of the olefinically unsaturated compound and the carbon dioxide is contacted with an aqueous solution of hypohalite.
Claim 19
Dependent Claim
21 words
A process according to claim 11 in which the aqueous solution contains from 2 to 5 wt percent of metal hypohalite.
Claim 20
Dependent Claim
31 words
A process according to claim 1 in which the olefinically unsaturated compound and the carbon dioxide are contacted with an aqueous solution containing up to 6 wt percent of meTal hypohalite.
Claim 21
Dependent Claim
13 words
A process according to claim 1 in which the hypohalite is sodium hypochlorite.
Claim 22
Dependent Claim
16 words
A process according to claim 1 in which the olefinically unsaturated compound is ethylene or propylene.
Claim 23
Dependent Claim
170 words
A process as claimed in claim 1 comprising the steps of: i. forming an aqueous solution containing a metal hypohalite by electrolysis of an aqueous solution of metal halide, ii. intimately contacting an olefinically unsaturated compound and carbon dioxide with the aqueous solution containing metal hypohalite formed in step (i) so as to form an aqueous solution containing substantially equimolar quantities of metal bicarbonate and vic-halohydrin; iii. heating at least a portion of said aqueous solution formed in step (ii) to a temperature resulting in reaction together of vic-halohydrin and aqueous metal bicarbonate contained in said aqueous solution to form a product mixture comprising an oxirane compound together with metal halide, carbon dioxide and water; iv. separately recovering carbon dioxide, an aqueous solution of metal halide and a product stream comprising oxirane compound from the product mixture formed in step (iii); v. recycling carbon dioxide from step (iv) for use in step (ii) and vi. recycling aqueous metal halide solution from step (iv) for electrolysis in accordance with step (i).
Claim 24
Dependent Claim
30 words
A process according to claim 16 in which the concentration of the aqueous metal halide subjected to electrolysis is adjusted to within the range from 15 to 27 wt percent.
Claim 25
Dependent Claim
164 words
A process as claimed in claim 1 comprising the steps of: i. electrolyzing an aqueous solution of a metal halide to form an aqueous solution containing metal hypohalite and metal halide; ii. contacting the aqueous solution formed in step (i) with carbon dioxide and an olefinically unsaturated compound at a superatmospheric pressure to form an aqueous product mixture comprising substantially equimolar quantities of metal bicarbonate and vic-halohydrin; iii. raising the temperature of said aqueous product mixture formed in step (ii) to effect reaction between the vic-halohydrin and aqueous metal bicarbonate contained therein to form a product mixture comprising oxirane compound, carbon dioxide and aqueous metal halide; iv. separately recovering oxirane compound, carbon dioxide and aqueous metal halide from the product mixture formed in step (iii); and v. recycling aqueous metal halide recovered in step (iv) for electrolysis according to step (i); and vi. recycling carbon dioxide recovered in step (iv) for use as or as part of the carbon dioxide requirement of step (ii).
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) | 1978-07-07 | 1979-01-06 | 1979-07-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-07-07 | 1983-01-06 | 1983-07-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-07-07 | 1987-01-06 | 1987-07-08 | $7700.00 | Window Closed / Lapsed |