US4008133A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Production of epoxy compounds from olefinic compounds
Assignee: Lummus Technology LLC
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Filing: 1976-03-23
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Granted: 1977-02-15
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Expires: 1996-03-23
Abstract
Abstract Olefin oxide is produced by reacting chlorine, obtained from an electrolysis cell, with a tertiary alkanol and an aqueous solution, containing sodium hydroxide and sodium chloride, obtained from the cathode of an electrolysis cell, to produce a tertiary alkyl hypochlorite. The hypochlorite is then reacted in a chlorohydrin reactor with an olefinically unsaturated compound and water, essentially free of chloride ions, to produce the corresponding chlorohydrin. The chlorohydrin is recovered and saponified with cell liquor, containing sodium hydroxide and sodium chloride, obtained from the cathode compartment of the cell to produce the olefin oxide.
Inventors
- 👤 Abraham P. Gelbein
- 👤 Joon Taek Kwon
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:50
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/64; C07C29/66
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
248 words
A process for converting an olefinically unsaturated compound to the corresponding epoxy compound, comprising: a. producing gaseous chlorine by the electrolysis of an aqueous brine solution in an electrolytic cell including an anode compartment and a cathode compartment, said gaseous chlorine being produced in the anode compartment and hydrogen in the cathode compartment; b. contacting in a first reaction zone gaseous chlorine from the cell, an aqueous solution containing sodium chloride and sodium hydroxide from the cathode compartment of the electrolytic cell and a tertiary alkanol to produce a tertiary alkyl hypochlorite; c. recovering from the first reaction zone an aqueous brine phase and an organic phase containing the tertiary alkyl hypochlorite; d. introducing the recovered aqueous brine phase as electrolyte into the electrolytic cell; e. contacting in a second reaction zone the organic phase containing the tertiary alkyl hypochlorite, an olefinically unsaturated compound and water, essentially free of chloride ions, to produce the corresponding chlorohydrin and a tertiary alkanol; f. recovering the chlorohydrin and tertiary alkanol from the second reaction zone; g. passing recovered tertiary alkanol to the first reaction zone; h. contacting in a third reaction zone the chlorohydrin with an aqueous solution of sodium hydroxide and sodium chloride obtained from the cathode compartment of the electrolytic cell to produce the corresponding epoxy compound; i. recovering epoxy compound and an aqueous brine solution from the third reaction zone; and j. introducing aqueous brine solution recovered from the third reaction zone into the electrolytic cell as electrolyte.
Claim 2
Dependent Claim
248 words
A process for converting an olefinically unsaturated compound to the corresponding epoxy compound, comprising: a. producing gaseous chlorine by the electrolysis of an aqueous brine solution in an electrolytic cell including an anode compartment and a cathode compartment, said gaseous chlorine being produced in the anode compartment and hydrogen in the cathode compartment; b. contacting in a first reaction zone gaseous chlorine from the cell, an aqueous solution containing sodium chloride and sodium hydroxide from the cathode compartment of the electrolytic cell and a tertiary alkanol to produce a tertiary alkyl hypochlorite; c. recovering from the first reaction zone an aqueous brine phase and an organic phase containing the tertiary alkyl hypochlorite; d. introducing the recovered aqueous brine phase as electrolyte into the electrolytic cell; e. contacting in a second reaction zone the organic phase containing the tertiary alkyl hypochlorite, an olefinically unsaturated compound and water, essentially free of chloride ions, to produce the corresponding chlorohydrin and a tertiary alkanol; f. recovering the chlorohydrin and tertiary alkanol from the second reaction zone; g. passing recovered tertiary alkanol to the first reaction zone; h. contacting in a third reaction zone the chlorohydrin with an aqueous solution of sodium hydroxide and sodium chloride obtained from the cathode compartment of the electrolytic cell to produce the corresponding epoxy compound; i. recovering epoxy compound and an aqueous brine solution from the third reaction zone; and j. introducing aqueous brine solution recovered from the third reaction zone into the electrolytic cell as electrolyte.
Claim 3
Dependent Claim
32 words
The process of claim 1 wherein the tertiary alkyl hypochlorite introduced into the second reaction zone contains no greater than 7 moles of active chlorine per 100 moles of tertiary alkyl hypochlorite.
Claim 4
Dependent Claim
66 words
The process of claim 2 wherein the aqueous solution containing sodium chloride and sodium hydroxide from the cathode compartment of the electrolytic cell is contacted with gaseous chlorine from the electrolytic cell prior to introduction into the first reaction zone to produce sodium hypochlorite, whereby the aqueous solution from the cathode compartment of the electrolytic cell employed in the first reaction zone further contains sodium hypochlorite.
Claim 5
Dependent Claim
22 words
The process of claim 2 wherein the first reaction zone is operated at a temperature from about 50° to about 220° F.
Claim 6
Dependent Claim
44 words
The process of claim 4 wherein the tertiary alkyl hypochlorite is produced by employing a mole ratio of chlorine to sodium hydroxide from about 0.5:1 to about 1.05:1 and a mole ratio of tertiary alkanol to sodium hydroxide from about 0.75:1 to about 1.1:1.
Claim 7
Dependent Claim
22 words
The process of claim 5 wherein the second reaction zone is operated at a temperature from about 32° to about 160° F.
Claim 8
Dependent Claim
67 words
The process of claim 6 wherein an effluent containing tertiary alkanol, water, chlorohydrin and organic by-products is withdrawn from the second reaction zone; said effluent being subjected to distillation to recover a water chlorohydrin mixture which is introduced into the third reaction zone, a water-tertiary alkanol mixture which is recycled to the first reaction zone, water which is recycled to the second reaction zone and organic by-products.
Claim 9
Dependent Claim
87 words
The process of claim 7 wherein the effluent recovered from the second reaction zone is mixed with cell liquor from the cathode compartment of said electrolytic cell to neutralize hydrogen chloride, and at least a portion of the water recovered from the distillation prior to recycle to the second reaction zone is subjected to evaporation to evaporate water and recover an aqueous brine solution, the evaporated water being recycled to the second reaction zone and the aqueous brine solution being introduced as electrolyte into the electrolytic cell.
Claim 10
Dependent Claim
70 words
The process of claim 8 wherein the organic by-products include chlorinated derivatives, and further comprising burning the chlorinated derivatives with molecular oxygen to produce a combustion effluent containing hydrogen chloride; contacting the combustion effluent with water to absorb the hydrogen chloride and produce a hydrochloric acid solution; and mixing the hydrochloric acid solution with the aqueous brine solution from the first reaction zone prior to introduction into the electrolytic cell.
Claim 11
Dependent Claim
28 words
The process of claim 6 wherein the third reaction zone is operated as a stripping zone with epoxy compound being recovered as overhead and aqueous brine as bottoms.
Claim 12
Dependent Claim
12 words
The process of claim 6 wherein the olefinically unsaturated compound is propylene.
Claim 13
Dependent Claim
13 words
The process of claim 11 wherein the tertiary alkanol is tertiary butyl alcohol.
Claim 14
Dependent Claim
85 words
The process of claim 1 wherein the olefinically unsaturated compound has the following structural formula: R.sub.1 - CH = CH - R.sub.2 wherein R 1 and R 2 are each separately selected from the group consisting of alkyl and phenyl, naphthyl and halo substituted alkyl; phenyl and halo- and alkyl substituted phenyl; naphthyl and halo and alkyl substituted naphthyl; alkenyl and halo substituted alkenyl and wherein R 1 and R 2 are linked together to form a cycloalkene of from 5 to 10 carbon atoms.
Claim 15
Dependent Claim
12 words
The process of claim 1 wherein the olefinically unsaturated compound is styrene.
Claim 16
Dependent Claim
13 words
The process of claim 1 wherein the olefinically unsaturated compound is allyl chloride.
Claim 17
Dependent Claim
12 words
The process of claim 1 wherein the olefinically unsaturated compound is butadiene.
Claim 18
Dependent Claim
12 words
The process of claim 1 wherein the olefinically unsaturated compound is stilbene.
Claim 19
Dependent Claim
20 words
The process of claim 1 wherein the olefinically unsaturated compound is an alkene having from 2 to 4 carbon atoms.
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) | 1980-02-15 | 1980-08-16 | 1981-02-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-15 | 1984-08-16 | 1985-02-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-15 | 1988-08-16 | 1989-02-15 | $7700.00 | Window Closed / Lapsed |