US4393227A
Expired / Lapsed
US
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Process for dechlorinating organic compounds
Assignee: EIDP Inc
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Filing: 1981-08-12
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Granted: 1983-07-12
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Expires: 2001-08-12
Abstract
Abstract Olefinic compounds are made from their vicinally chlorinated organic precursors by dechlorination with metallic magnesium in the presence of a mercury-based promoter, which may be a water-soluble mercury salt or metallic mercury, and of a catalytic amount of iodine. This process is particularly suitable for dechlorinating 4,5-dichloro-dioxolanes to the corresponding dioxoles. 4,5-Difluoro-2,2 bis(trifluoromethyl)-1,3-dioxole, which can be made by this process in a reproducible manner from 4,5-dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane, is a useful monomer for making amorphous homopolymers and copolymers with tetrafluoroethylene, which are well suited for wire coating, finishes, and transparent glazing for corrosive service.
Inventors
- 👤 Edward N. Squire
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 09:06
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/10; C07D317/32; C07D317/42
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
127 words
A process for dechlorinating an organic compound selected from the group consisting of ##STR4## where each of Y and Z independently is hydrogen, chlorine or fluorine, provided at least one of Y and Z is fluorine; and each of R 3 and R 4 independently is hydrogen, fluorine or trifluoromethyl to the ethylenically unsaturated compound, said process comprising contacting the organic chlorine-containing compound with at least a stoichiometric amount of metallic magnesium, a mercury based promoter selected from water-soluble mercury salts and metallic mercury, and iodine in the presence of tetrahydrofuran at a temperature from about room temperature to at least the boiling point of tetrahydrofuran at the operating pressure; with a proviso that magnesium amalgam can be used in lieu of magnesium and the mercury-based promoter.
Claim 2
Dependent Claim
127 words
A process for dechlorinating an organic compound selected from the group consisting of ##STR4## where each of Y and Z independently is hydrogen, chlorine or fluorine, provided at least one of Y and Z is fluorine; and each of R 3 and R 4 independently is hydrogen, fluorine or trifluoromethyl to the ethylenically unsaturated compound, said process comprising contacting the organic chlorine-containing compound with at least a stoichiometric amount of metallic magnesium, a mercury based promoter selected from water-soluble mercury salts and metallic mercury, and iodine in the presence of tetrahydrofuran at a temperature from about room temperature to at least the boiling point of tetrahydrofuran at the operating pressure; with a proviso that magnesium amalgam can be used in lieu of magnesium and the mercury-based promoter.
Claim 3
Dependent Claim
23 words
The process of claim 1 wherein each of Y and Z is fluorine, and each of R 3 and R 4 is trifluoromethyl.
Claim 4
Dependent Claim
25 words
The process of claim 1 wherein each of Y and Z is hydrogen, and each of R 3 and R 4 is trifluoromethyl or fluorine.
Claim 5
Dependent Claim
17 words
The process of claim 1 wherein each of Y, Z, R 3 and R 4 is fluorine.
Claim 6
Dependent Claim
23 words
The process of claim 1 wherein Y is hydrogen; Z is fluorine; and each of R 3 and R 4 fluorine or trifluoromethyl.
Claim 7
Dependent Claim
24 words
The process of claim 1 wherein Y is chlorine; Z is fluorine; and each of R 3 and R 4 is trifluoromethyl or fluorine.
Claim 8
Dependent Claim
62 words
The process of claim 1 wherein the starting dioxolane is added gradually over a suitable period to a hot reaction medium consisting of tetrahydrofuran, magnesium, mercuric chloride, and iodine, and liquid is distilled from the reaction medium at such a rate that its volume, in milliliters, is greater than the amount of the starting dioxolane, in grams, added during the same period.
Claim 9
Dependent Claim
29 words
The process of claim 7 wherein the ratio of the volume of liquid recovered by distillation, in mL/min, to the weight of dioxolane added, in g/min, is about 1.1-10.
Claim 10
Dependent Claim
12 words
The process of claim 8 wherein the ratio is about 1.5-8 mL/g.
Claim 11
Dependent Claim
12 words
The process of claim 9 wherein the ratio is about 1.5-5 mL/g.
Claim 12
Dependent Claim
22 words
The process of claim 1 wherein the amount of magnesium is 1.1-8 gram-atoms per two gram-atoms of vicinal chlorine to be removed.
Claim 13
Dependent Claim
19 words
The process of claim 10 wherein the amount of magnesium is 2-6 gram-atoms per two gram-atoms of vicinal chlorine.
Claim 14
Dependent Claim
22 words
The process of claim 1 wherein the water-soluble mercury salt is selected from mercuric nitrate, mercuric chloride, mercuric acetate, and mercurous nitrate.
Claim 15
Dependent Claim
30 words
The process of claim 13 wherein the weight ratio of magnesium to mercury salt is 1:0.01 to 1:0.15, and the weight ratio of magnesium to iodine is 1:0.75 to 1:0.002.
Claim 16
Dependent Claim
38 words
The process of claim 14 wherein the mercury salt is a mercuric salt, and the weight ratio of magnesium to mercuric salt is 1:0.01 to 1:0.07, and the weight ratio of magnesium to iodine is 1:0.35 to 1:0.01.
Claim 17
Dependent Claim
30 words
The process of claim 15 wherein the weight ratio of magnesium to mercuric salt is 1:0.02 to 1:0.04, and the weight ratio of magnesium to iodine is 1:0.07 to 1:0.05.
Claim 18
Dependent Claim
25 words
The process of claim 1 wherein the mercury-based promoter is metallic mercury, and the weight ratio of magnesium to mercury is about 100:1 to 0.2:1.
Claim 19
Dependent Claim
25 words
A process of claim 1 which is carried out at atmospheric pressure within the temperature range of room temperature to the boiling temperature of tetrahydrofuran.
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) | 1986-07-11 | 1987-01-10 | 1987-07-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-07-11 | 1991-01-10 | 1991-07-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-07-11 | 1995-01-10 | 1995-07-12 | $7700.00 | Window Closed / Lapsed |