GB2027697A - Stabilization of Cyclohexene Oxide - Google Patents
Stabilization of Cyclohexene Oxide Download PDFInfo
- Publication number
- GB2027697A GB2027697A GB7924630A GB7924630A GB2027697A GB 2027697 A GB2027697 A GB 2027697A GB 7924630 A GB7924630 A GB 7924630A GB 7924630 A GB7924630 A GB 7924630A GB 2027697 A GB2027697 A GB 2027697A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexene oxide
- composition
- weight
- percent
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 title claims abstract description 38
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 230000006641 stabilisation Effects 0.000 title description 6
- 238000011105 stabilization Methods 0.000 title description 6
- 239000002904 solvent Substances 0.000 claims abstract description 37
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 18
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims abstract 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 14
- LOWMYOWHQMKBTM-UHFFFAOYSA-N 1-butylsulfinylbutane Chemical group CCCCS(=O)CCCC LOWMYOWHQMKBTM-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000000354 decomposition reaction Methods 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- -1 alkoxynitriles Chemical class 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 229910001250 2024 aluminium alloy Inorganic materials 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000007514 turning Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- 239000013527 degreasing agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- DCWQZPJHHVLHSV-UHFFFAOYSA-N 3-ethoxypropanenitrile Chemical compound CCOCCC#N DCWQZPJHHVLHSV-UHFFFAOYSA-N 0.000 description 1
- 229910001008 7075 aluminium alloy Inorganic materials 0.000 description 1
- 238000010953 Ames test Methods 0.000 description 1
- 231100000039 Ames test Toxicity 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- JDOADFHRSNEOPC-UHFFFAOYSA-N C1CO1.C1CCC2OC2C1 Chemical class C1CO1.C1CCC2OC2C1 JDOADFHRSNEOPC-UHFFFAOYSA-N 0.000 description 1
- 235000004237 Crocus Nutrition 0.000 description 1
- 241000596148 Crocus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- PSACHCMMPFMFAJ-UHFFFAOYSA-N nmm n-methylmorpholine Chemical compound CN1CCOCC1.CN1CCOCC1 PSACHCMMPFMFAJ-UHFFFAOYSA-N 0.000 description 1
- 230000002352 nonmutagenic effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000003617 peroxidasic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/36—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
Abstract
The invention provides a composition comprising cyclohexene oxide containing a stabilizing amount of dialkyl sulfoxide represented by the general formula R2S=O wherein R is an aliphatic radical containing from 2 to 8 carbon atoms having at least one hydrogen atom on a beta-carbon atom. It also provides a composition comprising a chlorinated solvent containing a stabilizing amount of cyclohexene oxide, the cyclohexene oxide being stabilized with dialkyl sulphoxide represented by the general formula R2S=O wherein R is an aliphatic radical containing from 2 to 8 carbon atoms having at least one hydrogen atom on a beta-carbon atom.
Description
SPECIFICATION
Stabilization of Cyclohexene Oxide
Oxirane compounds such as epichlorohydrin, cyclohexene oxide, glycidol, glycidyl ethers, and the like, usually in combination with other compounds such as alkoxynitriles, amines, amides, alcohols, and esters, are commonly used to stabilize chlorinated solvents, such as perchloroethylene, against metal induced decomposition.
Of the oxirane compounds, epichlorohydrin is perhaps most commonly used due to its proven effectiveness and ready availability. However, since epichlorohydrin has been shown by the Ames Test to exhibit mutagenic activity, its continued permissable use in chlorinated solvent stabilization systems is questionable for reasons of health and safety.
Cyclohexene oxide has been demonstrated to be an acceptable non-mutagenic substitute for epichlorohydrin in chlorinated solvent stabilization systems; however, cyclohexene oxide suffers from the disadvantage that it, itself, is unstable and develops acidity upon storage, especially when exposed to air.
It is believed that cyclohexene oxide autoperoxidizes to form a decomposition product which is believed to be cyclopentane carboxylic acid, which decomposition product causes severe pitting and corrosion of metals, particularly aluminum. Consequently, before cyclohexene oxide can be effectively used to stablize chlorinated solvents against metal induced decomposition, the cyclohexene oxide itself must be stablized against perioxidative decomposition.
Cyclohexene oxide is usually stabilized against decomposition by the inclusion of a stebilizing amount of butyiated hydroxytoluene (BHT). However, it has been found that BHT stabilized cyclohexenes oxide is not very effective in stabilizing unsaturated chlorinated solvents, for example, perchloroethylene, against metal, particularly aluminum, induced decomposition, especially when the solvent is used in degreasing operations.
It is desirable, therefore, to devise means of stabilizing cyclohexene oxide against decomposition which stabilized cyclohexene oxide would be particularly effective in stabilizing unsaturated chlorinated solvents against metal induced decomposition in addition to having the capacity to neutralize any hydrochloric acid decomposition product.
In accordance with this invention, it has been found that cyclohexene oxide is stabilized against peroxidative decomposition by the inclusion therein of a stabilizing amount of di-n-butyl sulfoxide.
Although di-n-butyl sulfoxide has been found to be particularly effective in stabilizing cyclohexene oxide against perioxidative decomposition, it is contemplated that other dialkyl sulfoxides would be suitable for use in the invention. Such other dialkyl sulfoxides may be represented by the general formula,
R2S=O, wherein R is a C2 to Ca, preferably C2to C4, aliphatic radical that must contain at least one hydrogen atom on a beta-carbon atom. Sone other aliphatic radicals of which R is representative include, for example, ethyl, n-propyl, isopropyl, t-butyl, sec-butyl,isobutyl, hexyl, cyclohexyl, 2ethylhexyl, 2-phenoxyethyl, and the like.The quantity of dialkyl sulfoxide used to stabilize cyclohexene oxide may vary over a range of from about 0.3 percent to 20 percent by weight, preferably from about 0.5 percent to 5.0 percent by weight, and most preferably from about 0.9 percent to 2.0 percent by weight based on the weight of cyclohexene oxide.
The diaikyl sulfoxide stabilized cyclohexene oxide is particularly effective in stabilizing chlorinated solvents such as perchloroethylene against aluminum induced decomposition. When used to stabilize chlorinated solvents, the dialkyl sulfoxide stabilized cyclohexene oxide is employed in typical stabilizing amount, usually from about 0.01 to 0.5 percent, preferably from about 0.1 to 0.3 percent by weight of cyclohexene oxide based on the weight solvent, although as much as 5.0 percent by weight may be used.
The cyclohexene oxide may be stabilized with dialkyl sulfoxide prior to stabilizing the solvent or unstabilized cyclohexene oxide and dialkyl sulfoxide may be added separately to the solvent thus stabilizing the cyclohexene oxide in situ.
The stabilization afforded cyclohexene oxide by dialkyl sulfoxide is not appreciably affected by the presence of stabilizing amounts of other commonly used chlorinated solvent stabilizing components such as, for example, phenols, alcohols, esters, amines, amides, nitriles, and the like.
The invention is further illustrated but is not intended to be limited by the following examples.
Example 1
A series of stabilized perchloroethylene samples was prepared using the following stabilization systems. The stabilizing materials are expressed as percent by weight based on the weight of perchloroethylene:
Sample No. 1 2 3 4 5
CHO 0.27 0.27 0.27 0.27 0.27
HQMME 0.01 0.01 0.01 0.01 0.01
NMM 0.005 0.005 0.005 0.005 0.005
EPN 0.06 0.06 0.06 0.06 0.06
BHT - 0.00135(a) - -
DNBS - - 0.001(b) 0.0025(c) 0.005(d)
(a) 0.5 weight percent BHT based on weight of CHO
(b) 0.37 weight percent DNBS based on weight of CHO
(c) 0.93 weight percent DNBS based on weight of CHO
(d) 1.86 weight percent DNBS based on weight of CHO
Legend:CHO -cyclohexene oxide
HQMME -hydroquinone monomethyl ether
NMM --N-methylmorpholine EPN -beta-ethoxypropionitrile BHT -butylated hydroxytoluene
DNBS -di-n-butyl sulfoxide
100 milliliters of each of the above stabilized solvents were placed in individual 250 milliliter Erlenmeyerflasks. A2024 aluminum coupon measuring 1/2 inchx4 inchesxl/32 inch was placed in each flask. Each coupon was polished with a crocus cloth and cleaned with acetone immediately prior to its being placed in its respective flask. Each flask was provided with a reflux condenser and heated to refluxing temperature.The flask contents were refluxed until visible signs of corrosion, i.e., black spots, appeared on the coupons. Under the microscope, these spots appeared as small craters covered with a reddish-brown powder.
The results of the reflux tests are as follows:
Days Until Days Until
Sample Corrosion Observed Test Terminated
1 5 5
2 6 6
3 10 10
4 None 35
5 None 35
Example 2
A simulated glass degreaser was constructed from a three-liter capacity, one-neck, round bottom flask, a two-liter capacity flask, and a water-cooled condenser.
The condenser outlet was connected by rubber tubing to a safety trap and a silver nitrate trap connected in series. The two-liter flask was modified by inserting and fusing a piece of glass tubing with a 24/40 T male joint through the bottom of the flask. One end of the tube extended about halfway into the flask such that about one liter of solvent could be collected before overflowing back into the bottom three-liter flask (simulated boiling sump). Before starting the test, about 60 grams each of 2024 and 7075 aluminum turnings, 200 milliliters of Limex#78 oil and two liters of perchloroethylene were added to the boiling sump. The modified two-liter flask (simulated rinse tank) was fitted to the three-liter flask and 500 milliliters of perchloroethylene were added to the two-liter flask.The assembly was heated to and maintained at reflux temperature by means of a Variac controlled heating mantle.
Solvent decomposition was indicated by the appearance of a white silver chloride precipitate in the silver nitrate trap.
One test was run using perchloroethylene that was stabilized by the addition thereto of 0.27 weight percent cyclohexene oxide, 0.005 weight percent di-n-butyl sulfoxide, 0.01 weight percent hydroquinone monomethyl ether, 0.06 weight percent beta-ethoxy-propionitrile and 0.005 weight percent N-methyl-morpholine (solvent A).
Another test was run using perchloroethylene stabilized as above except that no di-n-butyl sulfoxide was added (solvent B).
Samples of perchloroethylene was taken from the boiling sump at periodic intervals and analyzed acid acceptance. The results of these tests are summarized as follows:
Solvent A Solvent B
Days Acid Acid Reflux pH Acceptance /O pH Acceptance % 0 8.60 0.101 8.35 0.1043
1 - - 8.40 0.0859
6 8.35 0.0818 11 8.41 0.0818 7.55 0.276 13 8.43 0.0818 - 14 -- -- 5.15 -0.0356 18 8.36 0.0815 - 25 8.33 0.0807 As seen from the above, perchloroethylene stabilized with unstabilized cyclohexene oxide (solvent B) develops acidity quite rapidly under simulated degreasing conditions as compared with perchloroethylene stabilized with di-n-butyl sulfoxide stabilized cyclohexene oxide (solvent A).
Moreover, examination of the aluminum turnings showed no attack from solvent A whereas the aluminum turnings were severely pitted from solvent B.
The acid acceptance of the solvent is a measure of the capacity of the solvent to neutralize hydrochloric acid and is expressed in percent by weight of equivalent sodium hydroxide. The acid acceptance is determined as follows. To an Erlenmeyer flask is added 25 milliliters of 0.1 N hydrochloric acid in isopropyl alcohol, 10 milliliters of solvent, and 25 milliliters of isopropyl alcohol.
The contents of the flask are thoroughly mixed, the flask is stoppered and aliowed to stand for 10 minutes at room temperature. Three drops of bromophenol blue indicator are added and the flask contents are titrated with 0.1 N sodium hydroxide to the blue-green end point.
A blank determined is made by titrating 25 milliliters of 0.1 N hydrochloric acid in isopropyi alcohol and 25 milliliters of isopropyl alcohol with 0.1 N sodium hydroxide to the blue-green bromophenol blue end point.
Acid acceptance in weight percent equivalent sodium hydroxide is calculated as follows: (K-S)Nx0.04x 100
Acid Acceptance=
W wherein:
K=milliliters of NaOH solution required for the blank titration
S=milliliters of NaOH solution required for the sample titration;
N=normality of the NaOH solution; and
W=grams of sample (volume in millilitersxspecific gravity).
Example 3
The perchloroethylene solvents A and B prepared as described in Example 2 were tested in
Baron-Blakeslee model MVW-125 vapor-spray degreaser.
After 814 hours of operation, a sample of solvent A taken from the boiling sump had a pH of 7.91 and an acid acceptance of 0.112 percent. No sign of corrosion was observed on a 2024 aluminum test panel that had been immersed in the solvent in the boiling sump throughout the test period.
After 574 hours of operation, a sample of solvent B taken from the boiling sump had a pH of 7.7 and an acid acceptance of 0.094 percent. A 2024 aluminum test panel that had been immersed in the boiling sump throughout the test period was severely corroded and pitted.
Although the invention has been described with specific references and specific details of embodiments thereof, it is to be understood that it is not intended to be so limited since changes and alterations therein may be made by those skilled in the art which are within the full intended scope of this invention as defined by the appended claims.
Claims (12)
1. A composition comprising cyclohexene oxide containing a stabilizing amount of dialkyl sulfoxide represented by the general formula R2S=O wherein R is an aliphatic radical containing from 2 to 8 carbon atoms having at least one hydrogen atom on a beta-carbon atom.
2. A composition as claimed in claim 1 wherein R contains from 2 to 4 carbon atoms.
3. A composition as claimed in claim 1 wherein the dialkyl sulfoxide is di-n-butyl sulfoxide.
4. A composition as claimed in claim 1,2 or 3 wherein the cyclohexene oxide contains from about 0.3 percent to about 20 percent by weight dialkyl sulfoxide based on the weight of cyclohexene oxide.
5. A composition as claimed in claim 4 wherein the cyclohexene oxide contains from about 0.5 percent to 5.0 percent by weight dialkyl sulfoxide based on the weight of cyclohexene oxide.
6. A composition as claimed in claim 5 wherein the cyclohexene oxide contains from about 0.9 percent to 2.0 percent by weight dialkyl sulfoxide based on the weight of cyclohexene oxide.
7. A composition comprising cyciohexene oxide containing a stabilizing amount of dialkyl sulphoxide substantially as herein described with reference to and as illustrated in any of the Examples.
8. A composition comprising a chlorinated solvent containing a stabilizing amount of a composition as claimed in any of claims 1 to 7.
9. A composition as claimed in claim 8 wherein the solvent is perchloroethylene.
10. A composition as claimed in claim 8 or 9 containing from about 0.01 percent to 5.0 percent by weight cyclohexene oxide based on the weight of solvent.
11. A composition as claimed in claim 10 containing from about 0.1 to 0.3 percent by weight cyclohexene oxide based on the weight of solvent.
12. A composition comprising a chlorinated solvent containing a stabilizing amount of cyclohexene oxide, the cyclohexene oxide being stabilized with a dialkyl sulphoxide, substantially as herein described with reference to and as illustrated in any of the Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92526878A | 1978-07-17 | 1978-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2027697A true GB2027697A (en) | 1980-02-27 |
Family
ID=25451484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7924630A Withdrawn GB2027697A (en) | 1978-07-17 | 1979-07-16 | Stabilization of Cyclohexene Oxide |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5515467A (en) |
| BE (1) | BE877684A (en) |
| DE (1) | DE2928640C3 (en) |
| FR (1) | FR2431527A1 (en) |
| GB (1) | GB2027697A (en) |
| IT (1) | IT1122190B (en) |
| SE (1) | SE7906116L (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1342814A1 (en) * | 2002-03-06 | 2003-09-10 | Shell Internationale Researchmaatschappij B.V. | A method for inhibiting the autopolymerization of ethylene oxide caused by rust using redox chemistry |
| US8858820B2 (en) | 2011-10-07 | 2014-10-14 | American Pacific Corporation | Bromofluorocarbon compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5028933A (en) * | 1973-07-13 | 1975-03-24 | ||
| JPS5028929A (en) * | 1973-07-13 | 1975-03-24 |
-
1979
- 1979-07-09 JP JP8681379A patent/JPS5515467A/en active Granted
- 1979-07-13 SE SE7906116A patent/SE7906116L/en unknown
- 1979-07-13 BE BE0/196284A patent/BE877684A/en not_active IP Right Cessation
- 1979-07-16 FR FR7918395A patent/FR2431527A1/en active Granted
- 1979-07-16 GB GB7924630A patent/GB2027697A/en not_active Withdrawn
- 1979-07-16 IT IT7924378A patent/IT1122190B/en active
- 1979-07-16 DE DE2928640A patent/DE2928640C3/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1342814A1 (en) * | 2002-03-06 | 2003-09-10 | Shell Internationale Researchmaatschappij B.V. | A method for inhibiting the autopolymerization of ethylene oxide caused by rust using redox chemistry |
| US6723404B2 (en) | 2002-03-06 | 2004-04-20 | Shell Oil Company | Inhibition of ethylene oxide autopolymerization |
| US8858820B2 (en) | 2011-10-07 | 2014-10-14 | American Pacific Corporation | Bromofluorocarbon compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE877684A (en) | 1980-01-14 |
| FR2431527A1 (en) | 1980-02-15 |
| IT7924378A0 (en) | 1979-07-16 |
| DE2928640A1 (en) | 1980-02-28 |
| SE7906116L (en) | 1980-01-18 |
| FR2431527B1 (en) | 1982-12-31 |
| DE2928640B2 (en) | 1981-04-16 |
| JPS5734267B2 (en) | 1982-07-22 |
| IT1122190B (en) | 1986-04-23 |
| DE2928640C3 (en) | 1982-04-01 |
| JPS5515467A (en) | 1980-02-02 |
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