US2672484A - Stabilization of levinstein mustard gas - Google Patents
Stabilization of levinstein mustard gas Download PDFInfo
- Publication number
- US2672484A US2672484A US591291A US59129145A US2672484A US 2672484 A US2672484 A US 2672484A US 591291 A US591291 A US 591291A US 59129145 A US59129145 A US 59129145A US 2672484 A US2672484 A US 2672484A
- Authority
- US
- United States
- Prior art keywords
- levinstein
- mustard
- stabilization
- mustard gas
- morpholine
- 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.)
- Expired - Lifetime
Links
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 title claims description 33
- 230000006641 stabilisation Effects 0.000 title description 5
- 238000011105 stabilization Methods 0.000 title description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 10
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 241000219198 Brassica Species 0.000 description 25
- 235000003351 Brassica cretica Nutrition 0.000 description 25
- 235000003343 Brassica rupestris Nutrition 0.000 description 25
- 235000010460 mustard Nutrition 0.000 description 25
- 238000000034 method Methods 0.000 description 8
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- 229920001021 polysulfide Polymers 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RWOBLAUPXQBIAW-UHFFFAOYSA-N 1,1-dichloro-2-(2,2-dichloroethylsulfanyl)ethane Chemical compound ClC(Cl)CSCC(Cl)Cl RWOBLAUPXQBIAW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000012822 chemical development Methods 0.000 description 1
- 239000002575 chemical warfare agent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
Definitions
- This invention relates to the stabilization of Levinstein mustard.
- the most important chem ical warfare vesicant agent known to date is the agent known as mustard gas. Chemically, pure mustard gas or mustard is bis-(beta-chloroethyl) sulfide, Although there are several processes for manufacturing mustard, the most important method in this country is the socalled Levinstein process. The product of the Levinstein process is commonly known to those skilled in the art as Levinstein mustard.
- Levinstein mustard is a relatively impure product, and the dichlorethyl sulfide content thereof is in the neighborhood or" 70%.
- the impurities in Levinstein mustard are of a complex nature and have not been completely determined to this date, but are essentially polysulfides of the composition (C1CH2CH2)2SI-
- Levinstein mustard has very effective vesicant properties, and is substantially equivalent to pure mustard from the vesicant standpoint, it does have the serious objection of being unstable over long periods of storage in steel containers, especially at temperatures of 110 to 158 F. l'he exact reasons for the degradation of Levinstein mustard in storage have not been fully determined in all respects.
- the object of this invention is to provide a practical effective means of stabilizing Levinstein mustard. so as to prevent to a large degree its deterioration in storage.
- the means of stabilizing Levinstein mustard provided by this invention consists in adding thereto small amounts of certain amines which have been found effective for this purpose.
- the amines, which are presently preferred as stabilizers of Levinstein mustard are: morpholine, hexamethylenetetramine, dimethyl amine, triethylene tetramine, and tetraethylene pentamine.
- a stabilized mixture consisting essentially of bis-(beta chlorethyl) sulphide and sulphides having the formula ('ClCHzCHz) 281 and morpholine, said morpholine constituting by Weight 1% of said mixture.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Mar. 16, 1954 STABILIZATION OF LEVINSTEIN MUSTARD GAS Rudolph Macy, Baltimore; Md., assignor to the Unitedstates of America as represented by the Secretary of War narrating; Application May 1, 1945,
1. ser al 2 Claims. (01." 260-609) (Granted under Title 35, u. s. ooae*(1952-);-
sec. 266) The invention described herein may be manufactured and used by Or for the Government, for governmental purposes, without the payment to me of any royalty thereon.
This invention relates to the stabilization of Levinstein mustard. The most important chem ical warfare vesicant agent known to date is the agent known as mustard gas. Chemically, pure mustard gas or mustard is bis-(beta-chloroethyl) sulfide, Although there are several processes for manufacturing mustard, the most important method in this country is the socalled Levinstein process. The product of the Levinstein process is commonly known to those skilled in the art as Levinstein mustard.
Levinstein mustard is a relatively impure product, and the dichlorethyl sulfide content thereof is in the neighborhood or" 70%. The impurities in Levinstein mustard are of a complex nature and have not been completely determined to this date, but are essentially polysulfides of the composition (C1CH2CH2)2SI- Although Levinstein mustard has very effective vesicant properties, and is substantially equivalent to pure mustard from the vesicant standpoint, it does have the serious objection of being unstable over long periods of storage in steel containers, especially at temperatures of 110 to 158 F. l'he exact reasons for the degradation of Levinstein mustard in storage have not been fully determined in all respects. However, it is known that the instability is due to certain impurities present, since the pure product is not unstable under normal storage conditions. A number of theories have been advanced from various sources as to the causes of the instability of Levinstein mustard. Corrosion of steel containers by the mustard molecule is probably due to its inner salt nature, and in the case or Levinstein mustard this is enhanced by presence of polysulfides containing labile sulfur. Because of these polysulfides, iron actually dissolves in Levinstein mustard at slightly elevated temperature. Levinstein mustard is very stable in glass containers, or in steel containers coated with a properly haired-on suitable lacquer.
Regardless of the exact reasons for the instability of Levinstein mustard, the problem is fully recognized and is extremely serious during time of war and national emergency when it becomes necessary to build up a, very great strategic reserve of this chemical warfare agent in contemplation of the fact that chemical warfare may, at any time, be resorted to.
From a practical standpoint it is necessary to store the bulk of the stool; pile of Levinstein mustard in steel drums. Logistical reasons make it necessary to have a sizable proportion of Levinstein mustard supply located in tropical, or near tropical, regions. The high temperatures in such regions greatly hasten the deterioration or degradation of the Levinstein mustard stored in such regions. During the spoilage or deterioration of Levinstein mustard, pressures develop in the steel drums, and eventually, if the product is not used, the deterioration is carried to the point where it is necessary to destroy the portion of the supply which has so deteriorated.
Although the above outlined problem has been known since World War I, when Levinstein mustard was produced and stored on a large scale, there has been heretofore no satisfactory method or means of stabilizing Levinstein mustard with respect to chemical decomposition and development of pressure. A great amount of research efiort has been devoted to the problem. However, prior to this invention, the net results of such previous research and investigation of the problem only indicated that ammonia was a partially effective stabilizer for Levinstein mustard, and that partial stabilization could be obtained by the use of small amounts of strong bases. However, none of these methods or means of stabilization were at all satisfactory from a practical standpoint.
Accordingly, the object of this invention is to provide a practical effective means of stabilizing Levinstein mustard. so as to prevent to a large degree its deterioration in storage. Briefly stated, the means of stabilizing Levinstein mustard provided by this invention, consists in adding thereto small amounts of certain amines which have been found effective for this purpose. The amines, which are presently preferred as stabilizers of Levinstein mustard, are: morpholine, hexamethylenetetramine, dimethyl amine, triethylene tetramine, and tetraethylene pentamine.
Specifically, 0.5% hexamethylenetetramine, 1% of dimethyl amine, and 1% of morpholine have been found to be effective.
The nature of this invention having been broadly outlined above, and preferred embodiments of the invention having been described, it will be apparent that certain modifications and additional formulations will suggest themselves to those skilled in the art. Accordingly, it is intended that the foregoing descriptive material 3 shall be interpreted as illustrative and not in a limiting sense. Iclaim:
1. A stabilized mixture consisting essentially of bis-(beta chlorethyl) sulphide and sulphides having the formula ('ClCHzCHz) 281 and morpholine, said morpholine constituting by Weight 1% of said mixture.
2. The method of stabilizing a mixture consisting essentially of bis-(beta chlorethyl) sulphide and sulphides having the composition (C1CH2CH2)2S1:, said method consisting essentially in adding morpholine to said mixture in an amount constituting, by Weight, 1% of the weight of said mixture.
RUDOLPH MACY.
4 References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 1,719,168 Chamberlain July 2, 1929 1,903,287 Cox Apr. 4, 1933 2,043,259 Messbach June 9, 1936 2,268,608 McNulty Jan. 6, 1942 2,498,684 I-Ium Feb. 28, 1950 OTHER REFERENCES Lawson et al., Journal Am. Chem. Soc," vol. 47, pp. 282l-S6l1925). (Copy in Scientific Library.)
Mann et a1., Industrial 8; Eng. Chem., vol. 28., No. 2, Feb. 1936, pp. 159-163. (Copy in Scientific Library.)
Claims (1)
1. A STABILIZED MIXTURE CONSISTING ESSENTIALLY OF BIS-(BETA CHLORETHYL) SULPHIDE AND SULPHIDES HAVING THE FORMULA (CLCH2CH2) 2SX AND MORPHOLINE, SAID MORPHOLINE CONSTITUTING BY WEIGHT 1% OF SAID MIXTURE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US591291A US2672484A (en) | 1945-05-01 | 1945-05-01 | Stabilization of levinstein mustard gas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US591291A US2672484A (en) | 1945-05-01 | 1945-05-01 | Stabilization of levinstein mustard gas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2672484A true US2672484A (en) | 1954-03-16 |
Family
ID=24365886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US591291A Expired - Lifetime US2672484A (en) | 1945-05-01 | 1945-05-01 | Stabilization of levinstein mustard gas |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2672484A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1719168A (en) * | 1927-01-11 | 1929-07-02 | Vanderbilt Co R T | Pickling of metals, etc. |
| US1903287A (en) * | 1932-04-25 | 1933-04-04 | Carbide & Carbon Chem Corp | Corrosion inhibitor |
| US2043259A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Stabilized carbon tetrachloride |
| US2268608A (en) * | 1939-12-05 | 1942-01-06 | Standard Oil Dev Co | Lubricants |
| US2498684A (en) * | 1945-05-01 | 1950-02-28 | Jack K Y Hum | Chemical product |
-
1945
- 1945-05-01 US US591291A patent/US2672484A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1719168A (en) * | 1927-01-11 | 1929-07-02 | Vanderbilt Co R T | Pickling of metals, etc. |
| US1903287A (en) * | 1932-04-25 | 1933-04-04 | Carbide & Carbon Chem Corp | Corrosion inhibitor |
| US2043259A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Stabilized carbon tetrachloride |
| US2268608A (en) * | 1939-12-05 | 1942-01-06 | Standard Oil Dev Co | Lubricants |
| US2498684A (en) * | 1945-05-01 | 1950-02-28 | Jack K Y Hum | Chemical product |
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