US1904450A - Stabilization of halogenated hydrocarbons - Google Patents
Stabilization of halogenated hydrocarbons Download PDFInfo
- Publication number
- US1904450A US1904450A US519894A US51989431A US1904450A US 1904450 A US1904450 A US 1904450A US 519894 A US519894 A US 519894A US 51989431 A US51989431 A US 51989431A US 1904450 A US1904450 A US 1904450A
- Authority
- US
- United States
- Prior art keywords
- amylene
- stabilization
- composition
- chlorinated
- matter
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
Definitions
- This invention relates to the stabilization of chlorinated hydrocarbons.
- Com ounds of this class for example, trichloret ylene, tetrachlorethane or methylene 5 chloride, tend to undergo decomposition during storage with the formation of substances of acid character. This decomposition makes the product objectionable for such purposes as extraction'and produces an acidity that corrodes storage tanks. While this type of decomposition is more or less general in all chlorinated hydrocarbons, it has been found that materials added to 16 and as such may be very satisfactory for the stabilization of one or more compounds but are not necessarily satisfactory for all others.
- Hydrocarbons for instance gasoline
- stabilizers for trichlorethylene Hydrocarbons, for instance gasoline, have been proposed as stabilizers for trichlorethylene. These are objectionable when the solvent is used in certain processes because a comparatively large amount of gasoline is 4 required to stabilize and the hydrocarbon heavy ends may be deposited in and contaminate the product.
- the object of this invention is to provide an efiective stabilizer for chlorinated hydrotb carbons which need be applied only in small Application filed march 8,
- chlorinated hydrocarbon decomposition with the resultant development of acidity, may be prevented by the addition of amylene in appropriate amounts.
- My process of stabilization consists in mixing a small amount, for instance, 0.0001- 01%, of the stabilizer with the chlorinated hydrocarbon.
- a preferred method of mixing consists in transferring the required amount of a strong stock solution of amylene, made up by weight to known concentration in the chlorinated hydrocarbon to be stabilized, into a known volume of that chlorinated hydrocarbon.
- composition of matter comprising a an chlorinated hydrocarbon and stabilizing amounts of amylene.
- composition of matter comprising a chlorinated hydrocarbon of the group comprising methylene chloride, trichlorethylene,
- composition of matter comprising a chlorinated hydrocarbon and from about M 0.0001% to about 1% by weight of amylene.
- composition of matter comprising methylene chloride and stabilizing amounts ot' amylene.
- composition of matter comprising methylene chloride and from about 0.0001% to about 1% by weight of amylene.
- composition of matter comprising trichlorethylene and stabilizing amounts of am lene. 5w A. composition of matter comprising trichlorethylene and from about 0.000196 to about 1% by weight of amylene.
- composition of matter comprising tetrachlorethane and stabilizing amounts of w amylene.
- composition of matter comprising tetrachlorethane and from about 0.0001% to about 1% by weight of amylene.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Patented Apr. 18, 1933 11m n STATES PATENT OFFICE CHARLES ROBERTS HARRIS, OF NIAGARA FALLS, NEW YORK, ABSIGNOB TO THE BOSSSLER & KABSLACHER ICAL COMPANY, OF NEW YORK, N. Y A CORPORA- 'IION OF DELAWARE STABILIZATION OF HALOGENA'IED HYDROCABBONB Ho Drawing.
This invention relates to the stabilization of chlorinated hydrocarbons.
Com ounds of this class, for example, trichloret ylene, tetrachlorethane or methylene 5 chloride, tend to undergo decomposition during storage with the formation of substances of acid character. This decomposition makes the product objectionable for such purposes as extraction'and produces an acidity that corrodes storage tanks. While this type of decomposition is more or less general in all chlorinated hydrocarbons, it has been found that materials added to 16 and as such may be very satisfactory for the stabilization of one or more compounds but are not necessarily satisfactory for all others.
Such varied substances as xylene, phenols,
20 toluene, resorcinol, guaiacol, thymol, methanol and carbon tetrachloride, have been proposed as stabilizers for chloroform. W e
ave found that these materials are'not of general applicability to all chlorinated hydrocarbons but that the action of the inhibitors is specific in efiect and of a catalytic nature. Some of these substances are very poor stabilizers for certain chlor-hydrocarbons, and must be used in large amounts.
Such amounts of stabilizer renders the chlorinated hydrocarbon useless, for example in certain extractions; poor stabilization results in acidity.
Hydrocarbons, for instance gasoline, have been proposed as stabilizers for trichlorethylene. These are objectionable when the solvent is used in certain processes because a comparatively large amount of gasoline is 4 required to stabilize and the hydrocarbon heavy ends may be deposited in and contaminate the product. v
The object of this invention is to provide an efiective stabilizer for chlorinated hydrotb carbons which need be applied only in small Application filed march 8,
romote stability behave as inhibitory cata ysts 1931. Serial N0. 519,884.
concentrations and which does not'develop an objectionable odor.
I have discovered that chlorinated hydrocarbon decomposition, with the resultant development of acidity, may be prevented by the addition of amylene in appropriate amounts.
My process of stabilization consists in mixing a small amount, for instance, 0.0001- 01%, of the stabilizer with the chlorinated hydrocarbon. A preferred method of mixing consists in transferring the required amount of a strong stock solution of amylene, made up by weight to known concentration in the chlorinated hydrocarbon to be stabilized, into a known volume of that chlorinated hydrocarbon. Other methods according to particular situations that might arise, will readily suggest themselves to one skilled in the art.
To measure the instability of a chlorinated hydrocarbon, I have determined the acidity developed over various periods of time.
Ewamples m A number of chlorinated hydrocarbons were stabilized with small concentrations of amylene as shown in the table below. The formation of acidity in some cases was not only inhibited, but was even reduced. On the other hand the stabilizing action of amylene varies from one chlorinated hydrocarbon to others similar thereto as the table beso low shows. This invention is particularly applicable to trichlorethylene, tetrachlorethane, methylene chloride and perchlorethylene.
To measure instability the acidity developed over various periods of time has been determined. In the following table the acidity is stated in terms of the number of cubic centimeters of 0.01 normal sodium hydroxide solution required to neutralize 25 cc. of W thechlorinated' hydrocarbon, using phenolphthalein as indicator.
mobilization with amulene Maxi- Oman Initial De mum Chlorinated h dxocarbon tmtlon o! mbmm m m 'Irlchloroth lone None 0.8 a 28 1 0 y o. 05% o. a a a Tetraohlorethmic None 0. 2 89 too 0 0. 06% 0. 2 at t. 7 Methylene chloride--. None 0. 8 57 275 o 0. 1% 0. 8 M 0. 0 Perchlorethylene None 0.2 to 150 0. 05% o. a a5 4 N one 0. 2 53 83 0.05% 0. 1 53 80 This invention is not limited to specific roportions of stabilizers. 0.0001 per cent y weight of amylene for any one of a numher of chlorinated hydrocarbons, according to the proposed utility of the composition, is a quite markedly eifective. Practical purposes may demand as high as about 1.0 per cent. The amount added will depend on the spew cific stabilizing agent, the particular compound to be stabilized the problem of its use and the degree of stability desired.
I claim: 1. A composition of matter comprising a an chlorinated hydrocarbon and stabilizing amounts of amylene.
2. A. composition of matter comprising a chlorinated hydrocarbon of the group comprising methylene chloride, trichlorethylene,
35 tetrachlorethane, dichlorethylene and perchlorethylene and stabilizing amounts of amylene.
3. A composition of matter comprising a chlorinated hydrocarbon and from about M 0.0001% to about 1% by weight of amylene.
t. A composition of matter comprising methylene chloride and stabilizing amounts ot' amylene.
5. A composition of matter comprising methylene chloride and from about 0.0001% to about 1% by weight of amylene.
6. A composition of matter comprising trichlorethylene and stabilizing amounts of am lene. 5w A. composition of matter comprising trichlorethylene and from about 0.000196 to about 1% by weight of amylene.
'8. A composition of matter comprising tetrachlorethane and stabilizing amounts of w amylene.
r 9. A composition of matter comprising tetrachlorethane and from about 0.0001% to about 1% by weight of amylene.
Signed at Niagara Falls, in the county of W Niagara and State of New York, this 20th day of February, A. D. 1931.
CHARLES ROBERTS HARRIS.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US519896A US2008680A (en) | 1931-03-03 | 1931-03-03 | Stabilization of halogenated hydrocarbons |
US519894A US1904450A (en) | 1931-03-03 | 1931-03-03 | Stabilization of halogenated hydrocarbons |
FR732569D FR732569A (en) | 1931-03-03 | 1932-03-02 | Chlorinated hydrocarbon stabilization process |
DER84258D DE562820C (en) | 1931-03-03 | 1932-03-03 | Process for stabilizing low molecular weight chlorinated hydrocarbons |
BE386905D BE386905A (en) | 1931-03-03 | 1932-03-03 | |
DER84259D DE573105C (en) | 1931-03-03 | 1932-03-03 | Process for stabilizing low molecular weight chlorinated hydrocarbons |
GB6435/32A GB397915A (en) | 1931-03-03 | 1932-03-03 | Improvements in or relating to the stabilisation of chlorinated hydrocarbons |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US519896A US2008680A (en) | 1931-03-03 | 1931-03-03 | Stabilization of halogenated hydrocarbons |
US519894A US1904450A (en) | 1931-03-03 | 1931-03-03 | Stabilization of halogenated hydrocarbons |
Publications (1)
Publication Number | Publication Date |
---|---|
US1904450A true US1904450A (en) | 1933-04-18 |
Family
ID=27059988
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US519896A Expired - Lifetime US2008680A (en) | 1931-03-03 | 1931-03-03 | Stabilization of halogenated hydrocarbons |
US519894A Expired - Lifetime US1904450A (en) | 1931-03-03 | 1931-03-03 | Stabilization of halogenated hydrocarbons |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US519896A Expired - Lifetime US2008680A (en) | 1931-03-03 | 1931-03-03 | Stabilization of halogenated hydrocarbons |
Country Status (5)
Country | Link |
---|---|
US (2) | US2008680A (en) |
BE (1) | BE386905A (en) |
DE (2) | DE573105C (en) |
FR (1) | FR732569A (en) |
GB (1) | GB397915A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3029297A (en) * | 1960-04-07 | 1962-04-10 | Frontier Chemical Company | Stabilization of chlorinated hydrocarbons |
US3099694A (en) * | 1960-05-27 | 1963-07-30 | Ethyl Corp | Stable methylchloroform compositions |
US3113154A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Stable methylchloroform compositions |
FR2219248A1 (en) * | 1973-02-23 | 1974-09-20 | Diamond Shamrock Corp | Stabilising dichloromethane degreasing compsns. - against reaction with aliphatic cpds. in presence of metals |
FR2219247A1 (en) * | 1973-02-23 | 1974-09-20 | Diamond Shamrock Corp | Stabilising dichloromethane compsn. - using eg diisopropylamine, N-methylpyrrole, butylene oxide etc. |
US3898195A (en) * | 1973-02-23 | 1975-08-05 | Diamond Shamrock Corp | Stabilized methylene chloride composition |
US4032584A (en) * | 1976-05-03 | 1977-06-28 | Stauffer Chemical Company | Stabilized methylene chloride |
US4263464A (en) * | 1977-10-24 | 1981-04-21 | Solvay & Cie. | Stabilized compositions containing methylene chloride |
US11034637B2 (en) | 2016-01-15 | 2021-06-15 | AGC Inc. | Solvent composition, cleaning method, method of forming a coating film, heat transfer fluid, and heat cycle system |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3000977A (en) * | 1961-09-19 | Method of stabilizing trichloroethyl- | ||
US2421035A (en) * | 1942-06-10 | 1947-05-27 | Bell Telephone Labor Inc | Composition for and method of extinguishing fires |
US2426549A (en) * | 1943-09-10 | 1947-08-26 | Sun Oil Co | Lubricant composition |
US2525473A (en) * | 1945-06-16 | 1950-10-10 | Westinghouse Electric Corp | Dielectric |
US2432807A (en) * | 1945-11-26 | 1947-12-16 | Gulf Research Development Co | Petroleum oil compositions |
US2432806A (en) * | 1945-11-26 | 1947-12-16 | Gulf Research Development Co | Petroleum oil compositions |
US2548636A (en) * | 1946-05-29 | 1951-04-10 | Hawley Products Co | Stabilized cuprammonium hydroxide solution and method of preparing the same |
DE1038035B (en) * | 1953-09-25 | 1958-09-04 | Diamond Alkali Co | Stabilization of technical tetrachlorethylene |
US2947792A (en) * | 1954-02-16 | 1960-08-02 | Diamond Alkali Co | Stabilization of tetrachloroethylene with a mixture of a hydroxy alkyne and isoeugenol |
US2751421A (en) * | 1954-02-18 | 1956-06-19 | Du Pont | Stabilization of trichloroethylene |
US3031412A (en) * | 1954-07-23 | 1962-04-24 | Detrex Chem Ind | Composition and method of inhibiting corrosion of ferrous metals by aminestabilized chlorinated hydrocarbons |
NL96889C (en) * | 1954-07-26 | |||
US2958711A (en) * | 1954-07-26 | 1960-11-01 | Diamond Alkali Co | Stabilization of chlorinated hydrocarbons with carboxylic acid esters of acetylenic alcohols |
GB787726A (en) * | 1955-06-16 | 1957-12-11 | Columbia Southern Chem Corp | A method in or relating to stabilization of halogenated hydrocarbons |
US2945895A (en) * | 1956-02-08 | 1960-07-19 | Air Reduction | Stabilization of chlorinated hydrocarbons with a synergistic combination of a tertiary acetylenic monohydric alcohol and 2, 6-di-tert-butyl-paracresol |
US2911449A (en) * | 1956-02-08 | 1959-11-03 | Air Reduction | Stabilization of chlorinated hydrocarbons with a synergistic combination of a tertiary acetylenic monohydric alcohol and certain phenolic compounds |
US2906782A (en) * | 1956-12-21 | 1959-09-29 | Sicedison Spa | Stabilization of the trichloroethylene and stabilizing product therefor |
US2959556A (en) * | 1957-12-05 | 1960-11-08 | Dow Chemical Co | Halogenated hydrocarbons inhibited with organic peroxides |
US3002029A (en) * | 1959-03-26 | 1961-09-26 | Phillips Petroleum Co | Stabilizer for bromo-substituted acetylenic compounds |
US3092981A (en) * | 1960-07-15 | 1963-06-11 | Gen Motors Corp | Refrigeration apparatus |
US3228806A (en) * | 1961-08-04 | 1966-01-11 | Du Pont | Stabilization of chlorohydrocarbons in phosphoric acid coating baths |
DE1215136B (en) * | 1961-10-12 | 1966-04-28 | Vulcan Materials Co | Stabilization of di-, tri- and tetrachloroethylene as well as other lower aliphatic chlorinated hydrocarbons and their mixtures |
NL125376C (en) * | 1962-01-10 | |||
US3297495A (en) * | 1962-11-29 | 1967-01-10 | Hooker Chemical Corp | Process and composition for phosphatizing metals |
NL300188A (en) * | 1962-11-13 | |||
US3230175A (en) * | 1963-04-01 | 1966-01-18 | Du Pont | Stabilized trichloroethylene and a process for treating metals therewith |
US3314884A (en) * | 1964-01-02 | 1967-04-18 | Mobil Oil Corp | Fuels and lubricants containing inclusion compounds |
JPS4816486B1 (en) * | 1967-08-16 | 1973-05-22 | ||
GB1288565A (en) * | 1969-03-24 | 1972-09-13 | ||
US3657120A (en) * | 1970-03-23 | 1972-04-18 | Feuerloschgeratewerk Neuruppin | Method of stabilizing bromine-containing fire extinguishing halogenated hydrocarbon composition |
BE1005713A3 (en) * | 1992-03-02 | 1993-12-28 | Solvay | Process of stabilization and hydrofluoroalkane compositions including at least one hydrofluoroalkane. |
US6534688B2 (en) * | 2001-06-11 | 2003-03-18 | Vulcan Chemicals | Dehydrochlorination stabilization of polychlorinated alkanes |
JP2014221727A (en) * | 2013-05-13 | 2014-11-27 | 昭和電工株式会社 | Dichloromethane purification method and method of producing difluoromethane using the same |
-
1931
- 1931-03-03 US US519896A patent/US2008680A/en not_active Expired - Lifetime
- 1931-03-03 US US519894A patent/US1904450A/en not_active Expired - Lifetime
-
1932
- 1932-03-02 FR FR732569D patent/FR732569A/en not_active Expired
- 1932-03-03 BE BE386905D patent/BE386905A/xx unknown
- 1932-03-03 DE DER84259D patent/DE573105C/en not_active Expired
- 1932-03-03 GB GB6435/32A patent/GB397915A/en not_active Expired
- 1932-03-03 DE DER84258D patent/DE562820C/en not_active Expired
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3029297A (en) * | 1960-04-07 | 1962-04-10 | Frontier Chemical Company | Stabilization of chlorinated hydrocarbons |
US3099694A (en) * | 1960-05-27 | 1963-07-30 | Ethyl Corp | Stable methylchloroform compositions |
US3113154A (en) * | 1960-05-27 | 1963-12-03 | Ethyl Corp | Stable methylchloroform compositions |
FR2219248A1 (en) * | 1973-02-23 | 1974-09-20 | Diamond Shamrock Corp | Stabilising dichloromethane degreasing compsns. - against reaction with aliphatic cpds. in presence of metals |
FR2219247A1 (en) * | 1973-02-23 | 1974-09-20 | Diamond Shamrock Corp | Stabilising dichloromethane compsn. - using eg diisopropylamine, N-methylpyrrole, butylene oxide etc. |
US3898195A (en) * | 1973-02-23 | 1975-08-05 | Diamond Shamrock Corp | Stabilized methylene chloride composition |
US4032584A (en) * | 1976-05-03 | 1977-06-28 | Stauffer Chemical Company | Stabilized methylene chloride |
US4263464A (en) * | 1977-10-24 | 1981-04-21 | Solvay & Cie. | Stabilized compositions containing methylene chloride |
US11034637B2 (en) | 2016-01-15 | 2021-06-15 | AGC Inc. | Solvent composition, cleaning method, method of forming a coating film, heat transfer fluid, and heat cycle system |
US11718574B2 (en) | 2016-01-15 | 2023-08-08 | AGC Inc. | Solvent composition, cleaning method, method of forming a coating film, heat transfer fluid, and heat cycle system |
Also Published As
Publication number | Publication date |
---|---|
DE573105C (en) | 1933-03-29 |
DE562820C (en) | 1932-10-29 |
GB397915A (en) | 1933-09-04 |
US2008680A (en) | 1935-07-23 |
BE386905A (en) | 1932-04-30 |
FR732569A (en) | 1932-09-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US1904450A (en) | Stabilization of halogenated hydrocarbons | |
US2838458A (en) | Inhibited methyl chloroform | |
MXPA03011433A (en) | Inbition of the dehydrochlorination reaction of polychlorinated alkanes. | |
US2721883A (en) | Stabilization of halogenated hydrocarbons | |
US2155723A (en) | Stabilization of trichlorethylene | |
US2981759A (en) | Stabilization of chlorinated hydrocarbons with a synergistic combination of a tertiary acetylenic alcohol, dioxane, and a volatile basic organic nitrogen-containing organic compound | |
US2841625A (en) | Stabilization of chlorinated hydrocarbons with 2, 5-dimethyl-1, 5-hexadiene-3-yne andsynergistic mixtures containing same | |
US2130080A (en) | Inhibition of peroxide formation in aliphatic ethers | |
US2107069A (en) | Stabilization of aliphatic symmetrical iso ethers | |
US3314892A (en) | Stabilization of halohydrocarbons | |
US2114832A (en) | Stabilization of aliphatic mixed ethers | |
US1917073A (en) | Method of stabilizing chlorinated aliphatic hydrocarbons | |
US2517895A (en) | Stabilized chlorohydrocarbon cleaning composition | |
US1925602A (en) | Stabilized solvent | |
US2719181A (en) | Stabilization of chlorinated hydrocarbons with 2-hydroxy-2-methyl-3-butanone | |
US2737532A (en) | Stabilization of perchloroethylene with alkoxyalkylnitriles | |
US3641169A (en) | Stabilization of chlorinated solvents | |
DE69310248T2 (en) | Process for stabilizing a fluorocarbon and mixtures containing at least one fluorocarbon | |
US7507702B2 (en) | Stabilisation of trans-1,2-dichloroethylene | |
US3152191A (en) | Liquid halogenated hydrocarbon stabilized with a primary alkanol and an alkyl aldehyd hydrazone | |
US2964572A (en) | Chemical composition and process | |
US2561916A (en) | Stabilized vinyl aromatic compounds | |
US3397246A (en) | Stabilized chlorinated hydrocarbons | |
US2121009A (en) | Stabilizing vinylidene chloride | |
US4032584A (en) | Stabilized methylene chloride |