US3424805A - Chlorinated hydrocarbon compositions - Google Patents
Chlorinated hydrocarbon compositions Download PDFInfo
- Publication number
- US3424805A US3424805A US599367A US3424805DA US3424805A US 3424805 A US3424805 A US 3424805A US 599367 A US599367 A US 599367A US 3424805D A US3424805D A US 3424805DA US 3424805 A US3424805 A US 3424805A
- Authority
- US
- United States
- Prior art keywords
- chlorinated hydrocarbon
- trichlorethylene
- weight percent
- hours
- pyrrole
- 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
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 title description 15
- 239000000203 mixture Substances 0.000 title description 4
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 16
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 16
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 14
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 14
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 14
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000000087 stabilizing effect Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002926 oxygen Chemical class 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- -1 dichlorethylene, trichlorethylene, perchlorethylene Chemical group 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UAIVFDJJMVMUGY-UHFFFAOYSA-N 1,2,4-trimethylpiperazine Chemical compound CC1CN(C)CCN1C UAIVFDJJMVMUGY-UHFFFAOYSA-N 0.000 description 1
- KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical group ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101100079846 Homo sapiens NEU1 gene Proteins 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 102100028760 Sialidase-1 Human genes 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
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
- Example 2 In a test made in accordance with Example 1, 200 ml. trichlorethylene with an additive of 0.004 weight percent diisopropylamine and 0.004 weight percent ethylene diamine are refluxed for 48 hours. After that period, and even after 450 hours heating the test is still alkaline.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
United States Patent W 40,491 US. Cl. 260-6525 2 Claims Int. Cl. C07c 21 /04, 21/10, 21/12 ABSTRACT OF THE DISCLOSURE Stable chlorinated hydrocarbon compositions are prepared by adding to the chlorinated hydrocarbon an amine of the general formula H NANH where A is a bivalent aliphatic alkyl radical with 23 C atoms, together with pyrrole or N-methyl-pyrrole.
This invention relates to stabilizing chlorinated hydrocarbons and it has for its object to provide a novel and improved process for this purpose.
Another object of the invention is to enable chlorinated hydrocarbons to be effectively stabilized by the addition thereto of very small quantities of specific compounds hereinafter described.
Numerous solvents are used for degreasing metals, for dry cleaning and for extraction purposes. Among these the unsaturated chlorinated aliphatic hydrocarbons are preferred because of their high solvent effect and their incombustibility, especially, for instance, trichlorethylene. However, the advantage of their strong solvent effect is offset by the drawback of their poor stability which makes their use without prior stabilization very ditficult.
The decomposition of trichlorethylene, for instance, is caused by light and oxygen and is catalyzed by heat and contact with metals. Therefore small quantities of additives are used to stabilize the trichloroethylene or to neutralize the hydrogen chloride formed during decomposition. Particularly valuable additives are acid-binding substances, like the basic amines which are customarily used to keep trichlorethylene under alkaline conditions.
In order to retard oxidation it has also been suggested to use small quantities of alcohols, phenols, N-alkyl pyrroles or epoxy compounds.
It is also known that the simultaneous addition of an alcohol and of certain amines gives the chlorinated hydrocarbons good stability against daylight.
We have now discovered that chlorinated hydrocarbons can be stabilized effectively by adding diamines, triamines or polyamines of the general formula \NA (-I|-A u R2 \R to the chlorinated hydrocarbon either singly or in mixtures. The letters in this formula represent:
R =R =R =R =R =H aliphatic alkyl radical with 1-3 carbon atoms, hydroxy alkyl radical with 1-3 carbon atoms or hydrogenated heterocyclic radical with 4-5 carbon atoms; A=bivalent 3,424,805 Patented Jan. 28, 1969 aliphatic unsaturated alkyl radical with 2-3 carbon atoms or phenylene radical; x=14; and n=04.
The addition of 0.001-002 weight percent of these compounds (referred to the chlorinated hydrocarbon) to the chlorinated hydrocarbon to be stabilized, e.g. dichlorethylene, trichlorethylene, perchlorethylene, increases their resistance against iron and aluminum.
By using diamines, e.g. ethylene diamine, trimethylene diamine, triethylene diamine, l,2-di-(N,Nmorpholine-) ethane, 1,2-di-(N,N-piperidine-) ethane, or triamines, e.g. diethylene triamine, or polyamines, e.g. tetraethylene pentamine, it is possible to obtain an excellent stabilizing eflect. This can be increased by the addition of aliphatic monoamines, e.g. diisopropyl amine or pyrrole or N-alkylpyrrols, e.g., N-methyl pyrrole. It has been found that even quantities of 0002-0005 weight percent, referred to the chlorinated hydrocarbon, have a surprising elfect.
The tabulated results of the stabilizing eifects show clearly the high degree of stabilization achieved by our invention. The stabilizing effect of various diamines, triamines and polyamines which are used to improve the resistance of, for instance, trichlorethylene against decomposition by light and oxygen, is proven by the accelerated oxidation test as per MIL-T4003 or Federal Specification 0T-634/ a, which is carried out as follows:
200 ml. of the trichlorethylene sample are placed in a retort. A steel strip measuring /2 x 2" x $4 is hung up with a copper wire in the reflux condenser and another steel strip measuring /4" x x ,4 is placed on the bottom of the retort. The input pipe for the water-saturated oxygen must reach down to within A" from the bottom of the retort. The diameter and immersion depth of the pipe below the water surface for controlling the pressure of the oxygen are fixed in such a manner that a stream of oxygen of about 10-12 bubbles per minute, measured by a bubble counter, is produced. The heat source is a frosted lamp of watts which is mounted underneath the retort. After 48 hours of reflux a sample is drawn, it is allowed to cool to room temperature and the acidity of the sample is then determined in an aqueous extract by titration with 0.1 N NaOH against phenolphthalein as the indicator. After a 48 hour test the acidity must not exceed the value of 0.02 weight percent HCl, referred to trichlorethylene.
Example 1 4 samples of 200 m1. trichlorethylene which is stabilized with 0.004 weight percent ethylene diamine are refluxed in a water-saturated oxygen stream, a frosted lamp of 150 watts serving as the heat source. Small steel plates are mounted in the liquid and in the vapor phase. A sample is drawn after 48 hours and, after the sample has cooled, the acid components are extracted with 25 ml. water. The aqueous extract is then titrated with 0.1 N NaOH against phenolphthalein as an indicator to determine the acidity of the sample. After a 48 hour test treatment the sample is still alkaline. The heating is stopped when the acidity has exceeded the limit of 0.02 Weight percent HCl, referred to trichlorethylene. In the case of 4 samples 0.020, 0.017, 0.021 and 0.019 weight percent HCl were titrimetrically determined after 240 hours of refluxing, or an average of 0.019 weight percent HCl. Thus after 240 hours of refluxing the acidity limit is not yet exceeded.
TABLE 1 Acidity Duration Acidity Test. N Additive (mg/kg. triehlorethylene) (percent HCl) (hours) (percent after 48 hrs. HO
1 0. 024 48 0. 089 96 0. 044 188 0. 055 240 0. 019 480 0. 011 Triethylenediamine (200) 336 0. 014 8 Trimethylenediamine (200) 504 0.011 9 1,2-propylenediamine (200) 456 0. 011 0 N,N '-triethylethylenediamine (200) 240 0.022 1 N,N,NN-tetramethylcthylenediamine (200) 312 0.013 12 N,Ndimethylethylenediamine (200) 528 0.015 13 Diethylenetriamine (200)..." 216 0. 020 4.- Tetraethylenepentamine (200) 144 0.015 15 1,2,4-trimethylpiperazine (200) 336 0.004 16.- N-oxethylpiperazine (200) Under 0.001... 264 0.010 17 1,2-di-(N,N-morpholine) ethane (200). "do 168 0. 019
The results of tests 5, 6, 7, 8 and 9 show the considerably stronger inhibiting effect of a diamine over that of a monoamine (tests 2, 3, 4). The table also shows that ethylene diamine (tests 5, 6) and trimethylene diamine (test 8), i.e. the simple aliphatic non-substituted diamines have the best effect.
Example 2 In a test made in accordance with Example 1, 200 ml. trichlorethylene with an additive of 0.004 weight percent diisopropylamine and 0.004 weight percent ethylene diamine are refluxed for 48 hours. After that period, and even after 450 hours heating the test is still alkaline.
Example 3 We proceed as in Example 1, using small iron plates, where each time 20 ml. trichlorethylene are used to which stabilizing mixtures are added. The trichlorethylene which has been prepared in such a manner is then treated for several hours under reflux in a water-saturated oxygen stream. Table 2 shows the results of these tests.
TABLE 2 Acidity Test Additive (mg.[k (Percent Duration Acidity No. trichlorothylene Hgl) (hours) (pfirccgnipt a or 48 hrs.
1 .{Di-isopropylamine (40) {Alkaline 192 0. 019
Ethylenediamine 2 .{Di-isopropylamine (40). .do 450 Ethylenediamine (40). 3 .{Di-isopropylamine (30) 0.015 62 0. 080
N -methylpyrrole (50)- 4 .-{Dl-isopropylamine (30).-.. 0.005 168 0.023
N-methylpyrrole (80) 5 --{Ethylenediamine (30)- {Alkaline. 432 0. 001
N-methylpyrrole (50). 6 .{Ethylenediamine (30).- ..do 816 0.010
N-methylpyrrole (80).- 7 {Di-isopropy1am1ne (30).-..{0 003 264 0. 029
N -methylpyrrole (100) 8 .-{Ethylenediamine (30)- {A1k81l118- 830 0. 023
N -metl1ylpyrrole (100) Di-isopropylamine (30) 9 Ethylenedlamine (10)-- do 508 0. 017
N-rnethylpyrrole (100) 10 Di'isoprogoylamtne (3 96 0.038
yrro e 11 .{Ethylenediamine (30). .{Alkaline. 312 0. 009
Pyrrole (50) l Alkaline.
The test results shown in Table 2 demonstrate the synergism of the combinations ethylene diamine/N- methyl pyrrole and pyrrole and di-isopropylarnine/ethylene diamine. The table shows that the effect of the addition of 0.003 weight percent ethylene diamine and 0.01 weight percent N-methyl pyrrole to trichlorethylene during the oxidation test results in a resistance of trichlorethylene of more than 800 hours. Furthermore, the combination of di-isopropylamine/N-methyl pyrrole shows an acidity content of 0.08% I-ICl after 52 hours heating, while for the combination ethylene diamine/N-methyl pyrrole after 432 hours an acidity of only 0.001% HCl is found.
The invention claimed is:
1. A chlorinated hydrocarbon selected from the group consisting of dichlorethylene, trichlorclhylene and perchlorethylene containing from 0.001 to 0.02 weight percent, related to said chlorinated hydrocarbon, of an amine selected from the group consisting of ethylene diamine, trimethylene diamine and 1,2-propy1ene diamine, and 0.005 to 0.01 weight percent, related to said chlorinated hydrocarbon, of a substance selected from the group consisting of pyrrole and N-methyl pyrrole.
2. A process for inhibiting the deccomposition of a chlorinated hydrocarbon selected from the group consisting of dichlorethylene, trichlorethylene and perchlorethylene during contact with metals which comprises maintaining dissolved therein from 0.001 to 0.02 weight percent of an amine selected from the group consisting of ethylene diamine, trimethylene diamine and 1.2-propylene diamine, and 0.005 to 0.01 weight 5 of a subtsance selected from the group consisting of pyrrole and N-methyl pyrrole.
References Cited UNITED STATES PATENTS 2,043,257 6/1936 Missbach 260-6525 3,189,552 6/1965 Sims 260-6525 2,803,676 8/1957 Willis et a1 260-6525 FOREIGN PATENTS 601,666 7/1960 Canada.
LEON ZIVER, Primary Examiner.
M. JACOBS, Assistant Examiner.
US. Cl. X.R. 252-153
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW40491A DE1275531B (en) | 1965-12-10 | 1965-12-10 | Stabilization of dichloroethylene, trichlorethylene or perchlorethylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3424805A true US3424805A (en) | 1969-01-28 |
Family
ID=7602484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US599367A Expired - Lifetime US3424805A (en) | 1965-12-10 | 1966-12-06 | Chlorinated hydrocarbon compositions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3424805A (en) |
| DE (1) | DE1275531B (en) |
| FR (1) | FR1505678A (en) |
| GB (1) | GB1163778A (en) |
| SE (1) | SE320060B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293433A (en) * | 1980-06-02 | 1981-10-06 | Diamond Shamrock Corporation | Perchloroethylene dielectric fluid containing pyrrole and phenol |
| US4942267A (en) * | 1986-12-22 | 1990-07-17 | Occidential Chemical Corporation | Perchloroethylene stabilization |
| US5080767A (en) * | 1989-04-07 | 1992-01-14 | Mitsui Toatsu Chemicals, Inc. | Process for preparing aromatic compounds having chlorinated side chains and method for stabilizing monochloro-side chain aromatic compounds |
| WO1999031031A1 (en) * | 1997-12-18 | 1999-06-24 | The Dow Chemical Company | Stabilizer composition |
| US20090176686A1 (en) * | 2005-07-15 | 2009-07-09 | Ulrich Tribelhorn | Stabilizer for organic solvents |
| EP2108464A1 (en) | 2008-04-09 | 2009-10-14 | Dow Global Technologies Inc. | Process for cleaning articles |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3936731A1 (en) * | 1989-11-04 | 1991-05-08 | Hoechst Ag | METHOD FOR STABILIZING CHLORINE PARAFFINS |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2043257A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Preservation of chlorinated hydrocarbons |
| US2803676A (en) * | 1954-04-20 | 1957-08-20 | Dow Chemical Co | Trichloroethylene stabilized with propargyl alcohol and pyrrole |
| CA601666A (en) * | 1960-07-12 | George R. Lusby | Stabilization of halohydrocarbons | |
| US3189552A (en) * | 1963-02-05 | 1965-06-15 | Ethyl Corp | Stable solvent composition |
-
1965
- 1965-12-10 DE DEW40491A patent/DE1275531B/en active Pending
-
1966
- 1966-11-28 GB GB53148/66A patent/GB1163778A/en not_active Expired
- 1966-12-06 US US599367A patent/US3424805A/en not_active Expired - Lifetime
- 1966-12-07 SE SE16785/66A patent/SE320060B/xx unknown
- 1966-12-08 FR FR86644A patent/FR1505678A/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA601666A (en) * | 1960-07-12 | George R. Lusby | Stabilization of halohydrocarbons | |
| US2043257A (en) * | 1933-10-09 | 1936-06-09 | Stauffer Chemical Co | Preservation of chlorinated hydrocarbons |
| US2803676A (en) * | 1954-04-20 | 1957-08-20 | Dow Chemical Co | Trichloroethylene stabilized with propargyl alcohol and pyrrole |
| US3189552A (en) * | 1963-02-05 | 1965-06-15 | Ethyl Corp | Stable solvent composition |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293433A (en) * | 1980-06-02 | 1981-10-06 | Diamond Shamrock Corporation | Perchloroethylene dielectric fluid containing pyrrole and phenol |
| US4942267A (en) * | 1986-12-22 | 1990-07-17 | Occidential Chemical Corporation | Perchloroethylene stabilization |
| US5080767A (en) * | 1989-04-07 | 1992-01-14 | Mitsui Toatsu Chemicals, Inc. | Process for preparing aromatic compounds having chlorinated side chains and method for stabilizing monochloro-side chain aromatic compounds |
| WO1999031031A1 (en) * | 1997-12-18 | 1999-06-24 | The Dow Chemical Company | Stabilizer composition |
| US20090176686A1 (en) * | 2005-07-15 | 2009-07-09 | Ulrich Tribelhorn | Stabilizer for organic solvents |
| US7674340B2 (en) | 2005-07-15 | 2010-03-09 | Dow Global Technologies, Inc. | Stabilizer for organic solvents |
| EP2108464A1 (en) | 2008-04-09 | 2009-10-14 | Dow Global Technologies Inc. | Process for cleaning articles |
| US20110030736A1 (en) * | 2008-04-09 | 2011-02-10 | Konrad Geissler | Process for cleaning articles |
| US8066820B2 (en) | 2008-04-09 | 2011-11-29 | Dow Global Technologies Llc | Process for cleaning articles |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1163778A (en) | 1969-09-10 |
| SE320060B (en) | 1970-02-02 |
| DE1275531B (en) | 1968-08-22 |
| FR1505678A (en) | 1967-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3424805A (en) | Chlorinated hydrocarbon compositions | |
| US3043888A (en) | Stabilization | |
| US3839087A (en) | Perchloroethylene vapor degreasing process | |
| US2935537A (en) | Process for the stabilisation of chlorinated hydrocarbons | |
| NO132631B (en) | ||
| US2096735A (en) | Stabilized chlorinated solvents and method of stabilizing such solvent | |
| US2803676A (en) | Trichloroethylene stabilized with propargyl alcohol and pyrrole | |
| GB391156A (en) | Improvements in or relating to the stabilisation of chlorinated hydrocarbons | |
| US2387976A (en) | Method of forming carboxylic substituted amines | |
| DE2164394A1 (en) | Stabilized trichlorethylene or tetrachlorethylene | |
| US3406213A (en) | Process for stabilizing halogenated hydrocarbons | |
| GB1567652A (en) | Stabilised 1,1,1-trichloroethane | |
| JPS595563B2 (en) | Stabilization of 1,1,1-trichloroethane | |
| US2781406A (en) | Stabilization of halogenated hydrocarbons | |
| DE2925968A1 (en) | STABILIZED 1,1,1-TRICHLORAETHANE | |
| US3403190A (en) | Stabilized halogenated hydrocarbon compositions of matter | |
| US2319261A (en) | Stabilizing chlorinated hydrocarbons | |
| CA2614908C (en) | Stabilizer for organic solvents | |
| US3479414A (en) | Stabilized chlorinated hydrocarbon compositions and process therefor | |
| US4783560A (en) | Stabilized compositions of 1,1,1-trichloroethane | |
| US3714052A (en) | Chlorinated hydrocarbons stabilized with alkoxyaldehyde hydrazone andglycidol | |
| GB717680A (en) | Improvements in and relating to the stabilisation of alkylated phenylene diamines | |
| USRE26025E (en) | Stabilization of methyl chloroform | |
| US2964563A (en) | Stabilizing unsaturated amines | |
| US3118955A (en) | Stable solvent compositions containing triisopropanolamine borate |