Table Of ContentAppendix 1
Synopses of Selected Patents from
the Art of Solvent Stabilization
1,925,602, 1933; Pitman, for E.I. Du Pont de Nemours & Co., Inc., USA
Notes that TCE, PCE, and DCM form acids upon decomposition that corrode metal storage tanks.
Gasoline has been used to stabilize TCE—but large volumes are required. Notes that other s tabilizers
have boiling point differences causing fractionation upon distillation. Seeks a stabilizer that boils
with TCE and is not malodorous. Claims that triethylamine meets these criteria, at 0.0001–0.1 vol%.
If TCE is not exposed to light, only 0.0005% triethylamine is needed, and more if storage includes
exposure to light. Presents data for storage stability of PCE, chloroform, and TCE. No discussion of
solvent breakdown in vapor degreasing.
1,971,318, 1934; Smith and De Pree, for Dow Chemical Co., USA
Stabilizes CCl and PCE with small amounts of natural resins, such as gum mastic, sandarac, and
4
rosin. Adds 0.006–0.13% to protect solvents during storage when in contact with iron or copper.
2,108,390, 1938; Price, for Westvaco Chlorine Products Corp., USA
Stabilizes TCE with thiocyanate esters at 0.001–1.0% (preferably methyl thiocyanate). Notes that
the stabilizer itself must be stable, and stand up to repeated phase transitions from liquid to vapor
and vapor to liquid.
2,111,253, 1938; Stoesser and Alquist, for Dow Chemical Co., USA
Observes that all chlorinated aliphatic hydrocarbons decompose in the presence of moisture, l eading
to corrosion of metal surfaces. Proposes the addition of a piperazine compound such as tetramethyl
piperazine or piperzine hydrate to stabilize chlorinated aliphatic hydrocarbons (PCE in particular)
against breakdown from exposure to light and against formation of acid.
2,155,723, 1939; Levine and Cass, for E.I. Du Pont de Nemours & Co., Inc., USA
Notes that TCE decomposes during recovery (distillation, condensation) if not restabilized at this
point in the solvent life cycle. “In order to combat this tendency to decompose during storage, use,
and recovery, it has been usual to dissolve in the TCE an agent [p-tert-butyl phenol] which will
stabilize the solvent under the conditions at which these operations are normally carried out.”
2,371,644, 1945; Petering and Aitchison, for Westvaco Chlorine Products Corp., USA
Emphasizes the addition of oxygen-containing organic compounds such as organic oxides, oximes,
ethers, and alcohols. The more alcohol or other oxygen compound present, the more effective the
composition in restraining the “metal-induced” decomposition of solvents. Recommends using
1 mol oxygen compound per 99 mol chlorohydrocarbon. Emphasizes that alcohols boil with the
487
© 2010 by Taylor and Francis Group, LLC
488 Appendix 1: Synopses of Selected Patents from the Art of Solvent Stabilization
solvent. A minor amount of oxygen-containing compound results in a marked decrease in metal-
induced decomposition. Claims that n-butyl alcohol and isoamyl alcohol stabilize TCE.
2,435,312, 1948; Klabunde, for E.I. Du Pont de Nemours & Co., Inc., USA
Stabilizes TCE with di-isobutylene to inhibit the condensation decomposition reaction catalyzed by
aluminum or iron. Notes that when exposed to air, light, or heat, TCE degrades by oxidation to form
dichloracetyl chloride, HCl, and phosgene. At higher temperatures, TCE undergoes a condensation-
type decomposition to form HCl together with a resinous material. Describes di-isobutylene as an
unsaturated organic compound boiling at about 102°C. Uses di-isobutylene to stabilize TCE at
0.1–1.0%. Recommends addition of an antioxidant.
2,517,894, 1950; Larchar, for E.I. Du Pont de Nemours & Co., Inc., USA
Proposes adding cyclohexene at 0.02–0.25% to TCE to stabilize against reactions with metals.
Notes that cyclohexene boils with TCE, allowing recovery on distillation. Finds that cylohexene
protects against solvent breakdown in the presence of alkali metals 17 times more effectively than
cyclohexane. Also fi nds that cyclohexene in TCE is 3 times more effective than aniline.
2,721,883, 1955; Stevens, for Columbia-Southern Chemical Corp., USA
The decomposition of perchloroethylene is more pronounced when in contact with iron or copper.
Products of PCE decomposition materially injure its benefi cial effect, causing metal corrosion.
Notes that perchloroethylene shows poor light stability; fl uorescent and ultraviolet light cause PCE
to decompose, producing a measurable decrease in pH. Compounds previously used to stabilize
PCE, such as benzaldehyde, cyclohexane, toluene, benzyl chloride, amylene hexylresorcinols, butyl
mercaptan, ethyl acetate, guanidine, and pyridine, have been found to be unsatisfactory because
they are ineffective or their odors or color are objectionable. Proposes N-methylmorpholine as a
stabilizer to protect PCE against UV-light attack.
2,751,421, 1956; Stauffer, for E.I. Du Pont de Nemours & Co., Inc., USA
Claims that tert-butyl-4-hydroxyanisole (BHA, the food preservative) stabilizes TCE in storage,
which otherwise oxidizes and decomposes resulting in the formation of acids. This decomposition
is accelerated by heat, light, moisture, and contact with metals. The use of amines is disadvanta-
geous because they are dissipated by reaction with the acids that the solvent may encounter during
normal use. Amines have a further disadvantage: the production of amine salts accelerates the
corrosion of metals.
2,775,624, 1956; Skeeters and Baldridge, for Diamond Alkali Co., USA
Claims that acetylenic alcohols, particularly the methyl butynol and methyl pentynols (e.g., 2- methyl-
3-butyne-2-ol, 3-methyl-1-pentyne-3-ol, and propargyl alcohol), stabilize PCE against oxidation.
Provides boiling ranges for several acetylenic alcohols that fall within or slightly below PCE’s
b oiling range of 119–122°C. Discusses methods for purifying PCE to remove trace lower aliphatics
that lead to decomposition. Asserts that acetylenic alcohols perform better than all other stabilizers
for metal degreasing and wood dehydration using PCE.
2,795,623, 1957; Starks, for F.W. E.I. Du Pont de Nemours & Co., Inc., USA
Presents a stabilizer for a stabilizer: N-methyl pyrrole. Pyrroles added to TCE and PCE at
0.001–1 wt% are somewhat unstable and may decompose when exposed to light, heat, or oxygen.
TCE containing N-methyl pyrrole will show discoloration on exposure to bright sunlight in as little
as 2–4 h. The solvent in which N-methyl pyrrole has become unstable will itself destabilize and
deposit black tar. This invention uses organometallic chelate compounds to stabilize N-methyl
p yrrole added at 0.001 wt% and claims copper butylacetoacetate, copper salicylate, aluminum
methylsalicylate, and aluminum ethylacetoacetate.
© 2010 by Taylor and Francis Group, LLC
Appendix 1: Synopses of Selected Patents from the Art of Solvent Stabilization 489
2,797,250, 1957; Copelin, for E.I. Du Pont de Nemours & Co., Inc., USA
Proposes the use of an organic oxide, preferably epichlorohydrin, in combination with a basic
amine, such as triethylamine, to act as antacids for TCE and PCE. Basic amines are commonly
used to impart alkaline conditions to chlorinated hydrocarbons. HCl formation is a problem
because it catalyzes the rusting of iron or steel workpieces cleaned in the machine or in the degreas-
ing apparatus itself. Even small amounts of HCl will catalyze the rusting of iron or steel work-
pieces put through the degreasing machine. If HCl formation occurs, or if metallic salts—particularly
aluminum chloride—are formed, the operator must shut down the degreasing production line to
neutralize the solvent.
2,811,252, 1957; Bachtel, for Dow Chemical Company, USA
Bachtel presents the fi rst formulation for stabilizing methyl chloroform against reaction with metals
using 1,4-dioxane at a preferred ratio of 4% by volume. Adding 1,4-dioxane provides stability in the
presence of aluminum, even when boiling, a result that enables the use of methyl chloroform for
vapor degreasing products containing aluminum and iron for the fi rst time. Bachtel notes that over
2 months, the mixture of methyl chloroform with 1,4-dioxane stored in black iron drums will show
a rusty discoloration; however, the discoloration can be prevented by including sec-butyl alcohol,
tert-amyl alcohol, or 2-octanol as a stabilizer (any of these alcohols at 0.1–0.5% by volume). The
patent presents experimental data showing that the 1,4-dioxane is carried over to the vapor phase,
such that methyl chloroform vapors remain stable in the presence of aluminum.
2,838,458, 1958; Bachtel, for Dow Chemical Company, USA
In this patent, Bachtel improves upon his fi rst formulation for stabilizing methyl chloroform against
reaction with metals using 1,4-dioxane. He notes that 1,4-dioxane is not entirely effective at preventing
corrosion of aluminum or iron exposed to vapors of methyl chloroform entrained with liquid at boil-
ing temperatures, which is a disadvantage for vapor degreasing. Bachtel solves this problem by
including a lower aliphatic monohydric acetylenic alcohol, preferably 2-methyl-3-butyn-2-ol (also
called dimethyl ethynyl carbinol). The ratios tested include 1,4-dioxane at 2.5–4% by volume with
2-methyl-3-butyn-2-ol at 0.1–0.3% by volume. The effectiveness of 2-methyl-3-butyn-2-ol is not
compared to the performance of the pairing of 1,4-dioxane with sec-butyl alcohol claimed in his fi rst
patent. Bachtel’s 1958 patent seems to be an alternate embodiment of his 1957 patent, possibly to
retain the rights for all combinations of effective stabilizer mixtures that include 1,4-dioxane.
2,818,446, 1957; Starks, for E.I. Du Pont de Nemours & Co., Inc., USA
Notes that many other stabilizers increase the solubility of HCl. Invention claims synergistic com-
bination of an epoxide and an ester to stabilize TCE. The preferred combination is 0.2 wt% of ethyl
acetate and 0.3 wt% of epichlorohydrin. Claims this combination provides a stabilizing effect from
7- to 20-fold greater than that of either component used singly. Notes that it may still be necessary
to add a stabilizing amount of a phenolic antioxidant.
2,947,792, 1960; Skeeters, for Diamond Alkali Co., USA
Lists numerous stabilizers of PCE and suggests they have light stabilizing properties. This invention
claims isoeugenol (4-hydroxy-3-methoxy-1-propenylbenzene) as a light stabilizer of PCE, and
recommends it should be used in combination with methyl pentynol.
3,049,571, 1962; Brown, for Dow Chemical Co., USA
Notes that methyl chloroform (TCA) will react with zinc in the boiling vapor when stabilized with
1,4-dioxane, nitromethane, and sec-butyl alcohol. It is the stabilizers themselves that catalyze the
reaction with zinc. This is a problem for reclaiming spent solvent from cold degreasing using TCA,
because much solvent recycling equipment has galvanized iron containing zinc. Zinc-lined stills
commonly used in solvent recycling would be damaged. Zinc causes degradation of the solvent
© 2010 by Taylor and Francis Group, LLC
490 Appendix 1: Synopses of Selected Patents from the Art of Solvent Stabilization
vapor and evolves acid, which attacks and liberates more zinc. This patent claims the addition of
vicinal monoepoxides to methyl chloroform (aliphatic epoxides containing an ethylene oxide group).
1,2-Butylene oxide is the example tested.
3,133,885, 1964; Petering and Callahan, for Detrex Chemical Industries, Inc., USA
Provides stabilizers, primarily epoxides, for amine-stabilized PCE and TCE, noting that these for-
mulations will react with iron and copper in the absence of water. Notes that most stabilizers have
high boiling points, but the wide difference in boiling points between the solvent and the stabilizers
is undesirable because of the diffi culty of stabilizing the vapor phase. This patent teachers that distil-
lation of solvent may result in complete loss of stabilizer if boiling point differences are large.
990,302 (Great Britain), 1965; Tect, Inc. (USA)
Notes that the utility of methyl chloroform (TCA) as a cold cleaning agent was recognized as a
preferable replacement to the more toxic carbon tetrachloride (CT) since 1950, but it was not until
1954 that addition of stabilizers enabled the use of TCA for cold cleaning without the formation of
a tarry mass or releasing phosgene gas and HCl. This 1965 patent notes that until recently TCA was
not considered stable for hot solvent vapor degreasing. Invention was successful in stabilizing TCA
for degreasing for up to 7200 h. This patent claims a stabilizer package including 1,4-dioxane,
methyl pentynol, propargyl alcohol, and sec-butyl alcohol.
3,326,988, 1967; Stack, for Pittsburg Plate Glass Company, USA
Alcohol-containing compositions of methyl chloroform (TCA) can be better stabilized by adding
perchloroethylene to form an azeotrope. Addition of PCE at 0.5–5% weight increases the rate of
TCA evaporation. Alcohol-stabilized TCA will leave spots on the work if PCE is not added. Most
common TCA formulations contain 1–2% alcohol (saturated and unsaturated monohydric aliphatic
alcohols, e.g., sec-butyl alcohol).
3,878,256, 1975; Richtzenhain and Rudolf, for Dynamit Nobel AG, Germany
Tests different proportions of a four-component system using the MIL-T-7003 metal strip method
with aluminum, zinc, and iron. Finds that the best stabilizing mixture was methoxyacetonitrile, 0.5%;
1,2-epoxybutane, 0.8%; 1,4-dioxane, 2%; and nitromethane, 1%. This mixture caused no corrosion of
metal strips in a 168 h test.
4,032,584, 1977; Irani, for Stauffer Chemical Co., USA
Notes that dichloromethane is the least toxic of the chloromethanes, is more stable than PCE, TCE,
and MC, and has a lower boiling point. Dichloromethane is also resistant to photochemical activity
and therefore does not produce smog. Dichloromethane can react with aromatic and aliphatic
c ompounds in the presence of metals, metal halides, and combinations thereof, including a luminum,
zinc, and iron, and their halides. The reaction product is generally an objectionable, high-boiling
tarry substance that renders the dichloromethane unsuitable for further use. Compounds that react
with methylene chloride are generally introduced from various cutting oils and lubricants used in
metal fabricating operations. Stabilizers are added to dichloromethane to prevent degradation and
other types of deterioration such as oxidation, hydrolysis, and pyrolysis. Stabilizing amounts of
mixed amylenes, propylene oxide, butylene oxide, and tertiary butylamine are added.
© 2010 by Taylor and Francis Group, LLC
Appendix 2
Fate and Transport Properties of
Solvent-Stabilizer Compounds
491
© 2010 by Taylor and Francis Group, LLC
Chemical Boiling Water Solubility Henry’s Law Vapor Vapor Vapor Density
Stabilizer Abstract Service Point (°C @ Solubility Measurement Constant Pressure Temperature (@ 25°C) Relative 4
9
Compound Registry Number 760 mm Hg) (mg/L @ 25°C Temperature (°C) log K log K [(atm m3)/mol] (mm Hg) (°C) to Air (unitless) 2
ow oc
1,2-Butylene oxide 106-88-7 63.3 [1] 95,000 25 [12] 0.9 [22] 0.9 [12] 0.00018 [32] 180 25 [32] 2.2 [32]
1,3,5-Trioxane 110-88-3 114.5 [2] 212,000 25 [3] –0.47 [23] –0.43 [31] — [23] 10 20 [23] — —
1,3-Dioxolane 646-06-0 78 [1] Miscible 25 [1] –0.37 [24] 1.17 [32] 0.000024 [23] 70 20 [6] 2.6 [51]
1,4-Dioxane 123-91-1 101.1 [3] Miscible 25 [13] –0.27 [24] 1.23 [22] 4.8 × 10−6 [34] 38.09 25 [38] 3.03 [6]
2,6-di-tert-Butyl-p- 128-37-0 265 [4] 0.4 20 [14] 5.1 [25] — — 0.00059 [25] — — — 7.6 [6]
cresol (BHT) A
p
2-Butanone 78-93-3 79.6 [4] 353,000 10 [14] 0.29 [24] 1.5 [23] 0.000047 [35] 91 25 [45] 2.41 [14] p
e
2-Methyl-3-butyn-2-ol 115-19-5 103.5 [5] Miscible 20 [5] 0.318 [5] 1.55 [5] 9.9 × 10−7 [5] 15 20 [5] 2.49 [52] nd
Acetonitrile 75-05-8 81.6 [4] Miscible 25 [15] –0.34 [24] 1.2 [32] 0.000035 [36] 88.8 25 [46] 1.42 [46] ix
2
Butoxymethyl oxirane 2426-08-6 164 [6] 20,000 20 [16] 0.63 [24] 0.24 [33] 0.000027 [33] 3.2 25 [33] 3.78 [16] : F
a
Cyclohexane 110-82-7 80.7 [4] 0 25 [4] 3.44 [24] 2.2 [32] 0.15 [37] 97 25 [47] 2.98 [53] te
Diisobutylene 107-40-4 104.9 [1] 0 25 [1] 4 [25] 2.44 [32] 0.88 [32] 35.9 25 [32] 3.8 [32] a
n
Diisopropylamine 108-18-9 84 [7] 11,000 25 [10] 1.4 [24] 2.15 [32] 0.000096 [38] 79.4 25 [38] 3.5 [51] d
T
Epichlorohydrin 106-89-8 117.9 [4] 65,900 25 [17] 0.45 [27] 1.6 [32] 0.00003 [32] 16.4 25 [32] 3.29 [6] ra
n
Ethanol 108-01-0 135 [4] Miscible 25 [4] –0.31 [24] — — — — — — — 3.03 [6] s
p
Ethyl acetate 141-78-6 77 [4] 64,000 25 [18] 0.73 [29] 1.77 [29] 0.00013 [29] 79.4 25 [38] 3.04 [4] o
r
Nitroethane 79-24-3 114 [4] 45,000 20 [17] 0.18 [24] 1.48 [32] 0.000048 [32] 20.80 25 [32] 2.58 [6] t P
r
Nitromethane 75-52-5 101.2 [4] 11,100 25 [15] –0.35 [24] 0.28 [32] 0.000026 [32] 35.8 25 [38] 2.11 [6] o
p
N-Methylmorpholine 109-02-4 113 [8] Miscible 25 [8] –0.35 [26] 0.791 [26] 2.5 × 10−7 [26] 18.7 25 [26] 3.5 [8] e
r
N-Methyl pyrrole 96-54-8 112 [9] 0 25 [9] 0.75 [24] 2.162 [26] 0.00019 [26] 19.5 25 [26] 2.8 [9] tie
s
Phenol 108-95-2 181.75 [10] 82,800 25 [19] 1.46 [24] 1.2 [32] 3.3 × 10−7 [36] 0.35 25 [32] 3.24 [54] o
1,2-Propylene oxide 75-56-9 34.23 [4] 590,000 25 [12] 0.03 [24] 1.4 [32] 0.000070 [32] 538 25 [48] 2 [16] f S
o
p-tert-Amyl phenol 80-46-6 262.5 [4] 168 25 [17] 4.03 [28] 2.41 [22] 2.0 × 10−6 [39] 0.008 25 [38] — — lv
e
Pyridine 110-86-1 115.2 [4] Miscible 20 [10] 0.65 [24] 1.7 [22] 0.00001 [40] 20.8 25 [32] 0.982 [55] n
Resorcinol 108-46-3 280 [4] 71,700 25 [17] 0.8 [24] 1.81 [32] 1.1 × 10−11 [32] 0.00049 25 [49] 3.79 [16] t-S
t
a
sec-Butyl alcohol 78-92-2 99.5 [11] 181,000 25 [10] 0.61 [24] 1.7 [32] 9.1 × 10−6 [41] 18.3 25 [38] 2.6 [51] b
tert-Amyl alcohol 75-85-4 102.4 [1] 110,000 25 [20] 0.89 [24] 0.46 [32] 0.00073 [42] 16.8 25 [38] 3.0 [56] iliz
e
tert-Butyl alcohol 75-65-0 82.41 [4] Miscible 25 [15] 0.35 [24] 1.57 [32] 9.1 × 10−6 [43] 40.7 25 [38] 2.55 [32] r C
tert-Butyl phenol 128-37-0 265 [4] 0.6 25 [21] 6.2 [30] 2.77 [30] 0.0030 [21] 0.18825 25 [30] 7.6 [6] o
m
Thymol 89-83-8 233 [6] 1000 25 [4] 3.3 [24] — — — — 0.095 40 [32] — — p
o
Triethylamine 121-44-8 89.3 [1] 15,000 20 [14] 1.45 [24] 2.16 [29] 0.00015 [44] 57.1 24 [50] 3.49 [16] u
n
d
Notes: References are listed by number in brackets and italics to the right of each value; see the list of references on the pages following. Dashes indicate that reliable values were not found. s
© 2010 by Taylor and Francis Group, LLC
Appendix 2: Fate and Transport Properties of Solvent-Stabilizer Compounds 493
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Appendix 3
Compilation of Instrumental
Parameters in Literature
Studies of 1,4-Dioxane Analyses
of Various Media
497
© 2010 by Taylor and Francis Group, LLC
