Morpholine
MORPHOLINE
Introduction ..................................................................... 2 Vapor Pressure Versus Temperature
Sales Specifications/Analytical Procedures ..................... 2 of Morpholine ............................... Figure 9 ...... 15
Applications .................................................................... 3 Viscosity of Aqueous Morpholine
Rubber Chemicals .................................................... 3 at 20°C ........................................ Figure 10 .... 16
Catalysts .................................................................. 3 Chemical Properties ...................................................... 17
Corrosion Inhibitors .................................................. 3 Reaction with Acids and Acid Derivatives ................ 17
Separating Agents .................................................... 4 Reaction with Isocyanates and Isothiocyanates ...... 18
Optical Brighteners ................................................... 4 Reaction with Amines and Amides .......................... 18
Pharmaceutical Chemicals ....................................... 4 The Mannich and Related Reactions ...................... 18
Bactericides, Fungicides, and Herbicides .................. 5 Reaction with Aldehydes ........................................ 19
Antioxidants .............................................................. 5 The Leuckart-Wallach Reaction .............................. 19
Wax Emulsifiers and Surface-Active Agents ............. 5 Alkylation ................................................................ 19
Miscellaneous Applications ....................................... 6 Arylation ................................................................. 19
Physical Properties ......................................................... 7 Addition to Unsaturation ......................................... 20
Solubility ................................................................... 7 Reaction with Epoxides and Imines ........................ 20
pH Value of Aqueous Morpholine ....... Figure 1 ........ 8 Willgerodt Reaction ................................................ 20
Flash Point of Aqueous Morpholine ....Figure 2 ........ 9 Reaction with Oxidizing Agents ............................... 21
Freezing Point of Aqueous The Hofman Degradation ....................................... 22
Morpholine ................................... Figure 3 ........ 9 Direct Chlorination .................................................. 22
Refractive Index of Aqueous Complex Formation ................................................ 22
Morpholine at 20°C ......................Figure 4 ...... 10 Miscellaneous Reactions ........................................ 22
Specific Gravity of Aqueous Handling and Storage ................................................... 23
Morpholine at 20°C ......................Figure 5 ...... 11 General .................................................................. 23
Specific Gravity of Morpholine Maintaining Specifications ...................................... 23
Versus Temperature ....................Figure 6 ...... 12 Transfer Lines ........................................................ 23
Surface Tension of Aqueous Pumps .................................................................... 24
Morpholine at 20°C ......................Figure 7 ...... 13 Unloading in Cold Weather ..................................... 24
Vapor-Liquid Equilibria for Aqueous New Facilities and Cleaning .................................... 24
Morpholine at Atmospheric Shipping Information ..................................................... 25
Pressure ......................................Figure 8 ...... 14 Safety and Toxicity ........................................................ 26
Huntsman Sales Offices ................................................ 28
Quality Policy Product Safety Policy
Huntsman Corporation is committed to providing prod- It is the product safety policy of Huntsman Corporation
ucts and services that consistently conform to our to provide our customers with information on the safe
customers� requirements. handling and use of our products. The Material Safety
To fulfill this commitment, the employees of Hunts- Data Sheet (MSDS) should always be read and under-
man Corp. are dedicated to “being the best� through stood thoroughly before handling the product, and
continuous improvement. adequate safety procedures should be followed. Infor-
In implementing its quality policy, Huntsman Corp. mation on the toxicity, environmental, and industrial
is committed to the use of statistical methods. hygiene aspects of our products may be found in the
MSDS.
1
INTRODUCTION
Morpholine, CAS Number 110-91-8, is a colorless, mobile, Fatty acid derivatives of morpholine are used as
hygroscopic liquid with a characteristic amine-like odor. It emulsifiers in the manufacture of waxes and polishes.
is completely miscible with water and a large number of Other derivatives have found applications as bactericides,
organic solvents, and is itself a solvent for a large variety pharmaceutical chemicals, and antioxidants for lubricating
of organic materials, including resins, dyes, waxes, oils. Morpholine derivatives are particularly useful in the
shellac, and casein. textile industry, where they are employed as textile
Morpholine is an extremely versatile chemical with lubricants and sizing emulsifiers.
many important applications. It is used as an intermediate Chemically, morpholine is an amino ether. The ether
in the manufacture of rubber chemicals and optical function of the molecule is typically inert and most of the
brighteners. It is also used extensively as a corrosion reactions of morpholine involve the secondary amine
inhibitor in steam boiler systems. group.
SALES SPECIFICATIONS/ANALYTICAL PROCEDURES
Sales Specifications Analytical Procedures
The following sales specifications are subject to change Abbreviated forms of the standard methods of test for use
without notice. Appropriate analytical procedures for these with morpholine specifications are presented here. Copies
specifications may be found to the right. of the methods in detail are available from our Technical
Services Section in Austin, Texas, upon request.
Method of APPEARANCE (Method No. ST-30.1) is determined
Determination by visual inspection of DIGLYCOLAMINE agent in a
100-ml tall-form Nessler tube.
Appearance Clear liquid, ST-30.1
substantially COLOR (Method No. ST-30.12) is determined visually
free from in a 40-ml tube with APHA color disc standards, or in a
suspended 100-ml tall-form Nessler tube with liquid platinum cobalt
matter (APHA) standards.
Color, Pt-Co scale 15 max. ST-30.12 MORPHOLINE ASSAY (Method No. ST-35.77) is used
to determine morpholine and impurities by gas chromatog-
Morpholine, wt. % 99.0 min. ST-35.77
raphy.
Water, wt. % 0.3 max. ST-31.53
WATER (Method No. ST-31.53) is determined by the
Procedure 6
standard Karl Fischer method, the end point being de-
tected electrometrically.
2
APPLICATIONS
Rubber Chemicals Corrosion Inhibitors
A major use of morpholine is as an intermediate in the Morpholine is widely used as a neutralizing amine in
production of delayed-action type rubber accelerators. combating carbonic acid corrosion in condensate return
Accelerators are added to rubber before fabrication to lines of steam boiler systems. The morpholine volatilizes
increase the rate of vulcanization. Since during fabrication with the steam from the boiler and condenses when the
there is a danger of prevulcanization, particularly if high steam does, thereby affording protection to the lines,
temperatures are involved or if furnace black rather than which otherwise would be subjected to corrosion by the
channel black is present, delayed-action accelerators are carbonic acid present in the steam condensate.
highly desirable. Morpholine vapors protect silver and other metals
Morpholine-based delayed-action accelerators are against corrosion and tarnish by acid fumes, such as
usually made by reacting morpholine with 2-mercapto- sulfur dioxide and hydrogen sulfide. The morpholine is
benzothiazole. Several other morpholine-based accelera- supplied by evaporation from solution in a solid, such as
tors have been reported in the literature. camphor, or by sublimation from morpholinium
N,N'-oxydiethylenecarbamate.
Catalysts Morpholine is a component of a corrosion inhibitor
Morpholine has been employed as a catalyst for the system that prevents decomposition of a chlorinated
condensation of aldehydes and ketones which contain hydrocarbon in a composition containing the chlorinated
active methyl or methylene groups. The condensates may hydrocarbon and a large amount of water.
be hydrogenated to polyhydroxy compounds which can be Corrosion of metal aerosol containers and valves can
sulfated to form surface-active agents. be prevented by the use of low levels of morpholine.
Small quantities of morpholine are used in the emul- Morpholine is one of several amines employed as
sion polymerization of monomers, such as butadiene and phosphates for inhibiting the corrosive action of grease-
isoprene, as well as their copolymerization with styrene, proof paper on steel and other metals. Di-4-morpholinyl
acrylonitrile, and the like. polysulfides have been claimed as corrosion inhibitors to
Morpholine has been used as a temperature sensitive be added to mineral lubricating oils. Turbine oils, espe-
polymerization inhibitor. Small amounts permit complete cially, are quickly contaminated with water, and to protect
impregnation of porous materials with molten vinylpyrrole- the machinery against rusting, 4,4'-alkylidenedimorpho-
type monomers just above their melting points, but still lines and poly (4-morpholinylmethyl) phenols have been
allow complete polymerization at slightly higher tempera- used. Storage tanks, pipes, and other devices for handling
tures. petroleum distillates must be protected against corrosion,
Morpholine has also been used as a gelling agent in and for this purpose 4,4'-butylmercaptomorpholine,
the preparation of alumina catalysts for the treatment of morpholinium mahogany sulfonates, and morpholine in
hydrocarbons. Catalysts of fine particle size suitable for conjunction with ammonium mahogany sulfonates have
fluidized solid techniques result from this procedure. been suggested.
3
APPLICATIONS
Separating Agents Pharmaceutical Chemicals
The physical and chemical properties of morpholine make The physiological activity of the morpholine nucleus is
it useful in various purification procedures. Marked differ- attested by the number of pharmaceutical applications
ences in the solubility of the methyl amines in morpholine which have been found for it.
have led to a convenient extractive method for separating The hydroperiodide is suitable for incorporation in
these volatile amines. The addition of morpholine to ointments for the treatment of skin disorders, such as
styrene-containing hydrocarbon mixtures makes possible athlete’s foot.
the isolation of substantially pure styrene by azeotropic A number of morpholine derivatives have been
distillation. It is claimed that aldehydo or keto derivatives described as analgesics and local anesthetics. The
of morpholine, e.g., 4-formylmorpholine, are useful for 4-benzyl morpholines are particularly effective. 4-(4-
separating low-viscosity components from mineral, animal, Bromobenzyl) morpholine, for instance, is reported to be
vegetable, and fish oils. It is reported that morpholine is only 25% as toxic as procaine, but almost equal to it in
the preferred amine to use in an oil-amine mixture for activity.
scrubbing organic sulfur compounds from fuel gas. Several morpholine-derived chemicals are useful as
Morpholine is also used in the purification of acetylene and respiratory and vasomotor stimulants. The
certain olefins. N,N'-ethylenebis (N-alkyl-4-morpholinecarboxamides) are
especially valuable, since the ratio of active dose to toxic
Optical Brighteners dose is low. The dibutyl derivative, for example, shows 12
Morpholine is an important intermediate in the manufac- times the activity of nikethamide.
ture of optical brighteners. Optical brighteners are em- Other pharmaceutical fields in which morpholine has
ployed by the soap and detergent industry in the found application include choleretics, antispasmodics,
compounding of detergents. The diaminostilbene triazine analeptics, and antimalarials. In addition, the use of
type brightener with morpholine as a substituent on one of morpholine as a peptizing agent for preparing aqueous
the triazine rings is particularly effective on cellulosics. dispersions of phenothiazines for anthelmintic purposes
Having greater stability to chlorine bleaches than other has been claimed. Likewise, the use of morpholine in
types of brighteners, they are particularly suitable for preparing soluble salts of certain sulfanilamides has been
home laundry detergents. patented, and various derivatives are claimed to have
therapeutic value.
4
APPLICATIONS
Bactericides, Fungicides, and Herbicides Wax Emulsifiers and Surface-Active Agents
A number of morpholine derivatives have been shown to When morpholine is reacted with fatty acids, it forms
possess bactericidal activity. For example, morpholinium soaps possessing excellent emulsifying properties. The
salts of certain acylated sulfonamides possess strong oleic soap is a particularly important emulsifier used in the
bacteriostatic or bactericidal properties, and morpholine formulation of self-polishing waxes and polishes. One of
hydroperiodide has been used as a water disinfectant. the main advantages of morpholine-based emulsifiers is
The reaction of morpholine with 3,4,5-trichloro-2,6- the similar boiling points of morpholine and water. When
pyridinedicarbonitrile yields a product which is useful in the the loosely bound fatty acid-morpholine compound breaks
control of fungi. down, the morpholine component evaporates at approxi-
Morpholine is used in preparing compounds that are mately the same rate as the water. Consequently, the
excellent herbicides and that can be applied either to the resultant wax film is left dry and void of morpholine, and is
soil before the weeds emerge or to the growing plants. then highly water resistant. This is a very desirable feature
in household and automobile waxes and polishes.
Antioxidants The reaction products of morpholine and tung oil or
In addition to its use as a corrosion inhibitor, 4-t- linseed oil have been found to be good emulsifying and
butylmercaptomorpholine has been employed as an dispersing agents. Also, the quaternary alkyl ammonium
antioxidant for lubricating oils. Di-4-morpholinyl sulfates of Mannich bases from morpholine and mono- or
monosulfide has been claimed as a lubricating oil stabi- polyhydric phenols have been patented as emulsifying
lizer, and multifunctional oil additives that possess antioxi- and wetting agents.
dant properties can be prepared from wax-phenols, A number of other morpholine-containing compounds
formaldehyde, and morpholine. have been used as wetting agents, and it is said that
Small quantities of morpholine and 1-ascorbic acid are morpholinium linoleate is an especially good surface
claimed to show marked synergistic antioxidant properties tension depressor for use in rust-preventive compositions
for use in fatty products. The morpholine salt of gallic acid because it tends to harden the rust-preventive film.
is an oil-soluble antioxidant for glyceridic oils and a The morpholine salt of a polymeric maleamic acid has
stabilizer for vitamin A and carotene, and 4-alkyl been used in compositions for coating paper, cloth, etc.
morpholines have been found to act as stabilizers for Small quantities of morpholine have been incorporated in
2-chlorothiophene. fireproofing materials, and the stability of certain asphalt
emulsions has been improved by the addition of
morpholine. This amine has also been used as an equaliz-
ing and dispersing agent in dye baths and printing pastes,
and its quaternary alkyl ammonium sulfates have been
patented as general surface-active agents.
5
APPLICATIONS
Miscellaneous Applications enables the user to modify his original graphic representa-
Morpholine derivatives have found application in the textile tion almost immediately.
industry. Thus, a biquaternary compound derived from A strongly basic ion-exchange resin can be prepared
4,4'-ethylenedimorpholine is suitable as a softening agent by treating a polymerized 4,4'-diallylmorpholinium bromide
for natural or regenerated cellulose. In viscose spinning, with alkali, and it is reported that a quaternary morpho-
small amounts of quaternary morpholine derivatives, linium ethosulfate is useful as a hair conditioner and
introduced into either the viscose solution or regenerating deodorant in popular wave formulations. The ethosulfate
bath, prevent fouling of the spinnerets during extrusion. is also found in shampoos and mouthwashes. A process
Compounds of this type are also useful as textile lubri- for citric acid by fermentation includes a small quantity of
cants and sizing emulsifiers. A superior whitening agent morpholine in the mash, and it has been found that
for textiles includes morpholine in the formula, and α-4- dimorpholinium oxalate is an excellent precipitant for
morpholinylacrylic esters have been claimed as textile trivalent gold. A rapid test for acrylates and acrylonitrile
adjuvants. depends upon reaction with morpholine as a first step.
A compound prepared from sulfur dioxide and Morpholine may be used alone to thermally stabilize
morpholine is useful in photographic developers, and a cellulose materials. Electric graded kraft papers treated
small amount of morpholine in the recipe improves the with morpholine will retain a higher degree of their original
keeping qualities of a fine grain developer. tensile strength after subjection to heat aging.
Morpholinium salts of sulfonated azo dye components Morpholine is used to prevent the deterioration of
are used in dry mixtures for the production of dye images paper, especially in books. The paper is impregnated with
by electrolytic recording methods. gaseous morpholine, thereby raising the pH of the paper
Morpholine is used in an ink eradicator formulation and removing the acidic conditions which cause its
that is used to remove a graphic arts ink. The eradicator deterioration.
6
PHYSICAL PROPERTIES
The following physical properties are for the pure com-
pound.
Autoignition temperature, °F Molar polarization, P � in benzene
590 75.3
Boiling point, 760 mm Hg, °C 128.3 Molecular weight 87.12
Conductivity, mho/cm x 1010 6 pK b 5.64
Density, 20°C, g/cc 0.999 Refractive index, nD , 20°C 1.4545
Dielectric constant, esu 7.176 Specific gravity, 20/20°C 1.0017
Dipole moment, Debyes 1.58 Surface tension, 20°C, dynes/cm 37.5
Flash point, TCC, °F 95 Vapor pressure, 20°C, mm Hg 7
Freezing point, °C -4.9 Viscosity, 20°C, centipoises 2.23
Heat capacity, 25°C, cal/mol/ deg 41.6 Weight, 20°C, Ib/gal 8.3
Heat of vaporization, 45-129°C, cal/ mol 9510
Solubility
The solvent power of morpholine is said to exceed
that of benzene, pyridine, and dioxane. Listed below are
the solubilities of some commom materials in morpholine.
g Solute in g Solute in g Solute in
100 g 100 g 100 g
Morpholine Morpholine Morpholine
Substance at 25°C Substance at 25°C Substance at 25°C
� �
Acetone 2-Ethylbutanol Paraffin wax (hot) >5
� �
Beeswax <1 Ethylene glycol Pine oil
� �
Benzene Ethyl ether Polyvinyl acetate >5
�
Benzyl cellulose >5 Methyl glycol ether Polyvinyl butyral >5
� �
Butyl ether n-Heptane Polyvinyl chloride >5
� �
Carbon tetrachloride 2-Hexanone Resin >5
� �
Castor oil Linseed oil Shellac >5
�
Cellulose acetate >5 Methanol Sulfur <5
�
Cellulose nitrate >5 Methylamine (gaseous) 33 Toluene
�
Copal gum >5 Methylcyclohexanol Trimethylamine (gaseous) 34
�
Dimethylamine (gaseous) 109 Naphtha >5 Turpentine
�
Ester gum >55 Paraffin oil <1 Water
� �
Ethanol Xylene
7
PHYSICAL PROPERTIES
Additional physical properties pertinent to the han-
dling and use of morpholine are presented in the pages
that follow.
Property Figure
pH Value of Aqueous Morpholine ...................................................................................................................................... 1
Flash Point of Aqueous Morpholine ................................................................................................................................... 2
Freezing Point of Aqueous Morpholine .............................................................................................................................. 3
Refractive Index of Aqueous Morpholine at 20°C............................................................................................................... 4
Specific Gravity of Aqueous Morpholine at 20°C ................................................................................................................ 5
Specific Gravity of Morpholine Versus Temperature .......................................................................................................... 6
Surface Tension of Aqueous Morpholine at 20°C .............................................................................................................. 7
Vapor-Liquid Equilibria for Aqueous Morpholine at Atmospheric Pressure......................................................................... 8
Vapor Pressure Versus Temperature of Morpholine .......................................................................................................... 9
Viscosity of Aqueous Morpholine at 20°C ........................................................................................................................ 10
Figure 1
pH Value of Aqueous Morpholine
12
11
pH VALUE
10
Concentration
Morpholine pH
9 0 7.0
0.001 8.8
0.01 9.4
0.1 10.0
8
1.0 10.6
10.0 11.2
7
0 10 20 30 40 50 60 70 80 90 100
MORPHOLINE, wt. %
8
PHYSICAL PROPERTIES
Figure 2
Flash Point of Aqueous Morpholine
190
180
170
160
FLASH POINT, °F
150
140
130
120
110
100
90
100 95 90 85 80 75 70 65 60 55 50
MORPHOLINE, wt. %
Figure 3
Freezing Point of Aqueous Morpholine
0 0
�5 �5
�10 �10
FREEZING POINT, °C
�15 �15
�20 �20
�25 �25
�30 �30
�35 �35
�40 �40
�45 �45
�50 �50
�55 �55
�60 �60
0 10 20 30 40 50 60 70 80 90 100
MORPHOLINE, wt. %
9
PHYSICAL PROPERTIES
Figure 4
Refractive Index of Aqueous Morpholine at 20°C
1.50
1.48
1.46
1.44
REFRACTIVE INDEX
1.42
1.40
1.38
1.36
1.34
1.32
0 10 20 30 40 50 60 70 80 90 100
MORPHOLINE, wt. %
10
PHYSICAL PROPERTIES
Figure 5
Specific Gravity of Aqueous Morpholine at 20°C
1.050
1.045
1.040
1.035
1.030
SPECIFIC GRAVITY
1.025
1.020
1.015
1.010
1.005
1.000
0.995
0.990
0 10 20 30 40 50 60 70 80 90 100
MORPHOLINE, wt. %
11
PHYSICAL PROPERTIES
Figure 6
Specific Gravity of Morpholine Versus Temperature
1.040
1.030
1.020
1.010
1.000
0.990
SPECIFIC GRAVITY
0.980
0.970
0.960
0.950
0.940
0.930
0.920
0.910
0.900
0 10 20 30 40 50 60 70 80 90 100
TEMPERATURE, °C
12
PHYSICAL PROPERTIES
Figure 7
Surface Tension of Aqueous Morpholine at 20°C
90
80
70
60
SURFACE TENSION, dynes/cm
50
40
30
20
10
0
0 10 20 30 40 50 60 70 80 90 100
MORPHOLINE, wt. %
13
PHYSICAL PROPERTIES
Figure 8
Vapor-Liquid Equilibria for Aqueous Morpholine at Atmospheric Pressure
100
90
80
WATER VAPOR, MOLE %
70
60
50
40
30
20
10
0
0 10 20 30 40 50 60 70 80 90 100
WATER IN LIQUID, MOLE %
14
PHYSICAL PROPERTIES
Figure 9
Vapor Pressure Versus Temperature of Morpholine
1000
900
800
700
600
500
400
300
200
VAPOR PRESSURE, mm Hg
100
90
80
70
60
50
40
30
20
10
0 10 20 30 40 50 60 70 80 90 100 110 120 130 140
TEMPERATURE, °C
15
PHYSICAL PROPERTIES
Figure 10
Viscosity of Aqueous Morpholine at 20°C
13.00
12.00
11.00
10.00
9.00
8.00
VISCOSITY, cp
7.00
6.00
5.00
4.00
3.00
2.00
1.00
0 10 20 30 40 50 60 70 80 90 100
MORPHOLINE, wt. %
16
CHEMICAL PROPERTIES
Because of the chemical inertness of ethers in general, The last reaction is an important one, for it offers a
most of the chemical reactions of morpholine involve the clean-cut route to mono-substituted acetoacetic esters via
alkylation of the β-4-morpholinylcrotonic ester. Alkyl
secondary amine function of the molecule. An outline of
the chemistry of morpholine is given in the following halides or sulfates are satisfactory alkylation reagents.
The mechanism of alkylation of ethyl β-4-morpholinyl-
sections. Reaction yields are given where they are
available. crotonate permits the attack of only one alkyl group and
treatment of the adduct with hot water leads to the
Reaction with Acids and Acid Derivatives mono-alkyl acetoacetic ester.
Like most secondary amines, morpholine reacts with Although reaction of morpholine with dialkyl sulfates
carboxylic acids and their anhydrides, chlorides, and and trialkyl phosphates results in 4-alkyl morpholines, the
esters to give the corresponding morpholides. related acid chlorides lead to morpholides.
O NH + (C2H5O)2POCI O 79%
(C2H5O)2PO N
O NH + CH3CHCOOCH3 CH3CHCO N O 83%
350C
OH OH
It is interesting that in the particular case cited, other O NH + (C2H5)2NSO2Cl (C2H5)2NSO2 N O 97%
secondary amines, such as diethylamine or diphenyl-
amine, were essentially unreactive.
Ethylene carbonate reacts smoothly with morpholine It is expected that ethyl chlorosulfonate would react
at temperatures below 100°C to give β-hydroxyethyl with morpholine in a similar manner.
N,N'-oxydiethylenecarbamate. Dibenzyl phosphite undergoes oxidation when treated
with morpholine and carbon tetrachloride and yields the
corresponding phosphoramidate.
NCOOCH2CH2OH 96%
O NH + O O
O
O O NH + (C6H5CH2O)2POH + CCl4
A morpholide is not formed, however, with β-propio-
(C6H5CH2O)2PO N
lactone or ethyl acetoacetate. 86%
O
Morpholine reacts with carbon dioxide to form a
O
carbamate that sublimes unchanged at about 95 to 100°C.
NCH2CH2COOH
O NH + O
Carbon disulfide gives the corresponding dithiocarbamate.
O
O NH + CS2 NCSSH � HN O
O
CH3
CHCOOC2H5
O NH + CH3COCH2COOC2H5 O NC
The action of potassium ferricyanide on the dithiocar-
bamate yields N,N,N',N'-bis (oxydiethylene) thiuram
disulfide.
NCSSH � HN
O NCS4C N
O + K3Fe(CN)6 O
O
17
CHEMICAL PROPERTIES
In the presence of certain water-soluble cyanides and Morpholine also reacts with 2-benzothiazolesulfen-
oxidizing agents, N,N,N',N'-bis (oxydiethylene) thiuram amide to give the substituted sulfenamide.
sulfide is obtained from the dithiocarbamate salts. N N
O NH + CSNH2 CSN O
NCSSNa + NaCN + (NH4)2S2O8
O NCS3C N O
O S S
The Mannich and Related Reactions
The monosulfide can also be obtained by treating the
Morpholine has been found to enter into the Mannich
disulfide with potassium cyanide.
reaction in the broadest sense. Thus, phenols, ketones,
nitroalkanes, and amides react with morpholine and
Reaction with Isocyanates and Isothiocyanates
formaldehyde to give corresponding 4-morpholinylmethyl
Reactions of morpholine with isocyanates give the corre-
compounds.
sponding substituted ureas, and isothiocyanates yield
thioureas.
OH CH2N O
O NH + + HCHO
OH
CHCH2NHCS N O
CH2
CHCH2NCS
O NH + CH2 82%
O NH + KCNS + HCl NH2CS N O
O NH + CH3COCH3 + HCHO O NCH2CH2COCH3
Reaction with Amines and Amides
Mannich bases, such as β-dimethylaminopropiophenone,
and Betti bases, e.g.,1-α-dimethylaminobenzyl-2-naph-
thol, undergo amine exchange when heated with
morpholine. O NH + CH3CH2CH2NO2 + HCHO
O NCH2CHCH2CH3 68%
O NH + C6H5COCH2CH2N(CH3)2
NO2
C6H5COCH2CH2 N O 78%
The amine function of certain amides, too, can be
caused to exchange with morpholine. Heating the latter O NH + H2NCONH2 + HCHO O NCH2NHCONH2 92%
with urea in a nitrogen atmosphere gives 4-morpholine-
carboxamide.
NCONH2 96%
O
O NH + H2NCONH2
O NH + C2H5OOCNHNO2 + HCHO
O NCH2NCOOC2H5
NO2
18
CHEMICAL PROPERTIES
No reaction occurs with a simple aliphatic nitrile, but preparing 4-substituted morpholines. Certain activated
if the effect of the nitrile group is augmented by that of a ethers also react with morpholine to give morpholine
phenyl group, reaction does occur. Thus, phenylaceto- derivatives and, under vigorous conditions,
nitrile reacts, but acetonitrile does not. polymethylene glycols have been found to give low
yields of ω -4-morpho-linylalkanols and 4,4'-
Alcohols enter this reaction to give 4-morpholinyl-
methyl ethers. polymethylenemorpholines. Examples of these reactions
are:
O
O NH + C2H5OH + HCHO NCH2OC2H5 59% O
O NH + (C2H5O)2SO2 + NaOH NC2H5
Reaction with Aldehydes
O
O NH + n - C12H25Br + K2CO3 NC12H25
Two molecules of morpholine condense with an alde-
hyde to form a 4,4'-alkylidenedimorpholine. When the
aldehyde bears an alpha hydrogen atom, the appropri-
ate enamines form upon gentle heating.
NH + CH3CHCN KCN O
O NCHCN
NH + n - C3H7CHO O NCHN
O O CH3
OH
C3H7
O NCH 95%
CHC2H5
O
O NH + CH3OCH2CH2CN NCH2CH2CN
150 - 2300C
The Leuckart-Wallach Reaction
The addition of formic acid to a mixture of morpholine
Catalyst
and aldehyde leads to reductive alkylation of the O NH + HO(CH2)8OH O N(CH2)8OH 26%
Heat
morpholine. This is the Leuckart-Wallach reaction. Pressure
+O N(CH2)8 N 41%
O
O NH + (CH3)2CHCHO + HCOOH
O NCH2CH(CH3)2 Arylation
73%
Morpholine can be arylated by aryl halides that possess
relatively labile halogens.
Some ketones, e.g., cyclohexanone, can be used
instead of aldehydes. NH + Cl
O NO2 + Na2CO3
reflux
Alkylation
In addition to the Mannich and Leuckart-Wallach reac- O N NO2
tions, morpholine can be alkylated by several other
methods. Dialkyl sulfates, trialkyl phosphates, alkyl
halides, and cyanhydrins are effective reagents for
Morpholine reacts more slowly than does piperidine
in this respect, but it is equally favored by the absence of
by-products and the morpholine derivatives are, in
general, higher melting.
19
CHEMICAL PROPERTIES
Aryl halides characterized by reduced aromaticity, Reaction with Epoxides and Imines
e.g., halogenated anthraquinones or Morpholine reacts with alkylene oxides to give the
corresponding β-4-morpholinylalkanols.
2-chloro-6-methoxy-benzothiazole, also arylate
morpholine. O
N N
58% O NH + CH2 O NCH2CH2OH
CH2
O NH + CIC O NC
reflux
OCH3
S S OCH3
Polyoxyethylene derivatives also can be obtained.
O
Addition to Unsaturation
Like most secondary amines, morpholine adds to α, β- O NH + (n + 1) CH2 O N(CH2CH2O)nCH2CH2 OH
CH2
unsaturated ketones, esters, and nitriles in a manner
presumed to be typical 1,4-addition.
Ethylenimine and morpholine yield 4-(2-aminoethyl)-
O NH + CH2 CHCOOC2H5 morpholine.
reflux
H
N
O NCH2CH2COOC2H5 86%
H2SO4
55%
O NH + CH2 O NCH2CH2NH2
CH2
In certain instances, however, apparently as a
Willgerodt Reaction
consequence of enolization, reaction occurs at an allylic
As originally reported, yellow ammonium sulfide was
position rather than at the normal olefinic linkage.
employed in the Willgerodt reaction to convert aryl alkyl
O NH + C6H5COCH CCH3
ketones to ω -aryl fatty acid amides. The volatility of
COC6H5 ammonium polysulfide required that the reaction be
carried out in a closed vessel at 150°C. The disadvan-
C6H5COCH2CHCH2 N O tage was overcome when morpholine and sulfur were
substituted for the volatile sulfide. Since then, the
COC6H5
reaction has been the subject of considerable investiga-
tion, much of it employing morpholine, although other
In the presence of cuprous chloride, morpholine high-boiling amines can be used.
reacts with phenylacetylene to give 3-(4-morpholinyl)- The nucleus may be heterocyclic as well as homo-
1,4-diphenyl-1-butyne. cyclic. Thus, 4-acetylpyridine gives
4-pyridylthioacetomor-pholide.
Cu2Cl2
O NH + C6H5C O NCHC
CH CC6H5
CH2C6H5 O NH + N COCH3 + S N CH2CSN O 76%
reflux
20
CHEMICAL PROPERTIES
Acetylphenylacetylene and benzalacetone have Acetylene gives 54% dithioöxalomorpholide and
been found to behave as typical aryl alkyl ketone, giving 45% acetothiomorpholide.
γ-phenylethylthioacetomorpholide and γ-phenylvinylthio- Aryl alkyl ethers give β-aryloxypropiothiomorpholides
acetomorpholide, respectively. when refluxed with morpholine and sulfur, but vinyl
ethers and esters are cleaved at the oxygen to give
thioaceto-morpholide.
CCOCH3 + S
O NH + C6H5C reflux
CCH2CS N O
C6H5C 51% CH3CS N O
O NH + C4H9OCH CH2 + S
When α-tetralone is the ketone employed, no
Reaction with Oxidizing Agents
thiomorpholide is possible without ring rupture and the
Morpholine reacts with aqueous sodium hypochlorite in
product is 4-(2-naphthyl)-morpholine.
the cold to give a quantitative yield of
O
4-chloromorpholine. Sodium hypobromite reacts simi-
larly.
+S
O NH +
reflux O NH + NaOCl O NCl
N O
In addition to aryl alkyl ketones, the reaction has
Essentially quantitat ive yields of 4-cyanomorpholine
been found to be applicable to aldehydes, alcohols,
result when a cold ethereal solution of morpholine is
mercaptans, amines, olefins, and acetylenes. Thus,
treated with cyanogen bromide.
benzaldehyde, benzylamine, and benzylmercaptan give
benzothiomorpholide when refluxed with equivalent O NH + CNBr O NCN
quantities of morpholine and sulfur.
On the other hand, if a benzene solution of
O NH + C6H5CHO + S C6H5CS N O
reflux
morpholine and cyanogen chloride is refluxed, the
product is the hydrochloride of
Styrene and vinylnaphthalene yield the correspond-
1,1,3,3-bis(oxydiethylene)-quanidine. The hydrobromide
ing aryl acetothiomorpholides under the conditions of the
of the same base results from reaction of 4-
Willgerodt reaction.
cyanomorpholine with morpholine hydrobromide.
NH
O NC N O � HCl
O NH + CNCl
C6H5CH2CS N O 52%
O NH + C6H5CH CH2 + S reflux
reflux
Morpholine reacts with aqueous hydrogen peroxide
to give low yields of 4-hydroxymorpholine.
O NH + H2O2 O NOH
O0C
21
CHEMICAL PROPERTIES
Oxidative condensation of morpholine with anhydrous condition some of them are stable to tem-
2-mercap-tobenzothiazole in the presence of iodine peratures in excess of 200°C. The decomposition
yields 2-(4 mor-pholinylmercapto)-benzothiazole. temperatures of several of the halide complexes are:
N N
Halide Decomposition Halide Decomposition
O 86%
CSH + I2 CSH
O NH +
Complex Range,°C Complex Range,°C
S S
CdBr2 250-252 ZnCI2 200-210
Cdl2 205-210 ZnBr2 230-240
The Hofman Degradation
HgBr2 131-135 SnCI4 215-235
Thermal decomposition of quaternary morpholinium
hydroxides may result in either retention or rupture of the
Cuprous chloride combined in a 1:1 molecular ratio
morpholine ring.
with aqueous morpholine hydrochloride at temperatures
CH CH2
below 50°C gives a 90% yield of a complex which melts
with decomposition at 110.5 to 112°C. Cupric chloride,
O N O NCH2
+ under the same conditions, gives a complex containing
OH-
two moles of morpholine hydrochloride per mole of
cupric chloride. This complex melts at 160°C.
O N NCH2CH2OCH CH2 Miscellaneous Reactions
+
Morpholine attacks chloral in the same fashion as does
OH-
sodium hydroxide; the products are chloroform and
Direct Chlorination 4-formylmorpholine.
An excess of morpholine reacts with chlorine to form
4-chloromorpholine and an equivalent amount of mor- O NH + CCl3CHO O NCHO + CHCl3 92%
pholinium chloride.
The latter is formed in equally good yield from
2O NH + Cl2 O N - Cl + O NH2Cl
morpholine and formic acid.
Aryl diazonium salts treated with morpholine give
4-aryl-azomorpholines. These compounds are readily
Complex Formation purified and are reported to be remarkably stable in the
The addition of certain metallic halides to hot morpholine solid state.
results in the formation of addition complexes which
contain two moles of morpholine per mole of metallic
NN O
O NH + C6H5N2Cl C6H5N
halide. The complexes are sensitive to moisture, but in
22
HANDLING AND STORAGE
an General temperature of the morpholine will exceed 150°F.
The handling and storage of morpholine presents no Neither should it be used in contact with aqueous
unusual problems. Huntsman Corporation's Technical morpholine solutions at any temperature.
Service Section is available to assist those who may In areas where the temperature is expected to fall
desire additional information. below 23°F, steam coils of a suitable area to heat the
Commercial morpholine is liquid at room tempera- tank contents using low-pressure steam should be built
ture, but will solidify at approximately 23°F. into the tank about 6 inches above the floor. The coils
The vapor pressure of morpholine is less than 7 mm should be constructed in such a manner as to allow the
of mercury at 20°C. Being an organic compound, it will condensate to drain. Stainless steel is the preferred
undergo combustion, and it is classified as flammable by material of construction for the coils, particularly when
the Department of Transportation. Although not consid- low color of the morpholine is important. When steam
ered poisonous, morpholine is moderately toxic and heat is to be used continuously to prevent freezing of the
should not be ingested or allowed to come in contact morpholine, a temperature regulator that throttles either
with the skin. In case of contact with the eyes, flush the steam or condensate should be installed.
immediately with plenty of water for at least 15 minutes In situations where the ambient temperature is low,
and obtain medical attention. (See toxicity statement on insulation of the tank will probably be desirable. The
pages 26-27.) temperature of the morpholine in the tank should not
exceed 100°F if the low color is to be maintained.
Maintaining Specifications If a dry gas pad is used, pressure relief and vacuum
Morpholine is hygroscopic and, if its water content is to relief valves of suitable capacities should be installed.
be minimized, a dry gas pad under a few ounces of The dry gas system may consist of a cylinder of nitrogen
pressure should be used on storage tanks. Since and a line to the top of the storage tank. Tanks should
morpholine is basic, it will react with acidic gases, hence be diked and electrically bonded and grounded.
carbon dioxide and natural gas containing acidic sulfur
compounds cannot be used. Nitrogen is quite suitable. Transfer Lines
Nitrogen should also be used if low color is important, Transfer lines, preferably not less than 2 inches in
since absorbed atmospheric oxygen will cause diameter, constructed of carbon steel and joined by
morpholine to develop color. welds or flanges are suitable. Screwed joints are subject
Morpholine will react with copper to form complex to failure unless back-welded. Morpholine will leach
salts. Because of this, the use of copper and alloys conventional pipe dopes. However, threads can be
containing copper should be avoided in equipment which wrapped with Teflon tape. Garlock 7021 gasket material,
will contact morpholine or its aqueous solutions. or its equivalent, is satisfactory for use with flanged
Other factors that should be considered in the connections in morpholine service.
installation of storage and handling facilities are the If the ambient temperature is low, the transfer line
solvent properties and alkaline nature of morpholine. should be steam-traced and insulated. Steam-tracing
Storage tanks constructed according to a recognized can be accomplished by affixing copper tubing, approxi-
mately 3/8-inch diameter, to the underside of the line,
code, using carbon steel as a material of construction,
generally are satisfactory. In those cases where low insulating, and using low-pressure steam in the tubing.
color is needed, stainless steel or aluminum should be For flexible connections, stainless steel metal hose is
used. However, aluminum should not be used if the preferred to rubber, since rubber will generally deterio-
rate in morpholine service.
23
HANDLING AND STORAGE
Systems which are insulated and steam-traced Morpholine which has frozen in drums may be
should be preheated in cool weather before being put thawed in a hot room at about 100°F. The thawing
into service. Normally,15 to 30 minutes of applying should be expected to require two days.
steam to the tracing will adequately warm, but not
New Facilities and Cleaning
overheat, the system.
Prior to putting storage vessels into service, it is some-
Transfer piping and pumps may be equipped with an
times desirable to purge with inert gas to remove oxygen
inert gas padding system so that the morpholine can be
from the tank atmosphere. Although cleaning tanks and
pressured out of the lines when an extended idle period
transfer lines frequently is not recommended, it is
is due. This practice will help to reduce losses and
sometimes necessary as the result of contamination or
increases in color that would result if the morpholine was
accumulation of foreign material in the system. For such
allowed to remain in the lines.
cleaning, a water wash is generally satisfactory.
Pumps Tank cleaning is normally accomplished by thor-
Rotary or centrifugal pumps of all-iron construction can oughly sluicing the interior of the tank with a water jet
be used with morpholine, although a centrifugal pump is and following this with cloth or chamois drying. Unless
preferred. Rotary pumps should be equipped with excessive rust scale makes it necessary, the interior of
externally lubricated bearings. John Crane Type 9 the tank should not be wire-brushed or sand-blasted
Mechanical Seal is suitable. Where pump packing is because the oxides of iron are relatively inert to
needed, Garlock 234, Garlock 239, or equivalent is morpholine. Once clean and dry, the tank should be
considered satisfactory. Provision should be made for sealed and purged with dry inert gas to avoid undue
preheating pumps that are exposed to the cold. This can condensation and rust formation.
be done by playing live steam on the uninsulated pump, New systems frequently introduce line scale, rust,
or by having the pump wrapped with copper tubing and and the like, which will be a source of contamination and
insulated, then applying low-pressure steam to the possible plugging. These solids can be effectively
tubing. removed with either a “y� strainer, using a 150-200 mesh
stainless steel screen, or with a commercial-type cloth
Unloading in Cold Weather filter. A good grade of woven cotton canvas,12-ounce or
Thawing a tank or tank car of morpholine is accom- heavier, is suitable as a cloth filter medium. Wool and
plished by applying steam at 50 pounds maximum synthetic fibers have been found to be unsatisfactory.
pressure to the coils of the tank or tank car. The liquid Most of what has just been described concerns
temperature should be kept below 100°F to avoid commercial, essentially anhydrous, morpholine. Its
discoloring the product. aqueous solutions have lower freezing points and lower
As the morpholine melts, solids will remain in the viscosities, so storage and handling may be simplified
bottom and on the sides of the tank while the warmer considerably by dilution in storage if the morpholine is to
liquid rises. The thawing may be accelerated by using a be used as an aqueous solution.
liquid circulating pump. As soon as the flow of steam to
the coils is discontinued, they should be blown free of
condensate with dry air to prevent freezing of the
condensate and rupturing of the coils.
24
SHIPPING INFORMATION
Delivery of morpholine can be made in 10,000- and Packing Group III flammable liquid, does not address the
20,000-gallon tank cars. These cars are constructed of potential dermal corrosivity hazards of morpholine.
welded carbon steel, and have bottom-unloading fittings Huntsman has recently sponsored DOT dermal
and steam coils. In areas within reasonable proximity of corrosivity studies using morpholine which indicate that
bulk storage points, deliveries can be made in full or morpholine should be reclassified as a Packing Group I
compartmented, insulated, stainless-steel tank wagons dermal corrosive. On the basis of these studies, Hunts-
with steam coils. If requested, tank wagons can be man has petitioned the DOT for a change in the Hazard-
equipped with unloading pumps and hoses. Drums of ous Materials Table entry for morpholine, from Packing
morpholine can be shipped promptly from local ware- Group III flammable liquid to Packing Group I corrosive
houses in carload, truckload, or smaller quantities. The liquid with a subsidiary hazard of flammability. Until the
net weight of a drum is 460 pounds, approximately 55 DOT rules on our petition for this change, we will con-
gallons per drum. Drums are UN1A1 or UN1H1, nonre- tinue to identify morpholine as a Packing Group III
turnable. flammable liquid on our MSDS, product labels, and
Under US Department of Transportation (DOT) and shipping papers, to minimize any confusion which could
Canadian Transportation of Dangerous Goods (TDG) result from a discrepancy between our DOT Packing
regulations, the proper shipping name for this product is Group determination and the existing DOT classification
“morpholine,� identification number UN 2054. This for morpholine. However, to ensure employee, cus-
product is considered a flammable material (TDG hazard tomer and public safety, Huntsman will handle and
class 3.3) and requires a “FLAMMABLE� label for transport morpholine as a Packing Group I corro-
shipping. Please note: The Department of Transporta- sive, using appropriate shipping containers and
tion (DOT) classification for morpholine, UN 2054, as a handling procedures.
For further information, please refer to the Material
Safety Data Sheet (MSDS) for this product.
25
SAFETY AND TOXICITY
HANDLING AND STORAGE
MORPHOLINE FDA CLEARANCES UNDER 21 CFR ogy, and histopathology were normal in the exposed
groups and comparable to the control animals. There
Direct Additives were no exposure-related adverse changes in the liver,
172.235 173.310 kidney, brain, intestine, lung, or any other internal organ
or tissue. The incidences of neoplasia were comparable
Indirect Additives among all groups (including controls), and were typical
175.105 176.210 for the strain and age of rat used in this study. Not
175.300 177.1200 unexpectedly, irritation of the eyes, nose, and skin was
176.170 177.1210 observed during the course of this study. Chronic
176.180 178.3120 exposure to morpholine vapors produced inflammation
176.200 178.3300 of the cornea (keratitis) at the highest exposure concen-
tration.
Nasal effects included nasal cavity irritation and
TOXICITY STUDIES
necrosis at the highest exposure concentration. Poste-
rior nasal structures (trachea, bronchial tree, and lungs)
Acute Toxicity
were histologically normal.
The results of acute toxicity testing using morpholine
The results of this chronic exposure study demon-
indicate that this product is moderately toxic by single
strate that morpholine is neither carcinogenic nor
oral and single dermal exposures. The oral LD50 in rats
systemically toxic. These exposures did result in local
and the dermal LD50 in rabbits are 1.05 g/kg and 1.21 g/
(ocular, nasal, and dermal) irritation, consistent with the
kg, respectively.
known irritation properties of morpholine.
Acute irritation studies have shown this product to
be extremely irritating/corrosive to the skin of rabbits,
Genetic Toxicity
with a Draize dermal irritation score of 8.0 (maximum
A battery of in vitro genetic toxicity studies, employing an
score 8.0). Rabbit eye irritation studies using morpholine
Ames assay, a Cell Transformation assay, an Unsched-
have shown that this product is extremely irritating to the
uled DNA Synthesis (UDS) assay, and a Sister Chroma-
eyes, with a Draize ocular irritation score of >80 (maxi-
tid Exchange (SCE) assay, were equivocal in their
mum score 110).
responses to morpholine. Morpholine was negative in
the Ames and UDS assays, and weakly positive in the
Chronic Toxicity
Mouse Lympho-ma Forward Mutation and SCE assays.
A chronic inhalation (vapor) study of morpholine was
Morpholine was active (positive) in the Cell Transforma-
conducted using Sprague-Dawley rats at exposure
tion assay. The interpretation of these assays may be
concentrations of 0, 10, 50, and 150 ppm for 6 hours per
confounded by the contribution of the pH of the test
day, 5 days per week, over a period of 104 weeks.
medium (after introduction of morpholine) to the ob-
Survival, body weight gains, organ weights, hematol-
served genotoxic activity in these assays. The possible
ogy/clinical chemistry blood parameters, gross pathol-
presence of nitrosating agents in the test system may
26
SHIPPING AND TOXICITY
SAFETY INFORMATION
also contribute to genotoxic activity in these assays, due produce dermal sensitization (allergic skin reaction) in
to the potential formation of genetically active nitro- sensitive exposed individuals.
samines. If morpholine is accidentally ingested and the
individual is conscious and can swallow, he or she
Aquatic Toxicity should be given two large glasses of water, after which a
The acute toxicity (LC50) of morpholine to freshwater fish physician should be consulted. Since this product is
has been reported to range from 180 to 380 mg/l (Salmo expected to produce severe irritation/corrosion of
species). The acute toxicity (LC50) to freshwater crusta- mucous membranes, vomiting should not be induced,
ceans (Daphnia species) has been reported to range due to the possibility of lung damage from aspiration of
from 100 to 119 mg/l. The toxicity threshold (EC50) to the product into the lungs during vomiting.
algae has been reported to be 1.7 to 28 mg/l. Under usual circumstances, exposure to harmful
quantities of vapor should not be a health problem;
HUMAN HEALTH EFFECTS AND FIRST AID however, exposure to appreciable concentrations of
On the basis of these animal toxicity studies, the princi- morpholine vapors can result in irritation to the eyes,
pal health hazard from accidental exposures to nose, and throat, and may produce temporary and
morpholine is a moderate to severe irritation/corrosion reversible hazy or blurred vision. These symptoms
of the eyes, skin, and mucous membranes. disappear when exposure to morpholine is terminated.
Chemical-type goggles with face shield must be worn Adequate ventilation should be provided where a large
during handling or use of the undiluted product or quantity of product is exposed, or where mists or vapors
concentrated solutions. Contact lenses should not be are generated. Spills in confined areas should be
worn. Protective clothing and gloves resistant to chemi- cleaned up promptly, using appropriate personal protec-
cals and petroleum distillates must be worn. tive equipment.
Should accidental eye contact occur, flush eyes with The Threshold Limit Value (TLV ) for morpholine, as
large amounts of water for at least 15 minutes, after established by the American Conference of Governmen-
which a physician should be consulted. During flushing tal Industrial Hygienists (ACGIH) is 20 ppm (71 mg/m3),
of the eyes, eyelids should be held apart to permit calculated as an 8-hour time weighted average (TWA).
rinsing of entire surface of eye and lids. The TLV for morpholine also includes a “skin� notation,
For skin contact, immediately flush skin with large warning of the potential significant contribution to the
amounts of water for at least 15 minutes. Clothing wet overall exposure by the cutaneous route. The Occupa-
with the product must be removed immediately and tional Safety and Health Administration (OSHA) has
laundered before reuse. Morpholine has been known to established a Permissible Exposure Limit (PEL) for
morpholine at 20 ppm, and a Short Term Exposure Limit
(STEL) of 30 ppm. Exposures should be kept below
these values to avoid symptoms of irritation to eyes,
nose, and throat.
For further information, please refer to the Material
Safety Data Sheet (MSDS) for this product.
27
FOR MORE LITERATURE OR INFORMATION
Please Call the Nearest Huntsman Corporation Office
Huntsman Belgium BVA
Huntsman (Singapore) Pte Ltd Everslaan, 45
HUNTSMAN CORPORATION 3078 Everberg
150 Beach Road
10003 Woodloch Forest Dr. Belgium
#14-05/08 Gateway West
The Woodlands, TX 77380 Tel: +32-2-758-92 11
SINGAPORE 189720
Tel: 281-719-6000 Technical Service:
Tel: (65) 6390-0370
Fax: 281-719-7555 Tel: +32-2-758-93 92
Fax: (65) 6296-3368
Fax: +32-2-758-92 12
Research and Development Huntsman do Brazil
8600 Gosling Rd. do Participacoes Ltda.
The Woodlands, TX 77381 Rua Andre do Leao, 2101
Tel: 281-719-7780 04762-030 -- Sao Paulo - SP
Fax: 281-719-7555 Brazil
Tel: +55-11-5696-9311 / 9312
Huntsman Corporation C.A.
Multicentro Paseo El Parral
Fax: + 55-11-5521-9933
Huntsman de Mexico, S.A. de C.V.
Piso 06, Oficina 11
CUSTOMER SERVICE Montecito 38 Piso Ofna. 38
(Las Cuatro Avenidas) Urb. El Parral
Col. Napoles.
REPRESENTATIVES Valencia Estado Carabobo
03810 Mexico, D.F.
VENEZUELA
Tel: +5255-5488-2911/2912
Tel: (58) 41-25-4547
TTel+5255-5488-2913
Fax: (58) 41-25-2267
Tel: 1-800-852-4957
Fax: +5255-5488-2910
Emergency Assistance
For transportation emergencies only,
call CHEMTREC 1-800-424-9300.
For all other emergencies,
call 409-722-8381, our 24-hour
emergency number in Port Neches,
Texas.
Copyright © 2005 1080-0905
Huntsman Corporation
Huntsman Corporation warrants only that its products meet the specifications stated herein. Typical properties, where stated, are to be considered as
representative of current production and should not be treated as specifications. While all the information presented in this document is believed to be reliable
and to represent the best available data on these products, NO GUARANTEE, WARRANTY, OR REPRESENTATION IS MADE, INTENDED, OR IMPLIED AS
TO THE CORRECTNESS OR SUFFICIENCY OF ANY INFORMATION, OR AS TO THE SUITABILITY OF ANY CHEMICAL COMPOUNDS FOR ANY
PARTICULAR USE, OR THAT ANY CHEMICAL COMPOUNDS OR USE THEREOF ARE NOT SUBJECT TO A CLAIM BY A THIRD PARTY FOR INFRINGE-
MENT OF ANY PATENT OR OTHER INTELLECTUAL PROPERTY RIGHT. EACH USER SHOULD CONDUCT A SUFFICIENT INVESTIGATION TO
ESTABLISH THE SUITABILITY OF ANY PRODUCT FOR ITS INTENDED USE. Products may be toxic and require special precautions in handling. For all
products listed, user should obtain detailed information on toxicity, together with proper shipping, handling, and storage procedures, and comply with all
applicable safety and environmental standards.
Main Offices: Huntsman Corporation / 10003 Woodloch Forest Dr. / The Woodlands, Texas 77380 / 281-719-6000
Technical Services Section: 8600 Gosling Rd. / The Woodlands, Texas 77381 / 281-719-7780
28
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