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4-Ethylmorpholin

Ethylmorpholine

HCID 7525
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Grundinformationen

CAS
100-74-3
Standard-SMILES
CCN1CCOCC1
InChIKey
HVCNXQOWACZAFN-UHFFFAOYSA-N
Summenformel
C6H13NO
Durchschnittliche Molmasse
115,17 g/mol
Monoisotopische Masse
115,09971404

Überblick

N-ethyl morpholine appears as a colorless liquid with a strong ammonia-like odor. Severely irritates skin, eyes, and mucous membranes. Moderately soluble in water and less dense than water. Flash point 83 °F.

Namen und Bezeichner

Bevorzugter Name
Ethylmorpholine
IUPAC
4-ethylmorpholine
Lokaler Name
4-Ethylmorpholin
Englischer Name
N-Ethylmorpholine
Summenformel
C6H13NO
Molmasse
115.17

Namen und Synonyme

4-EthylmorpholineN-ETHYLMORPHOLINE100-74-3Morpholine, 4-ethyl-EthylmorpholineN-EthylmorfolinDTXSID5025312ECM0G991FQNSC-6110DTXCID205312RefChem:163360202-885-0
Weitere Namen anzeigen
HEMTexacat NEMToyocat -NEMLUPRAGEN(R) N 1044-ethyl-morpholin4-Ethylmorhpoline
N-ethyl morpholineNSC 61104-ethyl-morpholineMFCD00006177N-Ethylmorfolin [Czech]N-ethyl-morpholineCCRIS 4818HSDB 1644

Datenbank-Bezeichner

CAS
100-74-3
PubChem CID
7525
DTXSID
DTXSID5025312
ChEMBL
CHEMBL3561880
UNII
ECM0G991FQ
EC Number
202-885-0
Nikkaji
J4.428H

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0
Polarare Oberfläche (TPSA)
12,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
8
Formalladung
0
Komplexität
59,5

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Morpholines

Flammable agents - 3rd degree

SpringerMaterials PropertiesViscosity
Odor · 2 Einträge

AMMONIACAL ODOR

Ammonia-like odor.

Density · 4 Einträge

0.916 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8996 @ 20 °C/4 °C

Relative density (water = 1): 0.99

0.90

Viscosity1.08 mPa S @ 20 °C
Color/Form · 2 Einträge

COLORLESS LIQUID

Colorless liquid.

Solubility · 4 Einträge

greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)

SOL IN ALL PROPORTIONS IN WATER, ETHANOL & ETHER; SOL IN ACETONE

Solubility in water: miscible

Miscible

Flash Point · 5 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 1% (5 of 484) of reports.

Danger

H226 (99%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 484 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Morpholine, 4-ethyl-

Morpholine, 4-ethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Morpholine, 4-ethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-01-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/17727

4-Ethylmorpholine: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 2 Einträge

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as ammonia, nitrogen oxides, and carbon monoxide, may be formed when involved in fire.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 32 °C explosive vapour/air mixtures may be formed.

Chemie und Industrie

Pharmakologische Informationen

Absorption, Distribution and Excretion...ABSORBED THROUGH UNBROKEN SKIN.

Verwendung und Herstellung

Uses · 5 Einträge

Used as a catalyst in the production of polyurethane foam; [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

URETHANE FOAM CATALYST

INTERMEDIATE FOR DYESTUFFS, PHARMACEUTICALS, RUBBER ACCELERATORS & EMULSIFYING AGENTS; SOLVENT FOR DYES, RESINS, OILS

COMMONLY USED SUBSTRATE FOR ENZYME REACTIONS

U.S. Production2023: 50,000 - <250,000 lb
Consumer UsesCatalyst
Industry UsesCatalyst
Methods of ManufacturingREACTION OF MORPHOLINE WITH DIETHYL SULFATE
Formulations/PreparationsGRADE: TECHNICAL.
Household ProductsInformation on 1 consumer products that contain N-Ethylmorpholine in the following categories is provided:
General Manufacturing Information · 2 Einträge

Plastics Product Manufacturing

Morpholine, 4-ethyl-: ACTIVE

Anwendungen

VerwendenN-Ethylmorpholine is a component of the buffer used in basic peptide separation through anion-exchange chromatography. Further, it acts as a catalyst in the preparation of polyurethane foam.

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82 °F (NTP, 1992)

32 °C

90 °F (32 °C) (OPEN CUP)

32 °C

(oc) 90 °F

Boiling Point · 4 Einträge

280 to 282 °F at 760 mmHg (NTP, 1992)

138-139 °C @ 763 MM HG

138 °C

281 °F

Melting Point · 4 Einträge

-81 °F (NTP, 1992)

-62.78 °C

-63 °C

-81 °F

Vapor Density · 3 Einträge

4 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

4.0 (AIR= 1)

Relative vapor density (air = 1): 4.0

Odor ThresholdOdor Threshold Low: 0.08 [ppm]

Physikochemische Eigenschaften

Schmelzpunkt
-63 °C · -63 °C (lit.)
Siedepunkt
139 °C · 139 °C (lit.)
Dichte
0.91 g/mL · 0.91 g/mL at 20 °C (lit.)
Dampfdruck
8.1 hPa · 8.1 hPa (20 °C)
Brechungsindex
20 · n20/D 1.441(lit.)
Flammpunkt
82 °F · 82 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
miscible
Aggregatzustand
Powder
pka
7.67 · 7.67(at 25℃)
Farbe
Cream to beige to brown-grey
Geruch (Odor)
Foul odor
PH
11.8 · 11.8 (100g/l, H2O, 20℃)
Explosionsgrenze
1.9 % · 1.9%(V)
Wasserlöslichkeit
miscible
BRN
102969 · 102969
Henry's Law Constant
4 · 4.0×102 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Stable. Flammable. Incompatible with strong oxidizing agents. Slightly air sensitive.
InChI
1S/C6H13NO/c1-2-7-3-5-8-6-4-7/h2-6H2,1H3
InChIKey
HVCNXQOWACZAFN-UHFFFAOYSA-N
SMILES
CCN1CCOCC1 || CCN1CCOCC1
LogP
0.08 at · 0.08 at 24.6℃
CAS Datenbank
100 · 100-74-3(CAS DataBase Reference)
NIST chemische Informationen
4 · Morpholine, 4-ethyl-(100-74-3)
EPA chemische Informationen
N-Ethylmorpholine (100-74-3)
Absorption
300 nm · cut-off at 300nm
Fire Potential...A DANGEROUS FIRE HAZARD...
Health HazardsExposure can cause irritation of eyes, nose and throat. Contact with eyes may result in foggy vision and seeing halos around lights. (USCG, 1999)
Hazards SummaryHas potential to cause corneal damage; [ACGIH]
Reactive GroupAmines, Phosphines, and Pyridines
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
Reactivity AlertsHighly Flammable
OSHA Standards · 2 Einträge

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 20 ppm (94 mg/cu m). Skin Designation.

Vacated 1989 OSHA PEL TWA 5 ppm (23 mg/cu m), skin designation, is still enforced in some states.

Reactivity ProfileN-ETHYL MORPHOLINE can react vigorously with oxidizing materials. It dissolves LiAlH4. (NTP, 1992)
Chemical DangersDecomposes on heating. This produces toxic gases and vapours (ammonia, nitrogen oxides, carbon monoxide). Reacts violently with strong oxidants. This generates fire and explosion hazard. Attacks plastics, rubber and coatings.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use water spray, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink.

First Aid · 2 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants.
Fire Fighting Procedures · 2 Einträge

ALCOHOL FOAM, FOAM, CARBON DIOXIDE, DRY CHEMICAL.

WATER MAY BE INEFFECTIVE.

Storage ConditionsStore in a detached storehouse without any ignition source.
Cleanup Methods · 2 Einträge

1) REMOVE ALL IGNITION SOURCES. 2) VENTILATE AREA OF SPILL OR LEAK. 3) FOR SMALL QUANTITIES, ABSORB ON PAPER TOWELS. EVAPORATE IN SAFE PLACE (SUCH AS A FUME HOOD). ALLOW SUFFICIENT TIME FOR EVAPORATING VAPORS TO COMPLETELY CLEAR HOOD DUCTWORK. BURN PAPER IN SUITABLE LOCATION AWAY FROM COMBUSTIBLE MATERIALS.

Cover with the 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton, stuffed with ruffled paper. Burn in an open furnace with the utmost care or in the furnace with afterburner and scrubber.

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 2 Einträge

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

LARGE QUANTITIES CAN BE COLLECTED & ATOMIZED IN A SUITABLE COMBUSTION CHAMBER EQUIPPED WITH AN APPROPRIATE EFFLUENT GAS CLEANING DEVICE.

Spillage Disposal · 1 Eintrag

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 5 Einträge

...GOOD VENTILATION IS VERY IMPORTANT. /MORPHOLINE/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet should be immediately removed due to its flammability hazard.

Take off the clothing followed by drying and washing or disposing. Dispose shoes by incineration.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Toxikologische Informationen

Target OrgansEyes, respiratory system
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Using a structure estimation method based on molecular connectivity indexes(1), the Koc for N-ethylmorpholine can be estimated to be about 12(SRC). According to a suggested classification scheme(2), this estimated Koc value suggests that N-ethylmorpholine has very high soil mobility(SRC). Insufficient data are available to predict the relative importance or rate of biodegradation in soil(SRC). Volatilization of N-ethylmorpholine is expected from dry soils(SRC) based on an experimental vapor pressure of 5 mm Hg(3,SRC), but not important from moist soils(SRC) based on an estimated Henry's Law constant of 2.74X10-8 atm-cu m/mole(4,SRC).

AQUATIC FATE: Based on a suggested classification scheme(2), N-Ethylmorpholine will be essentially non-volatile from water(SRC) based upon an estimated Henry's Law constant of 2.74X10-8 atm-cu m/mol(1,SRC). Insufficient data are available to predict the relative importance or rate of biodegradation in natural waters(SRC).

ATMOSPHERIC FATE: Based on an experimental vapor pressure of approximately 5 mm Hg at 25 °C(1), and a suggested classification scheme(2), N-ethylmorpholine will exist primarily in the vapor phase in the atmosphere(SRC). It will degrade in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of 2.5 hours(3,SRC). Removal of atmospheric N-ethylmorpholine may occur through wet deposition(SRC).

Exposure Routes · 2 Einträge

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms · 4 Einträge

Cough. Sore throat.

Redness.

Redness. Pain. Blurred vision.

irritation eyes, nose, throat; visual disturbance: corneal edema, blue-gray vision, colored haloes

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indexes(1), the Koc for N-ethylmorpholine can be estimated to be about 12(SRC). According to a suggested classification scheme(2), this estimated Koc value suggests that N-ethylmorpholine has very high soil mobility(SRC).

Human Toxicity Excerpts · 3 Einträge

... Ten humans exposed at 100 ppm N-ethylmorpholine for 2.5 min experienced irritation to the eyes, nose, and throat and olfactory fatigue. Irritation was slight with the same duration of exposure at 50 ppm and absent at 25 ppm.

Corneal edema was observed in workers exposed at 40 ppm and more N-ethylmorpholine for several hr. The lesions appeared near the end of the work shift and cleared within 3 to 4 hr after cessation of exposure. Other investigators have also reported that corneal edema caused by amine vapors is reversible. Distortion of vision is experienced at concn below those which produce eye or respiratory irritation. Another study reported that workers exposed at concn generally in the 3 to 4 ppm N-ethylmorpholine range, and never above 11 ppm, complained of drowsiness, optical halos, and foggy vision.

... An epidemic of neurogenic urinary retention from a company, employing 141 and 75 people at 2 different plants, manufacturing polyurethane foam products ... Abnormalities in vision, upper respiratory irritation, dermatitis, and pulmonary abnormalities also occurred but appeared to be related to the presence of other chemicals including N-ethylmorpholine and toluene diisocyanate.

Artificial Pollution SourcesN-Ethylmorpholine's use as an intermediate for dyestuffs, pharmaceuticals, rubber accelerators, and emulsifying agents(1) may result in its release to the environment through various waste streams(SRC).
Environmental BioconcentrationBecause it is miscible in water(2), bioconcentration in aquatic organisms is not expected to be an important fate process for N-ethylmorpholine(1,SRC).
Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for N-ethylmorpholine can be estimated to be 2.47X10-8 atm-cu m/mole(SRC) using a structure estimation method(1). This value of Henry's Law constant indicates that N-ethylmorpholine will be essentially non-volatile from water(2).

Non-Human Toxicity Excerpts · 4 Einträge

ALL /N-SUBSTITUTED MORPHOLINES TESTED INCLUDING N-ETHYL MORPHOLINE/ EXHIBITED A LOW DEGREE OF ORAL TOXICITY ... N-ETHYL DERIVATIVES PRESENT THE HIGHEST POTENTIAL HAZARD FROM VAPOR EXPOSURE ... .

TESTED IN LIQUID FORM BY APPLYING A DROP FULL-STRENGTH TO RABBIT'S EYE... CAUSES THE CORNEA TO BECOME HAZY IN ABOUT FIVE MINUTES & EPITHELIUM TO SLOUGH FROM THE SURFACE. STANDARDIZED TESTING & GRADING ON RABBIT EYES GIVES A GRADE 7 INJURY ON A SCALE OF 1 TO 10. /MOST SEVERE INJURIES ARE RATED 10/

A DIRECT MUTAGENIC EFFECT WAS FOUND WITH N-ETHYLMORPHOLINE IN MUTAGENICITY TESTS WITH SALMONELLA TYPHIMURIUM STRAINS TA1535 & TA100, WITH & WITHOUT METABOLIC ACTIVATION BY LIVER PREPN FROM SPRAGUE-DAWLEY RATS. TESTS INDICATE OCCURRENCE OF AN ALKYLATING IMPURITY IN N-ETHYLMORPHOLINE.

... 1 of 6 rats died after a 4-hr inhalation exposure at 2000 ppm.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of N-ethylmorpholine with photochemically produced hydroxyl radicals has been estimated to be approximately 1.49X10-10 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 2.5 hours at an atmospheric concentration of 5x10+5 hydroxyl radicals per cu cm(1,SRC).

Probable Routes of Human Exposure · 2 Einträge

...HAS PECULIARLY DISTURBING ACTION ON CORNEAL EPITHELIUM...CAUSING TRANSIENT EDEMA OF CORNEAL EPITHELIUM IN WORKERS EXPOSED TO 40 PPM OR MORE IN AIR DURING WORK DAY, CAUSING ONSET OF BLUE-GREY VISION OR COLORED HALOS AROUND LIGHTS A FEW HOURS AFTER EXPOSURE.

Occupational exposure to morpholines, such as N-ethylmorpholine, can occur through inhalation, dermal contact and ingestion(1).

Sicherheitsdaten

F
8-23
OEB
A
OEL
TWA: 5 ppm (23 mg/m3) [skin]
wgk
1
IDLA
100 ppm
tsca
TSCA listed
ridadr
UN 2920 8/PG 2
hs_code
29349990
RTECS-Nr.
QE4025000
risk_code
10-21/22-34
Toxizität
LD50 orally in Rabbit: 1640 mg/kg LD50 dermal Rabbit 900 mg/kg
hazard_code
C
safety_code
26-36/37/39-45-16
hazard_class
8
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
100-74-3(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 OralEye Dam. 1Flam. Liq. 3Skin Corr. 1B
Selbstentzündungstemperatur
160 °C

Darstellung

synthetischeN-Ethylmorpholine is synthesized by the reaction of morpholine with bromoethane.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

MorpholinDiethylenglykolBromethanAmmoniak, wasserfrei4-Ethylmorpholin-4-oxid2-Morpholinoethyl isocyanideα-Methyl-4-morpholineacetonitrileN-EthyldiethanolaminN-methyl ,ethyl-Morpholinium iodide

Nachgelagerte Produkte

Water quality stabilizerTrandolapril