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Home > Encyclopedia > N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide

N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide

N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide structure

N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide 

structure
  • CAS No:

    2873-97-4

  • Formula:

    C9H15NO2

  • Chemical Name:

    N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide

  • Synonyms:

    2-Propenamide,N-(1,1-dimethyl-3-oxobutyl)-;Acrylamide,N-(1,1-dimethyl-3-oxobutyl)-;N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide;N-(1,1-Dimethyl-3-oxobutyl)acrylamide;Diacetone acrylamide;NSC 130565;Diacetonylacrylamide;Kohsylmer DAAM;19910-59-9;45002-23-1;56891-28-2;66251-70-5

  • Categories:

    Industrial Coatings  >  Coating Additive

Description

white to cream crystalline powder or flakes


Diacetone acrylamide appears as white crystals. (NTP, 1992)|DryPowder


Diacetone acrylamide appears as white crystals. (NTP, 1992)

N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide Basic Attributes

169.22100

169.22

220-713-2

3Z8J3430Z2

130565

DTXSID1024916

White crystalline solid

2924199090

Characteristics

46.17000

0.4

Diacetone acrylamide appears as white crystals. (NTP, 1992)

0.965g/cm3

57-58 °C

120 °C @ Press: 8 Torr

>110ºC

1.449

H2O: soluble ;soluble in chloroform

Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition so

0.000224mmHg at 25°C

LD50 orally in mice: 7.7 mmol/kg (Hashimoto)

Hygroscopic

Water soluble.

Amides and Imides

Polymerizable

DIACETONE ACRYLAMIDE forms polymers in solution, in bulk, or in emulsion. May react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with both acids and bases. May undergo autoxidation upon exposure to the air to form explosive peroxides.

Safety Information

NONH for all modes of transport

1

R22

S23; S24/25

AS3475000

Xn

50% NEUTRAL WATER SOLN IS STABLE @ PH 7.5-7.7 FOR UP TO 6 MO; HIGHLY REACTIVE VINYL MONOMER.

P264, P270, P301+P312, P330, P501

H302

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.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501|Aggregated GHS information provided by 320 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501

A fire in your laboratory involving this chemical should be extinguished with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. RECOMMENDED GLOVE MATERIALS: Permeation data indicate that butyl rubber gloves may provide protection to contact with this compound. Butyl rubber over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)

Toxicity

LD50 Rat oral 1770 mg/kg|LD50 Mouse oral 1303 mg/kg

Drug Information

ACUTE/CHRONIC HAZARDS: Toxic. Irritant. Flammable. Hazardous decomposition products. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

DAAm compound

N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide Use and Manufacturing

Methods of Manufacturing

Under argon protection, 11.2 g of acetic anhydride and 25.6 g were addedN - (2-methyl-4-oxapentan-2-yl) -3-morpholinopropionamideThe raw material is mixed with 250 ml of toluene, and the temperature is slowly increased from room temperature to 60 to 80 DEG C and stirred for 2 hours. After stirringMix and then add 0.2 g inhibitor BHT and 0.1 g cuprous chloride and 10.8 g triethylamine, and gradually warmed to reflux reactionNight, the reaction system was concentrated under reduced pressure to give the crude product which was directly separated by silica gel column chromatography with hexane-ethyl acetate14.1 grams of purified pure acrylamide (85percent yield) and 9.8 grams of pure N-acetylmorpholine (76percent yield).EXAMPLE 1Use of a Spiral Heat-Exchanger for the First Residence Time UnitA reaction solution with a stoichiometric molar ratio of acrylonitrile (AN) to diacetone alcohol (DiAOH) to HEXAMPLES 2-6Execution was analogous to example 1. Table 1 shows starting materials used, residence times, temperatures, and yields:; EXAMPLE 1Use of a Spiral Heat-Exchanger for the First Residence Time UnitA reaction solution with a stoichiometric molar ratio of acrylonitrile (AN) to diacetone alcohol (DiAOH) to H

Uses

Important vinyl monomer. The homopolymer produced by polymerization is insoluble in water, but has ~~"water respiration~~". The water absorption rate can reach 20-25% of the resin~"s own weight, and when the ambient humidity is lower than 60%, the moisture absorbed by the polymer is released again. The moisture acts as a plasticizer for the polymer. Using this peculiar nature, a variety of applications can be developed. (1) Resins for perm with good moisture resistance Japan uses it for resins for perm with moisture resistance. The hairstyle is kept for a long time, and it is not deformed by rain and rinse. (2) Photosensitive resin This product is used as a part of the raw material of photosensitive resin, which can have the following characteristics: fast photosensitive speed; easy removal of non-image parts after exposure can obtain clear images; can obtain good strength, solvent resistance and water resistance Layout. In addition, it can also be used as a cross-linking agent for unsaturated polyester resins, a cross-linking agent for diallyl phthalate, a curing agent for epoxy resins, such as for ~~"water breathing~~" resin (contact glasses, prevent Glass fogging, ship bottom coatings, etc.), pressure-sensitive adhesives, adhesive modifiers, non-woven fabric adhesives, water-absorbing films, leather finishes and modifiers, paper strength enhancers, antistatic polymers, inks, etc. This product can be used in the production of water treatment agents, such as scale inhibitors, flocculants; temperature and salt resistance drilling fluid loss control agents, oil well cement fluid loss control agents and temperature and salt resistance polymer oil displacement agents. It can also be used in the modification of fiber materials, daily chemicals, printing, papermaking, electronics and photography, medicine and health.


Paint additives and coating additives not described by other categories


Personal care products

Production

1,000,000 - 10,000,000 lb|(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US

Purity 99+%

Paint and coating manufacturing|2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-: ACTIVE|Similar to acrylic esters in polymerization behavior. Forms high mol wt polymers in bulk, soln, or emulsion. Esp suitable for electropolymerization.

Computed Properties

Molecular Weight:169.22
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:169.110278721
Monoisotopic Mass:169.110278721
Topological Polar Surface Area:46.2
Heavy Atom Count:12
Complexity:207
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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