Iodopropynyl butylcarbamate Chemical Properties

Melting point:

64-68 °C(lit.)

Boiling point:

321.8±25.0 °C(Predicted)

Density 

1.606±0.06 g/cm3(Predicted)

vapor pressure 

0.005Pa at 25℃

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

soluble in Methanol

form 

Solid

pka

12.03±0.46(Predicted)

color 

White to Almost white

Water Solubility 

168mg/L at 20℃

Merck 

14,5069

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

WYVVKGNFXHOCQV-UHFFFAOYSA-N

LogP

2.81 at 25℃

CAS DataBase Reference

55406-53-6(CAS DataBase Reference)

EPA Substance Registry System

3-Iodo-2-propynyl butylcarbamate (55406-53-6)

Safety Information

Hazard Codes 

N

Risk Statements 

50/53-50

Safety Statements 

60-61-29

RIDADR 

3077

WGK Germany 

3

RTECS 

EZ0950000

HazardClass 

9

PackingGroup 

III

HS Code 

29241990

Hazardous Substances Data

55406-53-6(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 1580 mg/kg; dermally in rabbit: >2000 mg/kg; LC50 (96 hr) in bluegill sunfish, rainbow trout, bobwhite quail: 1.12, 0.31, >7683 ppm; LC50 (8 day) in mallard duck: >7182 ppm (Hansen)

MSDS

• Language:English Provider:SigmaAldrich

Iodopropynyl butylcarbamate Usage And Synthesis

Description

Iodopropynyl butylcarbamate is a preservative that has been used as an industrial fungicide since the 1970s and more recently has been combined with formaldehydereleasing agents for use in cosmetics. The North American Contact Dermatitis Group patch tested with 0.1%iodopropynyl butylcarbamate in petrolatum and found 0.2% of their patch test clinic patients had positive reactions to this chemical. Most cosmetic applications appear to require less than 0.012% of this preservative.

Chemical Properties

Liquid

Uses

Glycacil(R) 2000 is used as a preservative in personal care formulations.

Uses

Glycacil(R) L is used as a preservative in personal care formulations.

Uses

Glycacil(R) S is used as a preservative in personal care formulations.

Uses

iodopropynyl butylcarbamate is a preservative with broad fungicidal activity used in skin care products. It is recommended for use in difficult formulation systems.

Uses

An antibacterial agent.

Uses

Fungicide; mildewcide; preservative in cosmetics, paints and coatings, metal working fluids; wood protection.

Application

1. Cosmetics 2. Wood preservatives 3. Paints 4. Metalworking fluids 5. Household products 6. Moistened toilet tissues 7. Contact lenses 8. Building materials 9. Cooling water 10. Adhesives 11. Textiles 12. Paper

Definition

ChEBI: A carbamate ester that is carbamic acid in which the nitrogen has been substituted by a butyl group and in which the hydrogen of the carboxy group is replaced by a 1-iodoprop-2-yn-3-yl group. A fungicide, it is used as a preservative and sapstain control c emical in wood products and as a preservative in adhesives, paints, latex paper coating, plastic, water-based inks, metal working fluids, textiles, and numerous consumer products.

General Description

Off-white solid.

Reactivity Profile

Iodopropynyl butylcarbamate is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Flammability and Explosibility

Not classified

Contact allergens

Iodopropynyl butylcarbamate has produced slight irritation in rabbits. However, it was not found to be either a skin sensitizer or a photo sensitizer in guinea pigs. Cosmetic formulations containing up to 0.125% of iodopropynyl butylcarbamate produce no significant irritation or sensitization reactions in human repeated insult patch tests. Iodopropynyl butylcarbamate did not cause crosssensitization reactions in patients who had demonstrated sensitivity to related dithiocarbamate compounds. In the European Union, it is approved as a preservative up to 0.05% and is not to be used in oral hygiene or lip care products. If the concentration exceeds 0.02% in leave-on products, a warning label must indicate that the product contains iodine.

Contact allergens

Iodopropynyl butylcarbamate (IPBC) is a broad-spec- trum preservative used for years because of its wide field of application, in polymer emulsions and pigment dispersions such as water-based paints and adhesives, cements and inks, as a wood preservative, in metal- working fluids, household products, and cosmetics. Allergic contact dermatitis to IPBC was reported due to cosmetics, from sanitary wipes, and in metalworkers.

Clinical Use

Iodopropynyl butylcarbamate (3-iodo-2-propynyl-butylcarbamate) is a highly effective fungicide as well as a bactericide. It was first used in the 1970s as a film fungicide for paint and then as a wood preservative, where final use concentration up to 4% was permitted. For paint and coatings usually no more than 0.5% iodopropynyl butylcarbamate is used. For metalworking fluids, adhesives, textiles, and paper, concentrations between 0.1%and 0.2% are common. The Cosmetic Ingredient Review Expert Panel concluded that iodopropynyl butylcarbamate is safe as a cosmetic ingredient in concentrations less than or equal to 0.1%and that it should not be used in products intended to be aerosolized. By 1996, iodopropynyl butylcarbamate was used in 122 formulations reported to the United States Food and Drug Administration. Iodopropynyl butylcarbamate is found in a wide variety of occupational and consumer products, including shampoos, lotions, powders, makeup, baby products, paints, coatings, metalworking fluids, household products, cooling water, building materials, and contact lenses. It is an irritant, although at low concentrations few problems have been reported.

Synthesis

1) 68kg of 3-propynyl-1-hydroxy-3-acrylate and 45kg of n-butylamine were accurately weighed in 150L of dimethoxydimethyl ether, mixed and transferred to three reactors. The reaction system was cooled to 0-5 °C and 16 kg of concentrated hydrochloric acid solution was slowly added dropwise. After the dropwise addition, the reaction temperature was raised to 120°C and maintained at this temperature for 12 hours. Upon completion of the reaction, the system was cooled to 5-10 °C, followed by the addition of 11 kg of sodium iodide. The reaction mixture was heated to 25-30°C and the reaction was continued for 24 hours. At the end of the reaction, the solvent was removed by distillation under reduced pressure and 800 mL of water was added to the residue and stirred for 30 minutes. The reaction mixture was filtered and the filter cake was dried to give a final 157 kg of iodopropynyl butylcarbamate. The yield was 91% as n-butylamine.

References

[1] Patent: CN107963983, 2018, A. Location in patent: Paragraph 0007; 0021-0024

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