53057-53-7

Basic information

• Product Name: 1,21-DOCOSADIENE
• Synonyms: 1,21-DOCOSADIENE;docosa-1,21-diene;1,21-DOCASADIENE);Einecs 258-333-4;1,21-Docosadiene, tech-95, contains isoMers
• CAS NO: 53057-53-7
• Molecular Formula: C₂₂H₄₂
• Molecular Weight: 306.56888
• EINECS: 258-333-4
• Mol File: 53057-53-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 31-33 °C
• Boiling Point: 162-164 °C/2 mmHg(lit.)
• Flash Point: 162.3 °C
• Appearance: /
• Density: 0.802 g/cm³
• Vapor Pressure: 1.28E-05mmHg at 25°C
• Refractive Index: 1.454
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,21-DOCOSADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,21-DOCOSADIENE(53057-53-7)
• EPA Substance Registry System: 1,21-DOCOSADIENE(53057-53-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 53057-53-7(Hazardous Substances Data)

Usage

General Description

1,21-Docosadiene, also known as Erucic acid, is a long-chain unsaturated hydrocarbon that belongs to the class of alkenes. It is a colorless, odorless liquid that is insoluble in water and highly flammable. 1,21-Docosadiene is commonly found in various natural sources such as certain vegetable oils, particularly rapeseed oil, and serves as a precursor for the synthesis of various industrial chemicals. It is also used in the production of plastics, lubricants, and surfactants. However, it has been linked to potential health concerns, as high levels of erucic acid consumption have been associated with heart damage in certain animal studies, leading to regulations on its presence in food products.

InChI:InChI=1/C22H42/c1-3-5-7-9-11-13-15-17-19-21-22-20-18-16-14-12-10-8-6-4-2/h3-4H,1-2,5-22H2

Upstream product

• 7766-50-9 1-undecen-11-ylbromide 
• 79186-26-8 12-hydroxydocosa-1,21-dien-11-one 
• 923-06-8 bromosuccinic acid 
• 925-90-6 ethylmagnesium bromide 
• 108712-21-6 10-undecenylmagnesium chloride 
• 5414-21-1 5-bromopentan-1-nitrile 
• 1119-46-6 5-chloro-valeric acid 
• 16696-65-4 1,11-dibromoundecane 
• 65921-65-5 5-iodopentyl acetate 
• 88476-93-1 10-undecen-1-ylmagnesium bromide 
• 2623-82-7 2-bromooctanoic acid 

Downstream Products

• 2424-92-2 octadecane-1,18-dicarboxylic acid 

Relevant articles and documents

Syntheses and palladium, platinum, and borane adducts of symmetrical trialkylphosphines with three terminal vinyl groups, P((CH2) mCH=CH2)3

Reactions of Br(CH2)mCH=CH2 with Mg powder and then PCl3 (0.33 equiv.) afford P((CH2)m-CH=CH 2)3 (1; m = a, 4; b, 5; c, 6; d, 7; e, 8; f, 9; 52-87 %). Reactions of 1a-c, e with PdX2(COD) (X = Cl, Br) give trans-PdX 2(P((CH2)mCH=CH2)3) 2 (35-92 %). Reactions of 1b-e with PtCl2 in benzene give mainly trans-PtCl2(P((CH2)mCH=CH 2)3)2 (trans-5b-e; 52-75 %), whereas those with K2PtCl4 in water give mainly cis-5b-e (33-70 %). The reaction of equimolar quantities of 1c and H3B.S(CH3) 2 gives the 1 : 1 adduct H3B·P((CH 2)6CH=CH2)3 (85 %). In none of these transformations are by-products derived from the C=C linkages observed.

Synthesis of ω-Unsaturated Acids

A short, high-yield method for the synthesis of ω-unsaturated acids have been developed that precludes any double-bond migration or hydrogenation.Key is the coupling reaction between Grignards of ω-unsaturated alkyl halides and the bromomagnesium salt of ω-bromo fatty acids.The reaction has been successfully extended to ω-bromo nitriles.The use of ω-chloro acids or α-bromo acids gives lower yields of heterocoupling products and substantial homocoupling.A catalyst study shows Li2CuCl4 to yield the most heterocoupling of several catalysts tried for the chloro acids, and Ni(II) or Cu(I) are best for the α-bromo acids.