112-84-5

Basic information

• Product Name: cis-13-Docosenoamide
• Synonyms: 13-Docosenamide,(Z)-;Armid E;cis-13-docosenamid;Crodamide E, ER;Erucic acid amide;erucicacidamide;Euracamide;Kemamide E
• CAS NO: 112-84-5
• Molecular Formula: C₂₂H₄₃NO
• Molecular Weight: 337.58
• EINECS: 204-009-2
• Product Categories: Amides;Chiral Compounds
• Mol File: 112-84-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 79-81 °C(lit.)
• Boiling Point: 473.86°C (rough estimate)
• Flash Point: 230 °C
• Appearance: solid
• Density: 0.9417 (rough estimate)
• Vapor Pressure: 3.69E-09mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Soluble in DMSO (up to at lease 40 mg/ml) or in Water (up to at least 25 mg/ml with warming)
• PKA: 16.61±0.40(Predicted)
• Water Solubility: PRACTICALLY INSOLUBLE
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: cis-13-Docosenoamide(CAS DataBase Reference)
• NIST Chemistry Reference: cis-13-Docosenoamide(112-84-5)
• EPA Substance Registry System: cis-13-Docosenoamide(112-84-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 1
• Hazardous Substances Data: 112-84-5(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 112-84-5 differently. You can refer to the following data:
1. Cis-13-Docosenoamide is also known as Erucamide or Erucylamide. It is in the form of white flakes or beads. It is soluble in isopropanol, slightly soluble in alcohol and acetone.1 In industry, cis-13-docosenoamide is used in the formulations of anti-adhesive agents, lubricants, and lubricant additives to reduce their friction coefficient and to make films easier to handle.2 It is used as a standard to determine fatty acid amides in polyethylene packaging film by GC/MS.3
2. 13-Docosenamide is the amide of docosenoic acid. It was first identified in the cerebrospinal fluid of sleep-deprived cats. It has also been detected in the cerebrospinal fluid of rats and humans. 13-Docosenamide causes reduced mobility and slightly lessened awareness in rats, whereas 9-octadecenamide induces physiological sleep.

Reference

B. van Lierop, L. Castle, A. Feigenbaum, A. Boenke, Spetra for the Identification of Additives in Food Packaging, 1998, ISBN 0-7923-4986-5 https://pubchem.ncbi.nlm.nih.gov/compound/Erucylamide#section=Use-and-Manufacturing https://www.sigmaaldrich.com/catalog/product/aldrich/280577?lang=de®ion=DE

Chemical Properties

Solid. Soluble in isopropanol; slightly soluble in alcohol and acetone. Combustible.

Uses

Different sources of media describe the Uses of 112-84-5 differently. You can refer to the following data:
1. 13-Docosenamide is the amide of docosenoic acid. It was first identified in the cerebrospinal fluid of sleep-deprived cats. It has also been detected in the cerebrospinal fluid of rats and humans. 13-Docosenamide causes reduced mobility and slightly lessened awareness in rats, whereas 9-octadecenamide induces physiological sleep.[Cayman Chemical]
2. Plastic additive 21 is a plasticizer; used in preparation of natural mineral modified degradable polymer flame-retardant composite material.

General Description

Erucamide is a migratory additive that is commonly placed in polyolefin films to reduce their coefficient of friction (COF), a good attribute for high speed packaging operations.

Flammability and Explosibility

Nonflammable

References

1) Li et al. (2017), Antidepressant and anxiolytic-like behavioral effects of erucamide, a bioactive fatty acid amide, involving the hypothalamus-pituitary-adrenal axis in mice; Neurosci. Lett. 640 6

InChI:InChI=1/C22H43NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h9-10H,2-8,11-21H2,1H3,(H2,23,24)/b10-9-

Synthetic route

cis-13-docosenoic acid (112-86-7) → Unislip 1753 (112-84-5)

Conditions	Yield
With ammonia; zircornium(IV) n-propoxide at 165℃; for 6h; Reagent/catalyst;	98.8%
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / Inert atmosphere 2: ammonium hydroxide View Scheme

erucic acid chloride (59044-32-5, 7459-29-2) → Unislip 1753 (112-84-5)

Conditions	Yield
With ammonium hydroxide

Unislip 1753 (112-84-5) → cis-docos-13-enylamine (26398-95-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 12h; Reflux;	100%

Unislip 1753 (112-84-5) → erucyl alcohol (629-98-1)

Conditions	Yield
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 18h; Inert atmosphere; chemoselective reaction;	94%

[hydroxy(tosyloxy)iodo]benzene (27126-76-7) + Unislip 1753 (112-84-5) → cis-12-heneicosenylammonium tosylate (116749-38-3)

Conditions	Yield
In acetonitrile at 65 - 70℃; for 0.0333333h;	63%

Unislip 1753 (112-84-5) → (3R)-N-{(3R,6R,9R,12S,15R,18S,19R)-6-(3-amino-3-oxopropyl)-15-[(2S)-butan-2-yl]-12-(4-hydroxybenzyl)-9-[(1R)-1-hydroxyethyl]-3,19-dimethyl-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentaazacyclononadecan-18-yl}-15-carbamimidamido-3-hydroxypentadecanamide

Conditions

Yield

Multi-step reaction with 9 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere 6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / -78 - 20 °C / Inert atmosphere 7.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; tert-butyl alcohol / 2 h / 20 °C 8.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h 8.2: 70 h / 20 °C 9.1: trifluoroacetic acid / dichloromethane; water / 1 h / 20 °C View Scheme

Unislip 1753 (112-84-5) → 9H-fluoren-9-ylmethyl (13Z)-docos-13-en-1-yl-carbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C View Scheme

Unislip 1753 (112-84-5) → 9H-fluoren-9-yl-methyl (13-hydroxyhexadec-15-en-1-yl)carbamate

Conditions

Yield

Multi-step reaction with 4 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C View Scheme

Unislip 1753 (112-84-5) → di-tert-butyl [(E)-{[13-(methoxymethoxy)hexadec-15-en-1-yl]amino}methylylidene]biscarbamate

Conditions

Yield

Multi-step reaction with 5 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere View Scheme

Unislip 1753 (112-84-5) → di-tert-butyl [(E)-{[13-(methoxymethoxy)-15-oxopentadecyl]amino}methylylidene]biscarbamate

Conditions

Yield

Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere 6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / -78 - 20 °C / Inert atmosphere View Scheme

Unislip 1753 (112-84-5) → di-tert-butyl [(E){[(13R)-15-({(3R,6R,9R,12S,15R,18S,19R)-6-(3-amino-3-oxopropyl)-15-[(2S)-butan-2-yl]-12-(4-hydroxybenzyl)-9-[(1R)-1-hydroxyethyl]-3,19-dimethyl-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentaazacyclononadecan-18-yl}amino)-13-(methoxymethoxy)-15-oxopentadecyl]amino}methylylidene]biscarbamate

Conditions

Yield

Multi-step reaction with 8 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere 6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / -78 - 20 °C / Inert atmosphere 7.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; tert-butyl alcohol / 2 h / 20 °C 8.1: 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h 8.2: 70 h / 20 °C View Scheme

Unislip 1753 (112-84-5) → 15-[N',N''-bis(tert-butoxycarbonyl)carbamimidamido]-3-(methoxymethoxy)pentadecanoic acid

Conditions

Yield

Multi-step reaction with 7 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere 4.1: (R,R)-(η5-cyclopentadienyl)chloro[(4R,trans)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato]titanium / tetrahydrofuran; diethyl ether / 4 h / 0 - 20 °C 4.2: 16 h / -78 - 20 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 13 h / 0 - 20 °C 5.2: 12 h / 20 °C 5.3: 120 h / Inert atmosphere 6.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / -78 - 20 °C / Inert atmosphere 7.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; tert-butyl alcohol / 2 h / 20 °C View Scheme

Unislip 1753 (112-84-5) → 9H-fluoren-9-yl-methyl (13-oxotridecyl)carbamate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 12 h / Reflux 2.1: sodium hydrogencarbonate / 1,4-dioxane; water / 14 h / 0 - 20 °C 3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 - 10 °C / Inert atmosphere View Scheme

Upstream product

• 59044-32-5 erucic acid chloride 
• 112-86-7 cis-13-docosenoic acid 

Downstream Products

• 629-98-1 erucyl alcohol 
• 26398-95-8 cis-docos-13-enylamine 
• 116749-38-3 cis-12-heneicosenylammonium tosylate 

Relevant articles and documents

Method and apparatus for manufacturing carboxylic acid amide compound

The present invention relates to a process and an apparatus for producing a carboxylic acid amide compound, and more particularly, to a process for producing a carboxylic acid amide compound which alternately performs a reaction process of a first manufacturing process that promotes the reaction between a first carboxylic acid and a first ammonia in the presence of a first catalyst and a reaction process of a second manufacturing process that promotes the reaction between a second carboxylic acid and a first ammonia in the presence of a second catalyst wherein each of them is progressed alternately between each preparation process so that the reaction between the carboxylic acid and the ammonia, which is intermittently carried out by the respective preparation processes, can be continuously performed, and moreover, the time required for the respective preparation processes is shortened, so that the carboxylic acid amide compound can be produced in a large amount in a short time.