871-70-5

Basic information

• Product Name: OCTADECANEDIOIC ACID
• Synonyms: 1,18-Octadecadioic acid;1,18-Octadecanedioic acid;Hexadecanedicarboxylic acid;1,16-HEXADECANEDICARBOXYLIC ACID;OCTADECANEDIOIC ACID;OCTADECANEDIOIC ACID 95+%;Octadecandisure;Octadecane-1,18-dicarboxylic acid
• CAS NO: 871-70-5
• Molecular Formula: C₁₈H₃₄O₄
• Molecular Weight: 314.46
• Product Categories: alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;canedioic acid
• Mol File: 871-70-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 125°C
• Boiling Point: 480.9 °C at 760 mmHg
• Flash Point: 258.8 °C
• Appearance: /Liquid
• Density: 0.998 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: within almost transparency in hot Methanol
• PKA: 4.48±0.10(Predicted)
• Water Solubility: 148.5μg/L at 25℃
• CAS DataBase Reference: OCTADECANEDIOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: OCTADECANEDIOIC ACID(871-70-5)
• EPA Substance Registry System: OCTADECANEDIOIC ACID(871-70-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24
• Hazardous Substances Data: 871-70-5(Hazardous Substances Data)

Usage

Uses

Octadecanedioic Acid is one of the fine particle pollutant emissions from the fireplace combustion of woods grown in Southern USA.

Definition

ChEBI: An alpha,omega-dicarboxylic acid that is octadecane in which both terminal methyl groups have been replaced by carboxy groups.

InChI:InChI=1S/C18H34O4/c19-17(20)15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(21)22/h1-16H2,(H,19,20)(H,21,22)

Synthetic route

9-heptadecenoic acid (10136-52-4) + carbon monoxide (201230-82-2) → octadecanedioic acid (871-70-5)

Conditions	Yield
With sulfuric acid; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; water; palladium(II) acetylacetonate; acetic acid at 20 - 100℃; under 30003 Torr; for 20h; Inert atmosphere; Autoclave;	99%

octadeca-7,11-dienedioic acid (1002-25-1) → octadecanedioic acid (871-70-5)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 40℃; for 12h; Solvent; Time;	99%

C26H42O8 (81393-30-8) → octadecanedioic acid (871-70-5)

Conditions	Yield
With hydrogenchloride In water Heating;	98%

dimethyl 1,18-octadecanedioate (1472-93-1) → octadecanedioic acid (871-70-5)

Conditions	Yield
With methanol; water; sodium hydroxide at 50℃; for 24h; Reagent/catalyst; Temperature;	92%
With sodium hydroxide In methanol
With water at 100 - 225℃; under 18617.8 Torr; for 8h; Temperature; Sealed tube; Inert atmosphere;

1,18-octadecanedioic acid monomethyl ester (72849-35-5) → octadecanedioic acid (871-70-5)

Conditions	Yield
With water; lithium hydroxide at 20℃; for 24h;	81%
(saponification);

eicosa-1,19-diene (14811-95-1) → octadecanedioic acid (871-70-5)

Conditions	Yield
With chromium(VI) oxide; acetic acid

1,14-dibromotetradecane (37688-96-3) + sodium diethylmalonate (996-82-7) → octadecanedioic acid (871-70-5)

Conditions	Yield
Beim Verseifen des Reaktionsprodukts und Erhitzen;

18-hydroxystearic acid (3155-42-8) → octadecanedioic acid (871-70-5)

Conditions	Yield
With potassium dichromate; sulfuric acid at 125℃;

dimethyl 1,18-octadecanedioate (1472-93-1) → octadecanedioic acid (871-70-5) + 1,18-octadecanedioic acid monomethyl ester (72849-35-5)

Conditions	Yield
With methanol; potassium hydroxide
With methanol; barium dihydroxide at 40 - 50℃;

5,14-dioxo-octadecanedioic acid (872824-69-6) → octadecanedioic acid (871-70-5)

Conditions	Yield
With sodium; hydrazine hydrate; ethylene glycol
With hydrogenchloride; amalgamated zinc; acetic acid
With sodium hydroxide; hydrazine hydrate; diethylene glycol

6,13-dioxo-octadecanedioic acid (109094-90-8) → octadecanedioic acid (871-70-5)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate; diethylene glycol at 200℃;

cyclooctadecanone (6907-37-5) → octadecanedioic acid (871-70-5)

Conditions	Yield
With chromium(VI) oxide; acetic acid

nonanoic acid (112-05-0) → octadecanedioic acid (871-70-5)

1,16-dicyanododecane (7735-45-7) → octadecanedioic acid (871-70-5)

Conditions	Yield
With sulfuric acid; acetic anhydride In water Heating;

octadec-7-ynedioic acid (102175-43-9) → octadecanedioic acid (871-70-5)

Conditions	Yield
With hydrogen; nickel
With hydrogen; platinum

Dihydroardisiaquinone A (21551-67-7) → octadecanedioic acid (871-70-5)

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide

β-Propiolactone (57-57-8) + 1,12-bis(bromomagnesio)dodecane → octadecanedioic acid (871-70-5)

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran at 0℃; for 3h;

C18H28O6(2-)*2Na(1+) → octadecanedioic acid (871-70-5)

Conditions	Yield
With potassium hydroxide; hydrazine hydrate 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h; Multistep reaction;

4-oxo-hexadecane-dicarboxylic acid-(1.16) → octadecanedioic acid (871-70-5)

Conditions	Yield
With hydrogenchloride; amalgamated zinc

potassium salt of sebacic acid monoethyl ester → octadecanedioic acid (871-70-5)

Conditions	Yield
With water at 50℃; Electrolysis.und Verseifen des entstehenden Diaethylesters durch siedende, ueberschuessige alkoholische Kalilauge;

Adipic acid (124-04-9) + disodium-salt of/the/ adipic acid → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / 1 h / 50 °C 2: 1.) triethylamine; 2.) 20percent HCl / 1.) chloroform, 35 deg C, 5 h; 2.) chloroform, reflux, 5 h 3: sodium hydroxide / ethanol / 1 h / Heating 4: 1.) hydrazine hydrate; 2.) potassium hydroxide / 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h View Scheme

1,6-Bis(2-oxocyclohexyl)-1,6-hexandion (14208-97-0) → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 1 h / Heating 2: 1.) hydrazine hydrate; 2.) potassium hydroxide / 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h View Scheme

Adipic acid dichloride (111-50-2) → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) triethylamine; 2.) 20percent HCl / 1.) chloroform, 35 deg C, 5 h; 2.) chloroform, reflux, 5 h 2: sodium hydroxide / ethanol / 1 h / Heating 3: 1.) hydrazine hydrate; 2.) potassium hydroxide / 1.) triethanolamine, 130 deg C; reflux, 4 h; 2.) triethanolamine, 200 deg C, 9 h View Scheme

sebacoyl chloride (111-19-3) → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: benzene / Hydrieren des Reaktionsprodukts an Palladium/Strontiumcarbonat in Butanon und erwaermen des Reaktionsgemisches. 2: aq.-ethanolic NaOH-solution 3: sodium hydroxide; diethylene glycol; hydrazine hydrate View Scheme
Multi-step reaction with 3 steps 1: benzene / Hydrieren des Reaktionsprodukts an Palladium/Strontiumcarbonat in Butanon; Erwaermen des Reaktionsgemisches. 2: aq.-ethanolic NaOH-solution 3: sodium hydroxide; diethylene glycol; hydrazine hydrate View Scheme

5,14-dioxo-octadecanedinitrile → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq.-ethanolic NaOH-solution 2: sodium hydroxide; diethylene glycol; hydrazine hydrate View Scheme

ethyl 6-chloro-6-oxohexanoate (1071-71-2) → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: benzene 2: aq. NaOH solution 3: hydrazine hydrate; potassium hydroxide; diethylene glycol / 200 °C View Scheme

N-methyladipinimide (25077-25-2) → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether / Erwaermen des Reaktionsprodukts mit Benzol 2: aqueous sulfuric acid 3: ethylene glycol; sodium; hydrazine hydrate View Scheme

1,14-tetradecanediol (19812-64-7) → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: HBr / 130 - 150 °C 2: Beim Verseifen des Reaktionsprodukts und Erhitzen View Scheme

1,13-dimethoxy-tetradecane → octadecanedioic acid (871-70-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: HBr / 130 - 150 °C 2: Beim Verseifen des Reaktionsprodukts und Erhitzen View Scheme

methanol (67-56-1) + octadecanedioic acid (871-70-5) → dimethyl 1,18-octadecanedioate (1472-93-1)

Conditions	Yield
With sulfuric acid for 16h; Reflux;	99%
With sulfuric acid for 2h; Heating;	97%
With sulfuric acid Reflux;	97%

octadecanedioic acid (871-70-5) → octadecane-1,18-diol (3155-43-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Reflux;	94%
Stage #1: octadecanedioic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 125h; Inert atmosphere; Reflux; Stage #2: With water; sodium hydroxide In tetrahydrofuran pH=Ca. 10; Inert atmosphere;	77%
Multi-step reaction with 2 steps 1: 97 percent / H2SO4 / 2 h / Heating 2: 82 percent / Red-Al / tetrahydrofuran / 3 h / 20 °C View Scheme

octadecanedioic acid (871-70-5) → Hexadecane (544-76-3) + carbon monoxide (201230-82-2)

Conditions	Yield
With hydrogen at 200℃; under 7500.75 Torr; for 24h; Microwave irradiation;	A 92% B n/a

octadecanedioic acid (871-70-5) + podofilox (518-28-5) → C62H74O18

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6h; Inert atmosphere;	88%

octadecanedioic acid (871-70-5) + benzyl alcohol (100-51-6) → 18-(benzyloxy)-18-oxooctadecanoic acid

Conditions	Yield
With sulfuric acid In toluene Reagent/catalyst; Reflux;	88%

octadecanedioic acid (871-70-5) + toluene-4-sulfonic acid (104-15-4) → 1,16-hexadecyldiammonium ditosylate

Conditions	Yield
Stage #1: octadecanedioic acid With sodium azide; sulfuric acid In chloroform at 50℃; for 2h; Schmidt Reaction; Stage #2: toluene-4-sulfonic acid	87%

octadecanedioic acid (871-70-5) → oxacyclononadecane-2,19-dione

Conditions	Yield
With acetic anhydride In dichloromethane at 20℃; for 3h;	77%

7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid + octadecanedioic acid (871-70-5) → C56H70F2N6O12 (1350462-78-0)

Conditions	Yield
Stage #1: octadecanedioic acid With caesium carbonate In N,N-dimethyl-formamide at 50℃; for 1h; Stage #2: 7-[4-(2-chloroacetyl) piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 50℃; for 72h;	70%

octadecanedioic acid (871-70-5) + taxol (33069-62-4) → C65H83NO17

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	60%

octadecanedioic acid (871-70-5) + C38H67N5O24 (1354944-97-0) → C94H164N10O50

Conditions	Yield
Stage #1: octadecanedioic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dimethyl sulfoxide for 0.166667h; Stage #2: C38H67N5O24 In dimethyl sulfoxide at 20℃; for 3h;	59%

octadecanedioic acid (871-70-5) + benzyl bromide (100-39-0) → 18-(benzyloxy)-18-oxooctadecanoic acid

Conditions	Yield
With potassium hydrogencarbonate In 2-methyltetrahydrofuran; water at 75℃; for 30h;	58.2%

octadecanedioic acid (871-70-5) + N,N-dimethylformamide di-tert-butyl acetal (36805-97-7) → 1,18-octadecanedioic acid mono-tert-butyl ester (843666-40-0)

Conditions	Yield
In toluene Concentration; Reflux;	57.4%
In n-heptane; dichloromethane; toluene

carbazitaxel (183133-96-2) + octadecanedioic acid (871-70-5) → C108H144N2O30

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 24h;	56.5%

octadecanedioic acid (871-70-5) + ciprofloxacin (85721-33-1) → C52H66F2N6O8 (1350462-72-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	53%

octadecanedioic acid (871-70-5) + (6aR)-O10-(3-aminopropyl)apomorphine dihydrochloride + trifluoroacetic acid (76-05-1) → N1,N18-bis(3-(6aR)-(apomorphin-O10-yl)propyl)octadecanediamide ditrifluoroacetate

Conditions	Yield
Stage #1: octadecanedioic acid; (6aR)-O10-(3-aminopropyl)apomorphine dihydrochloride With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: trifluoroacetic acid In water; acetonitrile	42%

triisopropylsilyl chloride (13154-24-0) + octadecanedioic acid (871-70-5) → octadecanedioic acid mono-triisopropylsilyl ester

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	41%
With triethylamine In N,N-dimethyl-formamide at 60℃; Inert atmosphere;	41%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + octadecanedioic acid (871-70-5) → N-(17-carboxyheptadecanoyloxy)-succinimide

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h;	40%

octadecanedioic acid (871-70-5) + 6-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine → 1,18-bis(4-(3-isopropyl-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-1H-indol-5-yl)piperidin-1-yl)octadecane-1,18-dione

Conditions	Yield
Stage #1: octadecanedioic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h; Stage #2: 6-(3-isopropyl-5-(piperidin-4-yl)-1H-indol-2-yl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine In N,N-dimethyl-formamide for 2h;	35.5%

octadecanedioic acid (871-70-5) + benzyl alcohol (100-51-6) → 18-(benzyloxy)-18-oxooctadecanoic acid + dibenzyl octadecanedioate

Conditions	Yield
Stage #1: octadecanedioic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; Stage #2: benzyl alcohol In tetrahydrofuran at 0 - 20℃; for 16h;	A 28% B 38 %Chromat.

diazomethane (186581-53-3, 908094-01-9) + octadecanedioic acid (871-70-5) → 9,10-dibromo-octadecanedioic acid dimethyl ester (23550-16-5)

p-cresol (106-44-5) + octadecanedioic acid (871-70-5) → octadecanedioic acid di-p-tolyl ester (119039-48-4)

Conditions	Yield
With naphthalene-2-sulfonate; xylene Entfernen des entstehenden H2O;

1,10-Decanediol (112-47-0) + octadecanedioic acid (871-70-5) → 1,12-dioxa-cyclotriacontane-13,30-dione

Conditions	Yield
at 200℃; under 2 Torr; Erhitzen des Reaktionsprodukts mit wenig Zinn(II)-chlorid-dihydrat unter 1 Torr auf 270grad;

Upstream product

• 1472-93-1 dimethyl 1,18-octadecanedioate 
• 6907-37-5 cyclooctadecanone 
• 123166-89-2 18-Hydroxyoctadeca-cis-9,trans-11,trans-13 trienoic acid 
• 1002-25-1 octadeca-7,11-dienedioic acid 
• 14811-95-1 eicosa-1,19-diene 
• 34450-18-5 17-octadecynoic acid 
• 19117-94-3 9,10-dibromooctadecanoic acid 
• 79912-54-2 ethyl dibromooleate 
• 112-79-8 Elaidic Acid 
• 6512-99-8 ethyl oleate 
• 41059-02-3 9-bromononanoic acid 
• 505-54-4 thapsic acid 
• 821-38-5 1,14-tetradecanedioic acid 
• 1931-63-1 methyl ester of azelaic acid aldehyde 

Downstream Products

• 1472-93-1 dimethyl 1,18-octadecanedioate 
• 3661-77-6 cycloheptadecanone 
• 103170-10-1 1,18-bis-(2,4-dihydroxy-phenyl)-octadecane-1,18-dione 
• 2380-32-7 methyl 17-oxooctadecanoate 
• 72849-35-5 1,18-octadecanedioic acid monomethyl ester 
• 1622913-88-5 bis{4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl} octadecanedioate 
• 119039-48-4 octadecanedioic acid di-p-tolyl ester 
• 189625-51-2 18-(benzyloxy)-18-oxooctadecanoic acid 
• 544-76-3 Hexadecane 
• 843666-40-0 1,18-octadecanedioic acid mono-tert-butyl ester 
• 1118767-15-9 17-(4-(S)-1-tert-butoxycarbonyl-3-{2-[2-({2-[2-(2,5-dioxopyrrolidin-1-yloxycarbonylmethoxy)ethoxy]ethylcarbamoyl}methoxy)ethoxy]ethylcarbamoyl}propylcarbamoyl)heptadecanoic acid tert-butyl ester 
• 201230-82-2 carbon monoxide 

Related news

Infrared study of adsorption in situ at the liquid-solid interface. V. Adsorption of octadecanol, octadecylamine, and OCTADECANEDIOIC ACID (cas 871-70-5) on silica, and a criterion for considering competitive adsorption07/16/2019

Infrared spectra were recorded in situ of octadecanol (A), octadecylamine (B), and octadecanedioic acid (C) adsorbed from CC14 solutions onto highly degassed silica. Adsorbed A interacted with silanols and caused a shift, ΔvOH, of the silanol band of ∼275 cm−1; the data suggest that A dimers i...detailed

Selective conversion of stearic acid into high-added value OCTADECANEDIOIC ACID (cas 871-70-5) using air and transition metal acetate bromide catalyst: Kinetics, pathway and process optimization07/13/2019

Liquid phase selective homogeneous catalytic oxidation of stearic acid (SA) was carried out to obtain industrially important carbon neutral high-added value octadecanedioic acid (ODDA). The oxidation was carried using air, cobalt(II)-acetate, manganese(II)-acetate and HBr catalyst in acetic acid...detailed

Relevant articles and documents

Method for synthesizing straight-chain octadecanedioic acid

The invention provides a method for synthesizing straight-chain octadecanedioic acid, which comprises the following steps of: carrying out double decomposition reaction on a compound shown in a formula (I) under the condition of a Grubbs catalyst to generate an unsaturated acid compound shown in a formula (II); and reducing the compound as shown in the formula (II) into a compound as shown in a formula (III) through palladium-carbon hydrogenation. The method disclosed by the invention is convenient to operate, simple in process, simple and easily available in raw materials and low in cost, and is suitable for small-scale preparation in a laboratory and industrial production.

Preparation method of long-chain aliphatic dicarboxylic acid mono-tert-butyl ester

The invention provides a method for obtaining the long-chain aliphatic dicarboxylic acid mono-tert-butyl ester through monohydrolysis of the long-chain aliphatic dicarboxylic acid di-tert-butyl ester by controlling the reaction conditions of monohydrolysis; and the raw material cost is low, the yield is high, the post-treatment method is simple, and the method is suitable for industrial production.

Preparation method of long-chain alkyl diacid mono-tert-butyl ester

The invention relates to a preparation method of long-chain alkyl diacid mono-tert-butyl ester, belonging to the technical field of organic synthesis. According to the invention, long-chain alkyl diacid is used as an initial raw material and reacts with oxalyl chloride to generate long-chain monoacyl chloride, and the long-chain monoacyl chloride and tert-butyl alcohol are subjected to an esterification reaction to generate the long-chain alkyl diacid mono-tert-butyl ester. According to the invention, a novel synthesis route is adopted, and raw material cost is reduced; and the method has the characteristics of mild reaction conditions, simple process operation, high product purity, high production efficiency and the like, and has good application prospects.