2104-19-0

Basic information

• Product Name: AZELAIC ACID MONOMETHYL ESTER
• Synonyms: NONANEDIOIC ACID MONOMETHYL ESTER;MONOMETHYL NONANEDIOATE;MONO-METHYL NONANEDIONATE;MONO-METHYL AZELATE;AZELAIC ACID MONOMETHYL ESTER;METHYL HYDROGEN AZELATE;8-METHOXYCARBONYLOCTANOIC ACID;8-Carbomethoxyoctanoic acid
• CAS NO: 2104-19-0
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.25
• EINECS: 218-275-2
• Product Categories: All Aliphatics;Aliphatics
• Mol File: 2104-19-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 22-24 °C(lit.)
• Boiling Point: 159-160 °C3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.045 g/mL at 20 °C(lit.)
• Vapor Pressure: 6.72E-05mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: Freezer
• Solubility: Chloroform, DMSO (Slightly), Methanol (Slightly)
• PKA: 4.77±0.10(Predicted)
• Water Solubility: Not miscible in water.
• BRN: 1775786
• CAS DataBase Reference: AZELAIC ACID MONOMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: AZELAIC ACID MONOMETHYL ESTER(2104-19-0)
• EPA Substance Registry System: AZELAIC ACID MONOMETHYL ESTER(2104-19-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2104-19-0(Hazardous Substances Data)

Usage

Chemical Properties

Low Melting Solid

Uses

Methyl hydrogen azelate is used as pharmaceutical intermediates.

InChI:InChI=1/C10H18O4/c1-14-10(13)8-6-4-2-3-5-7-9(11)12/h2-8H2,1H3,(H,11,12)

Synthetic route

Dimethyl azelate (1732-10-1) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With porcine liver esterase; sodium hydroxide; phosphate buffer for 6h;	97%
With barium dihydroxide In methanol 4 d, - 10 deg C; 10 h, RT;	85%
With barium dihydroxide In methanol Ambient temperature;	84%

methanol (67-56-1) + azelaic acid (123-99-9) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With sulfuric acid	92%

dimethyl 8,8'-(oxirane-2,3-diyl)dioctanoate (347308-58-1) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With dihydrogen peroxide; 3C8H17NO3S*3H(1+)*Mo12O40P(3-) In water at 85℃; for 8h; Temperature;	91.27%

methyl 9-[(tetrahydro-2H-pyran-2-yl)oxy]nonanoate (75949-34-7) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With jones reagent In acetone at 0℃;	79%

methanol (67-56-1) + azelaic acid (123-99-9) → Dimethyl azelate (1732-10-1) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With aluminum oxide at 25℃; for 48h; Green chemistry; chemoselective reaction;	A 9% B 73%
With sulfuric acid
With sulfuric acid at 120℃; for 3h;

Methyl oleate (112-62-9) → nonanoic acid (112-05-0) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With potassium permanganate; sodium periodate; potassium carbonate In water; tert-butyl alcohol for 66h;	A 64% B 40%
With potassium permanganate; sodium periodate; potassium carbonate In water; tert-butyl alcohol for 66h;	A 62% B 40%
With potassium permanganate; silica gel Yield given. Yields of byproduct given. Title compound not separated from byproducts;

diethyl azelate (624-17-9) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With methanol; potassium hydroxide; acetonitrile In diethyl ether at 0℃; for 50h;	62%

azelaic acid (123-99-9) + butanoic acid methyl ester (623-42-7) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With DOWEX 50W-X2 In Petroleum ether for 4h; Heating;	60%

stearolic acid methyl ester (1120-32-7) → azelaic monomethyl ester (2104-19-0) + 9,10-dioxooctadecanoic acid methyl ester (7108-68-1) + methyl 11-oxo-10-nitrooctadecanoate (113482-53-4) + methyl 10-oxo-11-nitrooctadecanoate (113482-54-5)

Conditions	Yield
With nitric acid; sodium nitrite In acetic acid	A 12% B 37% C 39% D n/a
With nitric acid; sodium nitrite In acetic acid other acetylenic fatty acid ester;	A 12% B 37% C 39% D n/a

methanol (67-56-1) + azelaic acid (123-99-9) + Dimethyl azelate (1732-10-1) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With hydrogenchloride; dibutyl ether
With hydrogenchloride In dibutyl ether Heating; 1.) 30 min, 2.) 2 h;	12.2 g

9-cis,11-trans,13-cis-octadecatrienoic acid (544-72-9) → methyl ester of azelaic acid aldehyde (1931-63-1) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
bei Ueberfuehrung in den Methylester und folgender Ozonspaltung;

Methyl oleate (112-62-9) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With acetic acid durch Zersetzung des Ozonids in Gegenwart von Wasserstoffperoxyd;

methyl ester of azelaic acid aldehyde (1931-63-1) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
oxydiert sich an der Luft;
an der Luft;

Methyl oleate (112-62-9) + acetic acid (64-19-7) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
bei der Ozonisierung und Zersetzung in Gegenwart von Wasserstoffperoxyd;

azelaic acid (123-99-9) + Dimethyl azelate (1732-10-1) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
In diethylene glycol dimethyl ether

diazomethane (186581-53-3, 908094-01-9) + azelaic acid (123-99-9) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With aluminum oxide In cyclohexane; N,N-dimethyl-formamide Product distribution; study of selectivity of methylation on alumina surface;

ozonide of ricinolic acid methyl ester → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With sodium carbonate

azelaic acid (123-99-9) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 46.6 g / H2SO4 / 2 h / Heating 2: 24.3 g / Ba(OH)2 / methanol / 20 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 70 percent / H2SO4 conc. / 10 h / Heating 2: 84 percent / Ba(OH)2*8H2O / methanol / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / Reflux 2: barium hydroxide octahydrate / methanol / 45 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / dichloromethane / Dean-Stark; Heating 2: barium(II) hydroxide / methanol / 12 h / 20 °C View Scheme

azelaic acid (123-99-9) + heptyloic acid → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / conc. H2SO4 2: 37 percent / Ba(OH)2*8H2O / methanol View Scheme

methyl 9-hydroxynonanoate (34957-73-8) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / PTSA / CH2Cl2 / 4 h / Ambient temperature 2: 79 percent / Jones reagent / acetone / 0 °C View Scheme

methyl 9,10-dihydroxy stearate (1115-01-1) + epoxidized methyl oleate (2566-91-8) → nonanoic acid (112-05-0) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; oxygen; sodium tungstate; cobalt(II) acetate In water at 75 - 80℃; for 5 - 6h; pH=3;
With oxygen; cobalt(II) chloride In water at 75 - 80℃; for 6h; Product distribution / selectivity;

Methyl oleate (112-62-9) → nonan-1-al (124-19-6) + nonanoic acid (112-05-0) + methyl ester of azelaic acid aldehyde (1931-63-1) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
Stage #1: Methyl oleate With ozone In water at 20℃; for 2h; Ionic liquid; Stage #2: With oxygen In water at 20℃; for 5h; Ionic liquid;	A 16 %Chromat. B 34 %Chromat. C 15 %Chromat. D 35 %Chromat.

Methyl oleate (112-62-9) → Octanoic acid (124-07-2) + nonanoic acid (112-05-0) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
Stage #1: Methyl oleate With dihydrogen peroxide; ortho-tungstic acid In water at 62℃; under 75.0075 - 150.015 Torr; Stage #2: With water; oxygen; cobalt(II) diacetate tetrahydrate at 60 - 62℃; under 16501.7 Torr; for 6h; Product distribution / selectivity;

Methyl oleate (112-62-9) → azelaic acid (123-99-9) + nonanoic acid (112-05-0) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
Stage #1: Methyl oleate With ozone In water; propionic acid for 1h; Stage #2: With dihydrogen peroxide; sulfuric acid In water; propionic acid at 100℃; for 1.25h;

Methyl oleate (112-62-9) → Octanoic acid (124-07-2) + nonanoic acid (112-05-0) + azelaic monomethyl ester (2104-19-0) + hexadecanoic acid methyl ester (112-39-0) + Methyl stearate (112-61-8)

Conditions	Yield
Stage #1: Methyl oleate With dihydrogen peroxide; ortho-tungstic acid In water at 62℃; under 75.0075 - 150.015 Torr; Industry scale; Stage #2: With oxygen; cobalt(II) diacetate tetrahydrate In water at 60℃; under 150.015 Torr; for 3.5h; Product distribution / selectivity;

methyl 9-decenoate (25601-41-6) → formic acid (64-18-6) + azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; water; dihydrogen peroxide In tert-butyl alcohol at 80℃; for 24h;	A n/a B 53 %Chromat.

Methyl oleate (112-62-9) → nonan-1-al (124-19-6) + nonanoic acid (112-05-0) + methyl ester of azelaic acid aldehyde (1931-63-1) + azelaic monomethyl ester (2104-19-0) + methyl 9,10-dihydroxy stearate (1115-01-1) + methyl 9(10)-hydroxy 10(9)-oxo octadecanoate (7297-29-2) + 10-hydroxy-9-ketostearic acid methyl ester (7108-21-6) + epoxidized methyl oleate (2566-91-8)

Conditions	Yield
With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; water; dihydrogen peroxide In tert-butyl alcohol at 80℃; for 24h; pH=2.92; Mechanism;

...Expand

Methyl oleate (112-62-9) → nonanoic acid (112-05-0) + azelaic monomethyl ester (2104-19-0) + 9,10-dioxooctadecanoic acid methyl ester (7108-68-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide; water / tert-butyl alcohol / 16 h / 40 °C / pH 2.9 2: ruthenium trichloride; dihydrogen peroxide / tert-butyl alcohol; water / 2.25 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide; water / tert-butyl alcohol / 24 h / 80 °C / pH 2.92 2: ruthenium trichloride; dihydrogen peroxide / tert-butyl alcohol; water / 2.25 h / 80 °C View Scheme
Multi-step reaction with 3 steps 1: tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide / tert-butyl alcohol; water / 16 h / 20 °C / pH 2.9 2: sulfuric acid; water / tert-butyl alcohol / 4 h / 80 °C / pH 2.4 3: ruthenium trichloride; dihydrogen peroxide / tert-butyl alcohol; water / 2.25 h / 80 °C View Scheme

azelaic monomethyl ester (2104-19-0) → methyl 9-hydroxynonanoate (34957-73-8)

Conditions	Yield
With borane-THF In tetrahydrofuran for 16h; Ambient temperature;	100%
With borane-THF In tetrahydrofuran at -18 - 20℃;	100%
With borane-THF In tetrahydrofuran at -20 - 20℃; for 4h;	99%

ethene (74-85-1) + azelaic monomethyl ester (2104-19-0) → 9-oxo-undec-10-enoic acid methyl ester (82120-15-8)

Conditions	Yield
With thionyl chloride; triethylamine; AlCl3 In dichloromethane	100%

azelaic monomethyl ester (2104-19-0) + dibenzylamine (103-49-1) → methyl 9-(dibenzylamino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	100%

azelaic monomethyl ester (2104-19-0) → 9-hydroxynonanoic acid (3788-56-5)

Conditions	Yield
With sodium tetrahydroborate; water In 1,4-dioxane at 25℃;	99%
Stage #1: azelaic monomethyl ester With sodium tetrahydroborate In 1,4-dioxane; water at 20℃; Stage #2: With hydrogenchloride; water In 1,4-dioxane at 0℃;

pyrrolidine (123-75-1) + azelaic monomethyl ester (2104-19-0) → methyl 9-oxo-9-(pyrrolidin-1-yl)nonanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	95%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	68%

azelaic monomethyl ester (2104-19-0) + 1-[4-(trifluoromethyl)phenyl]piperazine (30459-17-7) → methyl 9-oxo-9-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)nonanoate (1432445-32-3)

Conditions	Yield
Stage #1: azelaic monomethyl ester With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-[4-(trifluoromethyl)phenyl]piperazine In dichloromethane for 16h; Inert atmosphere;	98%
Stage #1: azelaic monomethyl ester With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: 1-[4-(trifluoromethyl)phenyl]piperazine In dichloromethane for 16h; Inert atmosphere;	98%

azelaic monomethyl ester (2104-19-0) + phenethylamine (64-04-0) → methyl 9-oxo-9-(phenethylamino)nonanoate

Conditions	Yield
Stage #1: azelaic monomethyl ester With fur-2-ylboronic acid In dichloromethane for 0.166667h; Molecular sieve; Inert atmosphere; Stage #2: phenethylamine In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;	98%

azelaic monomethyl ester (2104-19-0) + 3-α-acetoxy-4-β-amino-24-norurs-12-ene (108015-89-0) → methyl 9-((3-α-acetoxy-24-norurs-12-en-4-yl)amino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 16.5h;	95%

azelaic monomethyl ester (2104-19-0) + 4-methoxy-N-methylbenzylamine (702-24-9) → methyl 9-((4-methoxybenzyl)(methyl)amino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	95%

azelaic monomethyl ester (2104-19-0) → methyl 9-chloro-9-oxononanoate (56555-02-3)

Conditions	Yield
With thionyl chloride	94%
With oxalyl dichloride for 2h; Heating;	91%
With oxalyl dichloride In benzene for 2h; Reflux;	90%

diisobutylamine (110-96-3) + azelaic monomethyl ester (2104-19-0) → methyl 9-(diisobutylamino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	94%

3-α-o-acetoxy-4β-amino-11-oxo-24-norurs-12-ene (872090-58-9) + azelaic monomethyl ester (2104-19-0) → methyl 9-((3-α-acetoxy-11-oxo-24-norurs-12-en-4-yl)amino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 0 - 20℃; for 16.5h;	93%

azelaic monomethyl ester (2104-19-0) + (S)-Methyl mandelate (21210-43-5) → (S)-(+)-(Methoxycarbonyl)benzyl methyl 1,9-nonanedioate (111975-73-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	88%

azelaic monomethyl ester (2104-19-0) → methyl 8-bromooctanoate (26825-92-3)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; potassium bromide at 25℃; Irradiation;	88%
With bromine; mercury(II) oxide In tetrachloromethane at 75℃; for 2h;	33.4%

azelaic monomethyl ester (2104-19-0) + (2,4-bis(benzyloxy)-5-isopropylphenyl)(5-aminoisoindolin-2-yl)methanone (913000-10-9) → methyl 9-((2-(2,4-bis(benzyloxy)-5-isopropylbenzoyl)isoindolin-5-yl) amino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h;	86%

azelaic monomethyl ester (2104-19-0) → (+/-)-8-Hydroxynonansaeure methylester (88785-23-3)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at -20 - 20℃;	85%

azelaic monomethyl ester (2104-19-0) → oct-7-enoic acid methyl ester (15766-90-2)

Conditions	Yield
With acridine; chloropyridinecobaloxime(III) In dichloromethane; acetonitrile at 25 - 27℃; for 36h; Irradiation;	83%
With lead(IV) acetate; copper diacetate In pyridine; benzene for 2h; Heating;	80%
With lead(IV) acetate

azelaic monomethyl ester (2104-19-0) + triisopropylsilyloxymethyl(dodecyl)sulfane (1332721-91-1) → triisopropylsiloxymethyl methyl nonanedioate

Conditions	Yield
With triethylamine; copper(I) bromide In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere; Molecular sieve;	83%

azelaic monomethyl ester (2104-19-0) → methyl ester of azelaic acid aldehyde (1931-63-1)

Conditions	Yield
Stage #1: azelaic monomethyl ester With borane-THF In tetrahydrofuran at -18 - 20℃; for 4.5h; Stage #2: With pyridinium chlorochromate In dichloromethane at 20℃; for 4h; Inert atmosphere;	82%
With dihydrogen peroxide; tetrabutylammonium borohydride 1.) CHCl3, reflux, 5 h, 2.) H2O; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: B2H6 / tetrahydrofuran 2: (COCl)2; DMSO; Et3N View Scheme

azelaic monomethyl ester (2104-19-0) → methyl octanate (111-11-5) + oct-7-enoic acid methyl ester (15766-90-2) + dimethyl hexadecanedioate (19102-90-0)

Conditions	Yield
With potassium hydroxide In methanol at 45℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 220 mA cm-2; current consumption: 1.4 F mol-1; cell voltage 20 V; Yield given;	A n/a B n/a C 80%
With potassium hydroxide In methanol at 45℃; electrolysis: anode: platinum foil; current source: galvanostat; current density 220 mA cm-2; current consumption: 1.4 F mol-1; cell voltage 20 V; Yields of byproduct given;	A n/a B n/a C 80%

azelaic monomethyl ester (2104-19-0) + O-tritylhydroxylamine (31938-11-1) → 8-trityloxycarbamoyloctanoic acid methyl ester (1019683-19-2)

Conditions	Yield
Stage #1: azelaic monomethyl ester With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -15℃; for 0.166667h; Stage #2: O-tritylhydroxylamine In tetrahydrofuran at -15 - 20℃; Further stages.;	80%

azelaic monomethyl ester (2104-19-0) + (R)-1-benzyl-3-aminopyrrolidine (114715-39-8) → (R)-methyl 9-((1-benzylpyrrolidin-3-yl)amino)-9-oxononanoate

Conditions	Yield
With boric acid In toluene for 3h; Molecular sieve; Inert atmosphere; Reflux; chemoselective reaction;	80%

azelaic monomethyl ester (2104-19-0) + (3S)-1-benzyl-3-pyrrolidinamine (114715-38-7) → (S)-methyl 9-((1-benzylpyrrolidin-3-yl)amino)-9-oxononanoate

Conditions	Yield
With boric acid In toluene for 3h; Molecular sieve; Inert atmosphere; Reflux; chemoselective reaction;	80%

N-methyl-N-allylamine (627-37-2) + azelaic monomethyl ester (2104-19-0) → methyl 9-(allyl(methyl)amino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	80%

azelaic monomethyl ester (2104-19-0) + 1,4-phenylenediamine (106-50-3) → methyl 9-((4-aminophenyl)amino)-9-oxononanoate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	80%

11-bromoundecanoic acid (2834-05-1) + azelaic monomethyl ester (2104-19-0) → 1,20-dibromoeicosane (14296-16-3) + 18-Bromooctadecansaeure-methylester (83483-69-6)

Conditions	Yield
In methanol at 20℃;	A 54% B 79%

Upstream product

• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 186581-53-3 diazomethane 
• 123-99-9 azelaic acid 
• 67-56-1 methanol 
• 1732-10-1 Dimethyl azelate 
• 624-17-9 diethyl azelate 
• 1120-32-7 stearolic acid methyl ester 
• 75949-34-7 methyl 9-[(tetrahydro-2H-pyran-2-yl)oxy]nonanoate 
• 623-42-7 butanoic acid methyl ester 
• 1115-01-1 (threo)-9,10-dihydroxyoctadecanoic acid methyl ester 
• 347308-58-1 dimethyl 8,8'-(oxirane-2,3-diyl)dioctanoate 
• 112-80-1 cis-Octadecenoic acid 
• 7108-21-6 10-hydroxy-9-ketostearic acid methyl ester 
• 112-62-9 Methyl oleate 

Downstream Products

• 1002-84-2 palmitic acid 
• 506-12-7 heptadecanoic acid 
• 112-05-0 nonanoic acid 
• 19102-90-0 dimethyl hexadecanedioate 
• 638-53-9 tridecanoic acid 
• 25886-80-0 methyl 3'-carboxy-2',4',6'-triiodo-5'-(N-methylacetamido)azelanilate 
• 62358-96-7 Methyl-9-oxo-12-phenylthiododecanat 
• 2575-07-7 methyl 9-oxodecanoate 
• 164472-89-3 8-[(S)-4-({Amino-[(E)-4-methoxy-2,3,6-trimethyl-benzenesulfonylimino]-methyl}-amino)-1-((S)-1-diethoxymethyl-3-methyl-butylcarbamoyl)-butylcarbamoyl]-octanoic acid methyl ester 
• 111-11-5 methyl octanate 
• 15766-90-2 oct-7-enoic acid methyl ester 
• 1931-63-1 methyl ester of azelaic acid aldehyde 
• 852619-53-5 8-phenylcarbamoyl-octanoic acid methyl ester 
• 885701-90-6 8-(1H-2-indolyl)-N-(o-methylphenyl)octanoylamide 

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Biobased Aldehydes from Fatty Epoxides through Thermal Cleavage of β-Hydroxy Hydroperoxides**

The ring-opening of epoxidized methyl oleate by aqueous H2O2 has been studied using tungsten and molybdenum catalysts to form the corresponding fatty β-hydroxy hydroperoxides. It was found that tungstic acid and phosphotungstic acid gave the highest selectivities (92–93 %) towards the formation of the desired products, thus limiting the formation of the corresponding fatty 1,2-diols. The optimized conditions were applied to a range of fatty epoxides to give the corresponding fatty β-hydroxy hydroperoxides with 30–80 % isolated yields (8 examples). These species were fully characterized by 1H and 13C NMR spectroscopy and HPLC-HRMS, and their stability was studied by differential scanning calorimetry. The thermal cleavage of the β-hydroxy hydroperoxide derived from methyl oleate was studied both in batch and flow conditions. It was found that the thermal cleavage in flow conditions gave the highest selectivity towards the formation of aldehydes with limited amounts of byproducts. The aldehydes were both formed with 68 % GC yield, and nonanal and methyl 9-oxononanoate were isolated with 57 and 55 % yield, respectively. Advantageously, the overall process does not require large excess of H2O2 and only generates water as a byproduct.

Synthesis of Branched Biolubricant Base Oil from Oleic Acid

The mature manufacturing of synthetic lubricants (poly-α-olefins, PAO) proceeds through oligomerization, polymerization, and hydrogenation reactions of petrochemical ethylene. In this work, we utilize the inexpensive bio-derived oleic acid as raw material to synthesize a crotch-type C45 biolubricant base oil via a full-carbon chain synthesis without carbon loss. It contains several cascade chemical processes: oxidation of oleic acid to azelaic acid (further esterification to dimethyl azelate) and nonanoic acid (both C9 chains). The latter is then selectively hydrogenated to nonanol and brominated to the bromo-Grignard reagent. In a next step, a C45 biolubricant base oil is formed by nucleophilic addition (NPA) of excessive C9 bromo-Grignard reagent with dimethyl azelate, followed by subsequent hydrodeoxygenation. The specific properties of the prepared biolubricant base oil are almost equivalent to those of the commercial lubricant PAO6 (ExxonMobil). This process provides a new promising route for the production of value-added biolubricant base oils.