79-41-4

Basic information

• Product Name: 2-Methyl-2-propenoic acid
• Synonyms: Methacrylicacid (8CI);2-Methyl-2-propenoic acid;2-Methylacrylic acid;Acryester MAA;GE110;Light Ester A;Loctite 3298;MAA;NSC 7393;NorsocrylMAA;a-Methacrylic acid;a-Methylacrylic acid;α-Methylacrylic acid
• CAS NO: 79-41-4
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.08924
• EINECS: 201-204-4
• Mol File: 79-41-4.mol
• Article Data: 246

Chemical Properties

• Melting Point: 16℃
• Boiling Point: 160.499 °C at 760 mmHg
• Flash Point: 74.172 °C
• Appearance: colourless liquid or crystals with an unpleasant odour
• Density: 1.015 g/cm³
• Refractive Index: 1.4295-1.4315
• PKA: 4.58±0.11(Predicted)
• Water Solubility: 9.7 g/100 mL (20℃)
• CAS DataBase Reference: 2-Methyl-2-propenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-2-propenoic acid(79-41-4)
• EPA Substance Registry System: 2-Methyl-2-propenoic acid(79-41-4)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R21/22:; R35:
• Safety Statements: S26:; S36/37/39:; S45:
• RIDADR: 2531 (stabilized)
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 79-41-4(Hazardous Substances Data)

Usage

General Description

2-Methyl-2-propenoic acid is a colorless liquid compound with a pungent odor. It is also known by its common name, tiglic acid. This chemical is a carboxylic acid with the molecular formula C5H8O2. It is primarily used in the manufacturing of fragrances, flavorings, and pharmaceuticals. 2-Methyl-2-propenoic acid is also a key intermediate in the synthesis of various organic compounds. Additionally, it can be found in certain plant and vegetable sources, including the oil of Lapsana communis and croton oil. Its reactivity and ability to form esters and amides make it a versatile compound in organic chemistry and industrial applications.

InChI:InChI=1/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)

Synthetic route

methacrylonitrile (126-98-7) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With potassium phosphate buffer at 30℃; for 16h; Rhodococcus sp. AJ270 cells;	98%
With bradyrhizobium species BTAi1 (A5EKU8); water Reagent/catalyst; Enzymatic reaction;

4-Fluorophenol (371-41-5) + 1,1,1-trichloro-2-methyl-2-propanol (57-15-8) → poly(methacrylic acid) (79-41-4) + 2-(4-fluorophenoxy)-2-methylpropanoic acid (587-11-1)

Conditions	Yield
With sodium hydroxide In acetone for 16h; Ambient temperature;	A n/a B 88%

2-bromoprop-1-ene (557-93-7) + carbon dioxide (124-38-9) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
Stage #1: 2-bromoprop-1-ene With magnesium In tetrahydrofuran at 20℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran at -70 - 20℃; under 750.075 Torr; Stage #3: With hydrogenchloride; ammonium chloride Product distribution / selectivity; more than 3 stages;	87%
Stage #1: 2-bromoprop-1-ene; carbon dioxide With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide In water; toluene at 95℃; under 750.075 Torr; for 2h; Stage #2: With hydrogenchloride In water pH=< 7; Product distribution / selectivity;	60%

2-(1-benzyl-4-methyl-1H-pyrazol-3-yloxy)-2-methyl-propionic acid (68430-08-0) → poly(methacrylic acid) (79-41-4) + 1-benzyl-4-methyl-1,2-dihydro-pyrazol-3-one (53409-18-0)

Conditions	Yield
at 150℃; for 5h;	A n/a B 85.1%

2-(1-benzyl-4-chloro-1H-pyrazol-3-yloxy)-2-methyl-propionic acid (68429-96-9) → poly(methacrylic acid) (79-41-4) + 1-benzyl-4-chloro-3-hydroxy-1H-pyrazole

Conditions	Yield
Heating;	A n/a B 83.8%

1,3,5-Trioxan (110-88-3) + propionic acid (802294-64-0) → propene (187737-37-7) + poly(methacrylic acid) (79-41-4)

Conditions	Yield
V-Si-P ternary oxide at 300℃; Product distribution; other temperatures; other contact times; other concentrations of the educts; or with water vapor;	A n/a B 82%
V-Si-P ternary oxide at 300℃;	A n/a B 82%

(R)-(-)-citramalic acid (6236-10-8) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
sodium hydroxide In water at 300℃; under 262201 Torr; Product distribution / selectivity;	80.8%

2-(1-Benzyl-1H-pyrazol-3-yloxy)-2-methyl-propionic acid (62299-19-8) → poly(methacrylic acid) (79-41-4) + 1-benzyl-3-hydroxy-1H-pyrazole (21074-40-8)

Conditions	Yield
Heating;	A n/a B 80.2%

tert-butyl alcohol (75-65-0) → 2-methylpropenal (78-85-3) + poly(methacrylic acid) (79-41-4) + isobutene (115-11-7)

Conditions	Yield
With oxygen; silica-alumina In water at 355℃; Product distribution / selectivity;	A 78.4% B 1.9% C 1.1%
With oxygen; silica-alumina In water at 355℃; Product distribution / selectivity;	A 78.1% B 2.2% C 1%
With oxygen; 5% Pd/zirconia In water at 130℃; under 36003.6 Torr; Product distribution / selectivity; autoclave;
With oxygen; palladium on silica gel In water at 130℃; under 36003.6 Torr; Product distribution / selectivity; autoclave;

chloroform (67-66-3) + acetone (67-64-1) + 1-benzyl-4-methyl-1,2-dihydro-pyrazol-3-one (53409-18-0) → poly(methacrylic acid) (79-41-4) + 2-methyllactic acid (594-61-6) + 2-chloro-2-methylpropanoic acid (594-58-1) + 2-(1-benzyl-4-methyl-1H-pyrazol-3-yloxy)-2-methyl-propionic acid (68430-08-0)

Conditions	Yield
With sodium hydroxide at 49 - 54℃; Further byproducts given;	A 0.07 mol B 0.15 mol C n/a D 77.2%

2-methylpropenal (78-85-3) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With oxygen In water at 280 - 355℃; for 1h; Product distribution / selectivity;	77%
With potassium phosphate; oxygen; 4-methoxy-phenol; palladium 10% on activated carbon In water; acetic acid at 90℃; under 18751.9 - 26252.6 Torr; Product distribution / selectivity;	76.9%
With phosphoric acid; oxygen; 4-methoxy-phenol; palladium 10% on activated carbon In water; acetic acid at 90℃; under 18751.9 - 26252.6 Torr; Product distribution / selectivity;	74.1%

2-methylpropenal (78-85-3) + isobutene (115-11-7) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
	74.1%
	74.1%

methanol (67-56-1) + 1,1,1-trichloro-2-methyl-2-propanol (57-15-8) → poly(methacrylic acid) (79-41-4) + methacrylic acid methyl ester (80-62-6)

Conditions	Yield
at 200℃; Reagent/catalyst; Temperature; Inert atmosphere; Gas phase;	A 6.7% B 72.3%

methacryloyl anhydride (760-93-0) + phenylboronic acid (98-80-6) → poly(methacrylic acid) (79-41-4) + 2-methyl-1-phenylprop-2-en-1-one (769-60-8)

Conditions	Yield
With P(p-CH3OC6H4)3; palladium diacetate In tetrahydrofuran; water at 60℃; for 16h;	A n/a B 71%

1,1,1-trichloro-2-methyl-2-propanol (57-15-8) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With water In chloroform at 200℃; for 3h; Inert atmosphere; Gas phase;	70.1%
With zinc phosphate; water at 330℃;
With cuprous phosphate; water at 330℃;
With tin(IV) phosphate; water at 330℃;

3,3,6,6-Tetramethyl-1,4-dioxane-2,5-dione (6713-72-0) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
α-hydroxyisobutyric acid potassium salt In acetone at 225℃; under 760.051 Torr; for 4.16667h;	70%

2-bromo-2-methylpropionic acid (2052-01-9) + sodium ethanolate (141-52-6) → poly(methacrylic acid) (79-41-4) + 2-ethoxy-2-methyl-propanoic acid (15001-71-5)

Conditions	Yield
In ethanol	A 20% B 70%

isobutene (115-11-7) → 2-methylpropenal (78-85-3) + poly(methacrylic acid) (79-41-4) + acetic acid (64-19-7)

Conditions	Yield
With air; water; CoMoTeO at 425℃;	A 68.2% B 9% C 1%
With air; V-Mo-Te-O at 405℃;	A 59% B 6% C 3%
With air; water; CoMoTeO at 375℃; Product distribution; Thermodynamic data; direct catalytic oxidation; varying: temperatures: 300 to 450 deg C; reactant composition;	A 27.5% B 39.5% C 4%

isobutyric Acid (79-31-2) → propene (187737-37-7) + poly(methacrylic acid) (79-41-4) + acetone (67-64-1)

Conditions	Yield
With water; oxygen; phosphovanadomolybdic acid at 320℃; for 0.0001h; Product distribution; other catalysts with the general formula H4PMo(11-x)WxVO40 and various stoichiometric ratios of W : Mo; also with 25percent silica-supported catalysts;	A 13.8% B 68% C 15.8%
With iron(II) phosphate; oxygen at 400℃; under 760 Torr; for 0.000111111h; other compounds as 1-butene, crotonaldehyde, methacrylaldehyde, propionaldehyde, butyrylaldehyde, isibutyrylaldehyde, propionic acid, butyric acid; var. temp. and time;
With oxygen; K2HPMo12O40 at 266.85℃; for 8h; Kinetics; Further Variations:; time;

2-methylenesuccinic acid (97-65-4) → poly(methacrylic acid) (79-41-4) + citraconic acid (498-23-7) + Mesaconic acid (498-24-8)

Conditions	Yield
With 5% Pt/Al2O3; sodium hydroxide In water at 250℃; for 1h; Reagent/catalyst; Temperature; Inert atmosphere;	A 68% B n/a C n/a
With sodium hydroxide In water at 180℃; under 112511 Torr; for 0.241667h;	A 27.26 %Spectr. B 36.48 %Spectr. C 16.23 %Spectr.
With sodium hydroxide at 280℃; for 0.0583333h;	A 57.08 %Chromat. B 5.91 %Chromat. C 5.72 %Chromat.
With sodium hydroxide at 250℃; for 0.25h; Reagent/catalyst;

2-chloropropene (557-98-2) + carbon dioxide (124-38-9) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetraethylammonium iodide; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;	68%

2-methylenesuccinic acid (97-65-4) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With Pt/Al2O3; sodium hydroxide at 250℃; under 30003 Torr; for 1h; Reagent/catalyst; Temperature;	67.8%
With hydrogenchloride at 26.85℃; pH=0.8; Kinetics; Further Variations:; Temperatures; pH-values;
With dodecacarbonyl-triangulo-triruthenium In water at 240℃; under 5171.62 Torr; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Glovebox;
With hydrotalcite, calcined at 400 °C at 250℃; for 0.5h; Reagent/catalyst; Concentration; Time;

N-acetyl methacrylamide (44810-87-9) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With acetic acid; zinc(II) chloride at 180℃; for 3h;	60%

2-methylenesuccinic acid (97-65-4) → propene (187737-37-7) + poly(methacrylic acid) (79-41-4) + 2-methyllactic acid (594-61-6) + carbon dioxide (124-38-9) + 2-oxo-propionic acid (127-17-3) + acetone (67-64-1)

Conditions	Yield
With barium hexa-aluminate In water at 250℃; under 15001.5 Torr; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere;	A n/a B 50% C n/a D n/a E n/a F n/a

methacrylonitrile (126-98-7) → poly(methacrylic acid) (79-41-4) + Methacrylamide (79-39-0)

Conditions	Yield
With potassium phosphate buffer at 30℃; for 0.5h; Rhodococcus sp. AJ270 cells;	A 44.5% B 43.4%

citric acid (77-92-9) → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With Pt/Al2O3; sodium hydroxide at 250℃; under 30003 Torr; for 1h; Reagent/catalyst; Temperature;	34.5%
With sodium hydroxide at 250℃; for 1h; Catalytic behavior; Temperature; Reagent/catalyst;

isobutene (115-11-7) → poly(methacrylic acid) (79-41-4) + methacryloyl anhydride (760-93-0)

Conditions	Yield
With oxygen; silica gel; Te/Pd-containing-silica-supported catalyst In water; tert-butyl alcohol at 75℃; under 18001.8 - 36003.6 Torr; for 0.75h; Product distribution / selectivity; Autoclave;	A 34.2% B 17.5%

trans-PtH(OCOC(CH3)=CH2) (PCy3)2 → poly(methacrylic acid) (79-41-4)

Conditions	Yield
With carbon monoxide In dichloromethane for 24h; Ambient temperature;	29%

poly(methacrylic acid) (79-41-4) + 1-Decanol (112-30-1) → decyl methacrylate (3179-47-3)

Conditions	Yield
With sulfuric acid at 20℃; for 48h;	100%
With toluene-4-sulfonic acid for 3h; Heating; Fluorinert Fluid, Dean-Stark trap;	91.5%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;	70%
With sulfuric acid; benzene unter Entfernen des entstehenden Wassers;
With phosphoric acid; (p-tolueneslfonic acid, sulfosalicylic acid, resin KU-2x8); hydroquinone In toluene Heating;

poly(methacrylic acid) (79-41-4) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C22H18O11PS3(3-)*3Na(1+) (115524-87-3)

Conditions	Yield
In water	100%

poly(methacrylic acid) (79-41-4) + trisodium tris(3-sulfophenyl)phosphine (63995-70-0) → C22H17(2)HO11PS3(3-)*3Na(1+) (115524-88-4)

Conditions	Yield
With water-d2	100%

poly(methacrylic acid) (79-41-4) + sodium 3-(diphenylphosphanyl)benzenesulfonate (63995-75-5) → C22H20O5PS(1-)*Na(1+) (122865-79-6)

Conditions	Yield
In water	100%

poly(methacrylic acid) (79-41-4) + sodium 3-(diphenylphosphanyl)benzenesulfonate (63995-75-5) → C22H19(2)HO5PS(1-)*Na(1+) (122865-81-0)

Conditions	Yield
With water-d2	100%

poly(methacrylic acid) (79-41-4) + C69H16O3 → C73H20O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 10h; Ambient temperature;	100%

methoxy poly(n=25)ethylene glycol + poly(methacrylic acid) (79-41-4) → C55H108O27

Conditions	Yield
With 10H-phenothiazine; toluene-4-sulfonic acid In cyclohexane at 115℃; for 20h;	100%

poly(methacrylic acid) (79-41-4) + benzyltriphenylphosphonium chloride (1100-88-5) + phenylmethanethiol (100-53-8) → 3-benzylthio-2-methylpropanoic acid (106664-91-9)

Conditions	Yield
With sodium hydroxide; sodium bicarbonate	100%

poly(methacrylic acid) (79-41-4) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate-co-methacrylic acid), Mn = 21000, Mw = 56500, Mw/Mn = 2.690, MMA:MAA = 91:9; monomer(s): methacrylic acid; methyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol at 82℃; for 18h;	100%

poly(methacrylic acid) (79-41-4) + methacrylic acid methyl ester (80-62-6) → poly(methyl methacrylate-co-methacrylic acid), Mn = 21100, Mw = 52600, Mw/Mn = 2.493, MMA:MAA = 94:6; monomer(s): methacrylic acid; methyl methacrylate

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol at 82℃; for 18h;	100%

poly(methacrylic acid) (79-41-4) + cis-RuH2(PMe3)4 (134002-31-6, 76171-49-8) → [Ru{OC(O)CMe=CH2-k2O,O’}(PMe3)4]+[CH2=CMeCO2]- (402828-65-3)

Conditions	Yield
In methanol at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;	100%

poly(methacrylic acid) (79-41-4) + (S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) → (S)-1,1′-binaphthyl-2-2′-diyl dimetacrylate

Conditions	Yield
With phosphoric acid; trifluoroacetic anhydride In water at 20℃; for 0.25h;	100%

poly(methacrylic acid) (79-41-4) + 1,1'-bi-2-naphthol (602-09-5) → (±)-1,1′-binaphthyl-2-2′-diyl dimetacrylate (159701-51-6, 96499-45-5)

Conditions	Yield
With phosphoric acid; trifluoroacetic anhydride In water at 20℃; for 0.25h;	100%

poly(methacrylic acid) (79-41-4) + 2-(dimethylamino)ethyl methacrylate (2867-47-2) → methacrylic acid,2-dimethylaminoethyl methacrylate

Conditions	Yield
at 20℃; Cooling with ice; Large scale;	100%

poly(methacrylic acid) (79-41-4) + 1-bromo-4-tert-butylbenzene (3972-65-4) → C14H17O2(1-)*Na(1+)

Conditions	Yield
Stage #1: poly(methacrylic acid) With sodium carbonate In water Stage #2: With palladium dichloride Stage #3: 1-bromo-4-tert-butylbenzene With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In water at 130 - 135℃; under 9000.9 - 12001.2 Torr; for 2h; Autoclave; Inert atmosphere;	99.6%

poly(methacrylic acid) (79-41-4) → methacryloyl anhydride (760-93-0)

Conditions	Yield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 0.5h;	99%
With magnesium dimethacrylate; di-tert-butyl dicarbonate at 25℃; for 4h; Reagent/catalyst;	99%
With 10H-phenothiazine; trifluorormethanesulfonic acid; acetic anhydride at 95℃; Reagent/catalyst; Temperature;	95%

poly(methacrylic acid) (79-41-4) + benzyl alcohol (100-51-6) → benzyl methacrylate (2495-37-6)

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In benzene for 40h; Heating;	99%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	90%
toluene-4-sulfonic acid In benzene for 15h; Heating;	85%

poly(methacrylic acid) (79-41-4) + thioacetic acid (507-09-5) → 3-(acetylthio)-2-methylpropanoic acid (33325-40-5)

Conditions	Yield
In tetrahydrofuran Heating;	99%
With hydroquinone at 90℃; for 1h;	89.2%
In hexane for 5h; Reflux;	80%

poly(methacrylic acid) (79-41-4) + dimethyldioctadecylammonium bromide (3700-67-2) + anion ionexchange resin (Rexyn 201, hydroxide form) → dioctyldecyldimethylammonium methacrylate (7524-96-1)

Conditions	Yield
In methanol	99%

poly(methacrylic acid) (79-41-4) → Poly(methacrylic acid)

Conditions	Yield
With methyl 2-dimethylbismuthanyl-2-methylpropanoate; 2,2'-azobis(isobutyronitrile) In toluene at 60℃; for 20h; Product distribution / selectivity;	99%
With 2,2'-azobis(isobutyronitrile) In ethanol at 75℃; for 5h;	86%
With 2,2'-azobis(isobutyronitrile) In hexane at 69.85℃; for 2h;
With 2-propylbenzo[d][1,3,2]dioxaborole at 20℃;
Stage #1: poly(methacrylic acid) With ethyl cellulose; methyl cellulose; sodium hydroxide; polyoxyethylene(40)isooctylpheyl ether; N,N'-Methylenebisacrylamide In dichloromethane; chloroform; water pH=5 - 6; Stage #2: With 2,2’-azobis[2-(2-imidazolin)propane] dihydrochloride In dichloromethane; chloroform; water at 20 - 51℃; for 21.5833h;

poly(methacrylic acid) (79-41-4) + norbornene (498-66-8) → exo-methacrylic acid bicyclo[2.2.1]hept-2-yl ester

Conditions	Yield
iron(III) trifluoromethanesulfonate In dibutyl ether at 80℃; for 18h;	99%

poly(methacrylic acid) (79-41-4) + zirconium tetrapropoxide (23519-77-9) → [Zr6(OH)4O4(methacrylate)12]

Conditions	Yield
In propan-1-ol (argon); closed vessel, room temp., 1 d;	99%

methoxypolyethyleneglycol monomethylacrylate PEG550MA + poly(methacrylic acid) (79-41-4) → poly(methoxypolyethyleneglycol monomethacrylate-co-methacrylic acid)

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate) In ethanol; water at 75 - 80℃; for 8h;	99%

methoxypolyethyleneglycol monomethylacrylate PEG350MA + poly(methacrylic acid) (79-41-4) + 2-(dimethylamino)ethyl methacrylate (2867-47-2) → poly(methoxypolyethyleneglycol monomethacrylate-co-methacrylic acid-co-dimethylaminoethyl methacrylate)

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate) In ethanol; water at 75 - 80℃; for 8h;	99%

methoxy polyethylene glycol monomethacrylate + poly(methacrylic acid) (79-41-4) + 2-(dimethylamino)ethyl methacrylate (2867-47-2) → poly((methoxy(polyethylene glycol 350)monomethacrylate)-co-(methacrylic acid)-co-(dimethylaminoethyl methacrylate))

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate) In ethanol; water at 75 - 80℃; for 8h;	99%

titanium tetra-n-propoxide (3087-37-4) + yttrium tris(2-methoxyethoxide) + poly(methacrylic acid) (79-41-4) → Ti4Y2(μ3-O)4(μ2-methacrylate)12(μ1-methacrylate)2(methacrylic acid)2

Conditions	Yield
In propan-1-ol; 2-methoxy-ethanol (Ar), methacrylic acid added dropwise at room temp. to a stirred mixt. of Ti complex in propanol and Y complex in methoxyethanol (Ti/Y=18), reacted at room temp. for 8 d; separated, dried (vac.), elem. anal.;	99%

poly(methacrylic acid) (79-41-4) + zirconium tetrapropoxide (23519-77-9) → [Zr4O2(O2CC(CH3)CH2)12]

Conditions	Yield
In propan-1-ol (argon); closed vessel, room temp., 7 d;	99%

poly(methacrylic acid) (79-41-4) + cinnamyl chloride (2687-12-9) → (E)-(-)-1-phenylallyl methacrylate

Conditions	Yield
With C32H40N2O2PRu(1+)*F6P(1-); sodium carbonate In tetrahydrofuran at 25℃; for 4h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%

diglycidyl succinate (21739-14-0) + poly(methacrylic acid) (79-41-4) → C18H26O10

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 75℃; for 1h;	99%
With 1-n-butyl-3-methylimidazolim bromide In neat (no solvent) at 75℃; for 1h;	2 g

poly(methacrylic acid) (79-41-4) + 3-chlorophenylthiol (2037-31-2) → 7-chloro-3-methylthiochroman-4-one

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 110℃; for 0.0833333h; Microwave irradiation; Inert atmosphere; Sealed tube;	99%

Upstream product

• 814-78-8 3-Methyl-3-buten-2-one 
• 6386-71-6 isopropenyllithium 
• 15719-64-9 methylammonium carbonate 
• 600-00-0 ethyl 2-bromoisobutyrate 
• 78-85-3 2-methylpropenal 
• 3393-64-4 4-hydroxy-3-methyl-2-butanone 
• 2648-57-9 3,3-Dichloro-2-butanone 
• 594-58-1 2-chloro-2-methylpropanoic acid 
• 2052-01-9 2-bromo-2-methylpropionic acid 
• 16674-04-7 (R)-(+)-β-chloro-isobutyric acid 
• 56970-78-6 3-bromo-2-methylpropionic acid 
• 857345-56-3 dimethylaminomethyl-methyl-malonic acid 
• 42069-15-8 2-bromo-2-methylpropanoic anhydride 
• 876480-54-5 2,2,5-trimethyl-3-oxo-3λ⁴-thia-adipic acid 

Downstream Products

• 868-77-9 2-methyl-2-propenoic acid 2-hydroxyethyl ester 
• 10535-52-1 methacrylic acid tetrahydropyran-2-ylmethyl ester 
• 760-93-0 methacryloyl anhydride 
• 18351-62-7 β-(methoxy-phenyl-phosphinoyl)-isobutyric acid methyl ester 
• 26473-47-2 2-methyl-3-sulfanylpropanoic acid 
• 4245-37-8 vinyl methacrylate 
• 1011-87-6 2-Chloro-2-methyl-3-phenylpropanoic acid 
• 2157-01-9 n-octyl methacrylate 
• 97-63-2 methyl methacrylate 
• 109313-50-0 β-diethoxyphosphoryl-isobutyric acid propyl ester 
• 762-04-9 phosphonic acid diethyl ester 
• 97-90-5 EDMA 
• 10552-43-9 α,ω-bis(methacryloylethyleneglycol)phthalate 
• 2387-65-7 di(triethylene glycol)phthalate dimethacrylate 

Relevant articles and documents

Ni-Catalyzed enantioselective reductive arylcyanation/cyclization of: N -(2-iodo-aryl) acrylamide

A Ni/(S,S)-BDPP-catalyzed intramolecular Heck cyclization of N-(2-iodo-aryl) acrylamide with 2-methyl-2-phenylmalononitrile was developed to give oxindoles with good enantioselectivities. We found that utilizing such an electrophilic cyanation reagent cou

Ligand-controlled divergent dehydrogenative reactions of carboxylic acids via C–H activation

Dehydrogenative transformations of alkyl chains to alkenes through methylene carbon-hydrogen (C–H) activation remain a substantial challenge. We report two classes of pyridine-pyridone ligands that enable divergent dehydrogenation reactions through palladium-catalyzed b-methylene C–H activation of carboxylic acids, leading to the direct syntheses of a,b-unsaturated carboxylic acids or g-alkylidene butenolides. The directed nature of this pair of reactions allows chemoselective dehydrogenation of carboxylic acids in the presence of other enolizable functionalities such as ketones, providing chemoselectivity that is not possible by means of existing carbonyl desaturation protocols. Product inhibition is overcome through ligand-promoted preferential activation of C(sp3)–H bonds rather than C(sp2)–H bonds or a sequence of dehydrogenation and vinyl C–H alkynylation. The dehydrogenation reaction is compatible with molecular oxygen as the terminal oxidant.

High-performance 3D printing UV-curable resins derived from soybean oil and gallic acid

Developing sustainable 3D printing materials has attained intensive interest due to the rapid growth of the 3D printing industry and the concerns on depletion of fossil resources and environmental pollution. In this work, a novel biobased UV-curable oligomer (GMAESO) was firstly synthesized from epoxidized soybean oil (ESO) and gallic acid (GA) via a 'green' one pot method. The obtained biobased oligomer possessed a biobased content of 82.9%. By co-photopolymerization of the obtained oligomer with a hydroxyethyl methacrylate (HEMA) diluent, a series of UV-curable materials were prepared, and their properties as well as curing behaviors were investigated. Notably, the resulting GMAESO resins with high HEMA contents (50-60%) showed low viscosities (52-93 mPa s) and excellent thermal and mechanical properties (a Tg of 128-130 °C, Tp >430 °C, a tensile strength of 42.2-44.4 MPa, etc.) which were comparable or superior to a commercial product. Furthermore, the optimal resin (GMAESO with 50% HEMA) was used for digital light processing (DLP) 3D printing. The resin showed lower penetration depth (0.277 mm) than the commercial resin, thus different-structured objects with high resolution were successfully printed. In general, the developed bio-based UV-curable resins are very promising for application in the 3D printing industry.