818-57-5

Usage

Uses

Used in Chemical Synthesis:
METHYL 4-PENTENOATE is used as a chemical intermediate for the synthesis of various organic compounds. Its reactivity in amidation and metathesis reactions makes it a valuable component in the creation of complex molecules and materials.
Used in Polymerization Processes:
As a chain transfer agent, METHYL 4-PENTENOATE plays a crucial role in the polymerization of specific compounds, such as exo,exo-5,6-bis(methoxymethyl)-7-oxabicyclo[2.2.1]hept-2-ene. Its use in this capacity can influence the molecular weight and architecture of the resulting polymers, which can be tailored for specific applications.
Used in Fragrance Industry:
Given its medium strength odor, METHYL 4-PENTENOATE can be utilized in the fragrance industry as a component in creating various scent profiles. Its unique aroma can contribute to the development of distinct and appealing fragrances for a range of products.
Used in Research and Development:
Due to its unique chemical properties and reactivity, METHYL 4-PENTENOATE is also used in research and development settings. Scientists and chemists can explore its potential applications in new chemical reactions, material development, and other innovative uses that have yet to be discovered.

InChI:InChI=1/C6H10O2/c1-3-4-5-6(7)8-2/h3H,1,4-5H2,2H3

Upstream product

• 67-56-1 methanol 
• 21035-54-1 crotylamine 
• 201230-82-2 carbon monoxide 
• 74-85-1 ethene 
• 124-38-9 carbon dioxide 
• 106-99-0 buta-1,3-diene 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 25055-91-8 methyl 3-(3-methyldiazirin-3-yl)propanoate 
• 25055-86-1 3-(3-methyl-3H-diazirine-3-yl)propionic acid 
• 123-76-2 levulinic acid 
• 818-58-6 methyl (E)-pent-3-enoate 
• 74785-94-7 methyl 4-phenylselenylpentanoate 
• 627-91-8 adipic acid monomethyl ester 
• 5454-83-1 5-bromovaleric acid methyl ester 

Downstream Products

• 136061-61-5 5-Azido-4-phenylselanyl-pentanoic acid methyl ester 
• 13141-45-2 (Z)-1,4-diphenylbut-1-ene-3-yne 
• 13343-79-8 (E)-1,4-Diphenylbut-1-en-3-yne 
• 848653-50-9 5-(3-acetoxy-4-methoxy-phenyl)-4-hydroxy-pentanoic acid methyl ester 
• 21876-11-9 6-oxo-6-phenyl-hexanoic acid methyl ester 
• 15790-87-1 Methyl (E)-2-pentenoate 
• 624-24-8 methyl valerate 
• 526-55-6 2-(3-indole)-ethanol 
• 268232-21-9 methyl 5-{3-[2-(3-ethoxymethoxy-5-ethoxymethoxymethylphenyl)vinyl]phenyl}pentanoate 
• 1401831-95-5 C₁₄H₁₈O₄ 
• 80945-33-1 1-Methyl-1-(phenylsulfonyl)-5-hexen-2-one 
• 6654-36-0 methyl 6-oxohexanoate 

Relevant academic research and scientific papers

Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes

Dialkyldiazirines have emerged as reagents of choice for biological photoaffinity labeling studies. The mechanism of crosslinking has dramatic consequences for biological applications where instantaneous labeling is desirable, as carbene insertions display different chemoselectivity and are much faster than competing mechanisms involving diazo or ylide intermediates. Here, deuterium labeling and diazo compound trapping experiments are employed to demonstrate that both carbene and diazo mechanisms operate in the reactions of a dialkyldiazirine motif that is commonly utilized for biological applications. For the fraction of intermolecular labeling that does involve a carbene mechanism, direct insertion is not necessarily involved, as products derived from a carbonyl ylide are also observed. We demonstrate that a strained cycloalkyne can intercept diazo compound intermediates and serve as a bioorthogonal probe for studying the contribution of the diazonium mechanism of photoaffinity labeling on a model protein under aqueous conditions.

Nylon Intermediates from Bio-Based Levulinic Acid

Use of ZrO2/SiO2 as a solid acid catalyst in the ring-opening of biobased γ-valerolactone with methanol in the gas phase leads to mixtures of methyl 2-, 3-, and 4-pentenoate (MP) in over 95 % selectivity, containing a surprising 81 % of M4P. This process allows the application of a selective hydroformylation to this mixture to convert M4P into methyl 5-formyl-valerate (M5FV) with 90 % selectivity. The other isomers remain unreacted. Reductive amination of M5FV and ring-closure to ?-caprolactam in excellent yield had been reported before. The remaining mixture of 2- and 3-MP was subjected to an isomerising methoxycarbonylation to dimethyl adipate in 91 % yield.

Selective Production of Terminally Unsaturated Methyl Esters from Lactones Over Metal Oxide Catalysts

Metal oxide catalysts were studied for their selectivity for the production of a terminally unsaturated methyl ester, methyl 5-hexenoate (M5H), from a 6 carbon, 6-membered ring lactone, δ-hexalactone (DHL). A 15?wt% Cs/SiO2 catalyst had a selectivity of 55% to M5H. This selectivity was the highest of the metal oxide catalysts studied, which were Cs/SiO2, MgO, SrO, CeO2, ZrO2, Ta2O5, MgAl2O4, and a Mg–Zr mixed oxide. The Cs/SiO2 catalyst was utilized for the ring-opening of γ-valerolactone (GVL), a 5 carbon, 5-membered ring lactone. The catalyst was 88% selective to the terminally unsaturated methyl ester, methyl 4-pentenoate (M4P). Weight hourly space velocity studies determined that the unsaturated ester distributions remained constant and no C=C double bond isomerization occurred. Liquid phase transesterification reactions with DHL and methanol and nuclear magnetic resonance spectroscopy confirmed that DHL undergoes ring-opening transesterification to produce an?ω-1 hydroxy methyl ester, methyl 5-hydroxyhexanoate (M5HH). Liquid phase transesterification reactions and thermochemistry calculations established that the equilibrium for GVL transesterification with methanol was favored towards the ring-closed lactone instead of the ring-opened hydroxy ester because of the decreased ring strain of GVL compared to DHL. The difference in terminally unsaturated methyl ester selectivity between GVL and DHL manifests from the difference in ring-strain energy. DHL passes through the M5HH intermediate as a result of greater ring strain, while the production of M4P from GVL most likely occurs through a direct, concerted mechanism. Graphical Abstract: [Figure not available: see fulltext.].

METHOD FOR PRODUCING PENTENOIC ACID ESTER

PROBLEM TO BE SOLVED: To provide a production method capable of obtaining a pentenoic acid ester in high yield even without using a large amount of alcohol while suppressing by-production of an ether. SOLUTION: There is provided a method for producing a pentenoic acid ester, which comprises a step of synthesizing a pentenoic acid ester containing at least one selected from the group consisting of formulas (2), (3) and (4) by bringing γ-valerolactone and an alcohol of the formula (1) into contact with each other in the presence of a catalyst containing X type zeolite. [In the formula (1), R represents an alkyl group having 1 to 6 carbon atoms. In the formulas (2), (3) and (4), R represents an alkyl group having 1 to 6 carbon atoms]. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Efficient and sustainable transformation of gamma-valerolactone into nylon monomers

Herein, we reported the facile synthesis of dicarboxylic esters from biomass derived gamma-valerolactone (GVL) aiming for nylon monomer preparation via a novel synthetic route which improved the efficiency and overcame the need for toxic carbon monoxide for the synthesis of dicarboxylic esters from GVL.

Methyl 4-methoxypentanoate: A novel and potential downstream chemical of biomass derived gamma-valerolactone

Lignocellulosic derived gamma-valerolactone was effectively converted into methyl 4-methoxypentanoate, a potential liquid biofuel, solvent and fragrance, by the catalysis of a hydrogen exchanged ultra-stable Y zeolite (HUSY) and insoluble carbonates such as CaCO3. The catalytic competing generation process between methyl 4-methoxypentanoate and pentenoate esters was also analysed.

PROCESS TO PREPARE EPSILON-CAPROLACTAM

The invention is directed to a process to prepare ε-caprolactam and/or unsaturated ε-caprolactam from a pentenamide by contacting the pentenamide with a mixture of hydrogen and carbon monoxide in the presence of a solvent and a catalyst system comprising of a Group 8-10 metal and a phosphorus-donor ligand. The ligand may be a xantphos-type ligand.

PROCESS FOR THE PREPARATION OF FORMYLVALERIC ACID AND ADIPIC ACID

The invention relates to a process for the production of 5-formylvaleric acid and adipic acid or esters thereof from an isomeric mixture of pentenoic acid or esters thereof said mixture comprising at least 4-pentenoic acid or esters thereof, and further comprising 3-pentenoic acid and/or 2-pentenoic acid or esters thereof, theprocess comprising: (a) subjecting the isomeric mixture of pentenoic acid to a hydroformylation reaction comprising a hydroformylation catalyst which is non-isomerizing towards the pentenoic acid or esters thereof to obtain a mixture comprising 5-formylvaleric acid or esters thereof and further comprising 3-pentenoic acid and/or 2-pentenoic acid, or esters thereof; (b) separating the 3-pentenoic acid and/or 2-pentenoic acid, or esters thereof from the 5-formylvaleric acid or esters thereof; (c) subjecting the separated pentenoic acids or esters thereof to a carbonylation reaction comprising an isomerizing carbonylation catalyst to obtain adipic acid or esters thereof; (d) optionally isolating the adipic acid or ester thereof; and (e) optionally isolating the separated 5-formylvaleric acid or esters thereof. The process allows for efficient production of two different intermediates for producing polyamide using a single process, with good selectivity, little waste, in an economically efficient fashion. The process is very suitable to use an isomeric pentenoic acid mixture obtained from valerolactone, and can be used to produce renewable polyamide intermediates using a single process.

Ionic-liquid-catalyzed efficient transformation of γ-valerolactone to methyl 3-pentenoate under mild conditions

Green nylons! Acidic ionic-liquid catalysis for the transformation of g-valerolactone into methyl 3-pentenoate (M3P) is shown to be performed efficiently under mild conditions. M3P is obtained selectively from a reaction at 1708C for 3.5 h in the presence of an acidic ionic liquid that has a low vapor pressure, high thermal stability, and excellent catalytic performance. A possible reaction pathway for this conversion is also presented.

PROCESS TO PRODUCE ALKENOIC ACID ESTERS FROM LACTONES

This invention relates to a process for the preparation of alkenoic acid esters comprising contacting a lactone with an alcohol and an acidic heterogeneous catalyst, characterised in that the process is carried out in the presence of at least 20 ppm of an acid having a pKa of 5 or less, relative to the amount of the lactone. The presence of at least 20 ppm of an acid having a pKa of 5 or less may stabilise the catalyst during the reaction and may also be used for reactivating an acidic heterogeneous catalyst. The improved yield advantageously allows energy conservation.