59719-74-3

Usage

Uses

Used in Chemical Synthesis:
1,3-Cyclopentanediol is used as a key intermediate in the synthesis of various chemical compounds for different applications. It is particularly used in the synthesis of 1,3-cyclopentanediol bis(4-methylbenzenesulfonate) and β-hydroxy-substituted cyclic carbonyl compounds, which are important in the development of pharmaceuticals and other specialty chemicals.
Used in Chiral Analysis:
1,3-Cyclopentanediol is used as a chiral reference compound in the direct enantiomer resolution of diols without derivatization on a chiral polysiloxane by capillary gas chromatography. This application is crucial in the pharmaceutical industry for the separation and analysis of enantiomers, which can have different biological activities and effects.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,3-Cyclopentanediol is used as a building block for the development of new drugs and drug candidates. Its unique chemical structure allows for the creation of novel compounds with potential therapeutic applications.
Used in Specialty Chemicals:
1,3-Cyclopentanediol is also used in the production of specialty chemicals, such as additives, coatings, and polymers, where its unique properties can enhance the performance of the final product.

InChI:InChI=1/C5H10O2/c6-4-1-2-5(7)3-4/h4-7H,1-3H2/t4-,5-/m0/s1

Upstream product

• 16326-97-9 1,3-dihydroxycyclopentane 
• 98-00-0 (2-furyl)methyl alcohol 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 542-92-7 cyclopenta-1,3-diene 
• 3859-41-4 1,3-cyclopentadione 
• 98-01-1 furfural 
• 16326-98-0 (+/-)-trans-1,3-cyclopentanediol 

Downstream Products

• 76152-69-7 toluene-4-sulfonic acid 3-toluenesulfonyloxy-cyclopentyl ester 
• 3212-60-0 cyclopent-2-enol 
• 14320-38-8 cyclopent-3-enol 
• 77-73-6 endo-<2+4>-Dicyclopentadien 
• 16326-97-9 trans-1,3-cyclopentanediol 
• 905961-61-7 1-benzyloxyl-3-hydroxylcyclopentane 
• 110047-62-6 Cyclopentandiol-(1,3)-ditosylat 
• 862311-15-7 3-(4-[(3-hydroxycyclopentyl)oxy]phenyl)-2-methyl-4(3H)-quinazolinone 
• 874650-39-2 3-hydroxycyclopentyl 4-methylbenzenesulfonate 
• 908288-84-6 4-[(3-hydroxycyclopentyl)oxy]-benzonitrile 
• 247568-60-1 3-hydroxycyclopentyl benzoate 
• 1073136-13-6 (+/-)-cis/trans-3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}cyclopentanol 
• 1233361-16-4 2-{3-[5-(3-hydroxycyclopentyloxy)pyrimidin-2-yl]benzyl}-6-(1-methyl-1H-pyrazol-4-yl)-2H-pyridazin-3-one 
• 1417346-99-6 C₂₄H₃₁ClN₄O₅ 

Relevant academic research and scientific papers

Application of hierarchical pore molecular sieve in preparation process of cyclopentadiene and JP-10 aviation fuel

The invention relates to an application of a hierarchical pore molecular sieve in a the preparation process of cyclopentadiene and JP-10 aviation fuel. The hierarchical pore molecular sieve is one or two or more of an H-ZSM-5 molecular sieve, an H-beta molecular sieve, an H-Y molecular sieve, an H-USY molecular sieve, a La-Y molecular sieve and an H-MOR molecular sieve with a hierarchical pore structure, a sulfonated SBA-15 molecular sieve, a sulfonated MCM-41 molecular sieve, a sulfonated Ti-SBA-15 molecular sieve, a sulfonated MCM-41 molecular sieve, a sulfonated Zr-MCM-41 molecular sieve and a sulfonated Zr-SBA-15 molecular sieve; and the hierarchical pore structure comprises micropores and mesopores. The catalyst and the raw materials used in the method are cheap and easy to obtain, the preparation process is simple, and the hierarchical pore molecular sieve has high activity and selectivity for rearrangement reaction of furfuryl alcohol, hydrogenation reaction of hydroxyl cyclopentenone and dehydration reaction. The invention provides a cheap and efficient synthesis method for synthesizing the JP-10 aviation fuel from a lignocellulose-based platform compound furfuryl alcohol.

Chemoselective formation of cyclo-aliphatic and cyclo-olefinic 1,3-diolsviapressure hydrogenation of potentially biobased platform molecules using Kn?lker-type catalysts

The hydrogenative conversions of the biobased platform molecules 4-hydroxycyclopent-2-enone and cyclopentane-1,3-dione to their corresponding 1,3-diols are established using a pre-activated Kn?lker-type iron catalyst. The catalyst exhibits a high selectivity for ketone reduction, and does not induce dehydration. Moreover, by using different substituents of the ligand, thecis-transratio of the products can be affected substantially. A decent compatibility of this catalytic system with various structurally related substrates is demonstrated.

SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES

Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

Making JP-10 Superfuel Affordable with a Lignocellulosic Platform Compound

The synthesis of renewable jet fuel from lignocellulosic platform compounds has drawn a lot of attention in recent years. So far, most work has concentrated on the production of conventional jet fuels. JP-10 is an advanced jet fuel currently obtained from fossil energy. Due to its excellent properties, JP-10 has been widely used in military aircraft. However, the high price and low availability limit its application in civil aviation. Here, we report a new strategy for the synthesis of bio-JP-10 fuel from furfuryl alcohol that is produced on an industrial scale from agricultural and forestry residues. Under the optimized conditions, bio-JP-10 fuel was produced with high overall carbon yields (≈65 %). A preliminary economic analysis indicates that the price of bio-JP-10 fuel can be greatly decreased from ≈7091 US$/ton (by fossil route) to less than 5600 US$/ton using our new strategy. This work makes the practical application of bio-JP-10 fuel forseeable.

Method for preparing JP-10 aviation fuel from furfuryl alcohol

The invention relates to a method for preparing JP-10 aviation fuel from furfuryl alcohol. The method for preparing JP-10 aviation fuel by taking the furfuryl alcohol as a raw material is totally divided into six reactions as follows: a first reaction of carrying out a rearrangement reaction on a furfuryl alcohol solution in the presence of a base catalyst or under the condition that any catalystis not added to prepare hydroxy cyclopentenone; a second reaction of reacting the hydroxy cyclopentenone and hydrogen under catalysis of a hydrogenation catalyst so as to prepare 1,3-cyclopendiol; a third reaction of dehydrating the 1,3-cyclopendiol to prepare cyclopentadiene; a fourth reaction of carrying out a D-A reaction on the cyclopentadiene to produce dicyclopentadiene; a fifth reaction ofhydrogenating the dicyclopentadiene to produce endo-tetrahydrodicyclotadiene; and a sixth reaction of performing isomerization on the endo-tetrahydrodicyclotadiene to produce hanging type tetrahydrodicyclopentadiene, wherein the prepared hanging type tetrahydrodicyclopentadiene can directly serve as the JP-10 aviation fuel. The invention provides a cheap high-efficiency synthetic method for synthesizing the JP-10 aviation fuel from a lignocelluloses-based platform chemical compound, namely furfuryl alcohol.

Method for preparation of cyclopentadiene or dicyclopentadiene by furfuryl alcohol

The invention relates to a method for preparation of cyclopentadiene or dicyclopentadiene by furfuryl alcohol. The method for preparation of cyclopentadiene or dicyclopentadiene by furfuryl alcohol as a raw material comprises the three-step reaction: a first step, under a condition with an alkali catalyst or under a condition with no addition of a catalyst, carrying out a rearrangement reaction of a furfuryl alcohol solution to prepare hydroxy cyclopentenone; a second step, under catalysis of a hydrogenation catalyst, carrying out a reaction of hydroxy cyclopentenone with hydrogen gas to prepare 1,3-cyclopendiol; and a third step, dehydrating 1,3-cyclopendiol to prepare cyclopentadiene or dicyclopentadiene. The used catalyst and raw materials are inexpensive and easy to obtain, the preparation process is simple, and high activity and selectivity are achieved for rearrangement reaction of furfuryl alcohol, hydrogenation reaction of hydroxy cyclopentenone and dehydration reaction of 1,3-cyclopendiol. The invention provides the cheap and efficient synthesis method for synthesis of cyclopentadiene or dicyclopentadiene with the lignocellulose based platform compound furfuryl alcohol.

Method for preparing JP-10 aviation fuel from furfuryl alcohol

The invention relates to a method for preparing JP-10 aviation fuel from furfuryl alcohol. The method for preparing the JP-10 aviation fuel by adopting the furfuryl alcohol as a raw material comprises the following five steps: step I, enabling a furfuryl alcohol solution to have a rearrangement reaction to prepare hydroxylcyclopentenone under the condition of an alkaline catalyst or no catalyst; step II, enabling the hydroxylcyclopentenone to react with hydrogen under the catalysis of a hydrogenation catalyst to prepare 1,3-cyclopentanediol; step III, preparing cyclopentadiene or dicyclopentadiene by dehydrating the 1,3-cyclopentanediol; step IV, enabling the cyclopentadiene and the dicyclopentadiene to have an isomerization reaction to generate hanging dicyclopentadiene; and step V, hydrogenating the hanging dicyclopentadiene to generate hanging tetrahydro-dicyclopentadiene, and then rectifying and purifying to obtain the JP-10 aviation fuel. Raw materials used in the method are cheap and easy to obtain, the preparation process is simple, and the activity and selectivity for the rearrangement reaction of the furfuryl alcohol, the hydrogenation reaction of the hydrocyclopentenone and the dehydration reaction is relatively high. The invention provides a synthetic method with low cost and high efficiency for synthesizing the cyclopentadiene or the dicyclopentadiene from lignocelluloses-based platform compound and furfuryl alcohol.

Method for preparing 1,3-cyclopentanediol from furfuryl alcohol

The invention relates to a method for preparing 1,3-cyclopentanediol from furfuryl alcohol. According to the method, furfuryl alcohol is used as a raw material, and 1,3-cyclopentanediol is prepared through two steps of reactions. The method comprises a first step of subjecting a furfuryl alcohol solution to a rearrangement reaction in the presence of an alkaline catalyst or in the absence of any catalyst so as to prepare hydroxycyclopentenone and a second step of reacting hydroxycyclopentenone with hydrogen under the catalysis of a hydrogenation catalyst so as to prepare 1,3-cyclopentanediol. The catalysts and raw materials used in the invention are cheap and easily available; the preparation method is simple in process; and high activity and selectivity are obtained in the rearrangement reaction of furfuryl alcohol and the hydrogenation reaction of hydroxycyclopentenone. The method provided by the invention is high-efficiency synthetic method for preparing 1,3-cyclopentanediol from a lignocelluloses-based platform compound, i.e., furfuryl alcohol.

Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose

A new route for the selective synthesis of renewable 1,3-cyclopentanediol was developed by the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone followed by hydrogenation. The presence of a small amount of base catalysts is beneficial for the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone. Such a promotion effect of base catalysts can be rationalized by restraining the generation of levulinic acid which may catalyze the polymerization of furfuryl alcohol. In the hydrogenation of 4-hydroxycyclopent-2-enone to 1,3-cyclopentanediol, an evident solvent effect was noticed. Higher carbon yields of 1,3-cyclopentanediol were obtained when tetrahydrofuran was used as the solvent. In the large scale tests with high initial concentrations of feedstocks, a high overall carbon yield (72.0%) of 1,3-cyclopentanediol was achieved over cheap catalysts (MgAl-HT and RANEY Ni). As a potential application, 1,3-cyclopentanediol as obtained was successfully used as a monomer in the synthesis of polyurethane.

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

A new class of poly-N-vinylpyrrolidinones containing an asymmetric center at C5 of the pyrrolidinone ring were synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1,3- and 1,2-trans-cycloalkanediols and desymmetrization of meso cis-diols took place with 0.15 mol % Pd/Au (3:1)-17 under oxygen atmosphere in water to give excellent chemical and optical yields of (S)-hydroxy ketones. Various alkenes were oxidized with 0.5 mol % Pd/Au (3:1)-17 under 30 psi of oxygen in water to give the dihydroxylated products in >93% ee. Oxidation of (R)-limonene at 25 °C occurred at the C-1,2-cyclic alkene function yielding (1S,2R,4R)-dihydroxylimonene 49 in 92% yield. Importantly, cycloalkanes were oxidized with 1 mol % Cu/Au (3:1)-17 and 30% H2O2 in acetonitrile to afford chiral ketones in very good to excellent chemical and optical yields. Alkene function was not oxidized under the reaction conditions. Mechanisms were proposed for the oxidation reactions, and observed stereo- and regio-chemistry were summarized.