Synthesis of terpineol from α-pinene by homogeneous acid catalysis

Román-Aguirre, Manuel; Torre-Sáenz, L. De la; Antúnez-Flores, W.; Robau-Sánchez, Alejandro; Elguézabal, Alfredo Aguilar

doi:10.1016/j.cattod.2005.07.061

Cited by 44 publications

(34 citation statements)

References 7 publications

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“…The acid transfers a proton to double bond of the alkene forming an intermediate of carbocation. The carbocation can lose a proton and generate monocyclic and bicyclic hydrocarbons or, in the presence of a nucleophile, give to monocyclic and bicyclic alcohol [2,8]. In the hydration of terpenes, variation products might be obtained depending on the catalyst and reaction conditions.…”

Section: Effect Of Reaction Temperaturementioning

confidence: 99%

“…Apart from this, complete separation of homogeneous acid from the product is very difficult to be performed because dehydration of terpineol occurs in the downstream process [7][8]10,14]. Hence, the use of heterogeneous catalyst is highly recommended for this reaction as it offers several engineering benefits and provides a favorable distribution of alcohol in the two liquid phase [9,12].…”

Section: Introductionmentioning

confidence: 99%

“…Several studies on hydration of α-pinene using homogeneous and heterogeneous solid acids had been reported [7][8][9][10]. Vital et al [4] reported the use of solid acid catalysts such as zeolites and impregnated phosphomolybdic acid (HPMo) on polymeric membranes for α-pinene hydration to give 100% conversion with selectivity for α-terpineol between 50% and 70% although it required 150 h of reaction time.…”

Section: Introductionmentioning

confidence: 99%

“…Experiments with the supported catalyst showed considerable decrease in conversion and the appearance of large percentage of isomerization products. Román-Aguirre et al [8] utilized oxalic and chloroacetic acid for the transformation of α-pinene and obtained conversion of 80% with selectivity of 70% for α-terpineol after 4 h but the dissolved acid had to be separated. Mochida et al [9] reported the use of zeolites and obtained 100% conversion but with low selectivity for alcohols (about 57%).…”

Section: Introductionmentioning

confidence: 99%

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The Acid Catalyzed Reaction of α-Pinene Over Y-Zeolite

Wijayati¹,

Pranowo²,

Jumina³

et al. 2013

Indones. J. Chem.

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Section: Effect Of Reaction Temperaturementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Acid Catalyzed Reaction of α-Pinene Over Y-Zeolite

Wijayati¹,

Pranowo²,

Jumina³

et al. 2013

Indones. J. Chem.

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“…10 devido a essa enorme demanda, o terpineol utilizado no mercado mundial é obtido, em grande parte, por via sintética, e vários métodos para tal são disponíveis, com especial destaque àqueles que utilizam pinenos ou a própria terebintina como materiais de partida. 11 Preparações a partir de outros monoterpenos como limoneno 12 ou nerol 13 também são descritas, sendo que o limoneno é interessante pela disponibilidade, facilidade de obtenção em alta pureza química e óptica e possibilidade de reações de adição seletivas, sendo bastante útil em estudos acadêmicos que visam demonstrar a aplicabilidade de diferentes catalisadores ácidos. 12 assim, com todo esse conjunto de informações, decidimos revisitar as metodologias para obtenção do (+)-α-terpineol (1) a partir do (+)-limoneno (3) e adaptá-la aos nossos laboratórios.…”

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Preparação do (+)-±-terpineol a partir do (+)-limoneno: monoterpenos de odor agradável em um projeto para química orgânica experimental

Baptistella¹,

Imamura²,

Melo³

et al. 2009

Quím. Nova

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Recebido em 4/7/08; aceito em 24/10/08; publicado na web em 12/2/09 PREPaRatIoN of (+)-α-tERPINEoL fRoM (+)-LIMoNENE: MoNotERPENES wIth PLEaSaNt odoR IN a PRojECt foR UNdERgRadUatE oRgaNIC ChEMIStRy LaBoRatoRy. a synthesis of (+)-α-terpineol from (+)-limonene was proposed as a project for undergraduate organic laboratory course. terpineol is a useful flavor and fragrance compound, and several aspects of this preparation are suited for experimental organic classes, including basic techniques for extraction and analyses of essential oils, different reaction types and the possibility of a high degree of student interest.Keywords: terpineol; limonene; project for undergraduate organic laboratory.Substâncias naturais que exibem ampla gama de atividades bioló-gicas e grande importância comercial sempre despertam a atenção dos estudantes. Se, aliado a isso, elas puderem ser obtidas por etapas sintéticas simples a partir de outras substâncias naturais facilmente disponíveis em nosso país, com certeza podem se tornar excelentes alvos de estudo em disciplinas experimentais de cursos de graduação em Química. Unindo essas considerações ao nosso interesse por seqüências sintéticas adequadas a tais disciplinas na área de química orgânica, 1 este artigo descreve a preparação do (+)-α-terpineol (1) a partir do (+)-limoneno (3), conhecido constituinte majoritário do óleo da casca de laranja.o α-terpineol (1) é um monoterpeno de odor agradável encontrado em uma grande variedade de óleos essenciais, 2 com ampla aplicação industrial. assim, é usado em indústrias de produtos de perfumaria 3 como constituinte de sabonetes e cosméticos, em indústrias de produtos de limpeza como repelente de insetos, 4 desinfetante 5 e aromatizante, 6 em indús-trias farmacêuticas como antifúngico 7 e anti-séptico 8 e em indústrias de processamento de minerais como agente de flotação. 9 Ultimamente, tem sido também empregado como substrato na preparação de copolímeros. 10 devido a essa enorme demanda, o terpineol utilizado no mercado mundial é obtido, em grande parte, por via sintética, e vários métodos para tal são disponíveis, com especial destaque àqueles que utilizam pinenos ou a própria terebintina como materiais de partida. 11 Preparações a partir de outros monoterpenos como limoneno 12 ou nerol 13 também são descritas, sendo que o limoneno é interessante pela disponibilidade, facilidade de obtenção em alta pureza química e óptica e possibilidade de reações de adição seletivas, sendo bastante útil em estudos acadêmicos que visam demonstrar a aplicabilidade de diferentes catalisadores ácidos. 12 assim, com todo esse conjunto de informações, decidimos revisitar as metodologias para obtenção do (+)-α-terpineol (1) a partir do (+)-limoneno (3) e adaptá-la aos nossos laboratórios. tomamos como base uma antiga patente japonesa, 14 cujo resumo cita a reação do limoneno com ácidos cloroacéticos, entre eles o ácido tricloroacético, seguida por hidrólise. o Esquema 1 mostra a seqüência sintética por nós adotada.os melhores resultados para este projeto são c...

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p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

Tibbetts

Bull

2021

Advanced Sustainable Systems

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the upgrading of biomass into biofuels and platform chemicals will need to be developed and integrated into new/existing chemical processes. [2] The large volumes and wide geographical distribution of lignocellulosic biomass means that it will undoubtedly play a key role as a biorenewable feedstock for bulk chemical production. [3] In this approach, fermentative processes are used to depolymerize lignocellulose biomass into sugars (e.g., glucose and fructose), with these monomers then transformed into low-value feedstocks such as bioethanol, succinic acid, glutamic acid, and 5-hydroxymethylfurfural. [4] Although highly promising, technological difficulties associated with large-scale catalytic upgrading of these highly oxygenated biopolymers cause significant problems that still need to be overcome before lignocellulose-based biorefineries become more widely established. [5] Monoterpenes (and monoterpenoids) represent an alternative biomass source for the production of biofuels, polymers, and chemicals that are available in significant volumes at low cost. Significant amounts of commercially available monoterpenes are currently produced as products and waste from the forestry and agricultural industries, all of which can be considered as potentially useful biorenewable feedstocks for fuel and chemical production. These include turpentine (≈360 000 tonnes pa), limonene-containing citrus oil (≈30 000 tonnes pa), mentholcontaining mint oil (≈20 000 tonnes pa), and 1,8-cineole from eucalyptus oil (≈7000 tonnes pa with an estimated multimillion tonne production potential per annum). [6] The structures of these energy-dense, lightly oxygenated, alkene-containing C 10 building blocks more closely resemble those of petroleum-based hydrocarbons, which means they can potentially be catalytically upgraded using existing refining technologies to produce a wide range of chemical products (including aromatics).Crude sulfate turpentine (CST) is the cheapest and most widely available source of monoterpene biomass, with around 260 000 tonnes of CST produced as a waste by-product of the paper industry annually. High pressure cooking of wood chips to produce paper pulp in the Kraft process generates around 15 kg of CST per tonne of pulp, [7] which is comprised of a mixture of monoterpenes and around 5% volatile sulfur compounds (e.g., Me 2 S). [6a] A further annual 100 000 tonnes of pinene-rich gum turpentine (GT) is also produced through sustainable tapping of the trunks of living trees. The major monoterpene components of turpentine are α-pinene, β-pinene, 3-carene, and limonene, along with small amounts of camphene and C 15 A terpene-based biorefinery is described that uses crude sulfate turpentine (CST) and gum turpentine (GT) to produce mixtures of p-menthadienes (p-MeDs) as biorenewable terpene feedstocks. An acid catalyzed ring opening reaction (6 m aq. H 2 SO 4 , 90 °C) is first used to convert the major bicyclic monoterpenes (α-pinene, β-pinene, and 3-carene) in untreated CST (or GT with 5 mol% Me 2 S) into mixtures of ...

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Synthesis of terpineol from α-pinene by homogeneous acid catalysis

Cited by 44 publications

References 7 publications

The Acid Catalyzed Reaction of α-Pinene Over Y-Zeolite

The Acid Catalyzed Reaction of α-Pinene Over Y-Zeolite

Preparação do (+)-±-terpineol a partir do (+)-limoneno: monoterpenos de odor agradável em um projeto para química orgânica experimental

p‐Menthadienes as Biorenewable Feedstocks for a Monoterpene‐Based Biorefinery

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