FR3028854B1 - Nouveaux procedes d'obtention d'acide p-toluique et de ses derives - Google Patents

Nouveaux procedes d'obtention d'acide p-toluique et de ses derives

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Publication number
FR3028854B1
FR3028854B1 FR1461434A FR1461434A FR3028854B1 FR 3028854 B1 FR3028854 B1 FR 3028854B1 FR 1461434 A FR1461434 A FR 1461434A FR 1461434 A FR1461434 A FR 1461434A FR 3028854 B1 FR3028854 B1 FR 3028854B1
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France
Prior art keywords
derivatives
acid
toluic acid
obtaining
absence
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
FR1461434A
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English (en)
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FR3028854A1 (fr
Inventor
Damien Delcroix
Christophe Vallee
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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Priority to FR1461434A priority Critical patent/FR3028854B1/fr
Publication of FR3028854A1 publication Critical patent/FR3028854A1/fr
Application granted granted Critical
Publication of FR3028854B1 publication Critical patent/FR3028854B1/fr
Active legal-status Critical Current
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
    • C07C2523/14—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production d'acide p-toluique et de ses dérivés comprenant une étape a) de réaction de Diels-Alder entre l'acide sorbique et/ou ses dérivés, et l'éthylène pour obtenir l'acide 4-méthylcyclohex-2-ène-oïque et/ou ses dérivés correspondants, en présence ou non d'un catalyseur et en présence ou non d'un solvant, ladite étape a) opérant à une température comprise entre 0°C et 400°C et à une pression comprise entre 0,1 et 20 MPa, une étape b) d'aromatisation de l'acide 4-méthylcyclohex-2-ène-oïque et/ou de ses dérivés correspondants obtenus à l'issue de l'étape a) pour former l'acide p-toluique et/ou ses dérivés, en présence d'un ou plusieurs catalyseurs et en présence ou non d'un agent oxydant, ladite étape b) opérant à une température comprise entre 50°C et 400°C et à une pression comprise entre 0,1 et 20 MPa. L'acide p-toluique ou ses dérivés ainsi obtenus peut ensuite avantageusement être converti en p-xylène qui peut être oxydé en acide térephtalique. L'acide p-toluique ou ses dérivés peut également être converti en acide térephtalique.
FR1461434A 2014-11-25 2014-11-25 Nouveaux procedes d'obtention d'acide p-toluique et de ses derives Active FR3028854B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR1461434A FR3028854B1 (fr) 2014-11-25 2014-11-25 Nouveaux procedes d'obtention d'acide p-toluique et de ses derives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1461434A FR3028854B1 (fr) 2014-11-25 2014-11-25 Nouveaux procedes d'obtention d'acide p-toluique et de ses derives

Publications (2)

Publication Number Publication Date
FR3028854A1 FR3028854A1 (fr) 2016-05-27
FR3028854B1 true FR3028854B1 (fr) 2017-01-13

Family

ID=52392097

Family Applications (1)

Application Number Title Priority Date Filing Date
FR1461434A Active FR3028854B1 (fr) 2014-11-25 2014-11-25 Nouveaux procedes d'obtention d'acide p-toluique et de ses derives

Country Status (1)

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FR (1) FR3028854B1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112824361B (zh) * 2019-11-21 2022-03-25 中国科学院大连化学物理研究所 一种由镍铁双金属催化剂高效催化4-甲基-3-环己烯甲醛转化制备对二甲苯的方法
CN114605245B (zh) * 2020-12-09 2023-07-07 中国科学院大连化学物理研究所 一种制备芳香醛的方法
WO2023059603A2 (fr) * 2021-10-05 2023-04-13 Celanese International Corporation Procédé de fabrication d'acide sorbique à partir de matériaux renouvelables

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120027531A (ko) * 2009-06-16 2012-03-21 아미리스 인코퍼레이티드 시클로헥센 1,4-카르복실레이트

Also Published As

Publication number Publication date
FR3028854A1 (fr) 2016-05-27

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