WO2019199459A1 - Préparation et utilisation d'acides biphényl carboxyliques, d'alcools et d'esters - Google Patents

Préparation et utilisation d'acides biphényl carboxyliques, d'alcools et d'esters Download PDF

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Publication number
WO2019199459A1
WO2019199459A1 PCT/US2019/024303 US2019024303W WO2019199459A1 WO 2019199459 A1 WO2019199459 A1 WO 2019199459A1 US 2019024303 W US2019024303 W US 2019024303W WO 2019199459 A1 WO2019199459 A1 WO 2019199459A1
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compound
formula
catalyst
produce
biphenyl
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PCT/US2019/024303
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English (en)
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Kapil KANDEL
Michael Salciccioli
Alex E. CARPENTER
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Exxonmobil Chemical Patents Inc.
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Publication of WO2019199459A1 publication Critical patent/WO2019199459A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional 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
    • C07C67/327—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 by elimination of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms

Definitions

  • This disclosure relates to the preparation and use of biphenyl carboxylic acids, alcohols, and esters.
  • Biphenyl carboxylic acids, alcohols, and esters are useful intermediates in the production of a variety of commercially valuable products, including polyesters and plasticizers for PVC and other polymer compositions.
  • biphenyl mono- and dicarboxylic acids can be converted to plasticizers by esterification with long chain alcohols.
  • diphenyl dicarboxylic acids are potential precursors, either alone or as a modifier for polyethylene terephthalate (PET), in the production of polyester fibers, engineering plastics, liquid crystal polymers for electronic and mechanical devices, and films with high heat resistance and strength.
  • PET polyethylene terephthalate
  • the 4-monocarboxylic acid and the 4,4’-dicarboxylic acid isomers are the most desired due to the properties of the resulting products and hence have the broadest application.
  • biphenyl carboxylic acids can be prepared by oxidation of dimethylbiphenyl (DMBP) compounds, which in turn may be produced by hydroalkylation of toluene followed by dehydrogenation of the resulting (methylcyclohexyl)toluene (MCHT).
  • DMBP dimethylbiphenyl
  • MCHT methylcyclohexyl
  • the DMBP product comprises a mixture of all six DMBP isomers, namely 2,2’, 2,3’ 2,4’, 3,3’, 3,4’, and 4,4’ DMBP, in which the 3,4’ isomer is usually the most abundant and the 4,4’ isomer normally comprises less than 20% of the overall isomer mixture.
  • the 3,4’ isomer is usually the most abundant and the 4,4’ isomer normally comprises less than 20% of the overall isomer mixture.
  • most of the product must be recycled to an isomerization reactor, which increases the cost and complexity of the process.
  • biphenyl-4- carboxylic acid and biphenyl-4,4’ -dicarboxylic acid and their corresponding alcohols and esters can be formed by a process including (1) reaction of benzene and/or toluene with certain furanyl compounds, particularly 2-substituted furan compounds (2) followed by tandem Diels- Alder/dehydration reaction of the reaction product with a dienophile, particularly ethylene. Since furfural or 2-furaldehyde can be produced from renewable hemi-cellulose, this process provides an attractive route to these biphenyl compounds.
  • the present disclosure resides in a process for producing a biphenyl carboxylic acid, alcohol, and/or ester, the process comprising:
  • R 1 is -H, -CH 3 , -CHO, -CH 2 OH, -COOH or -COOR 2 and R 2 is an alkyl group having from 1 to 20 carbon atoms, in the presence of a first catalyst under conditions effective to produce a compound having the formula (II):
  • each R n is independently selected from the group consisting of -R 3 , -H, -CH3, -CHO, - CH2OH, -COOH or -COOR 3 , R 3 is an alkyl group having from 1 to 20 carbon atoms, and where each R n can be the same or different, under cycloaddition reaction conditions and in the presence of a second catalyst to produce a bicyclic ether; and
  • the present disclosure resides in a process for producing a biphenyl carboxylic acid, alcohol, and/or ester, the process comprising:
  • R 1 is -H, -CH 3 , -CHO, CH 2 OH, -COOH or -COOR 2 and R 2 is an alkyl group having from 1 to 20 carbon atoms, in the presence of a first catalyst under conditions effective to produce a compound having the formula (V):
  • each R n is independently selected from the group consisting of -R 3 , -H, -CH3, -CHO, - CH2OH, -COOH or -COOR 3 , R 3 is an alkyl group having from 1 to 20 carbon atoms, and where each R n can be the same or different, under cycloaddition reaction conditions and in the presence of a second catalyst to produce a bicyclic ether; and
  • the present disclosure resides in a product composition comprising a mixture of the compound of formula (II) and the compound of formula (IV).
  • the present disclosure resides in a product composition comprising a mixture of the compound of formula (V) and the compound of formula (VI).
  • Described herein is a novel process for producing biphenyl-4-carboxylic acid, biphenyl-4,4’ -dicarboxylic acid, and their corresponding alcohols and esters.
  • the process comprises initially reacting a feedstock comprising benzene and/or toluene with a furanyl compound, preferably a 2-substituted furan compound, having the formula (I):
  • R 1 is -H, -CH 3 , -CHO, -CH 2 OH, -COOH or -COOR 2 and R 2 is an alkyl group having from 1 to 20 carbon atoms, in the presence of a first catalyst under conditions effective to produce a compound having the formula (II) when the feedstock comprises benzene:
  • each R n is independently selected from the group consisting of -R 3 , -H, -CH3, -CHO, - CH2OH, -COOH or -COOR 3 , R 3 is an alkyl group having from 1 to 20 carbon atoms, and where each R n can be the same or different, under cycloaddition reaction conditions and in the presence of a second catalyst to produce a bicyclic ether in a combined Diels-Alder addition and dehydration sequence to produce biphenyl compounds having the formula (IV) and/or (VI):
  • Compounds (IV) and (VI) can be recovered as the desired acid, alcohol, or ester, where R 1 is -COOH, -CH2OH or -COOR 2 .
  • compound (IV) may be oxidized to produce the desired compound, e.g. acid, where R 1 is -CH3, -CHO, or -CH2OH, or alkylated and then oxidized to produce the desired compound, e.g. acid, where R 1 is -H.
  • compound (VI) may be oxidized to produce the desired compound, e.g. acid, where R 1 is -H, -CH 3 , -CHO, or -CH 2 OH, or alkylated and then oxidized to produce the desired acid where R 1 is -H.
  • the starting furanyl compound of formula (I) is, or is derived from, furfural and especially furfural produced from renewable sources, such as hemi-cellulose.
  • the initial reaction between the benzene and/or toluene and the compound of formula (I) comprises oxidative coupling and the first catalyst comprises at least one metal or compound thereof from Groups 8 to 13 of the Periodic Table, such as at least one of palladium or a palladium compound, zinc or a zinc compound, or a mixture thereof.
  • Suitable reaction conditions for such an oxidative coupling step are described in 2(8) ACS Catal. 1787-1791 (2012), the entire contents of which are incorporated herein by reference, and include a temperature from 30°C to 250°C, such as from 50°C to l50°C.
  • the reaction may be conducted in the presence of an inorganic or organic oxidant.
  • Preferred suitable oxidants include oxygen or an oxygen containing gas, preferably at an oxygen partial pressure up to 5500 kPa-a, as well as copper or silver based oxidants described in 2(8) ACS Catal, (above), e.g., AgOAc.
  • the initial reaction between the benzene and/or toluene and the compound of formula (I) comprises alkylation and the first catalyst comprises a bifunctional catalyst comprising a molecular sieve and at least one dehydrogenation metal.
  • Suitable molecular sieves for use in the bifunctional alkylation catalyst comprise
  • BEA, FAU, and MWW structure type molecular sieves and mixtures thereof include zeolite beta, which is described in US 3,308,069 and Re. No. 28,341.
  • FAU structure type molecular sieves include zeolite Y, ultrastable Y (USY which is described in US 3,293,192 and 3,449,070), dealuminized Y (Deal Y which is described in US 3,442,795 and zeolite UHP-Y which is described in US 4,401,556.
  • MWW structure type molecular sieves include MCM-22 (described in US 4,954,325), PSH-3 (described in US 4,439,409), SSZ-25 (described in US 4,826,667), ERB-l (described in EP 0293032), ITQ-l (described in US 6,077,498), ITQ-2 (described in WO 97/17290), MCM-36 (described in US 5,250,277), MCM-49 (described in US 5,236,575), MCM-56 (described in US 5,362,697), and mixtures thereof.
  • Suitable dehydrogenation metals for use in the bifunctional alkylation catalyst comprise include palladium, ruthenium, nickel, zinc, tin, and cobalt, with palladium being particularly advantageous.
  • the amount of dehydrogenation metal present in the catalyst is between 0.05 and 10 wt %, such as between 0.1 and 5 wt%, of the catalyst.
  • Suitable conditions for the alkylation reaction comprise a temperature from 200°C to 600°C and a pressure from 1,400 kPa-a to 14,000 kPa-a, preferably such that the reaction mixture is predominantly (>50 wt%) in the liquid phase.
  • the high reactivity of the alpha-hydrogen next to the furanic oxygen means that the reaction product will contain a large concentration, typically at least 50%, such as at least 80%, even up to 100%, of the desired furanyl derivative, namely the compound of formula (II) or (V), by weight of the total converted materials.
  • Concentrations of the 2,3- and 2,4-furanyl derivatives are typically less than 20%, such as less than 10%, by weight of the total converted materials.
  • any unreacted species such as the benzene, toluene and/or furanyl starting materials (e.g., 2-fumayl starting materials)
  • at least part of the compound of formula (II) or (V) is then reacted with the dienophile of formula (III), preferably ethylene, over a second catalyst via a Diels-Alder addition reaction to produce a phenyl- substituted bicyclic ether.
  • the Diels-Alder product is a low-concentration intermediate with unfavorable equilibrium and readily dehydrates in-situ to the biphenyl compound of formula (IV) or (VI) respectively.
  • the dienophile of formula (III) is symmetric, i.e., each R n in the dienophile of formula (III) and in the produced biphenyl compound of formula (IV) or (VI) are the same.
  • a preferred symmetric dienophile is ethylene.
  • the dienophile of formula (III) may be asymmetric, as shown in formula (Ilia): (Ilia) ,
  • R p and R q are independently selected from the group consisting of -R 3 , -H, -CH 3 , -CHO, -CH 2 OH, -COOH or -COOR 3 , where R 3 is an alkyl group having from 1 to 20 carbon atoms, and where R p and R q are different.
  • the compound of formula (IV) typically comprises one or more of the following compounds as shown in formulas (IVa)-(IVb):
  • the compound of formula (VI) typically comprises one or more of the following compounds as shown in formulas (Vla)-(VIb):
  • dienophiles include propylene and methyl acrylate. Often, two or more dienophiles may be used.
  • the Diels-Alder reaction is conducted in the presence of an acidic second catalyst, preferably with Lewis acidity.
  • the second catalyst comprises an acidic molecular sieve such as an aluminosilicate molecular sieve having a silica to alumina molar ratio less than 75, for example less than 50, such as less than 30.
  • Suitable molecular sieves may comprise MFI, BEA, FAU, MOR, MTW, MFS, FER, CHA, and MWW structure type molecular sieves, and mixtures thereof.
  • Brpnsted and/or Lewis acids can be used as the second catalyst.
  • Suitable Brpnsted acid catalysts include acetic acid and its halogenated analogs, e.g., trifluoroacetic acid, trichloroacetic acid, hexachloroanbtimonate ( HSbCL), trifluoromethanesulfonic acid (HSO3CF3), and p-toluenesulfonic acid (HSO3T0S).
  • Suitable Lewis acids include BX 3, AlX 3 , RAIX2, R 2 AlX, TiX 4 , SnX 2 , SnX 4 , ZnX 2 , SbX 3 , SbX 5 , ScX 3 , where X is selected from F, Cl, Br, and where R is an alkyl group having from 1 to 22 carbon atoms.
  • Additional suitable Lewis acids include, but are not limited to, Sc(OTf)3, lanthanide (III) species, Lewis acidic transition metal complexes, and Ti(OR 4 ) 4 , where R 4 comprises an alkoxide or phenoxide group having from 1 to 22 carbon atoms.
  • Suitable conditions for the cycloaddition/dehydration reaction include a temperature from l00°C to 400°C and a pressure of 25 to 5000 psig (270 to 34600 kPa-a).
  • the rate of the Diels-Alder reaction may be enhanced by employing strategies described in Pindur et ah, Acceleration Selectivity Enhancement of Diels-Alder Reactions by “Special Catalytic Methods,” 93 Chem. Rev. 741-61 (1993), the entire contents of which are incorporated herein by reference.
  • the product of the cycloaddition/dehydration reaction will generally contain a mixture of the compound of formula (IV) together with some unreacted compound of formula (II), optionally together with unreacted dienophile, such as ethylene, and water by-product.
  • the desired compound of formula (IV) can then be recovered by known separation methods, including distillation and phase separation. Preferably, water may be removed as the cycloaddition/dehydration reaction proceeds.
  • the product of the cycloaddition/dehydration reaction will generally contain a mixture of the compound of formula (VI) together with some unreacted compound of formula (V), together with unreacted dienophile, such as ethylene, and water by-product.
  • the desired compound of formula (VI) can then be recovered by known separation methods, including distillation and phase separation. Preferably, water may be removed as the cycloaddition/dehydration reaction proceeds.
  • R 1 in the starting furanyl compound (I) is -CHO, -CH2OH, -COOH or -COOR 2
  • compound (II) or (V) may be desirable to reduce compound (II) or (V) to the corresponding 2-methyl derivative prior to Diels-Alder/dehydration reaction to increase the rate of the reaction with the dienophile, such as ethylene.
  • dienophile such as ethylene
  • Compound (IV) can be oxidized to produce the desired compound, e.g. biphenyl-4- carboxylic acid, in aspects where R 1 in the starting furanyl compound (I) is -CH 3 , -CHO, or - CH 2 OH, or alkylated followed by oxidation produce the desired compound, e.g. biphenyl-4- carboxylic acid and/or biphenyl-4,4’ -carboxylic acid, where R 1 in the starting furanyl compound (I) is -H.
  • compound (VI) can be oxidized to the desired compound, e.g.
  • biphenyl-4-carboxylic acid and/or biphenyl-4,4’-carboxylic acid in aspects where R 1 in the starting furanyl compound (I) is -H, -CH 3 , -CHO, or -CH 2 OH, or alkylated followed by oxidation to the desired compound, e.g. biphenyl-4-carboxylic acid and/or biphenyl-4,4’ - carboxylic acid, where R 1 in the starting furanyl compound (I) is -H.
  • oxidation and, optionally, alkylation may be conducted by methods well known in the art.
  • compound (IV) or compound (VI) may be oxidized by reaction with an oxidant, such as oxygen, ozone or air, or any other oxygen source, such as hydrogen peroxide, in the presence of a catalyst and with or without a promoter, such as Br, at temperatures from 30°C to 300°C, such as from 60°C to 200°C.
  • oxidant such as oxygen, ozone or air, or any other oxygen source, such as hydrogen peroxide
  • a catalyst and with or without a promoter, such as Br at temperatures from 30°C to 300°C, such as from 60°C to 200°C.
  • Suitable catalysts comprise Co or Mn or a combination of both metals.
  • the oxidation is normally conducted in solution, generally in acetic acid as solvent.

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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

La présente invention concerne un procédé de production d'un acide biphényl carboxylique, d'un alcool et/ou d'un ester, qui consiste à faire réagir du benzène ou du toluène avec un composé furanyle de formule (I) dans laquelle R1 est -H, -CH3, -CHO, -CH2OH, -COOH ou -COOR2 et R2 est un groupe alkyle ayant de 1 à 20 atomes de carbone en présence d'un premier catalyseur dans des conditions efficaces pour produire un composé furane substitué par 2-R1, 5 -phényle. Ce dernier est ensuite mis à réagir avec un diénophile dans des conditions de réaction de cycloaddition et en présence d'un second catalyseur pour produire un éther bicyclique et l'éther bicyclique est déshydraté en un composé biphényle.
PCT/US2019/024303 2018-04-12 2019-03-27 Préparation et utilisation d'acides biphényl carboxyliques, d'alcools et d'esters WO2019199459A1 (fr)

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