GB633354A - Process for the production of dibasic carboxylic acids - Google Patents

Process for the production of dibasic carboxylic acids

Info

Publication number
GB633354A
GB633354A GB35436/46A GB3543646A GB633354A GB 633354 A GB633354 A GB 633354A GB 35436/46 A GB35436/46 A GB 35436/46A GB 3543646 A GB3543646 A GB 3543646A GB 633354 A GB633354 A GB 633354A
Authority
GB
United Kingdom
Prior art keywords
oxidation
mixture
nitric acid
acid
oxidized
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.)
Expired
Application number
GB35436/46A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB633354A publication Critical patent/GB633354A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C07C51/316—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with oxides of nitrogen or nitrogen-containing mineral acids

Landscapes

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

Abstract

Dicarboxylic acids are obtained by partially oxidizing a cycloparaffin, the oxidation involving the reaction of 0.5 to 2.0 moles of oxygen per mole of cycloparaffin oxidized, separating the unreacted cycloparaffin only from the reaction mixture, and further oxidizing the residue with nitric acid without separating its ingredients. Cyclohexane is thus oxidized to adipic acid, or cyclopentane and cyclobutane to glutaric and succinic acids. The nitric acid oxidation may be in presence of copper, vanadium, or manganese salts, and may be in two stages, viz. at 40-90 DEG C., and at a higher temperature, e.g. 90-120 DEG C.; the first stage may be carried out by circulating the mixture in an endless duct, jacketed for maintaining the desired temperature, the mixture flowing thence through a preheater to a second jacketed duct maintained at the desired higher temperature. One-stage nitric acid oxidation, at 50-150 DEG C., may also be used. Examples describe (1) the liquid phase oxidation of cyclohexane using a cobalt naphthenate catalyst to give a mixture comprising, after removal of unconverted cyclohexane, cyclohexanone, cyclohexanol, cyclohexenyl, cyclohexyl ether, cyclohexyl esters, cyclohexandiol-1.2, adipic esters, d -formyl valeric acid, e -hydroxycaproic acid and its esters, which mixture is oxidized with nitric acid in two stages to give adipic acid; (2) the vapour phase oxidation of cyclohexane using a silver oxide catalyst, followed by treatment as in (1); (3) further nitric acid oxidations of the mixture obtained under (1) with details of working - up the products. Comparative examples are given describing a process in which the constituents of the reaction mixture from the first oxidation stage are separated before the nitric acid oxidation, and showing the improvement in yield when cyclohexyl valerate and cyclohexanol are oxidized in admixture to adipic acid, as compared with separate oxidation. Specification 572,260 is referred to.
GB35436/46A 1945-11-30 1946-11-29 Process for the production of dibasic carboxylic acids Expired GB633354A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US632081A US2439513A (en) 1945-11-30 1945-11-30 Adipic acid process

Publications (1)

Publication Number Publication Date
GB633354A true GB633354A (en) 1949-12-12

Family

ID=24533992

Family Applications (1)

Application Number Title Priority Date Filing Date
GB35436/46A Expired GB633354A (en) 1945-11-30 1946-11-29 Process for the production of dibasic carboxylic acids

Country Status (3)

Country Link
US (1) US2439513A (en)
FR (1) FR953498A (en)
GB (1) GB633354A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2978473A (en) * 1958-09-30 1961-04-04 Texaco Inc Dibasic acid manufacture

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US2557281A (en) * 1951-06-19 Oxidation op petroleum cyclohexane
US3260742A (en) * 1966-07-12 Upper layer
US2623072A (en) * 1946-09-27 1952-12-23 Phillips Petroleum Co Separation of cyclopentanone
US2565087A (en) * 1947-10-30 1951-08-21 Allied Chem & Dye Corp Process for oxidation of cycloaliphatic compounds
US2557282A (en) * 1949-03-31 1951-06-19 Du Pont Adipic acid process
US2617835A (en) * 1950-02-24 1952-11-11 Du Pont Polyhydric alcohol process
US2684984A (en) * 1952-03-31 1954-07-27 Shell Dev Production of cyclic alcohols and ketones
US2675407A (en) * 1952-04-10 1954-04-13 Standard Oil Dev Co Air oxidation of cycloalkanes
US2800504A (en) * 1952-10-15 1957-07-23 Distillers Co Yeast Ltd Production of lower aliphatic acids
US2825742A (en) * 1954-05-04 1958-03-04 Du Pont Liquid phase oxidation of cyclohexane
US2847431A (en) * 1955-02-07 1958-08-12 Celanese Corp Oxidation of ethylenically unsaturated fatty acids
US2831024A (en) * 1955-04-04 1958-04-15 Gulf Research Development Co Process for producing dibasic carboxylic acids
US2878276A (en) * 1955-05-03 1959-03-17 Gulf Research Development Co Process for producing dibasic carboxylic acids
US2982772A (en) * 1959-01-12 1961-05-02 Monsanto Chemicals Octahydro-5ah, 10ah, 4a, 9a-epoxydibenzo-p-dioxin-5a, 10a-diol
US3280183A (en) * 1963-04-11 1966-10-18 Wallace & Tiernan Inc Method of producing dicarboxylic acids
US3359308A (en) * 1963-05-17 1967-12-19 Du Pont Preparation of dicarboxylic acids by nitric acid oxidation
BE648422A (en) * 1963-05-27
FR1473174A (en) * 1965-01-20 1967-06-01
US3513194A (en) * 1965-11-15 1970-05-19 Toa Gosei Chem Ind Process for producing adipic acid
US5883292A (en) * 1996-01-17 1999-03-16 Twenty-First Century Research Corporation Reaction control by regulating internal condensation inside a reactor
US6143927A (en) 1996-06-24 2000-11-07 Rpc Inc. Methods for removing catalyst after oxidation of hydrocarbons
US6337051B1 (en) 1996-06-24 2002-01-08 Rpc Inc. Device for detecting formation of a second liquid phase
US5922908A (en) * 1996-06-24 1999-07-13 Twenty-First Century Research Corporation Methods for preparing dibasic acids
US6039902A (en) * 1996-06-24 2000-03-21 Rpc Inc. Methods of recycling catalyst in oxidations of hydrocarbons
US6288270B1 (en) 1996-06-24 2001-09-11 Rpc Inc. Methods for controlling the reaction rate of a hydrocarbon to an acid by making phase-related adjustments
WO1998007677A1 (en) 1996-08-21 1998-02-26 Twenty-First Century Research Corporation Methods and devices for controlling the reaction by adjusting the oxidant consumption rate
US5801273A (en) 1996-08-21 1998-09-01 Twenty-First Century Research Corporation Methods and devices for controlling the reaction rate of a hydrocarbon to an intermediate oxidation product by pressure drop adjustments
US20010053864A1 (en) * 1996-08-21 2001-12-20 Decoster David C. Devices for controlling the reaction rate and/or reactivity of hydrocarbon to an intermediate oxidation product by adjusting the oxidant consumption rate
US6103933A (en) * 1996-11-07 2000-08-15 Rpc Inc. Methods for controlling the oxidation rate of a hydrocarbon by adjusting the ratio of the hydrocarbon to a rate-modulator
US5817868A (en) * 1996-11-12 1998-10-06 Twenty-First Century Research Corporation Method and devices for controlling the oxidation of a hydrocarbon to an acid by regulating temperature/conversion relationship in multi-stage arrangements
US5824819A (en) * 1996-12-18 1998-10-20 Twenty-First Century Research Corporation Methods of preparing an intermediate oxidation product from a hydrocarbon by utilizing an activated initiator
US6037491A (en) * 1997-07-25 2000-03-14 Rpc Inc. Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio
US5929277A (en) * 1997-09-19 1999-07-27 Twenty-First Century Research Corporation Methods of removing acetic acid from cyclohexane in the production of adipic acid
US5908589A (en) * 1997-12-08 1999-06-01 Twenty-First Century Research Corporation Methods for separating catalyst from oxidation mixtures containing dibasic acids
AU2116599A (en) 1998-02-09 1999-08-23 Rpc, Inc. Process for treating cobalt catalyst in oxidation mixtures of hydrocarbons to dibasic acids
KR20010041050A (en) * 1998-02-19 2001-05-15 알피시 인코포레이티드 Methods and devices for separating catalyst from oxidation mixtures
KR20010052376A (en) * 1998-05-20 2001-06-25 알피시 인코포레이티드 Controlled oxidation of hydrocarbons to intermediate oxidation products
US6433221B1 (en) 1998-07-02 2002-08-13 Rpc Inc. Methods of separating catalyst in solution from a reaction mixture produced by oxidation of cyclohexane to adipic acid
US6340420B1 (en) 1998-07-06 2002-01-22 Rpc Inc. Methods of treating the oxidation mixture of hydrocarbons to respective dibasic acids
JP2002542214A (en) 1999-04-20 2002-12-10 アールピーシー インコーポレイテッド Method for replacing water and cyclohexanone with acetic acid in aqueous solution of catalyst
CN105969813A (en) 2011-06-17 2016-09-28 英威达技术有限责任公司 Use of hydrolases to increase monomer content in waste stream
BR112013033672A2 (en) 2011-06-30 2017-03-14 Invista Tech Sarl method for converting a compound, substantially pure host cell culture and isolated cell
US9102958B2 (en) 2011-12-16 2015-08-11 Invista North America S.á.r.l. Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage
US9102960B2 (en) 2011-12-16 2015-08-11 Invista North America S.á.r.l. Methods of producing 6-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage
US9790525B2 (en) 2012-12-14 2017-10-17 Invista North America S.A.R.L. Methods of producing 7-carbon chemicals via CoA-dependent carbon chain elongation associated with carbon storage
US10196657B2 (en) 2012-12-31 2019-02-05 Invista North America S.A.R.L. Methods of producing 7-carbon chemicals via methyl-ester shielded carbon chain elongation
EP2938735A2 (en) 2012-12-31 2015-11-04 Invista Technologies S.A R.L. Methods of producing 7-carbon chemicals via pyruvate and succinate semialdehyde aldol condensation
EP2938734A2 (en) 2012-12-31 2015-11-04 Invista Technologies S.A R.L. Methods of producing 7-carbon chemicals via aromatic compounds
US9580733B2 (en) 2012-12-31 2017-02-28 Invista North America S.A.R.L. Methods of producing 6-carbon chemicals via methyl-ester shielded carbon chain elongation
EP2938731A2 (en) 2012-12-31 2015-11-04 Invista Technologies S.A R.L. Methods of producing 7-carbon chemicals via carbon chain elongation associated with cyclohexane carboxylate synthesis
US9920336B2 (en) 2012-12-31 2018-03-20 Invista North America S.A.R.L. Methods of producing 7-carbon chemicals from long chain fatty acids via oxidative cleavage
US9580731B2 (en) 2012-12-31 2017-02-28 Invista North America S.A.R.L. Methods of producing 7-carbon chemicals via c1 carbon chain elongation associated with coenzyme B synthesis
EP3143152A1 (en) 2014-05-15 2017-03-22 Invista Technologies S.à r.l. Methods of producing 6-carbon chemicals using 2,6-diaminopimelate as precursor to 2-aminopimelate
BR112016029375A2 (en) 2014-06-16 2017-10-17 Invista Tech Sarl methods, reagents and cells to biosynthesize compounds
EP3155105A1 (en) 2014-06-16 2017-04-19 Invista Technologies S.A R.L. Methods, reagents and cells for biosynthesizing compounds
US9777302B2 (en) 2014-06-16 2017-10-03 Invista North America S.A.R.L. Methods, reagents and cells for biosynthesizing compounds
EP3155111A1 (en) 2014-06-16 2017-04-19 Invista Technologies S.à r.l. Process for producing glutarate and glutaric acid methyl ester
KR20170100573A (en) 2014-12-22 2017-09-04 로디아 오퍼레이션스 Cycloalkane oxidation catalysts and method to produce alcohols and ketones
WO2022029583A1 (en) 2020-08-07 2022-02-10 Inv Nylon Chemicals Americas, Llc Production of dinitriles
CN113651685B (en) * 2021-09-25 2024-02-09 侯凤芹 Process for preparing dicarboxylic acids by two-stage oxidation of cyclic alkanes

Family Cites Families (13)

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US1921101A (en) * 1926-02-12 1933-08-08 Du Pont Production of aliphatic di-car-boxylic acids
US1960211A (en) * 1932-11-03 1934-05-22 Dow Chemical Co Preparation of adipic acids
US2168844A (en) * 1936-04-03 1939-08-08 Union Oil Co Production of glutaric acid
US2223493A (en) * 1938-07-12 1940-12-03 Du Pont Oxidation of cyclic compounds
NL53438C (en) * 1938-10-08
US2223494A (en) * 1939-06-06 1940-12-03 Du Pont Production of cyclic alcohols and ketones
US2285914A (en) * 1939-12-28 1942-06-09 Du Pont Oxidation of cyclohexanol
US2228261A (en) * 1940-02-23 1941-01-14 Du Pont Oxidation of cyclohexane
US2285601A (en) * 1940-02-29 1942-06-09 Shell Dev Oxidation of alicyclic hydrocarbons
US2286559A (en) * 1940-02-29 1942-06-16 Shell Dev Oxidation of alicyclic ketones
US2291211A (en) * 1940-07-09 1942-07-28 Du Pont Oxidation of ketones
US2343534A (en) * 1940-07-30 1944-03-07 Du Pont Preparation of adipic acid
US2386372A (en) * 1944-04-20 1945-10-09 Phillips Petroleum Co Production of cyclic ketones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2978473A (en) * 1958-09-30 1961-04-04 Texaco Inc Dibasic acid manufacture

Also Published As

Publication number Publication date
US2439513A (en) 1948-04-13
FR953498A (en) 1949-12-07

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