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WO1998037045A1 - Traitement d'une charge d'alimentation organique renfermant des composes organiques oxygenes indesirables - Google Patents

Traitement d'une charge d'alimentation organique renfermant des composes organiques oxygenes indesirables Download PDF

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Publication number
WO1998037045A1
WO1998037045A1 PCT/GB1998/000570 GB9800570W WO9837045A1 WO 1998037045 A1 WO1998037045 A1 WO 1998037045A1 GB 9800570 W GB9800570 W GB 9800570W WO 9837045 A1 WO9837045 A1 WO 9837045A1
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WO
WIPO (PCT)
Prior art keywords
feedstock
hydroxide
liquid
process according
alcohol
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.)
Ceased
Application number
PCT/GB1998/000570
Other languages
English (en)
Inventor
Herman Preston
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.)
Sasol Chemicals Europe Ltd
Sasol Technology Pty Ltd
Original Assignee
Sasol Chemicals Europe Ltd
Sasol Technology Pty Ltd
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 Sasol Chemicals Europe Ltd, Sasol Technology Pty Ltd filed Critical Sasol Chemicals Europe Ltd
Priority to AU63021/98A priority Critical patent/AU6302198A/en
Publication of WO1998037045A1 publication Critical patent/WO1998037045A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound

Definitions

  • THIS INVENTION relates to the treatment of an organic feedstock containing undesired oxygenated organic compounds. It relates in particular to a process for ameliorating a liquid organic feedstock containing undesired oxygenated organic compounds such as esters, aldehydes and/or organic acids.
  • a process for ameliorating a liquid organic feedstock containing at least one undesired oxygenated organic compound comprises admixing the liquid organic feedstock, a liquid alcohol and a hydroxide; and allowing the hydroxide to react with the undesired oxygenated organic compound, to form a salt of the undesired organic compound.
  • the Applicant believes that the process of the invention will find particular application in the treatment of a liquid organic feedstock comprising oxygenated organic compounds.
  • the liquid organic feedstock may be that obtained by hydroformylating an olefin-rich feedstock, eg a Fischer-Tropsch derived olefinic product.
  • Such a liquid organic feedstock thus is aldehyde and/or alcohol based. Typically, it comprises alcohols having from 8 to 17 carbon atoms, ie Co to C ⁇ 7 alcohols.
  • the feedstock When the feedstock is Fischer-Tropsch derived, it can, for example, be the product from a reactor such as that commonly known as a Synthol reactor.
  • the unwanted oxygenated organic compounds can be esters, aldehydes and/or organic acids, but the principal unwanted compounds are normally esters in such a hydroformylation derived feedstock.
  • the liquid alcohol which is admixed with the liquid organic feedstock preferably has fewer carbon atoms than the alcohol (s) in the feedstock, and may have from 1 to 5 carbon atoms.
  • the liquid alcohol may be methanol, ethanol or propanol.
  • the hydroxide may be a hydroxide of a metal of Group IA, Group IIA or Group I IB of the Periodic Table of Elements.
  • the metal of the metal hydroxide is sodium, potassium, rubidium, cesium, barium or calcium.
  • the metal hydroxide may be sodium hydroxide, due to its high solubility in the preferred alcohols, its high reactivity and its relatively low cost.
  • the reaction of the hydroxide with the undesired oxygenated organic compound will thus take place in a reaction zone provided by a suitable vessel or reactor.
  • the liquid alcohol and the hydroxide can be added separately to the vessel, but are preferably added as a premixture .
  • the esters are transformed by an irreversible hydrolysis reaction (1) involving the hydroxide:
  • the liquid alcohol in the first instance acts as a solvent for the hydroxide.
  • the alcohol also reacts with the hydroxide to form small amounts of an alkoxide in accordance with reaction (2) : MOH + R"OH ⁇ R"0 ⁇ M + + H 2 0 (2) wherein M is as hereinbefore defined, and R" is a hydrocarbon radical.
  • the Applicant has further surprisingly found that the alkoxide, ROM, is a catalyst for the hydrolysis reaction (1) .
  • the salts of the unwanted compounds and excess hydroxide and alkoxide can be removed from the treated liquid organic feedstock. It will form part of a heavy tail of the organic feedstock and can be removed, eg by means of distillation, if required.
  • the process may also include separating the liquid alcohol from the treated feedstock, eg by means of a stripper.
  • the reaction temperature may be between 20°C and 100°C, typically about 75 °C.
  • the pressure in the vessel may be atmospheric pressure.
  • the retention time of the feedstock in the vessel will be sufficient for reaction (1) to be completed, and may thus be between 5 and 20 minutes.
  • the relative proportions of the liquid organic feedstock, the hydroxide and the liquid alcohol will depend on the amounts of esters present in the organic feedstock. However, typically the volumetric proportion of feedstock to liquid alcohol can be in the range 5:1 to about 10:1, eg about 6:1.
  • the proportion of hydroxide used will depend on the quantities of unwanted esters in the feedstock, but can typically be in the range of 0,5g per 100m£ feedstock and 5g per lOOmf feedstock, eg about 2g of hydroxide per 100m£ feedstock.
  • reference numeral 10 generally indicates a process according to the invention for ameliorating a liquid organic feedstock containing undesired oxygenated organic compounds .
  • the process 10 includes a caustic make-up vessel 12, with a methanol flow line 14 leading into the vessel 12.
  • a caustic or sodium hydroxide make-up flow line 16 also leads into the vessel 12.
  • a flow line 18 leads from the vessel 12 to an ester transformation reactor 20.
  • a liquid organic feedstock flow line 22 also leads into the • reactor 20, while a treated feedstock withdrawal line 24 leads from the reactor 20 to a stripper 26.
  • a methanol recycle line 28 leads from the top of the stripper 26 to the vessel 12, while a treated feedstock or product withdrawal line 30 leads from the bottom of the stripper 26.
  • a feedstock comprising C ⁇ to C ⁇ alcohols and obtained from the hydroformylation of SYNTHOL (trademark) products as described in, for example, PCT/GB96/01563 which is hence incorporated herein by reference, is fed into the vessel 20 along the flow line 22, together with a premix of methanol and sodium hydroxide entering the vessel 20 along the flow line 18.
  • the vessel 20 is sized such that the retention time of the feedstock in the vessel is between 5 and 20 minutes.
  • Unwanted esters in the organic feedstock react in accordance with reaction (1) , to be transformed into their corresponding salts, with reaction (1) being assisted by the alkoxide formed in accordance with reaction (2) .
  • M of reaction (1) is Na
  • R" of reaction (2) is CH3.
  • the reaction conditions in the vessel 20 are moderate.
  • the temperature in the reactor can be controlled at about 75 °C, and the vessel 20 can operate at atmospheric pressure.
  • a C j 2_i3 oxo alcohol liquid feedstock, as produced in accordance with Example 10 of our co-pending PCT/GB96/01563 was used as feedstock in this example. It was thus obtained by the hydroformylation of a Fischer-Tropsch derived olefinic product. 300m£ of the feedstock was placed in a 500m round bottom flask equipped with a condenser. The feedstock was heated up to about 70°C by means of a hot plate, and l,5g of sodium hydroxide, dissolved in 50m£ methanol and preheated to 65°C, was added to the organic feedstock.
  • the retention time was drastically shortened to between 5 and 20 minutes.
  • the retention times can be up to 3 to 5 hours.
  • the operating conditions in the process according to the invention are much milder with the reaction temperature being approximately 75°C compared to a reaction temperature of about 100°C in the known processes.
  • the process is more economical to operate, since substantially less sodium hydroxide is required than in the known processes.
  • typically 6g of sodium hydroxide dissolved in 200m of methanol can be used to treat 1kg of organic feed.
  • lOOg of sodium hydroxide dissolved in 500m£ of water is typically required to treat the same quantity of feedstock.
  • no caustic waste water is generated with the process according to the invention, whereas large quantities are produced in the known processes.
  • the use of an alcohol as opposed to water results in a 1-phase system with no associated mixing difficulties in the reaction vessel, giving rise to the very short retention times. The alcohol can also be recycled leading to little alcohol wastage .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé permettant d'améliorer une charge d'alimentation organique liquide renfermant au moins un composé organique oxygéné indésirable, consistant à mélanger la charge d'alimentation organique liquide, un alcool liquide et un hydroxyde. On fait réagir l'hydroxyde avec le composé organique oxygéné indésirable, afin de former un sel du composé organique indésirable.
PCT/GB1998/000570 1997-02-24 1998-02-24 Traitement d'une charge d'alimentation organique renfermant des composes organiques oxygenes indesirables Ceased WO1998037045A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU63021/98A AU6302198A (en) 1997-02-24 1998-02-24 Treatment of an organic feedstock containing undesired oxygenated organic compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ZA97/1571 1997-02-24
ZA971571 1997-02-24

Publications (1)

Publication Number Publication Date
WO1998037045A1 true WO1998037045A1 (fr) 1998-08-27

Family

ID=25586256

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/000570 Ceased WO1998037045A1 (fr) 1997-02-24 1998-02-24 Traitement d'une charge d'alimentation organique renfermant des composes organiques oxygenes indesirables

Country Status (2)

Country Link
AU (1) AU6302198A (fr)
WO (1) WO1998037045A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014138590A3 (fr) * 2013-03-07 2014-11-13 Ls9, Inc. Traitement en aval de compositions d'alcool gras produites par des cellules hôtes recombinantes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2595763A (en) * 1949-12-31 1952-05-06 Standard Oil Dev Co Treatment of oxo alcohols by caustic and air
US2993078A (en) * 1958-12-22 1961-07-18 Gen Aniline & Film Corp Purification of butynediol
US3761534A (en) * 1971-12-29 1973-09-25 Dow Chemical Co Removal of acidic contaminants from process streams

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2595763A (en) * 1949-12-31 1952-05-06 Standard Oil Dev Co Treatment of oxo alcohols by caustic and air
US2993078A (en) * 1958-12-22 1961-07-18 Gen Aniline & Film Corp Purification of butynediol
US3761534A (en) * 1971-12-29 1973-09-25 Dow Chemical Co Removal of acidic contaminants from process streams

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014138590A3 (fr) * 2013-03-07 2014-11-13 Ls9, Inc. Traitement en aval de compositions d'alcool gras produites par des cellules hôtes recombinantes
KR20150125711A (ko) * 2013-03-07 2015-11-09 알이지 라이프 사이언시스, 엘엘씨 재조합 숙주 세포에 의해 생성된 지방알코올 조성물들의 하류 공정
CN105324358A (zh) * 2013-03-07 2016-02-10 Reg生命科学有限责任公司 由重组宿主细胞生产的脂肪醇组合物的下游处理
JP2016510761A (ja) * 2013-03-07 2016-04-11 アールイージー ライフ サイエンシズ リミテッド ライアビリティ カンパニー 組み換え宿主細胞により産生された脂肪族アルコール組成物の下流処理
AU2014225436B2 (en) * 2013-03-07 2018-05-10 Genomatica, Inc. Downstream processing of fatty alcohol compositions produced by recombinant host cells
JP2018076346A (ja) * 2013-03-07 2018-05-17 アールイージー ライフ サイエンシズ リミテッド ライアビリティ カンパニー 組み換え宿主細胞により産生された脂肪族アルコール組成物の下流処理
EP3770142A1 (fr) * 2013-03-07 2021-01-27 Genomatica, Inc. Traitement en aval de compositions d'alcool gras produites par des cellules hôtes recombinantes
KR102271255B1 (ko) * 2013-03-07 2021-06-30 게노마티카 인코포레이티드 재조합 숙주 세포에 의해 생성된 지방알코올 조성물들의 하류 공정
US11053184B2 (en) 2013-03-07 2021-07-06 Genomatica, Inc. Downstream processing of fatty alcohol compositions produced by recombinant host cells
KR20220025905A (ko) * 2013-03-07 2022-03-03 게노마티카 인코포레이티드 재조합 숙주 세포에 의해 생성된 지방알코올 조성물들의 하류 공정
JP2022045359A (ja) * 2013-03-07 2022-03-18 ジェノマティカ， インコーポレイテッド 組み換え宿主細胞により産生された脂肪族アルコール組成物の下流処理
KR102456004B1 (ko) * 2013-03-07 2022-10-18 게노마티카 인코포레이티드 재조합 숙주 세포에 의해 생성된 지방알코올 조성물들의 하류 공정

Also Published As

Publication number Publication date
AU6302198A (en) 1998-09-09

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