WO1998037045A1 - Treatment of an organic feedstock containing undesired oxygenated organic compounds - Google Patents
Treatment of an organic feedstock containing undesired oxygenated organic compounds Download PDFInfo
- 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
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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 .
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- 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
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. The hydroxide is allowed to react with the undesired oxygenated organic compound, to form a salt of the undesired organic compound.
Description
TREATMENT OF AN ORGANIC FEEDSTOCK CONTAINING UNDESIRED OXYGENATED ORGANIC COMPOUNDS
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.
According to the invention, there is provided a process for ameliorating a liquid organic feedstock containing at least one undesired oxygenated organic compound, which process 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.
While any liquid organic feedstock containing, eg contaminated with, the undesired oxygenated organic compounds, can in principle be used, 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. Thus, 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 Cι7 alcohols. 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. In particular, 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. Preferably, the metal of the metal hydroxide is sodium, potassium, rubidium, cesium, barium or calcium. In particular, 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:
RCOOR' + MOH → RCOO"M+ + R'OH (1) wherein R and R' are hydrocarbon radicals, and M is a metal of Group IA, Group IIA or Group IIB.
The liquid alcohol in the first instance acts as a solvent for the hydroxide. However, it was surprisingly found that 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+ + H20 (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) .
If desired, 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.
Similarly, 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.
The invention will now be described by way of non-limiting example and by way of the following simplified flow diagram of a process according to the invention for ameliorating a liquid organic feedstock.
In the drawing, 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.
In use, 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) . Thus, in the process 10, M of reaction (1) is Na, while R" of reaction (2) is CH3. It will be appreciated that only small quantities of the methanol react with the sodium hydroxide to form the alkoxide. Due to the high efficiency of the process of the invention for transforming the esters into their corresponding salts, the reaction conditions in the vessel 20 are moderate. Thus, the temperature in the reactor can be controlled at about 75 °C, and the vessel 20 can operate at atmospheric pressure.
The process 10 was demonstrated on laboratory scale by means of the following non-limiting example.
EXAMPLE
A Cj2_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 mixture was stirred by means of a magnetic stirrer, while the temperature was maintained at 75 °C by means of the condenser. After 10 minutes, the methanol was flashed off, and the
alcohol separated from its heavy tail (and thus also from the sodium salts of the esters which had formed) by means of vacuum distillation. The feedstock sample was then analyzed for esters with the following results: CP-13 alcohol sample before ester removal Esters = 2,5mgKOH/g
C12.13 alcohol sample after ester removal Esters = 0,02mgKOH/g
It was thus surprisingly found that in the process of the present invention, which uses a liquid alcohol as a solvent for sodium hydroxide rather than water which is used as a solvent in known processes for removal of esters from organic feedstocks, the retention time was drastically shortened to between 5 and 20 minutes. In the known processes, the retention times can be up to 3 to 5 hours.
Furthermore, 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. Still further, the process is more economical to operate, since substantially less sodium hydroxide is
required than in the known processes. For example, in the process of the invention, typically 6g of sodium hydroxide dissolved in 200m of methanol can be used to treat 1kg of organic feed. In contrast, in known processes, lOOg of sodium hydroxide dissolved in 500m£ of water, is typically required to treat the same quantity of feedstock. Further, no caustic waste water is generated with the process according to the invention, whereas large quantities are produced in the known processes. Still further, 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 .
Claims
1. A process for ameliorating a liquid organic feedstock containing at least one undesired oxygenated organic compound, which process 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.
2. A process according to Claim 1, wherein the liquid organic feedstock is that obtained by hydrofcrmyiating an olefin-rich feedstock, so that the liquid organic feedstock is alcohol based, with esters, aldehydes and/or organic acids being present therein as undesired oxygenated compounds.
3. A process according to Claim 2, wherein the liquid alcohol which is admixed with the liquid organic feedstock has fewer carbon atoms than the alcohol (s) in the feedstock.
4. A process according to Claim 3, wherein the liquid alcohol is methanol, ethanol or propanol .
5. A process according to any one of Claims 1 to 4 inclusive, wherein the hydroxide is a hydroxide of a metal of Group IA, Group IIA or Group IIB of the Periodic Table of Elements.
6. A process according to Claim 5, wherein the metal of the hydroxide is sodium, potassium, rubidium, cesium, barium or calcium.
7. A process according to Claim 6, wherein the metal hydroxide is sodium hydroxide.
8. A process according to any one of Claims 1 to 7 inclusive, wherein the reaction of the hydroxide with the undesired oxygenated organic compound takes place in a reaction zone provided by a suitable vessel, with the liquid alcohol and the hydroxide being added to the vessel as a premixture .
9. A process according to Claim 8, wherein the reaction temperature in the reaction zone is between 20°C and 100°C, the pressure in the vessel is about atmospheric pressure, and the retention time of the liquid organic feedstock in the reactor is between 5 and 20 minutes.
10. A process according to any one of Claims 1 to 9 inclusive, wherein the volumetric proportion of the liquid organic feedstock to liquid alcohol is in the range 5:1 to about 10:1, while the proportion of hydroxide used is in the range of 0,5g per lOOmf feedstock and 5g per 100m feedstock.
11. A novel process of ameliorating a liquid organic feedstock, substantially as described and illustrated herein.
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 (en) | 1998-08-27 |
Family
ID=25586256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1998/000570 Ceased WO1998037045A1 (en) | 1997-02-24 | 1998-02-24 | Treatment of an organic feedstock containing undesired oxygenated organic compounds |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU6302198A (en) |
| WO (1) | WO1998037045A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014138590A3 (en) * | 2013-03-07 | 2014-11-13 | Ls9, Inc. | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
Citations (3)
| 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 |
-
1998
- 1998-02-24 AU AU63021/98A patent/AU6302198A/en not_active Abandoned
- 1998-02-24 WO PCT/GB1998/000570 patent/WO1998037045A1/en not_active Ceased
Patent Citations (3)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014138590A3 (en) * | 2013-03-07 | 2014-11-13 | Ls9, Inc. | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| KR20150125711A (en) * | 2013-03-07 | 2015-11-09 | 알이지 라이프 사이언시스, 엘엘씨 | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| CN105324358A (en) * | 2013-03-07 | 2016-02-10 | Reg生命科学有限责任公司 | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| JP2016510761A (en) * | 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 | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| AU2014225436B2 (en) * | 2013-03-07 | 2018-05-10 | Genomatica, Inc. | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| JP2018076346A (en) * | 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 | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| EP3770142A1 (en) * | 2013-03-07 | 2021-01-27 | Genomatica, Inc. | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| KR102271255B1 (en) * | 2013-03-07 | 2021-06-30 | 게노마티카 인코포레이티드 | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| US11053184B2 (en) | 2013-03-07 | 2021-07-06 | Genomatica, Inc. | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| KR20220025905A (en) * | 2013-03-07 | 2022-03-03 | 게노마티카 인코포레이티드 | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| JP2022045359A (en) * | 2013-03-07 | 2022-03-18 | ジェノマティカ， インコーポレイテッド | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
| KR102456004B1 (en) * | 2013-03-07 | 2022-10-18 | 게노마티카 인코포레이티드 | Downstream processing of fatty alcohol compositions produced by recombinant host cells |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6302198A (en) | 1998-09-09 |
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