WO2013186305A1 - Process for preparing an internal olefin sulfonate - Google Patents
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- WO2013186305A1 WO2013186305A1 PCT/EP2013/062258 EP2013062258W WO2013186305A1 WO 2013186305 A1 WO2013186305 A1 WO 2013186305A1 EP 2013062258 W EP2013062258 W EP 2013062258W WO 2013186305 A1 WO2013186305 A1 WO 2013186305A1
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- internal olefin
- nucleophile
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- containing solution
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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Abstract
The invention relates to a process for preparing an internal olefin sulfonate, comprising sulfonating an internal olefin into sulfonated internal olefin, reacting sulfonated internal olefin with a nucleophile, with the proviso that the nucleophile is not water or hydroxide ion, and contacting the thus obtained reaction mixture with a base containing solution under reduced pressure.
Description
PROCESS FOR PREPARING AN INTERNAL OLEFIN SULFONATE
Field of the invention
The present invention relates to a process for preparing an internal olefin sulfonate.
Background of the invention
It is known to prepare internal olefin sulfonates by first sulfonating internal olefins, for example by contacting with sulfur trioxide as the sulfonating agent. This first sulfonation step results in a mixture which comprises sultones and alkene sulfonic acids, if any.
This is followed by contacting said mixture with a nucleophile. Generally, the nucleophile is water or hydroxide ion. In a case where the nucleophile is
hydroxide ion, added for example in the form of an aqueous sodium hydroxide (NaOH) containing solution, said alkene sulfonic acids are converted into alkene
sulfonates and said sultones are converted into hydroxy alkane sulfonates and possibly alkene sulfonates.
However, it is also known to contact said
intermediate mixture comprising sultones and alkene sulfonic acids with a nucleophile which is not water or hydroxide ion. For example, EP0446971A1 discloses that suitable other nucleophiles are aliphatic or aromatic (thio ) alcohols or alkoxides thereof, (capped)
polyethylene glycols or propylene glycols or their alkoxides, aliphatic or aromatic amines or the amides thereof, ammonia or heterocyclic nitrogen compounds.
Further, EP0446971A1 discloses that after the reaction with the nucleophile the product thus obtained can be converted into a surface active ionic form by reaction with a base, for example sodium hydroxide (NaOH) . For example, in a case where the nucleophile is an alcohol,
the reaction product would comprise an alkoxy alkane sulfonic acid. As taught by EP0446971A1, in order to make an anionic surfactant from such product, a subsequent treatment with a base can be performed resulting in alkoxy alkane sulfonate. In addition, such treatment with a base would also convert any alkene sulfonic acid into the corresponding sulfonate.
Usually, in the above-mentioned reaction with a nucleophile, the nucleophile is used in a molar excess over the compounds which need to be converted. Further, said reaction with a nucleophile may be performed in a solvent for the nucleophile, as also disclosed in
EP0446971A1 (e.g. n-hexane) . The consequence is that after such reaction, the remaining amount of the
nucleophile and possibly said solvent for the
nucleophile, if such solvent is used, is still present in the reaction mixture which should be separated therefrom. The presence of such nucleophile or solvent may have a detrimental effect on the properties of the final
product. Such remaining nucleophile and solvent may be separated from the reaction mixture after treatment with a base as discussed above.
However, it is cumbersome having to apply one or more additional separation steps after said treatment with a base. An object of the present invention is to provide a process for preparing an internal olefin sulfonate which is more efficient than known processes for preparing internal olefin sulfonates, in respect of the removal of remaining nucleophile and any solvent for the
nucleophile.
Summary of the invention
Surprisingly it was found that said object is
achieved by a process wherein after sulfonating an
internal olefin and after reacting the thus obtained sulfonated internal olefin with a nucelophile other than water or hydroxide ion, the thus obtained reaction mixture is contacted with a base containing solution under reduced pressure.
Accordingly, the present invention relates to a process for preparing an internal olefin sulfonate, comprising sulfonating an internal olefin into sulfonated internal olefin, reacting sulfonated internal olefin with a nucleophile, with the proviso that the nucleophile is not water or hydroxide ion, and contacting the thus obtained reaction mixture with a base containing solution under reduced pressure.
Advantageously, the present invention results in that (i) the step of contacting the reaction mixture obtained by reacting sulfonated internal olefin with a
nucleophile, other than water or hydroxide ion, with a base containing solution, and (ii) the step of removing remaining nucleophile and any solvent for the
nucleophile, are performed at the same time, since the pressure at which this is performed is a reduced
pressure, meaning that it is lower than atmospheric pressure, enabling remaining nucleophile and any solvent for the nucleophile to be removed at the same time. Doing both steps simultaneously is more efficient than having to perform both steps one after another. Thus, enormous savings in throughput time and operational costs may be obtained .
Detailed description of the invention
The process of the present invention is a process for preparing an internal olefin sulfonate (IOS) from an internal olefin. Within the present specification, an internal olefin and an IOS comprise a mixture of internal
olefin molecules and a mixture of IOS molecules,
respectively. That is to say, within the present
specification, "internal olefin" as such refers to a mixture of internal olefin molecules whereas "internal olefin molecule" refers to one of the components from such internal olefin. Analogously, within the present specification, "IOS" or "internal olefin sulfonate" as such refers to a mixture of IOS molecules whereas "IOS molecule" or "internal olefin sulfonate molecule" refers to one of the components from such IOS.
Branched IOS molecules are IOS molecules derived from internal olefin molecules which comprise one or more branches. Linear IOS molecules are IOS molecules derived from internal olefin molecules which are linear, that is to say which comprise no branches (unbranched internal olefin molecules) . An internal olefin may be a mixture of linear internal olefin molecules and branched internal olefin molecules. Analogously, an IOS may be a mixture of linear IOS molecules and branched IOS molecules.
Within the present specification, an internal olefin or IOS may be characterised by its carbon number, branched content and/or molecular weight. In case
reference is made to an average carbon number and/or average molecular weight, this means that the internal olefin or IOS in question is a mixture of molecules which differ from each other in terms of carbon number and/or molecular weight.
Within the present specification, said average carbon number is determined by multiplying the number of carbon atoms of each internal olefin molecule or IOS molecule by the weight fraction of that molecule and then adding the products, resulting in a weight average carbon number.
The average carbon number may be determined by GC
analysis .
Within the present specification, branched content is determined by dividing the amount of branched molecules by the total amount of branched and unbranched molecules.
The branched content may be determined by GC analysis.
Within the present specification, said average molecular weight is determined by multiplying the
molecular weight of each internal olefin molecule or IOS molecule by the mole fraction or weight fraction of that molecule and then adding the products, resulting in a number average or weight average molecular weight, respectively. The molecular weight may be determined by GC analysis.
In the present invention, an internal olefin
sulfonate is prepared from an internal olefin in a process comprising sulfonation followed by reaction with a nucleophile and finally by contacting the reaction mixture with a base containing solution.
In the sulfonation step of the present process, an internal olefin is sulfonated. In the present invention, the internal olefin may have an average carbon number of from 5 to 40, suitably 10 to 35, more suitably 15 to 30, most suitably 18 to 24.
Further, in the present invention, the branched content of the internal olefin used in the sulfonation step may be of from 0.1 to 30 wt.%, preferably 1 to 25 wt . % . Branches in the above-mentioned internal olefin molecules may include methyl, ethyl and/or higher
molecular weight branches including propyl branches.
In the present invention, the number average
molecular weight for the internal olefin may vary within
wide ranges, such as from 200 to 600, suitably 250 to 500, more suitably 300 to 400 g/mole.
An IOS molecule is made from an internal olefin molecule whose double bond is located anywhere along the carbon chain. Internal olefin molecules may be made by double bond isomerization of alpha-olefin molecules whose double bond is located at a terminal position. Generally, such isomerization results in a mixture of internal olefin molecules whose double bonds are located at different internal positions. The distribution of the double bond positions is mostly thermodynamically
determined. Further, that mixture may also comprise a minor amount of non-isomerized alpha-olefins . Still further, because the starting alpha-olefin may comprise a minor amount of paraffins (non-olefinic alkanes), the mixture resulting from alpha-olefin isomeration may likewise comprise that minor amount of unreacted
paraffins .
In the present invention, the amount of alpha-olefins in the internal olefin may be up to 5%, for example 1 to
4 wt . % based on total composition. Further, in the present invention, the amount of paraffins in the
internal olefin may be up to 15 wt.%, for example up to 12 wt.% based on total composition.
Suitable processes for making an internal olefin include those described in US5510306, US5633422,
US5648584, US5648585, US5849960, EP0830315B1 and "Anionic Surfactants: Organic Chemistry", Surfactant Science
Series, volume 56, Chapter 7, Marcel Dekker, Inc., New York, 1996, ed. H.W. Stacke.
In the sulfonation step of the present process, the internal olefin is contacted with a sulfonating agent. Reaction of the sulfonating agent with an internal olefin
leads to the formation of cyclic intermediates known as beta-sultones , which can undergo isomerization to
unsaturated sulfonic acids and the more stable gamma- and delta-sultones .
In the present invention, the sulfonating agent may be sulfur trioxide (SO3), sulfuric acid or oleum, of which sulfur trioxide is preferred. Further, in the present invention, the mole ratio of sulfonating agent to internal olefin may be 0.5:1 to 2:1, more suitably 0.8:1 to 1.8:1, most suitably 1:1 to 1.6:1.
In case sulfur trioxide is the sulfonating agent in the present process, the sulfur trioxide is preferably provided as a gas stream comprising a carrier gas and the sulfur trioxide. The carrier gas may be air or an inert gas, such as nitrogen. The concentration of sulfur trioxide in said gas stream may be 1 to 10 vol.%, more suitably 2 to 8 vol.%, most suitably 2 to 7 vol.%, based on the volume of the carrier gas.
The sulfonation reaction with SO3 is preferably carried out in a film reactor, for example a "falling- film reactor", where the olefin feed is continuously fed onto the inside surfaces of a tube and gaseous SO3 is fed into the tube to react with the (falling) olefin film in a controlled manner. The reactor may be cooled with a cooling means, which is preferably water, having a temperature preferably not exceeding 90 °C, especially a temperature in the range of from 10 to 70 °C, more suitably 20 to 60 °C, most suitably 20 to 55 °C, for example by flowing the cooling means at the outside walls of the reactor.
The present process may be carried out batchwise, semi-continuously or continuously, preferably
continuously. In particular, the sulfonation step may be
carried out batchwise, semi-continuously or continuously. Preferably, the sulfonation step is carried out
continuously .
In the present invention, after sulfonating the internal olefin into sulfonated internal olefin, the latter is contacted with a nucleophile causing reaction of sulfonated internal olefin with that nucleophile. In the present invention, said nucleophile is not water or hydroxide ion. A nucleophile is a molecule capable of attacking a positive centre or a positively polarized site in e.g. another molecule. Suitable nucleophiles in the present invention may be selected from the group consisting of aliphatic and aromatic (thio) alcohols and alkoxides thereof, (capped) polyethylene glycols and propylene glycols and their alkoxides, aliphatic and aromatic amines and the amides thereof, ammonia and heterocyclic nitrogen compounds. Preferably, the
nucleophile in the present invention is selected from the group consisting of aliphatic and aromatic
(thio ) alcohols , (capped) polyethylene glycols and
propylene glycols, and aliphatic and aromatic amines, most preferably aliphatic alcohols and aliphatic amines. It is preferred to react the sulfonated internal olefin, comprising sultones such as beta-sultones , with a
nucleophile which is selected from the group consisting of methanol, ethanol, propanol, isopropanol, n-pentanol, triethylene glycol mono-methyl ether, ethanolamine, n- butylamine, sodium n-propyl thiolate, sodium ethoxide and sodium phenolate, more preferably methanol, ethanol, propanol, isopropanol, n-pentanol, triethylene glycol mono-methyl ether, ethanolamine and n-butylamine .
Such sultones can react with the nucleophile in several ways. For a description thereof, reference is
made to EP0446971A1, the disclosure of which is
incorporated herein by reference. For example, in a case where in the present invention, the nucleophile is an alcohol, the reaction product would comprise an alkoxy alkane sulfonic acid, part of which may have been
dehydrated into an alkene sulfonic acid. It is preferred that in the reaction of sulfonated internal olefin with the nucleophile, the nucleophile is used in a molar excess over said sulfonated internal olefin to ensure a complete conversion of said sulfonated internal olefin.
Preferably, the mole ratio of the nucleophile to
sulfonated internal olefin is of from greater than 1:1 to 1.6:1, more preferably 1.05:1 to 1.5:1, most preferably 1.1:1 to 1.4:1. Further, such amount of the nucleophile may be used that the mole ratio of the nucleophile to sulfonating agent is of from greater than 1:1 to 1.6:1, more preferably 1.05:1 to 1.5:1, most preferably 1.1:1 to 1.4:1.
The step wherein the nucleophile is reacted with sulfonated internal olefin in the present process may be carried out batchwise, semi-continuously or continuously. Preferably, said step is carried out continuously.
Further, a continuously stirred tank reactor (CSTR) and/or a plug flow reactor may be used in this step.
Suitably, two or more CSTRs in series are used.
After the reaction of sulfonated internal olefin with the nucleophile and before contacting the thus obtained reaction mixture with a base containing solution, any remaining nucleophile may be neutral or may have a negative charge. For example, where the nucleophile is an alkoxide, it will have a negative charge. In both cases, such remaining nucleophile has to be removed. In
addition, in some cases, it may be desired to use a
solvent for the nucleophile, especially in a case where the nucleophile is negatively charged. Suitable solvents for the nucleophile are disclosed in EP0446971A1, the disclosure of which is incorporated herein by reference. For example, in Example 12 of EP0446971A1, lithium ethoxide is the nucleophile which is added in a solvent mixture of n-hexane and tetrahydrofuran . In case a solvent for the nucleophile is used in the present invention, then after the reaction of sulfonated internal olefin with the nucleophile, also such solvent remains in addition to any remaining nucleophile.
As discussed above, in a case where the nucleophile is for example an alcohol, the reaction product comprises an alkoxy alkane sulfonic acid. In order to make an anionic surfactant from this, a subsequent treatment with a base is needed. In the present invention, the reaction mixture obtained by reacting sulfonated internal olefin with the nucleophile is contacted with a base containing solution. Within the present specification, "base
containing solution" implies that the base is dissolved in a solvent, thereby forming said solution, when the base is contacted with said reaction product. Said solvent is thus a solvent for the base, which solvent is preferably water.
The base to be used may be a water soluble base, which is preferably selected from the group consisting of hydroxides, carbonates and bicarbonates of an alkali metal ion, such as sodium or potassium, or of ammonium ion, and amine compounds. Suitable examples are sodium hydroxide and sodium carbonate, most suitably sodium hydroxide. Further, preferably, the solvent for the base is water. Preferably, in this step, an aqueous solution of a water soluble base, such as described hereinabove,
especially sodium hydroxide, is used as the base
containing solution.
The reaction in this step is generally carried out with an excessive molar amount of base. It is preferred that the final internal olefin sulfonate product is not acidic because this may lead to corrosion of process equipment and/or to disintegration of the internal olefin sulfonate. Therefore, it is preferred that the final internal olefin sulfonate product contains a certain amount of base, for example 0.1 to 2 wt . % based on 100% of the active matter. This may be achieved by choosing the amount of base to be added such that the molar ratio of (i) the amount of base fed to the step wherein the reaction mixture, obtained by reacting sulfonated
internal olefin with the nucleophile, is contacted with the base containing solution to (ii) the amount of sulfonating agent (e.g. SO3) fed to the sulfonation step is higher than 1, suitably higher than 1 up to 1.4, more suitably 1.1 to 1.3.
The base and the solvent for the base may be added separately. Preferably, the base is added as part of a solution as described above. Additional solvent may be added separately in addition to such base containing solution. If the base is added as part of a solution, the concentration of the base in such solution, based on total solution, is suitably at most 60 wt.%, more
suitably 10 to 55 wt.%, most suitably 20 to 55 wt.%.
The temperature at which the treatment with the base containing solution in the present process is carried out may vary within wide ranges, for example 0 to 250 °C.
Further, the treatment time may also vary within wide ranges, for example 5 minutes to 4 hours.
The step wherein the treatment with the base
containing solution in the present process is carried out may be carried out batchwise, semi-continuously or continuously. Preferably, said step is carried out continuously.
US4183867, US4248793 and EP0351928A1, the disclosures of all of which are incorporated herein by reference, disclose processes which can be used to make internal olefin sulfonates in the process of the present
invention. Further, the internal olefin sulfonates may be synthesized in a way as described by Van Os et al . in "Anionic Surfactants: Organic Chemistry", Surfactant Science Series 56, ed. Stacke H.W., 1996, Chapter 7:
Olefin sulfonates, pages 367-371, the disclosure of which is incorporated herein by reference.
Further, such reactor should be used in the step of the treatment with the base containing solution that allows for the treatment to take place under reduced pressure. As mentioned above, "reduced pressure" within the present specification means that the pressure is lower than atmospheric pressure. Further, preferably, the temperature is sufficiently high for remaining
nucleophile and any solvent for the nucleophile to be separated and removed. A suitable reactor for this step is a film evaporator, preferably a wiped film evaporator
(WFE) . Further, it is preferred that the temperature and pressure in this step are chosen such that the solvent for the base containing solution, which solvent is preferably water as discussed above, is not separated and removed or is separated and removed to only a small extent. It is therefore preferred that the nucleophile is more volatile than said solvent for the base containing solution. This means that at a given pressure, the
temperature is suitably maintained below the boiling point of said solvent for the base containing solution, but at or above the boiling point of said remaining nucleophile and any solvent for the nucleophile.
In the present invention, it is preferred that in the step of the treatment with the base containing solution, the pressure is of from 0.01 bar to lower than 1 bar, more preferably of from 0.05 bar to lower than 1 bar, most preferably of from 0.05 bar to 0.5 bar. Preferably, said pressure is at most 0.9 bar, more preferably at most
0.7 bar, more preferably at most 0.5 bar, more preferably at most 0.3 bar, most preferably at most 0.2 bar.
Further, preferably, said pressure is at least 0.01 bar, more preferably at least 0.03 bar, more preferably at least 0.05 bar, more preferably at least 0.07 bar, most preferably at least 0.09 bar. Further, the temperature in this step is preferably of from 0 to lower than 100 °C, more preferably of from 10 to lower than 100 °C, more preferably of from 15 to lower than 100 °C, more
preferably of from 20 to lower than 100 °C, more
preferably of from 20 to 80 °C, most preferably of from 20 to 60 °C.
Applying said treatment at a reduced pressure, for example in a WFE, enables removing remaining nucleophile and any solvent for the nucleophile at the same time when turning acidic reaction product, obtained by reaction with the nucleophile, into the desired internal olefin sulfonate anionic surfactant. In addition, any remaining negatively charged nucleophile would be neutralized and directly removed at the same time. One of the advantages of the present invention is that any nucleophile and possibly said solvent for the nucleophile that remain after the reaction of sulfonated internal olefin with the
nucleophile, are removed in the same step wherein the treatment with the base containing solution is carried out. Therefore, advantageously, no separate step for removing said nucleophile and solvent is needed. Doing both steps simultaneously is more efficient than having to perform both steps one after another. Thus, enormous savings in throughput time and operational costs may be obtained .
After the treatment with the base containing solution in the present process, the internal olefin sulfonate (IOS) product may be diluted, for example by adding additional solvent (e.g. water), for example in case one wishes to facilitate the handling of that product in the application for which the IOS product is intended, for example in the application as a surfactant.
The internal olefin sulfonate (IOS) prepared by the present process for preparing an internal olefin
sulfonate may be used as a surfactant in any kind of process, for example in a method of chemical Enhanced Oil Recovery (cEOR) for maximising the yield of hydrocarbons (oil) from a subterranean reservoir.
Claims
1. Process for preparing an internal olefin sulfonate, comprising sulfonating an internal olefin into sulfonated internal olefin, reacting sulfonated internal olefin with a nucleophile, with the proviso that the nucleophile is not water or hydroxide ion, and contacting the thus obtained reaction mixture with a base containing solution under reduced pressure.
2. Process according to claim 1, wherein contacting the reaction mixture with the base containing solution is carried out under reduced pressure in a film evaporator, preferably a wiped film evaporator.
3. Process according to any one of the preceding claims, which is carried out continuously.
4. Process according to any one of the preceding claims, wherein the base is a water soluble base and the solvent for the base is water.
5. Process according to claim 4, wherein the water soluble base is selected from the group consisting of hydroxides, carbonates and bicarbonates of an alkali metal ion, such as sodium or potassium, or of ammonium ion, and amine compounds.
6. Process according to claim 5, wherein the water soluble base is sodium hydroxide.
7. Process according to any one of the preceding claims, wherein the temperature at which the reaction mixture is contacted with the base containing solution is 0 to 250 °C.
8. Process according to any one of the preceding claims, wherein the nucleophile is selected from the group consisting of aliphatic and aromatic (thio) alcohols and
alkoxides thereof, (capped) polyethylene glycols and propylene glycols and their alkoxides, aliphatic and aromatic amines and the amides thereof, ammonia and heterocyclic nitrogen compounds.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12171761.5 | 2012-06-13 | ||
| EP12171761 | 2012-06-13 |
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| Publication Number | Publication Date |
|---|---|
| WO2013186305A1 true WO2013186305A1 (en) | 2013-12-19 |
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ID=48607291
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2013/062258 WO2013186305A1 (en) | 2012-06-13 | 2013-06-13 | Process for preparing an internal olefin sulfonate |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10035746B2 (en) | 2015-05-07 | 2018-07-31 | Rhodia Operations | Process for the decarboxylative ketonization of fatty acids or fatty acid derivatives |
| US11267781B2 (en) | 2016-11-08 | 2022-03-08 | Rhodia Operations | Method for making end compounds from internal ketones issued from the decarboxylative ketonization of fatty acids or fatty acid derivatives |
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| US3755429A (en) * | 1971-10-12 | 1973-08-28 | Procter & Gamble | Process for the preparation of sulfonated detergent composition |
| US4183867A (en) | 1977-08-25 | 1980-01-15 | The Lion Fat & Oil Co. | Method for preparation of internal olefin sulfonate |
| US4248793A (en) | 1979-09-26 | 1981-02-03 | The Lion Fat & Oil Co., Ltd. | Process for the production of internal olefin sulfonate |
| EP0293913A1 (en) * | 1987-06-04 | 1988-12-07 | Raschig AG | Process for the preparation of ethanesulfone compounds which may be substituted |
| EP0351928A1 (en) | 1988-07-20 | 1990-01-24 | Shell Internationale Researchmaatschappij B.V. | A process for the preparation of internal olefin sulphonates |
| EP0446971A1 (en) | 1990-01-12 | 1991-09-18 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of substituted sulphonic acids and/or sulphonates |
| US5510306A (en) | 1993-12-29 | 1996-04-23 | Shell Oil Company | Process for isomerizing linear olefins to isoolefins |
| US5648585A (en) | 1993-12-29 | 1997-07-15 | Murray; Brendan Dermot | Process for isomerizing linear olefins to isoolefins |
| US5849960A (en) | 1996-11-26 | 1998-12-15 | Shell Oil Company | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
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|---|---|---|---|---|
| US3755429A (en) * | 1971-10-12 | 1973-08-28 | Procter & Gamble | Process for the preparation of sulfonated detergent composition |
| US4183867A (en) | 1977-08-25 | 1980-01-15 | The Lion Fat & Oil Co. | Method for preparation of internal olefin sulfonate |
| US4248793A (en) | 1979-09-26 | 1981-02-03 | The Lion Fat & Oil Co., Ltd. | Process for the production of internal olefin sulfonate |
| EP0293913A1 (en) * | 1987-06-04 | 1988-12-07 | Raschig AG | Process for the preparation of ethanesulfone compounds which may be substituted |
| EP0351928A1 (en) | 1988-07-20 | 1990-01-24 | Shell Internationale Researchmaatschappij B.V. | A process for the preparation of internal olefin sulphonates |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10035746B2 (en) | 2015-05-07 | 2018-07-31 | Rhodia Operations | Process for the decarboxylative ketonization of fatty acids or fatty acid derivatives |
| US11267781B2 (en) | 2016-11-08 | 2022-03-08 | Rhodia Operations | Method for making end compounds from internal ketones issued from the decarboxylative ketonization of fatty acids or fatty acid derivatives |
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