EP0562914B1 - Verfahren zum Waschen fester Teilchen mit einer Sophoroside enthaltenden Lösung - Google Patents

Verfahren zum Waschen fester Teilchen mit einer Sophoroside enthaltenden Lösung Download PDF

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Publication number
EP0562914B1
EP0562914B1 EP93400673A EP93400673A EP0562914B1 EP 0562914 B1 EP0562914 B1 EP 0562914B1 EP 93400673 A EP93400673 A EP 93400673A EP 93400673 A EP93400673 A EP 93400673A EP 0562914 B1 EP0562914 B1 EP 0562914B1
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EP
European Patent Office
Prior art keywords
sophorosides
washing
solution
cuttings
solid particles
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 - Lifetime
Application number
EP93400673A
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English (en)
French (fr)
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EP0562914A1 (de
Inventor
Marc Baviere
Didier Degouy
Jacqueline Lecourtier
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.)
Sophor SA
Original Assignee
IFP Energies Nouvelles IFPEN
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the present invention relates to a method using a solution containing sophorosides, said method being suitable for cleaning solid particles impregnated with hydrocarbons. This process is more particularly intended for washing petroleum drill cuttings.
  • drilling fluids containing hydrocarbons to solve drilling problems in reactive formations in the presence of water, for example certain clays or salt.
  • Drilling fluids suitable for high temperatures can also be based on mineral oil.
  • mineral oil In particular, in the North Sea, around 75% of wells are drilled with oil-based fluids. In these cases, the cuttings that rise to the surface are impregnated with a relatively large amount of hydrocarbon.
  • the first two choices may not be viable for technical and / or economic reasons. It will be advantageous to use the third technique by having an efficient and economical means for washing the cuttings on site.
  • Document EP-A-0330379 discloses an aqueous formulation intended for cleaning surfaces soaked in oil, for example drill cuttings.
  • said solids are drill cuttings.
  • the solution can include sophorosides in a concentration between 0.1 to 30 g / liter.
  • the washing solution can comprise at least one other compound suitable for one of the following functions: adjusting the pH of the solution, dissolving the hydrocarbons, inhibiting swelling and / or dispersion of the solid particles.
  • Said washing solution can be separated from said polluting fluid by decantation and / or centrifugation.
  • sophorosides can now be considered because the patent application FR-90/16211 of the applicant discloses a particularly advantageous process for the manufacture of sophorosides. Indeed, before knowledge of this process, it was particularly difficult and very expensive to manufacture industrial quantities of this product. However, this family of products, known for its use in cosmetology or in the food industry, reveals interesting properties, in particular for washing drill cuttings.
  • lactone and ester of sophorosides are specified below.
  • sophorosides are described from 1961 in particular by Gorin et al. in Can. J. Chem., 39, 846-55 (1961), Asmer et al. in J. American Oil Chem. Soc., 65 (9), 1460-6 (Sept. 1988) and by Spencer et al. (US 3205150).
  • Sophorosides are glycosides resulting from the association of a sugar, sophorose, formed by yeast from two glucose molecules, and a hydroxy fatty acid also produced by yeast from substrates such as hydrocarbons. , saturated or unsaturated fatty acids, fatty acid esters including glycerides, and vegetable oils: rapeseed, sunflower, palm or soybean oils, methyl or ethyl esters of these oils.
  • the hydroxylation of the fatty acid takes place in position ⁇ or most often in ⁇ - 1 with respect to the carboxylic acid function.
  • Sophorosides are considered to be a mixture of compounds, the structures of which can be represented by the formulas (1) and (2) below:
  • R1 represents hydrogen or an acetyl group (CH3CO-)
  • R2 represents hydrogen or an alkyl radical containing 1 to 9 carbon atoms when R3 is a saturated hydrocarbon radical comprising 7 with 16 carbon atoms
  • R2 represents hydrogen or a methyl group when R3 is an unsaturated hydrocarbon radical containing 13 to 17 carbon atoms.
  • the cyclization of the fatty acid form (formula (1)) to give the lactone form (formula (2)) can be carried out as indicated in formula (2) or on other sites of the sophorose radical, for example those indicated by the arrows.
  • Sophorosides therefore consist of a mixture of numerous compounds, in particular isomers and homologs.
  • the composition of this mixture depends on the nature of the substrate and the fermentation conditions. Reference may be made to document FR-2399438 cited in application FR90 / 16211.
  • the sophorosides can be used as amphiphilic agents thanks to the presence in the molecule of a hydrophilic part formed by the sophorose group and of a lipophilic part constituted by the fatty acid.
  • the amphiphilic character is highlighted in particular by the surface-active properties, for example, lowering of the surface tension of water (Abe et al., US4297340) or of interfacial tension water-hydrocarbon (Gutnick and Minas, Biochem. Soc. Trans., 22S-35S (1987)), emulsifiers or demulsifiers (Cooper and Paddock, Applied and Environmental Microbiology, 47 (1), 173-6 (1984)), wetting agents , etc.
  • the properties of the direct fermentation product can be modulated depending on the desired result or application. Indeed, by a judicious choice of the substrate, that is to say more precisely the structure and the molecular mass of the hydrocarbons, fatty acids or fatty acid esters involved in the fermentation manufacturing process. , it is possible to adjust, to some extent, the HLB of the product.
  • HLB Hydrophilic-Lipophilic Balance
  • the concept of HLB or Hydrophilic-Lipophilic Balance has been described by Griffin in J. Soc. Cosmetic Chemists, 1, 311-24 (1949).
  • the product obtained will tend to preferably form emulsions of the water in oil type. Above this value, the emulsions formed will preferably be of the oil in water type.
  • the direct fermentation product can subsequently be the subject of chemical modifications making it possible to better adapt the structure, and therefore the properties of the majority compounds, to the requirements of the application.
  • sophorosides are both fully biodegradable and non-toxic, unlike the surfactants generally used in the technical field of the present invention, whether they are ionic, for example alkylaryl sulfonates, or nonionic, for example, polyethoxylated derivatives. These characteristics represent a very interesting advantage over ecological problems.
  • the cuttings and the solution are mixed by stirring for 15 minutes using a magnetic bar.
  • the mixture is then centrifuged at 1500 rpm for 15 minutes, to separate the cuttings from the washing solution.
  • the cuttings are then rinsed with 10 ml of sea water.
  • a second centrifugation is then carried out to remove the rinsing water, followed by a second rinsing.
  • the mixture is filtered on a Millipore filter of 8 micrometers of mesh opening.
  • Table 1 gives the results of washing the cuttings with a solution of sophoroside in seawater: Table 1 WASHING WITH SOPHOROSIDE SOLUTION Concent. in SO1 MODEL DEBLAIS NATURAL DISCOUNTS (g / l) Residual oil (g / kg) Efficiency (%) Residual oil (g / kg) Efficiency (%) 0 56 83 95 40 0.1 11 97 0.5 11 97 1.0 10 97 74 53 2.5 18 95 75 52 5.0 6.7 98 73 54 10 16 95 67 58 20 7.5 98 WASHING OF CUT MODELS BY PRODUCT A Washing fluid Residual oil (g / kg) Efficiency (%) Sea water 56 83 Seawater and Concurrent Product (g / l) 0.01 34 90 0.02 27 92 0.05 23 93 0.5 9 97 1.00 11 97 2.50 23 93 5.00 20 94 10.0 71 79
  • the initial quantity of oil measured is approximately 330 g / kg.
  • the quantity of initial oil measured is approximately 160 g / kg.
  • Efficiency is the ratio, expressed as a percentage, between the quantity of oil removed from the cuttings by washing and the quantity of initial oil in the cuttings considered.
  • Table 3 above gives the results of washing of actual cuttings, with sea water, with a solution of product A according to two concentrations in sea water and with solutions of products B: B1-B2- B3-B4 and B5 having respectively the following HLB values: 8.8-10.8-12.2-13.3 and 16.5.
  • the solutions containing sophorosides show a speed of separation, by simple decantation between the oil and the initial solution, greater in comparison with that of the solutions containing the product A or B. This quality is very advantageous for obtain a good efficiency of the washing process and an optimal re-use of the washing fluid.
  • washing solutions containing sophorosides according to the invention can have formulations comprising other compounds, for example solvents, flocculants or even other surfactants.
  • the volume concentrations of solvents can be between 10 and 20% of the total volume of the solution.
  • flocculants of fine clay particles are also recommended. Indeed, the spoils of a clay nature do not disperse or little in the oil-based drilling fluid. On the other hand, in contact with the aqueous washing solution, they generally tend to react and swell. It is well known that this swelling causes destabilization and dispersion of the solid particles. This dispersion is unfavorable for cleaning because it increases the specific surface of said particles.
  • the role of flocculating products is therefore in particular to avoid dispersion of the particles, which facilitates cleaning and at the same time the separation of the solids from the liquid phase.
  • These products can be, for example, polymers of the anionic or cationic polyacrylamide type, polyethylene oxides, mineral salts or quaternary ammonium salts.
  • the solid phase recovered can be rejected if it is sufficiently clean, or subjected to further washing (second step).
  • the washing solution is then recycled to the washing tank in step 2.
  • the polluting fluid is either stored or recycled in the drilling fluid.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (5)

  1. Verfahren zum Reinigen von mit einer verunreinigenden Flüssigkeit, die Kohlenwasserstoffe enthält, getränkten Feststoffteilchen, wobei man bei dem Verfahren die Feststoffe mit einer Waschlösung zusammenbringt, dadurch gekennzeichnet, daß die Lösung Sophoroside umfaßt und daß die Feststoffe Bohrklein sind.
  2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß die Lösung Sophoroside in einer Konzentration, die zwischen einschließlich 0,1 bis 30 g/l enthalten ist, umfaßt.
  3. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, daß die Waschlösung wenigstens eine an eine der nachfolgenden Funktionen angepaßte Verbindung umfaßt: Einstellen des pH-Wertes der Lösung, Löslichmachen der Kohlenwasserstoffe, Inhibieren des Anschwellens und/oder der Verteilung der Feststoffteilchen.
  4. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, daß man die gereinigten Feststoffe von der Waschlösung durch wenigstens eine der nachfolgenden Maßnahmen abtrennt: Dekantieren, Sieben, Zentrifugieren, Filtrieren oder Zyklonieren.
  5. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, daß man die Waschlösung von der verunreinigenden Lösung durch Dekantieren und/oder Zentrifugieren abtrennt.
EP93400673A 1992-03-26 1993-03-15 Verfahren zum Waschen fester Teilchen mit einer Sophoroside enthaltenden Lösung Expired - Lifetime EP0562914B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9203787 1992-03-26
FR9203787A FR2689138B1 (fr) 1992-03-26 1992-03-26 Procede de lavage de particules solides comportant une solution de sophorosides.

Publications (2)

Publication Number Publication Date
EP0562914A1 EP0562914A1 (de) 1993-09-29
EP0562914B1 true EP0562914B1 (de) 1996-03-20

Family

ID=9428211

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93400673A Expired - Lifetime EP0562914B1 (de) 1992-03-26 1993-03-15 Verfahren zum Waschen fester Teilchen mit einer Sophoroside enthaltenden Lösung

Country Status (5)

Country Link
US (1) US5326407A (de)
EP (1) EP0562914B1 (de)
DE (1) DE69301849T2 (de)
FR (1) FR2689138B1 (de)
NO (1) NO302421B1 (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2699928B1 (fr) * 1992-12-30 1995-01-27 Inst Francais Du Petrole Composition contenant un composé tensio-actif et des sophorolipides et procédé de décontamination d'un milieu poreux pollué par des hydrocarbures.
DE19708499A1 (de) * 1997-03-03 1998-09-10 Henkel Kgaa Verfahren zur Entfernung von bei der Erdölproduktion anfallenden festen Asphaltenrückständen
JP2003013093A (ja) * 2001-06-27 2003-01-15 Saraya Kk 低泡性洗浄剤組成物
DE102009045077A1 (de) * 2009-09-29 2011-03-31 Evonik Goldschmidt Gmbh Verwendung von Sophorolipiden und deren Derivaten in Kombination mit Pestiziden als Adjuvant/Additiv für den Pflanzenschutz und den industriellen non-crop Bereich
JP6697662B2 (ja) * 2015-11-09 2020-05-27 アライドカーボンソリューションズ株式会社 ソホロリピッドを利用した油分回収方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3205150A (en) * 1961-11-27 1965-09-07 Ca Nat Research Council Hydroxy fatty acid production
US3622344A (en) * 1969-04-02 1971-11-23 Pfizer Sophoroside esters in prepared food products
JPS54109914A (en) * 1978-02-17 1979-08-29 Kao Corp Preparation of glycolipid methyl ester
JPS6037086B2 (ja) * 1978-09-26 1985-08-24 花王株式会社 化粧料
JPS6037087B2 (ja) * 1978-09-28 1985-08-24 花王株式会社 化粧料
GB2116579B (en) * 1982-01-07 1985-08-29 Albright & Wilson Composition and method for cleaning hydrocarbon oil from hard surfaces
US4645608A (en) * 1984-10-10 1987-02-24 Sun Drilling Products, Corp. Method of treating oil contaminated cuttings
US4836302A (en) * 1986-12-03 1989-06-06 Heilhecker Joe K Apparatus and method for removing and recovering oil and/or other oil-based drilling mud additives from drill cuttings
EP0330379A3 (de) * 1988-02-26 1990-04-18 The British Petroleum Company p.l.c. Reinigungsmittel
CA2060698C (en) * 1991-02-12 1997-09-30 Peter J. Hall Detergent compositions

Also Published As

Publication number Publication date
FR2689138B1 (fr) 1994-05-20
NO931088L (no) 1993-09-27
EP0562914A1 (de) 1993-09-29
DE69301849D1 (de) 1996-04-25
FR2689138A1 (fr) 1993-10-01
NO302421B1 (no) 1998-03-02
NO931088D0 (no) 1993-03-24
DE69301849T2 (de) 1996-08-01
US5326407A (en) 1994-07-05

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