WO2017174417A1 - Tensioactifs de diamines appropriés comme émulsifiants - Google Patents

Tensioactifs de diamines appropriés comme émulsifiants Download PDF

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Publication number
WO2017174417A1
WO2017174417A1 PCT/EP2017/057418 EP2017057418W WO2017174417A1 WO 2017174417 A1 WO2017174417 A1 WO 2017174417A1 EP 2017057418 W EP2017057418 W EP 2017057418W WO 2017174417 A1 WO2017174417 A1 WO 2017174417A1
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WO
WIPO (PCT)
Prior art keywords
formula
diamine
acid
mixture
linear
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PCT/EP2017/057418
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English (en)
Inventor
Olivier BACK
Philippe Marion
Hélène MARTIN
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Rhodia Operations
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Publication of WO2017174417A1 publication Critical patent/WO2017174417A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/09—Diamines
    • C07C211/11—Diaminopropanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C07C209/28—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with other reducing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
    • C08L95/005—Aqueous compositions, e.g. emulsions

Definitions

  • the present invention relates to specific diamines useful as surfactants, especially as emulsifier, especially for bitumen emulsions.
  • Bitumen emulsions are well known compositions including droplets of bitumen dispersed in an aqueous medium.
  • emulsifiers that allow the emulsification and avoid the collapse of the emulsion for a more or less long period.
  • amines are commonly used, especially for stabilizing the so-called “cationic emulsions”.
  • An object of the present invention is to provide a new familiy of amine suitable as surfactant and that are suitable, inter alia, as emulsifier for bitumen emulsion.
  • the instant invention proposes to make use of specific diamines molecules, which are obtained via a new process route and that were not known in the prior art to the best knowledge of the inventors.
  • one subject-matter of the instant invention is a surfactant of the formula (I):
  • each of R a and R b which are identical or different, is a linear or branched, saturated or unsaturated, hydrocarbon chain, that may be interrupted and/or substituted by at least a monocyclic or polycyclic group, that may be, but not neceassarily, an aryl group,
  • each of R a and R b being typically :
  • R a and R b typically carrying from 7 to 17 carbon atoms ; it being independently preferred that the sum of the number of carbon in Ra and Rb is of at least 7, preferably of at least 10 and typically of at least 14);
  • each of Rc and Rd which are identical or different, is a a linear or branched alkyl chain having 1 to 10 carbon atoms, typically 1 to 4 carbon atoms.
  • R a and R b are preferably linear groups, typically linear hydrocarbon groups.
  • the compositions of the invention do not need to make use of branched R a and R b groups which are more costly than linear R a and R b groups.
  • the invention relates to a method for preparing the surfactant having the formula (I) as defined herein-above.
  • step 1 reacting two acids Ra-COOH and Rb-COOH (the reaction being obtained by reacting a population of acids including these two acids), wherein Ra and Rb are identical or different, via a Piria decarboxylating ketonization, whereby a internal ketone is obtained having the formula (II) :
  • step 2 reacting the internal ketone (II) obtained in step 1 with a diamine of formula H 2 N-(E1 )-NR c R d in a reductive amination reaction
  • the surfactants of the invention may be easily prepared from cheap and available (typically naturally occuring) raw materials of relatively low cost, which is a first disadvantage.
  • the hydrophobic part of the surfactants of the invention can be entirely saturated, which provides stability against oxidation when compared to unsaturated products.
  • the diamines and mixtures of diamines used in the scope of the invention are preferably liquids at a temperature of 10 to 30°C. Accordingly, the invention may make use of at least one diamine liquid between 10 and 30°C (to this end, it is advantageous to make use of amines having a number of carbon as low as possible in the groups R a and R b ), or of mixtures that are mixtures liquid between 10 and 30°C even if they contain amines that are, individually, not liquid in this range of temperature (these mixtures preferably contain a liquid diamine in addition to the non liquid diamine, the liquid diamine having preferably a number of carbon as low as possible in the groups R a and R b ).
  • a subject-matter of the invention is the use of a diamine of formula (I) (or of a mixture of amines comprising at least two diamines of formula (I) or of a formulation comprising at least a diamine of formula (I) or a mixture of such diamines) as an emulsifier in a bitumen emulsion.
  • the invention also relates to a method for preparing a bitumen emulsion comprising a step wherein a bitumen is mixed together with an aqueous medium (typically water) under shear rate and in the presence of at least a diamine of formula (I), said at least one diamine of formula (I) being preferably premixed with the aqueous phase.
  • aqueous medium typically water
  • bitumen emulsions obtained in the scope of the invention that comprise a continuous aqueous phase, droplets of bitumen dispersed therein and at least a diamine (more preferably a mixture of at least two distinct amines of formula I) constitute an other subject-matter of the instant invention.
  • R a and R b groups present in the surfactants of formula (I) may be defined by the acids R a COOH and R b COOH from which they are prepared in step 1 as defined herein-above (and also referred herewith as " fatty acids"), or from which they could have been prepared in the case they are not prepared by making use of this step.
  • Preferred fatty acids from which the surfactants of formula (I) are actually derived are caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid , naphthenic acids, isostearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid or mixtures thereof and preferred acid derivatives are the esters and anhydrides of these acids.
  • Preferred are caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, naphthenic acids, isostearic acids or mixture thereof.
  • fatty acids from which the surfactants of formula (I) are actually derived comprise one or more double bonds in the chain and include for example oleic acid, linoleic acid, linolenic acid and erucic acid to name only a few examples.
  • naphthenic acid generally denotes a complex mixture of saturated monocarboxylic acids containing cyclopentyl and/ot cyclohexyl fragments containing usually 9 to 20 carbon atoms. Naphthenic acids are obtained by oxidation of the naphtha fraction of crude oil and their composition varies with the crude oil composition and the conditions during refining and oxidation.
  • the diamines of formula (I) are actually prepared from an internal ketone obtained from fatty acids according to step 1 of the process as defined herein-above.
  • the surfactants of formula (I) may either be obtained from a single fatty acid RaCOOH or from a starting fatty acids mixture.
  • said mixture may be for example a so-called "cut” as typically obtained from vegetable or animal oils through saponification or alcoholysis. More preferably, it may be a fatty acid cut derived from coconut oil or palm kernel oil, that preferably contains a mixture of fatty acids which can comprise fatty acids having 8 carbon atoms up to 18 carbon atoms.
  • Internal ketones used in step 2 of the process described herein above can alternatively be obtained through cross-ketonization reactions starting from a mixture of linear fatty acids and naphthenic acids, or through cross-ketonization starting from a mixture of aliphatic fatty acids and benzoic acid.
  • Step 1 decarboxylative ketonization of fatty acids
  • fatty acids preferably saturated straight chain fatty acids
  • II the internal ketone
  • This reaction is typically conducted with the fatty acids in a liquid phase and preferably by continuously removing water formed during the reaction from the reaction mixture.
  • Step 1 can be applied to a single fatty acid or to a cut of fatty acids generating therefore a cut of fatty ketones of formual (II).
  • step 1 may be catalyzed by at least one metal compound, advantageously selected from the group consisting of Mg, Ca, Al, Ga, In, Ge, Sn, Pb, As, Sb, Bi, Cd and transition metals having an atomic number of from 21 to 30 or a mixture thereof or an oxide of these metals or a mixture thereof, preferably in an oxydized state (the metal in its oxidized state may be generated in situ by introducing the corresponding metal at a non oxidized state).
  • at least one metal compound advantageously selected from the group consisting of Mg, Ca, Al, Ga, In, Ge, Sn, Pb, As, Sb, Bi, Cd and transition metals having an atomic number of from 21 to 30 or a mixture thereof or an oxide of these metals or a mixture thereof, preferably in an oxydized state (the metal in its oxidized state may be generated in situ by introducing the corresponding metal at a non oxidized state).
  • step 1 is adexcellentously catalyzed by compounds of oxydized iron, typically at least one iron oxide, such as magnetite Fe 3 0 4 , and/or Fe 2 0 3 , or FeO, the at least one iron oxide being preferably generated in situ in step 1 by introducing metallic iron, typically iron powder (namely : Fe (0) ) which has the advantage to be a very cheap and abundant material.
  • metallic iron typically iron powder (namely : Fe (0) ) which has the advantage to be a very cheap and abundant material.
  • the metal compound and a first part of the fatty acids are mixed in a molar ratio of from 1 :0.8 to 1 :3.5 (molar ratio metal: carboxyl group equivalent) and reacted for a period of from 5 to 300 min at a temperature of from 180 to 270 °C, preferably from 190 to 260°C for a duration of from 5 to 240 min, fo example o from 15 to 120 min, and preferably in the substantial absence of added solvents, and
  • step 1 .2 is preferably conducted in the substantial absence of added solvents
  • stage (1 .2) it can be interesting to separate the metallic compounds from the products (that may be done using conventional techniques) and then to recycle the metallic compounds, e.g. for the conversion of another batch of fatty acids
  • the fatty acids used in the two stages (1 .1 ) and (1 .2) preferably comprise at least 10 mol%, based on the entire amount of fatty acids, of fatty acids having 12 carbon atoms or less.
  • the fatty acids are selected from butanoic acid, hexanoic acid, isostearic acids, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid or mixtures thereof, and more preferably the fatty acids comprises 8 to 18 carbon atoms.
  • Stages 1 .1 and 1 .2 can also be operated on fatty acid derivatives preferably selected from esters and anhydrides, such as esters or anhydrides of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid or mixtures thereof (these derivatives preferably contain with 8 to 18 carbon atoms).
  • Step 1 of the process may for example be conducted by :
  • step (b) the temperature of the reaction mixture obtained by step (a) is risen above 290°C, preferably to about 300°C (whereby carboxylate salts of iron decompose to iron oxide, fatty ketone and C0 2 ) and maintained at this temprature and the remaining fatty acids are added to the liquid mixture.
  • the rest oft he fatty acids introduced in step (b) is added over a period of from 2 to 12 hours.
  • the ketone (II) acts also as a high boiling point solvent and the water generated during the reaction can therefore be trapped e.g. thanks to a dean- stark apparatus.
  • the products fatty ketone can be separated from iron compounds, for example as follows:
  • Step 2 preparation of the sought diamine (I)
  • This step allows a reductive amination of the ketone (II) obtained in step 1 .
  • This amination is preferably performed by reacting the ketone (II) and the diamine of formula H 2 N-(E1 )-NR c R d as defined herein-above in the presence of a transition metal (e.g. Ni, Co, Cu, Fe, Pd, Pt) based catalyst (typically Pd/C), under hydrogen pressure (typically between 1 atm. and 200 bar).
  • a transition metal e.g. Ni, Co, Cu, Fe, Pd, Pt
  • Pd/C platinum/C
  • the reaction is carried out in a solvent.
  • a solvent such as a solvent
  • the exact nature of the solvent, if any, may be determined by the skilled person.
  • suitable solvents include, without limitation, methanol, ethanol, isopropanol and mixtures thereof.
  • Step 2 is usually carried out at a temperature ranging from 15°C to 300°C.
  • Step 2 may be conducted batchwise, semi-continuously or continuously and generally performed either in a batch mode or in a continuous mode using a fixed-bed catalyst (gas-solid or gas-liquid-solid process).
  • a diamine of formula H 2 N-(E 1 )-NR c R d suitable for step 2 is dimethylaminopropylamine (DMAPA). This amine can be employed in stoichiometric amounts or in excess.
  • DMAPA dimethylaminopropylamine
  • diamines suitable in step 2 include Aminoethylethanolamine (AEEA) and Ethylendiamine (EDA).
  • AEEA Aminoethylethanolamine
  • EDA Ethylendiamine
  • the group -(E 1 )- of the diamine of formula H 2 N- (E1 )-NR c R d may comprise an amine vicinity (in that case, the amine may be a triamine or a polyamine : the term "diamine" as used in step 2 intend to encompass compounds including at least two amine group, and optionally more).
  • amines with more that two amine groups include for example diethylene triamine (DETA), triethylenetetramine (TETA), tetraethylene pentamine (TEPA)
  • diamines may also be used, including for example mixture of D ETA/E D A/AE E A
  • the diamine (I) produced in step 2 can be recovered after catalyst separation and removal of solvent and DMAPA excess. Finally the product can be purified, e.g. using standard technics such as distillation.
  • the diamines according to the invention are surfactants that are suitable as emulsifiers of hydrophobic droplets in an aqueous phase. They are especially of interest for bitumen emulsions.
  • the diamines as used individually according to the invention, or the mixture of diamines when they are use as such are preferably liquids at a temperature of 10°C to 30°C, and preferably in a wider range of temperature, advantageously at least between 0°C to 40°C . To this end, it is advantageous to make use of
  • mixtures of amines containing distinct groups R a and R b may be e.g. obtained from mixtures of ketones (II) obtained from mixtures of fatty acids in step 1 as defiend above, for example from cuts of C 8 -Ci 8 fatty acids.
  • Non restrictive examples of diamine of specific interest include the compounds of formula (I) wherein :
  • Ra and Rb are a mixture of fatty chain (alyl chains typically) of between C 8 and C18 (having between 8 and 18 carbon atoms)
  • a diamine of formula (I) (or of a mixture of amines comprising at least two diamines of formula (I) or of a formulation comprising at least a diamines of formula (I) or a mixture of such diamines) is used as an emulsifier in an emulsion, especially in a bitumen emulsion, it is typically used at a content of 0.05% to 5%, for example from 0.1 to 2 % by weight, on the basis of the total weight of the emulsion.
  • emulsions as obtained in the scope of the invention comprising an emulsion of a bitumen (modified or not) in an aqueous medium and including the diamines (I) are typically cationic emulsions that may especially be selected from :
  • Step 1 synthesis of an internal ketone
  • reaction was carried out under argon in a round bottom flask equipped with mechanical stirring, dean stark apparatus and an addition funnel.
  • the addition funnel was replaced by a distillation apparatus and the products were distilled off at 290°C-340°C under 50 mbars pressure.
  • distillation apparatus was again replaced by the addition funnel containing a new amount of 5g + 15g of fatty acids and the operations described above were repeated for another cycle.
  • step 1 the residue in the flask remaining after distillation is efficient to convert the next batch of acids.
  • a cut of saturated straight chain fatty acids with a distribution representative of natural coconut oil (C8: 7 wt%, C10: 8 wt%, C12: 48 wt%, C14: 17 wt%, C16: 10 wt% and C18: 10 wt%) was used in this case.
  • reaction was carried out under argon in a round bottom flask equipped with mechanical stirring, dean stark apparatus and an addition funnel.
  • the suspension was filtered on a silica plug (600g) and the remaining product was eluted with additional volume of CHCI 3 . After evaporation of the solvent, 140g of the sought product (82% isolated yield) was recovered as a white wax.
  • step 2 synthesis of the diamine
  • the organic phase of the filtrate is separated from the aqueous phase and is washed twice with 500 mL of aq. NaOH solution (0.5 M) followed by 500 mL of brine.
  • the organic phase is dried over MgS0 4 , filtered and evaporated to give a pale yellow oil.
  • the product is finally purified by flash chromatography on silica gel using CH 2 CI 2 : MeOH as eluent (from 70:30 to 60:40) to obtain 6 g of the product as a transparent oil. (48% yield).
  • the diamines as obtained in examples 1 .2.1 and 1 .2.2. are suitable for emulsifying bitumen in water and allow to obtain cationic emulsion.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Civil Engineering (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

La présente invention concerne des diamines de formule (I) dans laquelle : ▪ Ra et Rb représentent chacun une chaîne hydrocarbonée, ▪ Rc et Rd représentent chacun une chaîne alkyle ayant de 1 à 10 atomes de carbone, ▪ (E1) représente une chaîne hydrocarbonée divalente. L'invention concerne également la préparation de ces diamines et leur utilisation en tant que tensioactifs, en particulier dans des émulsions de bitume.
PCT/EP2017/057418 2016-04-08 2017-03-29 Tensioactifs de diamines appropriés comme émulsifiants WO2017174417A1 (fr)

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EP16305410 2016-04-08

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109593376A (zh) * 2018-12-26 2019-04-09 祺农化工科技(上海)有限公司 一种用于sbs改性沥青乳化的双y型液体快裂阳离子乳化剂及应用
US10906857B2 (en) 2017-06-16 2021-02-02 Rhodia Operations Process for the catalytic decarboxylative cross-ketonization of aryl and aliphatic carboxylic acid
WO2021120090A1 (fr) * 2019-12-19 2021-06-24 Solvay Sa Processus de synthèse de triamines à double queue

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GB1277947A (en) * 1968-08-22 1972-06-14 Armour Ind Chem Co Compositions and method for controlling insect pests
US20120295832A1 (en) * 2011-05-17 2012-11-22 Arrowhead Research Corporation Novel Lipids and Compositions for Intracellular Delivery of Biologically Active Compounds
US20140371293A1 (en) * 2011-10-18 2014-12-18 Dicerna Pharmaceuticals, Inc. Amine Cationic Lipids and Uses Thereof

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10906857B2 (en) 2017-06-16 2021-02-02 Rhodia Operations Process for the catalytic decarboxylative cross-ketonization of aryl and aliphatic carboxylic acid
US11708317B2 (en) 2017-06-16 2023-07-25 Rhodia Operations Process for the catalytic decarboxylative cross-ketonization of aryl and aliphatic carboxylic acid
CN109593376A (zh) * 2018-12-26 2019-04-09 祺农化工科技(上海)有限公司 一种用于sbs改性沥青乳化的双y型液体快裂阳离子乳化剂及应用
CN109593376B (zh) * 2018-12-26 2021-04-06 祺农化工科技(上海)有限公司 一种用于sbs改性沥青乳化的双y型液体快裂阳离子乳化剂及应用
WO2021120090A1 (fr) * 2019-12-19 2021-06-24 Solvay Sa Processus de synthèse de triamines à double queue
CN114845987A (zh) * 2019-12-19 2022-08-02 索尔维公司 用于合成双尾三胺的方法
CN114845987B (zh) * 2019-12-19 2024-06-11 索尔维公司 用于合成双尾三胺的方法

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