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EP1742899A1 - Method for production of diphenylethylene - Google Patents

Method for production of diphenylethylene

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Publication number
EP1742899A1
EP1742899A1 EP05769668A EP05769668A EP1742899A1 EP 1742899 A1 EP1742899 A1 EP 1742899A1 EP 05769668 A EP05769668 A EP 05769668A EP 05769668 A EP05769668 A EP 05769668A EP 1742899 A1 EP1742899 A1 EP 1742899A1
Authority
EP
European Patent Office
Prior art keywords
mixture
diphenyl
dpe
solvent
dpa
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.)
Withdrawn
Application number
EP05769668A
Other languages
German (de)
French (fr)
Inventor
Alain Riondel
Christophe Navarro
Jean-Philippe Gendarme
Bernard Wechtler
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.)
Arkema France SA
Original Assignee
Arkema France SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Arkema France SA filed Critical Arkema France SA
Publication of EP1742899A1 publication Critical patent/EP1742899A1/en
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed

Definitions

  • the invention relates to a process for the preparation of diphenyl ethylene (DPE) by catalytic dehydrogenation of diphenyl ethane (DPA).
  • DPE diphenyl ethylene
  • DPA diphenyl ethane
  • SBM Styrene Butadiene Methyl Methacrylate
  • the synthesis of DPE by catalytic dehydrogenation in the presence of water from DPA is known for example from SU472166.
  • Document DE19814457 describes the preparation of DPE from DPA by catalytic dehydrogenation.
  • the purification of the DPE obtained is carried out on a distillation column with packing, in the presence of a third body which is sodium hydroxide.
  • a third body which is sodium hydroxide.
  • the document DE19814459 describes the synthesis of DPE from DPA in the presence of water on a catalyst, the reaction being carried out at the same time as the reaction for dehydrogenation of ethylbenzene (EB) to styrene.
  • EB ethylbenzene
  • DPE is obtained as a mixture with DPA, EB and styrene.
  • the DPE is again separated from the styrene by distillation or then used as it is at the application level.
  • the invention provides a method of manufacturing diphenyl ethylene comprising the steps of: (a) catalytic dehydrogenation of diphenyl ethane in the presence of water; (b) adding a light organic solvent to the mixture obtained in step (a); and (c) decanting the mixture obtained in step (b) and recovering a stream containing diphenyl ethylene in admixture with the solvent added in step (b).
  • the light organic solvent is ethylbenzene.
  • the amount of solvent added represents, relative to the combined mass of diphenyl ethylene and diphenyl ethane, from 10 to 50% by weight, preferably from 15 to 30% by weight.
  • the method further comprises, after the decantation step, a step (d) dehydration on a molecular sieve.
  • the stream containing diphenyl ethylene comprises, by weight relative to the total weight of the stream: 40 to 80% of DPE; 1 to 30% of DPA; 5 to 50% solvent; preferably: 50 to 70% of DPE; - 5 to 20% of DPA; 10 to 30% solvent.
  • Another subject of the invention is this mixture as well as its use in polymerization, in particular in polymerization of SBM.
  • DETAILED PRESENTATION OF EMBODIMENTS OF THE INVENTION The first step of the process for the synthesis of DPE is a catalytic dehydration of DPA to DPE in the presence of water.
  • This first step is classic and known in the art. Those skilled in the art know the operating parameters to be used during this reaction. In general, this reaction is typically carried out under the following operating conditions: - temperature from: 400 to 700 ° C; pre-spraying temperature: 270 to 400 ° C; pressure: typically of the order of atmospheric or less; WH: 0.05 to 5 h "1 ; - water / DPA mass ratio of between 1: 1 and 10: 1.
  • the catalyst is any dehydrogenation catalyst for 1, 1-diarylethane, in particular DPA. .
  • catalysts of the range of Styromax ® can also mention the following documents, which provide a general description of the catalytic dehydrogenation step: SU472166, DE19814457, DE19814459, US4365103, US2450334, JP01013048, JP01013052, JP2215-734, EP0282066 and W09949967.
  • a reaction mixture comprising predominantly DPE, DPA and water is obtained at the end of this first step.
  • the ratio DPE + DPA / water corresponds substantially to the starting ratio DPA / water (taking account selectivity of the conversion of DPA to DPE).
  • the ratio DPE / DPA varies within the conventional limits.
  • This mixture is added with a light organic solvent (density less than 0.95, preferably between 0 .95 and 0.85.)
  • a light organic solvent density less than 0.95, preferably between 0 .95 and 0.85.
  • Advantageously 1 ethylbenzene EB is used (in the following description is given with reference to this product but any other suitable solvent is substitutable).
  • the amount, relative to the sum DPE + DPA, is generally between 10 and 50%, preferably 15 to 30%.
  • a decantation phase is then carried out in a decanter, for a residence time which can be between 120 and 10 minutes, preferably between 60 and 15 minutes.
  • the decanter is any conventional decanter, for example of the Grignard type, centrifugal, by coalescence, etc.
  • the temperature at which one can operate this decantation can be between 50 and 20 ° C, preferably between 35 and 25 ° C.
  • Two phases are obtained, one aqueous and the other organic.
  • the organic phase contains the light solvent and the DPE and DPA dissolved in it.
  • This organic phase current mainly comprises DPE in EB, with traces of water. These traces of water can be removed, for example by percolation on a molecular sieve.
  • Those skilled in the art know the molecular sieves suitable for the mixtures to be separated.
  • a stream is obtained at the outlet of the molecular sieve mainly comprising DPE with a small amount of DPA in EB, and which contains less than 100 ppm, preferably less than 50 ppm, of water.
  • the relative proportions of DPE, DPA and EB in the solution are variable and depend on the performance of the catalytic dehydrogenation step and the water / DPA starting ratio, and on the amount of EB which is added to the dehydrogenate.
  • a mixture in a solvent optionally monomeric, can be used directly in SBM synthesis.
  • the invention also relates to such a particular mixture, which comprises, by weight relative to the total weight of the mixture: 40 to 80% of DPE, preferably 50 to 70%; 1 to 30% of DPA, preferably 5 to 20%; - 5 to 50% of EB, preferably 10 to 30%; possibly other components in an amount less than 15%, preferably 10%.
  • Such a mixture can be used directly in synthesis, in particular in SBM synthesis.
  • ethylbenzene is added at a rate of 13 g / h and separation is carried out by decantation at room temperature over 15 minutes.
  • An organic phase is obtained which then comprises: - DPE: 61.2%; CCA: 11.9%; EB: 19.4%; other products: 6.5%; and water: 500ppm.
  • 1560 g of DPE are thus recovered which are then treated on a molecular sieve (NK30 from CECA) to remove the water.
  • This dehydration is implemented by feeding from below a column of 1m and diameter 24mm containing 285g of molecular sieve.
  • the flow rate in DPE is 456 g / h. After percolation on the sieve, the water content of the product is around 45 ppm.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention relates to a method for production of diphenylethylene (DPE) comprising the steps of: (a) catalytic dehydrogenation of diphenylethane (DPA) in the presence of water, (b) addition of a light organic solvent to the mixture from step (a) and (c) decanting the mixture from step (b) with recovery of a flow comprising diphenylethylene as a mixture with the solvent added in step (b). The invention further relates to a given mixture of DPE, DPA and solvent and use thereof in polymerisation.

Description

PROCEDE DE FABRICATION DE DIPHENYL ETHYLENE PROCESS FOR PRODUCING DIPHENYL ETHYLENE
DOMAINE TECHNIQUE L'invention a pour objet un procédé de préparation de diphényl éthylène (DPE) par déshydrogénation catalytique de diphényl éthane (DPA) . ETAT DE LA TECHNIQUE Le diphényl éthylène (DPE) est utilisé par exemple en synthèse de polymères triblocs, notamment SBM (Styrène Butadiène Méthacrylate de méthyle) . La synthèse de DPE par déshydrogénation catalytique en présence d'eau à partir de DPA est connue par exemple de SU472166. Le document DE19814457 décrit la préparation de DPE à partir de DPA par déshydrogénation catalytique. La purification du DPE obtenu est effectuée sur une colonne à distiller avec garnissage, en présence d'un tiers corps qui est de la soude .Le document DE19814459 décrit la synthèse de DPE à partir de DPA en présence d'eau sur un catalyseur, la réaction étant conduite en même temps que la réaction de déshydrogénation d' éthylbenzène (EB) en styrène. Le DPE est obtenu en mélange avec le DPA, 1 ' EB et le styrène . Le DPE est à nouveau séparé du styrène par distillation ou alors utilisé tel quel au niveau applicatif. Dans le cas classique de la synthèse par déshydrogénation catalytique à partir de DPA en présence d'eau, le DPE brut (mélange de DPE et de DPA) est difficile à séparer de l'eau par décantation. En effet, en mélange avec le DPA et l'eau, il ne se produit pas de décantation en raison de l'absence d'écart significatif de densité entre les produits. L'eau présente en effet une densité de 1 tandis qu'un mélange 50/50 en masse DPA/DPE présente une densité de 1,0045. La séparation du DPE dans les procédés ci-dessus n'est pas satisfaisante au niveau de la simplicité du procédé. L'invention vise donc à améliorer la séparation de DPE à partir d'un mélange réactionnel contenant DPE/DPA/eau. RESUME DE L ' INVENTION L'invention fournit un procédé de fabrication de diphényl éthylène comprenant les étapes de: (a) déshydrogénation catalytique de diphényl ethane en présence d'eau; (b) addition d'un solvant organique léger au mélange obtenu à l'étape (a); et (c) décantation du mélange obtenu à l'étape (b) et récupération d'un flux contenant du diphényl éthylène en mélange avec le solvant ajouté à l'étape (b) . Selon un mode de réalisation, le solvant organique léger est 1 ' éthylbenzène . Selon un mode de réalisation, la quantité de solvant ajoutée représente, par rapport à la masse combinée de diphényl éthylène et diphényl ethane, de 10 à 50% en poids, de préférence de 15 à 30% en poids. Selon un mode de réalisation, le procédé comprend en outre après l'étape de décantation une étape (d) déshydratation sur tamis moléculaire. Selon un mode de réalisation, le flux contenant le diphényl éthylène comprend, en poids par rapport au poids total du flux: 40 à 80% de DPE; 1 à 30% de DPA; 5 à 50% de solvant; de préférence: 50 à 70% de DPE; - 5 à 20% de DPA; 10 à 30% de solvant. L'invention a encore pour objet ce mélange ainsi que son utilisation en polymérisation, en particulier en polymérisation du SBM. EXPOSE DETAILLEE DE MODES DE REALISATION DE L'INVENTION La première étape du procédé de synthèse de DPE est une déshydratation catalytique de DPA en DPE en présence d'eau. Cette première étape est classique et connue dans l'art. L'homme du métier connaît les paramètres opératoires à utiliser lors de cette réaction. A titre général, cette réaction est typiquement mise en œuvre dans les conditions opératoires suivantes : - température de: 400 à 700°C; température de prévaporisation: 270 à 400°C; pression: typiquement de l'ordre de l'atmosphérique ou moins ; WH: 0, 05 à 5 h"1; - ratio massique eau/DPA compris entre 1:1 et 10:1. Le catalyseur est tout catalyseur de déshydrogénation de 1, 1-diaryléthane, en particulier de DPA. On peut mentionner les catalyseurs de la gamme des Styromax®. On peut encore mentionner les documents suivants, qui fournissent une description générale de cette étape de déshydrogénation catalytique: SU472166, DE19814457, DE19814459, US4365103, US2450334, JP01013048, JP01013052, JP2215-734, EP0282066 et W09949967. On obtient en sortie de cette première étape un mélange reactionnel comprenant de façon prépondérante du DPE, du DPA et de l'eau. Dans ce mélange, le ratio DPE+DPA/eau correspond sensiblement au ratio de départ DPA/eau (en tenant compte de la sélectivité de la conversion du DPA en DPE) . Dans ce mélange toujours, le ratio DPE/DPA varie dans les limites classiques. Ce mélange est additionné d'un solvant organique léger (densité inférieure à 0.95, de préférence comprise entre 0.95 et 0.85.) On utilise avantageusement 1 ' éthylbenzène EB (dans ce qui suit la description est donnée en référence à ce produit mais tout autre solvant approprié est substituable) . La quantité, par rapport à la somme DPE+DPA, est en général comprise entre 10 et 50%, de préférence 15 à 30%. On opère ensuite une phase de décantation dans un decanteur, pendant un temps de séjour qui peut être compris entre 120 et 10 minutes, de préférence entre 60 et 15 minutes. Le decanteur est tout decanteur classique, par exemple de type Grignard, centrifuge, par coalescence, etc.. La température à laquelle on peut opérer cette décantation peut être comprise entre 50 et 20°C, de préférence entre 35 et 25°C. On obtient deux phases, l'une aqueuse et l'autre organique. La phase organique contient le solvant léger et le DPE et DPA dissous dans celui-ci. Ce courant de phase organique comprend de façon prépondérante du DPE dans de l'EB, avec des traces d'eau. Ces traces d'eau peuvent être éliminées par exemple par percolation sur tamis moléculaire. L'homme de l'art connaît les tamis moléculaires adaptés aux mélanges à séparer. On obtient en sortie du tamis moléculaire un flux comprenant majoritairement du DPE avec une quantité faible de DPA dans EB, et qui contient moins de lOOppm, de préférence moins de 50ppm, d'eau. Les proportions relatives de DPE, DPA et EB dans la solution sont variables et dépendent des performances de 1 ' étape de déshydrogénation catalytique et du ratio de départ eau/DPA, et de la quantité de EB qui est ajoutée au déshydrogénat . Un tel mélange dans un solvant, éventuellement monomère, est utilisable directement en synthèse SBM. L'invention vise aussi un tel mélange particulier, qui comprend, en poids par rapport au poids total du mélange: 40 à 80% de DPE, de préférence 50 à 70%; 1 à 30% de DPA, de préférence 5 à 20%; - 5 à 50% de EB, de préférence 10 à 30%; éventuellement d'autres composants en un quantité inférieure à 15%, de préférence 10%. Un tel mélange est utilisable directement en synthèse, en particulier en synthèse SBM. Par rapport à un procédé de synthèse en parallèle DPA/DPE et EB/S tel que décrit par exemple dans DE19814459, le mélange contient une part plus important de DPE. En effet, dans le document DE19814459, au tableau 2, pour le cas le plus favorable d'une synthèse à partie d'un mélange EB/DPE 50/50, la quantité de DPE n'est que d'environ 38% en poids du mélange final. EXEMPLES Les exemples suivants illustrent 1 ' invention sans la limiter. On utilise un réacteur tubulaire de 45mm de diamètre, chauffé à 570°C sous une pression de 0,5bar et contenant 170ml de catalyseur Styromax® 3. Ce réacteur est alimenté par du DPA et de l'eau préalablement vaporisés à 310°C, à des débits respectifs de 52 et 156g/h. En sortie de réacteur, après refroidissement du mélange reactionnel, on ajoute de 1 ' éthylbenzène, à raison de 13g/h et on opère une séparation par décantation à température ambiante sur 15 minutes . On obtient une phase organique qui comprend alors : - DPE: 61,2%; DPA: 11,9%; EB: 19,4%; autres produits: 6,5%; et eau: 500ppm. Après 24h de fonctionnement on récupère ainsi 1560g de DPE qui sont ensuite traités sur tamis moléculaire (NK30 de CECA) pour éliminer l'eau. Cette déshydratation est mise en œuvre en alimentant par le bas une colonne de 1m et de diamètre 24mm contenant 285g de tamis moléculaire. Le débit en DPE est de 456g/h. Après percolation sur la tamis, la teneur en eau du produit est d'environ 45ppm. TECHNICAL FIELD The invention relates to a process for the preparation of diphenyl ethylene (DPE) by catalytic dehydrogenation of diphenyl ethane (DPA). STATE OF THE ART Diphenylethylene (DPE) is used for example in the synthesis of triblock polymers, in particular SBM (Styrene Butadiene Methyl Methacrylate). The synthesis of DPE by catalytic dehydrogenation in the presence of water from DPA is known for example from SU472166. Document DE19814457 describes the preparation of DPE from DPA by catalytic dehydrogenation. The purification of the DPE obtained is carried out on a distillation column with packing, in the presence of a third body which is sodium hydroxide. The document DE19814459 describes the synthesis of DPE from DPA in the presence of water on a catalyst, the reaction being carried out at the same time as the reaction for dehydrogenation of ethylbenzene (EB) to styrene. DPE is obtained as a mixture with DPA, EB and styrene. The DPE is again separated from the styrene by distillation or then used as it is at the application level. In the classic case of synthesis by catalytic dehydrogenation from DPA in the presence of water, the crude DPE (mixture of DPE and DPA) is difficult to separate from water by decantation. Indeed, when mixed with DPA and water, no settling occurs due to the absence of a significant difference in density between the products. Water has a density of 1 while a 50/50 mixture by mass of DPA / DPE has a density of 1.0045. The separation of DPE in the above processes is not satisfactory in terms of the simplicity of the process. The invention therefore aims to improve the separation of DPE from a reaction mixture containing DPE / DPA / water. SUMMARY OF THE INVENTION The invention provides a method of manufacturing diphenyl ethylene comprising the steps of: (a) catalytic dehydrogenation of diphenyl ethane in the presence of water; (b) adding a light organic solvent to the mixture obtained in step (a); and (c) decanting the mixture obtained in step (b) and recovering a stream containing diphenyl ethylene in admixture with the solvent added in step (b). According to one embodiment, the light organic solvent is ethylbenzene. According to one embodiment, the amount of solvent added represents, relative to the combined mass of diphenyl ethylene and diphenyl ethane, from 10 to 50% by weight, preferably from 15 to 30% by weight. According to one embodiment, the method further comprises, after the decantation step, a step (d) dehydration on a molecular sieve. According to one embodiment, the stream containing diphenyl ethylene comprises, by weight relative to the total weight of the stream: 40 to 80% of DPE; 1 to 30% of DPA; 5 to 50% solvent; preferably: 50 to 70% of DPE; - 5 to 20% of DPA; 10 to 30% solvent. Another subject of the invention is this mixture as well as its use in polymerization, in particular in polymerization of SBM. DETAILED PRESENTATION OF EMBODIMENTS OF THE INVENTION The first step of the process for the synthesis of DPE is a catalytic dehydration of DPA to DPE in the presence of water. This first step is classic and known in the art. Those skilled in the art know the operating parameters to be used during this reaction. In general, this reaction is typically carried out under the following operating conditions: - temperature from: 400 to 700 ° C; pre-spraying temperature: 270 to 400 ° C; pressure: typically of the order of atmospheric or less; WH: 0.05 to 5 h "1 ; - water / DPA mass ratio of between 1: 1 and 10: 1. The catalyst is any dehydrogenation catalyst for 1, 1-diarylethane, in particular DPA. . catalysts of the range of Styromax ® can also mention the following documents, which provide a general description of the catalytic dehydrogenation step: SU472166, DE19814457, DE19814459, US4365103, US2450334, JP01013048, JP01013052, JP2215-734, EP0282066 and W09949967. A reaction mixture comprising predominantly DPE, DPA and water is obtained at the end of this first step. In this mixture, the ratio DPE + DPA / water corresponds substantially to the starting ratio DPA / water (taking account selectivity of the conversion of DPA to DPE). In this mixture always, the ratio DPE / DPA varies within the conventional limits. This mixture is added with a light organic solvent (density less than 0.95, preferably between 0 .95 and 0.85.) Advantageously 1 ethylbenzene EB is used (in the following description is given with reference to this product but any other suitable solvent is substitutable). The amount, relative to the sum DPE + DPA, is generally between 10 and 50%, preferably 15 to 30%. A decantation phase is then carried out in a decanter, for a residence time which can be between 120 and 10 minutes, preferably between 60 and 15 minutes. The decanter is any conventional decanter, for example of the Grignard type, centrifugal, by coalescence, etc. The temperature at which one can operate this decantation can be between 50 and 20 ° C, preferably between 35 and 25 ° C. Two phases are obtained, one aqueous and the other organic. The organic phase contains the light solvent and the DPE and DPA dissolved in it. This organic phase current mainly comprises DPE in EB, with traces of water. These traces of water can be removed, for example by percolation on a molecular sieve. Those skilled in the art know the molecular sieves suitable for the mixtures to be separated. A stream is obtained at the outlet of the molecular sieve mainly comprising DPE with a small amount of DPA in EB, and which contains less than 100 ppm, preferably less than 50 ppm, of water. The relative proportions of DPE, DPA and EB in the solution are variable and depend on the performance of the catalytic dehydrogenation step and the water / DPA starting ratio, and on the amount of EB which is added to the dehydrogenate. Such a mixture in a solvent, optionally monomeric, can be used directly in SBM synthesis. The invention also relates to such a particular mixture, which comprises, by weight relative to the total weight of the mixture: 40 to 80% of DPE, preferably 50 to 70%; 1 to 30% of DPA, preferably 5 to 20%; - 5 to 50% of EB, preferably 10 to 30%; possibly other components in an amount less than 15%, preferably 10%. Such a mixture can be used directly in synthesis, in particular in SBM synthesis. Compared to a parallel synthesis process DPA / DPE and EB / S as described for example in DE19814459, the mixture contains a larger proportion of DPE. Indeed, in the document DE19814459, in Table 2, for the most favorable case of a synthesis starting from a mixture EB / DPE 50/50, the amount of DPE is only about 38% by weight of the final mixture. EXAMPLES The following examples illustrate the invention without limiting it. Using a tubular reactor of diameter 45 mm, heated to 570 ° C under a pressure of 0.5bar and containing 170ml of catalyst Styromax ® 3. This reactor was supplied with DPA and water previously vaporized at 310 ° C, at respective flow rates of 52 and 156g / h. At the outlet of the reactor, after cooling the reaction mixture, ethylbenzene is added at a rate of 13 g / h and separation is carried out by decantation at room temperature over 15 minutes. An organic phase is obtained which then comprises: - DPE: 61.2%; CCA: 11.9%; EB: 19.4%; other products: 6.5%; and water: 500ppm. After 24 hours of operation, 1560 g of DPE are thus recovered which are then treated on a molecular sieve (NK30 from CECA) to remove the water. This dehydration is implemented by feeding from below a column of 1m and diameter 24mm containing 285g of molecular sieve. The flow rate in DPE is 456 g / h. After percolation on the sieve, the water content of the product is around 45 ppm.

Claims

REVENDICATIONS
1. Procédé de fabrication de diphényl éthylène comprenant les étapes de: (a) déshydrogénation catalytique de diphényl ethane en présence d'eau; (b) addition d'un solvant organique léger au mélange obtenu à l'étape (a); et (c) décantation du mélange obtenu à l'étape (b) et récupération d'un flux contenant du diphényl éthylène en mélange avec le solvant ajouté à l' étape (b) .1. A process for the manufacture of diphenyl ethylene comprising the steps of: (a) catalytic dehydrogenation of diphenyl ethane in the presence of water; (b) adding a light organic solvent to the mixture obtained in step (a); and (c) decanting the mixture obtained in step (b) and recovering a stream containing diphenyl ethylene in admixture with the solvent added in step (b).
2. Procédé selon la revendication 1, dans lequ el le solvant organique léger est 1 ' éthylbenzène .2. Method according to claim 1, in which the light organic solvent is ethylbenzene.
3. Procédé selon la revendication 1 ou 2 , dans lequel la quantité de solvant ajoutée représente, par rapport à la masse combinée de diphényl éthylène et diphényl ethane, de 10 à 50% en poids.3. The method of claim 1 or 2, wherein the amount of solvent added represents, relative to the combined mass of diphenyl ethylene and diphenyl ethane, from 10 to 50% by weight.
4. Procédé s elon la revendication 3 , dans lequel la quantité de solvant ajoutée représente, par rapport à la masse combinée de diphényl éthylène et diphényl ethane, de 15 à 30% en poids .4. A process according to claim 3, in which the amount of solvent added represents, relative to the combined mass of diphenyl ethylene and diphenyl ethane, from 15 to 30% by weight.
5. Procédé selon l'une des revendications 1 à 4, comprenant en outre après l'étape de décantation une étape: (d) déshydratation sur tamis moléculaire.5. Method according to one of claims 1 to 4, further comprising after the decantation step a step: (d) dehydration on molecular sieve.
6. Procédé selon l'une des revendications 1 à 5, dans lequel le flux contenant le diphényl éthylène comprend, en poids par rapport au poids total du flux: 40 à 80% de diphényl éthylène; - 1 à 30 de diphényl ethane; 5 à 50% de solvant. 6. Method according to one of claims 1 to 5, in which the stream containing diphenyl ethylene comprises, by weight relative to the total weight of the stream: 40 to 80% of diphenyl ethylene; - 1 to 30 of diphenyl ethane; 5 to 50% solvent.
7. Procédé selon la revendication 6, dans lequel le flux contenant le diphényl éthylène comprend, en poids par rapport au poids total du flux: 50 à 701 de diphényl éthylène; - 5 à 20% de diphényl ethane; 10 à 30% de solvant.7. The method of claim 6, wherein the stream containing diphenyl ethylene comprises, by weight relative to the total weight of the stream: 50 to 701 of diphenyl ethylene; - 5 to 20% of diphenyl ethane; 10 to 30% solvent.
8. Mélange comprenant, en poids par rapport au poids total du mélange: - 40 à 80% de diphényl éthylène; 1 à 30% de diphényl ethane; 5 à 50% de solvant monomère.8. Mixture comprising, by weight relative to the total weight of the mixture: - 40 to 80% of diphenyl ethylene; 1 to 30% diphenyl ethane; 5 to 50% of monomeric solvent.
9. Mélange selon la revendication 8, comprenant, en poids par rapport au poids total du mélange : 50 à 701 de diphényl éthylène; 5 à 20% de diphényl ethane; 10 à 30% de solvant monomère. 9. A mixture according to claim 8, comprising, by weight relative to the total weight of the mixture: 50 to 701 of diphenyl ethylene; 5 to 20% diphenyl ethane; 10 to 30% of monomer solvent.
10. Utilisation du mélange selon la revendication 8 ou 9 ou du mélange susceptible d'être obtenu par le procédé selon l'une quelconque des revendications 2 à 7 en polymérisation.10. Use of the mixture according to claim 8 or 9 or of the mixture capable of being obtained by the process according to any one of claims 2 to 7 in polymerization.
11. Utilisation selon la revendication 10, dans laquelle. la polymérisation est la polymérisation du SBM. 11. Use according to claim 10, in which. polymerization is the polymerization of SBM.
EP05769668A 2004-05-07 2005-05-03 Method for production of diphenylethylene Withdrawn EP1742899A1 (en)

Applications Claiming Priority (2)

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FR0404943A FR2869901B1 (en) 2004-05-07 2004-05-07 PROCESS FOR PRODUCING DIPHENYL ETHYLENE
PCT/FR2005/001102 WO2005121056A1 (en) 2004-05-07 2005-05-03 Method for production of diphenylethylene

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EP1742899A1 true EP1742899A1 (en) 2007-01-17

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Publication number Priority date Publication date Assignee Title
US2402740A (en) * 1942-02-17 1946-06-25 Union Oil Co Production of styrenes
US2450334A (en) * 1945-08-21 1948-09-28 American Cyanamid Co Production of aryl substituted ethylenic compounds
SU412166A1 (en) * 1971-04-26 1974-01-25 Р. Н. Волков, В. П. Панова , Л. Н. Сорокина METHOD OF OBTAINING 1,1-DIPHENYLETHYLENE
US4365103A (en) * 1981-12-04 1982-12-21 The Dow Chemical Company Process for the preparation of bis(1-phenylethenyl) compounds
JPH07100678B2 (en) * 1987-03-12 1995-11-01 日本石油化学株式会社 Method for producing α- (3-benzoylphenyl) propionic acid
JPH02209817A (en) * 1989-02-10 1990-08-21 Asahi Chem Ind Co Ltd Purification method of 1,1-diphenylethylene
DE19814457A1 (en) * 1998-04-01 1999-10-07 Basf Ag Production of 1,1-diphenyl ethylene useful in production of copolymers with styrene
DE19814459A1 (en) * 1998-04-01 1999-10-07 Basf Ag Simultaneous production of 1,1-diphenylethylene and styrene, useful in copolymer production

Non-Patent Citations (1)

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Title
See references of WO2005121056A1 *

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FR2869901A1 (en) 2005-11-11
FR2869901B1 (en) 2006-07-07
WO2005121056A1 (en) 2005-12-22
US20080255399A1 (en) 2008-10-16

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