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WO2007090768A1 - Procede d'obtention de composes vinyle par evaporation - Google Patents

Procede d'obtention de composes vinyle par evaporation Download PDF

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Publication number
WO2007090768A1
WO2007090768A1 PCT/EP2007/050926 EP2007050926W WO2007090768A1 WO 2007090768 A1 WO2007090768 A1 WO 2007090768A1 EP 2007050926 W EP2007050926 W EP 2007050926W WO 2007090768 A1 WO2007090768 A1 WO 2007090768A1
Authority
WO
WIPO (PCT)
Prior art keywords
vinyl compounds
tube evaporator
helical tube
process according
evaporator
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2007/050926
Other languages
German (de)
English (en)
Inventor
Ortmund Lang
Bernd Rumpf
Hans-Jürgen Weyer
Christoph Sigwart
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of WO2007090768A1 publication Critical patent/WO2007090768A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/0082—Regulation; Control
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/16—Evaporating by spraying
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/10—Vacuum distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
    • C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation

Definitions

  • the present invention relates to a process for recovering vinyl compounds from a viscous solution containing vinyl compounds.
  • Vinyl compounds such as vinyl hydroxybutyl ether, vinyl imidazole, vinyl caprolactam, are important industrial chemicals and are used in the manufacture of numerous intermediates and consumables. Among vinyl compounds here are mainly intermediate products, which have a great importance as monomers for polymers, to understand.
  • the vinyl group undergoes the usual addition reactions of aliphatic double bonds, such as addition of HCl, HCN and halogens.
  • General preparation methods for vinyl compounds are the reaction of acetylene with compounds containing active hydrogen.
  • X can be, for example, Cl, RO, RS, RCOO, R 2 N-.
  • reaction discharge is usually carried out in continuously operated evaporators, e.g. Thin-film evaporators separated.
  • the liquid withdrawn residue containing the high boilers and still residues of desired product is usually disposed of thermally.
  • the distillate, which contains low boilers and the main amount of the desired product is further processed in a further distillation device.
  • the workup of the reaction effluent may be due to solids formation and / or polymerization and the high viscosity of the residue (1000 to 100000 mPa s, viscosity determination, for example, with capillary or falling ball viscometer) of the separated the residue can be carried out usually only by the addition of flow aids such as white oils in evaporators such as thin-film evaporators.
  • the object of the present invention was therefore to find a process for the evaporation of viscous vinyl compounds, which the vinyl compounds while avoiding the o.g. Disadvantages of equal or improved quality in terms of color, color stability, odor and purity provides. In addition, losses of value product due to residual contents in the sump discharge had to be minimized.
  • a process for the recovery of vinyl compounds from a viscous solution containing vinyl compounds is found, which is characterized in that the solution is fed to a preheater and heated, then expanded via a downstream pressure-holding device and fed the resulting two-phase mixture to a helical tube evaporator and there by evaporation reduces the liquid phase in its content of vinyl compounds and dissipates a gaseous product stream having an increased concentration of vinyl compounds.
  • the inventive method allows the use of a technically relatively simple helical tube evaporator for separating the vinyl compounds from the viscous residue, wherein moreover the use of additional flow aids can be avoided.
  • a helical tube evaporator - certainly not without the use of flow aids - would not have been considered by the expert here.
  • Helical tube evaporators are well known, they are described for example in US 3,550,669.
  • an evaporator is described in which the mechanical force to keep the heat exchange surface is not effected by rotating internals, but by flow forces.
  • This evaporator consists of only a single, coiled tube, which is heated from the outside.
  • This monotube evaporator is now operated so that the solution or suspension is superheated under pressure fed into the apparatus, so that already At the beginning of the apparatus evaporate a part of the volatile components of the solution. This steam takes over the function of transporting the viscous solution or suspension through the apparatus and ensures that the heat exchanger surface is kept clear.
  • reaction effluent The solution to be worked up (“reaction effluent") with a concentration of vinyl compounds of 50-98% by weight is fed and heated via line (1) to a preheater (2) operated with heat transfer oil Pressure usually between 80 ° C to 250 ° C.
  • the heated solution is removed from the preheater via line (3) .
  • the pressure in the preheater is adjusted by a downstream pressure-maintaining valve (4) so that no evaporation of the solution takes place at any point in the preheater
  • Conventional types of apparatus such as tube bundle apparatus, plate heat exchangers, spiral heat exchangers, etc. are used as preheaters
  • the mixture overheated to pressure in the downstream system components is expanded by the pressure-maintaining valve. 5) by appropriate choice of geometry , the total quantity flow and the gas portion after the expansion, a wavy film flow is set in the tube.
  • the viscous liquid flows in the form of a stream on the tubesheet.
  • the liquid accumulates and the dynamic pressure generated thereby eventually causes the pent-up mass rolls with increased flow velocity due to the evaporation in the form of a mass wave on the base layer, the tips tear off, temporarily entrained in the gas and then on the tube walls are deposited, whereby a thin film in the region of the pipe wall is formed (ring flow).
  • gas is continuously incorporated into the viscous liquid, so that the product continues to foam up over the run length.
  • increasing speed ie with increasing vapor content as a result of the evaporation, the liquid is distributed more evenly over the circumference of the pipe.
  • the product heating depending on the vinyl compound and pressure typically between 100 ° C to 270 0 C.
  • the to be reached evaporation rate - and thus the concentration of the desired product in the bottom product - is determined by the choice of the heating temperature and the pressure in the separator and can be determined for example by experiments.
  • evaporation rate is meant the ratio of distillate quantity and feed quantity.
  • the heating of the helical tube evaporator may e.g. by condensing steam or by means of a tempered oil circuit. An electric heating is possible.
  • a downstream vapor separator (6) liquid and gas are separated from each other.
  • the vapor stream may be in conventional capacitors e.g. Rohrbündelapparaten or Quenchkondensatoren - condensed.
  • the resulting condensates which in addition to low boilers contain the desired product (vinyl compounds) can be worked up in conventional distillation equipment or recycled directly.
  • the concentration of the desired product (vinyl compound) in the condensate is usually between 50 and 99.9% by weight.
  • the bottom stream from the Brüdenabscheider contains substantially the high boilers formed in the reaction and the content of product value is here depending on the driving at less than 70 wt .-% of vinyl compounds, preferably less than 20 wt .-%, more preferably less than 15 wt .-% vinyl compounds.
  • the pressure in the vapor space within the vapor separator is set at 1 to 10 4 mbar, preferably 1 to 10 3 mbar, particularly preferably 1 to 100 mbar.
  • parts of the bottom product are passed from the vapor separator back into the preheater. This is done to re-evaporate the product of value that has not yet evaporated.
  • the return of the bottom product from the Brüdenabscheider to the preheater is 1 to 80 wt .-%, preferably 10 to 50 wt .-% recycled.
  • a stripping gas such as nitrogen. This can be recommended in order to achieve the desired flow form in the helical tube evaporator or to increase the residence time of the solution in the helical tube. Adjust tube evaporator or stripping to remove light residues from the solution.
  • the Strippgasmenge to Wendelrohrverdampfer is 0 to 50 wt .-% based on the total feed stream (product + stripping gas), preferably 0 to 20 wt .-% fed.
  • the residence time can be specified by the flow velocity or the geometry of the helical tube evaporator (diameter and length).
  • the residence time in the helical tube evaporator and the associated piping system is - depending on the polymerization tendency of the mixture to be worked up - advantageously limited to 0.5 to 10 minutes, preferably 0.5 to 2 minutes. As a result, the formation of polymers and / or solid failure is reduced.
  • the process is usually carried out continuously, but in principle it is also possible to carry out the separation in batches.
  • the spiral tube may be particularly advisable to tap the spiral tube inside and / or outside.
  • This improvement is achieved both by providing a larger heat transfer area and by generating additional turbulence.
  • the process according to the invention offers a process-technically simple solution for the production of vinyl compounds.
  • the equipment cost is greatly reduced and the inventive method has long service lives and low operating costs.
  • the use of flow aids can be avoided. Examples
  • Example 1 (not according to the invention):
  • Concentration of a solution containing 97 wt .-% vinylimidazole (desired product), in a thin-film evaporator was equipped with an evaporator tube 51 * 350 mm (heat transfer area about 0.05 m 2 ). The pressure in the vapor chamber was set to 8 mbar. The feed quantity was 6 kg / h of product and 0.5 kg / h of white oil, which was used as flow aid. The heating temperature was about 150 ° C. The evaporation rate achieved was about 86%, so that there was a lump loss of value product in the bottom of 14% (based on the amount of desired product in the feed). The solution could be worked up without problems in the thin-film evaporator.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)

Abstract

L'invention concerne un procédé d'obtention de composés vinyle à partir d'une solution visqueuse contenant des composés vinyle, la solution étant passée et réchauffée dans un réchauffeur, puis détendue dans un dispositif de maintien de la pression placé en série, et le mélange biphasique résultant étant passé dans un évaporateur à spirales, où, par évaporation de la phase liquide, sa teneur en composés vinyles est réduite et un courant de produit sous forme gazeuse présentant une concentration élevée en composés vinyle est obtenu.
PCT/EP2007/050926 2006-02-09 2007-01-31 Procede d'obtention de composes vinyle par evaporation Ceased WO2007090768A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06101468.4 2006-02-09
EP06101468 2006-02-09

Publications (1)

Publication Number Publication Date
WO2007090768A1 true WO2007090768A1 (fr) 2007-08-16

Family

ID=37944820

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/050926 Ceased WO2007090768A1 (fr) 2006-02-09 2007-01-31 Procede d'obtention de composes vinyle par evaporation

Country Status (1)

Country Link
WO (1) WO2007090768A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010066769A3 (fr) * 2008-12-12 2010-11-25 Basf Se Procédé de préparation continue de copolyamides à partir de lactames et de sels de diamines et d'acides dicarboxyliques
WO2022157370A1 (fr) * 2021-01-25 2022-07-28 Basf Se Procédé continu de production d'acrylate de 2-éthylhexyle

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3550669A (en) * 1967-09-04 1970-12-29 Bayer Ag Apparatus for carrying out evaporations and reactions accompanied by the evolution of gases
GB1282992A (en) * 1969-04-25 1972-07-26 Bayer Ag Process for concentrating polymer solutions by evaporation
US3834441A (en) * 1969-04-25 1974-09-10 Bayer Ag Process for concentrating polymer solutions by evaporation
EP0451602A1 (fr) * 1990-04-07 1991-10-16 Bayer Ag Procédé continu pour concentrer des solutions polymères jusqu'à une spécification demandée des solvants résiduels
DE19827852A1 (de) * 1998-06-23 1999-12-30 Bayer Ag Verfahren zur Isolierung von Polymeren aus Lösungen
US6069228A (en) * 1998-08-17 2000-05-30 E. I. Du Pont De Nemours And Company Process for preparing polyamides
WO2000064554A1 (fr) * 1999-04-24 2000-11-02 Bayer Aktiengesellschaft Procede et dispositif pour concentrer par evaporation des solutions de polymeres thermoplastiques, et polycarbonate pouvant etre obtenu par evaporation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3550669A (en) * 1967-09-04 1970-12-29 Bayer Ag Apparatus for carrying out evaporations and reactions accompanied by the evolution of gases
GB1282992A (en) * 1969-04-25 1972-07-26 Bayer Ag Process for concentrating polymer solutions by evaporation
US3834441A (en) * 1969-04-25 1974-09-10 Bayer Ag Process for concentrating polymer solutions by evaporation
EP0451602A1 (fr) * 1990-04-07 1991-10-16 Bayer Ag Procédé continu pour concentrer des solutions polymères jusqu'à une spécification demandée des solvants résiduels
DE19827852A1 (de) * 1998-06-23 1999-12-30 Bayer Ag Verfahren zur Isolierung von Polymeren aus Lösungen
US6069228A (en) * 1998-08-17 2000-05-30 E. I. Du Pont De Nemours And Company Process for preparing polyamides
WO2000064554A1 (fr) * 1999-04-24 2000-11-02 Bayer Aktiengesellschaft Procede et dispositif pour concentrer par evaporation des solutions de polymeres thermoplastiques, et polycarbonate pouvant etre obtenu par evaporation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010066769A3 (fr) * 2008-12-12 2010-11-25 Basf Se Procédé de préparation continue de copolyamides à partir de lactames et de sels de diamines et d'acides dicarboxyliques
US9200115B2 (en) 2008-12-12 2015-12-01 Basf Se Process for continuously preparing copolyamides from lactams and salts of diamines and dicarboxylic acids
WO2022157370A1 (fr) * 2021-01-25 2022-07-28 Basf Se Procédé continu de production d'acrylate de 2-éthylhexyle
JP2024505499A (ja) * 2021-01-25 2024-02-06 ベーアーエスエフ・エスエー ２－エチルヘキシルアクリレートを得るための連続方法
JP7778798B2 (ja) 2021-01-25 2025-12-02 ベーアーエスエフ・エスエー ２－エチルヘキシルアクリレートを得るための連続方法

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