DE2713863C2 - - Google Patents

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Publication number
DE2713863C2
DE2713863C2 DE19772713863 DE2713863A DE2713863C2 DE 2713863 C2 DE2713863 C2 DE 2713863C2 DE 19772713863 DE19772713863 DE 19772713863 DE 2713863 A DE2713863 A DE 2713863A DE 2713863 C2 DE2713863 C2 DE 2713863C2
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DE
Germany
Prior art keywords
ozone
reactors
characterized
feed mixture
reactor
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
Application number
DE19772713863
Other languages
German (de)
Other versions
DE2713863A1 (en
Inventor
Franz-J. Dipl.-Chem. Dr. 5657 Haan De Carduck
Axel 4000 Duesseldorf De Draeger
Gunter Dipl.-Ing. 4019 Monheim De Effey
Suresh Dipl.-Chem. Dr. 5657 Haan De Majmudar
Martin Dipl.-Chem. Dr. 4000 Duesseldorf De Witthaus
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE19772713863 priority Critical patent/DE2713863C2/de
Publication of DE2713863A1 publication Critical patent/DE2713863A1/en
Priority claimed from US05/966,948 external-priority patent/US4185025A/en
Application granted granted Critical
Publication of DE2713863C2 publication Critical patent/DE2713863C2/de
Expired legal-status Critical Current

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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24Stationary reactors without moving elements inside
    • B01J19/245Stationary reactors without moving elements inside placed in series
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24Stationary reactors without moving elements inside
    • B01J19/2415Tubular reactors
    • B01J19/242Tubular reactors in series
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049Controlling or regulating processes
    • B01J2219/00051Controlling the temperature
    • B01J2219/00074Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00094Jackets
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049Controlling or regulating processes
    • B01J2219/00051Controlling the temperature
    • B01J2219/00121Controlling the temperature by direct heating or cooling
    • B01J2219/00128Controlling the temperature by direct heating or cooling by evaporation of reactants

Description

The invention relates to a method and a device for continuous Production of hydroperoxides by ozonization of higher molecular weight Olefins, oleic acid or linoleic acid in the presence of water and one reactive solvent.

Through ozonization (ozone deposition) of long-chain, unsaturated compounds Ozonides can be produced that can be split into short-chain fragments are. These fragments exist depending on the type of ozonized Product and the cleavage, which can be oxidative or reductive, especially from acids, aldehydes, ketones or alcohols. Becomes For example, treated technical oleic acid (oleic) with ozone, so decays the resulting ozonide is exothermic (with the addition of oxygen) in Pelargonic acid and azelaic acid. If olefins are ozonized, they are formed in the case of oxidative cleavage corresponding carboxylic acids and Carbonyl compounds and in the case of reductive cleavage alcohols and Carbonyl compounds.

The invention relates to the ozonization of olefins, both with one as well as with more than one double bond, as well as oleic acid and linoleic acid. The method according to the invention and the device for carrying it out however, the process does not involve cleavage of the ozonized product. This is the subject of a subsequent process step or Systems.

The ozonization of unsaturated compounds can be described by the following reaction equation:  

The enthalpy of reaction Δ H of this ozonization reaction is approximately 100 kcal / mol of double bonds or approximately 2000 kcal / kg of reacted ozone. It is difficult to remove this large amount of heat since the reaction is supposed to take place at a relatively low temperature in order to avoid premature onset of the ozonide cleavage. This is because ozonides are relatively unstable and begin to decompose at room temperature - also in an exothermic reaction.

As I said, the ozonized product - here the ozonide - can only be split in a subsequent step. The For example, cleavage can be oxidative at about 100 ° C according to the following Run reaction equation:

To prevent the ozonide cleavage according to equation (2) prematurely uses and takes an uncontrolled course, you can Ozonization of the unsaturated compounds according to (1) in the presence of organic acids or alcohols as reactive solvents carry out. The resulting ozonides react according to equation (1) this procedure with organic acids to ester hydroperoxides or with alcohols to alkoxyhydroxyperoxides, which in turn are essential are more stable than the ozonides. Are organic acids considered reactive Solvent used, the reaction proceeds according to the following Reaction equation:

The resulting ozonized products - here are ester hydroperoxides and aldehydes - can then be separated Reaction step by hydrolytic-oxidative cleavage are converted into the corresponding acids as follows:

The solvent (R ′ ′ COOH) can be removed by distillation be returned to the process.

Analogous to the reaction scheme above, the ozonization proceeds in Presence of alcohols as a reactive solvent. That as Intermediate alkoxy hydroperoxide decomposes at hydrolytic-oxidative cleavage in those used as solvents Alcohol, the corresponding carboxylic acid and water.

When ozonizing, the viscosity of the ozonized product decreases significantly. However, the viscosity can be affected by that in the reaction (3) reactive solvents used for stabilization be reduced. For example, it is from the US PS 28 13 113 known to reduce the viscosity of the liquid Phase in the ozonization reactor during the ozonolysis of oleic acid to add pelargonic acid to the feed mixture, after the oxidative cleavage of the ozonide the added and the resulting Pelargonic acid separated from the azelaic acid produced becomes.

Besides the problem, the viscosity of the ozonized product To keep it low, there is always - as I said - that Task, the heat of reaction of the ozonization reaction at least to the extent that the splitting of the ozonized  Product, e.g. B. the ozonide, the ester hydroperoxide or the alkoxy hydroperoxide is sufficiently delayed. To for this purpose the reaction temperature should be approx. 50 ° C if possible do not exceed.  

To remove the heat of reaction by evaporative cooling, is in US Pat. No. 2,865,937, the organic Add 100 to 600% water mix. The heat of reaction is then evaporation of water and removal of the Water vapor eliminated with the exhaust gas. By the heat of reaction however, only about 4 kg of water are evaporated per kg of ozone converted. The remaining water remains in the ozonized product and must be evaporated with considerable effort. Aggravating Added to this is the fact that, in particular, short-chain reaction products are volatile in water. It doesn't just cause a loss of usable products but also generates exhaust air or wastewater problems. Even according to the US PS 28 13 113 is said to be the presence of a substantial amount of Water (more than 10 to 15%) disadvantageous in the ozonized product impact.

However, the heat of reaction is in accordance with indirect cooling U.S. Patent 28 13 113 dissipated because of the desired low Temperature of 25 to 45 ° C a large expenditure on equipment combined with high energy and cooling water requirements for discharge the heat of reaction required.

It is fundamental for economic and technical reasons required that both reactants be virtually quantitative be implemented. Mostly because of air pollution and the toxic nature of ozone - maximum permissible workplace - Concentration (MAK) = 0.1 ppm - should be all ozone be used so that it does not escape into the open with the exhaust gas. Otherwise there would be extensive ozone depletion plants required. According to the known method according to US-PS 28 13 113, should therefore be used a countercurrent reactor in which the liquid phase from top to bottom and the ozone-containing gas from flows from bottom to top. In ozonization, however, is a Counterflow reactor because of the large gas-liquid ratio and the high viscosity of the ozonized product very complex. In contrast, a direct current driving style enable 20 to 30 times the gas velocity in the reactor, so that the latter could be designed accordingly smaller.  

With DC mode of operation, however, is a quantitative implementation the reaction participant has not yet been able to be implemented easily.

The invention is therefore based on the object of a method and a device for ozonization according to the aforementioned To create genre that without the complex countercurrent procedure in the reactor for a practical quantitative implementation of the feed mixture to be ozonized with at most negligible low excess ozone. The solution should also be take into account the fact that the ozonization reaction is so rapid that the diffusion of ozone from the Gas phase in the liquid phase of the speed-determining Step is. Therefore, funds should also be created which ensure that the liquid reactant phase is not only a large but also a constantly renewing surface forms. By these means an intensive mixture of two phases, which should be all the more intense, the more the individual reactants are used up. To take into account that ozone-containing gas with a concentration from only 0.5 to 2.5 vol% and a pre-pressure of in usually less than 2 bar is available that the volume Ratio of liquid phase to gas phase (in the invention Process) is about 1 in 1500 to 4000 and that the viscosity increases with increasing degree of ozonization. It should also be noted that the heat of reaction in the Ozonization is about 8400 kJ / kg ozone, but that Temperature in the reactor is to be limited to 10 to 50 ° C, so that the ozonide cleavage does not start prematurely.

The invention should in particular an ozonization process for Be made available on the one hand in devices with economically feasible dimensions, but that on the other hand, a practically complete consumption of the used Ensures ozone so that the exhaust gas resulting from the process increases does not cause pollution or damage to the environment.  

The task presented is described by the following Ozonization process and the device for carrying it out solved.

The invention relates to a process for continuous Production of hydroperoxides by ozonization of higher molecular weight Olefins, oleic acid or linoleic acid in the presence of water and

  • a) in the presence of an organic acid or
  • b) in the presence of an alcohol in aldehydes

whereby according to the procedure a) ester hydroperoxides and Aldehydes and b) alkoxy hydroperoxides and aldehydes be preserved. This method is characterized in that continuously fresh mixture to be ozonized, which contains 2 to 49% Contains water, can react in cocurrent with an ozone-containing gas, which was previously used to ozonize an already partially ozonized one Mixture was used and already partially ozonized feed mixture in cocurrent with fresh ozone-containing gas treated.

The invention further relates to a device for carrying it out of the method defined above, which is characterized in that a reactor system with at least 2 switched in counterflow, but individually of the feed mixture to be ozonized and the ozone-containing one Gas in co-current flow reactors is provided.

According to the invention, the two are made from a Organic feed mixture containing 2% to 49% water on the one hand and ozone-containing gas on the other  Reactants each in cocurrent through at least two reactors of a reactor system connected in countercurrent headed. The reactants and reaction products should for the control of ozonization as well as for even discharge the reaction enthalpy in situ evaporative cooling in the reactors are constantly mixed intensively. The simultaneous outer countercurrent mode and inner cocurrent mode is in one with at least two reactors Reactor system achieved in that the ozonized Mixture of the reactor system from one side and supplies the ozone-containing gas from the other side, so that the reactants the reactors in the opposite order but flow through each reactor in the same direction.

To the required water content of 2 to 49% of that to be ozonized Mixture of use is to be said that at least as much water is to be used as for the in situ dissipation of the reaction enthalpy is required during ozonization. Preferably that is additionally for the subsequent hydrolytic-oxidative cleavage required water for the mixture to be ozonized (organic phase) added.

The invention ensures that even with relative small-sized reactors with relatively high-viscosity products can work if one of two or more DC Reactors existing reactor system used, in which the individual reactors are connected to each other in countercurrent. This procedure or the corresponding device have as desired, an almost quantitative implementation of the reactants - namely the feed mixture to be ozonized and the ozone - result.

At the same time, the in situ evaporative cooling without additional indirect cooling the reaction temperature in very narrow limits within the desired temperature range self-regulating are kept constant. The equilibrium temperature becomes essentially for a given reaction mixture determined by the ozone concentration.  

As is known, ozone is generated by silent electrical discharges. The power consumption is approx. 18 to 25 kWh / kg ozone, when air is used as an oxygen source. The specific one The lower the ozone concentration, the lower the power consumption is in the ozonized air. Already with one Reduction of the ozone concentration in the air from 2% to 1% the specific electricity consumption is reduced by approx. 30%. Therefore it is energetically advantageous with lower ozone concentration to work. With the lowering of the ozone concentration however, inevitably involves handling larger amounts of air, that is, with conventional counterflow operation in a column would require very large column cross sections.

The invention also ensures that air with a low ozone concentration can and still the reactors become relatively small, both of which Ozone as well as the unsaturated compounds practically quantitative be implemented.

According to another invention in the as DC columns trained reactors static mixing elements of this type and arrangements provided that one with increasing degree of ozonization more intense mix of reactants, including the water, and the reaction products is guaranteed. Because of this intense mix of reactants and reaction products can according to the invention - as opposed to the case according to US-PS 28 65 937 - with a water content of only about 2 to 49% to ozonizing feed mixture (organic phase) always sufficiently low viscosity of the liquid phase. It is not necessary to use the reactors fully equipped with the static mixing elements.

The static mixers used according to the invention, that is not contain moving components, e.g. B. from be built up individual mixing elements, each of which corrugated slats and which are stacked in such a way are that open, intersecting channels are formed. In the latter, the fluid is split into individual streams. At  each intersection is a subset in the crossing channel sheared. An inhomogeneity is the same in the first mixing element two-dimensionally and in the following, um Twisted 90 °, three-dimensional (see company brochure Sulzer AG, Winterthur, Switzerland, No. 22.85.06-Cgc 40). It other static mixers can also be used, e.g. B. one consisting of a number of stationary right-handed and left-handed arranged in a tubular housing Elements (coils). This is allotted in operation mixing medium at the leading edge of each element in two Partial streams and follows two semicircular channels. At every subsequent element edge, the two partial flows are again divided and simultaneously with a partial stream of the opposite semi-circular channel reunited, (see US Pat. Nos. 32 86 992, 36 63 638 and 37 04 006).

Experience has shown that the static mixing elements can be partially or completely replaced by packing. Such fillers are particularly suitable, despite larger ones Surface does not break the emulsion, no liquid nests create and have only a small hold-up. The column reactors can also be operated by tube bundle reactors are replaced, which then with appropriate packing or static mixing elements. In principle all so-called static mixers can be used.

Both column and tube bundle reactors can be equipped with cooling or heating jacket. This will apply when used the additional possibility given by the in situ evaporative cooling resulting equilibrium temperature regardless of the selected ozone concentration and / or the selected Concentration of unsaturated compounds in the feed mixture adjust as needed.

Partly based on the schematic drawing of three exemplary embodiments further details are explained:  

According to FIG. 1, the reactor system according to the invention consists of at least two reactors 1 and 2 , which are connected to one another in such a way that the gas phase and the liquid emulsion are in countercurrent in the system, but flow through the individual reactors in cocurrent. To a certain extent, this combination combines the advantages of countercurrent and cocurrent operation. The circuit thus avoids the reaction between the concentrated reactants freshly entering the reactor system, namely the feed mixture 4 and the ozone-containing gas 5 . For this reason alone, the heat of reaction is better distributed in the reactors and temperature jumps are avoided. However, since there is direct current within the reactors, a relatively high gas velocity is possible, and the reactors can therefore be dimensioned accordingly small. This enables the use of an inexpensive mixture of ozone with air in a low ozone concentration.

According to the scheme of FIG. 1, the feed mixture 4, consisting of an organic phase and water in finely divided form to the reactor 1 and fresh ozone-containing gas 5 is supplied to the reactor 2. In the exemplary embodiment, the ozone-containing waste gas 8 from reactor 2 with the fresh feed mixture should primarily be converted almost quantitatively in the reactor 1 . In the reactor 2 , on the other hand, the ozonization of the partially converted feed mixture 4 from reactor 1 with fresh gas 5 containing ozone is completed.

In FIG. 2, a reactor system is shown with an additional reactor 3. The additional reactor 3 makes the driving style more flexible and intercepts fluctuations and malfunctions. The reactants flow through the reactor 3 , like the reactors 1 and 2, in cocurrent, but it is connected in countercurrent to the other reactors. With this procedure, the main reaction conversion takes place in reactor 2 . In the reactor 1 , the residual ozone is washed out of the exhaust gas from the reactor 2 with fresh feed mixture. In contrast, the unreacted feed mixture from reactor 2 is completely converted in reactor 3 with fresh ozone-containing gas. The partially converted feed mixture from reactor 1 flows through line 10 into reactor 2 . The partially ozone-containing gas also flows from reactor 3 into reactor 2 via line 7 . The two reactants are largely implemented in reactor 2 . The pumps 13 in the lines 9, 10, 11 and 12 are provided for the conveyance of the liquid products.

In the arrangement according to FIG. 3, the feed mixture 4 is fed directly into the reactor 1, whereas the ozone-containing gas is divided into two streams 14 and 15 5, so that the larger current 14 in the reactor 2 and the smaller current 15 in the Reactor 3 arrives. The exhaust gas stream 16 from the reactor 3 is fed to the reactor 1 .

In the device according to FIG. 3, the liquid and gaseous phases of the reactants and reaction products are first separated in a downstream container 17 to 19 . The corresponding exhaust gas flows are indicated by arrows 20 to 22 pointing upwards. The liquid phase flows down through closable valves 23 to 25 to intermediate containers 26 to 28 and via pumps 29 to 31 to the next reactor or into the outlet 32 . It should be noted that the feed mixture and the ozone gas can of course also be added at the top of the individual reactors. The two reactants then flow into the reactor - as shown in FIGS. 1 and 2 - from top to bottom.

The greatest ozone conversion takes place in the reactor 2 according to FIG. 3 and its waste gas 21 is practically ozone-free. The last ozonizable traces of the feed mixture are reacted in the reactor 3 with the aid of fresh ozone-containing gas (line 15 ), so that the feed mixture is completely ozonized. The exhaust gas 22 from the reactor 3 still contains a considerable amount of ozone, which is washed out in the reactor 1 with fresh feed mixture.

The subsequent hydrolytic-oxidative cleavage is proportionate run moderately small amounts of air. It will be about 10 to 15% of the amount of air needed for ozonization is needed.  

Traces of ozone are known to favor this fission. An advantage of the arrangement according to FIG. 3 is therefore that the amount of gas in the reactor 2 can be selected so that the exhaust gas is obtained in the amount that may be required for the hydrolytic-oxidative cleavage. Furthermore, the ozone conversion in the reactor 2 can be controlled so that the exhaust gas 21 still contains the amount of ozone required for the hydrolytic-oxidative cleavage.

The reactors of the systems shown in FIG. 1, 2 and 3 are preferably equipped with the above-mentioned static mixers. These are, for example, static mixers 34 with mixing elements consisting of corrugated fins and joined together to form intersecting open channels, and / or static mixers with successive, alternating right and left-handed helical gears. In contrast, the reactor 3 in FIG. 2 is a packed column, and such a column can therefore also be used.

The mixing elements are responsible for the three phases (organic Phase, water and ozone-containing gas) bring, that is, the two liquid phases very fine emulsify and mix the gas phase with the emulsion intensively. This is done in the mixers by reducing the drop size and their redistribution, i.e. by constantly creating new surfaces, combined with multiple redirection of the gas flow.

It is particularly advantageous that the arrangement of the Mixing elements or packing or both in the reactor the reaction is controlled and promoted so that the heat of reaction not suddenly in a small room, but evenly throughout the room distributed arises. This ensures that the heat of reaction through uniform water evaporation (without temperature and pressure fluctuations in the reactor) can be dissipated. According to the invention, it is a quasi isothermal driving style possible.

Another way to avoid local overheating consists in the return of the flowing liquid in the  Reactor head.

The static mixer or packing in the inventive Reactors are designed and arranged so that they come from the Mixture of the aqueous and organic phases form stable emulsion and this emulsion with the ozone-containing Mix the gas well and constantly create new surfaces. Therefore used ozone is added to the liquid surface and the phase transition or the diffusion of ozone into unreacted organic phase is promoted. The targeted arrangement of the Mixing elements also results in a sudden mix and so that a spontaneous reaction cannot take place that The reaction therefore takes place along the entire route in the individual Reactors evenly, although the viscosity of the liquid phase with the degree of ozonization increases.

The method according to the invention and the corresponding device are also advantageous because the new reactor system has a quantitative Conversion of the reactants without expensive countercurrent Reactors allowed. Residual ozone falls only in negligible Amount of. Through intensive gas / liquid contact a high implementation speed possible. Here is the Liquid hold up in the individual reactors is very small. In spite of relatively small amount of water - because of the intense Mixture - a stable water-in-oil emulsion is formed. Because only small amounts of water are used, the reprocessing costs and the product losses compared to the corresponding State of the art reduced. The wastewater problem is also defused. When you finally use tube bundle reactors, the mean reaction temperature can also be determined by indirect Heating or cooling can be set as desired.

By using static mixers or fillers and their targeted arrangement in the reactors is relatively small Even heat dissipation at low temperature in the reactors and thus a high level of technical security reached. The amount of water used in the invention is  at least as much as for the in situ dissipation of the reaction enthalpy is required, plus a surplus for Lowering the viscosity of the ozonized product. It however, water is no longer used as for the subsequent one Cleavage is required anyway. This makes it possible the required amount of water based on 2 to 49% restrict the feed mixture (organic phase). The water essentially has the task of exothermic heat of reaction intercept the temperature in each reactor too control and the viscosity of the reaction product particularly to reduce towards the end of the reaction.

The invention finally achieves that for Ozonization used relatively small-sized reactors can be. By using static mixing elements and / or special packing and their targeted Arrangement in the individual reactors is achieved that the Liquid hold up in the individual reactors is very small is held. This is very advantageous for security reasons since, as is well known, ozonized products for explosive Tend to decompose.

List of reference numbers

1-3 = reactors
4 = insert mixture
5 = gas containing ozone
6 = exhaust gas
7, 8 = lines for ozone gas
9-12 = lines for feed mixture or ozonide
13 = pumps
14-16 = lines for ozone gas
17-19 = container
20-22 = exhaust gas
23-25 = valves
26-28 = intermediate container
29-31 = pumps
32 = outlet
33 = free space
34 = mixer.

Claims (9)

1. Process for the continuous production of hydroperoxides by ozonization of higher molecular weight olefins, oleic acid or linoleic acid in the presence of water and
  • a) in the presence of an organic acid or
  • b) in the presence of an alcohol,
whereby after the procedure a) ester hydroperoxides and aldehydes and after the procedure b) alkoxy hydroperoxides and aldehydes are obtained, characterized in that continuously fresh to be ozonized feed mixture ( 4 ), which contains 2 to 49% water, in cocurrent with an ozone-containing gas ( 5 ) can react, which was previously used to ozonize an already partially ozonized feed mixture, and at the same time treated already partially ozonized feed mixture in cocurrent with fresh ozone-containing gas.
2. The method according to claim 1, characterized in that the ozonizing feed mixture ( 4 ) a reactor system with at least two reactors ( 1, 2 ) from one side ( 9 ) and ozone-containing gas ( 5 ) from the other side ( 7 ) supplies and can react within the individual reactors, in particular at about 10 to 50 ° C, in cocurrent.
3. The method according to claims 1 and 2, characterized in that you have an ozone-containing gas with an ozone concentration from 0.1% to 1% ozone.
4. An apparatus for carrying out the method according to claim 1, characterized in that a reactor system with at least two reactors ( 1, 2 ) which are switched in countercurrent but individually by the feed mixture to be ozonized ( 4 ) and the ozone-containing gas ( 5 ) in cocurrent. is provided.
5. The device according to claim 4, characterized in that in the reactors ( 1, 2 ) static mixing elements ( 34 ) such type and arrangement are provided that a more intensive mixture of reactants, including the water and the reaction products is guaranteed with increasing degree of ozonization.
6. The device according to claim 5, characterized in that Tube bundle reactors are provided.
7. The device according to claim 6, characterized in that in the reactors ( 1, 2 and 3 ) packing, static mixer or a combination of static mixer and packing are provided.
8. The device according to claim 4, characterized in that the reactors ( 1, 2 ) have a cooling or heating jacket.
DE19772713863 1977-03-29 1977-03-29 Expired DE2713863C2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE19772713863 DE2713863C2 (en) 1977-03-29 1977-03-29

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19772713863 DE2713863C2 (en) 1977-03-29 1977-03-29
NL7802549A NL7802549A (en) 1977-03-29 1978-03-08 Method and device for the continuous ozonization.
BE186302A BE865357A (en) 1977-03-29 1978-03-28 Method and ozonization device continuously
US05/966,948 US4185025A (en) 1977-03-29 1978-12-06 Continuous process for ozonizing unsaturated compounds

Publications (2)

Publication Number Publication Date
DE2713863A1 DE2713863A1 (en) 1978-10-12
DE2713863C2 true DE2713863C2 (en) 1989-06-01

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DE19772713863 Expired DE2713863C2 (en) 1977-03-29 1977-03-29

Country Status (3)

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BE (1) BE865357A (en)
DE (1) DE2713863C2 (en)
NL (1) NL7802549A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2754366A1 (en) * 1977-12-07 1979-06-13 Henkel Kgaa An apparatus for continuously ozonate
DE2942279C2 (en) * 1979-10-19 1986-01-09 Chemische Werke Huels Ag, 4370 Marl, De
DE3005514A1 (en) * 1980-02-14 1981-10-01 Henkel Kgaa Method for continuous ozonolysis of olefins
DE3722566A1 (en) * 1987-07-08 1989-01-19 Henkel Kgaa Method for continuous ozonization of unsatured organic compounds
EP0555472B1 (en) * 1991-08-06 1995-11-29 Lion Corporation Process for ozonizing unsaturated fatty acid or lower alkyl ester thereof and oxidative decomposition of the resulting ozonide
JP2000219886A (en) 1999-02-01 2000-08-08 Masatoshi Matsumura Method and apparatus for conversion of vegetable oil (virgin) or waste vegetable oil to fuel for diesel engine
AT500489A1 (en) * 2001-03-09 2006-01-15 Dsm Fine Chem Austria Gmbh Process for the production of mono or biscarbonyl or hydroxyl compounds
CN102657927A (en) * 2012-05-18 2012-09-12 西安费斯达自动化工程有限公司 Method for treating linoleic acid with ozone

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2813113A (en) * 1953-05-07 1957-11-12 Emery Industries Inc Method of making azelaic acid
US2865937A (en) * 1956-03-06 1958-12-23 Welsbach Corp Processes for the production of dibasic and monobasic acids

Also Published As

Publication number Publication date
DE2713863A1 (en) 1978-10-12
BE865357A (en) 1978-09-28
BE865357A1 (en)
NL7802549A (en) 1978-10-03

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