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WO2000001476A1 - Procede pour effectuer une reaction chimique exothermique et appareil conçu a cet effet - Google Patents

Procede pour effectuer une reaction chimique exothermique et appareil conçu a cet effet Download PDF

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Publication number
WO2000001476A1
WO2000001476A1 PCT/JP1999/003579 JP9903579W WO0001476A1 WO 2000001476 A1 WO2000001476 A1 WO 2000001476A1 JP 9903579 W JP9903579 W JP 9903579W WO 0001476 A1 WO0001476 A1 WO 0001476A1
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WO
WIPO (PCT)
Prior art keywords
stage
reactors
reactor
supplied
mixture
Prior art date
Application number
PCT/JP1999/003579
Other languages
English (en)
Japanese (ja)
Inventor
Yorozu Yokomori
Takashi Kumamoto
Tomoyasu Ishiguro
Kouichi Tani
Original Assignee
Kyowa Yuka Co., Ltd.
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 Kyowa Yuka Co., Ltd. filed Critical Kyowa Yuka Co., Ltd.
Priority to JP2000557913A priority Critical patent/JP4391694B2/ja
Priority to AU43967/99A priority patent/AU4396799A/en
Publication of WO2000001476A1 publication Critical patent/WO2000001476A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0006—Controlling or regulating processes
    • B01J19/0013—Controlling the temperature of the process
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2415—Tubular reactors
    • B01J19/2435—Loop-type reactors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/245—Stationary reactors without moving elements inside placed in series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxo-reaction combined with reduction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00054—Controlling or regulating the heat exchange system
    • B01J2219/00072—Mathematical modelling
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00076—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements inside the reactor

Definitions

  • the present invention relates to a method for performing an exothermic chemical reaction in a reactor using three or more reactors, particularly a method for performing a hydroformylation reaction.
  • BACKGROUND OF THE INVENTION 1 Field of the Invention The present invention relates to a method with excellent control and low differential pressure throughout the reactor, and an apparatus for performing the method.
  • Japanese Unexamined Patent Publication (Kokai) No. 9-501006 discloses a method of supplying a part of the raw materials to the first reactor and the second reactor.
  • the problem of temperature control is slightly improved, but for example, in the method disclosed in the embodiment of the publication, the differential pressure is reduced in the entire reactor because the reactor is connected in series. If it does, there is a problem. -Disclosure of the invention
  • An object of the present invention is to provide a method for performing an exothermic chemical reaction, particularly a hydroformylation reaction in a reactor using three or more reactors, in which the temperature control inside the reactor is excellent and the differential pressure throughout the reactor is small, And an apparatus for performing the method.
  • the present invention provides a method for performing an exothermic chemical reaction in a reactor including n (n 3) reactors, wherein the reactants are supplied to m (n> m 2) first-stage reactors out of n reactors. Supply independently, and then return from the m reactors Provided is a method characterized in that a primary mixture of a reaction material and a reaction product is supplied to a second or subsequent reactor without passing through another first reactor.
  • the present invention also includes one or more supply sources for supplying the reaction raw materials, and n ( ⁇ 3) reactors each having an inlet and an outlet, and the ⁇ reactors At least m (n> m 2) are the first-stage reactors, and the remaining reactors are the second-stage and subsequent reactors, where one or more supply sources are supplied via a reaction material supply passage.
  • the first stage reactor is connected to the inlet of each first stage reactor, and the outlet of each first stage reactor is connected to the inlet of the second and subsequent reactors via a supply path for supplying a mixture of reaction raw materials and reaction products.
  • a first-stage reactor a device for exothermic chemical reaction characterized by having no communication path.
  • the present invention relates to a method wherein m (n> m ⁇ 2) first-stage reactors are used to supply a reaction material containing an olefin and a synthesis gas (carbon monoxide Z hydrogen) to n (n ⁇ 3) reactors. Independently supplied and reacted, then the primary mixture of reaction raw materials and reaction products from the m first-stage reactors was passed through the first and second reactors without passing through the other first-stage reactors. And reacting them sequentially to provide a process for producing an aldehyde or alcohol having one more carbon atom than the olefin.
  • FIG. 1 is a flow chart schematically showing an embodiment in which the primary mixture is supplied from the first reactor to the second and subsequent reactors.
  • -FIG. 2 is a flow diagram schematically showing another mode of supplying the primary mixture from the first reactor to the second and subsequent reactors.
  • FIG. 3 is a flow chart schematically showing another mode of supplying the primary mixture from the first reactor to the second and subsequent reactors.
  • FIG. 4 is a flow chart schematically showing another embodiment in which the primary mixture is supplied from the first-stage reactor to the second and subsequent reactors.
  • FIG. 5 is a flow chart schematically showing a preferred embodiment of the method of the present invention.
  • FIG. 6 is a flow chart schematically showing a preferred embodiment of the method of the present invention.
  • FIG. 7 is a flow diagram schematically showing one embodiment of a reactor series in the method of the present invention.
  • FIG. 8 is a flow diagram schematically showing one typical example of a series of reactors including six reactors.
  • FIG. 9 is a schematic diagram showing one typical example of a reactor series including six reactors.
  • -FIG. 10 is a flow diagram schematically showing one typical example of a reactor series including six reactors.
  • FIG. 11 is a flow chart schematically showing one typical example of a series of reactors including six reactors.
  • FIG. 12 is a schematic diagram of a specific example of the apparatus of the present invention including a loop pre-actor.
  • 01 is the first loop reactor (first-stage reactor 1)
  • 02 is the second loop reactor.
  • 03 is 3rd loop reactor (1st stage reactor)
  • 04 is 4th loop reactor (3rd stage reactor)
  • 05 is 5th loop reactor (4th stage) 2)
  • 2 1, 2 2, 2 3, 2 4 and 2 5 are inlets
  • 3 1, 3 2, 3 3, 3 4 and 3 5 are outlets
  • 1 1, 1 2, 1 3, 1 4 and 15 represent heat exchangers.
  • FIG. 13 is a flow chart schematically showing one embodiment of a reactor series including nine reactors in the method of the present invention.
  • FIG. 14 is a front view schematically showing a comparative example of a reactor series including nine reactors. Detailed description of the invention
  • the source for supplying the reaction raw material may be one or more.
  • a total of three or more reactors are used, at least two of which are first-stage reactors, and the others are second-stage and subsequent reactors. There is at least one reactor after the second stage.
  • the flow path that passes through the maximum number of reactors is selected, and the first-stage reactor and the second-stage reactor are sequentially selected from the supply side. If there is more than one such flow channel, it is called the i-th reactor, and in order for each flow channel, it is called the first-stage reactor, the second-stage reactor, and the i-th reactor. Want).
  • the reactors that first receive the reactants from the supply source are all first-stage reactors, and no substance is supplied between the i-stage reactors. No mixture of J and reaction products is supplied).
  • a reaction raw material is divided and supplied to a plurality of first-stage reactors from one or more supply sources.
  • the supply method from the supply source does not matter.
  • a mixture of the reaction raw materials and the reaction products is supplied from the first-stage reactor to the second and subsequent reactors (in this specification, the mixture of the reaction raw materials and the reaction products from the i-th reactor is referred to as an i-th mixture. That).
  • the supply method to the second and subsequent reactors is not limited as long as the reaction material is supplied from the supply source while being divided into the first-stage reactor.
  • the primary mixture may be supplied to the second and subsequent reactors independently after mixing or without mixing, and the same applies to the secondary mixture.
  • the i-th mixture coming from them can be fed to subsequent reactors either after mixing or independently without mixing).
  • the primary mixture coming out of m first-stage reactors is independently supplied to separate m second-stage reactors without mixing.
  • all the primary mixtures from the m first-stage reactors are mixed, and the resulting mixture is supplied to one second-stage reactor.
  • some of the primary mixtures coming out of the m first-stage reactors are mixed, and the obtained mixture and each of the remaining primary mixtures are independently separated into second-stage reactors. (Example of this is shown in Fig. 1), or they are supplied to one second-stage reactor (Example of this is shown in Fig. 2).
  • some of the primary mixture exiting from the m first-stage reactors is supplied to the third and subsequent reactors without being supplied to the second-stage reactor. (An example of this is shown in Figure 3).
  • a mixture obtained by mixing some of the primary mixtures exiting from the m first-stage reactors and some of the remaining primary mixtures are represented by 2 It is supplied to the third and subsequent reactors without supplying to the first reactor (an example of this is shown in Fig. 4).
  • n reactors there are a total of n reactors,
  • n 8
  • the reaction raw materials are supplied from one or a plurality of sources to two first-stage reactors, and each first-stage reactor is connected in series to the second-stage reactor.
  • a mixture of the reaction raw material and the reaction product is supplied to the third-stage and then the fourth-stage reactor (this embodiment is shown in FIG. 6).
  • the quaternary mixture from one of the two fourth-stage reactors may be fed to one fifth-stage reactor.
  • the above embodiment is a preferable embodiment in view of the stability of the reaction temperature in the reactor and the small differential pressure generated in the entire reactor.
  • the flow once converged can be divided in the second and subsequent reactors, and such a mode is also within the scope of the present invention.
  • the reaction raw material is not supplied to only one (first) reactor at the head of the series, but is supplied separately to a plurality of reactors. 3 ⁇ 4H generated in the entire reactor can be improved. For this reason, compared with the case where the same number of reactors are connected in series, the processing amount of the entire reactor can be increased.
  • the number of reactors to which the reaction raw materials are divided and supplied is large. As the number of reactors decreases, the throughput of reaction raw materials and reaction products in each first-stage reactor decreases, the reaction temperature stability increases, and the differential pressure generated in the apparatus decreases.
  • Such a method of the present invention is suitably applied to a hydroformylation reaction using olefin, hydrogen and carbon monoxide as reaction raw materials.
  • the hydroformylich reaction refers to a reaction of reacting carbon monoxide with hydrogen and olefin to produce an aldehyde or alcohol having one more carbon atom than the olefin.
  • the hydroformylation reaction is carried out in the presence of a catalyst by the method of the present invention, the reaction is carried out under the following conditions.
  • hydrocobalt carbonyl or dicobalt octacarbonyl is used, and the ratio thereof is 0.05 to 3% by weight as a metal based on the supply weight of olefin. / 0 , and even 0.05 to 1 weight. / 0 , preferably 0.25 to 0.5 weight. / 0 is more preferable.
  • the catalyst is preferably in a state of being dissolved or dispersed in the olefin.
  • the molar ratio between synthesis gas (carbon monoxide, Z hydrogen) and olefins is usually between 0.5: 1 and
  • the volume ratio of hydrogen to carbon monoxide in the synthesis gas is usually a force of 0.5: 1 to 3: 1; preferably 9: 1 to 2: 1. , 1: 1 to 1.5: 1.
  • the reaction temperature is not limited by the type and supply amount of the starting material, but is usually from 120 to 190 ° C.
  • the temperature of the first reactor is preferably 140 to 160 ° C, and when the temperature exceeds 160 ° C, the polymer of octene, a by-product, is produced. Increase in the production of
  • the inside of the reaction system by using a water jacket or the like for each reactor and maintain the temperature within a predetermined temperature range. Further, the supply amount of the orientation is preferably such that the first reactor 1 is maintained in a predetermined temperature range.
  • the reaction pressure is usually 150 to 400 kg / cm 2 .
  • the olefins having 2 to 20 carbon atoms are used, more preferably 4 to 10 carbon atoms are preferable, and 6 to 8 carbon atoms are more preferably used.
  • a loop reactor is preferably used as the reactor.
  • the reaction raw material is divided and supplied to two first-stage reactors, and the discharged reaction liquid (a mixture of the reaction raw material and the reaction product (primary mixture)) is mixed.
  • the subsequent flow to four reactors arranged in series (Fig. 8), the method of splitting and supplying two reactors of three reactors each (Fig. 9), and the two reactants The reactor is divided and supplied to the first-stage reactor, and the reaction solution flowing out of one of the reactors is supplied to the next reactor (second-stage reactor 1). And the reaction solution from the remaining one reactor that was supplied with the raw material, and then mixed in series to form three subsequent reactors (third-stage reactor, fourth-stage reactor one, and fifth-stage reactor) (Fig. 10).
  • the raw materials are supplied to the first, second, and third reactors (three first-stage reactors), and the reaction solution discharged from the first and second reactors is supplied to the fourth reactor (the second-stage reactor).
  • a style in which each reactor is connected and reacted so that the reaction solution from the third and fourth reactors can be supplied to the fifth reactor (third reactor) and further to the sixth reactor (fourth reactor) In Fig. 11 1), the concentration of the supplied catalyst can be adjusted, so that the reaction temperature stability is increased and the generation in the apparatus is reduced.
  • the invention also provides an apparatus for performing the method of the invention as described above.
  • the apparatus of the present invention includes one or more sources for supplying the reactants and n (n 3) reactors each having an inlet and an outlet. At least m (n> m 2) of the n reactors are the first stage Is the second and subsequent reactor.
  • one or more supply sources are connected to the inlet of each first-stage reactor via the reaction material supply path, and the outlet of each first-stage reactor supplies a primary mixture of the reaction material and reaction product
  • the reactor is connected to the inlet of the second and subsequent reactors through a supply channel for the reactor.
  • the meaning of the i-th reactor is the same as described above.
  • Another feature of the apparatus of the present invention is that there is no communication path between the first-stage reactors.
  • the communication path means a supply path of the reaction mixture.
  • the number of first-stage reactors and the number of second-stage reactors are the same, and the outlet of each first-stage reactor is one of the second-stage reactors. It communicates with the inlet.
  • the outlet of the first-stage reactor is connected to the -inlet of one third-stage reactor through the secondary mixture supply channel, and this is repeated in order.
  • the apparatus of the present invention includes one source, two first-stage reactors, two second-stage reactors, and two three-stage reactors.
  • the reactor includes a first-stage reactor and two fourth-stage reactors, and the supply source communicates with the inlets of the two first-stage reactors via a reactant supply path, and the outlets of each first-stage reactor Communicates with the inlet of one second-stage reactor via the primary mixture supply channel, and the outlet of each second-stage reactor has one third-stage reactor via the secondary mixture supply channel
  • the outlet of each third-stage reactor is connected to the inlet of one fourth-stage reactor via the tertiary mixture supply channel (see Fig. 6).
  • the meaning of the i-th mixture is the same as described above, and the i-th mixture supply passage means a supply passage for supplying the i-th mixture to the subsequent reactor.
  • the number of second-stage reactors is one, and one mixer for mixing m (n> m 2) primary mixtures from the first-stage reactors
  • the inlet of the mixer communicates with each outlet of m first-stage reactors via a primary mixture supply passage, and the outlet of the mixer supplies the mixture of the primary mixture.
  • FIG. 1 One embodiment of an apparatus comprising a series of loop reactors constructed according to the present invention is shown in FIG.
  • the first loop reactor (01) is provided with an inlet (21) and an outlet (31), and a heat exchanger (11) is provided below a right vertical portion of the loop reactor (1). Cooling water is passing through.
  • the second to fifth reactors (02 to 05) also have an inlet (22 to 25), an outlet (32 to 35) and a heat exchanger (12 to).
  • the reaction raw materials are divided and supplied to the inlet (21) of the first reactor (01) (first-stage reactor) and the inlet (23) of the third reactor (03) (first-stage reactor).
  • the outlet (31) of the first reactor (01) is connected to the inlet (22) of the second reactor (02) (second-stage reactor 1).
  • the outlet (32) of the second reactor (02) is combined with the outlet (33) of the third reactor (03) to form the 3 ⁇ 4 inlet (24) of the fourth reactor (04) (the third stage reactor). ), And the outlet (34) of the fourth reactor (04) is connected to the inlet (25) of the fifth reactor (05) (the fourth stage reactor).
  • the reactants are circulating in the direction of the arrow (other reactors—the reactants are also circulating in the direction of the arrow), and the heat generated in the reaction is passed through the heat exchanger (11). It is controlled by the flow rate of the cooling water whose temperature is controlled. A small portion of the reaction mixture is removed from the outlet (31) and transferred to the second reactor (02). Most of the reaction mixture continues to circulate in the first reactor (01) ⁇ . Its internal circulation speed is generally 5 to 30 times the liquid supply flow rate.
  • Olefin conversion (%) [(A-B) / A] X I 00 (%)
  • Orefin feedstock was supplied to a series of five reactors represented in Figure 12 above.
  • the feedstock of the olefin to the first and third reactors pressure of the first and third reactors: 200 to 210 kg / cm 2
  • cobalt measured as metal
  • the temperature inside the first and third reactors was constant at 155 ° C.
  • the conversion of olefins at the outlet of the final reactor was 97%.
  • Orefin raw material was supplied to a series of five reactors represented in FIG. 12 described above.
  • the ratio of the supply of the olefin to the first reactor and the third reactor is set to 0.7: 0.3.
  • the conversion was 97%.
  • the reaction temperature can be easily controlled and the differential pressure can be reduced.
  • the maximum throughput of the reaction solution flowing through the entire reactor system is 1.33 times that of connecting five reactors in series. We were able to.
  • Example 4 In a series using eight reactors, the reactors were switched to two series in which four reactors were arranged in series, and the first reactor of each of the two series (the first reactor pressure: 200 ⁇ At 210 kg / cm 2 ), the same raw materials as in Example 1 were supplied at a feed ratio of 1: 1 and the hydroformylation reaction was carried out (see Fig. 6). £ J generated in the reactor is 12 kg / cm 2 , and the temperature inside the two first-stage reactors that supply the raw materials has a small temperature range of 155 to 158 ° C. Was. The conversion of the olefin at the outlet of the final reactor was 97%.
  • Example 4 Example 4
  • the raw material was supplied to a series of nine reactors shown in Fig.13.
  • the supply amount (velocity) of the olefin to the first reactor and the second reactor was 7000 L / hr and 8000 L / hr.
  • the pressure of the first reactor and the second reactor 193 kg / cm 2
  • the ratio of the supply amount of the raw materials to the first reactor and the second reactor 1: 1.14.
  • the hydroxyformylation reaction was carried out in the same manner as in Example 3 except that eight reactors were connected in series and the raw material was supplied only to the first reactor.
  • Example 4 The reaction was carried out in the same manner as in Example 4 except that the reaction conditions were the same as those in Example 4, except for the series of nine reactors shown in FIG. As a result, the temperature inside the first reactor is 1
  • the temperature inside the second reactor is between 154 and 1
  • a method for performing an exothermic chemical reaction in a reactor using three or more reactors particularly a method for performing a hydroformylation reaction, a method in which the temperature inside the reactor is excellently controlled and a differential pressure in the entire reactor is small, And an apparatus for performing the method are provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)

Abstract

L'invention concerne un procédé pour effectuer une réaction chimique exothermique dans un appareil de réaction qui contient n réacteurs (n ≥ 3). Le procédé est caractérisé en ce que un réactif est alimenté de façon indépendante dans m réacteurs de premier stade (n > m ≥ 2) de n réacteurs et que les mélanges de réactifs et de produits de réaction provenant de m premiers réacteurs sont alimentés dans les réacteurs de second stade ou de stade suivant sans passer par un réacteur de premier stade. Dans la pratique des réactions chimiques exothermiques, notamment de celle de hydroformylation effectuée dans un appareil de réaction utilisant trois réacteurs ou plus, on peut utiliser ce procédé pour mieux réguler la température à l'intérieur des réacteurs et pour diminuer les différences de pression parmi tous les réacteurs.
PCT/JP1999/003579 1998-07-06 1999-07-02 Procede pour effectuer une reaction chimique exothermique et appareil conçu a cet effet WO2000001476A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2000557913A JP4391694B2 (ja) 1998-07-06 1999-07-02 発熱化学反応の実施方法およびそのための装置
AU43967/99A AU4396799A (en) 1998-07-06 1999-07-02 Method for practicing exothermic chemical reaction and apparatus therefor

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Application Number Priority Date Filing Date Title
JP19018398 1998-07-06
JP10/190183 1998-07-06

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WO2000001476A1 true WO2000001476A1 (fr) 2000-01-13

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5998042A (ja) * 1982-10-25 1984-06-06 エルプロヒ−ネ・アクチエンゲゼルシヤフト メチレン橋含有ポリアリ−ルアミンの製造方法
JPH0347140A (ja) * 1989-05-11 1991-02-28 Amoco Corp 分割流れの炭化水素供給を有する多段階エチルベンゼン脱水素方法
JPH09500106A (ja) * 1993-06-14 1997-01-07 エクソン ケミカル パテンツ インコーポレイテッド ループ型装置で実施する発熱方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5998042A (ja) * 1982-10-25 1984-06-06 エルプロヒ−ネ・アクチエンゲゼルシヤフト メチレン橋含有ポリアリ−ルアミンの製造方法
JPH0347140A (ja) * 1989-05-11 1991-02-28 Amoco Corp 分割流れの炭化水素供給を有する多段階エチルベンゼン脱水素方法
JPH09500106A (ja) * 1993-06-14 1997-01-07 エクソン ケミカル パテンツ インコーポレイテッド ループ型装置で実施する発熱方法

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AU4396799A (en) 2000-01-24

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