US3336399A - Dehydrogenating hydroxy-and oxocycloaliphatic compounds - Google Patents

Dehydrogenating hydroxy-and oxocycloaliphatic compounds Download PDF

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US3336399A
US3336399A US305763A US30576363A US3336399A US 3336399 A US3336399 A US 3336399A US 305763 A US305763 A US 305763A US 30576363 A US30576363 A US 30576363A US 3336399 A US3336399 A US 3336399A
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catalyst
naphthalene
tetrahydro
naphthol
hydroxy
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Gac Robert
Zeppieri Louis
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Progil SARL
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Progil SARL
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/72—Copper
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/755—Nickel
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • B01J37/0027—Powdering
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • B01J37/18—Reducing with gases containing free hydrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring

Definitions

  • This invention relates to a process for the manufacture of heavy phenols from corresponding oxygenated cycloaliphatic compounds and, more particularly, to the production of naphthols by the dehydrogenation of alcohols and ketones derived from more or less hydrogenated naphthalene and alpha naphthol, from 1 hydroxy- 1,2,3,4 tetrahydro-naphthalene or 1 oxo -l,2,3,4 tetra hydro-naphthalene.
  • a principal object of this invention is the provision of a method for dehydrogen-ating hydroxyand oxo-cycloaliphatic compounds and, more particularly, from l-hydroxy 1,2,3,4 tetrahydro naphthalene or 1 oxol,2,3,4 tetrahydro naphthalene of the corresponding naphthols with a high rate of transformation, practically free from tetrahydronaphthol.
  • the single figure is a schematic diagram of apparatus for performing the process of the invention.
  • the invention consists in the discovery of special catalysts to be used in the dehydrogenation of oxygenated cycloaliphatic compounds for the purpose of obtaining the corresponding heavy phenols. It has been discovered that, in "order for the dehydrogenation of the aliphatic ring to take place selectively, the catalytic mass 3,336,399 Patented Aug. 15, 1967 The new process consists, in the first place, of subjecting oxygenated cycloaliphatic compounds in the liquid state to heating in the presence of a dehydrogenation catalyst made up of one or more finely divided catalytic metals deposited on an oxide support of a basic or entirely neutral character and not containing any composition of an acid character in the free state.
  • Catalytic metals which can be used as part of the catalyst of the invention may be one or more of the metals selected from the group consisting of nickel, copper, iron, cobalt, chromium, platinum, or other metals of the platinum group, such as iridium, palladium, and rhodium.
  • Carriers which can be used with the catalyst include the basic oxides, particularly those of metals of Groups I and II of the Periodic Table, especially calcium oxide, magnesium oxide, copper oxide, strontium oxide, barium oxide, and zirconium oxide. Some oxides, such as silica, may be used, but only in a perfectly neutral form, such as kieselguhr, which does not contain any acid foci.
  • Catalysts may be prepared in accordance with the invention by using 20 to parts by Weight of the finely divided catalytic metal per 100 parts of carrier.
  • the catalytic metal makes up 50 to 100 parts per each 100 parts by weight of carrier.
  • a preparation of these catalysts can be carried out in the usual manner. For instance, a mixture of a desired metal oxide with a selected support powder may take place by co-precipitation, by tabletting, or by granulation and reduction in hydrogen, preferably at a temperature equal to or in the vicinty of that at which the catalyst is to be used.
  • the dehydrogenation take place at temperatures which are in the vicinity of the boiling point of the reaction liquid. It is particularly advantageous to work under boiling conditions at atmospheric pressure -or at any pressure from 1 to 5 atmospheres.
  • the oxygenated cycloaliphatic compound which is to be treated is l oxo 1,2,3,4 tetrahydro naphthalene
  • the best temperature to use for ob taining alpha-naphthol is in the range from 200 C. to 350 C.
  • the velocity of the reaction and the rate of conversion increases with the temperature and the results are particularly favorable at the boiling point of the reaction mixture, which lies between 256 C. and 290 C. at atmospheric pressure. If the process is carried out at a slightly higher pressure in the range from absolute pressures from 1 to 3 kilograms per centimeter square, the
  • favorable temperature range would be in the range from 305 C. to 340 C.
  • the temperature at which dehydrogenation should take place is about 240 C.
  • the process of the invention being preferably carried out in a paI- ticular manner; that is to say, by carrying out the reaction in two stages; (1) heating the mixture to boiling under reduced pressure with a contact time in the catalytic space, which is short (just long enough to convert virtually all of the 1 hydroxy 1,-2,3,4 tetrahydro naphthalene to 1 oxo 1,2,3,4 tetrahydro naphthalene, and (2) treatment at a higher temperature as indicated above in relation to 1 oxo 1,2,3,4 tetrahydro naphthalene.
  • the first stage can advantageously be carried out at a pressure of 400 to 760 millimeters Hg which corresponds to boiling temperatures of about 225 C. to 250 C.
  • the efiiciency of the process is increased by a vigorous agitation of the liquid while in contact with the catalyst. In the case of a fixed bed catalyst this agitation is obtained by a very rapid passage of liquid to be treated through the bed.
  • Another means is by the bubbling of an inert gas (for example, nitrogen) through the liquid in contact with the catalyst. This bubbling should take place at regulated rates within certain limits, particularly 150 to 200 times the volume of the catalytic space per hour.
  • the process of the invention can be carried out in two different ways: With a fixed catalytic bed, or with catalyst particles in suspension in the reaction medium.
  • a fixed catalytic bed or with catalyst particles in suspension in the reaction medium.
  • the catalyst be in the form of granules or particles of a size from 0.5 to 10 millimeters and, preferably, in the range from 2 to millimeters.
  • the linear rates of flow for the reaction liquid through the catalytic bed are preferably from 4 to 100 meters per hour, and, preferably, from to 40 meters per hour, calculated for the theoretically empty apparatus.
  • the preferred dimensions of the catalytic granules are less than that used in a fixed bed. They can be in the range from 0.1 to 5 millimeters, but preferably are in the range from 0.1 to 1 millimeter.
  • the suspension can contain 10 to 40 parts by weight of the latter per 100 parts of liquid. However, the preferred proportions are from to parts per 100.
  • This process can be carried out continuously or discontinuously. In the former case, it is recommended that several reactors be employed in series in order to take into account the rapid decrease in the rate of conversion as a function of time, which is characteristic of the reaction in question.
  • the novel process can be carried out by use of various types of apparatus which allow operation with a fixed bed catalyst or a suspended catalyst.
  • the apparatus is provided with a flask 11 which serves for the intermediate storage of liquid obtained by a dehydrogenation which takes place in a reactor 14 of the starting material obtained from a reservoir 15.
  • a supply pump 16 causes the liquid to pass from the reservoir 15 into the bed of catalyst in the reactor 14.
  • the bed receives the treated liquid from the flask 11 by way of a circulation pump 12.
  • the liquid passes through a preheater 13 and arrives at a catalytic bed at the desired temperature, for instance, 250 C.
  • the reactor 14 is provided with a heater 28 which permits the catalyst bed in the reactor 14 to be preheated.
  • the reactor is provided with an enlargement 25 provided with an overflow pipe 26 which leads back to the flask 11.
  • the top of the enlargement 25 is provided with a column 17 through which the vapors evolved by the reaction pass and, eventually, reach a condenser 18.
  • a separator 20 is provided at the bottom of the condenser 18 in which water recovered separates out and is removed through the pipe 21. The hydrogen escapes through a vent 19 at the top of the separator.
  • the decanted liquid from the separator 20 returns to the flask 11 through a pipe 22.
  • a vent 24 at the top of the flask 11 is provided with a cooler for avoiding the escape of naphtholic vapors into the atmosphere.
  • Withdrawal of the finished product is made by way of a takeoff valve 23 and a valve 27 regulates the flow of liquid from the pump 16 to the reactor 14.
  • the reaction can also be carried out with a single passage of the reaction mixture through a tubular apparatus of sufficient length but which is divided into several sections for eliminating the hydrogen produced in each section. However, in order to achieve high rates of flow of liquid, in accordance with the invention, it is generally more advantageous to recirculate the reaction mass in a closed circuit through the catalyst in order to obtain the desired rate of conversion.
  • the apparatus shown in the drawing is particularly suitable for this type of operation.
  • a predetermined volume of the primary material is withdrawn from the reservoir 15 and the pump 16 forces it into the reactor 14.
  • the valve 27 is then closed and operation takes place using the circulation pump 12.
  • the liquid circulates around the various circuits, while the hydrogen formed in the reactor 14 is released through the pipe 19.
  • the flask 11 contains the desired naphthol (or other heavy phenol) content
  • the material is withdrawn through the valve 23 and a new charge of starting material from the reservoir 15 is introduced into the apparatus.
  • A represents a catalyst prepared in the following manner:
  • cupric oxide CuO
  • ZnO zinc oxide
  • Two kinds of particles were prepared in this manner: (1) Tablets in the form of cylinders which are 3 millimeters long and 3 millimeters in diameter, and (2) Granules of selected sizes from 0.2 to 0.5 millimeter; 0.5 to 1 millimeter; 1 to 2 millimeters; and 2 to 5 millimeters; formed by grinding and screening the tablets.
  • the catalyst is reduced in hydrogen between C. and 275 C. to effect complete transformation of the CuO into finely divided metallic copper.
  • the catalyst designated B in certain of the following examples is made up of metal deposited on kieselguhr, in the well-known manner.
  • the catalyst contains 50% by weight of nickel and includes no acid foci.
  • Kieselguhr is a mineral of completely neutral SiO
  • This catalyst was made in two forms similar to those in catalyst A, that is to say, (1) cylindrical pastilles of 5 x 5 millimeters, and (2) four series of granules of pre-determined size in the range from 0.2 to 0.5 millimeter; 0.5 to 1 millimeter; 1 to 2 millimeters; and 2 to 5 millimeters; after reduction of the nickel oxide to metallic nickel is was superficially re-oxidized in order to stabilize the catalyst.
  • Example I In an apparatus of the kind shown in the accompanying drawing, the reactor 14 had an internal diameter of T8 square centimeters and was filled with 1,000 grams of catalyst A in rods 3 millimeters long and 3 millimeters in diameter and preheated by means of the heater 28 to 250 C. 1700 grams of tetralone were preheated to 250 C. in the flask 11 and then circulated at the rate of 7.5 litres per hour, namely, at a linear velocity of 10 meters per hour through the catalyst bed. The composition of the mixture obtained as a function of time is given in Table I.
  • Example II The operation proceeded in the same manner as Example I, but at temperatures of 230 C. and 200 C., re-
  • Example IV and withdrawal were carried on cont1nuously at the rate
  • 1,000 grams of catalyst B was introduced, as described in Example II, in the form of rods of 5 millimeters diameter and 5 millimeters long.
  • the operation proceeded with 2,000 grams of 'tetralone at 250 C. with circulation at the rate of 10 meters per hour.
  • Table II The results are tabulated in Table II below.
  • Example V The operation took place exactly as in Example IV but at boiling temperature, namely 258 to 280 C.
  • Example VI The operation took place exactly as in Example V but the linear velocity of the liquid over the catalyst was increased to 24 meters per hour. The results are shown in Table II.
  • Example IX The process took place in the same manner as in Example VI using 1,000 grams of catalyst B. The mixture was at its boiling point but the charge was made up of 2,000 grams of mixture of 76% l-oxo-l,2,3,4-tetrahydronaphthalene and 24% 1 hydroxy-1,2,3,4 tetrahydronaphthalene. After one-half hour the rate of conversion was 100% for l-hydroxy-1,2,3,4-tetrahydro-naphthalene and 45% for l-oxo-l,2,3,4-tetrahydro-naphthalene. The mixture obtained contained 44% of alpha-naphthol.
  • Example X Two forms of apparatus analogous to those in the drawing were mounted in series. The first was charged with 1,000 grams of catalyst A and an absolute pressure of 600 mm. Hg was maintained. The second was charged with 1,000 grams of catalyst B at atmospheric pressure. The assembly was supplied continuously with a mixture containing 62% 1-oxo-1,2,3,4 tetrahydro-naphthalene, and 38% 1-hydroxy-1,2,3,4 tetrahydro-naphthalene at the rate of 2,000 grams per hour. The two units were maintained at the boiling point of the liquid mixture.
  • the yield in utilizable products with respect to the l-oxo- 1,2,3,4-tetrahydro-naphthalene varied between 97% and 92.5% in accordance with the duration of the reaction.
  • Example X genation catalyst constituted by at least one divided metal selected from the groups consisting of nickel, copper, 01161115011 Was analogous to Example XIII but at the iron, cobalt, chromium, platinum, iridium, palladium, and boiling Point, namely Q and with rhodium, deposited on an inert carrier, the improvement chanical agitation using 250 grams of catalyst A in g which consists in heating a feed material consisting of ules of 1 to 2 mm.
  • Example XVIII 3 A process in accordance with claim 1, wherein the The Operation was carried out in the same manner as catalyst is nickel and the carrier completely neutral sili- Example XVI but replacing the 1-oXo-1,2,3,4-tetrahydro- 2 naphthalene with a mixture of 24% 1-hydroxy-1,2,3,4- d process .reclted 1n.cla1.m.1wherem saldcatilyst tetrahydro-naphthalene and 76% 1-oXo-1,2,3,4 tetrag on i d W.” 15 m the form of parades hydro-naphthalene.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US305763A 1962-08-30 1963-08-30 Dehydrogenating hydroxy-and oxocycloaliphatic compounds Expired - Lifetime US3336399A (en)

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FR908203A FR1344298A (fr) 1962-08-30 1962-08-30 Fabrication de phénols lourds

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3514492A (en) * 1967-01-04 1970-05-26 Inst Francais Du Petrole Dehydrogenation catalyst and a process for dehydrogenating cyclic alcohols and ketones
US3534110A (en) * 1965-12-08 1970-10-13 Inst Francais Du Petrole Production of phenol by the catalytic dehydrogenation of cyclohexanol and/or cyclohexanone
US20070281203A1 (en) * 2006-05-30 2007-12-06 Toda Kogyo Corporation Catalyst for removing metal carbonyl, process for producing mixed reformed gas containing hydrogen, process for removing metal carbonyl, and fuel cells system

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2501770A1 (de) * 1975-01-17 1976-07-22 Hoechst Ag Verfahren zur herstellung von 2-hydroxynaphthalinen

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2321551A (en) * 1941-07-17 1943-06-08 Du Pont Catalytic dehydrogenation and hydrogenation
US2503641A (en) * 1947-04-09 1950-04-11 Ici Ltd Dehydrogenation of organic compounds

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2321551A (en) * 1941-07-17 1943-06-08 Du Pont Catalytic dehydrogenation and hydrogenation
US2503641A (en) * 1947-04-09 1950-04-11 Ici Ltd Dehydrogenation of organic compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3534110A (en) * 1965-12-08 1970-10-13 Inst Francais Du Petrole Production of phenol by the catalytic dehydrogenation of cyclohexanol and/or cyclohexanone
US3514492A (en) * 1967-01-04 1970-05-26 Inst Francais Du Petrole Dehydrogenation catalyst and a process for dehydrogenating cyclic alcohols and ketones
US20070281203A1 (en) * 2006-05-30 2007-12-06 Toda Kogyo Corporation Catalyst for removing metal carbonyl, process for producing mixed reformed gas containing hydrogen, process for removing metal carbonyl, and fuel cells system

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GB1038147A (en) 1966-08-10
FR1344298A (fr) 1963-11-29
DE1518091A1 (de) 1969-12-18

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