US3827972A - Method of producing aromatic hydrocarbons - Google Patents

Method of producing aromatic hydrocarbons Download PDF

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Publication number
US3827972A
US3827972A US00200064A US20006471A US3827972A US 3827972 A US3827972 A US 3827972A US 00200064 A US00200064 A US 00200064A US 20006471 A US20006471 A US 20006471A US 3827972 A US3827972 A US 3827972A
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catalyst
platinum
lead
percent
hydrogen
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Expired - Lifetime
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K Ohki
N Kominami
T Iwaisako
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Asahi Kasei Corp
Asahi Chemical Industry Co Ltd
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Asahi Chemical Industry Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G35/00—Reforming naphtha
    • C10G35/04—Catalytic reforming
    • C10G35/06—Catalytic reforming characterised by the catalyst used
    • C10G35/085—Catalytic reforming characterised by the catalyst used containing platinum group metals or compounds thereof
    • C10G35/09—Bimetallic catalysts in which at least one of the metals is a platinum group metal
    • 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
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
    • C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation
    • C07C5/393—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation with cyclisation to an aromatic six-membered ring, e.g. dehydrogenation of n-hexane to benzene
    • C07C5/41—Catalytic processes
    • C07C5/415—Catalytic processes with metals
    • C07C5/417—Catalytic processes with metals of the platinum group
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • This invention relates to a method of producing aromatic hydrocarbons from petroleum sources at high yields. More particularly, it is concerned with a method of producing a distillate of high aromatic concentration in high yield by highly selectively subjecting naphthenic hydrocarbons to dehydrogenation and paraftinic hydrocarbons to dehydrocyclization.
  • the present invention derived from the discovery, is concerned with a method of producing aromatic hydrocarbons which comprises treating a hydrocarbon or a hydrocarbon mixture at a temperature from 300 C. to 650 C.
  • a catalyst comprising platinum and lead or a catalyst comprising platinum, lead and at least a member selected from lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, zinc, cadmium, mercury, germanium, bismuth, chromium, molybdenum, tungsten, uranium, rhenium, ruthenium, rhodium, palladium, osmium and iridium.
  • the catalyst is prepared by an impregnation procedure.
  • benzene, toluene, Xylenes and polymethylbenzenes are produced by quite simple procedures at low cost because of high concentration and yield of aromatics in the reformate produced according to this invention.
  • a distillate of higher boiling point than toluene or xylene in the reaction product contains neither paraffin nor naphthene and then separation can be effected by distillation only, without application of solvent extraction.
  • Such a distinction from the prior processes is ascribed to high activity and selectivity of the catalyst of this invention in terms of aromatic formation, namely dehydrogenation or dehydrocyclization reactions.
  • life of the catalyst of this invention is so long that frequency in regeneration of the catalyst is reduced under normal reaction conditions in industrial operation.
  • the catalyst of this invention is operative at lower pressures than in prior processes.
  • the rate of degradation in activity in the prior catalysts is much more drastic and they become inoperative during long operation, and, therefore, the process on an industrial scale d has to be carried out under high pressures.
  • the catalyst of this invention is stable in the course of a long operation to give a high yield of aromaties.
  • the platinum component of the catalyst there may be used, for example, the hydroxide, platinum halides, chloroplatinic acid or hydrate or ammonium salt thereof.
  • substances containing a halogen are due to the fact that in a compound containing platinum and halogen, the halogen and especially chlorine present in the compound advantageously contribute to the catalytic activity li-ke in other platinum reforming catalysts.
  • the preferable amount of chlorine contained in the catalyst of the present invention is in the range of l 0.1-2.0% by Weight and particularly in the range of 0.5-
  • catalyst components there may be employed halogenides, inorganic and organic salts, hydroxide, oxide and the like.
  • the element used as the third component may be in the form of its oxide, hydroxide, halide or other inorganic and organic salt or complex.
  • the platinum, lead and the third components may be in the form of a salt containing each of them.
  • Contents of the platinum, lead and the third components are 0. ⁇ l5% by weight, Q01-5% by weight and 0-3% by weight, respectively, and preferably 0.05-l% by weight, Q01-3% by weight and 0-1% by weight, respectively based on the total weight of catalyst components, with the ratio of lead to platinum ranging from 0.1 to 3.
  • the catalyst is prepared by simultaneously supporting platinum and lead on a carrier by conventional impregnation methods; or by supporting lead on a carrier and thereafter supporting platinum on the carrier, again using conventional impregnation methods.
  • Preferred Pb/Pt ratios, lead and platinum contents, and third component content with the two impregnation methods are as follows:
  • the catalyst is prepared by immersing a carrier in an aqueous solution containing a lead compound such as, eg., lead nitrate and lead chloride, to support the lead component on the carrier, drying the resulting material and then calcining the dried product at a temperature ranging from 300 C. to 800 C.
  • the calcined product is then immersed in an aqueous solution containing a platinum compound such as, eg., chloroplatinic acid, to support the platinum component thereon, drying the resulting assembly and then calcining the dried product at a temperature ranging from 400 C. to 700 C., preferably from 450 C. to 600 C.
  • amounts of platinum, lead and a third component contained in the solution of platinum compound, lead compound and third component are, in general, 0.01-5 wt. percent platinum; 0.01-5 wt. percent lead and 0-3 wt. percent third component.
  • the ranges preferably are 0.1-l wt. percent platinum; 0.1-2 wt. percent lead and 0-1 wt. percent third component.
  • the ranges preferably are 0.1-1 Wt. percent platinum; 0.1-2.5 wt. percent lead and 0-1 Wt. percent third component.
  • Lead to platinum weight ratio in the solution generally ranges from 0.1 to 3.0, and preferably, in the simultaneous impregnation method, it ranges from 0.3 to 2.0, and in the sequential impregnation method, it ranges from 0.3 to 2.5.
  • the effective Pb/Pt ratio varies depending upon the process for the preparation of catalyst and upon the reaction pressure.
  • the maximum effective Pb/ Pt ratios are 3.8, 3.5, 3.2 and 3.0, respectively. This will be illustrated by the examples as set forth hereinafter.
  • the proportion of contents of the components depends, for example, upon the type of carrier, surface area, order of the addition, method of the calcination and the like.
  • a carrier such as silica alumina, alumina, alumina hydrate, silica, zeolite, kaolin, acid clay or bentonite is effective and preferable carriers are alumina, silica alumina, zeolite and the like.
  • hydrocarbons which may be used in the present invention as the starting material include those mainly comprising paraffins, olelins and naphthenes having a boiling point Within the range of from 40 to 350 C., which may be used alone or in admixture of two or more kinds.
  • Preferable hydrocarbons are those having from 6 to l2 carbon atoms.
  • Feeding ratio of hydrogen to hydrocarbon in gas volume is from 0.5 to l5 and preferably from 2 to l0.
  • the catalyst Prior to the reaction, the catalyst may be pretreated with hydrogen at or near the reaction temperature to activate it.
  • Feeding rate of the hydrocarbon in terms of LHSV which stands for liquid hourly space velocity (the feeding amount of hydrocarbon per unit time, per unit volume of catalyst, in ml.) is from 0.2 to l0 hr.1 and preferably from 0.5 to 5 hrl.
  • the reaction pressure is dependent upon the desired quality of product and economy and may be optionally chosen within the range of from 1 to 50 kg./cm.2 and preferably from 5 to 20 kg./cm.2. In order to. improve the space time yield in the commercial productlon, the reaction is preferably carried out under an elevated pressure.
  • Example 1 In an aqueous solution of a mixture of chloroplatinic acid and lead chloride was immersed fy-alumina. After being dried, the resulting mass was calcined at 550 C. for 2 hours to prepare a catalyst with a composition: 0.5% Pt-0.25% Pb-Al2O3. Percent is by weight herein unless otherwise noted.
  • Example 2 A hundred milliliters of a catalyst prepared by the same method as in Example 1, the composition being 0.5% Pt-0.5% Pb-A12O3, was heated under hydrogen at 500 C. for 2 hours. Through the catalyst layer -was passed a gaseous mixture of hydrogen and naphtha with the composition given below at a feeding ratio of 3:1 (by gas volume) at an LHSV of 2.0 hr.1 under a total reaction pressure of 10 kg./cm.2 (gauge) continuously for 48' hours, 'while maintaining the layer at a temperature of 500 C. Yields by weight of the products were: Hydrogen 4.5%, benzene 5.4%, toluene 15.3%, xylenes 30.6% and the total aromatics 76.7%.
  • Example 3 Composition of the starting material (percent by volume):
  • Example 4 With 100 cc. of a catalyst composition comprising 0.5% platinum, 0.5% lead and 'y-alumina was supported 0.3% potassium carbonate by impregnation and after the catalyst was reduced by hydrogen for an hour at 530 C., a gaseous mixture of hydrogen and naphtha having a composition shown below in a volume ratio of 10:1 was passed therethrough at an LHSV of 1.0 hr.-1 at a reaction temperature of 480 C. under a reaction pressure of 4 kg./ cm.2 (gauge).
  • Catalyst composition Pt-Pb-KzCOs
  • Example 5 'y-Alumina granulated in a ball of a diameter of 2 mm. was immersed in an aqueous solution of rubidium hydroxide, followed by drying and calcination at 570 C. to give a carrier of the composition 0.21% rubidium- 99.79% A1203. The carrier was then immersed in an aqueous solution of a mixture of chloroplatinic acid and lead chloride. After being dried in 2 hours and calcined at 550 C. for 2 hours, there was prepared a catalyst of the composition: 0.5%Pt0.5%Pb-0.2%Rb-Al203.
  • a reactor 1.25 inches in diameter was filled with the catalyst and treated under hydrogen for 45 minutes during which period the temperature was raised from 410 C. to 530 C.
  • a gaseous mixture of hydrogen and naphtha with the composition given below in a ratio of 7.5 :1 was passed through the reaction tube at an LHSV of 2.0 hr.-1 and a temperature of 510 C. under a pressure of 10 kg./ cm?. Yields by weight on average of the products after 25 hrs., on the naphtha basis, were: Benzene 4.4%, toluene 14.9%, xylenes 33.6% and the total aromatics 77.9%.
  • composition of the naphtha source (percent by volume):
  • Example catalyst h y Stam t 1 (molar As shown in Table 1I, following, the resulting catalyst (e ement) weg t) g ma em percent) had a composition of 0.3-1.0 Wt. percent Pt; 0.3-5.0 Wt.
  • Example 28 In 200 cc. of an aqueous solution containing 0.0128 mol/liter of chloroplatinic acid and 00036-00605 mol/ liter of lead nitrate were immersed 140 cc. of ry-alumina having a particle size of 2-3 mm. diameter as a carrier. The resulting product was evaporated to dryness, and then calcined at 550 C. for 3 hours. As shown in Table I, following, compositions of the resulting catalysts are 0.5 wt. percent Pt; 0.l5-2.50 wt. percent Pb and A1203, while Pb/Pt ratio is from 0.3 to 5.0. After cc. of the resulting catalyst were heated at 500 C.
  • Example 30 In 200 cc. of an aqueous solution containing 0.0121 mol/liter of lead chloride were immersed cc. of 'yalumina as a carrier. They resulting product was vaporized to dryness, calcined at 550 C. for 3 hours, and, subsequently, immersed in 200 cc. of an aqueous solution containing 0.0128 mol/liter of chloroplatinic acid, followed by vaporizing to dryness and calcining at 550 C. for 3 hours.
  • the resulting catalyst had a composition of 0.5 wt. percent Pt; 0.5 wt. percent Pb and A1203, while Pb/Pt ratio is 1.0.
  • Chloro- Lead added ratio toluene xyleno platinc acid nitrate wt. (by produced (mol Run number (mol/liter) (mol/liter) percent) wt.) percent) 6 (comparative) 0. 0128 0. 0505 2. 50 5. 0 23. 1
  • Example 29 at 500 C. under atmospheric pressure at a liquid hourly In 200 cc. of an aqueous solution containing 0.0072- 0.122 mol/liter of lead nitrate were immersed 140 cc. of
  • the molar yield of total aromatic hydrofy-alumina having a particle size of 2-3 mm. diameter as 75 carbons produced based ori heptane was 78.3%.
  • COMPARATIVE EXAMPLE 1 20 cc. of a known catalyst comprising 0.5% Pt and 99.5 'y-alumina were heated at 500 C. under a hydrogen stream for an hour. Then, there was passed a mixed gas consisting of hydrogen and n-heptane in a molar ratio of 3:1 through the catalyst layer maintained at 500 C. under atmospheric pressure at a liquid hourly space velocity of 0.5 hr.-1. As a result, molar yields of the resulting products were as follows:
  • COMPARATIVE EXAMPLE 2 Twenty milliliters of a known catalyst consisting of 0.5% platinum and 99.5% y-alumina were heated under hydrogen at 500 C. for 1 hour. Through the catalyst layer was passed a gaseous mixture of hydrogen and n-heptane at an LHSV of 0.5 hr.-1 under atmospheric pressure, while maintaining the layer at 510 C. Molar yields of the products were: Benzene 8.7%, toluene 36.7%, xylenes 3.8% and the total aromatics 49.2% after a reaction time of 1 hour.
  • Method of producing aromatic hydrocarbons which comprises hydroforming a mixture of hydrogen and a hydrocarbon over a catalyst at a temperature of from 300 C. to 650 C. under a pressure of from 5 to 20 kg./cm.2, said catalyst consisting essentially of from about 0.01 to about 5 wt. percent platinum and from about 0.01 to about 5 wt.
  • percent lead up to about 1% by weight of a component selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, zinc, cadmium, mercury, germanium, bismuth, chromium, molybdenum, tungsten, uranium, rhenium, ruthenium, rhodium, palladium, osmium and iridium, up to 2.0% by weight of a halogen and a carrier, wherein the ratio of lead to platinum is within the range of from 0.1 to 3.0, and being prepared by simultaneously supporting said platinum and lead components on a carrier by impregnation, or first supporting said lead component on a carrier by impregnation and thereafter supporting said platinum component on said carrier by impregnation.
  • a component selected from the group consisting of lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, zinc, cadmium
  • Method of producing aromatic hydrocarbons which comprises hydroforming a mixture of hydrogen and a hydrocarbon ofver a catalyst at a temperature of from 300 C. to 650 C. under a pressure of from 5 to 20 kg./cm.2, said catalyst consisting essentially of from about 0.01 to about 5 wt. percent platinum and from about 0.01 to about 5 wt. percent lead and a carrier, wherein the ratio of lead to platinum is within the range of from 0.1 to 3.0, and being prepared by simultaneously supporting said platinum and lead components on a carrier by impregnation, or rst supporting said lead component on a carrier by impregnation and thereafter supporting said platinum component on said carrier by impregnation.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00200064A 1969-02-10 1971-11-18 Method of producing aromatic hydrocarbons Expired - Lifetime US3827972A (en)

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JP948869 1969-02-10
JP6761769 1969-08-28
JP10381769 1969-12-25

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US00200065A Expired - Lifetime US3827988A (en) 1969-02-10 1971-11-18 Pt-pb catalyst compositions
US00200071A Expired - Lifetime US3827973A (en) 1969-02-10 1971-11-18 Reforming with a coprecipitated platinum-lead catalyst

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DE (1) DE2005828C3 (enrdf_load_stackoverflow)
GB (1) GB1305137A (enrdf_load_stackoverflow)
NL (1) NL162353C (enrdf_load_stackoverflow)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3875048A (en) * 1971-07-05 1975-04-01 Asahi Chemical Ind Reforming process using platinum-lead-third component catalyst and catalyst therefor
US3900387A (en) * 1972-03-10 1975-08-19 Universal Oil Prod Co Hydrocarbon conversion with a multimetallic catalytic composite
US3915846A (en) * 1973-04-23 1975-10-28 Universal Oil Prod Co Hydrocarbon conversion with a trimetallic catalytic composite
US3928177A (en) * 1972-01-10 1975-12-23 Universal Oil Prod Co Hydrocarbon conversion with a multimetallic catalytic composite
US3940329A (en) * 1974-01-24 1976-02-24 Universal Oil Products Company Hydrocarbon conversion with a multimetallic catalytic composite
US4028225A (en) * 1974-06-13 1977-06-07 Uop Inc. Hydrocarbon conversion with a sulfided acidic multimetallic catalytic composite
US4053389A (en) * 1974-06-13 1977-10-11 Uop Inc. Hydrocarbon conversion with an acidic multi-metallic catalytic composite
US4130597A (en) * 1975-07-21 1978-12-19 Wilhelm Frederick C Dehydrogenation using multimetallic catalyst
US4520125A (en) * 1983-02-26 1985-05-28 Basf Aktiengesellschaft Catalyst for the preparation of methyl methacrylate
EP1369175A1 (fr) * 2002-06-07 2003-12-10 Institut Français du Pétrole Lit homogène de catalyseur et procédé de transformation d'hydrocarbures en composés aromatiques avec ledit lit

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1390182A (en) * 1971-03-16 1975-04-09 Johnson Matthey Co Ltd Catalysis
US4072602A (en) * 1972-01-10 1978-02-07 Uop Inc. Dehydrogenation method and nonacidic multimetallic catalytic composite for use therein
US3980726A (en) * 1973-06-01 1976-09-14 Universal Oil Products Company Dehydrogenation with a nonacidic multimetallic catalyst
US4899012A (en) * 1988-10-17 1990-02-06 Uop Catalyst for the isomerization of aromatics
FR2666249B1 (fr) * 1990-09-03 1994-07-22 Inst Francais Du Petrole Catalyseur et procede d'aromatisation des hydrocarbures contenant 2 a 4 atomes de carbone par molecule.
US5268522A (en) * 1990-09-03 1993-12-07 Institut Francais De Petrole Process for the aromatization of hydrocarbons containing 5 to 9 carbon atoms per molecule in the presence of a particular catalyst
FR2674769B1 (fr) * 1991-04-04 1994-04-29 Inst Francais Du Petrole Catalyseur du type galloaluminosilicate contenant du gallium, un metal noble de la famille du platine et au moins un metal additionnel, et son utilisation en aromatisation des hydrocarbures.
US9242233B2 (en) 2012-05-02 2016-01-26 Saudi Basic Industries Corporation Catalyst for light naphtha aromatization
US9180441B2 (en) 2012-09-20 2015-11-10 Saudi Basic Industries Corporation Method of forming zeolite shaped body with silica binder
US9782758B2 (en) 2013-04-23 2017-10-10 Saudi Basic Industries Corporation Method of preparing hydrocarbon aromatization catalyst, the catalyst, and the use of the catalyst
CN112742382B (zh) * 2019-10-29 2024-01-05 中国石油化工股份有限公司 一种催化重整催化剂的制备方法

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3875048A (en) * 1971-07-05 1975-04-01 Asahi Chemical Ind Reforming process using platinum-lead-third component catalyst and catalyst therefor
US3928177A (en) * 1972-01-10 1975-12-23 Universal Oil Prod Co Hydrocarbon conversion with a multimetallic catalytic composite
US3900387A (en) * 1972-03-10 1975-08-19 Universal Oil Prod Co Hydrocarbon conversion with a multimetallic catalytic composite
US3915846A (en) * 1973-04-23 1975-10-28 Universal Oil Prod Co Hydrocarbon conversion with a trimetallic catalytic composite
US3940329A (en) * 1974-01-24 1976-02-24 Universal Oil Products Company Hydrocarbon conversion with a multimetallic catalytic composite
US4028225A (en) * 1974-06-13 1977-06-07 Uop Inc. Hydrocarbon conversion with a sulfided acidic multimetallic catalytic composite
US4053389A (en) * 1974-06-13 1977-10-11 Uop Inc. Hydrocarbon conversion with an acidic multi-metallic catalytic composite
US4130597A (en) * 1975-07-21 1978-12-19 Wilhelm Frederick C Dehydrogenation using multimetallic catalyst
US4520125A (en) * 1983-02-26 1985-05-28 Basf Aktiengesellschaft Catalyst for the preparation of methyl methacrylate
EP1369175A1 (fr) * 2002-06-07 2003-12-10 Institut Français du Pétrole Lit homogène de catalyseur et procédé de transformation d'hydrocarbures en composés aromatiques avec ledit lit

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Publication number Publication date
DE2005828C3 (de) 1974-03-07
NL7001852A (enrdf_load_stackoverflow) 1970-08-12
NL162353C (nl) 1980-05-16
DE2005828B2 (de) 1973-08-09
DE2005828A1 (de) 1970-09-03
US3827973A (en) 1974-08-06
NL162353B (nl) 1979-12-17
GB1305137A (enrdf_load_stackoverflow) 1973-01-31
US3827988A (en) 1974-08-06

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