Production of Phenol and Acetone From Oxidation of Cumene Starts

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THE CHEMICAL WORLD THIS WEEK servations in the value of research, did Dr. Britton learn the full import of the honor he was t o receive. A gold key to the laboratory building was presented to Dr. Brittou by Mark E . Putnam, executive vice president of Dow, after which Dow's president, Leland I. Doan, announced that t h e building h a d been officially named t h e "Edgar C. Britton Research Laboratory." As a further honor to Dr. Britton, D o w has established a graduate fellowship for research in organic chemistry at the University of Michigan. The fellowship, announced b y Dow's research director, R. H. Boundy, will b e known as the Edgar C. Britton Fellowship. A large bronze plaque, proclaiming the name of the laboratory .building and the date of its dedication, was hurriedly installed during the dedication ceremony, which was attended by D o w executives, members of t h e general research committee, and the organic research laboratories staff. Following the more ''formal" portion of the program, d i e group adjourned to tour the research facilities, and to view the bronze plaque, which had remained hidden prior to t h e dedication. The research building, completed in April, contains about 42,000 square feet of working space and will accommodate about 100 workers, including a technical staff of 6 0 . T h e major portion of the space is devoted to eight six-man research laboratories and two three-man laboratories; additional rooms are provided for operations which require exceptionally tall equipment or the use of large or noisy machinery. T w o development or "pilotplant" rooms have b e e n provided, and a storeroom, a darkroom, and a cold storage room complete die research facilities. Offices, a record storage vault, a library and reading room, conference room, and a work shop make t h e laboratory virtually self-sufficient. Laboratory furniture is steel and bench tops are formica-covered plywood. If desired, one of t h e lattice bench islands in each laboratory may b e covered with a hood. Any of t h e large laboratories can be rather easily converted to t w o small ones by building a tile partition. Even if this is done each room will be independent as to ventilation and services. Visitors to t h e new laboratory during a two-day open house following the dedication were presented with a pamphlet explaining the n e w facilities, and introducing (to those few who d i d not already know h i m ) the laboratory director. In its opening paragraphs, the pamphlet states: "Few things today are untouched by chemistry, and the research of the D o w organic chemist is as close t o you as your cigarette (humectants), your bluejeans ( indigo ) , or your soap . . . . gasoline . . . . television lens. "This laboratory is dedicated to a man whose leadership was instrurnental in helping this company make trie progress of the past, and to the self-starting men he has gathered around him, as the best assurance of even better things for all of us in the future."

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This plant of B. A.-Shawinigan is the first to produce phenol and acetone from petroleum through cumene. In the background is British American's Montreal East refinery from which cumene is piped to the plant owned jointly with Shawinigan Chemicals

Production of Phenol and Acetone From Oxidation of Cumene Starts C a n a d i a n plant is first to use Hercules Powder-Distillers petrochemical process 'T^HE first plant to produce phenol and acetone from petroleum, through oxidation of cumene, w e n t into operation last week when B. A.-Shawinigan Ltd. officially opened its plant at Montreal. The company, owned jointly by Shawinigan Chemicals and British American Oil Co., Ltd., is operating under license from Hercules Powder and Distillers Co., Ltd. The $ 4 million petrochemical plant is adjacent to a B. A. refinery where cumene is made by reaction of benzene with propylene. The phenol plant, occupying five acres of a 20-acre site, has open construction to avoid undue vapor concentrations. Use of this type design is unusual in Canada and requires about 20 miles of steam tracing line to assure year-round operation. It utilizes a process whereby cumene is air-oxidized to cumene hydroperoxide, which is catalytically split to phenol and acetone.

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Cumene from neighboring B. A. refinery

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By-products: a-methylstyrene, none, and mesityl oxide

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CHEMICAL

When ultimate production rates are reached, the plant will produce some 13 million pounds of phenol annually, 8 million pounds of acetone, and 1 million pounds of a-methylstyrene, a s well as several hundred thousand pounds of acetophenone and mesityl oxide. The company says that the capacity for both phenol and acetone is sufficient to supply Canadian demand, making the country independent of the U. S. i n the case of phenol, and releasing several hundred tons of calcium carbide to Shawinigan Chemicals for use other than acetone production. T h e plant was constructed b y M. W. Kellogg Co., 'who is also building the $8 million plant, using t h e same process, for Hercules near Gibbstown, N . J. Five other large-scale plants using die same process are under construction in the U . S. and abroad. This same basic oxidation-cleavage process is being used b y Hercules for the production of high-purity p-cresol, resorcinol, hydroquinone, and other phenols.

A D M Plans Higher Alcohol Plant in Ohio Unsaturated higher alcohols will b e produced at a chemical plant planned by Archer-Daniels-Midland at Ashtabula, Ohio. Ground for the plant will b e broken this month, and production of both saturated and unsaturated alcohols is expected 12 months later. The company says that many of the alcohols which will be made at the plant are not commercially available today. Vegetable, animal, and ma-

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THE CHEMICAL WORLD THIS WEEK rine fats and oils will serve as the prin­ cipal raw materials. T h e plant will be located on a 4 0 acre site near Ashtabula's harbor on Lake Erie. The site, which was purchased last N o ­ vember, has an adequate supply of water and is located close t o a source of metallic sodium, both of which are essential to the operation of the plant. While alcohols will be the major prod­ ucts of the plant, glycerol and caustic soda will b e important by-products.

much like styrene and m a y be used to re­ place it in such products as synthetic rub­ ber, paint vehicles, and polyester resins. Dow development work indicates that vinyltoluene will react to form clear paint vehicles with all of the commercially im­ portant drying oils. Styrene will react with only a limited number of these drying oils. Quantities of vinyltoluene sufficient for developmental work are now available from pilot plant production.

Plant f o r Steel Alloying Material Ν e a r s Completion

p-Xylene Separation Plant Planned f o r Midwest Standard Oil ( Ind. ) will soon begin con­ struction of a plant to separate p-xylene. This unit will be at the company's refinery at Whiting, Ind. It is expected t o b e in operation b y Jan. 1, 1955. Anticipated production is 14 million pounds annually. T h e Whiting plant for separating p-xylene from other aromatic hydrocarbons is being engineered by Badger Mfg. Co. The operation will involve the use of pres­ ent hydroforming facilities, and is asso­ ciated with the company's benzene produc­ tion. Company research has developed two recent methods of hydroforming-one is a fluid hydroformer using finely divided molybdena catalyst, and the other a low pressure fixed bed process using platinum catalyst.

D o w Vinyltoluene Plant Under Construction Completion by the end of the year, with volume production early next year, i s ex­ pected by D o w for a vinyltoluene plant now under construction at Midland, Mich. Production of vinyltoluene is expected to broaden the horizon of the styrene family of compounds. It behaves chemically very

Facilities for producing a steel alloying material are now nearing completion at Marietta, Ohio. T h e plant is part of an alloys expansion program being carried out b y Electro Metallurgical Co., a Divi­ sion of Union Carbide & Carbon Corp. By the end of this year, the company's alloy producing capacity will be triple what it was i n 1940. One unit of this plant is for production of chromium alloy, containing only 0 . 0 1 % carbon, for use in making stainless s t e e l Simplex ferrochrome. It is made in the form of pellets about the size of a walnut. The building in which this alloy is being made covers an area of 7 . 5 acres. The pel­ lets are specially "baked" in immense furnaces, about a million of them going into the furnace i n a single charge. The fourth of eight furnaces h a s just been fired, and t h e balance w i l l be in production by the end of the year. In this "push button" plant, Walkie-Talkie sets are used for fast communication. There are about 20 buildings on the 750-acre plant site, where construction was started in 1949. Final installations are ex­ pected to be completed i n spring of 1954. The plant handles about 1500 tons of raw materials a day. These include ores

This vinyltoluene plant will b e completed by the e n d of the year by D o w Chemical Co.

coming mostly from Africa, Turkey, N e w Caledonia, Cuba, and the Philippines. When in full-scale operation^ the plant will burn about 40 carloads of coal a day.

Lilly Wins Suit O v e r Penicillin P a t e n t The Federal District Court in Indian­ apolis has upheld the Eli Lilly patent on procaine penicillin. Schenley Laboratories, defendant in a suit filed in 1951, has been enjoined for t h e full term of the patent from making, using, or selling procaine penicillin in any of its forms. T h e case has been referred to a special master to be designated by the court to determine the amount of damages. Other infringement suits involving the same patent have been brought in Federal District Courts against Heyden Chemical Co. and J. T. Baker Chemical C o . All other companies making procaine penicillin operate under license from Lilly. Schenley plans t o appeal t o the U. S. District Court of Appeals in Chicago. Both sides have indicated that d i e final decision in t h e case would have to b e made by the Supreme Court, regardless of which side wins. A n appeal bond of $75,000 has been fixed. Damages are not ex­ pected to exceed this amount, according to company attorneys. Schenley d i d not contest the infringe­ ment allegation, but held that the Lilly process could not b e patented, since it considers the process a scientific discovery in which no single firm should have mo­ nopoly control.

Commercial Solvents t o Double N i t r o g e n O u t p u t The first post war plant for nitrogen compounds will b e completed by Com­ mercial Solvents in time for production for the 1953-ί>4 fertilizer year. The facilities are part of the company's Sterlington, La., plant, and will double its present output of nitrogen for agricultural and indus­ trial use. In addition to increasing present output of anhydrous ammonia, two other nitro­ gen sources will b e added t o C S C s agri­ cultural chemical line. These are Dixsol nitrogen solutions for mixed fertilizers and crystalline ammonium nitrate fertilizer for direct application t o the soil. T h e n e w facilities were built at a cost of $20 million. They are the first of the chemical industry's privately financed nitrogen expansion programs aimed at a 70% increase in production b y 1956.

Shell A g r i c u l t u r a l Research Consolidated a t Denver All future agricultural research activities to b e conducted b y Shell companies in the U. S. will b e consolidated under the newly organized agricultural research divi­ sion of Shell Development Co. with head­ quarters in Denver, Colo. The newly created division will b e responsible for the development and testing of chemical

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PROPIONIC ACID BUTYRIC ACID

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Propionic Acid and Butyric Acid production in tankcar quantities at the Celanese Pomp a plant in Texas, -will b e welcome n e w s to m a n y manu­ facturers of plasticizers, flavors, surface coatings, plastics, mold inhibitors, and pharmaceuticals. These manufacturers a s well a s other users of organic acids are invited to examine samples of Celanese synthetically-produced Propionic Acid and Butyric Acid. Specifications a n d other information will be sent upon request. For your convenience, u s e coupon below.

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Celanese C o r p o r a t i o n of America Chemical Division, D e p t . 554-F 180 M a d i s o n A v e n u e , New York Τ 6, Ν . Υ.

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Propionic Acid sample

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Butyric Acid sample

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ADDRESS CITY

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C e l a n e s e C o r p o r a t i o n of A m e r i c a , C h e m i c a l Division 180 M a d i s o n A v e n u e , N e w York

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THE CHEMICAL WORLD THIS WEEK products for use in agriculture. This consolidation makes possible close coordination between the agricultural research division and the product development activities of the Julius Hyman & Co., Division of Shell Chemical Corp. In addition to the agricultural research laboratories at Denver, Shell Development also operates a laboratory and experimental farm near Modesto, Calif., where Shell has been active in the study and development of fertilizers, insecticides, nematicides, and fungicides. T h e Modesto installation n o w becomes a part of the newly organized division.

W a t e r Level Survey Will Be Made on D e l a w a r e River Industries that might b e affected have put up $100,000 for a private engineering survey o f water supplies in t h e Delaware River. T h e project grows out of objections to a proposed deepening of the river from t h e Philadelphia Navy Yard to N e w bold's Island near Trenton. T h e deeper channel would give ocean-going ships access to the n e w Fairless Works of U. S. Steel at Morrisville. Camden and most of the municipalities along the N e w Jersey side of the river are concerned over the possibility of intrusion of salt water into their water supplies if the channel is deepened. The survey, it is hoped, will settle the effect of the project, which w a s recommended by the Army Engineers. If no objections are found, it is thought by persons concerned that Congress will authorize necessary funds. T h e study, which will take a full year on a 24-hour a day basis, will compile data on river flow, rise and fall of tides, volume of water, temperatures, water analyses, and whether salinity w o u l d reach a higher level in the river. The survey was initiated b y Campbell Soup Co., t h e largest user of water in South Jersey. Joining in the project are U. S. Steel, Kind and Knox Gelatine, and American Water Works, which supplies water t o t w o wards of Camden, as well as towns of Laurel Springs, Riverton, and Beverly. Engineers engaged for the survey are Sheppard T. Powell, consulting chemical engineer of Baltimore, and Ralph M. Leggette of N e w York City.

NEWS BRIEFS M. W . Kellogg C o . has appointed Flek Corp., 2 2 5 2 East 37th St., Los Angeles, Calif., as its exclusive warehousing distributor for Kel-F molding powder on the West Coast. While a major portion of Kel-F stocks are still allocated to defense production, some molding powder is available for nondefense purposes. Pioneer Rubber C o . , Willard, Ohio, has appointed T h e Andrew Co., 2 7 7 Broadway,

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N e w Yorl\ as distributor of their Stanzoil industrial gloves for the N e w England and Mid-Atlantic states. Warwick Wax Co., Inc., subsidiary of Sun Chemical Corp., has appointed N. S. Wilson Co., 150 Causeway St., Boston, Mass., as the exclusive N e w England distributor of Warwick Waxes. Salt Lake Pipe Line Co., a Standard Oil Co. of Calif, subsidiary, is proceeding with the construction of the 135 mile oil products pipe line from Pasco to Spokane. Completion is scheduled for October 1953. Cost of the project will total approximately $4 million. Garden Research Laboratories. Madison, N. J., and Huber Hoge & Sons, Inc., 600 Madison Ave., N e w York, have been cited b y the Federal Trade Commission for claiming that RX-15, a liquid fertilizer, is a super-powerful plant food. T h e first hearing will be held June 10 in N e w York. Norton C o . , Worcester, Mass., has corrected our mistake in a former issue (C&EN, April 6, page 1 4 2 0 ) . Only the N e w York City domestic sales offices of the abrasive division, grinding machine division, and refractories division were moved to Green and North Sts., Teterboro,

N. J. C e l a n e s e Corp. of America's plastics division has established a district sales office in the Hanna Bldg., 1 4 2 2 Euclid Ave., Cleveland, Ohio. T h e n e w headquarters replace the branch office formerly in Detroit, Mich. T h e Cleveland office will handle sales of Celanese plastic films, sheeting, and molding materials in Ohio, Michigan, West Virginia, eastern Kentucky, western Pennsylvania, and western N e w York. D. W . Moor Rubber Corp. is t h e new corporate name of Lithox Corp., Wapakoneta, Ohio. The company manufactures corded rubber, floor matting, and stair treads. Vosco Industrial Chemical Products Ltd. has built a plant in Montreal, Canada, for production of the main types of detergents. The capacity of the plant is 6 to 10 million pounds per year. Babcock & Wilcox C o . will open an engineering office in Miami, Fla., with a staff of 30. The firm has two other offices in Florida—St. Petersburg and Tampa. De Loire, Inc., has opened offices at 114 East 32nd St., N e w York City. This firm replaces the former D e Laire Division of D o d g e & Olcott, Inc., which association was terminated with the formation of the n e w corporation. Seymour Dress & Blouse Co., 462 Seventh Ave., N e w York City, has been ordered by the Federal Trade Commission to discontinue the sale of flammable garments without sufficient warning as to the danger involved. Kenneth Tator A s s o c , Coraopolis, Fa., »

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has established a corrosion testing service for manufacturers of industrial coatings. Test stations will b e located i n the plants of industrial companies where direct exposures can b e made to various fume environments. Shield Coatings Corp.. 251 Grove Ave., Verona, N. J., has changed its name to Shield Chemical Corp., in order to describe more accurately the enlarged scope of its activities. MMM Industrial Division has been issued a writ of perpetual injunction prohibiting sale of pressure-sensitive adhesive tapes under the trade marks "Econoscotch" and "MMM," b y the U. S. District Court of the Southern District of Calif. The court stated that it has infringed trade mark registrations and competed unfairly with the Minnesota Mining and Mfg. Co. J. T. Baker Chemical Co., because of increased sales activities, has moved its Philadelphia sales office to larger quarters at 6908 Market St., Upper Darby, Pa. Engineering Research Assoc, has leased space in the Midway Terminal Warehouse Bldg., 2295 University Ave., St. Paul, Minn., to accommodate expanded electronic computer and precision instrument development and production. ERA's main plant is at 1902 West Minnehaha Ave., St. Paul. Bostwick Laboratories, Inc., 706 Bostwick Ave., Bridgeport, Conn., has been cited by the Federal Trade Commission for several of its · advertising claims. Among those mentioned are the safety and/or effectiveness of Bostwick SuperAerosol Insect Killer, H e p Aerosol Insect Killer, Safe-lex Aerosol Insect Killer, and Bostwick Moth Proofer. It w a s also cited for representing that D D T has been barred for use near children and pets by government agencies and that the Department of Agriculture has recommended methoxychlor be substituted for D D T except for control of flies around dairy barns.

GOVERNMENT Geochemical Study f o r Arkansas Niobium, Titanium A detailed geochemical study of the Magnet Cove and Potash Sulfur Springs, Ark., niobium and titanium deposits has been undertaken by the Geological Survey. Moreover, the area is being remapped at an appropriate scale in order to gain a further knowledge of the petrology, intrusive history, and structure of the lock and its relation to the surrounding sedimentary rocks. In order to determine the distribution and average content of niobium i n the larger titanium deposits, drill-core and channel samples have been analyzed in addition to concentrates and single crystals. Results indicate the niobium is present in rutile, brookite, and perovskite, and in other minerals still under investigation.

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