US1975663A - Process and apparatus for making ketene - Google Patents

Process and apparatus for making ketene Download PDF

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Publication number
US1975663A
US1975663A US591151A US59115132A US1975663A US 1975663 A US1975663 A US 1975663A US 591151 A US591151 A US 591151A US 59115132 A US59115132 A US 59115132A US 1975663 A US1975663 A US 1975663A
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United States
Prior art keywords
ketene
copper
iron
temperature
chambers
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Expired - Lifetime
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US591151A
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English (en)
Inventor
George H Reid
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Carbide and Carbon Chemicals Corp
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Carbide and Carbon Chemicals Corp
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
Priority to BE393839D priority Critical patent/BE393839A/xx
Application filed by Carbide and Carbon Chemicals Corp filed Critical Carbide and Carbon Chemicals Corp
Priority to US591151A priority patent/US1975663A/en
Priority to FR749245D priority patent/FR749245A/fr
Priority to GB1970/33A priority patent/GB413709A/en
Application granted granted Critical
Publication of US1975663A publication Critical patent/US1975663A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • C07C45/87—Preparation of ketenes or dimeric ketenes
    • C07C45/88—Preparation of ketenes or dimeric ketenes from ketones

Definitions

  • the invention relates to a process and apparatus for making ketene (CH2:QO) by the pyrolysis of organic compounds which can be thermally decomposed to yield products including ketene. are examples of such compounds.
  • Ketene is a useful acetylating reagent for choice of suitable many organic syntheses, but industrial applications of the reactions of ketene have heretofore 10 been barred by the difficulties involved both in its production and utilization.
  • the principal object of my invention is to provide a process and apparatus for making ketene in. a simplified and economical manner which l5 largely avoids the existing difficulties in the production of ketene.
  • Ketene is an extremely active compound of unstable nature, and will decompose or polymerize at its formation temperature. For this reason the period during which the material from which ketene is made is exposed to cracking temperatures must be closely controlled and the temperatures of pyrolysis must be carefully regulated.
  • the material of the pyrolytic chamber must be a good conductor of heat. Also, the material must be able to withstand continued heating at the cracking temperature and the accompanying oxidizing effects. These requirements for the material of the cracking chamber practically limit the available material to non-metallic refractory materials and the higher melting metals and alloys. In general,
  • non-metallic refractory materials are not satisfactory because of their mechanical and physical characteristics, and the list is thus restricted to metals and alloys.
  • Early investigators have shown that iron, nickel and related metals or their alloys are unsatisfactory because they apparently exert a catalytic effect upon ketene or the pyrolytic reaction by which it is formed and cause carbon to be formed and deposited on the metal.
  • Copper is satisfactory and has been successfully employed in cracking chambers for making ketene.
  • the use of copper involves many difficulties. Copper oxidizes readily at the temperatures used, which range from atmospheric temperature at the cool end of the vaporizer in a typical apparatus, to 750 C. at the outlet end of the cracking zone. For this reason, the copper must be protected from the air. This may be done by surrounding the copper equipment in an inert or reducing atmosphere, or by providinga sheath or shell of a more resistant metal or alloy over the copper tubes. Either .method of protection is difficult and makes the production of ketene expensive.
  • the fabri- 8o cation of duo-metal cracking chambers in which copper forms the inner portion is further complicated by the thermal expansion of copper which is greater than that of iron or its alloys.
  • the invention broadly comprises the use of an apparatus which does not employ copper except for the zone of actual pyrolysis.
  • iron alloys containing a substantial proportion of chromium may be used without causing carbon deposition or otherwise deleteriously affecting the reactions.
  • the substance to be thermally decomposed to yield ketene e. g. acetone
  • ketene e. g. acetone
  • the pipe 10 is connected to a vaporizer section 12 within 110 a furnace 13.
  • the furnace 13 is provided with heating means, such as a gas burner 20 supplied with gaseous fuel by a pipe 21 and a valve 22 to control the flow of the fuel.
  • the vaporizer 12 may be formed of steel, iron or any convenient metal or alloy and is of suflicient length and heated sufiiicently to vaporize the acetone and to heat thevapors to a temperature which, assuming throughout this description that acetone is being cracked, does not exceed about 300 C. at a point 14.
  • the vapor is passed into a tube 15 which is formed of a heat and oxidation resistant alloy or metal free from nickel, for example, chrome-iron (26% to 29% Cr.).
  • the tube 15 is of sufiicient length and is heated so that the vapors are heated to or slightly above about 500 C. where incipient cracking of the acetone will occur. This temperature may be as high as 550 or 575 C. at a point 16.
  • the vapors, now at a stage approximating cracking conditions are passed into a cracking tube 17.
  • the cracked products of pyrolysis including ketene are removed from the furnace 13 by a pipe 19 to be utilized.
  • the tube 17 is preferably made of copper, but other materials having the requisite properties for the pyrolysis of acetone and which do not deleteriously afiect the reaction as defined above may be used.
  • the copper cracking tube 17 as shown. is protected by a shell 18 formed of a metal or alloy which is more resistant to high temperatures and to oxidation than is copper, e. g. chrome-iron or the like may be used. Instead of the shell 18 other protective means may be used.
  • the protective means for the cracking tube is not an essential part of my invention.
  • the contact time of the vapors with cracking temperatures preferably should be between about 0.25 and about 0.75 seconds. That is, the vapors preferably have a space velocity in the cracking zone of about 2500 to about 3500 liters of vapor per liter of volume in the cracking zone per hour. The conversion of acetone to ketene under these conditions is about 15% to 22% per pass. While the foregoing conditions have been found to be desirable, they may be varied within a considerable range.
  • the temperature in the zone of actual pyrolysis should be between about 600 and 750 C., and pressures and gas velocities should be used which will permit the contact time of the vapors to be kept within the above limits.
  • An apparatus for thermally decomposing organic substances to obtain products including ketene which comprises a series of metallic chambers, one of which is composed of an alloy of iron and chromium and which immediately precedes and is connected to the last of said chambers in the series, said last chamber being composed of a metallic material consisting predominantly of copper, the whole of said series forming a single continuous passage, means for supplying the substance to be decomposed to said series of chambers, means for removing the products including ketene from said last chamber, and means for heating said chambers.
  • An apparatus for thermally decomposing organic substances to obtain products including ketene which comprises a series of metallic chambers, one of which is composed of an alloy of'iron and chromium containing between about 10% and about 30% chromium and which immediately precedes and is connected to the last of said chambers in the series, said last chamber being composed of a metallic material consisting predominantly of copper, the wholeof'said series forming a single continuous passage, means for supplying the substance to be decomposed to said series of chambers, means for removing the products including ketene from said last chamber, and means for heating said chambers.
  • An apparatus for thermally decomposing in organic substances to obtain products including ketene which comprises a series of metallic chambers, one of which is composed of an alloy of iron and chromium and which immediately precedes and is connected to the last of said chambers, said last chamber being composed of copper, the whole of said series forming a single continuous passage, means for protecting said last chamber from oxidizing conditions, means for vsupplying the substance to be decomposed to 130 organic substances to obtain products'including ketene which comprises a series of metallic chambers, one of which is composed of an alloy of iron and.
  • said last chamber being composed of 14g copper and provided with a shield of heat resistant metal to protect said copper chamber from oxidizing conditions, the whole of said series forming a single continuous passage, means for supplying the substance to be decomposed to said series, means for removing the products including ketene from said last chamber, and means for heating said chambers.
  • Process for making ketene which comprises passing organic substances which can be decomposed to yield products including ketene successively through a chamber formed of an alloy of iron and chromium which is heated to the lowest temperature decomposition of said substances is initiated, and then through a metallic chamber composed predominantly of copper I tree from iron and nickel, which is heated to a temperature such that said substances are decomposed into products including ketene.
  • Process for making ketene which comprises passing acetone vapors successively through a chamber formed of an alloy of iron and chromium containing between about 10% and about 30% chromium which is heated to a temperature not exceeding about 550 C. and then through a chamber composed essentially of copper and heated to between about 600 and 750 C.
  • ketene which comprises passing acetone vapors successively through a chamber formed of an alloy of chromium and iron which is heated to a temperature not exceeding about 550 C. and then through a chamber formed of copper which is heated to between about 600 and about 750 C. said acetone vapors being under about 5 pounds per square inch of gage pressure.
  • Process for making ketene which comprises passing acetone vapors successively through a chamber formed of an alloy of chromium and iron which is heated to a temperature not exceeding about 550 C., and then through a chamber formed of copper which is heated to between about 600 and about 750 C., said acetone vapors being under about 5 pounds per square inch of gage pressure, and having a maximum space velocity through said chambers of between about 2500 and 3500 liters per liter per hour.
  • Process for making ketene which comprises passing acetone vapors successively through a chamber formed of an alloy of chromium and iron containing more than about 10% of chromium, which is heated to a temperature not exceeding about 550 C., and then through a chamber formed of copper which is heated to between about 600 and about 750 C., said acetone vapors being under about 5 pounds per square inch 01' gage pressure, and having a maximum space velocity through said chambers of between about 2500 and 3500 liters per liter per hour.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Manufacture And Refinement Of Metals (AREA)
US591151A 1932-02-05 1932-02-05 Process and apparatus for making ketene Expired - Lifetime US1975663A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE393839D BE393839A (xx) 1932-02-05
US591151A US1975663A (en) 1932-02-05 1932-02-05 Process and apparatus for making ketene
FR749245D FR749245A (fr) 1932-02-05 1933-01-19 Procédé et appareil pour la fabrication du cétène
GB1970/33A GB413709A (en) 1932-02-05 1933-01-20 Improvements in or relating to process of and apparatus for making ketene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US591151A US1975663A (en) 1932-02-05 1932-02-05 Process and apparatus for making ketene

Publications (1)

Publication Number Publication Date
US1975663A true US1975663A (en) 1934-10-02

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US591151A Expired - Lifetime US1975663A (en) 1932-02-05 1932-02-05 Process and apparatus for making ketene

Country Status (4)

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US (1) US1975663A (xx)
BE (1) BE393839A (xx)
FR (1) FR749245A (xx)
GB (1) GB413709A (xx)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2467993A (en) * 1943-11-10 1949-04-19 Cabot Godfrey L Inc Manufacture of formaldehyde and apparatus therefor
US2521207A (en) * 1945-10-23 1950-09-05 Shawinigan Chem Ltd Gaseous reaction furnace and controller
US2541471A (en) * 1947-07-11 1951-02-13 Eastman Kodak Co Furnace for pyrolyzing ketenizable organic compounds
US5475144A (en) * 1994-06-08 1995-12-12 The University Of Delaware Catalyst and process for synthesis of ketenes from carboxylic acids

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1101403B (de) * 1958-08-01 1961-03-09 Hoffmann La Roche Verfahren zur Herstellung von Keten

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2467993A (en) * 1943-11-10 1949-04-19 Cabot Godfrey L Inc Manufacture of formaldehyde and apparatus therefor
US2521207A (en) * 1945-10-23 1950-09-05 Shawinigan Chem Ltd Gaseous reaction furnace and controller
US2541471A (en) * 1947-07-11 1951-02-13 Eastman Kodak Co Furnace for pyrolyzing ketenizable organic compounds
US5475144A (en) * 1994-06-08 1995-12-12 The University Of Delaware Catalyst and process for synthesis of ketenes from carboxylic acids

Also Published As

Publication number Publication date
GB413709A (en) 1934-07-20
BE393839A (xx)
FR749245A (fr) 1933-07-20

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