US1894266A - Diaryl containing wax-like solid - Google Patents

Diaryl containing wax-like solid Download PDF

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Publication number
US1894266A
US1894266A US398084A US39808429A US1894266A US 1894266 A US1894266 A US 1894266A US 398084 A US398084 A US 398084A US 39808429 A US39808429 A US 39808429A US 1894266 A US1894266 A US 1894266A
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United States
Prior art keywords
benzol
diphenyl
bath
temperature
solid
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Expired - Lifetime
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US398084A
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Charles B Durgin
Russell L Jenkins
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SWANN RES Inc
SWANN RESEARCH Inc
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SWANN RES Inc
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Priority to US398084A priority Critical patent/US1894266A/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/76Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S585/00Chemistry of hydrocarbon compounds
    • Y10S585/929Special chemical considerations
    • Y10S585/946Product is waxy polymer

Definitions

  • This invention relates to a new diarylcontaining wax-like solid.
  • a irther object of this invention is to provide a means whereby the complex character of the product as determined by the boilin points of its various fractions can be varie at will.
  • a still further object of this invention is to provide a product which is useful in producing a chlorinated diaryl which does not become crystalline at the higher chlorine content.
  • the amount of the more complex hydrocarbon can be materially increased by increasing thetemperature of the lead bath, and also by changing the composition of the benzol used as a starting material. Further, we have found that the material thus produced is of great value, since when chlorinated its tendency to crystallize is greatly minimized.
  • Eceo/mple I Commercially pure liquid benzol which distils within a range of 2 C. is pumped through a coil of pipe which is immersed in a bath of a molten substance inert with re spect to the benzol, such as lead or aluminum, and which is maintained at the maximum temperature at which substantially no di phenyl is formed.
  • This coil acts as a preheater and serves to vaporize the liquid benzol and preheat the henzolw vapor to a point in the neighborhood of the diphenyl formation temperature.
  • the coil which is at the bottom of the bath is perforated, and the vapor streams out and in rising through the molten sub- I stance, in physical contact therewith, agitates the bath in such a manner as to maintain a practically uniform temperature throughout the bath.
  • the preheated vapor After the preheated vapor emerges from the preheater bath, it is immediately passed into a converter bath which is of similar design and arrangement as the preheater.
  • the vapor passes to the bottom of the bath and streams out through holes in a distributor, and then bubbles up through the bath in a manner similar to that described for the preheater.
  • the converter bath is kept at a temperature range of from 750 to 850, referably around the latter temperature.
  • percent of the fraction boiling between 200 and 270 C.) with 750 C. converter temperature is approximately 4.5% of the total condensate, while the fraction boiling above 270 C. is approximately 0.4% of the total.
  • the crude diphenyl fraction (200- 270 C.) increases to approximately 8% of the total condensate, while the high-boiling fraction (above 270 C.) increases approxi- 3 inately to 1% of the total.
  • the crude diphenyl fraction increases to approximately 15.5% of the total condensate, while the highboiling fraction increases to approximately 5% 0f the total.
  • Example I I Instead of the commercially pure benzol used in Example I, pass commercial benzol through the converter units described in example I, and exactly in the same manner.
  • Commercial 90% benzol contains certain percentages of other aromatic hydrocarbons, especially toluene and xylene. It is identified by its distillation range. For example, it starts distillation at 762 (3.; dis tils up to C.; and all distils below C. 55 The new product formed in this case is somewhat different in composition from that formed in Example I.
  • Example [[1 High-boiling compound (above 270 C.) in new roduct (above200 Bath temperature Commer- Commerclal 90 per 0181 benzol cent benzol is not suitable or is too expensive. It may also be chlorinated and a non-crystalline solid obtained which is fire-retarding and has excellent properties making it valuable for electrical insulating purposes.
  • the advantages of this invention are that a new product containing varying amounts of high-boiling substances may be cheaply produced.
  • the new product may have a varying composition which is obtained at will by varying the starting materials or the temperature of the reactions.
  • the value of the new product lies in the fact that the physical properties of the diphenyl-containing product may be varied at will within the range above set out.
  • the new product distills above 200 C.
  • the process for producing a diphenyl containing wax-like solid comprising volatilizing commercial 90% benzol, contacting the thus formed vapors with molten lead maintained at diphenyl forming tempera tures, condensing the resulting vapors and heating said condensate to remove hydrocarbons boiling below 200 C. 6.
  • a process of producing diphenyl by thermal synthesis from benzol by contacting benzol with a heated inert molten substance

Description

Patented Jan. 17, 1 933 UNITED STATES.
PATENT 7 OFFICE CHARLES B. DURGIN AN D RUSSELL L. JENKINS, OF ANNISTOH, ALABAMA, ASSIGHOBS TO SWANN RESEARCH, INC A CORPORATIOR OF ALABAMA DIARYL CONTAINING WAX-LIKE SOLID In Drawing.
This invention relates to a new diarylcontaining wax-like solid.
It has been known that when benzol is assed through a red-hot tube, diphenyl is ormed. The composition of the product produced in this way varies with the temperature of the hot tube, the filling material used in the tube, the velocity of the vapors and the presence of such gases as hydrogen n or nitrogen mixed with the benzol. We have discovered that further variation in the composition of the product is obtained when such com ounds as toluene and Xylene arepres ent in the benzol treated in this manner, and that highly condensed complex hydrocarhens are formed.
It has recently been discovered that when benzol is passed through a bath of molten lead, heated to a temperature about 700 0.,
o diphenyl and hydrogen are formed. However, it has not heretofore been known so far as we are aware, that't'he'complex products mentioned above are roduced together with diphenyl in the lea bath method of treating benzol, nor how the composition of the product could be varied at will; It is one of the objects of this invention to provide a new diaryl-containing wax-like solid of high boilin point.
A irther object of this invention is to provide a means whereby the complex character of the product as determined by the boilin points of its various fractions can be varie at will. A still further object of this invention is to provide a product which is useful in producing a chlorinated diaryl which does not become crystalline at the higher chlorine content.
These objects are accomplished, in the fol- 1o lowing manner: We have discovered that when benzol. is passed into andthrough a bath of molten lead heated to between 700 and 800 0., considerable amounts of diphenyl together with a mixture of more complex hydrocarbons are formed. We have further Application filed September 27, 1929. Serial No. 398,084.
found that the amount of the more complex hydrocarbon can be materially increased by increasing thetemperature of the lead bath, and also by changing the composition of the benzol used as a starting material. Further, we have found that the material thus produced is of great value, since when chlorinated its tendency to crystallize is greatly minimized.
The particular'manner in which our invention may be carried out and the new product produced may be illustrated by the following examples:
Eceo/mple I Commercially pure liquid benzol which distils within a range of 2 C. is pumped through a coil of pipe which is immersed in a bath of a molten substance inert with re spect to the benzol, such as lead or aluminum, and which is maintained at the maximum temperature at which substantially no di phenyl is formed. This coil acts as a preheater and serves to vaporize the liquid benzol and preheat the henzolw vapor to a point in the neighborhood of the diphenyl formation temperature.
The coil which is at the bottom of the bath is perforated, and the vapor streams out and in rising through the molten sub- I stance, in physical contact therewith, agitates the bath in such a manner as to maintain a practically uniform temperature throughout the bath. By employing a large mass in the bath, we are enabled to prevent over-heating of the vapor due-to the heat capacity of the bath, and by means of a thermocouple immersed therein to observe temperature changes which may occur and this is the optimum temperature range for continuous operation.
After the preheated vapor emerges from the preheater bath, it is immediately passed into a converter bath which is of similar design and arrangement as the preheater. The vapor passes to the bottom of the bath and streams out through holes in a distributor, and then bubbles up through the bath in a manner similar to that described for the preheater. The converter bath is kept at a temperature range of from 750 to 850, referably around the latter temperature. on the vapor passes from the converter bath it is passed, at a high velocity, directly into a water-cooled condenser, so constructed that the vapor is quickly cooled and the unconverted benzene and the diphenyl are condensed and collected, while the hydrogen which is liberated when diphenyl is formed is vented through a water seal.
We have found that when operating in this manner with commercially pure benzole, the percentage of crude diphenyl (i. e., the
percent of the fraction boiling between 200 and 270 C.) with 750 C. converter temperature is approximately 4.5% of the total condensate, while the fraction boiling above 270 C. is approximately 0.4% of the total.
If now the converter temperature be raised to 800 (1, the crude diphenyl fraction (200- 270 C.) increases to approximately 8% of the total condensate, while the high-boiling fraction (above 270 C.) increases approxi- 3 inately to 1% of the total. By further increasing the temperature to 850 C., the crude diphenyl fraction increases to approximately 15.5% of the total condensate, while the highboiling fraction increases to approximately 5% 0f the total.
Example I I Instead of the commercially pure benzol used in Example I, pass commercial benzol through the converter units described in example I, and exactly in the same manner. Commercial 90% benzol contains certain percentages of other aromatic hydrocarbons, especially toluene and xylene. It is identified by its distillation range. For example, it starts distillation at 762 (3.; dis tils up to C.; and all distils below C. 55 The new product formed in this case is somewhat different in composition from that formed in Example I.
In the following table, these products are compared. These results were obtained by so fractionally distilling the new product ob tained as heretofore outlined (boiling above 200 G.) into two fractions, one distilling between 200 C. and 270 C. and the second distilling above 27 0 C. The latter fraction 05 (above 270 C.) is termed high boiling compound while the fraction boiling between 200 and 270 C. is termed mainly diphenyl.
Example [[1 High-boiling compound (above 270 C.) in new roduct (above200 Bath temperature Commer- Commerclal 90 per 0181 benzol cent benzol is not suitable or is too expensive. It may also be chlorinated and a non-crystalline solid obtained which is fire-retarding and has excellent properties making it valuable for electrical insulating purposes.
The advantages of this invention are that a new product containing varying amounts of high-boiling substances may be cheaply produced. The new product may have a varying composition which is obtained at will by varying the starting materials or the temperature of the reactions. The value of the new product lies in the fact that the physical properties of the diphenyl-containing product may be varied at will within the range above set out.
The new product distills above 200 C.
and is comprised of two classes of compound,-
namely, crude diphenylboiling between 200 and 270 and high boiling compound boiling above 270 and below the decomposition temperature of the compound which is in the neighborhood of 350 to 400 C.
\Vhat we claim is:
1. The process for producinga diphenyl 700 C. and 800 0., condensing the resulting vapors and heating said condensate to 200 C. to-remove low boiling constituents.
3. The process for producing a diphenyl containing wax-like solid, comprising volatilizing benzol admixed with substantial quantities of toluol and xylol, contacting said vapor with a fluid'mass maintained at diphenyl forming temperatures, condensing the resulting vapors and heating said con densate to 200 C. to remove low-boiling constituents.
4. The process for producing a diphenyl containing wax-like solid, comprising volatilizing commercial 90% benzol, contacting the thus formed vapors with an inert liquid mass maintained at diphenyl forming temperatures, condensing the resulting vapors and heating said condensate to remove hydrocarbons boiling below 200 C.
5. The process for producing a diphenyl containing wax-like solid, comprising volatilizing commercial 90% benzol, contacting the thus formed vapors with molten lead maintained at diphenyl forming tempera tures, condensing the resulting vapors and heating said condensate to remove hydrocarbons boiling below 200 C. 6. In a process of producing diphenyl by thermal synthesis from benzol by contacting benzol with a heated inert molten substance,
the step of controlling the percentage of com plex hydrocarbons boiling above 27 0 C. by
controlling the temperature of said substance.
v 7. In a process of producing diphenyl by thermal synthesis from benzol by contacting benzol with a heated inert molten substance, the step of controlling the percentage of complex hydrocarbons boiling 'above 270 C. by maintaining the temperature of said substance at above 800 C. p 8. In a'process of producing diphenyl by thermal synthesis from benzol by contacting benzol with a heated inert molten substance comprising vaporizing commercial 90% benzol, and subjecting the vapors by contact with said molten substance to a temperature of from 800 to 850 C. to increase the production (23f complex hydrocarbons boiling above 270 a 9. In a process of producing diphenyl by thermal synthesis from benzol by contacting benzol with a heated inert molten substance comprising, vaporizing a mixture of commercial benzol and commercial benzol,
and subjecting the vapors by contact with said molten substance to a temperature of from 800 to 850 C. to increase'the produ'ction of complex hydrocarbons boiling above 270 C. In testimony whereof we aflix our signatures.
CHARLES B. DURGIN. RUSSELL L, JENKINS.
US398084A 1929-09-27 1929-09-27 Diaryl containing wax-like solid Expired - Lifetime US1894266A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6340024B1 (en) 1993-01-07 2002-01-22 Dme Corporation Protective hood and oral/nasal mask

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6340024B1 (en) 1993-01-07 2002-01-22 Dme Corporation Protective hood and oral/nasal mask

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