4 Rewrite summary
source | link

I seriously doubt the "vigorous" conditions.

What are the precise conditions under which Benzene undergoes ozonolysis?

In Über das Ozobenzol, an early German publication on the reaction of benzene with ozone, Ber. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1–2 Stunden lang bei einer Temperatur von 5–10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […]

Lässt man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. Selbst beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5–10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions.

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005–1019, (DOI) notes that the ozonisation of benzene was performed in chloroform at a temperature of 242 K (–31 °C).


In the late 1960s, ozonization of benzene again gained some interest as a possible source for glyoxal in industrial synthesis.

In Glyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI), the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at temperatures between –20 °C and 15 °C.


In summary, claimsSummary

All anyone can tell me is that it undergoes ozonolysis under "vigorous" conditions.

Apparently, your sources never bothered to check the literature! While the ozonide itself may detonate on touch, claims on the "vigorous" conditions necessary for its synthesis seem to be fully unsubstantiated by the literature!

I seriously doubt the "vigorous" conditions.

In Über das Ozobenzol, an early German publication on the reaction of benzene with ozone, Ber. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1–2 Stunden lang bei einer Temperatur von 5–10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […]

Lässt man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. Selbst beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5–10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions.

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005–1019, (DOI) notes that the ozonisation of benzene was performed in chloroform at a temperature of 242 K (–31 °C).


In the late 1960s, ozonization of benzene again gained some interest as a possible source for glyoxal in industrial synthesis.

In Glyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI), the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at temperatures between –20 °C and 15 °C.


In summary, claims on the "vigorous" conditions seem to be fully unsubstantiated by the literature!

What are the precise conditions under which Benzene undergoes ozonolysis?

In Über das Ozobenzol, an early German publication on the reaction of benzene with ozone, Ber. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1–2 Stunden lang bei einer Temperatur von 5–10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […]

Lässt man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. Selbst beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5–10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions.

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005–1019, (DOI) notes that the ozonisation of benzene was performed in chloroform at a temperature of 242 K (–31 °C).


In the late 1960s, ozonization of benzene again gained some interest as a possible source for glyoxal in industrial synthesis.

In Glyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI), the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at temperatures between –20 °C and 15 °C.


Summary

All anyone can tell me is that it undergoes ozonolysis under "vigorous" conditions.

Apparently, your sources never bothered to check the literature! While the ozonide itself may detonate on touch, claims on the "vigorous" conditions necessary for its synthesis seem to be fully unsubstantiated by the literature!

3 Apparantly, your OCR was off. I checked against the original publication and changed to the spelling used there.
source | link

I seriously doubt the "vigorous" conditions.

In Über das Ozobenzol, an early German publication on the reaction of benzene with ozone, Ber. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1-21–2 Stunden lang bei einer Temperatur von 5-10°5–10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […][…]

LaestLässt man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. SelbStSelbst beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5-105–10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions.

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005-10191005–1019, (DOI) notes that the ozonisation of benzene was performed in chloroform at a temperature of 242 K (-31–31 °C).


In the late 1960s, ozonization of benzene again gained some interest as a possible source for glyoxal in industrial synthesis.

In Glyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI), the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at temperatures between -20–20 °C and 15 °C.


In summary, claims on the "vigorous" conditions seem to be fully unsubstantiated by the literature!

I seriously doubt the "vigorous" conditions.

In Über das Ozobenzol, an early German publication on the reaction of benzene with ozone, Ber. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1-2 Stunden lang bei einer Temperatur von 5-10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […]

Laest man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. SelbSt beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5-10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions.

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005-1019, (DOI) notes that the ozonisation of benzene was performed in chloroform at a temperature of 242 K (-31 °C).


In the late 1960s, ozonization of benzene again gained some interest as a possible source for glyoxal in industrial synthesis.

In Glyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI), the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at temperatures between -20 °C and 15 °C.


In summary, claims on the "vigorous" conditions seem to be fully unsubstantiated by the literature!

I seriously doubt the "vigorous" conditions.

In Über das Ozobenzol, an early German publication on the reaction of benzene with ozone, Ber. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1–2 Stunden lang bei einer Temperatur von 5–10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […]

Lässt man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. Selbst beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5–10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions.

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005–1019, (DOI) notes that the ozonisation of benzene was performed in chloroform at a temperature of 242 K (–31 °C).


In the late 1960s, ozonization of benzene again gained some interest as a possible source for glyoxal in industrial synthesis.

In Glyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI), the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at temperatures between –20 °C and 15 °C.


In summary, claims on the "vigorous" conditions seem to be fully unsubstantiated by the literature!

2 Add various references, text exercepts and translation for ozonization of benzene at low temperatures
source | link

I seriously doubt the "vigorous" conditions. I seriously doubt the "vigorous" conditions.

To my knowledgeIn Über das Ozobenzol, an early German publication on the ozonolysisreaction of benzene with ozone, as described by W. PBer. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1-2 Stunden lang bei einer Temperatur von 5-10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […]

Laest man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. SelbSt beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5-10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions. Keaveney

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005-1019, (DOI) notes that the ozonisation of benzene was carried outperformed in chloroform at low temperaturesa temperature of 242 K (-531 °C) in solvents of low molecular weight.


In the late 1960s, typically mixturesozonization of alkanoic acids and nitroalkanesbenzene again gained some interest as a possible source for glyoxal in industrial synthesis. Conversion rates

In (based on benzeneGlyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI) were about 25%, the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at besttemperatures between -20 °C and 15 °C.


In summary, claims on the "vigorous" conditions seem to be fully unsubstantiated by the literature!

I seriously doubt the "vigorous" conditions.

To my knowledge, the ozonolysis of benzene, as described by W. P. Keaveney, was carried out at low temperatures (-5 °C) in solvents of low molecular weight, typically mixtures of alkanoic acids and nitroalkanes. Conversion rates (based on benzene) were about 25% at best.

I seriously doubt the "vigorous" conditions.

In Über das Ozobenzol, an early German publication on the reaction of benzene with ozone, Ber. Dtsch. Chem. Ges., 1904, 337, 3431-3433 (DOI) , the authors write

Leitet man in solches Benzol 1-2 Stunden lang bei einer Temperatur von 5-10° einen 5-procentigen Ozonstrom, so scheidet sich eine gelatinöse Masse aus, welche stark opalisirt. […]

Laest man das unangegriffene Benzol verdunsten, so bildet es eine weisse, amorphe Masse von furchtbar explosiven Eigenschaften. SelbSt beim Uebergiessen mit warmem Wasser detonirte diese Substanz heftig.

Uebergiesst man aber das gelatinöse Product mit eiskaltem Wasser, so entsteht eine krystallinische Modification, die wohl möglich noch heftiger als die amorphe bei der geringsten Berührung, ähnlich wie Jodstickstoff, explodirt.

To sum this up:

  • The authors prepared the primary triozonide of benzene by passing a stream of ozone though it at a temperature of 5-10 °C.

  • Once the remaining benzene evaporated at room temperature, a white, amorphous mass with frightfully explosive properties was obtained.

  • When warm water was poured over it, this mass detonated.

  • When cold water was poured over the amorphous, jelly-like mass, a crystalline modification was obtained, which detonated on the slightest touch, similar to to nitrogen triiodide.


In the 1950s, a group of Dutch researchers published a series of articles about their kinetic experiments on the ozonization reactions.

The second article in the series, Recl. Trav. Chim. Pays-Bas, 1951, 70, 1005-1019, (DOI) notes that the ozonisation of benzene was performed in chloroform at a temperature of 242 K (-31 °C).


In the late 1960s, ozonization of benzene again gained some interest as a possible source for glyoxal in industrial synthesis.

In Glyoxal from Ozonolysis of Benzene, published in Ind. Eng. Chem. Prod. Res. Dev., 1969, 8, 89–92 DOI), the authors describe the ozonolysis of benzene in a mixture of acetic acid and nitromethane at temperatures between -20 °C and 15 °C.


In summary, claims on the "vigorous" conditions seem to be fully unsubstantiated by the literature!

1
source | link