Hive Novel Discourse

	Main Index Search Register Login Who's Online FAQ Links
	Main Index Search Register Login Who's Online FAQ Links

	1 Online, 0 Active		You are not logged in

This is a historical archiveThe forum is read-only. Private information has been removed. It is not possible to login.

	Novel Discourse

All 26 posts Subject: Phenylacetic acid another way Please login to post Down

Elementary
(Hive Addict)
04-14-02 20:25
No 296888
User Picture       Phenylacetic acid another way
(Rated as: excellent)

Method of preparing Phenylacetaldehyde or Phenylacetic acid

1. Production of Phenylethanol from benzene and ethylene oxide

Patent No US1944959

Abstract

In a suitable container in which there has been placed 500 g of anhydrous AlCl₃ there is added 800 g of benzene under stiring, 180 grams ethylene oxide in gaseous form and an equal amount of air are passed through the mixture at 45-55°C until only a small amount of AlCl₃ has been left. The reaction container is constantly externally cooled with circulating water to maintain the desired temperature. The temperature is kept preferably withing the range of about substantially 45°C to about subtantially 55°C but as hereafter seen can range from -20°C upwards. The reaction product obtained is treated in the usual way with ice, seperated and vacuum distilled. In this reaction about 173 g phenylethyl alcohol and only 2 g dibenzyl were formed.

2. Ethylene Oxide

Ethanol is mixed with excess of conc sulphuric acid. Ethyl Hydrogen Sulphate is formed in the cold, but on heating to about 170°C it decomposes into ethylene and sulphuric acid.

When ethylene is mixed with air or oxygen and passed over a silver catalyst at 300°C, it is converted into ethylene oxide, a colourless liquid, BP 11C.

3. Oxidisation Of Phenylethanol (phenyl ethyl alcohol)

According to the strength of the oxidising agent used, phenylethanol can be oxidised to phenylacetaldehyde or phenylacetic acid.

Nobodys home

Aurelius
(Hive Bee)
04-14-02 21:13
No 296904
      Temperature

if the temp can range from -22°C on up, then why not chill to 0°C in a salt/water bath? that way everything is liquid phase and the bubbling is no longer a necessity. (good post though)

terbium
(Old P2P Cook)
04-14-02 21:50
No 296923
      This is a patent.

if the temp can range from -22°C on up, then why not chill to 0°C in a salt/water bath? that way everything is liquid phase and the bubbling is no longer a necessity.
Because it probably doesn't work very well at that temperature. The patent states that the best temperature is 45-55°C. When reading patents you have to remember that the purpose of a patent is not to claim just the optimal conditions but, just the opposite, to claim all possible conditions.

Aurelius
(Hive Bee)
04-15-02 04:15
No 297038
      Thanks

Terbium, thanks. that's kinda what aurelius figured but thought it was worth a shot.

PrimoPyro
(Hive Prodigy)
04-15-02 04:33
No 297042
      Propylene Oxide --> P2Pol

Would usage of propylene oxide afford P2Pol?
Vivent Longtemps La Ruche!

Rhodium
(Chief Bee)
04-15-02 04:43
No 297044
User Picture       P2Pol

PP: Yes.

PrimoPyro
(Hive Prodigy)
04-15-02 04:46
No 297045
      Forgive My Intrusion

But will nonaqueous hypochlorite coordinate with aluminum chloride? (please say no) wink
Vivent Longtemps La Ruche!

Aurelius
(Hive Bee)
04-15-02 05:25
No 297063
      P2P

Going for a one-pot-shot at P2P?... smile wink

PrimoPyro
(Hive Prodigy)
04-15-02 05:32
No 297067
      Why Yes I Am. ;)

Do you remember Post 270904 (PrimoPyro: "Grignard P2Pol In Situ Oxidation", Novel Discourse)? T'would be a neat trick to pull off in one pot, would it not? smile

PrimoPyro
Vivent Longtemps La Ruche!

Aurelius
(Hive Bee)
04-15-02 05:35
No 297069
      results

PrimoPyro, give it a whirl and post the results. It would be AWESOME to see a synth like that.

Elementary
(Hive Addict)
04-15-02 13:46
No 297177
User Picture       Propylene rambles

The patent also mentions phenylpropyl alcohol and isomers from benzene and propylene oxide.

Propylene Oxide

Propylene could probably be made by the depolymerisation of Polypropylene, or in the usual way with conc sulphuric acid and isopropyl alcohol.

Propylene > Propylene oxide (watch this space)

Phenyl(iso?)propyl alcohol can then be worked up to goodies

Nobodys home

Elementary
(Hive Addict)
04-15-02 13:56
No 297178
User Picture       Alkylene Oxides from Glycols
(Rated as: excellent)

When Ethylene glycol is treated with HCl it is converted to Ethylene Chlorhydrin.

Strong alkali converts Chlorhydrins into Alkylene Oxides

EDIT Chlorine water converts olefins (ethylene/propylene) to chlorohydrins as well.

Nobodys home

foxy2
(Distinctive Doe)
04-15-02 16:49
No 297226
      this to

2,3-propanediol should work with HCl as well. It would bee easier to get than gaseous propylene.
Those who give up essential liberties for temporary safety deserve neither liberty nor safety

PrimoPyro
(Hive Prodigy)
04-15-02 20:43
No 297341
      Oh My

You people did know that propylene oxide is available as a fuel additive for racing cars by the multigallon drum, did you not?

I mean come on now, what was I thinking when I bought that 5 gallon drum of methanol, 1 gallon of nitromethane, and 1 gallon of propylene oxide for my dragster? wink

PrimoPyro
Vivent Longtemps La Ruche!

terbium
(Old P2P Cook)
04-15-02 20:54
No 297348
      NHRA permitted?

I was vaguely under the impression that propylene oxide was not a permitted additive.

PrimoPyro
(Hive Prodigy)
04-15-02 20:59
No 297351
      You Can Buy It In The US

Well, it is up for sale as an additive in the US, and available for the same at a few Online Places as well.

Check your PMs for details.

   PrimoPyro
Vivent Longtemps La Ruche!

Osmium
(Stoni's sexual toy)
04-15-02 21:19
No 297360
User Picture       OMG! They sell propylene oxide to the fucking ...

OMG! They sell propylene oxide to the fucking public?? That shit isn't healthy at all.
And I'm not sure if I like to see inexperienced bees working with stuff like ethylene oxide, propylene oxide or even epichlorohydrin either.
I'm not fat just horizontally disproportionate.

Elementary
(Hive Addict)
05-08-02 02:47
No 306038
User Picture       Help ! Can any body help me with another name for ...

Help !

Can any body help me with another name for 2,3-propanediol that foxy mentioned earlier, or even a formula ?

What do you think about the possiblity of changing aluminium chloride for another lewis acid (Iron chloride) in the reaction between benzene and the propylene oxide ?
Don't cry for me I'm the cleaner

Rhodium
(Chief Bee)
05-08-02 04:24
No 306058
User Picture       2,3-propanediol = 1,2-propanediol

Elementary: The proper name is 1,2-propanediol (propylene glycol).

Elementary
(Hive Addict)
05-08-02 23:02
No 306420
      The patent mentions that the usage of propylene ...

The patent mentions that the usage of propylene oxide will afford phenylpropyl alcohol and isomers.

So I guess the main products will be :

Phenylpropyl Alcohol (Hydrocinnamic Alcohol ?)
Phenylisopropyl Alcohol
Any others ?

So if phenylisopropyl alcohol can be oxidised to 1 Phenyl 2 Propanone (P2P), what does phenylpropyl alcohol get oxidised to ?

And what determines if an secondary alcohol oxidises to an aldehyde(then to an acid) or an ketone ?

Don't cry for me I'm the cleaner

PrimoPyro
(Hive Prodigy)
05-08-02 23:13
No 306426
      Elementary

Secondary alcohols never become aldehydes or acids. Primary alcohols go through those reactions, and secondary alcohols become ketones.

The other side product of this reaction would be 2-phenyl-1-propanol, which would oxidize to 2-phenylpropanal, which in turn can stil be changed into P2P a la Rhodium's site, with H2SO4 or HgCl2.

The phenylpropyl alcohol would oxidize to phenylpropanal, the aldehyde, or phenylpropionic acid, the carboxylic acid.

   PrimoPyro
Vivent Longtemps La Ruche!

Elementary
(Hive Addict)
05-08-02 23:17
No 306429
User Picture       phenylpropyl alcohol

The phenylpropyl alcohol would oxidize to phenylpropanal, the aldehyde, or phenylpropionic acid, the carboxylic acid.

So does phenylpropyl alcohol not behave like a secondary alcohol then ?
Don't cry for me I'm the cleaner

PrimoPyro
(Hive Prodigy)
05-09-02 00:23
No 306465
      PhPrOH = Primary

Phenylpropyl alcohol is a primary alcohol. Phenylpropanol is 1-phenyl-3-propanol, and is a primary alcohol.

Phenylisopropanol is 1-phenyl-2-propanol, and is a secondary alcohol.

2-phenyl-1-propanol is also a primary alcohol, and yields 2-phenylpropanal upon oxidation.

PrimoPyro
Vivent Longtemps La Ruche!

terbium
(Old P2P Cook)
05-14-02 06:02
No 308250
      Secondary alcohol oxidation.

Secondary alcohols never become aldehydes or acids.
Not true, especially when the hydrogens next to the alcohol are benzylic, the secondary alcohol can be oxidzed to an acid.

PrimoPyro
(Hive Prodigy)
05-14-02 09:21
No 308325
      True

But only when accompanied by either a rearrangement or a C-C fission, which I had omitted the possibility of for this thread's topic.

   PrimoPyro
Vivent Longtemps La Ruche!

lugh
(Moderator)
06-26-04 22:52
No 515621
      Propylene Chlorohydrin
(Rated as: good read)

This article from Journal of Applied Chemistry USSR (Engl. Trans.) 32, 891-4 (1959) by Etlis and Grobov may bee of interest to some bees wink

smile

Chemistry is our Covalent Bond

	https://the-hive.archive.erowid.org	the-hive@erowid.org



Powered by Pornucopia(TM) Version 3.20.1b, © 2014-2019, UTFSE-Soft
Links Erowid Rhodium

	All 26 posts		Subject: Phenylacetic acid another way		Please login to post		Down


		Elementary (Hive Addict) 04-14-02 20:25 No 296888				Phenylacetic acid another way (Rated as: excellent)
						Method of preparing Phenylacetaldehyde or Phenylacetic acid 1. Production of Phenylethanol from benzene and ethylene oxide Patent No US1944959 Abstract In a suitable container in which there has been placed 500 g of anhydrous AlCl₃ there is added 800 g of benzene under stiring, 180 grams ethylene oxide in gaseous form and an equal amount of air are passed through the mixture at 45-55°C until only a small amount of AlCl₃ has been left. The reaction container is constantly externally cooled with circulating water to maintain the desired temperature. The temperature is kept preferably withing the range of about substantially 45°C to about subtantially 55°C but as hereafter seen can range from -20°C upwards. The reaction product obtained is treated in the usual way with ice, seperated and vacuum distilled. In this reaction about 173 g phenylethyl alcohol and only 2 g dibenzyl were formed. 2. Ethylene Oxide Ethanol is mixed with excess of conc sulphuric acid. Ethyl Hydrogen Sulphate is formed in the cold, but on heating to about 170°C it decomposes into ethylene and sulphuric acid. When ethylene is mixed with air or oxygen and passed over a silver catalyst at 300°C, it is converted into ethylene oxide, a colourless liquid, BP 11C. 3. Oxidisation Of Phenylethanol (phenyl ethyl alcohol) According to the strength of the oxidising agent used, phenylethanol can be oxidised to phenylacetaldehyde or phenylacetic acid. Nobodys home



		Aurelius (Hive Bee) 04-14-02 21:13 No 296904				Temperature
						if the temp can range from -22°C on up, then why not chill to 0°C in a salt/water bath? that way everything is liquid phase and the bubbling is no longer a necessity. (good post though)



		terbium (Old P2P Cook) 04-14-02 21:50 No 296923				This is a patent.
						if the temp can range from -22°C on up, then why not chill to 0°C in a salt/water bath? that way everything is liquid phase and the bubbling is no longer a necessity. Because it probably doesn't work very well at that temperature. The patent states that the best temperature is 45-55°C. When reading patents you have to remember that the purpose of a patent is not to claim just the optimal conditions but, just the opposite, to claim all possible conditions.



		Aurelius (Hive Bee) 04-15-02 04:15 No 297038				Thanks
						Terbium, thanks. that's kinda what aurelius figured but thought it was worth a shot.



		PrimoPyro (Hive Prodigy) 04-15-02 04:33 No 297042				Propylene Oxide --> P2Pol
						Would usage of propylene oxide afford P2Pol? Vivent Longtemps La Ruche!



		Rhodium (Chief Bee) 04-15-02 04:43 No 297044				P2Pol
						PP: Yes.



		PrimoPyro (Hive Prodigy) 04-15-02 04:46 No 297045				Forgive My Intrusion
						But will nonaqueous hypochlorite coordinate with aluminum chloride? (please say no) Vivent Longtemps La Ruche!



		Aurelius (Hive Bee) 04-15-02 05:25 No 297063				P2P
						Going for a one-pot-shot at P2P?...



		PrimoPyro (Hive Prodigy) 04-15-02 05:32 No 297067				Why Yes I Am. ;)
						Do you remember Post 270904 (PrimoPyro: "Grignard P2Pol In Situ Oxidation", Novel Discourse)? T'would be a neat trick to pull off in one pot, would it not? PrimoPyro Vivent Longtemps La Ruche!



		Aurelius (Hive Bee) 04-15-02 05:35 No 297069				results
						PrimoPyro, give it a whirl and post the results. It would be AWESOME to see a synth like that.



		Elementary (Hive Addict) 04-15-02 13:46 No 297177				Propylene rambles
						The patent also mentions phenylpropyl alcohol and isomers from benzene and propylene oxide. Propylene Oxide Propylene could probably be made by the depolymerisation of Polypropylene, or in the usual way with conc sulphuric acid and isopropyl alcohol. Propylene > Propylene oxide (watch this space) Phenyl(iso?)propyl alcohol can then be worked up to goodies Nobodys home



		Elementary (Hive Addict) 04-15-02 13:56 No 297178				Alkylene Oxides from Glycols (Rated as: excellent)
						When Ethylene glycol is treated with HCl it is converted to Ethylene Chlorhydrin. Strong alkali converts Chlorhydrins into Alkylene Oxides EDIT Chlorine water converts olefins (ethylene/propylene) to chlorohydrins as well. Nobodys home



		foxy2 (Distinctive Doe) 04-15-02 16:49 No 297226				this to
						2,3-propanediol should work with HCl as well. It would bee easier to get than gaseous propylene. Those who give up essential liberties for temporary safety deserve neither liberty nor safety



		PrimoPyro (Hive Prodigy) 04-15-02 20:43 No 297341				Oh My
						You people did know that propylene oxide is available as a fuel additive for racing cars by the multigallon drum, did you not? I mean come on now, what was I thinking when I bought that 5 gallon drum of methanol, 1 gallon of nitromethane, and 1 gallon of propylene oxide for my dragster? PrimoPyro Vivent Longtemps La Ruche!



		terbium (Old P2P Cook) 04-15-02 20:54 No 297348				NHRA permitted?
						I was vaguely under the impression that propylene oxide was not a permitted additive.



		PrimoPyro (Hive Prodigy) 04-15-02 20:59 No 297351				You Can Buy It In The US
						Well, it is up for sale as an additive in the US, and available for the same at a few Online Places as well. Check your PMs for details. PrimoPyro Vivent Longtemps La Ruche!



		Osmium (Stoni's sexual toy) 04-15-02 21:19 No 297360				OMG! They sell propylene oxide to the fucking ...
						OMG! They sell propylene oxide to the fucking public?? That shit isn't healthy at all. And I'm not sure if I like to see inexperienced bees working with stuff like ethylene oxide, propylene oxide or even epichlorohydrin either. I'm not fat just horizontally disproportionate.



		Elementary (Hive Addict) 05-08-02 02:47 No 306038				Help ! Can any body help me with another name for ...
						Help ! Can any body help me with another name for 2,3-propanediol that foxy mentioned earlier, or even a formula ? What do you think about the possiblity of changing aluminium chloride for another lewis acid (Iron chloride) in the reaction between benzene and the propylene oxide ? Don't cry for me I'm the cleaner



		Rhodium (Chief Bee) 05-08-02 04:24 No 306058				2,3-propanediol = 1,2-propanediol
						Elementary: The proper name is 1,2-propanediol (propylene glycol).



		Elementary (Hive Addict) 05-08-02 23:02 No 306420				The patent mentions that the usage of propylene ...
						The patent mentions that the usage of propylene oxide will afford phenylpropyl alcohol and isomers. So I guess the main products will be : Phenylpropyl Alcohol (Hydrocinnamic Alcohol ?) Phenylisopropyl Alcohol Any others ? So if phenylisopropyl alcohol can be oxidised to 1 Phenyl 2 Propanone (P2P), what does phenylpropyl alcohol get oxidised to ? And what determines if an secondary alcohol oxidises to an aldehyde(then to an acid) or an ketone ? Don't cry for me I'm the cleaner



		PrimoPyro (Hive Prodigy) 05-08-02 23:13 No 306426				Elementary
						Secondary alcohols never become aldehydes or acids. Primary alcohols go through those reactions, and secondary alcohols become ketones. The other side product of this reaction would be 2-phenyl-1-propanol, which would oxidize to 2-phenylpropanal, which in turn can stil be changed into P2P a la Rhodium's site, with H2SO4 or HgCl2. The phenylpropyl alcohol would oxidize to phenylpropanal, the aldehyde, or phenylpropionic acid, the carboxylic acid. PrimoPyro Vivent Longtemps La Ruche!



		Elementary (Hive Addict) 05-08-02 23:17 No 306429				phenylpropyl alcohol
						The phenylpropyl alcohol would oxidize to phenylpropanal, the aldehyde, or phenylpropionic acid, the carboxylic acid. So does phenylpropyl alcohol not behave like a secondary alcohol then ? Don't cry for me I'm the cleaner



		PrimoPyro (Hive Prodigy) 05-09-02 00:23 No 306465				PhPrOH = Primary
						Phenylpropyl alcohol is a primary alcohol. Phenylpropanol is 1-phenyl-3-propanol, and is a primary alcohol. Phenylisopropanol is 1-phenyl-2-propanol, and is a secondary alcohol. 2-phenyl-1-propanol is also a primary alcohol, and yields 2-phenylpropanal upon oxidation. PrimoPyro Vivent Longtemps La Ruche!



		terbium (Old P2P Cook) 05-14-02 06:02 No 308250				Secondary alcohol oxidation.
						Secondary alcohols never become aldehydes or acids. Not true, especially when the hydrogens next to the alcohol are benzylic, the secondary alcohol can be oxidzed to an acid.



		PrimoPyro (Hive Prodigy) 05-14-02 09:21 No 308325				True
						But only when accompanied by either a rearrangement or a C-C fission, which I had omitted the possibility of for this thread's topic. PrimoPyro Vivent Longtemps La Ruche!



		lugh (Moderator) 06-26-04 22:52 No 515621				Propylene Chlorohydrin (Rated as: good read)
						This article from Journal of Applied Chemistry USSR (Engl. Trans.) 32, 891-4 (1959) by Etlis and Grobov may bee of interest to some bees Chemistry is our Covalent Bond

All 26 posts	End of thread	Top