Hydratropic--->p2p Success!

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BooWho
(Hive Bee)
08-09-02 09:43
No 343493




Hydratropic--->p2p Success!
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First off special thanks to Jan1983, who initially brought this to Boo's attention in one of his posts Post 319753 (Jan1983: "Succsess story: 85ml H2SO4 96% 18ml Hydratropic ...", Stimulants).

Poor Jan who is now in flight from authorities. Boo is sending you good thoughts of successful escape, Jan.

IT works!!! Hydratropic Aldehyde + H2SO4-->p2p.

One thing to note... near the end of Jan's write-up it is a little unclear.
Separate the organic phase (top layer) from the acid/water layer (bottom). Then begin the extraction of the p2p. Boo used toulene instead of ether with no problems at all.
Also after letting it sit overnight, the p2p separated from the toulene and was floating on top.
Boo vacuum distilled half of it... taking the distillate that came over at 92degrees. In comparing the two (distilled and non-distilled) there appears to be no difference. It may be possible to skip the distillation if allowed to sit and separate.
Will run them separately in the next stage of rxns to compare final product.
AHHHHH!
Boo's successful first stage of his master plan
------ GO GO from No Go!!! ------ is complete.
Now on to stage 2... Chromic's methylamine synth!

boo
Boo loves karma
   karma corn, karma apples, karma chameleon

pimpmaster
(Hive Bee)
08-15-02 13:26
No 345703




Congratulations Boo. First I would like to ask ...
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Congratulations Boo. First I would like to ask you a few Questions
1.How much Hydratropic aldehyde did you use?
2.How much of H2SO4 did you use and what % was the H2SO4?
3.What kind of vessel did you use for the reaction?
4.What did you use for stirring?
5.What did you use in your cold bath ice/NaCl or something else?
Secondly Swims most experienced new hoe told swim that she will be trying this synth out next week and will post about the results in next week. Whish her luck

Ps go for the eyes Boo, go for the eyes Boo

trans
(Newbee)
08-15-02 17:01
No 345771




Jann on the Lamm?
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What happened to Jan1983? I am curious there boo.

Osmium
(Stoni's sexual toy)
08-15-02 17:31
No 345782




> Also after letting it sit overnight, the p2p ...
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> Also after letting it sit overnight, the p2p separated
> from the toulene and was floating on top

Wow. I guess this makes workup even easier!

Where did you find the hydratropic aldehyde?
I'm not fat just horizontally disproportionate.

PrimoPyro
(Hive Prodigy)
08-15-02 18:37
No 345801




Hahaha, Os
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You're mean, but it's funny.

What does hydratropic aldehyde smell like anyway? Is it particularlu pungnent in odor, or is it lightly aromatic?

PrimoPyro

BooWho
(Hive Bee)
08-15-02 19:47
No 345828




I'd like to buy you a coke....
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H -T-A was 36mls and h2so4 was 170 mls of the 96% and both left overnight in freezer prior to rxn.
Boo froze a 1 ltr erlenmeyer half way up in a block of ice and wet it down with rock salt and acetone to keep it at
-15 degrees... and used a battery powered screwdriver fitted with an improvised melamine paddle. An oversized rubber stopper drilled with 2 holes for stirrer and tip of separatory funnel for timed 1drop every 3 seconds addition of H-T-A.

hee hee hee... whitebread kitchen cornpone handmedown chemistry...

Now Os... PM Boo for sources....
You trying to get Boo into some bad karma shit.....?

H -T-A smells like pickled frogs mixed with a bottle of chanel no 5.... very sickly aromatic... like my butt!

After it sits up in the crushed ice the smell changes completely...

As far as Boo knows Jan is still a fugitive from european authorities... at least at the time of this posting Jan is still NOT in custody and will hopefully be able to VANISH....

Beyond this tiny experiment, know that you people, the founder bees, are the heart of our motivation. Lillenthal, Rhodium, WizardX, Osmium, Primo, Curbshot, Strike... to name a few...
You are our ideal.

boo

Imsurethissongwouldhaveneverbeenwroteiftheprettygirlhadofbeenmilkinghergoatbutthegoatwasntfeelingwellanyhowsotheprettygirlwasmilkinghercow
Boo loves karma
   karma corn, karma apples, karma chameleon

Bwiti
(PVC-Analog Taste-Tester)
08-15-02 22:29
No 345879




Every supplier I contact regarding hydratropic ...
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Every supplier I contact regarding hydratropic aldehyde gives me the cold shoulder.
Love my country, fear my government.

wareami
(Hive Addict)
08-16-02 02:02
No 345927




YaaaaY! YeeBeeDabbaBOOBEE! (:ï?
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Very Impressive Boo!
Ibee had half a mind to inquire recently about the progress!
And now he sees by SWIB'S victorious endeavors and results that he may need a full mind for the added boosts in the task management/procrastination department!
Seems the "FullyAutomated BatteryPowered SwiftKicker" aint what it use to bee.
Swib's timing couldn't have been time-lEer! Switching GEARS is becoming a virtualreality as the clutchof Eggs has seen better daze!
A well deserved from Ibee, Ware and The KIDZ at UP-AWE-NITE.

Primo: Since Jan1983 is beeing temporarily inconvienced at the moment, I'll take the liberty of transfering some info and links that SWIJ shared regarding the aromas in question!

smell and taste of
Hydratropic Aldehyde:
http://www.execpc.com/~goodscnt/data/rw1006391.html
It burns if it came intouch of skin or if it is put into mouth. (swims expirience)
Odor Description : Fresh Sharp Green Hyacinth Leaf Lilac

P2P:
http://www.speclab.com/compound/c103797.htm
the stuff that was made had a Pleasant Fragrance.
but wasnt melting at -16?C it was a viscous paste.

Peaceof the reaction
Have FUN-Bee SAFE

Everything Ibee says should be taken with a Large Grain of Sympathomimetic Amine Salt
ÙøÙWareami

Jan1983
(Hive Bee)
08-16-02 09:35
No 345979




Nice to hear. Good boys, i am happy that some ...
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Nice to hear.

Good boys, i am happy that some more are trying the experiments.

I am back to normal, another city a new life and no more amph stuff for me (only experimenting no selling or taking or whatever).

Smell:

First time you smell it it smells ok then you smell a nice odor then i got a headache from smelling it then i got sick from it (5hours of smelling that stuff in low concentracion).

its hard to get rid of the smell. so be safe that no drops are falling down. only thing that was able to get rid of the smell was a shitload of Centrifugal (normaly an antitranspirant) i sprayed it everywhere and after a hour the smell went.

Greets and be/stay safe guys
Chemistry are not only the things that stink. Smile

BooWho
(Hive Bee)
08-20-02 02:14
No 346986




Good to hear from you Jan!!
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Glad you are still among the free bees.

Boo is very happy for you....

What a scare to read your posts when they were closing in....

Very smart to take the path you did...

boo
onewayoranother
I'llgetyaI'llgetyaI'llgetyagetyagetyagetya

bartleby
(Stranger)
04-10-03 20:42
No 425545




distill
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Have you had a chance to compare distilled vs non-distilled in the end product?

RepVip
(Hive Bee)
04-10-03 21:28
No 425553




BooWho MIA
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Don't expect a reply from BooWho - he hasn't been around for awhile.

Maybe some other bee has an answer to your question

<sniff> we miss ya boo

freedom_lover
04-13-03 14:59




That sucks
(Rated as: insignificant)
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UncleFester
(Popular Author)
04-16-03 21:06
No 427452




TRPS source material
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Here's one I have been sitting on for a while. I don't know if it has been covered here. It is my understanding that turpentine replacement paint solvent contains a large amount of cumene. It is easily distilled out to get pure material. Cumene is converted to hydratropic aldehyde in fair yield with CrO3 + HCl. Sounds like a winner to me if TRPS does indeed contain a large amount of cumene.

UncleFester
(Popular Author)
04-17-03 20:31
No 427699




improving 1800's techniques
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The ref for making hydratropic aldehyde from cumene with fair yield dates to the late 1800's. This method could be improved by adding some acetone into the reaction mixture to prevent the chrome from over oxidizing the product. One could then expect to get a "good" yield.

foxy2
(Distinctive Doe)
04-17-03 21:36
No 427713




Fester Thats interesting, do you have the...
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Fester
Thats interesting, do you have the actual reference?

UncleFester
(Popular Author)
04-18-03 16:25
No 427901




damn closed libraries
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It's Easter weekend, so all the college libraries are closed up tight as a drum, however I found the reference in Org Syn. They have a recipe for hydratropic aldehyde which isn't particulary clandestine suitable. It uses sodium metal and other things which you can't pull off the hardware store shelf. At the end of the write up, they list other methods of making hydratropic with the references. One of them was the method using cumene plus chrome and HCl.
The original article is in either german or french as I recall. Wait until Tuesday when the libraries reopen and I'll put up the reference.

Aurelius
(Hive Addict)
04-18-03 17:39
No 427919




Synthesis
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In english, please? I've really got to learn german (... and japanese, latin, spanish...)

lugh
(Moderator)
04-18-03 19:03
No 427944




Hydratropaldehyde
(Rated as: excellent)
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Fortunately, SWIL's library is open, from Organic Syntheses Cumulative Volume III, p 733

Hydratropaldehyde has been prepared by hydrolysis of phenylmethylglycidic ester (1-3), by chromyl chloride oxidation of cumene (4), by the elimination of halogen acid or water from halohydrins or glycols (5-7), and by the distillation at ordinary pressure of methylphenylethylene oxide (8,9).
Hydratropaldehyde has also been prepared by the catalytic addition of hydrogen and carbon monoxide to styrene (10).

1. Claisen Ber 38 703 (1905)
2. Patent DE602816
3. Dutta J Indian Chem Soc 18 235 (1941)
4. v. Miller and Rohde Ber 24 1359 (1889)
5. Bougault Ann Chim Phys (7) 25 548 (1902)
6. Tiffeneau Bull Soc Chim France (3) 27 643 (1902); Comptes Rendus 134 846 (1902), 137 1261 (1903), 142 1538 (1906); Ann Chim Phys ( Cool

10 353 (1907)
7. Stoermer Ber 39 2298 (1905)
8. Klages Ber 38 2298 (1906)
9. Tiffeneau Comptes Rendus 140 1459 (1902); Ann Chim Phys ( Cool

10 192 (1907)
10. Adkins and Krack JACS 70 383 (1948)

In english, please?

Sorry to say it's very doubtful von Miller and Rhode published their paper in English, you'll have to settle for a translation by a hive bee

Cumene (isopropylbenzene) has been synthesized from propylene/isopropanol and benzene Ind Eng Chem 39 154 (1947); JACS 64 1576 (1942); JACS 66 1309 (1944); Bull Chim Soc Fran 12 452 (1945) & JACS 67 2209 (1945); and by alkylation of the hydrocarbon (benzene) by the olefin (propylene) in a solution of aluminum chloride with a nitroparaffin Patent US2385303. Chlorosulfonic acid was used to catalyze the reaction between the aryl hydrocarbon and an aliphatic alcohol JACS 68 191 (1946). Two moles of benzene and 1 mole of 2-chloropropane were reacted for four hours at 25 ? with 75% iron (III) chloride saturated with hydrogen chloride gave 66% isopropylbenzene Comptes Rendus 246 3477 (1958). A preparation from benzene and 1-bromopropane can bee found in Zh Obshch Khim 26 2185 (1956)

Chemistry is our Covalent Bond

algebra
(Stranger)
04-19-03 11:13
No 428070




chromyl chloride
(Rated as: excellent)
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chromyl chloride

K2Cr2O7 + 2HCl -----> 2KCrO3Cl + H2O
2KCrO3Cl + 2H2SO4 -----> CrO3 + CrO2Cl2 + 2KHSO4 + H2O

Peligot's Salt (Potassium chlorochromate): First prepared by the nineteenth century French chemist, Eugene Melchior Peligot (better known as the first chemist to isolate metallic uranium), potassium chlorochromate is a salt of chlorochromic acid in which one of the HO groups of chromic acid has been replaced by chlorine. Thus it is intermediate between chromic acid and chromyl chloride:

To prepare this salt place 6 grams of potassium dichromate in a 100 mL beaker and add 8 grams (6.7 mL) conc. hydrochloric acid and 1 mL water. Warm the mixture gently; if carefully done the dichromate will dissolve without the evolution of chlorine. On cooling the beaker in an ice bath the solution will deposit long orange-red crystals of Peligot's salt, KCrO3Cl:
Eq. 4    K2Cr2O7 + 2HCl -----> 2KCrO3Cl + H2O
An excellent, practically quantitative, yield should be obtained. Dry the crystals on a porous tile and preserve in a tightly stoppered bottle.

Potassium chlorochromate is very stable in air, but is hydrolyzed by water. It dissolves and the solution on evaporation yields potassium dichromate and HCl, the reverse of the reaction in equation 4.

To a milliliter or so of conc. sulfuric acid in a test tube add a small quantity of Peligot's salt. Copious red fumes of chromyl chloride are evolved and condense as a red liquid in the upper part of the tube. Apparently a disproportionation reaction occurs resulting in further chlorination of part of the chromium:
Eq. 5 2KCrO3Cl + 2H2SO4 -----> CrO3 + CrO2Cl2 + 2KHSO4 + H2O
When heated, Peligot's salt parts with all of its chlorine, and on further heating yields chromic oxide, Cr2O3. The salt itself possesses a sharp odor of chlorine.

source: http://www.sas.org/E-Bulletin/2002-08-23/chem/body.html

UncleFester
(Popular Author)
04-19-03 17:09
No 428132




a better recipe
(Rated as: good idea!)
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Inorg Syn, Vol. 2 page 205 has a better recipe using CrO3 and HCl. These are even more readily available industrial chemicals. The thousands of tons of CrO3 used for chrome plating each month make an excellent cover, and the price is now around 90 cents per pound. Check it out. Make note that the chromyl chloride will burn and blister skin, as will CrO3. If any gets on one's self, a good rinse is called for and some sodium metabisulfite(available at brew shops) as a follow up to reduce the chromium to +3 state.

lugh
(Moderator)
04-21-03 15:46
No 428458




Inorganic Syntheses Vol II, p 205-7
(Rated as: excellent)
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63. CHROMYL CHLORIDE [Chromium(VI) Dioxychloride]

Among the more common methods used for the prepara?tion of chromyl chloride are the distillation of a mixture of concentrated sulfuric acid with the solid formed by melting together sodium chloride and an alkali metal chromate or dichromate; the reaction of chromium(VI) oxide with an acid chloride such as phosphorus pentachloride or chloro?sulfonic acid ; and the reaction of chromium(VI) oxide with concentrated hydrochloric acid in the presence of a strong dehydrating agent such as concentrated sulfuric acid. An equivalent quantity of a soluble chromate or dichromate may be substituted in the last procedure. In either case, the third method is convenient and leads to good yields of chromyl chloride.

Procedure
A solution of 150 g. of chromium(VI) oxide (c.p.) in 100 ml. of water is placed in a 1500-m1. three-necked flask fitted with a dropping funnel, a mechanical stirrer, a thermometer, and a tube to carry away the vapors of chromyl chloride and hydrochloric acid. * A mechanical stirrer of the type described on p. 33 of "Organic Syn?theses," Collective Vol. 1, 2d ed., John Wiley & Sons, Inc., New York, 1941, is especially suitable. The reaction should be carried out in a hood since the fumes are offensive and poisonous.
Three hundred thirty milliliters of concentrated hydrochloric acid is added, and the solution is cooled to 0? by an ice-salt mixture. While the solution is stirred, 450 ml. of concentrated sul?furic acid is added drop by drop from the dropping funnel. Ice is added to the cooling bath as needed, and the rate of addition of the sulfuric acid is regulated so that the tem?perature of the reaction mixture does not rise above 15 to 20?. When all the sulfuric acid has been added, the reac?tion mixture is transferred to a separatory funnel. After the two liquid layers have separated, the lower layer of chromyl chloride is drawn off into a glass-stoppered con?tainer. Yield 189 g. (81 per cent).
The product is distilled through an 18-in. Vigreux column. The fraction boiling between 115 and 116? at 735 mm. amounts to 65 per cent of the crude product. Since chromyl chloride reacts with stopcock grease and has a tendency to cause glass joints to stick, ground-glass appara?tus is not recommended for this distillation.
If chromium(VI) oxide is not available, a saturated solu?tion of an equivalent quantity of sodium dichromate is used. In this case, crystallization of white solids (pre?sumably sodium sulfate and chloride) takes place during the reaction. These solids are removed before separation of the chromyl chloride by filtering the reaction mixture through sintered glass or glass wool.
If chromyl chloride is to be kept for any length of time, traces of hydrochloric acid should be removed by bubbling dry air through the liquid. The liquid should be carefully distilled, sealed in glass tubes, and stored in the dark. Even then it sometimes slowly decomposes, with the formation of solids. The boiling range of the remaining liquid, however, indicates that it is still fairly pure chromyl chloride. The upper layer may be disposed of safely by pouring it slowly into 1500 ml. of water, in a 2L beaker, which is stirred continuously during the operation. When the synthesis was checked, a yield of 90 per cent was obtained. The higher yield is believed to be due to the fact that the temperature was kept below 10?.

Properties
Chromyl chloride is a dark-red liquid of density 1.92, boiling point 117? (760 mm.), and freezing point -96.5?. In odor and appearance in the liquid and vapor states it resembles bromine. It hydrolyzes vigorously and fumes in moist air. Chromyl chloride reacts vigorously with ammonia in the vapor or liquid state. It has extremely strong oxidizing properties, inflaming many organic com?pounds. Its solution in carbon tetrachloride is fairly stable.

References
1. Etard: Ann. chim. phys., [5122, 218 (1881).
2. Fry: J. Am. Chem. Soc., 33, 697 (1911).
3. Liebknecht: German patent 524559 (1926); Chem. Abstracts, 25, 4367 (1931).
4. Low and Perkins: J. Chem. Soc., 91, 191 (1907).

Chemistry is our Covalent Bond