"The Cyalume lightstick contains dilute hydrogen peroxide in a
phthalic ester solvent contained in a thin glass ampoule, which is
surrounded by a solution containing a phenyl oxalate ester and the
fluorescent dye 9,10-bis(phenylethynyl)anthracene...When the ampoule is broken, the H2O2 and oxalate ester react.."
Re: How to make chemical light ?
From: chideste@pt.Cyanamid.COM (Dale Chidester) Date: Mon, 13 Mar 1995
The following produce rather spectacular results. Chemicals are
available through Fluka and Aldrich. The dyes are expensive.
Dyes:-
9,10-bis(phenylethynyl)anthracene (BPEA) (yellow) [10075-85-1] Fluka 15146
9,10-diphenylanthracene (DPA) (blue) [1499-10-1] Fluka 42785
5,6,11,12-tetraphenylnaphthacene (rubrene) (red) [517-51-1] Fluka 84027
Other reagents required:-
bis(2-carbopentyloxy-3,5,6-trichlorophenyl)oxalate (CPPO)
[75203-51-9] Aldrich 39,325-8
bis(2-ethylhexyl)phthalate (DOP) (solvent) [117-81-7] Fluka 80032
sodium salicylate (catalyst) [54-21-7] Fluka 71945
35% hydrogen peroxide [7722-84-1] Fluka 95299
Saturate solvent with dye and CPPO. Sonicate to help solvation. Start with
about 50 mg dye (BPEA, DPA or rubrene) in 10 g solvent with 50 mg CPPO and
5 mg sodium salicylate. CPPO is limiting reagent.
Put small quantity (20 drops) in a small vial and add equal volume of
hydrogen peroxide. Mix vigorously. There will be two phases. Avoid skin
contact! Don't cap tightly!
The following explanation of the chemistry was provided:-
From: sbonds@jarthur.claremont.edu (007)
All of the material below is taken from a chemical demonstrations book
[[1], v.1, p.146 ].
The oxidant is hydrogen peroxide contained in a phthalate ester solvent.
The concentration is very low, less than 0.5%. The fluorescing solution
consists of a phenyl oxalate ester and a fluorescent dye. The dye used is
9,10-bis-(phenylethynyl)anthracene (for green) or 9,10-diphenylanthracene
(for blue).
Here is the reaction sequence:
1) (Ph)-O-CO-CO-O-(Ph) + H2O2 --> (Ph)-O-CO-CO-O-OH + (Ph)-OH
2) (Ph)-O-CO-CO-O-OH --> O-O
| | + (Ph)-OH
OC-CO
3) C2O4 + Dye --> Dye* + 2CO2
4) Dye* --> Dye + hv
In 1) The hydrogen peroxide oxidizes the phenyl oxalate ester to a
peroxyacid ester and phenol. The unstable peroxyacid ester decomposes to
the cyclic peroxy compound and more phenol in step 2). The cyclic peroxy
compound is again unstable and gives off energy to the dye as it decomposes
to the very stable carbon dioxide. The dye then radiates this energy as
light.
An alternative chemiluminescence demonstration involves the H2O2 oxidation
of lucigenin ( bis-N-methylacridinium nitrate [2315-97-1] Aldrich B4,920-3 ),
[ [1] v.1 p.180-185 ] which has recently been modified to provide a slow
colour change across the visible spectrum [2]. One of the reagents in that
lucigenin oxidation ( Rhodamine B ) is a mutagen and suspected carcinogen.
18.2 How do hand warmers work?, and how can I make one?
They consist of an aqueous solution of sodium acetate with a small "clicker"
disk to impart a physical shock. The solute is dissolved into solution by
prior warming. when the heat is required, the disk is "clicked" to shock the
solution, and this causes the sodium acetate to crystallise from the now
supersaturated solution. The heat of crystallisation is slowly released.
18.3 What are the chemicals that give fruity aromas?
Most of the desirable food aromas come from low to medium molecular weight
organic compounds - usually alcohols, aldehydes, esters, ketones, and
lactones. These may be " natural " ( extracted from natural sources ),
" nature-identical " ( synthetic, but identical to known natural compounds ),
and " artificial " ( synthetic, not found in nature ). The perceived aroma of
molecules can change dramatically with minor isomeric or structural changes,
and common fruity aromas are usually complex mixtures of several compounds.
Because man-made chemicals are frequently made from chemicals derived from
fossil fuels, the isotopic ratios of the carbon atoms has been used to
discriminate between natural and nature-identical chemicals. Natural
processes usually involve the use of enzymes that selectively produce a
specific isomer, and some man-made aromas are now produced enzymatically.
Chiral chemistry, often utilising chiral chromatography that was initially
developed for pharmaceuticals, is now also being used for the production
and testing of man-made aromas, as enantiomerically-pure aroma chemicals
command premium prices.
Some chemicals are listed below, along with their use in either fragrances
and/or flavours, and boiling point ( 760 mmHg, unless otherwise stated ).
Some of them are also considered toxic, and thus their use may be controlled.
Volume A11 of Ullmann has an excellent monograph on flavours and fragrances,
and more detail can be obtained from the journal Perfumer and Flavorist.
The catalogues of well-known suppliers such as Dragoco GmbH ( Germany ),
L.Givaudin and Cie ( Switzerland ), and Takasago Perfumery Company ( Japan ),
also contain information on chemical composition and health and safety.
Chemical BP CAS RN Application
C (mmHg)
acetoin 148 [513-86-0] butter
acetophenone 202 [98-86-2] orange blossom
benzyl acetate 206 [140-11-4] jasmine
butyl acetate 125 [123-86-4] apple
2,3-butanedione 88 [431-03-8] butter
(+)-carvone 230 [2244-16-8] caraway, dill
(-)-carvone 230 [6485-40-1] spearmint
citral 229 [5392-40-5] lemon
citronellal 207 [2385-77-5] balm mint
decanal 208 [112-31-2] citrus
dihydromyrcenol 78 (1) [18479-58-8] lavender
2,6-dimethyl-2-heptanol 171 [13254-34-7] freesia
ethyl butyrate 120 [105-54-4] pineapple
ethyl 2t-4c-decadienoate 71 (45) [3025-30-7] pear
ethyl hexanoate 168 [123-66-0] pineapple
ethyl isovalerate 132 [108-64-4] blueberry
ethyl 2-methylbutyrate 133 [7452-79-1] apple
geraniol 229 [1066-24-1] roselike
hexyl acetate 169 [142-92-7] pear
hexyl salicylate 168 (12) [6259-76-3] azalea
1-(4-hydroxyphenyl)-3-butanone [5471-51-2] raspberry
isoamyl acetate 143 [123-92-2] banana
(+)-limonene 176 [5989-27-5] lemon
linalool 198 [78-70-6] lily of the valley
linalyl acetate 220 [115-95-7] bergamot
8-mercapto-p-menthan-3-one 57 (8) [38462-22-5] blackcurrant
1-p-methene-8-thiol 40 (1) [71159-90-5] grapefruit
3-methyl-2-cyclopenten-2-ol-1-one [80-71-7] caramel
4-methyl-2(2-methyl-1-propenyl)tetrahydropyran
70 (12) [16490-43-1] rose
myrcenol 78 (50) [543-39-5] lime
2t-6c-nonadien-1-ol 98 (11) [28069-72-9] violet
3-octanol 175 [20296-29-1] mushroom
1-octen-3-ol 84 (25) [3391-86-4] mushroom
phenethyl acetate 238 [103-45-7] rose
phenethyl alcohol 220 [60-12-8] rose
phenethyl isoamyl ether [56011-02-0] chamomile
2-propenyl hexanoate pineapple
alpha-pinene 156 [80-56-8] pine
alpha-terpineol 217 [98-55-5] lilac
alpha-trichloromethylbenzyl acetate [90-17-5] rose
18.4 What is the most obnoxious smelling compound?
Many low molecular weight sulfur-containing compounds tend to induce adverse
reactions in people, even if they have not encountered them before, eg the
glandular emissions of skunk (n-butyl mercaptan, dicrotyl sulfide).
Butyric acid reminds people of vomit, and cadaverine ( 1,5 Pentadiamine )
reminds people of rotten tissue, but without an earlier association, they
may not regard them as unusually obnoxious.
18.5 What is the nicest smelling compound?
Aside from thinking about your stomach, when the smell of cooking foods
is attractive, then most people like the smell of flowers and citrus fruits.
These are volatile, aromatic, oils, whose major components are complex
mixtures of medium volatility compounds, often derived from terpenes, eg
Oil of Rose ( 70 - 75% geraniol = (E)-3,7-dimethyl-2,6-octadiene-1-ol ),
Oil of Bergamot ( 36 - 45% linalyl acetate = 3,7-dimethyl-1,6-octadien-3-yl
acetate ). Many aromatic oils are mixtures of terpene esters ( oil of
geranium = 20 - 35% geraniol esters ) or aldehydes ( oil of lemon grass =
75 - 85% citral = 3,7-dimethyl-2,6-octadienal ). Merck briefly describes
nearly 100 volatile oils, from Oil of Amber to Oil of Yarrow, along with
typical applications. Flower perfumes are complex blends of compounds, and
detailed compositions of your favourite smell are often available in the
journal " Perfumer and Flavorist ".
Expensive flower petal perfumes, such as rose and jasmine, are produced
using extracts obtained by the traditional "enfleurage" process ( refer to
Section 24.4 ).
nn vnlig sjl som skulle kunna verstta detta till "lekmanssvenska"
