T. E. (Thomas Edward) Thorpe.

A dictionary of applied chemistry online

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alcohol with Na amalgam and H^O (Lourenpo,
Annalen, 120, 92). Oxidised by CrO, to chlor-
acetio acid (Kriwaxin, Zeitsch. Chem. 1871,
265) ; with KOH, yields ethylene oxide.

Ethylene chlorobromide CHaCl-CHjBr ; b.p.
107°-108° (Lescoeur, Bull. Soc. chim. [u.] 29,484);
sp.gr. 1-79 at 0° (L.), 1-705 at 11° (Mont-
golfier and Giraud, ibid. 33, 12), 1-689 at 19°.
By action of Br upon CHaCl-CHal (Henry,
Annalen, 156, 14); from CaHjBra and Sbdj
(Lossner, J. pr. Chem. [2] 13. 421) or CaHjBra
and Hgda at 150°-180° (M. and G.) ; by action
of Br upon C2H4C1(0H) at 130° (Demole, Ber. 9,
556). To prepare it, first chlorine and then
ethylene is passed into Br, kept under a mixture
of equal vols, of strong HCl and water (James,
J. pr. Chem. [2] 26, 380; also Simpson, Proo.
Roy. Soc. 27, 118) ; decomposed by alcoholic
KOH, with formation of C^^sCl.

Ethylene chloriodlde CH2CI-CH2I ; m.p.
— 15-6° (Schneider, Zeitsch. physikal. Chem. 19,
157), b.p. 140° (SoroKn, Zeitsch. Chem. 1870, 519),
140-1° (corr.) (Thorpe, Chem. Soc. Trans. 37,
189), 137°-138° (Meyer and Wurster, Ber. 6,
964); sp.gr. 2-151 at 0° (S.), 2-16439 at 0°,
2-13363 at 15-3°/0° (T.). ]?rom CHal-CHjI
and ICl ; from C2H4 and an aqueous solution
of ICl (Simpson, Proc. Roy. Soc. 12, 278).
Decomposed by alcoholic KOH into HI and
C2H3CI; nascent H yields HCl, HI, and C2H4;
moist AgzO at 160° produces glycol (Simpson).
Knely divided silver at 160° yields CjH, and
CHaCl-CHaa (Priedel and SUva, Bull. Soc.
chim. [ii.] 17, 242). Heated with HI solution,
yields C2H4 and CjHiIj (Sorokin).

Ethylene cyanhydrin HO-GHa-CHjGN ; b.p.
220°-222° at 723-5 mm. ; sp.gr. 1-0588 at 0°.
By long digestion of C2H4O (ethylene oxide)
with anhydrous HON at 50°-60° (Erlenmeyer,
Annalen, 191, 273) ; misoible with alcohol and
water ; 100 parts ether dissolve 2-3 parts
C2H4(0H)CN at 15° ; insoluble in CSj. Porms
a chloride with PClj, which boUs at 174°-
176° under 752 mm., and has sp.gr. 1-443 at



376



ETHYL.



18-5° (Henry, BuU. Acad. Roy. Belg. iu. 36,
360).

Ethylene cyanide C2H4(CN)2, Succinonitrih ;
m.p. 64-5° (Nevole and Tsohemiak, Bull. Soc.
chim. [ii.] 30, 101), 51''-52'' (Henry, ibid. 43, 618) ;
b.p. 158''-160° at 20 mm. (Pinner, Ber. 16,
360), 265'»-267° (H.) ; sp.gr. 1-023 at 45°. By
heating on a water-bath CHjBr-CHjjBr with
KCN and alcohol (sp.gr. 0-84) (Simpson, Proc.
Roy. Soo. 10, 574) ; the liquid is filtered from
the KBr, and distilled, when the alcohol is first
removed ; then the distillation is conducted
under diminished pressure ; also is produc^by
electrolysis of potassium oyanaoetate (Moore,^er.
4, 520) ; is a white amorphous mass soluble in
water, chloroform, and alcohol ; slightly in
carbon disulphide and ether ; decomposed when
distilled at ordinary pressure. Decomposed by
heating with KOH or HCl into NHj and
succinic acid ; with AgNO, forms plates of
C2Hi(CN)2,4AgNOs, which is soluble iu water
and alcohol, and explodes when heated (Simpson).

Ethylene diamine NHa-CaHi-NHa ; m.p. S-S"
(Kraut, Annalen, 212, 251); b.p. 116-5°;
sp.gr. 0-902 at IS" (Kraut). By heating
C2H4CI2 or CjjHjBrj with alcoholic NH3 to
100° (Oloez, J. 1863, 468); by distillation of
a0-diaminopropionic acid (Neuberg* and Nei-
mann, Zeitsch. physikal. Chem. 46, 110) ; by
treatment of C2H4(0N)a with Sn and HCl
(Fairley, Annalen, Suppl. 3, 372). 42 grams
of OHaCa-CHaa and 510 o.c. aqueous NH3
are heated for 6 hours to 115°-120° ia a
sealed tube ; the product is then evaporated
until it begins to crystallise, and is then pre-
cipitated with 3 times its volume of absolute
alcohol ; the precipitated C2Hj(NH2)2,2HCl is
then washed with alcohol and the base set free
by distillation with powdered NaOH (Kraut, I.e. ;
also Hofmann, Ber. 4, 666). The by-product
from the manufacture of chloral, consisting of
CHjCa-CHja, CHj-CHaa, &o., can be used. A
thick oily liquid, with faint ammoniacal smell,
soluble in water, not miscible with ether or
benzene ; the aqueous liquid, which contains
C2H4(NH2)2,H20, cannot be freed from water by
BaO, but only by distillation over Na. Caro's
acid oxidises it to glyoxime (Bamberger and Selig-
man, Ber. 36, 3831). With HCIO and HBrO,
yields tetrachloro and tetrabromo derivatives ;
e.g. Br2N-C2Hi-NBr2 (Chattaway, Chem. Soc.
Trans. 1905, 381). Decomposed by HNO2 into
ethylene oxide and Oxalic acid (Hofmann, J.
1859, 386) ; is a strong base and forms salts ;
combines with CS2 to form crystals of

C2H4(NH2)2-0S2,

soluble in water, insoluble in alcohol and ether.
C2H4(NH.).,2HC1. long silvery needles insoluble
in alcohol' " C2H4(NH2)2HCa,Pta4, yellow leaf-
lets, slightly soluble in water (Greiss and Martins,
Annalen, 120, 327) ; C2H4(NH2)2(HCNS)j, large
prisms, very soluble in water, m.p. 145°
(Hofmann, Ber. 5, 245). Forms many com-

Souuds with metallic salts and a periodide
2Hi(NH2)HI-l4, which melts at 218°.
Diethylene diamine, Piperazine

(C2H4)2(NH)2 OE C.H4<3Jg>C8H4 ;

m.p. 104° (Berthelot) ; b.p. 170° (Hofmann, J.
1868, 343), 145°-146° (Berthelot), 140°



(Rosdalsky). R-om ethylene chloride and
alcoholic NH, (doez; Hofmann, Natansou,
Annalen, 98, 291) ; from sodium ethylene
glyooUate and acid derivatives of ethylene
diamine by heating at 250°-350° (D. R. P.
67811); by heating the sodium compound of
s^ro-diacyl ethylene diamine with anhydrous
glycol or ethylene bromide at 200° (D. R. P.
73354) ; by reduction of ethylene oxamide
with zinc-dust and KOH (D. R. P. 66461). (For
other methods of preparation, see D. R. P.
70055, 70056, 73125, 74628, 79121, 98031,
100232.)

Forms a hydrate OjHioNj.OHaO ; m.p. 44°
(Berthelot). Fiperazine is not changed by
heating with HCl or H2SO4 at 200°. With
carbonyl chloride it forms tricarbonyl piperazine.
It forms a periodide C4Hi„N2-2HI-l4,3H20,
m.p. 283°. The anhydrous periodide melts
at 280° (Herz, Ber. 30, 1585). Piperazine
reacts with 2 molecules HBrO to form an additive
compound, which, on treatment with dilute
alkali or piperaziae solution, yields m-dibromo-
piperazine. This latter can form an additive
compound with 2 molecules of HBrO (Chattaway,
Chem. Soc. Trans. 1905, 951). Piperazine reacts
with an excess of EtI at temperature of water-
bath to form triethyl piperazonium iodide ;
m.p. 240°. Colourless needles, insoluble in cold
water, ligroin, OaCls) CeH„ and CS2 ; soluble in
warm alcohol (Van Rijn, Chem. Zentr. 1898,
1, 727) {v. Piperazine).

sym-Diethy\ene diethyldiamine

(C2H4)2(NH-C2H5)2,H20 ;
b.p, 165° (Schmidt and Wichmann, Ber.
24, 3247); from (C2H4)2(NH2)2 and C2H5I,
or from C^HjBrj and NH2-C2H5 (Hofmann, J.
1859, 389) ; from piperazine and an excess of
KEtSOj in aqueous solution (Van Rijn, Chem.
Zentr. 1898, i. 727). It combines with salts of
Cd, Cr, Zn, and Ni.

a£-Diethylene diethyldiamine

NH2-CjH4-N(CaH5)2;
mobile liquid; b.p. 145°; sp. gr. 0-827 at 18-5°/
18-5°; from bromethylphthalimide and diethyl-
amine .with subsequent hydrolysis, yields a
platinochhride, m.p. 230°; an aurocMoride, m.Tp.
161°-163°; and apicrate, m.p. 211° (Ristenpart,
Ber. 1896, 29, 2526).

Triethylene diamine (C2H4)3N2; b.p. 210°;
soluble in water (Hofmann, J. 1868, 343, Harries,
Annalen, 294, 350).

Diethylene triamine

NH2-C2H4-NH-CjH4-NHj ;
b.p. (with slight decomposition) 208°; formed
with other products by action of NHj upon
CjHiBra ; the double salt with PtCl4 being less
soluble than that of triethylene triamine, it can
be separated from that body (Hofmann, J. 1861,
514).

A strongly alkaline liquid miscible with
water and alcohol. Its salts are soluble in water,
less so in alcohol, 2[(C2H4)2NaH5,3Ha]3Pta4
forms golden-yellow needles.

Trietliylene tiiamme

CBH<^g:g:i:>NH;

b.p. 216° (Hofmann, J. 1861, 514); forms salts ;
[(02H4),H,N3,3HCl],PtCl4; long golden-yeUow
needles moderately soluble in water ; with



ETHYL.



377



hydrobromic acid gives (0aH4)aN3H3,3HBr from
aoid solutions ; from weaker acid solution
(0,Hj3N,H„2HBr.

Teiraethylene trlamine (C2Hi)iN3H:s ; by
action of alcoholic NH3 upon C2H4Br2 (Hof-
mann, Ber. 3, 762) ; forms 3 series of salts with
1, 2, or 3 molecules of monobasic acid : the
hydrobromides are amorphous bodies, almost
insoluble in water, alcohol, and ether.

Triethylene tetramine
NHj-CjH^-NH-CjHj-NH-CaHi-NHj ;
m.p. +12"; b.p. 266''-267'' ; sp.gr. 0-9817 at 15° ;
a strongly alkaline syrup from C2H4CI2 and
C2Hj(NH2)2, or from C2H4Br2 and alcoholic NH,
(Hofmann, J. 1861, 519) ; yields

CjHi8Nj-4HCl-2PtCli ;
a yeUow amorphous powder almost insoluble in
water.

Ethylene diformin C2H4(CH02)2; b.p. 174°;
by heating glycol with pure formic acid (Hen-
inger, Ber. 7, 263) ; also by heating oxalic aoid
with glycol (Lorin, BuU. Soc. chim. [ii.] 22, 104).
Decomposed when heated at 220° in sealed tube
into CO 2, CO, HjO, and OaHj.

Ethylene lerrous chloiide G2H4Fea2,2H20 ;
by heating Fedj and ether to 150° (Kachler,
Ber. 2, 510) ; forms prisms fairly soluble in
water. The corresponding compound

C2H4reBr2,2H20
is prepared by leading CaHj into a strong
aqueous solution of !FeBr2 in sunlight (Chojnacki,
Zeitsoh. Chem. 1870, 420) ; forms light-green
deliquescent crystals.

Ethylene iodide CHal-CHjI; m.p. 81°-82°
(Aronstein and Kramps, Ber. 13, 489) ; sp.gr.
2-07 ; from C2H4 and I in sunlight (Faraday,
Gm. 4, 682), also in the shade, especially if
warmed (Regnault, Annalen, 16, 67) ; a mixture
of I and alcohol (absolute) is saturated with
C2H4 with repeated agitation (Semenow, J.
1864, 483).

Crystalline plates or prisms decomposed by
heating ; when warmed wilih alcohol to 70°,
I02H4-OC2H5 is produced ; Hgdj gives in the
cold CaHjICI.and on heating CaHjCla (Maumene',
J. 1869, 345) ; alcoholic KOH converts it into
G^S-al (Regnault, Annalen, 15, 63).

Ethylene iodohydrin CHal-OHaOH; from
C2H4(0H)2 and gaseous HI (Simpson, ibid. 113,
121) r also by heating C2H4(0H)C1 with KI
(Butlerow and Ossokin, ibid. 144, 42).

An oil, b.p. 85725 mm.; sp.gr. 2-1649 at
18-6° (Henry, Ber. 24 Eef. 75).

Ethylene nitrate NO 3CH2-CH2-NO3; b.p. 114°
-116° with explosion (Demjanow, Chem. Zentr.
1899, i. 1064) ; sp.gr. 1-5099 at 4°, 1-4960 at
15°, 1-4860 at 25° (Perkiu). Is formed when
glycol is treated with HNO3 and H2SO4, also by
interaction of CjHj and N2O5 in the cold
(Demjanow) ; an oily liquid which is inflam-
mable, explodes on percussion, and is poisonous;
KOH converts it into alcohol (Henry, Ber. 3,
529; also Champion, Compt. rend. 73, 571).
On reduction yields CH.CHO, C2H4(NH2),, and
H2N-CH2-CH20H.

Ethylene nitrite

02H4(NO)2 or NO2-CH2OH2-NO2 ;
m.p. below -15°; b.p. 96-8°; sp.gr. 1-2156 at
0° Bertoni). Is prepared by distilling glycerol
trinitrite with more than ai equivalent amount



of glycol. Soluble in alcohol to form C2H|,0N0
(Bertoni, Gazz. chim. ital. 15, 353) ; insoluble in
and slowly decomposed' by water. ,
CH,



Ethylene oxide



L>



b.p. 12-5°; sp.gr.



0-8909 at 474°; 0-8824 at 10°/10° (Perkin,
Chem. Soc. Trans. 1893,488). From C2Hi(0H)Cl
and KOH (Wuriz, Annalen, 110, 125 ; Ann.
Chim. Phys. [3] 69, 317); also from C2H4(0H)C1
and C2H4(OH)ONa (Scheitz, Zeitsch. Chem.
1868, 379); also from C2H4I2 and Ag20 at 150°;
from C2H4Br2 and AgjO at 250°; or from
C2H4Br2 and Na20 at 180° (Greene, J. 1877,
522) ; also by treatment of C2H4a(OCaH30)
with KOH (Demole, Annalen, 173, 125); by
dropping chlorethylacetate on to a cooled
mixture of powdered KOH and sand (Boithner,
Monatsh. 16, 666).

A pleasant-smelling liquid miscible with
water ; when heated with water in a closed
tube, yields glycol, and polyethylene glycol.
Has strong basic properties, although not an
alkaline reaction. It combines with acids, and
precipitates metallic hydroxides from solu-
tions of Mg, Al, Fe, aind Cu salts. With-Na
amalgam forms CaHgO. Pt black oxidises it
to glycoUic acid ; PCI5 produces CHjCl-CHjCl
(Wurtz, Ann. Chim. Phys. [3] 69, 317, and
355).

Equal molecules of C2H4O and Br at 0° form
C2H4(OH)Br, C2H4Br2 and other bodies (Demole,
Ber. 9, 47), but 2 molecules CaH40 and 1
molecule Br, on standing, yield large red or
small yellow prisms of (02H40)2Br2 ; m.p.
65° ; b.p. with decomposition at 95° ; they are
insoluble in water, but soluble in alcohol. HjS
or contact with Hg separates the Br and leaves
dioxyethylene (Wurtz, Ann. Chim. Phys. [3] 69,
321). By long contact with ZnClj or KHO, a
polymeride which melts at 56° and is in-
soluble in ether, is produced (Wurtz, Bull.
Soc. chim. [ii.] 29, 530).

CH2-O-CH,

Dioxyethylene, DiethyUne dioxide | I ;

CHj-O-CHs
m.p. 9° ; b.p. 102° ; sp.gr. 1-0482 at 0°. From
(C2H4)20a-Br2, and H^ by contact at ordinary
temperature. The mixture is then distilled,
and distillate rectified over KOH (Wurtz,
Ann. Chim. Phys. [3] 69, 323) ; has no marked
basic properties, but combines slightly with
acetic aoid on heating to 120°. Louren<;o
{ibid. [3] 67, 288) oWained it by heating
C2H4(0H)2 and C2H4Br2 to 160°, but the
product boiled at 95°. Fords an iodide with
2 atoms of I, m.p. 84°, which is decomposed
by water and air, but soluble in benzene ; also a
sulphate and a piorate melting respectively at
100° and 66°. It also forms a compound with
HgCl2, soluble in, but slowly decomposed by,
water (Faworsky, J. Russ. Phys. Chem. Soc.
38, 741 ; Patemb and SpaUino, Atti. R. Acad.
Lincei, [v.] 16, i. 87).

Chlorethylene oxide C2H3CIO ; b.p. 70°-80°.
By long contact of acetylene chloriodide
CHChCHI with 40-50 vols, of water at 200°-
220° (Sabanejeff, Annalen, 216, 268) ; difficultly
soluble in water.

Bromethylene oxide C2H3Br-0 ; b.p. 89°-92°.
From bromoglyool bromhydrin CHBrj-CHjOH
and KOH (Demole, Ber. 9, 51) ; soluble in water.



378



ETHYL.



Ethylene phosphides v. Phosphobus, Okqanio

COMPOTTNDS OF.

Ethylene selenocyanate C2H4(SeCN)is ; m.p.
128° (Proskauer), 138° (Hagelberg, Bar. 23,
1092). lYom CHjBr-CHjBr and alcoholic
KONSe (Proskauer, ibid. 7, 1281). Colourless
needles, insoluble in cold water or ether,
difficultly soluble in hot water or cold al-
cohol ; dissolves unchanged in strong HNO3,
but on heating gives ethylene selenious acid
C2H4(Se03H)2. With alcoholic alkali, yields
ethylene diaelenide (Hagelberg).

methylene disulphide S<^^2;^g2->S ; m.p.

111°-H2°; b.p. 199°-200°; V.d!=4-28 (Huse-
mann, Annalen, 126, 280), From CaHiBrj
and KjS (Crafts, ibid. 124, 110; 128, 220);
also by heating CjHiCS. or G,HjS,Hg with

Crystallises from alcohol in needles or leaflets,
from ether in thick prisms which are volatile at
ordinary temperatures ; combines with Br and
certain salts, but not with NH3 ; oxidised by
HNO3 to (OaHJ^SjOis. The bromide

(C,H4),S,Br.
is a lemon-yellow amorphous body, m.p. 96°,
very unstable; the iodide (CaHJ^Sali, m.p.
132°-133°, forms iron-black monoolinic needles,
insoluble in water. The oxide (C2Hi)2S202 can
also be obtained by decomposition of the chloride
or bromide ; with water, forms crystals which
decompose without fusion on heating, and are
soluble in water, almost insoluble in alcohol.
The peroxide (C2H4)2S20i, obtained by heating
•(GjHJjSj with fuming HNOj to 150° (Crafts,
Annalen, 125, 124), crystallises from strong HNO3
in small crystals which are insoluble in water.

Ethylene hydroxysulphide 02H4(OH)SH
{TUoethylene glycol), from HO-CHaCHja and
alcoholic KHS ; the KCl is filtered ofE and the
filtrate acidified with dilute HCl and evaporated
at 30°-40° (Carius, Annalen, 124, 258). Is a
heavy liquid, almost insoluble in water, soluble
in alcohol ; the salts are fairly soluble in alcohol;
the mercury compound Hg(C2H50S)2 crystallises
from alcohol in needles.

TModiethyUne glycol (C2H40H)2S is formed
when the above compound is heated, HjS being
evolved. It is a crystaUine solid ; m.p. under
60°, soluble in alcohol, insoluble in water, forms
salts and double compounds with metaUie salts.

Ethylene mercaptan C2H4(HS);i ; b.p. 146° ;
sp.gr. 1-123 at 23-5°. From CHaCl-CHaCl (or
bromide, Werner, J. 1862, 424) and alcoholic
KHS (Lowig and Weidmann, Annalen, 36,
322). A colourless liquid, soluble in alcohol
and alkalis, forms insoluble mercaptides with
heavy metals. Pb(C2H4)S2 yellow ; Cu(C2H4)Sa
chrome green. Ethylene dimethyl sulphide
C2H4(SCH8)2, b.p. 183°, from C2H4Br2 and
CH,SNa (Ewerlof, Ber. 4, 716). Ethylene
diethyl stJ^hide CaHi(SC2H5)2, b.p. 210°-213°
(E.) gives on oxidation first (CjH5S0)2C2H4,
m.p. 170°; and next (C2HjS02)2C2H4, m.p.
136-5'' (Beckmann, .J. pr. Chem. [2] 17, 469).

Ethylene thiocaibonates.

1. Ethylene dithiocarhonate CaHjCOSj,
ethylene oxythiocarbonate ; m.p. 31° ; by action
of HNO3 upon C2H4CS3 in the cold (Husemann,
Annalen, 126, 269) ; forms long thin tables,
insoluble in water, soluble in alcohol, ether, and
chloroform.



2. Ethylene trithiocarbonate C2H4CS3 ; m.p.
39-5° (Husemann), 33-4'> (Konowalow), 39°
(Frasetti) ; sp.gr. 1-4768. From CaH4Br2 and
NajCSs in presence of absolute alcohol (Huse-
mann, Annalen, 123, 83) ; by action of water
upon AlBra-CjHiBrj-CSa (Konowalow); by
action of alcoholic KOH upon ethylene xanthate

02H4(S-CS-OEt)2+K:OH

=KS-GO-OEt+02H4CS3+EtOH,

a theoretical yield; it reacts with dil. KOH thus :

C2H4CSa+EtOH-f3KOH

=KS-00-OEt+C2H4S2K2+2H30

(Frasetti, Ber. 38, 488). Forms golden-yellow,
rhombic prisms ; slowly soluble in alcohol,
easily soluble in ether, very soluble in CSj,
CHCI3, and CeHe.

Ethylene thiochlorides (Guthrie, Chem. Soc.
Trans. 1861, 13, 35 ; 1862, 14, 128).

1. Ethylene thiodichloride CJH4SCI2. by pass-
ing CaHj into cooled SCla- ^ ^ liquid with a
smell resembling mustard oil, and is decomposed
on heating.

2. Ethylene dithiodichloride (C2H4)2S2Cl2, by
action of CaHjUpon SaOlaat 100°. A liquid with
a pungent odour.

CMorethylene dithiodichloride (C2H,Cl)2SaCl2 ;
by action of CjHj upon boiling S2CI2 i ^ light-
yeUow liquid with pleasant smell.

Ethylenethlocyanate C2H4(SCN)2; m.p. 90°.
From CHjCl-CHaa and alcohoUc KCNS (Sou-
uensohein, J. 1856, 609 ; Buff, Annalen, 100,
229); CH2Br-CH2Brmay be used with advantage
(Glutz, ibid. 153, 313) ; forms rhombic plates
slightly soluble in cold water, more so in hot,
and in alcohol, decomposed by heat, volatile
in steam ; its vapour excites tears.

EthyUdene acetamide CH3CH(NHC2H30)2 ;
m.p. 169° ; formed by acting on acetamide with
aldehyde ; forms large prisms decomposed by
acids (Tawildarow, Ber. 5, 477).

EthyUdene acetate CH3-CH(C2H302)2 ; b.p.
169° ; sp.gr. 1-061 at 12°. From aldehyde and
(C2H30)20 at 180° (Geuther, Annalen, 106, 249) ;
from aloohoUc C2HJO2K and CH8CHCI-C2H3O2
(Schiff, Ber. 9, 304) ; has » smell like that of
onions, and is decomposed by water into aldehyde
and acetic acid.

EthyUdene azine CH3CH:N-N:CHCHs; b.p.
95°-96° at 760 mm. ; sp.gr. 0-832 at 17°. Pre.
pared by shaking an ethereal solution of aldehyde
with an aqueous solution of hydrazine hydrate.
At 180° it is unchanged, but at a higher tempera-
ture gives ofE nearly aU its N as gas. It is faMy
stable to alkalis, but is hydrolysed by acids into
aldehyde and hydrazine (Curtius and Linkeisen,
J. pr. Chem. 1898, [ii.] 68, 310).

EthyUdene biuret ]SrH<^^^;^|^CH-CH3,

Trigenic acid, by leading HCNO into well-cooled
aldehyde (Liebig and Wohler, Annalen, 59, 296),
crystallises in small prisms, sUghtly soluble in
water, nearly insoluble in alSohol, has a slightly
acid taste. When heated, liberates COj, NH3,
and traces of oollidine CaHuN (Herzig, Monatsh.
2, 398). Is hardly decomposed by NaBrO.
HNO3 decomposes it and liberates cyanurio acid.
The silver compound AgC4H5N302 forms
amorphous precipitate, soluble in boiling water.
EthyUdene bromide CHjCHBrj, b.p. 114°-
115° (Tawildarow, ibid. 176, 12), 109°-110° at
751 mm. (Denzel, ibid. 195, 202), 110-5° at



ETHYL.



379



760 mm. (Ansohutz, ibid. 221, 137), 108°-110°
(oorr.) (Perkin, Chem. Soo. .Trans. 45, 523) ;
b.p. 107°-108<' (V. Meyer and MuUer, J. pr.
Chem. [21 46, 168); sp.gr. 2-129 at 10° (T.),
2-1001 at 17-574°, 2-0891 at 20-5°/4° (Ansohiitz)
2-0822 at 21-5°/4°, 2-1029 at 15°, 2-0854
at 25° (P.). Prom CjHjBr and Br at 170°
(Hofmaim, Proo. Roy. Soo. 10, 619 ; Caventou,
Compt. rend. 52, 1330). Is produced by action
of PCljBrj but not of PBr^ upon aldehyde
(Paternb and Pisati, Ber. 5, 289) ; also by
heating CH2 : CHBr with HBr to 100° (Reboul,
Compt. rend. 70,398). Aheavy liquid; alcoholic
KHS has no action upon it. On heating with
water and PbO to 130°, aldehyde and HBr are
produced (T.). With Sba^ gives CHj-CHCla
(Henry, Bull. Soo. ohim. [ii.] 42, 262).

Ethylidenebromiodide CHsCHBrI ; m.p. below
-20°; b.p. 142°-143°; sp.gr. 2-50 at 1°,
2-452 at 16°. From O^HsBr and HI in the cold
(Ptaundler, J. 1865, 483; Beboul, Annalen,
155, 212); by shaking CH3CHI2 with IBr
solution (Simpson, BuU. Soo. chim. [ii.] 31, 412) ;
decomposed by alcoholic KOH or Ag^O into HI
and CaHaBr ; Br yields CHaCHBra.

Ethylidene chlorobromide CHjCHClBr ; m.p.
16-6° (corr.) (Schneider, Zeitsoh. physikal. Chem.
19, 157) ; b.p. 84°-84-5° at 750 mm., 82-7° at
760 mm. (Stadel, Ber. 15, 2563); sp.gr. 1-667
at 16°. From CjHjBr and concentrated HCl
at 100° (Reboul, Annalen, 155, 215); from
C2H5CI and Br in sunlight (Denzel, ibid. 195,
193). By action of CI upon OaHjBr (Lescceur,
Bull. Soo. ohim. [ii.] 29, 483). Is decomposed at
ordinary temperature by alcoholic KOH on long
standing ; with Ag^O gives aldehyde ; and with
AgCaHjOj forms 8h,CH(C2H,Os,)2 (L.).

EthyUdene chlorlodide CH3CHCII ; b.p.
117°-119° ; sp.gr. 2-054 at 19°. By agitating a
mixture of CHjCHIj and ICl ; formed also from
CHaCHCla and Al-Ij (Simpson, Bull. Soo. chim.
[ii.] 31, 411).

EthyUdene or Ethidene chloride CH3CHCI2 ;
m.p. —101-5° (Schneider, Zeitsoh. physikal.
Chem. 22, 233), b.p. 59-9° (corr.), sp.gr.
1-2044 at 0°, 1-1863 at 12-24°/4° (Thorpe, Chem.
Soc. Trans. 37, 183) ; b.p. 57-4°-g7-6° at 750-9
mm., sp.gr. 1-1743 at 20°/4° (Bruhl, Annalen,
203, 11), 1-2124 at 0°, 1-1805 at 22°/0°; re-
fractive index ^^ (at 24-7°) = 1-405724. R_
= 34-1 (Kanonnikow) ; b.p. 57°-57-7° at 738-7
mm., sp.gr. 1-2013 at 0° (Pribram and Handl,
Monatsh. 2, 650) ; b.p. 56-7°-56-9° at 749-1 mm.,
sp.gr. 1-1895 at 9-8°/4°, 1-11425 at 56-7°/4° (R.
Schiff, Annalen, 220, 96) ; crit. temp. 254-5°
(Pawlewsky, Ber. 16, 2633) ; H.C.p. = 267-1
oals. (Berthelot and Ogier, Bull. Soc. chim. [ii.] 36
68). Prom C2H5CI and CI (Regnault, Annalen,
33, 312) ; from C^HjO and PCI;, (Beilstein). By
action of HCl upon copper acetylene (Sabanejeff,
ibid. 178, 111). Is prepared by passing a
mixture of chlorine and OaHjCl over animal char-
coal heated to 250°-400° (Damoiseau, Bull. Soc,-
ohim. [ii.] 27, 113). Is obtained as a by-product
in the manufacture of chloral. Is decomposed
by alcoholic KOH into HCl and G^B.^Cl. Sodium
produces at 180°-200° hydrogen, acetylene,
ethylene, ethane, and C2H3CI (ToUens,
Annalen, 137, 311). By action of CI, CHjCaa
and CHjCl-CHClj are produced.

Ethylidene dl-iso-nitramine is formed bv the



interaction of C0(Et)2, or COEtMe, and NO, in
CjHjONa. The lead salt is anhydrous and
crystallises in cubes. The dimethyl ether
forms rhombic crystals, and melts at 75°.
The 8«o-nitramine itself is hydrolysed by
mineral acids into aoetaldelyde NHjOH and
oxides of N. With Na amalgam, is reduced to
hydrazine (Traube, Annalen, 300, 120). ,
Ethylidene diethyl ether

CH3-CH(002H5)2 («. AOETAL).

Ethylidene dimethyl ether CH3CH(0CH3)2,
DimRthyl acetal ; b.p. 64-4° (Dancer, Annalen,
132, 240), 62-7°-63-3° at 757-6 mm. (R. Schiff,
ibid. 220, 104) ; sp.gr. 0-8787 at 0°, 0-8690 at 14°,
0-8476 at 25° (D.), 0-8013 at 62-7°/4° (S.) ;
capillarity constant at b.p. a" = 4-092 (Schiff,
Annalen, 223, 74) ; occurs in crude wood spirit
(D. ) : 2 volumes of wood spirit, 1 volume aldehyde,
and J volume of glacial acetic acid are heated to
100° (Alsberg, J. 1864, 485) ; also by oxidation of
CH30HandC2H50HbyMuOjandH2SOi(Wurtz).

Ethylidene methyl propyl ether
CH3-CH(OCH3)(OC3H,);
b.p. 103°-105° (Baohmann, Annalen, 218, 46).

EthyUdene ethyl propyl ether

CH3-CH(OC,H,)(OC3H,);
b.p. 124°-126° (Bachmann, I.e.).

Ethylidene dipropyl ether GH3-CH(OC3H,)2;
b.p. 146°-148°, sp.gr. 0-825 at 22° (Girard, J.
1880, 695).

EthyUdene methyl isohntyl ether
CH3-CH(OCH3)(OC,H,);
b.p. 125°-127° (Claus and Trainer, Ber. 19.
3005; Bachmann, Z.C.).

Ethylidene ethyl isohutyl ethei

CH3-CH(OC2H3)(OC4H,);
b.p. 155° (Claus and Trainer, I.e.).

Ethylidene diisobutyl ether CH3-CH(0C4Hi,)2 ;
b.p. 168°-170, sp.gr. 0-816 at 22° (Claus -and
Trainer, I.e.; Girard, I.e.).

EthyUdene methyl isoamyl ether



Online LibraryT. E. (Thomas Edward) ThorpeA dictionary of applied chemistry → online text (page 89 of 183)