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Functional Food Safety Aspects Symposium
Forschungsberichte DFG 1st Edition Senate Commission
On Food Safety Sklm Digital Instant Download
Author(s): Senate Commission on Food Safety SKLM
ISBN(s): 9783527606429, 3527606424
Edition: 1
File Details: PDF, 4.31 MB
Year: 2004
Language: english
Deutsche
Forschungsgemeinschaft

Functional Food:
Safety Aspects

Symposium

edited by the
Senate Commission on Food Safety
SKLM
Gerhard Eisenbrand (Chairman)

Scientific Secretariat
Sabine Guth, Monika Kemény
and Doris Wolf
Deutsche
Forschungsgemeinschaft
Functional Food:
Safety Aspects
Symposium
Deutsche
Forschungsgemeinschaft

Functional Food:
Safety Aspects

Symposium

edited by the
Senate Commission on Food Safety
SKLM
Gerhard Eisenbrand (Chairman)

Scientific Secretariat
Sabine Guth, Monika Kemény
and Doris Wolf
Deutsche Forschungsgemeinschaft
Geschäftsstelle: Kennedyallee 40, D-53175 Bonn
Postanschrift: D-53170 Bonn
Telefon: ‡ ‡ 49/228/885-1
Telefax: ‡ ‡ 49/228/885-2777
E-Mail: (Internet RFC 822): postmaster@dfg.de
Internet: http://www.dfg.de

This book was carefully produced. Nevertheless, editors, authors and publisher do
not warrant the information contained therein to be free of errors. Readers are
advised to keep in mind that statements, data, illustrations, procedural details or
other items may inadvertently be inaccurate.

Library of Congress Card No.: applied for

A catalogue record for this book is available from the British Library.

Bibliographic information published by Die Deutsche Bibliothek

Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie;
detailed bibliographical data is available in the Internet at http://dnb.ddb.de.

ISBN 3-527-27765-X

c 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Printed on acid-free and chlorine-free paper.
All rights reserved (including those of translation into other languages). No part of this
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not specifically marked as such, are not to be considered unprotected by law.
Cover Design and Typography: Dieter Hüsken
Composition: Hagedorn Kommunikation, Viernheim
Printing: betz-druck gmbh, Darmstadt
Bookbinding: J. Schäffer GmbH & Co. KG, Grünstadt
Printed in the Federal Republic of Germany
Inhaltsverzeichnis

Vorwort . . . . . . . . . . . . . . . . . . . . . . . . . . . . . XI
Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . XIII
I Hauptschlussfolgerungen und Empfehlungen . . . . . . . . . . . 1
1 Einleitung . . . . . . . . . . . . . . . . . . . . . . . . . . 1
2 Allgemeine Aspekte der Sicherheitsbewertung . . . . . . . . . 3
3 Spezielle Aspekte der Sicherheitsbewertung . . . . . . . . . . 4
4 Erkenntnislücken und Empfehlungen zum Forschungsbedarf für
die Sicherheitsbewertung . . . . . . . . . . . . . . . . . . . 6
5 Literatur . . . . . . . . . . . . . . . . . . . . . . . . . . . 8
II Kriterien zur Beurteilung Funktioneller Lebensmittel . . . . . . . 9
1 Vorbemerkung . . . . . . . . . . . . . . . . . . . . . . . . 9
2 Abgrenzung von Funktionellen Lebensmitteln gegenüber
anderen Lebensmitteln und Produkten . . . . . . . . . . . . 10
3 Bewertung der gesundheitlichen Unbedenklichkeit . . . . . . 11
4 Funktionalität und Auslobung . . . . . . . . . . . . . . . . . 15
5 Beobachtung nach Markteinführung . . . . . . . . . . . . . . 17
6 Schlussbemerkung . . . . . . . . . . . . . . . . . . . . . . 17
7 Literatur . . . . . . . . . . . . . . . . . . . . . . . . . . . 17
III Main Conclusions and Recommendations . . . . . . . . . . . . . 19
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . 19
2 General Aspects of the Safety Evaluation . . . . . . . . . . . 21
3 Special Aspects of the Safety Evaluation . . . . . . . . . . . . 22
4 Gaps in Knowledge and Recommendations for Research for the
Safety Evaluation . . . . . . . . . . . . . . . . . . . . . . . 23
5 References . . . . . . . . . . . . . . . . . . . . . . . . . . 25

V
 Inhaltsverzeichnis

IV Criteria for the Evaluation of Functional Foods . . . . . . . . . . 27

1 Preamble . . . . . . . . . . . . . . . . . . . . . . . . . . . 27
2 Differentiation of Functional Foods From Other Foodstuffs and
Products . . . . . . . . . . . . . . . . . . . . . . . . . . . 28
3 Evaluation of the Safety to Health . . . . . . . . . . . . . . . 29
4 Functionality and Claims . . . . . . . . . . . . . . . . . . . 32
5 Observation after the Market Introduction . . . . . . . . . . . 34
6 Concluding Remarks . . . . . . . . . . . . . . . . . . . . . 34
7 References . . . . . . . . . . . . . . . . . . . . . . . . . . 35
V Contributions . . . . . . . . . . . . . . . . . . . . . . . . . . 37
1 Diet, Genes, and Cancer Risk . . . . . . . . . . . . . . . . . 37
Cornelia M. Ulrich
2 Regulatory Requirements for Functionality and Safety:
A European View . . . . . . . . . . . . . . . . . . . . . . 50
Burckhard Viell
3 Functional Foods Research and Regulation in Japan . . . . . . 67
Shaw Watanabe
4 Aspect on the Chinese Functional Food and their Safety . . . . 85
Yi-Min Wei
5 Regulatory Framework for Functionality and Safety:
A North American Perspective . . . . . . . . . . . . . . . . 90
Barbara O. Schneeman
6 Dose-Response Relationships with Special Reference to
Antioxidants . . . . . . . . . . . . . . . . . . . . . . . . . 98
Aalt Bast and Guido R. M. M. Haenen
7 Low Dose Competition of Flavonoids with Endogenous Thyroid
Transport Proteins: Potential Relevance to the Thyroid Hormone
Axis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 112
Josef Köhrle
8 Host Factors Relevant for Bioavailability: Transporters,
Metabolizing Enzymes and Genetic Polymorphisms . . . . . . 137
Dieter Schrenk
9 Food Matrix and Related Factors Affecting Bioavailability . . . 144
Karin H. van het Hof and Johan M. M. van Amelsvoort
10 Toxicokinetics/Toxicodynamics . . . . . . . . . . . . . . . . 152
Ron Walker
11 Biomarkers to Assess Safety Aspects and Functional Effects of
Food . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164
Beatrice L. Pool-Zobel
12 Biomarkers Relevant to Cardiovascular Disease . . . . . . . . 178
Margreet R. Olthof
13 Biomarkers of Effect on the Immune System . . . . . . . . . . 179
Raymond Pieters

VI
 Inhaltsverzeichnis

14 Mechanistic Understanding of Potential Adverse Effects of

b-Carotene Supplementation . . . . . . . . . . . . . . . . . 189
Xiang-Dong Wang
15 Potential Adverse Mechanisms of Antioxidants During Cancer
Therapy . . . . . . . . . . . . . . . . . . . . . . . . . . . 216
Hans Konrad Biesalski
16 Cholesterol Lowering Vegetable Oil Spreads: Results of a Post
Launch Monitoring Programme . . . . . . . . . . . . . . . . 217
Linda J. Lea
17 Effect of Flavonoids on Human Topoisomerases . . . . . . . . 231
Doris Marko
18 Risk/Benefit Aspects of Phytoestrogen Consumption . . . . . . 237
Catherine Boyle
19 Influence of Phytoestrogens on the Biotransformation of
Endogenous Estrogens . . . . . . . . . . . . . . . . . . . . 238
Manfred Metzler
20 How Selective are Prebiotics? . . . . . . . . . . . . . . . . . 247
Walter P. Hammes
21 Pathogen or Probiotic – Where is the Boundary? . . . . . . . . 264
Maria Saarela

VI Posters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 279
1 In vitro Study of Prebiotic Properties of Levan-Type Exopoly-
saccharides from Lactobacilli and non-Digestible Carbohydrates
using Denaturing Gradient Gel Electrophoresis . . . . . . . . 279
F. Dal Bello, J. Walter, C. Hertel, and W. P. Hammes
2 Effects of Butyrate on Glutathione S-Transferase P1 Expression
in Human Colonic Adenoma Cells . . . . . . . . . . . . . . 281
G. Festag, N. Haag, G. Beyer-Sehlmeyer, M. N. Ebert,
B. Marian and B. L. Pool-Zobel
3 In vitro Fermentation Supernatants of Inulin-associated
Prebiotics Modulate Proliferation and Glutathione S-Transferase
Activity in Human Colon HT29 Cells . . . . . . . . . . . . . 284
Eva Gietl, Annett Klinder, Stella Pistoli, Beatrice Pool-Zobel
4 b-Carotene Effects in a Tobacco Smoke Carcinogen-induced
Lung Cancer Model in vivo . . . . . . . . . . . . . . . . . . 289
R. Goralczyk, H. Bachmann, G. Riss, C.-P. Aebischer, B. Lenz,
and K. Wertz
5 Influence of Daidzein and its Metabolites on the Expression of
Catalase in Rat Hepatoma Cells . . . . . . . . . . . . . . . . 293
A. Kampkötter, E. Röhrdanz, K. Iwami, S. Ohler, W. Wätjen,
Y. Chovolou, S. E. Kulling, and R. Kahl1
6 Flavonoids and the Central Nervous System: The Anxiolytic
Flavone Hispidulin . . . . . . . . . . . . . . . . . . . . . . 299
D. Kavvadias, P. Sand, P. Riederer, E. Richling, P. Schreier

VII
 Inhaltsverzeichnis

7 Comparative Bioavailability of Synthetic and Tomato-Based

Lycopene in Humans? . . . . . . . . . . . . . . . . . . . . 303
Peter P. Hoppe, Klaus Kraemer, Henk van den Berg, Gery
Steenge, Trinette van Vliet
8 The Mycotoxin Ochratoxin A Induced DNA Damage in MDCK
Cells and Primary Cultured Porcine Urinary Bladder Epithelial
Celles (PUBEC) in vitro . . . . . . . . . . . . . . . . . . . . 308
S. Lebrun, H. Schulze, and W. Föllmann
9 Genotoxic Potential of the Phytoestrogen Resveratrol in Cultured
V79 Chinese Hamster Fibroblasts . . . . . . . . . . . . . . . 315
Leane Lehmann, Erika Pfeiffer, and Manfred Metzler
10 Investigation of Oxidative Stress in H4IIE Cells: Modulation by
the Flavonoid Kaempferol . . . . . . . . . . . . . . . . . . . 319
P. Niering, W. Wätjen, S. Ohler, I. Köhler, Y. Chovolou,
A. Kampkötter, Q.-H. Tran-Thi, and R. Kahl
11 In Vitro Studies on the Estrogenic Activity and the Metabolism
of Curcumin . . . . . . . . . . . . . . . . . . . . . . . . . 325
Erika Pfeiffer, Harald L. Esch, Simone Höhle, Aniko M. Solyom,
Barbara N. Timmermann and Manfred Metzler
12 Structural Studies of Sphingolipids, a Class of Chemopreventive
Compounds in Food . . . . . . . . . . . . . . . . . . . . . 329
W. Seefelder, N. Bartke, T. Gronauer, S. Fischer, H.-U. Humpf
13 Modulation of (Oxidative) DNA Damage by Constituents of
Carob Fibre . . . . . . . . . . . . . . . . . . . . . . . . . 334
S. Schäfer, H. G. Kamp, C. Müller, B. Haber, G. Eisenbrand,
C. Janzowski
14 Pro- and Antiapoptotic Effects of Flavonoids in H4IIE-Cells:
Implication of Oxidative Stress . . . . . . . . . . . . . . . . 338
W. Wätjen, Y. Chovolou, P. Niering, A. Kampkötter,
Q.-H. Tran-Thi, and R. Kahl
15 Analysis of the Hypotheses on b-Carotene/Tobacco Smoke
Interactions in the A/J Mouse Lung Cancer Model . . . . . . . 345
Goralczyk, R., Wertz, K., Riss, G., Bachmann, H., Buchwald,
P., Hansen, T., Niehof, M., Dangers, M., and Borlak J.
16 Carob Fibre – Functional Effects on Human Colon Cell Line
HT29 . . . . . . . . . . . . . . . . . . . . . . . . . . . . 346
Stefanie Klenow, Michael Glei, Gabriele Beyer-Sehlmeyer,
Bernd Haber, Beatrice L. Pool-Zobel
17 Influence of Food Constituents on Cytochrome P450 1A Activity 351
Annette Baumgart, Melanie Schmidt, Hans-Joachim Schmitz,
and Dieter Schrenk
18 Red Grape Products and Ethanol Modulate Coagulation and
Fibrinolysis in Healthy Male Volunteers . . . . . . . . . . . . 355
Achim Bub, Bernhard Watzl, Gerhard Rechkemmer

VIII
 Inhaltsverzeichnis

19 Long-Term Treatment with a Prebiotic Modulates the

Gut-Associated Immune System of Azoxymethane-Treated
F344 Rats . . . . . . . . . . . . . . . . . . . . . . . . . . 356
M. Roller, G. Caderni, G. Rechkemmer, B. Watzl
20 b-Carotene Inhibits Growth of Human Colon Carcinoma Cells
(HT 29) in vitro by Induction of Apoptosis . . . . . . . . . . . 357
Karlis Briviba, Kerstin Schnäbele, Elke Schwertle, Gerhard
Rechkemmer
21 The Influence of Short-Chain Fatty Acids on Intracellular pH
and Calcium-Concentration in the HT-29 Colon Carcinoma Cell
Line . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 358
Kerstin Rebscher, Stephan W. Barth, Gerhard Rechkemmer
22 Effect of Short Chain Fatty Acids on Cytotoxicity, Proliferation,
and Apoptosis in Human Colon Carcinoma Cell Lines . . . . . 359
Silvia Roser, Heike Lang, Gerhard Rechkemmer
23 Investigation of the Antihormonal Potential of Xanthohumol, the
Major Prenylated Flavonoid of Humulus Lupulus . . . . . . . . 361
Anette Höll, Sabine Guth, Gerhard Eisenbrand
24 Anthocyanidins Potently Interfere with Signalling Cascades
Regulating Cell Proliferation . . . . . . . . . . . . . . . . . 368
Doris Marko, Monika Kemény, Michael Habermeyer, Edda
Bernardy, Susanne Meiers, Ulrike Weyand

VII Participants and Contributors of the Symposium . . . . . . . . . 377

IX
Vorwort

Der Begriff „Funktionelle Lebensmittel“ wird für solche Lebensmittel ver-

wendet, für die über den reinen Ernährungszweck hinaus, gesundheitlich
vorteilhafte Wirkungen beansprucht werden. Solche „Funktionellen Lebens-
mittel“ (FLM) dürfen keine unerwünschten, gesundheitlich nachteiligen
Effekte auslösen. Daher ist eine wissenschaftlich fundierte Sicherheitsbewer-
tung als integraler Bestandteil einer Risiko/Nutzen-Analyse unerlässlich. Die
gesundheitliche Unbedenklichkeit muss hinreichend belegt sein, bevor
Untersuchungen zur Funktionalität am Menschen durchgeführt werden kön-
nen.
Rechtliche Regelungen für das Inverkehrbringen von FLM existieren in
Deutschland und anderen europäischen Ländern bisher nicht. Allerdings
bestehen in einigen europäischen Staaten, z. B. in Schweden, dem Vereinig-
ten Königreich oder den Niederlanden, bereits rechtsähnliche Vereinbarun-
gen („Codes of Practice“), bzw. befinden sich solche in Vorbereitung, in
denen insbesondere die Verwendung gesundheitsbezogener Auslobungen
und deren wissenschaftlicher Beleg überprüft werden.
Die Senatskommission der Deutschen Forschungsgemeinschaft (DFG)
zur Beurteilung der gesundheitlichen Unbedenklichkeit von Lebensmitteln
(SKLM) hat vom 5. bis 7. Mai 2002 unter Beteiligung von Experten aus
dem In- und Ausland ein Symposium zu „Funktionellen Lebensmitteln“
abgehalten, bei dem der thematische Schwerpunkt auf den Sicherheitsas-
pekten lag. Ziel war eine kritische Bestandsaufnahme und Bewertung des
gegenwärtigen Erkenntnisstands. In Wahrnehmung ihres Beratungsauftrags
hat die SKLM hierzu Schlussfolgerungen und Empfehlungen erarbeitet. Die
SKLM hat darüber hinaus als Resultat gründlicher wissenschaftlicher Bera-
tungen und unter Auswertung der Ergebnisse des Symposiums „Kriterien
zur Beurteilung Funktioneller Lebensmittel“ erarbeitet (Teil II), die in Ver-
bindung mit den Symposiumsbeiträgen (Teil V) sowie den Hauptschlussfol-
gerungen und Empfehlungen (Teil I) in diesem Symposiumsband veröffent-
licht werden.
Mein Dank gilt den Teilnehmern des Symposiums für ihre wissenschaft-
lichen Beiträge sowie den Mitgliedern und Gästen der Senatskommission für
ihre Mithilfe bei der Abfassung der vorliegenden Veröffentlichung. Beson-

XI
 Vorwort

ders zu danken ist der Arbeitsgruppe „Funktionelle Lebensmittel“ für die

Erarbeitung der „Kriterien zur Beurteilung Funktioneller Lebensmittel“. Die
SKLM vertraut darauf, dass die hier vorgelegten Schlussfolgerungen und
Empfehlungen in Verbindung mit den „Kriterien zur Beurteilung funktionel-
ler Lebensmittel“ auf breite Beachtung stoßen werden.
Das wissenschaftliche Sekretariat der SKLM mit Dr. S. Guth, Dr. M.
Kemény und Dr. D. Wolf hat wesentlich zum Zustandekommen dieses
Bandes beigetragen. Ihnen gilt mein herzlicher Dank, ebenso der Leiterin
des Fachreferats Frau Dr. H. Velke und dem Lektorat der Deutschen
Forschungsgemeinschaft. Die SKLM dankt der Deutschen Forschungs-
gemeinschaft dafür, dass sie dieses Symposium und die Veröffentlichung er-
möglicht hat.

Prof. Dr. Gerhard Eisenbrand

Vorsitzender der DFG-Senatskommission
zur Beurteilung der gesundheitlichen Unbedenklichkeit
von Lebensmitteln

XII
Random documents with unrelated
content Scribd suggests to you:
hydrocarbons, &c., proceeds otherwise at lower
temperatures, as we will now consider.
A very important epoch in the history of chemistry
was inaugurated by the discovery of Dumas and
Laurent that chlorine is able to displace and replace
hydrogen. This discovery is important from the fact
that chlorine proved to be an element which
combines with great ease simultaneously with both
the hydrogen and the element with which the
hydrogen was combined. This clearly proved that
there is no opposite polarity between elements
forming stable compounds. Chlorine does not
combine with hydrogen because it has opposite
properties, as Dumas and Laurent stated previously,
accounting hydrogen to be electro-positive and
chlorine electro-negative; this is not the reason of
their combining together, for the same chlorine which
combines with hydrogen is also able to replace it
without altering many of the properties of the
resultant substance. This substitution of hydrogen by
chlorine is termed metalepsis. The mechanism of this
substitution is very constant. If we take a hydrogen
compound, preferably a hydrocarbon, and if chlorine
acts directly on it, then there is produced on the one
hand hydrochloric acid and on the other hand a
compound containing chlorine in the place of the
hydrogen—so that the chlorine divides itself into two
equal portions, one portion is evolved as hydrochloric
acid, and the other portion takes the place of the
hydrogen thus liberated. Hence this metalepsis is
always accompanied by the formation of hydrochloric
acid.[22] The scheme of the process is as follows:
Cn H m X + Cl2 = Cnm-1ClX + HCl
Free Product of Hydrochloric
Hydrocarbon
chlorine metalepsis acid
Or, in general terms—
RH+ Cl2 =RCl+HCl.
The conditions under which metalepsis takes place
are also very constant. In the dark chlorine does not
usually act on hydrogen compounds, but the action
commences under the influence of light. The direct
action of the sun's rays is particularly propitious to
metalepsis. It is also remarkable that the presence of
traces of certain substances,[23] especially of iodine,
aluminium chloride, antimony chloride, &c., promotes
the action. A trace of iodine added to the substance
subjected to metalepsis often produces the same
effect as sunlight.[24]
If marsh gas be mixed with chlorine and the
mixture ignited, then the hydrogen is entirely taken
up from the marsh gas and hydrochloric acid and
carbon formed, but there is no metalepsis.[25] But if a
mixture of equal volumes of chlorine and marsh gas
be exposed to the action of diffused light, then the
greenish yellow mixture gradually becomes
colourless, and hydrochloric acid and the first
product of metalepsis—namely, methyl chloride—are
formed:
CH4 + Cl2 = CH3Cl + HCl
Marsh Methyl Hydrochloric
Chlorine
gas chloride acid
The volume of the mixture remains unaltered. The
methyl chloride which is formed is a gas. If it be
separated from the hydrochloric acid (it is soluble in
acetic acid, in which hydrochloric acid is but sparingly
soluble) and be again mixed with chlorine, then it
may be subjected to a further metalepsical
substitution—the second atom of hydrogen may be
substituted by chlorine, and a liquid substance,
CH2Cl2, called methylene chloride, will be obtained.
In the same manner the substitution may be carried
on still further, and CHCl3, or chloroform, and lastly
carbon tetrachloride, CCl4, will be produced. Of these
substances the best known is chloroform, owing to
its being formed from many organic substances (by
the action of bleaching powder) and to its being used
in medicine as an anæsthetic; chloroform boils at 62°
and carbon tetrachloride at 78°. They are both
colourless odoriferous liquids, heavier than water.
The progressive substitution of hydrogen by chlorine
is thus evident, and it can be clearly seen that the
double decompositions are accomplished between
molecular quantities of the substance—that is,
between equal volumes in a gaseous state.
Carbon tetrachloride, which is obtained by the
metalepsis of marsh gas, cannot be obtained directly
from chlorine and carbon, but it may be obtained
from certain compounds of carbon—for instance,
from carbon bisulphide—if its vapour mixed with
chlorine be passed through a red-hot tube. Both the
sulphur and carbon then combine with the chlorine.
It is evident that by ultimate metalepsis a
corresponding carbon chloride may be obtained from
any hydrocarbon—indeed, the number of chlorides of
carbon CnCl2m already known is very large.
As a rule, the fundamental chemical characters of
hydrocarbons are not changed by metalepsis; that is,
if a neutral substance be taken, then the product of
metalepsis is also a neutral substance, or if an acid
be taken the product of metalepsis also has acid
properties. Even the crystalline form not unfrequently
remains unaltered after metalepsis. The metalepsis
of acetic acid, CH3·COOH, is historically the most
important. It contains three of the atoms of the
hydrogen of marsh gas, the fourth being replaced by
carboxyl, and therefore by the action of chlorine it
gives three products of metalepsis (according to the
amount of the chlorine and conditions under which
the reaction takes place), mono-, di-, and tri-
chloracetic acids—CH2Cl·COOH, CHCl2·COOH, and
CCl3·COOH; they are all, like acetic acid, monobasic.
The resulting products of metalepsis, in containing
an element which so easily acts on metals as
chlorine, possess the possibility of attaining a further
complexity of molecules of which the original
hydrocarbon is often in no way capable. Thus on
treating with an alkali (or first with a salt and then
with an alkali, or with a basic oxide and water, &c.)
the chlorine forms a salt with its metal, and the
hydroxyl radicle takes the place of the chlorine—for
example, CH3·OH is obtained from CH3Cl. By the
action of metallic derivatives of hydrocarbons—for
example, CH3Na—the chlorine also gives a salt, and
the hydrocarbon radicle—for instance, CH3—takes
the place of the chlorine. In this, or in a similar
manner, CH3·CH3, or C2H6 is obtained from CH3Cl and
C6H5·CH3 from C6H6. The products of metalepsis also
often react on ammonia, forming hydrochloric acid
(and thence NH4Cl) and an amide; that is, the
product of metalepsis, with the ammonia radicle NH2,
&c. in the place of chlorine. Thus by means of
metalepsical substitution methods were found in
chemistry for an artificial and general means of the
formation of complex carbon compounds from more
simple compounds which are often totally incapable
of direct reaction. Besides which, this key opened the
doors of that secret edifice of complex organic
compounds into which man had up to then feared to
enter, supposing the hydrocarbon elements to be
united only under the influence of those mystic
forces acting in organisms.[26]
It is not only hydrocarbons which are subject to
metalepsis. Certain other hydrogen compounds,
under the action of chlorine, also give corresponding
chlorine derivatives in exactly the same manner; for
instance, ammonia, caustic potash, caustic lime, and
a whole series of alkaline substances.[27] In fact, just
as the hydrogen in marsh gas can be replaced by
chlorine and form methyl chloride, so the hydrogen
in caustic potash, KHO, ammonia, NH3, and calcium
hydroxide, CaH2O2 or Ca(OH)2, may be replaced by
chlorine and give potassium hypochlorite, KClO,
calcium hypochlorite, CaCl2O2, and the so-called
chloride of nitrogen, NCl3. For not only is the
correlation in composition the same as in the
substitution in marsh gas, but the whole mechanism
of the reaction is the same. Here also two atoms of
chlorine act: one takes the place of the hydrogen
whilst the other is evolved as hydrochloric acid, only
in the former case the hydrochloric acid evolved
remained free, and in the latter, in presence of
alkaline substances, it reacts on them. Thus, in the
action of chlorine on caustic potash, the hydrochloric
acid formed acts on another quantity of caustic
potash and gives potassium chloride and water, and
therefore not only KHO + Cl2 = HCl + KClO, but also
KHO + HCl = H2O + KCl, and the result of both
simultaneous phases will be 2KHO + Cl2 = H2O + KCl
+ KClO. We will here discuss certain special cases.
The action of chlorine on ammonia may either
result in the entire breaking up of the ammonia, with
the evolution of gaseous nitrogen, or in a product of
metalepsis (as with CH4). With an excess of chlorine
and the aid of heat the ammonia is decomposed,
with the disengagement of free nitrogen.[28] This
reaction evidently results in the formation of sal-
ammoniac, 8NH3 + 3Cl2 = 6NH4Cl + N2. But if the
ammonium salt be in excess, then the reaction takes
the direction of the replacement of the hydrogen in
the ammonia by chlorine. The principal result is that
NH3 + 3Cl2 forms NCl3 + 3HCl.[29] The resulting
product of metalepsis, or chloride of nitrogen, NCl3,
discovered by Dulong, is a liquid having the property
of decomposing with excessive ease not only when
heated, but even under the action of mechanical
influences, as by a blow or by contact with certain
solid substances. The explosion which accompanies
the decomposition is due to the fact that the liquid
chloride of nitrogen gives gaseous products, nitrogen
and chlorine.[29 bis]
Chloride of nitrogen is a yellow oily liquid of sp. gr.
1·65, which boils at 71°, and breaks up into N + Cl3
at 97°. The contact of phosphorus, turpentine, india-
rubber, &c. causes an explosion, which is sometimes
so violent that a small drop will pierce through a
thick board. The great ease with which chloride of
nitrogen decomposes is dependent upon the fact
that it is formed with an absorption of heat, which it
evolves when decomposed, to the amount of about
38,000 heat units for NCl3, as Deville and
Hautefeuille determined.
Chlorine, when absorbed by a solution of caustic
soda (and also of other alkalis) at the ordinary
temperature, causes the replacement of the
hydrogen in the caustic soda by the chlorine, with
the formation of sodium chloride by the hydrochloric
acid, so that the reaction may be represented in two
phases, as described above. In this manner, sodium
hypochlorite, NaClO, and sodium chloride are
simultaneously formed: 2NaHO + Cl2 = NaCl +
NaClO + H2O. The resultant solution contains NaClO
and is termed ‘eau de Javelle.’ An exactly similar
reaction takes place when chlorine is passed over dry
hydrate of lime at the ordinary temperature:
2Ca(HO)2 + 2Cl2 = CaCl2O2 + CaCl2 + 2H2O. A
mixture of the product of metalepsis with calcium
chloride is obtained. This mixture is employed in
practice on a large scale, and is termed ‘bleaching
powder,’ owing to its acting, especially when mixed
with acids, as a bleaching agent on tissues, so that it
resembles chlorine in this respect. It is however
preferable to chlorine, because the destructive action
of the chlorine can be moderated in this case, and
because it is much more convenient to deal with a
solid substance than with gaseous chlorine.
Bleaching powder is also called chloride of lime,
because it is obtained from chlorine and hydrate of
lime, and contains[30] both these substances. It may
be prepared in the laboratory by passing a current of
chlorine through a cold mixture of water and lime
(milk of lime). The mixture must be kept cold, as
otherwise 3Ca(ClO)2 passes into 2CaCl2 + Ca(ClO3)2.
In the manufacture of bleaching powder in large
quantities at chemical works, the purest possible
slaked lime is taken and laid in a thin layer in large
flat chambers, M (whose walls are made of Yorkshire
flags or tarred wood, on which chlorine has no
action), and into which chlorine gas is introduced by
lead tubes. The distribution of the plant is shown in
the annexed drawing (fig. 67).

Fig. 67.—Apparatus for the manufacture of

bleaching powder (on a small scale) by the
action of chlorine, which is generated in the
vessels C, on lime, which is charged into M.
The products of the metalepsis of alkaline
hydrates, NaClO and Ca(ClO)2, which are present in
solutions of ‘Javelle salt’ and bleaching powder (they
are not obtained free from metallic chlorides), must
be counted as salts, because their metals are
capable of substitution. But the hydrate HClO
corresponding with these salts, or hypochlorous acid,
is not obtained in a free or pure state, for two
reasons: in the first place, because this hydrate, as a
very feeble acid, splits up (like H2CO3 or HNO3) into
water and the anhydride, or chlorine monoxide, Cl2O
= 2HClO - H2O; and, in the second place, because, in
a number of instances, it evolves oxygen with great
facility, forming hydrochloric acid: HClO = HCl + O.
Both hypochlorous acid and chlorine monoxide may
be regarded as products of the metalepsis of water,
because HOH corresponds with ClOH and ClOCl.
Hence in many instances bleaching salts (a mixture
of hypochlorites and chlorides) break up, with the
evolution of (1) chlorine, under the action of an
excess of a powerful acid capable of evolving
hydrochloric acid from sodium or calcium chlorides,
and this takes place most simply under the action of
hydrochloric acid itself, because (p. 462) NaCl +
NaClO + 3HCl = 2NaCl + HCl + Cl2 + H2O; (2)
oxygen, as we saw in Chapter III.—The bleaching
properties and, in general, oxidising action of
bleaching salts is based on this evolution of oxygen
(or chlorine); oxygen is also disengaged on heating
the dry salts—for instance, NaCl + NaClO = 2NaCl +
O; (3) and, lastly, chlorine monoxide, which contains
both chlorine and oxygen. Thus, if a little sulphuric,
nitric, or similar acid (not enough to liberate
hydrochloric acid from the CaCl2) be added to a
solution of a bleaching salt (which has an alkaline
reaction, owing either to an excess of alkali or to the
feeble acid properties of HClO), then the
hypochlorous acid set free gives water and chlorine
monoxide. If carbonic anhydride (or boracic or a
similar very feeble acid) act on the solution of a
bleaching salt, then hydrochloric acid is not evolved
from the sodium or calcium chlorides, but the
hypochlorous acid is displaced and gives chlorine
monoxide,[31] because hypochlorous acid is one of
the most feeble acids. Another method for the
preparation of chlorine monoxide is based on these
feeble acid properties of hypochlorous acid. Zinc
oxide and mercury oxide, under the action of
chlorine in the presence of water, do not give a salt
of hypochlorous acid, but form a chloride and
hypochlorous acid, which fact shows the incapacity
of this acid to combine with the bases mentioned.
Therefore, if such oxides as those of zinc or mercury
be shaken up in water, and chlorine be passed
through the turbid liquid,[32] a reaction occurs which
may be expressed in the following manner: 2HgO +
2Cl2 = Hg2OCl2 + Cl2O. In this case, a compound of
mercury oxide with mercury chloride, or the so-called
mercury oxychloride, is obtained: Hg2OCl2 = HgO +
HgCl2. This is insoluble in water, and is not affected
by hypochlorous anhydride, so that the solution will
contain hypochlorous acid only, but the greater part
of it splits up into the anhydride and water.[32 bis]
Chlorine monoxide, which corresponds to
bleaching and hypochlorous salts, containing as it
does the two elements oxygen and chlorine, forms a
characteristic example of a compound of elements
which, in the majority of cases, act chemically in an
analogous manner. Chlorine monoxide, as prepared
from an aqueous solution by the abstraction of water
or by the action of dry chlorine on cold mercury
oxide, is, at the ordinary temperature, a gas or
vapour which condenses into a red liquid boiling at
+20° and giving a vapour whose density (43 referred
to hydrogen) shows that 2 vols. of chlorine and 1 vol.
of oxygen give 2 vols. of chlorine monoxide. In an
anhydrous form the gas or liquid easily explodes,
splitting up into chlorine and oxygen. This
explosiveness is determined by the fact that heat is
evolved in the decomposition to the amount of about
15,000 heat units for Cl2O.[33] The explosion may
even take place spontaneously, and also in the
presence of many oxidisable substances (for
instance, sulphur, organic compounds, &c.), but the
solution, although unstable and showing a strong
oxidising tendency, does not explode.[34] It is evident
that the presence of hypochlorous acid, HClO, may
be assumed in an aqueous solution of Cl2O, since
Cl2O + H2O = 2HClO.
Hypochlorous acid, its salts, and chlorine monoxide
serve as a transition between hydrochloric acid,
chlorides, and chlorine, and a whole series of
compounds containing the same elements combined
with a still greater quantity of oxygen. The higher
oxides of chlorine, as their origin indicates, are
closely connected with hypochlorous acid and its
salts:
Cl2 NaCl HCl hydrochloric acid.
Cl2O NaClO HClO hypochlorous acid.
Cl2O3 NaClO2 HClO2 chlorous acid.[35]
Cl2O5 NaClO3 HClO3 chloric acid.
Cl2O7 NaClO4 HClO4 perchloric acid.
When heated, solutions of hypochlorites undergo a
remarkable change. Themselves so unstable, they,
without any further addition, yield two fresh salts
which are both much more stable; one contains more
oxygen than MClO, the other contains none at all.
3MClO = MClO3 + 2MCl
hypochlorite chlorate chlorate
Part of the salt—namely, two-thirds of it—parts
with its oxygen in order to oxidise the remaining
third.[36] From an intermediate substance, RX, two
extremes, R and RX3 are formed, just as nitrous
anhydride splits up into nitric oxide and nitric
anhydride (or nitric acid). The resulting salt, MClO3,
corresponds with chloric acid and potassium chlorate,
KClO3. It is evident that a similar salt may be
obtained directly by the action of chlorine on an
alkali if its solution be heated, because RClO will be
first formed, and then RClO3; for example, 6KHO +
3Cl2 = KClO3 + 5KCl + 3H2O. Chlorates are so
prepared; for instance, potassium chlorate, which is
easily separated from potassium chloride, being
sparingly soluble in cold water.[37]
If dilute sulphuric acid be added to a solution of
potassium chlorate, chloric acid is liberated, but it
cannot be separated by distillation, as it is
decomposed in the process. To obtain the free acid,
sulphuric acid must be added to a solution of barium
chlorate.[38] The sulphuric acid gives a precipitate of
barium sulphate, and free chloric acid remains in
solution. The solution may be evaporated under the
receiver of an air-pump. This solution is colourless,
has no smell, and acts as a powerful acid (it
neutralises sodium hydroxide, decomposes sodium
carbonate, gives hydrogen with zinc, &c.); when
heated above 40°, however, it decomposes, forming
chlorine, oxygen, and perchloric acid: 4HClO3 =
2HClO4 + H2O + Cl2 + O3. In a concentrated
condition the acid acts as an exceedingly energetic
oxidiser, so that organic substances brought into
contact with it burst into flame. Iodine, sulphurous
acid, and similar oxidisable substances form higher
oxidation products and reduce the chloric acid to
hydrochloric acid. Hydrochloric acid gas gives
chlorine with chloric acid (and consequently with
KClO3 also) acting in the same manner as it acts on
the lower acids: HClO3 + 5HCl = 3H2O + 3Cl2.
By cautiously acting on potassium chlorate with
sulphuric acid, the dioxide (chloric peroxide), ClO2,[39]
is obtained (Davy, Millon). This gas is easily liquefied
in a freezing mixture, and boils at +10°. The vapour
density (about 35 if H = 1) shows that the molecule
of this substance is ClO2.[40] In a gaseous or liquid
state it very easily explodes (for instance, at 60°, or
by contact with organic compounds or finely divided
substances, &c.), forming Cl and O2, and in many
instances[41] therefore it acts as an oxidising agent,
although (like nitric peroxide) it may itself be further
oxidised.[42] In dissolving in water or alkalis chloric
peroxide gives chlorous and hypochlorous acids—
2ClO2 + 2KHO = KClO3 + KClO2 + H2O—and
therefore, like nitric peroxide, the dioxide may be
regarded as an intermediate oxide between the
(unknown) anhydrides of chlorous and chloric acids:
4ClO2 = Cl2O3 + Cl2O3.[43]
As the salts of chloric acid, HClO3, are produced by
the splitting up of the salts of hypochlorous acid, so
in the same way the salts of perchloric acid, HClO4,
are produced from the salts of chloric acid, HClO3.
But this is the highest form of the oxidation of HCl.
Perchloric acid, HClO4, is the most stable of all the
acids of chlorine. When fused potassium chlorate
begins to swell up and solidify, after having parted
with one-third of its oxygen, potassium chloride and
potassium perchlorate have been formed according
to the equation 2KClO3 = KClO4 + KCl + O2.
The formation of this salt is easily observed in the
preparation of oxygen from potassium chlorate,
owing to the fact that the potassium perchlorate
fuses with greater difficulty than the chlorate, and
therefore appears in the molten salt as solid grains
(see Chapter III. Note 12). Under the action of
certain acids—for instance, sulphuric and nitric—
potassium chlorate also gives potassium perchlorate.
This latter may be easily purified, because it is but
sparingly soluble in water, although all the other salts
of perchloric acid are very soluble and even
deliquesce in the air. The perchlorates, although they
contain more oxygen than the chlorates, are
decomposed with greater difficulty, and even when
thrown on ignited charcoal give a much feebler
deflagration than the chlorates. Sulphuric acid (at a
temperature not below 100°) evolves volatile and to
a certain extent stable perchloric acid from
potassium perchlorate. Neither sulphuric nor any
other acid will further decompose perchloric acid as it
decomposes chloric acid. Of all the acids of chlorine,
perchloric acid alone can be distilled.[44] The pure
hydrate HClO4[45] is a colourless and exceedingly
caustic substance which fumes in the air and has a
specific gravity 1·78 at 15° (sometimes, after being
kept for some time, it decomposes with a violent
explosion). It explodes violently when brought into
contact with charcoal, paper, wood, and other
organic substances. If a small quantity of water be
added to this hydrate, and it be cooled, a crystallo-
hydrate, ClHO4,H2O, separates out. This is much
more stable, but the liquid hydrate HClO4,2H2O is still
more so. The acid dissolves in water in all
proportions, and its solutions are distinguished for
their stability.[46] When ignited both the acid and its
salts are decomposed, with the evolution of oxygen.
[47]
 On comparing chlorine as an element not only with
nitrogen and carbon but with all the other non-
metallic elements (chlorine has so little analogy with
the metals that a comparison with them would be
superfluous), we find in it the following fundamental
properties of the halogens or salt-producers. With
metals chlorine gives salts (such as sodium chloride,
&c.); with hydrogen a very energetic and monobasic
acid HCl, and the same quantity of chlorine is able by
metalepsis to replace the hydrogen; with oxygen it
forms unstable oxides of an acid character. These
properties of chlorine are possessed by three other
elements, bromine, iodine, and fluorine. They are
members of one natural family. Each representative
has its peculiarities, its individual properties and
points of distinction, in combination and in the free
state—otherwise they would not be independent
elements; but the repetition in all of them of the
same chief characteristics of the family enables one
more quickly to grasp all their various properties and
to classify the elements themselves.
In order to have a guiding thread in forming
comparisons between the elements, attention must
however be turned not only to their points of
resemblance but also to those of their properties and
characters in which they differ most from each other.
And the atomic weights of the elements must be
considered as their most elementary property, since
this is a quantity which is most firmly established,
and must be taken account of in all the reactions of
the element. The halogens have the following atomic
weights—
F = 19, Cl = 35·5, Br = 80, I = 127.
All the properties, physical and chemical, of the
elements and their corresponding compounds must
evidently be in a certain dependence on this
fundamental point, if the grouping in one family be
natural.[47 bis] And we find in reality that, for instance,
the properties of bromine, whose atomic weight is
almost the mean between those of iodine and
chlorine, occupy a mean position between those of
these two elements. The second measurable
property of the elements is their equivalence or their
capacity for forming compounds of definite forms.
Thus carbon or nitrogen in this respect differs widely
from the halogens. Although the form ClO2
corresponds with NO2 and CO2, yet the last is the
highest oxide of carbon, whilst that of nitrogen is
N2O5, and for chlorine, if there were an anhydride of
perchloric acid, its composition would be Cl2O7, which
is quite different from that of carbon. In respect to
the forms of their compounds the halogens, like all
elements of one family or group, are perfectly
analogous to each other, as is seen from their
hydrogen compounds:
HF, HCl, HBr, HI.
Their oxygen compounds exhibit a similar analogy.
Only fluorine does not give any oxygen compounds.
The iodine and bromine compounds corresponding
with HClO3 and HClO4 are HBrO3 and HBrO4, HIO3
and HIO4. On comparing the properties of these
acids we can even predict that fluorine will not form
any oxygen compound. For iodine is easily oxidised—
for instance, by nitric acid—whilst chlorine is not
directly oxidised. The oxygen acids of iodine are
comparatively more stable than those of chlorine;
and, generally speaking, the affinity of iodine for
oxygen is much greater than that of chlorine. Here
also bromine occupies an intermediate position. In
fluorine we may therefore expect a still smaller
affinity for oxygen than in chlorine—and up to now it
has not been combined with oxygen. If any oxygen
compounds of fluorine should be obtained, they will
naturally be exceedingly unstable. The relation of
these elements to hydrogen is the reverse of the
above. Fluorine has so great an affinity for hydrogen
that it decomposes water at the ordinary
temperature; whilst iodine has so little affinity for
hydrogen that hydriodic acid, HI, is formed with
difficulty, is easily decomposed, and acts as a
reducing agent in a number of cases.
From the form of their compounds the halogens
are univalent elements with respect to hydrogen and
septivalent with respect to oxygen, N being trivalent
to hydrogen (it gives NH3) and quinqui-valent to
oxygen (it gives N2O5), and C being quadrivalent to
both H and O as it forms CH4 and CO2. And as not
only their oxygen compounds, but also their
hydrogen compounds, have acid properties, the
halogens are elements of an exclusively acid
character. Such metals as sodium, potassium, barium
only give basic oxides. In the case of nitrogen,
although it forms acid oxides, still in ammonia we
find that capacity to give an alkali with hydrogen
which indicates a less distinctly acid character than in
the halogens. In no other elements is the acid-giving
property so strongly developed as in the halogens.
In describing certain peculiarities characterising
the halogens, we shall at every step encounter a
confirmation of the above-mentioned general
relations.
As fluorine decomposes water with the evolution of
oxygen, F2 + H2O = 2HF + O, for a long time all
efforts to obtain it in free state by means of methods
similar to those for the preparation of chlorine
proved fruitless.[48] Thus by the action of hydrofluoric
acid on manganese peroxide, or by decomposing a
solution of hydrofluoric acid by an electric current,
either oxygen or a mixture of oxygen and fluorine
were obtained instead of fluorine. Probably a certain
quantity of fluorine[48 bis] was set free by the action of
oxygen or an electric current on incandescent and
fused calcium fluoride, but at a high temperature
fluorine acts even on platinum, and therefore it was
not obtained. When chlorine acted on silver fluoride,
AgF, in a vessel of natural fluor spar, CaF2, fluorine
was also liberated; but it was mixed with chlorine,
and it was impossible to study the properties of the
resultant gas. Brauner (1881) also obtained fluorine
by igniting cerium fluoride, 2CeF4 = 2CeF3 + F2; but
this, like all preceding efforts, only showed fluorine
to be a gas which decomposes water, and is capable
of acting in a number of instances like chlorine, but
gave no possibility of testing its properties. It was
evident that it was necessary to avoid as far as
possible the presence of water and a rise of
temperature; this Moissan succeeded in doing in
1886. He decomposed anhydrous hydrofluoric acid,
liquefied at a temperature of -23° and contained in a
U-shaped tube (to which a small quantity of
potassium fluoride had been added to make it a
better conductor), by the action of a powerful electric
current (twenty Bunsen's elements in series).
Hydrogen was then evolved at the negative pole, and
fluorine appeared at the positive pole (of iridium
platinum) as a pale green gas which decomposed
water with the formation of ozone and hydrofluoric
acid, and combined directly with silicon (forming
silicon fluoride, SiF4), boron (forming BF3), sulphur,
&c. Its density (H = 1) is 18, so that its molecule is
F2. But the action of fluorine on metals at the
ordinary temperature is comparatively feeble,
because the metallic fluoride formed coats the
remaining mass of the metals; it is, however,
completely absorbed by iron. Hydrocarbons (such as
naphtha), alcohol, &c., immediately absorb fluorine,
with the formation of hydrofluoric acid. Fluorine
when mixed with hydrogen can easily be made to
explode violently, forming hydrofluoric acid.[49]
In 1894, Brauner obtained fluorine directly by
igniting the easily formed[49 bis] double lead salt
HF,3KF,PbF4, which first, at 230°, decomposes with
the evolution of HF, and then splits up forming
3KF,PbF2 and fluorine F2, which is recognised by the
fact that it liberates iodine from KI and easily
combines with silicon, forming SiF4. This method
gives chemically pure fluorine, and is based upon the
breaking up of the higher compound—tetrafluoride of
lead, PbF4, corresponding to PbO2, into free fluorine,
F2, and the lower more stable form—bifluoride of
lead, PbF2, which corresponds to PbO; that is, this
method resembles the ordinary method of obtaining
chlorine by means of MnO2, as MnCl4 here breaks up
into MnCl2 and chlorine, just as PbF4 splits up into
PbF2 and fluorine.
Among the compounds of fluorine, calcium
fluoride, CaF2, is somewhat widely distributed in
nature as fluor spar,[50] whilst cryolite, or aluminium
sodium fluoride, Na3AlF6, is found more rarely (in
large masses in Greenland). Cryolite, like fluor spar,
is also insoluble in water, and gives hydrofluoric acid
with sulphuric acid. Small quantities of fluorine have
also in a number of cases been found in the bodies
of animals, in the blood, urine, and bones. If
fluorides occur in the bodies of animals, they must
have been introduced in food, and must occur in
plants and in water. And as a matter of fact river, and
especially sea, water always contains a certain,
although small, quantity of fluorine compounds.
Hydrofluoric acid, HF, cannot be obtained from
fluor spar in glass retorts, because glass is acted on
by and destroys the acid. It is prepared in lead
vessels, and when it is required pure, in platinum
vessels, because lead also acts on hydrofluoric acid,
although only very feebly on the surface, and when
once a coating of fluoride and sulphate of lead is
formed no further action takes place. Powdered fluor
spar and sulphuric acid evolve hydrofluoric acid
(which fumes in the air) even at the ordinary
temperature, CaF2 + H2SO4 = CaSO4 + 2HF. At 130°
fluor spar is completely decomposed by sulphuric
acid. The acid is then evolved as vapour, which may
be condensed by a freezing mixture into an
anhydrous acid. The condensation is aided by
pouring water into the receiver of the condenser, as
the acid is easily soluble in cold water.
In the liquid anhydrous form hydrofluoric acid boils
at +19°, and its specific gravity at 12·8° = 0·9849.
[51]
It dissolves in water with the evolution of a
considerable amount of heat, and gives a solution of
constant boiling point which distils over at 120°;
showing that the acid is able to combine with water.
The specific gravity of the compound is 1·15, and its
composition HF,2H2O.[52] With an excess of water a
dilute solution distils over first. The aqueous solution
and the acid itself must be kept in platinum vessels,
but the dilute acid may be conveniently preserved in
vessels made of various organic materials, such as
gutta-percha, or even in glass vessels having an
interior coating of paraffin. Hydrofluoric acid does
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