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Subject: 11. Traditional Specialist Chemical Information Sources

11.1  Where can I find spectral libraries/databases?

The most likely place is near to an instrument. These are not usually
in general technical libraries, but are kept near the instruments.
A polite request to the person in charge of the instrument should identify
who to contact for permission to use the library or database. There is
some spectral information in reference texts, such as the Rubber Handbook
and the Merck Index, but most compilations are now so large that they cover
several volumes. There are several compilations that are available
commercially, either in hard copy (HC) or CD-ROM (CD) - which is usually
more expensive because of the included searching software. Chemical
manufacturers, such as Aldrich, may also sell spectral libraries, eg
IR $495(HC) [1], FT-IR $875(HC) or $1578(CD) [2], 60MHz H1 NMR $495(HC) [3],
and 300MHz H1 + 75MHz C13 NMR $1072(HC) [4], as well as offering
compilations from government agencies, eg the NIST/EPA/NIH Mass Spectral
database $1320(CD)[5]. The databases are also sold by several instrument
manufacturers. One commercial supplier of spectral information ( Fiveash
Data Management, Inc. ) is accessible via the Internet [6].

11.2  Where can I find polymer chemistry information?

The first stop should be the multi-volume Encyclopedia of Polymer Science
and Engineering [7], which should be in most technical libraries. Specific
polymers are covered in much less detail in Kirk Othmer. There are
several journals devoted to polymer science and chemistry, including the
Journal of Polymer Science.

11.3  Where can I find analytical chemistry information?

There is a sci.chem.analytical group where specific questions can be
posted after you have attempted to find the information in the following
sources. For qualitative information, the spot test books by Fiegl [8,9]
and "Semi-micro Vogel"[10], are good starting points. For introductory
quantitative analysis, "Quantitative Inorganic" [11],"Practical Organic
Chemistry"[12] by Vogel are good introductions to non-instrumental
techniques. The multi-volume "Treatise on Analytical Chemistry" by
Kolthoff and Elving [13] comprehensively discusses most techniques, and
several volumes of the ACS Series "Techniques in Chemistry" [14] also cover
analytical procedures. " Instrumental Methods of Analysis" by Willard,
Merritt, Dean and Settle [15], and "Analytical Instrumentation Handbook" by
Ewing [16] provide a good introduction to chemical instrumentation. Most
educational institutions will have equivalent texts if they are not using the
above.

For specific analyses it is often desirable to use standard procedures,
especially if your laboratory is seeking ISO 9001 accreditation, or if the
results are likely to be disputed. Some well known compilations of standard
methods include:-

Laboratory Reagents
- usually specified by manufacturers or chemical societies
  BDH 'Analar' Standards for Laboratory Chemicals [17]
  ACS Reagent Chemicals [18]

Materials, Industrial Chemicals, and Finished Products.
- usually the monographs in the following volumes also specify assay and
  impurity limits, as well as detailing the analytical procedure.
  ASTM - Issued annually, cover physical and chemical testing of a wide range
         of industrial products. Often require specialised test equipment.
  ISO - International standards, usually derived from US(ASTM), UK(BSI) or
        FRG(DIN) standards. Similar to above.

Pharmaceuticals
- usually the pharmacopoeia have monographs and methods, but some methods
  are also specified in National Formulary or Pharmaceutical Codex volumes,
  which may be separate from the pharmacopoeia.
- common pharmacopoeia are USP, BP, and EP - with Martindale [19] often used
  to ascertain where and when a specific monograph appeared.

Food
- often the procedures specified in Government legislation.
- The Official Methods of the AOAC [20] covers many routine US methods.

Environmental Pollution
- the procedures are usually specified in the relevant legislation, and
  frequently US EPA procedures are used. Several common EPA procedures are
  now available on computer disk [21,22].

Petroleum
- usually covered by ASTM, ISO or DIN, but there are some unique IP
  ( Institute of Petroleum - UK ) procedures that are also used.
- "Chromatography in Petroleum Analysis"[23], summarises popular techniques.

Gases
- instrument manufacturers have fairly detailed procedures for process gases.
- "The Analysis of Gases by Chromatography"[24], provides useful examples.

Water and Wastewater
- the APHA/WWA/WPCF standard methods are most often used [25]
- many tests are also covered by ASTM, ISO, and DIN procedures
- alternative techniques are described in "Water Analysis" [26]
- organics in water are covered by Crompton [27]
- most aspects of water chemistry are detailed in Franks [28]

Sample Preparation
- consumable and instrument manufacturers often provide detailed manuals
  and guides free.
- "Methods of Decomposition in Inorganic Analysis" [29] covers a wide range
  of preparations for spectroscopy.
- The "Handbook of Analytical Derivatization Reactions" [30] and the
  " Handbook of Derivatives for Chromatography" [31] cover many of the
  techniques for gas and liquid chromatography.

Obviously there are several journals devoted to various aspects of
analytical chemistry. The April issue of Analytical Chemistry publishes
a review of papers published during the previous two years. The review
alternates between Fundamental and Application Reviews and is a quick means
of catching current trends if you are unable to locate an expert.

11.4  Where can I find environmental chemistry information?

There are several standard texts used by environmental chemistry classes
that provide good general introductions, eg "Environmental Chemistry" [32]
"Fundamentals of Environmental Chemistry [33], and "Environmental Organic
Chemistry" [34]. They should be available in most technical libraries. The
monthly journal "Environmental Science and Technology" covers most aspects
of environment chemistry. "Chemosphere" concentrates on toxins such as PCBs
and Dioxin, and " Science of the Total Environment also covers many aspects.
Government agencies such as the EPA also publish large amounts of
information, and many environmental groups also provide significant amounts
of technical information. There are a range of specialist texts that cover
specific pollutants, eg "Metals and their Compounds in the Environment:
Occurrence, Analysis and Biological Relevance" [35].

The sci.environment Usenet group may well be a better place to request
environmental chemistry information than sci.chem, but please remember
to move discussions to talk.environment.

11.5  Where can I find physical chemistry information?

General introductory information will be available in any technical library
where chemistry is taught, and one of the more popular modern texts is
"Physical Chemistry" by P.W.Atkins [36], and a classical text is
"Textbook of Physical Chemistry" by S.Glasstone [37]. The multi-volume ACS
series "Physical Methods of Chemistry"[38] also covers many physical
chemistry techniques. There are also the Journal of Chemical Physics and the
Journal of Physical Chemistry. Frankly, I would not have a clue where else
to go.

11.6  Where can I find inorganic chemistry information?

General introductory information will be available in any technical library
where chemistry is taught. One popular text is "Inorganic Chemistry" by
D.F.Shriver, P.W.Atkins, and C.H.Langford [39], which also has the answers
available as a separate book. "Inorganic Vogel"[40], also discusses the theory
of the analyses. There are three major multi-volume inorganic encyclopedias.
Mellor is frequently found in public libraries, and provides a broad cover
of the field, however the more comprehensive is Gmelin [41], which will be
available in most institution libraries. The more recent developments and
mechanisms are covered in the multi-volume "Encyclopedia of Inorganic
Chemistry" [42], which may be difficult to find due to its $2500 price.
"Advanced Inorganic Chemistry" [43] by F.A.Cotton and G.Wilkinson provides a
good base to start. There are several journals that cover aspects of
inorganic chemistry.

11.7  Where can I find organic chemistry information?

General introductory information will be available in any technical library
where chemistry is taught. One popular modern text is " Organic Chemistry "
by T.W.G.Solomons [44], but my favourite is "Organic Chemistry"[45] by Fieser
and Fieser - a much more practical discussion of organic molecules.
Once you are familiar with organic chemistry mechanisms then "Advanced
Organic Chemistry" by Carey and Sandberg [46] is a good overview.

There are several compilations of organic synthesis techniques to assist
researchers. The multi-volume sets "Organic Reactions" [47], and "Reagents
for Organic Synthesis" [48], are examples of sets that will be available from
institution libraries. There are some good theoretical texts available, eg
"The Logic of Chemical Synthesis" [49]. For specific preparation and
properties of individual compounds, then Heilbron [50] and Beilstein [51],
are the initial resources of choice. There are several journals devoted to
organic chemistry in general, including Journal of Organic Chemistry,
Tetrahedron, etc.. Specific branches of organic chemistry, such as
Carbohydrates, Lipids, or Proteins have their own journals, as do
applications such as pharmaceuticals and pesticides.

11.8  Where can I find industrial chemistry information?

The best single volume remains Shreve's "Chemical Process Industries" [52].
There are three major multi-volume encyclopedias, Kirk Othmer, Ullmann,
and McKetta, that cover many aspects of industrial chemistry and at
least one is usually available in a public library. There are also several
journals that provide good overviews of industrial chemistry, the easiest
to read being C&EN, and Chemtech. Research is usually published
in Industrial and Engineering Chemistry ( which is an excellent source
for historical research ),  and specialist chemical engineering journals.

11.9  Where can I find pharmaceutical chemistry information?

Pharmaceutical research often is initially reported in patent literature,
consequently patent searching is a good place to start. The Merck Index is
focused on pharmaceuticals, and also provides excellent leads to the
research literature. There are several pharmaceutical chemistry books, such
as Goodman and Gilman [53], and "Essentials of Medicinal Chemistry" [54],
that provide overviews of the field. The Journal of Pharmaceutical Chemistry
is a good source for research articles. Details of chemicals appearing in
formulated products can be found in the "Handbook of Pharmaceutical
Excipients" [55].

------------------------------

Subject: 12. Nomenclature

12.1  What are CAS Registry Numbers?

When chemicals are first encountered by the Chemical Abstracts Service, they
are assigned a unique number when they are registered. These numbers are not
related to any structure or property of the molecule, they are arbitrarily
assigned. It should be remembered that occasionally a compound may be
accidentally assigned two or more numbers - especially industrial products
that have not been completely characterised. When this is discovered, one of
the numbers is no longer used. The numbers usually take the form of
[xx-yy-z to xxxxxx-yy-z] and square brackets are often used in monographs to
identify the CAS Registry Number [RN]. The easiest way to locate the CAS RN
for commercially-available chemicals is to look in suppliers catalogues
( eg Aldrich) or compilations ( eg Merck or Hawley ), almost all chemical
texts now list the RN, and several ( eg Merck Index and Aldrich ) have a
cross-reference Index. The RN is extremely useful for on-line searching of
Chemical Abstracts and several other popular chemistry-related databases,
but is not particularly useful for the hardcopy version, except to confirm
compound identity.

12.2  What are the correct names of recently-discovered elements?

The Transfermium Working Group was established in 1986 by the International
Union of Pure and Applied Chemistry (IUPAC) and the International Union of
Pure and Applied Physics (IUPAP). The working  group published several
reports, and then recommended that elements should not be named after living
persons [1]. This greatly upset the USA - who wanted to name an element after
G. Seaborg. After protracted negotiations, a compromise selection of names
was finally approved by the IUPAC Commission on Nomenclature in Inorganic
Chemistry, the IUPAC Inorganic Division, the IUPAC Bureau, and the selection
was eventually ratified by the IUPAC Council meeting in Geneva during August
1997 [2].

101      Mendelevium    Md             D. Mendeleev (Russia)
102      Nobelium       No             Nobel Institute (Sweden)
103      Lawrencium     Lr             E. Lawrence (USA)
104      Rutherfordium  Rf             E. Rutherford (NZ)
105      Dubnium        Db             Dubna = Russian Research Centre
106      Seaborgium     Sg             G. Seaborg (USA)
107      Bohrium        Bh             N. Bohr (Denmark)
108      Hassium        Hs             Latin name for German state of Hesse
109      Meitnerium     Mt             L. Meitner (Austria)

Note that Hesse is where the German heavy-element laboratory is based.
The Gesellschaft fur Schwerionenforschung (GSI) was responsible for the
first man-made creation of elements 107-110. The compromise will now move
attention to the naming the recently-discovered elements 110-112.

12.3  What is the nomenclature system for CFCs/HCFCs/HFCs?

The CFC naming system was developed by T.Midgley,Jr. and A.L.Henne in 1929,
and further refined by J.D.Park. Originally, organic molecules that contained
Chlorine and Fluorine were all referred to as CFCs. Today, the group is
subdivided into CFCs, HCFCs, and HFCs. The naming system consists of:-

CFC-01234a  where 0 = number of double bonds ( omitted if zero )
                  1 = Carbon atoms - 1 ( omitted if 0 )
                  2 = Hydrogen atoms + 1
                  3 = Fluorine atoms
                  4 = Chlorine atoms replaced by Bromine ("B" prefix added )
                  a = letter added to identify isomers, the "normal" isomer
                     in any number has the smallest mass difference on each
                     carbon, and a, b, or c are added as the masses diverge
                     from normal.

If the compound is cyclic, then the number is prefixed with "C". There are
several other refrigerants, some of which are hydrocarbons, hydrocarbon
blends, or CFC blends. Full details of the nomenclature system are specified
in ANSI/ASHRAE Standard 34-1992 with additional annual supplements. Chemical
names are frequently used in place of the numbers for common materials
- such as trichloroethylene and chloroform. The specified ANSI/ASHRAE
prefixes were FC ( FluoroCarbon ), or R ( Refrigerant ), but today most are
prefixed by more specific classifications - such as CFC, HCFC, and HFC.

CFC-11     CCl3F        trichlorofluoromethane                   [75-69-4]
CFC-12     CCl2F2       dichlorodifluoromethane                  [75-71-8]
CFC-113    CCl2F-CClF2  1,1,2-trichlorotrifluoroethane           [76-13-1]
HCFC-22    CHClF2       chlorodifluoromethane                    [75-45-6]
HCFC-123   CHCl2-CF3    2,2-dichloro-1,1,1-trifluoroethane       [306-83-2]
HCFC-123a  CHClF-CClF2  1,2-dichloro-1,1,2-trifluoroethane       [354-23-4]
HFC-23     CHF3         trifluoromethane                         [75-46-7]
HFC-134    CHF2-CHF2    1,1,2,2-tetrafluoroethane                [359-35-3]
HFC-134a   CH2F-CF3     1,2,2,2-tetrafluoroethane                [811-97-2]
R-20       CHCl3        chloroform                               [67-66-3]
R-22B1     CHBrF2       bromodifluoromethane                     [1511-62-2]
R-1120     CHCl=CCl2    trichloroethylene                        [79-01-6]
R-1150     CH2=CH2    ethylene                                 [74-85-1]
R-C316     C4Cl2F6      1,2-dichlorohexafluorocyclobutane

Another technique for naming CFCs uses the addition of 90 to the CFC number
to produce a "def" number which corresponds to the CHF composition. If
(e + f) < (2d + 2), then additional atoms are required for saturation. This
technique has been described in detail in the Journal of Chemical Education
[3].

ASHRAE     +90     Empirical Composition    Formula
                   C  H  F   (+Cl)
CFC-11     101     1  -  1     3            CCl3F
CFC-12     102     1  -  2     2            CCl2F2
HCFC-22    112     1  1  2     1            CHClF2
HCFC-123   213     2  1  3     2            CHCl2-CF3
HFC-134a   224     2  2  4     -            CH2F-CF3

Halons are numbered according to a totally different system developed by
the US Army Corps of Engineers, and the prefix term is always "Halon".
Hydrogen is not numbered, and terminal zeros are not expressed.

Halon-0123  where 0 = number of carbon atoms
                  1 = number of fluorine atoms
                  2 = number of chlorine atoms
                  3 = number of bromine atoms

Halon-1211 CBrClF2      bromochlorodifluoromethane               [353-59-3]
Halon-1301 CBrF3        bromotrifluoromethane                    [75-63-8]
Halon-2402 CBrF2-CBrF2  1,2-dibromo-1,1,2,2-tetrafluoroethane    [124-73-2]

12.4  How can I get the IUPAC chemical name from traditional names?

It depends. Usually the quickest way is to look the name up in a chemical
supplier's catalog, MSDS, or a standard text like Merck or Hawley. You can
also often find the correct name if you refer to an old chemistry text that
lists both the traditional and IUPAC naming conventions. Some traditional
or common names also refer to mixtures of chemicals, eg aqua regia, piranha
solution.

One reason why traditional names have been replaced is because the same name
could be used for different compounds. An example is the use of caprylic to
describe 1-Octanol and 2-Octanol, and attempts to qualify the name with
"primary" and "secondary" were less than successful. Octyl alcohol has been
used to describe both 1-octanol and 2-ethylhexanol, thus explaining why the
well known dioctyl phthalate (DOP) is actually bis(2-ethylhexyl) phthalate.
The following examples highlight the diversity of names often encountered.

Carbon   Alkane        Alcohol               Aldehyde         Acid

1        methane       methanol              form-            formic
                       carbinol
2        ethane        ethyl                 acet-            acetic
                       methyl carbinol
3      n-propane       n-propyl              propion-         propionic
                       ethyl carbinol
4      n-butane        n-butyl               n-butyr-         n-butyric
                       propyl carbinol
5      n-pentane       n-amyl                n-valer-         n-valeric
                       butyl carbinol
6      n-hexane        hexyl                 capro-           caproic
                       amyl carbinol         caproic
7      n-heptane       enanthyl              enanth-          enanthic
                       enanthic
                       hexyl carbinol
8a     n-octane        capryl                capryl-          caprylic
                       primary caprylic      caprylic
                       heptyl carbinol
                       1-octanol
8b                     capryl
                       secondary caprylic
                       methyl hexyl carbinol
                       2-octanol
9      n-nonane        pelargonic            pelargonic       pelargonic
                       octyl carbinol
10     n-decane        capric                capr-            capric
                       nonyl carbinol        capric
12     n-dodecane      lauryl                laur-            lauric
                       lauric                lauryl
14     n-tetradecane   myristyl              myrist-          myristic
16     n-hexadecane    cetyl                 palmit-          palmitic
       cetane
18     n-octadecane    stearyl                                stearic
20     n-eicosane      arachidyl                              arachidic

Primary
 - alcohol    R1CH2OH
 - amine      R1NH2
 eg normal    straight chain    normal octane     n-octane
                                normal butanol    1-butanol
    iso       branched chain    iso-butane        2-methylpropane
                                iso-butanol       2-methyl-1-propanol
                                iso-octane        2,2,4-trimethylpentane

Secondary
 - alcohol    R1R2CHOH
 - amine      R1R2NH
 eg                             sec-butanol       2-butanol
                                iso-propanol      2-propanol

Tertiary
 - alcohol    R1R2R3COH
 - amine      R1R2R3N
 eg                             tert-butanol      2-methyl-2-propanol

- substitution onto the benzene ring
  1,2 = ortho                ortho-xylene
  1,3 = meta                 meta-xylene
  1,4 = para                 para-xylene

However other names get more tricky, especially historical names, where
several names may be used for the same chemical and, even worse, different
chemicals can be described by the same name. Examples include:-
- calcium carbonate = limestone, chalk, calcite.
- calcium hydroxide = slaked lime, hydrated lime, caustic lime.
- calcium oxide = calx, lime, quicklime, unslaked lime, burnt lime.
- hydrochloric acid = muriatic acid, spirits of salts.
- nitric acid = aqua fortis.
- potassium carbonate = potash, artificial alkali, vegetable alkali.
- potassium hydroxide = caustic potash, lye.
- sodium carbonate - any form = soda, natural alkali, mineral alkali.
                   - anhydrous = soda ash.
                   - dodecahydrate = sal soda, washing soda.
                   - monohydrate = soda crystals.
- sodium chloride = rock salt.
- sodium hydroxide = caustic soda, lye, soda lye.
- sulfuric acid = oil of vitriol

Some old chemical terms are seldom encountered these days, but have very
specific meanings, eg
" flowers " described any product of sublimation, hence "flowers of sulfur".
" specific " in front of any quantity means " divided by mass ", hence
    "specific gravity".
" ether " described a volatile liquid, not only compounds with the Cx-O--Cy
    structure, and also often known today as "spirit".
" aromatic " described a liquid that had an aroma, not only those derived
    from benzene, or which benzene ring structure.
" oil " described a liquid that was not miscible with water, thus it
    described different products in different chemical industries :-
  - Essential oils = volatile and odoriferous liquid plant extracts.
    Essential oils can be obtained by extraction or distillation ( steam ),
    often contain terpenes ( based on the isoprene structure ), are usually
    smelly ( aromatic ), and are used for perfumes, flavours and aromas, eg
    lemon oil and pine oil.
  - Triglyceride oils = fats and oils based on the glycerol molecule that
    can be obtained from plant and animal material, frequently by melting or
    cold pressing. They are a significant, and important, component in our
    diet, eg soya oil, lard, fish oils, and anhydrous milk fat.
  - Petroleum oil = a mixture of a large number of hydrocarbons that are
    usually derived from 0.1 to 3 billion-year-old organic matter. Crude oil
    can contain hundreds of hydrocarbons with one to sixty carbon atoms, and
    the hydrocarbons are usually grouped and reported by type, eg alkane
    ( paraffin ), alkene ( olefin ), or arene ( aromatic ).

Almost all old industries had easy-to-remember names for chemicals they
commonly encountered, but today many of those names can cause confusion
if used outside the industry. Some common examples, just from the petroleum
industry alone are:-
- " ether " is a volatile hydrocarbon fraction that does not contain the
    Cx-O-Cy structure, eg petroleum ether ( aka petroleum spirit ).
- " naphthene " is a cyclic paraffin, does not contain naphthalene, and is
    not a major component of naphtha ( refer Section 27.5 ).
- Benzene, toluene and xylene are often called benzol, toluol, and xylol,
    even though they do not contain an -OH group.
- Benzine ( ligroin ) was a saturated hydrocarbon fraction that boiled
    between 20C and 135C. Gasoline/petrol fractions are still called benzine
    by some older people.
- Diesel fuel is often called "gas oil", which is a historical term for
    hydrocarbon distillate fractions. Atmospheric gas oil has a boiling
    range between 220C - 450C, and vacuum gas oil boils from 350C to 550C.

12.5  What does "omega-3 fatty acids" mean?

Chemists recognise that they should always number carbon chains from the
end with the functional group, so the location of double bonds in
unsaturated fatty acids are numbered from the carboxylic acid end, and
are usually designated by "delta" in their abbreviated names.

Biochemists are more interested in the actual role that chemicals play,
consequently they will consider the position from the end that is important.
In the case of natural fatty acids the double bonds are usually cis
configured, and it is the distance of the first double bond from the
terminal end of the carbon chain that is important. They use "omega" to
signify that the double bond is cis, and they are counting from the other
end. The great advantage is that chain length can be ignored, and compounds
that are subjected to the same biochemical processes are grouped together.

In 1967, the IUPAC/IUB commission responsible for lipid nomenclature
recommended that for unsaturated fatty acids with cis double bonds, that
the "omega" symbol be replaced with "n-x", where n = the length of the
carbon chain, and x is the distance from the terminal end.

Some examples:-

Common            Chemical                            Chemical    Biochemical
 Name               Name                             d = delta     o = omega

Oleic           cis-9-octadecenoic                    c-C18:1d9     C18:1o9
Elaidic         trans-9-octadecenoic                  t-C18:1d9        -
Ricinoleic      D-(+)-12-hydroxy-octadec-cis-9-enoic  c-C18:1d9-12OH   -
Linoleic        cis-9,12-octadecadienoic              c-C18:2d9     C18:2o6
alpha Linolenic cis-9,12,15-octadecatrienoic          c-C18:3d9     C18:3o3
gamma Linolenic cis-6,9,12-octadecatrienoic           c-C18:3d6     C18:3o6
Arachidonic     cis-5,8,11,14-eicosatetraenoic        c-C20:4d5     C20:4o6
EPA             cis-5,8,11,14,17-eicosapentaenoic     c-C20:5d5     C20:5o3
Erucic          cis-13-docosenoic                     c-C22:1d13    C22:1o9
DHA             cis-4,7,10,13,16,19-docosahexaenoic   c-C22:6d4     C22:6o3

EPA and DHA are widely known as the omega-3 fatty acids present in high
concentrations in marine lipids, and are considered beneficial in diet,
although research is not complete [4,5].

12.6  What is Conjugated Linoleic Acid?

Conjugated linoleic acid describes the group of positional and geometric
isomers of linoleic acid ( cis-9,12-octadecadienoic acid ) that have a
conjugated double bond system starting at carbon 9, 10, or 11. They can be
either cis or trans, or various combinations of them. The more abundant
isomers in food are believed to be the cis-9, trans-11, and the trans-10,
cis-12 isomers. It's very difficult to separate the cis-9, trans-11 and
trans-9, cis-11 isomers, however the cis-9, trans-11 form is usually
considered the important and usually dominant isomer.

They are typically produced by bacteria in the rumen of ruminants because
the hydrolysis of fats in the rumen produces more unesterified linoleic
acid than is available to bacteria in other digestive systems. Plants
also contain conjugated linoleic acid, but there is much less of the
cis-9, trans-11 isomer, which is believed to be the biologically active
isomer. Foods that contain CLA are lamb, beef, turkey and dairy fat products,
ranging from 2.5 - 11 mg/g of fat - of which 75% or more is the cis-9,
trans-11 ( or trans-9, cis-11 ) isomer. CLA is of interest because it has
displayed antimutagenic activity in animals and human cell tests [6,7].

12.7  What are "heavy" metals?

There appears to be no standard definition, however the general consensus
appears to be all metals with a density greater than 4 or 5 [8,9,10]. If
you also consider the conventional analytical chemistry definition of "heavy
metals" ( precipitation of sulfides from acidic solutions ), you obtain
quite a diverse mixture of possible candidates. Moving the density limit
from 4 to 5 really only just impacts on Ti, Y and Se. Some other texts use
more complex definitions that may also include accepted "light" metals with
densities less than 4, eg Hawley uses "A metal of atomic weight greater
than sodium (22.9) that forms soaps on reaction with fatty acids. e.g.,
aluminum, lead, cobalt". The term " heavy-element " is commonly used to
describe the transfermium elements, - elements with an atomic number
greater than 100.

12.8  What is the difference between Molarity and Normality?.

A Molar solution contains one gram molecular weight ( aka mole ) of the
reagent in one litre of solution, and is represented by " M ". In modern
usage, "molar" is intended to only mean " divided by amount of substance",
and is not supposed to be used to describe 1M solutions. There are already
exceptions to the rule ( molar conductivity, molar extinction coefficient ),
so I would only worry about correct usage in exams, as in the real world
most chemists use Molar to describe 1M solutions.

A Molal solution is one gram molecular weight of the reagent in 1 kilogram
of solvent, and is usually represented by "m". This concentration unit is
relatively uncommon in the real world, so it's worth checking that the "m"
is not a "M" typo.

A Normal solution contains one gram equivalent weight ( aka equivalent )
of the reagent in one litre of solution, and is represented by " N ".
The equivalent weight of a reagent may vary according to the reaction, but
if considering just acid and base moles and equivalents, then:-

1M H2SO4 + 2M NaOH -> 2H2O + Na2SO4
1N H2SO4 + 1N NaOH -> H20 + 0.5Na2SO4
1N HCl + 1N NaOH -> H2O + NaCl

So you can see that the equivalent weight of an acid is that which contains
1.0078 grams of replaceable hydrogen which, in the case of sulfuric acid,
would be half the mole weight, but, in the case of hydrochloric acid, would
be the mole weight.

The equivalent weight of a base is that which contains one replaceable
hydroxyl group ( ie 17.008g of ionisable hydroxyl ). Thus the equivalent
weight of sodium hydroxide ( NaOH ) and potassium hydroxide ( KOH ) would
be the mole weight, but for calcium hydroxide ( Ca(OH)2 ) it would be half
the mole weight.

The equivalent weight of an oxidising or reducing agent is that weight of
the reagent that reacts with or contains 1.008 grams of available hydrogen
or 8.000 grams of available oxygen. "Available" means being able to be
utilised in oxidation or reduction reactions. The equivalent weight of an
oxidising agent is determined by the change in oxidation number which the
reduced element experiences, eg the reduction of potassium permanganate in
dilute H2SO4 gives;-
                              K Mn O4   -->   Mn S  O4
(Oxidation Number)           +1 +7 -8         +2 +6 -8
This results in a change of the manganese from +7 to +2, so the equivalent
weight is 1/5 of a mole. However, in neutral solution the change would only
be 3 because the product is MnO2, giving an equivalent weight of 1/3 of a
mole. If reacted in strongly alkaline solution the product is MnO4--, giving
an equivalent weight of one mole.

The equivalent weight of a reducing agent is determined by the change in
oxidation number that the oxidised element undergoes. For the conversion of
ferrous sulfate into ferric sulfate;-
                           2 (Fe SO4)  -->    Fe2 (SO4)3
(Oxidation Number)         2x(+2 -2 )       (+3)x2 (-2)x3
The change in oxidation number per atom of iron is 1, so the equivalent
weight of ferrous sulfate is 1 mole.

There are wide range of rules about the determination of the oxidation
number, but if you have been taught to use molarity, I would not bother too
much about normality, as it is mainly used these days by analytical
chemists - because it is convenient for many common titrations. Analysts
assume that 1 ml of 1N reagent will react with 1 ml of 1N reagent. However,
there has been a recent Journal of Chemical Education article that claims
using normality and equivalent weight does help students understand
chemistry, but those concepts are unlikely to become widespread again [11].

12.9  Where can I find the composition of common named reagents?.

Often the best place to start are MSDS sheets or catalogues from commercial
suppliers. Some textbooks include a list of named reagents and their
composition that are mentioned in the text. The very common reagents are
usually also detailed in Hawley or the Merck Index. One chemistry field that
has a lot of named reagents is analytical chemistry, especially in Thin Layer
Chromatography, where many of the spray detection reagents have common names.
Merck produces a handy guide describing the composition and production of
common TLC spray reagents [12].

Some common reagents include:-
- aqua regia = 1 part nitric acid and 3 or 4 parts hydrochloric acid.
- piranha solution = highly dangerous ( explodes on contact with traces of
    organics ), warm (65C), 70:30 mixture of 100% sulfuric acid and 30%
    hydrogen peroxide. It is used, with comprehensive safety precautions,
    in the semiconductor industry, and also in some laboratories to clean
    glassware [13,14,15]. Many chemical laboratories prohibit it, and there
    are much safer, equally effective, alternatives available - refer
    Section 16.7.

------------------------------

Subject: 13. Illicit and Government Controlled Substances

Contributed by : Yogi Shan <[e-mail]>
[ mutilated by Bruce Hamilton, who agrees with what Yogi has written, but
  has tried to make the FAQ format consistent, and added his opinion. ]

13.1  What newsgroups/mailing lists discuss illegal drugs?

Current Usenet Newsgroups:
    alt.drugs
    alt.drugs.chemistry
    alt.drugs.hard
    alt.drugs.pot
    alt.drugs.psychedelic
    alt.psychoactives
    alt.hemp
    talk.politics.drugs
    alt.rave
    alt.consciousness
    rec.drugs.chemistry

Mailing lists:
    mdma/ecstasy/"E":
      To subscribe, send mail to [e-mail] with the message:
      SUBSCRIBE mdma <your name>
    psychedelics:
      Leri-L (Leri-L Metaprogramming Mail Service)
      Contact: [e-mail]
   TTIL is a moderated mailing list whose purpose is the respectful
      discussion of Psychedelic Religion.
      To subscribe send email to:  [e-mail] and put in the body
      of the message:  subscribe ttil <your email address>

There are several useful FAQs available in alt.drugs - start there with
Yogi's Clandestine Chemistry FAQ. Comprehensive overviews of illicit drug
information available on the Internet are maintained at several sites, eg
http://hyperreal.com/drugs/

13.2  Where can I obtain a list of illegal drugs?

From the "Law" Section of the "alt.drugs Clandestine Chemistry Primer/FAQ"
by Yogi Shan ([e-mail]), reproduced by permission:
   The drug statutes (possession, conspiracy, and sale), including Schedules
   I to V of the Controlled Substances Act (listing all banned and federally
   regulated drugs and precursors) are in Title 21 [of the United States
   Code] Sections 800-900 (21 USC 800-900).

   The US Code is available on the Internet:
   http://www.pls.com:8001/his/usc.html
   http://thorplus.lib.purdue.edu/gpo/

   or as gzip compressed files (by Title):
   ftp://etext.archive.umich.edu/pub/Politics/Conspiracy/AJTeel/USC/

   A current list of proscribed drugs may be obtained by writing to:
                 Drug Enforcement Administration
                 Attn: Drug Control Section
                 1405 "I" Street, N.W.
                 Washington, D.C.  20537

13.3  What is the chemical structure of common illegal drugs?

See the Merck Index for the chemical structure of your favourite poison.
Heilbron ( aka "Dictionary of Organic Compounds ), a multi-volume set,
is also excellent, and more up to date, though less commonly available.
Serious structure chasers should also check Beilstein, which often provides
far more detail of properties and structure than Merck or Heilbron.

13.4  How do I obtain chemical information on illegal drugs?

Merck, Heilbron and Beilstein all provide information on drugs that have
a significant presence in the market. Lesser-known homebake and analogues
are usually not covered, and a search of Chemical Abstracts may not even
provide information. Because of the various techniques used to "refine"
and "cut" the active ingredients, most illegal drugs are seldom
sufficiently pure to match published data. The drugs are marketed on their
pharmacological and psychological activity, rather than chemical purity
- similar to vitamin units of activity :-).  I suggest you start by reading
the various alt.drugs FAQs - they all list hardcopy references, and if they
do not identify an information source, try posting to alt.drugs or rec.drugs.

13.5  Where are the synthesis instructions for illegal drugs?

By asking the question in sci.chem, you already have signalled your level
of knowledge of illicit chemistry discussions on Usenet. You should be in
alt.drugs.* hierarchy and perhaps other groups in section 13.1 :-).

For the short answer, refer to Merck, Heilbron or Beilstein, they will
provide references to the original synthesis papers. Note that large scale
production techniques often use procedures that were developed later, and
street procedures often are significantly different, usually due to
financial, equipment, or chemical feedstock constraints.

For the long answers, see the "alt.drugs Clandestine Chemistry Primer/FAQ"
by Yogi Shan ([e-mail]), and visit some sites listed in the Network
Resources FAQ available in alt.drugs. For a fairly comprehensive overview,
( but no warranty implied for info available there ), you could start at:
http://hyperreal.com/drugs/

An interesting article on the link between methylenedioxymethamphetamine
( MDMA, ecstasy, XTC, Adam ) illegal synthesis and the sassafras tree is
available [1].

13.6  Should I post detailed recipes for illegal chemicals?

Well, if you do a lot of people will hate you. On the other hand many people
will love you. Of course, most people won't care one way or another.
Or maybe they'll just roll their eyes back, mumble something about
"dissipated/mis-spent youth", and hit the "next" button.

Posting them to sci.chem means you will be attempting to teach grandmother
how to suck eggs, most regulars of sci.chem *know* where to find the
complete instructions, how to perform the synthesis, and have authorised
access to all the equipment and chemicals. The readers of sci.chem are
probably not your target audience, and may be a little annoyed that you had
such a low opinion of their chemistry abilities. If you do not want a
lot of flames, try posting to the groups in section 13.1, they will probably
appreciate your contribution more, but will still flame you if it is wrong.

This is Usenet, do what you want as long as you think you can get away with
it. And don't ever let anyone tell you that you can't. It's a truism on
Usenet that whatever you do, someone's going to be mad at you. For every
anarchistic Free Spirit (TM), there's going to be at least one anal-retentive
busy-body who has nothing better to do that feign outrage at something or
other. Some idiot in Australia even had the nerve to flame me for posting my
Clandestine Chemistry FAQ to sci.chem, and I think drugs are terrible, and
said so. So go figure.

The only caveat to this is that posting mis-information, or information
that you personally do not understand, is likely to result in a lot of
flames. If you attempt to post anonymously to sci.chem, it is likely that
you will encounter far more opposition than if you use your email address.
As with all of Usenet, posters who sign their names to posts will be held
accountable for the content, so posting obviously incorrect or incomplete
syntheses to a group where knowledgeable chemists hang out is more likely to
harm your credibility. Your posts are unlikely to gain you further knowledge
of the synthesis, because if you post incorrect details, readers will be
pointed to the more accurate Clandestine Chemistry FAQ, and also directed to
the groups in section 13.1 to find the latest details.

In the late 1980s, and early 1990s a poster began to post all the detailed
synthesis methods from PiKAL to sci.chem. "PiKAL" is Alexander and Ann
Shulgin's standard text " Phenethylamines I Have Known and Loved [2]".
From vague memory, the poster was just listing the recipes, and not entering
into discussions or responding to questions or comments. There was the usual
outrage, but I believe he had to stop because of copyright violation of the
book he was posting - he could not demonstrate to his access provider that
he had approval from the copyright holder :-). Shulgin has now made Part Two
of PiKAL freely available, and copies are littered around the Internet, so
check out the various alt.drugs FAQs for their location.

13.7  What newsgroups/mailing lists discuss explosives?

Rec.pyrotechnics and alt.engr.explosives are two newsgroups that discuss
explosives, much to the consternation of some subscribers to the former.
The rec.pyrotechnics FAQ is excellent, and is posted regularly to
rec.pyrotechnics, news.answers, and rec.answers.

There's an "Anarchist Cookbook FAQ" posted semi-regularly to rec.pyrotechnics
and alt.engr.explosives that tells you why the AC is lousy. See also:
http://www.cwi.nl/cwi/people/Jack.Jansen/spunk/cookbook.html
    This review goes a little overboard: the mercury fulminate and picric
    acid recipes the he refers to are fine by my estimation.

See also [but no warranty implied for info available on]:
http://paradox1.denver.colorado.edu
http://www.wiretap.spies.com

13.8 What is the chemical structure of common explosives?

Exothermic oxidation-reduction reactions are the source of energy, and they
can be produced from mixtures of discrete fuels and oxidisers, or from
molecular decomposition - such as from nitroglycerine. Propellants and
explosives produce large volumes of gases, whereas pyrotechnics do not.
                                             Gas     Reaction  Ignition
                                           Volume      Heat   Temperature
                                           (cm3/g)   (MJ/KG)     (C)
Photoflash (30:40:30 Ba(NO3)2:Al:KClO4)      15       8.989      700
TNT                                         710       4.560      310

Most explosives are organic compounds or mixtures that contain carbon,
hydrogen, oxygen and nitrogen. Metallic fuels ( eg aluminium ) may be
added to increase the heat of reaction. Industrial dynamites traditionally
used nitroglycerine, nitrocellulose, and inorganic salts as sources of
oxygen, but these have been replaced by formulations that use ammonium
nitrate as the primary oxygen source. Note that the specific energy is
usually lower than the combustion of common fuels in air because the fuels
obtain their oxygen from air.

Many explosive can either burn or detonate, usually depending on the
type of initiation, confinement, and physical properties of the fuel.
When initiated, burning first occurs at an increasing rate during the first
few microseconds as it creates a high velocity, high pressure shock wave
that exothermically decomposes the explosive as it passes. The wave is
sustained by the transfer of energy from the reacted explosive to the
unreacted explosive via shock compression. The reaction rate depends on
the rate of propagation of the shock wave, rather than the rate of heat
transfer - as occurs during burning.

Explosives are usually classified into:
Low Explosives or Propellants
   eg colloidal cellulose nitrate ( smokeless powder ), black powders,
      gun and rocket propellants.
   - they are usually mixtures of chemical compounds that produce large
     volumes of high temperatures gases at controllable rates, and do not
     require atmospheric oxygen. Ammonium perchlorate and ammonium nitrate
     are commonly used as oxidisers.

Initiating or Primary Explosives ( detonators )
   eg lead azide, mercury fulminate, diazodinitrophenol (DDNP).
   - they are used to initiate the next component of an explosive chain, and
     are usually dense, organometallic compounds.
   - these are sensitive materials and fairly dangerous to handle as they
     can be ignited by heat, shock and electrostatic energy.
                                            Lead     Mercury     DDNP
                                            Azide    Fulminate
Density             (g/cm3)                 4.0        4.2       1.60
Heat of Combustion  (MJ/KG)                 2.64       3.93     13.58
Heat of Detonation  (MJ/KG)                 1.54       1.79      3.43
Gas Volume          (cm3/g at STP)           308        316       876

Detonation Velocity (m/s)                   5100       5400      6900

High or Secondary Explosives
There is a distinction between secondary and high, however many of the
common explosives are considered "secondary high explosives".
   eg cyclotrimethylenetrinitramine (RDX), 2,4,6-trinitrotoluene (TNT),
      cyclotetramethylenetetranitramine (HMX), ammonium picrate (AP).
"Secondary explosives" include trinitrophenylmethylnitramine (Tetryl),
nitrocellulose (NC) nitroglycerine (NG), pentaerythritol tetranitrate
(PETN), and nitromethane.  High and secondary explosives require explosive
shock to initiate their detonation, otherwise they would only burn if
unconfined or unshocked.
                               NG      TNT    AP    RDX    HMX   Tetryl
Density             (g/cm3)   1.59    1.65   1.72   1.85   1.90   1.70
Heat of Combustion  (MJ/KG)   6.80   15.02  12.09   9.46   9.88  12.24
Heat of Detonation  (MJ/KG)   6.29    4.23   4.31   4.54   5.67   4.63
Gas Volume          (cm3/g)    715     710    680    780    755    760
Detonation Velocity (m/s)     7600    6940   7050   8570   9160   7920
Detonation Pressure (GPa)      -      18.9     -    33.8   39.3   26.2

RDX and HMX are substantially desensitized when mixed with TNT or coating
with polymer/elastomer binders. Most RDX in the USA is converted into
"Composition B" (59.5:39.5:1 RDX:TNT:Wax)
"A5" (98.5:1.5 RDX:Stearic Acid)
"C4" (91:5.3:2.1:1.6  RDX:dioctyl sebacate:polyisobutylene:oil).
                                     Amatol                      AN
                                B     80/20   C4    AN   ANFO  Slurry
Density             (g/cm3)   1.72     -     1.64  1.72  0.93   1.40
Heat of Combustion  (MJ/KG)  11.67    4.19    -    2.62   -      -
Heat of Detonation  (MJ/KG)   5.28    4.10   6.61  2.63  3.76   3.05
Gas Volume          (cm3/g)    -       860    -     980   -      -
Detonation Velocity (m/s)     7900    5200   8340  2700  4560   6050
Detonation Pressure (GPa)     29.5     -     25.7   1.1   6.0   10.4

Note that explosives usually have less potential energy than gasoline, but
it is the high rate of energy release that produces the blast pressure.
TNT has a detonation velocity of 6,940 m/s compared to 1,680 m/s for the
detonation of pentane in air, and the 0.34 m/s stoichiometric flame speed
of gasoline combustion in air.

Other than ammonium nitrate/fuel oil (ANFO), most common explosives are
trinitrated organic compounds. Nitroglycerine (glyceryl nitrate),
trinitrotoluene (TNT), picric acid, C4 (plasticized RDX/Cyclonite),
and tetryl (2,4,6-trinitrophenylmethylnitramine), fall into this category.
Refer to Merck or Kirk Othmer for chemical structures of common explosives.

A range of Semtex plastic explosives were produced by the Semtin Glassworks
in Czechoslovakia ( now known as VCHZ Synthesia ). Semtex-H is commonly used
by terrorists and, although examples are of variable composition, it
typically contains approximately 8% oil, 9% rubber, and approximately equal
quantities of RDX and PETN, but with known composition ranges of >21.5% RDX
and <64.5% of PETN. [3,4].

ANFO was proposed in 1867, but it was the development of anti-caking agents
in the 1950s that made ANFO suitable for rock blasting. Typical commercial
ANFO blasting agents consist of 94% ammonium nitrate prills (coated with an
anti-caking agent) and 6% fuel oil. They are reclassified as blasting
explosives if the formulation is sensitised by the addition of high
explosive. ANFO explosives are usually initiated by a high-explosive booster
such as formulation B. Maximum sensitivity to initiation occurs around 2-4%
fuel oil, with the presence of water decreasing sensitivity. The recent bomb
in Oklahoma City (estimated 1800kg ANFO)[5], demonstrated the destructive
capacity of ANFO explosives.

There were solubility problems using ANFO in wet drill holes, so aqueous-
based slurries were developed. These are usually thickened suspensions
dispersed in a saturated salt solution that has been made water resistant
by the addition of hydrophilic colloids that inhibit water migration.
Ammonium nitrate-based explosives account for 97% of the US industrial
explosives.

The infamous nitrogen tri-iodide ( touch powder ) produced by the reaction
of ammonia with iodine, is not actually NI3, but a nitrogen iodide/ammonia
complex with the structure NI3(NH3)n where n = 1, 3, or 5 - depending on
conditions. NI3 has only recently been isolated, and is stable at -196C,
decomposes slowly at -78C, and decomposes spontaneously at 0C [6]. Refer to
an older inorganic chemistry text, such as "The Chemical Elements and their
Compounds"[7], for further details and references.

Recently, there has been great interest in the development of more energetic
materials, and several new compounds are expected to replace existing
materials - once manufacturing costs are reduced. Examples include;- ADN
(Ammonium Dinitramide - NH4N(NO2)2, used as a propellant by the Soviet Union),
CL-20 (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexazaisowurtzitane, aka HNIW,
the most powerful single-component explosive known - which, when combined
with a polymer binder is also known as LX19), and TNAZ
(1,3,3-trinitroazetidine) [8,9,10].

13.9  How do I obtain chemical information on common explosives?

There is an excellent, well-referenced "Explosives and Propellants" monograph
in Kirk Othmer [11] and there are also the popular books "Explosives" by Meyer
[12], and "Chemistry of Powder and Explosives" by Davis [13]. Many of the
relevant properties of fuels and explosives are found in an easily-accessible
Bureau of Mines report "Investigations of Fire and Explosion Accidents in the
Chemical, Mining, and Fuel-Related Industries - A Manual" by J.M.Kuchta [14].
There is also the "Propellants, Explosives and Pyrotechnics" journal. Merck
lists most common, and many uncommon explosives, giving their structure,
selected properties, and pointers to synthesis and more detailed information.
Shreve and Kirk Othmer also discuss explosives manufacture.

Tadeusz Urbanski wrote a massive four-volume reference set on explosives
"The Chemistry and Technology of Explosives" [15] that should be available
in any university science library (it's something like US$700 otherwise).

The "Encyclopedia of Explosives and Related Items", aka "PATR 2700"
(Picatinny Arsenal Technical Report) [16], is a U.S. Army (Picatinny
Arsenal, Dover, NJ), all-encompassing compilation (10 volumes) of
explosives properties and chemistry.  Like Urbanski, it's also quite
expensive.

13.10  What newsgroups/mailing lists discuss pyrotechnics?

rec.pyrotechnics is the "official" newsgroup for fireworks/pyrotechnics
discussions, though many have fled to the mailing lists due to the large
numbers of juvenile "mad bomber" type posts that abound.

Mark A. Buda < [e-mail] >
  The original rec.pyro exile fireworks list.
  "Mad Bomber" posts forbidden.
The Pyro Mailing List is a "Real" pyrotechnic discussion group moderated by
   a pyrotechnician.  No mad bombers.
   To subscribe apply to [e-mail] and follow the instructions.
   One must supply the info and there are reasonable guidelines to follow.
Murr Rhame <[e-mail]>
   Show-Fire entertainment pyrotechnics mailing list.
   "Mad Bomber" posts forbidden.
   To subscribe send the following one line message to [e-mail]:
   subscribe show-fire [e-mail]
Ken Harthun <[e-mail]>
   PyroTechniques, The Newsletter for Pyrotechnic Enthusiasts.  It is FREE
   for the asking. Just email me with a request to be added to the list.

See also:
   http://mercury.aichem.arizona.edu/~tip/pyro.html
   http://nickel.ucs.indiana.edu/~flinn/pyro/pyro.html
   http://fireworks.com/

------------------------------

Subject: 14. Academic Course Information

14.1  Where do I find information on US courses?

The advent of the WWW has meant that many educational institutions now have
their courses listed. A WWW search should reveal the address of most
institutions, and several of the more popular chemical courses are linked to
some of the general chemistry education sites listed in section 7.2.
Note that most US educational institutions will have a *.edu (education)
Internet address. Also check out the various Chemical Society homepages.

14.2  Where do I find information on other nations' courses?

Once again, try using the WWW, as many educational institutions worldwide
are placing course information on their home pages. It is worth remembering
that not all countries use *.edu (education), as the educational institution
address, some countries use *.ac (academic) eg vuw.ac.nz is Victoria
University in Wellington, New Zealand.

------------------------------