Journal of Scientific & Industrial Research

SAMUEL et al: NEW OPPORTUNITIES FOR RESEARCH IN COAL DERIVED CHEMICALS

Vol. 67, December 2008, pp. 1051-1058

1051

New opportunities for research in coal derived chemicals

P Samuel, S Maity, Samit Khan and S C Roy*
Central Institute of Mining and Fuel Research, Digwadih Campus, Dhanbad 828 108
Received 08 February 2008; revised 07 August 2008; accepted 26 August 2008
Some specialty chemicals are monomers for new variety of aromatic engineering plastics. Some of these monomers can
be prepared from 1-4 ring aromatics (alkylated benzenes, biphenyl, anthracene, phenanthrene, pyrene, phenol and carbazole).
Among these, 2, 6-dialkyl naphthalenes, 4, 4- dialkyl benzenes assume greater importance. By oxidation of coal and lignite
using alkaline group I metal oxide, it is possible to isolate phenolic acids and naphthalene di-carboxylic acid, which are also
important monomers for engineering plastics. By developing critical aromatic chemicals from coal, carbo-chemical resources
could contribute to high technology development leading to reduction in the cost of basic monomers. Markets with large
volume of carbo-chemicals can be further stimulated through high performance industrial carbons such as graphite, carbon
fibre as also by developing processes for manufacture of adsorbents for environmental applications such as air and water
purification.
Keywords: Coal-derived chemicals (CDCs), Carbo-chemicals, Engineering plastics

Introduction
Petroleum and natural gas presently account for more
than 90% of organic chemicals. However, principal
sources of aromatic chemicals are petroleum and coal
tar, a by-product of coal carbonization. Annual world
consumption of aromatic compounds is about 25 million
tonnes (Mt) for BTX (benzene, toluene, and xylene)
and 5 Mt for naphthalene, anthracene and other 2-4 ring
aromatic compounds1,2. Of these, about 95% of 2-4 ring
polyaromatic and heterocyclic chemicals and about
15-25% BTX are obtained from coal tar. Supplies of
petroleum will eventually dwindle, and any steep rise in
crude price brings again the need for exploiting synfuels
from coal as well as coal-derived liquids (CDLs) as
replacement for petrochemical feedstocks. There is
expanding demand for specialty materials (aromatic
engineering plastics, carbon-based materials), and
monomers that are used as feedstock to make these
materials. This is a significant new opportunity for
reviving coal-based technology.
Role of Coal in 21st Century

Secure supply of liquid hydrocarbons and direct

liquefaction to produce transportation fuels has been
*Author for correspondence
E-mail: scroy_cfri@rediffmail.com

extensively studied3,4. Even if new petroleum resources

are identified, it is not going to last beyond this century.
Thus, in 21 st century, it seems that with declining
petroleum production, CDLs will become viable options.
However, CDLs are still not effective with petroleum,
and do not seem to compete with petroleum in the near
future. Environmentally, CDLs are highly aromatic, and
need to be upgraded to a hydrogen-rich aliphatic fraction,
which would cost considerably. Middle distillates from
catalytic-catalytic-two-stage liquefaction (CCTL) contain
primarily 2-4 ring polyaromatics and conversion of these
to distillates rich in aliphatic for transportation fuels
would require extensive hydrotreating5,6. Jet fuels derived
from extensive hydrotreatment of CDLs are found to be
superior to petroleum derived jet fuels 5.
This review presents an account of research on coalderived chemicals (CDCs).
Chemicals from Coal- An Overview
Tars7 (3-4% of coal wt.) are perhaps the most generally
known source of CDCs. Coal tar components have been
used as raw materials for the production of dyes, plastics,
synthetic fibres, and pharmaceuticals and solvents8. Coal
tars and their distillate fractions are very complex
mixtures of hundreds of individual compounds,

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J SCI IND RES VOL 67 DECEMBER 2008

Fig. 1General pathways for production of some important chemicals through

pyrolysis of coal

separation and purification of which from coal tar

fractions is complex (Fig. 1).
Rise of petrochemical processing in two decades after
World War II had a major impact on coal tar chemical
industry. During first half of the last century, entire
worlds benzene supply was derived from coal. In next
10 years, this share had dropped to 50% and by 1980
only 4% worlds benzene was coal derived. At present,
catalytic reforming of petroleum feedstock or hydro
dealkylation of toluene produces most of the benzene.
Since the availability of tar world over is also decreasing
due to better technologies adopted in steel making as
also alternative routes substituting metallurgical coke,
coal tar does not seem to contribute substantially to meet
the increasing demand for aromatic chemicals. By the
early 1970s, world prices of coal tar, benzole and

ammonium sulphate had fallen to same level of the price

per ton as coal9, as a result, price of coke had to be
stepped up to reflect accurately coal prices neglecting
by-product credits for coal tar chemicals.
Use of synthesis gas (CO+H2) to produce synthetic
liquid fuels and chemicals is a well-known technology1.
Best known example, SASOL complexes, require a high
capital investment. Another successful venture by
Eastman Chemical Company at Kingsport, Tennessee
(USA) is Texaco gasification to produce syngas from
900 tpd coal. Coal liquefaction, a source of potential
feedstocks for chemicals, could be prospective market
for coal (130 MTA)10. However, it could be possible for
exclusive aromatic nature of CDLs9; some of these can
be exploited as high value specialty chemicals
(engineering polymers). Occidental Research

SAMUEL et al: NEW OPPORTUNITIES FOR RESEARCH IN COAL DERIVED CHEMICALS

Corporation (ORC) developed a process for oxidation

of bituminous coal in presence of potassium acetate and
water with a yield of 34% terephthalic acid11. Direct coalto-chemicals conversion is a new approach adopted by
ORC. A hypothetical example of the ideal target might
be the synthesis of high yields of naphthalenes and
decalins by carefully selecting a coal feedstock to be
rich in naphthalene moieties and catalytically
hydrogenating coal to remove aliphatic cross links and
reduce ring systems12.
Carbo Chemicals - New Approach

While fractions of coal tars may have non-substituted

aromatics, coal liquefaction products have alkyl
substituents to ring system. This problem can be
overcome by either pyrolytic liquefaction (short-contacttime) followed by catalytic dealkylation13 or catalytic
liquefaction at lower temperatures followed by thermal
hydrodealkylation at a higher temperature. These
approaches may become promising for large volume
aromatics and can become competitive if improved
separation methods emerge. An alternative is to explore
introducing a reagent into coal to cleave certain specific
bonds. A significant number of aromatic systems in low
rank coals (lignite and sub-bituminous coals) contain
only 1-2 rings14,15. Major aromatic structures of low-rank
coals are phenol, alkyl phenols, catechol, alkyl catechols,
toluenes, xylenes and other alkyl benzenes as well as
some alkyl naphthalenes in small quantities. High rank
coals represent 2-4 ring aromatic structures. A careful
oxidation should be able to produce large yields of
benzene carboxylic acids. Long chain aliphatic units may
be present in some coals, which can be recovered by
clipping chain ends.
Use of Aromatic Chemicals in Polymers - Value Addition

Worldwide consumption of synthetic polymers is:

plastics, 56; fibers, 18; synthetic rubber, 11; and coatings
& adhesives, 15%. In general, polymers are divided into
thermoplastic and thermosetting materials; later being
epoxy and phenol formaldehyde resins. Based on end
use, plastics can be divided into commodity plastics
(polyethylene, polypropylene, polyvinyl chloride and
polystyrene) and engineering plastics [polyamide/nylon
(PA), polyacetal (PA), polycarbonate (PC),
polyphenylene oxides (PPO)]. Thermoplastic polyesters
include polybutylene terephthalate (PBT), polyethylene
terephthalate (PET), polyarylate (PAR) and high
temperature heat resistant polymers [polyimides (PI) and

1053

polyamide imide (PAI)]. Engineering plastics (EPs), being

superior in mechanical properties and possessing high
durability, compete with metals, ceramics and glasses in
a variety of applications. EPs are primarily used in
transportation (cars, trucks and airoplanes), construction
(housing, plumbing and hardware), electrical and
electronic parts (business mechanics and computers),
communications (VCR, TV, telephones) and consumer
goods (cookware) (Table 1).
Heat resistant polymers (Table 2) have significant,
commercial impact. Du Pont started production of high
performance polyimide film (Kapton), which is produced
from pyromellitic dianhydride (PMDA) and bis
4-aminophenyl ether. Another type of heat resistant resin,
a polyester (mp 450C) produced by condensation of
p-hydroxybenzoic acid, is marketed by Sumitomo
(Ekonol E 101). Polybenzimidazole (PBI) is produced
by reaction of 3, 3'- diaminobenzidine with diphenyl
isophthalate.
Liquid crystalline polymers (LCPs) are divided into
thermotropic and lyotropic groups. Thermotropic
polymers exhibit crystallinity in molten state while
lyotropic in solution state. Thermotropic LCP containing
naphthalene or biphenyl rings are capable of replacing
metals and ceramics in many applications. Xydar
marketed by Amoco has three monomers (4, 4-biphenol,
p- hydroxybenzoic acid and terephthalic acid). Xydar
was originally developed for use in cookware and can be
used at 240C for 100,000 h. There are several
commercial grades of Vectra LCPs, including bulk LCP
and its composites with glass fibres, carbon fibres and
minerals. Conductive and heat resistant polymer films
can be prepared by electrochemical polymerization of
naphthalene/ carbazole.
Polyaromatics (pyrene and phenanthrene) can be used
to make condensed polynuclear aromatics (COPNA)
resins. Coumarone (benzofuran)-indene resins (coal tar
resins) are also thermoplastic aromatic resins, which are
made from catalytic polymerization of coal tar naphtha
fraction freed from acids and bases, and used in coatings
together with film-forming materials such as drying oils.
Coal derived Aromatic Chemicals

Large volume applications of EPs, high temperature

heat resistant resins and thermotropic and lyotropic LCPs
depend on the availability and cost of monomer. Coal is
intrinsically rich in aromatics, and coal liquids are
composed primarily of 1-4 ring aromatic and phenolic
compounds, which could contribute to further
development of aromatic monomers. Many aromatic and

1054

J SCI IND RES VOL 67 DECEMBER 2008

HO

HOOC

OH

COOH

HOOC

P-hydroxy benzoic acid

Terephthalic acid

4-4'biphenol

OH

OH

COOH

HO

HOOC

COOH
HO

2,6dihydroxy naphthalene
2,6-naphthalene dicarboxylic acid

6-hydroxy-2naphthoic acid
O

OH

HO

4,4'dihydroxy diphenyl

COOH

HOOC

4,4'diphenyl dicarboxylic acid

O
O

O
O
pyromelletic dianhydride

O
O
O
Phthalic anhydride

Scheme 1
heteroatom containing compounds can be converted into
monomers for high performance polymers (Scheme 1).
Many of these monomers can be obtained by oxidation
of corresponding alkyl aromatics. Because alkyl chains
on aromatic rings can be readily oxidized to COOH or
OH groups, investigation should be to prepare 2, 6 dialkyl
naphthalene (2, 6 DAN) and 4-4' dialkyl biphenyl (4, 4
DAB). Oxidation of these two compounds readily give
2, 6 naphthalene dicarboxylic acid (2, 6-NDCA) and
4, 4 -biphenyl dicarboxylic acid (4, 4 BDCA)
respectively. There is a possibility to synthesize 2, 6
NDCA from coal chemicals. Catalytic synthesis of 1, 4
- xylene, terephthalic acid and p-hydroxybenzoic acid
can be extended for synthesis of disubstituted naphthalene
and disubstituted biphenyl derivatives. Shape selective
catalysts can be used in preparing 4, 4' - disubstituted

biphenyl derivatives and 2, 6 - dialkyl naphthalenes12.

Carbonylation of alkylated or halogenated naphthalene
under mild conditions can also yield derivatives of
naphthalene. Mitsubishi Gas has developed a process
for producing 2, 6 NDCA from methyl naphthalene
+ CO (HF - BF3 catalyst).
Pyromelletic dianhydride (PMDA) is prepared by
carbonylation of trimethyl benzene, while trimelletic
anhydride (TMA) is prepared by carbonylation of xylene
using HF - BF3 acid as catalysts followed by oxidation
and dehydration. Celanese is sole manufacturer of
napthalene tetra carboxylic acid (NTCA), which is
prepared by oxidation of pyrene, which on further
dehydration gives NTCADA (dianhydride). NTCADA
with 3, 3'-diamino benzidine or 1, 2, 4, 5 - tetra aminobenzene reacts to provide heat resistant materials.

1055

SAMUEL et al: NEW OPPORTUNITIES FOR RESEARCH IN COAL DERIVED CHEMICALS

Table 1Aromatic polymer plastics and their utility

1. Polyethylene terephthalate (PET)
6. Polysulphones (PS)

CH3

(CH2)2

CH3

Uses % As a fibre in tyre cords, yacht sails, electrical insulations,

manufacture of gear wheels, base for photographic films, typewriter
ribbon, and magnetic tapes including VCR tapes, soft drink bottles.
2. Polybutylene terephthalate (PBT)

Uses % Can withstand repeated steam sterilization used for medical

devices. Used in pipe, flow meters, fuel cells, membranes, microwave
cookware and electrical application. Used in combination with
polydimethyl siloxane for gas separation.
7. Polyether ether ketone (PEEK)

(CH2)4

Uses % Material with high thermal resistant (up to 140C) and

mechanical properties. Blends with PET and PC.

Uses % High melting point (330C) used in military and radiation

resistant parts. Wire/ cable insulation, compressor and machine parts

3. Polyethylene naphthalate (PEN)

8. Polyimides (PI)
C

(CH2)2

O
O

O
n

Uses % Films and VCR tapes, optical brightness

n

4. Polyarylates (PAR)
Uses % Light weight- heat resistant (400C) materials for aerospace
industry. Infusible, flame resistant and insoluble in all solvents. Also
used in seals, bearings, gear wheels pistons, back up rings and disk
brakes. Electronic PCBs, slot liners, wire and cable insulators and
wire enamels.

CH3
C

CH3
n

Uses % Electronics/ medical/ mechanical/ automotive products,

traffic lights, aircraft parts.

5. Polyphenylene oxide (PPO)

CH 3

9. Polybenzimidazole (PBI)

H
N

H
N

N
H

N
H

O
CH 3

Uses % High softening point (210C), used in automotive parts,

computer, electrical, business and telecommunication equipment.

Uses % Flame resistant (450C) fibres for safety gloves, astronauts

clothing, and membranes for reverse osmosis

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J SCI IND RES VOL 67 DECEMBER 2008

10. Poly P- phenylene terephthalamide

11 Polycarbonates (PC)
O

O
HN

NH

CH3

(PPTA)

C
O

CH3

Uses % Used with polyester blends in the manufacture of transparent

materials in medical appliances, automobile parts

Uses % Used in tyre cord, special clothing (bullet proof vests),

components of helicopters

S-OHA

S-OHP
O

HOOC

COOH

HOOC

COOH

Scheme 2
O

COOH

9, 10 phenanthraquinone
HOOC

Diphenic acid

HOOC

COOH

4, 4-BDCA

Scheme 3
Phenanthrene can be obtained in relatively high yields
from coal pyrolysis. During hydrogenation of anthracene
(Lewis acid), sym-Octahyrophenanthrene (s-OHP) and
phenanthrene were produced 16,17. s-OHA was also
produced from phenanthrene during its reaction over some
acidic catalysts12-17. Therefore, s-OHP can be obtained
in good yield18-19 by using Ni-W / Al2O3 catalysts and
further isomerization of s-OHP to s-OHA (Scheme 2).
Dehydrogenation of s-OHA gives anthracene, which
has large volume application in dye industry and also an

intermediate for H2O2 and pulping agent (anthraquinone).

PMDA is an important monomer for polyimides (Du
Ponts Kapton). Another way of utilizing phenanthrene
is the synthesis of 4, 4 biphenyl di carboxylic acid
(Scheme 3).
Biphenyl compounds are not abundant in coal liquids,
which contain phenanthrenes, beside fluorenes,
dibenzofurans and dibenzothiophenes, which can be
converted to biphenyl type compounds through catalytic
hydrocracking.

SAMUEL et al: NEW OPPORTUNITIES FOR RESEARCH IN COAL DERIVED CHEMICALS

1057

Table 2Typical aromatic polymer materials

Polymer material
General
Polyethyleneterephthalate(PET), m p
Engineering
260C
Plastics
Polybutyleneterephthalate(PBT), m p
228C
Polyarylate (PAR), m p 234-235C
Polyethylene naphthalate (PEN), m p 255C
Polycarbonates (PC), m p 267C
Polyphenylene oxides (PPO), m p 250C
Polysulphones (PS), m p 350C
Polyether ether ketone (PEEK), m p 314C
High
temperature
heat resistant
plastics

Polyimides (PI), mp 400C

Polyimide sulphone (PIS), m p 200350C
Polyamide imide (PAI), m p 489C
Polybenzimidazole (PBI), m p 760C

Liquid
Crystalline
Polymers

Thermotropic co-polyesters
p-Hydroxybenzoic acid(HBA)+4,4'biphenol+ Terephthalic acid (TPA)
HBA+ 6, hydroxy - 2 naphthoic acid +
TPA
HBA+Polyethylene terephthalate
Lyotropic LCP
Poly-phenylene terephthalamide (PPTA)

Oxidation of Coal using Group I Metal Oxide as Catalyst

P- hydroxy benzoic acid, a phenolic acid and

2,6-naphthalene- di carboxylic acid are important
monomers for EPs. By oxidation of coal/lignite using an
alkaline group I metal oxide catalyst26, it is possible to
isolate phenolic acids and naphthalene- di carboxylic acid
(Scheme 4).
MIO-NaOH
RO

CH2 OR

OH

COOH

P-hydroxy benzoic acid

[R= Alkyl (C

2),aryl]
Scheme 4

Currently, coal tar pitch and bituminous coal used for

coke making are major feedstocks for coal based carbon
materials. In future, heavy liquids from coal liquefaction
and low temperature pyrolysis tars and coals of all ranks
can become feedstocks. Adsorbent carbons for water/
air purification, medical applications and developing
carbon molecular sieves should be main uses from such

Manufacturer/Trade name
Eastman (Kodapak), Goodyear (Cleartuf),
Celanese, ICI
G.E (Valox, VCT); Celanese (Celanex)
Unitika (U-polymer), Amoco (Ardel), Du Pont (Arylon),
Celanese (Durel).
Teijin (Q-film), Amoco (PEN)
GE (Lexan), Mobay (Mark rolon); Dow (Calibre)
G.E (Noryl)
Union carbide (Udel); ICI (Vitrox)
ICI (Victrex)
DuPont (Kapton), Ubekosan (PI)
NASA (PIS)
Amoco (Torlon)
Celanese (Celazole)

Amoco(Xyder), Sumitomo (Ekonol E

2000, E 6000)
Hoechst Celanese (Vectra), ICI (Victrex,
SRP -2)
Eastman (X++++7G), unitilea (LC), Mitsubishi (EPE)
Du Pont (Kevlar), Akzo (Twaron)

feedstock. Coal used worldwide for the production of

activated carbons and carbon molecular sieves is
estimated at 200000 TPA and 3000 TPA respectively.
Application of carbon molecular sieves in pressure-swing
adsorption is commercially viable and Air Products are
using for air separation. Kureha Kagaku first marketed
petroleum pitch carbon fibres in 1970. Singer had
pioneered in carbon fibres from mesophase pitch, which
led to Union Carbides process for making mesophase
pitch-based high-performance carbon fibre20. Carbon
fibres are now commercially produced by Kureha (950
TPA), Amoco (acquisition from union carbide, 230 TPA)
Ashland petroleum (95 TPA), Nippon Sekiyu Kagaku
(50 TPA) Kagoshima at its subsidiary (Petoca Ltd., 12
TPA) and recently by Du Pont and Idemitzu. Mitsubishi
chemicals (500 TPA) and Osaka Gas (300 TPA) have
announced commercial production through their
subsidiaries12.
Graphites and other advanced carbon materials offer
a new market opportunity for anthracites. Developing
schemes to replace petroleum products would add
significant value besides creating demand for anthracite.

1058

J SCI IND RES VOL 67 DECEMBER 2008

Replacing 25% of petroleum coke would create a market

of 1.5 Mt for anthracite.
Third allotropic carbon (fullerenes of C60 and C70
carbon clusters) can be prepared from graphite and
coal20-21. Kratschmer et al22 developed a method using
an electric arc to produce C60 and C70. Preparation of
fullerenes (yield 2-3%) from coals is also carried out at
CSIRO, Australia23,24. Coal is initially converted to coke
at 1000-1300C and subsequently subjected to electric
arcing in helium atmosphere25.
Conclusions
For coal-to-chemicals, there is need to give fresh
emphasis on evaluation of existing basic data and fill
gaps by further research on structural aspects of coal,
reactivity, catalytic conversions, and new pretreatments,
novel reactions, super critical extractions, and advanced
coal liquefaction methods. In new approach, coal to
aromatic chemicals to specialty chemicals (2,6dialkylnaphthalene), may give value addition through
engineering plastics. In India, where petroleum and gas
reserve are less compared to coal reserve, reassessment
is needed.
Acknowledgements
Authors thank Director,CIMFR, Dhanbad for
permission to publish the paper. Authors also thank Dr
A Sarker, Scientist, CIMFR,Digwadih Campus, for
valueable discussion in writing the manuscript.

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