Übersichtsbeiträge/Reviews
Oleochemical esters – environmentally compatible raw
materials for oils and lubricants from renewable resources*
Due to the increasing market relevance of environmentally labelled
products, the ecological properties of oleochemical esters have been
intensively studied within the last couple of years. In general, their
aquatic toxicity is very low or almost negligible, and they are readily
biodegradable in most cases. They have not to be labelled as “danger-
ous for the environment” according to the EU Dangerous Substance
Directive. Their origin from renewable resources results in lower net
CO2-emissions (”global warming”) compared to petrochemical prod-
ucts. Not many lubricants have such rather positive ecological profiles.
Thus, most of them are classified in the most favourable water hazard
class, i.e. in WGK 0. In addition, they fulfill the requirements of
several European environmental labels, e.g. “Blauer Engel”. These
favourable ecological properties together with their well established
technical performance recommend the oleochemical esters as suitable
base oils for the development of high performance “green” oil and
lubricant products.
1 Introduction
Today the general public is quite sensitive for environ-
mental issues, and consumers (including industrial cus-
tomers) demand environmentally compatible oil and lubri-
cant products with a good technical performance at a reason-
able price. Whereas mineral oil based products can fulfill the
last two criteria quite well, they are less favourable from an
ecological point of view. Oleochemical esters (i. e. synthetic
esters derived from renewable resources like natural fats and
oils) could be a “green” alternative, exhibiting very good or
even superior technical performance combined with very
favourable ecological properties. These properties have been
thoroughly studied over the last couple of years. The studies
show that oleochemical esters are easily biodegradable in
soil and in the aquatic environment, and that they have a low
aquatic toxicity. The excellent biodegradability of the oleo-
1 Henkel KGaA, Düsseldorf, Germany.
* Paper presented at the 52nd International Congress and Expo of the
DGF, September 13–15, 1998, Magdeburg, Germany.
192 Fett/Lipid 101 (1999), Nr. 6, S. 192–198 © WILEY-VCH Verlag GmbH, D-69451 Weinheim, 1999
Andreas Willing1
Oleochemische Ester – umweltverträgliches Ausgangsmaterial
für Öle und Schmierstoffe aus nachwachsenden Rohstoffen.
Die Öffentlichkeit ist heutzutage in Fragen des Umweltschutzes sehr
sensibel, und die Verbraucher (insbesondere auch die industriellen
Kunden) verlangen zunehmend Produkte mit entsprechend günstigen
Umweltkennzeichnungen. Vor diesem Hintergrund sind die ökolo-
gischen Eigenschaften oleochemischer Ester (d. h. synthetische Ester,
deren Säure- und/oder Alkoholkomponenten aus nachwachsenden
Rohstoffen wie tierischen oder pflanzlichen Ölen und Fetten stammen)
in den letzten Jahren eingehend untersucht worden. Dabei zeigte sich,
daß oleochemische Ester für Wasserorganismen weitgehend untoxisch
und unter Umweltbedingungen (sowohl im Boden als auch im Wasser)
schnell und leicht biologisch abbaubar sind. Ihre gute biologische Ab-
baubarkeit und die Tatsache, daß sie aus nachwachsenden Rohstoffen
stammen (Verminderung der CO2-Emission und des Beitrags zum
„Treibhauseffekt“), zeichnen die oleochemischen Ester dabei gegen-
über vergleichbaren Mineralölprodukten aus. Aufgrund ihrer guten
ökologischen Eigenschaften sind oleochemische Ester nicht als „um-
weltgefährlich“ (gemäß der 1994 in Kraft getretenen 4. Novelle der Ge-
fahrstoffverordnung) zu kennzeichnen. Hinsichtlich der in Deutschland
besonders wichtigen Einstufung in Wassergefährdungsklassen sind die
meisten oleochemischen Ester in die günstigste Wassergefährdungs-
klasse (d. h. WGK 0, im allgemeinen nicht wassergefährdend) einge-
stuft. Ferner erfüllen die oleochemischen Ester i.d.R. die Anforderun-
gen verschiedener Umweltzeichen für besonders umweltverträgliche
Schmierstoffprodukte, wie des in Deutschland gebräuchlichen „Blauen
Engels“. Ihre hervorragenden ökologischen und anwendungstechni-
schen Eigenschaften machen oleochemische Ester somit in idealer Wei-
se als Rohstoffe für die Entwicklung von Hochleistungsschmierstoffen
für die verschiedenen industriellen Anwendungsbereiche geeignet.
chemical esters originating from renewable resources gives
them an ecological advantage over comparable products
from petrochemical origin. With regard to the German Water
Hazard Class (“Wassergefährdungsklasse”, WGK) most of
them are classified as WGK 0 (“in general not water pollut-
ing”). According to the forthcoming WGK classification
scheme – the so-called “R-phrase”2 concept –, which cur-
rently is under development by the German authorities, oleo-
chemical esters could even become non-classified due to
their non-water polluting properties. These favourable eco-
logical properties, together with their well established tech-
nical performance, make oleochemical esters ideally suited
as raw materials for the development of ecologically superi-
or high performance lubricants for many different industrial
and automotive applications, e.g. hydraulic oils, metal work-
ing fluids, and gear oils (Fig. 1). This article gives an over-
view about the physico-chemical and ecological properties
2 R-phrase refers to the risk phrases of the EU Dangerous Substance
Directive, e. g. R-22, harmful if swallowed.
0931-5985/99/0606-0192$17.50+.50/0

Fig. 1. Field of technical application of oleochemical esters.
of oleochemical esters, and focusses on the environmental
compatibility and classification of the different groups of the
oleochemical esters.
2 Structure and Physico-Chemical
Properties of Oleochemical Esters
The structure of oleochemical esters is characterized by
one or more carbon ester bonds in the molecule and by alkyl
chains originating from oils and fats, i.e. the energy storage
molecules of plants and animals. A typical animal fat is
tallow (less common fish oil). Plant oils are mainly produced
from coconuts, palm, and palm kernel, rapeseed, soy bean,
and sunflowers. Due to their biochemical synthesis the cor-
responding fatty acids and their derivatives (e.g. the fatty
alcohols) have even numbered, linear alkyl chains, ranging
from 8 to 22 carbon atoms (C8–C22). The specific structure
of their alkyl chains determines to a great extent the physico-
chemical as well as the ecological properties of the oleo-
chemical esters, especially their biodegradability. From a
chemist’s point of view, oleochemical esters can be divided
into four groups (Fig. 2).
The physico-chemical properties of oleochemical esters
can cover the complete spectrum of technical requirements
for the development of high-performance industrial oils and
lubricants (e. g. excellent lubricating properties, good heat
stability, high viscosity index, low volatility, and superior
shear stability). For a comprehensive review of their techni-
cal properties see [1]. A drawback, however, is their higher
Fig. 2. Structure of the different types of oleochemical esters.
Fett/Lipid 101 (1999), Nr. 6, S. 192–198
price compared to mineral oil based products. Although all
members of the above-mentioned groups have some physico-
chemical characteristics in common (low water solubility,
low vapour pressure), additional structural features have a
significant influence on their physico-chemical and technical
properties. Polyol esters are more heat stable than glycerol
esters due to the presence of a quarternary carbon atom. The
presence of double bonds, on the other hand, makes the
esters susceptible to oxidation and reduces their temperature
stability. Branched alkyl chains of the alcohol component
improve the low temperature properties and the hydrolytic
stability of the molecules, but reduce their viscosity index.
Thus, the different oleochemical esters have different techni-
cal properties, and some of the desirable properties do indeed
exclude each other. However, referring to the know-how of
research and development (R&D) and application experts,
for almost all applications a suited oleochemical ester can be
selected from the great variety of existing structures.
3 Ecological Assessment of
Oleochemical Esters – Basic Aspects
The intention of an ecological (risk)assessment is to
answer the question, if the use of the substance under con-
sideration is environmentally compatible or not. Therefore,
any ecological assessment has to cover the following two
aspects: the inherent ecotoxicological properties of a sub-
stance (hazard) and the environmental fate of the substance
(exposure scenario). A comprehensive discussion of the
systematics of an ecological safety assessment can be found
in [2].
3.1 Ecotoxicity
Ecotoxicity data describe the toxic effects of chemicals on
organisms in the environment. Because it is not feasible to
investigate all the different wildlife species in the laboratory,
it has generally been agreed to evaluate the ecotoxicity of a
substance by testing only certain standard species, represent-
ing the different levels of the natural food chain (Fig. 3). For
the aquatic compartment the fish, daphnia, algae, and bacte-
ria are the most relevant test organisms, and standardized test
methods, such as laid down for example in the OECD
“Green pages”, i.e. OECD methods 201-210 [3], have been
established for these end points (Tab. 1). The ecotoxicologi-
cal tests can be divided into two groups: acute tests investi-
gate the effects of high concentrations of chemicals during a
relatively short time of exposure (determination of lethality
= LC50-value or of other relevant effects = EC50-value),
whereas subchronic and chronic tests investigate long-term
effects at sublethal concentrations (determination of the No
Observed Effect Concentration = NOEC). The environmen-
tal classification of substances is usually based on data from
acute tests. If a substance is readily biodegradable and acute
Tab. 1. Standard ecotoxicity tests.
Type Test organism Test method
Acute tests Algae OECD 201
Daphnia OECD 202/1
Fish OECD 203
Bacteria OECD 209
Chronic tests Daphnia OECD 202/2
Fish OECD 204
193
 Fig. 3. Scheme of the aquatic food chain indicating the
different trophic levels for ecotoxicity testing.

test data do not indicate an increased ecotoxicity, there is

generally no need to conduct the more costly chronic tests.
On the other hand, for high volume chemicals, that are
forseen to be quantitatively discharged into the waste water
(like e.g. detergent components), determination of chronic
data is necessary to conduct a reliable risk assessment.
3.2 Environmental fate
The most important aspect with regard to the environ-
mental fate of a substance is its biodegradability. Biodegrad-
ability means that a substance is susceptible to biochemical
breakdown by the action of microorganisms (Fig. 4). The
first breakdown step (i. e. the disappearance of the original
molecule) is called primary degradation. Determination of
primary degradability is of main relevance for surfactants
due to specific legal requirements (detergent law). Of con-
siderably more general importance is the determination of
the ultimate degradability (mineralization) of substances to
CO2 and H2O (and, at the same time, the formation of bio-
mass). A very special test is the so-called CEC test, original-
ly developed for two-stroke engine oils, because it does not
clearly differentiate between primary and ultimate degrada-
tion [4]. Nowadays the CEC test is of relevance only for the
German environmental label “Blauer Engel”, but will be re-
placed in the near future by tests for true ultimate biodegrad-
ability. Ultimate biodegradability guarantees the safe reinte-
gration of the organic material in the natural carbon cycle.
Simple but rather stringent standardized test methods have
been established for the investigation of ultimate biodegrad-
Tab. 2. Standard screening tests for ready biodegradability.
Type Species Parameter* Method
“official” DDAT DOC OECD 301 A
screening Sturm test CO2 OECD 301 B
tests MITI test DOC OECD 301 C
Closed Bottle test BOD/COD OECD 301 D
MOST DOC OECD 301 E
Manometric BOD/COD OECD 301 F
Respirometry test
Fig. 4. Primary and ultimate biodegradation of organic substances.
ability (Tab. 2). They are laid down for example in the
OECD “Yellow pages”, i. e. OECD methods 301 A-F [3], or
ISO standard methods, e. g. ISO 10707 and 10708. Sub-
stances surpassing the biodegradation limiting values for
“ready biodegradability” in these tests (i. e. 60% of CO2-evo-
lution or oxygen consumption (BOD/COD) or 70% removal
of dissolved organic carbon (DOC), and fulfilling the 10-day
time window criteria) are regarded as fast and ultimately
biodegradable in the environment. The evaluation if a sub-
stance is readily biodegradable or not is very important for
its environmental classification, and the determination of its
water hazard class. For some applications, e. g. drilling fluids
for off-shore oil production, also degradability under anaer-
obic conditions, as encountered on the seafloor, is highly
desirable. In addition to biodegradability, bioaccumulation
behaviour (i.e. the potential of a chemical to concentrate in
animal tissues) is also important with regard to the evalua-
tion of a possible long-lasting adverse impact to biota3.
However, the ester linkage of the oleochemical esters is sus-
ceptible to enzymatic cleavage, and the liberated natural fat-
ty acid and alcohol components can be metabolized. There-
fore, oleochemical esters are not expected to bioaccumulate
in biota despite of their log Pow4 >> 3.

other screening BODIS test BOD/COD ISO 10708

tests CO2-Headspace test CO2 ISO 14593
* The limiting value for ready biodegradability is 60% (BOD/COD or 3 biota = all living organisms, i.e. animals, plants and microorganisms.
CO2) and 70% (DOC), respectively, within 10 days after the onset of 4 Pow = partition coefficient of a substance between an octanol and a
degradation. water phase.

194 Fett/Lipid 101 (1999), Nr. 6, S. 192–198


Fig. 5. Elements of an ecological risk assessment.
3.3 Ecological risk assessment
Ecotoxicity as well as biodegradability tests determine the
environmentally relevant substance-inherent properties of
chemicals and do not include the aspect “exposure”. Thus,
the fact that a substance is toxic to aquatic organisms or that
it is poorly biodegradable does not per se mean that this sub-
stance actually exerts adverse effects to the environment. To
address this question a risk assessment has to be conducted.
A schematic view of the elements of an ecological risk
assessment is shown in Fig. 5. Very generally speaking, an
ecological risk assessment simply compares the predicted
environmental concentration (PEC) of the chemical under
consideration with the predicted ecotoxicological limit con-
centration (PNEC) that is expected to be tolerated even by
the most sensitive aquatic organisms without adverse effects.
If the quotient PEC/PNEC is lower than 1, the use of such a
substance is considered to be environmentally compatible.
4 Testing of Water-Insoluble Substances
The experimental investigation and the assessment of the
ecological properties of water-insoluble substances (like
Fett/Lipid 101 (1999), Nr. 6, S. 192–198
oleochemical esters) is not trivial. However, the problems
associated have been overlooked for a long time. Testing of
poorly watersoluble substances requires special knowledge
and experimental skills. The first difficulty is to get the
necessary information about the water solubility of a test
substance. Usually water solubilities are not determined very
precisely (e.g. in mg/l). Instead, verbal descriptions are
given in the Safety Data Sheet like “insoluble” or “of low
solubility”. Whereas the statement “insoluble” could still
mean a solubility of 0.1% (i. e. of 1,000 mg/l), determination
of the real water solubility of substances described as “of
low solubility” could yield values in the range of < 20 µg/l.
Thus, if there is any uncertainty about the water solubility of
a test substance it is advisable to determine this parameter
experimentally or, in the case of degradation tests, determine
at least the TOC/DOC ratio (total organic carbon/dissolved
organic carbon). Whereas it is rather trivial that degradation
tests, which are analytically based on the DOC-parameter,
are not suitable for the investigation of insoluble substances,
the proper choice between the other available test systems is
not easy. The situation is even more complicated with re-
spect to ecotoxicity testing. Especially the determination of
EC50-values for algae and daphnia can be biased by insolu-
ble portions of the test substance floating on the surface of
the test media. If these small test organisms get to the sur-
face, they can be physically trapped in the organic layer. This
phenomenon is in fact hardly distinguishable from immobi-
lization caused by systemic toxicity of the test substance.
Thus, an overestimation of the toxicity may be the result.
To avoid such misleading results industry and the German
Environmental Protection Agency (UBA) have agreed on a
special test protocol for water insoluble substances (Fig. 6).
It is based on testing of Water Accommodated Fractions
(WAF). WAFs are prepared by stirring the test substance for
at least 24 h in water, and subsequently removing the insolu-
ble portions by an appropriate method, e.g. by filtration. If it
has been shown that WAFs up to a loading of 100 mg/l are
not toxic, an EC50 > 100 mg/l can be used for environmental
classification. However, with regard to WGK 0 it has to be
shown that even up to a loading of 10,000 mg/l the resulting
WAF is not toxic.
Fig. 6. Scheme for testing and evaluating
water-insoluble substances.
195
5 Ecological Properties of
Oleochemical Esters
5.1 Fatty acid esters
The common fatty acid esters for lubricants consist of
long-chain linear fatty acids of 8 to 18 carbon atoms (from
plant or animal feedstock), that are esterified with short to
medium-chain length synthetic (mainly branched) alcohols
of 4 to 13 carbon atoms. Against fish and bacteria these
mono esters are only scarcely or not toxic (LC50-values in
the range of 1,000–10,000 mg/l), certainly due to their very
low water solubility (Tab. 3). In the 301 A–F OECD tests for
ready biodegradability, or comparable stringent ISO tests
(e.g. the BODIS-test, Biological Oxygen Demand of Insol-
uble Substances, ISO 10708), they exhibit high degradation
rates, generally exceeding the level for ready biodegradabil-
ity (Tab. 4). This result might be a surprise for those expect-
ing poor biodegradability of insoluble substances. Although
degradation of water insoluble substances is, compared to
homogeneously distributed soluble substances, certainly
rendered more difficult due to the limited bioavailability of
the test substance, these results show that biodegradability is
mainly determined by chemical structure and less by water
solubility. Mineral oils are degraded under these conditions
to only 20–50% BOD/COD, i.e. they cannot be regarded as
readily biodegradable. Fatty acid esters are classified in
WGK 0, whereas mineral oil, due to its limited biodegrad-
ability, is generally classified in WGK 1. In addition, fatty
acid esters are biodegradable under anaerobic conditions,
too, whereas mineral oils are not [5].
5.2 Glycerol esters
Glycerol esters consist of the natural, tri-functional alco-
hol glycerol esterified with one to three moles of linear fatty
acids. Both components usually originate from renewable
resources. Their identity with natural lipid structures results
in the very favourable ecological properties of the glycerol
esters (Tab. 3 and 4). They are not toxic for fish and bacteria,
and they are almost quantitatively biodegraded within 28
days, even under the stringent OECD screening test condi-
tions. In addition, they are easily biodegradable under anaer-
obic conditions, too. Therefore, glycerol esters are officially
classified as WGK 0 by the Commission for the Evaluation
of Water Polluting Substances (KBwS).
5.3 Polyol esters
Polyol esters consist of multifunctional synthetic alcohols
esterified with long-chain linear fatty acids of 8 to 18 carbon
atoms (of plant or animal origin). In contrast to glycerol,
which is devoid of a quarternary carbon atom, the synthetic
polyol esters contain at least one quarternary carbon atom,
which improves the chemical stability of the molecule.
This increased stability is reflected by the slightly reduced
degradation rates compared to the glycerol esters (Tab. 4).
However, polyol esters are still readily biodegradable, and
reach sufficiently high degradation rates even in degradation
tests with reduced bacterial inoculum (i.e. surface-water
conditions, as required for a WGK 0 classification). Like
glycerol esters, polyol esters are almost not toxic for aquatic
organisms (Tab. 3). Because of their great economic im-
portance due to their excellent technical performance, the
ecological properties of these substances have been exten-
sively investigated (i. e. data for additional aquatic species
like algae and/or chronic toxicity studies are available,
too). On the basis of these data the polyol esters certainly
qualify for WGK 0, even with regard to the aggravated
requirements of the latest amendment of the corresponding
administrative regulation (VwVwS) of April 18, 1996 (see
below) [6].
5.4 Complex esters
Like polyol esters, complex esters consist of a multifunc-
tional synthetic alcohol and long-chain linear fatty acids of
preferably 18 carbon atoms (of plant or animal origin). They
differ from the normal polyol esters by the fact that esterifi-
cation is done in presence of suitable dicarboxylic acids like
adipic acid acting as a cross-linker. Depending on the type
and the molar ratio of the educts, medium- to high-viscosity
products with special technical properties are obtained via
this synthetic pathway. The toxicity of the complex esters
towards fish, daphnia, and bacteria is comparable to the
normal polyol esters, i.e. it is rather low (Tab. 3). Biodegrad-
ability, however, is significantly influenced by the degree of
cross-linking in the molecule (Fig. 7). Whereas the 68 cSt-
and 140 cSt viscosities are readily biodegradable even under

Tab. 3. Ecotoxicological properties of representative oleochemical esters.

Ester type Substance (example) Fish toxicity (LC50) Daphnia toxicity (EC50) Bacteria toxicity (EC0)
Fatty acid ester 2-Ethylhexylcocoate 10,000 mg/l >> water solubility* 10,000 mg/l
Glycerol esters Glycerol-tri-oleate 10,000 mg/l >> water solubility* 10,000 mg/l
Polyol esters Trimethylolpropane-tri-oleate 5,500 mg/l > 1,000 mg/l 10,000 mg/l
Complex esters TMP mixed esters with adipinic- 5,500 mg/l >> water solubility* 10,000 mg/l
and oleic acid
* water accommodated fraction (WAF) tested after removal of insoluble organic material.

Tab. 4. Anaerobic and aerobic biodegradability of representative oleochemical esters.

Ester type Substance Ultimate (aerobic) biodegradability* Anaerobic biodegradability#

Fatty acid ester 2-Ethylhexylcocoate 95% 77%
Glycerol esters Glycerol-tri-oleate 100% 86%
Polyol esters Trimethylolpropane-tri-oleate 86% 75%
Complex esters TMP mixed esters with adipinic- and oleic acid depending on viscosity depending on viscosity
* BOD/COD: the limiting value for ready biodegradability is 60% BOD/COD in OECD 301 tests.
# CH +CO evolution.
4 2

196 Fett/Lipid 101 (1999), Nr. 6, S. 192–198

Fig. 7. Biodegradability of complex esters: viscosity-dependent decrease
of degradability.
low inoculum conditions, the higher viscosity types (320 cSt
and 1,000 cSt) do not surpass the OECD limiting values for
ready biodegradability. Thus, only the medium viscosity
products up to 140 cSt qualify for WGK 0.
6 Environmental Classification and
Labelling of Oleochemical Esters
6.1 Water hazard class
In 1986, as a result of a great fire in a Sandoz storage
facility, large amounts of chemicals were flushed into the
river Rhine by the fire fighting measures and caused a
tremendous dying of fish. To avoid such environmental dis-
asters in the future it is required in Germany that all chemi-
cal products (raw materials and formulations) produced or
marketed are to be classified in one out of four water hazard
classes (WGK) depending on their water endangering prop-
erties (Fig. 8). This classification has to be stated in Chapter
15 of the EU Safety Data Sheet, indicating the possible en-
vironmental impact that may result in case of a spill or an ac-
cident. Depending on the WGK-classification, more or less
severe (costly) precaution measures are required for hand-
ling and storage facilities. The WGK-classification is based
on the acute oral toxicity, the fish toxicity, and the bacterial
toxicity of the substance. In addition, other positive (readily
biodegradable = Bonus) and/or negative (carcinogenic =
Malus) properties have to be considered. For WGK 0 addi-
tional data are required (toxicity data for a second aquatic
species, e.g. algae or daphnia, and even more stringent
degradability requirements). These requirements are laid
down in a special administrative regulation (“Verwal-
tungsvorschrift wassergefährdender Stoffe”, VwVwS). Until
1996, besides official classifications by the German Com-
mission for Water Endangering Substances (KBwS), self-
classification by industry was accepted by the authorities,
provided that it was done according to the acknowledged
guidelines (the VCI-scheme, as developed by the German
Chemical Industry Association (VCI)). After the revised
WGK-directive has come into force (VwVwS of April 18,
1996) [6], only official classifications issued by the KBwS
and “preliminary safe” classifications are accepted. To be
regarded as “preliminary safe”, the classification has to be
offically documented, i.e. the corresponding test data includ-
ing the calculation of the WGK must be submitted to the
KBwS. Substances that are not considered as “preliminary
safe” have to be considered as WGK 3-substances. For for-
mulations, the WGK has to be calculated from the WKGs of
Fett/Lipid 101 (1999), Nr. 6, S. 192–198
Fig. 8. German water hazard classification scheme for chemicals.
their components (mixing rule, “Mischungsregel”). Only in
cases where calculation would obviously result in a mislead-
ing classification, a direct experimental determination of the
relevant ecotoxicological properties of the formulation is
permitted. In such cases the classification has to be approved
by the KBwS.
However, the current VwVwS has several drawbacks. It is
a rather complex regulation still giving some room for un-
certainties (e. g. when to give a Bonus/Malus) and, most im-
portantly, it is considered as a trade barrier by other coun-
tries. Therefore, the German Ministry of the Environment
(BMU) is currently developing a new classification scheme
that is based on the risk phrases (“R-Sätze”) laid down in
the EU Dangerous Substance Directive. Although recently a
“final” draft version of the new concept had been issued [7]
and had passed the first legislative hurdle in Federal Assem-
bly, it was rejected by the Federal Council. Thus, at the
moment the possible consequences for the WGK-classifica-
tion of oleochemical esters and comparable mineral oil based
products are still unclear.
6.2 Environmentally dangerous
Whereas the EU Dangerous Preparation Directive has
required an indication of dangerous toxicological (e. g. Xi,
irritating) and physico-chemical (e.g. F, flammable) proper-
ties of substances on the package for many years, a corre-
sponding environmental labelling was not required until
1994. However, since May 1994 chemical substances (raw
materials, but not formulations) have to be environmentally
classified in Germany on the basis of their aquatic toxicity
(fish, daphnia, and algae), their biodegradability, and their
bioaccumulation potential (Tab. 5). Substances classified as
dangerous for the environment have to be labelled with N,
and the pictogram “Dead fish, dead tree” (Fig. 9). However,
oleochemical esters are not environmentally dangerous due
to their low aquatic toxicity (LC/EC50-values >> 100 mg/l),
their ready biodegradability, and their low bioaccumulation
potential. With regard to the EU Dangerous Substance Di-
rective no classification and labelling is required.
6.3 Eco-labels
Whereas the EU environmental classification scheme has
the intention to indicate dangerous properties, eco-labels
work just the opposite way. They indicate that a certain prod-
uct is, from an ecological point of view, better than others.
Ideally thinking, as a consequence of an increased consumer
demand for these “greener” products, the whole market will
shift to more environmentally compatible products. In the
197
Tab. 5. European environmental classification and labelling scheme for chemicals.

Aquatic toxicity Long-term presence Environmental labelling R-phrases*

(LC/EC50 fish, daphnia, algae) in the environment expected?
(biodegradability, bioaccumulation)
≤ 1 mg/l yes N R-50/53
no N R-50
1–10 mg/l yes N R-51/53
no – –
> 10 mg/l no# – –
* R-50 = very toxic for aquatic organisms, R-52 = harmful for aquatic organisms,
R-51 = toxic for aquatic organisms, R-53 = long-term adverse effects possible.
# refers to “inherent” biodegradability.

application field of hydraulic oils and lubricants there are
two eco-labels being of general importance. The first to men-
tion is the German “Blauer Engel”, which is issued for
biodegradable hydraulic fluids, biodegradable loss lubri-
cants, and slab oils and biodegradable power saw chain lu-
bricants. Secondly, there is the Swedish “Clean Lubricants”
label, also for hydraulic oils. Both labels require a ready
biodegradation, and that the products, i.e. base oils plus ad-
ditives, are not harmful for aquatic organisms. In addition,
for products to be classified in the best category, the “Clean
Lubricants” label requires an origin of the products – at least
partly – from renewable resources (Fig. 10). Oleochemical
esters fulfill the requirements (except for some less degrad-
able complex esters) of these eco-labels. However, the addi-
tives necessary to achieve the required technical perfor-
mance are often the limiting components.

Abbreviations
BOD = Biological Oxygen Demand
BODIS = Biological Oxygen Demand (test) for Insoluble
Substances
COD = Chemical Oxygen Demand
DDAT = DOC Die Away Test
DOC = Dissolved Organic Carbon
MITI = (Japanese) Ministery of International Trade and
Industry
MOST = Modified OECD Screening Test
OECD = Organization for Economic Cooperation and
Development.

References
Fig. 9. Label for chemicals “environmentally dangerous”.
[1] F. Bongardt: Synthetic Esters as Multipurpose Basestocks for
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[3] Organisation for Economic Cooperation and Development, OECD
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[4] N. S. Battersby, P. A. Fieldwick, T. Ablitt, S. A. Lee, and G. R. Moys,
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Chemosphere 28 (1994), 787–800.
[5] J. Steber, C.-H. Herold, and J. M. Limia, Comparative Evaluation
of Anaerobic Biodegradability of Hydrocarbons and Fatty Deriva-
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[6] Verwaltungsvorschrift wassergefährdender Stoffe (VwVwS),
April 18, 1996.
[7] “R-Satz Konzept”, Verwaltungsvorschrift wassergefährdender
Stoffe (VwVwS), Draft from 17.9.98.

Address of the author: Dr. Andreas Willing, Henkel KGaA, 40191

Düsseldorf, Germany.
Fig. 10. Eco-labels for environmentally compatible oils and lubricants. [Received: January 28, 1999; accepted: March 17, 1999].

198 Fett/Lipid 101 (1999), Nr. 6, S. 192–198