Special

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PRODUCT PROFILE

Sebacic Acid: A Techno-Commercial Profile

PANKAJ DUTIA
pankaj@chemicalweekly.com
INTRODUCTION
Sebacic acid is a bi-carboxylic acid
with structure (HOOC)(CH 2)8(COOH), and
is naturally occurring. It was named from
the Latin sebaceus (tallow candle) or
sebum (tallow), in reference to its use in
the manufacture of candles.
In its pure state it is a white flake or
powdered crystal. The product is described as non-hazardous, though in its
powdered form can be prone to flash ignition (a typical risk in handling fine organic powders).

Sebacic acid is a derivative of castor

oil, with the vast majority of world production being done in China, which annu-

ally exports over 20,000-tons, representing over 90% of global trade of the product. In the industrial setting, uses of sebacic acid and its analogs such as azelaic
acid can be found in plasticizers, lubricants, hydraulic fluids, cosmetics,
candles, etc. Sebacic acid is also used as
an intermediate for aromatics, antiseptics and painting materials.
Properties
Sebacic acid is a white flake or powdered crystal. It is resolved in ethanol,
ether and soluble slightly in water.
Sebacic acid and its derivatives such
as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc.
It is used in the synthesis of polyamide
and alkyd resins. It is also used as an
intermediate for aromatics, antiseptics
and painting materials.

Table 1
Physical properties of sebacic acid

Table 2
Sale specifications of
commercial sebacic acid
Parameter

Value

Appearance

White powder

Sebacic acid

99.5% minimum

Ash

0.03% max

Moisture

0.3% max

Melting point

131-134.5 C

Packaging

25-kg, 1000-kg bags

There are almost infinite esters obtained from thousands of potential starting materials. Esters are formed by removal of water from an acid and an alcohol, e.g., carboxylic acid esters, phosphoric acid esters, and sulfonic acid esters. Carboxylic acid esters are used as
in a variety of direct and indirect applications.
Lower chain esters are used as
flavouring base materials, plasticizers,
solvent carriers and coupling agents.
Higher chain compounds are used as
components in metalworking fluids, surfactants, lubricants, detergents, oiling
agents, emulsifiers, wetting agents textile treatments and emollients.

Parameter

Value

Chemical name

Decanedioic acid

Chemical formula

C10H18O4

Molecular weight

202.25 g/mol

CAS no

[111-20-6]

Boiling point

294.4C at 100 mm Hg

Melting point

131-134.5C

Synonyms

8-Octanedicarboxylic acid; decanedioic acid;

They are also used as intermediates for the manufacture of a variety

of target compounds.

1,10-decanedioic acid; n-decanedioic acid; acide

sebacique; dicarboxylic acid C10; sebacinsaure;
decanedioic acid
Chemical Weekly July 31, 2007

The almost infinite esters provide a

wide range of viscosity, specific gravity, vapor pressure, boiling point, and other physical and chemical properties for the proper
application selections.
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Table 3
Derivatives of sebacic acid
Product
1,1'-Isosebacoylbis
(2-ethylaziridine)
1,1'-Sebacoylbisaziridine
1,4-Dioxatetradecane-5,
14-dione

CAS RN
25853-47-8
2798-06-3
5578-82-5

1,6-Dioxacyclohexadecane-7,
16-dione
58296-43-8
2,2,9,9-Tetramethylsebacic
acid

22092-62-2

2-Ethylhexyl 2,2,
5-trimethylhexyl sebacate 71607-40-4
2-Ethylhexyl nonyl sebacate
2-Hydroxysebacic acid

5137-28-0
103963-71-9

Bis(tetrahydrofurfuryl) sebacate
Butyl 2,3-dihydroxypropyl
sebacate
Cadmium sebacate

4650-79-7
94109-50-9
4476-04-4

Cerium(3+) sebacate

25418-94-4

Cerium(4+) sebacate

94232-56-1

Choline, chloride sebacate

28492-70-8

Cupric sebacate

58783-12-3

25418-93-3

Lithium hydrogen sebacate

94042-76-9

Dicyclohexyl sebacate

4121-15-7

Neodymium(3+) sebacate

25418-96-6

Ammonium hydrogen 9,10

dihydroxysebacate

84753-04-8

Ammonium octyl sebacate

4913-33-1

Diethyl Sebacate

42233-75-0
110-40-7

Perfluorosebacic acid

307-78-8

Polifeprosan 20

90409-78-2

Poly(ethylenesebacate)

25037-32-5

Poly(hexamethylene
sebacate)

26745-88-0

Dimethyl hexadecafluorosebacate 4590-24-3

Praseodymium(3+) sebacate

25418-95-5

Di-n-butyl Sebacate

109-43-3

Sebacic acid

Di-n-decyl sebacate

2432-89-5

Di-n-dodecyl sebacate

2432-88-4

Di-n-hexadecyl sebacate

19370-86-6

26719-48-2

Di-n-hexyl sebacate

2449-10-7

Di-n-octadecyl sebacate

3072-03-5

Bis(2-methylbutyl) sebacate 93805-24-4

Di-n-octyl sebacate

2432-87-3

Bis(3,5-dibromosalicyl)
sebacate

Di-n-tetradecyl sebacate

23394-16-3

Lanthanum(3+) sebacate

818-88-2

5,5'-Sebacoyldi(oxytryptamine)
diacetate
52671-00-8

Bis(cholest-5-en-3beta-yl)
sebacate

5591-33-3

Methyl hydrogen sebacate

Dilithium sebacate

Bis(3-methylbutyl) sebacate 10340-42-8

Iosefamic acid

3137-00-6

7491-02-3

74134-05-7

92739-54-3

Diallyl sebacate

Diisopropyl sebacate

624-10-2

Dodecyl hydrogen sebacate

Di-2-ethylhexyl isosebacate 29590-28-1

28473-19-0

Bis(2-ethoxyethyl) sebacate

93819-99-9

Lithium, dimethyl sebacate,

12-hydroxyoctadecanoate
naphthenate complex
68919-36-8

122-62-3

Diisodecyl sebacate

52829-07-9

Docosyl hydrogen sebacate

Di-2-ethylhexyl sebacate

3,3'-(Sebacoyldiimino)bis(5(propionamidomethyl)-2,
4,6-triiodobenc acid)
25901-42-2

Bis(2,2,6,6-tetramethyl-4piperidinyl) sebacate

10355-50-7

Lithium, 12-hydroxyoctadecanoate
sebacate complex
68815-49-6

Didocosyl sebacate

19856-32-7

Divinyl sebacate

Decanedioic acid bis(1,2,2,6,6-penta

methyl-4-piperidinyl)ester 41556-26-7

3,3'-(Sebacoyldiimino)bis
(5-(acetamidomethyl)-2,4,6triiodobenzoic acid)
25901-36-4

Barium sebacate

Di-tert-butyl bisperoxysebacate 22537-96-8

Dipentyl sebacate

26719-47-1
6819-09-6

Dipotassium sebacate

52457-55-3

Dipropyl sebacate

15419-91-7

111-20-6

Sebacic acid 1,3,5-triazine2,4,6-triamine salt

31970-90-8

Sebacic acid 1,3,5-triazine2,4,6-triamine salt

94159-18-9

Sebacic acid 2,2',2'nitrilotriethanol complex

94202-16-1

Sebacic acid 2,2',2'nitrilotriethanol complex

85030-06-4

Sebacic acid 2,2',2'nitrilotriethanol complex

70103-35-4

Sebacic acid 2,2'iminodiethanol complex

81189-11-9

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Sebacic acid 2,2'iminodiethanol complex
Sebacic acid 2,2'iminodiethanol complex

84145-30-2
94200-21-2

Sebacic acid 2-aminoethanol

complex
82801-62-5
Sebacic acid 2-butoxyethyl
ester

68186-66-3

Sebacic acid bis(2-(2butoxyethoxy)ethyl) ester

70900-46-8

Sebacic acid bis(2-butoxyethyl)

ester
141-19-5
Sebacic acid bis
(2-mercaptoethyl) ester

60642-69-5

Sebacic acid bis

(2-methoxyethyl) ester

71850-03-8

Sebacic acid bis

(phenylmethyl) ester
Sebacic acid dihydrazide

Report

Sebacic acid diisooctyl ester 27214-90-0

Sebacic acid lead(2+) salt

Sebacic acid ditridecyl ester

Sebacic acid methyl 1,2,2,6,6

pentamethyl-4-piperidinyl
ester
82919-37-7

Sebacic acid morpholine

complex

2741-62-0
84522-37-2

Sebacic acid N-(2-aminoethyl)N-(2-((2-aminoethyl)amino)

ethyl)ethane-1,2-diamine salt 84501-59-7
Sebacic acid 1,3,5-triazine2,4,6-triamine salt
Sebacic acid
1, 6-hexanediamine salt
Sebacic acid aluminum salt

94159-19-0

Sebacic acid monoethyl ester

29473-77-6

693-55-0

Sebacinyl-bis(1-methylpiperazine4-methyl iodide)
61167-37-1
Sebacinyldicholine

7095-43-4

6422-99-7

Sebacoyl chloride

111-19-3

5505-62-4

Sebacoyldioxybis
(tributylstannane)

30099-72-0

Sodium hydrogen sebacate

14047-57-5

Sebacic acid bis((17-beta-hydroxy17-methylandrosta-1,4-dien3-ylidene)hydrazide)

15437-53-3
Sebacic acid dimethyl ester

106-79-6

Tetradecyl hydrogen sebacate

93819-98-8

140-24-9

Sebacic acid dinonyl ester

4121-16-8

925-83-7

Sebacic acid disodium salt

17265-14-4

Tetrahydrofurfuryl hydrogen
sebacate

4650-83-3

Applications
Sebacic acid is used as a reactant
in making chemical compounds,
(mostly esters and polymer resins).
Sebacic acid is also polymerized to
make nylon 6/10, which, in turn, is fabricated into products such as toothbrush bristles, fishing lines and paper
machine felts. It also may be polymerized to produce polyester resins, coatings and adhesives. Sebacic acid may
also be reacted with various alcohols to
produce sebacate esters. These esters are
used as plasticizers (which soften stiff
plastics and resins) in polyvinyl chloride
(PVC) films to provide low temperature
flexibility and freedom from cracking. Sebacic acid is also used directly in formulated products such as antifreeze coolants, as corrosion inhibitors in cutting
and metal-working fluids, and in other
formulated products such as coatings,
and lubricants.

Product substitution
In order of importance, two products
may be substituted for sebacic acid: azelaic acid and adipic acid. Azelaic acid can
be used as a substitute in HMPA (hot
melt polyamide); while adipic acid could
be used as a substitute for HMPA, esters, and nylon. In corrosion inhibitors
too alternative products not containing
sebacic acid are available.
Other substitutions possible include:
w In metal treatment: replacing sebacic
acid with dodecandioic acid;
w In anti-freeze production: replacing
sebacic acid with 2-ethyl hexanoic acid;
or replacing dioctyl sebacate with dioctyl azelate.
Manufacture
In theory, sebacic acid can be produced in a number of ways including
from petrochemical feedstocks but

Chemical Weekly July 31, 2007

the primary commercial route begins

with castor oil.
Castor oil is obtained from castor
seed, the fruit of Ricinus communis, a
subtropical shrub, by mechanical
pressing and/or solvent extraction.
Some castor seed is traded internationally, but most castor oil is produced in those countries that grow
castor seed, principally India, China,
and Brazil. Countries producing castor
oil consume a large portion of their
own castor oil output, though a considerable amount is also traded internationally.
As a natural vegetable oil, castor oil
contains an array of identifiable chemicals, most important among them being
fatty acids. Castor oil contains approximately 89.5% ricinoleic acid, along with
lesser amounts of dihydroxystearic acid,
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palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, eicosanoic
acid, and other fatty acids.

cic acid to precipitate from the solution.

It is then filtered, water washed, and finally dried.

Sebacic acid is made from the ricinoleic acid in castor oil. One of the manufacturing process challenges is how to
deal with the other fatty acids and constituents contained in castor oil without
losing their intrinsic value as potential
by- or co-products.

A number of process improvements

have been described, and include the use
of white mineral oil having a boiling range
of 300-400C or the use of a mixture of
cresols. These materials act to reduce
the reaction mixtures viscosity, thus
improving mixing. Higher sebacic acid
yields are claimed by the use of catalysts such as barium salts, cadmium
salts, lead oxide, and salts.

From castor oil

There were two recognized production processes for sebacic acid: a batch
caustic fusion process and an integrated,
continuous process reportedly used by
several of the larger Chinese producers.
The castor oil or ricinoleic acid and
caustic are fed to a reactor (usually
Monel or nickel) at a temperature of 180270C where the ricinoleic acid undergoes a series of reactions with evolution
of hydrogen to give disodium sebacate
and capryl alcohol.
When the reaction is complete, the
soaps are dissolved in water and acidified to a pH of about 6. At this pH, the
soaps of the monobasic acids (C-16 to
C-20 plus dimer acids) are converted to
free acids that are insoluble in water. The
disodium sebacate is only partially neutralized to the half acid salt, which is
water soluble. The oil and aqueous layers are separated. The aqueous layer
containing the half salt is acidulated to a
pH of about 2 causing the resulting seba-

Indian Institute of Chemical Technology (IICT, Hyderabad) has developed an

efficient laboratory process for the
preparation of sebacic acid from castor
oil in excellent yields and purity.
In this process castor oil is split to
produce fatty acids, which are subjected
to alkali fusion. The products are neutralized to separate 2-octanol and other
fatty acids. Sebacic acid is obtained on
further acidification, which is separated
and purified. Processing is simpler and
cost effective.The process-upscaling
work by batch and continuous processing modes is in progress with partial funding from TIFAC (DST).
Electrooxidation process
An electrooxidation process was developed by Asahi Chemical Industry in
Japan, and was also piloted by BASF in
Germany. It produces high purity sebacic acid from readily available adipic

Table 4
Powder sebacic acid quality index
Special High-grade
Sebacic acid content
Ash content
Moisture content
Alkali fusion chromaticity (APHA)
Melting point range

99.5 min
0.02 max
0.3 max
5 max
131-134.5

High-grade I

High-grade II

99.5 min
0.03 max
0.3 max
15 max
131-134.5

99.5 min
0.05 max
0.3 max
25 max
131-134.5

Source: Vikram Ricinol Derivatives Ltd.

acid. The process consists of three

steps.
1. Adipic acid is partially esterified to the
monomethyl adipate;
2. Electrolysis of the potassium salt of
monomethyl adipate in a mixture of
methanol and water gives dimethyl
sebacate; and
3. The last step is the hydrolysis of dimethyl sebacate to sebacic acid.
Overall yields are reported to be about
85%.
From butadiene
Another alternative method to produce
sebacic acid involves a four-step process.
First, butadiene is oxycarbonylated to methyl pentadienoate, which is then dimerized, using a palladium catalyst, to give a
triply unsaturated dimethyl sebacate intermediate. This unsaturated intermediate is
hydrogenated to dimethyl sebacate, which
can be hydrolyzed to sebacic acid.
Small amounts of branched chain isomers are removed through solvent crystallizations, giving sebacic acid purities
of greater than 98%.
In another method based on butadiene, it is dimerized in the presence of
sodium to form an isomeric mixture of
disodiooctadiene. Carbonation of the
mixture using dry ice gives the unsaturated acids, 3,7-decadienedioic acid, 2vinyl-5-octenoic acid, and 2,5divinyladipic acid in a ratio of about
3.5:5:1, respectively. Hydrogenation of
this mixture gives the saturated dibasic
acid product consisting of approximately
51% 2-ethylsuberic, 38% sebacic and 11%
2,5-diethyl-adipic. Sebacic acid is separated by fractional crystallization in about
35% yield. By-product acids, consisting
of 72-80% 2-ethylsuberic, 12-18%
diethyladipic, and 5-10% sebacic acids
are obtained and referred to as
isosebasic acid.
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Status of Indian industry
Vikram Ricinol Derivatives Ltd.
(VRDL) claims to be the only manufacturer of sebacic acid in India. The company has established a manufacturing

plant near Ahmedabad for sebacic acid,

2-octanol and glycerine with a capacity of 2,000-tpa. Products are available
for marketing in India and abroad (except West Europe & North America).

Table 6
Imports & exports of azelaic acid, sebacic acid and their salts &
esters
[Quantity in tons; value in Rs. Million]
Imports
2001-02
2002-03
2003-04
2004-05
2005-06

Exports

Quantity

Value

Quantity

Value

77.27
59.04
112.40
140.20
198.10

120.96
123.21
184.40
160.66
223.01

20.12
54.00
50.00
n.a
n.a

12.63
48.91
33.97
n.a
n.a

Table 7
Countrywise imports of azelaic acid, sebacic acid and their salts &
esters
[Quantity in kgs; value in Rs.]
Country

2001-02
Quantity
Value

Quantity

2002-03
2003-04
Value Quantity
Value

Belgium
China
Germany
Italy
Japan
Malaysia
Netherlands
UK
USA

40
13,610
6,685
50
500
43,200
750
105
12,338

5,041
1,384,230
4,361,564
9,138
325,967
2,895,143
113,634
17,062
2,984,923

0
0
48,940 4,658,573
1,952
329,094
0
0
350
221,249
1,000
334,938
1,460
318,897
560
221,998
4,779 6,236,705

40
10,380
98,350 12,154,845
454
155,195
50
12,063
550
395,831
4,115 1,237,855
2,735
521,545
365
81,169
5,766 3,871,314

Total

77,278 12,096,702

59,041 12,321,454

112,425 18,440,197

Table 8
Countrywise exports of azelaic acid, sebacic acid and their salts &
esters
[Quantity in tons; value in Rs. Million]
Country

2001-02
Quantity
Value

2002-03
2003-04
Quantity
Value Quantity
Value

Jordan
Pakistan
USA

0
0
20,120

0
0
1,263,159

0
0
0
0
54,000 4,891,395

16,000
16,000
18,000

627,307
1,150,380
1,619,664

Total

20,120

1,263,159

54,000 4,891,395

50,000

3,397,351

Chemical Weekly July 31, 2007

Report

Jayant Oils and Derivatives Ltd., (formerly known as Jayant Vegoils & Chemicals P. Ltd.) is a fully integrated producer
of castor oil and its derivative
products.manufacturing unit and seed
crushing plant at Makarpura in Baroda,
Gujarat, where castor oil of various
grades and its derivatives are manufactured here.
Table 5
Grain sebacic acid quality index
Index name

Index

Sebacic acid content

Ash content
Moisture content
Alkali fusion
chromaticity (APHA)
Melting point range
Granularity

99.5 min
0.03 max
0.1 max
15 max
131-134.5
95% or more

Demand assessment
Generally speaking, sebacic acid
finds use in the following applications:
w Manufacture of Nylon 6,10 & Nylon 11
w Plasticizers like dioctyl, dibutyl,
isooctyl, benzyl and methyl sebacate.
w Synthetic resins like alkyd resin and
saturated polyester resin
w Lubricating oils and hydraulic fluid.
Nylon 6,10 & Nylon 11
The polyamide nylon 6,10 obtained by
reaction of sebacic acid with hexamethylenediamine (HMDA), no longer has
any industrial significance. Nylon 11 too is
not produced in the country.
Sebacate plasticizers
Sebacic acid is used in the manufacture of number of sebacates like dioctyl
sebacate, dibutyl sebacate, diethyl
sebacate, diisoctyl sebacate, which are
used as plasticizers. Sebacate plasticizers
are primarily used because of their superior low temperature properties compared
to the phthalate plasticizers. Dioctyl
sebacate and dibutyl sebacate are used as
part plasticizers to resist migration and to
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Table 9
Imports & exports of sebacic acid, salts & esters from China
[Quantity in tons; value in thousand US$]
Month
May 2007
April 2007
Mar 2007
Feb 2007
Jan 2007
Dec 2006
Nov 2006

Imports
Quantity
47.290
84.772
38.919
81.793
84.441
44.001
53.576

Value
395
856
214
609
685
188
437

Exports
Quantity
2,612.024
2,866.935
3,054.860
2,765.524
3,008.205
2,922.081
2,656.330

Value
6,085
6,677
7,055
6,371
6,816
6,663
5,745

Source: China Chemical Reporter

increase sulphur staining. It is used as stabilizers for PVC products requiring low temperature properties. Some producers of
sebacate plasticizers are:
w Krishna Anti-oxidants P. Ltd. (Mumbai)
w Subhash Chemical Industries (Pune)
w Subray Catal Chem P. Ltd. (Thane)
w Kaival Chemicals P. Ltd. (Vadodara)
The estimated demand for sebacic
acid for sebacate plasticizers is around
3,000-tons per annum.
Synthetic resins
Sebacic acid is also used in the manufacture of saturated/unsaturated polyester
resin. It is also used in the manufacture of
alkyd resins. There are a number of substitutes for sebacic acid for synthetic resin
manufacture and its use level in the synthetic resins industry is negligible.
Lubricant industry
Sebacic acid is used as additives for low
temperature lubricants at high altitudes. They
are used as additive in lubricants for aircrafts
engines and also as additives in hydraulic
fluids. The use of sebacic acid in lubricants
is confined to aircrafts for use at high altitude levels. Synthetic lubricating oils are
generally used instead of Sebacic acid.The
present Indian demand for sebacic acid is
estimated to be around 3,500-tons per annum, with a modest growth rate of 6-7 per
cent per annum.

Trade in India
India has been importing as well as
exporting small quantities of sebacic acid.
Global scenario
China
China is a major supplier of sebacic acid
in the world having a share of about 60% of
the global market. The total global market
is estimated to be in the region of 65,000
tons. Most imports of sebacic acid into India are also from China. According to data
available with customs, imports of sebacic acid in the period January 1, 2005 to
May 31, 2007 (29 months) were about 442tons, almost all of which came from China.
Prices of imported material have hovered
around Rs. 110-120 over this period.
Some producers of sebacic acid in
China include:
w Hengshui Dongfeng Chemical Co.Ltd.
w Hengshui Ok Enterprise Co., Ltd
w Jiheng Chemical
w Kong Associates
w Qingdao Great Chemical Inc.
w Shandong Haihua Tianhe Organic Chemical Co., Ltd
w Shandong Weifang Import And Export
Co., Ltd
w Shanghai AiLiJiu Import And Export Co.,
Ltd.
w Shijiazhuang Summit Chemcial Co., Ltd.
w Tonliao Xinghe Chemical Co., Ltd
w Wuhan Xinda E&T Dev. Co., Ltd.

USA
Between 1991 and 2002, Union Camp
of Wayne, NJ, was the sole U.S. producer
of sebacic acid in the USA. In May 1999,
Union Camp was acquired by Arizona
Chemicals of Jacksonville, FL, a subsidiary of International Paper. Arizona Chemicals ceased production of sebacic acid in
December 2002, but continued to sell sebacic acid from inventory through 2003. The
company no longer has any employees, facilities, or other resources in place for the
production, sale, or marketing of sebacic
acid, though it does continue to import sebacic acid. Caschem Inc., a subsidiary of
Cambrex Corporation, began manufacturing and producing sebacic acid with a proprietary manufacturing process and a dedicated, fully automated plant in Bayonne,
N.J. in August 1999.
The facility also produced 2-octanone
and 2-octanol at higher purities than products on the market. The US sebacic acid
industry changed significantly in December 2002 with the exit of two players,
Caschem and Arizona Chemical, and the
entrance of a newcomer, Genesis Chemical Inc., which began producing sebacic
acid at its Loveland, Ohio plant. The two
companies both opted to leave the market
late-2001 under pressure from low-priced
sebacic acid imports from China and high
production costs.
For the next two years, Genesis was the
sole US producer of sebacic acid, but the
company ceased production of sebacic acid
in 2004, again owing to pressure from cheap
Chinese supplies. Sebacic acid is one of the
strategic materials stored in the National
Defense Stockpile maintained by the U.S.
Department of Defense. These materials
would be needed to supply the military, industrial, and essential civilian needs of the
United States during a national emergency
and are not found or produced in the United
States in sufficient quantities to meet such
need. The proposed stockpile of sebacic
acid for fiscal year 2005 is 600,000 lbs.
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