Japanese National treasurethe World Cultural Heritage in 1993 Himeji Castle in spring(Himeji City HP)
Dr.Takashi Arai and
Yuichirou Hirai
Daicel Corporation,JAPAN
Technologies and Market Outlook on Bio-Chemical Extraction from Biomass
Incorporated Sept. 8, 1919Employees ca. 1,972Head Office TokyoConsolidated Sales US$ 3.86 billion
DAICEL was established under the name of
through a merger of eight celluloid producers in 1919
Fiscal year ending March 31, 2010. 1US$=¥83
DAI nippon CEL luloid CO. Ltd.DAICEL Corporation
AboutDAICEL Corporation
was renamed
Since 1979, our company name has long contained the phrase “chemical industry.” However, the nature of our business has now expanded beyond this exclusive industry to encompass businesses related to assembly processes, as represented by the automotive airbag inflator segment, which has grown to become a core business.We changed our trade name to "Daicel Corporation" in order to demonstrate our company’s intention to continue expanding beyond the chemical industry segment by employing the proprietary technologies and unique expertise that evolved from the chemical-based foundation of our business.We are striving to become a truly global company in harness the energy of all members of our group worldwide.
Our company was renamed Daicel Corporation on October 1, 2011.
Principal Affiliates (Overseas)
Zhejiang, ChinaNingbo Da-an Chemical Industries Co., Ltd.
TaiwanPolyplastics Taiwan Co., Ltd.
Pennsylvania, U.S.AChiral Technologies, I
Kentucky, U.S.A.Daicel Safety Systems Topas Advanced Polym
New JeDaicel (U
Jiangsu, ChinaDaicel Safety Systems (Jiangsu) Co., Ltd.PTM Engineering Plastics (Nantong) Co., Ltd.
Shanghai, ChinaDaicel (China) Investment Co., Ltd.Shanghai Daicel Polymers, Ltd.Daicel Trading (Shanghai) Ltd.Polyplastics Trading (Shanghai) Ltd.Polyplastics (Shanghai) Ltd.Daicel Chiral Technologies (China) Co., Ltd.Shanghai Da-shen Cellulose Plastics Co., Ltd.
Hong KongDaicel Polymer (Hong Kong) Ltd.Polyplastics (China) Ltd.
SingaporeDaicel (Asia) Pte. Ltd.Polyplastics Asia Pacific Singapore Pte. Ltd.
Guangxi, ChinaDaicel Nanning Food Ingredients Co., Ltd.
Shaanxi, ChinaXi’an Huida Chemical Industries Co., Ltd.
ThailandDaicel Safety Systems (Thailand) Co., Ltd.Polyplastics Marketing (T) Ltd.
MalaysiaPolyplastics Asia Pacific Sdn Bhd
Mumbai, India Polyplastics Marketing (India) Pvt. Ltd.
Hyderabad, India Daicel Chiral Technologies (India) Pvt. Ltd.
KoreaDaicel Safety Systems Korea, Inc.Germany
Daicel (Europa) GmbHTopas Advanced Polymers GmbH
PolandDaicel Safety Systems Europe Sp. z o. o.
FranceChiral Technologies Europe S.A.S.
New Oxidation Catalyst Technology
Intellectual and IntegratedProduction System
Incombustible Celluloid
Celluloid & Cellulose Nitrate
Expanding Core Technologies
Chiral Technology
Fine Chemicals
C1 Chemicals
Peracetic Acid
Petrochemistry
Water-soluble Polymers
Spun Acetate Tow
TAC photographic film Base
Cellulose Acetate
Cellulose
Organic Chemicals
Polymer Chemicals
Explosives Engineering
Gunpowder & Propellants
Pyrotechnic Systems Acetate Plastics
Pilot Emergency-escape Systems
Plastics Processing
Assembly Processing
Engineering Plastics
Polymer Alloys Inflators
TAC for LCD Optical Films
Cellulose Acetate for LCD Optical Films TAC (Tri-Acetyl Cellulose) (No.1 maker in Japan)
Cellulosic Derivatives
Cellulose Company
Tri-Acetyl Cellulose is used in protective films for LCD polarizing panels, which are an indispensable component of LCD TVs, notebook computers, cell phones, and other LCD applications.The potential scope of application for Tri-Acetyl Cellulose is expected to grow as the market for high-performance LCDs undergoes greater expansion in the future.
HOME PAGE
Social and Environmental Initiatives
Social and Environmental Initiatives②
Using Bio-ethanol as a Raw Material in Chemical Manufacturing
We are developing a sustainable chemical industry that does not depend on fossil fuels. At Daicel, our approach is to manufacture chemicals from raw materials derived from bio-ethanol, which is produced from biomass.
In 2007, Raw material of ethyl amines was converted to bio-ethanol. In 2009, Begins production of ethyl acetate using esterification process.
Ethyl amines
Ethyl acetate
Sugarcane
Copyright © DAICEL CHEMICAL INDUSTRIES,LTD. All rights reserved.
Himeji Research Center The Himeji Research Center, the nucleus of our R&D initiatives, undertakes basic research while also developing products and technologies for each industry. It
conducts research on elemental technologies for the entire company.
Ohtake Plant
Himeji Research Center
Aboshi Plant
Harima Plant
Himeji Technology Head Office
Hyogo prefecture
Break away from petroleum-dependent societyto a more sustainable society with biomass resources
Not a one-way carbon flow But a carbon cycling
NatureKey step;development of this route
Carbon Neutral and Biomass Conversion Catalyst
Development of Conversion Item from Biomass-derived Resources into Existing Chemical Products for General-Use ・Target: Reduction, Hydrogenation. Petrochemistry is oxidation chemistry ・Demand for High Selectivity
Convert only target OH group
OH
HO
H
HO
H
OHOHH H
OH
HO OHOH HO
OH
OHOHOH
PetrochemicalsGasolinePlasticsOrganic solvents Consume
Waste
Glucose bio-ethanol glycerol erythritol
Biomass-derived Resources
Consume
Waste
Biomass resources
Photosynthesis
Biomass energyBiomass products
Derived Oil Biodiesel Fuel(BDF)
Antifreeze LiquidFor Airplane
NPR, IPA
n-propyl acetate(alternative for toluene)
1,3-PD
1,2-PD
Feedstock forEngineering-Plastic
C OOO OC C H23
n
MoisturizerFor Cosmetics
10,000t/y
Strategy for Glycerol Conversion Business
Surplus GLYCEROL
Palm
with
Chemical / Biological ProcedureUnder Development in Daicel
O
CO/H2
OH O OH OH
Shell
DuPont
Glucose OH OHOH
OH O OH OHCorn starch
Degussa
O
Acrolein
OH O OH OH
3-HPA
BIO
CHEM CHEM
CHEM CHEM
1,3-PD
Lab. (Klebsiella pneumoniae, etc.)
OH OHOH
OH O OH OH
13PD: Production Methods
Discontinued
Recombinant Coli
Anaerobic Bacteria
Discontinued
Chemical Procedure
Biological Procedure
There is no production of 13PD with chemical procedure at this moment.
DuPont Bio-13PD (Zemea, Susterra) High Grade: Purity 99.98%
1,3PD PTTMakers Plant
Procedure Capacity Plan CapacityRemarks
Shell Chemicals USA EO (73,000) (20,000) Discontinued in 2009
German Acrolein ( 9,000) Discontinued in 2006Evonik, Degussa
USA Acrolein (45,000)
Plan aborted
DuPont Tate & Lyle USA Bio 45,000 Running since 2006
DuPont USA 42,000 Enhancement +30,000t (2008)
Glory China 30,000 Running since 2007
Sum Total 45,000 72,000
1,3PD、PTT Current Capacity and Enhancement Plan (order:T)
Enhancement
Withdrawn
13PD Makers in the World
Withdrawn
グリセリン輸入実績
0
2,000
4,000
6,000
8,000
10,000
12,000
14,000
16,000
2000 1
Q
2001 1
Q
2002 1
Q
2003 1
Q
2004 1
Q
2005 1
Q
2006 1
Q
2007 1
Q
2008 1
Q
2009 1
Q
2010 1
Q
数量
[T]
-
20
40
60
80
100
120
140
160
180
200
単価
[円/kg
]
GL輸入(数量)
GL輸入(単価)
粗グリセリン輸入実績
-
500
1,000
1,500
2,000
2,500
3,000
3,500
4,000
2000 1
Q
2001 1
Q
2002 1
Q
2003 1
Q
2004 1
Q
2005 1
Q
2006 1
Q
2007 1
Q
2008 1
Q
2009 1
Q
2010 1
Q
数量
[T]
-
10
20
30
40
50
60
70
80
90
100
単価
[円/kg
]
粗GL輸入(数量)
粗GL輸入(単価)
Purified-Glycerol : Malaysia>Philippines>Indonesia
Raw-Glycerol : Indonesia>Malaysia, Singapore, EU countries (Spot)
Ref. Foreign trade statistics (Japan Finance Ministry)
Raw- and Purified-Glycerol Import Trend
Purified-Glycerol Import Experience Raw-Glycerol Import Experience
Quantity (T) Quantity (T)
Cost (¥/kg)Cost (¥/kg)
Quantity (T)Cost (¥/kg)
Quantity (T)Cost (¥/kg)
HO OH
HO
OH
HO OH
OH
1,2-Propanediol
1,3-Propanediol
internal OHhydrogenolysis
terminal OHhydrogenolysisConventional Technology
Cu catalyst(Cu-Cr, Raney Cu, Cu/Al2O3)
Rare metal composite catalyst
HO OH
OH
with >95% selectivity
~200℃
120℃
with ~70% selectivity
Technical Platform for 13PD Production
Innovation Technology
Our Technology possesses;
・High selectivity for internal OH hydrogenolysis・Higher reactivity than Cu catalyst at the same temp.
China,
Nanjing Univ.
Tendency of GLY Conversion Research
Korea,
Yonsei Univ.
Green Chem., 2011, 13, 2004–2007
Green Chem., 2010, 12, 1466~1472.
GlycerolBy-product of BiodieselProduced about 1,000,000T/YNo application for use
1,3PDProduction goal; 10,000T/YMonomer of Polytorimethylen-telephtalate (PTT)
1,3PDProduction goal; 10,000T/YMonomer of Polytorimethylen-telephtalate (PTT)
HOOH
HOOH
Our Work
+ H2 + H2OOH OHOH
OH OHSolid Catalyst
Our Technical Superiority ・High Selectivity for 13PD
・Accomplishable production with reasonable catalyst cost ・Applicable to high concentration reaction (Small solvent)
Realization of Industrial Continuous Process!! ・Scale-up about 108 times step-by-step ・Ensuring of catalyst life over 1 years ・Construction of purification process
Catalyst Activity with various GLY Sources
Less impurity in GLY source, longer the catalyst life.
GlycerolConversion
Continuous Reaction Time
Containing less impurities
Containing more impurities
We need…high-grade GLYCEROL resource following;・Containing less mineral salt (K, Na, Mg, Cl…)
・Containing less amino acid-derived compounds(-COOH, -NH2, -SH…)
C2 Frac.ethylene
C3 Frac.propylene
C4 Frac.Butadiene
PetroleumNaphtha
Benzene
Toluene
Xylene
Fractionating Tower
Although materials of petroleum product is naphtha fraction, it comes to be altered with biomass-derived materials.
・Bio-ethanol
・Bio-glycerol (from bio-diesel)
・Bio-propanol
We are also trying development of switch of C4 material from naphtha fraction to biomass.
Practical Application of C4-Chemistry with Biomass
OH
HO
H
HO
H
OHOHH H
OHHO
OHOH
OH
HOOH
HOOH
O
O
Mitsubishi Chemical Problems in cost and production efficiency.
14BD already available from butadiene.
Genomatica(USA) Collaboration with Mitsubishi Chemical for
commercialization since 2011.
HOOH
HOOH
OH
OH +
+
H2
OH
HOOH
O
OHO
OHO
Overview of a C4-tree from Glucose
Glucose Erythritol
Fermentation
14BD is also useful for engineering plastic monomer.(PBT; Polybutylene Telephtalate)
Daicel
OH
HO
H
HO
H
OHOHH H
OHHO
OHOH
OH HOOH
OH
OH +
+
OHGlucose Erythritol
Novelty and Superiority of Our Business
Novelty and Superiority
①AccessibilityAs fermentation technique of glucose is ensured, erythritol iscommercially available.
②Bi-product is also valuable; 1,3-Butanediol Our existing product for moisturizer in cosmetics or shampoo. We are Japanese No. 1 maker, and enhanced the production equipment
in 2009. ③Variety of use application
Plastics ・Cosmetics ・Solvents ・Paint etc.
Daicel
Fermentation(Available)
①Promotion ②Suppression
percent conversion 55%
11%
11%36%
16%
21%
2% 1%
4%
Regulation of Production Selectivity
Target Products
Future outlook・The expansion of novel catalysts in combination with
the ability to design the chemical catalyst to fit the process.
・We believe that the industrial production of as many chemicals as possible with a catalyst using the assemblyarrangement techniques will result in decreased production cost, thereby leading to the construction of an innovative substance production system that can save energy in harmony with the environment.
This study was supported by a NEDOGrant for Innovation Promotion Program.※NEDO=New Energy and Industrial Technology Development Organization
I would like to receive any question by email. [email protected] Thank you!