JP2016501929A - バイオ燃料を製造する方法 - Google Patents
バイオ燃料を製造する方法 Download PDFInfo
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- JP2016501929A JP2016501929A JP2015541148A JP2015541148A JP2016501929A JP 2016501929 A JP2016501929 A JP 2016501929A JP 2015541148 A JP2015541148 A JP 2015541148A JP 2015541148 A JP2015541148 A JP 2015541148A JP 2016501929 A JP2016501929 A JP 2016501929A
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- fatty acid
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- 239000002551 biofuel Substances 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims abstract description 85
- 229940074076 glycerol formal Drugs 0.000 claims abstract description 60
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 54
- 229930195729 fatty acid Natural products 0.000 claims abstract description 54
- 239000000194 fatty acid Substances 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 49
- 150000002148 esters Chemical class 0.000 claims abstract description 30
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 30
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 121
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000002815 homogeneous catalyst Substances 0.000 claims description 14
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003377 acid catalyst Substances 0.000 claims description 8
- 239000003456 ion exchange resin Substances 0.000 claims description 8
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 8
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 titanium alkoxide Chemical class 0.000 claims description 4
- 150000004703 alkoxides Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 1
- 239000003225 biodiesel Substances 0.000 abstract description 15
- 239000000446 fuel Substances 0.000 description 12
- 238000004821 distillation Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 150000003626 triacylglycerols Chemical class 0.000 description 7
- 239000003549 soybean oil Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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Abstract
Description
1.2030年までに現在のレベルから、例えば、同時に発生する熱パワー、プロセス強化、新規なエネルギー節減プロセスの導入、およびプロセスサイクル内における再生可能なエネルギー源の革新的な導入の組合せによる、化石燃料のエネルギー量における30%までの削減。
(A)トリグリセリド、グリセロール、好ましくは含水グリセロール、およびジアルコキシメタン、好ましくはジメトキシメタンを、酸触媒の存在下で反応させる工程であって、好ましくは、トリグリセリドのジアルコキシメタンに対するモル比は1から6の間および1から30の間であり、トリグリセリドのグリセロールに対するモル比は1から3の間および1から7の間であり、およびジアルコキシメタンは3から9個の炭素原子を含有し、従って反応が終了したときに2層を形成する工程。
上の説明で示したように、以下のプロセスはいずれも上で説明したことにさらに追加する事項を含むことができる。
実施例1.均一触媒
実施例2.均一触媒
実施例3.不均一触媒
実施例4.不均一触媒
実施例5
80.5gのダイズ油(0.09モル、1.0当量)、25.9gのグリセロール(99%グリセロールw/w)(0.28モル、3当量)、215.3gのジメトキシメタン(2.82モル、30当量)、および6.4gの硫酸を閉じた容器に加えた。該混合物を270rpmで攪拌して70℃で加熱した。反応混合物を70℃および1.5バールに4時間保ち、得られた2層を分離した。脂肪酸メチルエステルと脂肪酸グリセロールホルマールエステルの混合物と一緒に過剰のジメトキシメタンおよびメタノールを含有する上層を、30gの硫酸のメタノール性溶液(5%w/w)と共に還流させた。2層を分離した上層をイオン交換樹脂(塩基性型)を使用して中和した。濾過後、過剰のジメトキシメタンおよびメタノールを留去して脂肪酸メチルエステル含有する78.1gの生成物(組成物III)を得た。下層中のグリセロールホルマールを留出させて26gの純粋生成物(組成物II)を得た。未反応のグリセロールおよび硫酸を含む蒸留残渣は、その後のバッチで再使用した。
実施例6
グリセロールホルマール(1354g、13.0モル、2当量)および脂肪酸メチルエステル(1900g、6.5モル、1当量)を、真空蒸留系を備えた反応装置に加えた。混合物を100℃に加熱してチタンイソプロポキシドを加えた。反応混合物を100℃および10ミリバールの圧力に12時間保った。留出したメタノール(190g、5.93モル、0.91当量)を蒸留コレクターに収集した。反応が終了したら、過剰のグリセロールホルマールを20mmHgの減圧で留去した。90℃で留出する分画が純グリセロールホルマールに対応する。それに続いて反応混合物を室温に冷却した。触媒を加水分解するために、水(190g)を加えて反応混合物を30分間攪拌した。加水分解された触媒を遠心分離により除去してヘキセンで洗浄し、続いて蒸発により乾燥させた。生じた橙色油を0.45マイクロメートルのフィルタで濾過して1735gの脂肪酸グリセロールホルマールエステルを得た。
Claims (10)
- 脂肪酸アルキルエステル、グリセロールホルマールおよびバイオエステル脂肪酸グリセロールホルマールエステルを含む数種類の組成物を同時に得る方法であって、
(A)トリグリセリド、グリセロールおよびジアルコキシメタンを、均一または不均一な酸触媒の存在下で反応させ、その結果2層を形成させる工程であり、上層が脂肪酸アルキルエステル、脂肪酸グリセロールホルマールエステルおよび過剰のジアルコキシメタンおよびアルキルアルコールの混合物を含み、下層がグリセロールホルマール、過剰グリセロール、および均一触媒が反応で使用された場合には均一触媒、の混合物を含む工程、
(Bl)脂肪酸アルキルエステルおよび脂肪酸グリセロールホルマールエステルを含む組成物を得るために、ジアルコキシメタンおよびアルキルアルコールを、上層から分離する工程、
(B2)グリセロールホルマールを含む組成物を得るために、グリセロールホルマールを未反応のグリセロール、および均一触媒が工程(A)で使用された場合には、均一触媒を、下層から分離する工程、
(C)脂肪酸アルキルエステルを含む組成物およびグリセロールホルマールを含む組成物を得るために、工程(A)により得られた上層からの化合物を、アルキルアルコールと酸触媒の混合物と反応させる工程、
(D)工程(Bl)で得られた組成物または工程(C)で得られた脂肪酸アルキルエステルを含む組成物と、工程(C)で得られたグリセロールホルマールを含む組成物との間のエステル交換反応を、均一なまたは不均一なエステル交換触媒の存在下で実施して、脂肪酸グリセロールホルマールエステルを含む組成物を形成させる工程、
を含む方法。 - 工程(A)で使用されるグリセロールが水をさらに含有する、請求項1に記載の方法。
- 工程(A)においてトリグリセリドのジアルコキシメタンに対するモル比が、1から6の間および1から30の間であり、トリグリセリドのグリセロールに対するモル比が1から3の間および1から7の間であり、且つジアルコキシメタンが3から9個の炭素原子を含有する、請求項1または2に記載の方法。
- 工程(A)においてジアルコキシメタンがジメトキシメタンである場合に、脂肪酸メチルエステルおよびメタノールが、上層中で脂肪酸グリセロールホルマールエステルおよび過剰のジメトキシメタンと一緒に得られる、請求項1〜3のいずれか一項に記載の方法。
- 工程(A)で使用される酸触媒が、硫酸である均一触媒または酸性イオン交換樹脂である不均一触媒である、請求項1〜4のいずれか一項に記載の方法。
- 工程(A)の反応温度が55℃と85℃の間である、請求項1〜5のいずれか一項に記載の方法。
- 工程(D)で使用されるエステル交換触媒がチタンアルコキシドであり、該アルコキシド基は1から6個の炭素原子を含有する、請求項1〜6のいずれか一項に記載の方法。
- 工程(Bl)からの過剰のジアルコキシメタンおよびアルキルアルコール並びに工程(B2)からの未反応のグリセロールおよび工程(A)で均一触媒が使用された場合には均一触媒を、再使用するかまたは方法にリサイクルすることができる、請求項1〜7のいずれか一項に記載の方法。
- 工程(C)において、アルキルアルコールはメタノールであり、前記工程(C)においてジメトキシメタンが反応剤として使用された場合には、脂肪酸アルキルエステルは脂肪酸メチルエステルである、請求項1〜8のいずれか一項に記載の方法。
- 工程(C)で使用される酸触媒は、硫酸である均一触媒であるか、または酸性イオン交換樹脂である不均一触媒である、請求項1〜9のいずれか一項に記載の方法。
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ARP130102941A AR094626A1 (es) | 2012-11-09 | 2013-08-20 | Proceso de fabricación de biocombustibles |
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PL411868A1 (pl) | 2015-04-02 | 2016-10-10 | Biotim Spółka Z Ograniczoną Odpowiedzialnością | Instalacja do produkcji bioestrów metylowych z jednoczesnym przerobem surowej odpadowej fazy glicerynowej - metodą przemienną |
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CN104812745B (zh) | 2017-04-05 |
CN104812745A (zh) | 2015-07-29 |
AR094626A1 (es) | 2015-08-19 |
EP2730567A1 (en) | 2014-05-14 |
MX2015005870A (es) | 2016-03-31 |
JP6336462B2 (ja) | 2018-06-06 |
US20150307794A1 (en) | 2015-10-29 |
PL2917199T3 (pl) | 2016-10-31 |
SI2917199T1 (sl) | 2016-07-29 |
ECSP15021231A (es) | 2016-01-29 |
CA2890805A1 (en) | 2014-05-15 |
EP2917199A1 (en) | 2015-09-16 |
MX359138B (es) | 2018-09-17 |
AU2013343475A1 (en) | 2015-06-04 |
HK1211925A1 (zh) | 2016-06-03 |
ES2577112T3 (es) | 2016-07-13 |
WO2014072453A1 (en) | 2014-05-15 |
DK2917199T3 (en) | 2016-07-04 |
US9157039B1 (en) | 2015-10-13 |
AU2013343475B2 (en) | 2017-07-13 |
CY1117590T1 (el) | 2017-04-26 |
MY171741A (en) | 2019-10-27 |
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BR112015010699A2 (pt) | 2017-07-11 |
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