JPS62502375A - エステル化方法 - Google Patents

エステル化方法

Info

Publication number: JPS62502375A
Authority: JP; Japan
Prior art keywords: formula; carboxylic acid; aryl; tables; alkylene
Prior art date: 1985-02-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP61501411A

Other languages

English (en)

Japanese (ja)

Inventor

ゴドトフレドセン，スベン　エリク

ブンドゴールド，ペーター

アンデレセン，オツトー

Original Assignee

ノボ　インダストリ　アクテイ−ゼルスカブ

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-02-27

Filing date

1986-02-27

Publication date

1987-09-17

1986-02-27 Application filed by ノボ　インダストリ　アクテイ−ゼルスカブ filed Critical ノボ　インダストリ　アクテイ−ゼルスカブ

1987-09-17 Publication of JPS62502375A publication Critical patent/JPS62502375A/ja

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 52
230000032050 esterification Effects 0.000 title description 18
238000005886 esterification reaction Methods 0.000 title description 18
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
108090000790 Enzymes Proteins 0.000 claims description 18
102000004190 Enzymes Human genes 0.000 claims description 18
230000015572 biosynthetic process Effects 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 12
-1 hydroxy, amino, carboxyl Chemical group 0.000 claims description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
150000001733 carboxylic acid esters Chemical class 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
108090001060 Lipase Proteins 0.000 claims description 7
239000004367 Lipase Substances 0.000 claims description 7
102000004882 Lipase Human genes 0.000 claims description 7
230000018044 dehydration Effects 0.000 claims description 7
238000006297 dehydration reaction Methods 0.000 claims description 7
235000019421 lipase Nutrition 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
150000001728 carbonyl compounds Chemical class 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
150000002772 monosaccharides Chemical class 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
108090000371 Esterases Proteins 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
150000001720 carbohydrates Chemical group 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
108010093096 Immobilized Enzymes Proteins 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229930091371 Fructose Natural products 0.000 claims 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 1
239000005715 Fructose Substances 0.000 claims 1
LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims 1
150000001241 acetals Chemical class 0.000 claims 1
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims 1
229930182830 galactose Natural products 0.000 claims 1
239000008103 glucose Substances 0.000 claims 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
239000002253 acid Substances 0.000 description 19
229920005862 polyol Polymers 0.000 description 13
150000003077 polyols Chemical class 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 6
238000013519 translation Methods 0.000 description 6
LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 5
OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000012937 correction Methods 0.000 description 4
238000005907 ketalization reaction Methods 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000012071 phase Substances 0.000 description 3
150000003626 triacylglycerols Chemical class 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 2
FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
238000006359 acetalization reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
150000004665 fatty acids Chemical group 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000008176 lyophilized powder Substances 0.000 description 2
YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
239000001993 wax Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
LEVONNIFUFSRKZ-UHFFFAOYSA-N 3-(carboxymethyl)-2,2-dimethylcyclobutane-1-carboxylic acid Chemical compound CC1(C)C(CC(O)=O)CC1C(O)=O LEVONNIFUFSRKZ-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
241000352320 Amegilla aeruginosa Species 0.000 description 1
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
206010039509 Scab Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003599 detergent Substances 0.000 description 1
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
238000010586 diagram Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000006911 enzymatic reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000002243 furanoses Chemical class 0.000 description 1
150000002303 glucose derivatives Chemical class 0.000 description 1
239000003292 glue Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
150000004072 triols Chemical class 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Saccharide Compounds (AREA)

JP61501411A 1985-02-27 1986-02-27 エステル化方法 Pending JPS62502375A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DK87785A DK87785A (da)	1985-02-27	1985-02-27	Esterificeringsmetode
DK877/85		1985-02-27
DK5147/85		1985-11-07

Publications (1)

Publication Number	Publication Date
JPS62502375A true JPS62502375A (ja)	1987-09-17

Family

ID=8098539

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61501411A Pending JPS62502375A (ja)	1985-02-27	1986-02-27	エステル化方法

Country Status (2)

Country	Link
JP (1)	JPS62502375A (da)
DK (1)	DK87785A (da)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59118094A (ja) *	1982-12-24	1984-07-07	Nippon Oil & Fats Co Ltd	モノグリセリドの製造法

1985
- 1985-02-27 DK DK87785A patent/DK87785A/da not_active Application Discontinuation
1986
- 1986-02-27 JP JP61501411A patent/JPS62502375A/ja active Pending

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS59118094A (ja) *	1982-12-24	1984-07-07	Nippon Oil & Fats Co Ltd	モノグリセリドの製造法

Also Published As

Publication number	Publication date
DK87785A (da)	1986-08-28
DK87785D0 (da)	1985-02-27

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