JPS62273982A - ２，６−ビス（４−ヒドロキシ−３，５−ジメトキシフエニル）−３，７−ジオキサビシクロ〔３．３．０〕オクタンの製造法 - Google Patents

２，６−ビス（４−ヒドロキシ−３，５−ジメトキシフエニル）−３，７−ジオキサビシクロ〔３．３．０〕オクタンの製造法

Info

Publication number: JPS62273982A
Authority: JP; Japan
Prior art keywords: syringaresinol; water; dioxabicyclo; dimethoxyphenyl; bis
Prior art date: 1986-05-22
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.): Granted

Application number

JP11800286A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0515716B2 (fr

Inventor

Norio Matsukura

松倉　紀男

Kazuo Terasawa

寺沢　一雄

Kihachiro Oshima

大島　喜八郎

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Jujo Paper Co Ltd

Original Assignee

Jujo Paper Co Ltd

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.)

1986-05-22

Filing date

1986-05-22

Publication date

1987-11-28

1986-05-22 Application filed by Jujo Paper Co Ltd filed Critical Jujo Paper Co Ltd

1986-05-22 Priority to JP11800286A priority Critical patent/JPS62273982A/ja

1987-11-28 Publication of JPS62273982A publication Critical patent/JPS62273982A/ja

1993-03-02 Publication of JPH0515716B2 publication Critical patent/JPH0515716B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 13
KOWMJRJXZMEZLD-UHFFFAOYSA-N syringaresinol Chemical compound COC1=C(O)C(OC)=CC(C2C3C(C(OC3)C=3C=C(OC)C(O)=C(OC)C=3)CO2)=C1 KOWMJRJXZMEZLD-UHFFFAOYSA-N 0.000 title description 48
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 60
229920005610 lignin Polymers 0.000 claims abstract description 32
-1 ether ketone Chemical class 0.000 claims abstract description 9
239000003960 organic solvent Substances 0.000 claims abstract description 9
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 4
150000002148 esters Chemical class 0.000 claims abstract description 4
238000010411 cooking Methods 0.000 claims description 16
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
HYKQSAMEQTXOBX-UHFFFAOYSA-N 1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan Chemical compound C1OCC2COCC21 HYKQSAMEQTXOBX-UHFFFAOYSA-N 0.000 claims 1
XNWFXTOHNKPYMK-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydrocyclopenta[c]dioxole Chemical compound C1OOC2CCCC21 XNWFXTOHNKPYMK-UHFFFAOYSA-N 0.000 claims 1
GBXPNSIDOADMPA-UHFFFAOYSA-N 4-(3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-yl)-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(C23C(COC2)COC3)=C1 GBXPNSIDOADMPA-UHFFFAOYSA-N 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
150000002170 ethers Chemical class 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
150000001875 compounds Chemical class 0.000 abstract description 3
239000004215 Carbon black (E152) Substances 0.000 abstract description 2
229930195733 hydrocarbon Natural products 0.000 abstract description 2
150000002430 hydrocarbons Chemical class 0.000 abstract description 2
230000029087 digestion Effects 0.000 abstract 3
LVUPFEOCDSHRBL-UHFFFAOYSA-N syringaresinol Natural products COc1cccc(OC)c1C2OCC3C2COC3c4c(OC)cccc4OC LVUPFEOCDSHRBL-UHFFFAOYSA-N 0.000 description 47
241000196324 Embryophyta Species 0.000 description 23
238000000034 method Methods 0.000 description 23
239000007787 solid Substances 0.000 description 11
239000002023 wood Substances 0.000 description 11
239000007788 liquid Substances 0.000 description 10
239000002994 raw material Substances 0.000 description 10
239000000047 product Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229920002488 Hemicellulose Polymers 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000011121 hardwood Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
239000013078 crystal Substances 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000000862 absorption spectrum Methods 0.000 description 4
JMFRWRFFLBVWSI-NSCUHMNNSA-N coniferol Chemical compound COC1=CC(\C=C\CO)=CC=C1O JMFRWRFFLBVWSI-NSCUHMNNSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000010903 husk Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000863480 Vinca Species 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
235000008216 herbs Nutrition 0.000 description 3
239000012535 impurity Substances 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000002699 waste material Substances 0.000 description 3
235000013162 Cocos nucifera Nutrition 0.000 description 2
244000060011 Cocos nucifera Species 0.000 description 2
229940119526 coniferyl alcohol Drugs 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
238000006356 dehydrogenation reaction Methods 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
229930182470 glycoside Natural products 0.000 description 2
150000002338 glycosides Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000009776 industrial production Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000004537 pulping Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
VJOBNGRIBLNUKN-BMHXQBNDSA-N (+)-Medioresinol Natural products C1=C(O)C(OC)=CC([C@@H]2[C@@H]3[C@@H]([C@H](OC3)C=3C=C(OC)C(O)=C(OC)C=3)CO2)=C1 VJOBNGRIBLNUKN-BMHXQBNDSA-N 0.000 description 1
VJOBNGRIBLNUKN-UHFFFAOYSA-N (+)-medioresinal Natural products C1=C(O)C(OC)=CC(C2C3C(C(OC3)C=3C=C(OC)C(O)=C(OC)C=3)CO2)=C1 VJOBNGRIBLNUKN-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
QMPOHKDJNKTEHF-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1-benzofuran Chemical compound O1C2=CC=CC=C2CC1C1=CC=CC=C1 QMPOHKDJNKTEHF-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
VJOBNGRIBLNUKN-ITZZLVQVSA-N 4-[(3s,3ar,6ar)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenol Chemical compound C1=C(O)C(OC)=CC([C@@H]2[C@@H]3[C@@H](C(OC3)C=3C=C(OC)C(O)=C(OC)C=3)CO2)=C1 VJOBNGRIBLNUKN-ITZZLVQVSA-N 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
235000003826 Artemisia Nutrition 0.000 description 1
235000003261 Artemisia vulgaris Nutrition 0.000 description 1
240000006891 Artemisia vulgaris Species 0.000 description 1
235000017166 Bambusa arundinacea Nutrition 0.000 description 1
235000017491 Bambusa tulda Nutrition 0.000 description 1
235000018185 Betula X alpestris Nutrition 0.000 description 1
235000018212 Betula X uliginosa Nutrition 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
241000238557 Decapoda Species 0.000 description 1
241001632410 Eleutherococcus senticosus Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
240000000731 Fagus sylvatica Species 0.000 description 1
235000010099 Fagus sylvatica Nutrition 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
240000004371 Panax ginseng Species 0.000 description 1
235000002789 Panax ginseng Nutrition 0.000 description 1
244000082204 Phyllostachys viridis Species 0.000 description 1
235000015334 Phyllostachys viridis Nutrition 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
235000009052 artemisia Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011425 bamboo Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
230000007123 defense Effects 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
235000008434 ginseng Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000002655 kraft paper Substances 0.000 description 1
229930013686 lignan Natural products 0.000 description 1
150000005692 lignans Chemical class 0.000 description 1
235000009408 lignans Nutrition 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229920001542 oligosaccharide Polymers 0.000 description 1
150000002482 oligosaccharides Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000005325 percolation Methods 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
239000011122 softwood Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
PTNLHDGQWUGONS-OWOJBTEDSA-N trans-p-coumaryl alcohol Chemical compound OC\C=C\C1=CC=C(O)C=C1 PTNLHDGQWUGONS-OWOJBTEDSA-N 0.000 description 1
229930189508 virginol Natural products 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP11800286A 1986-05-22 1986-05-22 ２，６−ビス（４−ヒドロキシ−３，５−ジメトキシフエニル）−３，７−ジオキサビシクロ〔３．３．０〕オクタンの製造法 Granted JPS62273982A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP11800286A JPS62273982A (ja)	1986-05-22	1986-05-22	２，６−ビス（４−ヒドロキシ−３，５−ジメトキシフエニル）−３，７−ジオキサビシクロ〔３．３．０〕オクタンの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11800286A JPS62273982A (ja)	1986-05-22	1986-05-22	２，６−ビス（４−ヒドロキシ−３，５−ジメトキシフエニル）−３，７−ジオキサビシクロ〔３．３．０〕オクタンの製造法

Publications (2)

Publication Number	Publication Date
JPS62273982A true JPS62273982A (ja)	1987-11-28
JPH0515716B2 JPH0515716B2 (fr)	1993-03-02

Family

ID=14725620

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11800286A Granted JPS62273982A (ja)	1986-05-22	1986-05-22	２，６−ビス（４−ヒドロキシ−３，５−ジメトキシフエニル）−３，７−ジオキサビシクロ〔３．３．０〕オクタンの製造法

Country Status (1)

Country	Link
JP (1)	JPS62273982A (fr)

1986
- 1986-05-22 JP JP11800286A patent/JPS62273982A/ja active Granted

Also Published As

Publication number	Publication date
JPH0515716B2 (fr)	1993-03-02

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