JPS60237085A - α−トコフエロ−ルの製造法 - Google Patents

α−トコフエロ−ルの製造法

Info

Publication number: JPS60237085A
Authority: JP; Japan
Prior art keywords: tocopherol; reaction; formaldehyde; alpha; alkali metal
Prior art date: 1984-05-11
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

JP9297584A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0522708B2 (fr

Inventor

Hiroaki Yuge

弓削　博昭

Yoji Tachibana

陽二橘

Hitoshi Toyoda

豊田　仁

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.)

Nisshin Seifun Group Inc

Nisshin Chemical Co Ltd

Original Assignee

Nisshin Seifun Group Inc

Nisshin Chemical 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.)

1984-05-11

Filing date

1984-05-11

Publication date

1985-11-25

1984-05-11 Application filed by Nisshin Seifun Group Inc, Nisshin Chemical Co Ltd filed Critical Nisshin Seifun Group Inc

1984-05-11 Priority to JP9297584A priority Critical patent/JPS60237085A/ja

1985-11-25 Publication of JPS60237085A publication Critical patent/JPS60237085A/ja

1993-03-30 Publication of JPH0522708B2 publication Critical patent/JPH0522708B2/ja

Status Granted legal-status Critical Current

Links

GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 title claims abstract description 87
235000004835 α-tocopherol Nutrition 0.000 title claims abstract description 42
229940087168 alpha tocopherol Drugs 0.000 title claims abstract description 37
229960000984 tocofersolan Drugs 0.000 title claims abstract description 37
239000002076 α-tocopherol Substances 0.000 title claims abstract description 37
238000004519 manufacturing process Methods 0.000 title claims description 3
GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 claims abstract description 26
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 24
235000010389 delta-tocopherol Nutrition 0.000 claims abstract description 15
GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 claims abstract description 13
239000002446 δ-tocopherol Substances 0.000 claims abstract description 13
-1 alkali metal bisulfate Chemical class 0.000 claims abstract description 10
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 6
229920000642 polymer Polymers 0.000 claims abstract description 6
239000011732 tocopherol Substances 0.000 abstract description 25
229960001295 tocopherol Drugs 0.000 abstract description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 abstract description 17
229930003799 tocopherol Natural products 0.000 abstract description 14
235000010384 tocopherol Nutrition 0.000 abstract description 13
229930040373 Paraformaldehyde Natural products 0.000 abstract description 6
229920002866 paraformaldehyde Polymers 0.000 abstract description 6
WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 abstract description 4
230000000694 effects Effects 0.000 abstract description 3
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 abstract description 3
239000003960 organic solvent Substances 0.000 abstract description 3
229930003427 Vitamin E Natural products 0.000 abstract description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 2
229940046009 vitamin E Drugs 0.000 abstract description 2
235000019165 vitamin E Nutrition 0.000 abstract description 2
239000011709 vitamin E Substances 0.000 abstract description 2
239000011590 β-tocopherol Substances 0.000 abstract description 2
235000007680 β-tocopherol Nutrition 0.000 abstract description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
235000010382 gamma-tocopherol Nutrition 0.000 abstract 1
HPCCWDVOHHFCKM-UHFFFAOYSA-M lithium;hydrogen sulfate Chemical compound [Li+].OS([O-])(=O)=O HPCCWDVOHHFCKM-UHFFFAOYSA-M 0.000 abstract 1
239000002478 γ-tocopherol Substances 0.000 abstract 1
QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 19
238000000034 method Methods 0.000 description 12
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
235000012424 soybean oil Nutrition 0.000 description 8
239000003549 soybean oil Substances 0.000 description 8
239000012141 concentrate Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
239000001257 hydrogen Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
238000011084 recovery Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
150000003772 α-tocopherols Chemical class 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000002994 raw material Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
WGPAQYSVWYWZKT-UHFFFAOYSA-N [C].[Ra] Chemical compound [C].[Ra] WGPAQYSVWYWZKT-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000007806 chemical reaction intermediate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 2
LTUDISCZKZHRMJ-UHFFFAOYSA-N potassium;hydrate Chemical compound O.[K] LTUDISCZKZHRMJ-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000126 substance Substances 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
150000003789 δ-tocopherols Chemical class 0.000 description 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229940066595 beta tocopherol Drugs 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
ZJVTYKZWDWVIFD-UHFFFAOYSA-N zinc;hydrochloride Chemical compound Cl.[Zn] ZJVTYKZWDWVIFD-UHFFFAOYSA-N 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pyrane Compounds (AREA)

JP9297584A 1984-05-11 1984-05-11 α−トコフエロ−ルの製造法 Granted JPS60237085A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP9297584A JPS60237085A (ja)	1984-05-11	1984-05-11	α−トコフエロ−ルの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP9297584A JPS60237085A (ja)	1984-05-11	1984-05-11	α−トコフエロ−ルの製造法

Publications (2)

Publication Number	Publication Date
JPS60237085A true JPS60237085A (ja)	1985-11-25
JPH0522708B2 JPH0522708B2 (fr)	1993-03-30

Family

ID=14069398

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9297584A Granted JPS60237085A (ja)	1984-05-11	1984-05-11	α−トコフエロ−ルの製造法

Country Status (1)

Country	Link
JP (1)	JPS60237085A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997007113A1 (fr) *	1995-08-17	1997-02-27	Eastman Chemical Company	PREPARATION DE α-TOCOPHEROL

1984
- 1984-05-11 JP JP9297584A patent/JPS60237085A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997007113A1 (fr) *	1995-08-17	1997-02-27	Eastman Chemical Company	PREPARATION DE α-TOCOPHEROL

Also Published As

Publication number	Publication date
JPH0522708B2 (fr)	1993-03-30

Legal Events

Date	Code	Title	Description
2004-03-30	LAPS	Cancellation because of no payment of annual fees

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JPS60237085A - α−トコフエロ−ルの製造法 - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=14069398

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Also Published As

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