JPS6330906B2 - - Google Patents
Info
- Publication number
- JPS6330906B2 JPS6330906B2 JP14998479A JP14998479A JPS6330906B2 JP S6330906 B2 JPS6330906 B2 JP S6330906B2 JP 14998479 A JP14998479 A JP 14998479A JP 14998479 A JP14998479 A JP 14998479A JP S6330906 B2 JPS6330906 B2 JP S6330906B2
- Authority
- JP
- Japan
- Prior art keywords
- tocopherol
- acetate
- reaction
- mol
- zinc
- Prior art date
- 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.)
- Expired
Links
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 22
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 claims description 19
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 18
- 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 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229930003799 tocopherol Natural products 0.000 claims description 14
- 239000011732 tocopherol Substances 0.000 claims description 14
- 229940042585 tocopherol acetate Drugs 0.000 claims description 13
- 235000010384 tocopherol Nutrition 0.000 claims description 12
- 229960001295 tocopherol Drugs 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- 235000005074 zinc chloride Nutrition 0.000 claims description 11
- 239000011592 zinc chloride Substances 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 9
- FOYKKGHVWRFIBD-UHFFFAOYSA-N gamma-tocopherol acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 FOYKKGHVWRFIBD-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 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 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 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 description 4
- 229960000984 tocofersolan Drugs 0.000 description 4
- 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 description 4
- DFUSDJMZWQVQSF-XLGIIRLISA-N (2r)-2-methyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol Chemical class OC1=CC=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 DFUSDJMZWQVQSF-XLGIIRLISA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 235000001809 DL-alpha-tocopherylacetate Nutrition 0.000 description 3
- 239000011626 DL-alpha-tocopherylacetate Substances 0.000 description 3
- 229940066595 beta tocopherol Drugs 0.000 description 3
- 239000013076 target substance Substances 0.000 description 3
- 235000007680 β-tocopherol Nutrition 0.000 description 3
- 239000011590 β-tocopherol Substances 0.000 description 3
- 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 description 3
- 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 description 2
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 2
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 229940087168 alpha tocopherol Drugs 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 235000010389 delta-tocopherol Nutrition 0.000 description 2
- 229940117373 dl-alpha tocopheryl acetate Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000010382 gamma-tocopherol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000019149 tocopherols Nutrition 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- 235000004835 α-tocopherol Nutrition 0.000 description 2
- 239000002076 α-tocopherol Substances 0.000 description 2
- 239000002478 γ-tocopherol Substances 0.000 description 2
- 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 2
- 239000002446 δ-tocopherol Substances 0.000 description 2
- 235000002414 D-alpha-tocopherylacetate Nutrition 0.000 description 1
- 239000011740 D-alpha-tocopherylacetate Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940039770 d-alpha-tocopheryl acetate Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、トコフエロ−ルアセテ−トの製造方
法に関する。更に詳しくは、トコフエロ−ルと無
水酢酸を反応せしめてトコフエロ−ルアセテ−ト
を製造するにあたり、塩化水素または塩酸と、亜
鉛または塩化亜鉛の一つまたは二つとの混合物の
存在下に反応をおこなうことを特徴とするトコフ
エロ−ルアセテ−トの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing tocopheryl acetate. More specifically, in producing tocopherol acetate by reacting tocopherol and acetic anhydride, the reaction is carried out in the presence of hydrogen chloride or hydrochloric acid and zinc or a mixture of one or two of zinc chloride. The present invention relates to a method for producing tocopherol acetate characterized by the following.
トコフエロ−ルすなわちビタミンＥは、食品，
医薬品，化粧品，飼料添加剤などに広く用途を有
し、構造的には、α−トコフエロ−ル、β−トコ
フエロ−ル、γ−トコフエロ−ル、δ−トコフエ
ロ−ルなどのトコ−ル誘導体である。しかしなが
ら、トコフエロ−ル自体は、その構造において遊
離フエノ−ル性水酸基を有すため、空気、光など
により酸化を受けやすく不安定であるので、実際
に使用する場合は、トコフエロ−ルを安定な種々
の誘導体とすることがしばしばおこなわれてい
る。これらの誘導体のうち、最も代表的な例とし
てはトコフエロ−ルの酢酸エステル、すなわちト
コフエロ−ルアセテ−トがあり、食品，医薬品，
化粧品，飼料添加剤などの種々の分野で広く用い
られている。 Tocopherols, or vitamin E, are found in foods,
It has a wide range of uses in pharmaceuticals, cosmetics, feed additives, etc., and is structurally composed of tocol derivatives such as α-tocopherol, β-tocopherol, γ-tocopherol, and δ-tocopherol. be. However, tocopherol itself has a free phenolic hydroxyl group in its structure, making it susceptible to oxidation by air and light, making it unstable. Various derivatives are often used. Among these derivatives, the most representative example is tocopherol acetate, which is used in foods, pharmaceuticals, and other products.
It is widely used in various fields such as cosmetics and feed additives.
本発明におけるトコフエロ−ルとは、上述した
α−トコフエロ−ル、β−トコフエロ−ル、γ−
トコフエロ−ル、δ−トコフエロ−ルなどのトコ
−ル誘導体のいずれでもよく、またこれらのトコ
−ル誘導体はその化学構造上から、ｄ−体、dl−
体、−体がそれぞれ存在するが、これらの異性
体のいずれでもよい。したがつて、本発明の目的
物質であるトコフエロ−ルアセテ−トは、上述し
たトコフエロ−ルの定義に対応するトコフエロ−
ルアセテ−トである。すなわち、本発明方法によ
つて製造されるトコフエロ−ルアセテ−トとは、
α−トコフエロ−ルアセテ−ト、β−トコフエロ
−ルアセテ−ト、γ−トコフエロ−ルアセテ−
ト、δ−トコフエロ−ルアセテ−トなどのトコ−
ル誘導体のアセテ−トをすべて含み、かつこれら
のそれぞれの異性体、すなわち、ｄ−体、dl−
体、−体のいずれをも含む。これらの化合物の
うち、工業的見地、ビタミンＥとしての薬理作用
上の見地から、dl−α−トコフエロ−ルアセテ−
ト，ｄ−α−トコフエロ−ルアセテ−トなどが最
も多く用いられる。 The tocopherols in the present invention include the above-mentioned α-tocopherol, β-tocopherol, and γ-tocopherol.
Any tocol derivatives such as tocopherol and δ-tocopherol may be used.Due to their chemical structure, these tocol derivatives may be d-form, dl-form, etc.
There are two isomers, one isomer and the other isomer, but any of these isomers may be used. Therefore, tocopherol acetate, which is the target substance of the present invention, is a tocopherol that corresponds to the above-mentioned definition of tocopherol.
It is ruacetate. That is, tocopherol acetate produced by the method of the present invention is:
α-tocopherol acetate, β-tocopherol acetate, γ-tocopherol acetate
Tocolytes such as
including all acetate derivatives and their respective isomers, i.e., d-form, dl-
It includes both body and -body. Among these compounds, dl-α-tocopheryl acetate has been considered from an industrial standpoint and from a pharmacological standpoint as vitamin E.
and d-α-tocopheryl acetate are most commonly used.
トコフエロ−ルアセテ−トを製造する方法とし
ては、トコフエロ−ルに無水酢酸を反応させる方
法が一般的であるが、その際、触媒としてピリジ
ン、酢酸ソ−ダなどを使用する方法が知られてい
る。 A common method for producing tocopheryl acetate is to react tocopherol with acetic anhydride, but methods using pyridine, sodium acetate, etc. as catalysts are also known. .
しかしながら、この方法は、これらの触媒の活
性が低いため、無水酢酸が大過剰必要となり、そ
の結果反応時間が長くなり、加熱還流が必要とさ
れる。したがつて、この方法では、多量の酢酸が
副生し、そのため危険な加熱還流の制御が必要と
なるので、必ずしも工業的に有利な方法とはいい
難い。そこで本発明者等は、上述の従来法の技術
的欠点を解決すべく、鋭意研究を長期間にわたつ
ておこなつてきた結果、触媒として塩化水素また
は塩酸と、亜鉛または塩化亜鉛の一つまたは二つ
との混合物を用いれば、所期の目的を達成できる
ことを見い出した。すなわち、トコフエロ−ルと
無水酢酸を反応せしめてトコフエロ−ルアセテ−
トを製造するにあたり、塩化水素または塩酸と、
亜鉛または塩化亜鉛の一つまたは二つとの混合物
の存在下に反応をおこなえば、室温の温和な条件
で、当量からわずかに過剰量の無水酢酸を用い
て、短時間に収率よく目的物質のトコフエロ−ル
アセテ−トを製造できることを見い出し、本発明
を完成した。 However, this method requires a large excess of acetic anhydride due to the low activity of these catalysts, resulting in long reaction times and the need for heating to reflux. Therefore, in this method, a large amount of acetic acid is produced as a by-product, and dangerous heating and reflux control is therefore required, so it cannot necessarily be said to be an industrially advantageous method. Therefore, the present inventors have conducted intensive research over a long period of time in order to solve the technical drawbacks of the above-mentioned conventional methods. It has been found that the intended purpose can be achieved by using a mixture of the two. That is, tocopheryl acetate is produced by reacting tocopherol and acetic anhydride.
In producing the above, hydrogen chloride or hydrochloric acid and
If the reaction is carried out in the presence of zinc or a mixture of zinc chloride or zinc chloride, the target substance can be obtained in a short time and in good yield under mild conditions at room temperature using an equivalent to a slight excess of acetic anhydride. It was discovered that tocopheryl acetate can be produced, and the present invention was completed.
したがつて、本発明の目的は、工業的に極めて
有利で新規なトコフエロ−ルアセテ−トの製造方
法を提供するにある。 Therefore, an object of the present invention is to provide a novel method for producing tocopherol acetate which is industrially extremely advantageous.
更に本発明の目的は、トコフエロ−ルと無水酢
酸を反応せしめてトコフエロ−ルアセテ−トを製
造するに際し、大過剰量の無水酢酸を必要としな
い、安全でかつ工業的に極めて有利なトコフエロ
−ルアセテ−トの新規製造方法を提供するにあ
る。 A further object of the present invention is to produce tocopherol acetate which is safe and industrially extremely advantageous and which does not require a large excess amount of acetic anhydride when producing tocopherol acetate by reacting tocopherol and acetic anhydride. - To provide a new method for manufacturing sheets.
更に本発明の目的は、収率がよく、かつ経済的
なトコフエロ−ルアセテ−トの新規製造方法を提
供するにある。 A further object of the present invention is to provide a new method for producing tocopherol acetate which is economical and has a good yield.
本発明において使用される触媒は、塩化水素ま
たは塩酸と、亜鉛または塩化亜鉛の一つまたは二
つとの混合物である。すなわち、塩化水素または
塩酸と、亜鉛または塩化亜鉛を適宜組み合わせて
使用するが、この際、塩化水素または塩酸と、亜
鉛、塩化亜鉛の三者を組み合わせて使用してもよ
い。好ましい組み合わせとしては、(1)塩酸と亜鉛
または(2)塩酸と塩化亜鉛である。 The catalyst used in the invention is a mixture of hydrogen chloride or hydrochloric acid and one or both of zinc or zinc chloride. That is, hydrogen chloride or hydrochloric acid and zinc or zinc chloride are used in appropriate combinations, but in this case, hydrogen chloride or hydrochloric acid, zinc, and zinc chloride may be used in combination. Preferred combinations include (1) hydrochloric acid and zinc or (2) hydrochloric acid and zinc chloride.
上述の触媒の使用量は、反応条件によつて異な
るが、通常はトコフエロ−ル１モルに対して、塩
化水素または塩酸0.01〜0.2モル、好ましくは0.02
〜0.06モル、亜鉛0.01〜0.2モル、好ましくは0.02
〜0.06モル、塩化亜鉛0.001〜0.1モル、好ましく
は0.01〜0.05モルの範囲で、２ないし３者を組み
合わせて用いられる。 The amount of the above-mentioned catalyst used varies depending on the reaction conditions, but is usually 0.01 to 0.2 mol of hydrogen chloride or hydrochloric acid, preferably 0.02 mol, per 1 mol of tocopherol.
~0.06 mol, zinc 0.01-0.2 mol, preferably 0.02
~0.06 mol, zinc chloride 0.001 to 0.1 mol, preferably 0.01 to 0.05 mol, and two or three of them are used in combination.
また、この際出発物質の一方である無水酢酸の
使用量は、トコフエロ−ルと当量か、あるいはわ
ずかに過剰量を用いることにより十分反応する
が、工業的にはトコフエロ−ル１モルに対し、無
水酢酸約1.2〜1.5モルの使用量が好ましい。 In addition, in this case, the amount of acetic anhydride used as one of the starting materials is equivalent to that of tocopherol, or a slight excess amount is used to achieve a sufficient reaction, but industrially, per mole of tocopherol, An amount of about 1.2 to 1.5 moles of acetic anhydride is preferred.
本発明方法における反応は溶媒の存在下若しく
は不存在下に実施することができる。溶媒を使用
する場合、反応に対して不活性で、かつ塩基性で
ないものであればいかなる溶媒でもよく特に制限
はないが、好ましくは本反応が発熱反応であるの
で、反応熱を潜熱で十分に吸収して有効に利用で
きるトルエン等が用いられる。 The reaction in the method of the invention can be carried out in the presence or absence of a solvent. When using a solvent, any solvent may be used as long as it is inert to the reaction and not basic, but there are no particular restrictions. However, since this reaction is exothermic, it is preferable that the reaction heat be sufficiently absorbed by the latent heat. Toluene, etc., which can be absorbed and used effectively, is used.
反応温度は約10〜30℃の室温程度の温度で十分
反応が進行する。 The reaction proceeds sufficiently at a reaction temperature of about 10 to 30°C, which is about room temperature.
反応時間は、触媒量、反応温度などにより異な
るが、通常は30分〜２時間程度で十分である。 The reaction time varies depending on the amount of catalyst, reaction temperature, etc., but usually about 30 minutes to 2 hours is sufficient.
反応終了後、反応混合物より触媒を分離したの
ち、溶媒を留去後必要に応じて洗滌乾燥し、更に
必要により、通常の方法例えば蒸留・カラムクロ
マトグラフイーなどの方法により、目的物質トコ
フエロ−ルアセテ−トを分離精製することができ
る。 After the completion of the reaction, the catalyst is separated from the reaction mixture, the solvent is distilled off and then washed and dried if necessary. If necessary, the target substance tocopheryl acetate is removed by a conventional method such as distillation or column chromatography. - can be separated and purified.
以下に、本発明の代表的実施例を掲げるが、本
発明がこれらのみに限定されることがないことは
いうまでもない。 Typical examples of the present invention are listed below, but it goes without saying that the present invention is not limited to these only.
実施例 １
dl−α−トコフエロ−ル86ｇ（0.2モル）をト
ルエン54mlに溶解し、室温で混合撹拌下亜鉛末
0.5ｇ、濃塩酸１ml、および無水酢酸27ｇ（0.26
モル）を加える。反応温度は、無水酢酸添加後、
22℃から約10分間で56℃まで上昇し、その後徐々
に低下する。反応液を水洗し、不溶物を分離後、
溶媒を留去し、dl−α−トコフエロ−ルアセテ−
ト91ｇ（収率96％）を得た。Example 1 86 g (0.2 mol) of dl-α-tocopherol was dissolved in 54 ml of toluene, and zinc powder was mixed with stirring at room temperature.
0.5 g, 1 ml of concentrated hydrochloric acid, and 27 g of acetic anhydride (0.26
mol). The reaction temperature is after adding acetic anhydride.
The temperature rises from 22℃ to 56℃ in about 10 minutes, and then gradually decreases. After washing the reaction solution with water and separating the insoluble matter,
The solvent was distilled off and dl-α-tocopherol acetate
91 g (yield: 96%) of the product was obtained.
実施例 ２
ｄ−β−トコフエロ−ル82ｇ（0.2モル）、トル
エン50ml、亜鉛末500mg、濃塩酸１ml、および無
水酢酸27ｇ（0.26モル）を用いて、実施例１と同
様の操作をおこない、ｄ−β−トコフエロ−ルア
セテ−ト87ｇ（収率95％）を得た。Example 2 The same operation as in Example 1 was carried out using 82 g (0.2 mol) of d-β-tocopherol, 50 ml of toluene, 500 mg of zinc powder, 1 ml of concentrated hydrochloric acid, and 27 g (0.26 mol) of acetic anhydride. 87 g (yield 95%) of -β-tocopheryl acetate was obtained.
実施例 ３
ｄ−γ−トコフエロ−ル82ｇ（0.2モル）、トル
エン50ml、塩化亜鉛400mg、濃塩酸１ml、無水酢
酸27ｇ（0.26モル）を用いて、実施例１と同様の
操作をおこない、ｄ−γ−トコフエロ−ルアセテ
−ト88ｇ（収率96％）を得た。Example 3 The same operation as in Example 1 was carried out using 82 g (0.2 mol) of d-γ-tocopherol, 50 ml of toluene, 400 mg of zinc chloride, 1 ml of concentrated hydrochloric acid, and 27 g (0.26 mol) of acetic anhydride. 88 g (yield 96%) of γ-tocopheryl acetate was obtained.
実施例 ４
dl−α−トコフエロ−ル86ｇ（0.2モル）、トル
エン54ml、亜鉛末300mg、塩化亜鉛200mg、濃塩酸
１mlおよび無水酢酸27ｇ（0.26モル）を用いて、
実施例１と同様の操作をおこないdl−α−トコフ
エロ−ルアセテ−ト91.5ｇ（収率97％）を得た。Example 4 Using 86 g (0.2 mol) of dl-α-tocopherol, 54 ml of toluene, 300 mg of zinc powder, 200 mg of zinc chloride, 1 ml of concentrated hydrochloric acid, and 27 g (0.26 mol) of acetic anhydride,
The same operation as in Example 1 was carried out to obtain 91.5 g (97% yield) of dl-α-tocopheryl acetate.
Claims (1)
コフエロ−ルアセテ−トを製造するにあたり、塩
化水素または塩酸と、亜鉛または塩化亜鉛の一つ
または二つとの混合物の存在下に反応をおこなう
ことを特徴とするトコフエロ−ルアセテ−トの製
造法。1. In producing tocopherol acetate by reacting tocopherol and acetic anhydride, the reaction is carried out in the presence of hydrogen chloride or hydrochloric acid and zinc or a mixture of one or both of zinc chloride. A method for producing tocopherol acetate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14998479A JPS5673081A (en) | 1979-11-21 | 1979-11-21 | Preparation of tocopherol acetate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14998479A JPS5673081A (en) | 1979-11-21 | 1979-11-21 | Preparation of tocopherol acetate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5673081A JPS5673081A (en) | 1981-06-17 |
| JPS6330906B2 true JPS6330906B2 (en) | 1988-06-21 |
Family
ID=15486918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14998479A Granted JPS5673081A (en) | 1979-11-21 | 1979-11-21 | Preparation of tocopherol acetate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5673081A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100413373B1 (en) * | 2000-03-23 | 2003-12-31 | 에스케이 주식회사 | The improved method for the preparation of DL-α-tocopherol acetate |
| KR100408991B1 (en) * | 2000-03-23 | 2003-12-11 | 에스케이 주식회사 | The improved method for the preparation of DL-α-tocopherol acetate |
| WO2005121115A1 (en) | 2004-06-11 | 2005-12-22 | Dsm Ip Assets B.V. | PROCESS FOR THE MANUFACTURE OF CHROMAN DERIVATIVES, ESPECIALLY α-TOCOPHEROL AND ALKANOATES THEREOF |
-
1979
- 1979-11-21 JP JP14998479A patent/JPS5673081A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5673081A (en) | 1981-06-17 |
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