JPH0581574B2 - - Google Patents

Info

Publication number
JPH0581574B2
JPH0581574B2 JP1111920A JP11192089A JPH0581574B2 JP H0581574 B2 JPH0581574 B2 JP H0581574B2 JP 1111920 A JP1111920 A JP 1111920A JP 11192089 A JP11192089 A JP 11192089A JP H0581574 B2 JPH0581574 B2 JP H0581574B2
Authority
JP
Japan
Prior art keywords
formula
ethylidene norbornene
molar ratio
alkyl
compounds
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 - Lifetime
Application number
JP1111920A
Other languages
English (en)
Other versions
JPH01316338A (ja
Inventor
Ee Supuretsukaa Maaku
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.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
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.)
Filing date
Publication date
Priority claimed from US06/200,012 external-priority patent/US4311861A/en
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Publication of JPH01316338A publication Critical patent/JPH01316338A/ja
Publication of JPH0581574B2 publication Critical patent/JPH0581574B2/ja
Granted legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/188—Unsaturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
    • C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
    • C11D17/047—Arrangements specially adapted for dry cleaning or laundry dryer related applications
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Cosmetics (AREA)
  • Catalysts (AREA)
  • Detergent Compositions (AREA)
  • Paints Or Removers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

【発明の詳細な説明】
本発明は香料、芳香製品あるいはコロンの芳香
を増大あるいは増強させるための一般式
【化】 あるいは
【化】 （式中ＲはC3〜C5アルキル；C3〜C6アルケニ
ル；C5〜C10アラルキル；ヒドロキシ−C2〜C6−
アルキル；C1〜C4−アルコキシ−C2〜C6−アル
キルあるいはC5〜C8シクロアルキルを表わす）
で表わされる化合物の製造法に関するものであ
る。 こういつた化合物群はガルバナムトツプノート
ならびに葯様、アニース様アンダートーンを有す
る持続性の、フレツシユ、グリーンビーン、バラ
様、柑橘類、ブチグレン様、果物様、アニス様、
グリーン、生バレイシヨ様、小枝様、草本様、甘
い、汗様、グリーンピー様、チヨコレート様、人
参様、クリーム様芳香ニユアンスを有す。 本発明の化合物は式
【化】 で表わされるエチリデンノルボルネンとROHの
アルコール（式中ＲはC3〜C6アルキル；C3〜C6
アルケニル；C6〜10アラルキル；ヒドロキシ−C2
〜C6−アルキル；C1〜C4アルコキシ−C2〜C6ア
ルキルあるいはC5〜C6シクロアルキルを表わす）
とを鉱酸あるいはルイス酸触媒の存在下に反応せ
しめることにより製造せられる。鉱酸触媒の例は
硫酸、リン酸、パラトルエンスルホン酸、メタン
スルホン酸および酸イオン交換樹脂である。触媒
として用いうるルイス酸の例にはボロントリフル
オライドエーテレート、塩化アルミニウム、塩化
亜鉛、塩化第二スズ、塩化第一スズ、臭化亜鉛、
ジエチルアルミニウムクロライド、エチルアルミ
ニウムジクロライド、エチルアルミニウムジブロ
マイド、ジエチルアルミニウムブロマイドがあ
る。反応は好ましくは不活性溶媒例えばテトラハ
イドロフラン、トルエン、ベンゼンの存在下に実
施される。反応は不活性溶媒の不存在下、アルコ
ール反応原料を過剰に用い（過剰のアルコールが
溶媒として用いられる）実施することもできる。 反応温度は約25℃〜120℃で、還流温度が好ま
しい。還流温度は反応器中の圧力、使用せられる
溶媒の種類ならびにその濃度によりことなる。酸
触媒対エチリデンノルボルネンのモル比は約１：
99〜約１：10と変更可能である。エチリデンノル
ボルネン対ROHアルコール反応原料のモル比は
約１：１〜約１：２でノルボルネン：アルコール
＝１：1.5のモル比が好ましい。本発明の化合物
を合成する反応は下記の如く示すことができる。
【化】 本発明の化合物は通常構造式
【式】 の化合物と
【式】 の化合物との混合物で作られる。 しかしながらこういつた化合物は蒸留、抽出お
よび分取GLC法で分離され
【化】 なる化合物と
【化】 なる化合物とに分けられる。 また
【化】 と
【化】 の化合物は各種異性体の形で存在し、混合物で製
造せられる。こういつた「エンド」、「エクソ」、
「シス」および「トランス」異性体の混合物は通
常の分離法例えば分取GLC法で分離され、個々
に利用することができる。これら異性体の構造は
下記の通りである。
【化】
【化】
【化】
【化】
【化】 および
【化】 上記方法で製造された本発明の有用な化合物の
特定例を下記第１表に示す。
【表】 実施例３により製造

Claims (1)

  1. 【特許請求の範囲】 １ 式 【化】 で表わされるエチリデンノルボルネンと式 Ｒ−OH （ＲはC3〜C6アルキル；C3〜C6アルケニル；
    C6〜C10アラルキル；ヒドロキシ−C2〜C6−アル
    キル；C1〜C4−アルコキシ−C2〜C6アルキルあ
    るいはC5〜C8シクロアルキルを表わす）で表わ
    されるアルコールを鉱酸触媒あるいはルイス酸触
    媒の存在下、不活性溶媒の存在あるいは過剰のア
    ルコール反応原料の存在下に混合する工程からな
    り、反応温度は25℃〜120℃の範囲であり、触媒
    対式 【化】 で表わされるエチリデンノルボルネンのモル比は
    １：99〜１：10であり、またエチリデンノルボル
    ネン対ROHアルコール反応原料のモル比は１：
    １〜１：２であることを特徴とする式 【化】 あるいは 【化】 （式中Ｒは前記と同じ）で表わされる化合物の
    製造方法。
JP1111920A 1980-10-23 1989-04-28 ノルボルニルエーテルの製造法 Granted JPH01316338A (ja)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US06/200,012 US4311861A (en) 1980-10-23 1980-10-23 Norbornyl ethers
US200012 1980-10-23
US06/220,351 US4308159A (en) 1980-10-23 1980-12-29 Use of norbornyl ethers in augmenting or enhancing the aroma of fabric softener articles
US220351 1980-12-29

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
JP62112224A Division JPS6366140A (ja) 1980-10-23 1987-05-08 ノルボルニルエ−テル

Publications (2)

Publication Number Publication Date
JPH01316338A JPH01316338A (ja) 1989-12-21
JPH0581574B2 true JPH0581574B2 (ja) 1993-11-15

Family

ID=26895380

Family Applications (1)

Application Number Title Priority Date Filing Date
JP1111920A Granted JPH01316338A (ja) 1980-10-23 1989-04-28 ノルボルニルエーテルの製造法

Country Status (6)

Country Link
US (1) US4308159A (ja)
EP (1) EP0051404B1 (ja)
JP (1) JPH01316338A (ja)
CA (1) CA1327976C (ja)
DE (1) DE3164217D1 (ja)
ES (1) ES8206412A1 (ja)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374746A (en) * 1981-02-19 1983-02-22 International Flavors & Fragrances Inc. Cyclohexyl phenethylether derivatives, process for preparing same and uses thereof in combatting tobacco beetles and in augmenting or enhancing the aroma of perfumes, colognes and perfumed articles
US7381697B2 (en) * 2002-04-10 2008-06-03 Ecolab Inc. Fabric softener composition and methods for manufacturing and using
US7087572B2 (en) 2002-04-10 2006-08-08 Ecolab Inc. Fabric treatment compositions and methods for treating fabric in a dryer
US7786069B2 (en) * 2002-04-10 2010-08-31 Ecolab Inc. Multiple use solid fabric conditioning compositions and treatment in a dryer
JP5391002B2 (ja) * 2009-09-08 2014-01-15 Ｊｘ日鉱日石エネルギー株式会社 ビニルエーテル重合体
JP5492711B2 (ja) * 2009-09-10 2014-05-14 Ｊｘ日鉱日石エネルギー株式会社 イソブチレン系重合体
WO2024027922A1 (en) * 2022-08-05 2024-02-08 Symrise Ag A fragrance mixture (ii)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3632396A (en) * 1969-04-28 1972-01-04 Procter & Gamble Dryer-added fabric-softening compositions
JPS4920569B1 (ja) * 1969-05-16 1974-05-25
US4076853A (en) * 1977-02-04 1978-02-28 International Flavors & Fragrances Inc. Flavoring with substituted norbornane derivatives
US4140724A (en) * 1977-08-11 1979-02-20 Rohm And Haas Company Selective preparation of polyol monoethers of dicyclopentadiene
JPH032920A (ja) * 1989-05-31 1991-01-09 Hitachi Ltd 情報処理システムにおけるメッセージ出力処理方式

Also Published As

Publication number Publication date
EP0051404B1 (en) 1984-06-13
ES507007A0 (es) 1982-08-16
US4308159A (en) 1981-12-29
ES8206412A1 (es) 1982-08-16
DE3164217D1 (en) 1984-07-19
JPH01316338A (ja) 1989-12-21
CA1327976C (en) 1994-03-22
EP0051404A1 (en) 1982-05-12

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