JPS6032740A - Production of o-benzylphenol - Google Patents
Production of o-benzylphenolInfo
- Publication number
- JPS6032740A JPS6032740A JP58142084A JP14208483A JPS6032740A JP S6032740 A JPS6032740 A JP S6032740A JP 58142084 A JP58142084 A JP 58142084A JP 14208483 A JP14208483 A JP 14208483A JP S6032740 A JPS6032740 A JP S6032740A
- Authority
- JP
- Japan
- Prior art keywords
- benzyl alcohol
- phenol
- catalyst
- reaction
- orthobenzylphenol
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 title 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 75
- 238000006243 chemical reaction Methods 0.000 claims abstract description 27
- 235000019445 benzyl alcohol Nutrition 0.000 claims abstract description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 4
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PGEBXGLGFFYYFX-UHFFFAOYSA-N 2,3-dibenzylphenol Chemical compound C=1C=CC=CC=1CC=1C(O)=CC=CC=1CC1=CC=CC=C1 PGEBXGLGFFYYFX-UHFFFAOYSA-N 0.000 description 1
- 241001377695 Polygonum arenastrum Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、オルソベンジルフェノ−＃ （７）製法に関
する。更に計しくは、触媒の存在下、フェノールとベン
ジルアルコールとを反応させるこトニよりオルソベンジ
ルフェノールを製造する方法の改良法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing orthobenzylpheno-# (7). More particularly, the present invention relates to an improved method for producing orthobenzylphenol by reacting phenol with benzyl alcohol in the presence of a catalyst.
オルソベンジルフェノールは、有機化合物、特に医薬の
合成中間体として有用な化合物であシ、製造法としては
、フェノールとベンジルアルコールとを、γ−アルミナ
等の触媒の存在下、反応させることが知られている。し
かしながら、この方法を実施する場合は、通常、フェノ
ール合、反応混合物中にベンジルフェニルエーテル及び
ジベンジルエーテルが多量に含有されるという欠点があ
る。また、このベンジルフェニルエーテル及びジベンジ
ルニーテルハ、オルソベンジルフェノールと沸点が近い
ため、蒸留による分離が困難である。Orthobenzylphenol is a compound useful as an intermediate in the synthesis of organic compounds, especially pharmaceuticals.It is known that the production method involves reacting phenol and benzyl alcohol in the presence of a catalyst such as γ-alumina. ing. However, this process usually has the disadvantage that the phenol reaction mixture contains large amounts of benzyl phenyl ether and dibenzyl ether. Furthermore, since the benzyl phenyl ether, dibenzyl ether, and orthobenzyl phenol have similar boiling points, separation by distillation is difficult.
そこで、本発明者らは、副生物の生成を抑制し、また、
オルソベンジルフェノールの選択率を向上させるべく鋭
意研究を行った結果、フェノールとベンジルアルコール
を一括して反応器に仕込むことなく、予め、フェノール
及び触媒を散水として仕込んだ後、これにベンジルアル
コールを添加して反応を行えば、ベンジル７エ二ルエー
テル及びジベンジルエーテル含有量の少ない反応生成物
が得られることを見い出し、本発明に到達した。Therefore, the present inventors suppressed the production of by-products, and
As a result of intensive research to improve the selectivity of orthobenzylphenol, we discovered that instead of charging phenol and benzyl alcohol into the reactor all at once, we first charged the phenol and catalyst as water spray and then added benzyl alcohol to this. It was discovered that a reaction product with low benzyl 7-enyl ether and dibenzyl ether contents can be obtained by carrying out the reaction, and the present invention was achieved based on these findings.
すなわち、本発明の要旨は、触媒の存在下、フェノール
とベンジルアルコールとを反応サセてオルソベンジルフ
ェノールを製造するに際し、触媒を含有するフェノール
中に、ベンジルアルコールを添加して反応を行うことを
特徴とするオルソベンジルフェノールの製法に存する。That is, the gist of the present invention is that when producing orthobenzylphenol by reacting phenol and benzyl alcohol in the presence of a catalyst, the reaction is carried out by adding benzyl alcohol to phenol containing a catalyst. The invention consists in a method for producing orthobenzylphenol.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
本発明に使用される触媒としては、通常、γ−アルミナ
、酸化マグネシウム、酸化マンガン、酸化鉄、酸化クロ
ム等の金属酸化物；ナトリウム金属、ナトリウムハイド
ライド等のアルカリ金属またはその水嵩化物；塩化アル
ミニウム、塩化亜鉛等の金践塩化物：および硫酸等が挙
げられ、特に全域酸化物が好ましい。Catalysts used in the present invention are usually metal oxides such as γ-alumina, magnesium oxide, manganese oxide, iron oxide, and chromium oxide; alkali metals such as sodium metal and sodium hydride, or their hydroxides; aluminum chloride; Examples include metal chlorides such as zinc chloride and sulfuric acid, with full range oxides being particularly preferred.
触媒の使用量は、通常、ベンジルアルコールに対して０
．０！；−１０重量倍、好ましくは、０．７〜５重量倍
である。The amount of catalyst used is usually 0 based on benzyl alcohol.
．． 0! -10 times by weight, preferably 0.7 to 5 times by weight.
また、反応は、通常、第三成分としての溶媒を用いるこ
となく、過剰量のフェノールを用いて行なわれるが、必
要に応じて、有機溶媒を用いても良い。有機溶媒を用い
る場合には、通常、フェノールよシも沸点が高く、ま九
、本発明の反応条件下で変化しないものが用いられ、例
えば、ウンデカン、ドデカン尋の脂肪族炭化水素 ３−
等が挙げられる。Further, the reaction is usually carried out using an excess amount of phenol without using a solvent as a third component, but an organic solvent may be used if necessary. When an organic solvent is used, it is usually one that has a high boiling point such as phenol and does not change under the reaction conditions of the present invention, such as aliphatic hydrocarbons such as undecane and dodecane. Can be mentioned.
第三成分としての溶媒を用いない場合のフエ／ −＃
ｆ） 使用量は、通常、ベンジルアルコールに対して、
７６０３〜５モル倍、好ましくは、７．３〜３モル倍で
ある。Fe/-# without solvent as third component
f) The amount used is usually based on benzyl alcohol.
7603 to 5 times by mole, preferably 7.3 to 3 times by mole.
反応温度は通常、／ｊＴＯ−コよ０℃、好ましくは１７
０〜１１０℃であシ、反応圧力は通常、常圧であるが、
加圧してもよい。反応温度があまり高い場合には、副生
物であるジベンジルフェノールが生成し、逆に、あ′！
シ低い場合には、反応速度が遅くなるので好ましくない
。また、反応時間は通常、ｉｏ分〜ｉｏ時間、好ましく
は３０分〜ｊ時間である。The reaction temperature is usually 0°C, preferably 17°C.
The temperature is 0 to 110°C, and the reaction pressure is usually normal pressure.
Pressure may be applied. If the reaction temperature is too high, dibenzylphenol, a by-product, will be produced, and conversely, ah!
If the value is low, the reaction rate becomes slow, which is not preferable. Further, the reaction time is usually io minutes to io hours, preferably 30 minutes to j hours.
本発明では予め、フェノールを散水として反応器に仕込
み、反応条件下で、これにベンジルアルコールを添加し
て反応を行なうことを必須の要件とする。この際に、通
常、触媒もフェノールとともに予め、反応器に仕込むの
が好ましい。In the present invention, it is essential to charge phenol in the form of water spray into a reactor in advance, and to carry out the reaction by adding benzyl alcohol thereto under reaction conditions. At this time, it is usually preferable to charge the catalyst together with the phenol into the reactor in advance.
もし、ベンジルアルコールとフェノール中添 ４−
加順序が逆の場合、又はベンジルアルコール及びフェノ
ールを一緒にして仕込んだ場合には、本発明で目的とす
るような効果は得られない。If the addition order of benzyl alcohol and phenol is reversed, or if benzyl alcohol and phenol are added together, the desired effects of the present invention cannot be obtained.
本発明におけるベンジルアルコールの供給速度は反応条
件によシ異なるが、通常、反応系内の未反応ベンジルア
ルコール濃度が１０１ｒ以下に保持されるように供給さ
れる。The feeding rate of benzyl alcohol in the present invention varies depending on the reaction conditions, but it is usually fed so that the concentration of unreacted benzyl alcohol in the reaction system is maintained at 101r or less.
本発明を具体的に実施するには、例えば、還流冷却器、
加熱器及び攪拌機を有する反応器に、所定量の７エノー
ル及び触媒を仕込み、これを所定の反応温度に加熱した
後、攪拌下、ベンジルアルコールを一定速度で添加する
ことによシ反応を行なうことができる。そして、反応に
より生成した水はフェノールと共沸し、系外に除去され
（反応温度は水−フェノール共沸温度よシも高いので）
、反応が進行する。また、ベンジルアルコールを添加し
た後は、反応の押し切シのために引き続き、同条件下で
攪拌処理される。To specifically implement the present invention, for example, a reflux condenser,
A predetermined amount of 7 enol and a catalyst are charged into a reactor equipped with a heater and a stirrer, and after heating this to a predetermined reaction temperature, a reaction is carried out by adding benzyl alcohol at a constant rate while stirring. I can do it. Then, the water produced by the reaction azeotropes with phenol and is removed from the system (because the reaction temperature is higher than the water-phenol azeotrope temperature).
, the reaction proceeds. Further, after the benzyl alcohol is added, the mixture is continuously stirred under the same conditions in order to drive the reaction through.
反応後の混合物は、通常、ｐ過して触媒を分離した後、
蒸留することによシ、先ず、未反応フェノールを留去し
、次いで、目的とするオルソベンジルフェノールを留出
させて回収する。After the reaction, the mixture is usually subjected to p-filtration to separate the catalyst, and then
By distilling, first, unreacted phenol is distilled off, and then the target orthobenzylphenol is distilled off and recovered.
次に本発明ｔ−実施例により更に詳細に説明するが、本
発明は、その要旨を超えない限夛、以下の実施例により
限定されない。EXAMPLES Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited by the following examples as long as it does not exceed the gist thereof.
実施例
還流冷却器、温度調節機及び攪拌機を有するｘｔの反応
器に、７ ｘ／−ルＡ ＆ Ｏｆ （ＡＪｊｔｍｏｂ
）及びγ−ムＬ２０８タデ、ｇｔを仕込み、油浴にて加
熱昇温した。内温が１７コ℃となったところで、滴下漏
斗からベンジルアルコール＋１３１ｙ（４，θｍｏｂ）
の滴下を開始した。約４０分間で全量滴下后、内温は／
１−℃となつ九。この后約コ００℃で１時間反応させた
ところ、ベンジルフェニルエーテルおよヒシベンジルエ
ーテルは検出されなくなｐ１反応が完結した。EXAMPLE In a xt reactor with a reflux condenser, a temperature regulator and a stirrer, 7x/-l A & Of (AJjtmob
) and γ-mu L208 knotweed, gt were added, and the mixture was heated and heated in an oil bath. When the internal temperature reaches 17°C, add benzyl alcohol + 131y (4,θmob) from the dropping funnel.
dripping was started. After dropping the entire amount in about 40 minutes, the internal temperature is /
1-℃ and nine days. After this, the reaction was carried out at 00° C. for 1 hour, and no benzyl phenyl ether or hishibenzyl ether was detected, and the p1 reaction was completed.
冷却層、触媒ｔ−Ｆ別し、オルソベンジルフェノールを
含むＰ液ｔ／！ｒｔｔ−取得した。Cooling layer, catalyst t-F separated, P liquid containing orthobenzylphenol t/! rtt-obtained.
Ｐ液をガスクロマトグラフィーにて分析したところ、フ
ェノールｌｔ、ｓｓ重量％、オルソベンジルフェノール
Ａ ３．Ｉｆ 、を重量％であシ、Ｆ液中のオルソベン
ジルフェノール量は、Ｓ２θ、ｌ／、ｒ（θ、３．ｔｌ
Ｉｍｏ１）であった。オルソベンジルフェノールの収率
はベンジルアルコール基準で、ｔざ、タチであった。When the P solution was analyzed by gas chromatography, phenol lt, ss wt%, orthobenzylphenol A 3. If, is weight%, the amount of orthobenzylphenol in liquid F is S2θ, l/, r(θ, 3.tl
Imo1). The yield of orthobenzylphenol was about 100% based on benzyl alcohol.
比較例
実施例の方法において、ベンジルアルコールをフェノー
ルとともに、予め、一括して反応器に仕込んだ以外は全
く同様にして、一時間反応を行なった。Comparative Example A reaction was carried out for one hour in exactly the same manner as in the example except that benzyl alcohol and phenol were charged into the reactor all at once.
その結果を前記実施例の結果と併せて、下記表に示す。The results are shown in the table below together with the results of the above examples.
Claims (1)
ルとを反応させてオルンペンジルフェノールｔｌ″製造
するに際し、触媒を含有するフェノール中に、ベンジル
アルコールを添加して反応を行うことを特徴とするオル
ソベンジルフェノールの製法。 （２、特許請求の範囲第１項記載の方法において、第三
成分としての溶媒を用いることなく、過剰量のフェノー
ルを用いて反応を行うことを特徴とするオルソベンジル
フェノールの製法。 （３）特許請求の範囲第７項記載の方法において、反応
温度が１１０〜１３０℃であることを特徴とするオルソ
ベンジルフェノールの製法。 （４）特許請求の範囲第１項記載の方法において、触媒
がＴ−アルミナであることを特徴とするオルソベンジル
フェノールの製法。 （５）特許請求の範囲第１項記載の方法において、反応
系内の未反応ベンジルアルコールの濃度を１ｏｆｒ以下
に保持するように、ベンジルアルコールの供給速度を調
節することを特徴とするオルソベンジルフェノールの製
法。[Scope of Claims] (1) When producing olumpenzylphenol tl'' by reacting phenol and benzyl alcohol in the presence of a catalyst, the reaction is carried out by adding benzyl alcohol to phenol containing a catalyst. A method for producing orthobenzylphenol, characterized in that the method according to claim 1 is characterized in that the reaction is carried out using an excess amount of phenol without using a solvent as a third component. (3) A method for producing orthobenzylphenol according to claim 7, characterized in that the reaction temperature is 110 to 130°C. (4) Claims A method for producing orthobenzylphenol, characterized in that the catalyst is T-alumina. (5) A method for producing orthobenzylphenol, characterized in that the catalyst is T-alumina. A method for producing orthobenzylphenol, characterized in that the feeding rate of benzyl alcohol is adjusted so as to maintain the concentration at 1 ofr or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58142084A JPS6032740A (en) | 1983-08-03 | 1983-08-03 | Production of o-benzylphenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58142084A JPS6032740A (en) | 1983-08-03 | 1983-08-03 | Production of o-benzylphenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6032740A true JPS6032740A (en) | 1985-02-19 |
| JPS6217980B2 JPS6217980B2 (en) | 1987-04-21 |
Family
ID=15307054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58142084A Granted JPS6032740A (en) | 1983-08-03 | 1983-08-03 | Production of o-benzylphenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6032740A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62162285U (en) * | 1985-12-04 | 1987-10-15 | ||
| WO2007027375A3 (en) * | 2005-08-29 | 2010-05-06 | General Electric Company | Method of making benzylated phenols |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014518095A (en) | 2011-09-06 | 2014-07-28 | ブリティッシュ アメリカン タバコ （インヴェストメンツ） リミテッド | Smoking material heating |
| GB201207039D0 (en) | 2012-04-23 | 2012-06-06 | British American Tobacco Co | Heating smokeable material |
| EP4147596B1 (en) | 2013-10-29 | 2024-04-24 | Nicoventures Trading Limited | Apparatus for heating smokable material |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093667A (en) * | 1977-03-14 | 1978-06-06 | Continental Oil Company | Preparation of 4-n-hexylresorcinol |
| US4105699A (en) * | 1977-02-16 | 1978-08-08 | Continental Oil Company | Preparation of o-benzylphenol |
| US4108909A (en) * | 1976-01-19 | 1978-08-22 | Continental Oil Company | N-alkylated cresylic acids via direct alkylation in a liquid phase |
| US4117243A (en) * | 1977-03-07 | 1978-09-26 | Continental Oil Company | Preparation of o-benzylphenol |
-
1983
- 1983-08-03 JP JP58142084A patent/JPS6032740A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4108909A (en) * | 1976-01-19 | 1978-08-22 | Continental Oil Company | N-alkylated cresylic acids via direct alkylation in a liquid phase |
| US4105699A (en) * | 1977-02-16 | 1978-08-08 | Continental Oil Company | Preparation of o-benzylphenol |
| US4117243A (en) * | 1977-03-07 | 1978-09-26 | Continental Oil Company | Preparation of o-benzylphenol |
| US4093667A (en) * | 1977-03-14 | 1978-06-06 | Continental Oil Company | Preparation of 4-n-hexylresorcinol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62162285U (en) * | 1985-12-04 | 1987-10-15 | ||
| WO2007027375A3 (en) * | 2005-08-29 | 2010-05-06 | General Electric Company | Method of making benzylated phenols |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6217980B2 (en) | 1987-04-21 |
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