JPH02295936A - Production of 2,6-dialkylnaphthalene - Google Patents
Production of 2,6-dialkylnaphthaleneInfo
- Publication number
- JPH02295936A JPH02295936A JP1114995A JP11499589A JPH02295936A JP H02295936 A JPH02295936 A JP H02295936A JP 1114995 A JP1114995 A JP 1114995A JP 11499589 A JP11499589 A JP 11499589A JP H02295936 A JPH02295936 A JP H02295936A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alkylating agent
- naphthalene
- mordenite
- catalyst
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 229940100198 alkylating agent Drugs 0.000 claims abstract description 16
- 239000002168 alkylating agent Substances 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 7
- 239000010457 zeolite Substances 0.000 claims abstract description 7
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052680 mordenite Inorganic materials 0.000 claims description 12
- 150000002790 naphthalenes Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 29
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract description 22
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 abstract description 4
- 238000009835 boiling Methods 0.000 abstract description 3
- 239000007810 chemical reaction solvent Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000007791 liquid phase Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 150000001336 alkenes Chemical class 0.000 abstract description 2
- 150000001350 alkyl halides Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000004020 conductor Substances 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 14
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 6
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- -1 diisopropyl compound Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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】
（産業上の利用分野）
この発明は、ナフタレン類の芳香核にイソプロピル基等
のアルキル基を導入して、高機能性プラスチックや導電
材料の原料となる２、６−ジアルキルナフタレンを製造
する方法に関するものである。Detailed Description of the Invention (Industrial Field of Application) This invention aims to introduce alkyl groups such as isopropyl groups into the aromatic nucleus of naphthalenes to produce 2,6- The present invention relates to a method for producing dialkylnaphthalene.
（従来の技術）
置換基としてアルキル基を有するナフタレン類は、ポリ
マー原料等を製造するための中間体として有用である。(Prior Art) Naphthalenes having an alkyl group as a substituent are useful as intermediates for producing polymer raw materials and the like.
例えばナフタレンのβ−位にアルキル基を有する２、６
−ジアルキルナフタレンは、その側鎖を酸化することよ
り、ポリエステルを製造する上で有用なナフタレン−２
，６−ジカルボン酸や６−ヒドロキシ−２−ナフトエ酸
を容易に製造することができる。For example, 2,6 with an alkyl group in the β-position of naphthalene
-Dialkylnaphthalene is useful for producing polyester by oxidizing its side chain.
, 6-dicarboxylic acid and 6-hydroxy-2-naphthoic acid can be easily produced.
このようなアルキル置換ナフタレンを製造する方法とし
ては、無水塩化アルミニウム、三フッ化ホウ素、酸化鉄
等を触媒として液相反応によりアルキル化するフリーデ
ルクラフッ反応や固体シリカ、アルミナ触媒を使用する
気相反応等が知られている。しかしながら、フリーデル
クラフッ反応の場合には、一般に反応副生成物として高
沸点化合物が比較的多量に生じるほか、反応後の後処理
として触媒を分解するための水洗中和工程が必要になり
、しかも、この後処理の際に大量の酸性廃液が発生し、
また、触媒の再使用が不可能であり、しかも、触媒が吸
湿性で取扱づらいという問題もある。また、シリカ・ア
ルミナ触媒等の固体酸触媒を使用する気相反応も、高温
を必要とし、しかも、多くの副反応が生じて目的物の収
率や選択率が悪いという問題がある（特開昭６４−９，
９４３号公報、特開昭６３−２１５，６４７号公報）。Methods for producing such alkyl-substituted naphthalene include the Friedel-Crauff reaction, which involves alkylation through a liquid phase reaction using anhydrous aluminum chloride, boron trifluoride, iron oxide, etc. as a catalyst, and the gaseous reaction using solid silica or alumina catalysts. Phase reactions are known. However, in the case of the Friedel-Crach reaction, a relatively large amount of high-boiling compounds are generally produced as reaction by-products, and a water washing and neutralization step is required to decompose the catalyst as a post-treatment after the reaction. Moreover, a large amount of acidic waste liquid is generated during this post-treatment.
Another problem is that the catalyst cannot be reused and is hygroscopic and difficult to handle. Furthermore, gas phase reactions using solid acid catalysts such as silica/alumina catalysts also require high temperatures and have the problem of poor yields and selectivity of the target product due to the occurrence of many side reactions (Unexamined Japanese Patent Publication No. 1986-9,
No. 943, Japanese Patent Application Laid-open No. 63-215,647).
（発明が解決しようとする課題）
本発明は、かかる観点に鑑みて創案されたもので、その
目的とするところは、目的物が高選択率かつ高収率で得
られ、しかも、反応終了後の後処理の際に酸性廃液の問
題がなく、また、触媒の取扱が容易でその再使用も可能
である２、６−ジアルキルナフタレンの製造法を提供す
ることにある。(Problems to be Solved by the Invention) The present invention was devised in view of this point of view, and its purpose is to obtain the target product with high selectivity and high yield, and to obtain the desired product after the completion of the reaction. The object of the present invention is to provide a method for producing 2,6-dialkylnaphthalene that does not cause the problem of acidic waste liquid during post-treatment, and also allows easy handling of the catalyst and reuse thereof.
（課題を解決するための手段）
すなわち、本発明は、Ｈ−モルデナイト型ゼオライト触
媒の存在下に、ナフタレン類とイソプロピル化剤とを反
応させる２、６−ジアルキルナフタレンの製造法である
。(Means for Solving the Problems) That is, the present invention is a method for producing 2,6-dialkylnaphthalenes in which naphthalenes and an isopropylation agent are reacted in the presence of an H-mordenite type zeolite catalyst.
本発明で使用する触媒は、Ｈ−モルデナイト型ゼオライ
ト触媒であり、Ｘ線回折によりモルデナイト構造を示す
ものであって、ナトリウムが水素で置換されているもの
を使用することができる。The catalyst used in the present invention is an H-mordenite type zeolite catalyst, which shows a mordenite structure by X-ray diffraction, and in which sodium is replaced with hydrogen.
このようなモルデナイトは約０．７μｍの孔径を６する
。Such mordenite has a pore size of approximately 0.7 μm.
本発明で使用するナフタレン類は、ナフタレンまたは２
−アルキルナフタレンであるが、他のアルキルナフタレ
ンが混入していても差し支えない。The naphthalene used in the present invention is naphthalene or
- Although it is an alkylnaphthalene, there is no problem even if other alkylnaphthalenes are mixed.
例えば、ナフタレンとアルキル化剤との反応で得られた
モノアルキルナフタレンを主体とし、少量のナフタレン
またはジアルキルナフタレンを含む反応混合物またはそ
の留分てあっても使用することができる。For example, a reaction mixture or a fraction thereof, which is mainly composed of monoalkylnaphthalene obtained by reacting naphthalene with an alkylating agent and contains a small amount of naphthalene or dialkylnaphthalene, can also be used.
本発明で使用するアルキル化剤としては、オレフィン、
アルコール、エーテル、エステル、アルキルハライド等
の公知のアルキル化剤の他、ポリアルキルベンゼン等の
トランスアルキル化反応に使用されるアルキル化剤等を
挙げることができる。The alkylating agents used in the present invention include olefins,
In addition to known alkylating agents such as alcohols, ethers, esters, and alkyl halides, alkylating agents used in transalkylation reactions such as polyalkylbenzene can be mentioned.
また、アルキル化剤の炭素数による区分としては、メチ
ル化剤、エチル化剤、プロピル化剤、ブチル化剤等、任
意の炭素数のものを挙げることができるが、好ましくは
エチル化剤、プロピル化剤およびブチル化剤であり、特
に好ましくはプロピル化剤である。In addition, alkylating agents can be categorized by carbon number, such as methylating agents, ethylating agents, propylating agents, butylating agents, etc., but preferably ethylating agents, propylating agents, and butylating agents. and butylating agents, particularly preferably propylating agents.
本発明方法により２６−ジアルキルナフタレン
ンを製造する際の反応は、流通反応形式であっても、バ
ッチ反応形式であってもよいが、工業的レベルでの大量
生産を行なう場合には触媒固定床の流通反応形式が適し
ている。そして、反応条件については、原料として使用
するナフタレン類およびアルキル化剤の種類や、反応溶
媒を使用するか否か等によって適宜選択し得るものであ
るが、例えばアルキル化剤としてアルコール類を使用す
る液相加圧下の反応の場合には、デカン、ウンデカン、
ドデカン、シクロドデカン、デカリン等の高沸点飽和炭
化水素類を反応溶媒とし、反応温度１５０〜３００℃、
好ましくは２００〜２８０℃である。アルキル化剤の量
はナフタレンに対して１〜４倍モル、好ましくは１．５
〜３倍モルであり、モノアルキナフタレンに対して０．
５〜１．５倍モル、好ましくは０．７〜１．０倍モルで
行なうのがよい。反応時間または接触時間は、通常０゜
１〜１０時間の範囲である。The reaction for producing 26-dialkylnaphthalene by the method of the present invention may be carried out in a flow reaction format or in a batch reaction format, but in the case of mass production at an industrial level, a fixed catalyst bed is used. The flow reaction format is suitable. The reaction conditions can be selected as appropriate depending on the types of naphthalenes and alkylating agents used as raw materials, whether or not a reaction solvent is used, etc., but for example, alcohols may be used as the alkylating agent. In the case of reactions under liquid phase pressure, decane, undecane,
High-boiling saturated hydrocarbons such as dodecane, cyclododecane, and decalin are used as the reaction solvent, and the reaction temperature is 150 to 300°C.
Preferably it is 200-280°C. The amount of alkylating agent is 1 to 4 times mole based on naphthalene, preferably 1.5
~3 times the mole, and 0.
The amount is preferably 5 to 1.5 times the molar amount, preferably 0.7 to 1.0 times the molar amount. The reaction time or contact time is usually in the range of 0°1 to 10 hours.
（実施例）
以下、実施例に基づいて、本発明方法を具体的に説明す
る。ただし、実施例の反応条件は、−例であり特定する
ものではない。(Example) Hereinafter, the method of the present invention will be specifically explained based on Examples. However, the reaction conditions in Examples are examples and are not specific.
実施例１
６．６ｇの２−イソプロピルナフタレンと、１゜７ｇの
イソプロピルアルコール、ｎ−ウンデカン２０ｍ１．Ｈ
−モルデナイト１．０ｇを、８０ｍ１のステンレス製オ
ートクレーブに入れ、２４０℃、５時間加熱撹拌した。Example 1 6.6 g of 2-isopropylnaphthalene, 1.7 g of isopropyl alcohol, 20 ml of n-undecane. H
- 1.0 g of mordenite was placed in an 80 ml stainless steel autoclave and heated and stirred at 240°C for 5 hours.
反応生成物を、ガスクロマトグラフィーにより分析した
結果、２−イソプロピルナフタレン転化率７％、ジイソ
プルピル体の生成比は、２，６一体 ５１．９％、１．
６一体９．９％、１，３一体 ７．１％、１．７一体１
１．８％、２，７一体 １９．４％であった。Analysis of the reaction product by gas chromatography revealed that the conversion rate of 2-isopropylnaphthalene was 7%, the production ratio of diisopropyl compound was 51.9% as 2,6 monomer, and 1.
6 unit 9.9%, 1,3 unit 7.1%, 1.7 unit 1
1.8%, 2,7 unit 19.4%.
実施例２
６．６ｇの２−イソプルピルナフタレンと、１゜７ｇの
イソプロピルアルコール、ｎ−ウンデカン２０ｍ１、Ｈ
−モルデナイト（Ｓ ｉ／ＡＩ２ ＝２３）１．０ｇを
、８００１１のステンレス製オートクレーブに入れ、２
４０°Ｃ１５時間加熱撹拌した。反応生成物をガスクロ
マトグラフィーにより分析した結果、２−イソプロピル
ナフタレン転化率４０％、ジイソプルピル体の生成比は
、２．６一体 ５５゜１％、１．６一体 ９．１％、１
，３一体 ６゜０％、１，７一体 ７．８％、２，７一
体 ２２゜１％であった。Example 2 6.6 g of 2-isopropylnaphthalene, 1.7 g of isopropyl alcohol, 20 ml of n-undecane, H
- Put 1.0 g of mordenite (S i / AI2 = 23) into an 80011 stainless steel autoclave, and
The mixture was heated and stirred at 40°C for 15 hours. As a result of analyzing the reaction product by gas chromatography, the conversion rate of 2-isopropylnaphthalene was 40%, and the production ratio of diisopropyl form was 2.6 units 55°1%, 1.6 units 9.1%, 1
,3 unit 6゜0%, 1,7 unit 7.8%, 2,7 unit 22゜1%.
実施例３
６．６ｇの２−イソプロピルナフタレンと、１゜７ｇの
イソプロピルアルコール、ｎ−ウンデカン２０ｍ１、Ｈ
−モルデナイト（Ｓ ｉ ／Ａ １２ ＝ １０、ツー
トン社製）１．０ｇを、８０ｍ１のステンレス製オート
クレーブに入れ、２４０℃、５時間加熱撹拌した。反応
生成物を、ガスクロマトグラフィーにより分析した結果
、２−イソプロピルナフタレン転化率８％、ジイソプル
ピル体の生成比は、２．６一体 ３８．４％、１．６一
体 １４．０％、］、３一体 １２．４％、１．７一体
１７゜０％、２，７一体 １７．３％であった。Example 3 6.6 g of 2-isopropylnaphthalene, 1.7 g of isopropyl alcohol, 20 ml of n-undecane, H
- 1.0 g of mordenite (S i /A 12 = 10, manufactured by Two-Tone) was placed in an 80 ml stainless steel autoclave and heated and stirred at 240° C. for 5 hours. As a result of analyzing the reaction product by gas chromatography, the conversion rate of 2-isopropylnaphthalene was 8%, and the production ratio of diisopropyl forms was 38.4% for 2.6 units, 14.0% for 1.6 units, ], 3 It was 12.4% for one piece, 17°0% for 1.7 piece, and 17.3% for 2,7 piece.
実施例４
６．６ｇの２−イソプロピルナフタレンと、１゜７ｇの
イソプロピルアルコール、ｎ−ウンデカン２０ｍ１．Ｈ
−モルデナイト（Ｓ ｉ ／Ａ １２ ＝ １５）１．
０ｇを、８０ｍ１のステンレス製オートクレーブに入れ
、２４０℃、５時間加熱撹拌した。反応生成物を、ガス
クロマトグラフィーにより分析した結果、２−イソプロ
ピルナフタレン転化率４８％、ジイソプルピル体の生成
比は、２，６一体５４．３％、１，６一体 ９．１％、
１，３一体６．１％、１．７一体 ８．８％、２．７一
体１９．７％であった。Example 4 6.6 g of 2-isopropylnaphthalene, 1.7 g of isopropyl alcohol, and 20 ml of n-undecane. H
-Mordenite (S i /A 12 = 15)1.
0 g was placed in an 80 ml stainless steel autoclave, and heated and stirred at 240° C. for 5 hours. As a result of analyzing the reaction product by gas chromatography, the conversion rate of 2-isopropylnaphthalene was 48%, and the production ratio of diisopropyl forms was 54.3% for 2,6 monomers, 9.1% for 1,6 monomers,
6.1% for 1.3 units, 8.8% for 1.7 units, and 19.7% for 2.7 units.
実施例５
４．１６ｇナフタレンと、３．３２ｇのイソプロピルア
ルコール、ｎ−ウンデカン２０ｍ１ＳＨ−モルデナイト
（Ｓ ｉ／Ａ１２ ＝２３）１．０ｇを、８０ｍ１のス
テンレス製オートクレーブに入れ、２４０℃、８時間加
熱撹拌した。反応生成物を、ガスクロマトグラフィーに
より分析した結果、ナフタレン転化率７３％、ジイソプ
ルピル体収率３５％、ジイソプロピルの生成比は、２，
６一体 ６０．８％、１，６一体 １０．９％、１，３
一体３．４％、１，７一体 ３．７％、２，７一体２１
．２％であった。Example 5 4.16 g of naphthalene, 3.32 g of isopropyl alcohol, 20 ml of n-undecane, and 1.0 g of SH-mordenite (Si/A12 = 23) were placed in an 80 ml stainless steel autoclave, and heated and stirred at 240°C for 8 hours. did. As a result of analyzing the reaction product by gas chromatography, the naphthalene conversion rate was 73%, the yield of diisopropyl compound was 35%, and the production ratio of diisopropyl was 2,
6 unit 60.8%, 1,6 unit 10.9%, 1,3
3.4%, 1,7 3.7%, 2,7 21
．． It was 2%.
実施例６
６．６ｇの２−イソプロピルナフタレンと、ｎ−ウンデ
カン２０ｍ１、Ｈ−モルデナイト（Ｓｔ／ＡＩ２ ＝２
３）１．０ｇを、８０ｍ１のステンレス製オートクレー
ブに入れ、プロピレンを５ ｍｇ ／ ｃＪ封入し、２
４０°Ｃ，５時間加熱撹拌した。反応生成物を、ガスク
ロマトグラフィーにより分析した結果、２−イソプロピ
ルナフタレン転化率４６％、ジイソプルピル体の生成比
は、２，６一体 ４６゜９％、１，６一体 １１．５％
、１，３一体 ８゜１％、１，７一体 １２．６％、２
，７一体 ２１．０％であった。Example 6 6.6 g of 2-isopropylnaphthalene, 20 ml of n-undecane, H-mordenite (St/AI2 = 2
3) Put 1.0g into an 80ml stainless steel autoclave, fill with 5mg/cJ of propylene, and
The mixture was heated and stirred at 40°C for 5 hours. As a result of analyzing the reaction product by gas chromatography, the conversion rate of 2-isopropylnaphthalene was 46%, and the production ratio of diisopropyl derivatives was 46.9% for 2,6 monomers and 11.5% for 1,6 monomers.
, 1,3 integrated 8°1%, 1,7 integrated 12.6%, 2
, 7 was 21.0%.
比較例１
６．６ｇの２−イソプロピルナフタレンと、１゜７ｇの
イソプロピルアルコール、ｎ−ウンデカン２０ｍ１．Ｈ
ＺＳＭ ５ （Ｓ Ｌ／Ａ １２ ＝７０）１．０ｇ
を、８００１１のステンレス製オートクレーブに入れ、
２４０℃、５時間加熱撹拌した。反応生成物を、ガスク
ロマトグラフィーにより分析した結果、２−イソプロピ
ルナフタレン転化率２％、ジイソプルピル体の生成比は
、２．６一体 ２３゜４％、１，６一体 １５．５％、
１，３一体 １５．９％、１，７一体 ２０．６％、２
，７一体２４．７％であった。Comparative Example 1 6.6 g of 2-isopropylnaphthalene, 1.7 g of isopropyl alcohol, and 20 ml of n-undecane. H
ZSM 5 (SL/A 12 =70) 1.0g
into an 80011 stainless steel autoclave,
The mixture was heated and stirred at 240°C for 5 hours. As a result of analyzing the reaction product by gas chromatography, the conversion rate of 2-isopropylnaphthalene was 2%, the production ratio of diisopropyl compound was 23.4% for 2.6 units, 15.5% for 1,6 units,
1,3 integrated 15.9%, 1,7 integrated 20.6%, 2
, 7 was 24.7%.
比較例２
６．６ｇの２−イソプロピルナフタレンと、１゜７ｇの
イソプロピルアルコール、ｎ−ウンデカン２０ｍ１およ
びＹ−ゼオライト、１．０ｇを、８０ｍ１のステンレス
製オートクレーブに入れ、２４０℃、５時間加熱撹拌し
た。反応生成物を、ガスクロマトグラフィーにより分析
した結果、２−イソプロピルナフタレン転化率６９％、
ジイソプルピル体の生成比は、２，６一体 ３９．０％
、１゜６一体 ８．１％、１，３一体 ６．８％、１゜
７一体 ６．７％、２．７一体 ３９．４％であった。Comparative Example 2 6.6 g of 2-isopropylnaphthalene, 1.7 g of isopropyl alcohol, 20 ml of n-undecane, and 1.0 g of Y-zeolite were placed in an 80 ml stainless steel autoclave, and heated and stirred at 240° C. for 5 hours. . Analysis of the reaction product by gas chromatography revealed that the conversion rate of 2-isopropylnaphthalene was 69%;
The production ratio of diisopropyl compound is 2,6 monomer 39.0%
, 1°6 integrated 8.1%, 1,3 integrated 6.8%, 1°7 integrated 6.7%, and 2.7 integrated 39.4%.
（発明の効果）
以」二述べたように、本発明は、Ｈ−モルデナイト型ゼ
オライト触媒の存在下に、ナフタレン類とアルキル化剤
を反応させることを特徴とする２゜６−ジアルキルナフ
タレンの製造方法であるから、２．６−ジアルキルナフ
タレンを選択的に高い収率で得ることができるのである
。(Effects of the Invention) As described above, the present invention provides a method for producing 2゜6-dialkylnaphthalene, which is characterized by reacting naphthalenes with an alkylating agent in the presence of an H-mordenite type zeolite catalyst. This method makes it possible to selectively obtain 2,6-dialkylnaphthalene in high yield.
Claims (2)
ナフタレン類とアルキル化剤を反応させることを特徴と
する２，６−ジアルキルナフタレンの製造方法。(1) In the presence of H-mordenite type zeolite catalyst,
A method for producing 2,6-dialkylnaphthalene, which comprises reacting naphthalenes with an alkylating agent.
載の２，６−ジアルキルナフタレンの製造方法。(2) The method for producing 2,6-dialkylnaphthalene according to claim 1, wherein the alkylating agent is a propylating agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1114995A JPH02295936A (en) | 1989-05-10 | 1989-05-10 | Production of 2,6-dialkylnaphthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1114995A JPH02295936A (en) | 1989-05-10 | 1989-05-10 | Production of 2,6-dialkylnaphthalene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02295936A true JPH02295936A (en) | 1990-12-06 |
Family
ID=14651703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1114995A Pending JPH02295936A (en) | 1989-05-10 | 1989-05-10 | Production of 2,6-dialkylnaphthalene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02295936A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992002473A1 (en) * | 1990-07-27 | 1992-02-20 | Nippon Steel Chemical Co., Ltd. | Process for producing 2-alkyl-6-ethyl-naphthalene |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62226931A (en) * | 1986-03-29 | 1987-10-05 | Nippon Steel Chem Co Ltd | Production of 2,6-diisopropylnaphthalene |
| JPH04500808A (en) * | 1988-10-05 | 1992-02-13 | コーク ケミカル カンパニー，ア ディビィジョン オブ コーク リファイニング カンパニー，エル．ピー． | Method for selective diisopropylation of naphthyl compounds using shape-selective acidic crystalline molecular sieve catalysts |
-
1989
- 1989-05-10 JP JP1114995A patent/JPH02295936A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62226931A (en) * | 1986-03-29 | 1987-10-05 | Nippon Steel Chem Co Ltd | Production of 2,6-diisopropylnaphthalene |
| JPH04500808A (en) * | 1988-10-05 | 1992-02-13 | コーク ケミカル カンパニー，ア ディビィジョン オブ コーク リファイニング カンパニー，エル．ピー． | Method for selective diisopropylation of naphthyl compounds using shape-selective acidic crystalline molecular sieve catalysts |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992002473A1 (en) * | 1990-07-27 | 1992-02-20 | Nippon Steel Chemical Co., Ltd. | Process for producing 2-alkyl-6-ethyl-naphthalene |
| US5321182A (en) * | 1990-07-27 | 1994-06-14 | Nippon Steel Chemical Co., Ltd. | Process for preparing 2-alkyl-6-ethylnaphthalene |
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