JPH03106836A - Production of dimethylnaphthalene by disproportionation reaction of methylnaphthalene - Google Patents
Production of dimethylnaphthalene by disproportionation reaction of methylnaphthaleneInfo
- Publication number
- JPH03106836A JPH03106836A JP24395889A JP24395889A JPH03106836A JP H03106836 A JPH03106836 A JP H03106836A JP 24395889 A JP24395889 A JP 24395889A JP 24395889 A JP24395889 A JP 24395889A JP H03106836 A JPH03106836 A JP H03106836A
- Authority
- JP
- Japan
- Prior art keywords
- methylnaphthalene
- catalyst
- carried out
- dimethylnaphthalene
- reaction
- 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
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000007323 disproportionation reaction Methods 0.000 title claims abstract description 8
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 11
- 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 11
- 239000010457 zeolite Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 5
- -1 saturated alicyclic hydrocarbon Chemical class 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 abstract description 22
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract description 6
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 abstract description 4
- 239000012013 faujasite Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 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 abstract description 3
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- 230000009849 deactivation Effects 0.000 abstract 1
- YGYNBBAUIYTWBF-UHFFFAOYSA-N 2,6-dimethylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C)=CC=C21 YGYNBBAUIYTWBF-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- XYTKCJHHXQVFCK-UHFFFAOYSA-N 1,3,8-trimethylnaphthalene Chemical compound CC1=CC=CC2=CC(C)=CC(C)=C21 XYTKCJHHXQVFCK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052849 andalusite Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229910052851 sillimanite Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/123—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of only one hydrocarbon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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】
産業上の利用分野
本発明は、メチルナフタレンの不均化反応により、ジメ
チルナフタレンを製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a method for producing dimethylnaphthalene by a disproportionation reaction of methylnaphthalene.
従来技術とその問題点
ジメチルナフタレンには、１０種の異性体が存在してい
る。このうち、２，６一体は、ポリエステルフィルム、
ポリエステル繊維などの原料となる２，６−ナフタレン
ジカルボン酸の中間体として特に有用である。Prior art and its problems Dimethylnaphthalene has 10 types of isomers. Of these, 2 and 6 are polyester films,
It is particularly useful as an intermediate for 2,6-naphthalene dicarboxylic acid, which is a raw material for polyester fibers and the like.
メチルナフタレンの不均化方法としては、下記の様な方
法が知られている：
（イ）シリカーアルミナ触媒、クロミアーシリカーアル
ミナ触媒を使用する方法がある（Ｂｕｌｌ．Ｃｈｅｍ．
Ｓｏｃ． Ｊａｐ． ３７（７），１０２５（１９６
４））。The following methods are known for disproportionation of methylnaphthalene: (a) There is a method using a silica alumina catalyst or a chromia silica alumina catalyst (Bull. Chem.
Soc. Jap. 37(7), 1025(196
4)).
（ロ）硫酸で活性化されたシリマナイト、アンダルサイ
ト、キャノナイトなどを触媒とする方法がある（Ｔｒ．
Ｍｏｓｋ． Ｉｎｓｔ． Ｎｅｆｔｅｋｈ１ｍ． Ｇ
ａｚｏｖ．Ｐｒｏｍ．６９ ４７（１９６７）。(b) There is a method using sillimanite, andalusite, cannonite, etc. activated with sulfuric acid as a catalyst (Tr.
Mosque. Inst. Neftekh1m. G
azov. Prom. 69 47 (1967).
（ハ）主空洞の入口が酸素１０員環からなるゼオライト
を触媒とする方法がある（特開昭６０＝９２２２７号公
報）。(c) There is a method in which the entrance of the main cavity uses a zeolite containing a 10-membered oxygen ring as a catalyst (Japanese Unexamined Patent Publication No. 1988-92227).
しかしながら、これらの公知技術は、触媒寿命が短く、
またジメチルナフタレンの生成収率が低いため、実用的
には問題がある。However, these known techniques have a short catalyst life and
Furthermore, since the production yield of dimethylnaphthalene is low, there is a problem in practical use.
問題点を解決するための手段
本発明者は、上記の如き技術の現状に鑑みて種々研究を
重ねた結果、特定の固体酸触媒の存在下にメチルナフタ
レンの不均化反応を行う場合には、高収率且つ高い選択
性で２，６−ジメチルナフタレンが得られることを見出
した。Means for Solving the Problems The present inventor has conducted various studies in view of the current state of the technology as described above, and has found that when carrying out the disproportionation reaction of methylnaphthalene in the presence of a specific solid acid catalyst, It has been found that 2,6-dimethylnaphthalene can be obtained in high yield and high selectivity.
すなわち、本発明は、下記の方法を提供するものである
：
■加熱下にフォージャサイト型ゼオライトにメチルナフ
タレンを接触させることを特徴とするメチルナフタレン
の不均化反応によるジメチルナフタレンの製造方法。That is, the present invention provides the following method: (1) A method for producing dimethylnaphthalene by a disproportionation reaction of methylnaphthalene, which comprises bringing methylnaphthalene into contact with a faujasite-type zeolite under heating.
■溶媒として飽和脂環族炭化水素の存在下に実施する請
求項（１）に記載の方法。(2) The method according to claim (1), which is carried out in the presence of a saturated alicyclic hydrocarbon as a solvent.
本発明で原料として使用するメチルナフタレンは、１−
メチルナフタレン（以下１−ＭＮという）および２−メ
チルナフタレン（以下２−ＭＮという）のいずれであっ
ても良い。また、原料の２０％程度を超えない範囲で混
合物としてナフタレン、ジメチルナフタレンなどを含ん
でいても良い。Methylnaphthalene used as a raw material in the present invention is 1-
It may be either methylnaphthalene (hereinafter referred to as 1-MN) or 2-methylnaphthalene (hereinafter referred to as 2-MN). Further, naphthalene, dimethylnaphthalene, etc. may be included as a mixture within a range not exceeding about 20% of the raw materials.
本発明で使用する触媒は、フォージャサイト型ゼオライ
トであり、その代表例としてＹ型ゼオライトがある。触
媒としては、酸型体として使用する。フォージャサイト
型ゼオライトは、そのまま使用しても良く、或いはシリ
カ、アルミナ、粘土鉱物などのバインダー成分とともに
成形して使用することも出来る。本発明で使用する特定
の触媒が、本発明の特に優れた効果、すなわち高い２．
６−ジメチルナフタレン選択性および高収率をもたらす
理由については、未だ十分に解明されていない。しかし
ながら、本発明で使用する以外の触媒を使用する場合に
は、本発明の所望の効果は、達成されないことは比較例
の結果からも明確である。The catalyst used in the present invention is a faujasite type zeolite, and Y type zeolite is a typical example thereof. The catalyst is used in acid form. Faujasite type zeolite may be used as it is, or may be molded together with a binder component such as silica, alumina, or clay mineral. The specific catalyst used in the present invention has a particularly excellent effect of the present invention, that is, a high 2.
The reasons for the 6-dimethylnaphthalene selectivity and high yield have not yet been fully elucidated. However, it is clear from the results of comparative examples that the desired effects of the present invention cannot be achieved if a catalyst other than that used in the present invention is used.
本発明方法は、必要に応じ、溶媒としての飽和脂環式炭
化水素の存在下に行なっても良い。溶媒の使用により、
触媒の活性低下を抑制することが出来、触媒寿命の延長
が可能となる。溶媒としては、特に限定されるものでは
ないが、デカリン、ビシクロヘキシルなどが例示される
。The method of the present invention may be carried out in the presence of a saturated alicyclic hydrocarbon as a solvent, if necessary. Due to the use of solvents,
Decrease in catalyst activity can be suppressed and the life of the catalyst can be extended. Examples of the solvent include, but are not limited to, decalin, bicyclohexyl, and the like.
本発明による不均化反応は、上記のフオージャサイト型
ゼオライト触媒の存在下に、メチルナフタレンを加熱す
ることにより実施される。反応は、気相或いは液相のい
ずれでも行うことができる。The disproportionation reaction according to the present invention is carried out by heating methylnaphthalene in the presence of the faujasite-type zeolite catalyst described above. The reaction can be carried out in either gas phase or liquid phase.
反応時の条件は、特に限定されるものではないが、通常
温度２００〜５００℃程度、好ましくは２００〜４００
℃程度、特に好ましくは２５０〜４００℃程度で、圧力
常圧〜１０ ０ ｋｇ／ （Ｊ程度、より好ましくは常
圧〜３０ｋｇ／ｃｆＩｌ程度で行なう。Conditions during the reaction are not particularly limited, but the temperature is usually about 200 to 500°C, preferably 200 to 400°C.
It is carried out at a temperature of about 0.degree. C., particularly preferably about 250 to 400.degree. C., and a pressure of about normal pressure to about 100 kg/(J), more preferably about normal pressure to about 30 kg/cfIl.
反応を加圧下に行なう場合には、水素による加圧を行う
ことが好ましい。或いは、Ｎ２、ＣＯ２、ＣＨ４などを
系内に導入しても良い。触媒の使用量も、特に限定され
ないが、通常メチルナフタレン重量の５〜４０％程度で
ある。When the reaction is carried out under pressure, it is preferable to pressurize with hydrogen. Alternatively, N2, CO2, CH4, etc. may be introduced into the system. The amount of catalyst used is also not particularly limited, but is usually about 5 to 40% of the weight of methylnaphthalene.
本発明方法終了後の系内には、未反応のメチルナフタレ
ン、触媒、溶媒、２，６−ジメチルナフタレンおよびそ
の異性体などが混在している。この様な混合物を精密蒸
留して、２．６−ジメチルナフタレンおよびその異性体
を分離した後、これを圧力晶析に供することにより、２
，６−ジメチルナフタレンを収得することができる。After completing the method of the present invention, unreacted methylnaphthalene, catalyst, solvent, 2,6-dimethylnaphthalene and its isomers, etc. are mixed together. After precision distilling such a mixture to separate 2,6-dimethylnaphthalene and its isomers, this is subjected to pressure crystallization to obtain 2.6-dimethylnaphthalene and its isomers.
, 6-dimethylnaphthalene can be obtained.
発明の効果 本発明によれば、下記の様な効果が達成される。Effect of the invention According to the present invention, the following effects are achieved.
（イ）触媒活性の劣化が抑制される。(a) Deterioration of catalyst activity is suppressed.
（ロ）ジメチルナフタレンの収率が高い。(b) High yield of dimethylnaphthalene.
（ハ）生成するジメチルナフタレン中に占める２，６一
体の比率が高い。(c) The proportion of 2,6 monomers in the dimethylnaphthalene produced is high.
（ホ）したがって、生成混合物に含まれる２，６一ジメ
チルナフタレンの精製が容易である。(e) Therefore, it is easy to purify the 2,6-dimethylnaphthalene contained in the product mixture.
実施例
以下に実施例および比較例を示し、本発明の特徴とする
ところをより一層明確にする。EXAMPLES Examples and comparative examples are shown below to further clarify the features of the present invention.
実施例１
容量１００ｍｌの回転攪拌機付きのオートクレープに２
−ＭＮ２０ｍｌ、デカリン２０ｍｌおよび触媒として粉
末状水素イオン交換Ｙ型ゼオライト（商標“ＴＳＺ３２
０１１０Ａ″東ソー（株）製）４ｇを封入し、内部をＮ
２ガスにより置換した後、攪拌しつつ３５０ｋｇ／ｃｄ
、３５０℃で３時間反応させた。Example 1 In an autoclave with a capacity of 100 ml and equipped with a rotary stirrer, 2
-20 ml of MN, 20 ml of decalin, and powdered hydrogen ion-exchanged Y-type zeolite (trademark "TSZ32") as a catalyst.
Enclose 4g of 0110A" manufactured by Tosoh Corporation, and seal the inside with N.
After replacing with 2 gases, 350kg/cd while stirring.
, and reacted at 350°C for 3 hours.
反応終了後、触媒を濾別し、反応液の組成をガスクロマ
トグラフィーにより分析し、反応成績を計算した。After the reaction was completed, the catalyst was filtered off, the composition of the reaction solution was analyzed by gas chromatography, and the reaction results were calculated.
結果を第１表に示す。The results are shown in Table 1.
比較例１
触媒として特開昭６０−９２２２７号公報に開示された
ものと同様の市販品（商標“Ｈ−ｚｓｍ−５”モービル
社製）を使用する以外は実施例１と同様にして、反応を
行なった。Comparative Example 1 The reaction was carried out in the same manner as in Example 1, except that a commercially available product (trademark "H-zsm-5" manufactured by Mobil Corporation) similar to that disclosed in JP-A-60-92227 was used as a catalyst. I did this.
結果を第１表に併せて示す。The results are also shown in Table 1.
第１表
実施例１ 比較例１
２−ＭＮ転化率
（％）
生成物選択率（％）
ジメチルナフタレン ４５． ４ １３． ５２
，６一体 ２０． ３ １５． ８トリメチ
ルナフタレン ２０． ４ ７８． ６３５．７
１６．２
第１表に示す結果から、本発明においては、メチルナフ
タレンの転化率が高く、且っジメチルナフタレンの選択
率にも優れていることが明らかである。Table 1 Example 1 Comparative Example 1 2-MN Conversion (%) Product Selectivity (%) Dimethylnaphthalene 45. 4 13. 52
, 6 one piece 20. 3 15. 8 Trimethylnaphthalene 20. 4 78. 635.7
16.2 From the results shown in Table 1, it is clear that in the present invention, the conversion rate of methylnaphthalene is high and the selectivity of dimethylnaphthalene is also excellent.
（以 上）(that's all)
Claims (2)
ナフタレンを接触させることを特徴とするメチルナフタ
レンの不均化反応によるジメチルナフタレンの製造方法
。(1) A method for producing dimethylnaphthalene by a disproportionation reaction of methylnaphthalene, which comprises bringing methylnaphthalene into contact with faujasite-type zeolite under heating.
る請求項（１）に記載の方法。(2) The method according to claim (1), which is carried out in the presence of a saturated alicyclic hydrocarbon as a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24395889A JPH03106836A (en) | 1989-09-19 | 1989-09-19 | Production of dimethylnaphthalene by disproportionation reaction of methylnaphthalene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24395889A JPH03106836A (en) | 1989-09-19 | 1989-09-19 | Production of dimethylnaphthalene by disproportionation reaction of methylnaphthalene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03106836A true JPH03106836A (en) | 1991-05-07 |
Family
ID=17111571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24395889A Pending JPH03106836A (en) | 1989-09-19 | 1989-09-19 | Production of dimethylnaphthalene by disproportionation reaction of methylnaphthalene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03106836A (en) |
-
1989
- 1989-09-19 JP JP24395889A patent/JPH03106836A/en active Pending
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