JPH0441442A - Purification of cyclohexene - Google Patents
Purification of cyclohexeneInfo
- Publication number
- JPH0441442A JPH0441442A JP14528390A JP14528390A JPH0441442A JP H0441442 A JPH0441442 A JP H0441442A JP 14528390 A JP14528390 A JP 14528390A JP 14528390 A JP14528390 A JP 14528390A JP H0441442 A JPH0441442 A JP H0441442A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexene
- methylcyclopentenes
- crude
- cyclohexane
- extractive distillation
- 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
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 title claims abstract description 108
- 238000000746 purification Methods 0.000 title description 2
- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical class CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 claims abstract description 39
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000000895 extractive distillation Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000002994 raw material Substances 0.000 abstract description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract description 5
- 238000002156 mixing Methods 0.000 abstract description 4
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract description 3
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 abstract description 2
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 14
- CXOZQHPXKPDQGT-UHFFFAOYSA-N 3-Methylcyclopentene Chemical compound CC1CCC=C1 CXOZQHPXKPDQGT-UHFFFAOYSA-N 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid group Chemical group C(CCCCC(=O)O)(=O)O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FWMRUAODTCVEQK-UHFFFAOYSA-N 4-methylcyclopentene Chemical compound CC1CC=CC1 FWMRUAODTCVEQK-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、シクロヘキセンの精製方法に関する。[Detailed description of the invention] (Industrial application field) The present invention relates to a method for purifying cyclohexene.
さらに詳しくは、メチルシクロペンテン類を含有する粗
シクロヘキセンよりメチルシクロペンテン類を除去する
方法に関する。More specifically, the present invention relates to a method for removing methylcyclopentenes from crude cyclohexene containing methylcyclopentenes.
シクロヘキセンは、アジピン酸、リジン粗原料、溶剤、
その他の中間原料として極めて有用な化合（従来の技術
）
高純度のシクロヘキセンを得る方法としては、ヘンゼン
を部分水素化してシクロヘキセンとシクロヘキサンおよ
び未反応のヘンゼンの混合物とし、該混合物より抽出蒸
留により分離取得する方法がある（例えば、特開昭５２
−１４４６４９号公報、特開昭５８−１６４５２４号公
報）。Cyclohexene is adipic acid, lysine crude raw material, solvent,
Compounds extremely useful as other intermediate raw materials (prior art) A method for obtaining high-purity cyclohexene is to partially hydrogenate henzene to form a mixture of cyclohexene, cyclohexane, and unreacted henzene, and separate it from the mixture by extractive distillation. There is a method to do this (for example, JP-A-52
-144649, JP-A-58-164524).
一方、メチルシクロペンテン類を含有するシクロヘキセ
ンは、例えば、シクロヘキセンの酸触媒を用いた水和反
応によるシクロヘキサノールの製造方法において得られ
る（例えば、特公平１−３３４５３号公報）。すなわち
、未反応のシクロヘキセンとシクロヘキセンの異性化で
副生ずるメチルシクロペンテンの混合物として得られる
ものである。この方法で得られるシクロヘキサノールは
極めて高純度であるが、メチルシクロペンテン類を含有
する粗シクロヘキセンを繰り返し水和反応の原料に供し
た場合には、メチルシクロペンテン類の蓄積が生じ、さ
らには、メチルシクロペンテン類より精製する不純物が
シクロヘキサノール中に増加、著しい純度の低下をきた
すこととなる。On the other hand, cyclohexene containing methylcyclopentenes can be obtained, for example, in a method for producing cyclohexanol by a hydration reaction of cyclohexene using an acid catalyst (for example, Japanese Patent Publication No. 1-33453). That is, it is obtained as a mixture of unreacted cyclohexene and methylcyclopentene, which is a by-product from the isomerization of cyclohexene. Cyclohexanol obtained by this method has extremely high purity, but when crude cyclohexene containing methylcyclopentenes is repeatedly used as a raw material for hydration reactions, methylcyclopentenes accumulate, and furthermore, methylcyclopentenes accumulate. The impurities that are purified from the cyclohexanol increase in cyclohexanol, resulting in a significant decrease in purity.
したがって、ここに従来にないメチルシクロペンテンを
含有する粗シクロヘキセンが得られ、なおかつ、該混合
物よりメチルシクロペンテン類を除去する新しい分離技
術が必要となるのである。Therefore, crude cyclohexene containing methylcyclopentene, which has not been seen before, is obtained, and a new separation technique is required to remove methylcyclopentenes from the mixture.
以上、メチルシクロペンテン類を含有する粗シクロヘキ
センの例を示したが、本発明を適用できる範囲は、当然
のことながらこの例に限られるものではない。Although an example of crude cyclohexene containing methylcyclopentenes has been shown above, the scope to which the present invention can be applied is not limited to this example, as a matter of course.
（発明が解決しようとする課Ｎ）
メチルシクロペンテン類を含有する粗シクロヘキセンよ
り、メチルシクロペンテン類を除去しようとした場合、
これを単なる蒸留操作によって分離しようとすると、シ
クロヘキセンとメチルシクロペンテン類との比揮発度が
極めて１に近いために、実質的に不可能である。また、
液々抽出も、溶解特性が極めて似かよっているため困難
である。(Question N to be solved by the invention) When attempting to remove methylcyclopentenes from crude cyclohexene containing methylcyclopentenes,
If an attempt is made to separate this by a simple distillation operation, it is virtually impossible because the relative volatility of cyclohexene and methylcyclopentenes is extremely close to 1. Also,
Liquid-liquid extraction is also difficult because the solubility properties are very similar.
さらには、このような混合物の分離方法として考えられ
る抽出蒸留においても、構造的にも極めて似かよってい
るメチルシクロペンテン類とシクロヘキセンのようなも
のに対する効果は知られていない。Furthermore, extractive distillation, which is considered as a method for separating such mixtures, is not known to have any effect on substances such as methylcyclopentenes and cyclohexene, which are structurally very similar.
（課題を解決するための手段）
本発明者らは、かかるメチルシクロペンテン類を含有す
る粗シクロヘキセンよりメチルシクロペンテン類を除去
する方法を鋭意検討した結果、驚（べきことに、抽出蒸
留による分離が可能なことを見出し、さらには、シクロ
ヘキサンとの混合物とした後、抽出蒸留することで、容
易にメチルシクロペンテン類を除去できることをも見出
し、本発明の完成に至ったものである。(Means for Solving the Problems) As a result of intensive studies by the present inventors on a method for removing methylcyclopentenes from crude cyclohexene containing such methylcyclopentenes, it was surprisingly possible to separate them by extractive distillation. They also discovered that methylcyclopentenes can be easily removed by extractive distillation after forming a mixture with cyclohexane, leading to the completion of the present invention.
すなわち、本発明は、メチルシクロペンテン類を含有す
る粗シクロヘキセンより、抽出蒸留によってメチルシク
ロペンテン類を除去することを特徴とするシクロヘキセ
ンの精製方法であり、さらには、該粗シクロヘキセンを
シクロヘキサノール中した後、抽出蒸留することを特徴
とするシクロヘキセンの精製方法である。That is, the present invention is a cyclohexene purification method characterized by removing methylcyclopentenes from crude cyclohexene containing methylcyclopentenes by extractive distillation, and further, after the crude cyclohexene is dissolved in cyclohexanol, This is a method for purifying cyclohexene characterized by extractive distillation.
以下、本発明の実施態様を説明する。Embodiments of the present invention will be described below.
本発明方法によって精製しようとする粗シクロヘキセン
とは、主に、メチルシクロペンテン類を不純物として含
有するものである。ここでメチルシクロペンテン類とは
、１−メチルシクロペンテン、３−メチルシクロペンテ
ンおよび４−メチルシクロペンテンを言い、特にｌ−メ
チルシクロペンテンを言う。メチルシクロペンテン類の
含有量としては、該粗シクロヘキセン中の重量分率とし
て０．Ｏｌないし数十％である。また、該粗シクロヘキ
セン中にはメチルシクロペンテン類以外の他の不純物、
例えば、微量のベンゼンあるいは溶解水を含んでいても
さしつかえない。The crude cyclohexene to be purified by the method of the present invention mainly contains methylcyclopentenes as impurities. Here, methylcyclopentene refers to 1-methylcyclopentene, 3-methylcyclopentene and 4-methylcyclopentene, and particularly refers to 1-methylcyclopentene. The content of methylcyclopentenes is 0.0% as a weight fraction in the crude cyclohexene. It ranges from Ol to several tens of percent. In addition, the crude cyclohexene contains other impurities other than methylcyclopentenes,
For example, it may contain trace amounts of benzene or dissolved water.
該粗シクロヘキセンとシクロヘキサンを混合スる場合は
、特に粗シクロヘキセン中のメチルシクロペンテン類の
濃度が低い場合に効果があり、例えば、粗シクロヘキセ
ン中のメチルシクロペンテン類の重量分率として０．０
１〜数％において特に有効である。Mixing the crude cyclohexene and cyclohexane is particularly effective when the concentration of methylcyclopentenes in the crude cyclohexene is low; for example, the weight fraction of methylcyclopentenes in the crude cyclohexene is 0.0.
It is particularly effective at 1 to several percent.
また、該粗シクロヘキセンとシクロヘキサンを混合する
場合の割合は、粗シクロヘキセンとシクロヘキサンの合
計に対し、シクロヘキサンの重量分率として０．１ない
し数十％である。Further, when the crude cyclohexene and cyclohexane are mixed, the proportion by weight of cyclohexane is 0.1 to several tens of percent with respect to the total of crude cyclohexene and cyclohexane.
抽出蒸留に使用する抽剤は、シクロヘキサンとシクロヘ
キセンの混合物より各成分の分離可能なものを用いる。The extractant used in the extractive distillation is one that can separate each component from a mixture of cyclohexane and cyclohexene.
例えば、アジポニトリル、スルホラン、Ｎ、Ｎ−ジメチ
ルアセトアミド、マロン酸ジメチル、コハク酸ジメチル
等の溶剤が、あるいはアジポニトリルとＮ、Ｎ−ジメチ
ルアセトアミドの混合溶剤、スルホランとＮ、Ｎ−ジメ
チルアセトアミドの混合溶剤が挙げられる。For example, solvents such as adiponitrile, sulfolane, N,N-dimethylacetamide, dimethyl malonate, and dimethyl succinate, mixed solvents of adiponitrile and N,N-dimethylacetamide, and mixed solvents of sulfolane and N,N-dimethylacetamide are used. Can be mentioned.
使用する抽剤量は、用いる抽剤によって多少異なるが、
抽剤と粗シクロヘキセン、あるいは抽剤と粗シクロヘキ
センおよびシクロヘキサンの混合物の総量に対し、重量
分率として３０〜９５％、好ましくは４０〜９５％であ
る。The amount of extractant used varies somewhat depending on the extractant used, but
The weight fraction is 30 to 95%, preferably 40 to 95%, based on the total amount of the extraction agent and crude cyclohexene, or the mixture of the extraction agent and crude cyclohexene and cyclohexane.
抽出蒸留を実施する場合の操作圧力は、常圧、加圧、減
圧のいずれでもよく、エネルギーの有効利用をはかるた
めに多重効用システムを採用する場合には、減圧系を組
合わせることが望ましい。The operating pressure when performing extractive distillation may be normal pressure, increased pressure, or reduced pressure. When a multiple effect system is employed to effectively utilize energy, it is desirable to combine a reduced pressure system.
粗シクロヘキセンを抽出蒸留分離した場合、シクロヘキ
センは塔底より抽剤との混合物として取り出される。さ
らに、該混合物は蒸留塔において分離され、塔頂より高
純度のシクロヘキセンが取得される。また、粗シクロヘ
キセンとシクロヘキサンの混合物を用いた場合も同様で
ある。When crude cyclohexene is separated by extractive distillation, cyclohexene is taken out from the bottom of the column as a mixture with an extractant. Further, the mixture is separated in a distillation column, and highly purified cyclohexene is obtained from the top of the column. The same applies to the case where a mixture of crude cyclohexene and cyclohexane is used.
以上のごとき本発明方法によって得られるシクロヘキセ
ンの純度は、工業的に要求される純度として充分以上で
あり、具体的には９９％以上、また９９．５％以上、さ
らには９９．９％以上のシクロヘキセンを取得すること
ができる。The purity of cyclohexene obtained by the method of the present invention as described above is more than sufficient for industrially required purity, specifically, 99% or more, 99.5% or more, and even 99.9% or more. Cyclohexene can be obtained.
（発明の効果）
本発明によってメチルシクロペンテン類を含有する粗シ
クロヘキセンを精製して、極めて高純度のシクロヘキセ
ンを取得することができ、その工業的価値は高い。(Effects of the Invention) According to the present invention, crude cyclohexene containing methylcyclopentenes can be purified to obtain extremely pure cyclohexene, which has high industrial value.
（実施例）
以下、実施例をもって本発明をさらに詳細に説明するが
、本発明は、この実施例によってなんら限定されるもの
ではない。(Examples) Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例１
実段数６０段のシーブトレイ型精留塔を用い、下から３
０段目に、粗シクロヘキセンにシクロヘキサンを混合し
た後の組成が重量分率で１−メチルシクロペンテンが０
．１２％、３−メチルシクロペンテンが０．０２％、シ
クロヘキサンが２１゜５９％である混合物を１０ｋｇ／
Ｈで供給した。Example 1 Using a sieve tray type rectification column with 60 plates, 3 from the bottom
In the 0th stage, the composition after mixing cyclohexane with crude cyclohexene is 0 in weight fraction of 1-methylcyclopentene.
．． A mixture of 12% 3-methylcyclopentene, 0.02% 3-methylcyclopentene, and 21°59% cyclohexane was added at a rate of 10 kg/
It was supplied with H.
一方、抽剤としてＮ、Ｎ−ジメチルアセトアミドを使用
し、原料に対しモル比９で、下から５５段目に供給し、
還流比１１．０で常圧にて運転を行ったところ、塔頂留
出液中のシクロヘキセン濃度は０．５５％であり、１−
メチルシクロペンテンは０．３６％、３−メチルシクロ
ペンテンは０゜０５％、他はシクロヘキサンであった。On the other hand, N,N-dimethylacetamide was used as an extraction agent and was supplied to the 55th stage from the bottom at a molar ratio of 9 to the raw material.
When the operation was carried out at normal pressure with a reflux ratio of 11.0, the concentration of cyclohexene in the top distillate was 0.55%, and 1-
Methylcyclopentene was 0.36%, 3-methylcyclopentene was 0.05%, and the rest was cyclohexane.
また、塔底液を実段数４０段のシーブトレイ型精留塔を
用いて、下から２０段目に供給し、還流比４．０で常圧
にて運転したところ、塔頂より、１−メチルシクロペン
テン０．００５％を含むシクロヘキセンが９９．８％の
純度で７．７ｋｇ／Ｈで取得できた。なお、３−メチル
シクロペンテンは検出されなかった。In addition, when the bottom liquid was supplied to the 20th stage from the bottom using a 40-stage sieve tray rectification tower and operated at normal pressure with a reflux ratio of 4.0, 1-methyl Cyclohexene containing 0.005% of cyclopentene was obtained at 7.7 kg/H with a purity of 99.8%. Note that 3-methylcyclopentene was not detected.
比較例１
実段数６０段のシーブトレイ型精留塔を用い、下から３
０段目に、実施例１と同じ組成の原料を１０ｋｇ／Ｈで
供給し、抽剤を供給することなしに蒸留を行った。Comparative Example 1 Using a sieve tray type rectification column with 60 plates, 3 from the bottom
A raw material having the same composition as in Example 1 was supplied to the 0th stage at a rate of 10 kg/H, and distillation was performed without supplying an extractant.
還流比１１で常圧にて運転を行ったところ、塔底より７
．７ｋｇ／Ｈで抜き出されたシクロヘキセン中の各濃度
は、１−メチルシクロペンテン０．１１％、３−メチル
シクロペンテン０．０１％、シクロヘキサン２３．０１
％であり、メチルシクロペンテン類をほとんど分離でき
なかった。When operating at normal pressure with a reflux ratio of 11, 7
．． The respective concentrations in cyclohexene extracted at 7 kg/H are 1-methylcyclopentene 0.11%, 3-methylcyclopentene 0.01%, and cyclohexane 23.01%.
%, and methylcyclopentenes could hardly be separated.
Claims (2)
センより、抽出蒸留によってメチルシクロペンテン類を
除去することを特徴とするシクロヘキセンの精製方法。(1) A method for purifying cyclohexene, which comprises removing methylcyclopentenes from crude cyclohexene containing methylcyclopentenes by extractive distillation.
、抽出蒸留する請求項１記載の方法。(2) The method according to claim 1, wherein the crude cyclohexene is mixed with cyclohexane and then subjected to extractive distillation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2145283A JP2802674B2 (en) | 1990-06-05 | 1990-06-05 | Purification method of cyclohexene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2145283A JP2802674B2 (en) | 1990-06-05 | 1990-06-05 | Purification method of cyclohexene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0441442A true JPH0441442A (en) | 1992-02-12 |
| JP2802674B2 JP2802674B2 (en) | 1998-09-24 |
Family
ID=15381561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2145283A Expired - Lifetime JP2802674B2 (en) | 1990-06-05 | 1990-06-05 | Purification method of cyclohexene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2802674B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08195275A (en) * | 1995-01-19 | 1996-07-30 | Nichifu Co Ltd | Linear heating element |
| JP2003040079A (en) * | 2001-07-30 | 2003-02-13 | Nifco Inc | Seat belt guide |
-
1990
- 1990-06-05 JP JP2145283A patent/JP2802674B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08195275A (en) * | 1995-01-19 | 1996-07-30 | Nichifu Co Ltd | Linear heating element |
| JP2003040079A (en) * | 2001-07-30 | 2003-02-13 | Nifco Inc | Seat belt guide |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2802674B2 (en) | 1998-09-24 |
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