JPH0267264A - Production of bis(2,2,6,6-tetramethyl-4-piperidino)sebacate - Google Patents
Production of bis(2,2,6,6-tetramethyl-4-piperidino)sebacateInfo
- Publication number
- JPH0267264A JPH0267264A JP21951288A JP21951288A JPH0267264A JP H0267264 A JPH0267264 A JP H0267264A JP 21951288 A JP21951288 A JP 21951288A JP 21951288 A JP21951288 A JP 21951288A JP H0267264 A JPH0267264 A JP H0267264A
- Authority
- JP
- Japan
- Prior art keywords
- tetramethyl
- sebacate
- piperidino
- catalyst
- piperidinol
- 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
- 229940116351 sebacate Drugs 0.000 title claims abstract description 12
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- BVFSYZFXJYAPQJ-UHFFFAOYSA-N butyl(oxo)tin Chemical compound CCCC[Sn]=O BVFSYZFXJYAPQJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 claims abstract 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N n-Decanedioic acid Natural products OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- -1 sebacic acid ester Chemical class 0.000 claims description 6
- 238000005809 transesterification reaction Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 229940014772 dimethyl sebacate Drugs 0.000 abstract description 4
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000004611 light stabiliser Substances 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract 5
- 238000002845 discoloration Methods 0.000 abstract 1
- 239000002861 polymer material Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- KKZZSTCINUMTGD-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidin-4-ol Chemical compound CC1C(O)CCN(C)C1(C)C KKZZSTCINUMTGD-UHFFFAOYSA-N 0.000 description 1
- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HMOFGLGHQFZQDS-UHFFFAOYSA-N bis(2-methylpropyl) decanedioate Chemical compound CC(C)COC(=O)CCCCCCCCC(=O)OCC(C)C HMOFGLGHQFZQDS-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- NGDPCAMPVQYGCW-UHFFFAOYSA-N dibenzothiophene 5-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3C2=C1 NGDPCAMPVQYGCW-UHFFFAOYSA-N 0.000 description 1
- 229940031954 dibutyl sebacate Drugs 0.000 description 1
- GQIDSVPVVYHXAP-UHFFFAOYSA-N dihexyl decanedioate Chemical compound CCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCC GQIDSVPVVYHXAP-UHFFFAOYSA-N 0.000 description 1
- 229940031569 diisopropyl sebacate Drugs 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- WZURZWRVLHOHAS-UHFFFAOYSA-N dipentyl decanedioate Chemical compound CCCCCOC(=O)CCCCCCCCC(=O)OCCCCC WZURZWRVLHOHAS-UHFFFAOYSA-N 0.000 description 1
- XFKBBSZEQRFVSL-UHFFFAOYSA-N dipropan-2-yl decanedioate Chemical compound CC(C)OC(=O)CCCCCCCCC(=O)OC(C)C XFKBBSZEQRFVSL-UHFFFAOYSA-N 0.000 description 1
- UHGPEWTZABDZCE-UHFFFAOYSA-N dipropyl decanedioate Chemical compound CCCOC(=O)CCCCCCCCC(=O)OCCC UHGPEWTZABDZCE-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003329 sebacic acid derivatives Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ビス（２，２，６，６−テトラメチル−４−
ピペリジノ）セバケートの改良された製造方法を提供す
るものである０本発明で製造されるビス（２，２，６，
６−テトラメチル−４−ピペリジノ）セバケートは高分
子材料の光安定剤として近年、特にその有用性が重視さ
れている化合物である。Detailed Description of the Invention [Industrial Field of Application] The present invention provides bis(2,2,6,6-tetramethyl-4-
The present invention provides an improved method for producing bis(2,2,6,
6-Tetramethyl-4-piperidino) sebacate is a compound whose usefulness has been particularly emphasized in recent years as a light stabilizer for polymeric materials.
ビス（２，２，６，６−テトラメチル−４−ピペリジノ
）セバケートを製造する方法としては、（１） ２．
２，６．６−テトラメチル−４−ピペリジノールと酸ク
ロライドとをピリジンなどの脱酸剤を使用してエステル
化する方法（Ｂｅｒ、、 ４５２０６０ （１９１２）
？特公昭４６−４２６１８号公報〕、または
（２）Ｎ−メチル−４−ピペリジノールとカルボン酸ア
ステルとから、ナトリウムエトキシドなどの触媒を使っ
てエステル交換反応により製造する方法〔英国特許第８
９０６０５号〕、などが知られている。The method for producing bis(2,2,6,6-tetramethyl-4-piperidino)sebacate includes (1) 2.
A method of esterifying 2,6.6-tetramethyl-4-piperidinol and acid chloride using a deoxidizing agent such as pyridine (Ber, 452060 (1912))
? Japanese Patent Publication No. 46-42618], or (2) a method of producing it by transesterification reaction from N-methyl-4-piperidinol and a carboxylic acid ester using a catalyst such as sodium ethoxide [British Patent No. 8
No. 90605], etc. are known.
前記（１１の酸クロライドを用いるエステル化法におい
てはセバシン酸誘導体の中でも高価で工業的規模での入
手が困難なセバシン酸りａライドを使用せねばならず、
さらにピリジンなどの脱酸剤を多量に使わなければなら
ないなど経済的に有利な製造方法とは言い難い。In the esterification method using acid chloride (11), sebacic acid a-ride, which is expensive among sebacic acid derivatives and difficult to obtain on an industrial scale, must be used.
Furthermore, it is difficult to say that it is an economically advantageous production method because a large amount of a deoxidizing agent such as pyridine must be used.
また、前記（２）のエステル交換法によれば、（１）に
比べ原料的には改善されたといえるが、触媒のナトリウ
ムエトキシドやナトリウムメトキシドは比較的不安定な
化合物であり、反応原料中や空気中の水分などにより水
酸化ナトリウムに加水分解されやすい、そのため、原料
であるセバシン酸エステルが生じた水酸化ナトリウムに
よって反応中に加水分解を受け、反応物の着色および収
率の低下を来たすなどの問題点が存在し、満足すべき方
法とは言い難い。In addition, according to the transesterification method (2) above, it can be said that the raw materials are improved compared to (1), but the catalysts, sodium ethoxide and sodium methoxide, are relatively unstable compounds, and the reaction raw materials It is easily hydrolyzed to sodium hydroxide due to moisture in the air or in the air. Therefore, sebacic acid ester, a raw material, is hydrolyzed by the generated sodium hydroxide during the reaction, resulting in coloration of the reaction product and a decrease in yield. However, it is difficult to say that this is a satisfactory method, as there are problems such as problems such as nuisance.
（！Ｉ！！題を解決するための手段〕
本発明者らは、上記課題を克服するために鋭意研究を行
なった結果、有機錫化合物であるモノブチル錫オキサイ
ド（以下、ＭＢＴＯと略すこともある）およびジブチル
錫オキサイド（以下、ＤＢＴｏと略すこともある）が、
エステル交換触媒として極めて触媒活性が高（、かつ前
記問題点の解消された優れた方法であることを見い出し
、本発明を完成するに至った。(!I!!Means for solving the problem) As a result of intensive research to overcome the above problems, the present inventors found that monobutyltin oxide (hereinafter sometimes abbreviated as MBTO), which is an organic tin compound, ) and dibutyltin oxide (hereinafter sometimes abbreviated as DBTo),
We have discovered that this is an excellent method that has extremely high catalytic activity as a transesterification catalyst (and has solved the above problems), and has completed the present invention.
即ち、本発明は２．２，６．６−テトラメチル−４−ピ
ペリジノールと一般式
％式％（１）
（式中、Ｒは炭素数１〜８個のアルキル基を示す、）
で表わされるセバシン酸エステルをエステル交換反応に
付すことによってビス（２，２，６，６−テトラメチル
−４−ピペリジノ）セバケートを製造する方法において
、モノブチル錫オキサイドおよびジブチル錫オキサイド
を単独または併用にて触媒として用いることを特徴とす
るビス（２，２゜６．６−テトラメチル−４−ピペリジ
ノ）セバケートの製造方法に関する。That is, the present invention relates to 2.2,6.6-tetramethyl-4-piperidinol represented by the general formula % (1) (wherein R represents an alkyl group having 1 to 8 carbon atoms) In a method for producing bis(2,2,6,6-tetramethyl-4-piperidino) sebacate by subjecting sebacic acid ester to transesterification reaction, monobutyltin oxide and dibutyltin oxide are used alone or in combination as a catalyst. The present invention relates to a method for producing bis(2,2°6,6-tetramethyl-4-piperidino)sebacate, which is characterized in that it is used.
触媒として用いられるＭＢＴＯおよびＤＢＴＯは単独ま
たは併用して使用してもよく、その使用量は原料の２．
２．６．６−テトラメチル−４−ピペリジノールに対し
０．００１重量％以上で、好適には０．Ｏ１〜１．０重
量％である。MBTO and DBTO used as catalysts may be used alone or in combination, and the amount used is determined by the amount of 2.0% of the raw material.
0.001% by weight or more, preferably 0.001% by weight or more based on 2.6.6-tetramethyl-4-piperidinol. O is 1 to 1.0% by weight.
また、原料として用いられる一般式（りの化合物として
は、例えばセバシン酸ジメチル、セバシン酸ジエチル、
セバシン酸ジプロピル、セバシン酸ジイソプロピル、セ
バシン酸ジブチル、セバシン酸ジイソブチル、セバシン
酸ジ第３級ブチル、セバシン酸ジペンチル、セバシン酸
ジヘキシル、セバシン酸ジヘブチルおよびセバシン酸ジ
オクチルなどがあげられるが、好適にはセバシン酸ジメ
チルおよびセバシン酸ジエチルが用いられる。In addition, compounds with the general formula (RI) used as raw materials include, for example, dimethyl sebacate, diethyl sebacate,
Examples include dipropyl sebacate, diisopropyl sebacate, dibutyl sebacate, diisobutyl sebacate, ditertiary butyl sebacate, dipentyl sebacate, dihexyl sebacate, dihebutyl sebacate, and dioctyl sebacate. Preferably, sebacate Dimethyl and diethyl sebacate are used.
溶媒は特に必要ではないが、反応の制御、温度コントロ
ールなど操作性の向上からトルエンおよびキシレンなど
の不活性溶媒を使用することが好ましい。Although a solvent is not particularly necessary, it is preferable to use an inert solvent such as toluene and xylene in order to improve operability such as reaction control and temperature control.
反応温度は溶媒使用の有無、使用溶媒の種類、またはそ
の他反応条件により異なるが、８０〜２００℃でよく、
例えばトルエンを用いた常圧での反応においては１００
〜１４０’ｃが好適である。The reaction temperature varies depending on whether or not a solvent is used, the type of solvent used, and other reaction conditions, but may be between 80 and 200°C.
For example, in a reaction using toluene at normal pressure, 100
-140'c is suitable.
原料の２．２．６．６−テトラメチル−４−ピペリジノ
ールとセバシン酸エステルの使用比率は化学量論的量で
よいが、微量の未反応物の除去のため２．２，６．６−
テトラメチル−４−ピペリジノールを少し過剰に使用す
ることが好ましい。The ratio of raw materials 2.2.6.6-tetramethyl-4-piperidinol and sebacic acid ester may be stoichiometric, but 2.2.6.6-tetramethyl-4-piperidinol and sebacic acid ester may be used in stoichiometric amounts, but 2.2.6.6-
It is preferred to use a slight excess of tetramethyl-4-piperidinol.
本発明によりビス（２，２，６，６−テトラメチル−４
−ピペリジノ）セバケートを製造すると、下記実施例第
１表から明らかな通り、従来のナトリウムメトキシド触
媒を用いた場合に比べて収率、反応物の着色の点で特に
優れていることが理解される。According to the present invention, bis(2,2,6,6-tetramethyl-4
-Piperidino) sebacate is understood to be particularly superior in terms of yield and coloring of the reactant, as is clear from Example Table 1 below, compared to when conventional sodium methoxide catalysts are used. Ru.
（実施例〕
以下、実施例により本発明を具体的に説明するが、本発
明はこれらにより何ら限定されるものではない。(Examples) Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited by these in any way.
実施例１
温度計、分溜塔、攪拌機付き２００１容フラスコにセバ
シン酸ジメチル２３．０ｇ、２．２，６゜６−テトラメ
チル−４−ピペリジノール３５．０ｇ。Example 1 23.0 g of dimethyl sebacate and 35.0 g of 2.2,6°6-tetramethyl-4-piperidinol were placed in a 2001-volume flask equipped with a thermometer, a fractionator, and a stirrer.
トルエン３０１１および触媒としてＤＢＴＯｏ、０５ｇ
を仕込み、内温１２０〜１３０℃に保ち副生するメタノ
ールを分溜塔を通し溜去させた。メタノールの溜出がな
くなるまで約４時間分溜した後、反応液を冷却後トルエ
ン１００ｍ１で希釈し、５％炭酸水素ナトリウム水溶液
５０ｍ１で２回、さらに水５０ｍ１で２回洗浄後、減圧
下にトルエンを溜去すると融点８１〜８３℃のビス（２
，２，ｌｌｉ、 ６−テトラメチル−４−ピペリジノ
）セバケート４７、０ ｇが得られた。ガスクロマトグ
ラフィーによる分析で純度は９８．２％、収率はセバシ
ン酸ジメチルを基準にして９７．９％であった。Toluene 3011 and DBTOo as catalyst, 05g
was charged, the internal temperature was maintained at 120 to 130°C, and by-produced methanol was distilled off through a fractionation column. After fractional distillation for about 4 hours until methanol no longer distilled out, the reaction solution was cooled, diluted with 100 ml of toluene, washed twice with 50 ml of 5% aqueous sodium bicarbonate solution and twice with 50 ml of water, and then diluted with toluene under reduced pressure. When the is distilled off, bis(2
,2,lli,6-tetramethyl-4-piperidino)sebacate 47.0 g was obtained. Analysis by gas chromatography showed that the purity was 98.2% and the yield was 97.9% based on dimethyl sebacate.
以下、原料のセバシン酸エステルおよび触媒をかえて実
施例１と同様に反応させた場合を実施例２〜４として第
１表に示す、また、対照として従来のナトリウムメトキ
シド（ＮａＯＣＨｓ）触媒を用いた比較例を同時に示し
、各実施例の収率、ガスクロマトグラフィーによる分析
純度（Ｇ、 Ｃ。Table 1 below shows Examples 2 to 4 in which the reaction was carried out in the same manner as in Example 1 by changing the raw material sebacic acid ester and the catalyst. Comparative examples are also shown, and the yield and purity analyzed by gas chromatography (G, C) of each example are also shown.
純度）および着色度（ＡＰＨＡ標準色列）について比較
した。但し、表中の実施例および比較例はすべて２．２
．６．６−テトラメチル−４−ピペリジノール３５．０
ｇを用いた場合についてである。Purity) and degree of coloration (APHA standard color series) were compared. However, all examples and comparative examples in the table are 2.2.
．． 6.6-tetramethyl-4-piperidinol 35.0
This is about the case where g is used.
−以下余白一-Less than 1 margin
Claims (1)
一般式 ＲＯＯＣ（ＣＨ＿２）＿３ＣＯＯＲ （式中、Ｒは炭素数１〜８個のアルキル基を示す。） で表わされるセバシン酸エステルをエステル交換反応に
付すことによってビス（２，２，６，６−テトラメチル
−４−ピペリジノ）セバケートを製造する方法において
、モノブチル錫オキサイドおよびジブチル錫オキサイド
を単独または併用にて触媒として用いることを特徴とす
るビス（２，２，６，６−テトラメチル−４−ピペリジ
ノ）セバケートの製造方法。[Claims] 2,2,6,6-tetramethyl-4-piperidinol represented by the general formula ROOC(CH_2)_3COOR (wherein R represents an alkyl group having 1 to 8 carbon atoms) In a method for producing bis(2,2,6,6-tetramethyl-4-piperidino) sebacate by subjecting sebacic acid ester to transesterification reaction, monobutyltin oxide and dibutyltin oxide are used alone or in combination as a catalyst. A method for producing bis(2,2,6,6-tetramethyl-4-piperidino)sebacate, characterized in that it is used.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21951288A JPH0267264A (en) | 1988-09-01 | 1988-09-01 | Production of bis(2,2,6,6-tetramethyl-4-piperidino)sebacate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21951288A JPH0267264A (en) | 1988-09-01 | 1988-09-01 | Production of bis(2,2,6,6-tetramethyl-4-piperidino)sebacate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0267264A true JPH0267264A (en) | 1990-03-07 |
Family
ID=16736627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21951288A Pending JPH0267264A (en) | 1988-09-01 | 1988-09-01 | Production of bis(2,2,6,6-tetramethyl-4-piperidino)sebacate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0267264A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5498751A (en) * | 1993-09-03 | 1996-03-12 | Cps Chemical Company, Inc. | Organotin catalyzed transesterification |
| US5606103A (en) * | 1993-09-03 | 1997-02-25 | Cps Chemical Company, Inc. | Organotin catalyzed transesterification |
-
1988
- 1988-09-01 JP JP21951288A patent/JPH0267264A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5498751A (en) * | 1993-09-03 | 1996-03-12 | Cps Chemical Company, Inc. | Organotin catalyzed transesterification |
| US5554785A (en) * | 1993-09-03 | 1996-09-10 | Cps Chemical Company, Inc. | Organotin catalyzed transesterification products |
| US5606103A (en) * | 1993-09-03 | 1997-02-25 | Cps Chemical Company, Inc. | Organotin catalyzed transesterification |
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